Modularity and three-dimensional isostructurality of...

IUCrJ Volume 2 (2015)

Supporting information for article

Modularity and three-dimensional isostructurality of novel synthons in sulfonamidendashlactam cocrystals

Geetha Bolla Sudhir Mittapalli and Ashwini Nangia

IUCrJ (2015) 2 doi101107S2052252515004960 Supporting information sup-1

Table S1 Hydrogen bonding parameters in benzene sulfonamide cocrystals

Compound Interactions HmiddotmiddotmiddotA

Aring

DmiddotmiddotmiddotA Aring DndashHmiddotmiddotmiddotA ordm Symmetry

2ABSAndashCPR N1ndashH1AmiddotmiddotmiddotO3 218(2) 2910(2) 159 12+x12-y12+z

N1ndashH1BmiddotmiddotmiddotO3 196(2) 2855(3) 171 12-x12+y12-z

N2ndashH2AmiddotmiddotmiddotO2 228 3108(2) 162 12+x12-y12+z

N2ndashH2BmiddotmiddotmiddotO1 218 2892(2) 140 Intermolecular

N3ndashH3AmiddotmiddotmiddotO3 213 2968(2) 165 1-x-y-z

2ClBSAndashVLM N1ndashH1AmiddotmiddotmiddotO3 203 2829(3) 169 a

N1ndashH1BmiddotmiddotmiddotCl1 281 3295(2) 118 Intermolecular

N1ndashH1BmiddotmiddotmiddotO1 216 2922(2) 151 x12-y-12+z

N2ndashH2AmiddotmiddotmiddotO3 208 2939(3) 177 1-x-y1-z

C5ndashH5middotmiddotmiddotO2 253 3238(3) 133 -x-12+y12-z

2ClBSAndashCPR N1ndashH1AmiddotmiddotmiddotO3 197 2871(1) 176 a

N1ndashH1BmiddotmiddotmiddotO2 235 3088(1) 151 x12-y12+z


4BrBSAndashVLM N1ndashH1AmiddotmiddotmiddotO3 206 2866(4) 170 a

N1ndashH1BmiddotmiddotmiddotO3 200 2879(3) 171 12-x12+y12-z

N2ndashH2AmiddotmiddotmiddotN1 250 3172(4) 154 12-x12+y12-z

4BrBSAndashCPR N1ndashH1AmiddotmiddotmiddotO3 196 2887(5) 169 -x12+y12-z

N1ndashH1BmiddotmiddotmiddotO3 231 2960(5) 159 12-x-y-12+z

N2ndashH2AmiddotmiddotmiddotN1 258 3301(6) 144 1-x-12+y12-z

C5ndashH5middotmiddotmiddotO2 240 3151(5) 138 -1+xyz

4ClBSAndashVLM N1ndashH1AmiddotmiddotmiddotO3 208 2881(4) 164 12-x12+y12-z

N1ndashH1BmiddotmiddotmiddotO3 204 2855(5) 172 a


4ClBSAndashCPR N1ndashH1AmiddotmiddotmiddotO3 219 2908(1) 147 1-x12+y12-z


N2ndashH2AmiddotmiddotmiddotN1 256 3285(2) 142 -y12+z

C3ndashH3middotmiddotmiddotO1 239 3145(1) 138 1+xyz

BSAndashVLM N1ndashH1AmiddotmiddotmiddotO3 205 2890(1) 164 12+x12-y12+z


N2ndashH2AmiddotmiddotmiddotN1 248 3270(1) 152 1+xyz

BSAndashCPR N1ndashH1AmiddotmiddotmiddotO3 204 2871(2) 159 12-x1-y frac12+z


N1ndashH1BmiddotmiddotmiddotO3 210 2859(1) 170 1-x12+y 32-z



BSAndashAZL N1ndashH1AmiddotmiddotmiddotO3 212 2879(3) 158 12+x12-y12+z

N1ndashH1BmiddotmiddotmiddotO3 203 2905(4) 169 12-x-12+y12-z

N2ndashH2AmiddotmiddotmiddotO3 218 2999(3) 168 1-x1-y-z

OTSAndashVLM N1ndashH1AmiddotmiddotmiddotO3 203 2857(2) 161 12-x-12+y12-z

N1ndashH1BmiddotmiddotmiddotO1 210 2988(2) 157 1+xyz

N2ndashH2AmiddotmiddotmiddotO3 209 2948(1) 175 1-x1-y1-z

PTSAndashVLM N1ndashH1AmiddotmiddotmiddotO1 226 3015(3) 163 1+xyz


N2ndashH2AmiddotmiddotmiddotO3 215 2904(3) 176 -x1-y-z

SNAndashCPR N1ndashH1AmiddotmiddotmiddotO3 216 2902(5) 150 12-x-y-12+z

N1ndashH1BmiddotmiddotmiddotO3 196 2845(5) 164 -x12+y12-z

N2ndashH2AmiddotmiddotmiddotO1 241 3264(5) 166 1-x-12+y12-z

N2ndashH2BmiddotmiddotmiddotO2 226 2998(5) 142 -x-12+y12-z


C3ndashH3middotmiddotmiddotO2 257 3482(5) 168 1-x-12+y12-z

a Molecules in the same asymmetric unit



Aring




















































a Moleculesions in the same asymmetric unit


Table S2 Classification of primary sulfonamides based on synthons present and their CSD REFCODEs

Sulfonamides (220)

Alternative dimers (5)

PECTOI RIBQID VUSMEC WOBHUR ZEBYEM

Anti Catemer (50)

ADAGUI AFIMEJ AMEVAP AZADAH AZAGUE BAPYIB BAPYIB BIZPIK

BIZPOQ BSBTHP AZACOU CIVBAK10 DIBBUL DUCVED EWUHAF EXICIX

EXICIX FAVWIJ FAXZIO GEQYIK GODRUM HCSBTZ ICUTOR JEFNOY

JIGCUX KIKCUD KUSVEZ KUZWIM MESXIR PIMZAO POHYER PUFHUU

QUYKOL QUYRIM SODGID SULAMD03 SULTAM SULTAM01 ULIDOJ VUXPUZ

WEPMAH ZEBYOW BATNOB CAFVUA COYVER GOMSAE JEFPAM LAWKUP

NIWPAL OCAMUB

Dimer discrete (9)

AZADEL GUFQED IDIMOY JEFNAK KIXHEF RIHGOF TIGLOL VABFAH

XAVKUB

Continuous dimers (7)

AFONAM GUCMEW JABJAY PERQOT SETHEE USOBAG TIYXII

Finite catemers (7)

IFAXAX JAWHOF SEQJUT VOHZIC ZAPJAD ENIROI GOFYIL

Finite dimers (21)

CIKJAI CSBSMP EFOFAH EVAGUE GODSAT KIXHEF LAPNAT LAPPEZ

LISKUU MEWXAP MUWCUD SEBPAQ SEQKEE WACJIT WAWNAK XETFAF

ZAHBEP ATDZSA CEFMUX PODPUU LISLAB

Rings forms dimers (4)

AMAVIT AZADIP JEFPIU PODQEF

Syn Catemers (16)

CIKSIA CUDDEL ETOMUV GAQBUX HUCSUU JEFMUD JEFNIS LOMWIT

PAVBUL PODQAB PUMPOD PUMPUJ QUYTIO WAWMUD NIGNEY MOKMIJ

Tetramer rings (21)


BUDYEF JABJEC JEFMAJ JEFNEO JEFNUE JEFPOA KIFZUV KUSVEZ

MESXUD MSULPH01 MUBVOV NIGNEY PERQEJ QISQOZ TIBPAW UJIBAR

WEBWUV ZZZULS01 DOLDIT EXICOD HUFVOU

Three point synthons (4)

ADAGUI FIYYES FOGVIG01 RIFVIM

Miscellaneous (76)

ADILOP AZAMEU BIXMUR BUFMAR CADTEG CANWIX CBSTHP CIKJAI

CIKSIA CIMKOA CSBSMP DOSDOE EFOFAH EVAGUE EVAWAA FUZXUU

GEVBAL GODSAT GOMKUP HABSOS HILRAW HSLSTZ IFAFAX IPSULF

JAWHOF JAZVEL10 JAZVIP10 JAZVOV10 JAZZOZ10 JEFPEQ KEFROC KIXHEF

KIXPIQ KUVFIR LAPNAT LAPPEZ LEFFAF LESZUG LISKUU MUWCUD

PEDBOR PEHWEF PILPIK PODQAB POWBUZ PUMPOD PYMSBZ11 QAKXUX

SEBPAQ SEQJUT SEQKEE SODGID SOJNEK SULPIA10 TELWAI UJIBEV

UJIBIZ UJIBOF VAWMOV VOHZIC VUXPUZ WACJIT WAWNAK WIGXIU

WIXGIV XETFAF YIKZUP ZAHBEP ZAPJAD ZEBYOW XAVKUB01 XAVKUB

DOPVIP GOMRUX MESXOX NARVUZ


BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM

Figure S1 2D sheet like structure propagation of the catemer chain Synthon 1 in cocrystal structures

(a) 2ABSAndashCPR

(b) BSAndashAZL

Figure S2 Head to face packing thorugh dimer-cyclic ring motif Synthon 2 in cocrystals 2ABSAndashCPR

and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM

Figure S3 2D packing of OTSAndashVLM and PTSAndashVLM cocrystals in the bc-plane


Figure S4 Powder X-ray diffraction patterns of the 3D isostructural catemer synthon cocrystals pairs The

near identical PXRD lines support isostructurility and isomorphous nature of the structures


AQUFEY

NndashHmiddotmiddotmiddotO

BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM

SO2NH2middotmiddotmiddotN-oxide

IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL

SO2NH2middotmiddotmiddotP-oxide

JAYCAN

SO2NH2middotmiddotmiddotAs-oxide

LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ

NndashHmiddotmiddotmiddotOndash

PIRLUZ


PIRXUL


VIGDAR


VOMMUF

NndashHmiddotmiddotmiddotN

XAVTEV


(a)

ADECIW


AGOKUC


EXANEX

2-amino-PymiddotmiddotmiddotCOOH

EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO


2-amino-PymiddotmiddotmiddotCOOH 2-amino-PymiddotmiddotmiddotCOOH 2-amino-PymiddotmiddotmiddotCOOH 2-amino-PymiddotmiddotmiddotCOOH

EXAPAV

2-amino-PymiddotmiddotmiddotCONH

EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP

2-amino-Pymiddotmiddotmiddothetrocylic N


UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)

BSA catemer chains forms rings

OTSA results ring motifs

PTSA catemer chains forms rings

2ABSA catemer chains forms rings

2ClBSA catemer chains forms rings



4BRBSA catemer chains forms rings

SNA-form I catemer chains forms

rings

SNA form II dimer and

discrete H bond

SNA Form III dimer followed by dimer

VLM lactam hydrate

CPR dimer synthon

AZL shows catemer synthon

(c)

Figure S5 (a) Reported primary sulfonamides cocrystal along with their Refcodes and interactions

presented with coformers (b) Secondary sulfonamides cocrystals along with their Refcodes and interactions

presented with coformers (c) All the sulfonamides as well as coformers crystals structures along with their


synthons reported in CSD database The trend is that most of the sulfonamide structuress are contains

catemer chains

Table S3 The percentage of intermolecular interactions present in cocrystal structures from Hirshfeld

surface analysis

Cocrystal NhellipH OhellipH XhellipH ChellipH Others

2ABSAndashCPR 43 293 ----- 129 535

2ClBSAndashVLM 28 256 117 57 542

2ClBSAndashCPR 29 318 110 88 455

4BrBSAndashVLM 43 299 135 25 498

4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570

SNAndashCPR 52 299 112 537


BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH

Figure S6 Hirshfeld 2D finger print plots of the interactions present in sulfonamide-lactam cocrystals


Figure S7 Percentage intermolecular contacts contributions to the Hirshfeld surface area in sulfonamide-

lactam cocrystals

Analysis of sulfonamide cocrystals by Vibrational Spectroscopy FT-IR spectroscopy is one of the

prominent analytical methods for studying polymorphscocrystals in solid state chemistry Hypsochromic

bathochromic shift of the vibrational frequency values for the ground adducts with starting individuals

confirm new product formation Broad NndashH stretching vibrations for sulfonamides and lactams are observed

in the range 3490ndash3330 cm-1 respectively due to intermolecular hydrogen bonding Asymmetric and

symmetric S=O stretching vibrations appear as strong absorption peaks in the range 1344ndash1305 cm-1 and

1178ndash1144 cm-1 see Table S4 All the spectra comparisons for sulfonamide cocrystals were kept in Figure

S7 SI

Table S4 IR frequency (cmndash1) of sulfonamide-lactam cocrystals

Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599







Figure S8 IR spectra of all sulfopnamidendashlactam cocrystals along with starting materials


Furosemide-Isonicotinamide (11)


Furosemide-Nicotinamide (IV)

Furosemide-Nicotinamide (III)

Hydrochlorothiazide-Isonicotinamide

Hydrochlorothiazide-Nicotinamide


Hydrochlorothiazide-succinamide

Acetazolamide-Picolinamide

Celecoxib-Nicotinamide

Sulfonamide-2Pyridone

Figure S9 2D Packing visualization of the primary sulfonamides with amide coformers reported with

sulfonamide-carboxamide heterosynthon in the CSD database


Table S1 Hydrogen bonding parameters in benzene sulfonamide cocrystals


Aring























































Aring























































Sulfonamides (220)



Anti Catemer (50)







NIWPAL OCAMUB

Dimer discrete (9)


XAVKUB



Finite catemers (7)


Finite dimers (21)






Syn Catemers (16)



Tetramer rings (21)







Miscellaneous (76)












BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599












































Aring























































Sulfonamides (220)



Anti Catemer (50)







NIWPAL OCAMUB

Dimer discrete (9)


XAVKUB



Finite catemers (7)


Finite dimers (21)






Syn Catemers (16)



Tetramer rings (21)







Miscellaneous (76)












BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599













































Sulfonamides (220)



Anti Catemer (50)







NIWPAL OCAMUB

Dimer discrete (9)


XAVKUB



Finite catemers (7)


Finite dimers (21)






Syn Catemers (16)



Tetramer rings (21)







Miscellaneous (76)












BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599




























Miscellaneous (76)












BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























BSAndashVLM

BSAndashCPR

4ClBSAndashCPR

4BrBSAndashCPR

SNAndashCPR


4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























4ClBSAndashVLM

4BrBSAndashVLM


(a) 2ABSAndashCPR

(b) BSAndashAZL


and BSAndashAZL


(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























(a) OTSAndashVLM

(b) PTSAndashVLM






AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599


























AQUFEY


BEYZEM


DATFAH


FEFYAS


HSLSTZ


IWERIM


IWERUY


IWERAE


IWEQEX


IWEREI


IWEROS


DATFEL


SANAPY


DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























DATFIP


RUYGIC


STHSAM01



JACWEL


JAYCAN


LIQPUY


LIQQIN


LIQQEJ


LIQQAF


LOFLAV


LOFLEZ


LOFLID


MUPPIX


NARWAG



NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























NETDIZ


PIRLUZ


PIRXUL


VIGDAR


VOMMUF


XAVTEV


(a)

ADECIW


AGOKUC


EXANEX


EXANAT


EXANIB

EXANOH

EXANUN

FEVKUO



EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599
























EXAPAV


EXAPID


EXAPUP


EXAPUZ


HOCCOT


HOCCUZ


HORNEI


OTESAI


PAVKUU


PIRLUZ


PIRXOF


PIRQUL


RILQUA


SACCAF


SMZPMP



UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























UFERED

UNEZAO01

Amide dimer type

VIGFOH


VUGMIT


VUGMOJ


VUHFIO


YANNEH


YESKIR


SORWEB


SORWIF


PAVKUU


SABDOQ


WXAMUM


XEXCIE


XOBCOH


YIZQAA



XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























XEXCAE


HOCCEJ


SACCAF01


ZIMHIO01


(b)










rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599

























rings


discrete H bond


VLM lactam hydrate

CPR dimer synthon


(c)






catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599
























catemer chains


surface analysis


2ABSAndashCPR 43 293 ----- 129 535




4BrBSAndashCPR 26 271 127 124 452


4ClBSAndashCPR 21 271 123 125 460

BSAndashVLM 35 324 --- 127 514

BSAndashCPR 36 345 ----- 101 518

BSAndashAZL 23 327 ---- 123 527

OTSAndashVLM 42 276 ---- 88 594

PTSAndashVLM 44 310 ---- 76 570



BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























BSAndashVLM All

BSAndashVLM OH

BSAndashVLM CH

BSAndashVLM NH

BSAndashCPR All

BSAndashCPR OH

BSAndashCPR CH

BSAndashCPR NH

4ClBSAndashCPR All

4ClBSAndashCPR OH

4ClBSAndashCPR CH

4ClBSAndashCPR NH

SNAndashCPR All

SNAndashCPR OH

SNAndashCPR CH

SNAndashCPR NH


2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























2ClBSAndashVLM All

2ClBSAndash VLM OH

2ClBSAndash VLM CH

2ClBSAndash VLM NH

2BrBSAndashVLM All

2BrBSAndashVLM OH

2BrBSAndashVLM CH

2BrBSAndashVLM NH

2ABSAndashCPR All

2ABSAndashCPR OH

2ABSAndashCPR CH

2ABSAndashCPR NH

BSAndashAZL All

BSAndashAZL OH

BSAndashAZL CH

BSAndashAZL NH


2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























2ClBSAndashVLM All

2ClBSAndashVLM OH

2ClBSAndashVLM CH

2ClBSAndashVLM NH

2ClBSAndashCPR All

2ClBSAndashCPR OH

2ClBSAndashCPR CH

2ClBSAndashCPR NH

PTSAndashVLM All

PTSAndashVLM OH

PTSAndashVLM CH

PTSAndashVLM NH

OTSAndashVLM All

OTSAndashVLM OH

OTSAndashVLM CH

OTSAndashVLM NH




lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599
























lactam cocrystals








S7 SI


Singlebinary

components

S=O asymsym

stretch (cmndash1)

NndashH stretch

(cmndash1)

NndashH bend

(cmndash1)

C=O stretch

(cmndash1)

BSA 1334111595 33552 14804 -----

BSAndashVLM 1334211559 33525 14990 16347

BSAndashCPR 1332911606 33521 14817 16490

BSAndashAZL 1344111615 32923 14475 16303

2ClBSA 1333211775 33551 14532 -----

2ClBSAndashVLM 1338011597 33572 14532 16514


2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599























2ClBSAndashCPR 1326411575 33483 14875 16447

4BrBSA 1328011482 33311 14699 -----

4BrBSAndashVLM 1349211658 33310 14687 16210

4BrBSAndashCPR 1335511600 33702 14881 16286

4ClBSA 1331711513 33345 14750 -----

4ClBSAndashVLM 1348411627 33288 14685 16228

4ClBSAndashCPR 1341111787 33675 14767 16313

2ABSA 1308311444 34813 14799 -----

2ABSAndashCPR 1312211402 34529 14809 16440

OTSA 1316311487 33905 14723 -----

OTSAndashVLM 1337011610 33802 14761 16639

PTSA 1323911503 ----- 14957 -----

PTSAndashVLM 1340211565 32963 15003 16593

SNA 1313811461 34781 15040 -----

SNAndashCPR 1309511456 34657 ----- 16360

VLM ----- 32732 14975 16324

CPR ----- 34299 14872 16360

AZL ----- ----- 14757 16599






















Modularity and three-dimensional isostructurality of...

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Transcript of Modularity and three-dimensional isostructurality of...