Supporting Information

© Wiley-VCH 2007

69451 Weinheim, Germany

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Cyclic Triolborates: Air- and Water-Stable Ate Complexes of Organoboronic Acids

Y. Yamamoto,* M. Takizawa, X.-Q. Yu and N. Miyaura* Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University,

Sapporo 060-8628 (Japan) Fax: (+81) 11-706-6561, E-mail: yasuyama@eng.hokudai.ac.jp and miyaura@eng.hokudai.ac.jp

List of Content

Crystal data of tetrabutylammonium phenyltriolborate (11) S2

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Experimental Data Collection A colorless block crystal of C28H54BO4N having approximate dimensions of 0.80 x 0.60 x 0.60 mm was mounted on a glass fiber. All measurements were made on a Rigaku RAXIS RAPID imaging plate area detector with graphite monochromated Mo-Kα radiation. Indexing was performed from 3 oscillations that were exposed for 90 seconds. The crystal-to-detector distance was 127.40 mm. Cell constants and an orientation matrix for data collection corresponded to a C-centered monoclinic cell with dimensions: a = 22.102(15) Å b = 16.568(11) Å β = 107.53(5)o c = 17.512(11) Å V = 6115.4(70) Å3 For Z = 8 and F.W. = 479.55, the calculated density is 1.042 g/cm3. Based on the systematic absences of: hkl: h+k ± 2n h0l: l ± 2n packing considerations, a statistical analysis of intensity distribution, and the successful solution and refinement of the structure, the space group was determined to be:

C2/c (#15) The data were collected at a temperature of 23 + 1oC to a maximum 2θ value of 55.0o. A total of 110 oscillation images were collected. A sweep of data was done using ω scans from 130.0 to 190.0o in 2.0o step, at χ=45.0o and φ = 0.0o. The exposure rate was 60.0 [sec./o]. A second sweep was performed using ω scans from 0.0 to 160.0o in

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2.0o step, at χ=45.0o and φ = 180.0o. The exposure rate was 60.0 [sec./o]. The crystal-to-detector distance was 127.40 mm. Readout was performed in the 0.100 mm pixel mode. Data Reduction Of the 29236 reflections that were collected, 7018 were unique (Rint = 0.039); equivalent reflections were merged. The linear absorption coefficient, µ, for Mo-Kα radiation is 0.669 cm-1. An empirical absorption correction was applied which resulted in transmission factors ranging from 0.569 to 0.961. The data were corrected for Lorentz and polarization effects. A correction for secondary extinction1 was applied (coefficient = 61.244000). Structure Solution and Refinement The structure was solved by direct methods2 and expanded using Fourier techniques3. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined using the riding model. The final cycle of full-matrix least-squares refinement4 on F2 was based on 7018 observed reflections and 362 variable parameters and converged (largest parameter shift was 0.00 times its esd) with unweighted and weighted agreement factors of:

R1 = Σ ||Fo| - |Fc|| / Σ |Fo| = 0.0696

wR2 = [ Σ ( w (Fo2 - Fc2)2 )/ Σ w(Fo2)2]1/2 = 0.1991 The standard deviation of an observation of unit weight5 was 0.98. A Sheldrick weighting scheme was used. Plots of Σ w (|Fo| - |Fc|)2 versus |Fo|, reflection order in data collection, sin θ/λ and various classes of indices showed no unusual trends. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.53 and -0.35 e-/Å3, respectively. Neutral atom scattering factors were taken from Cromer and Waber6. Anomalous dispersion effects were included in Fcalc7; the values for ∆f' and ∆f" were those of Creagh and McAuley8. The values for the mass attenuation coefficients are those of

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Creagh and Hubbell9. All calculations were performed using the CrystalStructure10,11 crystallographic software package.

References (1) Larson, A.C. (1970), Crystallographic Computing, 291-294. F.R. Ahmed, ed. Munksgaard, Copenhagen (equation 22, with V replaced by the cell volume). (2) SIR92: Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. (3) DIRDIF99: Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., de Gelder, R., Israel, R. and Smits, J.M.M.(1999). The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. (4) Least Squares function minimized: Σw(Fo2-Fc2)2 where w = Least Squares weights. (5) Standard deviation of an observation of unit weight: [Σw(Fo2-Fc2)2/(No-Nv)]1/2 where: No = number of observations Nv = number of variables (6) Cromer, D. T. & Waber, J. T.; "International Tables for X-ray Crystallography", Vol. IV, The Kynoch Press, Birmingham, England, Table 2.2 A (1974). (7) Ibers, J. A. & Hamilton, W. C.; Acta Crystallogr., 17, 781 (1964). (8) Creagh, D. C. & McAuley, W.J .; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.6.8, pages 219-222 (1992). (9) Creagh, D. C. & Hubbell, J.H..; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.4.3, pages 200-206 (1992).

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(10) CrystalStructure 3.8: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC (2000-2006). 9009 New Trails Dr. The Woodlands TX 77381 USA. (11) CRYSTALS Issue 11: Carruthers, J.R., Rollett,J.S., Betteridge, P.W., Kinna, D., Pearce, L., Larsen, A., and Gabe, E. Chemical Crystallography Laboratory, Oxford, UK. (1999)

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EXPERIMENTAL DETAILS

A. Crystal Data Empirical Formula C28H54BO4N Formula Weight 479.55 Crystal Color, Habit colorless, block Crystal Dimensions 0.80 X 0.60 X 0.60 mm Crystal System monoclinic Lattice Type C-centered Indexing Images 3 oscillations @ 90.0 seconds Detector Position 127.40 mm Pixel Size 0.100 mm Lattice Parameters a = 22.102(15) Å b = 16.568(11) Å c = 17.512(11) Å β = 107.53(5) o V = 6115.4(70) Å3 Space Group C2/c (#15) Z value 8 Dcalc 1.042 g/cm3 F000 2128.00

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µ(MoKα) 0.669 cm-1

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B. Intensity Measurements Diffractometer Rigaku RAXIS-RAPID Radiation MoKα (λ = 0.71075 Å) graphite monochromated Detector Aperture 280 mm x 256 mm Data Images 110 exposures ω oscillation Range (χ=45.0, φ=0.0) 130.0 - 190.0o Exposure Rate 60.0 sec./o ω oscillation Range (χ=45.0, φ=180.0) 0.0 - 160.0o Exposure Rate 60.0 sec./o Detector Position 127.40 mm Pixel Size 0.100 mm 2θmax 55.0o No. of Reflections Measured Total: 29236 Unique: 7018 (Rint = 0.039) Corrections Lorentz-polarization Absorption (trans. factors: 0.569 - 0.961) Secondary Extinction (coefficient: 6.12440e+001)

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C. Structure Solution and Refinement Structure Solution Direct Methods (SIR92) Refinement Full-matrix least-squares on F2 Function Minimized Σ w (Fo2 - Fc2)2 Least Squares Weights 1/[0.0018Fo2+1.0000σ(Fo2)]/(4Fo2) 2θmax cutoff 55.0o Anomalous Dispersion All non-hydrogen atoms No. Observations (All reflections) 7018 No. Variables 362 Reflection/Parameter Ratio 19.39 Residuals: R1 (I>2.00σ(I)) 0.0696 Residuals: R (All reflections) 0.1568 Residuals: wR2 (All reflections) 0.1991 Goodness of Fit Indicator 0.980 Max Shift/Error in Final Cycle 0.000 Maximum peak in Final Diff. Map 0.53 e-/Å3 Minimum peak in Final Diff. Map -0.35 e-/Å3

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Table 1. Atomic coordinates and Biso/Beq atom x y z Beq O(1) 0.20182(8) -0.12674(12) 0.04065(10) 6.19(4) O(2) 0.17936(9) -0.00067(11) -0.02777(13) 6.95(5) O(3) 0.18939(8) -0.12036(11) -0.09982(10) 5.90(4) O(4) 0.24370(9) -0.25436(12) -0.15362(10) 6.88(5) N(1) 0.28928(10) 0.04368(13) 0.23478(11) 5.45(5) C(1) -0.01810(19) -0.0818(3) -0.1343(3) 13.50(17) C(2) 0.02679(14) -0.1200(2) -0.0673(2) 8.50(9) C(3) 0.09784(12) -0.10323(16) -0.05338(17) 5.79(6) C(4) 0.13647(13) -0.14491(18) 0.02277(17) 6.37(7) C(5) 0.11353(14) -0.01334(17) -0.0433(2) 7.09(8) C(6) 0.12299(13) -0.13387(18) -0.11906(16) 6.49(7) C(7) 0.28856(12) -0.05934(16) -0.00246(13) 4.72(5) C(8) 0.33274(13) -0.12035(19) 0.02192(15) 6.01(7) C(9) 0.39686(15) -0.1076(2) 0.04208(19) 7.33(9) C(10) 0.41967(16) -0.0312(3) 0.0380(2) 8.05(10) C(11) 0.37811(18) 0.0321(2) 0.01360(18) 7.42(9) C(12) 0.31324(14) 0.01723(18) -0.00645(14) 5.88(7) C(13) 0.33178(13) 0.09703(18) 0.29973(16) 6.17(7) C(14) 0.38939(16) 0.1319(2) 0.2841(2) 8.34(10) C(15) 0.4286(2) 0.1801(3) 0.3565(2) 12.00(15) C(16) 0.4873(2) 0.2105(4) 0.3546(3) 16.7(2) C(17) 0.32564(13) -0.02587(17) 0.21344(15) 6.10(7) C(18) 0.35844(16) -0.0815(2) 0.28058(18) 7.61(9) C(19) 0.40338(19) -0.1365(2) 0.2572(2) 9.91(11) C(20) 0.4352(2) -0.1954(3) 0.3155(3) 12.51(16) C(21) 0.23768(13) 0.01392(19) 0.26823(16) 6.33(7) C(22) 0.18770(16) -0.0394(2) 0.2126(2) 8.63(10) C(23) 0.1380(2) -0.0692(2) 0.2484(2) 10.81(14) C(24) 0.1613(3) -0.1334(3) 0.3026(4) 17.0(2) C(25) 0.26168(14) 0.0901(2) 0.15772(15) 6.79(7) C(26) 0.22041(18) 0.1629(2) 0.1617(2) 9.26(11) C(27) 0.2071(2) 0.2124(4) 0.0841(3) 15.3(2) C(28) 0.1608(3) 0.2096(5) 0.0311(3) 20.2(3) B(1) 0.21423(14) -0.07633(18) -0.02274(16) 4.76(6) Beq = 8/3 π2(U11(aa*)2 + U22(bb*)2 + U33(cc*)2 + 2U12(aa*bb*)cos γ + 2U13(aa*cc*)cos β + 2U23(bb*cc*)cos α)

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Table 2. Atomic coordinates and B iso involving hydrogens/Beq atom x y z Beq H(1) -0.0607 -0.0880 -0.1338 15.48 H(2) -0.0084 -0.0260 -0.1350 15.48 H(3) -0.0130 -0.1072 -0.1806 15.49 H(4) 0.0067 -0.1010 -0.0215 9.61 H(5) 0.0193 -0.1765 -0.0704 9.61 H(6) 0.1306 -0.2017 0.0173 7.75 H(7) 0.1222 -0.1263 0.0657 7.75 H(8) 0.1032 0.0052 0.0026 8.40 H(9) 0.0901 0.0165 -0.0889 8.39 H(10) 0.1027 -0.1056 -0.1672 7.41 H(11) 0.1149 -0.1900 -0.1271 7.40 H(12) 0.3247 -0.1642 0.0252 7.36 H(13) 0.4266 -0.1500 0.0602 8.85 H(14) 0.4640 -0.0220 0.0508 9.74 H(15) 0.3942 0.0848 0.0108 9.04 H(16) 0.2880 0.0546 -0.0177 7.11 H(17) 0.3067 0.1405 0.3088 7.44 H(18) 0.3463 0.0654 0.3470 7.43 H(19) 0.3762 0.1645 0.2374 10.30 H(20) 0.4159 0.0897 0.2760 10.32 H(21) 0.4039 0.2267 0.3575 14.79 H(22) 0.4331 0.1491 0.4036 14.80 H(23) 0.4839 0.2428 0.3087 20.27 H(24) 0.5131 0.1647 0.3539 20.26 H(25) 0.5061 0.2412 0.4016 20.25 H(26) 0.2977 -0.0566 0.1718 7.41 H(27) 0.3579 -0.0028 0.1947 7.39 H(28) 0.3269 -0.1123 0.2941 9.20 H(29) 0.3818 -0.0510 0.3258 9.20 H(30) 0.3795 -0.1644 0.2105 11.77 H(31) 0.4350 -0.1046 0.2450 11.77 H(32) 0.4435 -0.2430 0.2900 15.08 H(33) 0.4740 -0.1737 0.3486 15.09 H(34) 0.4085 -0.2082 0.3474 15.09 H(35) 0.2178 0.0595 0.2832 7.81 H(36) 0.2568 -0.0180 0.3142 7.80 H(37) 0.1650 -0.0065 0.1690 10.64

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Table 2. Atomic coordinates and Biso involving hydrogens/Beq (continued) atom x y z Beq H(38) 0.2073 -0.0826 0.1933 10.63 H(39) 0.0947 -0.1234 0.2328 13.78 H(40) 0.1257 -0.0267 0.2770 13.85 H(41) 0.1428 -0.1335 0.3450 20.90 H(42) 0.2057 -0.1251 0.3236 20.91 H(43) 0.1534 -0.1838 0.2755 20.91 H(44) 0.2960 0.1094 0.1407 8.14 H(45) 0.2367 0.0540 0.1187 8.16 H(46) 0.2405 0.1915 0.2097 11.12 H(47) 0.1804 0.1434 0.1635 11.12 H(48) 0.2446 0.2168 0.0685 17.79 H(49) 0.1958 0.2641 0.0988 17.79 H(50) 0.1326 0.1797 0.0519 23.56 H(51) 0.1384 0.2528 -0.0008 23.57 H(52) 0.1778 0.1752 -0.0007 23.57 H(53) 0.2278 -0.2140 -0.1264 8.46 H(54) 0.2628 -0.2910 -0.1084 8.48 Beq = 8/3 π2(U11(aa*)2 + U22(bb*)2 + U33(cc*)2 + 2U12(aa*bb*)cos γ + 2U13(aa*cc*)cos β + 2U23(bb*cc*)cos α)

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Table 3. Anisotropic displacement parameters atom U11 U22 U33 U12 U13 U23 O(1) 0.0704(11) 0.1022(14) 0.0649(10) -0.0010(10) 0.0238(8) 0.0189(9) O(2) 0.0733(12) 0.0570(11) 0.1266(17) 0.0005(9) 0.0195(11) -0.0106(10) O(3) 0.0812(12) 0.0843(12) 0.0579(10) -0.0131(9) 0.0197(8) -0.0153(9) O(4) 0.1158(15) 0.0867(13) 0.0655(11) 0.0056(11) 0.0373(10) 0.0051(9) N(1) 0.0827(14) 0.0828(15) 0.0450(11) 0.0144(11) 0.0246(10) -0.0089(10) C(1) 0.096(2) 0.176(4) 0.218(5) -0.003(2) 0.012(3) 0.026(4) C(2) 0.077(2) 0.102(2) 0.126(2) -0.0066(18) 0.0031(19) 0.004(2) C(3) 0.0677(16) 0.0692(17) 0.0802(18) -0.0040(13) 0.0178(14) -0.0030(14) C(4) 0.0788(18) 0.087(2) 0.0793(18) -0.0095(15) 0.0288(14) 0.0041(15) C(5) 0.080(2) 0.0684(19) 0.117(2) 0.0081(15) 0.0245(17) -0.0032(17) C(6) 0.087(2) 0.0797(19) 0.0679(17) -0.0079(16) 0.0050(14) -0.0047(14) C(7) 0.0759(16) 0.0666(16) 0.0396(12) -0.0037(14) 0.0214(11) -0.0029(11) C(8) 0.0771(19) 0.089(2) 0.0673(16) -0.0020(16) 0.0289(13) -0.0026(15) C(9) 0.072(2) 0.119(2) 0.089(2) 0.0025(19) 0.0266(16) 0.0022(19) C(10) 0.070(2) 0.155(3) 0.084(2) -0.014(2) 0.0271(17) -0.012(2) C(11) 0.103(2) 0.109(2) 0.0746(19) -0.039(2) 0.0338(18) -0.0105(18) C(12) 0.092(2) 0.080(2) 0.0530(15) -0.0114(16) 0.0249(13) -0.0049(13) C(13) 0.0906(19) 0.0857(19) 0.0596(15) 0.0085(16) 0.0249(14) -0.0133(14) C(14) 0.110(2) 0.110(2) 0.106(2) -0.001(2) 0.047(2) -0.022(2) C(15) 0.148(3) 0.179(4) 0.140(3) -0.069(3) 0.062(3) -0.061(3) C(16) 0.167(5) 0.282(7) 0.192(5) -0.064(5) 0.064(4) -0.075(5) C(17) 0.0854(18) 0.0868(19) 0.0620(16) 0.0162(15) 0.0261(14) -0.0150(14) C(18) 0.111(2) 0.091(2) 0.089(2) 0.028(2) 0.0339(18) 0.0019(18) C(19) 0.124(2) 0.120(3) 0.128(3) 0.050(2) 0.031(2) 0.012(2) C(20) 0.124(3) 0.152(4) 0.200(4) 0.041(3) 0.051(3) 0.036(3) C(21) 0.0920(19) 0.093(2) 0.0622(16) 0.0097(16) 0.0333(15) -0.0072(15) C(22) 0.106(2) 0.123(2) 0.108(2) -0.012(2) 0.045(2) -0.029(2) C(23) 0.157(3) 0.108(3) 0.173(4) 0.004(2) 0.092(3) 0.007(3) C(24) 0.299(7) 0.172(5) 0.190(5) -0.030(5) 0.099(5) -0.005(4) C(25) 0.099(2) 0.109(2) 0.0503(14) 0.0143(19) 0.0228(14) 0.0046(15) C(26) 0.121(2) 0.128(3) 0.103(2) 0.048(2) 0.034(2) 0.037(2) C(27) 0.144(4) 0.262(6) 0.158(4) 0.064(4) 0.020(3) 0.114(4) C(28) 0.188(6) 0.414(12) 0.145(5) 0.015(7) 0.016(4) 0.111(6) B(1) 0.0716(18) 0.0575(17) 0.0523(15) 0.0039(14) 0.0194(13) -0.0013(13) The general temperature factor expression: exp(-2π2(a*2U11h2 + b*2U22k2 + c*2U33l2 + 2a*b*U12hk + 2a*c*U13hl + 2b*c*U23kl))

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Table 4. Bond lengths (Å) atom atom distance atom atom distance O(1) C(4) 1.415(3) O(1) B(1) 1.479(3) O(2) C(5) 1.413(3) O(2) B(1) 1.460(3) O(3) C(6) 1.421(3) O(3) B(1) 1.486(3) N(1) C(13) 1.521(3) N(1) C(17) 1.515(3) N(1) C(21) 1.513(3) N(1) C(25) 1.513(3) C(1) C(2) 1.435(5) C(2) C(3) 1.540(4) C(3) C(4) 1.516(3) C(3) C(5) 1.527(3) C(3) C(6) 1.508(4) C(7) C(8) 1.381(3) C(7) C(12) 1.391(4) C(7) B(1) 1.598(3) C(8) C(9) 1.370(4) C(9) C(10) 1.372(6) C(10) C(11) 1.375(5) C(11) C(12) 1.392(4) C(13) C(14) 1.497(4) C(14) C(15) 1.528(5) C(15) C(16) 1.401(8) C(17) C(18) 1.499(3) C(18) C(19) 1.493(5) C(19) C(20) 1.434(6) C(21) C(22) 1.517(4) C(22) C(23) 1.503(6) C(23) C(24) 1.415(7) C(25) C(26) 1.527(5) C(26) C(27) 1.538(7) C(27) C(28) 1.156(7)

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Table 5. Bond lengths involving hydrogens (Å) atom atom distance atom atom distance O(4) H(53) 0.948 O(4) H(54) 0.986 C(1) H(1) 0.950 C(1) H(2) 0.950 C(1) H(3) 0.950 C(2) H(4) 1.074 C(2) H(5) 0.950 C(4) H(6) 0.950 C(4) H(7) 0.950 C(5) H(8) 0.950 C(5) H(9) 0.950 C(6) H(10) 0.950 C(6) H(11) 0.950 C(8) H(12) 0.755 C(9) H(13) 0.950 C(10) H(14) 0.950 C(11) H(15) 0.950 C(12) H(16) 0.817 C(13) H(17) 0.950 C(13) H(18) 0.950 C(14) H(19) 0.950 C(14) H(20) 0.950 C(15) H(21) 0.950 C(15) H(22) 0.950 C(16) H(23) 0.950 C(16) H(24) 0.950 C(16) H(25) 0.950 C(17) H(26) 0.950 C(17) H(27) 0.950 C(18) H(28) 0.950 C(18) H(29) 0.950 C(19) H(30) 0.950 C(19) H(31) 0.950 C(20) H(32) 0.950 C(20) H(33) 0.950 C(20) H(34) 0.950 C(21) H(35) 0.950 C(21) H(36) 0.950 C(22) H(37) 0.950 C(22) H(38) 0.950 C(23) H(39) 1.280 C(23) H(40) 0.950 C(24) H(41) 0.950 C(24) H(42) 0.950 C(24) H(43) 0.950 C(25) H(44) 0.950 C(25) H(45) 0.950 C(26) H(46) 0.950 C(26) H(47) 0.950 C(27) H(48) 0.950 C(27) H(49) 0.950 C(28) H(50) 0.950 C(28) H(51) 0.950 C(28) H(52) 0.950

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Table 6. Bond angles (o) atom atom atom angle atom atom atom angle C(4) O(1) B(1) 111.20(18) C(5) O(2) B(1) 112.2(2) C(6) O(3) B(1) 111.4(2) C(13) N(1) C(17) 111.87(19) C(13) N(1) C(21) 105.5(2) C(13) N(1) C(25) 111.4(2) C(17) N(1) C(21) 111.4(2) C(17) N(1) C(25) 105.5(2) C(21) N(1) C(25) 111.3(2) C(1) C(2) C(3) 118.1(3) C(2) C(3) C(4) 109.6(2) C(2) C(3) C(5) 112.3(2) C(2) C(3) C(6) 114.3(2) C(4) C(3) C(5) 107.1(2) C(4) C(3) C(6) 106.2(2) C(5) C(3) C(6) 107.0(2) O(1) C(4) C(3) 111.4(2) O(2) C(5) C(3) 110.6(2) O(3) C(6) C(3) 111.0(2) C(8) C(7) C(12) 115.6(2) C(8) C(7) B(1) 121.6(2) C(12) C(7) B(1) 122.8(2) C(7) C(8) C(9) 123.2(3) C(8) C(9) C(10) 119.8(3) C(9) C(10) C(11) 119.9(3) C(10) C(11) C(12) 119.0(3) C(7) C(12) C(11) 122.6(2) N(1) C(13) C(14) 117.1(2) C(13) C(14) C(15) 110.6(3) C(14) C(15) C(16) 117.8(4) N(1) C(17) C(18) 116.2(2) C(17) C(18) C(19) 111.4(2) C(18) C(19) C(20) 116.4(4) N(1) C(21) C(22) 115.4(2) C(21) C(22) C(23) 114.0(3) C(22) C(23) C(24) 111.2(4) N(1) C(25) C(26) 116.5(2) C(25) C(26) C(27) 109.8(3) C(26) C(27) C(28) 125.1(6) O(1) B(1) O(2) 108.4(2) O(1) B(1) O(3) 107.6(2) O(1) B(1) C(7) 110.08(18) O(2) B(1) O(3) 108.82(18) O(2) B(1) C(7) 110.5(2) O(3) B(1) C(7) 111.2(2)

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Table 7. Bond angles involving hydrogens (o) atom atom atom angle atom atom atom angle H(53) O(4) H(54) 99.5 C(2) C(1) H(1) 112.9 C(2) C(1) H(2) 109.7 C(2) C(1) H(3) 105.8 H(1) C(1) H(2) 109.5 H(1) C(1) H(3) 109.5 H(2) C(1) H(3) 109.5 C(1) C(2) H(4) 98.2 C(1) C(2) H(5) 108.8 C(3) C(2) H(4) 117.4 C(3) C(2) H(5) 109.7 H(4) C(2) H(5) 103.2 O(1) C(4) H(6) 109.4 O(1) C(4) H(7) 108.4 C(3) C(4) H(6) 109.8 C(3) C(4) H(7) 108.4 H(6) C(4) H(7) 109.5 O(2) C(5) H(8) 106.6 O(2) C(5) H(9) 110.8 C(3) C(5) H(8) 107.9 C(3) C(5) H(9) 111.3 H(8) C(5) H(9) 109.5 O(3) C(6) H(10) 108.1 O(3) C(6) H(11) 109.0 C(3) C(6) H(10) 109.0 C(3) C(6) H(11) 110.2 H(10) C(6) H(11) 109.5 C(7) C(8) H(12) 124.6 C(9) C(8) H(12) 112.2 C(8) C(9) H(13) 122.1 C(10) C(9) H(13) 118.1 C(9) C(10) H(14) 120.4 C(11) C(10) H(14) 119.7 C(10) C(11) H(15) 119.4 C(12) C(11) H(15) 121.6 C(7) C(12) H(16) 117.1 C(11) C(12) H(16) 120.2 N(1) C(13) H(17) 107.8 N(1) C(13) H(18) 107.6 C(14) C(13) H(17) 108.0 C(14) C(13) H(18) 106.8 H(17) C(13) H(18) 109.5 C(13) C(14) H(19) 108.6 C(13) C(14) H(20) 109.8 C(15) C(14) H(19) 111.6 C(15) C(14) H(20) 106.7 H(19) C(14) H(20) 109.5 C(14) C(15) H(21) 104.6 C(14) C(15) H(22) 108.8 C(16) C(15) H(21) 104.5 C(16) C(15) H(22) 111.1 H(21) C(15) H(22) 109.5 C(15) C(16) H(23) 112.7 C(15) C(16) H(24) 106.0 C(15) C(16) H(25) 109.7 H(23) C(16) H(24) 109.5 H(23) C(16) H(25) 109.5 H(24) C(16) H(25) 109.5 N(1) C(17) H(26) 109.1 N(1) C(17) H(27) 106.8 C(18) C(17) H(26) 108.7 C(18) C(17) H(27) 106.4 H(26) C(17) H(27) 109.5 C(17) C(18) H(28) 108.0 C(17) C(18) H(29) 109.8 C(19) C(18) H(28) 109.9 C(19) C(18) H(29) 108.3 H(28) C(18) H(29) 109.5 C(18) C(19) H(30) 106.8 C(18) C(19) H(31) 108.5 C(20) C(19) H(30) 107.9 C(20) C(19) H(31) 107.7 H(30) C(19) H(31) 109.5 C(19) C(20) H(32) 110.6

- S18 -

Table 7. Bond angles involving hydrogens (o) (continued) atom atom atom angle atom atom atom angle C(19) C(20) H(33) 109.6 C(19) C(20) H(34) 108.2 H(32) C(20) H(33) 109.5 H(32) C(20) H(34) 109.5 H(33) C(20) H(34) 109.5 N(1) C(21) H(35) 108.2 N(1) C(21) H(36) 108.4 C(22) C(21) H(35) 109.5 C(22) C(21) H(36) 105.7 H(35) C(21) H(36) 109.5 C(21) C(22) H(37) 106.8 C(21) C(22) H(38) 110.2 C(23) C(22) H(37) 104.3 C(23) C(22) H(38) 111.8 H(37) C(22) H(38) 109.5 C(22) C(23) H(39) 137.2 C(22) C(23) H(40) 109.8 C(24) C(23) H(39) 73.3 C(24) C(23) H(40) 107.9 H(39) C(23) H(40) 108.6 C(23) C(24) H(41) 111.7 C(23) C(24) H(42) 106.0 C(23) C(24) H(43) 110.6 H(41) C(24) H(42) 109.5 H(41) C(24) H(43) 109.5 H(42) C(24) H(43) 109.5 N(1) C(25) H(44) 107.8 N(1) C(25) H(45) 108.3 C(26) C(25) H(44) 106.9 C(26) C(25) H(45) 107.7 H(44) C(25) H(45) 109.5 C(25) C(26) H(46) 107.9 C(25) C(26) H(47) 107.8 C(27) C(26) H(46) 115.5 C(27) C(26) H(47) 106.1 H(46) C(26) H(47) 109.5 C(26) C(27) H(48) 110.1 C(26) C(27) H(49) 103.6 C(28) C(27) H(48) 114.2 C(28) C(27) H(49) 90.7 H(48) C(27) H(49) 109.4 C(27) C(28) H(50) 103.7 C(27) C(28) H(51) 128.3 C(27) C(28) H(52) 94.8 H(50) C(28) H(51) 109.5 H(50) C(28) H(52) 109.5 H(51) C(28) H(52) 109.5

- S19 -

Table 8. Torsion Angles(o) atom1 atom2 atom3 atom4 angle atom1 atom2 atom3 atom4 angle C(4) O(1) B(1) O(2) 60.9(2) C(4) O(1) B(1) O(3) -56.7(2) C(4) O(1) B(1) C(7) -178.1(2) B(1) O(1) C(4) C(3) -3.5(3) C(5) O(2) B(1) O(1) -57.5(2) C(5) O(2) B(1) O(3) 59.3(3) C(5) O(2) B(1) C(7) -178.3(2) B(1) O(2) C(5) C(3) -2.0(3) C(6) O(3) B(1) O(1) 60.8(2) C(6) O(3) B(1) O(2) -56.6(2) C(6) O(3) B(1) C(7) -178.6(2) B(1) O(3) C(6) C(3) -2.9(2) C(13) N(1) C(17) C(18) 58.3(3) C(17) N(1) C(13) C(14) 55.8(3) C(13) N(1) C(21) C(22) 178.4(2) C(21) N(1) C(13) C(14) 177.1(2) C(13) N(1) C(25) C(26) -60.3(3) C(25) N(1) C(13) C(14) -62.1(3) C(17) N(1) C(21) C(22) -60.0(2) C(21) N(1) C(17) C(18) -59.6(2) C(17) N(1) C(25) C(26) 178.2(2) C(25) N(1) C(17) C(18) 179.6(2) C(21) N(1) C(25) C(26) 57.2(3) C(25) N(1) C(21) C(22) 57.5(3) C(1) C(2) C(3) C(4) 176.5(3) C(1) C(2) C(3) C(5) 57.6(4) C(1) C(2) C(3) C(6) -64.5(4) C(2) C(3) C(4) O(1) -176.1(2) C(2) C(3) C(5) O(2) 177.8(2) C(2) C(3) C(6) O(3) -176.7(2) C(4) C(3) C(5) O(2) 57.5(3) C(5) C(3) C(4) O(1) -54.1(3) C(4) C(3) C(6) O(3) -55.8(2) C(6) C(3) C(4) O(1) 60.0(2) C(5) C(3) C(6) O(3) 58.4(2) C(6) C(3) C(5) O(2) -56.0(3) C(8) C(7) C(12) C(11) -0.7(3) C(12) C(7) C(8) C(9) 0.8(4) C(8) C(7) B(1) O(1) 46.4(3) C(8) C(7) B(1) O(2) 166.2(2) C(8) C(7) B(1) O(3) -72.8(2) B(1) C(7) C(8) C(9) -178.0(2) C(12) C(7) B(1) O(1) -132.2(2) C(12) C(7) B(1) O(2) -12.5(3) C(12) C(7) B(1) O(3) 108.5(2) B(1) C(7) C(12) C(11) 178.0(2) C(7) C(8) C(9) C(10) -0.3(4) C(8) C(9) C(10) C(11) -0.2(4) C(9) C(10) C(11) C(12) 0.2(4) C(10) C(11) C(12) C(7) 0.3(4) N(1) C(13) C(14) C(15) -177.0(2) C(13) C(14) C(15) C(16) 174.2(4) N(1) C(17) C(18) C(19) -167.9(2) C(17) C(18) C(19) C(20) -176.9(3) N(1) C(21) C(22) C(23) 178.8(2) C(21) C(22) C(23) C(24) -77.3(4) N(1) C(25) C(26) C(27) 169.0(3) C(25) C(26) C(27) C(28) 100.0(8) The sign is positive if when looking from atom 2 to atom 3 a clock-wise motion of atom 1 would superimpose it on atom 4.

- S20 -

Table 9. Distances beyond the asymmetric unit out to 3.60 Å atom atom distance atom atom distance O(1) O(4)1) 2.795(2) O(1) C(22) 3.439(4) O(2) C(25) 3.544(3) O(3) O(4) 2.818(2) O(3) C(21)2) 3.328(3) O(4) O(1)1) 2.795(2) O(4) O(3) 2.818(2) O(4) C(4)1) 3.376(3) O(4) C(6) 3.527(3) O(4) C(13)2) 3.494(3) O(4) C(26)2) 3.466(4) C(4) O(4)1) 3.376(3) C(6) O(4) 3.527(3) C(13) O(4)3) 3.494(3) C(21) O(3)3) 3.328(3) C(22) O(1) 3.439(4) C(25) O(2) 3.544(3) C(26) O(4)3) 3.466(4) Symmetry Operators: (1) -X+1/2,-Y+1/2-1,-Z (2) X,-Y,Z+1/2-1 (3) X,-Y,Z+1/2

- S21 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens atom atom distance atom atom distance O(1) H(26) 2.860 O(1) H(37) 3.284 O(1) H(38) 2.739 O(1) H(45) 3.285 O(1) H(53) 3.463 O(1) H(53)1) 3.198 O(1) H(54)1) 1.821 O(2) H(37) 3.556 O(2) H(40)2) 3.295 O(2) H(41)2) 3.077 O(2) H(42)2) 3.516 O(2) H(45) 2.654 O(2) H(50) 3.580 O(2) H(52) 2.955 O(3) H(17)2) 3.450 O(3) H(35)2) 2.526 O(3) H(36)2) 3.331 O(3) H(40)2) 3.278 O(3) H(53) 1.893 O(3) H(54) 3.286 O(4) H(6)1) 3.155 O(4) H(7)1) 3.509 O(4) H(11) 3.203 O(4) H(12) 3.445 O(4) H(12)1) 3.348 O(4) H(17)2) 2.547 O(4) H(21)2) 3.517 O(4) H(26)1) 3.251 O(4) H(28)1) 3.325 O(4) H(30)1) 2.929 O(4) H(35)2) 3.404 O(4) H(38)1) 3.067 O(4) H(46)2) 2.592 O(4) H(47)2) 3.592 C(1) H(3)3) 3.536 C(1) H(10)3) 3.439 C(1) H(32)4) 3.199 C(1) H(37)5) 3.444 C(1) H(40)5) 3.399 C(2) H(32)4) 3.468 C(4) H(12)1) 3.446 C(4) H(21)6) 3.293 C(4) H(37) 3.352 C(4) H(38) 3.102 C(4) H(54)1) 2.515 C(5) H(37) 3.548 C(5) H(40)2) 3.304 C(5) H(41)2) 3.304 C(5) H(45) 3.471 C(5) H(50) 3.573 C(5) H(52) 3.421 C(6) H(32)1) 3.554 C(6) H(35)2) 3.316 C(6) H(40)2) 3.234 C(6) H(53) 2.706 C(7) H(18)2) 3.258 C(7) H(26) 2.997 C(7) H(27) 3.459 C(7) H(36)2) 3.329 C(7) H(45) 3.287 C(7) H(53) 3.366 C(7) H(54)1) 3.540 C(8) H(6)1) 3.187 C(8) H(18)2) 3.295 C(8) H(22)2) 3.494 C(8) H(26) 3.135 C(8) H(27) 3.500 C(8) H(30) 3.233 C(8) H(53) 3.303 C(8) H(54)1) 3.291 C(9) H(6)1) 3.325 C(9) H(18)2) 3.333 C(9) H(22)2) 2.858 C(9) H(27) 3.506

- S22 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance C(9) H(30) 3.227 C(9) H(31) 3.397 C(9) H(33)7) 3.118 C(10) H(14)8) 3.495 C(10) H(18)2) 3.298 C(10) H(22)2) 3.142 C(10) H(27) 3.446 C(10) H(33)7) 3.497 C(11) H(18)2) 3.222 C(11) H(24)7) 3.555 C(11) H(27) 3.384 C(11) H(29)2) 3.329 C(11) H(44) 3.511 C(11) H(51)9) 3.583 C(12) H(18)2) 3.182 C(12) H(26) 3.465 C(12) H(27) 3.377 C(12) H(36)2) 3.010 C(12) H(44) 3.116 C(12) H(45) 3.205 C(13) H(53)10) 3.537 C(14) H(43)11) 3.273 C(15) H(6)11) 3.490 C(15) H(39)11) 3.581 C(15) H(43)11) 3.346 C(16) H(23)7) 3.158 C(16) H(39)11) 3.396 C(16) H(51)12) 3.584 C(20) H(3)13) 3.459 C(20) H(5)13) 3.117 C(20) H(13)7) 3.260 C(22) H(1)5) 3.450 C(22) H(7) 2.923 C(23) H(1)5) 3.415 C(23) H(2)5) 3.348 C(23) H(7) 3.253 C(23) H(9)10) 3.437 C(23) H(10)10) 3.447 C(24) H(9)10) 3.411 C(24) H(19)6) 3.470 C(24) H(21)6) 3.587 C(24) H(48)6) 3.572 C(24) H(49)6) 3.544 C(24) H(52)10) 3.424 C(25) H(16) 3.346 C(26) H(34)11) 3.526 C(27) H(34)11) 3.398 C(27) H(42)11) 3.421 C(27) H(48)9) 3.373 C(28) H(25)14) 3.583 C(28) H(34)11) 3.269 C(28) H(41)2) 3.405 C(28) H(48)9) 3.332 B(1) H(26) 3.366 B(1) H(35)2) 3.434 B(1) H(45) 3.210 B(1) H(53) 2.987 B(1) H(54)1) 3.108 H(1) C(22)5) 3.450 H(1) C(23)5) 3.415 H(1) H(8)5) 3.057 H(1) H(10)3) 3.339 H(1) H(32)4) 3.116 H(1) H(34)4) 3.441 H(1) H(37)5) 2.699 H(1) H(40)5) 3.130 H(1) H(47)5) 2.699 H(1) H(50)5) 2.875 H(2) C(23)5) 3.348 H(2) H(4)5) 3.447 H(2) H(8)5) 3.581 H(2) H(37)5) 3.374 H(2) H(39)5) 3.276 H(2) H(40)5) 3.128

- S23 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(3) C(1)3) 3.536 H(3) C(20)4) 3.459 H(3) H(3)3) 2.661 H(3) H(10)3) 2.803 H(3) H(32)4) 2.656 H(3) H(40)5) 3.383 H(4) H(2)5) 3.447 H(4) H(4)5) 3.461 H(4) H(8)5) 3.002 H(4) H(9)5) 3.572 H(4) H(25)6) 3.418 H(4) H(50)5) 3.238 H(5) C(20)4) 3.117 H(5) H(13)1) 3.097 H(5) H(25)6) 3.452 H(5) H(32)4) 2.846 H(5) H(33)4) 2.884 H(5) H(34)4) 3.097 H(5) H(50)5) 3.471 H(6) O(4)1) 3.155 H(6) C(8)1) 3.187 H(6) C(9)1) 3.325 H(6) C(15)6) 3.490 H(6) H(12)1) 2.629 H(6) H(13)1) 2.906 H(6) H(21)6) 2.794 H(6) H(22)6) 3.345 H(6) H(53)1) 3.435 H(6) H(54)1) 2.418 H(7) O(4)1) 3.509 H(7) C(22) 2.923 H(7) C(23) 3.253 H(7) H(21)6) 2.923 H(7) H(37) 2.659 H(7) H(38) 2.555 H(7) H(39) 3.163 H(7) H(54)1) 2.784 H(8) H(1)5) 3.057 H(8) H(2)5) 3.581 H(8) H(4)5) 3.002 H(8) H(37) 2.829 H(8) H(45) 3.143 H(8) H(50) 3.033 H(8) H(52) 3.274 H(9) C(23)2) 3.437 H(9) C(24)2) 3.411 H(9) H(4)5) 3.572 H(9) H(40)2) 2.696 H(9) H(41)2) 2.695 H(9) H(50) 3.589 H(9) H(52) 3.355 H(10) C(1)3) 3.439 H(10) C(23)2) 3.447 H(10) H(1)3) 3.339 H(10) H(3)3) 2.803 H(10) H(32)1) 3.261 H(10) H(35)2) 3.024 H(10) H(40)2) 2.514 H(10) H(53) 3.192 H(11) O(4) 3.203 H(11) H(12)1) 3.060 H(11) H(13)1) 3.144 H(11) H(30)1) 2.841 H(11) H(32)1) 2.969 H(11) H(53) 2.523 H(11) H(54) 3.599 H(12) O(4) 3.445 H(12) O(4)1) 3.348 H(12) C(4)1) 3.446 H(12) H(6)1) 2.629 H(12) H(11)1) 3.060 H(12) H(26) 3.323 H(12) H(30) 3.103 H(12) H(53) 2.983

- S24 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(12) H(53)1) 3.129 H(12) H(54) 3.136 H(12) H(54)1) 2.847 H(13) C(20)7) 3.260 H(13) H(5)1) 3.097 H(13) H(6)1) 2.906 H(13) H(11)1) 3.144 H(13) H(22)2) 2.788 H(13) H(30) 3.119 H(13) H(31) 3.274 H(13) H(33)7) 2.327 H(14) C(10)8) 3.495 H(14) H(14)8) 2.817 H(14) H(22)7) 3.571 H(14) H(22)2) 3.239 H(14) H(24)7) 3.479 H(14) H(29)7) 3.476 H(14) H(33)7) 3.138 H(15) H(24)7) 2.940 H(15) H(25)7) 3.448 H(15) H(29)2) 3.218 H(15) H(49)9) 3.408 H(15) H(51)9) 2.778 H(16) C(25) 3.346 H(16) H(36)2) 2.879 H(16) H(42)2) 3.058 H(16) H(44) 2.873 H(16) H(45) 2.937 H(16) H(48) 3.360 H(16) H(49)9) 3.388 H(16) H(51)9) 3.551 H(16) H(52) 3.234 H(17) O(3)10) 3.450 H(17) O(4)10) 2.547 H(17) H(43)11) 3.495 H(17) H(53)10) 2.648 H(17) H(54)10) 3.181 H(18) C(7)10) 3.258 H(18) C(8)10) 3.295 H(18) C(9)10) 3.333 H(18) C(10)10) 3.298 H(18) C(11)10) 3.222 H(18) C(12)10) 3.182 H(19) C(24)11) 3.470 H(19) H(24)7) 3.302 H(19) H(39)11) 3.582 H(19) H(43)11) 2.590 H(20) H(24)7) 3.368 H(21) O(4)10) 3.517 H(21) C(4)11) 3.293 H(21) C(24)11) 3.587 H(21) H(6)11) 2.794 H(21) H(7)11) 2.923 H(21) H(39)11) 2.949 H(21) H(43)11) 2.729 H(21) H(54)10) 3.513 H(22) C(8)10) 3.494 H(22) C(9)10) 2.858 H(22) C(10)10) 3.142 H(22) H(6)11) 3.345 H(22) H(13)10) 2.788 H(22) H(14)7) 3.571 H(22) H(14)10) 3.239 H(23) C(16)7) 3.158 H(23) H(23)7) 2.370 H(23) H(24)7) 3.147 H(23) H(39)11) 2.775 H(23) H(43)11) 3.190 H(24) C(11)7) 3.555 H(24) H(14)7) 3.479 H(24) H(15)7) 2.940 H(24) H(19)7) 3.302 H(24) H(20)7) 3.368 H(24) H(23)7) 3.147

- S25 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(24) H(24)7) 3.508 H(24) H(51)12) 3.432 H(25) C(28)12) 3.583 H(25) H(4)11) 3.418 H(25) H(5)11) 3.452 H(25) H(15)7) 3.448 H(25) H(39)11) 3.517 H(25) H(50)12) 3.470 H(25) H(51)12) 2.912 H(26) O(1) 2.860 H(26) O(4)1) 3.251 H(26) C(7) 2.997 H(26) C(8) 3.135 H(26) C(12) 3.465 H(26) B(1) 3.366 H(26) H(12) 3.323 H(26) H(54)1) 2.914 H(27) C(7) 3.459 H(27) C(8) 3.500 H(27) C(9) 3.506 H(27) C(10) 3.446 H(27) C(11) 3.384 H(27) C(12) 3.377 H(28) O(4)1) 3.325 H(28) H(46)6) 3.568 H(28) H(49)6) 2.919 H(29) C(11)10) 3.329 H(29) H(14)7) 3.476 H(29) H(15)10) 3.218 H(30) O(4)1) 2.929 H(30) C(8) 3.233 H(30) C(9) 3.227 H(30) H(11)1) 2.841 H(30) H(12) 3.103 H(30) H(13) 3.119 H(30) H(53)1) 3.120 H(30) H(54)1) 3.200 H(31) C(9) 3.397 H(31) H(13) 3.274 H(31) H(31)7) 2.827 H(31) H(33)7) 3.167 H(32) C(1)13) 3.199 H(32) C(2)13) 3.468 H(32) C(6)1) 3.554 H(32) H(1)13) 3.116 H(32) H(3)13) 2.656 H(32) H(5)13) 2.846 H(32) H(10)1) 3.261 H(32) H(11)1) 2.969 H(32) H(32)7) 3.212 H(33) C(9)7) 3.118 H(33) C(10)7) 3.497 H(33) H(5)13) 2.884 H(33) H(13)7) 2.327 H(33) H(14)7) 3.138 H(33) H(31)7) 3.167 H(34) C(26)6) 3.526 H(34) C(27)6) 3.398 H(34) C(28)6) 3.269 H(34) H(1)13) 3.441 H(34) H(5)13) 3.097 H(34) H(46)6) 3.554 H(34) H(47)6) 3.118 H(34) H(49)6) 2.778 H(34) H(50)6) 2.889 H(34) H(51)6) 3.224 H(35) O(3)10) 2.526 H(35) O(4)10) 3.404 H(35) C(6)10) 3.316 H(35) B(1)10) 3.434 H(35) H(10)10) 3.024 H(35) H(53)10) 2.982 H(36) O(3)10) 3.331 H(36) C(7)10) 3.329

- S26 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(36) C(12)10) 3.010 H(36) H(16)10) 2.879 H(37) O(1) 3.284 H(37) O(2) 3.556 H(37) C(1)5) 3.444 H(37) C(4) 3.352 H(37) C(5) 3.548 H(37) H(1)5) 2.699 H(37) H(2)5) 3.374 H(37) H(7) 2.659 H(37) H(8) 2.829 H(38) O(1) 2.739 H(38) O(4)1) 3.067 H(38) C(4) 3.102 H(38) H(7) 2.555 H(38) H(54)1) 2.761 H(39) C(15)6) 3.581 H(39) C(16)6) 3.396 H(39) H(2)5) 3.276 H(39) H(7) 3.163 H(39) H(19)6) 3.582 H(39) H(21)6) 2.949 H(39) H(23)6) 2.775 H(39) H(25)6) 3.517 H(40) O(2)10) 3.295 H(40) O(3)10) 3.278 H(40) C(1)5) 3.399 H(40) C(5)10) 3.304 H(40) C(6)10) 3.234 H(40) H(1)5) 3.130 H(40) H(2)5) 3.128 H(40) H(3)5) 3.383 H(40) H(9)10) 2.696 H(40) H(10)10) 2.514 H(41) O(2)10) 3.077 H(41) C(5)10) 3.304 H(41) C(28)10) 3.405 H(41) H(9)10) 2.695 H(41) H(48)6) 3.518 H(41) H(51)10) 3.371 H(41) H(52)10) 2.668 H(42) O(2)10) 3.516 H(42) C(27)6) 3.421 H(42) H(16)10) 3.058 H(42) H(46)6) 3.379 H(42) H(48)6) 3.224 H(42) H(49)6) 2.859 H(42) H(52)10) 3.417 H(43) C(14)6) 3.273 H(43) C(15)6) 3.346 H(43) H(17)6) 3.495 H(43) H(19)6) 2.590 H(43) H(21)6) 2.729 H(43) H(23)6) 3.190 H(43) H(46)6) 3.077 H(43) H(48)6) 3.398 H(43) H(49)6) 3.504 H(44) C(11) 3.511 H(44) C(12) 3.116 H(44) H(16) 2.873 H(45) O(1) 3.285 H(45) O(2) 2.654 H(45) C(5) 3.471 H(45) C(7) 3.287 H(45) C(12) 3.205 H(45) B(1) 3.210 H(45) H(8) 3.143 H(45) H(16) 2.937 H(46) O(4)10) 2.592 H(46) H(28)11) 3.568 H(46) H(34)11) 3.554 H(46) H(42)11) 3.379 H(46) H(43)11) 3.077 H(46) H(53)10) 2.990

- S27 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(46) H(54)10) 3.488 H(47) O(4)10) 3.592 H(47) H(1)5) 2.699 H(47) H(34)11) 3.118 H(48) C(24)11) 3.572 H(48) C(27)9) 3.373 H(48) C(28)9) 3.332 H(48) H(16) 3.360 H(48) H(41)11) 3.518 H(48) H(42)11) 3.224 H(48) H(43)11) 3.398 H(48) H(48)9) 2.716 H(48) H(49)9) 3.571 H(48) H(51)9) 3.192 H(48) H(52)9) 2.963 H(49) C(24)11) 3.544 H(49) H(15)9) 3.408 H(49) H(16)9) 3.388 H(49) H(28)11) 2.919 H(49) H(34)11) 2.778 H(49) H(42)11) 2.859 H(49) H(43)11) 3.504 H(49) H(48)9) 3.571 H(50) O(2) 3.580 H(50) C(5) 3.573 H(50) H(1)5) 2.875 H(50) H(4)5) 3.238 H(50) H(5)5) 3.471 H(50) H(8) 3.033 H(50) H(9) 3.589 H(50) H(25)14) 3.470 H(50) H(34)11) 2.889 H(51) C(11)9) 3.583 H(51) C(16)14) 3.584 H(51) H(15)9) 2.778 H(51) H(16)9) 3.551 H(51) H(24)14) 3.432 H(51) H(25)14) 2.912 H(51) H(34)11) 3.224 H(51) H(41)2) 3.371 H(51) H(48)9) 3.192 H(52) O(2) 2.955 H(52) C(5) 3.421 H(52) C(24)2) 3.424 H(52) H(8) 3.274 H(52) H(9) 3.355 H(52) H(16) 3.234 H(52) H(41)2) 2.668 H(52) H(42)2) 3.417 H(52) H(48)9) 2.963 H(53) O(1) 3.463 H(53) O(1)1) 3.198 H(53) O(3) 1.893 H(53) C(6) 2.706 H(53) C(7) 3.366 H(53) C(8) 3.303 H(53) C(13)2) 3.537 H(53) B(1) 2.987 H(53) H(6)1) 3.435 H(53) H(10) 3.192 H(53) H(11) 2.523 H(53) H(12) 2.983 H(53) H(12)1) 3.129 H(53) H(17)2) 2.648 H(53) H(30)1) 3.120 H(53) H(35)2) 2.982 H(53) H(46)2) 2.990 H(54) O(1)1) 1.821 H(54) O(3) 3.286 H(54) C(4)1) 2.515 H(54) C(7)1) 3.540 H(54) C(8)1) 3.291 H(54) B(1)1) 3.108 H(54) H(6)1) 2.418

- S28 -

Table 10. Distances beyond the asymmetric unit out to 3.60 Å involving hydrogens (continued) atom atom distance atom atom distance H(54) H(7)1) 2.784 H(54) H(11) 3.599 H(54) H(12) 3.136 H(54) H(12)1) 2.847 H(54) H(17)2) 3.181 H(54) H(21)2) 3.513 H(54) H(26)1) 2.914 H(54) H(30)1) 3.200 H(54) H(38)1) 2.761 H(54) H(46)2) 3.488 Symmetry Operators: (1) -X+1/2,-Y+1/2-1,-Z (2) X,-Y,Z+1/2-1 (3) -X,Y,-Z+1/2-1 (4) X+1/2-1,-Y+1/2-1,Z+1/2-1 (5) -X,-Y,-Z (6) -X+1/2,Y+1/2-1,-Z+1/2 (7) -X+1,Y,-Z+1/2 (8) -X+1,-Y,-Z (9) -X+1/2,-Y+1/2,-Z (10) X,-Y,Z+1/2 (11) -X+1/2,Y+1/2,-Z+1/2 (12) X+1/2,-Y+1/2,Z+1/2 (13) X+1/2,-Y+1/2-1,Z+1/2 (14) X+1/2-1,-Y+1/2,Z+1/2-1

- S29 -

ORTEP drawing of [C6H5B(OCH2)3CCH2CH3](n-Bu4N)(H2O)