Literature DB >> 23795064

2-(1-Amino-4-tert-butyl-cyclo-hex-yl)acetic acid (tBu-β(3,3)-Ac6c) hemihydrate.

Naiem Ahmad Wani1, Vivek K Gupta, Rajni Kant, Subrayashastry Aravinda, Rajkishor Rai.   

Abstract

The title compound, C12H23NO2·0.5H2O, crystallized with two 2-(1-amino-4-tert-butylcyclohexyl)acetic acid mol-ecules, which are present as zwitterions, and one water mol-ecule in the asymmetric unit. The mol-ecular structure of each zwitterion is stabilized by an intra-molecular six-membered (C 6 ) N-H⋯O hydrogen bond. In the crystal, the two independent zwitterions are linked head-to-head by N-H⋯O hydrogen bonds. Further O-H⋯O and N-H⋯O hydrogen bonds link the zwitterions and the water molecules, forming sandwich-like layers, with a hydrophilic filling and a hydrophobic exterior, lying parallel to the ab plane.

Entities:  

Year:  2013        PMID： 23795064      PMCID： PMC3685045          DOI： 10.1107/S1600536813012725

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the importance of β-amino acids, see: Politi et al. (2009 ▶); Jiang & Yu (2007 ▶); Hansen et al. (2011 ▶). For related structures, see: Seebach et al. (1998 ▶); Vasudev et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C12H23NO2·0.5H2O M = 222.32 Triclinic, a = 6.4164 (2) Å b = 10.8091 (3) Å c = 19.1335 (6) Å α = 96.843 (3)° β = 92.018 (3)° γ = 93.901 (3)° V = 1313.25 (7) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.3 × 0.08 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.830, T max = 1.000 22269 measured reflections 5701 independent reflections 3628 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.141 S = 1.02 5701 reflections 472 parameters All H-atom parameters refined Δρmax = 0.21 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012725/qm2098sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012725/qm2098Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813012725/qm2098Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H23NO2·0.5H2OZ = 4
Mr = 222.32F(000) = 492
Triclinic, P1Dx = 1.124 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4164 (2) ÅCell parameters from 8184 reflections
b = 10.8091 (3) Åθ = 3.4–27.0°
c = 19.1335 (6) ŵ = 0.08 mm−1
α = 96.843 (3)°T = 293 K
β = 92.018 (3)°Needle, color less
γ = 93.901 (3)°0.3 × 0.08 × 0.08 mm
V = 1313.25 (7) Å3
Oxford Diffraction Xcalibur Sapphire3 diffractometer5701 independent reflections
Radiation source: fine-focus sealed tube3628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 16.1049 pixels mm-1θmax = 27.0°, θmin = 3.4°
ω scanh = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −13→13
Tmin = 0.830, Tmax = 1.000l = −24→24
22269 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141All H-atom parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.0691P)2] where P = (Fo2 + 2Fc2)/3
5701 reflections(Δ/σ)max < 0.001
472 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
H7B2−0.105 (2)−0.1438 (16)−0.1669 (8)0.024 (4)*
H2N−0.023 (3)−0.403 (2)0.0878 (10)0.054 (6)*
H1D0.244 (3)−0.3888 (17)0.2864 (9)0.037 (5)*
H8B2−0.085 (2)−0.2797 (16)−0.1450 (9)0.028 (4)*
H5B10.436 (3)−0.0776 (16)−0.2082 (8)0.031 (4)*
H2B10.250 (3)−0.4631 (17)0.1574 (9)0.033 (5)*
H4B2−0.002 (3)−0.1735 (18)0.1900 (9)0.041 (5)*
H3B2−0.022 (3)−0.3159 (17)0.2047 (8)0.030 (4)*
H1B10.434 (3)−0.4057 (17)0.1126 (10)0.044 (5)*
H2A10.448 (3)−0.2078 (18)0.0782 (11)0.052 (6)*
H4A20.329 (3)−0.3383 (17)−0.2085 (10)0.036 (5)*
H6G10.313 (3)−0.2261 (17)−0.3029 (9)0.035 (5)*
H2D−0.074 (3)−0.0963 (19)−0.2916 (10)0.049 (5)*
H3N0.143 (3)−0.3572 (18)0.0340 (11)0.048 (6)*
H4N0.117 (3)−0.047 (2)−0.0832 (10)0.057 (6)*
H1G10.587 (3)−0.281 (2)0.2142 (10)0.053 (6)*
H6B10.213 (3)−0.0148 (19)−0.2038 (10)0.051 (6)*
H1A10.445 (3)−0.1392 (18)0.1528 (10)0.050 (5)*
H3G20.313 (3)−0.1358 (19)0.2638 (10)0.048 (5)*
H1N−0.034 (3)−0.271 (2)0.0632 (12)0.072 (7)*
H3A10.488 (3)−0.2635 (18)−0.1485 (10)0.049 (5)*
H6N0.209 (3)−0.164 (2)−0.0561 (11)0.055 (6)*
H7G2−0.234 (3)−0.2967 (19)−0.2592 (10)0.054 (6)*
H8G2−0.005 (3)−0.3538 (19)−0.2648 (10)0.051 (6)*
H2G10.557 (3)−0.422 (2)0.2258 (10)0.053 (6)*
H5G10.279 (3)−0.0874 (19)−0.3186 (11)0.051 (6)*
H5N0.366 (3)−0.0632 (19)−0.0826 (10)0.053 (6)*
H4G20.125 (3)−0.187 (2)0.3059 (12)0.059 (6)*
H1W0.271 (5)0.177 (3)0.0290 (17)0.111 (11)*
H2W0.394 (6)0.291 (3)0.0225 (17)0.123 (12)*
H11−0.018 (4)−0.413 (3)−0.3834 (14)0.085 (9)*
H10−0.021 (4)−0.368 (3)−0.4636 (17)0.104 (9)*
H40.400 (5)−0.273 (3)0.4587 (19)0.112 (10)*
H80.709 (5)−0.173 (3)0.3235 (18)0.108 (12)*
H90.702 (4)−0.168 (3)0.4047 (16)0.094 (8)*
H17−0.048 (4)−0.147 (3)−0.4749 (16)0.097 (9)*
H13−0.349 (4)−0.318 (3)−0.3683 (16)0.098 (10)*
H70.537 (6)−0.094 (4)0.359 (2)0.144 (15)*
H180.173 (5)−0.118 (3)−0.4312 (16)0.118 (11)*
H15−0.348 (5)−0.260 (3)−0.443 (2)0.122 (11)*
H30.657 (5)−0.401 (3)0.4112 (18)0.111 (10)*
H10.719 (8)−0.425 (5)0.328 (3)0.21 (2)*
H120.184 (5)−0.338 (3)−0.4072 (16)0.117 (12)*
H20.511 (6)−0.477 (4)0.358 (2)0.145 (17)*
H16−0.049 (5)−0.039 (3)−0.4076 (16)0.113 (11)*
H14−0.376 (6)−0.163 (4)−0.379 (2)0.157 (17)*
H50.257 (7)−0.196 (4)0.412 (2)0.17 (2)*
H60.221 (7)−0.341 (4)0.408 (2)0.152 (19)*
N10.0633 (2)−0.33395 (15)0.07518 (8)0.0329 (4)
C1B0.2122 (2)−0.28252 (15)0.13598 (8)0.0287 (4)
C1A0.3477 (3)−0.17329 (16)0.11343 (10)0.0324 (4)
C1'0.2390 (3)−0.06639 (16)0.08696 (8)0.0322 (4)
O10.35298 (19)0.02596 (12)0.07388 (7)0.0465 (4)
O20.04386 (18)−0.07591 (12)0.07914 (7)0.0472 (4)
C1B10.3463 (3)−0.38803 (18)0.15219 (10)0.0363 (4)
C1G10.4799 (3)−0.3539 (2)0.22047 (10)0.0417 (5)
C1D0.3481 (3)−0.31899 (19)0.28349 (9)0.0410 (5)
C1B20.0815 (3)−0.24555 (19)0.19973 (9)0.0355 (4)
C1G20.2166 (3)−0.2123 (2)0.26764 (10)0.0417 (5)
C10.6058 (8)−0.4031 (4)0.3647 (2)0.1059 (13)
C20.3211 (7)−0.2808 (6)0.41463 (15)0.1039 (13)
C30.6186 (6)−0.1766 (4)0.36012 (18)0.0875 (10)
C40.4739 (3)−0.2945 (2)0.35522 (10)0.0556 (6)
N20.2266 (3)−0.10896 (15)−0.08954 (8)0.0334 (4)
C2B0.2019 (3)−0.18188 (15)−0.16194 (8)0.0295 (4)
C2A0.3351 (3)−0.29428 (16)−0.16156 (9)0.0317 (4)
O30.2980 (2)−0.34430 (12)−0.04517 (6)0.0453 (4)
O40.1620 (2)−0.48186 (12)−0.13336 (7)0.0512 (4)
C2'0.2591 (3)−0.38243 (16)−0.10927 (9)0.0325 (4)
C2B10.2811 (3)−0.09492 (18)−0.21438 (9)0.0373 (4)
C2G10.2287 (3)−0.1492 (2)−0.29083 (10)0.0411 (5)
C2D−0.0054 (3)−0.18123 (19)−0.30538 (9)0.0402 (5)
C2G2−0.0794 (3)−0.2736 (2)−0.25466 (9)0.0405 (5)
C2B2−0.0309 (3)−0.21945 (19)−0.17772 (9)0.0352 (4)
C50.0283 (6)−0.3446 (3)−0.41124 (15)0.0771 (8)
C6−0.3038 (5)−0.2413 (5)−0.39376 (16)0.0922 (12)
C70.0084 (6)−0.1213 (4)−0.42883 (15)0.0823 (9)
C8−0.0661 (3)−0.2238 (2)−0.38415 (10)0.0533 (6)
O1W0.2635 (3)0.25362 (19)0.01566 (8)0.0595 (4)
U11U22U33U12U13U23
N10.0354 (8)0.0291 (9)0.0332 (8)−0.0036 (7)−0.0030 (7)0.0048 (6)
C1B0.0292 (8)0.0266 (9)0.0296 (9)0.0006 (7)−0.0028 (7)0.0026 (7)
C1A0.0287 (9)0.0290 (10)0.0385 (10)−0.0006 (8)−0.0020 (8)0.0027 (7)
C1'0.0357 (10)0.0291 (10)0.0306 (9)0.0013 (8)−0.0030 (7)0.0005 (7)
O10.0416 (7)0.0380 (8)0.0615 (9)−0.0044 (6)−0.0016 (6)0.0181 (6)
O20.0335 (7)0.0330 (8)0.0750 (10)0.0027 (6)−0.0116 (6)0.0102 (6)
C1B10.0413 (10)0.0315 (11)0.0366 (10)0.0075 (9)0.0005 (8)0.0033 (8)
C1G10.0412 (11)0.0421 (12)0.0431 (11)0.0108 (10)−0.0048 (8)0.0081 (9)
C1D0.0435 (11)0.0432 (12)0.0355 (10)−0.0062 (10)−0.0031 (8)0.0085 (8)
C1B20.0318 (9)0.0381 (11)0.0363 (10)0.0037 (9)0.0007 (7)0.0025 (8)
C1G20.0415 (11)0.0471 (13)0.0344 (10)0.0043 (10)0.0020 (8)−0.0044 (8)
C10.140 (3)0.105 (3)0.076 (2)0.028 (3)−0.051 (2)0.027 (2)
C20.106 (3)0.169 (4)0.0339 (15)−0.008 (3)−0.0028 (15)0.0161 (19)
C30.086 (2)0.102 (3)0.0660 (19)−0.032 (2)−0.0347 (17)0.0090 (17)
C40.0604 (13)0.0670 (15)0.0389 (11)−0.0024 (12)−0.0102 (10)0.0126 (10)
N20.0395 (9)0.0294 (9)0.0308 (8)0.0045 (8)−0.0030 (6)0.0022 (6)
C2B0.0356 (9)0.0257 (9)0.0266 (8)−0.0006 (7)0.0006 (7)0.0025 (7)
C2A0.0346 (10)0.0288 (10)0.0320 (10)0.0012 (8)0.0059 (7)0.0037 (7)
O30.0559 (8)0.0475 (8)0.0324 (7)−0.0048 (7)0.0018 (6)0.0090 (6)
O40.0638 (9)0.0327 (8)0.0546 (8)−0.0154 (7)0.0026 (7)0.0056 (6)
C2'0.0303 (9)0.0301 (10)0.0388 (10)0.0049 (8)0.0042 (7)0.0083 (8)
C2B10.0415 (11)0.0330 (11)0.0373 (10)−0.0047 (9)−0.0010 (8)0.0097 (8)
C2G10.0448 (11)0.0447 (12)0.0347 (10)−0.0058 (10)0.0024 (8)0.0134 (9)
C2D0.0419 (11)0.0464 (12)0.0324 (10)0.0047 (9)−0.0008 (8)0.0042 (8)
C2G20.0345 (10)0.0478 (13)0.0369 (10)−0.0060 (10)−0.0005 (8)0.0009 (8)
C2B20.0329 (9)0.0375 (11)0.0350 (10)0.0012 (9)0.0038 (7)0.0031 (8)
C50.094 (2)0.083 (2)0.0490 (16)0.0087 (18)−0.0020 (15)−0.0152 (14)
C60.0590 (17)0.163 (4)0.0507 (17)−0.003 (2)−0.0195 (13)0.011 (2)
C70.105 (3)0.107 (3)0.0371 (14)0.008 (2)−0.0058 (14)0.0227 (15)
C80.0503 (12)0.0753 (16)0.0332 (10)0.0041 (11)−0.0039 (9)0.0040 (10)
O1W0.0497 (10)0.0632 (11)0.0667 (10)−0.0001 (8)−0.0156 (7)0.0203 (8)
N1—C1B1.507 (2)N2—H4N1.00 (2)
N1—H2N0.96 (2)N2—H6N0.93 (2)
N1—H3N0.97 (2)N2—H5N0.99 (2)
N1—H1N0.99 (2)C2B—C2B11.531 (2)
C1B—C1B11.529 (2)C2B—C2B21.531 (2)
C1B—C1A1.531 (2)C2B—C2A1.532 (2)
C1B—C1B21.534 (2)C2A—C2'1.531 (2)
C1A—C1'1.517 (2)C2A—H4A20.962 (18)
C1A—H2A11.01 (2)C2A—H3A11.03 (2)
C1A—H1A10.98 (2)O3—C2'1.257 (2)
C1'—O11.252 (2)O4—C2'1.236 (2)
C1'—O21.252 (2)C2B1—C2G11.527 (3)
C1B1—C1G11.530 (3)C2B1—H5B10.997 (17)
C1B1—H2B11.004 (18)C2B1—H6B11.00 (2)
C1B1—H1B10.968 (19)C2G1—C2D1.526 (3)
C1G1—C1D1.522 (3)C2G1—H6G11.032 (18)
C1G1—H1G11.03 (2)C2G1—H5G10.95 (2)
C1G1—H2G10.93 (2)C2D—C2G21.537 (3)
C1D—C1G21.527 (3)C2D—C81.551 (3)
C1D—C41.553 (3)C2D—H2D1.06 (2)
C1D—H1D0.981 (18)C2G2—C2B21.531 (2)
C1B2—C1G21.528 (3)C2G2—H7G21.00 (2)
C1B2—H4B21.01 (2)C2G2—H8G21.02 (2)
C1B2—H3B20.992 (17)C2B2—H7B20.977 (17)
C1G2—H3G21.01 (2)C2B2—H8B21.009 (17)
C1G2—H4G20.98 (2)C5—C81.520 (4)
C1—C41.518 (4)C5—H111.00 (3)
C1—H30.94 (3)C5—H101.04 (3)
C1—H11.04 (5)C5—H121.00 (3)
C1—H20.96 (4)C6—C81.526 (3)
C2—C41.527 (4)C6—H131.04 (3)
C2—H40.96 (4)C6—H150.96 (4)
C2—H51.04 (5)C6—H141.01 (4)
C2—H60.88 (4)C7—C81.539 (4)
C3—C41.515 (4)C7—H170.94 (3)
C3—H80.93 (3)C7—H181.06 (3)
C3—H90.98 (3)C7—H161.03 (3)
C3—H71.06 (4)O1W—H1W0.90 (3)
N2—C2B1.508 (2)O1W—H2W0.90 (4)
C1B—N1—H2N109.8 (12)C2B—N2—H6N108.7 (13)
C1B—N1—H3N109.1 (11)H4N—N2—H6N108.0 (17)
H2N—N1—H3N112.0 (16)C2B—N2—H5N110.6 (11)
C1B—N1—H1N111.5 (13)H4N—N2—H5N108.7 (16)
H2N—N1—H1N106.4 (17)H6N—N2—H5N110.4 (17)
H3N—N1—H1N108.0 (17)N2—C2B—C2B1107.29 (13)
N1—C1B—C1B1107.24 (14)N2—C2B—C2B2108.19 (14)
N1—C1B—C1A108.17 (13)C2B1—C2B—C2B2109.69 (14)
C1B1—C1B—C1A110.82 (14)N2—C2B—C2A107.30 (14)
N1—C1B—C1B2107.71 (14)C2B1—C2B—C2A111.09 (14)
C1B1—C1B—C1B2109.03 (14)C2B2—C2B—C2A113.05 (14)
C1A—C1B—C1B2113.62 (14)C2'—C2A—C2B112.01 (13)
C1'—C1A—C1B118.24 (14)C2'—C2A—H4A2110.0 (10)
C1'—C1A—H2A1110.8 (11)C2B—C2A—H4A2108.2 (10)
C1B—C1A—H2A1108.4 (11)C2'—C2A—H3A1109.0 (11)
C1'—C1A—H1A1108.7 (11)C2B—C2A—H3A1109.5 (11)
C1B—C1A—H1A1108.7 (11)H4A2—C2A—H3A1108.1 (14)
H2A1—C1A—H1A1100.6 (15)O4—C2'—O3126.20 (16)
O1—C1'—O2124.32 (16)O4—C2'—C2A117.73 (16)
O1—C1'—C1A116.98 (15)O3—C2'—C2A116.04 (15)
O2—C1'—C1A118.70 (15)C2G1—C2B1—C2B112.51 (15)
C1B—C1B1—C1G1112.15 (15)C2G1—C2B1—H5B1108.3 (9)
C1B—C1B1—H2B1107.8 (10)C2B—C2B1—H5B1110.5 (10)
C1G1—C1B1—H2B1108.6 (10)C2G1—C2B1—H6B1109.5 (11)
C1B—C1B1—H1B1107.4 (11)C2B—C2B1—H6B1107.1 (11)
C1G1—C1B1—H1B1110.6 (11)H5B1—C2B1—H6B1108.9 (15)
H2B1—C1B1—H1B1110.2 (15)C2B1—C2G1—C2D112.37 (16)
C1D—C1G1—C1B1112.19 (16)C2B1—C2G1—H6G1108.9 (10)
C1D—C1G1—H1G1110.3 (11)C2D—C2G1—H6G1111.6 (10)
C1B1—C1G1—H1G1109.0 (11)C2B1—C2G1—H5G1105.8 (12)
C1D—C1G1—H2G1112.6 (12)C2D—C2G1—H5G1111.0 (12)
C1B1—C1G1—H2G1106.3 (13)H6G1—C2G1—H5G1106.8 (15)
H1G1—C1G1—H2G1106.2 (16)C2G1—C2D—C2G2108.11 (15)
C1G1—C1D—C1G2108.70 (16)C2G1—C2D—C8113.58 (15)
C1G1—C1D—C4114.32 (17)C2G2—C2D—C8114.75 (16)
C1G2—C1D—C4114.12 (17)C2G1—C2D—H2D104.7 (10)
C1G1—C1D—H1D107.8 (10)C2G2—C2D—H2D108.2 (10)
C1G2—C1D—H1D103.7 (10)C8—C2D—H2D106.9 (10)
C4—C1D—H1D107.4 (10)C2B2—C2G2—C2D111.36 (16)
C1G2—C1B2—C1B112.20 (15)C2B2—C2G2—H7G2106.5 (11)
C1G2—C1B2—H4B2110.7 (10)C2D—C2G2—H7G2113.4 (12)
C1B—C1B2—H4B2109.2 (10)C2B2—C2G2—H8G2108.8 (11)
C1G2—C1B2—H3B2110.2 (10)C2D—C2G2—H8G2109.1 (11)
C1B—C1B2—H3B2108.5 (9)H7G2—C2G2—H8G2107.6 (16)
H4B2—C1B2—H3B2105.8 (14)C2B—C2B2—C2G2112.75 (14)
C1D—C1G2—C1B2112.06 (16)C2B—C2B2—H7B2106.6 (9)
C1D—C1G2—H3G2109.0 (11)C2G2—C2B2—H7B2109.6 (9)
C1B2—C1G2—H3G2109.7 (11)C2B—C2B2—H8B2111.1 (9)
C1D—C1G2—H4G2112.5 (12)C2G2—C2B2—H8B2110.5 (9)
C1B2—C1G2—H4G2108.1 (12)H7B2—C2B2—H8B2106.0 (13)
H3G2—C1G2—H4G2105.2 (16)C8—C5—H11110.8 (15)
C4—C1—H3112 (2)C8—C5—H10107.8 (16)
C4—C1—H1119 (3)H11—C5—H10110 (2)
H3—C1—H1112 (3)C8—C5—H12112.9 (19)
C4—C1—H2106 (2)H11—C5—H12106 (2)
H3—C1—H2103 (3)H10—C5—H12110 (2)
H1—C1—H2103 (4)C8—C6—H13106.1 (16)
C4—C2—H4108.2 (19)C8—C6—H15111 (2)
C4—C2—H5106 (2)H13—C6—H15108 (3)
H4—C2—H5106 (3)C8—C6—H14113 (2)
C4—C2—H6111 (3)H13—C6—H14115 (3)
H4—C2—H6116 (3)H15—C6—H14103 (3)
H5—C2—H6109 (4)C8—C7—H17106.2 (17)
C4—C3—H8115 (2)C8—C7—H18109.3 (18)
C4—C3—H9108.7 (16)H17—C7—H18107 (2)
H8—C3—H9109 (3)C8—C7—H16107.5 (18)
C4—C3—H7113 (2)H17—C7—H16111 (2)
H8—C3—H7103 (3)H18—C7—H16115 (3)
H9—C3—H7108 (3)C5—C8—C6109.5 (3)
C3—C4—C1108.1 (3)C5—C8—C7108.8 (2)
C3—C4—C2108.9 (3)C6—C8—C7107.3 (3)
C1—C4—C2109.0 (3)C5—C8—C2D112.25 (19)
C3—C4—C1D111.70 (19)C6—C8—C2D109.20 (19)
C1—C4—C1D110.1 (2)C7—C8—C2D109.7 (2)
C2—C4—C1D109.0 (2)H1W—O1W—H2W106 (3)
C2B—N2—H4N110.4 (12)
N1—C1B—C1A—C1'55.6 (2)N2—C2B—C2A—C2'62.84 (18)
C1B1—C1B—C1A—C1'172.92 (15)C2B1—C2B—C2A—C2'179.82 (14)
C1B2—C1B—C1A—C1'−63.9 (2)C2B2—C2B—C2A—C2'−56.36 (19)
C1B—C1A—C1'—O1174.79 (15)C2B—C2A—C2'—O4104.87 (18)
C1B—C1A—C1'—O2−5.7 (2)C2B—C2A—C2'—O3−73.4 (2)
N1—C1B—C1B1—C1G1−170.80 (15)N2—C2B—C2B1—C2G1−169.63 (16)
C1A—C1B—C1B1—C1G171.3 (2)C2B2—C2B—C2B1—C2G1−52.3 (2)
C1B2—C1B—C1B1—C1G1−54.4 (2)C2A—C2B—C2B1—C2G173.4 (2)
C1B—C1B1—C1G1—C1D57.2 (2)C2B—C2B1—C2G1—C2D56.6 (2)
C1B1—C1G1—C1D—C1G2−56.2 (2)C2B1—C2G1—C2D—C2G2−57.4 (2)
C1B1—C1G1—C1D—C4175.04 (17)C2B1—C2G1—C2D—C8174.07 (17)
N1—C1B—C1B2—C1G2170.54 (15)C2G1—C2D—C2G2—C2B257.3 (2)
C1B1—C1B—C1B2—C1G254.5 (2)C8—C2D—C2G2—C2B2−174.78 (17)
C1A—C1B—C1B2—C1G2−69.7 (2)N2—C2B—C2B2—C2G2169.76 (15)
C1G1—C1D—C1G2—C1B256.1 (2)C2B1—C2B—C2B2—C2G253.0 (2)
C4—C1D—C1G2—C1B2−175.00 (16)C2A—C2B—C2B2—C2G2−71.6 (2)
C1B—C1B2—C1G2—C1D−57.0 (2)C2D—C2G2—C2B2—C2B−57.2 (2)
C1G1—C1D—C4—C368.5 (3)C2G1—C2D—C8—C563.8 (3)
C1G2—C1D—C4—C3−57.6 (3)C2G2—C2D—C8—C5−61.3 (3)
C1G1—C1D—C4—C1−51.7 (3)C2G1—C2D—C8—C6−174.6 (3)
C1G2—C1D—C4—C1−177.7 (3)C2G2—C2D—C8—C660.3 (3)
C1G1—C1D—C4—C2−171.2 (3)C2G1—C2D—C8—C7−57.3 (3)
C1G2—C1D—C4—C262.8 (3)C2G2—C2D—C8—C7177.6 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O21.00 (2)2.12 (2)2.792 (2)123.5 (15)
N1—H1N···O1Wi1.00 (2)2.11 (2)2.919 (2)137.8 (17)
O1W—H1W···O10.89 (3)2.03 (3)2.903 (2)166 (3)
N1—H2N···O4ii0.96 (2)1.81 (2)2.747 (2)166.0 (17)
O1W—H2W···O3iii0.90 (4)2.04 (4)2.929 (2)169 (3)
N1—H3N···O30.97 (2)1.86 (2)2.7903 (19)160.7 (17)
N2—H4N···O2i1.00 (2)1.73 (2)2.729 (2)170.5 (19)
N2—H5N···O1iii0.99 (2)1.818 (19)2.779 (2)163.1 (18)
N2—H6N···O30.93 (2)2.10 (2)2.836 (2)135.4 (17)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1N⋯O21.00 (2)2.12 (2)2.792 (2)123.5 (15)
N1—H1N⋯O1W i 1.00 (2)2.11 (2)2.919 (2)137.8 (17)
O1W—H1W⋯O10.89 (3)2.03 (3)2.903 (2)166 (3)
N1—H2N⋯O4ii 0.96 (2)1.81 (2)2.747 (2)166.0 (17)
O1W—H2W⋯O3iii 0.90 (4)2.04 (4)2.929 (2)169 (3)
N1—H3N⋯O30.97 (2)1.86 (2)2.7903 (19)160.7 (17)
N2—H4N⋯O2i 1.00 (2)1.73 (2)2.729 (2)170.5 (19)
N2—H5N⋯O1iii 0.99 (2)1.818 (19)2.779 (2)163.1 (18)
N2—H6N⋯O30.93 (2)2.10 (2)2.836 (2)135.4 (17)

Symmetry codes: (i) ; (ii) ; (iii) .

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