organic compounds
threo-2-(2,6-Dimethoxyphenoxy)-1-(4-ethoxy-3-methoxyphenyl)propane-1,3-diol
aInternational Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan, bInstitute of Sustainability Science, Kyoto University, Japan, and cResearch Institute for Sustainable Humanosphere, Kyoto University, Uji, Kyoto 611-0011, Japan
*Correspondence e-mail: masaharu@scl.kyoto-u.ac.jp
In the 20H26O7, a lignin model compound, the contains two molecules which adopt almost identical overall conformations with some deviation in the region of the terminal hydroxyl groups. The two molecules are linked by an intermolecular O—H⋯O hydrogen bond. They also develop intramolecular O—H⋯O hydrogen bonds.
of the title compound, CRelated literature
For the synthesis, see: von Unge et al. (1988). For the of two related guaiacylglycerol β-syringyl ether type lignin model dimers, see: Langer, Li et al. (2002); Langer, Lundquist et al. (2002). For the of several related syringylglycerol β-syringyl see: Langer & Lundquist (2001); Langer, Li et al. (2002); Langer, Lundquist et al. (2002); Langer et al. (2005); Lundquist et al. (2005); Stomberg & Lundquist (1989).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2006); cell CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Carruthers et al., 1999); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536809018431/bx2203sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018431/bx2203Isup2.hkl
The title compound was synthesized in two steps with a procedure similar to that reported in the literature (von Unge et al., 1988). Separation of the erythro and threo forms of the first step product was accomplished by recrystallization from methanol to give threo-3-(4-ethoxy-3-methoxyphenyl)-2-(2,6-Dimethoxyphenoxy)- -3-hydroxypropanoic acid 1. The title compound, threo-1-(4-ethoxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-1,3- propanediol, was synthesized from 1, and Single crystals of that suitable for X-ray crystallography were obtained from methanol.
All H atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 (aromatic), 0.96 (methyl), 0.97 (methylene), 0.98 (methine) and 0.82 Å (hydroxyl), and with Uiso(H) = xUeq (carrier atom), where x = 1.5 for methyl and hydroxyl groups and x = 1.2 for other H atoms.
Data collection: CrystalClear (Rigaku, 2006); cell
CrystalClear (Rigaku, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Carruthers et al., 1999); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2007).C20H26O7 | F(000) = 1616.00 |
Mr = 378.42 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 7455 reflections |
a = 9.929 (4) Å | θ = 3.0–27.5° |
b = 28.066 (10) Å | µ = 0.10 mm−1 |
c = 13.985 (5) Å | T = 173 K |
β = 100.954 (2)° | Block, colorless |
V = 3826 (2) Å3 | 0.50 × 0.50 × 0.40 mm |
Z = 8 |
Rigaku Saturn diffractometer | 3941 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.056 |
ω scans | θmax = 27.5° |
Absorption correction: numerical (CrystalClear; Rigaku, 2006) | h = −11→12 |
Tmin = 0.938, Tmax = 0.961 | k = −35→36 |
30389 measured reflections | l = −18→16 |
8726 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.074 | w = 1/[0.0018Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.227 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.59 e Å−3 |
8726 reflections | Δρmin = −0.67 e Å−3 |
539 parameters |
C20H26O7 | V = 3826 (2) Å3 |
Mr = 378.42 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.929 (4) Å | µ = 0.10 mm−1 |
b = 28.066 (10) Å | T = 173 K |
c = 13.985 (5) Å | 0.50 × 0.50 × 0.40 mm |
β = 100.954 (2)° |
Rigaku Saturn diffractometer | 8726 independent reflections |
Absorption correction: numerical (CrystalClear; Rigaku, 2006) | 3941 reflections with F2 > 2σ(F2) |
Tmin = 0.938, Tmax = 0.961 | Rint = 0.056 |
30389 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 539 parameters |
wR(F2) = 0.227 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.59 e Å−3 |
8726 reflections | Δρmin = −0.67 e Å−3 |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O(1) | 0.4275 (2) | 0.14739 (7) | 0.32648 (14) | 0.0342 (6) | |
O(2) | 0.6049 (2) | 0.07942 (7) | 0.34454 (14) | 0.0303 (5) | |
O(3) | 0.3267 (2) | 0.07866 (7) | 0.71410 (14) | 0.0320 (6) | |
O(4) | 0.5503 (2) | 0.23444 (8) | 0.73756 (17) | 0.0475 (7) | |
O(5) | 0.3404 (2) | 0.16987 (8) | 0.80643 (14) | 0.0327 (6) | |
O(6) | 0.1968 (2) | 0.09850 (8) | 0.86837 (14) | 0.0347 (6) | |
O(7) | 0.5527 (2) | 0.21120 (9) | 0.92951 (16) | 0.0478 (7) | |
O(8) | 0.9339 (2) | 0.15184 (8) | 0.33101 (15) | 0.0372 (6) | |
O(9) | 1.1062 (2) | 0.08238 (7) | 0.34465 (14) | 0.0308 (5) | |
O(10) | 0.8242 (2) | 0.07441 (7) | 0.71045 (14) | 0.0307 (5) | |
O(11) | 0.7854 (2) | 0.22309 (8) | 0.64640 (16) | 0.0475 (7) | |
O(12) | 0.8095 (2) | 0.16035 (7) | 0.80390 (14) | 0.0296 (5) | |
O(13) | 0.6895 (2) | 0.08724 (8) | 0.87353 (15) | 0.0357 (6) | |
O(14) | 1.0163 (2) | 0.20864 (9) | 0.91436 (17) | 0.0518 (8) | |
C(1) | 0.4133 (3) | 0.10906 (10) | 0.5791 (2) | 0.0241 (7) | |
C(2) | 0.3838 (3) | 0.13478 (10) | 0.49118 (19) | 0.0260 (7) | |
C(3) | 0.4498 (3) | 0.12462 (10) | 0.4152 (2) | 0.0262 (7) | |
C(4) | 0.5457 (3) | 0.08738 (10) | 0.42410 (19) | 0.0242 (7) | |
C(5) | 0.5741 (3) | 0.06160 (10) | 0.5105 (2) | 0.0262 (7) | |
C(6) | 0.5080 (3) | 0.07258 (10) | 0.5872 (2) | 0.0253 (7) | |
C(7) | 0.3190 (3) | 0.18146 (11) | 0.3079 (2) | 0.0390 (9) | |
C(8) | 0.6995 (3) | 0.04042 (10) | 0.3506 (2) | 0.0296 (8) | |
C(9) | 0.7502 (3) | 0.03888 (13) | 0.2561 (2) | 0.0419 (10) | |
C(10) | 0.3426 (3) | 0.12164 (10) | 0.6632 (2) | 0.0271 (7) | |
C(11) | 0.4245 (3) | 0.15808 (10) | 0.7333 (2) | 0.0268 (7) | |
C(12) | 0.4476 (3) | 0.20437 (11) | 0.6829 (2) | 0.0361 (9) | |
C(13) | 0.3800 (3) | 0.15276 (11) | 0.9010 (2) | 0.0310 (8) | |
C(14) | 0.3031 (3) | 0.11713 (12) | 0.9350 (2) | 0.0306 (8) | |
C(15) | 0.3344 (3) | 0.10274 (13) | 1.0327 (2) | 0.0364 (9) | |
C(16) | 0.4424 (3) | 0.12367 (13) | 1.0950 (2) | 0.0396 (9) | |
C(17) | 0.5179 (3) | 0.15965 (13) | 1.0630 (2) | 0.0394 (9) | |
C(18) | 0.4864 (3) | 0.17446 (12) | 0.9666 (2) | 0.0336 (8) | |
C(19) | 0.1179 (3) | 0.06067 (12) | 0.9001 (2) | 0.0399 (10) | |
C(20) | 0.6557 (4) | 0.23658 (15) | 0.9951 (2) | 0.0607 (13) | |
C(21) | 0.9136 (3) | 0.10908 (10) | 0.57963 (19) | 0.0245 (7) | |
C(22) | 0.8872 (3) | 0.13658 (10) | 0.4944 (2) | 0.0267 (7) | |
C(23) | 0.9542 (3) | 0.12739 (10) | 0.4183 (2) | 0.0267 (7) | |
C(24) | 1.0484 (3) | 0.08982 (10) | 0.4250 (2) | 0.0257 (7) | |
C(25) | 1.0758 (3) | 0.06276 (11) | 0.5098 (2) | 0.0275 (8) | |
C(26) | 1.0083 (3) | 0.07255 (10) | 0.5861 (2) | 0.0272 (7) | |
C(27) | 0.8261 (3) | 0.18541 (12) | 0.3144 (2) | 0.0431 (10) | |
C(28) | 1.1946 (3) | 0.04152 (11) | 0.3470 (2) | 0.0326 (8) | |
C(29) | 1.2407 (4) | 0.03979 (13) | 0.2500 (2) | 0.0456 (10) | |
C(30) | 0.8354 (3) | 0.11832 (10) | 0.66079 (19) | 0.0246 (7) | |
C(31) | 0.9029 (3) | 0.15579 (10) | 0.7346 (2) | 0.0273 (7) | |
C(32) | 0.9155 (3) | 0.20479 (11) | 0.6913 (2) | 0.0342 (9) | |
C(33) | 0.8574 (3) | 0.14663 (11) | 0.8994 (2) | 0.0301 (8) | |
C(34) | 0.7920 (3) | 0.10971 (12) | 0.9378 (2) | 0.0311 (8) | |
C(35) | 0.8316 (3) | 0.09725 (14) | 1.0365 (2) | 0.0433 (10) | |
C(36) | 0.9362 (3) | 0.12216 (15) | 1.0940 (2) | 0.0477 (11) | |
C(37) | 1.0023 (3) | 0.15938 (15) | 1.0574 (2) | 0.0494 (11) | |
C(38) | 0.9632 (3) | 0.17161 (12) | 0.9596 (2) | 0.0366 (9) | |
C(39) | 0.6114 (3) | 0.05122 (12) | 0.9101 (2) | 0.0439 (10) | |
C(40) | 1.1206 (4) | 0.23640 (16) | 0.9716 (3) | 0.0668 (14) | |
H(2) | 0.3186 | 0.1590 | 0.4841 | 0.031* | |
H(5) | 0.6376 | 0.0369 | 0.5173 | 0.031* | |
H(6) | 0.5278 | 0.0551 | 0.6446 | 0.030* | |
H(15) | 0.2826 | 0.0791 | 1.0553 | 0.045* | |
H(16) | 0.4646 | 0.1135 | 1.1594 | 0.048* | |
H(17) | 0.5897 | 0.1739 | 1.1059 | 0.047* | |
H(22) | 0.8237 | 0.1613 | 0.4891 | 0.032* | |
H(25) | 1.1393 | 0.0381 | 0.5156 | 0.033* | |
H(26) | 1.0273 | 0.0542 | 0.6425 | 0.033* | |
H(35) | 0.7879 | 0.0725 | 1.0626 | 0.053* | |
H(36) | 0.9629 | 0.1138 | 1.1592 | 0.057* | |
H(37) | 1.0721 | 0.1760 | 1.0976 | 0.059* | |
H(10A) | 0.2517 | 0.1348 | 0.6370 | 0.033* | |
H(11A) | 0.5124 | 0.1444 | 0.7652 | 0.033* | |
H(30) | 0.7429 | 0.1293 | 0.6318 | 0.030* | |
H(31) | 0.9930 | 0.1446 | 0.7682 | 0.033* | |
H(8A) | 0.7758 | 0.0454 | 0.4043 | 0.036* | |
H(8B) | 0.6536 | 0.0108 | 0.3602 | 0.036* | |
H(12A) | 0.3615 | 0.2216 | 0.6695 | 0.043* | |
H(12B) | 0.4760 | 0.1967 | 0.6221 | 0.043* | |
H(28A) | 1.2733 | 0.0447 | 0.3996 | 0.041* | |
H(28B) | 1.1448 | 0.0127 | 0.3563 | 0.040* | |
H(32A) | 0.9735 | 0.2025 | 0.6429 | 0.041* | |
H(32B) | 0.9570 | 0.2263 | 0.7428 | 0.041* | |
H(7A) | 0.2355 | 0.1658 | 0.2784 | 0.048* | |
H(7B) | 0.3409 | 0.2056 | 0.2648 | 0.048* | |
H(7C) | 0.3075 | 0.1959 | 0.3681 | 0.048* | |
H(19A) | 0.1582 | 0.0305 | 0.8892 | 0.049* | |
H(19B) | 0.0255 | 0.0619 | 0.8639 | 0.049* | |
H(19C) | 0.1172 | 0.0644 | 0.9682 | 0.049* | |
H(20A) | 0.6146 | 0.2630 | 1.0225 | 0.075* | |
H(20B) | 0.7239 | 0.2482 | 0.9605 | 0.075* | |
H(20C) | 0.6980 | 0.2156 | 1.0463 | 0.075* | |
H(27A) | 0.7432 | 0.1700 | 0.2827 | 0.053* | |
H(27B) | 0.8485 | 0.2106 | 0.2736 | 0.053* | |
H(27C) | 0.8130 | 0.1984 | 0.3754 | 0.052* | |
H(39A) | 0.6549 | 0.0209 | 0.9068 | 0.056* | |
H(39B) | 0.5204 | 0.0503 | 0.8717 | 0.055* | |
H(39C) | 0.6066 | 0.0582 | 0.9766 | 0.055* | |
H(40A) | 1.0798 | 0.2624 | 1.0002 | 0.081* | |
H(40B) | 1.1809 | 0.2486 | 0.9312 | 0.081* | |
H(40C) | 1.1720 | 0.2169 | 1.0221 | 0.081* | |
H(9A) | 0.6911 | 0.0188 | 0.2107 | 0.053* | |
H(9B) | 0.8418 | 0.0263 | 0.2672 | 0.053* | |
H(9C) | 0.7501 | 0.0705 | 0.2299 | 0.053* | |
H(3) | 0.3286 | 0.0846 | 0.7717 | 0.040* | |
H(29A) | 1.1769 | 0.0212 | 0.2048 | 0.058* | |
H(29B) | 1.3301 | 0.0255 | 0.2586 | 0.058* | |
H(29C) | 1.2446 | 0.0716 | 0.2253 | 0.058* | |
H(4) | 0.5138 | 0.2524 | 0.7713 | 0.058* | |
H(10) | 0.8214 | 0.0799 | 0.7677 | 0.038* | |
H(11) | 0.7260 | 0.2125 | 0.6741 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.0501 (14) | 0.0351 (12) | 0.0190 (10) | 0.0097 (10) | 0.0106 (9) | 0.0096 (8) |
O(2) | 0.0363 (13) | 0.0358 (11) | 0.0216 (10) | 0.0068 (10) | 0.0121 (9) | 0.0019 (8) |
O(3) | 0.0427 (13) | 0.0333 (11) | 0.0228 (10) | −0.0069 (10) | 0.0131 (9) | −0.0002 (8) |
O(4) | 0.0571 (17) | 0.0383 (13) | 0.0485 (14) | −0.0046 (12) | 0.0134 (12) | −0.0073 (11) |
O(5) | 0.0382 (13) | 0.0441 (13) | 0.0178 (10) | 0.0123 (10) | 0.0100 (9) | 0.0017 (9) |
O(6) | 0.0318 (12) | 0.0519 (14) | 0.0216 (10) | −0.0016 (10) | 0.0081 (9) | 0.0005 (9) |
O(7) | 0.0552 (17) | 0.0563 (15) | 0.0331 (12) | −0.0172 (13) | 0.0115 (11) | −0.0087 (11) |
O(8) | 0.0493 (15) | 0.0416 (13) | 0.0234 (10) | 0.0132 (11) | 0.0139 (10) | 0.0109 (9) |
O(9) | 0.0384 (13) | 0.0334 (11) | 0.0236 (10) | 0.0044 (9) | 0.0136 (9) | 0.0017 (8) |
O(10) | 0.0415 (13) | 0.0300 (11) | 0.0224 (10) | −0.0044 (9) | 0.0104 (9) | −0.0004 (8) |
O(11) | 0.0620 (18) | 0.0404 (13) | 0.0394 (13) | −0.0062 (12) | 0.0077 (12) | 0.0078 (10) |
O(12) | 0.0345 (12) | 0.0377 (12) | 0.0174 (9) | 0.0038 (10) | 0.0069 (8) | −0.0001 (8) |
O(13) | 0.0365 (13) | 0.0475 (13) | 0.0255 (11) | −0.0025 (10) | 0.0117 (9) | 0.0032 (9) |
O(14) | 0.0590 (17) | 0.0576 (16) | 0.0393 (14) | −0.0221 (14) | 0.0111 (12) | −0.0151 (12) |
C(1) | 0.0261 (16) | 0.0270 (15) | 0.0198 (13) | −0.0055 (12) | 0.0054 (11) | −0.0026 (11) |
C(2) | 0.0308 (17) | 0.0258 (15) | 0.0214 (14) | 0.0031 (13) | 0.0044 (12) | −0.0006 (11) |
C(3) | 0.0358 (18) | 0.0248 (15) | 0.0177 (13) | 0.0012 (13) | 0.0049 (12) | 0.0016 (11) |
C(4) | 0.0244 (15) | 0.0303 (15) | 0.0191 (13) | −0.0027 (12) | 0.0072 (11) | −0.0034 (11) |
C(5) | 0.0275 (16) | 0.0271 (15) | 0.0247 (14) | −0.0005 (13) | 0.0067 (12) | 0.0024 (11) |
C(6) | 0.0259 (16) | 0.0296 (15) | 0.0195 (13) | −0.0032 (13) | 0.0021 (12) | 0.0029 (11) |
C(7) | 0.056 (2) | 0.0333 (17) | 0.0290 (17) | 0.0142 (16) | 0.0112 (16) | 0.0086 (14) |
C(8) | 0.0323 (18) | 0.0249 (15) | 0.0332 (16) | 0.0015 (13) | 0.0106 (14) | 0.0002 (12) |
C(9) | 0.049 (2) | 0.048 (2) | 0.0348 (17) | 0.0028 (17) | 0.0235 (16) | −0.0029 (15) |
C(10) | 0.0289 (16) | 0.0329 (16) | 0.0199 (14) | −0.0009 (13) | 0.0062 (12) | 0.0012 (12) |
C(11) | 0.0300 (16) | 0.0321 (16) | 0.0194 (13) | 0.0027 (13) | 0.0076 (12) | 0.0004 (12) |
C(12) | 0.052 (2) | 0.0299 (16) | 0.0259 (15) | −0.0069 (15) | 0.0056 (15) | −0.0043 (13) |
C(13) | 0.0329 (18) | 0.0421 (18) | 0.0178 (13) | 0.0096 (15) | 0.0047 (12) | −0.0014 (12) |
C(14) | 0.0275 (17) | 0.0443 (19) | 0.0208 (14) | 0.0047 (14) | 0.0065 (12) | −0.0036 (13) |
C(15) | 0.0345 (18) | 0.058 (2) | 0.0200 (15) | 0.0029 (16) | 0.0121 (13) | 0.0029 (14) |
C(16) | 0.044 (2) | 0.057 (2) | 0.0189 (15) | 0.0063 (18) | 0.0094 (14) | 0.0012 (14) |
C(17) | 0.0332 (19) | 0.060 (2) | 0.0245 (16) | −0.0016 (17) | 0.0039 (14) | −0.0100 (15) |
C(18) | 0.0365 (19) | 0.0431 (19) | 0.0243 (15) | −0.0003 (15) | 0.0136 (13) | −0.0048 (13) |
C(19) | 0.036 (2) | 0.050 (2) | 0.0362 (18) | −0.0038 (16) | 0.0124 (15) | −0.0040 (15) |
C(20) | 0.071 (3) | 0.070 (2) | 0.046 (2) | −0.028 (2) | 0.024 (2) | −0.024 (2) |
C(21) | 0.0291 (16) | 0.0282 (15) | 0.0167 (13) | −0.0052 (13) | 0.0060 (11) | −0.0021 (11) |
C(22) | 0.0296 (17) | 0.0283 (15) | 0.0227 (14) | 0.0040 (13) | 0.0066 (12) | 0.0001 (12) |
C(23) | 0.0326 (17) | 0.0297 (15) | 0.0181 (13) | −0.0004 (13) | 0.0056 (12) | 0.0042 (11) |
C(24) | 0.0281 (16) | 0.0303 (16) | 0.0202 (14) | −0.0006 (13) | 0.0086 (12) | −0.0015 (11) |
C(25) | 0.0274 (16) | 0.0306 (16) | 0.0259 (15) | 0.0030 (13) | 0.0083 (12) | 0.0032 (12) |
C(26) | 0.0294 (17) | 0.0321 (16) | 0.0199 (14) | −0.0020 (13) | 0.0041 (12) | 0.0039 (12) |
C(27) | 0.055 (2) | 0.044 (2) | 0.0307 (17) | 0.0150 (18) | 0.0102 (16) | 0.0121 (15) |
C(28) | 0.041 (2) | 0.0267 (16) | 0.0339 (17) | 0.0018 (14) | 0.0170 (15) | 0.0001 (13) |
C(29) | 0.056 (2) | 0.048 (2) | 0.0412 (19) | 0.0014 (18) | 0.0292 (18) | −0.0037 (16) |
C(30) | 0.0278 (16) | 0.0270 (15) | 0.0197 (13) | −0.0041 (13) | 0.0061 (12) | −0.0014 (11) |
C(31) | 0.0279 (17) | 0.0344 (16) | 0.0207 (14) | −0.0015 (13) | 0.0077 (12) | −0.0029 (12) |
C(32) | 0.045 (2) | 0.0308 (16) | 0.0271 (16) | −0.0052 (15) | 0.0072 (14) | −0.0020 (13) |
C(33) | 0.0283 (17) | 0.0454 (19) | 0.0174 (13) | 0.0060 (14) | 0.0065 (12) | −0.0045 (13) |
C(34) | 0.0270 (17) | 0.0464 (19) | 0.0210 (14) | 0.0049 (14) | 0.0072 (12) | −0.0036 (13) |
C(35) | 0.043 (2) | 0.069 (2) | 0.0204 (15) | 0.0116 (19) | 0.0134 (15) | 0.0080 (15) |
C(36) | 0.047 (2) | 0.080 (2) | 0.0168 (15) | 0.011 (2) | 0.0063 (15) | −0.0012 (17) |
C(37) | 0.042 (2) | 0.084 (2) | 0.0226 (16) | 0.002 (2) | 0.0071 (15) | −0.0151 (18) |
C(38) | 0.0382 (19) | 0.048 (2) | 0.0244 (16) | 0.0035 (16) | 0.0074 (14) | −0.0080 (14) |
C(39) | 0.043 (2) | 0.046 (2) | 0.048 (2) | −0.0008 (17) | 0.0241 (17) | 0.0039 (17) |
C(40) | 0.057 (2) | 0.075 (3) | 0.071 (2) | −0.020 (2) | 0.018 (2) | −0.036 (2) |
O(1)—C(3) | 1.375 (3) | C(36)—C(37) | 1.383 (5) |
O(1)—C(7) | 1.427 (4) | C(37)—C(38) | 1.392 (4) |
O(2)—C(4) | 1.372 (3) | O(3)—H(3) | 0.819 |
O(2)—C(8) | 1.434 (3) | O(4)—H(4) | 0.821 |
O(3)—C(10) | 1.424 (3) | O(10)—H(10) | 0.820 |
O(4)—C(12) | 1.428 (3) | O(11)—H(11) | 0.820 |
O(5)—C(11) | 1.475 (3) | C(2)—H(2) | 0.930 |
O(5)—C(13) | 1.392 (3) | C(5)—H(5) | 0.930 |
O(6)—C(14) | 1.371 (3) | C(6)—H(6) | 0.930 |
O(6)—C(19) | 1.439 (4) | C(7)—H(7A) | 0.960 |
O(7)—C(18) | 1.377 (4) | C(7)—H(7B) | 0.960 |
O(7)—C(20) | 1.427 (4) | C(7)—H(7C) | 0.960 |
O(8)—C(23) | 1.381 (3) | C(8)—H(8A) | 0.970 |
O(8)—C(27) | 1.412 (4) | C(8)—H(8B) | 0.970 |
O(9)—C(24) | 1.371 (3) | C(9)—H(9A) | 0.960 |
O(9)—C(28) | 1.441 (3) | C(9)—H(9B) | 0.960 |
O(10)—C(30) | 1.429 (3) | C(9)—H(9C) | 0.960 |
O(11)—C(32) | 1.421 (4) | C(10)—H(10A) | 0.980 |
O(12)—C(31) | 1.469 (3) | C(11)—H(11A) | 0.980 |
O(12)—C(33) | 1.384 (3) | C(12)—H(12A) | 0.970 |
O(13)—C(34) | 1.376 (3) | C(12)—H(12B) | 0.970 |
O(13)—C(39) | 1.427 (4) | C(15)—H(15) | 0.930 |
O(14)—C(38) | 1.373 (4) | C(16)—H(16) | 0.930 |
O(14)—C(40) | 1.416 (4) | C(17)—H(17) | 0.930 |
C(1)—C(2) | 1.408 (3) | C(19)—H(19A) | 0.960 |
C(1)—C(6) | 1.380 (4) | C(19)—H(19B) | 0.960 |
C(1)—C(10) | 1.521 (4) | C(19)—H(19C) | 0.960 |
C(2)—C(3) | 1.381 (4) | C(20)—H(20A) | 0.960 |
C(3)—C(4) | 1.404 (4) | C(20)—H(20B) | 0.960 |
C(4)—C(5) | 1.391 (3) | C(20)—H(20C) | 0.960 |
C(5)—C(6) | 1.395 (4) | C(22)—H(22) | 0.930 |
C(8)—C(9) | 1.501 (4) | C(25)—H(25) | 0.930 |
C(10)—C(11) | 1.538 (3) | C(26)—H(26) | 0.930 |
C(11)—C(12) | 1.516 (4) | C(27)—H(27A) | 0.960 |
C(13)—C(14) | 1.395 (4) | C(27)—H(27B) | 0.960 |
C(13)—C(18) | 1.400 (4) | C(27)—H(27C) | 0.960 |
C(14)—C(15) | 1.402 (4) | C(28)—H(28A) | 0.970 |
C(15)—C(16) | 1.378 (4) | C(28)—H(28B) | 0.970 |
C(16)—C(17) | 1.383 (5) | C(29)—H(29A) | 0.960 |
C(17)—C(18) | 1.388 (4) | C(29)—H(29B) | 0.960 |
C(21)—C(22) | 1.402 (3) | C(29)—H(29C) | 0.960 |
C(21)—C(26) | 1.383 (4) | C(30)—H(30) | 0.980 |
C(21)—C(30) | 1.515 (4) | C(31)—H(31) | 0.980 |
C(22)—C(23) | 1.383 (4) | C(32)—H(32A) | 0.970 |
C(23)—C(24) | 1.401 (4) | C(32)—H(32B) | 0.970 |
C(24)—C(25) | 1.392 (3) | C(35)—H(35) | 0.930 |
C(25)—C(26) | 1.391 (4) | C(36)—H(36) | 0.930 |
C(28)—C(29) | 1.512 (5) | C(37)—H(37) | 0.930 |
C(30)—C(31) | 1.535 (3) | C(39)—H(39A) | 0.960 |
C(31)—C(32) | 1.518 (4) | C(39)—H(39B) | 0.960 |
C(33)—C(34) | 1.384 (4) | C(39)—H(39C) | 0.960 |
C(33)—C(38) | 1.403 (4) | C(40)—H(40A) | 0.960 |
C(34)—C(35) | 1.405 (4) | C(40)—H(40B) | 0.960 |
C(35)—C(36) | 1.377 (4) | C(40)—H(40C) | 0.960 |
O(1)···C(16)i | 3.335 (3) | H(36)···H(29C)ix | 3.017 |
O(1)···C(29)ii | 3.598 (4) | H(37)···O(4)iv | 3.219 |
O(2)···C(22) | 3.548 (3) | H(37)···O(11)iv | 3.525 |
O(3)···C(8)iii | 3.459 (3) | H(37)···C(7)xv | 3.456 |
O(3)···C(9)iii | 3.429 (4) | H(37)···C(15)vi | 3.567 |
O(3)···C(25)ii | 3.444 (3) | H(37)···H(15)vi | 3.545 |
O(3)···C(26)ii | 3.328 (3) | H(37)···H(7A)xv | 2.747 |
O(4)···O(11) | 2.882 (3) | H(37)···H(7B)xv | 3.303 |
O(4)···O(12) | 3.301 (3) | H(37)···H(4)iv | 3.289 |
O(4)···C(7)iv | 3.558 (4) | H(37)···H(11)iv | 3.558 |
O(4)···C(27)v | 3.475 (4) | H(10A)···C(21)ii | 3.378 |
O(6)···C(31)ii | 3.540 (3) | H(10A)···C(24)ii | 3.491 |
O(6)···C(38)ii | 3.513 (4) | H(10A)···C(25)ii | 3.021 |
O(8)···C(36)i | 3.422 (3) | H(10A)···C(26)ii | 2.958 |
O(9)···C(2)vi | 3.436 (3) | H(10A)···H(25)ii | 3.284 |
O(9)···C(3)vi | 3.569 (3) | H(10A)···H(26)ii | 3.187 |
O(9)···C(7)vi | 3.588 (4) | H(10A)···H(31)ii | 3.440 |
O(10)···C(5) | 3.387 (3) | H(10A)···H(32A)ii | 3.367 |
O(10)···C(6) | 3.283 (3) | H(10A)···H(20A)viii | 3.437 |
O(10)···C(19)vi | 3.570 (3) | H(11A)···O(12) | 2.930 |
O(10)···C(28)vii | 3.348 (3) | H(11A)···O(13) | 2.636 |
O(10)···C(29)vii | 3.336 (4) | H(11A)···C(33) | 3.580 |
O(11)···O(4) | 2.882 (3) | H(11A)···C(34) | 3.455 |
O(11)···C(7)iv | 3.479 (3) | H(11A)···C(39) | 3.341 |
O(11)···C(12) | 3.527 (4) | H(11A)···H(30) | 3.242 |
O(11)···C(40)viii | 2.903 (4) | H(11A)···H(39B) | 3.025 |
O(12)···O(4) | 3.301 (3) | H(11A)···H(10) | 3.556 |
O(13)···C(11) | 3.572 (3) | H(11A)···H(11) | 3.286 |
O(13)···C(18) | 3.571 (4) | H(30)···C(1) | 3.265 |
C(1)···C(25)ii | 3.553 (4) | H(30)···C(4) | 3.390 |
C(2)···O(9)ii | 3.436 (3) | H(30)···C(5) | 2.866 |
C(2)···C(24)ii | 3.517 (4) | H(30)···C(6) | 2.794 |
C(3)···O(9)ii | 3.569 (3) | H(30)···H(5) | 3.122 |
C(3)···C(28)ii | 3.442 (4) | H(30)···H(6) | 3.013 |
C(5)···O(10) | 3.387 (3) | H(30)···H(11A) | 3.242 |
C(5)···C(21) | 3.582 (4) | H(30)···H(12B) | 3.238 |
C(5)···C(30) | 3.407 (3) | H(31)···O(5)vi | 3.463 |
C(6)···O(10) | 3.283 (3) | H(31)···O(6)vi | 2.580 |
C(6)···C(30) | 3.465 (4) | H(31)···C(14)vi | 3.576 |
C(7)···O(4)viii | 3.558 (4) | H(31)···C(19)vi | 3.101 |
C(7)···O(9)ii | 3.588 (4) | H(31)···H(10A)vi | 3.440 |
C(7)···O(11)viii | 3.479 (3) | H(31)···H(19B)vi | 2.667 |
C(8)···O(3)iii | 3.459 (3) | H(8A)···C(21) | 3.132 |
C(8)···C(23) | 3.513 (4) | H(8A)···C(22) | 2.973 |
C(9)···O(3)iii | 3.429 (4) | H(8A)···C(23) | 2.889 |
C(10)···C(25)ii | 3.492 (3) | H(8A)···C(24) | 2.944 |
C(10)···C(26)ii | 3.566 (4) | H(8A)···C(25) | 3.101 |
C(11)···O(13) | 3.572 (3) | H(8A)···C(25)vii | 3.486 |
C(12)···O(11) | 3.527 (4) | H(8A)···C(26) | 3.186 |
C(16)···O(1)ix | 3.335 (3) | H(8A)···H(22) | 3.464 |
C(18)···O(13) | 3.571 (4) | H(8A)···H(25)vii | 2.663 |
C(19)···O(10)ii | 3.570 (3) | H(8A)···H(26)vii | 3.542 |
C(19)···C(33)ii | 3.536 (4) | H(8B)···O(3)iii | 2.738 |
C(21)···C(5) | 3.582 (4) | H(8B)···C(1)iii | 3.562 |
C(22)···O(2) | 3.548 (3) | H(8B)···C(6)iii | 3.006 |
C(23)···C(8) | 3.513 (4) | H(8B)···C(25)vii | 3.596 |
C(24)···C(2)vi | 3.517 (4) | H(8B)···H(6)iii | 2.573 |
C(25)···O(3)vi | 3.444 (3) | H(8B)···H(25)vii | 2.787 |
C(25)···C(1)vi | 3.553 (4) | H(8B)···H(3)iii | 3.275 |
C(25)···C(10)vi | 3.492 (3) | H(8B)···H(29B)ii | 3.283 |
C(26)···O(3)vi | 3.328 (3) | H(12A)···C(20)viii | 3.100 |
C(26)···C(10)vi | 3.566 (4) | H(12A)···C(27)v | 3.362 |
C(27)···O(4)x | 3.475 (4) | H(12A)···H(20A)viii | 2.917 |
C(28)···O(10)vii | 3.348 (3) | H(12A)···H(20B)viii | 3.100 |
C(28)···C(3)vi | 3.442 (4) | H(12A)···H(20C)viii | 2.764 |
C(29)···O(1)vi | 3.598 (4) | H(12A)···H(27B)v | 2.414 |
C(29)···O(10)vii | 3.336 (4) | H(12A)···H(40A)viii | 3.529 |
C(30)···C(5) | 3.407 (3) | H(12B)···O(11) | 3.115 |
C(30)···C(6) | 3.465 (4) | H(12B)···C(40)viii | 3.341 |
C(31)···O(6)vi | 3.540 (3) | H(12B)···H(30) | 3.238 |
C(33)···C(19)vi | 3.536 (4) | H(12B)···H(20B)viii | 3.408 |
C(36)···O(8)ix | 3.422 (3) | H(12B)···H(40A)viii | 2.438 |
C(38)···O(6)vi | 3.513 (4) | H(12B)···H(40C)viii | 3.556 |
C(40)···O(11)iv | 2.903 (4) | H(12B)···H(11) | 2.490 |
O(1)···H(16)i | 2.614 | H(28A)···O(1)vi | 3.506 |
O(1)···H(28A)ii | 3.506 | H(28A)···C(1)vi | 3.189 |
O(1)···H(27A) | 3.367 | H(28A)···C(2)vi | 2.950 |
O(1)···H(29C)ii | 2.975 | H(28A)···C(3)vi | 2.829 |
O(2)···H(16)i | 2.862 | H(28A)···C(4)vi | 2.918 |
O(2)···H(22) | 3.523 | H(28A)···C(5)vi | 3.129 |
O(2)···H(27A) | 3.090 | H(28A)···C(5)vii | 3.471 |
O(2)···H(29B)ii | 3.152 | H(28A)···C(6)vi | 3.256 |
O(3)···H(25)ii | 3.241 | H(28A)···H(2)vi | 3.419 |
O(3)···H(26)ii | 3.030 | H(28A)···H(5)vii | 2.643 |
O(3)···H(8B)iii | 2.738 | H(28A)···H(6)vii | 3.547 |
O(3)···H(39B) | 2.753 | H(28B)···O(10)vii | 2.656 |
O(3)···H(9A)iii | 2.949 | H(28B)···C(26)vii | 3.025 |
O(3)···H(9B)iii | 3.423 | H(28B)···H(5)vii | 2.877 |
O(4)···H(37)viii | 3.219 | H(28B)···H(26)vii | 2.541 |
O(4)···H(7A)iv | 3.339 | H(28B)···H(9B) | 3.053 |
O(4)···H(7B)iv | 3.299 | H(28B)···H(10)vii | 3.176 |
O(4)···H(7C)iv | 3.451 | H(32A)···C(20)x | 3.448 |
O(4)···H(27B)v | 2.652 | H(32A)···H(10A)vi | 3.367 |
O(4)···H(40A)viii | 3.388 | H(32A)···H(7B)iv | 3.483 |
O(4)···H(11) | 2.191 | H(32A)···H(20A)x | 2.576 |
O(5)···H(31)ii | 3.463 | H(32B)···C(7)iv | 3.143 |
O(5)···H(27B)v | 3.389 | H(32B)···H(7B)iv | 2.282 |
O(5)···H(40B)ii | 3.390 | H(32B)···H(7C)iv | 3.322 |
O(6)···H(26)ii | 3.512 | H(7A)···O(4)viii | 3.339 |
O(6)···H(31)ii | 2.580 | H(7A)···O(8)ii | 3.240 |
O(6)···H(39B) | 3.478 | H(7A)···O(9)ii | 2.905 |
O(7)···H(27B)v | 3.464 | H(7A)···C(29)ii | 3.560 |
O(7)···H(27C)v | 3.462 | H(7A)···C(37)xi | 3.496 |
O(8)···H(36)i | 2.694 | H(7A)···H(16)i | 3.397 |
O(8)···H(7A)vi | 3.240 | H(7A)···H(36)xi | 3.243 |
O(8)···H(9C) | 3.092 | H(7A)···H(37)xi | 2.747 |
O(8)···H(4)x | 2.966 | H(7A)···H(20B)viii | 3.527 |
O(9)···H(2)vi | 3.363 | H(7A)···H(29C)ii | 2.753 |
O(9)···H(36)i | 2.851 | H(7A)···H(4)viii | 3.169 |
O(9)···H(7A)vi | 2.905 | H(7B)···O(4)viii | 3.299 |
O(9)···H(9B) | 3.076 | H(7B)···O(11)viii | 2.589 |
O(10)···H(5) | 3.152 | H(7B)···O(14)viii | 3.437 |
O(10)···H(6) | 2.962 | H(7B)···C(16)i | 3.585 |
O(10)···H(28B)vii | 2.656 | H(7B)···C(32)viii | 2.867 |
O(10)···H(19B)vi | 2.663 | H(7B)···H(16)i | 3.325 |
O(10)···H(29A)vii | 2.935 | H(7B)···H(37)xi | 3.303 |
O(10)···H(29B)vii | 3.264 | H(7B)···H(32A)viii | 3.483 |
O(11)···H(37)viii | 3.525 | H(7B)···H(32B)viii | 2.282 |
O(11)···H(12B) | 3.115 | H(7B)···H(20B)viii | 3.426 |
O(11)···H(7B)iv | 2.589 | H(7B)···H(40C)xi | 3.503 |
O(11)···H(40A)viii | 2.632 | H(7B)···H(4)viii | 3.473 |
O(11)···H(40B)viii | 3.094 | H(7B)···H(11)viii | 2.764 |
O(11)···H(40C)viii | 2.526 | H(7C)···O(4)viii | 3.451 |
O(11)···H(4) | 3.577 | H(7C)···O(14)viii | 3.375 |
O(12)···H(11A) | 2.930 | H(7C)···C(20)viii | 3.168 |
O(12)···H(19B)vi | 3.501 | H(7C)···H(32B)viii | 3.322 |
O(12)···H(20B) | 3.507 | H(7C)···H(20A)viii | 3.352 |
O(13)···H(6) | 3.419 | H(7C)···H(20B)viii | 2.288 |
O(13)···H(11A) | 2.636 | H(7C)···H(40A)viii | 3.192 |
O(13)···H(19B)vi | 3.439 | H(7C)···H(4)viii | 3.309 |
O(13)···H(3) | 3.596 | H(19A)···C(9)iii | 3.075 |
O(13)···H(29A)vii | 3.574 | H(19A)···H(26)ii | 3.512 |
O(14)···H(7B)iv | 3.437 | H(19A)···H(35)xii | 2.994 |
O(14)···H(7C)iv | 3.375 | H(19A)···H(39A)xii | 3.414 |
O(14)···H(20B) | 3.285 | H(19A)···H(9A)iii | 2.629 |
C(1)···H(25)ii | 3.353 | H(19A)···H(9B)iii | 2.707 |
C(1)···H(30) | 3.265 | H(19A)···H(9C)iii | 3.496 |
C(1)···H(8B)iii | 3.562 | H(19B)···O(10)ii | 2.663 |
C(1)···H(28A)ii | 3.189 | H(19B)···O(12)ii | 3.501 |
C(2)···H(28A)ii | 2.950 | H(19B)···O(13)ii | 3.439 |
C(2)···H(40A)viii | 3.469 | H(19B)···C(30)ii | 3.479 |
C(3)···H(28A)ii | 2.829 | H(19B)···C(31)ii | 3.295 |
C(3)···H(40A)viii | 3.542 | H(19B)···C(33)ii | 3.001 |
C(3)···H(29B)ii | 3.600 | H(19B)···C(34)ii | 3.026 |
C(3)···H(29C)ii | 3.371 | H(19B)···C(35)ii | 3.505 |
C(4)···H(22) | 3.434 | H(19B)···C(38)ii | 3.460 |
C(4)···H(30) | 3.390 | H(19B)···H(26)ii | 3.107 |
C(4)···H(28A)ii | 2.918 | H(19B)···H(31)ii | 2.667 |
C(4)···H(29B)ii | 3.328 | H(19B)···H(9B)iii | 3.485 |
C(5)···H(5)iii | 3.450 | H(19B)···H(29A)iii | 3.110 |
C(5)···H(30) | 2.866 | H(19B)···H(10)ii | 2.267 |
C(5)···H(28A)ii | 3.129 | H(19C)···C(33)ii | 3.460 |
C(5)···H(28A)vii | 3.471 | H(19C)···C(34)ii | 3.422 |
C(6)···H(5)iii | 3.586 | H(19C)···C(35)ii | 3.292 |
C(6)···H(30) | 2.794 | H(19C)···C(36)ii | 3.188 |
C(6)···H(8B)iii | 3.006 | H(19C)···C(37)ii | 3.242 |
C(6)···H(28A)ii | 3.256 | H(19C)···C(38)ii | 3.368 |
C(7)···H(16)i | 3.345 | H(19C)···H(39A)xii | 3.521 |
C(7)···H(37)xi | 3.456 | H(19C)···H(29A)xiii | 3.467 |
C(7)···H(32B)viii | 3.143 | H(19C)···H(29C)xiii | 3.583 |
C(7)···H(20B)viii | 3.180 | H(20A)···C(22)v | 3.586 |
C(7)···H(29C)ii | 3.327 | H(20A)···C(32)v | 3.475 |
C(7)···H(4)viii | 3.507 | H(20A)···H(2)iv | 3.099 |
C(7)···H(11)viii | 3.543 | H(20A)···H(22)v | 3.545 |
C(8)···H(6)iii | 3.512 | H(20A)···H(10A)iv | 3.437 |
C(8)···H(25)vii | 3.128 | H(20A)···H(12A)iv | 2.917 |
C(9)···H(16)i | 3.577 | H(20A)···H(32A)v | 2.576 |
C(9)···H(26)vii | 3.540 | H(20A)···H(7C)iv | 3.352 |
C(9)···H(35)i | 2.957 | H(20A)···H(27C)v | 3.468 |
C(9)···H(36)i | 3.436 | H(20B)···O(12) | 3.507 |
C(9)···H(19A)iii | 3.075 | H(20B)···O(14) | 3.285 |
C(9)···H(3)iii | 3.558 | H(20B)···C(7)iv | 3.180 |
C(10)···H(25)ii | 3.501 | H(20B)···C(33) | 3.323 |
C(11)···H(11) | 3.596 | H(20B)···C(38) | 3.206 |
C(12)···H(27B)v | 2.958 | H(20B)···H(2)iv | 2.769 |
C(12)···H(40A)viii | 3.224 | H(20B)···H(12A)iv | 3.100 |
C(12)···H(11) | 2.800 | H(20B)···H(12B)iv | 3.408 |
C(13)···H(39B) | 3.255 | H(20B)···H(7A)iv | 3.527 |
C(13)···H(39C) | 3.511 | H(20B)···H(7B)iv | 3.426 |
C(13)···H(40B)ii | 3.412 | H(20B)···H(7C)iv | 2.288 |
C(13)···H(40C)ii | 3.421 | H(20B)···H(40A) | 3.494 |
C(14)···H(31)ii | 3.576 | H(20C)···C(33) | 3.423 |
C(14)···H(39B) | 3.112 | H(20C)···C(34) | 3.543 |
C(14)···H(39C) | 3.390 | H(20C)···C(35) | 3.590 |
C(14)···H(40C)ii | 3.410 | H(20C)···C(36) | 3.510 |
C(15)···H(37)ii | 3.567 | H(20C)···C(37) | 3.387 |
C(15)···H(39A)xii | 3.568 | H(20C)···C(38) | 3.339 |
C(15)···H(39B) | 3.497 | H(20C)···H(12A)iv | 2.764 |
C(15)···H(39C) | 3.208 | H(20C)···H(27A)ix | 3.494 |
C(15)···H(40C)ii | 3.578 | H(20C)···H(27B)ix | 3.248 |
C(15)···H(29C)xiii | 3.119 | H(27A)···O(1) | 3.367 |
C(16)···H(7B)ix | 3.585 | H(27A)···O(2) | 3.090 |
C(16)···H(39C) | 3.132 | H(27A)···C(17)i | 3.452 |
C(16)···H(9C)ix | 3.596 | H(27A)···H(16)i | 3.366 |
C(16)···H(29C)xiii | 3.267 | H(27A)···H(17)i | 2.649 |
C(17)···H(27A)ix | 3.452 | H(27A)···H(36)i | 3.413 |
C(17)···H(39C) | 3.279 | H(27A)···H(20C)i | 3.494 |
C(18)···H(39C) | 3.469 | H(27A)···H(40B)viii | 3.226 |
C(18)···H(40C)ii | 3.562 | H(27A)···H(9C) | 2.892 |
C(19)···H(26)ii | 3.547 | H(27A)···H(4)x | 3.485 |
C(19)···H(31)ii | 3.101 | H(27B)···O(4)x | 2.652 |
C(19)···H(9A)iii | 3.478 | H(27B)···O(5)x | 3.389 |
C(19)···H(9B)iii | 3.456 | H(27B)···O(7)x | 3.464 |
C(19)···H(10)ii | 3.212 | H(27B)···C(12)x | 2.958 |
C(20)···H(2)iv | 3.366 | H(27B)···H(17)i | 3.298 |
C(20)···H(12A)iv | 3.100 | H(27B)···H(36)i | 3.452 |
C(20)···H(32A)v | 3.448 | H(27B)···H(12A)x | 2.414 |
C(20)···H(7C)iv | 3.168 | H(27B)···H(20C)i | 3.248 |
C(21)···H(5) | 3.386 | H(27B)···H(40B)viii | 3.214 |
C(21)···H(10A)vi | 3.378 | H(27B)···H(4)x | 1.947 |
C(21)···H(8A) | 3.132 | H(27C)···O(7)x | 3.462 |
C(22)···H(8A) | 2.973 | H(27C)···C(40)viii | 3.127 |
C(22)···H(20A)x | 3.586 | H(27C)···H(20A)x | 3.468 |
C(23)···H(8A) | 2.889 | H(27C)···H(40A)viii | 3.340 |
C(23)···H(9B) | 3.586 | H(27C)···H(40B)viii | 2.220 |
C(23)···H(9C) | 3.401 | H(27C)···H(40C)viii | 3.593 |
C(24)···H(2)vi | 3.288 | H(27C)···H(4)x | 3.016 |
C(24)···H(10A)vi | 3.491 | H(39A)···C(15)xii | 3.568 |
C(24)···H(8A) | 2.944 | H(39A)···C(29)vii | 3.106 |
C(24)···H(9B) | 3.245 | H(39A)···H(15)xii | 2.902 |
C(25)···H(25)vii | 3.522 | H(39A)···H(19A)xii | 3.414 |
C(25)···H(10A)vi | 3.021 | H(39A)···H(19C)xii | 3.521 |
C(25)···H(8A) | 3.101 | H(39A)···H(29A)vii | 2.758 |
C(25)···H(8A)vii | 3.486 | H(39A)···H(29B)vii | 2.682 |
C(25)···H(8B)vii | 3.596 | H(39A)···H(29C)vii | 3.441 |
C(26)···H(10A)vi | 2.958 | H(39B)···O(3) | 2.753 |
C(26)···H(8A) | 3.186 | H(39B)···O(6) | 3.478 |
C(26)···H(28B)vii | 3.025 | H(39B)···C(13) | 3.255 |
C(27)···H(17)i | 3.393 | H(39B)···C(14) | 3.112 |
C(27)···H(36)i | 3.422 | H(39B)···C(15) | 3.497 |
C(27)···H(12A)x | 3.362 | H(39B)···H(6) | 3.192 |
C(27)···H(40B)viii | 3.012 | H(39B)···H(11A) | 3.025 |
C(27)···H(9C) | 3.468 | H(39B)···H(9A)iii | 2.931 |
C(27)···H(4)x | 2.703 | H(39B)···H(3) | 2.344 |
C(28)···H(5)vii | 3.165 | H(39B)···H(29B)vii | 3.328 |
C(28)···H(26)vii | 3.495 | H(39C)···C(13) | 3.511 |
C(28)···H(9B) | 3.495 | H(39C)···C(14) | 3.390 |
C(29)···H(15)xiv | 3.039 | H(39C)···C(15) | 3.208 |
C(29)···H(16)xiv | 3.449 | H(39C)···C(16) | 3.132 |
C(29)···H(36)i | 3.494 | H(39C)···C(17) | 3.279 |
C(29)···H(7A)vi | 3.560 | H(39C)···C(18) | 3.469 |
C(29)···H(39A)vii | 3.106 | H(39C)···H(16) | 3.507 |
C(29)···H(10)vii | 3.415 | H(39C)···H(9A)ix | 3.406 |
C(30)···H(5) | 3.407 | H(39C)···H(9C)ix | 3.575 |
C(30)···H(6) | 3.502 | H(40A)···O(4)iv | 3.388 |
C(30)···H(19B)vi | 3.479 | H(40A)···O(11)iv | 2.632 |
C(31)···H(19B)vi | 3.295 | H(40A)···C(2)iv | 3.469 |
C(32)···H(7B)iv | 2.867 | H(40A)···C(3)iv | 3.542 |
C(32)···H(20A)x | 3.475 | H(40A)···C(12)iv | 3.224 |
C(33)···H(11A) | 3.580 | H(40A)···H(2)iv | 3.379 |
C(33)···H(19B)vi | 3.001 | H(40A)···H(22)iv | 3.259 |
C(33)···H(19C)vi | 3.460 | H(40A)···H(12A)iv | 3.529 |
C(33)···H(20B) | 3.323 | H(40A)···H(12B)iv | 2.438 |
C(33)···H(20C) | 3.423 | H(40A)···H(7C)iv | 3.192 |
C(34)···H(11A) | 3.455 | H(40A)···H(20B) | 3.494 |
C(34)···H(19B)vi | 3.026 | H(40A)···H(27C)iv | 3.340 |
C(34)···H(19C)vi | 3.422 | H(40A)···H(11)iv | 2.679 |
C(34)···H(20C) | 3.543 | H(40B)···O(5)vi | 3.390 |
C(35)···H(17) | 3.497 | H(40B)···O(11)iv | 3.094 |
C(35)···H(19B)vi | 3.505 | H(40B)···C(13)vi | 3.412 |
C(35)···H(19C)vi | 3.292 | H(40B)···C(27)iv | 3.012 |
C(35)···H(20C) | 3.590 | H(40B)···H(22)iv | 2.937 |
C(35)···H(9C)ix | 3.061 | H(40B)···H(27A)iv | 3.226 |
C(36)···H(19C)vi | 3.188 | H(40B)···H(27B)iv | 3.214 |
C(36)···H(20C) | 3.510 | H(40B)···H(27C)iv | 2.220 |
C(36)···H(9C)ix | 3.235 | H(40B)···H(11)iv | 3.514 |
C(36)···H(29C)ix | 3.553 | H(40C)···O(11)iv | 2.526 |
C(37)···H(15)vi | 3.584 | H(40C)···C(13)vi | 3.421 |
C(37)···H(7A)xv | 3.496 | H(40C)···C(14)vi | 3.410 |
C(37)···H(19C)vi | 3.242 | H(40C)···C(15)vi | 3.578 |
C(37)···H(20C) | 3.387 | H(40C)···C(18)vi | 3.562 |
C(38)···H(19B)vi | 3.460 | H(40C)···H(12B)iv | 3.556 |
C(38)···H(19C)vi | 3.368 | H(40C)···H(7B)xv | 3.503 |
C(38)···H(20B) | 3.206 | H(40C)···H(27C)iv | 3.593 |
C(38)···H(20C) | 3.339 | H(40C)···H(11)iv | 2.880 |
C(39)···H(11A) | 3.341 | H(9A)···O(3)iii | 2.949 |
C(39)···H(3) | 3.232 | H(9A)···C(19)iii | 3.478 |
C(39)···H(29A)vii | 3.523 | H(9A)···H(16)i | 3.466 |
C(39)···H(29B)vii | 3.326 | H(9A)···H(35)i | 2.871 |
C(40)···H(22)iv | 3.491 | H(9A)···H(19A)iii | 2.629 |
C(40)···H(12B)iv | 3.341 | H(9A)···H(39B)iii | 2.931 |
C(40)···H(27C)iv | 3.127 | H(9A)···H(39C)i | 3.406 |
C(40)···H(11)iv | 3.170 | H(9A)···H(3)iii | 2.923 |
H(2)···O(9)ii | 3.363 | H(9B)···O(3)iii | 3.423 |
H(2)···C(20)viii | 3.366 | H(9B)···O(9) | 3.076 |
H(2)···C(24)ii | 3.288 | H(9B)···C(19)iii | 3.456 |
H(2)···H(28A)ii | 3.419 | H(9B)···C(23) | 3.586 |
H(2)···H(20A)viii | 3.099 | H(9B)···C(24) | 3.245 |
H(2)···H(20B)viii | 2.769 | H(9B)···C(28) | 3.495 |
H(2)···H(40A)viii | 3.379 | H(9B)···H(25)vii | 3.509 |
H(5)···O(10) | 3.152 | H(9B)···H(26)vii | 2.788 |
H(5)···C(5)iii | 3.450 | H(9B)···H(35)i | 3.094 |
H(5)···C(6)iii | 3.586 | H(9B)···H(36)i | 3.232 |
H(5)···C(21) | 3.386 | H(9B)···H(28B) | 3.053 |
H(5)···C(28)vii | 3.165 | H(9B)···H(19A)iii | 2.707 |
H(5)···C(30) | 3.407 | H(9B)···H(19B)iii | 3.485 |
H(5)···H(5)iii | 3.389 | H(9B)···H(3)iii | 3.536 |
H(5)···H(25)vii | 3.151 | H(9B)···H(29A) | 3.600 |
H(5)···H(30) | 3.122 | H(9C)···O(8) | 3.092 |
H(5)···H(28A)vii | 2.643 | H(9C)···C(16)i | 3.596 |
H(5)···H(28B)vii | 2.877 | H(9C)···C(23) | 3.401 |
H(5)···H(29B)vii | 3.552 | H(9C)···C(27) | 3.468 |
H(6)···O(10) | 2.962 | H(9C)···C(35)i | 3.061 |
H(6)···O(13) | 3.419 | H(9C)···C(36)i | 3.235 |
H(6)···C(8)iii | 3.512 | H(9C)···H(16)i | 3.067 |
H(6)···C(30) | 3.502 | H(9C)···H(17)i | 3.593 |
H(6)···H(30) | 3.013 | H(9C)···H(35)i | 2.441 |
H(6)···H(8B)iii | 2.573 | H(9C)···H(36)i | 2.777 |
H(6)···H(28A)vii | 3.547 | H(9C)···H(19A)iii | 3.496 |
H(6)···H(39B) | 3.192 | H(9C)···H(27A) | 2.892 |
H(6)···H(29B)vii | 2.865 | H(9C)···H(39C)i | 3.575 |
H(6)···H(10) | 3.168 | H(3)···O(13) | 3.596 |
H(15)···C(29)xiii | 3.039 | H(3)···C(9)iii | 3.558 |
H(15)···C(37)ii | 3.584 | H(3)···C(39) | 3.232 |
H(15)···H(37)ii | 3.545 | H(3)···H(26)ii | 3.300 |
H(15)···H(39A)xii | 2.902 | H(3)···H(8B)iii | 3.275 |
H(15)···H(29A)xiii | 2.991 | H(3)···H(39B) | 2.344 |
H(15)···H(29B)xiii | 3.171 | H(3)···H(9A)iii | 2.923 |
H(15)···H(29C)xiii | 2.486 | H(3)···H(9B)iii | 3.536 |
H(16)···O(1)ix | 2.614 | H(29A)···O(10)vii | 2.935 |
H(16)···O(2)ix | 2.862 | H(29A)···O(13)vii | 3.574 |
H(16)···C(7)ix | 3.345 | H(29A)···C(39)vii | 3.523 |
H(16)···C(9)ix | 3.577 | H(29A)···H(15)xiv | 2.991 |
H(16)···C(29)xiii | 3.449 | H(29A)···H(36)i | 3.341 |
H(16)···H(7A)ix | 3.397 | H(29A)···H(19B)iii | 3.110 |
H(16)···H(7B)ix | 3.325 | H(29A)···H(19C)xiv | 3.467 |
H(16)···H(27A)ix | 3.366 | H(29A)···H(39A)vii | 2.758 |
H(16)···H(39C) | 3.507 | H(29A)···H(9B) | 3.600 |
H(16)···H(9A)ix | 3.466 | H(29A)···H(10)vii | 2.863 |
H(16)···H(9C)ix | 3.067 | H(29B)···O(2)vi | 3.152 |
H(16)···H(29B)xiii | 3.241 | H(29B)···O(10)vii | 3.264 |
H(16)···H(29C)xiii | 2.788 | H(29B)···C(3)vi | 3.600 |
H(17)···C(27)ix | 3.393 | H(29B)···C(4)vi | 3.328 |
H(17)···C(35) | 3.497 | H(29B)···C(39)vii | 3.326 |
H(17)···H(35) | 3.577 | H(29B)···H(5)vii | 3.552 |
H(17)···H(27A)ix | 2.649 | H(29B)···H(6)vii | 2.865 |
H(17)···H(27B)ix | 3.298 | H(29B)···H(15)xiv | 3.171 |
H(17)···H(9C)ix | 3.593 | H(29B)···H(16)xiv | 3.241 |
H(22)···O(2) | 3.523 | H(29B)···H(8B)vi | 3.283 |
H(22)···C(4) | 3.434 | H(29B)···H(39A)vii | 2.682 |
H(22)···C(40)viii | 3.491 | H(29B)···H(39B)vii | 3.328 |
H(22)···H(8A) | 3.464 | H(29B)···H(10)vii | 3.306 |
H(22)···H(20A)x | 3.545 | H(29C)···O(1)vi | 2.975 |
H(22)···H(40A)viii | 3.259 | H(29C)···C(3)vi | 3.371 |
H(22)···H(40B)viii | 2.937 | H(29C)···C(7)vi | 3.327 |
H(25)···O(3)vi | 3.241 | H(29C)···C(15)xiv | 3.119 |
H(25)···C(1)vi | 3.353 | H(29C)···C(16)xiv | 3.267 |
H(25)···C(8)vii | 3.128 | H(29C)···C(36)i | 3.553 |
H(25)···C(10)vi | 3.501 | H(29C)···H(15)xiv | 2.486 |
H(25)···C(25)vii | 3.522 | H(29C)···H(16)xiv | 2.788 |
H(25)···H(5)vii | 3.151 | H(29C)···H(36)i | 3.017 |
H(25)···H(25)vii | 3.456 | H(29C)···H(7A)vi | 2.753 |
H(25)···H(26)vii | 3.597 | H(29C)···H(19C)xiv | 3.583 |
H(25)···H(10A)vi | 3.284 | H(29C)···H(39A)vii | 3.441 |
H(25)···H(8A)vii | 2.663 | H(4)···O(8)v | 2.966 |
H(25)···H(8B)vii | 2.787 | H(4)···O(11) | 3.577 |
H(25)···H(9B)vii | 3.509 | H(4)···C(7)iv | 3.507 |
H(26)···O(3)vi | 3.030 | H(4)···C(27)v | 2.703 |
H(26)···O(6)vi | 3.512 | H(4)···H(37)viii | 3.289 |
H(26)···C(9)vii | 3.540 | H(4)···H(7A)iv | 3.169 |
H(26)···C(19)vi | 3.547 | H(4)···H(7B)iv | 3.473 |
H(26)···C(28)vii | 3.495 | H(4)···H(7C)iv | 3.309 |
H(26)···H(25)vii | 3.597 | H(4)···H(27A)v | 3.485 |
H(26)···H(10A)vi | 3.187 | H(4)···H(27B)v | 1.947 |
H(26)···H(8A)vii | 3.542 | H(4)···H(27C)v | 3.016 |
H(26)···H(28B)vii | 2.541 | H(4)···H(11) | 2.938 |
H(26)···H(19A)vi | 3.512 | H(10)···C(19)vi | 3.212 |
H(26)···H(19B)vi | 3.107 | H(10)···C(29)vii | 3.415 |
H(26)···H(9B)vii | 2.788 | H(10)···H(6) | 3.168 |
H(26)···H(3)vi | 3.300 | H(10)···H(11A) | 3.556 |
H(35)···C(9)ix | 2.957 | H(10)···H(28B)vii | 3.176 |
H(35)···H(17) | 3.577 | H(10)···H(19B)vi | 2.267 |
H(35)···H(19A)xii | 2.994 | H(10)···H(29A)vii | 2.863 |
H(35)···H(9A)ix | 2.871 | H(10)···H(29B)vii | 3.306 |
H(35)···H(9B)ix | 3.094 | H(11)···O(4) | 2.191 |
H(35)···H(9C)ix | 2.441 | H(11)···C(7)iv | 3.543 |
H(36)···O(8)ix | 2.694 | H(11)···C(11) | 3.596 |
H(36)···O(9)ix | 2.851 | H(11)···C(12) | 2.800 |
H(36)···C(9)ix | 3.436 | H(11)···C(40)viii | 3.170 |
H(36)···C(27)ix | 3.422 | H(11)···H(37)viii | 3.558 |
H(36)···C(29)ix | 3.494 | H(11)···H(11A) | 3.286 |
H(36)···H(7A)xv | 3.243 | H(11)···H(12B) | 2.490 |
H(36)···H(27A)ix | 3.413 | H(11)···H(7B)iv | 2.764 |
H(36)···H(27B)ix | 3.452 | H(11)···H(40A)viii | 2.679 |
H(36)···H(9B)ix | 3.232 | H(11)···H(40B)viii | 3.514 |
H(36)···H(9C)ix | 2.777 | H(11)···H(40C)viii | 2.880 |
H(36)···H(29A)ix | 3.341 | H(11)···H(4) | 2.938 |
C(3)—O(1)—C(7) | 117.5 (2) | O(2)—C(8)—H(8B) | 110.0 |
C(4)—O(2)—C(8) | 117.0 (2) | C(9)—C(8)—H(8A) | 110.0 |
C(11)—O(5)—C(13) | 119.1 (2) | C(9)—C(8)—H(8B) | 110.1 |
C(14)—O(6)—C(19) | 117.8 (2) | H(8A)—C(8)—H(8B) | 109.5 |
C(18)—O(7)—C(20) | 117.9 (2) | C(8)—C(9)—H(9A) | 109.4 |
C(23)—O(8)—C(27) | 117.1 (2) | C(8)—C(9)—H(9B) | 109.5 |
C(24)—O(9)—C(28) | 116.8 (2) | C(8)—C(9)—H(9C) | 109.4 |
C(31)—O(12)—C(33) | 117.9 (2) | H(9A)—C(9)—H(9B) | 109.5 |
C(34)—O(13)—C(39) | 118.4 (2) | H(9A)—C(9)—H(9C) | 109.5 |
C(38)—O(14)—C(40) | 117.4 (2) | H(9B)—C(9)—H(9C) | 109.5 |
C(2)—C(1)—C(6) | 118.5 (2) | O(3)—C(10)—H(10A) | 109.0 |
C(2)—C(1)—C(10) | 120.4 (2) | C(1)—C(10)—H(10A) | 109.0 |
C(6)—C(1)—C(10) | 121.0 (2) | C(11)—C(10)—H(10A) | 109.0 |
C(1)—C(2)—C(3) | 121.1 (2) | O(5)—C(11)—H(11A) | 110.3 |
O(1)—C(3)—C(2) | 125.4 (2) | C(10)—C(11)—H(11A) | 110.3 |
O(1)—C(3)—C(4) | 114.6 (2) | C(12)—C(11)—H(11A) | 110.2 |
C(2)—C(3)—C(4) | 119.9 (2) | O(4)—C(12)—H(12A) | 108.8 |
O(2)—C(4)—C(3) | 115.9 (2) | O(4)—C(12)—H(12B) | 107.6 |
O(2)—C(4)—C(5) | 125.0 (2) | C(11)—C(12)—H(12A) | 108.2 |
C(3)—C(4)—C(5) | 119.1 (2) | C(11)—C(12)—H(12B) | 108.3 |
C(4)—C(5)—C(6) | 120.4 (2) | H(12A)—C(12)—H(12B) | 109.5 |
C(1)—C(6)—C(5) | 120.9 (2) | C(14)—C(15)—H(15) | 120.1 |
O(2)—C(8)—C(9) | 107.2 (2) | C(16)—C(15)—H(15) | 120.2 |
O(3)—C(10)—C(1) | 107.5 (2) | C(15)—C(16)—H(16) | 119.6 |
O(3)—C(10)—C(11) | 109.9 (2) | C(17)—C(16)—H(16) | 119.7 |
C(1)—C(10)—C(11) | 112.4 (2) | C(16)—C(17)—H(17) | 120.0 |
O(5)—C(11)—C(10) | 106.9 (2) | C(18)—C(17)—H(17) | 120.2 |
O(5)—C(11)—C(12) | 106.6 (2) | O(6)—C(19)—H(19A) | 109.5 |
C(10)—C(11)—C(12) | 112.5 (2) | O(6)—C(19)—H(19B) | 109.4 |
O(4)—C(12)—C(11) | 114.4 (2) | O(6)—C(19)—H(19C) | 109.4 |
O(5)—C(13)—C(14) | 119.8 (2) | H(19A)—C(19)—H(19B) | 109.5 |
O(5)—C(13)—C(18) | 121.0 (2) | H(19A)—C(19)—H(19C) | 109.5 |
C(14)—C(13)—C(18) | 118.8 (2) | H(19B)—C(19)—H(19C) | 109.5 |
O(6)—C(14)—C(13) | 116.2 (2) | O(7)—C(20)—H(20A) | 109.5 |
O(6)—C(14)—C(15) | 123.5 (2) | O(7)—C(20)—H(20B) | 109.5 |
C(13)—C(14)—C(15) | 120.3 (2) | O(7)—C(20)—H(20C) | 109.4 |
C(14)—C(15)—C(16) | 119.7 (3) | H(20A)—C(20)—H(20B) | 109.5 |
C(15)—C(16)—C(17) | 120.8 (2) | H(20A)—C(20)—H(20C) | 109.5 |
C(16)—C(17)—C(18) | 119.8 (2) | H(20B)—C(20)—H(20C) | 109.5 |
O(7)—C(18)—C(13) | 115.7 (2) | C(21)—C(22)—H(22) | 119.5 |
O(7)—C(18)—C(17) | 123.7 (2) | C(23)—C(22)—H(22) | 119.6 |
C(13)—C(18)—C(17) | 120.6 (3) | C(24)—C(25)—H(25) | 120.0 |
C(22)—C(21)—C(26) | 118.6 (2) | C(26)—C(25)—H(25) | 119.9 |
C(22)—C(21)—C(30) | 120.2 (2) | C(21)—C(26)—H(26) | 119.4 |
C(26)—C(21)—C(30) | 121.1 (2) | C(25)—C(26)—H(26) | 119.5 |
C(21)—C(22)—C(23) | 120.8 (2) | O(8)—C(27)—H(27A) | 109.4 |
O(8)—C(23)—C(22) | 125.2 (2) | O(8)—C(27)—H(27B) | 109.6 |
O(8)—C(23)—C(24) | 114.6 (2) | O(8)—C(27)—H(27C) | 109.5 |
C(22)—C(23)—C(24) | 120.1 (2) | H(27A)—C(27)—H(27B) | 109.5 |
O(9)—C(24)—C(23) | 116.0 (2) | H(27A)—C(27)—H(27C) | 109.5 |
O(9)—C(24)—C(25) | 124.8 (2) | H(27B)—C(27)—H(27C) | 109.5 |
C(23)—C(24)—C(25) | 119.2 (2) | O(9)—C(28)—H(28A) | 110.1 |
C(24)—C(25)—C(26) | 120.1 (2) | O(9)—C(28)—H(28B) | 110.0 |
C(21)—C(26)—C(25) | 121.1 (2) | C(29)—C(28)—H(28A) | 110.2 |
O(9)—C(28)—C(29) | 107.0 (2) | C(29)—C(28)—H(28B) | 110.0 |
O(10)—C(30)—C(21) | 108.3 (2) | H(28A)—C(28)—H(28B) | 109.5 |
O(10)—C(30)—C(31) | 109.2 (2) | C(28)—C(29)—H(29A) | 109.6 |
C(21)—C(30)—C(31) | 113.6 (2) | C(28)—C(29)—H(29B) | 109.4 |
O(12)—C(31)—C(30) | 104.7 (2) | C(28)—C(29)—H(29C) | 109.5 |
O(12)—C(31)—C(32) | 107.2 (2) | H(29A)—C(29)—H(29B) | 109.5 |
C(30)—C(31)—C(32) | 114.3 (2) | H(29A)—C(29)—H(29C) | 109.5 |
O(11)—C(32)—C(31) | 111.5 (2) | H(29B)—C(29)—H(29C) | 109.5 |
O(12)—C(33)—C(34) | 118.8 (2) | O(10)—C(30)—H(30) | 108.6 |
O(12)—C(33)—C(38) | 121.4 (2) | C(21)—C(30)—H(30) | 108.5 |
C(34)—C(33)—C(38) | 119.6 (2) | C(31)—C(30)—H(30) | 108.5 |
O(13)—C(34)—C(33) | 115.6 (2) | O(12)—C(31)—H(31) | 110.2 |
O(13)—C(34)—C(35) | 124.2 (3) | C(30)—C(31)—H(31) | 110.2 |
C(33)—C(34)—C(35) | 120.2 (2) | C(32)—C(31)—H(31) | 110.2 |
C(34)—C(35)—C(36) | 119.1 (3) | O(11)—C(32)—H(32A) | 109.0 |
C(35)—C(36)—C(37) | 121.7 (3) | O(11)—C(32)—H(32B) | 109.0 |
C(36)—C(37)—C(38) | 119.1 (3) | C(31)—C(32)—H(32A) | 108.9 |
O(14)—C(38)—C(33) | 114.3 (2) | C(31)—C(32)—H(32B) | 108.9 |
O(14)—C(38)—C(37) | 125.4 (3) | H(32A)—C(32)—H(32B) | 109.5 |
C(33)—C(38)—C(37) | 120.3 (3) | C(34)—C(35)—H(35) | 120.5 |
C(10)—O(3)—H(3) | 109.6 | C(36)—C(35)—H(35) | 120.4 |
C(12)—O(4)—H(4) | 108.8 | C(35)—C(36)—H(36) | 119.2 |
C(30)—O(10)—H(10) | 109.5 | C(37)—C(36)—H(36) | 119.1 |
C(32)—O(11)—H(11) | 109.6 | C(36)—C(37)—H(37) | 120.4 |
C(1)—C(2)—H(2) | 119.5 | C(38)—C(37)—H(37) | 120.5 |
C(3)—C(2)—H(2) | 119.4 | O(13)—C(39)—H(39A) | 109.3 |
C(4)—C(5)—H(5) | 119.8 | O(13)—C(39)—H(39B) | 109.6 |
C(6)—C(5)—H(5) | 119.8 | O(13)—C(39)—H(39C) | 109.5 |
C(1)—C(6)—H(6) | 119.5 | H(39A)—C(39)—H(39B) | 109.5 |
C(5)—C(6)—H(6) | 119.5 | H(39A)—C(39)—H(39C) | 109.5 |
O(1)—C(7)—H(7A) | 109.4 | H(39B)—C(39)—H(39C) | 109.5 |
O(1)—C(7)—H(7B) | 109.5 | O(14)—C(40)—H(40A) | 109.4 |
O(1)—C(7)—H(7C) | 109.5 | O(14)—C(40)—H(40B) | 109.6 |
H(7A)—C(7)—H(7B) | 109.5 | O(14)—C(40)—H(40C) | 109.4 |
H(7A)—C(7)—H(7C) | 109.5 | H(40A)—C(40)—H(40B) | 109.5 |
H(7B)—C(7)—H(7C) | 109.5 | H(40A)—C(40)—H(40C) | 109.5 |
O(2)—C(8)—H(8A) | 110.0 | H(40B)—C(40)—H(40C) | 109.5 |
C(7)—O(1)—C(3)—C(2) | −5.8 (4) | O(5)—C(13)—C(14)—C(15) | −174.1 (3) |
C(7)—O(1)—C(3)—C(4) | 172.3 (2) | O(5)—C(13)—C(18)—O(7) | −3.8 (4) |
C(4)—O(2)—C(8)—C(9) | −179.9 (2) | O(5)—C(13)—C(18)—C(17) | 174.8 (3) |
C(8)—O(2)—C(4)—C(3) | −177.8 (2) | C(14)—C(13)—C(18)—O(7) | −176.3 (3) |
C(8)—O(2)—C(4)—C(5) | 2.3 (3) | C(14)—C(13)—C(18)—C(17) | 2.2 (5) |
C(11)—O(5)—C(13)—C(14) | −109.4 (3) | C(18)—C(13)—C(14)—O(6) | 177.5 (2) |
C(11)—O(5)—C(13)—C(18) | 78.1 (3) | C(18)—C(13)—C(14)—C(15) | −1.4 (5) |
C(13)—O(5)—C(11)—C(10) | 107.7 (2) | O(6)—C(14)—C(15)—C(16) | −179.4 (3) |
C(13)—O(5)—C(11)—C(12) | −131.8 (2) | C(13)—C(14)—C(15)—C(16) | −0.5 (5) |
C(19)—O(6)—C(14)—C(13) | 178.1 (2) | C(14)—C(15)—C(16)—C(17) | 1.8 (5) |
C(19)—O(6)—C(14)—C(15) | −3.0 (4) | C(15)—C(16)—C(17)—C(18) | −1.0 (5) |
C(20)—O(7)—C(18)—C(13) | 175.9 (3) | C(16)—C(17)—C(18)—O(7) | 177.4 (3) |
C(20)—O(7)—C(18)—C(17) | −2.7 (5) | C(16)—C(17)—C(18)—C(13) | −1.1 (5) |
C(27)—O(8)—C(23)—C(22) | −7.1 (4) | C(22)—C(21)—C(26)—C(25) | −0.5 (4) |
C(27)—O(8)—C(23)—C(24) | 171.0 (2) | C(26)—C(21)—C(22)—C(23) | 0.1 (3) |
C(24)—O(9)—C(28)—C(29) | 177.8 (2) | C(22)—C(21)—C(30)—O(10) | 150.0 (2) |
C(28)—O(9)—C(24)—C(23) | −175.0 (2) | C(22)—C(21)—C(30)—C(31) | −88.5 (3) |
C(28)—O(9)—C(24)—C(25) | 4.3 (3) | C(30)—C(21)—C(22)—C(23) | −177.6 (2) |
C(31)—O(12)—C(33)—C(34) | −118.3 (3) | C(26)—C(21)—C(30)—O(10) | −27.7 (3) |
C(31)—O(12)—C(33)—C(38) | 66.7 (3) | C(26)—C(21)—C(30)—C(31) | 93.8 (3) |
C(33)—O(12)—C(31)—C(30) | 115.3 (2) | C(30)—C(21)—C(26)—C(25) | 177.2 (2) |
C(33)—O(12)—C(31)—C(32) | −123.0 (2) | C(21)—C(22)—C(23)—O(8) | 178.9 (2) |
C(39)—O(13)—C(34)—C(33) | −175.5 (2) | C(21)—C(22)—C(23)—C(24) | 0.9 (4) |
C(39)—O(13)—C(34)—C(35) | 4.6 (4) | O(8)—C(23)—C(24)—O(9) | −0.3 (3) |
C(40)—O(14)—C(38)—C(33) | 178.1 (3) | O(8)—C(23)—C(24)—C(25) | −179.7 (2) |
C(40)—O(14)—C(38)—C(37) | 0.8 (5) | C(22)—C(23)—C(24)—O(9) | 177.8 (2) |
C(2)—C(1)—C(6)—C(5) | 0.6 (4) | C(22)—C(23)—C(24)—C(25) | −1.5 (4) |
C(6)—C(1)—C(2)—C(3) | −1.4 (4) | O(9)—C(24)—C(25)—C(26) | −178.2 (2) |
C(2)—C(1)—C(10)—O(3) | 147.5 (2) | C(23)—C(24)—C(25)—C(26) | 1.1 (4) |
C(2)—C(1)—C(10)—C(11) | −91.4 (3) | C(24)—C(25)—C(26)—C(21) | −0.1 (3) |
C(10)—C(1)—C(2)—C(3) | 178.2 (2) | O(10)—C(30)—C(31)—O(12) | −60.8 (2) |
C(6)—C(1)—C(10)—O(3) | −32.9 (3) | O(10)—C(30)—C(31)—C(32) | −177.7 (2) |
C(6)—C(1)—C(10)—C(11) | 88.2 (3) | C(21)—C(30)—C(31)—O(12) | 178.2 (2) |
C(10)—C(1)—C(6)—C(5) | −179.0 (2) | C(21)—C(30)—C(31)—C(32) | 61.3 (3) |
C(1)—C(2)—C(3)—O(1) | 179.5 (2) | O(12)—C(31)—C(32)—O(11) | −57.1 (2) |
C(1)—C(2)—C(3)—C(4) | 1.5 (4) | C(30)—C(31)—C(32)—O(11) | 58.4 (3) |
O(1)—C(3)—C(4)—O(2) | 1.0 (3) | O(12)—C(33)—C(34)—O(13) | 4.8 (4) |
O(1)—C(3)—C(4)—C(5) | −179.0 (2) | O(12)—C(33)—C(34)—C(35) | −175.3 (3) |
C(2)—C(3)—C(4)—O(2) | 179.2 (2) | O(12)—C(33)—C(38)—O(14) | −2.5 (4) |
C(2)—C(3)—C(4)—C(5) | −0.9 (4) | O(12)—C(33)—C(38)—C(37) | 175.0 (3) |
O(2)—C(4)—C(5)—C(6) | −179.9 (2) | C(34)—C(33)—C(38)—O(14) | −177.5 (3) |
C(3)—C(4)—C(5)—C(6) | 0.1 (3) | C(34)—C(33)—C(38)—C(37) | 0.0 (4) |
C(4)—C(5)—C(6)—C(1) | 0.0 (3) | C(38)—C(33)—C(34)—O(13) | 180.0 (2) |
O(3)—C(10)—C(11)—O(5) | −64.6 (2) | C(38)—C(33)—C(34)—C(35) | −0.2 (4) |
O(3)—C(10)—C(11)—C(12) | 178.7 (2) | O(13)—C(34)—C(35)—C(36) | 179.7 (3) |
C(1)—C(10)—C(11)—O(5) | 175.7 (2) | C(33)—C(34)—C(35)—C(36) | −0.1 (4) |
C(1)—C(10)—C(11)—C(12) | 59.1 (3) | C(34)—C(35)—C(36)—C(37) | 0.6 (5) |
O(5)—C(11)—C(12)—O(4) | 78.0 (3) | C(35)—C(36)—C(37)—C(38) | −0.7 (6) |
C(10)—C(11)—C(12)—O(4) | −165.1 (2) | C(36)—C(37)—C(38)—O(14) | 177.6 (3) |
O(5)—C(13)—C(14)—O(6) | 4.8 (4) | C(36)—C(37)—C(38)—C(33) | 0.4 (5) |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z; (iii) −x+1, −y, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2; (vi) x+1, y, z; (vii) −x+2, −y, −z+1; (viii) x−1/2, −y+1/2, z−1/2; (ix) x, y, z+1; (x) x+1/2, −y+1/2, z−1/2; (xi) x−1, y, z−1; (xii) −x+1, −y, −z+2; (xiii) x−1, y, z+1; (xiv) x+1, y, z−1; (xv) x+1, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O6 | 0.82 | 2.09 | 2.772 (3) | 141 |
O4—H4···O7 | 0.82 | 2.46 | 2.758 (3) | 103 |
O10—H10···O13 | 0.82 | 2.17 | 2.878 (3) | 145 |
O11—H11···O4 | 0.82 | 2.19 | 2.882 (3) | 142 |
O3—H3···O5 | 0.82 | 2.44 | 2.859 (3) | 113 |
O10—H10···O12 | 0.82 | 2.32 | 2.760 (3) | 114 |
O11—H11···O12 | 0.82 | 2.36 | 2.795 (3) | 114 |
Experimental details
Crystal data | |
Chemical formula | C20H26O7 |
Mr | 378.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.929 (4), 28.066 (10), 13.985 (5) |
β (°) | 100.954 (2) |
V (Å3) | 3826 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | Numerical (CrystalClear; Rigaku, 2006) |
Tmin, Tmax | 0.938, 0.961 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 30389, 8726, 3941 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.227, 1.00 |
No. of reflections | 8726 |
No. of parameters | 539 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.67 |
Computer programs: CrystalClear (Rigaku, 2006), CrystalStructure (Rigaku/MSC, 2007), SIR2004 (Burla et al., 2005), CRYSTALS (Carruthers et al., 1999), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O6 | 0.819 | 2.089 | 2.772 (3) | 140.7 |
O4—H4···O7 | 0.821 | 2.461 | 2.758 (3) | 102.5 |
O10—H10···O13 | 0.820 | 2.165 | 2.878 (3) | 145.4 |
O11—H11···O4 | 0.820 | 2.191 | 2.882 (3) | 142.1 |
O3—H3···O5 | 0.820 | 2.44 | 2.859 (3) | 113 |
O10—H10···O12 | 0.820 | 2.32 | 2.760 (3) | 114 |
O11—H11···O12 | 0.820 | 2.36 | 2.795 (3) | 114 |
Acknowledgements
The authors thank the Ministry of Education, Culture, Sports, Science and Technology of Japan for financial support via Grants-in-Aid for Scientific Research on Priority Areas `Synergy of Elements' (MN, 18064006) and for Young Scientists from JSPS (S, MN, 2075003). Financial and facility support from the System for Development and Assessment of Sustainable Humanosphere, Center for Ecological Research, Research Institute for Sustainable Humanosphere, Kyoto University, is also acknowledged.
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Carruthers, J. R., Rollett, J. S., Betteridge, P. W., Kinna, D., Pearce, L., Larsen, A. & Gabe, E. (1999). CRYSTALS. Issue 11. Chemical Crystallography Laboratory, Oxford, England. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Langer, V., Li, S. & Lundquist, K. (2002). Acta Cryst. E58, o42–o44. Web of Science CSD CrossRef IUCr Journals Google Scholar
Langer, V. & Lundquist, K. (2001). Acta Cryst. E57, o1219–o1221. Web of Science CSD CrossRef IUCr Journals Google Scholar
Langer, V., Lundquist, K. & Miksche, G. E. (2005). Acta Cryst. E61, o1001–o1003. Web of Science CSD CrossRef IUCr Journals Google Scholar
Langer, V., Lundquist, K., Stomberg, R. & Unge, S. von (2002). Acta Cryst. E58, o90–o92. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lundquist, K., Li, S. & Langer, V. (2005). Acta Cryst. C61, o256–o258. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Stomberg, R. & Lundquist, K. (1989). J. Crystallogr. Spectrosc. Res. 19, 331–339. CSD CrossRef CAS Web of Science Google Scholar
Unge, S. von, Lundquist, K. & Stomberg, R. (1988). Acta Chem. Scand. B, 42, 469–474. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Lignin is a complex biopolymer consisting of p-hydroxyphenyl, guaiacyl and syringyl phenylpropanoid monomer units. Aryl glycerol β-syringyl ethers are the main structural elements in hardwood lignins. The crystal structure of threo-2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3- propanediol (Langer, Li et al., 2002; Langer, Lundquist et al., 2002) and several syringylglycerol β-syringyl ethers are reported. We have prepared a guaiacylglycerol β-syringyl ether type lignin model dimer having an ethyl ether substituent at 4-position, which does not show a similar packing structure or hydrogen bonding network to that of the methyl ether counterpart.
There are two molecules of the title compound in the asymmetric unit (Fig. 1). The conformations of two molecules are similar, as indicated by the torsion angles of 59.1 (3) and 61.3 (3)° along the phenylpropanoid skeleton (C1—C10—C11—C12 and C21—C30—C31—C32), respectively. They are connected with each other by the hydrogen bond of O11—H11···O4 through the terminal hydroxyl groups. Intramolecular hydrogen bonds of O3—H3···O6, O4—H4···O7 and O10—H10···O13 are also present (Table 1).