Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103011089/gd1253sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103011089/gd1253Isup2.hkl |
CCDC reference: 217154
Cyclododecanone (m.p. 332 K) was dissolved in hexane until the solution was almost saturated. Racemic gossypol was dissolved in this solution, and additional hexane was added to induce crystallization of the title compound at 298 (2) K.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C30H30O8·2C12H22O | Z = 2 |
Mr = 883.13 | F(000) = 956 |
Triclinic, P1 | Dx = 1.204 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2640 (4) Å | Cell parameters from 30511 reflections |
b = 14.4674 (4) Å | θ = 2.2–29.9° |
c = 15.1532 (5) Å | µ = 0.08 mm−1 |
α = 82.108 (1)° | T = 150 K |
β = 89.206 (1)° | Irregular, yellow |
γ = 66.264 (1)° | 0.6 × 0.5 × 0.4 mm |
V = 2435.32 (13) Å3 |
CCD area-detector diffractometer | 14038 independent reflections |
Radiation source: fine-focus sealed tube | 10049 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ϕ and ω scans | θmax = 29.9°, θmin = 1.9° |
Absorption correction: empirical (using intensity measurements) (SADABS in SAINT; Bruker, 1998) | h = −17→17 |
Tmin = 0.749, Tmax = 0.975 | k = −20→20 |
65791 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0993P)2 + 0.1464P] where P = (Fo2 + 2Fc2)/3 |
14038 reflections | (Δ/σ)max = 0.003 |
851 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C30H30O8·2C12H22O | γ = 66.264 (1)° |
Mr = 883.13 | V = 2435.32 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.2640 (4) Å | Mo Kα radiation |
b = 14.4674 (4) Å | µ = 0.08 mm−1 |
c = 15.1532 (5) Å | T = 150 K |
α = 82.108 (1)° | 0.6 × 0.5 × 0.4 mm |
β = 89.206 (1)° |
CCD area-detector diffractometer | 14038 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS in SAINT; Bruker, 1998) | 10049 reflections with I > 2σ(I) |
Tmin = 0.749, Tmax = 0.975 | Rint = 0.053 |
65791 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.39 e Å−3 |
14038 reflections | Δρmin = −0.29 e Å−3 |
851 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.36578 (10) | 0.57071 (8) | 0.12449 (7) | 0.0267 (2) | |
H101 | 0.399 (2) | 0.5052 (18) | 0.1360 (14) | 0.051 (6)* | |
C1 | 0.40439 (11) | 0.61630 (9) | 0.18289 (8) | 0.0183 (2) | |
C2 | 0.49403 (11) | 0.55884 (9) | 0.24742 (8) | 0.0182 (2) | |
O2 | 0.11778 (10) | 0.80886 (8) | −0.01200 (7) | 0.0345 (3) | |
O3 | 0.13017 (10) | 0.95960 (8) | 0.03875 (7) | 0.0322 (2) | |
H103 | 0.110 (2) | 0.9142 (19) | 0.0111 (17) | 0.069 (7)* | |
C3 | 0.53222 (11) | 0.60850 (9) | 0.30686 (9) | 0.0210 (2) | |
O4 | 0.21758 (11) | 1.04534 (7) | 0.14058 (8) | 0.0328 (3) | |
H104 | 0.168 (2) | 1.0638 (19) | 0.1011 (17) | 0.063 (7)* | |
C4 | 0.48070 (11) | 0.71350 (9) | 0.29869 (9) | 0.0204 (2) | |
H4 | 0.5102 (15) | 0.7446 (13) | 0.3397 (11) | 0.025 (4)* | |
O5 | 0.42745 (9) | 0.42681 (8) | 0.37143 (7) | 0.0261 (2) | |
H105 | 0.3967 (19) | 0.4911 (17) | 0.3578 (14) | 0.047 (6)* | |
C5 | 0.33946 (11) | 0.88493 (9) | 0.22666 (8) | 0.0190 (2) | |
O6 | 0.42043 (10) | 0.18390 (8) | 0.51183 (7) | 0.0329 (2) | |
C6 | 0.25995 (12) | 0.94089 (9) | 0.15704 (9) | 0.0222 (3) | |
O7 | 0.58833 (10) | 0.03797 (7) | 0.46574 (7) | 0.0284 (2) | |
H107 | 0.528 (3) | 0.075 (2) | 0.4985 (18) | 0.079 (8)* | |
C7 | 0.21522 (12) | 0.89354 (10) | 0.09880 (8) | 0.0221 (3) | |
O8 | 0.76705 (11) | −0.04280 (7) | 0.36718 (8) | 0.0330 (3) | |
H108 | 0.729 (2) | −0.0598 (17) | 0.4040 (16) | 0.055 (7)* | |
C8 | 0.25506 (12) | 0.78754 (9) | 0.10587 (8) | 0.0196 (2) | |
C9 | 0.34860 (11) | 0.72518 (9) | 0.17330 (8) | 0.0176 (2) | |
O9 | 0.43161 (10) | 0.37033 (8) | 0.10271 (7) | 0.0340 (2) | |
C10 | 0.38903 (11) | 0.77430 (9) | 0.23349 (8) | 0.0180 (2) | |
O10 | 0.28695 (10) | 0.62194 (8) | 0.39624 (8) | 0.0360 (3) | |
C11 | 0.19517 (14) | 0.75080 (11) | 0.04587 (10) | 0.0288 (3) | |
H11 | 0.2130 (19) | 0.6806 (17) | 0.0486 (14) | 0.053 (6)* | |
C12 | 0.37915 (12) | 0.93666 (10) | 0.29359 (9) | 0.0238 (3) | |
H12 | 0.4096 (14) | 0.8860 (12) | 0.3489 (11) | 0.021 (4)* | |
C13 | 0.48445 (16) | 0.96007 (13) | 0.25885 (13) | 0.0377 (4) | |
H13A | 0.4615 (19) | 1.0066 (16) | 0.2019 (15) | 0.049 (6)* | |
H13B | 0.5578 (18) | 0.8982 (16) | 0.2487 (13) | 0.043 (5)* | |
H13C | 0.5113 (18) | 0.9959 (16) | 0.3015 (14) | 0.049 (6)* | |
C14 | 0.27937 (15) | 1.03161 (11) | 0.32216 (11) | 0.0323 (3) | |
H14A | 0.2063 (16) | 1.0179 (13) | 0.3381 (11) | 0.028 (4)* | |
H14B | 0.2529 (16) | 1.0905 (14) | 0.2751 (12) | 0.033 (5)* | |
H14C | 0.3127 (18) | 1.0498 (16) | 0.3777 (14) | 0.049 (6)* | |
C15 | 0.62779 (15) | 0.54649 (11) | 0.37849 (12) | 0.0332 (3) | |
H15A | 0.606 (2) | 0.4959 (17) | 0.4206 (15) | 0.055 (6)* | |
H15B | 0.6469 (17) | 0.5918 (15) | 0.4156 (13) | 0.043 (5)* | |
H15C | 0.701 (2) | 0.5063 (18) | 0.3543 (15) | 0.058 (6)* | |
C16 | 0.51770 (11) | 0.38440 (9) | 0.31653 (8) | 0.0176 (2) | |
C17 | 0.55282 (11) | 0.44487 (9) | 0.25312 (8) | 0.0178 (2) | |
C18 | 0.64791 (12) | 0.39837 (9) | 0.19803 (9) | 0.0206 (2) | |
C19 | 0.70378 (11) | 0.29317 (9) | 0.20812 (9) | 0.0197 (2) | |
H19 | 0.7683 (16) | 0.2635 (13) | 0.1735 (12) | 0.029 (4)* | |
C20 | 0.73288 (11) | 0.11906 (9) | 0.28076 (8) | 0.0191 (2) | |
C21 | 0.70474 (12) | 0.06109 (9) | 0.34945 (9) | 0.0212 (3) | |
C22 | 0.60910 (12) | 0.10566 (9) | 0.40497 (8) | 0.0198 (2) | |
C23 | 0.54087 (11) | 0.21062 (9) | 0.39550 (8) | 0.0177 (2) | |
C24 | 0.57423 (11) | 0.27565 (9) | 0.32839 (8) | 0.0165 (2) | |
C25 | 0.67000 (11) | 0.22944 (9) | 0.27185 (8) | 0.0168 (2) | |
C26 | 0.44019 (13) | 0.24363 (11) | 0.45298 (10) | 0.0286 (3) | |
H26 | 0.3877 (19) | 0.3149 (17) | 0.4443 (14) | 0.050 (6)* | |
C27 | 0.83213 (13) | 0.06946 (10) | 0.21856 (10) | 0.0262 (3) | |
H27 | 0.8212 (16) | 0.1217 (14) | 0.1616 (12) | 0.035 (5)* | |
C28 | 0.83127 (16) | −0.02594 (11) | 0.18581 (11) | 0.0324 (3) | |
H28A | 0.8573 (17) | −0.0851 (15) | 0.2335 (13) | 0.036 (5)* | |
H28B | 0.7532 (19) | −0.0116 (16) | 0.1612 (14) | 0.047 (6)* | |
H28C | 0.8896 (19) | −0.0442 (16) | 0.1364 (15) | 0.052 (6)* | |
C29 | 0.95348 (14) | 0.04767 (14) | 0.26198 (15) | 0.0456 (4) | |
H29A | 0.9550 | 0.1116 | 0.2752 | 0.068* | |
H29B | 1.0164 | 0.0174 | 0.2211 | 0.068* | |
H29C | 0.9668 | 0.0001 | 0.3174 | 0.068* | |
C30 | 0.68741 (14) | 0.46307 (11) | 0.12909 (11) | 0.0322 (3) | |
H30A | 0.7582 | 0.4190 | 0.1009 | 0.048* | |
H30B | 0.7067 | 0.5115 | 0.1580 | 0.048* | |
H30C | 0.6230 | 0.5006 | 0.0836 | 0.048* | |
C31 | 0.43789 (13) | 0.28352 (11) | 0.12106 (10) | 0.0266 (3) | |
C32 | 0.52413 (14) | 0.19812 (13) | 0.07490 (13) | 0.0370 (4) | |
H32A | 0.5745 (17) | 0.2242 (15) | 0.0420 (13) | 0.038 (5)* | |
H32B | 0.5727 (18) | 0.1415 (16) | 0.1218 (14) | 0.044 (5)* | |
C33 | 0.45949 (16) | 0.15943 (13) | 0.01170 (12) | 0.0375 (4) | |
H33A | 0.4055 (18) | 0.1317 (15) | 0.0488 (13) | 0.042 (5)* | |
H33B | 0.522 (2) | 0.1004 (19) | −0.0135 (16) | 0.068 (7)* | |
C34 | 0.38379 (17) | 0.24218 (15) | −0.06214 (11) | 0.0390 (4) | |
H34A | 0.3433 (16) | 0.3099 (14) | −0.0370 (12) | 0.035 (5)* | |
H34B | 0.437 (2) | 0.2520 (19) | −0.1052 (17) | 0.072 (7)* | |
C35 | 0.28850 (18) | 0.21653 (18) | −0.10500 (13) | 0.0464 (5) | |
H35A | 0.263 (2) | 0.2604 (18) | −0.1601 (17) | 0.059 (7)* | |
H35B | 0.327 (2) | 0.1441 (19) | −0.1149 (16) | 0.060 (6)* | |
C36 | 0.18229 (16) | 0.22996 (13) | −0.04576 (13) | 0.0393 (4) | |
H36A | 0.1344 (18) | 0.1918 (15) | −0.0653 (13) | 0.043 (5)* | |
H36B | 0.2181 (16) | 0.1916 (14) | 0.0163 (13) | 0.034 (5)* | |
C37 | 0.09990 (16) | 0.34114 (13) | −0.04287 (12) | 0.0371 (4) | |
H37A | 0.1495 (18) | 0.3828 (16) | −0.0466 (14) | 0.046 (5)* | |
H37B | 0.0490 (19) | 0.3672 (16) | −0.0946 (15) | 0.049 (6)* | |
C38 | 0.02053 (15) | 0.35834 (13) | 0.03766 (12) | 0.0367 (4) | |
H38A | −0.0406 (19) | 0.4310 (16) | 0.0283 (14) | 0.046 (5)* | |
H38B | −0.0313 (18) | 0.3183 (15) | 0.0396 (13) | 0.044 (5)* | |
C39 | 0.08819 (16) | 0.33088 (15) | 0.12841 (12) | 0.0388 (4) | |
H39A | 0.1464 (16) | 0.2577 (14) | 0.1403 (12) | 0.032 (4)* | |
H39B | 0.030 (2) | 0.3332 (19) | 0.1775 (17) | 0.074 (8)* | |
C40 | 0.15712 (15) | 0.39564 (13) | 0.14277 (12) | 0.0368 (4) | |
H40A | 0.1962 (16) | 0.4091 (14) | 0.0826 (12) | 0.033 (4)* | |
H40B | 0.1004 (18) | 0.4607 (16) | 0.1587 (14) | 0.047 (5)* | |
C41 | 0.25568 (16) | 0.34570 (15) | 0.21722 (11) | 0.0380 (4) | |
H41A | 0.2853 (17) | 0.3974 (15) | 0.2325 (13) | 0.042 (5)* | |
H41B | 0.2239 (19) | 0.3222 (16) | 0.2691 (15) | 0.051 (6)* | |
C42 | 0.36188 (14) | 0.25550 (12) | 0.18965 (10) | 0.0307 (3) | |
H42A | 0.3344 (16) | 0.2036 (14) | 0.1695 (12) | 0.036 (5)* | |
H42B | 0.4225 (19) | 0.2145 (16) | 0.2380 (14) | 0.051 (6)* | |
C51 | 0.21609 (12) | 0.71094 (10) | 0.38704 (10) | 0.0259 (3) | |
C52 | 0.22181 (15) | 0.78177 (13) | 0.45000 (12) | 0.0354 (3) | |
H52A | 0.296 (2) | 0.7477 (17) | 0.4829 (15) | 0.055 (6)* | |
H52B | 0.2222 (16) | 0.8447 (15) | 0.4119 (13) | 0.038 (5)* | |
C53 | 0.11669 (16) | 0.80982 (13) | 0.51234 (11) | 0.0366 (4) | |
H53A | 0.0418 (18) | 0.8471 (15) | 0.4766 (13) | 0.041 (5)* | |
H53B | 0.1206 (19) | 0.8610 (17) | 0.5485 (15) | 0.056 (6)* | |
C54 | 0.11320 (16) | 0.71762 (14) | 0.57314 (11) | 0.0379 (4) | |
H54A | 0.1360 (18) | 0.6555 (16) | 0.5403 (14) | 0.045 (5)* | |
H54B | 0.178 (2) | 0.6968 (17) | 0.6215 (15) | 0.057 (6)* | |
C55 | −0.00892 (18) | 0.73609 (17) | 0.61230 (12) | 0.0456 (4) | |
H55A | −0.003 (2) | 0.6785 (19) | 0.6603 (17) | 0.066 (7)* | |
H55B | −0.030 (2) | 0.7975 (19) | 0.6372 (16) | 0.060 (6)* | |
C56 | −0.10273 (16) | 0.74278 (14) | 0.54312 (13) | 0.0406 (4) | |
H56A | −0.1010 (16) | 0.7903 (15) | 0.4936 (13) | 0.035 (5)* | |
H56B | −0.182 (2) | 0.7713 (18) | 0.5628 (16) | 0.062 (7)* | |
C57 | −0.08462 (18) | 0.63930 (13) | 0.51703 (13) | 0.0419 (4) | |
H57A | 0.0024 (18) | 0.5964 (15) | 0.5193 (13) | 0.041 (5)* | |
H57B | −0.113 (2) | 0.5987 (17) | 0.5659 (15) | 0.058 (6)* | |
C58 | −0.14430 (15) | 0.64438 (14) | 0.42861 (14) | 0.0431 (4) | |
H58A | −0.233 (2) | 0.6889 (16) | 0.4290 (14) | 0.051 (6)* | |
H58B | −0.1403 (19) | 0.5744 (17) | 0.4171 (14) | 0.054 (6)* | |
C59 | −0.09409 (15) | 0.68667 (15) | 0.34694 (13) | 0.0408 (4) | |
H59A | −0.0992 (17) | 0.7560 (16) | 0.3537 (13) | 0.043 (5)* | |
H59B | −0.147 (2) | 0.6955 (17) | 0.2936 (15) | 0.056 (6)* | |
C60 | 0.03520 (15) | 0.61949 (13) | 0.32883 (12) | 0.0359 (4) | |
H60A | 0.0828 (15) | 0.5900 (12) | 0.3878 (12) | 0.025 (4)* | |
H60B | 0.0366 (18) | 0.5610 (16) | 0.3017 (14) | 0.051 (6)* | |
C61 | 0.09552 (17) | 0.67702 (14) | 0.26836 (11) | 0.0369 (4) | |
H61A | 0.1730 (18) | 0.6303 (15) | 0.2457 (13) | 0.042 (5)* | |
H61B | 0.048 (2) | 0.7084 (17) | 0.2107 (16) | 0.062 (7)* | |
C62 | 0.11922 (14) | 0.75551 (11) | 0.31388 (10) | 0.0293 (3) | |
H62A | 0.0463 (17) | 0.8018 (14) | 0.3355 (12) | 0.036 (5)* | |
H62B | 0.1461 (17) | 0.7983 (14) | 0.2706 (13) | 0.038 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0378 (5) | 0.0156 (5) | 0.0247 (5) | −0.0066 (4) | −0.0074 (4) | −0.0085 (4) |
C1 | 0.0234 (6) | 0.0144 (5) | 0.0167 (6) | −0.0061 (5) | 0.0026 (5) | −0.0059 (4) |
C2 | 0.0208 (6) | 0.0118 (5) | 0.0204 (6) | −0.0043 (4) | 0.0027 (5) | −0.0047 (4) |
O2 | 0.0448 (6) | 0.0287 (5) | 0.0264 (5) | −0.0118 (5) | −0.0131 (5) | −0.0003 (4) |
O3 | 0.0445 (6) | 0.0192 (5) | 0.0248 (5) | −0.0058 (5) | −0.0117 (5) | 0.0021 (4) |
C3 | 0.0217 (6) | 0.0154 (6) | 0.0239 (6) | −0.0049 (5) | −0.0020 (5) | −0.0039 (5) |
O4 | 0.0492 (7) | 0.0114 (4) | 0.0315 (6) | −0.0066 (4) | −0.0097 (5) | 0.0010 (4) |
C4 | 0.0227 (6) | 0.0149 (6) | 0.0230 (6) | −0.0057 (5) | −0.0010 (5) | −0.0067 (5) |
O5 | 0.0309 (5) | 0.0157 (5) | 0.0278 (5) | −0.0039 (4) | 0.0138 (4) | −0.0084 (4) |
C5 | 0.0239 (6) | 0.0132 (5) | 0.0193 (6) | −0.0061 (5) | 0.0034 (5) | −0.0053 (4) |
O6 | 0.0378 (6) | 0.0278 (5) | 0.0298 (5) | −0.0110 (5) | 0.0143 (5) | −0.0023 (4) |
C6 | 0.0310 (7) | 0.0112 (5) | 0.0218 (6) | −0.0057 (5) | 0.0028 (5) | −0.0027 (5) |
O7 | 0.0398 (6) | 0.0180 (5) | 0.0245 (5) | −0.0099 (4) | 0.0091 (4) | −0.0001 (4) |
C7 | 0.0294 (7) | 0.0168 (6) | 0.0166 (6) | −0.0061 (5) | 0.0000 (5) | −0.0012 (5) |
O8 | 0.0436 (6) | 0.0121 (4) | 0.0322 (6) | −0.0011 (4) | 0.0110 (5) | 0.0003 (4) |
C8 | 0.0260 (6) | 0.0155 (6) | 0.0149 (5) | −0.0056 (5) | 0.0015 (5) | −0.0032 (4) |
C9 | 0.0206 (6) | 0.0138 (5) | 0.0171 (6) | −0.0049 (5) | 0.0023 (4) | −0.0043 (4) |
O9 | 0.0476 (6) | 0.0236 (5) | 0.0339 (6) | −0.0162 (5) | −0.0043 (5) | −0.0079 (4) |
C10 | 0.0214 (6) | 0.0128 (5) | 0.0186 (6) | −0.0050 (5) | 0.0026 (4) | −0.0042 (4) |
O10 | 0.0350 (6) | 0.0228 (5) | 0.0378 (6) | 0.0007 (4) | 0.0113 (5) | −0.0049 (4) |
C11 | 0.0374 (8) | 0.0211 (7) | 0.0256 (7) | −0.0094 (6) | −0.0081 (6) | −0.0025 (5) |
C12 | 0.0305 (7) | 0.0134 (6) | 0.0250 (7) | −0.0048 (5) | −0.0018 (5) | −0.0072 (5) |
C13 | 0.0359 (8) | 0.0310 (8) | 0.0519 (11) | −0.0170 (7) | 0.0012 (7) | −0.0138 (8) |
C14 | 0.0417 (9) | 0.0186 (7) | 0.0294 (8) | −0.0023 (6) | −0.0005 (6) | −0.0114 (6) |
C15 | 0.0359 (8) | 0.0177 (6) | 0.0399 (9) | −0.0037 (6) | −0.0181 (7) | −0.0054 (6) |
C16 | 0.0190 (5) | 0.0146 (5) | 0.0174 (6) | −0.0035 (4) | 0.0027 (4) | −0.0071 (4) |
C17 | 0.0207 (6) | 0.0113 (5) | 0.0197 (6) | −0.0037 (4) | 0.0005 (5) | −0.0053 (4) |
C18 | 0.0242 (6) | 0.0156 (6) | 0.0211 (6) | −0.0068 (5) | 0.0040 (5) | −0.0045 (5) |
C19 | 0.0210 (6) | 0.0148 (6) | 0.0209 (6) | −0.0039 (5) | 0.0059 (5) | −0.0056 (5) |
C20 | 0.0219 (6) | 0.0135 (5) | 0.0190 (6) | −0.0034 (5) | 0.0016 (5) | −0.0056 (4) |
C21 | 0.0262 (6) | 0.0119 (5) | 0.0213 (6) | −0.0030 (5) | 0.0005 (5) | −0.0032 (5) |
C22 | 0.0264 (6) | 0.0165 (6) | 0.0158 (6) | −0.0082 (5) | 0.0008 (5) | −0.0016 (4) |
C23 | 0.0211 (6) | 0.0163 (6) | 0.0153 (5) | −0.0066 (5) | 0.0009 (4) | −0.0040 (4) |
C24 | 0.0188 (5) | 0.0133 (5) | 0.0164 (5) | −0.0047 (4) | 0.0005 (4) | −0.0048 (4) |
C25 | 0.0192 (5) | 0.0129 (5) | 0.0169 (5) | −0.0042 (4) | 0.0012 (4) | −0.0052 (4) |
C26 | 0.0317 (7) | 0.0220 (7) | 0.0290 (7) | −0.0075 (6) | 0.0110 (6) | −0.0053 (6) |
C27 | 0.0333 (7) | 0.0145 (6) | 0.0265 (7) | −0.0042 (5) | 0.0107 (6) | −0.0071 (5) |
C28 | 0.0454 (9) | 0.0189 (7) | 0.0267 (7) | −0.0044 (6) | 0.0044 (7) | −0.0109 (6) |
C29 | 0.0282 (8) | 0.0415 (10) | 0.0701 (13) | −0.0105 (7) | 0.0174 (8) | −0.0310 (9) |
C30 | 0.0382 (8) | 0.0179 (6) | 0.0363 (8) | −0.0082 (6) | 0.0176 (6) | −0.0022 (6) |
C31 | 0.0279 (7) | 0.0215 (6) | 0.0295 (7) | −0.0074 (5) | −0.0073 (5) | −0.0077 (5) |
C32 | 0.0278 (7) | 0.0323 (8) | 0.0501 (10) | −0.0073 (7) | −0.0013 (7) | −0.0185 (7) |
C33 | 0.0367 (8) | 0.0322 (8) | 0.0444 (9) | −0.0097 (7) | 0.0028 (7) | −0.0222 (7) |
C34 | 0.0451 (9) | 0.0514 (10) | 0.0265 (8) | −0.0236 (8) | 0.0111 (7) | −0.0134 (7) |
C35 | 0.0525 (11) | 0.0581 (12) | 0.0304 (9) | −0.0183 (9) | 0.0010 (8) | −0.0253 (9) |
C36 | 0.0389 (9) | 0.0346 (9) | 0.0495 (10) | −0.0161 (7) | −0.0037 (8) | −0.0176 (8) |
C37 | 0.0411 (9) | 0.0318 (8) | 0.0350 (8) | −0.0099 (7) | −0.0089 (7) | −0.0075 (7) |
C38 | 0.0285 (7) | 0.0339 (8) | 0.0469 (10) | −0.0101 (7) | −0.0052 (7) | −0.0102 (7) |
C39 | 0.0348 (8) | 0.0472 (10) | 0.0366 (9) | −0.0174 (8) | 0.0034 (7) | −0.0112 (8) |
C40 | 0.0323 (8) | 0.0315 (8) | 0.0427 (9) | −0.0047 (7) | −0.0015 (7) | −0.0187 (7) |
C41 | 0.0415 (9) | 0.0494 (10) | 0.0251 (8) | −0.0161 (8) | 0.0028 (7) | −0.0197 (7) |
C42 | 0.0348 (8) | 0.0286 (7) | 0.0264 (7) | −0.0108 (6) | −0.0078 (6) | −0.0019 (6) |
C51 | 0.0256 (6) | 0.0217 (6) | 0.0292 (7) | −0.0076 (5) | 0.0106 (5) | −0.0064 (5) |
C52 | 0.0337 (8) | 0.0324 (8) | 0.0444 (9) | −0.0145 (7) | 0.0031 (7) | −0.0155 (7) |
C53 | 0.0413 (9) | 0.0327 (8) | 0.0334 (8) | −0.0085 (7) | 0.0027 (7) | −0.0175 (7) |
C54 | 0.0378 (8) | 0.0413 (9) | 0.0235 (7) | −0.0041 (7) | −0.0021 (6) | −0.0059 (7) |
C55 | 0.0498 (10) | 0.0539 (12) | 0.0264 (8) | −0.0115 (9) | 0.0120 (7) | −0.0153 (8) |
C56 | 0.0366 (9) | 0.0349 (9) | 0.0453 (10) | −0.0060 (7) | 0.0111 (7) | −0.0170 (8) |
C57 | 0.0478 (10) | 0.0281 (8) | 0.0466 (10) | −0.0122 (7) | 0.0186 (8) | −0.0066 (7) |
C58 | 0.0303 (8) | 0.0364 (9) | 0.0696 (13) | −0.0158 (7) | 0.0140 (8) | −0.0238 (9) |
C59 | 0.0316 (8) | 0.0466 (10) | 0.0410 (9) | −0.0101 (7) | −0.0033 (7) | −0.0133 (8) |
C60 | 0.0397 (8) | 0.0323 (8) | 0.0395 (9) | −0.0141 (7) | 0.0090 (7) | −0.0195 (7) |
C61 | 0.0468 (9) | 0.0392 (9) | 0.0259 (8) | −0.0153 (8) | 0.0093 (7) | −0.0166 (7) |
C62 | 0.0345 (8) | 0.0229 (7) | 0.0264 (7) | −0.0069 (6) | 0.0081 (6) | −0.0056 (6) |
O1—C1 | 1.3660 (15) | C30—H30B | 0.9800 |
O1—H101 | 0.86 (2) | C30—H30C | 0.9800 |
C1—C2 | 1.3880 (18) | C31—C42 | 1.508 (2) |
C1—C9 | 1.4294 (16) | C31—C32 | 1.516 (2) |
C2—C3 | 1.4167 (17) | C32—C33 | 1.544 (2) |
C2—C17 | 1.5005 (16) | C32—H32A | 0.95 (2) |
O2—C11 | 1.2468 (18) | C32—H32B | 0.99 (2) |
O3—C7 | 1.3470 (16) | C33—C34 | 1.521 (3) |
O3—H103 | 0.94 (3) | C33—H33A | 1.03 (2) |
C3—C4 | 1.3784 (17) | C33—H33B | 1.01 (3) |
C3—C15 | 1.5093 (19) | C34—C35 | 1.537 (3) |
O4—C6 | 1.3724 (15) | C34—H34A | 1.028 (19) |
O4—H104 | 0.80 (3) | C34—H34B | 0.95 (3) |
C4—C10 | 1.4176 (18) | C35—C36 | 1.534 (3) |
C4—H4 | 0.966 (17) | C35—H35A | 0.95 (2) |
O5—C16 | 1.3644 (15) | C35—H35B | 0.99 (2) |
O5—H105 | 0.85 (2) | C36—C37 | 1.523 (2) |
C5—C6 | 1.3703 (18) | C36—H36A | 1.02 (2) |
C5—C10 | 1.4542 (16) | C36—H36B | 1.028 (19) |
C5—C12 | 1.5300 (17) | C37—C38 | 1.534 (3) |
O6—C26 | 1.2457 (17) | C37—H37A | 1.01 (2) |
C6—C7 | 1.4252 (18) | C37—H37B | 0.94 (2) |
O7—C22 | 1.3485 (15) | C38—C39 | 1.534 (2) |
O7—H107 | 0.91 (3) | C38—H38A | 1.01 (2) |
C7—C8 | 1.3982 (17) | C38—H38B | 1.02 (2) |
O8—C21 | 1.3731 (15) | C39—C40 | 1.529 (2) |
O8—H108 | 0.80 (2) | C39—H39A | 1.003 (19) |
C8—C11 | 1.4541 (18) | C39—H39B | 1.01 (3) |
C8—C9 | 1.4560 (18) | C40—C41 | 1.538 (2) |
C9—C10 | 1.4343 (17) | C40—H40A | 1.055 (18) |
O9—C31 | 1.2196 (17) | C40—H40B | 0.98 (2) |
O10—C51 | 1.2189 (17) | C41—C42 | 1.530 (2) |
C11—H11 | 0.94 (2) | C41—H41A | 1.01 (2) |
C12—C13 | 1.531 (2) | C41—H41B | 0.95 (2) |
C12—C14 | 1.5387 (19) | C42—H42A | 1.021 (18) |
C12—H12 | 0.999 (16) | C42—H42B | 0.99 (2) |
C13—H13A | 0.99 (2) | C51—C62 | 1.510 (2) |
C13—H13B | 1.01 (2) | C51—C52 | 1.514 (2) |
C13—H13C | 1.02 (2) | C52—C53 | 1.539 (2) |
C14—H14A | 1.013 (18) | C52—H52A | 0.95 (2) |
C14—H14B | 0.978 (19) | C52—H52B | 1.01 (2) |
C14—H14C | 1.05 (2) | C53—C54 | 1.529 (3) |
C15—H15A | 1.02 (2) | C53—H53A | 0.98 (2) |
C15—H15B | 1.01 (2) | C53—H53B | 1.00 (2) |
C15—H15C | 0.95 (2) | C54—C55 | 1.537 (3) |
C16—C17 | 1.3912 (17) | C54—H54A | 1.02 (2) |
C16—C24 | 1.4269 (16) | C54—H54B | 1.01 (2) |
C17—C18 | 1.4160 (17) | C55—C56 | 1.532 (3) |
C18—C19 | 1.3815 (17) | C55—H55A | 1.01 (3) |
C18—C30 | 1.5115 (19) | C55—H55B | 0.95 (2) |
C19—C25 | 1.4165 (17) | C56—C57 | 1.530 (2) |
C19—H19 | 0.928 (18) | C56—H56A | 0.952 (19) |
C20—C21 | 1.3745 (18) | C56—H56B | 0.95 (2) |
C20—C25 | 1.4544 (16) | C57—C58 | 1.514 (3) |
C20—C27 | 1.5283 (18) | C57—H57A | 0.99 (2) |
C21—C22 | 1.4184 (18) | C57—H57B | 1.03 (2) |
C22—C23 | 1.3954 (17) | C58—C59 | 1.536 (3) |
C23—C26 | 1.4563 (18) | C58—H58A | 1.02 (2) |
C23—C24 | 1.4568 (17) | C58—H58B | 1.03 (2) |
C24—C25 | 1.4345 (16) | C59—C60 | 1.534 (2) |
C26—H26 | 0.96 (2) | C59—H59A | 1.00 (2) |
C27—C29 | 1.530 (2) | C59—H59B | 1.01 (2) |
C27—C28 | 1.533 (2) | C60—C61 | 1.532 (2) |
C27—H27 | 1.038 (19) | C60—H60A | 1.016 (17) |
C28—H28A | 0.986 (19) | C60—H60B | 0.98 (2) |
C28—H28B | 0.96 (2) | C61—C62 | 1.528 (2) |
C28—H28C | 1.01 (2) | C61—H61A | 1.01 (2) |
C29—H29A | 0.9800 | C61—H61B | 1.00 (2) |
C29—H29B | 0.9800 | C62—H62A | 0.962 (19) |
C29—H29C | 0.9800 | C62—H62B | 0.984 (19) |
C30—H30A | 0.9800 | ||
C1—O1—H101 | 112.0 (15) | C34—C33—C32 | 113.00 (14) |
O1—C1—C2 | 121.07 (11) | C34—C33—H33A | 108.9 (11) |
O1—C1—C9 | 116.59 (11) | C32—C33—H33A | 108.4 (11) |
C2—C1—C9 | 122.34 (11) | C34—C33—H33B | 111.3 (14) |
C1—C2—C3 | 119.67 (11) | C32—C33—H33B | 107.8 (14) |
C1—C2—C17 | 120.49 (11) | H33A—C33—H33B | 107.3 (18) |
C3—C2—C17 | 119.83 (11) | C33—C34—C35 | 113.17 (16) |
C7—O3—H103 | 100.6 (15) | C33—C34—H34A | 109.3 (10) |
C4—C3—C2 | 119.26 (12) | C35—C34—H34A | 109.4 (10) |
C4—C3—C15 | 120.72 (12) | C33—C34—H34B | 107.2 (15) |
C2—C3—C15 | 120.02 (11) | C35—C34—H34B | 111.1 (15) |
C6—O4—H104 | 106.8 (18) | H34A—C34—H34B | 106.4 (18) |
C3—C4—C10 | 122.41 (11) | C36—C35—C34 | 112.57 (13) |
C3—C4—H4 | 116.8 (10) | C36—C35—H35A | 110.5 (14) |
C10—C4—H4 | 120.8 (10) | C34—C35—H35A | 106.8 (14) |
C16—O5—H105 | 110.1 (14) | C36—C35—H35B | 109.0 (14) |
C6—C5—C10 | 118.09 (11) | C34—C35—H35B | 107.2 (13) |
C6—C5—C12 | 121.34 (11) | H35A—C35—H35B | 110.7 (19) |
C10—C5—C12 | 120.53 (11) | C37—C36—C35 | 113.50 (16) |
C5—C6—O4 | 121.95 (12) | C37—C36—H36A | 109.8 (11) |
C5—C6—C7 | 121.57 (11) | C35—C36—H36A | 110.8 (11) |
O4—C6—C7 | 116.47 (12) | C37—C36—H36B | 112.3 (10) |
C22—O7—H107 | 106.8 (17) | C35—C36—H36B | 106.0 (10) |
O3—C7—C8 | 123.63 (12) | H36A—C36—H36B | 104.0 (15) |
O3—C7—C6 | 114.18 (11) | C36—C37—C38 | 114.23 (15) |
C8—C7—C6 | 122.17 (12) | C36—C37—H37A | 108.7 (12) |
C21—O8—H108 | 103.1 (17) | C38—C37—H37A | 111.8 (12) |
C7—C8—C11 | 115.78 (12) | C36—C37—H37B | 109.7 (13) |
C7—C8—C9 | 117.76 (11) | C38—C37—H37B | 107.2 (13) |
C11—C8—C9 | 126.44 (11) | H37A—C37—H37B | 104.7 (17) |
C1—C9—C10 | 117.28 (11) | C39—C38—C37 | 114.77 (14) |
C1—C9—C8 | 123.60 (11) | C39—C38—H38A | 111.8 (12) |
C10—C9—C8 | 119.11 (11) | C37—C38—H38A | 108.5 (12) |
C4—C10—C9 | 119.03 (11) | C39—C38—H38B | 107.6 (11) |
C4—C10—C5 | 120.12 (11) | C37—C38—H38B | 111.4 (11) |
C9—C10—C5 | 120.83 (11) | H38A—C38—H38B | 102.1 (16) |
O2—C11—C8 | 122.82 (13) | C40—C39—C38 | 114.95 (16) |
O2—C11—H11 | 115.7 (13) | C40—C39—H39A | 106.8 (10) |
C8—C11—H11 | 121.5 (13) | C38—C39—H39A | 112.9 (10) |
C5—C12—C13 | 110.27 (12) | C40—C39—H39B | 111.1 (14) |
C5—C12—C14 | 114.96 (12) | C38—C39—H39B | 109.0 (14) |
C13—C12—C14 | 111.36 (12) | H39A—C39—H39B | 101.2 (17) |
C5—C12—H12 | 107.0 (9) | C39—C40—C41 | 113.57 (15) |
C13—C12—H12 | 106.5 (9) | C39—C40—H40A | 108.7 (10) |
C14—C12—H12 | 106.3 (9) | C41—C40—H40A | 108.7 (10) |
C12—C13—H13A | 110.5 (12) | C39—C40—H40B | 108.1 (12) |
C12—C13—H13B | 114.7 (11) | C41—C40—H40B | 108.3 (12) |
H13A—C13—H13B | 107.3 (17) | H40A—C40—H40B | 109.4 (16) |
C12—C13—H13C | 111.8 (12) | C42—C41—C40 | 112.09 (12) |
H13A—C13—H13C | 106.1 (16) | C42—C41—H41A | 108.2 (11) |
H13B—C13—H13C | 105.9 (16) | C40—C41—H41A | 109.6 (11) |
C12—C14—H14A | 110.9 (10) | C42—C41—H41B | 108.8 (13) |
C12—C14—H14B | 112.9 (11) | C40—C41—H41B | 109.3 (13) |
H14A—C14—H14B | 106.2 (14) | H41A—C41—H41B | 108.8 (17) |
C12—C14—H14C | 107.5 (12) | C31—C42—C41 | 115.16 (14) |
H14A—C14—H14C | 110.1 (15) | C31—C42—H42A | 110.8 (10) |
H14B—C14—H14C | 109.2 (15) | C41—C42—H42A | 110.5 (10) |
C3—C15—H15A | 113.3 (12) | C31—C42—H42B | 101.0 (12) |
C3—C15—H15B | 111.6 (11) | C41—C42—H42B | 115.2 (12) |
H15A—C15—H15B | 108.1 (16) | H42A—C42—H42B | 103.2 (16) |
C3—C15—H15C | 112.2 (14) | O10—C51—C62 | 122.30 (13) |
H15A—C15—H15C | 105.1 (18) | O10—C51—C52 | 120.64 (14) |
H15B—C15—H15C | 106.2 (17) | C62—C51—C52 | 117.06 (13) |
O5—C16—C17 | 121.23 (11) | C51—C52—C53 | 112.08 (13) |
O5—C16—C24 | 116.56 (11) | C51—C52—H52A | 106.8 (13) |
C17—C16—C24 | 122.21 (11) | C53—C52—H52A | 111.4 (14) |
C16—C17—C18 | 119.76 (11) | C51—C52—H52B | 107.0 (11) |
C16—C17—C2 | 119.50 (11) | C53—C52—H52B | 111.0 (11) |
C18—C17—C2 | 120.65 (11) | H52A—C52—H52B | 108.4 (17) |
C19—C18—C17 | 119.07 (11) | C54—C53—C52 | 113.30 (14) |
C19—C18—C30 | 120.57 (12) | C54—C53—H53A | 111.1 (11) |
C17—C18—C30 | 120.37 (11) | C52—C53—H53A | 109.3 (12) |
C18—C19—C25 | 122.57 (11) | C54—C53—H53B | 110.3 (13) |
C18—C19—H19 | 118.4 (11) | C52—C53—H53B | 109.0 (13) |
C25—C19—H19 | 119.0 (11) | H53A—C53—H53B | 103.4 (17) |
C21—C20—C25 | 118.11 (11) | C53—C54—C55 | 114.10 (15) |
C21—C20—C27 | 121.02 (11) | C53—C54—H54A | 111.6 (11) |
C25—C20—C27 | 120.79 (11) | C55—C54—H54A | 107.0 (11) |
O8—C21—C20 | 121.69 (12) | C53—C54—H54B | 107.2 (13) |
O8—C21—C22 | 116.76 (11) | C55—C54—H54B | 111.7 (13) |
C20—C21—C22 | 121.56 (11) | H54A—C54—H54B | 104.8 (17) |
O7—C22—C23 | 123.21 (12) | C56—C55—C54 | 113.16 (14) |
O7—C22—C21 | 114.35 (11) | C56—C55—H55A | 105.9 (14) |
C23—C22—C21 | 122.42 (11) | C54—C55—H55A | 110.9 (14) |
C22—C23—C26 | 115.74 (11) | C56—C55—H55B | 112.3 (14) |
C22—C23—C24 | 117.73 (11) | C54—C55—H55B | 104.6 (15) |
C26—C23—C24 | 126.51 (11) | H55A—C55—H55B | 110.0 (19) |
C16—C24—C25 | 117.50 (11) | C57—C56—C55 | 113.36 (17) |
C16—C24—C23 | 123.32 (11) | C57—C56—H56A | 112.8 (11) |
C25—C24—C23 | 119.18 (10) | C55—C56—H56A | 106.5 (11) |
C19—C25—C24 | 118.89 (11) | C57—C56—H56B | 106.2 (14) |
C19—C25—C20 | 120.45 (11) | C55—C56—H56B | 113.0 (14) |
C24—C25—C20 | 120.65 (11) | H56A—C56—H56B | 104.7 (18) |
O6—C26—C23 | 122.81 (13) | C58—C57—C56 | 114.92 (16) |
O6—C26—H26 | 119.8 (13) | C58—C57—H57A | 112.0 (11) |
C23—C26—H26 | 117.4 (13) | C56—C57—H57A | 108.2 (11) |
C20—C27—C29 | 110.03 (12) | C58—C57—H57B | 108.9 (13) |
C20—C27—C28 | 115.03 (12) | C56—C57—H57B | 110.5 (13) |
C29—C27—C28 | 111.15 (13) | H57A—C57—H57B | 101.5 (17) |
C20—C27—H27 | 108.1 (10) | C57—C58—C59 | 114.56 (14) |
C29—C27—H27 | 106.4 (10) | C57—C58—H58A | 109.6 (12) |
C28—C27—H27 | 105.7 (10) | C59—C58—H58A | 108.1 (12) |
C27—C28—H28A | 111.9 (11) | C57—C58—H58B | 112.9 (12) |
C27—C28—H28B | 109.9 (12) | C59—C58—H58B | 106.8 (12) |
H28A—C28—H28B | 111.2 (16) | H58A—C58—H58B | 104.4 (17) |
C27—C28—H28C | 108.2 (12) | C60—C59—C58 | 114.66 (16) |
H28A—C28—H28C | 107.5 (16) | C60—C59—H59A | 108.5 (11) |
H28B—C28—H28C | 107.9 (17) | C58—C59—H59A | 109.8 (12) |
C27—C29—H29A | 109.5 | C60—C59—H59B | 109.4 (13) |
C27—C29—H29B | 109.5 | C58—C59—H59B | 107.4 (13) |
H29A—C29—H29B | 109.5 | H59A—C59—H59B | 106.8 (17) |
C27—C29—H29C | 109.5 | C61—C60—C59 | 113.18 (15) |
H29A—C29—H29C | 109.5 | C61—C60—H60A | 109.4 (9) |
H29B—C29—H29C | 109.5 | C59—C60—H60A | 109.0 (10) |
C18—C30—H30A | 109.5 | C61—C60—H60B | 109.6 (12) |
C18—C30—H30B | 109.5 | C59—C60—H60B | 109.1 (12) |
H30A—C30—H30B | 109.5 | H60A—C60—H60B | 106.3 (15) |
C18—C30—H30C | 109.5 | C62—C61—C60 | 112.68 (13) |
H30A—C30—H30C | 109.5 | C62—C61—H61A | 108.3 (11) |
H30B—C30—H30C | 109.5 | C60—C61—H61A | 113.0 (11) |
O9—C31—C42 | 122.48 (14) | C62—C61—H61B | 111.9 (13) |
O9—C31—C32 | 120.64 (15) | C60—C61—H61B | 110.4 (14) |
C42—C31—C32 | 116.88 (13) | H61A—C61—H61B | 99.9 (17) |
C31—C32—C33 | 112.31 (13) | C51—C62—C61 | 114.94 (13) |
C31—C32—H32A | 107.1 (12) | C51—C62—H62A | 110.7 (11) |
C33—C32—H32A | 109.9 (12) | C61—C62—H62A | 110.0 (11) |
C31—C32—H32B | 107.8 (12) | C51—C62—H62B | 104.7 (11) |
C33—C32—H32B | 110.2 (11) | C61—C62—H62B | 110.5 (11) |
H32A—C32—H32B | 109.4 (16) | H62A—C62—H62B | 105.5 (16) |
O1—C1—C2—C3 | 179.86 (12) | C25—C20—C21—C22 | 6.37 (19) |
C9—C1—C2—C3 | 0.43 (19) | C27—C20—C21—C22 | −176.92 (12) |
O1—C1—C2—C17 | 1.43 (18) | O8—C21—C22—O7 | −3.28 (17) |
C9—C1—C2—C17 | −178.00 (11) | C20—C21—C22—O7 | 176.16 (12) |
C1—C2—C3—C4 | −0.96 (19) | O8—C21—C22—C23 | 178.24 (12) |
C17—C2—C3—C4 | 177.48 (12) | C20—C21—C22—C23 | −2.3 (2) |
C1—C2—C3—C15 | 178.69 (13) | O7—C22—C23—C26 | −2.94 (18) |
C17—C2—C3—C15 | −2.87 (19) | C21—C22—C23—C26 | 175.40 (12) |
C2—C3—C4—C10 | 1.0 (2) | O7—C22—C23—C24 | 178.79 (11) |
C15—C3—C4—C10 | −178.69 (14) | C21—C22—C23—C24 | −2.86 (18) |
C10—C5—C6—O4 | −173.66 (12) | O5—C16—C24—C25 | −179.52 (11) |
C12—C5—C6—O4 | 4.0 (2) | C17—C16—C24—C25 | −0.16 (17) |
C10—C5—C6—C7 | 7.51 (19) | O5—C16—C24—C23 | −0.68 (17) |
C12—C5—C6—C7 | −174.80 (12) | C17—C16—C24—C23 | 178.68 (11) |
C5—C6—C7—O3 | 174.46 (12) | C22—C23—C24—C16 | −175.13 (11) |
O4—C6—C7—O3 | −4.43 (18) | C26—C23—C24—C16 | 6.8 (2) |
C5—C6—C7—C8 | −4.0 (2) | C22—C23—C24—C25 | 3.68 (17) |
O4—C6—C7—C8 | 177.12 (12) | C26—C23—C24—C25 | −174.37 (12) |
O3—C7—C8—C11 | −2.5 (2) | C18—C19—C25—C24 | −0.14 (19) |
C6—C7—C8—C11 | 175.85 (13) | C18—C19—C25—C20 | −179.06 (12) |
O3—C7—C8—C9 | 179.33 (12) | C16—C24—C25—C19 | 0.31 (17) |
C6—C7—C8—C9 | −2.37 (19) | C23—C24—C25—C19 | −178.57 (11) |
O1—C1—C9—C10 | −179.34 (11) | C16—C24—C25—C20 | 179.23 (11) |
C2—C1—C9—C10 | 0.12 (18) | C23—C24—C25—C20 | 0.35 (17) |
O1—C1—C9—C8 | 0.05 (18) | C21—C20—C25—C19 | 173.53 (12) |
C2—C1—C9—C8 | 179.51 (12) | C27—C20—C25—C19 | −3.18 (18) |
C7—C8—C9—C1 | −174.63 (12) | C21—C20—C25—C24 | −5.37 (18) |
C11—C8—C9—C1 | 7.4 (2) | C27—C20—C25—C24 | 177.91 (12) |
C7—C8—C9—C10 | 4.74 (18) | C22—C23—C26—O6 | 5.3 (2) |
C11—C8—C9—C10 | −173.26 (13) | C24—C23—C26—O6 | −176.60 (13) |
C3—C4—C10—C9 | −0.40 (19) | C21—C20—C27—C29 | −81.66 (16) |
C3—C4—C10—C5 | −178.77 (12) | C25—C20—C27—C29 | 94.96 (15) |
C1—C9—C10—C4 | −0.14 (18) | C21—C20—C27—C28 | 44.78 (18) |
C8—C9—C10—C4 | −179.56 (11) | C25—C20—C27—C28 | −138.60 (13) |
C1—C9—C10—C5 | 178.21 (11) | O9—C31—C32—C33 | −110.88 (17) |
C8—C9—C10—C5 | −1.20 (18) | C42—C31—C32—C33 | 69.15 (19) |
C6—C5—C10—C4 | 173.41 (12) | C31—C32—C33—C34 | 60.0 (2) |
C12—C5—C10—C4 | −4.30 (18) | C32—C33—C34—C35 | −160.62 (15) |
C6—C5—C10—C9 | −4.93 (18) | C33—C34—C35—C36 | 75.7 (2) |
C12—C5—C10—C9 | 177.36 (12) | C34—C35—C36—C37 | 74.0 (2) |
C7—C8—C11—O2 | 3.9 (2) | C35—C36—C37—C38 | −160.00 (14) |
C9—C8—C11—O2 | −178.03 (14) | C36—C37—C38—C39 | 64.34 (19) |
C6—C5—C12—C13 | −86.01 (16) | C37—C38—C39—C40 | 64.0 (2) |
C10—C5—C12—C13 | 91.62 (15) | C38—C39—C40—C41 | −160.31 (15) |
C6—C5—C12—C14 | 40.87 (18) | C39—C40—C41—C42 | 72.10 (19) |
C10—C5—C12—C14 | −141.49 (13) | C40—C41—C42—C31 | 71.40 (18) |
O5—C16—C17—C18 | 179.15 (11) | O9—C31—C42—C41 | 14.9 (2) |
C24—C16—C17—C18 | −0.19 (18) | C32—C31—C42—C41 | −165.17 (13) |
O5—C16—C17—C2 | 2.61 (18) | O10—C51—C52—C53 | −109.20 (17) |
C24—C16—C17—C2 | −176.72 (11) | C62—C51—C52—C53 | 70.47 (18) |
C1—C2—C17—C16 | −99.92 (15) | C51—C52—C53—C54 | 61.67 (19) |
C1—C2—C17—C18 | 83.58 (16) | C52—C53—C54—C55 | −160.64 (15) |
C3—C2—C17—C16 | 81.65 (15) | C53—C54—C55—C56 | 71.7 (2) |
C3—C2—C17—C18 | −94.85 (15) | C54—C55—C56—C57 | 74.4 (2) |
C16—C17—C18—C19 | 0.37 (18) | C55—C56—C57—C58 | −159.30 (15) |
C2—C17—C18—C19 | 176.86 (12) | C56—C57—C58—C59 | 65.5 (2) |
C16—C17—C18—C30 | −179.75 (13) | C57—C58—C59—C60 | 65.9 (2) |
C2—C17—C18—C30 | −3.25 (19) | C58—C59—C60—C61 | −161.27 (14) |
C17—C18—C19—C25 | −0.21 (19) | C59—C60—C61—C62 | 69.47 (19) |
C30—C18—C19—C25 | 179.91 (13) | C60—C61—C62—C51 | 70.70 (18) |
C25—C20—C21—O8 | −174.22 (12) | O10—C51—C62—C61 | 15.3 (2) |
C27—C20—C21—O8 | 2.5 (2) | C52—C51—C62—C61 | −164.42 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O9 | 0.86 (2) | 1.96 (2) | 2.7451 (14) | 150 (2) |
O3—H103···O2 | 0.94 (3) | 1.57 (3) | 2.4700 (15) | 158 (2) |
O4—H104···O3 | 0.80 (3) | 2.08 (2) | 2.5904 (16) | 121 (2) |
O5—H105···O10 | 0.85 (2) | 1.99 (2) | 2.7272 (14) | 145 (2) |
O7—H107···O6 | 0.91 (3) | 1.63 (3) | 2.4598 (15) | 149 (3) |
O8—H108···O7 | 0.80 (2) | 2.05 (2) | 2.5935 (16) | 125 (2) |
Experimental details
Crystal data | |
Chemical formula | C30H30O8·2C12H22O |
Mr | 883.13 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 12.2640 (4), 14.4674 (4), 15.1532 (5) |
α, β, γ (°) | 82.108 (1), 89.206 (1), 66.264 (1) |
V (Å3) | 2435.32 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.6 × 0.5 × 0.4 |
Data collection | |
Diffractometer | CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS in SAINT; Bruker, 1998) |
Tmin, Tmax | 0.749, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 65791, 14038, 10049 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.701 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.163, 1.04 |
No. of reflections | 14038 |
No. of parameters | 851 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.29 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
C1—C2—C17—C16 | −99.92 (15) | C40—C41—C42—C31 | 71.40 (18) |
C1—C2—C17—C18 | 83.58 (16) | C32—C31—C42—C41 | −165.17 (13) |
C3—C2—C17—C16 | 81.65 (15) | C62—C51—C52—C53 | 70.47 (18) |
C3—C2—C17—C18 | −94.85 (15) | C51—C52—C53—C54 | 61.67 (19) |
C42—C31—C32—C33 | 69.15 (19) | C52—C53—C54—C55 | −160.64 (15) |
C31—C32—C33—C34 | 60.0 (2) | C53—C54—C55—C56 | 71.7 (2) |
C32—C33—C34—C35 | −160.62 (15) | C54—C55—C56—C57 | 74.4 (2) |
C33—C34—C35—C36 | 75.7 (2) | C55—C56—C57—C58 | −159.30 (15) |
C34—C35—C36—C37 | 74.0 (2) | C56—C57—C58—C59 | 65.5 (2) |
C35—C36—C37—C38 | −160.00 (14) | C57—C58—C59—C60 | 65.9 (2) |
C36—C37—C38—C39 | 64.34 (19) | C58—C59—C60—C61 | −161.27 (14) |
C37—C38—C39—C40 | 64.0 (2) | C59—C60—C61—C62 | 69.47 (19) |
C38—C39—C40—C41 | −160.31 (15) | C60—C61—C62—C51 | 70.70 (18) |
C39—C40—C41—C42 | 72.10 (19) | C52—C51—C62—C61 | −164.42 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O9 | 0.86 (2) | 1.96 (2) | 2.7451 (14) | 150 (2) |
O3—H103···O2 | 0.94 (3) | 1.57 (3) | 2.4700 (15) | 158 (2) |
O4—H104···O3 | 0.80 (3) | 2.08 (2) | 2.5904 (16) | 121 (2) |
O5—H105···O10 | 0.85 (2) | 1.99 (2) | 2.7272 (14) | 145 (2) |
O7—H107···O6 | 0.91 (3) | 1.63 (3) | 2.4598 (15) | 149 (3) |
O8—H108···O7 | 0.80 (2) | 2.05 (2) | 2.5935 (16) | 125 (2) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
Gossypol is a biologically active disesquiterpene found within the cotton plant and other members of the Malvaceae family. The compound is known to form inclusions complexes with many small molecular weight organic compounds. These complexes have been classified by Gdaniec et al. (1996) into 12 families on the basis of intermolecular hydrogen-bond and packing patterns. As part of a project to determine if gossypol would form complexes with larger molecules, experiments were conducted with cyclododecanone, and a structure was identified that represents a new family of gossypol inclusion complexes.
The complex contains two molecules of cyclododecanone per gossypol molecule (Figs. 1a and 1 b). No unusual bond lengths or valence angles were found. As is observed for most gossypol complexes, both halves of the gossypol moiety exist as aldehydes (Fig. 1a), and intramolecular hydrogen bonds are formed between the O3—H103···O2, O4—H104···O3, O7—H107···O6, and O8—H108···O7 atoms (Fig. 2). The naphthalene rings are approximately perpendicular, with an angle of 81.9° between the least-squares best-fit naphthalene planes. Both isopropyl moieties are orientated with the methyl groups pointing outward and away from the binaphthalene bridge.
Each cyclododecanone ring is characterized by a periodic ···gauche–gauche–trans··· arrangement of the ring torsion angles (Table 1), which results in a 'square' conformation (Figs. 1 b and 3). The distance between atoms along parallel sides of the square is \sim4.5 Å, and the distance between atoms across the diagonal is \sim5.5 Å (Fig. 2). A similar ring shape has been observed for crystalline cyclododecanone (Groth, 1979), cyclododecane (Dunitz and Shearer, 1960) and 2,12-dibromocyclododecanone (Dehli and Groth, 1969) and has been intrepreted as the solution conformation of cyclododecanone from NMR data (Anet et al., 1973; Rawdah, 1991).
In the gossypol complex, each cyclododecanone carbonyl group accepts a hydrogen bond from either the O1—H101 or the O5—H105 hydroxyl group of the gossypol molecule (Table 2 and Fig. 2). The cyclododecanone molecules are arranged such that the face of each ring is orientated parallel to the long axis of the gossypol group (parallel to the C2—C17 bond) and perpendicular to the planes of both naphthalene rings (Fig. 3).
There are no hydrogen-bond interactions between adjacent gossypol molecules, which is unusual among known gossypol complexes. The only other gossypol complex without direct gossypol-to-gossypol hydrogen bonds is gossypol–1,4-dioxane (1:3) (Ibragimov et al., 1993; Gdaniec et al., 1996). In this structure, two of the three dioxane molecules accept pairs of hydrogen bonds to form bridges between adjacent gossypol molecules. The gossypol–di-1,4-dioxane assemblies pack into a two-dimensional lattice. The third dioxane molecule sits in a channel formed within this lattice and interacts with the structure through van der Waals effects.
Within the gossypol–cyclododecanone complex, each cyclododecanone molecule accepts a single hydrogen bond from a host gossypol molecule, and no hydrogen-bond bridges are present. The gossypol molecules form a lattice that surrounds rectangular-shaped channels that run parallel to the c axis (Fig. 4). The channels are occupied by the cyclododecanone molecules, which are orientated with their faces perpendicular to the channel direction. Along the a direction, the chiral gossypol molecules separate into alternating enantiomorphic layers (Fig. 5), which interact only through van der Waals effects. Similar layering is also observed in gossypol inclusion compounds formed with small esters (Ibragimov et al., 1990; Gdaniec et al., 1996), although in these structures the gossypol molecules within enantiomorphic layers share hydrogen bonds.
In terms of guest size, the gossypol–cyclododecanone complex is the largest gossypol inclusion complex reported to date. The complex contains 26 non-H atoms of guest molecule per gossypol molecule. In comparison, the next highest gossypol-to-guest non-H-atom ratios are for gossypol–pyridine (1:3) gossypol–1,4-dioxane (1:3), and gossypol–tropolone (1:2), each of which contain 18 non-H atoms per gossypol molecule (Gdaniec et al., 1996; Talipov et al., 2002). The title complex is also the second example of gossypol forming an inclusion complex with a compound that is normally solid at room temperature.