The title compound, C30H52O2, crystallizes with two molecules in the asymmetric unit. The independent molecules differ in the conformation of the side chain attached to C17. Hydrogen bonds link the molecules in an infinite chain, graph-set C(8), parallel to the b axis.
Supporting information
CCDC reference: 180542
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.065
- wR factor = 0.137
- Data-to-parameter ratio = 10.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 6469
Count of symmetry unique reflns 6473
Completeness (_total/calc) 99.94%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
The synthesis of the title compound is described by Bastiaansen et al.
(1996). Crystals were obtained from n-hexane.
Due to a lack of significant anomalous scatterers, the absolute configuration
could not be determined ab initio. The chirality was chosen in
agreement with the well known stereochemistry of the cholesterol skeleton.
Only one Friedel pair was measured; these Friedel opposites were merged. The
hydroxyl H atoms were located in a difference Fourier map and their
coordinates were included as parameters in the refinement. The idealized H
atoms of each methyl moiety were included in rigid groups and were allowed to
rotate around the C—C bond. All other H atoms were included at calculated
positions, riding on their carrier atoms. Isotropic displacement parameters of
the H atoms were coupled to the equivalent isotropic displacement parameter of
their carrier atoms.
Data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PLATON.
Crystal data top
C30H52O2 | F(000) = 992 |
Mr = 444.72 | Least-squares Treatment of 25 SET4 setting angles (de Boer &
Duisenberg, 1984). |
Monoclinic, P21 | Dx = 1.096 Mg m−3 |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9017 (9) Å | Cell parameters from 25 reflections |
b = 12.0284 (10) Å | θ = 10.1–13.9° |
c = 18.8388 (11) Å | µ = 0.07 mm−1 |
β = 92.184 (5)° | T = 150 K |
V = 2695.0 (3) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.50 × 0.20 mm |
Data collection top
Enraf-Nonius CAD-4-Turbo diffractometer | Rint = 0.042 |
Radiation source: Rotating Anode | θmax = 27.5°, θmin = 1.7° |
Graphite monochromator | h = −10→15 |
ω scans with Δω=0.67+0.35 tan θ | k = 0→15 |
7483 measured reflections | l = −24→24 |
6469 independent reflections | 3 standard reflections every 60 min |
4258 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.15P] where P = (Fo2 + 2Fc2)/3 |
6469 reflections | (Δ/σ)max = 0.001 |
599 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Crystal data top
C30H52O2 | V = 2695.0 (3) Å3 |
Mr = 444.72 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.9017 (9) Å | µ = 0.07 mm−1 |
b = 12.0284 (10) Å | T = 150 K |
c = 18.8388 (11) Å | 0.50 × 0.50 × 0.20 mm |
β = 92.184 (5)° | |
Data collection top
Enraf-Nonius CAD-4-Turbo diffractometer | Rint = 0.042 |
7483 measured reflections | 3 standard reflections every 60 min |
6469 independent reflections | intensity decay: 2% |
4258 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.065 | 1 restraint |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.26 e Å−3 |
6469 reflections | Δρmin = −0.22 e Å−3 |
599 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.6970 (3) | 0.2377 (2) | −0.09412 (15) | 0.0376 (11) | |
O7 | 0.7817 (2) | −0.0651 (2) | 0.14793 (14) | 0.0262 (9) | |
C1 | 0.6725 (3) | 0.2995 (3) | 0.0842 (2) | 0.0210 (12) | |
C2 | 0.6264 (3) | 0.3227 (3) | 0.0087 (2) | 0.0238 (12) | |
C3 | 0.6465 (3) | 0.2266 (3) | −0.0397 (2) | 0.0226 (12) | |
C4 | 0.6017 (3) | 0.1148 (3) | −0.01599 (19) | 0.0207 (11) | |
C5 | 0.6415 (3) | 0.0969 (3) | 0.06343 (19) | 0.0195 (11) | |
C6 | 0.6013 (3) | −0.0124 (3) | 0.0944 (2) | 0.0244 (12) | |
C7 | 0.6660 (3) | −0.0466 (3) | 0.1634 (2) | 0.0238 (12) | |
C8 | 0.6657 (3) | 0.0483 (3) | 0.2186 (2) | 0.0197 (11) | |
C9 | 0.6928 (3) | 0.1632 (3) | 0.1854 (2) | 0.0193 (12) | |
C10 | 0.6238 (3) | 0.1929 (3) | 0.1164 (2) | 0.0187 (11) | |
C11 | 0.6878 (4) | 0.2541 (3) | 0.2416 (2) | 0.0299 (14) | |
C12 | 0.7637 (4) | 0.2332 (3) | 0.3075 (2) | 0.0294 (14) | |
C13 | 0.7391 (3) | 0.1208 (4) | 0.34140 (19) | 0.0235 (11) | |
C14 | 0.7479 (3) | 0.0314 (3) | 0.2827 (2) | 0.0226 (12) | |
C15 | 0.7518 (4) | −0.0778 (4) | 0.3245 (2) | 0.0301 (12) | |
C16 | 0.8205 (4) | −0.0483 (4) | 0.3928 (2) | 0.0330 (16) | |
C17 | 0.8292 (3) | 0.0799 (3) | 0.3964 (2) | 0.0249 (12) | |
C18 | 0.6224 (3) | 0.1200 (4) | 0.3731 (2) | 0.0347 (14) | |
C19 | 0.5000 (3) | 0.2128 (4) | 0.1331 (2) | 0.0287 (14) | |
C20 | 0.8271 (4) | 0.1230 (4) | 0.4738 (2) | 0.0356 (14) | |
C21 | 0.8306 (5) | 0.2509 (4) | 0.4780 (2) | 0.0497 (19) | |
C22 | 0.9274 (4) | 0.0746 (4) | 0.5177 (2) | 0.0373 (16) | |
C23 | 0.9328 (4) | 0.1020 (5) | 0.5960 (2) | 0.0408 (16) | |
C24 | 1.0376 (4) | 0.0571 (5) | 0.6341 (2) | 0.0441 (18) | |
C25 | 1.0600 (4) | 0.1008 (4) | 0.7095 (2) | 0.0382 (16) | |
C26 | 0.9690 (4) | 0.0676 (5) | 0.7590 (2) | 0.056 (2) | |
C27 | 1.1755 (4) | 0.0652 (6) | 0.7387 (3) | 0.069 (2) | |
C28 | 0.6513 (4) | 0.0241 (3) | −0.0621 (2) | 0.0275 (14) | |
C29 | 0.4727 (3) | 0.1157 (4) | −0.0305 (2) | 0.0296 (12) | |
C30 | 0.6115 (4) | −0.1531 (4) | 0.1889 (2) | 0.0359 (14) | |
O53 | 0.1765 (3) | 0.2166 (3) | −0.09155 (15) | 0.0404 (10) | |
O57 | 0.2714 (2) | −0.0562 (3) | 0.17580 (15) | 0.0315 (10) | |
C51 | 0.1817 (3) | 0.2996 (3) | 0.0854 (2) | 0.0223 (12) | |
C52 | 0.1286 (3) | 0.3168 (3) | 0.0109 (2) | 0.0237 (12) | |
C53 | 0.1361 (3) | 0.2143 (3) | −0.0334 (2) | 0.0235 (12) | |
C54 | 0.0915 (3) | 0.1075 (3) | −0.0018 (2) | 0.0224 (12) | |
C55 | 0.1385 (3) | 0.0971 (3) | 0.07693 (19) | 0.0200 (11) | |
C56 | 0.0950 (3) | −0.0041 (3) | 0.1160 (2) | 0.0240 (12) | |
C57 | 0.1555 (3) | −0.0276 (3) | 0.1874 (2) | 0.0251 (12) | |
C58 | 0.1594 (3) | 0.0763 (3) | 0.23514 (19) | 0.0212 (11) | |
C59 | 0.2068 (3) | 0.1748 (3) | 0.1920 (2) | 0.0210 (12) | |
C60 | 0.1321 (3) | 0.2011 (3) | 0.1245 (2) | 0.0210 (12) | |
C61 | 0.2374 (3) | 0.2798 (3) | 0.2353 (2) | 0.0233 (12) | |
C62 | 0.3018 (3) | 0.2555 (3) | 0.3047 (2) | 0.0237 (12) | |
C63 | 0.2389 (3) | 0.1734 (3) | 0.3496 (2) | 0.0223 (12) | |
C64 | 0.2270 (3) | 0.0641 (3) | 0.3061 (2) | 0.0233 (12) | |
C65 | 0.1873 (4) | −0.0197 (3) | 0.3617 (2) | 0.0287 (12) | |
C66 | 0.2443 (4) | 0.0176 (4) | 0.4325 (2) | 0.0313 (12) | |
C67 | 0.3018 (3) | 0.1304 (3) | 0.4180 (2) | 0.0259 (12) | |
C68 | 0.1245 (3) | 0.2218 (4) | 0.3684 (2) | 0.0276 (12) | |
C69 | 0.0118 (3) | 0.2317 (4) | 0.1462 (2) | 0.0270 (12) | |
C70 | 0.3071 (4) | 0.2060 (4) | 0.4842 (2) | 0.0293 (12) | |
C71 | 0.3699 (4) | 0.3143 (4) | 0.4718 (2) | 0.0357 (16) | |
C72 | 0.3544 (4) | 0.1469 (4) | 0.5507 (2) | 0.0333 (16) | |
C73 | 0.4769 (4) | 0.1090 (4) | 0.5482 (2) | 0.0390 (16) | |
C74 | 0.5228 (4) | 0.0633 (4) | 0.6188 (2) | 0.0466 (16) | |
C75 | 0.5318 (5) | 0.1456 (5) | 0.6801 (2) | 0.0485 (16) | |
C76 | 0.6084 (5) | 0.2433 (6) | 0.6640 (3) | 0.068 (3) | |
C77 | 0.5730 (6) | 0.0868 (6) | 0.7479 (3) | 0.090 (3) | |
C78 | 0.1326 (3) | 0.0102 (3) | −0.0462 (2) | 0.0258 (12) | |
C79 | −0.0379 (3) | 0.1123 (4) | −0.0090 (2) | 0.0285 (12) | |
C80 | 0.0958 (4) | −0.1277 (4) | 0.2197 (2) | 0.0402 (16) | |
H1A | 0.65490 | 0.36340 | 0.11500 | 0.0250* | |
H1B | 0.75530 | 0.29260 | 0.08360 | 0.0250* | |
H2A | 0.54470 | 0.33750 | 0.00980 | 0.0290* | |
H2B | 0.66320 | 0.38990 | −0.00990 | 0.0290* | |
H5 | 0.72500 | 0.08860 | 0.06200 | 0.0230* | |
H6A | 0.60940 | −0.07190 | 0.05860 | 0.0290* | |
H6B | 0.52040 | −0.00580 | 0.10410 | 0.0290* | |
H7D | 0.794 (4) | −0.126 (4) | 0.130 (2) | 0.0310* | |
H8 | 0.58820 | 0.05270 | 0.23710 | 0.0240* | |
H9 | 0.77300 | 0.15920 | 0.17170 | 0.0230* | |
H11A | 0.60920 | 0.26140 | 0.25640 | 0.0350* | |
H11B | 0.70950 | 0.32560 | 0.22000 | 0.0350* | |
H12A | 0.84340 | 0.23540 | 0.29420 | 0.0350* | |
H12B | 0.75220 | 0.29300 | 0.34260 | 0.0350* | |
H14 | 0.82470 | 0.04050 | 0.26370 | 0.0270* | |
H15A | 0.78940 | −0.13700 | 0.29750 | 0.0360* | |
H15B | 0.67520 | −0.10290 | 0.33550 | 0.0360* | |
H16A | 0.89640 | −0.08170 | 0.39180 | 0.0390* | |
H16B | 0.78250 | −0.07710 | 0.43490 | 0.0390* | |
H17 | 0.90400 | 0.10050 | 0.37790 | 0.0300* | |
H18A | 0.61050 | 0.04900 | 0.39710 | 0.0520* | |
H18B | 0.56480 | 0.12980 | 0.33500 | 0.0520* | |
H18C | 0.61720 | 0.18090 | 0.40740 | 0.0520* | |
H19A | 0.46990 | 0.14680 | 0.15620 | 0.0430* | |
H19B | 0.45660 | 0.22750 | 0.08880 | 0.0430* | |
H19C | 0.49460 | 0.27700 | 0.16490 | 0.0430* | |
H20 | 0.75610 | 0.09680 | 0.49510 | 0.0430* | |
H21A | 0.83110 | 0.27420 | 0.52780 | 0.0750* | |
H21B | 0.76410 | 0.28170 | 0.45270 | 0.0750* | |
H21C | 0.89870 | 0.27810 | 0.45600 | 0.0750* | |
H22A | 0.92580 | −0.00730 | 0.51260 | 0.0450* | |
H22B | 0.99750 | 0.10130 | 0.49680 | 0.0450* | |
H23A | 0.86580 | 0.07060 | 0.61830 | 0.0490* | |
H23B | 0.93060 | 0.18370 | 0.60190 | 0.0490* | |
H24A | 1.10320 | 0.07540 | 0.60550 | 0.0530* | |
H24B | 1.03180 | −0.02490 | 0.63620 | 0.0530* | |
H25 | 1.06000 | 0.18390 | 0.70690 | 0.0460* | |
H26A | 0.98410 | 0.10150 | 0.80570 | 0.0840* | |
H26B | 0.96790 | −0.01350 | 0.76390 | 0.0840* | |
H26C | 0.89590 | 0.09320 | 0.73960 | 0.0840* | |
H27A | 1.18880 | 0.09670 | 0.78630 | 0.1040* | |
H27B | 1.23330 | 0.09200 | 0.70720 | 0.1040* | |
H27C | 1.17870 | −0.01620 | 0.74150 | 0.1040* | |
H28A | 0.61560 | −0.04730 | −0.05190 | 0.0420* | |
H28B | 0.73240 | 0.01860 | −0.05170 | 0.0420* | |
H28C | 0.63770 | 0.04270 | −0.11240 | 0.0420* | |
H29A | 0.43830 | 0.05630 | −0.00310 | 0.0450* | |
H29B | 0.45600 | 0.10390 | −0.08120 | 0.0450* | |
H29C | 0.44220 | 0.18770 | −0.01620 | 0.0450* | |
H30A | 0.53640 | −0.13640 | 0.20570 | 0.0540* | |
H30B | 0.65780 | −0.18520 | 0.22780 | 0.0540* | |
H30C | 0.60510 | −0.20630 | 0.14960 | 0.0540* | |
H51A | 0.26350 | 0.28780 | 0.08150 | 0.0270* | |
H51B | 0.17100 | 0.36790 | 0.11370 | 0.0270* | |
H52A | 0.04860 | 0.33780 | 0.01490 | 0.0280* | |
H52B | 0.16740 | 0.37870 | −0.01270 | 0.0280* | |
H55 | 0.22080 | 0.08300 | 0.07280 | 0.0240* | |
H56A | 0.10220 | −0.07020 | 0.08520 | 0.0290* | |
H56B | 0.01400 | 0.00680 | 0.12400 | 0.0290* | |
H57D | 0.272 (4) | −0.114 (4) | 0.153 (3) | 0.0470* | |
H58 | 0.08020 | 0.09520 | 0.24640 | 0.0260* | |
H59 | 0.27960 | 0.14720 | 0.17380 | 0.0250* | |
H61A | 0.28330 | 0.32930 | 0.20610 | 0.0280* | |
H61B | 0.16740 | 0.32000 | 0.24580 | 0.0280* | |
H62A | 0.37660 | 0.22470 | 0.29440 | 0.0280* | |
H62B | 0.31350 | 0.32560 | 0.33150 | 0.0280* | |
H64 | 0.30470 | 0.04130 | 0.29400 | 0.0280* | |
H65A | 0.10440 | −0.01780 | 0.36450 | 0.0350* | |
H65B | 0.21070 | −0.09610 | 0.34950 | 0.0350* | |
H66A | 0.30070 | −0.03790 | 0.44910 | 0.0370* | |
H66B | 0.18780 | 0.02620 | 0.46930 | 0.0370* | |
H67 | 0.38100 | 0.11410 | 0.40540 | 0.0310* | |
H68A | 0.08820 | 0.17200 | 0.40170 | 0.0420* | |
H68B | 0.07680 | 0.22920 | 0.32510 | 0.0420* | |
H68C | 0.13550 | 0.29500 | 0.39040 | 0.0420* | |
H69A | 0.01610 | 0.27790 | 0.18910 | 0.0400* | |
H69B | −0.03020 | 0.16360 | 0.15580 | 0.0400* | |
H69C | −0.02650 | 0.27300 | 0.10760 | 0.0400* | |
H70 | 0.22780 | 0.22680 | 0.49400 | 0.0350* | |
H71A | 0.39380 | 0.34680 | 0.51760 | 0.0540* | |
H71B | 0.32020 | 0.36640 | 0.44580 | 0.0540* | |
H71C | 0.43610 | 0.29920 | 0.44390 | 0.0540* | |
H72A | 0.30720 | 0.08100 | 0.55950 | 0.0400* | |
H72B | 0.34760 | 0.19770 | 0.59170 | 0.0400* | |
H73A | 0.48280 | 0.05090 | 0.51130 | 0.0470* | |
H73B | 0.52380 | 0.17280 | 0.53420 | 0.0470* | |
H74A | 0.47400 | 0.00110 | 0.63290 | 0.0560* | |
H74B | 0.59850 | 0.03220 | 0.61150 | 0.0560* | |
H75 | 0.45490 | 0.17550 | 0.68800 | 0.0580* | |
H76A | 0.57320 | 0.28880 | 0.62620 | 0.1020* | |
H76B | 0.68090 | 0.21530 | 0.64870 | 0.1020* | |
H76C | 0.62020 | 0.28860 | 0.70690 | 0.1020* | |
H77A | 0.57980 | 0.14080 | 0.78670 | 0.1350* | |
H77B | 0.64640 | 0.05290 | 0.74040 | 0.1350* | |
H77C | 0.51900 | 0.02890 | 0.76000 | 0.1350* | |
H78A | 0.11160 | −0.06010 | −0.02390 | 0.0380* | |
H78B | 0.21460 | 0.01400 | −0.04900 | 0.0380* | |
H78C | 0.09790 | 0.01420 | −0.09420 | 0.0380* | |
H79A | −0.06470 | 0.17990 | 0.01400 | 0.0430* | |
H79B | −0.06980 | 0.04690 | 0.01390 | 0.0430* | |
H79C | −0.06150 | 0.11320 | −0.05940 | 0.0430* | |
H80A | 0.08500 | −0.18570 | 0.18350 | 0.0610* | |
H80B | 0.02250 | −0.10430 | 0.23640 | 0.0610* | |
H80C | 0.14170 | −0.15690 | 0.25970 | 0.0610* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.053 (2) | 0.0299 (18) | 0.0307 (17) | −0.0041 (16) | 0.0119 (15) | 0.0056 (14) |
O7 | 0.0294 (16) | 0.0225 (15) | 0.0266 (16) | 0.0089 (13) | −0.0010 (12) | −0.0045 (13) |
C1 | 0.022 (2) | 0.019 (2) | 0.022 (2) | 0.0007 (16) | −0.0005 (17) | −0.0002 (17) |
C2 | 0.028 (2) | 0.016 (2) | 0.027 (2) | −0.0018 (17) | −0.0024 (18) | 0.0047 (17) |
C3 | 0.024 (2) | 0.021 (2) | 0.022 (2) | 0.0005 (18) | −0.0105 (17) | 0.0014 (18) |
C4 | 0.022 (2) | 0.0176 (19) | 0.022 (2) | −0.0033 (17) | −0.0063 (16) | 0.0046 (17) |
C5 | 0.0155 (18) | 0.017 (2) | 0.026 (2) | −0.0035 (16) | 0.0002 (16) | 0.0015 (18) |
C6 | 0.026 (2) | 0.019 (2) | 0.028 (2) | −0.0061 (17) | −0.0015 (18) | 0.0024 (18) |
C7 | 0.026 (2) | 0.020 (2) | 0.025 (2) | −0.0053 (18) | −0.0035 (18) | 0.0017 (18) |
C8 | 0.0152 (18) | 0.019 (2) | 0.025 (2) | −0.0026 (16) | 0.0023 (16) | 0.0019 (17) |
C9 | 0.020 (2) | 0.016 (2) | 0.022 (2) | −0.0023 (16) | 0.0024 (17) | −0.0001 (16) |
C10 | 0.0133 (19) | 0.020 (2) | 0.023 (2) | 0.0023 (16) | 0.0014 (16) | −0.0005 (17) |
C11 | 0.041 (3) | 0.023 (2) | 0.025 (2) | 0.006 (2) | −0.0071 (19) | 0.0012 (19) |
C12 | 0.044 (3) | 0.020 (2) | 0.024 (2) | 0.001 (2) | −0.0011 (19) | −0.0049 (18) |
C13 | 0.025 (2) | 0.031 (2) | 0.0146 (19) | 0.0034 (19) | 0.0019 (16) | −0.0018 (18) |
C14 | 0.023 (2) | 0.023 (2) | 0.022 (2) | 0.0019 (18) | 0.0027 (17) | 0.0048 (17) |
C15 | 0.033 (2) | 0.033 (2) | 0.024 (2) | −0.006 (2) | −0.0031 (19) | 0.0041 (19) |
C16 | 0.035 (3) | 0.036 (3) | 0.028 (2) | −0.003 (2) | 0.000 (2) | 0.008 (2) |
C17 | 0.023 (2) | 0.030 (2) | 0.022 (2) | 0.0020 (18) | 0.0052 (17) | −0.0016 (18) |
C18 | 0.024 (2) | 0.056 (3) | 0.024 (2) | 0.007 (2) | 0.0005 (17) | 0.000 (2) |
C19 | 0.018 (2) | 0.037 (3) | 0.031 (2) | 0.0007 (19) | 0.0011 (17) | 0.003 (2) |
C20 | 0.035 (2) | 0.050 (3) | 0.022 (2) | 0.007 (2) | 0.0029 (19) | 0.000 (2) |
C21 | 0.072 (4) | 0.048 (3) | 0.028 (3) | 0.023 (3) | −0.013 (2) | −0.018 (2) |
C22 | 0.037 (3) | 0.054 (3) | 0.021 (2) | 0.003 (2) | 0.0013 (19) | 0.000 (2) |
C23 | 0.044 (3) | 0.054 (3) | 0.024 (2) | 0.009 (3) | −0.002 (2) | −0.002 (2) |
C24 | 0.044 (3) | 0.061 (4) | 0.027 (2) | 0.010 (3) | −0.001 (2) | 0.000 (2) |
C25 | 0.055 (3) | 0.034 (3) | 0.025 (2) | 0.003 (2) | −0.007 (2) | −0.002 (2) |
C26 | 0.064 (4) | 0.073 (4) | 0.031 (3) | 0.000 (3) | −0.003 (3) | 0.010 (3) |
C27 | 0.061 (4) | 0.112 (5) | 0.034 (3) | 0.015 (4) | −0.017 (3) | −0.008 (3) |
C28 | 0.040 (3) | 0.018 (2) | 0.024 (2) | 0.0012 (19) | −0.0051 (19) | −0.0012 (18) |
C29 | 0.025 (2) | 0.030 (2) | 0.033 (2) | −0.006 (2) | −0.0095 (18) | 0.002 (2) |
C30 | 0.051 (3) | 0.029 (2) | 0.027 (2) | −0.016 (2) | −0.008 (2) | 0.003 (2) |
O53 | 0.069 (2) | 0.0273 (17) | 0.0258 (16) | −0.0064 (16) | 0.0128 (15) | 0.0007 (14) |
O57 | 0.0364 (17) | 0.0221 (15) | 0.0357 (18) | 0.0082 (14) | −0.0045 (14) | −0.0054 (14) |
C51 | 0.023 (2) | 0.016 (2) | 0.028 (2) | −0.0033 (16) | 0.0017 (18) | 0.0012 (17) |
C52 | 0.022 (2) | 0.021 (2) | 0.028 (2) | 0.0000 (17) | −0.0005 (18) | 0.0001 (18) |
C53 | 0.025 (2) | 0.021 (2) | 0.024 (2) | 0.0004 (18) | −0.0067 (17) | 0.0024 (18) |
C54 | 0.022 (2) | 0.016 (2) | 0.029 (2) | 0.0016 (17) | −0.0027 (17) | 0.0023 (18) |
C55 | 0.0159 (18) | 0.020 (2) | 0.024 (2) | 0.0004 (16) | −0.0018 (16) | 0.0047 (18) |
C56 | 0.025 (2) | 0.021 (2) | 0.026 (2) | −0.0041 (17) | −0.0005 (18) | −0.0027 (18) |
C57 | 0.028 (2) | 0.017 (2) | 0.030 (2) | −0.0045 (17) | −0.0020 (18) | 0.0058 (18) |
C58 | 0.0195 (19) | 0.020 (2) | 0.024 (2) | 0.0000 (16) | −0.0003 (16) | 0.0080 (17) |
C59 | 0.021 (2) | 0.021 (2) | 0.021 (2) | −0.0016 (16) | −0.0003 (17) | 0.0023 (17) |
C60 | 0.015 (2) | 0.020 (2) | 0.028 (2) | 0.0011 (16) | 0.0019 (17) | 0.0038 (18) |
C61 | 0.026 (2) | 0.022 (2) | 0.022 (2) | 0.0002 (17) | 0.0034 (17) | 0.0006 (17) |
C62 | 0.025 (2) | 0.022 (2) | 0.024 (2) | −0.0050 (18) | 0.0012 (17) | 0.0013 (18) |
C63 | 0.021 (2) | 0.022 (2) | 0.024 (2) | 0.0043 (17) | 0.0029 (17) | −0.0010 (17) |
C64 | 0.021 (2) | 0.019 (2) | 0.030 (2) | 0.0001 (17) | 0.0018 (18) | 0.0038 (18) |
C65 | 0.034 (2) | 0.026 (2) | 0.026 (2) | −0.0006 (19) | 0.0010 (19) | 0.0069 (18) |
C66 | 0.038 (2) | 0.031 (2) | 0.025 (2) | 0.000 (2) | 0.0010 (19) | 0.004 (2) |
C67 | 0.030 (2) | 0.026 (2) | 0.022 (2) | 0.0062 (19) | 0.0040 (17) | 0.0025 (18) |
C68 | 0.023 (2) | 0.033 (2) | 0.027 (2) | 0.0027 (19) | 0.0027 (17) | −0.003 (2) |
C69 | 0.022 (2) | 0.027 (2) | 0.032 (2) | 0.0024 (18) | 0.0023 (17) | 0.0035 (19) |
C70 | 0.032 (2) | 0.031 (2) | 0.025 (2) | 0.000 (2) | 0.0036 (19) | −0.003 (2) |
C71 | 0.047 (3) | 0.035 (3) | 0.025 (2) | −0.004 (2) | 0.000 (2) | −0.007 (2) |
C72 | 0.043 (3) | 0.037 (3) | 0.020 (2) | 0.002 (2) | 0.0008 (19) | −0.0020 (19) |
C73 | 0.047 (3) | 0.044 (3) | 0.026 (2) | 0.008 (2) | 0.002 (2) | −0.008 (2) |
C74 | 0.058 (3) | 0.051 (3) | 0.030 (2) | 0.019 (3) | −0.009 (2) | −0.010 (2) |
C75 | 0.062 (3) | 0.059 (3) | 0.024 (2) | 0.016 (3) | −0.006 (2) | −0.004 (2) |
C76 | 0.062 (4) | 0.078 (5) | 0.064 (4) | −0.012 (4) | 0.002 (3) | −0.027 (4) |
C77 | 0.140 (6) | 0.091 (5) | 0.037 (3) | 0.022 (5) | −0.034 (4) | −0.004 (4) |
C78 | 0.026 (2) | 0.023 (2) | 0.028 (2) | 0.0015 (18) | −0.0037 (18) | 0.0027 (19) |
C79 | 0.026 (2) | 0.026 (2) | 0.033 (2) | −0.0021 (19) | −0.0068 (18) | −0.004 (2) |
C80 | 0.061 (3) | 0.025 (2) | 0.034 (3) | −0.013 (2) | −0.005 (2) | 0.005 (2) |
Geometric parameters (Å, º) top
O3—C3 | 1.215 (5) | C30—H30C | 0.9794 |
O7—C7 | 1.436 (4) | C30—H30B | 0.9793 |
O7—H7D | 0.82 (5) | C30—H30A | 0.9803 |
O53—C53 | 1.213 (5) | C51—C52 | 1.531 (5) |
O57—C57 | 1.446 (4) | C51—C60 | 1.526 (5) |
O57—H57D | 0.82 (5) | C52—C53 | 1.493 (5) |
C1—C10 | 1.541 (5) | C53—C54 | 1.520 (5) |
C1—C2 | 1.531 (5) | C54—C78 | 1.530 (5) |
C2—C3 | 1.497 (5) | C54—C79 | 1.542 (5) |
C3—C4 | 1.520 (5) | C54—C55 | 1.570 (5) |
C4—C29 | 1.549 (5) | C55—C56 | 1.523 (5) |
C4—C5 | 1.567 (5) | C55—C60 | 1.542 (5) |
C4—C28 | 1.527 (5) | C56—C57 | 1.528 (5) |
C5—C10 | 1.546 (5) | C57—C58 | 1.539 (5) |
C5—C6 | 1.523 (5) | C57—C80 | 1.536 (6) |
C6—C7 | 1.541 (5) | C58—C64 | 1.541 (5) |
C7—C8 | 1.544 (5) | C58—C59 | 1.555 (5) |
C7—C30 | 1.522 (6) | C59—C60 | 1.556 (5) |
C8—C14 | 1.538 (5) | C59—C61 | 1.540 (5) |
C8—C9 | 1.556 (5) | C60—C69 | 1.548 (5) |
C9—C10 | 1.553 (5) | C61—C62 | 1.519 (5) |
C9—C11 | 1.525 (5) | C62—C63 | 1.516 (5) |
C10—C19 | 1.537 (5) | C63—C67 | 1.554 (5) |
C11—C12 | 1.528 (6) | C63—C68 | 1.535 (5) |
C12—C13 | 1.528 (6) | C63—C64 | 1.553 (5) |
C13—C18 | 1.533 (5) | C64—C65 | 1.541 (5) |
C13—C14 | 1.549 (6) | C65—C66 | 1.540 (6) |
C13—C17 | 1.543 (5) | C66—C67 | 1.549 (6) |
C14—C15 | 1.531 (6) | C67—C70 | 1.543 (6) |
C15—C16 | 1.539 (6) | C70—C72 | 1.529 (6) |
C16—C17 | 1.547 (6) | C70—C71 | 1.524 (7) |
C17—C20 | 1.549 (5) | C72—C73 | 1.530 (7) |
C20—C22 | 1.540 (6) | C73—C74 | 1.521 (6) |
C20—C21 | 1.541 (7) | C74—C75 | 1.522 (6) |
C22—C23 | 1.510 (5) | C75—C76 | 1.525 (9) |
C23—C24 | 1.515 (7) | C75—C77 | 1.525 (8) |
C24—C25 | 1.528 (6) | C51—H51A | 0.9893 |
C25—C26 | 1.510 (6) | C51—H51B | 0.9902 |
C25—C27 | 1.522 (7) | C52—H52A | 0.9907 |
C1—H1A | 0.9902 | C52—H52B | 0.9904 |
C1—H1B | 0.9894 | C55—H55 | 1.0000 |
C2—H2B | 0.9898 | C56—H56A | 0.9899 |
C2—H2A | 0.9895 | C56—H56B | 0.9901 |
C5—H5 | 1.0002 | C58—H58 | 1.0002 |
C6—H6B | 0.9900 | C59—H59 | 1.0006 |
C6—H6A | 0.9906 | C61—H61A | 0.9892 |
C8—H8 | 0.9998 | C61—H61B | 0.9897 |
C9—H9 | 0.9994 | C62—H62A | 0.9903 |
C11—H11B | 0.9899 | C62—H62B | 0.9899 |
C11—H11A | 0.9902 | C64—H64 | 0.9992 |
C12—H12B | 0.9901 | C65—H65A | 0.9903 |
C12—H12A | 0.9906 | C65—H65B | 0.9898 |
C14—H14 | 1.0003 | C66—H66A | 0.9890 |
C15—H15B | 0.9898 | C66—H66B | 0.9895 |
C15—H15A | 0.9917 | C67—H67 | 1.0002 |
C16—H16B | 0.9904 | C68—H68A | 0.9796 |
C16—H16A | 0.9895 | C68—H68B | 0.9800 |
C17—H17 | 0.9995 | C68—H68C | 0.9798 |
C18—H18A | 0.9791 | C69—H69A | 0.9805 |
C18—H18C | 0.9803 | C69—H69B | 0.9800 |
C18—H18B | 0.9806 | C69—H69C | 0.9788 |
C19—H19C | 0.9810 | C70—H70 | 1.0004 |
C19—H19B | 0.9807 | C71—H71A | 0.9795 |
C19—H19A | 0.9797 | C71—H71B | 0.9800 |
C20—H20 | 1.0001 | C71—H71C | 0.9806 |
C21—H21C | 0.9805 | C72—H72A | 0.9892 |
C21—H21B | 0.9809 | C72—H72B | 0.9906 |
C21—H21A | 0.9789 | C73—H73A | 0.9901 |
C22—H22B | 0.9896 | C73—H73B | 0.9906 |
C22—H22A | 0.9899 | C74—H74A | 0.9896 |
C23—H23B | 0.9894 | C74—H74B | 0.9900 |
C23—H23A | 0.9902 | C75—H75 | 0.9998 |
C24—H24B | 0.9896 | C76—H76A | 0.9795 |
C24—H24A | 0.9901 | C76—H76B | 0.9798 |
C25—H25 | 1.0008 | C76—H76C | 0.9804 |
C26—H26C | 0.9803 | C77—H77A | 0.9789 |
C26—H26B | 0.9800 | C77—H77B | 0.9792 |
C26—H26A | 0.9801 | C77—H77C | 0.9804 |
C27—H27A | 0.9808 | C78—H78A | 0.9808 |
C27—H27C | 0.9812 | C78—H78B | 0.9804 |
C27—H27B | 0.9800 | C78—H78C | 0.9809 |
C28—H28B | 0.9798 | C79—H79A | 0.9804 |
C28—H28A | 0.9804 | C79—H79B | 0.9806 |
C28—H28C | 0.9811 | C79—H79C | 0.9799 |
C29—H29B | 0.9785 | C80—H80A | 0.9806 |
C29—H29C | 0.9807 | C80—H80B | 0.9799 |
C29—H29A | 0.9801 | C80—H80C | 0.9789 |
| | | |
C7—O7—H7D | 114 (3) | C7—C30—H30B | 109.49 |
C57—O57—H57D | 108 (3) | C52—C51—C60 | 113.2 (3) |
C2—C1—C10 | 113.0 (3) | C51—C52—C53 | 111.7 (3) |
C1—C2—C3 | 111.4 (3) | O53—C53—C54 | 122.0 (3) |
O3—C3—C4 | 122.4 (3) | C52—C53—C54 | 116.7 (3) |
C2—C3—C4 | 116.0 (3) | O53—C53—C52 | 121.3 (3) |
O3—C3—C2 | 121.6 (3) | C53—C54—C78 | 108.0 (3) |
C3—C4—C28 | 108.5 (3) | C53—C54—C79 | 107.2 (3) |
C3—C4—C29 | 107.4 (3) | C55—C54—C78 | 110.2 (3) |
C5—C4—C29 | 115.5 (3) | C55—C54—C79 | 113.9 (3) |
C28—C4—C29 | 107.9 (3) | C78—C54—C79 | 108.6 (3) |
C3—C4—C5 | 107.8 (3) | C53—C54—C55 | 108.7 (3) |
C5—C4—C28 | 109.6 (3) | C54—C55—C56 | 113.9 (3) |
C4—C5—C6 | 113.4 (3) | C56—C55—C60 | 110.0 (3) |
C6—C5—C10 | 110.2 (3) | C54—C55—C60 | 117.4 (3) |
C4—C5—C10 | 118.0 (3) | C55—C56—C57 | 114.6 (3) |
C5—C6—C7 | 113.5 (3) | O57—C57—C56 | 109.3 (3) |
O7—C7—C8 | 106.1 (3) | O57—C57—C58 | 105.9 (3) |
C6—C7—C8 | 110.9 (3) | C56—C57—C58 | 111.5 (3) |
C6—C7—C30 | 106.6 (3) | C56—C57—C80 | 106.5 (3) |
O7—C7—C30 | 110.9 (3) | O57—C57—C80 | 109.4 (3) |
O7—C7—C6 | 108.8 (3) | C58—C57—C80 | 114.2 (3) |
C8—C7—C30 | 113.4 (3) | C57—C58—C64 | 115.6 (3) |
C7—C8—C14 | 114.4 (3) | C59—C58—C64 | 109.8 (3) |
C9—C8—C14 | 107.3 (3) | C57—C58—C59 | 108.5 (3) |
C7—C8—C9 | 112.3 (3) | C58—C59—C61 | 115.6 (3) |
C8—C9—C11 | 110.1 (3) | C60—C59—C61 | 112.5 (3) |
C10—C9—C11 | 112.5 (3) | C58—C59—C60 | 112.0 (3) |
C8—C9—C10 | 115.5 (3) | C51—C60—C59 | 109.4 (3) |
C1—C10—C19 | 109.2 (3) | C51—C60—C69 | 108.8 (3) |
C5—C10—C9 | 106.7 (3) | C55—C60—C59 | 105.7 (3) |
C1—C10—C9 | 109.0 (3) | C55—C60—C69 | 114.4 (3) |
C9—C10—C19 | 110.2 (3) | C59—C60—C69 | 109.7 (3) |
C1—C10—C5 | 107.8 (3) | C51—C60—C55 | 108.7 (3) |
C5—C10—C19 | 113.8 (3) | C59—C61—C62 | 113.6 (3) |
C9—C11—C12 | 114.1 (3) | C61—C62—C63 | 111.2 (3) |
C11—C12—C13 | 111.6 (3) | C62—C63—C64 | 107.1 (3) |
C12—C13—C14 | 107.3 (3) | C62—C63—C68 | 110.1 (3) |
C12—C13—C18 | 111.1 (4) | C64—C63—C67 | 100.8 (3) |
C14—C13—C17 | 101.2 (3) | C64—C63—C68 | 112.3 (3) |
C17—C13—C18 | 110.7 (3) | C67—C63—C68 | 109.8 (3) |
C12—C13—C17 | 115.0 (3) | C62—C63—C67 | 116.5 (3) |
C14—C13—C18 | 111.1 (3) | C58—C64—C63 | 114.3 (3) |
C8—C14—C13 | 114.2 (3) | C58—C64—C65 | 119.2 (3) |
C8—C14—C15 | 121.5 (3) | C63—C64—C65 | 102.7 (3) |
C13—C14—C15 | 103.3 (3) | C64—C65—C66 | 105.2 (3) |
C14—C15—C16 | 103.7 (4) | C65—C66—C67 | 106.6 (3) |
C15—C16—C17 | 107.4 (3) | C63—C67—C66 | 103.6 (3) |
C13—C17—C20 | 119.3 (3) | C63—C67—C70 | 118.5 (3) |
C13—C17—C16 | 104.2 (3) | C66—C67—C70 | 112.2 (3) |
C16—C17—C20 | 111.8 (3) | C67—C70—C71 | 112.6 (3) |
C17—C20—C22 | 109.8 (3) | C67—C70—C72 | 113.0 (4) |
C21—C20—C22 | 109.3 (4) | C71—C70—C72 | 110.8 (4) |
C17—C20—C21 | 112.4 (3) | C70—C72—C73 | 115.8 (3) |
C20—C22—C23 | 116.4 (4) | C72—C73—C74 | 113.1 (3) |
C22—C23—C24 | 112.9 (4) | C73—C74—C75 | 116.2 (4) |
C23—C24—C25 | 115.4 (4) | C74—C75—C77 | 110.2 (5) |
C26—C25—C27 | 111.2 (4) | C76—C75—C77 | 110.4 (5) |
C24—C25—C26 | 112.3 (4) | C74—C75—C76 | 112.1 (4) |
C24—C25—C27 | 111.2 (4) | C52—C51—H51A | 108.92 |
C2—C1—H1A | 109.07 | C52—C51—H51B | 108.93 |
C10—C1—H1A | 108.91 | C60—C51—H51A | 108.93 |
C10—C1—H1B | 108.93 | C60—C51—H51B | 108.92 |
C2—C1—H1B | 109.06 | H51A—C51—H51B | 107.83 |
H1A—C1—H1B | 107.75 | C51—C52—H52A | 109.21 |
C1—C2—H2B | 109.27 | C51—C52—H52B | 109.26 |
C3—C2—H2A | 109.37 | C53—C52—H52A | 109.33 |
C3—C2—H2B | 109.38 | C53—C52—H52B | 109.33 |
H2A—C2—H2B | 108.00 | H52A—C52—H52B | 107.96 |
C1—C2—H2A | 109.34 | C54—C55—H55 | 104.76 |
C4—C5—H5 | 104.63 | C56—C55—H55 | 104.71 |
C6—C5—H5 | 104.55 | C60—C55—H55 | 104.65 |
C10—C5—H5 | 104.59 | C55—C56—H56A | 108.66 |
C5—C6—H6B | 108.87 | C55—C56—H56B | 108.57 |
C7—C6—H6A | 108.84 | C57—C56—H56A | 108.61 |
C5—C6—H6A | 108.83 | C57—C56—H56B | 108.63 |
H6A—C6—H6B | 107.71 | H56A—C56—H56B | 107.58 |
C7—C6—H6B | 108.90 | C57—C58—H58 | 107.50 |
C7—C8—H8 | 107.44 | C59—C58—H58 | 107.54 |
C14—C8—H8 | 107.51 | C64—C58—H58 | 107.63 |
C9—C8—H8 | 107.53 | C58—C59—H59 | 105.22 |
C10—C9—H9 | 105.95 | C60—C59—H59 | 105.23 |
C11—C9—H9 | 106.07 | C61—C59—H59 | 105.27 |
C8—C9—H9 | 106.00 | C59—C61—H61A | 108.88 |
C9—C11—H11A | 108.75 | C59—C61—H61B | 108.83 |
C12—C11—H11A | 108.75 | C62—C61—H61A | 108.86 |
C12—C11—H11B | 108.75 | C62—C61—H61B | 108.85 |
C9—C11—H11B | 108.66 | H61A—C61—H61B | 107.70 |
H11A—C11—H11B | 107.63 | C61—C62—H62A | 109.35 |
C11—C12—H12B | 109.30 | C61—C62—H62B | 109.37 |
C13—C12—H12A | 109.26 | C63—C62—H62A | 109.41 |
C11—C12—H12A | 109.40 | C63—C62—H62B | 109.45 |
H12A—C12—H12B | 107.91 | H62A—C62—H62B | 107.97 |
C13—C12—H12B | 109.27 | C58—C64—H64 | 106.58 |
C8—C14—H14 | 105.49 | C63—C64—H64 | 106.63 |
C15—C14—H14 | 105.53 | C65—C64—H64 | 106.62 |
C13—C14—H14 | 105.49 | C64—C65—H65A | 110.67 |
C14—C15—H15B | 111.05 | C64—C65—H65B | 110.68 |
C16—C15—H15A | 111.01 | C66—C65—H65A | 110.73 |
C14—C15—H15A | 110.95 | C66—C65—H65B | 110.67 |
H15A—C15—H15B | 109.00 | H65A—C65—H65B | 108.87 |
C16—C15—H15B | 111.07 | C65—C66—H66A | 110.40 |
C15—C16—H16A | 110.29 | C65—C66—H66B | 110.40 |
C17—C16—H16A | 110.24 | C67—C66—H66A | 110.37 |
C17—C16—H16B | 110.21 | C67—C66—H66B | 110.41 |
H16A—C16—H16B | 108.56 | H66A—C66—H66B | 108.68 |
C15—C16—H16B | 110.15 | C63—C67—H67 | 107.28 |
C16—C17—H17 | 106.91 | C66—C67—H67 | 107.27 |
C20—C17—H17 | 106.97 | C70—C67—H67 | 107.31 |
C13—C17—H17 | 106.99 | C63—C68—H68A | 109.43 |
C13—C18—H18B | 109.43 | C63—C68—H68B | 109.47 |
C13—C18—H18C | 109.45 | C63—C68—H68C | 109.46 |
H18A—C18—H18B | 109.48 | H68A—C68—H68B | 109.45 |
H18A—C18—H18C | 109.48 | H68A—C68—H68C | 109.49 |
H18B—C18—H18C | 109.43 | H68B—C68—H68C | 109.53 |
C13—C18—H18A | 109.55 | C60—C69—H69A | 109.43 |
C10—C19—H19A | 109.53 | C60—C69—H69B | 109.47 |
C10—C19—H19B | 109.38 | C60—C69—H69C | 109.49 |
H19A—C19—H19B | 109.54 | H69A—C69—H69B | 109.42 |
H19A—C19—H19C | 109.45 | H69A—C69—H69C | 109.44 |
C10—C19—H19C | 109.46 | H69B—C69—H69C | 109.57 |
H19B—C19—H19C | 109.46 | C67—C70—H70 | 106.67 |
C21—C20—H20 | 108.40 | C71—C70—H70 | 106.63 |
C22—C20—H20 | 108.35 | C72—C70—H70 | 106.59 |
C17—C20—H20 | 108.45 | C70—C71—H71A | 109.49 |
C20—C21—H21B | 109.41 | C70—C71—H71B | 109.45 |
C20—C21—H21C | 109.43 | C70—C71—H71C | 109.42 |
C20—C21—H21A | 109.52 | H71A—C71—H71B | 109.54 |
H21A—C21—H21C | 109.55 | H71A—C71—H71C | 109.50 |
H21B—C21—H21C | 109.47 | H71B—C71—H71C | 109.42 |
H21A—C21—H21B | 109.44 | C70—C72—H72A | 108.43 |
C20—C22—H22A | 108.20 | C70—C72—H72B | 108.28 |
C20—C22—H22B | 108.16 | C73—C72—H72A | 108.32 |
C23—C22—H22B | 108.22 | C73—C72—H72B | 108.30 |
H22A—C22—H22B | 107.32 | H72A—C72—H72B | 107.45 |
C23—C22—H22A | 108.17 | C72—C73—H73A | 108.97 |
C22—C23—H23B | 109.03 | C72—C73—H73B | 108.94 |
C24—C23—H23A | 108.96 | C74—C73—H73A | 109.03 |
C24—C23—H23B | 109.01 | C74—C73—H73B | 109.00 |
H23A—C23—H23B | 107.82 | H73A—C73—H73B | 107.71 |
C22—C23—H23A | 109.03 | C73—C74—H74A | 108.24 |
C23—C24—H24A | 108.36 | C73—C74—H74B | 108.27 |
C23—C24—H24B | 108.47 | C75—C74—H74A | 108.25 |
C25—C24—H24B | 108.39 | C75—C74—H74B | 108.25 |
H24A—C24—H24B | 107.52 | H74A—C74—H74B | 107.35 |
C25—C24—H24A | 108.42 | C74—C75—H75 | 107.98 |
C26—C25—H25 | 107.20 | C76—C75—H75 | 108.06 |
C27—C25—H25 | 107.27 | C77—C75—H75 | 108.01 |
C24—C25—H25 | 107.36 | C75—C76—H76A | 109.44 |
C25—C26—H26B | 109.51 | C75—C76—H76B | 109.48 |
C25—C26—H26C | 109.51 | C75—C76—H76C | 109.41 |
C25—C26—H26A | 109.46 | H76A—C76—H76B | 109.59 |
H26A—C26—H26C | 109.50 | H76A—C76—H76C | 109.43 |
H26B—C26—H26C | 109.45 | H76B—C76—H76C | 109.48 |
H26A—C26—H26B | 109.41 | C75—C77—H77A | 109.42 |
C25—C27—H27A | 109.50 | C75—C77—H77B | 109.42 |
C25—C27—H27C | 109.44 | C75—C77—H77C | 109.36 |
H27A—C27—H27B | 109.51 | H77A—C77—H77B | 109.59 |
C25—C27—H27B | 109.49 | H77A—C77—H77C | 109.51 |
H27B—C27—H27C | 109.52 | H77B—C77—H77C | 109.52 |
H27A—C27—H27C | 109.38 | C54—C78—H78A | 109.48 |
C4—C28—H28B | 109.49 | C54—C78—H78B | 109.48 |
C4—C28—H28C | 109.47 | C54—C78—H78C | 109.54 |
C4—C28—H28A | 109.54 | H78A—C78—H78B | 109.49 |
H28A—C28—H28C | 109.41 | H78A—C78—H78C | 109.39 |
H28B—C28—H28C | 109.48 | H78B—C78—H78C | 109.46 |
H28A—C28—H28B | 109.43 | C54—C79—H79A | 109.44 |
C4—C29—H29B | 109.53 | C54—C79—H79B | 109.48 |
C4—C29—H29C | 109.41 | C54—C79—H79C | 109.52 |
H29A—C29—H29B | 109.57 | H79A—C79—H79B | 109.45 |
H29A—C29—H29C | 109.43 | H79A—C79—H79C | 109.45 |
H29B—C29—H29C | 109.43 | H79B—C79—H79C | 109.49 |
C4—C29—H29A | 109.45 | C57—C80—H80A | 109.43 |
C7—C30—H30A | 109.53 | C57—C80—H80B | 109.46 |
C7—C30—H30C | 109.46 | C57—C80—H80C | 109.47 |
H30A—C30—H30B | 109.46 | H80A—C80—H80B | 109.45 |
H30A—C30—H30C | 109.41 | H80A—C80—H80C | 109.55 |
H30B—C30—H30C | 109.48 | H80B—C80—H80C | 109.48 |
| | | |
C2—C1—C10—C9 | 168.3 (3) | C60—C51—C52—C53 | −55.5 (4) |
C2—C1—C10—C5 | 52.8 (4) | C52—C51—C60—C55 | 53.2 (4) |
C2—C1—C10—C19 | −71.3 (4) | C52—C51—C60—C59 | 168.2 (3) |
C10—C1—C2—C3 | −56.4 (4) | C52—C51—C60—C69 | −71.9 (4) |
C1—C2—C3—C4 | 55.2 (4) | C51—C52—C53—C54 | 52.9 (4) |
C1—C2—C3—O3 | −123.8 (4) | C51—C52—C53—O53 | −126.7 (4) |
O3—C3—C4—C29 | −105.0 (4) | O53—C53—C54—C79 | −103.7 (4) |
C2—C3—C4—C5 | −49.2 (4) | O53—C53—C54—C78 | 13.2 (5) |
C2—C3—C4—C29 | 75.9 (4) | C52—C53—C54—C79 | 76.7 (4) |
O3—C3—C4—C5 | 129.9 (4) | C52—C53—C54—C55 | −46.8 (4) |
C2—C3—C4—C28 | −167.8 (3) | C52—C53—C54—C78 | −166.4 (3) |
O3—C3—C4—C28 | 11.3 (5) | O53—C53—C54—C55 | 132.8 (4) |
C28—C4—C5—C10 | 166.4 (3) | C78—C54—C55—C60 | 164.6 (3) |
C29—C4—C5—C6 | 59.5 (4) | C79—C54—C55—C56 | 57.6 (4) |
C29—C4—C5—C10 | −71.5 (4) | C79—C54—C55—C60 | −73.0 (4) |
C3—C4—C5—C6 | 179.5 (3) | C78—C54—C55—C56 | −64.8 (4) |
C28—C4—C5—C6 | −62.6 (4) | C53—C54—C55—C56 | 177.1 (3) |
C3—C4—C5—C10 | 48.5 (4) | C53—C54—C55—C60 | 46.4 (4) |
C6—C5—C10—C1 | 176.6 (3) | C54—C55—C56—C57 | 169.3 (3) |
C4—C5—C6—C7 | 163.4 (3) | C54—C55—C60—C69 | 71.3 (4) |
C4—C5—C10—C19 | 70.2 (4) | C56—C55—C60—C51 | 177.1 (3) |
C6—C5—C10—C9 | 59.6 (4) | C56—C55—C60—C59 | 59.7 (4) |
C6—C5—C10—C19 | −62.2 (4) | C56—C55—C60—C69 | −61.1 (4) |
C4—C5—C10—C1 | −51.0 (4) | C60—C55—C56—C57 | −56.5 (4) |
C4—C5—C10—C9 | −168.0 (3) | C54—C55—C60—C51 | −50.5 (4) |
C10—C5—C6—C7 | −61.8 (4) | C54—C55—C60—C59 | −167.9 (3) |
C5—C6—C7—O7 | −63.3 (4) | C55—C56—C57—O57 | −64.9 (4) |
C5—C6—C7—C30 | 177.1 (3) | C55—C56—C57—C58 | 51.9 (4) |
C5—C6—C7—C8 | 53.1 (4) | C55—C56—C57—C80 | 177.0 (3) |
C6—C7—C8—C14 | −168.0 (3) | C56—C57—C58—C64 | −175.3 (3) |
C6—C7—C8—C9 | −45.4 (4) | C80—C57—C58—C59 | −172.3 (3) |
C30—C7—C8—C9 | −165.3 (3) | C80—C57—C58—C64 | 63.9 (4) |
O7—C7—C8—C14 | −50.0 (4) | C56—C57—C58—C59 | −51.5 (4) |
O7—C7—C8—C9 | 72.7 (4) | O57—C57—C58—C59 | 67.3 (3) |
C30—C7—C8—C14 | 72.1 (4) | O57—C57—C58—C64 | −56.4 (4) |
C7—C8—C9—C10 | 49.5 (4) | C57—C58—C59—C60 | 60.4 (4) |
C7—C8—C14—C13 | −174.3 (3) | C57—C58—C64—C63 | 174.4 (3) |
C7—C8—C14—C15 | −49.4 (5) | C57—C58—C64—C65 | −63.7 (4) |
C9—C8—C14—C13 | 60.3 (4) | C59—C58—C64—C63 | 51.3 (4) |
C9—C8—C14—C15 | −174.8 (3) | C59—C58—C64—C65 | 173.2 (3) |
C14—C8—C9—C11 | −55.2 (4) | C64—C58—C59—C61 | −41.8 (4) |
C7—C8—C9—C11 | 178.2 (3) | C57—C58—C59—C61 | −169.0 (3) |
C14—C8—C9—C10 | 176.1 (3) | C64—C58—C59—C60 | −172.4 (3) |
C11—C9—C10—C5 | 177.2 (3) | C58—C59—C60—C51 | 178.9 (3) |
C10—C9—C11—C12 | −174.4 (3) | C61—C59—C60—C55 | 163.7 (3) |
C11—C9—C10—C19 | −58.8 (4) | C61—C59—C60—C69 | −72.5 (4) |
C8—C9—C11—C12 | 55.3 (4) | C58—C59—C61—C62 | 44.7 (4) |
C11—C9—C10—C1 | 61.0 (4) | C60—C59—C61—C62 | 175.0 (3) |
C8—C9—C10—C19 | 68.7 (4) | C58—C59—C60—C55 | −64.2 (4) |
C8—C9—C10—C1 | −171.4 (3) | C58—C59—C60—C69 | 59.6 (4) |
C8—C9—C10—C5 | −55.3 (4) | C61—C59—C60—C51 | 46.8 (4) |
C9—C11—C12—C13 | −55.4 (5) | C59—C61—C62—C63 | −54.6 (4) |
C11—C12—C13—C18 | −67.6 (4) | C61—C62—C63—C67 | 173.0 (3) |
C11—C12—C13—C17 | 165.7 (3) | C61—C62—C63—C68 | −61.2 (4) |
C11—C12—C13—C14 | 54.1 (4) | C61—C62—C63—C64 | 61.1 (4) |
C12—C13—C14—C15 | 166.3 (3) | C62—C63—C64—C65 | 167.8 (3) |
C17—C13—C14—C8 | 179.5 (3) | C68—C63—C64—C58 | 59.3 (4) |
C12—C13—C14—C8 | −59.6 (4) | C67—C63—C64—C58 | 176.1 (3) |
C14—C13—C17—C16 | −36.5 (4) | C67—C63—C64—C65 | 45.5 (3) |
C18—C13—C17—C16 | 81.4 (4) | C62—C63—C64—C58 | −61.6 (4) |
C18—C13—C17—C20 | −44.2 (5) | C64—C63—C67—C66 | −40.6 (3) |
C14—C13—C17—C20 | −162.0 (3) | C64—C63—C67—C70 | −165.7 (3) |
C12—C13—C17—C16 | −151.7 (3) | C68—C63—C67—C66 | 78.0 (4) |
C12—C13—C17—C20 | 82.7 (4) | C68—C63—C67—C70 | −47.1 (4) |
C18—C13—C14—C15 | −72.1 (4) | C68—C63—C64—C65 | −71.3 (4) |
C17—C13—C14—C15 | 45.4 (4) | C62—C63—C67—C66 | −156.0 (3) |
C18—C13—C14—C8 | 61.9 (4) | C62—C63—C67—C70 | 78.8 (4) |
C13—C14—C15—C16 | −36.2 (4) | C63—C64—C65—C66 | −33.0 (4) |
C8—C14—C15—C16 | −166.0 (3) | C58—C64—C65—C66 | −160.6 (3) |
C14—C15—C16—C17 | 13.2 (4) | C64—C65—C66—C67 | 7.6 (4) |
C15—C16—C17—C13 | 14.8 (4) | C65—C66—C67—C70 | 149.8 (4) |
C15—C16—C17—C20 | 145.0 (4) | C65—C66—C67—C63 | 20.8 (4) |
C13—C17—C20—C21 | −55.7 (5) | C63—C67—C70—C71 | −62.7 (5) |
C13—C17—C20—C22 | −177.7 (4) | C63—C67—C70—C72 | 170.8 (3) |
C16—C17—C20—C21 | −177.6 (4) | C66—C67—C70—C71 | 176.5 (4) |
C16—C17—C20—C22 | 60.5 (5) | C66—C67—C70—C72 | 49.9 (5) |
C17—C20—C22—C23 | −175.7 (4) | C71—C70—C72—C73 | −63.3 (5) |
C21—C20—C22—C23 | 60.6 (5) | C67—C70—C72—C73 | 64.2 (5) |
C20—C22—C23—C24 | −176.5 (4) | C70—C72—C73—C74 | 173.2 (4) |
C22—C23—C24—C25 | 168.4 (4) | C72—C73—C74—C75 | −64.9 (6) |
C23—C24—C25—C26 | 63.5 (6) | C73—C74—C75—C76 | −59.6 (6) |
C23—C24—C25—C27 | −171.2 (5) | C73—C74—C75—C77 | 177.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7D···O53i | 0.82 (5) | 2.06 (5) | 2.883 (4) | 176 (4) |
O57—H57D···O3i | 0.82 (5) | 2.14 (5) | 2.949 (4) | 171 (5) |
C5—H5···O7 | 1.00 | 2.53 | 2.985 (4) | 107 |
C59—H59···O57 | 1.00 | 2.45 | 2.902 (5) | 107 |
C64—H64···O57 | 1.00 | 2.54 | 2.915 (5) | 102 |
Symmetry code: (i) −x+1, y−1/2, −z. |
Experimental details
Crystal data |
Chemical formula | C30H52O2 |
Mr | 444.72 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 150 |
a, b, c (Å) | 11.9017 (9), 12.0284 (10), 18.8388 (11) |
β (°) | 92.184 (5) |
V (Å3) | 2695.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.50 × 0.50 × 0.20 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4-Turbo diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7483, 6469, 4258 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.137, 1.04 |
No. of reflections | 6469 |
No. of parameters | 599 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.22 |
Selected bond lengths (Å) topO3—C3 | 1.215 (5) | O53—C53 | 1.213 (5) |
O7—C7 | 1.436 (4) | O57—C57 | 1.446 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7D···O53i | 0.82 (5) | 2.06 (5) | 2.883 (4) | 176 (4) |
O57—H57D···O3i | 0.82 (5) | 2.14 (5) | 2.949 (4) | 171 (5) |
Symmetry code: (i) −x+1, y−1/2, −z. |
The structure determination of the title compound, (I), was carried out to confirm that the 7-hydroxy group is located on the α side of the steroid molecule (Bastiaansen et al., 1996).
The asymmetric unit of the crystal structure contains two molecules of the title compound (Fig. 1). The crystallographically independent molecules differ only in the conformation of the aliphatic side chain attached to C17 (C57 in molecule 2) of the steroid skeleton. In molecule 1 (atoms C1–C30), the side chain is fully extended (all torsion angles anti), whereas in molecule 2 (atoms C51–C80), the torsion angles of the chain C63—C67—C70—C72—C73—C74—C75—C77 (substract 50 from the numbers in these atom labels to obtain the standard cholesterol numbering scheme) adopt the conformations anti, +gauche, anti, -gauche and anti.
The orientation of the hydroxyl group is identical in both molecules. Hydrogen bonds (Table 2) link the molecules into an infinite chain parallel to the b axis. The chain can be described with grap- set symbol C(8) (Bernstein et al., 1995).