Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023310/ob6197sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023310/ob6197Isup2.hkl |
CCDC reference: 204669
The title compound, (I), was obtained by the reduction of tetrahydropyran-4-one with aluminium isopropoxide in propan-2-ol. The white solid was seperated by chromatography over silica gel and eluted with a hexane–dichloromethane mixture (1:10). Diffraction quality crystals of (I) were obtained by recrystallization from a dichloromethane–hexane mixture.
The H atoms of the hydroxyl groups were located from a difference Fourier map and their positions refined. The O—H distances were computed to be 0.84 (4) and 0.81 (3) Å. H atoms attached to C atoms were included in calculated positions, with displacement parameters fixed at 1.2 Ueq of their carrier atoms. The displacement paramaters of the H atoms of both the hydroxyl groups were fixed at 1.5Ueq of the respective O atoms during the refinement.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C19H20Cl2O2 | Least Squares Treatment of 25 SET4 setting angles. |
Mr = 351.25 | Dx = 1.273 Mg m−3 |
Monoclinic, P21/c | Melting point = 385–387 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 12.1315 (9) Å | Cell parameters from 25 reflections |
b = 11.7075 (19) Å | θ = 2–12° |
c = 26.177 (3) Å | µ = 0.36 mm−1 |
β = 99.728 (9)° | T = 298 K |
V = 3664.4 (8) Å3 | Plate, colourless |
Z = 8 | 0.2 × 0.2 × 0.1 mm |
F(000) = 1472 |
Enraf-Nonius CAD-4 diffractometer | 6670 independent reflections |
Radiation source: Rotating Anode | 5034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 18.4 pixels mm-1 | θmax = 25.3°, θmin = 1.6° |
ω–2θ scans | h = 0→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.650, Tmax = 0.999 | l = −31→31 |
7004 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.059P)2 + 2.0872P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6670 reflections | Δρmax = 0.50 e Å−3 |
423 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (5) |
C19H20Cl2O2 | V = 3664.4 (8) Å3 |
Mr = 351.25 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1315 (9) Å | µ = 0.36 mm−1 |
b = 11.7075 (19) Å | T = 298 K |
c = 26.177 (3) Å | 0.2 × 0.2 × 0.1 mm |
β = 99.728 (9)° |
Enraf-Nonius CAD-4 diffractometer | 6670 independent reflections |
Absorption correction: ψ scan (North et al., 1968) | 5034 reflections with I > 2σ(I) |
Tmin = 0.650, Tmax = 0.999 | Rint = 0.027 |
7004 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.50 e Å−3 |
6670 reflections | Δρmin = −0.42 e Å−3 |
423 parameters |
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. The asymmetric unit of the cell consists of two molecules with a total number of forty six non-hydrogen atoms which were anisotropically refined using the atomic scattering factors given in SHELX97 program. 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.02403 (7) | 0.24421 (7) | 0.04077 (4) | 0.0910 (3) | |
Cl2 | −0.15982 (8) | 1.11554 (10) | 0.23664 (4) | 0.1022 (4) | |
O1 | 0.14094 (14) | 0.75809 (15) | 0.12199 (7) | 0.0593 (6) | |
O8 | 0.40284 (16) | 0.84165 (17) | 0.10508 (7) | 0.0621 (6) | |
C2 | 0.2128 (2) | 0.6886 (2) | 0.09728 (10) | 0.0538 (8) | |
C3 | 0.3254 (2) | 0.6690 (2) | 0.13324 (10) | 0.0556 (8) | |
C4 | 0.3763 (2) | 0.7852 (2) | 0.15023 (9) | 0.0549 (8) | |
C5 | 0.2959 (2) | 0.8563 (2) | 0.17540 (10) | 0.0564 (8) | |
C6 | 0.1848 (2) | 0.8685 (2) | 0.13763 (10) | 0.0569 (8) | |
C7 | 0.4056 (2) | 0.5941 (3) | 0.10994 (13) | 0.0743 (11) | |
C9 | 0.3463 (3) | 0.9709 (3) | 0.19462 (12) | 0.0735 (11) | |
C10 | 0.1512 (2) | 0.5784 (2) | 0.08245 (10) | 0.0537 (8) | |
C11 | 0.1649 (2) | 0.5199 (2) | 0.03837 (10) | 0.0580 (9) | |
C12 | 0.1122 (2) | 0.4166 (2) | 0.02515 (11) | 0.0621 (9) | |
C13 | 0.0444 (2) | 0.3728 (2) | 0.05701 (12) | 0.0622 (9) | |
C14 | 0.0273 (2) | 0.4293 (3) | 0.10073 (13) | 0.0723 (11) | |
C15 | 0.0809 (2) | 0.5322 (3) | 0.11344 (12) | 0.0686 (10) | |
C16 | 0.0964 (2) | 0.9299 (2) | 0.16086 (10) | 0.0588 (9) | |
C17 | 0.0759 (3) | 1.0454 (3) | 0.15234 (14) | 0.0817 (11) | |
C18 | −0.0018 (3) | 1.1027 (3) | 0.17596 (15) | 0.0875 (15) | |
C19 | −0.0600 (2) | 1.0448 (3) | 0.20757 (12) | 0.0715 (11) | |
C20 | −0.0434 (3) | 0.9301 (3) | 0.21627 (12) | 0.0734 (11) | |
C21 | 0.0344 (2) | 0.8741 (3) | 0.19265 (12) | 0.0689 (10) | |
Cl1A | 0.22632 (11) | −0.05643 (9) | 0.32117 (5) | 0.1159 (5) | |
Cl2A | 0.67787 (10) | 0.87250 (9) | 0.28889 (4) | 0.1027 (4) | |
O1A | 0.39797 (14) | 0.47094 (14) | 0.39463 (6) | 0.0520 (6) | |
O8A | 0.32641 (19) | 0.53403 (18) | 0.51305 (7) | 0.0702 (7) | |
C2A | 0.3376 (2) | 0.3978 (2) | 0.42491 (9) | 0.0516 (8) | |
C3A | 0.2300 (2) | 0.4586 (2) | 0.43397 (10) | 0.0603 (9) | |
C4A | 0.2649 (2) | 0.5679 (2) | 0.46384 (10) | 0.0634 (9) | |
C5A | 0.3338 (2) | 0.6438 (2) | 0.43421 (10) | 0.0599 (9) | |
C6A | 0.4338 (2) | 0.5766 (2) | 0.42098 (9) | 0.0519 (8) | |
C7A | 0.1525 (3) | 0.3855 (3) | 0.46030 (13) | 0.0795 (11) | |
C9A | 0.3719 (3) | 0.7534 (3) | 0.46327 (13) | 0.0855 (13) | |
C10A | 0.3156 (2) | 0.2847 (2) | 0.39789 (10) | 0.0554 (8) | |
C11A | 0.3178 (3) | 0.1855 (3) | 0.42650 (11) | 0.0676 (10) | |
C12A | 0.2899 (3) | 0.0807 (3) | 0.40329 (13) | 0.0768 (11) | |
C13A | 0.2615 (3) | 0.0753 (3) | 0.35068 (13) | 0.0746 (12) | |
C14A | 0.2614 (3) | 0.1718 (3) | 0.32099 (12) | 0.0805 (11) | |
C15A | 0.2885 (3) | 0.2760 (3) | 0.34460 (10) | 0.0689 (10) | |
C16A | 0.4976 (2) | 0.6448 (2) | 0.38693 (9) | 0.0519 (8) | |
C17A | 0.6024 (2) | 0.6884 (2) | 0.40598 (10) | 0.0621 (9) | |
C18A | 0.6578 (3) | 0.7581 (3) | 0.37607 (12) | 0.0714 (11) | |
C19A | 0.6092 (3) | 0.7834 (2) | 0.32650 (11) | 0.0688 (10) | |
C20A | 0.5064 (3) | 0.7400 (3) | 0.30615 (11) | 0.0750 (11) | |
C21A | 0.4512 (2) | 0.6711 (3) | 0.33634 (10) | 0.0669 (10) | |
H2 | 0.22650 | 0.72720 | 0.06570 | 0.0650* | |
H3 | 0.30940 | 0.63020 | 0.16430 | 0.0670* | |
H4 | 0.44520 | 0.77350 | 0.17520 | 0.0660* | |
H5 | 0.28040 | 0.81400 | 0.20570 | 0.0680* | |
H6 | 0.19830 | 0.91040 | 0.10690 | 0.0680* | |
H8 | 0.463 (3) | 0.878 (3) | 0.1121 (14) | 0.1010* | |
H11 | 0.21090 | 0.55070 | 0.01680 | 0.0700* | |
H12 | 0.12280 | 0.37790 | −0.00470 | 0.0750* | |
H14 | −0.02000 | 0.39880 | 0.12170 | 0.0870* | |
H15 | 0.06940 | 0.57080 | 0.14320 | 0.0820* | |
H17 | 0.11510 | 1.08520 | 0.13040 | 0.0980* | |
H18 | −0.01400 | 1.18040 | 0.17020 | 0.1050* | |
H20 | −0.08390 | 0.89060 | 0.23780 | 0.0880* | |
H21 | 0.04540 | 0.79630 | 0.19840 | 0.0830* | |
H71 | 0.47340 | 0.58470 | 0.13450 | 0.1110* | |
H72 | 0.42240 | 0.62940 | 0.07900 | 0.1110* | |
H73 | 0.37200 | 0.52080 | 0.10150 | 0.1110* | |
H91 | 0.29300 | 1.01310 | 0.21040 | 0.1100* | |
H92 | 0.36490 | 1.01350 | 0.16590 | 0.1100* | |
H93 | 0.41260 | 0.95830 | 0.21970 | 0.1100* | |
H2A | 0.38480 | 0.38450 | 0.45860 | 0.0620* | |
H3A | 0.18860 | 0.48070 | 0.40000 | 0.0720* | |
H4A | 0.19780 | 0.60950 | 0.46930 | 0.0760* | |
H5A | 0.28640 | 0.66520 | 0.40150 | 0.0720* | |
H6A | 0.48420 | 0.55840 | 0.45330 | 0.0620* | |
H8A | 0.332 (3) | 0.585 (3) | 0.5343 (13) | 0.0900* | |
H11A | 0.33850 | 0.18900 | 0.46230 | 0.0810* | |
H12A | 0.29050 | 0.01500 | 0.42330 | 0.0920* | |
H14A | 0.24320 | 0.16710 | 0.28510 | 0.0970* | |
H15A | 0.28850 | 0.34120 | 0.32430 | 0.0820* | |
H17A | 0.63620 | 0.67050 | 0.43960 | 0.0750* | |
H18A | 0.72780 | 0.78760 | 0.38970 | 0.0860* | |
H20A | 0.47390 | 0.75680 | 0.27220 | 0.0900* | |
H21A | 0.38130 | 0.64180 | 0.32240 | 0.0800* | |
H71A | 0.13280 | 0.31770 | 0.44020 | 0.1190* | |
H72A | 0.08600 | 0.42790 | 0.46300 | 0.1190* | |
H73A | 0.18980 | 0.36460 | 0.49430 | 0.1190* | |
H91A | 0.41540 | 0.79800 | 0.44320 | 0.1280* | |
H92A | 0.41660 | 0.73480 | 0.49610 | 0.1280* | |
H93A | 0.30760 | 0.79650 | 0.46890 | 0.1280* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0801 (5) | 0.0643 (5) | 0.1260 (7) | −0.0307 (4) | 0.0096 (5) | −0.0023 (5) |
Cl2 | 0.0810 (6) | 0.1165 (8) | 0.1065 (7) | 0.0215 (5) | 0.0084 (5) | −0.0355 (6) |
O1 | 0.0544 (10) | 0.0557 (10) | 0.0674 (11) | −0.0073 (8) | 0.0093 (8) | −0.0041 (9) |
O8 | 0.0633 (11) | 0.0690 (12) | 0.0549 (10) | −0.0235 (9) | 0.0130 (9) | 0.0100 (9) |
C2 | 0.0550 (14) | 0.0504 (14) | 0.0569 (14) | −0.0083 (11) | 0.0119 (11) | 0.0055 (11) |
C3 | 0.0521 (14) | 0.0548 (15) | 0.0601 (15) | −0.0071 (11) | 0.0101 (11) | 0.0129 (12) |
C4 | 0.0549 (14) | 0.0589 (15) | 0.0495 (13) | −0.0129 (12) | 0.0051 (11) | 0.0120 (12) |
C5 | 0.0635 (15) | 0.0562 (15) | 0.0495 (13) | −0.0160 (12) | 0.0095 (11) | 0.0092 (12) |
C6 | 0.0648 (16) | 0.0517 (14) | 0.0542 (14) | −0.0084 (12) | 0.0098 (12) | 0.0077 (12) |
C7 | 0.0589 (17) | 0.0654 (18) | 0.099 (2) | −0.0033 (14) | 0.0148 (16) | 0.0051 (17) |
C9 | 0.082 (2) | 0.0678 (18) | 0.0711 (18) | −0.0237 (16) | 0.0140 (15) | −0.0006 (15) |
C10 | 0.0502 (13) | 0.0523 (14) | 0.0585 (14) | −0.0090 (11) | 0.0089 (11) | 0.0065 (12) |
C11 | 0.0549 (14) | 0.0547 (15) | 0.0665 (16) | −0.0099 (12) | 0.0162 (12) | 0.0048 (13) |
C12 | 0.0591 (16) | 0.0557 (15) | 0.0718 (17) | −0.0061 (13) | 0.0120 (13) | −0.0035 (13) |
C13 | 0.0495 (14) | 0.0521 (15) | 0.0818 (19) | −0.0103 (12) | 0.0021 (13) | 0.0059 (14) |
C14 | 0.0660 (17) | 0.0715 (19) | 0.084 (2) | −0.0208 (15) | 0.0261 (15) | 0.0102 (16) |
C15 | 0.0708 (18) | 0.0689 (18) | 0.0702 (17) | −0.0169 (15) | 0.0234 (14) | −0.0004 (15) |
C16 | 0.0641 (16) | 0.0532 (15) | 0.0579 (15) | −0.0035 (12) | 0.0066 (12) | 0.0019 (12) |
C17 | 0.098 (2) | 0.0628 (19) | 0.087 (2) | −0.0037 (17) | 0.0236 (19) | 0.0137 (17) |
C18 | 0.100 (3) | 0.0566 (18) | 0.106 (3) | 0.0126 (18) | 0.018 (2) | −0.0014 (18) |
C19 | 0.0617 (17) | 0.078 (2) | 0.0700 (18) | 0.0044 (15) | −0.0029 (14) | −0.0165 (16) |
C20 | 0.0662 (18) | 0.078 (2) | 0.077 (2) | −0.0013 (16) | 0.0150 (15) | −0.0009 (16) |
C21 | 0.0718 (18) | 0.0594 (17) | 0.0770 (19) | −0.0017 (14) | 0.0167 (15) | 0.0112 (14) |
Cl1A | 0.1483 (10) | 0.0920 (7) | 0.1186 (8) | −0.0418 (7) | 0.0546 (7) | −0.0428 (6) |
Cl2A | 0.1416 (9) | 0.0872 (6) | 0.0903 (6) | −0.0260 (6) | 0.0513 (6) | −0.0007 (5) |
O1A | 0.0570 (10) | 0.0522 (10) | 0.0480 (9) | 0.0117 (8) | 0.0123 (7) | −0.0012 (8) |
O8A | 0.0983 (15) | 0.0662 (13) | 0.0471 (10) | 0.0292 (11) | 0.0149 (10) | 0.0000 (9) |
C2A | 0.0515 (13) | 0.0585 (15) | 0.0445 (12) | 0.0122 (11) | 0.0076 (10) | 0.0052 (11) |
C3A | 0.0521 (14) | 0.0737 (18) | 0.0557 (14) | 0.0218 (13) | 0.0106 (11) | 0.0101 (13) |
C4A | 0.0661 (16) | 0.0662 (17) | 0.0611 (16) | 0.0332 (14) | 0.0196 (13) | 0.0103 (13) |
C5A | 0.0677 (16) | 0.0573 (15) | 0.0562 (14) | 0.0282 (13) | 0.0147 (12) | 0.0079 (12) |
C6A | 0.0588 (14) | 0.0508 (14) | 0.0449 (12) | 0.0161 (11) | 0.0053 (11) | −0.0010 (11) |
C7A | 0.0643 (18) | 0.095 (2) | 0.083 (2) | 0.0153 (17) | 0.0231 (16) | 0.0096 (18) |
C9A | 0.113 (3) | 0.0608 (18) | 0.091 (2) | 0.0255 (18) | 0.041 (2) | −0.0074 (17) |
C10A | 0.0517 (14) | 0.0630 (16) | 0.0519 (14) | 0.0085 (12) | 0.0100 (11) | 0.0004 (12) |
C11A | 0.0807 (19) | 0.0675 (18) | 0.0566 (15) | 0.0035 (15) | 0.0176 (14) | 0.0025 (14) |
C12A | 0.093 (2) | 0.0638 (18) | 0.079 (2) | −0.0050 (16) | 0.0298 (17) | 0.0030 (16) |
C13A | 0.076 (2) | 0.077 (2) | 0.076 (2) | −0.0107 (16) | 0.0274 (16) | −0.0162 (17) |
C14A | 0.096 (2) | 0.088 (2) | 0.0563 (16) | −0.0019 (19) | 0.0096 (16) | −0.0124 (17) |
C15A | 0.083 (2) | 0.0708 (19) | 0.0519 (15) | 0.0074 (15) | 0.0089 (14) | 0.0019 (14) |
C16A | 0.0613 (15) | 0.0481 (13) | 0.0457 (12) | 0.0163 (11) | 0.0071 (11) | −0.0022 (11) |
C17A | 0.0704 (17) | 0.0625 (16) | 0.0508 (14) | 0.0049 (14) | 0.0029 (13) | −0.0048 (13) |
C18A | 0.078 (2) | 0.0689 (19) | 0.0671 (18) | −0.0087 (15) | 0.0116 (15) | −0.0139 (15) |
C19A | 0.092 (2) | 0.0562 (16) | 0.0628 (17) | 0.0001 (15) | 0.0260 (16) | −0.0028 (13) |
C20A | 0.088 (2) | 0.083 (2) | 0.0534 (15) | 0.0078 (18) | 0.0100 (15) | 0.0139 (15) |
C21A | 0.0646 (17) | 0.079 (2) | 0.0541 (15) | 0.0040 (15) | 0.0013 (13) | 0.0092 (14) |
Cl1—C13 | 1.737 (3) | C14—H14 | 0.9298 |
Cl2—C19 | 1.744 (3) | C15—H15 | 0.9313 |
Cl1A—C13A | 1.745 (4) | C17—H17 | 0.9303 |
Cl2A—C19A | 1.740 (3) | C18—H18 | 0.9298 |
O1—C6 | 1.431 (3) | C20—H20 | 0.9308 |
O1—C2 | 1.425 (3) | C21—H21 | 0.9291 |
O8—C4 | 1.437 (3) | C2A—C3A | 1.540 (3) |
O8—H8 | 0.84 (4) | C2A—C10A | 1.504 (3) |
O1A—C2A | 1.447 (3) | C3A—C7A | 1.520 (4) |
O1A—C6A | 1.447 (3) | C3A—C4A | 1.522 (3) |
O8A—C4A | 1.431 (3) | C4A—C5A | 1.520 (3) |
O8A—H8A | 0.81 (3) | C5A—C9A | 1.523 (4) |
C2—C10 | 1.509 (3) | C5A—C6A | 1.534 (3) |
C2—C3 | 1.540 (4) | C6A—C16A | 1.505 (3) |
C3—C7 | 1.513 (4) | C10A—C11A | 1.380 (4) |
C3—C4 | 1.529 (3) | C10A—C15A | 1.382 (4) |
C4—C5 | 1.515 (3) | C11A—C12A | 1.385 (5) |
C5—C6 | 1.538 (4) | C12A—C13A | 1.363 (5) |
C5—C9 | 1.524 (4) | C13A—C14A | 1.371 (5) |
C6—C16 | 1.502 (3) | C14A—C15A | 1.382 (5) |
C10—C11 | 1.376 (4) | C16A—C21A | 1.383 (4) |
C10—C15 | 1.383 (4) | C16A—C17A | 1.383 (3) |
C11—C12 | 1.384 (3) | C17A—C18A | 1.381 (4) |
C12—C13 | 1.366 (4) | C18A—C19A | 1.364 (4) |
C13—C14 | 1.368 (4) | C19A—C20A | 1.368 (5) |
C14—C15 | 1.383 (5) | C20A—C21A | 1.379 (4) |
C16—C17 | 1.386 (4) | C2A—H2A | 0.9794 |
C16—C21 | 1.377 (4) | C3A—H3A | 0.9793 |
C17—C18 | 1.385 (5) | C4A—H4A | 0.9796 |
C18—C19 | 1.357 (5) | C5A—H5A | 0.9799 |
C19—C20 | 1.371 (5) | C6A—H6A | 0.9799 |
C20—C21 | 1.378 (5) | C7A—H71A | 0.9600 |
C2—H2 | 0.9806 | C7A—H72A | 0.9600 |
C3—H3 | 0.9790 | C7A—H73A | 0.9595 |
C4—H4 | 0.9798 | C9A—H91A | 0.9596 |
C5—H5 | 0.9799 | C9A—H92A | 0.9605 |
C6—H6 | 0.9793 | C9A—H93A | 0.9611 |
C7—H72 | 0.9613 | C11A—H11A | 0.9292 |
C7—H73 | 0.9597 | C12A—H12A | 0.9299 |
C7—H71 | 0.9609 | C14A—H14A | 0.9297 |
C9—H93 | 0.9598 | C15A—H15A | 0.9301 |
C9—H92 | 0.9603 | C17A—H17A | 0.9299 |
C9—H91 | 0.9608 | C18A—H18A | 0.9302 |
C11—H11 | 0.9310 | C20A—H20A | 0.9303 |
C12—H12 | 0.9308 | C21A—H21A | 0.9302 |
Cl1···C4Ai | 3.563 (3) | H3···C15 | 3.0864 |
Cl1···C7Aii | 3.585 (4) | H3···H5 | 2.4612 |
Cl1···H4Ai | 2.6102 | H3A···H5A | 2.4616 |
Cl2···H21iii | 2.9153 | H3A···C18i | 3.0994 |
Cl2···H21Aiii | 2.8808 | H3A···C19i | 3.0727 |
Cl2A···H15Aiv | 3.0803 | H4···H20A | 2.5116 |
O1A···O8v | 2.850 (3) | H4···H71 | 2.5022 |
O8···O8Avi | 2.833 (3) | H4···H93 | 2.5199 |
O8···O1Aiv | 2.850 (3) | H4A···H72A | 2.5122 |
O8A···C6Avii | 3.380 (3) | H4A···H93A | 2.5636 |
O8A···C17Avii | 3.377 (3) | H4A···Cl1iii | 2.6102 |
O8A···O8viii | 2.833 (3) | H5···C21 | 3.0288 |
O1···H21 | 2.5155 | H5···H3 | 2.4612 |
O1···H15 | 2.4561 | H5A···C21A | 2.8397 |
O1A···H15A | 2.5756 | H5A···H3A | 2.4616 |
O1A···H21A | 2.7364 | H5A···H21A | 2.5482 |
O1A···H8v | 2.04 (4) | H6···O8 | 2.6167 |
O8···H92 | 2.6537 | H6···H2 | 2.4505 |
O8···H8Avi | 2.09 (3) | H6···H17 | 2.4073 |
O8···H72 | 2.5984 | H6A···O8Avii | 2.5577 |
O8···H6 | 2.6167 | H6A···H2A | 2.3822 |
O8···H2 | 2.5864 | H6A···O8A | 2.6840 |
O8A···H2A | 2.4371 | H6A···H17A | 2.3398 |
O8A···H73A | 2.5782 | H6A···H92A | 2.5502 |
O8A···H92A | 2.6614 | H8···H92 | 2.5461 |
O8A···H17Avii | 2.6992 | H8···C9 | 2.98 (4) |
O8A···H6A | 2.6840 | H8···C6Aiv | 2.84 (4) |
O8A···H6Avii | 2.5577 | H8···O1Aiv | 2.04 (4) |
C4A···Cl1iii | 3.563 (3) | H8···C2Aiv | 2.76 (4) |
C6A···O8Avii | 3.380 (3) | H8···C10Aiv | 2.95 (4) |
C7···C11 | 3.308 (4) | H8···H8Avi | 2.40 (5) |
C7A···Cl1ix | 3.585 (4) | H8A···C9A | 2.81 (3) |
C7A···C11A | 3.299 (5) | H8A···O8viii | 2.09 (3) |
C9···C17 | 3.394 (5) | H8A···H8viii | 2.40 (5) |
C9···C21Aiv | 3.586 (5) | H8A···H92A | 2.3401 |
C9A···C17A | 3.473 (4) | H11···H2 | 2.4212 |
C11···C7 | 3.308 (4) | H11···H93Avi | 2.5779 |
C11···C13x | 3.481 (4) | H11A···H2A | 2.3626 |
C11···C12x | 3.568 (4) | H15···O1 | 2.4561 |
C11A···C7A | 3.299 (5) | H15A···O1A | 2.5756 |
C12···C12x | 3.427 (4) | H15A···Cl2Av | 3.0803 |
C12···C13x | 3.596 (4) | H17···H6 | 2.4073 |
C12···C11x | 3.568 (4) | H17A···O8Avii | 2.6992 |
C13···C12x | 3.596 (4) | H17A···H6A | 2.3398 |
C13···C11x | 3.481 (4) | H17A···H73Avii | 2.5267 |
C17···C9 | 3.394 (5) | H18A···C12iv | 3.0911 |
C17A···O8Avii | 3.377 (3) | H18A···C13iv | 3.0455 |
C17A···C9A | 3.473 (4) | H20A···H4 | 2.5116 |
C21A···C9v | 3.586 (5) | H21···O1 | 2.5155 |
C2A···H8v | 2.76 (4) | H21···Cl2i | 2.9153 |
C5A···H21A | 3.0772 | H21A···O1A | 2.7364 |
C6A···H8v | 2.84 (4) | H21A···Cl2i | 2.8808 |
C9···H8 | 2.98 (4) | H21A···C5A | 3.0772 |
C9A···H8A | 2.81 (3) | H21A···H5A | 2.5482 |
C10···H73 | 2.7253 | H71···H4 | 2.5022 |
C10A···H8v | 2.95 (4) | H71A···C10A | 2.6691 |
C10A···H71A | 2.6691 | H71A···C11A | 2.7988 |
C11···H73 | 2.7641 | H72···O8 | 2.5984 |
C11A···H71A | 2.7988 | H72A···H4A | 2.5122 |
C12···H18Av | 3.0911 | H73···C10 | 2.7253 |
C13···H18Av | 3.0455 | H73···C11 | 2.7641 |
C15···H3 | 3.0864 | H73A···O8A | 2.5782 |
C16···H91 | 2.6970 | H73A···H17Avii | 2.5267 |
C16A···H92v | 2.7996 | H91···C16 | 2.6970 |
C16A···H91A | 2.6225 | H91···C17 | 2.8349 |
C17···H91 | 2.8349 | H91A···C16A | 2.6225 |
C17A···H92v | 2.8536 | H91A···C17A | 2.9136 |
C17A···H91A | 2.9136 | H92···O8 | 2.6537 |
C18···H3Aiii | 3.0994 | H92···H8 | 2.5461 |
C18A···H92v | 3.0629 | H92···C16Aiv | 2.7996 |
C19···H3Aiii | 3.0727 | H92···C17Aiv | 2.8536 |
C21···H5 | 3.0288 | H92···C18Aiv | 3.0629 |
C21A···H5A | 2.8397 | H92···C21Aiv | 2.9033 |
C21A···H92v | 2.9033 | H92A···H8A | 2.3401 |
H2···H6 | 2.4505 | H92A···O8A | 2.6614 |
H2···H11 | 2.4212 | H92A···H6A | 2.5502 |
H2···O8 | 2.5864 | H93···H4 | 2.5199 |
H2A···O8A | 2.4371 | H93A···H4A | 2.5636 |
H2A···H6A | 2.3822 | H93A···H11viii | 2.5779 |
H2A···H11A | 2.3626 | ||
C2—O1—C6 | 114.78 (18) | C20—C21—H21 | 118.95 |
C4—O8—H8 | 111 (2) | C16—C21—H21 | 119.00 |
C2A—O1A—C6A | 112.57 (17) | O1A—C2A—C3A | 109.36 (19) |
C4A—O8A—H8A | 113 (2) | C3A—C2A—C10A | 113.1 (2) |
C3—C2—C10 | 112.3 (2) | O1A—C2A—C10A | 109.24 (19) |
O1—C2—C3 | 110.8 (2) | C2A—C3A—C4A | 107.4 (2) |
O1—C2—C10 | 106.90 (19) | C4A—C3A—C7A | 112.3 (2) |
C4—C3—C7 | 112.2 (2) | C2A—C3A—C7A | 114.5 (2) |
C2—C3—C7 | 113.9 (2) | O8A—C4A—C5A | 111.9 (2) |
C2—C3—C4 | 108.56 (19) | C3A—C4A—C5A | 111.0 (2) |
C3—C4—C5 | 110.9 (2) | O8A—C4A—C3A | 106.67 (19) |
O8—C4—C5 | 110.80 (19) | C4A—C5A—C6A | 109.85 (19) |
O8—C4—C3 | 107.79 (19) | C6A—C5A—C9A | 111.1 (2) |
C4—C5—C9 | 112.0 (2) | C4A—C5A—C9A | 112.6 (2) |
C6—C5—C9 | 112.9 (2) | O1A—C6A—C5A | 111.15 (19) |
C4—C5—C6 | 109.3 (2) | C5A—C6A—C16A | 111.54 (19) |
O1—C6—C5 | 110.07 (19) | O1A—C6A—C16A | 108.33 (18) |
C5—C6—C16 | 113.1 (2) | C2A—C10A—C11A | 120.0 (2) |
O1—C6—C16 | 106.96 (19) | C2A—C10A—C15A | 122.2 (2) |
C2—C10—C11 | 121.1 (2) | C11A—C10A—C15A | 117.7 (3) |
C11—C10—C15 | 118.1 (2) | C10A—C11A—C12A | 121.8 (3) |
C2—C10—C15 | 120.8 (2) | C11A—C12A—C13A | 119.0 (3) |
C10—C11—C12 | 121.9 (2) | Cl1A—C13A—C14A | 120.0 (3) |
C11—C12—C13 | 118.4 (2) | C12A—C13A—C14A | 120.7 (3) |
C12—C13—C14 | 121.4 (2) | Cl1A—C13A—C12A | 119.3 (3) |
Cl1—C13—C12 | 119.2 (2) | C13A—C14A—C15A | 119.8 (3) |
Cl1—C13—C14 | 119.4 (2) | C10A—C15A—C14A | 121.0 (3) |
C13—C14—C15 | 119.4 (3) | C6A—C16A—C21A | 121.2 (2) |
C10—C15—C14 | 120.7 (3) | C17A—C16A—C21A | 117.6 (2) |
C6—C16—C17 | 121.5 (2) | C6A—C16A—C17A | 121.1 (2) |
C17—C16—C21 | 117.3 (3) | C16A—C17A—C18A | 121.3 (3) |
C6—C16—C21 | 121.2 (2) | C17A—C18A—C19A | 119.6 (3) |
C16—C17—C18 | 121.2 (3) | Cl2A—C19A—C18A | 119.8 (3) |
C17—C18—C19 | 119.6 (3) | Cl2A—C19A—C20A | 119.6 (2) |
Cl2—C19—C20 | 119.1 (2) | C18A—C19A—C20A | 120.6 (3) |
Cl2—C19—C18 | 120.0 (3) | C19A—C20A—C21A | 119.5 (3) |
C18—C19—C20 | 120.9 (3) | C16A—C21A—C20A | 121.4 (3) |
C19—C20—C21 | 118.9 (3) | O1A—C2A—H2A | 108.32 |
C16—C21—C20 | 122.1 (3) | C3A—C2A—H2A | 108.46 |
O1—C2—H2 | 108.87 | C10A—C2A—H2A | 108.29 |
C3—C2—H2 | 108.96 | C2A—C3A—H3A | 107.48 |
C10—C2—H2 | 108.93 | C4A—C3A—H3A | 107.45 |
C4—C3—H3 | 107.36 | C7A—C3A—H3A | 107.39 |
C2—C3—H3 | 107.28 | O8A—C4A—H4A | 109.03 |
C7—C3—H3 | 107.29 | C3A—C4A—H4A | 109.09 |
C3—C4—H4 | 109.07 | C5A—C4A—H4A | 109.03 |
C5—C4—H4 | 109.03 | C4A—C5A—H5A | 107.66 |
O8—C4—H4 | 109.18 | C6A—C5A—H5A | 107.67 |
C6—C5—H5 | 107.47 | C9A—C5A—H5A | 107.74 |
C9—C5—H5 | 107.39 | O1A—C6A—H6A | 108.61 |
C4—C5—H5 | 107.46 | C5A—C6A—H6A | 108.57 |
C16—C6—H6 | 108.83 | C16A—C6A—H6A | 108.57 |
O1—C6—H6 | 108.85 | C3A—C7A—H71A | 109.44 |
C5—C6—H6 | 108.94 | C3A—C7A—H72A | 109.52 |
C3—C7—H73 | 109.52 | C3A—C7A—H73A | 109.47 |
C3—C7—H71 | 109.44 | H71A—C7A—H72A | 109.48 |
H71—C7—H73 | 109.51 | H71A—C7A—H73A | 109.41 |
H72—C7—H73 | 109.44 | H72A—C7A—H73A | 109.51 |
H71—C7—H72 | 109.49 | C5A—C9A—H91A | 109.48 |
C3—C7—H72 | 109.44 | C5A—C9A—H92A | 109.49 |
C5—C9—H92 | 109.45 | C5A—C9A—H93A | 109.46 |
H91—C9—H92 | 109.50 | H91A—C9A—H92A | 109.49 |
H91—C9—H93 | 109.39 | H91A—C9A—H93A | 109.51 |
C5—C9—H93 | 109.48 | H92A—C9A—H93A | 109.39 |
H92—C9—H93 | 109.55 | C10A—C11A—H11A | 119.17 |
C5—C9—H91 | 109.45 | C12A—C11A—H11A | 119.06 |
C12—C11—H11 | 119.05 | C11A—C12A—H12A | 120.49 |
C10—C11—H11 | 119.05 | C13A—C12A—H12A | 120.48 |
C13—C12—H12 | 120.83 | C13A—C14A—H14A | 120.09 |
C11—C12—H12 | 120.77 | C15A—C14A—H14A | 120.14 |
C13—C14—H14 | 120.28 | C10A—C15A—H15A | 119.56 |
C15—C14—H14 | 120.31 | C14A—C15A—H15A | 119.47 |
C14—C15—H15 | 119.55 | C16A—C17A—H17A | 119.32 |
C10—C15—H15 | 119.70 | C18A—C17A—H17A | 119.38 |
C18—C17—H17 | 119.38 | C17A—C18A—H18A | 120.13 |
C16—C17—H17 | 119.43 | C19A—C18A—H18A | 120.27 |
C17—C18—H18 | 120.21 | C19A—C20A—H20A | 120.30 |
C19—C18—H18 | 120.18 | C21A—C20A—H20A | 120.17 |
C19—C20—H20 | 120.62 | C16A—C21A—H21A | 119.34 |
C21—C20—H20 | 120.45 | C20A—C21A—H21A | 119.31 |
C6—O1—C2—C3 | 59.0 (3) | C17—C18—C19—Cl2 | −178.9 (3) |
C6—O1—C2—C10 | −178.4 (2) | Cl2—C19—C20—C21 | 179.1 (2) |
C2—O1—C6—C5 | −58.8 (3) | C18—C19—C20—C21 | 0.5 (5) |
C2—O1—C6—C16 | 178.0 (2) | C19—C20—C21—C16 | 0.4 (5) |
C2A—O1A—C6A—C5A | −58.4 (2) | O1A—C2A—C10A—C15A | −38.1 (3) |
C6A—O1A—C2A—C3A | 62.5 (2) | C10A—C2A—C3A—C7A | 51.7 (3) |
C6A—O1A—C2A—C10A | −173.23 (19) | O1A—C2A—C10A—C11A | 144.5 (3) |
C2A—O1A—C6A—C16A | 178.74 (18) | O1A—C2A—C3A—C4A | −60.9 (2) |
O1—C2—C3—C4 | −55.2 (3) | O1A—C2A—C3A—C7A | 173.6 (2) |
O1—C2—C10—C11 | 146.7 (2) | C10A—C2A—C3A—C4A | 177.1 (2) |
C10—C2—C3—C7 | 59.6 (3) | C3A—C2A—C10A—C15A | 83.9 (3) |
C10—C2—C3—C4 | −174.7 (2) | C3A—C2A—C10A—C11A | −93.5 (3) |
C3—C2—C10—C15 | 87.1 (3) | C2A—C3A—C4A—O8A | −63.9 (2) |
O1—C2—C10—C15 | −34.6 (3) | C7A—C3A—C4A—C5A | −175.0 (2) |
C3—C2—C10—C11 | −91.6 (3) | C2A—C3A—C4A—C5A | 58.2 (3) |
O1—C2—C3—C7 | 179.0 (2) | C7A—C3A—C4A—O8A | 62.8 (3) |
C7—C3—C4—C5 | −177.6 (2) | O8A—C4A—C5A—C6A | 64.4 (3) |
C2—C3—C4—C5 | 55.6 (3) | C3A—C4A—C5A—C9A | −179.1 (2) |
C2—C3—C4—O8 | −65.8 (2) | O8A—C4A—C5A—C9A | −60.0 (3) |
C7—C3—C4—O8 | 60.9 (3) | C3A—C4A—C5A—C6A | −54.7 (3) |
O8—C4—C5—C9 | −62.5 (3) | C9A—C5A—C6A—O1A | 178.4 (2) |
C3—C4—C5—C6 | −56.3 (3) | C9A—C5A—C6A—C16A | −60.6 (3) |
C3—C4—C5—C9 | 177.8 (2) | C4A—C5A—C6A—C16A | 174.2 (2) |
O8—C4—C5—C6 | 63.4 (2) | C4A—C5A—C6A—O1A | 53.2 (3) |
C9—C5—C6—C16 | −59.2 (3) | O1A—C6A—C16A—C21A | 54.6 (3) |
C4—C5—C6—C16 | 175.36 (19) | O1A—C6A—C16A—C17A | −128.8 (2) |
C9—C5—C6—O1 | −178.8 (2) | C5A—C6A—C16A—C21A | −68.0 (3) |
C4—C5—C6—O1 | 55.8 (3) | C5A—C6A—C16A—C17A | 108.6 (3) |
C5—C6—C16—C21 | −80.7 (3) | C2A—C10A—C11A—C12A | 175.1 (3) |
O1—C6—C16—C17 | −141.1 (3) | C11A—C10A—C15A—C14A | 1.8 (5) |
C5—C6—C16—C17 | 97.5 (3) | C15A—C10A—C11A—C12A | −2.4 (5) |
O1—C6—C16—C21 | 40.6 (3) | C2A—C10A—C15A—C14A | −175.6 (3) |
C2—C10—C11—C12 | 177.6 (2) | C10A—C11A—C12A—C13A | 1.2 (5) |
C15—C10—C11—C12 | −1.1 (4) | C11A—C12A—C13A—Cl1A | 180.0 (3) |
C11—C10—C15—C14 | 0.9 (4) | C11A—C12A—C13A—C14A | 0.6 (6) |
C2—C10—C15—C14 | −177.9 (3) | Cl1A—C13A—C14A—C15A | 179.5 (3) |
C10—C11—C12—C13 | 0.4 (4) | C12A—C13A—C14A—C15A | −1.1 (6) |
C11—C12—C13—Cl1 | 179.2 (2) | C13A—C14A—C15A—C10A | −0.1 (5) |
C11—C12—C13—C14 | 0.7 (4) | C21A—C16A—C17A—C18A | 1.6 (4) |
Cl1—C13—C14—C15 | −179.4 (2) | C6A—C16A—C21A—C20A | 175.6 (3) |
C12—C13—C14—C15 | −0.9 (4) | C6A—C16A—C17A—C18A | −175.1 (3) |
C13—C14—C15—C10 | 0.1 (4) | C17A—C16A—C21A—C20A | −1.1 (4) |
C21—C16—C17—C18 | 1.6 (5) | C16A—C17A—C18A—C19A | −0.9 (4) |
C6—C16—C17—C18 | −176.7 (3) | C17A—C18A—C19A—Cl2A | 179.3 (2) |
C6—C16—C21—C20 | 176.9 (3) | C17A—C18A—C19A—C20A | −0.3 (5) |
C17—C16—C21—C20 | −1.4 (4) | C18A—C19A—C20A—C21A | 0.7 (5) |
C16—C17—C18—C19 | −0.8 (5) | Cl2A—C19A—C20A—C21A | −178.8 (3) |
C17—C18—C19—C20 | −0.3 (5) | C19A—C20A—C21A—C16A | 0.0 (5) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) x, −y+3/2, z−1/2; (vii) −x+1, −y+1, −z+1; (viii) x, −y+3/2, z+1/2; (ix) x, −y+1/2, z+1/2; (x) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O1Aiv | 0.84 (4) | 2.04 (4) | 2.850 (3) | 163 (3) |
O8A—H8A···O8viii | 0.81 (3) | 2.09 (3) | 2.833 (3) | 152 (3) |
C2A—H2A···O8A | 0.98 | 2.44 | 2.827 (3) | 103 |
C4A—H4A···Cl1iii | 0.98 | 2.61 | 3.563 (3) | 164 |
C6A—H6A···O8Avii | 0.98 | 2.56 | 3.380 (3) | 141 |
Symmetry codes: (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (vii) −x+1, −y+1, −z+1; (viii) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20Cl2O2 |
Mr | 351.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.1315 (9), 11.7075 (19), 26.177 (3) |
β (°) | 99.728 (9) |
V (Å3) | 3664.4 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.2 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.650, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7004, 6670, 5034 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.146, 1.06 |
No. of reflections | 6670 |
No. of parameters | 423 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.42 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).
O1—C6 | 1.431 (3) | O1A—C2A | 1.447 (3) |
O1—C2 | 1.425 (3) | O1A—C6A | 1.447 (3) |
O8—C4 | 1.437 (3) | O8A—C4A | 1.431 (3) |
C2—O1—C6 | 114.78 (18) | O1—C6—C16 | 106.96 (19) |
C2A—O1A—C6A | 112.57 (17) | O1A—C2A—C10A | 109.24 (19) |
O1—C2—C10 | 106.90 (19) | O1A—C6A—C16A | 108.33 (18) |
C2—O1—C6—C16 | 178.0 (2) | C9—C5—C6—O1 | −178.8 (2) |
C2A—O1A—C6A—C16A | 178.74 (18) | C10A—C2A—C3A—C4A | 177.1 (2) |
C10—C2—C3—C4 | −174.7 (2) | C7A—C3A—C4A—C5A | −175.0 (2) |
C7—C3—C4—C5 | −177.6 (2) | C7A—C3A—C4A—O8A | 62.8 (3) |
C7—C3—C4—O8 | 60.9 (3) | O8A—C4A—C5A—C6A | 64.4 (3) |
O8—C4—C5—C6 | 63.4 (2) | C9A—C5A—C6A—O1A | 178.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O1Ai | 0.84 (4) | 2.04 (4) | 2.850 (3) | 163 (3) |
O8A—H8A···O8ii | 0.81 (3) | 2.09 (3) | 2.833 (3) | 152 (3) |
C4A—H4A···Cl1iii | 0.98 | 2.61 | 3.563 (3) | 164 |
C6A—H6A···O8Aiv | 0.98 | 2.56 | 3.380 (3) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z+1. |
Pyran derivatives are important constituents of many vitamin derivatives and antiulcer drugs, such as alpha tocopheral (vitamin E) (Finar, 1989) and methantheline (Parimoo, 1999). Persubstituted pyrans are easily synthesized, and their ring conformations would serve as comparative models for their cyclohexane counterparts. Molecules with a pyran ring can assume planar (Kumar et al., 1999), twist boat (Usman et al., 2002), sofa (Ray et al., 1998) and chair (Belakhov et al., 2002) conformations depending upon the level of unsaturation and the nature of the substituents on the ring. This investigation was undertaken to assign the conformation of the pyran ring and the orientation of the hydroxyl group in the title molecule, (I).
There are two molecules in the asymmetric unit of (I). The pyran rings are in chair conformations, as shown in Fig. 1. The torsion angles around the bonds involving the ring atoms deviate from the value of 56° expected for a perfect chair conformation (Kalsi, 1997). The bond lengths within the pyran ring are in the range 1.425 (3)—1.540 (4) Å (for molecule 1 containing O1 atom) and 1.447 (3)—1.540 (3) Å (for molecule 2 containing O1A atom). The ranges of bond angles are 108.56 (19)–114.78 (18)° (for molecule 1) and 107.4 (2)–112.57 (17)° (for molecule 2). The configurations of chiral atoms C2, C3, C5 and C6 in molecule 1 are found to be S, S, S and R, respectively, which are identical to those of their counterparts in molecule 2. However, the compound crystallizes as a racemic mixture in the corresponding space group P21/c. The relative orientation of the two chlorophenyl groups differ in the two molecules, as shown by the dihedral angles between the two rings of 44.01 (1)° in molecule 1 and 51.01 (1)° in molecule 2. The equatorial orientations of all substituents except the hydroxyl groups are confirmed by the torsion angles of about 180° comprising the external atom and the other three ring atoms as observed in the pentasubstituted cyclohexan-1-one derivative (Sarangarajan et al., 2002). The hydroxyl groups are oriented axially, as confirmed by the average of the C7—C3—C4—O8 torsion angles of 61.85 (3)°, which is close to the ideal value of 60° (Nasipuri, 1992).
In the crystal structure, the molecules are assembled in layers. The adjacent layers interact through O—H···O intermolecular hydrogen bonding involving atoms O8 and O1A(1 − x, 1/2 + y, 1/2 − z) at a distance of 2.850 (3) Å with an angle of 163 (3)° around atom H8. This is supplemented by another interaction between O8A and O8(x, 3/2 − y, 1/2 + z) at a distance of 2.833 (3) Å with an angle of 152 (3)° around atom H8A (Fig. 2 and Table 2).