Acta Cryst. (2008). E64, o777 [ doi:10.1107/S1600536808008428 ]
The title compound, C34H25Cl3O3S2·0.5CH3OH, was synthesized by the reaction of thiophene-2-carbaldehyde with acetophenone and NaOH under solvent-free conditions, using tetrabutylammonium bromide as a phase-transfer catalyst. The central six-membered ring adopts a chair conformation with the bulky thiophene, 4-chlorophenyl and 4-chlorobenzoyl substituents in equatorial positions. The hydroxyl group is in an axial position and forms an intramolecular O-H
O hydrogen bond to the carbonyl group of an adjacent 4-chlorobenzoyl substituent. The methanol solvent molecules are disordered equally over two positions within one-dimensional channels, with site occupancy factors of 0.25.
4-Chloroacetophenone (6.25 mmol), freshly distilled thiophene-2-carbaldehyde (3.125 mmol), NaOH (6.25 mmol) and tetrabutyl ammonium bromide (1 mmol) were mixed with a glass paddle in an open flask. The resulting mixture was washed several times with water to remove NaOH and recrystallized from methanol to give the title compound as a crystalline solid. Elemental analysis calculated: C 62.03, H 4.07%; found: C 62.08, H 4.02%.
H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5Ueq(C). The H atoms of hydroxyl groups were placed in idealized positions with O—H = 0.82 Å and refined as riding with Uiso(H) = 1.5Ueq(O). The crystal diffracted relatively weakly and the data are therefore limited to θmax = 22.5°, with ca 50% data observed at the 2σ(I) level. The resulting structure is therefore of relatively low precision. The methanol solvent molecule was refined as disordered over two orientations, each with 25% site occupancy to give reasonable displacement parameters. The C—O bonds were restrained to 1.45 (2) Å and the anisotropic displacement parameters of all atoms were restrained to have approximately equal components.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008)); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./bi2281fig1thm.gif)
| Fig. 1. Molecular stucture showing displacement ellipsoids at 20% probability. H atoms and the disordered methanol molecule is omitted. |
| C34H25Cl3O3S2·0.5CH4O | F000 = 2760 |
| Mr = 668.03 | Dx = 1.245 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 3877 reflections |
| a = 22.5660 (16) Å | θ = 2.4–19.6º |
| b = 12.1356 (12) Å | µ = 0.41 mm−1 |
| c = 26.030 (2) Å | T = 298 (2) K |
| V = 7128.4 (11) Å3 | Block, colourless |
| Z = 8 | 0.67 × 0.16 × 0.13 mm |
| Bruker SMART CCD diffractometer | 4502 independent reflections |
| Radiation source: fine-focus sealed tube | 2357 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.096 |
| T = 298(2) K | θmax = 22.5º |
| φ and ω scans | θmin = 2.1º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −24→21 |
| Tmin = 0.772, Tmax = 0.949 | k = −13→12 |
| 27584 measured reflections | l = −28→27 |
| 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)] = 0.080 | H-atom parameters constrained |
| wR(F2) = 0.290 | w = 1/[σ2(Fo2) + (0.1474P)2 + 3.8778P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max = 0.004 |
| 4502 reflections | Δρmax = 0.64 e Å−3 |
| 415 parameters | Δρmin = −0.40 e Å−3 |
| 50 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C34H25Cl3O3S2·0.5CH4O | V = 7128.4 (11) Å3 |
| Mr = 668.03 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 22.5660 (16) Å | µ = 0.41 mm−1 |
| b = 12.1356 (12) Å | T = 298 (2) K |
| c = 26.030 (2) Å | 0.67 × 0.16 × 0.13 mm |
| Bruker SMART CCD diffractometer | 4502 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2357 reflections with I > 2σ(I) |
| Tmin = 0.772, Tmax = 0.949 | Rint = 0.096 |
| 27584 measured reflections | θmax = 22.5º |
| R[F2 > 2σ(F2)] = 0.080 | 50 restraints |
| wR(F2) = 0.290 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.64 e Å−3 |
| 4502 reflections | Δρmin = −0.40 e Å−3 |
| 415 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 | Occ. (<1) | |
| Cl1 | 0.95396 (12) | 0.3492 (3) | −0.16180 (9) | 0.1142 (10) | |
| Cl2 | 1.09441 (11) | 0.3656 (2) | 0.12369 (13) | 0.1225 (11) | |
| Cl3 | 0.53719 (14) | 0.0925 (3) | 0.28831 (11) | 0.1374 (13) | |
| O1 | 0.8096 (2) | −0.0250 (4) | −0.02208 (17) | 0.0638 (13) | |
| H1 | 0.8436 | −0.0488 | −0.0231 | 0.096* | |
| O2 | 0.9156 (2) | −0.0200 (4) | 0.0317 (2) | 0.0713 (14) | |
| O3 | 0.7060 (2) | −0.1231 (5) | 0.1052 (2) | 0.0798 (16) | |
| O4 | 0.769 (2) | 0.641 (7) | 0.351 (3) | 0.26 (2) | 0.25 |
| H4 | 0.7863 | 0.6794 | 0.3305 | 0.395* | 0.25 |
| O5 | 0.747 (2) | 0.302 (6) | 0.304 (3) | 0.27 (2) | 0.25 |
| H5 | 0.7735 | 0.2800 | 0.2856 | 0.401* | 0.25 |
| S1 | 0.86979 (15) | −0.0641 (3) | 0.16254 (12) | 0.1253 (11) | |
| S2 | 0.62891 (9) | 0.23441 (18) | 0.03888 (10) | 0.0801 (7) | |
| C1 | 0.8106 (3) | 0.0886 (5) | −0.0078 (2) | 0.0512 (17) | |
| C2 | 0.8364 (3) | 0.1015 (5) | 0.0474 (2) | 0.0486 (16) | |
| H2 | 0.8321 | 0.1784 | 0.0583 | 0.058* | |
| C3 | 0.8012 (3) | 0.0259 (6) | 0.0853 (3) | 0.0547 (18) | |
| H3 | 0.8045 | −0.0502 | 0.0731 | 0.066* | |
| C4 | 0.7355 (3) | 0.0580 (6) | 0.0849 (2) | 0.0506 (17) | |
| H4A | 0.7308 | 0.1311 | 0.1004 | 0.061* | |
| C5 | 0.7092 (3) | 0.0585 (6) | 0.0302 (3) | 0.0531 (17) | |
| H5A | 0.7086 | −0.0177 | 0.0177 | 0.064* | |
| C6 | 0.7465 (3) | 0.1268 (6) | −0.0074 (3) | 0.0565 (18) | |
| H6A | 0.7301 | 0.1202 | −0.0417 | 0.068* | |
| H6B | 0.7449 | 0.2039 | 0.0024 | 0.068* | |
| C7 | 0.8479 (3) | 0.1562 (6) | −0.0462 (2) | 0.0551 (18) | |
| C8 | 0.8786 (3) | 0.1061 (7) | −0.0853 (3) | 0.073 (2) | |
| H8 | 0.8770 | 0.0298 | −0.0884 | 0.088* | |
| C9 | 0.9118 (4) | 0.1661 (9) | −0.1201 (3) | 0.084 (3) | |
| H9 | 0.9327 | 0.1301 | −0.1459 | 0.101* | |
| C10 | 0.9137 (3) | 0.2763 (8) | −0.1166 (3) | 0.071 (2) | |
| C11 | 0.8847 (4) | 0.3293 (8) | −0.0774 (3) | 0.080 (2) | |
| H11 | 0.8871 | 0.4055 | −0.0742 | 0.096* | |
| C12 | 0.8519 (4) | 0.2680 (7) | −0.0428 (3) | 0.069 (2) | |
| H12 | 0.8321 | 0.3041 | −0.0164 | 0.083* | |
| C13 | 0.9012 (3) | 0.0708 (6) | 0.0487 (3) | 0.0547 (18) | |
| C14 | 0.9471 (3) | 0.1467 (6) | 0.0680 (3) | 0.0529 (17) | |
| C15 | 0.9353 (3) | 0.2480 (6) | 0.0891 (3) | 0.078 (2) | |
| H15 | 0.8962 | 0.2710 | 0.0924 | 0.093* | |
| C16 | 0.9803 (4) | 0.3164 (7) | 0.1056 (4) | 0.090 (3) | |
| H16 | 0.9717 | 0.3859 | 0.1187 | 0.108* | |
| C17 | 1.0372 (3) | 0.2813 (8) | 0.1023 (3) | 0.072 (2) | |
| C18 | 1.0507 (4) | 0.1813 (8) | 0.0824 (3) | 0.079 (2) | |
| H18 | 1.0900 | 0.1588 | 0.0802 | 0.095* | |
| C19 | 1.0067 (3) | 0.1142 (7) | 0.0655 (3) | 0.070 (2) | |
| H19 | 1.0162 | 0.0454 | 0.0520 | 0.084* | |
| C20 | 0.8272 (3) | 0.0314 (6) | 0.1381 (3) | 0.0601 (19) | |
| C21 | 0.8207 (3) | 0.1219 (6) | 0.1774 (2) | 0.0587 (18) | |
| H21 | 0.7972 | 0.1844 | 0.1740 | 0.070* | |
| C22 | 0.8565 (5) | 0.0956 (10) | 0.2202 (4) | 0.112 (3) | |
| H22 | 0.8614 | 0.1430 | 0.2479 | 0.135* | |
| C23 | 0.8815 (5) | 0.0013 (12) | 0.2177 (4) | 0.120 (4) | |
| H23 | 0.9041 | −0.0280 | 0.2442 | 0.144* | |
| C24 | 0.7011 (3) | −0.0268 (7) | 0.1167 (3) | 0.0565 (18) | |
| C25 | 0.6618 (3) | 0.0078 (7) | 0.1602 (3) | 0.0610 (19) | |
| C26 | 0.6492 (4) | 0.1131 (8) | 0.1721 (3) | 0.083 (2) | |
| H26 | 0.6673 | 0.1691 | 0.1534 | 0.100* | |
| C27 | 0.6109 (4) | 0.1411 (9) | 0.2108 (4) | 0.096 (3) | |
| H27 | 0.6027 | 0.2146 | 0.2180 | 0.115* | |
| C28 | 0.5848 (4) | 0.0586 (10) | 0.2387 (3) | 0.085 (3) | |
| C29 | 0.5948 (5) | −0.0444 (10) | 0.2273 (4) | 0.109 (3) | |
| H29 | 0.5755 | −0.0999 | 0.2454 | 0.131* | |
| C30 | 0.6346 (4) | −0.0719 (8) | 0.1880 (3) | 0.090 (3) | |
| H30 | 0.6424 | −0.1456 | 0.1809 | 0.108* | |
| C31 | 0.6455 (3) | 0.0992 (6) | 0.0322 (3) | 0.0537 (17) | |
| C32 | 0.5939 (3) | 0.0334 (6) | 0.0320 (3) | 0.0607 (19) | |
| H32 | 0.5929 | −0.0427 | 0.0280 | 0.073* | |
| C33 | 0.5433 (3) | 0.1036 (8) | 0.0389 (3) | 0.080 (2) | |
| H33 | 0.5048 | 0.0766 | 0.0402 | 0.095* | |
| C34 | 0.5559 (3) | 0.2092 (8) | 0.0432 (3) | 0.078 (2) | |
| H34 | 0.5274 | 0.2637 | 0.0481 | 0.094* | |
| C35 | 0.756 (4) | 0.534 (7) | 0.328 (4) | 0.26 (2) | 0.25 |
| H35A | 0.7855 | 0.5181 | 0.3027 | 0.394* | 0.25 |
| H35B | 0.7177 | 0.5359 | 0.3126 | 0.394* | 0.25 |
| H35C | 0.7570 | 0.4783 | 0.3544 | 0.394* | 0.25 |
| C36 | 0.752 (3) | 0.420 (7) | 0.311 (4) | 0.26 (2) | 0.25 |
| H36A | 0.7377 | 0.4577 | 0.2814 | 0.394* | 0.25 |
| H36B | 0.7931 | 0.4391 | 0.3168 | 0.394* | 0.25 |
| H36C | 0.7294 | 0.4426 | 0.3408 | 0.394* | 0.25 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1111 (19) | 0.148 (3) | 0.0834 (16) | −0.0190 (16) | 0.0260 (13) | 0.0327 (16) |
| Cl2 | 0.0846 (17) | 0.096 (2) | 0.186 (3) | −0.0247 (14) | −0.0361 (17) | −0.0093 (18) |
| Cl3 | 0.131 (2) | 0.192 (3) | 0.0885 (19) | 0.017 (2) | 0.0507 (16) | 0.0001 (19) |
| O1 | 0.074 (3) | 0.047 (3) | 0.071 (3) | 0.001 (2) | 0.006 (2) | −0.013 (2) |
| O2 | 0.064 (3) | 0.053 (3) | 0.097 (4) | 0.008 (3) | 0.006 (3) | −0.017 (3) |
| O3 | 0.085 (4) | 0.056 (4) | 0.099 (4) | −0.012 (3) | 0.028 (3) | −0.003 (3) |
| O4 | 0.14 (3) | 0.34 (7) | 0.31 (5) | 0.05 (4) | −0.03 (2) | 0.05 (5) |
| O5 | 0.15 (2) | 0.34 (7) | 0.31 (5) | 0.05 (4) | −0.02 (2) | 0.04 (5) |
| S1 | 0.145 (3) | 0.110 (2) | 0.121 (2) | 0.0275 (19) | −0.0365 (18) | 0.0112 (18) |
| S2 | 0.0612 (12) | 0.0590 (14) | 0.1201 (18) | 0.0011 (10) | −0.0021 (11) | −0.0019 (12) |
| C1 | 0.055 (4) | 0.043 (4) | 0.056 (4) | 0.003 (3) | 0.007 (3) | −0.003 (3) |
| C2 | 0.048 (4) | 0.044 (4) | 0.055 (4) | −0.001 (3) | 0.010 (3) | 0.000 (3) |
| C3 | 0.054 (4) | 0.053 (4) | 0.057 (4) | 0.002 (3) | 0.008 (3) | −0.001 (3) |
| C4 | 0.045 (4) | 0.049 (4) | 0.058 (4) | −0.004 (3) | 0.003 (3) | 0.001 (3) |
| C5 | 0.049 (4) | 0.044 (4) | 0.066 (4) | −0.006 (3) | 0.000 (3) | −0.007 (3) |
| C6 | 0.049 (4) | 0.060 (5) | 0.060 (4) | −0.006 (3) | 0.004 (3) | 0.000 (4) |
| C7 | 0.053 (4) | 0.065 (5) | 0.048 (4) | −0.003 (3) | 0.004 (3) | 0.002 (4) |
| C8 | 0.084 (5) | 0.073 (6) | 0.062 (5) | 0.009 (4) | 0.021 (4) | 0.002 (4) |
| C9 | 0.089 (6) | 0.100 (8) | 0.063 (5) | 0.014 (5) | 0.025 (4) | 0.002 (5) |
| C10 | 0.060 (5) | 0.090 (7) | 0.061 (5) | −0.002 (5) | 0.008 (4) | 0.010 (5) |
| C11 | 0.084 (5) | 0.080 (6) | 0.076 (6) | −0.011 (5) | 0.013 (5) | 0.011 (5) |
| C12 | 0.088 (5) | 0.055 (5) | 0.063 (5) | −0.007 (4) | 0.021 (4) | 0.001 (4) |
| C13 | 0.057 (4) | 0.047 (5) | 0.060 (4) | 0.008 (4) | 0.009 (3) | 0.001 (4) |
| C14 | 0.046 (4) | 0.053 (5) | 0.059 (4) | −0.002 (3) | 0.001 (3) | 0.002 (3) |
| C15 | 0.052 (4) | 0.056 (5) | 0.125 (7) | 0.006 (4) | −0.010 (4) | −0.018 (5) |
| C16 | 0.082 (6) | 0.054 (5) | 0.136 (8) | 0.010 (5) | −0.018 (5) | −0.021 (5) |
| C17 | 0.053 (5) | 0.084 (7) | 0.079 (5) | −0.009 (4) | −0.013 (4) | 0.015 (5) |
| C18 | 0.057 (5) | 0.080 (6) | 0.101 (6) | 0.005 (5) | 0.002 (4) | −0.007 (5) |
| C19 | 0.048 (4) | 0.078 (6) | 0.084 (6) | 0.009 (4) | 0.006 (4) | −0.017 (4) |
| C20 | 0.060 (4) | 0.060 (5) | 0.060 (4) | −0.006 (4) | −0.002 (3) | 0.009 (4) |
| C21 | 0.072 (4) | 0.051 (4) | 0.053 (4) | 0.006 (3) | −0.028 (3) | −0.013 (3) |
| C22 | 0.128 (6) | 0.113 (6) | 0.097 (5) | −0.001 (5) | −0.023 (5) | −0.013 (5) |
| C23 | 0.118 (8) | 0.160 (12) | 0.082 (7) | −0.006 (8) | −0.037 (6) | 0.036 (7) |
| C24 | 0.065 (5) | 0.047 (5) | 0.057 (4) | −0.009 (4) | 0.005 (3) | −0.003 (4) |
| C25 | 0.051 (4) | 0.073 (6) | 0.059 (4) | −0.012 (4) | 0.001 (3) | 0.006 (4) |
| C26 | 0.091 (6) | 0.073 (7) | 0.085 (6) | 0.006 (5) | 0.024 (5) | 0.008 (5) |
| C27 | 0.109 (7) | 0.094 (7) | 0.085 (6) | 0.028 (6) | 0.033 (6) | 0.005 (6) |
| C28 | 0.077 (6) | 0.126 (9) | 0.052 (5) | 0.007 (6) | 0.010 (4) | −0.007 (6) |
| C29 | 0.156 (10) | 0.093 (8) | 0.078 (6) | −0.028 (7) | 0.036 (7) | 0.000 (6) |
| C30 | 0.116 (7) | 0.071 (6) | 0.082 (6) | −0.017 (5) | 0.021 (5) | 0.005 (5) |
| C31 | 0.048 (4) | 0.052 (4) | 0.061 (4) | −0.002 (3) | 0.000 (3) | −0.004 (3) |
| C32 | 0.033 (4) | 0.059 (5) | 0.090 (5) | −0.011 (3) | 0.006 (3) | −0.013 (4) |
| C33 | 0.041 (4) | 0.104 (8) | 0.094 (6) | −0.014 (4) | −0.002 (4) | −0.008 (5) |
| C34 | 0.060 (5) | 0.077 (7) | 0.097 (6) | 0.002 (4) | −0.002 (4) | 0.002 (5) |
| C35 | 0.15 (2) | 0.34 (7) | 0.31 (5) | 0.06 (4) | −0.04 (2) | 0.05 (5) |
| C36 | 0.14 (2) | 0.34 (7) | 0.31 (5) | 0.06 (4) | −0.04 (2) | 0.05 (5) |
| Cl1—C10 | 1.729 (8) | C12—H12 | 0.930 |
| Cl2—C17 | 1.739 (8) | C13—C14 | 1.475 (10) |
| Cl3—C28 | 1.730 (9) | C14—C15 | 1.374 (10) |
| O1—C1 | 1.428 (7) | C14—C19 | 1.402 (9) |
| O1—H1 | 0.820 | C15—C16 | 1.380 (11) |
| O2—C13 | 1.230 (8) | C15—H15 | 0.930 |
| O3—C24 | 1.211 (8) | C16—C17 | 1.355 (11) |
| O4—C35 | 1.45 (2) | C16—H16 | 0.930 |
| O4—H4 | 0.820 | C17—C18 | 1.354 (11) |
| O5—C36 | 1.45 (2) | C18—C19 | 1.358 (11) |
| O5—H5 | 0.820 | C18—H18 | 0.930 |
| S1—C20 | 1.633 (8) | C19—H19 | 0.930 |
| S1—C23 | 1.661 (12) | C20—C21 | 1.508 (10) |
| S2—C34 | 1.681 (8) | C21—C22 | 1.411 (13) |
| S2—C31 | 1.692 (7) | C21—H21 | 0.930 |
| C1—C6 | 1.519 (9) | C22—C23 | 1.279 (15) |
| C1—C7 | 1.543 (9) | C22—H22 | 0.930 |
| C1—C2 | 1.560 (9) | C23—H23 | 0.930 |
| C2—C13 | 1.509 (9) | C24—C25 | 1.498 (10) |
| C2—C3 | 1.564 (9) | C25—C26 | 1.346 (11) |
| C2—H2 | 0.980 | C25—C30 | 1.355 (11) |
| C3—C20 | 1.497 (10) | C26—C27 | 1.371 (11) |
| C3—C4 | 1.533 (9) | C26—H26 | 0.930 |
| C3—H3 | 0.980 | C27—C28 | 1.369 (13) |
| C4—C24 | 1.531 (9) | C27—H27 | 0.930 |
| C4—C5 | 1.544 (9) | C28—C29 | 1.304 (13) |
| C4—H4A | 0.980 | C29—C30 | 1.400 (13) |
| C5—C31 | 1.520 (9) | C29—H29 | 0.930 |
| C5—C6 | 1.535 (9) | C30—H30 | 0.930 |
| C5—H5A | 0.980 | C31—C32 | 1.411 (9) |
| C6—H6A | 0.970 | C32—C33 | 1.436 (11) |
| C6—H6B | 0.970 | C32—H32 | 0.930 |
| C7—C12 | 1.363 (10) | C33—C34 | 1.317 (11) |
| C7—C8 | 1.372 (10) | C33—H33 | 0.930 |
| C8—C9 | 1.383 (11) | C34—H34 | 0.930 |
| C8—H8 | 0.930 | C35—H35A | 0.960 |
| C9—C10 | 1.341 (12) | C35—H35B | 0.960 |
| C9—H9 | 0.930 | C35—H35C | 0.960 |
| C10—C11 | 1.372 (11) | C36—H36A | 0.960 |
| C11—C12 | 1.383 (10) | C36—H36B | 0.960 |
| C11—H11 | 0.930 | C36—H36C | 0.960 |
| C1—O1—H1 | 109.5 | C17—C16—H16 | 120.4 |
| C35—O4—H4 | 109.5 | C15—C16—H16 | 120.4 |
| C36—O5—H5 | 109.5 | C18—C17—C16 | 121.3 (7) |
| C20—S1—C23 | 95.2 (5) | C18—C17—Cl2 | 118.8 (6) |
| C34—S2—C31 | 92.7 (4) | C16—C17—Cl2 | 119.9 (7) |
| O1—C1—C6 | 106.3 (5) | C17—C18—C19 | 119.8 (7) |
| O1—C1—C7 | 110.7 (5) | C17—C18—H18 | 120.1 |
| C6—C1—C7 | 111.2 (5) | C19—C18—H18 | 120.1 |
| O1—C1—C2 | 110.0 (5) | C18—C19—C14 | 121.2 (8) |
| C6—C1—C2 | 108.6 (5) | C18—C19—H19 | 119.4 |
| C7—C1—C2 | 109.9 (5) | C14—C19—H19 | 119.4 |
| C13—C2—C1 | 110.9 (5) | C3—C20—C21 | 128.1 (6) |
| C13—C2—C3 | 109.5 (5) | C3—C20—S1 | 123.8 (6) |
| C1—C2—C3 | 109.4 (5) | C21—C20—S1 | 108.1 (5) |
| C13—C2—H2 | 109.0 | C22—C21—C20 | 108.3 (7) |
| C1—C2—H2 | 109.0 | C22—C21—H21 | 125.8 |
| C3—C2—H2 | 109.0 | C20—C21—H21 | 125.8 |
| C20—C3—C4 | 111.9 (5) | C23—C22—C21 | 114.5 (10) |
| C20—C3—C2 | 110.8 (5) | C23—C22—H22 | 122.7 |
| C4—C3—C2 | 109.8 (5) | C21—C22—H22 | 122.7 |
| C20—C3—H3 | 108.1 | C22—C23—S1 | 113.7 (8) |
| C4—C3—H3 | 108.1 | C22—C23—H23 | 123.2 |
| C2—C3—H3 | 108.1 | S1—C23—H23 | 123.2 |
| C24—C4—C3 | 108.4 (6) | O3—C24—C25 | 120.6 (6) |
| C24—C4—C5 | 107.8 (5) | O3—C24—C4 | 118.0 (6) |
| C3—C4—C5 | 112.3 (5) | C25—C24—C4 | 121.3 (7) |
| C24—C4—H4A | 109.4 | C26—C25—C30 | 117.3 (8) |
| C3—C4—H4A | 109.4 | C26—C25—C24 | 124.5 (7) |
| C5—C4—H4A | 109.4 | C30—C25—C24 | 118.2 (8) |
| C31—C5—C6 | 111.5 (6) | C25—C26—C27 | 122.6 (8) |
| C31—C5—C4 | 109.5 (5) | C25—C26—H26 | 118.7 |
| C6—C5—C4 | 112.3 (5) | C27—C26—H26 | 118.7 |
| C31—C5—H5A | 107.8 | C28—C27—C26 | 118.6 (9) |
| C6—C5—H5A | 107.8 | C28—C27—H27 | 120.7 |
| C4—C5—H5A | 107.8 | C26—C27—H27 | 120.7 |
| C1—C6—C5 | 111.3 (6) | C29—C28—C27 | 120.4 (8) |
| C1—C6—H6A | 109.4 | C29—C28—Cl3 | 120.4 (9) |
| C5—C6—H6A | 109.4 | C27—C28—Cl3 | 119.2 (9) |
| C1—C6—H6B | 109.4 | C28—C29—C30 | 120.4 (9) |
| C5—C6—H6B | 109.4 | C28—C29—H29 | 119.8 |
| H6A—C6—H6B | 108.0 | C30—C29—H29 | 119.8 |
| C12—C7—C8 | 117.2 (7) | C25—C30—C29 | 120.7 (9) |
| C12—C7—C1 | 121.5 (6) | C25—C30—H30 | 119.6 |
| C8—C7—C1 | 121.3 (7) | C29—C30—H30 | 119.6 |
| C7—C8—C9 | 121.7 (8) | C32—C31—C5 | 126.6 (6) |
| C7—C8—H8 | 119.2 | C32—C31—S2 | 111.5 (5) |
| C9—C8—H8 | 119.2 | C5—C31—S2 | 121.8 (5) |
| C10—C9—C8 | 119.9 (8) | C31—C32—C33 | 108.7 (7) |
| C10—C9—H9 | 120.0 | C31—C32—H32 | 125.7 |
| C8—C9—H9 | 120.0 | C33—C32—H32 | 125.7 |
| C9—C10—C11 | 120.1 (7) | C34—C33—C32 | 114.7 (7) |
| C9—C10—Cl1 | 118.8 (7) | C34—C33—H33 | 122.7 |
| C11—C10—Cl1 | 121.1 (7) | C32—C33—H33 | 122.7 |
| C10—C11—C12 | 119.2 (8) | C33—C34—S2 | 112.4 (6) |
| C10—C11—H11 | 120.4 | C33—C34—H34 | 123.8 |
| C12—C11—H11 | 120.4 | S2—C34—H34 | 123.8 |
| C7—C12—C11 | 121.9 (7) | O4—C35—H35A | 109.5 |
| C7—C12—H12 | 119.1 | O4—C35—H35B | 109.5 |
| C11—C12—H12 | 119.1 | H35A—C35—H35B | 109.5 |
| O2—C13—C14 | 119.8 (6) | O4—C35—H35C | 109.5 |
| O2—C13—C2 | 117.9 (6) | H35A—C35—H35C | 109.5 |
| C14—C13—C2 | 122.2 (6) | H35B—C35—H35C | 109.5 |
| C15—C14—C19 | 117.2 (7) | O5—C36—H36A | 109.5 |
| C15—C14—C13 | 124.0 (6) | O5—C36—H36B | 109.5 |
| C19—C14—C13 | 118.8 (7) | H36A—C36—H36B | 109.5 |
| C14—C15—C16 | 121.3 (7) | O5—C36—H36C | 109.5 |
| C14—C15—H15 | 119.4 | H36A—C36—H36C | 109.5 |
| C16—C15—H15 | 119.4 | H36B—C36—H36C | 109.5 |
| C17—C16—C15 | 119.2 (8) |
The authors acknowledge support from the National Natural Science Foundation of Liaocheng University (No. X051040).
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Huang, X.-Q. & Wang, J.-X. (2007). Acta Cryst. E63, o4168.
Luo, X. & Shan, Z. (2006). Acta Cryst. E62, o1631–o1632.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The title compound (Fig. 1) was synthesized by condensation and Michael addition of thiophene-2-carbaldehyde with 4-chloroacetophenone under solvent-free conditions, using tetrabutyl ammonium bromide as a phase-transfer catalyst. The bond lengths and angles are comparable to those observed in the related compounds 2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol (Luo & Shan, 2006) and 2,4-dibenzoyl-3,5-bis(2-thienyl)-1-phenylcyclohexanol (Huang & Wang, 2007). The hydroxyl group in the axial position forms an intramolecular O—H···O hydrogen bond to the carbonyl group of an adjacent para-chlorobenzoyl substituent (Table 1). The methanol solvent molecules lie within channels running along the crystallogaphic b axis, and are modelled as disordered along those channels.