organic compounds
2,4-Bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-di-2-thienylcyclohexanol methanol hemisolvate
aCollege of Life Sciences and Chemistry, Tianshui Normal University, Tianshui 741000, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: hxqqxh2008@163.com
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.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808008428/bi2281sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008428/bi2281Isup2.hkl
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
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).Fig. 1. Molecular stucture showing displacement ellipsoids at 20% probability. H atoms and the disordered methanol molecule is omitted. |
C34H25Cl3O3S2·0.5CH4O | F(000) = 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 = 2.4–19.6° |
b = 12.1356 (12) Å | µ = 0.41 mm−1 |
c = 26.030 (2) Å | T = 298 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) |
Graphite monochromator | Rint = 0.096 |
ϕ and ω scans | θmax = 22.5°, θmin = 2.1° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.290 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1474P)2 + 3.8778P] where P = (Fo2 + 2Fc2)/3 |
4502 reflections | (Δ/σ)max = 0.004 |
415 parameters | Δρmax = 0.64 e Å−3 |
50 restraints | Δρmin = −0.40 e Å−3 |
C34H25Cl3O3S2·0.5CH4O | V = 7128.4 (11) Å3 |
Mr = 668.03 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 22.5660 (16) Å | µ = 0.41 mm−1 |
b = 12.1356 (12) Å | T = 298 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 = 22.5° |
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) |
Experimental details
Crystal data | |
Chemical formula | C34H25Cl3O3S2·0.5CH4O |
Mr | 668.03 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 22.5660 (16), 12.1356 (12), 26.030 (2) |
V (Å3) | 7128.4 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.67 × 0.16 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.772, 0.949 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27584, 4502, 2357 |
Rint | 0.096 |
θmax (°) | 22.5 |
(sin θ/λ)max (Å−1) | 0.539 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.290, 1.09 |
No. of reflections | 4502 |
No. of parameters | 415 |
No. of restraints | 50 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.40 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008)), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors acknowledge support from the National Natural Science Foundation of Liaocheng University (No. X051040).
References
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, X.-Q. & Wang, J.-X. (2007). Acta Cryst. E63, o4168. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luo, X. & Shan, Z. (2006). Acta Cryst. E62, o1631–o1632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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.