2,4-Bis(4-chloro­benzo­yl)-1-(4-chloro­phen­yl)-3,5-di-2-thienylcyclo­hexa­nol methanol hemisolvate

Wang, X.-F.; Huang, X.-Q.

doi:10.1107/S1600536808008428

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o777

doi:10.1107/S1600536808008428

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2,4-Bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-di-2-thienylcyclohexanol methanol hemisolvate

Xiao-Fang Wang ^a and Xian-Qiang Huang ^b ^*

^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

(Received 1 February 2008; accepted 28 March 2008; online 2 April 2008)

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.

Related literature

For related structures, see: Luo & Shan (2006 ); Huang & Wang (2007 ).

Experimental

Crystal data

C₃₄H₂₅Cl₃O₃S₂·0.5CH₄O
M_r = 668.03
Orthorhombic, P b c a
a = 22.5660 (16) Å
b = 12.1356 (12) Å
c = 26.030 (2) Å
V = 7128.4 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 (2) K
0.67 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.772, T_max = 0.949
27584 measured reflections
4502 independent reflections
2357 reflections with I > 2σ(I)
R_int = 0.096
θ_max = 22.5°

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.290
S = 1.09
4502 reflections
415 parameters
50 restraints
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.19	2.772 (7)	128

Data collection: SMART (Bruker, 2001 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008428/bi2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008428/bi2281Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For related structures, see: Luo & Shan (2006); Huang & Wang (2007).

Experimental top

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%.

Computing details top

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).

Figures top

Fig. 1. Molecular stucture showing displacement ellipsoids at 20% probability. H atoms and the disordered methanol molecule is omitted.

2,4-Bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-di-2-thienylcyclohexanol methanol hemisolvate top

Crystal data top

C₃₄H₂₅Cl₃O₃S₂·0.5CH₄O	F(000) = 2760
M_r = 668.03	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	4502 independent reflections
Radiation source: fine-focus sealed tube	2357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scans	θ_max = 22.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→21
T_min = 0.772, T_max = 0.949	k = −13→12
27584 measured reflections	l = −28→27

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.290	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1474P)² + 3.8778P] where P = (F_o² + 2F_c²)/3
4502 reflections	(Δ/σ)_max = 0.004
415 parameters	Δρ_max = 0.64 e Å⁻³
50 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₃₄H₂₅Cl₃O₃S₂·0.5CH₄O	V = 7128.4 (11) Å³
M_r = 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

Data collection top

Bruker SMART CCD diffractometer	4502 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2357 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.949	R_int = 0.096
27584 measured reflections	θ_max = 22.5°

Refinement top

R[F² > 2σ(F²)] = 0.080	50 restraints
wR(F²) = 0.290	H-atom parameters constrained
S = 1.09	Δρ_max = 0.64 e Å⁻³
4502 reflections	Δρ_min = −0.40 e Å⁻³
415 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.19	2.772 (7)	128

Experimental details

Crystal data
Chemical formula	C₃₄H₂₅Cl₃O₃S₂·0.5CH₄O
M_r	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)
T_min, T_max	0.772, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	27584, 4502, 2357
R_int	0.096
θ_max (°)	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
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.40

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008)), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.19	2.772 (7)	128.1

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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Volume 64| Part 5| May 2008| Page o777

doi:10.1107/S1600536808008428

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,4-Bis(4-chloro­benzo­yl)-1-(4-chloro­phen­yl)-3,5-di-2-thienylcyclo­hexa­nol methanol hemisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,4-Bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-di-2-thienylcyclohexanol methanol hemisolvate