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

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ISSN: 2056-9890

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

(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[Luo, X. & Shan, Z. (2006). Acta Cryst. E62, o1631-o1632.]); Huang & Wang (2007[Huang, X.-Q. & Wang, J.-X. (2007). Acta Cryst. E63, o4168.]).

[Scheme 1]

Experimental

Crystal data
  • C34H25Cl3O3S2·0.5CH4O

  • Mr = 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.772, Tmax = 0.949

  • 27584 measured reflections

  • 4502 independent reflections

  • 2357 reflections with I > 2σ(I)

  • Rint = 0.096

  • θmax = 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

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.])); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

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.

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
[Figure 1] 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
C34H25Cl3O3S2·0.5CH4OF(000) = 2760
Mr = 668.03Dx = 1.245 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3877 reflections
a = 22.5660 (16) Åθ = 2.4–19.6°
b = 12.1356 (12) ŵ = 0.41 mm1
c = 26.030 (2) ÅT = 298 K
V = 7128.4 (11) Å3Block, colourless
Z = 80.67 × 0.16 × 0.13 mm
Data collection top
Bruker SMART CCD
diffractometer
4502 independent reflections
Radiation source: fine-focus sealed tube2357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
ϕ and ω scansθmax = 22.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2421
Tmin = 0.772, Tmax = 0.949k = 1312
27584 measured reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.290H-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 parametersΔρmax = 0.64 e Å3
50 restraintsΔρmin = 0.40 e Å3
Crystal data top
C34H25Cl3O3S2·0.5CH4OV = 7128.4 (11) Å3
Mr = 668.03Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 22.5660 (16) ŵ = 0.41 mm1
b = 12.1356 (12) ÅT = 298 K
c = 26.030 (2) Å0.67 × 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)
Tmin = 0.772, Tmax = 0.949Rint = 0.096
27584 measured reflectionsθmax = 22.5°
Refinement top
R[F2 > 2σ(F2)] = 0.08050 restraints
wR(F2) = 0.290H-atom parameters constrained
S = 1.09Δρmax = 0.64 e Å3
4502 reflectionsΔρmin = 0.40 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cl10.95396 (12)0.3492 (3)0.16180 (9)0.1142 (10)
Cl21.09441 (11)0.3656 (2)0.12369 (13)0.1225 (11)
Cl30.53719 (14)0.0925 (3)0.28831 (11)0.1374 (13)
O10.8096 (2)0.0250 (4)0.02208 (17)0.0638 (13)
H10.84360.04880.02310.096*
O20.9156 (2)0.0200 (4)0.0317 (2)0.0713 (14)
O30.7060 (2)0.1231 (5)0.1052 (2)0.0798 (16)
O40.769 (2)0.641 (7)0.351 (3)0.26 (2)0.25
H40.78630.67940.33050.395*0.25
O50.747 (2)0.302 (6)0.304 (3)0.27 (2)0.25
H50.77350.28000.28560.401*0.25
S10.86979 (15)0.0641 (3)0.16254 (12)0.1253 (11)
S20.62891 (9)0.23441 (18)0.03888 (10)0.0801 (7)
C10.8106 (3)0.0886 (5)0.0078 (2)0.0512 (17)
C20.8364 (3)0.1015 (5)0.0474 (2)0.0486 (16)
H20.83210.17840.05830.058*
C30.8012 (3)0.0259 (6)0.0853 (3)0.0547 (18)
H30.80450.05020.07310.066*
C40.7355 (3)0.0580 (6)0.0849 (2)0.0506 (17)
H4A0.73080.13110.10040.061*
C50.7092 (3)0.0585 (6)0.0302 (3)0.0531 (17)
H5A0.70860.01770.01770.064*
C60.7465 (3)0.1268 (6)0.0074 (3)0.0565 (18)
H6A0.73010.12020.04170.068*
H6B0.74490.20390.00240.068*
C70.8479 (3)0.1562 (6)0.0462 (2)0.0551 (18)
C80.8786 (3)0.1061 (7)0.0853 (3)0.073 (2)
H80.87700.02980.08840.088*
C90.9118 (4)0.1661 (9)0.1201 (3)0.084 (3)
H90.93270.13010.14590.101*
C100.9137 (3)0.2763 (8)0.1166 (3)0.071 (2)
C110.8847 (4)0.3293 (8)0.0774 (3)0.080 (2)
H110.88710.40550.07420.096*
C120.8519 (4)0.2680 (7)0.0428 (3)0.069 (2)
H120.83210.30410.01640.083*
C130.9012 (3)0.0708 (6)0.0487 (3)0.0547 (18)
C140.9471 (3)0.1467 (6)0.0680 (3)0.0529 (17)
C150.9353 (3)0.2480 (6)0.0891 (3)0.078 (2)
H150.89620.27100.09240.093*
C160.9803 (4)0.3164 (7)0.1056 (4)0.090 (3)
H160.97170.38590.11870.108*
C171.0372 (3)0.2813 (8)0.1023 (3)0.072 (2)
C181.0507 (4)0.1813 (8)0.0824 (3)0.079 (2)
H181.09000.15880.08020.095*
C191.0067 (3)0.1142 (7)0.0655 (3)0.070 (2)
H191.01620.04540.05200.084*
C200.8272 (3)0.0314 (6)0.1381 (3)0.0601 (19)
C210.8207 (3)0.1219 (6)0.1774 (2)0.0587 (18)
H210.79720.18440.17400.070*
C220.8565 (5)0.0956 (10)0.2202 (4)0.112 (3)
H220.86140.14300.24790.135*
C230.8815 (5)0.0013 (12)0.2177 (4)0.120 (4)
H230.90410.02800.24420.144*
C240.7011 (3)0.0268 (7)0.1167 (3)0.0565 (18)
C250.6618 (3)0.0078 (7)0.1602 (3)0.0610 (19)
C260.6492 (4)0.1131 (8)0.1721 (3)0.083 (2)
H260.66730.16910.15340.100*
C270.6109 (4)0.1411 (9)0.2108 (4)0.096 (3)
H270.60270.21460.21800.115*
C280.5848 (4)0.0586 (10)0.2387 (3)0.085 (3)
C290.5948 (5)0.0444 (10)0.2273 (4)0.109 (3)
H290.57550.09990.24540.131*
C300.6346 (4)0.0719 (8)0.1880 (3)0.090 (3)
H300.64240.14560.18090.108*
C310.6455 (3)0.0992 (6)0.0322 (3)0.0537 (17)
C320.5939 (3)0.0334 (6)0.0320 (3)0.0607 (19)
H320.59290.04270.02800.073*
C330.5433 (3)0.1036 (8)0.0389 (3)0.080 (2)
H330.50480.07660.04020.095*
C340.5559 (3)0.2092 (8)0.0432 (3)0.078 (2)
H340.52740.26370.04810.094*
C350.756 (4)0.534 (7)0.328 (4)0.26 (2)0.25
H35A0.78550.51810.30270.394*0.25
H35B0.71770.53590.31260.394*0.25
H35C0.75700.47830.35440.394*0.25
C360.752 (3)0.420 (7)0.311 (4)0.26 (2)0.25
H36A0.73770.45770.28140.394*0.25
H36B0.79310.43910.31680.394*0.25
H36C0.72940.44260.34080.394*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1111 (19)0.148 (3)0.0834 (16)0.0190 (16)0.0260 (13)0.0327 (16)
Cl20.0846 (17)0.096 (2)0.186 (3)0.0247 (14)0.0361 (17)0.0093 (18)
Cl30.131 (2)0.192 (3)0.0885 (19)0.017 (2)0.0507 (16)0.0001 (19)
O10.074 (3)0.047 (3)0.071 (3)0.001 (2)0.006 (2)0.013 (2)
O20.064 (3)0.053 (3)0.097 (4)0.008 (3)0.006 (3)0.017 (3)
O30.085 (4)0.056 (4)0.099 (4)0.012 (3)0.028 (3)0.003 (3)
O40.14 (3)0.34 (7)0.31 (5)0.05 (4)0.03 (2)0.05 (5)
O50.15 (2)0.34 (7)0.31 (5)0.05 (4)0.02 (2)0.04 (5)
S10.145 (3)0.110 (2)0.121 (2)0.0275 (19)0.0365 (18)0.0112 (18)
S20.0612 (12)0.0590 (14)0.1201 (18)0.0011 (10)0.0021 (11)0.0019 (12)
C10.055 (4)0.043 (4)0.056 (4)0.003 (3)0.007 (3)0.003 (3)
C20.048 (4)0.044 (4)0.055 (4)0.001 (3)0.010 (3)0.000 (3)
C30.054 (4)0.053 (4)0.057 (4)0.002 (3)0.008 (3)0.001 (3)
C40.045 (4)0.049 (4)0.058 (4)0.004 (3)0.003 (3)0.001 (3)
C50.049 (4)0.044 (4)0.066 (4)0.006 (3)0.000 (3)0.007 (3)
C60.049 (4)0.060 (5)0.060 (4)0.006 (3)0.004 (3)0.000 (4)
C70.053 (4)0.065 (5)0.048 (4)0.003 (3)0.004 (3)0.002 (4)
C80.084 (5)0.073 (6)0.062 (5)0.009 (4)0.021 (4)0.002 (4)
C90.089 (6)0.100 (8)0.063 (5)0.014 (5)0.025 (4)0.002 (5)
C100.060 (5)0.090 (7)0.061 (5)0.002 (5)0.008 (4)0.010 (5)
C110.084 (5)0.080 (6)0.076 (6)0.011 (5)0.013 (5)0.011 (5)
C120.088 (5)0.055 (5)0.063 (5)0.007 (4)0.021 (4)0.001 (4)
C130.057 (4)0.047 (5)0.060 (4)0.008 (4)0.009 (3)0.001 (4)
C140.046 (4)0.053 (5)0.059 (4)0.002 (3)0.001 (3)0.002 (3)
C150.052 (4)0.056 (5)0.125 (7)0.006 (4)0.010 (4)0.018 (5)
C160.082 (6)0.054 (5)0.136 (8)0.010 (5)0.018 (5)0.021 (5)
C170.053 (5)0.084 (7)0.079 (5)0.009 (4)0.013 (4)0.015 (5)
C180.057 (5)0.080 (6)0.101 (6)0.005 (5)0.002 (4)0.007 (5)
C190.048 (4)0.078 (6)0.084 (6)0.009 (4)0.006 (4)0.017 (4)
C200.060 (4)0.060 (5)0.060 (4)0.006 (4)0.002 (3)0.009 (4)
C210.072 (4)0.051 (4)0.053 (4)0.006 (3)0.028 (3)0.013 (3)
C220.128 (6)0.113 (6)0.097 (5)0.001 (5)0.023 (5)0.013 (5)
C230.118 (8)0.160 (12)0.082 (7)0.006 (8)0.037 (6)0.036 (7)
C240.065 (5)0.047 (5)0.057 (4)0.009 (4)0.005 (3)0.003 (4)
C250.051 (4)0.073 (6)0.059 (4)0.012 (4)0.001 (3)0.006 (4)
C260.091 (6)0.073 (7)0.085 (6)0.006 (5)0.024 (5)0.008 (5)
C270.109 (7)0.094 (7)0.085 (6)0.028 (6)0.033 (6)0.005 (6)
C280.077 (6)0.126 (9)0.052 (5)0.007 (6)0.010 (4)0.007 (6)
C290.156 (10)0.093 (8)0.078 (6)0.028 (7)0.036 (7)0.000 (6)
C300.116 (7)0.071 (6)0.082 (6)0.017 (5)0.021 (5)0.005 (5)
C310.048 (4)0.052 (4)0.061 (4)0.002 (3)0.000 (3)0.004 (3)
C320.033 (4)0.059 (5)0.090 (5)0.011 (3)0.006 (3)0.013 (4)
C330.041 (4)0.104 (8)0.094 (6)0.014 (4)0.002 (4)0.008 (5)
C340.060 (5)0.077 (7)0.097 (6)0.002 (4)0.002 (4)0.002 (5)
C350.15 (2)0.34 (7)0.31 (5)0.06 (4)0.04 (2)0.05 (5)
C360.14 (2)0.34 (7)0.31 (5)0.06 (4)0.04 (2)0.05 (5)
Geometric parameters (Å, º) top
Cl1—C101.729 (8)C12—H120.930
Cl2—C171.739 (8)C13—C141.475 (10)
Cl3—C281.730 (9)C14—C151.374 (10)
O1—C11.428 (7)C14—C191.402 (9)
O1—H10.820C15—C161.380 (11)
O2—C131.230 (8)C15—H150.930
O3—C241.211 (8)C16—C171.355 (11)
O4—C351.45 (2)C16—H160.930
O4—H40.820C17—C181.354 (11)
O5—C361.45 (2)C18—C191.358 (11)
O5—H50.820C18—H180.930
S1—C201.633 (8)C19—H190.930
S1—C231.661 (12)C20—C211.508 (10)
S2—C341.681 (8)C21—C221.411 (13)
S2—C311.692 (7)C21—H210.930
C1—C61.519 (9)C22—C231.279 (15)
C1—C71.543 (9)C22—H220.930
C1—C21.560 (9)C23—H230.930
C2—C131.509 (9)C24—C251.498 (10)
C2—C31.564 (9)C25—C261.346 (11)
C2—H20.980C25—C301.355 (11)
C3—C201.497 (10)C26—C271.371 (11)
C3—C41.533 (9)C26—H260.930
C3—H30.980C27—C281.369 (13)
C4—C241.531 (9)C27—H270.930
C4—C51.544 (9)C28—C291.304 (13)
C4—H4A0.980C29—C301.400 (13)
C5—C311.520 (9)C29—H290.930
C5—C61.535 (9)C30—H300.930
C5—H5A0.980C31—C321.411 (9)
C6—H6A0.970C32—C331.436 (11)
C6—H6B0.970C32—H320.930
C7—C121.363 (10)C33—C341.317 (11)
C7—C81.372 (10)C33—H330.930
C8—C91.383 (11)C34—H340.930
C8—H80.930C35—H35A0.960
C9—C101.341 (12)C35—H35B0.960
C9—H90.930C35—H35C0.960
C10—C111.372 (11)C36—H36A0.960
C11—C121.383 (10)C36—H36B0.960
C11—H110.930C36—H36C0.960
C1—O1—H1109.5C17—C16—H16120.4
C35—O4—H4109.5C15—C16—H16120.4
C36—O5—H5109.5C18—C17—C16121.3 (7)
C20—S1—C2395.2 (5)C18—C17—Cl2118.8 (6)
C34—S2—C3192.7 (4)C16—C17—Cl2119.9 (7)
O1—C1—C6106.3 (5)C17—C18—C19119.8 (7)
O1—C1—C7110.7 (5)C17—C18—H18120.1
C6—C1—C7111.2 (5)C19—C18—H18120.1
O1—C1—C2110.0 (5)C18—C19—C14121.2 (8)
C6—C1—C2108.6 (5)C18—C19—H19119.4
C7—C1—C2109.9 (5)C14—C19—H19119.4
C13—C2—C1110.9 (5)C3—C20—C21128.1 (6)
C13—C2—C3109.5 (5)C3—C20—S1123.8 (6)
C1—C2—C3109.4 (5)C21—C20—S1108.1 (5)
C13—C2—H2109.0C22—C21—C20108.3 (7)
C1—C2—H2109.0C22—C21—H21125.8
C3—C2—H2109.0C20—C21—H21125.8
C20—C3—C4111.9 (5)C23—C22—C21114.5 (10)
C20—C3—C2110.8 (5)C23—C22—H22122.7
C4—C3—C2109.8 (5)C21—C22—H22122.7
C20—C3—H3108.1C22—C23—S1113.7 (8)
C4—C3—H3108.1C22—C23—H23123.2
C2—C3—H3108.1S1—C23—H23123.2
C24—C4—C3108.4 (6)O3—C24—C25120.6 (6)
C24—C4—C5107.8 (5)O3—C24—C4118.0 (6)
C3—C4—C5112.3 (5)C25—C24—C4121.3 (7)
C24—C4—H4A109.4C26—C25—C30117.3 (8)
C3—C4—H4A109.4C26—C25—C24124.5 (7)
C5—C4—H4A109.4C30—C25—C24118.2 (8)
C31—C5—C6111.5 (6)C25—C26—C27122.6 (8)
C31—C5—C4109.5 (5)C25—C26—H26118.7
C6—C5—C4112.3 (5)C27—C26—H26118.7
C31—C5—H5A107.8C28—C27—C26118.6 (9)
C6—C5—H5A107.8C28—C27—H27120.7
C4—C5—H5A107.8C26—C27—H27120.7
C1—C6—C5111.3 (6)C29—C28—C27120.4 (8)
C1—C6—H6A109.4C29—C28—Cl3120.4 (9)
C5—C6—H6A109.4C27—C28—Cl3119.2 (9)
C1—C6—H6B109.4C28—C29—C30120.4 (9)
C5—C6—H6B109.4C28—C29—H29119.8
H6A—C6—H6B108.0C30—C29—H29119.8
C12—C7—C8117.2 (7)C25—C30—C29120.7 (9)
C12—C7—C1121.5 (6)C25—C30—H30119.6
C8—C7—C1121.3 (7)C29—C30—H30119.6
C7—C8—C9121.7 (8)C32—C31—C5126.6 (6)
C7—C8—H8119.2C32—C31—S2111.5 (5)
C9—C8—H8119.2C5—C31—S2121.8 (5)
C10—C9—C8119.9 (8)C31—C32—C33108.7 (7)
C10—C9—H9120.0C31—C32—H32125.7
C8—C9—H9120.0C33—C32—H32125.7
C9—C10—C11120.1 (7)C34—C33—C32114.7 (7)
C9—C10—Cl1118.8 (7)C34—C33—H33122.7
C11—C10—Cl1121.1 (7)C32—C33—H33122.7
C10—C11—C12119.2 (8)C33—C34—S2112.4 (6)
C10—C11—H11120.4C33—C34—H34123.8
C12—C11—H11120.4S2—C34—H34123.8
C7—C12—C11121.9 (7)O4—C35—H35A109.5
C7—C12—H12119.1O4—C35—H35B109.5
C11—C12—H12119.1H35A—C35—H35B109.5
O2—C13—C14119.8 (6)O4—C35—H35C109.5
O2—C13—C2117.9 (6)H35A—C35—H35C109.5
C14—C13—C2122.2 (6)H35B—C35—H35C109.5
C15—C14—C19117.2 (7)O5—C36—H36A109.5
C15—C14—C13124.0 (6)O5—C36—H36B109.5
C19—C14—C13118.8 (7)H36A—C36—H36B109.5
C14—C15—C16121.3 (7)O5—C36—H36C109.5
C14—C15—H15119.4H36A—C36—H36C109.5
C16—C15—H15119.4H36B—C36—H36C109.5
C17—C16—C15119.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.192.772 (7)128

Experimental details

Crystal data
Chemical formulaC34H25Cl3O3S2·0.5CH4O
Mr668.03
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)22.5660 (16), 12.1356 (12), 26.030 (2)
V3)7128.4 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.67 × 0.16 × 0.13
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.772, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
27584, 4502, 2357
Rint0.096
θmax (°)22.5
(sin θ/λ)max1)0.539
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.290, 1.09
No. of reflections4502
No. of parameters415
No. of restraints50
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O20.822.192.772 (7)128.1
 

Acknowledgements

The authors acknowledge support from the National Natural Science Foundation of Liaocheng University (No. X051040).

References

First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHuang, X.-Q. & Wang, J.-X. (2007). Acta Cryst. E63, o4168.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLuo, X. & Shan, Z. (2006). Acta Cryst. E62, o1631–o1632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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