2,4-Dibenzoyl-1-phenyl-3,5-di2-thien­ylcyclo­hexa­nol

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

doi:10.1107/S1600536807046843

2,4-Dibenzoyl-1-phenyl-3,5-di2-thienylcyclohexanol

The title compound, C₃₄H₂₈O₃S₂, was synthesized by the reaction of thiophene-2-carbaldehyde with acetophenone and NaOH under phase-transfer catalysis and solvent-free conditions. The central six-membered ring adopts a chair conformation and all the bulky side groups are located in equatorial positions. The hydroxyl group is involved in weak intramolecular hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046843/cv2306sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046843/cv2306Isup2.hkl Contains datablock I

CCDC reference: 287421

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.077
wR factor = 0.269
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.269
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C31    -   C32     ..       6.52 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C32    -   C33     ..       5.75 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In this paper, we present the title compound, (I), synthesized through the condensation and Micheal addition of thiophene-2-carbaldehyde with acetophenone under tetrabutyl ammonium bromide and solvent-free conditions.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the related compound (Luo et al., 2006). The hydroxyl group is involved in weak intramolecular hydrogen bonding (Table 1).

Related literature top

The crystal structure of 2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol was reported by Luo et al. (2006).

Experimental top

Acetophenone (6.25 mmol), freshly distilled thiophene-2-carbaldehyde (3.125 mmol) and NaOH (6.25 mmol), tetrabutyl ammonium bromide (1 mmol), were aggregated with a glass paddle in an open flask. The resulting mixture was washed with water several times to remove NaOH and was recrystallized from ethanol, affording the title compound as a crystalline solid. Elemental analysis: calculated for C₃₄H₂₈O₃S₂: C 74.42, H 5.14%; found: C 74.38, H 5.22%.

Structure description top

The crystal structure of 2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol was reported by Luo et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. ORTEP drawing of the title complex with atomic numbering scheme and displacement ellipsoids at 30% probability level.

2,4-Dibenzoyl-1-phenyl-3,5-di-2-thienylcyclohexanol top

Crystal data top

C₃₄H₂₈O₃S₂	D_x = 1.283 Mg m⁻³
M_r = 548.68	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3335 reflections
a = 19.477 (3) Å	θ = 2.6–25.6°
b = 12.1666 (19) Å	µ = 0.22 mm⁻¹
c = 23.970 (4) Å	T = 298 K
V = 5680.2 (16) Å³	Stick, colourless
Z = 8	0.53 × 0.17 × 0.08 mm
F(000) = 2304

Data collection top

Bruker SMART CCD area-detector diffractometer	4916 independent reflections
Radiation source: fine-focus sealed tube	2398 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→18
T_min = 0.892, T_max = 0.983	k = −14→14
26904 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.269	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1283P)² + 5.0247P] where P = (F_o² + 2F_c²)/3
4916 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₃₄H₂₈O₃S₂	V = 5680.2 (16) Å³
M_r = 548.68	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 19.477 (3) Å	µ = 0.22 mm⁻¹
b = 12.1666 (19) Å	T = 298 K
c = 23.970 (4) Å	0.53 × 0.17 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4916 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2398 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.983	R_int = 0.080
26904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.269	H-atom parameters constrained
S = 1.02	Δρ_max = 0.77 e Å⁻³
4916 reflections	Δρ_min = −0.61 e Å⁻³
352 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
O1	0.28423 (19)	0.6427 (3)	0.03495 (16)	0.0698 (11)
H1	0.2465	0.6726	0.0334	0.105*
O2	0.15784 (18)	0.6294 (3)	0.07682 (17)	0.0677 (11)
O3	0.3657 (2)	0.5494 (3)	0.20752 (16)	0.0656 (10)
S1	0.20614 (8)	0.29648 (12)	0.17794 (6)	0.0693 (5)
S2	0.52146 (10)	0.51469 (18)	0.11031 (9)	0.0962 (7)
C1	0.2765 (2)	0.5261 (4)	0.02428 (19)	0.0477 (12)
C2	0.2313 (2)	0.4741 (4)	0.07074 (19)	0.0434 (11)
H2	0.2255	0.3958	0.0625	0.052*
C3	0.2641 (2)	0.4855 (4)	0.12933 (18)	0.0430 (11)
H3	0.2678	0.5643	0.1373	0.052*
C4	0.3367 (2)	0.4390 (4)	0.12956 (18)	0.0418 (11)
H4	0.3345	0.3598	0.1223	0.050*
C5	0.3822 (2)	0.4937 (4)	0.0843 (2)	0.0487 (12)
H5	0.3842	0.5727	0.0920	0.058*
C6	0.3487 (2)	0.4774 (4)	0.0277 (2)	0.0511 (12)
H6A	0.3462	0.3993	0.0198	0.061*
H6B	0.3772	0.5111	−0.0007	0.061*
C7	0.2462 (3)	0.5062 (4)	−0.0332 (2)	0.0514 (12)
C8	0.2346 (4)	0.3995 (5)	−0.0542 (3)	0.086 (2)
H8	0.2420	0.3388	−0.0314	0.103*
C9	0.2124 (4)	0.3843 (6)	−0.1082 (3)	0.092 (2)
H9	0.2057	0.3135	−0.1218	0.110*
C10	0.2006 (3)	0.4698 (6)	−0.1410 (3)	0.0753 (17)
H10	0.1858	0.4575	−0.1774	0.090*
C11	0.2092 (3)	0.5711 (7)	−0.1239 (3)	0.086 (2)
H11	0.2008	0.6292	−0.1482	0.103*
C12	0.2301 (3)	0.5915 (4)	−0.0712 (2)	0.0579 (14)
H12	0.2341	0.6641	−0.0594	0.069*
C13	0.1598 (3)	0.5287 (4)	0.0718 (2)	0.0493 (12)
C14	0.0959 (3)	0.4646 (4)	0.0683 (2)	0.0504 (12)
C15	0.0930 (3)	0.3540 (4)	0.0557 (2)	0.0605 (14)
H15	0.1334	0.3148	0.0499	0.073*
C16	0.0307 (3)	0.3015 (5)	0.0517 (3)	0.0740 (17)
H16	0.0296	0.2270	0.0431	0.089*
C17	−0.0284 (3)	0.3552 (6)	0.0599 (3)	0.0797 (18)
H17	−0.0701	0.3184	0.0569	0.096*
C18	−0.0271 (3)	0.4650 (7)	0.0727 (3)	0.0821 (19)
H18	−0.0682	0.5019	0.0786	0.099*
C19	0.0338 (3)	0.5217 (5)	0.0771 (2)	0.0641 (15)
H19	0.0339	0.5962	0.0857	0.077*
C20	0.3696 (2)	0.4576 (4)	0.1866 (2)	0.0472 (12)
C21	0.4073 (2)	0.3687 (4)	0.2159 (2)	0.0514 (12)
C22	0.4086 (3)	0.2613 (5)	0.1975 (3)	0.0751 (17)
H22	0.3836	0.2411	0.1660	0.090*
C23	0.4472 (4)	0.1832 (6)	0.2260 (3)	0.096 (2)
H23	0.4461	0.1102	0.2145	0.115*
C24	0.4863 (4)	0.2127 (7)	0.2703 (3)	0.092 (2)
H24	0.5139	0.1608	0.2879	0.111*
C25	0.4850 (4)	0.3185 (8)	0.2891 (3)	0.099 (2)
H25	0.5108	0.3377	0.3203	0.119*
C26	0.4461 (3)	0.3978 (6)	0.2624 (2)	0.0746 (17)
H26	0.4458	0.4698	0.2755	0.089*
C27	0.2211 (2)	0.4357 (4)	0.17447 (19)	0.0461 (11)
C28	0.1907 (3)	0.4878 (5)	0.2192 (2)	0.0691 (16)
H28	0.1918	0.5633	0.2254	0.083*
C29	0.1577 (4)	0.4108 (7)	0.2542 (3)	0.099 (2)
H29	0.1347	0.4313	0.2865	0.119*
C30	0.1620 (3)	0.3066 (6)	0.2374 (3)	0.0780 (18)
H30	0.1429	0.2473	0.2563	0.094*
C31	0.4541 (3)	0.4490 (4)	0.0861 (2)	0.0549 (13)
C32	0.4758 (2)	0.3415 (4)	0.0676 (2)	0.0520 (13)
H32	0.4477	0.2907	0.0498	0.062*
C33	0.5462 (4)	0.3241 (7)	0.0806 (3)	0.096 (2)
H33	0.5686	0.2576	0.0746	0.116*
C34	0.5765 (3)	0.4104 (8)	0.1017 (3)	0.098 (3)
H34	0.6228	0.4136	0.1108	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.077 (3)	0.052 (2)	0.080 (3)	−0.0065 (18)	−0.008 (2)	0.0067 (19)
O2	0.063 (2)	0.043 (2)	0.097 (3)	0.0091 (17)	0.002 (2)	−0.006 (2)
O3	0.075 (3)	0.050 (2)	0.072 (2)	0.0017 (18)	−0.0136 (19)	−0.0172 (19)
S1	0.0824 (11)	0.0493 (9)	0.0763 (10)	−0.0061 (7)	0.0135 (8)	0.0047 (7)
S2	0.0794 (13)	0.1066 (16)	0.1025 (15)	−0.0131 (11)	−0.0025 (10)	−0.0136 (11)
C1	0.055 (3)	0.043 (3)	0.045 (3)	0.000 (2)	0.000 (2)	0.001 (2)
C2	0.048 (3)	0.033 (2)	0.050 (3)	0.002 (2)	−0.001 (2)	−0.003 (2)
C3	0.045 (3)	0.037 (3)	0.047 (3)	0.000 (2)	−0.005 (2)	−0.004 (2)
C4	0.043 (3)	0.034 (2)	0.049 (3)	−0.0024 (19)	−0.002 (2)	−0.002 (2)
C5	0.053 (3)	0.043 (3)	0.050 (3)	−0.005 (2)	0.003 (2)	0.004 (2)
C6	0.049 (3)	0.056 (3)	0.048 (3)	0.004 (2)	0.001 (2)	0.005 (2)
C7	0.053 (3)	0.053 (3)	0.048 (3)	0.004 (2)	−0.004 (2)	0.005 (2)
C8	0.139 (6)	0.053 (4)	0.066 (4)	0.015 (4)	−0.026 (4)	0.001 (3)
C9	0.118 (6)	0.088 (5)	0.069 (4)	0.005 (4)	−0.020 (4)	−0.017 (4)
C10	0.078 (4)	0.093 (5)	0.055 (4)	0.002 (4)	−0.006 (3)	0.006 (4)
C11	0.089 (5)	0.089 (5)	0.079 (5)	−0.001 (4)	−0.014 (4)	0.029 (4)
C12	0.058 (3)	0.048 (3)	0.067 (4)	−0.003 (2)	−0.012 (3)	0.023 (3)
C13	0.054 (3)	0.037 (3)	0.057 (3)	0.008 (2)	0.000 (2)	−0.006 (2)
C14	0.053 (3)	0.043 (3)	0.055 (3)	0.005 (2)	−0.004 (2)	0.003 (2)
C15	0.055 (3)	0.052 (3)	0.074 (4)	0.000 (3)	−0.003 (3)	−0.001 (3)
C16	0.065 (4)	0.069 (4)	0.089 (4)	−0.014 (3)	−0.009 (3)	−0.002 (3)
C17	0.059 (4)	0.086 (5)	0.095 (5)	−0.011 (3)	−0.010 (3)	0.006 (4)
C18	0.053 (4)	0.099 (5)	0.094 (5)	0.015 (3)	0.003 (3)	0.015 (4)
C19	0.045 (3)	0.067 (4)	0.081 (4)	0.010 (3)	0.006 (3)	0.007 (3)
C20	0.045 (3)	0.046 (3)	0.051 (3)	−0.003 (2)	−0.002 (2)	0.000 (2)
C21	0.046 (3)	0.060 (3)	0.049 (3)	0.002 (2)	−0.004 (2)	0.007 (2)
C22	0.090 (4)	0.046 (3)	0.090 (4)	0.006 (3)	−0.032 (3)	0.003 (3)
C23	0.106 (5)	0.068 (4)	0.114 (6)	0.020 (4)	−0.023 (5)	0.025 (4)
C24	0.086 (5)	0.097 (6)	0.094 (5)	0.026 (4)	−0.018 (4)	0.031 (4)
C25	0.100 (5)	0.131 (7)	0.066 (4)	0.032 (5)	−0.027 (4)	0.004 (4)
C26	0.075 (4)	0.091 (5)	0.058 (4)	0.015 (3)	−0.011 (3)	−0.008 (3)
C27	0.046 (3)	0.043 (3)	0.049 (3)	0.002 (2)	0.002 (2)	−0.001 (2)
C28	0.089 (4)	0.055 (4)	0.063 (3)	−0.003 (3)	0.025 (3)	−0.009 (3)
C29	0.117 (6)	0.110 (6)	0.069 (4)	−0.020 (5)	0.043 (4)	−0.006 (4)
C30	0.074 (4)	0.089 (5)	0.071 (4)	−0.018 (3)	0.015 (3)	0.013 (4)
C31	0.054 (3)	0.057 (3)	0.054 (3)	0.002 (2)	0.007 (2)	0.004 (2)
C32	0.025 (2)	0.034 (2)	0.097 (4)	0.0049 (18)	0.004 (2)	−0.010 (2)
C33	0.076 (5)	0.106 (6)	0.107 (6)	0.035 (4)	−0.006 (4)	−0.004 (5)
C34	0.052 (4)	0.181 (9)	0.062 (4)	−0.005 (5)	0.000 (3)	0.022 (5)

Geometric parameters (Å, º) top

O1—C1	1.450 (6)	C13—C14	1.471 (7)
O1—H1	0.8200	C14—C15	1.380 (7)
O2—C13	1.232 (6)	C14—C19	1.412 (7)
O3—C20	1.226 (6)	C15—C16	1.375 (8)
S1—C30	1.669 (6)	C15—H15	0.9300
S1—C27	1.721 (5)	C16—C17	1.338 (9)
S2—C31	1.643 (6)	C16—H16	0.9300
S2—C34	1.673 (9)	C17—C18	1.370 (9)
C1—C7	1.519 (7)	C17—H17	0.9300
C1—C6	1.527 (7)	C18—C19	1.375 (9)
C1—C2	1.554 (7)	C18—H18	0.9300
C2—C13	1.543 (7)	C19—H19	0.9300
C2—C3	1.549 (6)	C20—C21	1.484 (7)
C2—H2	0.9800	C21—C22	1.379 (7)
C3—C27	1.496 (6)	C21—C26	1.394 (7)
C3—C4	1.523 (6)	C22—C23	1.391 (8)
C3—H3	0.9800	C22—H22	0.9300
C4—C20	1.527 (6)	C23—C24	1.356 (10)
C4—C5	1.551 (6)	C23—H23	0.9300
C4—H4	0.9800	C24—C25	1.364 (10)
C5—C31	1.502 (7)	C24—H24	0.9300
C5—C6	1.519 (7)	C25—C26	1.383 (9)
C5—H5	0.9800	C25—H25	0.9300
C6—H6A	0.9700	C26—H26	0.9300
C6—H6B	0.9700	C27—C28	1.378 (7)
C7—C8	1.411 (8)	C28—C29	1.413 (8)
C7—C12	1.415 (7)	C28—H28	0.9300
C8—C9	1.378 (9)	C29—C30	1.332 (9)
C8—H8	0.9300	C29—H29	0.9300
C9—C10	1.323 (9)	C30—H30	0.9300
C9—H9	0.9300	C31—C32	1.444 (7)
C10—C11	1.309 (9)	C32—C33	1.422 (9)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.352 (8)	C33—C34	1.307 (10)
C11—H11	0.9300	C33—H33	0.9300
C12—H12	0.9300	C34—H34	0.9300
C13—O2	1.232 (6)

C1—O1—H1	109.5	C15—C14—C13	124.3 (5)
C30—S1—C27	93.2 (3)	C19—C14—C13	117.2 (5)
C31—S2—C34	95.7 (4)	C16—C15—C14	120.3 (5)
O1—C1—C7	110.9 (4)	C16—C15—H15	119.8
O1—C1—C6	106.0 (4)	C14—C15—H15	119.8
C7—C1—C6	110.2 (4)	C17—C16—C15	121.5 (6)
O1—C1—C2	109.3 (4)	C17—C16—H16	119.3
C7—C1—C2	111.4 (4)	C15—C16—H16	119.3
C6—C1—C2	109.0 (4)	C16—C17—C18	119.5 (6)
C13—C2—C3	108.6 (4)	C16—C17—H17	120.2
C13—C2—C1	110.4 (4)	C18—C17—H17	120.2
C3—C2—C1	112.3 (4)	C17—C18—C19	121.5 (6)
C13—C2—H2	108.5	C17—C18—H18	119.2
C3—C2—H2	108.5	C19—C18—H18	119.2
C1—C2—H2	108.5	C18—C19—C14	118.7 (6)
C27—C3—C4	111.5 (4)	C18—C19—H19	120.6
C27—C3—C2	112.8 (4)	C14—C19—H19	120.6
C4—C3—C2	110.7 (4)	O3—C20—C21	120.0 (4)
C27—C3—H3	107.1	O3—C20—C4	118.4 (4)
C4—C3—H3	107.1	C21—C20—C4	121.5 (4)
C2—C3—H3	107.1	C22—C21—C26	119.1 (5)
C3—C4—C20	109.7 (4)	C22—C21—C20	123.3 (5)
C3—C4—C5	111.6 (4)	C26—C21—C20	117.5 (5)
C20—C4—C5	108.8 (4)	C21—C22—C23	120.0 (6)
C3—C4—H4	108.9	C21—C22—H22	120.0
C20—C4—H4	108.9	C23—C22—H22	120.0
C5—C4—H4	108.9	C24—C23—C22	120.6 (7)
C31—C5—C6	112.2 (4)	C24—C23—H23	119.7
C31—C5—C4	111.0 (4)	C22—C23—H23	119.7
C6—C5—C4	108.8 (4)	C23—C24—C25	119.8 (6)
C31—C5—H5	108.2	C23—C24—H24	120.1
C6—C5—H5	108.2	C25—C24—H24	120.1
C4—C5—H5	108.2	C24—C25—C26	121.1 (7)
C5—C6—C1	113.1 (4)	C24—C25—H25	119.5
C5—C6—H6A	108.9	C26—C25—H25	119.5
C1—C6—H6A	108.9	C25—C26—C21	119.4 (6)
C5—C6—H6B	108.9	C25—C26—H26	120.3
C1—C6—H6B	108.9	C21—C26—H26	120.3
H6A—C6—H6B	107.8	C28—C27—C3	128.1 (4)
C8—C7—C12	114.3 (5)	C28—C27—S1	110.0 (4)
C8—C7—C1	122.2 (4)	C3—C27—S1	121.9 (3)
C12—C7—C1	123.5 (5)	C27—C28—C29	110.6 (5)
C9—C8—C7	120.6 (6)	C27—C28—H28	124.7
C9—C8—H8	119.7	C29—C28—H28	124.7
C7—C8—H8	119.7	C30—C29—C28	115.0 (6)
C10—C9—C8	120.5 (7)	C30—C29—H29	122.5
C10—C9—H9	119.8	C28—C29—H29	122.5
C8—C9—H9	119.8	C29—C30—S1	111.1 (5)
C11—C10—C9	122.1 (6)	C29—C30—H30	124.4
C11—C10—H10	118.9	S1—C30—H30	124.4
C9—C10—H10	118.9	C32—C31—C5	126.3 (5)
C10—C11—C12	120.3 (6)	C32—C31—S2	108.4 (4)
C10—C11—H11	119.8	C5—C31—S2	125.3 (4)
C12—C11—H11	119.8	C33—C32—C31	110.5 (5)
C11—C12—C7	122.2 (6)	C33—C32—H32	124.7
C11—C12—H12	118.9	C31—C32—H32	124.7
C7—C12—H12	118.9	C34—C33—C32	113.6 (7)
O2—C13—C14	120.4 (4)	C34—C33—H33	123.2
O2—C13—C14	120.4 (4)	C32—C33—H33	123.2
O2—C13—C2	117.2 (4)	C33—C34—S2	111.6 (5)
O2—C13—C2	117.2 (4)	C33—C34—H34	124.2
C14—C13—C2	122.3 (4)	S2—C34—H34	124.2
C15—C14—C19	118.5 (5)

O1—C1—C2—C13	59.8 (5)	O2—C13—C14—C19	−6.8 (7)
C7—C1—C2—C13	−63.1 (5)	C2—C13—C14—C19	171.8 (5)
C6—C1—C2—C13	175.2 (4)	C19—C14—C15—C16	0.3 (8)
O1—C1—C2—C3	−61.6 (5)	C13—C14—C15—C16	−178.1 (5)
C7—C1—C2—C3	175.5 (4)	C14—C15—C16—C17	−0.2 (9)
C6—C1—C2—C3	53.8 (5)	C15—C16—C17—C18	−0.2 (10)
C13—C2—C3—C27	57.6 (5)	C16—C17—C18—C19	0.4 (10)
C1—C2—C3—C27	−180.0 (4)	C17—C18—C19—C14	−0.3 (9)
C13—C2—C3—C4	−176.6 (4)	C15—C14—C19—C18	−0.1 (8)
C1—C2—C3—C4	−54.2 (5)	C13—C14—C19—C18	178.4 (5)
C27—C3—C4—C20	−57.1 (5)	C3—C4—C20—O3	−48.0 (6)
C2—C3—C4—C20	176.4 (4)	C5—C4—C20—O3	74.4 (5)
C27—C3—C4—C5	−177.8 (4)	C3—C4—C20—C21	133.8 (4)
C2—C3—C4—C5	55.7 (5)	C5—C4—C20—C21	−103.8 (5)
C3—C4—C5—C31	178.5 (4)	O3—C20—C21—C22	174.0 (5)
C20—C4—C5—C31	57.3 (5)	C4—C20—C21—C22	−7.8 (8)
C3—C4—C5—C6	−57.5 (5)	O3—C20—C21—C26	−9.7 (7)
C20—C4—C5—C6	−178.7 (4)	C4—C20—C21—C26	168.5 (5)
C31—C5—C6—C1	−177.8 (4)	C26—C21—C22—C23	1.3 (9)
C4—C5—C6—C1	59.0 (5)	C20—C21—C22—C23	177.6 (6)
O1—C1—C6—C5	60.3 (5)	C21—C22—C23—C24	−3.1 (11)
C7—C1—C6—C5	−179.7 (4)	C22—C23—C24—C25	3.6 (12)
C2—C1—C6—C5	−57.2 (5)	C23—C24—C25—C26	−2.2 (12)
O1—C1—C7—C8	178.9 (5)	C24—C25—C26—C21	0.4 (11)
C6—C1—C7—C8	61.9 (7)	C22—C21—C26—C25	0.0 (9)
C2—C1—C7—C8	−59.2 (7)	C20—C21—C26—C25	−176.4 (6)
O1—C1—C7—C12	1.9 (7)	C4—C3—C27—C28	117.7 (6)
C6—C1—C7—C12	−115.1 (5)	C2—C3—C27—C28	−117.0 (6)
C2—C1—C7—C12	123.8 (5)	C4—C3—C27—S1	−59.4 (5)
C12—C7—C8—C9	2.7 (9)	C2—C3—C27—S1	66.0 (5)
C1—C7—C8—C9	−174.6 (6)	C30—S1—C27—C28	−0.8 (5)
C7—C8—C9—C10	−1.1 (11)	C30—S1—C27—C3	176.7 (4)
C8—C9—C10—C11	−0.2 (12)	C3—C27—C28—C29	−176.5 (5)
C9—C10—C11—C12	−0.5 (11)	S1—C27—C28—C29	0.8 (7)
C10—C11—C12—C7	2.5 (10)	C27—C28—C29—C30	−0.4 (9)
C8—C7—C12—C11	−3.5 (8)	C28—C29—C30—S1	−0.3 (9)
C1—C7—C12—C11	173.8 (5)	C27—S1—C30—C29	0.6 (6)
O2—O2—C13—C14	0.0 (17)	C6—C5—C31—C32	−48.9 (7)
O2—O2—C13—C2	0.0 (17)	C4—C5—C31—C32	73.0 (6)
C3—C2—C13—O2	68.3 (6)	C6—C5—C31—S2	131.9 (4)
C1—C2—C13—O2	−55.2 (6)	C4—C5—C31—S2	−106.1 (5)
C3—C2—C13—O2	68.3 (6)	C34—S2—C31—C32	−2.9 (4)
C1—C2—C13—O2	−55.2 (6)	C34—S2—C31—C5	176.4 (5)
C3—C2—C13—C14	−110.3 (5)	C5—C31—C32—C33	−174.4 (5)
C1—C2—C13—C14	126.2 (5)	S2—C31—C32—C33	4.9 (6)
O2—C13—C14—C15	171.6 (5)	C31—C32—C33—C34	−5.2 (9)
O2—C13—C14—C15	171.6 (5)	C32—C33—C34—S2	3.0 (8)
C2—C13—C14—C15	−9.8 (8)	C31—S2—C34—C33	0.0 (6)
O2—C13—C14—C19	−6.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.08	2.663 (5)	127

Experimental details

Crystal data
Chemical formula	C₃₄H₂₈O₃S₂
M_r	548.68
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	19.477 (3), 12.1666 (19), 23.970 (4)
V (Å³)	5680.2 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.53 × 0.17 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.892, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	26904, 4916, 2398
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.269, 1.02
No. of reflections	4916
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.61

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).