5,7-Bis(1-benzothio­phen-2-yl)-2,3-dihydro­thieno[3,4-b][1,4]dioxine

Sugumar, P.; Ranjith, S.; Clement, J.A.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536808012324

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1049

doi:10.1107/S1600536808012324

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5,7-Bis(1-benzothiophen-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

P. Sugumar,^a S. Ranjith,^a J. Arul Clement,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 1 April 2008; accepted 28 April 2008; online 10 May 2008)

In the title compound, C₂₂H₁₄O₂S₃, the dioxane ring is disordered over two sites [site occupancies = 0.623 (3) and 0.377 (3)]; both components adopt half-chair conformations. The two benzothiophene ring systems are asymmetrically twisted away from the attached thiophene ring [dihedral angles = 20.57 (3) and 6.70 (3)°] and are oriented at an angle of 26.83 (3)°. No significant hydrogen bonding or π–π interactions are observed in the crystal structure.

Related literature

For related literature, see: Cohen et al. (1977 ); Csaszar & Morvay (1983 ); Dzhurayev et al. (1992 ); EI-Maghraby et al. (1984 ); Gewald et al. (1996 ); Lakshmi et al. (1985 ); Pellis & West (1968 ). For the synthesis, see: Amaladass et al. (2007 ).

Experimental

Crystal data

C₂₂H₁₄O₂S₃
M_r = 406.51
Monoclinic, P 2₁ /c
a = 16.1602 (5) Å
b = 8.3524 (3) Å
c = 14.1814 (4) Å
β = 107.428 (2)°
V = 1826.28 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 (2) K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: none
26571 measured reflections
7059 independent reflections
4551 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.142
S = 0.99
7059 reflections
251 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012324/ci2577sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012324/ci2577Isup2.hkl

checkCIF report

Comment top

Sulfur containing Schiff bases (Pellis & West, 1968; Cohen et al., 1977; Csaszar & Morvay,1983; Lakshmi et al., 1985) and their thiophen derivatives (EI-Maghraby et al., 1984; Dzhurayev et al., 1992) possess pharmacological activities such as anti-bacterial, anti-cancer, anti-inflammatory and anti-toxic properties (Gewald et al., 1996). Benzo[b]thiophene analogs have been shown to possess interesting estrogenic and antiestrogenic effects. We report here the crystal structure of the title compound.

The C1—C8/S3 and C15—C22/S2 benzothiophene ring systems are essentially planar and are oriented at angles of 20.57 (3)° and 6.70 (3)°, respectively, with respect to the thiophene ring. The dihedral angle between the two benzothiophene ring systems is 26.83 (3)°. Both the major and minor conformers of the disordered dioxane ring adopt half-chair conformations. The crystal packing is stabilized by van der Waals forces.

Related literature top

For related literature, see: Cohen et al. (1977); Csaszar & Morvay (1983); Dzhurayev et al. (1992); EI-Maghraby et al. (1984); Gewald et al. (1996); Lakshmi et al. (1985); Pellis & West (1968). For the synthesis, see: Amaladass et al. (2007).

Experimental top

The title compound was prepared according to the procedure reported by Amaladass et al. (2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation method.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disorder components are shown.

5,7-Bis(1-benzothiophen-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine top

Crystal data top

C₂₂H₁₄O₂S₃	F(000) = 840
M_r = 406.51	D_x = 1.478 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4583 reflections
a = 16.1602 (5) Å	θ = 2.8–33.8°
b = 8.3524 (3) Å	µ = 0.42 mm⁻¹
c = 14.1814 (4) Å	T = 293 K
β = 107.428 (2)°	Block, light green
V = 1826.28 (10) Å³	0.15 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4551 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 33.4°, θ_min = 2.8°
ω and ϕ scans	h = −24→24
26571 measured reflections	k = −12→10
7059 independent reflections	l = −21→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0749P)² + 0.444P] where P = (F_o² + 2F_c²)/3
7059 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.61 e Å⁻³
3 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₁₄O₂S₃	V = 1826.28 (10) Å³
M_r = 406.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1602 (5) Å	µ = 0.42 mm⁻¹
b = 8.3524 (3) Å	T = 293 K
c = 14.1814 (4) Å	0.15 × 0.13 × 0.10 mm
β = 107.428 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4551 reflections with I > 2σ(I)
26571 measured reflections	R_int = 0.028
7059 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.99	Δρ_max = 0.61 e Å⁻³
7059 reflections	Δρ_min = −0.43 e Å⁻³
251 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)
C1	−0.28863 (11)	0.4031 (2)	−0.01894 (14)	0.0499 (4)
H1	−0.2949	0.3569	−0.0804	0.060*
C2	−0.35994 (12)	0.4572 (3)	0.00498 (16)	0.0578 (5)
H2	−0.4145	0.4490	−0.0412	0.069*
C3	−0.35223 (12)	0.5241 (2)	0.09694 (18)	0.0597 (5)
H3	−0.4017	0.5590	0.1115	0.072*
C4	−0.27258 (12)	0.5395 (2)	0.16681 (16)	0.0533 (4)
H4	−0.2674	0.5837	0.2285	0.064*
C5	−0.19971 (10)	0.48665 (19)	0.14227 (13)	0.0419 (3)
C6	−0.20599 (10)	0.41809 (19)	0.05007 (12)	0.0400 (3)
C7	−0.12301 (10)	0.3765 (2)	0.03966 (13)	0.0430 (3)
H7	−0.1153	0.3287	−0.0164	0.052*
C8	−0.05619 (10)	0.41564 (19)	0.12239 (11)	0.0374 (3)
C9	0.03586 (9)	0.39615 (18)	0.13747 (11)	0.0364 (3)
C10	0.07580 (9)	0.29651 (18)	0.08760 (11)	0.0357 (3)
C11A	0.08383 (17)	0.1322 (5)	−0.0432 (2)	0.0502 (8)	0.623 (3)
H11A	0.0937	0.2125	−0.0881	0.060*	0.623 (3)
H11B	0.0543	0.0420	−0.0820	0.060*	0.623 (3)
C12A	0.16828 (17)	0.0790 (3)	0.0260 (2)	0.0485 (6)	0.623 (3)
H12A	0.1574	−0.0005	0.0707	0.058*	0.623 (3)
H12B	0.2022	0.0283	−0.0117	0.058*	0.623 (3)
C11B	0.0915 (3)	0.0850 (5)	−0.0061 (4)	0.0502 (8)	0.377 (3)
H11C	0.0623	0.0295	−0.0670	0.060*	0.377 (3)
H11D	0.1046	0.0059	0.0464	0.060*	0.377 (3)
C12B	0.1754 (3)	0.1472 (7)	−0.0147 (2)	0.0485 (6)	0.377 (3)
H12C	0.2092	0.0622	−0.0318	0.058*	0.377 (3)
H12D	0.1658	0.2309	−0.0643	0.058*	0.377 (3)
C13	0.16712 (9)	0.30254 (18)	0.12251 (11)	0.0365 (3)
C14	0.19858 (9)	0.40987 (19)	0.19816 (11)	0.0362 (3)
C15	0.28812 (9)	0.44752 (19)	0.24924 (11)	0.0352 (3)
C16	0.36041 (10)	0.3755 (2)	0.23942 (12)	0.0416 (3)
H16	0.3587	0.2893	0.1973	0.050*
C17	0.43920 (10)	0.44442 (19)	0.29966 (11)	0.0380 (3)
C18	0.52506 (11)	0.4008 (2)	0.30912 (15)	0.0512 (4)
H18	0.5366	0.3159	0.2725	0.061*
C19	0.59199 (11)	0.4840 (2)	0.37253 (15)	0.0521 (4)
H19	0.6489	0.4558	0.3781	0.062*
C20	0.57576 (11)	0.6105 (2)	0.42876 (14)	0.0483 (4)
H20	0.6220	0.6645	0.4722	0.058*
C21	0.49236 (11)	0.6563 (2)	0.42076 (13)	0.0469 (4)
H21	0.4816	0.7414	0.4578	0.056*
C22	0.42398 (9)	0.57260 (19)	0.35592 (11)	0.0374 (3)
O1	0.03162 (7)	0.19777 (15)	0.01304 (9)	0.0476 (3)
O2	0.21883 (7)	0.21067 (15)	0.08407 (9)	0.0467 (3)
S1	0.11311 (2)	0.50367 (5)	0.22588 (3)	0.04068 (11)
S2	0.31369 (3)	0.60648 (5)	0.33305 (3)	0.04677 (12)
S3	−0.09260 (3)	0.49989 (6)	0.21576 (3)	0.04834 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0415 (8)	0.0560 (10)	0.0467 (9)	−0.0071 (7)	0.0047 (7)	0.0089 (8)
C2	0.0338 (8)	0.0654 (12)	0.0667 (12)	−0.0030 (8)	0.0037 (8)	0.0162 (10)
C3	0.0355 (8)	0.0585 (11)	0.0856 (15)	0.0057 (8)	0.0188 (9)	0.0054 (10)
C4	0.0418 (9)	0.0515 (10)	0.0684 (12)	0.0037 (7)	0.0192 (8)	−0.0063 (9)
C5	0.0336 (7)	0.0393 (8)	0.0529 (9)	−0.0002 (6)	0.0131 (6)	0.0001 (7)
C6	0.0355 (7)	0.0390 (8)	0.0445 (8)	−0.0019 (6)	0.0103 (6)	0.0061 (6)
C7	0.0352 (7)	0.0473 (9)	0.0470 (8)	0.0003 (6)	0.0132 (6)	0.0079 (7)
C8	0.0331 (7)	0.0393 (8)	0.0401 (7)	0.0004 (5)	0.0114 (5)	0.0008 (6)
C9	0.0316 (6)	0.0395 (8)	0.0378 (7)	−0.0003 (5)	0.0098 (5)	0.0003 (6)
C10	0.0332 (6)	0.0376 (7)	0.0353 (7)	−0.0025 (5)	0.0086 (5)	−0.0015 (6)
C11A	0.0450 (11)	0.070 (2)	0.0369 (17)	−0.0104 (12)	0.0148 (13)	−0.0198 (14)
C12A	0.0432 (11)	0.0540 (18)	0.0478 (15)	0.0009 (11)	0.0128 (11)	−0.0150 (11)
C11B	0.0450 (11)	0.070 (2)	0.0369 (17)	−0.0104 (12)	0.0148 (13)	−0.0198 (14)
C12B	0.0432 (11)	0.0540 (18)	0.0478 (15)	0.0009 (11)	0.0128 (11)	−0.0150 (11)
C13	0.0340 (7)	0.0378 (8)	0.0383 (7)	0.0019 (5)	0.0116 (5)	−0.0024 (6)
C14	0.0317 (6)	0.0395 (8)	0.0368 (7)	−0.0001 (5)	0.0095 (5)	−0.0018 (6)
C15	0.0338 (7)	0.0372 (7)	0.0349 (7)	−0.0016 (5)	0.0106 (5)	−0.0026 (6)
C16	0.0363 (7)	0.0423 (8)	0.0461 (8)	−0.0022 (6)	0.0122 (6)	−0.0089 (7)
C17	0.0338 (7)	0.0402 (8)	0.0411 (7)	−0.0023 (6)	0.0130 (6)	−0.0008 (6)
C18	0.0364 (8)	0.0547 (10)	0.0645 (11)	0.0013 (7)	0.0181 (7)	−0.0109 (8)
C19	0.0328 (8)	0.0577 (11)	0.0659 (11)	−0.0027 (7)	0.0153 (7)	−0.0001 (9)
C20	0.0360 (8)	0.0509 (10)	0.0535 (9)	−0.0103 (7)	0.0066 (7)	0.0011 (8)
C21	0.0402 (8)	0.0486 (9)	0.0495 (9)	−0.0081 (7)	0.0096 (7)	−0.0090 (7)
C22	0.0324 (7)	0.0401 (8)	0.0394 (7)	−0.0029 (6)	0.0103 (5)	−0.0005 (6)
O1	0.0379 (6)	0.0534 (7)	0.0495 (6)	−0.0055 (5)	0.0100 (5)	−0.0169 (5)
O2	0.0355 (5)	0.0520 (7)	0.0520 (6)	0.0028 (5)	0.0121 (5)	−0.0160 (5)
S1	0.03413 (18)	0.0475 (2)	0.0409 (2)	−0.00031 (15)	0.01199 (14)	−0.00916 (16)
S2	0.03469 (19)	0.0501 (2)	0.0539 (2)	−0.00041 (16)	0.01081 (16)	−0.01687 (18)
S3	0.0361 (2)	0.0621 (3)	0.0464 (2)	0.00043 (17)	0.01175 (16)	−0.01084 (19)

Geometric parameters (Å, º) top

C1—C2	1.372 (3)	C11B—O1	1.434 (2)
C1—C6	1.405 (2)	C11B—C12B	1.490 (3)
C1—H1	0.93	C11B—H11C	0.97
C2—C3	1.390 (3)	C11B—H11D	0.97
C2—H2	0.93	C12B—O2	1.465 (3)
C3—C4	1.375 (3)	C12B—H12C	0.97
C3—H3	0.93	C12B—H12D	0.97
C4—C5	1.396 (2)	C13—O2	1.3627 (18)
C4—H4	0.93	C13—C14	1.373 (2)
C5—C6	1.403 (2)	C14—C15	1.445 (2)
C5—S3	1.7361 (17)	C14—S1	1.7325 (15)
C6—C7	1.435 (2)	C15—C16	1.358 (2)
C7—C8	1.375 (2)	C15—S2	1.7470 (15)
C7—H7	0.93	C16—C17	1.425 (2)
C8—C9	1.447 (2)	C16—H16	0.93
C8—S3	1.7496 (16)	C17—C22	1.400 (2)
C9—C10	1.372 (2)	C17—C18	1.401 (2)
C9—S1	1.7318 (15)	C18—C19	1.371 (3)
C10—O1	1.3622 (18)	C18—H18	0.93
C10—C13	1.410 (2)	C19—C20	1.395 (3)
C11A—O1	1.433 (2)	C19—H19	0.93
C11A—C12A	1.490 (3)	C20—C21	1.373 (2)
C11A—H11A	0.97	C20—H20	0.93
C11A—H11B	0.97	C21—C22	1.395 (2)
C12A—O2	1.467 (2)	C21—H21	0.93
C12A—H12A	0.97	C22—S2	1.7365 (15)
C12A—H12B	0.97

C2—C1—C6	119.47 (18)	C12B—C11B—H11D	107.8
C2—C1—H1	120.3	H11C—C11B—H11D	107.2
C6—C1—H1	120.3	O2—C12B—C11B	103.6 (3)
C1—C2—C3	121.26 (17)	O2—C12B—H12C	111.0
C1—C2—H2	119.4	C11B—C12B—H12C	111.0
C3—C2—H2	119.4	O2—C12B—H12D	111.0
C4—C3—C2	121.00 (18)	C11B—C12B—H12D	111.0
C4—C3—H3	119.5	H12C—C12B—H12D	109.0
C2—C3—H3	119.5	O2—C13—C14	123.51 (13)
C3—C4—C5	117.93 (19)	O2—C13—C10	122.83 (13)
C3—C4—H4	121.0	C14—C13—C10	113.66 (13)
C5—C4—H4	121.0	C13—C14—C15	127.90 (14)
C4—C5—C6	122.04 (16)	C13—C14—S1	109.79 (11)
C4—C5—S3	126.46 (15)	C15—C14—S1	122.30 (12)
C6—C5—S3	111.48 (12)	C16—C15—C14	127.96 (14)
C5—C6—C1	118.29 (16)	C16—C15—S2	111.78 (11)
C5—C6—C7	112.69 (14)	C14—C15—S2	120.24 (11)
C1—C6—C7	129.00 (17)	C15—C16—C17	113.66 (14)
C8—C7—C6	111.96 (15)	C15—C16—H16	123.2
C8—C7—H7	124.0	C17—C16—H16	123.2
C6—C7—H7	124.0	C22—C17—C18	118.81 (15)
C7—C8—C9	127.53 (14)	C22—C17—C16	111.87 (13)
C7—C8—S3	112.65 (12)	C18—C17—C16	129.32 (16)
C9—C8—S3	119.82 (11)	C19—C18—C17	119.69 (17)
C10—C9—C8	127.84 (14)	C19—C18—H18	120.2
C10—C9—S1	109.84 (11)	C17—C18—H18	120.2
C8—C9—S1	122.33 (12)	C18—C19—C20	120.82 (16)
O1—C10—C9	123.31 (13)	C18—C19—H19	119.6
O1—C10—C13	122.97 (13)	C20—C19—H19	119.6
C9—C10—C13	113.69 (13)	C21—C20—C19	120.79 (16)
O1—C11A—C12A	108.9 (2)	C21—C20—H20	119.6
O1—C11A—H11A	109.9	C19—C20—H20	119.6
C12A—C11A—H11A	109.9	C20—C21—C22	118.62 (17)
O1—C11A—H11B	109.9	C20—C21—H21	120.7
C12A—C11A—H11B	109.9	C22—C21—H21	120.7
H11A—C11A—H11B	108.3	C21—C22—C17	121.27 (15)
O2—C12A—C11A	113.1 (2)	C21—C22—S2	127.40 (13)
O2—C12A—H12A	109.0	C17—C22—S2	111.34 (11)
C11A—C12A—H12A	109.0	C10—O1—C11A	113.88 (16)
O2—C12A—H12B	109.0	C10—O1—C11B	108.6 (3)
C11A—C12A—H12B	109.0	C13—O2—C12B	114.2 (2)
H12A—C12A—H12B	107.8	C13—O2—C12A	109.99 (15)
O1—C11B—C12B	117.9 (4)	C9—S1—C14	92.98 (7)
O1—C11B—H11C	107.8	C22—S2—C15	91.35 (7)
C12B—C11B—H11C	107.8	C5—S3—C8	91.20 (8)
O1—C11B—H11D	107.8

C6—C1—C2—C3	−1.2 (3)	C15—C16—C17—C18	179.46 (17)
C1—C2—C3—C4	0.6 (3)	C22—C17—C18—C19	−0.2 (3)
C2—C3—C4—C5	0.4 (3)	C16—C17—C18—C19	−179.69 (18)
C3—C4—C5—C6	−0.7 (3)	C17—C18—C19—C20	0.8 (3)
C3—C4—C5—S3	177.48 (15)	C18—C19—C20—C21	−1.0 (3)
C4—C5—C6—C1	0.1 (2)	C19—C20—C21—C22	0.7 (3)
S3—C5—C6—C1	−178.33 (13)	C20—C21—C22—C17	−0.1 (3)
C4—C5—C6—C7	178.37 (16)	C20—C21—C22—S2	179.76 (14)
S3—C5—C6—C7	−0.02 (18)	C18—C17—C22—C21	−0.2 (2)
C2—C1—C6—C5	0.8 (2)	C16—C17—C22—C21	179.43 (15)
C2—C1—C6—C7	−177.15 (17)	C18—C17—C22—S2	179.96 (13)
C5—C6—C7—C8	−0.8 (2)	C16—C17—C22—S2	−0.43 (18)
C1—C6—C7—C8	177.27 (16)	C9—C10—O1—C11A	166.6 (2)
C6—C7—C8—C9	−177.96 (15)	C13—C10—O1—C11A	−15.2 (3)
C6—C7—C8—S3	1.29 (18)	C9—C10—O1—C11B	−166.3 (3)
C7—C8—C9—C10	−20.4 (3)	C13—C10—O1—C11B	11.9 (3)
S3—C8—C9—C10	160.45 (14)	C12A—C11A—O1—C10	43.7 (3)
C7—C8—C9—S1	159.31 (14)	C12A—C11A—O1—C11B	−39.6 (5)
S3—C8—C9—S1	−19.89 (18)	C12B—C11B—O1—C10	−46.7 (5)
C8—C9—C10—O1	0.2 (3)	C12B—C11B—O1—C11A	60.0 (5)
S1—C9—C10—O1	−179.48 (12)	C14—C13—O2—C12B	−160.2 (3)
C8—C9—C10—C13	−178.15 (15)	C10—C13—O2—C12B	19.4 (3)
S1—C9—C10—C13	2.15 (17)	C14—C13—O2—C12A	163.91 (19)
O1—C11A—C12A—O2	−62.3 (4)	C10—C13—O2—C12A	−16.4 (2)
O1—C11B—C12B—O2	64.4 (6)	C11B—C12B—O2—C13	−46.1 (4)
O1—C10—C13—O2	0.4 (2)	C11B—C12B—O2—C12A	43.8 (2)
C9—C10—C13—O2	178.81 (14)	C11A—C12A—O2—C13	47.1 (3)
O1—C10—C13—C14	−179.88 (14)	C11A—C12A—O2—C12B	−56.9 (4)
C9—C10—C13—C14	−1.5 (2)	C10—C9—S1—C14	−1.77 (12)
O2—C13—C14—C15	0.8 (3)	C8—C9—S1—C14	178.51 (13)
C10—C13—C14—C15	−178.84 (15)	C13—C14—S1—C9	0.95 (13)
O2—C13—C14—S1	179.79 (12)	C15—C14—S1—C9	179.96 (13)
C10—C13—C14—S1	0.11 (17)	C21—C22—S2—C15	−179.22 (16)
C13—C14—C15—C16	−6.2 (3)	C17—C22—S2—C15	0.63 (13)
S1—C14—C15—C16	174.99 (14)	C16—C15—S2—C22	−0.69 (13)
C13—C14—C15—S2	171.90 (13)	C14—C15—S2—C22	−179.06 (13)
S1—C14—C15—S2	−6.92 (19)	C4—C5—S3—C8	−177.68 (17)
C14—C15—C16—C17	178.79 (15)	C6—C5—S3—C8	0.63 (13)
S2—C15—C16—C17	0.57 (19)	C7—C8—S3—C5	−1.11 (13)
C15—C16—C17—C22	−0.1 (2)	C9—C8—S3—C5	178.20 (13)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄O₂S₃
M_r	406.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.1602 (5), 8.3524 (3), 14.1814 (4)
β (°)	107.428 (2)
V (Å³)	1826.28 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.15 × 0.13 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26571, 7059, 4551
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.774

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.143, 0.99
No. of reflections	7059
No. of parameters	251
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.43

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Acknowledgements

PS and SR thank Mr P. Charles for his help in solving the structure.

References

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