Bis(phenyl­sulfin­yl)methane

Wardell, S.M.S.V.; Lima, G.M. de; Wardell, J.L.; Tiekink, E.R.T.

doi:10.1107/S1600536810005957

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o653-o654

doi:10.1107/S1600536810005957

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Bis(phenylsulfinyl)methane

Solange M. S. V. Wardell,^a Geraldo M. de Lima,^b James L. Wardell ^c ‡ and Edward R. T. Tiekink ^d ^*

^aCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, ^bDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil, ^cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 11 February 2010; accepted 13 February 2010; online 20 February 2010)

Two independent molecules comprise the asymmetric unit of the title compound, C₁₃H₁₂O₂S₂, which differ in terms of minor variations in the relative orientations of the benzene rings [the O–S–C–C torsion angles for the first independent molecule are −6.66 (17) and −12.88 (19)° compared with −21.70 (18) and 4.83 (16)° for the second molecule]. Supramolecular chains sustained by C—H⋯O contacts and aligned along the a axis are found in the crystal structure. These are held in place in the three dimensional structure by C—H⋯π interactions.

Related literature

For the synthesis of bis(phenylsulfinyl)methane, see Shriner et al. (1930 ); Greene & Shevlin (1971 ); Hajipour et al. (2005 ). For separation of the meso and racemic forms, see Greene & Shevlin (1971). For the structure of the meso form, see: Kannan et al. (2003 ).

Experimental

Crystal data

C₁₃H₁₂O₂S₂
M_r = 264.37
Monoclinic, P 2₁ /c
a = 8.4368 (4) Å
b = 17.1966 (7) Å
c = 17.1387 (6) Å
β = 95.251 (3)°
V = 2476.12 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 120 K
0.32 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.636, T_max = 0.746
41505 measured reflections
5503 independent reflections
4545 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.02
5503 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C21–C26 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3	0.95	2.39	3.268 (2)	153
C5—H5⋯O1ⁱ	0.95	2.47	3.302 (3)	146
C12—H12⋯O2ⁱⁱ	0.95	2.57	3.240 (2)	128
C22—H22⋯O2	0.95	2.35	3.285 (2)	170
C24—H24⋯O4ⁱⁱⁱ	0.95	2.57	3.335 (2)	138
C4—H4⋯S2ⁱ	0.95	2.87	3.484 (2)	124
C9—H9⋯Cg1^iv	0.95	2.67	3.553 (2)	154
C16—H16⋯Cg2^v	0.95	2.78	3.682 (2)	159
C18—H18⋯Cg2^vi	0.95	2.96	3.744 (2)	141
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1; (iii) x-1, y, z; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) -x+1, -y, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810005957/pv2261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005957/pv2261Isup2.hkl

checkCIF report

Comment top

Crystals of the title compound, (I), a known species (Shriner et al., 1930; Greene & Shevlin, 1971; Hajipour et al., 2005), were obtained from an attempted co-crystallisation experiment (see Experimental section). Two independent molecules comprise the crystallographic asymmetric unit of (I), Figs 1 and 2. The conformations of the molecules differ only in the relative orientations of the benzene rings as illustrated in the overlay diagram, Fig. 3. These differences are quantified in terms of the O1–S1–C1–C7 and O2–S2–C8–C13 torsion angles of -6.66 (17) and -12.88 (19) °, respectively, for the first independent molecule, and for the second molecule of -21.70 (18) and 4.83 (16) °, respectively, for O3–S3–C15–C20 and O4–S4–C21–C26 torsion angles. The relative orientations of the sulfinyl groups are virtually identical as seen in the O1–S1–S2–O2 and O3–S3–S4–O4 torsion angles of -123.31 (8) and -125.32 (8) °, respectively. These are quite distinct from the equivalent value of -178.0 (1) ° found in the meso stereo-isomer (Kannan et al., 2003). Otherwise, the equivalent bond distances in the three molecules show no special trends.

The crystal packing comprises supramolecular chains of molecules aligned along the a axis. These are sustained by C–H···O interactions as well as C–H···S and C18–H···π contacts, Fig. 4 and Table 1. Chains stack in the crystal structure being held together by C–H···π contacts, Fig. 5.

Related literature top

For the synthesis of bis(phenylsulfinyl)methane, see Shriner et al. (1930); Greene & Shevlin (1971); Hajipour et al. (2005). For separation of the meso and racemic forms, see Greene & Shevlin (1971). For the structure of the meso form, see: Kannan et al. (2003).

Experimental top

The title compound was prepared in accord with literature procedures (Shriner et al., 1930; Greene & Shevlin, 1971; Hajipour et al., 2005). The compound was isolated unchanged on slow evaporation of an ethanol solution containing equimolar (1 mmol) amounts of bis(phenylsulfinyl)methane and H₂NCOCH₂CH₂SnCl₃. The sample used in the X-ray study was further recrystallised from EtOH; m.pt. 452-454 K. Lit. value 454-456 K.(Greene & Shevlin, 1971).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 3. An overlay diagram highlighting the different conformations found for the independent molecules in (I). The red molecule corresponds to the molecule shown in Fig. 1.
	Fig. 4. A view of a supramolecular chain aligned along the a axis in (I). The C–H···O interactions are shown as orange dashed lines. Hydrogen atoms not involved in C–H···O contacts are omitted for clarity.
	Fig. 5. A view in projection down the a axis of the unit cell contents in (I). The two shorter of the C–H···O interactions are shown as orange dashed lines, and C–H···π interactions are shown as purple dashed lines.

Bis(phenylsulfinyl)methane top

Crystal data top

C₁₃H₁₂O₂S₂	F(000) = 1104
M_r = 264.37	D_x = 1.418 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 114673 reflections
a = 8.4368 (4) Å	θ = 2.9–27.5°
b = 17.1966 (7) Å	µ = 0.42 mm⁻¹
c = 17.1387 (6) Å	T = 120 K
β = 95.251 (3)°	Block, colourless
V = 2476.12 (18) Å³	0.32 × 0.30 × 0.20 mm
Z = 8

Data collection top

Nonius KappaCCD area-detector diffractometer	5503 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	4545 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.045
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −22→22
T_min = 0.636, T_max = 0.746	l = −22→22
41505 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0584P)² + 1.1709P] where P = (F_o² + 2F_c²)/3
5503 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₃H₁₂O₂S₂	V = 2476.12 (18) Å³
M_r = 264.37	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4368 (4) Å	µ = 0.42 mm⁻¹
b = 17.1966 (7) Å	T = 120 K
c = 17.1387 (6) Å	0.32 × 0.30 × 0.20 mm
β = 95.251 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	5503 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	4545 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.746	R_int = 0.045
41505 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
5503 reflections	Δρ_min = −0.40 e Å⁻³
307 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.24251 (6)	0.13741 (2)	0.22205 (3)	0.02771 (12)
S2	0.04038 (6)	0.03440 (3)	0.30510 (3)	0.02665 (12)
S3	0.49132 (6)	0.19368 (3)	0.49191 (3)	0.02721 (12)
S4	0.28505 (6)	0.29593 (3)	0.39107 (3)	0.02590 (12)
O1	0.12552 (17)	0.12780 (8)	0.15191 (9)	0.0349 (3)
O2	0.02544 (18)	0.09565 (8)	0.36612 (9)	0.0376 (3)
O3	0.49884 (19)	0.13910 (9)	0.42450 (8)	0.0386 (4)
O4	0.39757 (17)	0.36142 (8)	0.41079 (8)	0.0333 (3)
C1	0.2401 (2)	0.04591 (10)	0.27607 (11)	0.0264 (4)
H1A	0.2674	0.0020	0.2425	0.032*
H1B	0.3182	0.0475	0.3228	0.032*
C2	0.4359 (2)	0.12423 (10)	0.18987 (11)	0.0252 (4)
C3	0.5695 (2)	0.14283 (10)	0.24020 (11)	0.0274 (4)
H3	0.5585	0.1599	0.2922	0.033*
C4	0.7181 (3)	0.13606 (10)	0.21331 (12)	0.0322 (5)
H4	0.8103	0.1479	0.2472	0.039*
C5	0.7339 (3)	0.11204 (12)	0.13709 (13)	0.0358 (5)
H5	0.8367	0.1079	0.1190	0.043*
C6	0.6003 (3)	0.09403 (12)	0.08740 (12)	0.0355 (5)
H6	0.6117	0.0773	0.0354	0.043*
C7	0.4492 (2)	0.10045 (11)	0.11357 (11)	0.0298 (4)
H7	0.3570	0.0887	0.0796	0.036*
C8	0.0703 (2)	−0.05729 (10)	0.35320 (10)	0.0233 (4)
C9	0.0409 (2)	−0.12363 (11)	0.30828 (11)	0.0276 (4)
H9	0.0134	−0.1198	0.2534	0.033*
C10	0.0522 (3)	−0.19562 (11)	0.34478 (12)	0.0309 (4)
H10	0.0335	−0.2417	0.3148	0.037*
C11	0.0907 (2)	−0.20043 (11)	0.42499 (12)	0.0315 (4)
H11	0.0983	−0.2499	0.4498	0.038*
C12	0.1184 (2)	−0.13364 (12)	0.46918 (11)	0.0310 (4)
H12	0.1448	−0.1374	0.5241	0.037*
C13	0.1076 (2)	−0.06116 (11)	0.43344 (10)	0.0267 (4)
H13	0.1255	−0.0151	0.4635	0.032*
C14	0.2918 (2)	0.23495 (10)	0.47830 (10)	0.0251 (4)
H14A	0.2699	0.2664	0.5245	0.030*
H14B	0.2113	0.1931	0.4712	0.030*
C15	0.4548 (2)	0.13864 (10)	0.57708 (10)	0.0237 (4)
C16	0.4973 (2)	0.17217 (11)	0.64956 (11)	0.0270 (4)
H16	0.5487	0.2213	0.6533	0.032*
C17	0.4632 (3)	0.13243 (12)	0.71669 (11)	0.0315 (4)
H17	0.4891	0.1550	0.7668	0.038*
C18	0.3916 (2)	0.06008 (12)	0.71060 (12)	0.0313 (4)
H18	0.3671	0.0335	0.7566	0.038*
C19	0.3554 (2)	0.02628 (11)	0.63801 (12)	0.0329 (4)
H19	0.3087	−0.0240	0.6344	0.040*
C20	0.3872 (2)	0.06544 (11)	0.57028 (11)	0.0288 (4)
H20	0.3628	0.0424	0.5202	0.035*
C21	0.0874 (2)	0.33204 (10)	0.39779 (10)	0.0231 (4)
C22	−0.0427 (2)	0.28285 (10)	0.38143 (10)	0.0258 (4)
H22	−0.0276	0.2294	0.3701	0.031*
C23	−0.1946 (2)	0.31345 (11)	0.38202 (11)	0.0303 (4)
H23	−0.2847	0.2806	0.3722	0.036*
C24	−0.2157 (2)	0.39202 (12)	0.39694 (11)	0.0303 (4)
H24	−0.3202	0.4127	0.3966	0.036*
C25	−0.0852 (3)	0.44035 (11)	0.41228 (11)	0.0313 (4)
H25	−0.1003	0.4940	0.4225	0.038*
C26	0.0681 (2)	0.41032 (11)	0.41268 (10)	0.0275 (4)
H26	0.1582	0.4431	0.4230	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0279 (3)	0.0202 (2)	0.0356 (3)	0.00118 (17)	0.0060 (2)	0.00111 (17)
S2	0.0245 (3)	0.0232 (2)	0.0328 (3)	0.00320 (17)	0.00547 (19)	0.00257 (17)
S3	0.0234 (3)	0.0320 (2)	0.0261 (2)	0.00392 (18)	0.00189 (18)	0.00415 (17)
S4	0.0247 (3)	0.0307 (2)	0.0223 (2)	0.00229 (17)	0.00193 (18)	0.00337 (17)
O1	0.0284 (8)	0.0322 (7)	0.0432 (8)	0.0031 (6)	−0.0023 (6)	0.0076 (6)
O2	0.0444 (9)	0.0238 (7)	0.0476 (8)	0.0039 (6)	0.0212 (7)	−0.0038 (6)
O3	0.0416 (9)	0.0494 (9)	0.0247 (7)	0.0163 (7)	0.0033 (6)	−0.0021 (6)
O4	0.0245 (8)	0.0385 (8)	0.0367 (8)	−0.0059 (6)	0.0008 (6)	0.0093 (6)
C1	0.0264 (11)	0.0237 (9)	0.0294 (9)	0.0006 (7)	0.0038 (8)	0.0020 (7)
C2	0.0281 (11)	0.0193 (8)	0.0281 (9)	−0.0013 (7)	0.0031 (7)	0.0043 (7)
C3	0.0320 (11)	0.0216 (9)	0.0276 (9)	−0.0030 (7)	−0.0022 (8)	0.0045 (7)
C4	0.0296 (12)	0.0230 (9)	0.0421 (11)	−0.0034 (7)	−0.0062 (9)	0.0094 (8)
C5	0.0267 (12)	0.0346 (11)	0.0474 (12)	0.0005 (8)	0.0105 (9)	0.0100 (9)
C6	0.0363 (13)	0.0401 (11)	0.0314 (10)	0.0000 (9)	0.0098 (9)	0.0014 (8)
C7	0.0313 (12)	0.0296 (10)	0.0276 (9)	−0.0019 (8)	−0.0018 (8)	0.0019 (7)
C8	0.0196 (10)	0.0242 (8)	0.0264 (9)	−0.0002 (7)	0.0033 (7)	0.0004 (7)
C9	0.0301 (11)	0.0277 (9)	0.0248 (9)	−0.0001 (8)	0.0010 (8)	−0.0024 (7)
C10	0.0325 (12)	0.0240 (9)	0.0366 (10)	−0.0004 (8)	0.0052 (8)	−0.0038 (7)
C11	0.0302 (12)	0.0281 (10)	0.0370 (11)	0.0028 (8)	0.0077 (8)	0.0080 (8)
C12	0.0270 (11)	0.0410 (11)	0.0249 (9)	0.0045 (8)	0.0025 (8)	0.0039 (8)
C13	0.0244 (10)	0.0295 (9)	0.0259 (9)	−0.0010 (7)	0.0008 (7)	−0.0052 (7)
C14	0.0223 (10)	0.0270 (9)	0.0258 (9)	0.0029 (7)	0.0010 (7)	0.0042 (7)
C15	0.0210 (10)	0.0241 (9)	0.0257 (9)	0.0049 (7)	0.0007 (7)	0.0001 (7)
C16	0.0273 (11)	0.0232 (9)	0.0300 (9)	0.0006 (7)	0.0002 (8)	−0.0035 (7)
C17	0.0320 (12)	0.0378 (11)	0.0243 (9)	0.0064 (8)	0.0005 (8)	−0.0028 (8)
C18	0.0273 (11)	0.0347 (10)	0.0329 (10)	0.0075 (8)	0.0072 (8)	0.0097 (8)
C19	0.0289 (11)	0.0252 (9)	0.0447 (12)	−0.0017 (8)	0.0034 (9)	0.0032 (8)
C20	0.0268 (11)	0.0283 (9)	0.0304 (10)	0.0004 (8)	−0.0029 (8)	−0.0038 (7)
C21	0.0255 (10)	0.0248 (9)	0.0184 (8)	0.0007 (7)	−0.0010 (7)	0.0024 (6)
C22	0.0303 (11)	0.0225 (8)	0.0241 (9)	−0.0015 (7)	−0.0008 (7)	0.0025 (7)
C23	0.0268 (11)	0.0352 (10)	0.0284 (10)	−0.0055 (8)	0.0004 (8)	0.0073 (8)
C24	0.0267 (11)	0.0401 (11)	0.0245 (9)	0.0070 (8)	0.0047 (8)	0.0043 (8)
C25	0.0365 (12)	0.0291 (9)	0.0276 (9)	0.0075 (8)	−0.0010 (8)	−0.0021 (7)
C26	0.0324 (11)	0.0249 (9)	0.0245 (9)	−0.0019 (8)	−0.0022 (8)	−0.0005 (7)

Geometric parameters (Å, º) top

S1—O1	1.4931 (15)	C10—H10	0.9500
S1—C2	1.784 (2)	C11—C12	1.384 (3)
S1—C1	1.8268 (18)	C11—H11	0.9500
S2—O2	1.4978 (14)	C12—C13	1.388 (3)
S2—C8	1.7864 (18)	C12—H12	0.9500
S2—C1	1.811 (2)	C13—H13	0.9500
S3—O3	1.4945 (14)	C14—H14A	0.9900
S3—C15	1.7898 (18)	C14—H14B	0.9900
S3—C14	1.8220 (19)	C15—C20	1.383 (3)
S4—O4	1.4917 (14)	C15—C16	1.386 (3)
S4—C21	1.7928 (19)	C16—C17	1.391 (3)
S4—C14	1.8225 (18)	C16—H16	0.9500
C1—H1A	0.9900	C17—C18	1.383 (3)
C1—H1B	0.9900	C17—H17	0.9500
C2—C7	1.385 (3)	C18—C19	1.382 (3)
C2—C3	1.393 (3)	C18—H18	0.9500
C3—C4	1.380 (3)	C19—C20	1.389 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.388 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—C26	1.383 (3)
C5—C6	1.384 (3)	C21—C22	1.394 (3)
C5—H5	0.9500	C22—C23	1.387 (3)
C6—C7	1.394 (3)	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.390 (3)
C7—H7	0.9500	C23—H23	0.9500
C8—C13	1.384 (2)	C24—C25	1.385 (3)
C8—C9	1.386 (2)	C24—H24	0.9500
C9—C10	1.386 (3)	C25—C26	1.392 (3)
C9—H9	0.9500	C25—H25	0.9500
C10—C11	1.386 (3)	C26—H26	0.9500

O1—S1—C2	107.03 (9)	C11—C12—C13	120.18 (17)
O1—S1—C1	105.99 (8)	C11—C12—H12	119.9
C2—S1—C1	95.76 (8)	C13—C12—H12	119.9
O2—S2—C8	108.42 (8)	C8—C13—C12	118.78 (17)
O2—S2—C1	104.77 (9)	C8—C13—H13	120.6
C8—S2—C1	97.34 (8)	C12—C13—H13	120.6
O3—S3—C15	108.72 (8)	S3—C14—S4	106.76 (10)
O3—S3—C14	104.46 (8)	S3—C14—H14A	110.4
C15—S3—C14	94.86 (8)	S4—C14—H14A	110.4
O4—S4—C21	107.47 (8)	S3—C14—H14B	110.4
O4—S4—C14	106.09 (8)	S4—C14—H14B	110.4
C21—S4—C14	96.09 (8)	H14A—C14—H14B	108.6
S2—C1—S1	106.69 (10)	C20—C15—C16	121.66 (17)
S2—C1—H1A	110.4	C20—C15—S3	120.88 (14)
S1—C1—H1A	110.4	C16—C15—S3	117.46 (14)
S2—C1—H1B	110.4	C15—C16—C17	118.74 (17)
S1—C1—H1B	110.4	C15—C16—H16	120.6
H1A—C1—H1B	108.6	C17—C16—H16	120.6
C7—C2—C3	121.43 (18)	C18—C17—C16	120.11 (18)
C7—C2—S1	119.05 (15)	C18—C17—H17	119.9
C3—C2—S1	119.39 (15)	C16—C17—H17	119.9
C4—C3—C2	118.86 (18)	C19—C18—C17	120.36 (18)
C4—C3—H3	120.6	C19—C18—H18	119.8
C2—C3—H3	120.6	C17—C18—H18	119.8
C3—C4—C5	120.52 (19)	C18—C19—C20	120.32 (18)
C3—C4—H4	119.7	C18—C19—H19	119.8
C5—C4—H4	119.7	C20—C19—H19	119.8
C6—C5—C4	120.2 (2)	C15—C20—C19	118.73 (17)
C6—C5—H5	119.9	C15—C20—H20	120.6
C4—C5—H5	119.9	C19—C20—H20	120.6
C5—C6—C7	120.09 (19)	C26—C21—C22	121.60 (18)
C5—C6—H6	120.0	C26—C21—S4	118.37 (14)
C7—C6—H6	120.0	C22—C21—S4	119.80 (14)
C2—C7—C6	118.90 (18)	C23—C22—C21	118.68 (17)
C2—C7—H7	120.5	C23—C22—H22	120.7
C6—C7—H7	120.5	C21—C22—H22	120.7
C13—C8—C9	121.68 (17)	C22—C23—C24	120.29 (18)
C13—C8—S2	120.71 (14)	C22—C23—H23	119.9
C9—C8—S2	117.37 (14)	C24—C23—H23	119.9
C8—C9—C10	118.88 (17)	C23—C24—C25	120.35 (19)
C8—C9—H9	120.6	C23—C24—H24	119.8
C10—C9—H9	120.6	C25—C24—H24	119.8
C11—C10—C9	120.08 (17)	C24—C25—C26	120.03 (18)
C11—C10—H10	120.0	C24—C25—H25	120.0
C9—C10—H10	120.0	C26—C25—H25	120.0
C10—C11—C12	120.39 (17)	C21—C26—C25	119.03 (18)
C10—C11—H11	119.8	C21—C26—H26	120.5
C12—C11—H11	119.8	C25—C26—H26	120.5

O2—S2—C1—S1	−69.82 (11)	O3—S3—C14—S4	−68.19 (11)
C8—S2—C1—S1	178.88 (9)	C15—S3—C14—S4	−178.96 (9)
O1—S1—C1—S2	−61.94 (11)	O4—S4—C14—S3	−65.87 (11)
C2—S1—C1—S2	−171.52 (10)	C21—S4—C14—S3	−176.05 (9)
O1—S1—C2—C7	−6.66 (17)	O3—S3—C15—C20	−21.70 (18)
C1—S1—C2—C7	102.03 (15)	C14—S3—C15—C20	85.36 (17)
O1—S1—C2—C3	169.22 (13)	O3—S3—C15—C16	158.16 (15)
C1—S1—C2—C3	−82.09 (15)	C14—S3—C15—C16	−94.78 (16)
C7—C2—C3—C4	−1.0 (3)	C20—C15—C16—C17	−3.3 (3)
S1—C2—C3—C4	−176.81 (13)	S3—C15—C16—C17	176.85 (15)
C2—C3—C4—C5	0.8 (3)	C15—C16—C17—C18	1.5 (3)
C3—C4—C5—C6	−0.5 (3)	C16—C17—C18—C19	0.9 (3)
C4—C5—C6—C7	0.4 (3)	C17—C18—C19—C20	−1.6 (3)
C3—C2—C7—C6	1.0 (3)	C16—C15—C20—C19	2.7 (3)
S1—C2—C7—C6	176.77 (15)	S3—C15—C20—C19	−177.49 (15)
C5—C6—C7—C2	−0.7 (3)	C18—C19—C20—C15	−0.2 (3)
O2—S2—C8—C13	−12.88 (19)	O4—S4—C21—C26	4.83 (16)
C1—S2—C8—C13	95.40 (17)	C14—S4—C21—C26	113.84 (14)
O2—S2—C8—C9	161.56 (15)	O4—S4—C21—C22	179.36 (13)
C1—S2—C8—C9	−90.15 (16)	C14—S4—C21—C22	−71.63 (15)
C13—C8—C9—C10	−1.2 (3)	C26—C21—C22—C23	−1.5 (3)
S2—C8—C9—C10	−175.59 (15)	S4—C21—C22—C23	−175.83 (13)
C8—C9—C10—C11	0.6 (3)	C21—C22—C23—C24	1.4 (3)
C9—C10—C11—C12	−0.1 (3)	C22—C23—C24—C25	−0.8 (3)
C10—C11—C12—C13	0.0 (3)	C23—C24—C25—C26	0.1 (3)
C9—C8—C13—C12	1.2 (3)	C22—C21—C26—C25	0.8 (3)
S2—C8—C13—C12	175.36 (15)	S4—C21—C26—C25	175.27 (14)
C11—C12—C13—C8	−0.5 (3)	C24—C25—C26—C21	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C21–C26 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.95	2.39	3.268 (2)	153
C5—H5···O1ⁱ	0.95	2.47	3.302 (3)	146
C12—H12···O2ⁱⁱ	0.95	2.57	3.240 (2)	128
C22—H22···O2	0.95	2.35	3.285 (2)	170
C24—H24···O4ⁱⁱⁱ	0.95	2.57	3.335 (2)	138
C4—H4···S2ⁱ	0.95	2.87	3.484 (2)	124
C9—H9···Cg1^iv	0.95	2.67	3.553 (2)	154
C16—H16···Cg2^v	0.95	2.78	3.682 (2)	159
C18—H18···Cg2^vi	0.95	2.96	3.744 (2)	141

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1; (iii) x−1, y, z; (iv) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂O₂S₂
M_r	264.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	8.4368 (4), 17.1966 (7), 17.1387 (6)
β (°)	95.251 (3)
V (Å³)	2476.12 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.32 × 0.30 × 0.20

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.636, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	41505, 5503, 4545
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.02
No. of reflections	5503
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.40

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C21–C26 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.95	2.39	3.268 (2)	153
C5—H5···O1ⁱ	0.95	2.47	3.302 (3)	146
C12—H12···O2ⁱⁱ	0.95	2.57	3.240 (2)	128
C22—H22···O2	0.95	2.35	3.285 (2)	170
C24—H24···O4ⁱⁱⁱ	0.95	2.57	3.335 (2)	138
C4—H4···S2ⁱ	0.95	2.87	3.484 (2)	124
C9—H9···Cg1^iv	0.95	2.67	3.553 (2)	154
C16—H16···Cg2^v	0.95	2.78	3.682 (2)	159
C18—H18···Cg2^vi	0.95	2.96	3.744 (2)	141

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1; (iii) x−1, y, z; (iv) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y, −z+1.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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Volume 66| Part 3| March 2010| Pages o653-o654

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