5-Bromo-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811003242

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o527

doi:10.1107/S1600536811003242

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5-Bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 18 January 2011; accepted 25 January 2011; online 29 January 2011)

In the asymmetric unit of the title compound, C₁₅H₁₇BrO₃S, there are two independent molecules. The cyclohexane rings in each adopt classic chair conformations. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and aromatic π–π interactions between the furan rings of symmetry-related molecules [centroid–centroid distance = 3.555 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For related structures, see: Choi et al. (2007 ); Seo et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₇BrO₂S
M_r = 341.26
Monoclinic, P 2₁ /c
a = 12.1842 (2) Å
b = 9.0281 (1) Å
c = 26.6191 (4) Å
β = 97.702 (1)°
V = 2901.69 (7) Å³
Z = 8
Mo Kα radiation
μ = 2.97 mm⁻¹
T = 173 K
0.31 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.579, T_max = 0.746
26831 measured reflections
6674 independent reflections
4944 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.04
6674 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.95	2.56	3.495 (3)	170
C25—H25⋯O2	1.00	2.57	3.409 (3)	142
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003242/lh5201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003242/lh5201Isup2.hkl

checkCIF report

Comment top

Many compounds involving a benzofuran ring have potential pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006; Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 5-bromo-2-methyl-3-methylsufinyl-1-benzofuran analogues (Choi et al., 2007, Seo et al., 2009), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. There are two independent molecules [A and B] in which the benzofuran unit is essentially planar in each with a mean deviation of 0.013 (2) Å and 0.014 (2) Å for A and B, respectively from the least-squares plane defined by the nine constituent atoms. The cyclohexyl rings are in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the oxygen atom of the S═O unit (Table 1; C5—H5···O2ⁱ), and the second one between a cyclohexyl H atom and the oxygen atom of the S═O unit (Table 1; C25—H25···O2). An intramolecular hydrogen bond exists between a cyclohexyl H atom and the oxygen atom of the S═O unit (Table 1; C25—H25···O2). Further stabilization is provided by aromatic π–π interactions between the furan rings of symmetry related molecules, with a Cg1···Cg2(1-x,1/2+y,3/2-z) distance of 3.555 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 and C16/C17/C22/O3/C23 furan rings, respectively).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2007); Seo et al. (2009).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (293 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 388–389 K; R_f = 0.45 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and π–π interactions (dotted lines) in the crystal packing of the title compound. [Symmetry codes: (i) x, y + 1, z; (ii) - x + 1, y + 1/2, - z + 3/2; (iii) x, - 1 +y,z .]

5-Bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran top

Crystal data top

C₁₅H₁₇BrO₂S	F(000) = 1392
M_r = 341.26	D_x = 1.562 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7002 reflections
a = 12.1842 (2) Å	θ = 2.4–24.9°
b = 9.0281 (1) Å	µ = 2.97 mm⁻¹
c = 26.6191 (4) Å	T = 173 K
β = 97.702 (1)°	Block, colourless
V = 2901.69 (7) Å³	0.31 × 0.22 × 0.18 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	6674 independent reflections
Radiation source: rotating anode	4944 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.041
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→11
T_min = 0.579, T_max = 0.746	l = −32→34
26831 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0465P)² + 0.1726P] where P = (F_o² + 2F_c²)/3
6674 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₅H₁₇BrO₂S	V = 2901.69 (7) Å³
M_r = 341.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1842 (2) Å	µ = 2.97 mm⁻¹
b = 9.0281 (1) Å	T = 173 K
c = 26.6191 (4) Å	0.31 × 0.22 × 0.18 mm
β = 97.702 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6674 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4944 reflections with I > 2σ(I)
T_min = 0.579, T_max = 0.746	R_int = 0.041
26831 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.04	Δρ_max = 0.41 e Å⁻³
6674 reflections	Δρ_min = −0.56 e Å⁻³
345 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.46756 (2)	0.86266 (3)	0.592298 (11)	0.04012 (9)
Br2	−0.07658 (2)	−0.22211 (3)	0.590592 (11)	0.04406 (10)
S1	0.73629 (5)	0.29635 (6)	0.65910 (2)	0.02434 (14)
S2	0.27538 (5)	0.26776 (7)	0.66785 (2)	0.02864 (15)
O1	0.87123 (13)	0.65573 (18)	0.72524 (6)	0.0277 (4)
O2	0.61309 (14)	0.28891 (19)	0.65360 (7)	0.0350 (4)
O3	0.36105 (14)	−0.13307 (18)	0.71689 (6)	0.0313 (4)
O4	0.15602 (15)	0.3032 (2)	0.65511 (7)	0.0401 (5)
C1	0.77497 (18)	0.4739 (2)	0.68179 (8)	0.0211 (5)
C2	0.71675 (18)	0.6108 (2)	0.66932 (8)	0.0202 (5)
C3	0.62204 (19)	0.6512 (3)	0.63733 (8)	0.0230 (5)
H3	0.5777	0.5803	0.6175	0.028*
C4	0.59557 (19)	0.8007 (3)	0.63584 (9)	0.0250 (5)
C5	0.6577 (2)	0.9072 (3)	0.66440 (9)	0.0299 (6)
H5	0.6357	1.0082	0.6619	0.036*
C6	0.7517 (2)	0.8665 (3)	0.69656 (9)	0.0294 (6)
H6	0.7951	0.9371	0.7169	0.035*
C7	0.77938 (19)	0.7179 (3)	0.69753 (9)	0.0239 (5)
C8	0.86624 (19)	0.5065 (3)	0.71497 (8)	0.0249 (5)
C9	0.9604 (2)	0.4162 (3)	0.73881 (10)	0.0353 (6)
H9A	0.9366	0.3131	0.7413	0.053*
H9B	0.9860	0.4546	0.7728	0.053*
H9C	1.0210	0.4210	0.7181	0.053*
C10	0.77442 (19)	0.3168 (3)	0.59584 (9)	0.0234 (5)
H10	0.7406	0.4100	0.5805	0.028*
C11	0.8996 (2)	0.3278 (3)	0.59887 (10)	0.0394 (7)
H11A	0.9343	0.2411	0.6174	0.047*
H11B	0.9257	0.4182	0.6179	0.047*
C12	0.9348 (3)	0.3334 (4)	0.54597 (12)	0.0561 (9)
H12A	0.9079	0.4266	0.5290	0.067*
H12B	1.0166	0.3327	0.5489	0.067*
C13	0.8886 (3)	0.2023 (4)	0.51411 (12)	0.0612 (10)
H13A	0.9092	0.2113	0.4795	0.073*
H13B	0.9211	0.1094	0.5293	0.073*
C14	0.7638 (3)	0.1964 (3)	0.51127 (10)	0.0487 (8)
H14A	0.7354	0.1095	0.4909	0.058*
H14B	0.7313	0.2866	0.4941	0.058*
C15	0.7284 (2)	0.1857 (3)	0.56366 (10)	0.0380 (6)
H15A	0.7561	0.0920	0.5801	0.046*
H15B	0.6465	0.1853	0.5608	0.046*
C16	0.28708 (19)	0.0766 (3)	0.68148 (8)	0.0242 (5)
C17	0.2120 (2)	−0.0437 (3)	0.66480 (9)	0.0245 (5)
C18	0.11013 (19)	−0.0572 (3)	0.63480 (8)	0.0255 (5)
H18	0.0730	0.0264	0.6189	0.031*
C19	0.0653 (2)	−0.1977 (3)	0.62917 (9)	0.0294 (6)
C20	0.1191 (2)	−0.3231 (3)	0.65164 (10)	0.0344 (6)
H20	0.0860	−0.4180	0.6461	0.041*
C21	0.2188 (2)	−0.3094 (3)	0.68142 (10)	0.0343 (6)
H21	0.2562	−0.3930	0.6972	0.041*
C22	0.2629 (2)	−0.1690 (3)	0.68765 (9)	0.0264 (5)
C23	0.3726 (2)	0.0180 (3)	0.71287 (9)	0.0280 (5)
C24	0.4728 (2)	0.0833 (3)	0.74241 (10)	0.0409 (7)
H24A	0.5345	0.0792	0.7223	0.061*
H24B	0.4921	0.0272	0.7739	0.061*
H24C	0.4581	0.1867	0.7505	0.061*
C25	0.33763 (19)	0.2705 (2)	0.60925 (8)	0.0228 (5)
H25	0.4133	0.2260	0.6165	0.027*
C26	0.3509 (2)	0.4326 (3)	0.59471 (9)	0.0308 (6)
H26A	0.2773	0.4808	0.5888	0.037*
H26B	0.3963	0.4853	0.6228	0.037*
C27	0.4067 (2)	0.4425 (3)	0.54673 (9)	0.0332 (6)
H27A	0.4125	0.5476	0.5369	0.040*
H27B	0.4825	0.4015	0.5536	0.040*
C28	0.3413 (2)	0.3575 (3)	0.50351 (10)	0.0354 (6)
H28A	0.3803	0.3627	0.4732	0.043*
H28B	0.2675	0.4035	0.4948	0.043*
C29	0.3274 (2)	0.1960 (3)	0.51799 (9)	0.0320 (6)
H29A	0.4009	0.1474	0.5233	0.038*
H29B	0.2813	0.1442	0.4899	0.038*
C30	0.2729 (2)	0.1827 (3)	0.56638 (9)	0.0268 (5)
H30A	0.1960	0.2204	0.5599	0.032*
H30B	0.2700	0.0772	0.5763	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03958 (16)	0.03535 (16)	0.04353 (17)	0.01601 (13)	−0.00135 (12)	0.00518 (12)
Br2	0.03332 (16)	0.0532 (2)	0.04619 (18)	−0.01426 (14)	0.00714 (13)	−0.00397 (14)
S1	0.0269 (3)	0.0171 (3)	0.0293 (3)	−0.0007 (2)	0.0049 (2)	0.0014 (2)
S2	0.0371 (4)	0.0203 (3)	0.0308 (3)	−0.0019 (3)	0.0129 (3)	−0.0023 (3)
O1	0.0235 (9)	0.0308 (9)	0.0279 (9)	−0.0036 (7)	0.0006 (7)	−0.0047 (7)
O2	0.0271 (9)	0.0309 (10)	0.0486 (11)	−0.0076 (8)	0.0112 (8)	−0.0029 (8)
O3	0.0353 (10)	0.0293 (10)	0.0293 (9)	0.0065 (8)	0.0042 (8)	0.0044 (7)
O4	0.0382 (11)	0.0323 (10)	0.0534 (12)	0.0061 (9)	0.0198 (9)	0.0080 (9)
C1	0.0218 (11)	0.0199 (12)	0.0220 (12)	−0.0012 (9)	0.0039 (9)	0.0018 (9)
C2	0.0228 (11)	0.0183 (11)	0.0208 (11)	0.0000 (9)	0.0082 (9)	0.0006 (9)
C3	0.0247 (12)	0.0204 (12)	0.0241 (12)	0.0001 (10)	0.0042 (10)	−0.0001 (10)
C4	0.0259 (13)	0.0246 (13)	0.0254 (12)	0.0037 (10)	0.0072 (10)	0.0033 (10)
C5	0.0348 (14)	0.0185 (12)	0.0387 (15)	0.0010 (11)	0.0134 (12)	−0.0005 (11)
C6	0.0327 (14)	0.0230 (13)	0.0335 (14)	−0.0071 (11)	0.0084 (11)	−0.0091 (11)
C7	0.0210 (12)	0.0294 (13)	0.0216 (12)	−0.0024 (10)	0.0042 (9)	−0.0036 (10)
C8	0.0259 (12)	0.0292 (13)	0.0199 (12)	0.0012 (10)	0.0044 (9)	0.0018 (10)
C9	0.0253 (13)	0.0486 (16)	0.0312 (14)	0.0070 (12)	0.0008 (11)	0.0059 (12)
C10	0.0250 (12)	0.0206 (12)	0.0248 (12)	0.0030 (10)	0.0039 (10)	−0.0004 (9)
C11	0.0257 (14)	0.0558 (18)	0.0375 (15)	0.0042 (13)	0.0071 (12)	−0.0041 (13)
C12	0.0397 (17)	0.086 (2)	0.0462 (19)	0.0061 (18)	0.0204 (14)	0.0000 (18)
C13	0.085 (3)	0.065 (2)	0.0386 (18)	0.024 (2)	0.0271 (18)	−0.0063 (16)
C14	0.076 (2)	0.0350 (16)	0.0340 (16)	0.0026 (16)	0.0017 (15)	−0.0115 (13)
C15	0.0502 (17)	0.0280 (14)	0.0344 (15)	−0.0021 (13)	0.0009 (13)	−0.0073 (12)
C16	0.0299 (13)	0.0203 (12)	0.0240 (12)	−0.0002 (10)	0.0091 (10)	−0.0014 (10)
C17	0.0309 (13)	0.0211 (12)	0.0235 (12)	0.0006 (10)	0.0110 (10)	0.0026 (10)
C18	0.0289 (13)	0.0240 (13)	0.0247 (13)	0.0003 (10)	0.0074 (10)	0.0036 (10)
C19	0.0293 (13)	0.0330 (14)	0.0273 (13)	−0.0056 (11)	0.0089 (10)	−0.0039 (11)
C20	0.0456 (17)	0.0212 (13)	0.0396 (16)	−0.0063 (12)	0.0168 (13)	−0.0025 (11)
C21	0.0450 (16)	0.0210 (13)	0.0397 (16)	0.0053 (12)	0.0163 (13)	0.0062 (11)
C22	0.0292 (13)	0.0255 (13)	0.0255 (13)	0.0035 (11)	0.0077 (10)	0.0014 (10)
C23	0.0300 (13)	0.0291 (13)	0.0264 (13)	−0.0010 (11)	0.0097 (10)	−0.0024 (11)
C24	0.0311 (14)	0.0576 (18)	0.0338 (15)	−0.0026 (14)	0.0037 (12)	−0.0087 (14)
C25	0.0241 (12)	0.0208 (12)	0.0243 (12)	−0.0005 (10)	0.0056 (10)	0.0000 (10)
C26	0.0340 (14)	0.0230 (13)	0.0373 (15)	−0.0050 (11)	0.0115 (11)	−0.0014 (11)
C27	0.0388 (15)	0.0271 (14)	0.0354 (15)	−0.0052 (12)	0.0107 (12)	0.0047 (11)
C28	0.0452 (16)	0.0323 (15)	0.0292 (14)	−0.0009 (13)	0.0065 (12)	0.0069 (11)
C29	0.0430 (16)	0.0286 (14)	0.0239 (13)	−0.0014 (12)	0.0028 (11)	−0.0005 (11)
C30	0.0303 (13)	0.0208 (12)	0.0290 (13)	−0.0037 (10)	0.0027 (10)	−0.0011 (10)

Geometric parameters (Å, º) top

Br1—C4	1.899 (2)	C13—H13B	0.9900
Br2—C19	1.902 (3)	C14—C15	1.517 (4)
S1—O2	1.4901 (18)	C14—H14A	0.9900
S1—C1	1.755 (2)	C14—H14B	0.9900
S1—C10	1.815 (2)	C15—H15A	0.9900
S2—O4	1.483 (2)	C15—H15B	0.9900
S2—C16	1.765 (2)	C16—C23	1.353 (3)
S2—C25	1.824 (2)	C16—C17	1.451 (3)
O1—C8	1.374 (3)	C17—C18	1.388 (3)
O1—C7	1.375 (3)	C17—C22	1.390 (3)
O3—C22	1.376 (3)	C18—C19	1.382 (3)
O3—C23	1.377 (3)	C18—H18	0.9500
C1—C8	1.357 (3)	C19—C20	1.401 (4)
C1—C2	1.442 (3)	C20—C21	1.364 (4)
C2—C3	1.388 (3)	C20—H20	0.9500
C2—C7	1.388 (3)	C21—C22	1.378 (3)
C3—C4	1.387 (3)	C21—H21	0.9500
C3—H3	0.9500	C23—C24	1.483 (3)
C4—C5	1.386 (3)	C24—H24A	0.9800
C5—C6	1.385 (4)	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800
C6—C7	1.383 (3)	C25—C30	1.521 (3)
C6—H6	0.9500	C25—C26	1.528 (3)
C8—C9	1.480 (3)	C25—H25	1.0000
C9—H9A	0.9800	C26—C27	1.528 (3)
C9—H9B	0.9800	C26—H26A	0.9900
C9—H9C	0.9800	C26—H26B	0.9900
C10—C11	1.520 (3)	C27—C28	1.517 (4)
C10—C15	1.524 (3)	C27—H27A	0.9900
C10—H10	1.0000	C27—H27B	0.9900
C11—C12	1.527 (4)	C28—C29	1.523 (3)
C11—H11A	0.9900	C28—H28A	0.9900
C11—H11B	0.9900	C28—H28B	0.9900
C12—C13	1.519 (5)	C29—C30	1.532 (3)
C12—H12A	0.9900	C29—H29A	0.9900
C12—H12B	0.9900	C29—H29B	0.9900
C13—C14	1.513 (5)	C30—H30A	0.9900
C13—H13A	0.9900	C30—H30B	0.9900

O2—S1—C1	107.19 (10)	C10—C15—H15A	109.7
O2—S1—C10	107.04 (11)	C14—C15—H15B	109.7
C1—S1—C10	97.81 (11)	C10—C15—H15B	109.7
O4—S2—C16	107.92 (11)	H15A—C15—H15B	108.2
O4—S2—C25	107.99 (11)	C23—C16—C17	107.3 (2)
C16—S2—C25	99.08 (10)	C23—C16—S2	122.95 (19)
C8—O1—C7	106.39 (17)	C17—C16—S2	129.71 (18)
C22—O3—C23	106.25 (18)	C18—C17—C22	119.5 (2)
C8—C1—C2	107.4 (2)	C18—C17—C16	136.0 (2)
C8—C1—S1	125.56 (18)	C22—C17—C16	104.4 (2)
C2—C1—S1	127.08 (17)	C19—C18—C17	116.9 (2)
C3—C2—C7	120.1 (2)	C19—C18—H18	121.6
C3—C2—C1	135.2 (2)	C17—C18—H18	121.6
C7—C2—C1	104.76 (19)	C18—C19—C20	122.7 (2)
C4—C3—C2	116.4 (2)	C18—C19—Br2	118.84 (19)
C4—C3—H3	121.8	C20—C19—Br2	118.43 (19)
C2—C3—H3	121.8	C21—C20—C19	120.2 (2)
C5—C4—C3	123.5 (2)	C21—C20—H20	119.9
C5—C4—Br1	118.29 (18)	C19—C20—H20	119.9
C3—C4—Br1	118.24 (18)	C20—C21—C22	117.1 (2)
C6—C5—C4	120.1 (2)	C20—C21—H21	121.4
C6—C5—H5	120.0	C22—C21—H21	121.4
C4—C5—H5	120.0	O3—C22—C21	125.5 (2)
C7—C6—C5	116.6 (2)	O3—C22—C17	111.0 (2)
C7—C6—H6	121.7	C21—C22—C17	123.5 (2)
C5—C6—H6	121.7	C16—C23—O3	111.0 (2)
O1—C7—C6	125.8 (2)	C16—C23—C24	133.1 (2)
O1—C7—C2	110.8 (2)	O3—C23—C24	116.0 (2)
C6—C7—C2	123.4 (2)	C23—C24—H24A	109.5
C1—C8—O1	110.7 (2)	C23—C24—H24B	109.5
C1—C8—C9	132.9 (2)	H24A—C24—H24B	109.5
O1—C8—C9	116.4 (2)	C23—C24—H24C	109.5
C8—C9—H9A	109.5	H24A—C24—H24C	109.5
C8—C9—H9B	109.5	H24B—C24—H24C	109.5
H9A—C9—H9B	109.5	C30—C25—C26	111.8 (2)
C8—C9—H9C	109.5	C30—C25—S2	113.65 (16)
H9A—C9—H9C	109.5	C26—C25—S2	107.45 (15)
H9B—C9—H9C	109.5	C30—C25—H25	107.9
C11—C10—C15	111.8 (2)	C26—C25—H25	107.9
C11—C10—S1	109.71 (17)	S2—C25—H25	107.9
C15—C10—S1	108.77 (17)	C27—C26—C25	110.0 (2)
C11—C10—H10	108.8	C27—C26—H26A	109.7
C15—C10—H10	108.8	C25—C26—H26A	109.7
S1—C10—H10	108.8	C27—C26—H26B	109.7
C10—C11—C12	110.9 (2)	C25—C26—H26B	109.7
C10—C11—H11A	109.5	H26A—C26—H26B	108.2
C12—C11—H11A	109.5	C28—C27—C26	110.9 (2)
C10—C11—H11B	109.5	C28—C27—H27A	109.4
C12—C11—H11B	109.5	C26—C27—H27A	109.4
H11A—C11—H11B	108.0	C28—C27—H27B	109.4
C13—C12—C11	111.1 (3)	C26—C27—H27B	109.4
C13—C12—H12A	109.4	H27A—C27—H27B	108.0
C11—C12—H12A	109.4	C27—C28—C29	110.9 (2)
C13—C12—H12B	109.4	C27—C28—H28A	109.5
C11—C12—H12B	109.4	C29—C28—H28A	109.5
H12A—C12—H12B	108.0	C27—C28—H28B	109.5
C14—C13—C12	110.5 (2)	C29—C28—H28B	109.5
C14—C13—H13A	109.6	H28A—C28—H28B	108.0
C12—C13—H13A	109.6	C28—C29—C30	111.3 (2)
C14—C13—H13B	109.6	C28—C29—H29A	109.4
C12—C13—H13B	109.6	C30—C29—H29A	109.4
H13A—C13—H13B	108.1	C28—C29—H29B	109.4
C13—C14—C15	111.4 (2)	C30—C29—H29B	109.4
C13—C14—H14A	109.4	H29A—C29—H29B	108.0
C15—C14—H14A	109.4	C25—C30—C29	110.5 (2)
C13—C14—H14B	109.4	C25—C30—H30A	109.6
C15—C14—H14B	109.4	C29—C30—H30A	109.6
H14A—C14—H14B	108.0	C25—C30—H30B	109.6
C14—C15—C10	109.8 (2)	C29—C30—H30B	109.6
C14—C15—H15A	109.7	H30A—C30—H30B	108.1

O2—S1—C1—C8	144.0 (2)	O4—S2—C16—C23	−152.5 (2)
C10—S1—C1—C8	−105.3 (2)	C25—S2—C16—C23	95.1 (2)
O2—S1—C1—C2	−35.5 (2)	O4—S2—C16—C17	25.0 (2)
C10—S1—C1—C2	75.1 (2)	C25—S2—C16—C17	−87.4 (2)
C8—C1—C2—C3	177.8 (2)	C23—C16—C17—C18	177.1 (3)
S1—C1—C2—C3	−2.5 (4)	S2—C16—C17—C18	−0.7 (4)
C8—C1—C2—C7	−0.7 (2)	C23—C16—C17—C22	−1.5 (2)
S1—C1—C2—C7	178.90 (17)	S2—C16—C17—C22	−179.34 (18)
C7—C2—C3—C4	−0.2 (3)	C22—C17—C18—C19	−0.5 (3)
C1—C2—C3—C4	−178.6 (2)	C16—C17—C18—C19	−179.0 (2)
C2—C3—C4—C5	−0.5 (3)	C17—C18—C19—C20	−0.9 (4)
C2—C3—C4—Br1	179.47 (16)	C17—C18—C19—Br2	177.68 (16)
C3—C4—C5—C6	0.0 (4)	C18—C19—C20—C21	1.4 (4)
Br1—C4—C5—C6	−179.90 (18)	Br2—C19—C20—C21	−177.15 (19)
C4—C5—C6—C7	1.0 (3)	C19—C20—C21—C22	−0.5 (4)
C8—O1—C7—C6	−179.9 (2)	C23—O3—C22—C21	−179.3 (2)
C8—O1—C7—C2	−0.7 (2)	C23—O3—C22—C17	0.4 (3)
C5—C6—C7—O1	177.4 (2)	C20—C21—C22—O3	178.7 (2)
C5—C6—C7—C2	−1.6 (4)	C20—C21—C22—C17	−0.9 (4)
C3—C2—C7—O1	−177.94 (19)	C18—C17—C22—O3	−178.2 (2)
C1—C2—C7—O1	0.9 (2)	C16—C17—C22—O3	0.7 (2)
C3—C2—C7—C6	1.3 (4)	C18—C17—C22—C21	1.4 (4)
C1—C2—C7—C6	−179.9 (2)	C16—C17—C22—C21	−179.6 (2)
C2—C1—C8—O1	0.3 (3)	C17—C16—C23—O3	1.9 (3)
S1—C1—C8—O1	−179.31 (15)	S2—C16—C23—O3	179.85 (15)
C2—C1—C8—C9	−175.8 (2)	C17—C16—C23—C24	−178.5 (2)
S1—C1—C8—C9	4.5 (4)	S2—C16—C23—C24	−0.5 (4)
C7—O1—C8—C1	0.2 (2)	C22—O3—C23—C16	−1.4 (3)
C7—O1—C8—C9	177.06 (19)	C22—O3—C23—C24	178.9 (2)
O2—S1—C10—C11	179.02 (18)	O4—S2—C25—C30	−48.50 (19)
C1—S1—C10—C11	68.28 (19)	C16—S2—C25—C30	63.80 (19)
O2—S1—C10—C15	−58.37 (19)	O4—S2—C25—C26	75.73 (18)
C1—S1—C10—C15	−169.11 (17)	C16—S2—C25—C26	−171.97 (17)
C15—C10—C11—C12	54.9 (3)	C30—C25—C26—C27	−56.7 (3)
S1—C10—C11—C12	175.7 (2)	S2—C25—C26—C27	177.98 (17)
C10—C11—C12—C13	−54.7 (4)	C25—C26—C27—C28	57.1 (3)
C11—C12—C13—C14	56.2 (4)	C26—C27—C28—C29	−57.3 (3)
C12—C13—C14—C15	−58.1 (3)	C27—C28—C29—C30	56.1 (3)
C13—C14—C15—C10	57.5 (3)	C26—C25—C30—C29	55.7 (3)
C11—C10—C15—C14	−56.0 (3)	S2—C25—C30—C29	177.52 (16)
S1—C10—C15—C14	−177.3 (2)	C28—C29—C30—C25	−55.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.95	2.56	3.495 (3)	170
C25—H25···O2	1.00	2.57	3.409 (3)	142

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇BrO₂S
M_r	341.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.1842 (2), 9.0281 (1), 26.6191 (4)
β (°)	97.702 (1)
V (Å³)	2901.69 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.97
Crystal size (mm)	0.31 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.579, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	26831, 6674, 4944
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.088, 1.04
No. of reflections	6674
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.56

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.95	2.56	3.495 (3)	170
C25—H25···O2	1.00	2.57	3.409 (3)	142

Symmetry code: (i) x, y+1, z.

References

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Volume 67| Part 2| February 2011| Page o527

doi:10.1107/S1600536811003242

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