3-(4-Bromo­phenyl­sulfon­yl)-5-cyclo­pentyl-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812019411

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1624

doi:10.1107/S1600536812019411

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3-(4-Bromophenylsulfonyl)-5-cyclopentyl-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 3 April 2012; accepted 30 April 2012; online 5 May 2012)

In the title compound, C₂₀H₁₉BrO₃S, the cyclopentyl ring adopts an envelope conformation. The 4-bromophenyl ring makes a dihedral angle of 82.09 (6)° with the mean plane [mean deviation = 0.026 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.309 (2) Å].

Related literature

For background information and the crystal structure of a related compound, see: Seo et al. (2011 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₉BrO₃S
M_r = 419.32
Monoclinic, P 2₁ /c
a = 6.8956 (2) Å
b = 17.1034 (3) Å
c = 15.7773 (3) Å
β = 97.533 (1)°
V = 1844.69 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.36 mm⁻¹
T = 173 K
0.38 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.469, T_max = 0.570
18310 measured reflections
4602 independent reflections
3416 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.093
S = 1.02
4602 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.95	2.51	3.169 (3)	126
Symmetry code: (i) x-1, y, 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/S1600536812019411/fy2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019411/fy2055Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019411/fy2055Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-cyclopentyl-2-methyl-1-benzofuran derivatives containing a 3-phenylsulfonyl substituent (Seo et al., 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.026 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformtion. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofurn fragment is 82.09 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O interactions (Table 1). The crystal packing (Fig. 2) also exhibits Br···O halogen-bonding interactions between the bromine atom and the O atom of the O═S═O unit [Br1···O3ⁱ = 3.309 (2) Å, C18—Br1···O3ⁱ = 153.82 (8)°] (Politzer et al., 2007).

Related literature top

For background information and the crystal structure of a related compound, see: Seo et al. (2011). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-cyclopentyl-2-methyl-1-benzofuran (310 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 10 h, 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 (benzene) to afford the title compound as a colorless solid [yield 71%, m.p. 423–424 K; R_f = 0.48 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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 the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and Br···O interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1, - y + 1/2, z - 1/2; (ii) x + 1, y, z; (iii) x + 1, - y + 1/2, z + 1/2; (iv) x + 1, y, z.]

3-(4-Bromophenylsulfonyl)-5-cyclopentyl-2-methyl-1-benzofuran top

Crystal data top

C₂₀H₁₉BrO₃S	F(000) = 856
M_r = 419.32	D_x = 1.510 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5006 reflections
a = 6.8956 (2) Å	θ = 2.4–26.9°
b = 17.1034 (3) Å	µ = 2.36 mm⁻¹
c = 15.7773 (3) Å	T = 173 K
β = 97.533 (1)°	Block, colourless
V = 1844.69 (7) Å³	0.38 × 0.34 × 0.27 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4602 independent reflections
Radiation source: rotating anode	3416 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.041
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→22
T_min = 0.469, T_max = 0.570	l = −21→19
18310 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0389P)² + 0.8231P] where P = (F_o² + 2F_c²)/3
4602 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₂₀H₁₉BrO₃S	V = 1844.69 (7) Å³
M_r = 419.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8956 (2) Å	µ = 2.36 mm⁻¹
b = 17.1034 (3) Å	T = 173 K
c = 15.7773 (3) Å	0.38 × 0.34 × 0.27 mm
β = 97.533 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4602 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3416 reflections with I > 2σ(I)
T_min = 0.469, T_max = 0.570	R_int = 0.041
18310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	Δρ_max = 0.58 e Å⁻³
4602 reflections	Δρ_min = −0.73 e Å⁻³
227 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	−0.32092 (5)	0.301064 (16)	0.016006 (19)	0.06550 (13)
S1	0.31357 (7)	0.28508 (3)	0.34905 (3)	0.02688 (12)
O1	0.2226 (2)	0.48448 (8)	0.45861 (10)	0.0398 (4)
O2	0.5019 (2)	0.27163 (8)	0.32240 (10)	0.0356 (3)
O3	0.2418 (2)	0.23232 (8)	0.40858 (9)	0.0363 (3)
C1	0.3124 (3)	0.37925 (11)	0.38922 (12)	0.0282 (4)
C2	0.4174 (3)	0.44557 (11)	0.36055 (13)	0.0288 (4)
C3	0.5464 (3)	0.45853 (11)	0.30148 (13)	0.0313 (4)
H3	0.5924	0.4161	0.2707	0.038*
C4	0.6077 (3)	0.53476 (12)	0.28803 (14)	0.0351 (5)
C5	0.5410 (4)	0.59592 (12)	0.33602 (15)	0.0406 (5)
H5	0.5841	0.6476	0.3268	0.049*
C6	0.4158 (4)	0.58411 (12)	0.39592 (15)	0.0408 (5)
H6	0.3735	0.6259	0.4286	0.049*
C7	0.3554 (3)	0.50843 (12)	0.40580 (14)	0.0338 (5)
C8	0.1965 (3)	0.40590 (12)	0.44621 (14)	0.0351 (5)
C9	0.0490 (4)	0.36946 (14)	0.49391 (18)	0.0509 (7)
H9A	−0.0824	0.3813	0.4652	0.076*
H9B	0.0634	0.3903	0.5523	0.076*
H9C	0.0685	0.3127	0.4959	0.076*
C10	0.7396 (4)	0.55251 (12)	0.22173 (16)	0.0426 (6)
H10	0.7525	0.6106	0.2187	0.051*
C11	0.6704 (5)	0.52353 (19)	0.13200 (18)	0.0642 (8)
H11A	0.5648	0.5574	0.1037	0.077*
H11B	0.6206	0.4693	0.1334	0.077*
C12	0.8493 (6)	0.52695 (18)	0.0848 (2)	0.0763 (11)
H12A	0.8563	0.4797	0.0491	0.092*
H12B	0.8435	0.5736	0.0474	0.092*
C13	1.0259 (6)	0.53131 (18)	0.1533 (3)	0.0822 (12)
H13A	1.0902	0.5830	0.1525	0.099*
H13B	1.1222	0.4902	0.1443	0.099*
C14	0.9451 (4)	0.5187 (2)	0.2377 (2)	0.0685 (9)
H14A	0.9416	0.4623	0.2519	0.082*
H14B	1.0253	0.5465	0.2850	0.082*
C15	0.1402 (3)	0.28833 (10)	0.25667 (12)	0.0257 (4)
C16	−0.0527 (3)	0.26893 (12)	0.26253 (14)	0.0339 (5)
H16	−0.0905	0.2530	0.3157	0.041*
C17	−0.1896 (3)	0.27292 (13)	0.19020 (15)	0.0402 (5)
H17	−0.3224	0.2596	0.1931	0.048*
C18	−0.1312 (3)	0.29636 (12)	0.11402 (15)	0.0377 (5)
C19	0.0603 (4)	0.31567 (12)	0.10699 (14)	0.0382 (5)
H19	0.0971	0.3315	0.0536	0.046*
C20	0.1983 (3)	0.31153 (11)	0.17929 (13)	0.0318 (4)
H20	0.3311	0.3244	0.1760	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0750 (2)	0.04795 (17)	0.0610 (2)	0.00540 (13)	−0.03790 (16)	−0.00334 (12)
S1	0.0311 (3)	0.0203 (2)	0.0284 (2)	0.00110 (17)	0.00070 (19)	−0.00012 (18)
O1	0.0528 (10)	0.0260 (7)	0.0438 (9)	−0.0022 (6)	0.0187 (8)	−0.0062 (6)
O2	0.0312 (8)	0.0323 (7)	0.0424 (9)	0.0064 (6)	0.0021 (7)	−0.0042 (6)
O3	0.0500 (10)	0.0247 (7)	0.0336 (8)	−0.0015 (6)	0.0034 (7)	0.0042 (6)
C1	0.0340 (11)	0.0227 (9)	0.0277 (10)	−0.0017 (8)	0.0030 (8)	−0.0015 (8)
C2	0.0317 (11)	0.0228 (9)	0.0306 (10)	−0.0021 (7)	−0.0001 (8)	−0.0017 (7)
C3	0.0334 (12)	0.0258 (10)	0.0349 (11)	−0.0007 (8)	0.0050 (9)	−0.0013 (8)
C4	0.0371 (13)	0.0282 (10)	0.0402 (12)	−0.0016 (8)	0.0057 (9)	0.0031 (9)
C5	0.0473 (14)	0.0229 (10)	0.0526 (14)	−0.0043 (9)	0.0098 (11)	−0.0004 (9)
C6	0.0527 (15)	0.0246 (10)	0.0466 (13)	−0.0029 (9)	0.0114 (11)	−0.0071 (9)
C7	0.0382 (13)	0.0291 (10)	0.0346 (11)	−0.0018 (8)	0.0068 (9)	−0.0031 (8)
C8	0.0435 (13)	0.0246 (10)	0.0377 (12)	−0.0023 (8)	0.0072 (9)	−0.0026 (8)
C9	0.0638 (18)	0.0349 (12)	0.0610 (16)	−0.0046 (11)	0.0349 (14)	−0.0037 (11)
C10	0.0514 (15)	0.0244 (10)	0.0551 (15)	−0.0008 (9)	0.0188 (12)	0.0070 (10)
C11	0.076 (2)	0.0694 (19)	0.0507 (17)	−0.0048 (15)	0.0195 (15)	0.0125 (14)
C12	0.113 (3)	0.0466 (16)	0.082 (2)	0.0057 (17)	0.061 (2)	0.0127 (15)
C13	0.075 (2)	0.0528 (18)	0.132 (3)	−0.0021 (16)	0.065 (3)	0.0032 (19)
C14	0.0474 (18)	0.072 (2)	0.088 (2)	−0.0004 (14)	0.0185 (16)	0.0145 (17)
C15	0.0281 (11)	0.0196 (8)	0.0291 (10)	0.0022 (7)	0.0027 (8)	−0.0020 (7)
C16	0.0303 (12)	0.0347 (11)	0.0378 (12)	−0.0025 (8)	0.0083 (9)	−0.0032 (9)
C17	0.0283 (12)	0.0408 (12)	0.0502 (14)	−0.0009 (9)	0.0006 (10)	−0.0085 (10)
C18	0.0420 (14)	0.0276 (10)	0.0389 (12)	0.0057 (8)	−0.0117 (10)	−0.0069 (9)
C19	0.0542 (15)	0.0315 (11)	0.0279 (11)	−0.0023 (9)	0.0014 (10)	0.0011 (8)
C20	0.0332 (12)	0.0295 (10)	0.0329 (11)	−0.0035 (8)	0.0041 (9)	−0.0007 (8)

Geometric parameters (Å, º) top

Br1—C18	1.892 (2)	C10—C11	1.517 (4)
Br1—O3ⁱ	3.3090 (16)	C10—C14	1.521 (4)
S1—O2	1.4348 (15)	C10—H10	1.0000
S1—O3	1.4362 (15)	C11—C12	1.523 (4)
S1—C1	1.7313 (19)	C11—H11A	0.9900
S1—C15	1.760 (2)	C11—H11B	0.9900
O1—C8	1.367 (2)	C12—C13	1.520 (5)
O1—C7	1.379 (3)	C12—H12A	0.9900
C1—C8	1.358 (3)	C12—H12B	0.9900
C1—C2	1.449 (3)	C13—C14	1.525 (4)
C2—C3	1.388 (3)	C13—H13A	0.9900
C2—C7	1.388 (3)	C13—H13B	0.9900
C3—C4	1.395 (3)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.404 (3)	C15—C16	1.386 (3)
C4—C10	1.504 (3)	C15—C20	1.392 (3)
C5—C6	1.376 (3)	C16—C17	1.384 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.375 (3)	C17—C18	1.377 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C9	1.480 (3)	C18—C19	1.380 (4)
C9—H9A	0.9800	C19—C20	1.388 (3)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	C20—H20	0.9500

C18—Br1—O3ⁱ	153.82 (8)	C14—C10—H10	107.4
O2—S1—O3	119.56 (9)	C10—C11—C12	105.5 (3)
O2—S1—C1	107.71 (9)	C10—C11—H11A	110.6
O3—S1—C1	109.06 (9)	C12—C11—H11A	110.6
O2—S1—C15	107.74 (9)	C10—C11—H11B	110.6
O3—S1—C15	107.85 (9)	C12—C11—H11B	110.6
C1—S1—C15	103.80 (9)	H11A—C11—H11B	108.8
C8—O1—C7	106.92 (16)	C13—C12—C11	106.2 (3)
C8—C1—C2	107.78 (17)	C13—C12—H12A	110.5
C8—C1—S1	125.88 (16)	C11—C12—H12A	110.5
C2—C1—S1	125.97 (15)	C13—C12—H12B	110.5
C3—C2—C7	119.27 (18)	C11—C12—H12B	110.5
C3—C2—C1	136.45 (18)	H12A—C12—H12B	108.7
C7—C2—C1	104.23 (18)	C12—C13—C14	105.3 (3)
C2—C3—C4	119.00 (19)	C12—C13—H13A	110.7
C2—C3—H3	120.5	C14—C13—H13A	110.7
C4—C3—H3	120.5	C12—C13—H13B	110.7
C3—C4—C5	119.2 (2)	C14—C13—H13B	110.7
C3—C4—C10	121.13 (19)	H13A—C13—H13B	108.8
C5—C4—C10	119.70 (18)	C10—C14—C13	103.9 (3)
C6—C5—C4	122.7 (2)	C10—C14—H14A	111.0
C6—C5—H5	118.6	C13—C14—H14A	111.0
C4—C5—H5	118.6	C10—C14—H14B	111.0
C7—C6—C5	116.3 (2)	C13—C14—H14B	111.0
C7—C6—H6	121.9	H14A—C14—H14B	109.0
C5—C6—H6	121.9	C16—C15—C20	121.06 (19)
C6—C7—O1	125.68 (19)	C16—C15—S1	119.38 (16)
C6—C7—C2	123.5 (2)	C20—C15—S1	119.55 (15)
O1—C7—C2	110.74 (17)	C17—C16—C15	119.4 (2)
C1—C8—O1	110.30 (18)	C17—C16—H16	120.3
C1—C8—C9	134.34 (19)	C15—C16—H16	120.3
O1—C8—C9	115.33 (18)	C18—C17—C16	119.2 (2)
C8—C9—H9A	109.5	C18—C17—H17	120.4
C8—C9—H9B	109.5	C16—C17—H17	120.4
H9A—C9—H9B	109.5	C17—C18—C19	122.2 (2)
C8—C9—H9C	109.5	C17—C18—Br1	118.42 (18)
H9A—C9—H9C	109.5	C19—C18—Br1	119.40 (18)
H9B—C9—H9C	109.5	C18—C19—C20	118.8 (2)
C4—C10—C11	116.0 (2)	C18—C19—H19	120.6
C4—C10—C14	116.3 (2)	C20—C19—H19	120.6
C11—C10—C14	101.7 (2)	C19—C20—C15	119.4 (2)
C4—C10—H10	107.4	C19—C20—H20	120.3
C11—C10—H10	107.4	C15—C20—H20	120.3

O2—S1—C1—C8	−155.71 (19)	C7—O1—C8—C9	−176.6 (2)
O3—S1—C1—C8	−24.5 (2)	C3—C4—C10—C11	53.8 (3)
C15—S1—C1—C8	90.2 (2)	C5—C4—C10—C11	−124.7 (3)
O2—S1—C1—C2	32.2 (2)	C3—C4—C10—C14	−65.7 (3)
O3—S1—C1—C2	163.33 (17)	C5—C4—C10—C14	115.8 (3)
C15—S1—C1—C2	−81.9 (2)	C4—C10—C11—C12	−164.0 (2)
C8—C1—C2—C3	−176.0 (2)	C14—C10—C11—C12	−36.8 (3)
S1—C1—C2—C3	−2.7 (4)	C10—C11—C12—C13	18.2 (3)
C8—C1—C2—C7	1.1 (2)	C11—C12—C13—C14	7.8 (3)
S1—C1—C2—C7	174.40 (16)	C4—C10—C14—C13	168.5 (2)
C7—C2—C3—C4	−1.2 (3)	C11—C10—C14—C13	41.6 (3)
C1—C2—C3—C4	175.6 (2)	C12—C13—C14—C10	−30.8 (3)
C2—C3—C4—C5	1.5 (3)	O2—S1—C15—C16	153.86 (15)
C2—C3—C4—C10	−177.0 (2)	O3—S1—C15—C16	23.52 (18)
C3—C4—C5—C6	−0.4 (4)	C1—S1—C15—C16	−92.10 (17)
C10—C4—C5—C6	178.1 (2)	O2—S1—C15—C20	−27.16 (18)
C4—C5—C6—C7	−1.0 (4)	O3—S1—C15—C20	−157.50 (15)
C5—C6—C7—O1	−176.3 (2)	C1—S1—C15—C20	86.88 (17)
C5—C6—C7—C2	1.4 (4)	C20—C15—C16—C17	−0.2 (3)
C8—O1—C7—C6	177.0 (2)	S1—C15—C16—C17	178.79 (16)
C8—O1—C7—C2	−1.0 (2)	C15—C16—C17—C18	−0.2 (3)
C3—C2—C7—C6	−0.4 (3)	C16—C17—C18—C19	0.4 (3)
C1—C2—C7—C6	−178.1 (2)	C16—C17—C18—Br1	179.82 (16)
C3—C2—C7—O1	177.66 (19)	O3ⁱ—Br1—C18—C17	−10.6 (3)
C1—C2—C7—O1	−0.1 (2)	O3ⁱ—Br1—C18—C19	168.84 (12)
C2—C1—C8—O1	−1.8 (3)	C17—C18—C19—C20	−0.2 (3)
S1—C1—C8—O1	−175.07 (15)	Br1—C18—C19—C20	−179.62 (15)
C2—C1—C8—C9	176.1 (3)	C18—C19—C20—C15	−0.2 (3)
S1—C1—C8—C9	2.8 (4)	C16—C15—C20—C19	0.4 (3)
C7—O1—C8—C1	1.7 (2)	S1—C15—C20—C19	−178.60 (15)

Symmetry code: (i) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱⁱ	0.95	2.51	3.169 (3)	126

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉BrO₃S
M_r	419.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.8956 (2), 17.1034 (3), 15.7773 (3)
β (°)	97.533 (1)
V (Å³)	1844.69 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.36
Crystal size (mm)	0.38 × 0.34 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.469, 0.570
No. of measured, independent and observed [I > 2σ(I)] reflections	18310, 4602, 3416
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.093, 1.02
No. of reflections	4602
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.73

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
C17—H17···O2ⁱ	0.95	2.51	3.169 (3)	126.1

Symmetry code: (i) x−1, y, z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311. Web of Science CrossRef PubMed CAS Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2223. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1624

doi:10.1107/S1600536812019411

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