5-Bromo-3-cyclo-pentyl-sulfinyl-2,7-dimethyl-1-benzofuran.

In the title compound, C(15)H(17)BrO(2)S, the cyclo-pentyl ring adopts an envelope conformation. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds. A slipped π-π inter-action occurs between the furan and benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.892 (3) Å and slippage = 1.786 (3) Å]. The crystal structure also exhibits a weak C-Br⋯π [2.919 (3) Å] inter-action.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C15H17BrO2S

M = 341.26

Orthorhombic,

a = 19.5624 (8) Å

b = 8.3501 (4) Å

c = 17.5346 (7) Å

V = 2864.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 3.01 mm−1

T = 173 K

0.36 × 0.19 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.414, T max = 0.899

14696 measured reflections

3561 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.094

S = 1.01

3561 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.51 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056091/xu5434sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056091/xu5434Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056091/xu5434Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H17BrO2S	F(000) = 1392
Mr = 341.26	Dx = 1.583 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2605 reflections
a = 19.5624 (8) Å	θ = 2.6–23.7°
b = 8.3501 (4) Å	µ = 3.01 mm−1
c = 17.5346 (7) Å	T = 173 K
V = 2864.2 (2) Å3	Block, colourless
Z = 8	0.36 × 0.19 × 0.04 mm

Bruker SMART APEXII CCD diffractometer	3561 independent reflections
Radiation source: rotating anode	2232 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.052
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −18→25
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.414, Tmax = 0.899	l = −23→17
14696 measured reflections

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0345P)2 + 1.0227P] where P = (Fo2 + 2Fc2)/3
3561 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.746477 (15)	0.35697 (4)	0.531719 (18)	0.04220 (13)
S1	0.58692 (4)	0.79730 (10)	0.30668 (4)	0.0302 (2)
O1	0.49506 (9)	0.7539 (2)	0.50628 (9)	0.0242 (4)
O2	0.61660 (12)	0.6477 (3)	0.27475 (11)	0.0467 (6)
C1	0.55893 (14)	0.7536 (3)	0.39992 (14)	0.0224 (6)
C2	0.59386 (14)	0.6560 (3)	0.45635 (14)	0.0210 (6)
C3	0.65304 (14)	0.5643 (3)	0.45788 (14)	0.0233 (6)
H3	0.6819	0.5542	0.4146	0.028*
C4	0.66740 (13)	0.4885 (3)	0.52599 (15)	0.0249 (6)
C5	0.62665 (13)	0.5023 (3)	0.59087 (15)	0.0236 (6)
H5	0.6400	0.4501	0.6366	0.028*
C6	0.56704 (14)	0.5911 (3)	0.58952 (15)	0.0215 (6)
C7	0.55264 (13)	0.6627 (3)	0.52041 (14)	0.0195 (6)
C8	0.50046 (14)	0.8064 (3)	0.43205 (15)	0.0239 (6)
C9	0.52221 (14)	0.6084 (3)	0.65801 (15)	0.0286 (7)
H9A	0.5216	0.7208	0.6742	0.043*
H9B	0.5400	0.5417	0.6995	0.043*
H9C	0.4757	0.5742	0.6452	0.043*
C10	0.44272 (14)	0.9041 (4)	0.40406 (17)	0.0332 (7)
H10A	0.4490	0.9265	0.3496	0.050*
H10B	0.4410	1.0053	0.4324	0.050*
H10C	0.3999	0.8455	0.4116	0.050*
C11	0.65806 (14)	0.9260 (3)	0.33175 (15)	0.0258 (7)
H11	0.6900	0.8687	0.3669	0.031*
C12	0.63212 (15)	1.0808 (4)	0.36924 (17)	0.0356 (8)
H12A	0.5815	1.0849	0.3686	0.043*
H12B	0.6480	1.0883	0.4227	0.043*
C13	0.66218 (16)	1.2156 (4)	0.32140 (17)	0.0371 (8)
H13A	0.6312	1.3092	0.3205	0.044*
H13B	0.7071	1.2495	0.3417	0.044*
C14	0.66965 (16)	1.1439 (4)	0.24250 (18)	0.0385 (8)
H14A	0.6252	1.1405	0.2156	0.046*
H14B	0.7027	1.2055	0.2114	0.046*
C15	0.69583 (15)	0.9771 (3)	0.25871 (15)	0.0298 (7)
H15A	0.7459	0.9779	0.2669	0.036*
H15B	0.6851	0.9037	0.2160	0.036*

	U11	U22	U33	U12	U13	U23
Br1	0.0393 (2)	0.0479 (2)	0.0394 (2)	0.01898 (17)	0.00616 (15)	0.00728 (15)
S1	0.0354 (5)	0.0370 (4)	0.0182 (4)	−0.0105 (4)	−0.0025 (3)	0.0023 (3)
O1	0.0247 (11)	0.0265 (11)	0.0214 (10)	−0.0013 (10)	0.0002 (8)	0.0014 (8)
O2	0.0728 (17)	0.0374 (13)	0.0298 (12)	−0.0144 (12)	0.0162 (11)	−0.0126 (10)
C1	0.0270 (16)	0.0230 (15)	0.0173 (14)	−0.0050 (13)	−0.0028 (12)	0.0002 (11)
C2	0.0232 (15)	0.0227 (15)	0.0169 (14)	−0.0049 (13)	−0.0009 (12)	−0.0021 (11)
C3	0.0249 (16)	0.0252 (15)	0.0199 (15)	−0.0049 (13)	0.0051 (12)	−0.0032 (12)
C4	0.0235 (16)	0.0217 (15)	0.0296 (16)	0.0029 (13)	−0.0017 (13)	−0.0022 (12)
C5	0.0305 (16)	0.0215 (14)	0.0189 (14)	−0.0019 (13)	0.0009 (12)	0.0010 (12)
C6	0.0267 (16)	0.0178 (14)	0.0199 (14)	−0.0047 (12)	0.0018 (12)	−0.0041 (11)
C7	0.0190 (15)	0.0193 (14)	0.0202 (14)	−0.0022 (12)	−0.0019 (12)	−0.0014 (11)
C8	0.0270 (17)	0.0226 (15)	0.0219 (14)	−0.0063 (13)	−0.0070 (12)	0.0015 (12)
C9	0.0303 (17)	0.0327 (17)	0.0229 (15)	0.0004 (14)	0.0052 (13)	0.0030 (12)
C10	0.0351 (18)	0.0300 (17)	0.0345 (18)	−0.0006 (14)	−0.0069 (14)	0.0026 (14)
C11	0.0230 (16)	0.0281 (16)	0.0262 (15)	0.0006 (13)	0.0001 (13)	0.0025 (12)
C12	0.0340 (19)	0.0309 (18)	0.0419 (19)	−0.0032 (15)	0.0092 (15)	−0.0070 (14)
C13	0.0345 (19)	0.0282 (18)	0.049 (2)	−0.0037 (15)	0.0022 (15)	−0.0062 (15)
C14	0.040 (2)	0.0314 (18)	0.044 (2)	−0.0028 (15)	−0.0053 (15)	0.0088 (15)
C15	0.0290 (17)	0.0310 (17)	0.0295 (16)	−0.0032 (15)	0.0038 (13)	0.0040 (13)

Br1—C4	1.900 (3)	C9—H9B	0.9800
S1—O2	1.487 (2)	C9—H9C	0.9800
S1—C1	1.762 (3)	C10—H10A	0.9800
S1—C11	1.813 (3)	C10—H10B	0.9800
O1—C8	1.378 (3)	C10—H10C	0.9800
O1—C7	1.382 (3)	C11—C12	1.536 (4)
C1—C8	1.349 (4)	C11—C15	1.539 (4)
C1—C2	1.453 (4)	C11—H11	1.0000
C2—C7	1.384 (3)	C12—C13	1.521 (4)
C2—C3	1.388 (4)	C12—H12A	0.9900
C3—C4	1.380 (3)	C12—H12B	0.9900
C3—H3	0.9500	C13—C14	1.514 (4)
C4—C5	1.394 (3)	C13—H13A	0.9900
C5—C6	1.382 (4)	C13—H13B	0.9900
C5—H5	0.9500	C14—C15	1.512 (4)
C6—C7	1.380 (3)	C14—H14A	0.9900
C6—C9	1.494 (4)	C14—H14B	0.9900
C8—C10	1.477 (4)	C15—H15A	0.9900
C9—H9A	0.9800	C15—H15B	0.9900
O2—S1—C1	107.27 (13)	C8—C10—H10B	109.5
O2—S1—C11	106.84 (13)	H10A—C10—H10B	109.5
C1—S1—C11	97.83 (12)	C8—C10—H10C	109.5
C8—O1—C7	106.4 (2)	H10A—C10—H10C	109.5
C8—C1—C2	107.3 (2)	H10B—C10—H10C	109.5
C8—C1—S1	125.7 (2)	C12—C11—C15	106.4 (2)
C2—C1—S1	127.0 (2)	C12—C11—S1	110.44 (19)
C7—C2—C3	119.5 (2)	C15—C11—S1	109.33 (19)
C7—C2—C1	104.8 (2)	C12—C11—H11	110.2
C3—C2—C1	135.6 (2)	C15—C11—H11	110.2
C4—C3—C2	116.0 (2)	S1—C11—H11	110.2
C4—C3—H3	122.0	C13—C12—C11	105.0 (2)
C2—C3—H3	122.0	C13—C12—H12A	110.8
C3—C4—C5	123.5 (3)	C11—C12—H12A	110.8
C3—C4—Br1	118.4 (2)	C13—C12—H12B	110.8
C5—C4—Br1	118.1 (2)	C11—C12—H12B	110.8
C6—C5—C4	120.9 (2)	H12A—C12—H12B	108.8
C6—C5—H5	119.6	C14—C13—C12	104.4 (2)
C4—C5—H5	119.6	C14—C13—H13A	110.9
C7—C6—C5	114.8 (2)	C12—C13—H13A	110.9
C7—C6—C9	122.9 (2)	C14—C13—H13B	110.9
C5—C6—C9	122.3 (2)	C12—C13—H13B	110.9
C6—C7—O1	124.2 (2)	H13A—C13—H13B	108.9
C6—C7—C2	125.2 (3)	C15—C14—C13	103.0 (2)
O1—C7—C2	110.6 (2)	C15—C14—H14A	111.2
C1—C8—O1	110.8 (2)	C13—C14—H14A	111.2
C1—C8—C10	133.6 (3)	C15—C14—H14B	111.2
O1—C8—C10	115.5 (2)	C13—C14—H14B	111.2
C6—C9—H9A	109.5	H14A—C14—H14B	109.1
C6—C9—H9B	109.5	C14—C15—C11	104.4 (2)
H9A—C9—H9B	109.5	C14—C15—H15A	110.9
C6—C9—H9C	109.5	C11—C15—H15A	110.9
H9A—C9—H9C	109.5	C14—C15—H15B	110.9
H9B—C9—H9C	109.5	C11—C15—H15B	110.9
C8—C10—H10A	109.5	H15A—C15—H15B	108.9
O2—S1—C1—C8	−139.5 (2)	C3—C2—C7—C6	3.7 (4)
C11—S1—C1—C8	110.1 (3)	C1—C2—C7—C6	−177.7 (3)
O2—S1—C1—C2	40.8 (3)	C3—C2—C7—O1	−177.3 (2)
C11—S1—C1—C2	−69.6 (3)	C1—C2—C7—O1	1.3 (3)
C8—C1—C2—C7	−1.7 (3)	C2—C1—C8—O1	1.5 (3)
S1—C1—C2—C7	178.1 (2)	S1—C1—C8—O1	−178.30 (18)
C8—C1—C2—C3	176.6 (3)	C2—C1—C8—C10	−177.6 (3)
S1—C1—C2—C3	−3.6 (5)	S1—C1—C8—C10	2.6 (5)
C7—C2—C3—C4	−1.9 (4)	C7—O1—C8—C1	−0.7 (3)
C1—C2—C3—C4	−179.9 (3)	C7—O1—C8—C10	178.6 (2)
C2—C3—C4—C5	−0.9 (4)	O2—S1—C11—C12	−177.07 (19)
C2—C3—C4—Br1	178.6 (2)	C1—S1—C11—C12	−66.3 (2)
C3—C4—C5—C6	2.1 (4)	O2—S1—C11—C15	66.2 (2)
Br1—C4—C5—C6	−177.4 (2)	C1—S1—C11—C15	177.0 (2)
C4—C5—C6—C7	−0.4 (4)	C15—C11—C12—C13	−5.9 (3)
C4—C5—C6—C9	−180.0 (2)	S1—C11—C12—C13	−124.4 (2)
C5—C6—C7—O1	178.7 (2)	C11—C12—C13—C14	28.9 (3)
C9—C6—C7—O1	−1.7 (4)	C12—C13—C14—C15	−41.2 (3)
C5—C6—C7—C2	−2.5 (4)	C13—C14—C15—C11	37.0 (3)
C9—C6—C7—C2	177.1 (3)	C12—C11—C15—C14	−19.3 (3)
C8—O1—C7—C6	178.5 (2)	S1—C11—C15—C14	100.0 (2)
C8—O1—C7—C2	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.60	3.465 (3)	152.
C9—H9B···O2i	0.98	2.55	3.489 (3)	161.
C10—H10B···O1ii	0.98	2.60	3.480 (3)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.60	3.465 (3)	152
C9—H9B⋯O2i	0.98	2.55	3.489 (3)	161
C10—H10B⋯O1ii	0.98	2.60	3.480 (3)	149

Symmetry codes: (i) ; (ii) .