5-Bromo-3-cyclo-pentyl-sulfinyl-2-methyl-1-benzofuran.

In the title compound, C(14)H(15)BrO(2)S, the cyclo-pentyl ring adopts an envelope conformation. In the cyclo-pentyl ring, two adjacent C atoms are disordered over two sets of sites with site-occupancy factors of 0.618 (11) and 0.382 (11). In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds.

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 structural studies of related 5-bromo-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C14H15BrO2S

M = 327.23

Monoclinic,

a = 9.4166 (6) Å

b = 9.5369 (7) Å

c = 15.1662 (11) Å

β = 100.033 (4)°

V = 1341.17 (16) Å3

Z = 4

Mo Kα radiation

μ = 3.21 mm−1

T = 173 K

0.31 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.531, T max = 0.746

12376 measured reflections

3098 independent reflections

2567 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.06

3098 reflections

182 parameters

83 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.64 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 datablocks global, I. DOI: 10.1107/S1600536811017120/qk2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017120/qk2009Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017120/qk2009Isup3.cml

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

C14H15BrO2S	F(000) = 664
Mr = 327.23	Dx = 1.621 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5053 reflections
a = 9.4166 (6) Å	θ = 2.5–27.4°
b = 9.5369 (7) Å	µ = 3.21 mm−1
c = 15.1662 (11) Å	T = 173 K
β = 100.033 (4)°	Block, colourless
V = 1341.17 (16) Å3	0.31 × 0.24 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3098 independent reflections
Radiation source: rotating anode	2567 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.2°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
Tmin = 0.531, Tmax = 0.746	l = −19→18
12376 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.9434P] where P = (Fo2 + 2Fc2)/3
3098 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.54 e Å−3
83 restraints	Δρmin = −0.64 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	Occ. (<1)
Br1	0.23192 (3)	0.05192 (3)	0.013362 (19)	0.03823 (12)
S1	0.16243 (6)	0.69180 (7)	0.10017 (4)	0.02871 (16)
O1	0.56646 (18)	0.5680 (2)	0.13602 (12)	0.0323 (4)
O2	0.0936 (2)	0.6788 (3)	0.00457 (13)	0.0467 (6)
C1	0.3266 (2)	0.5992 (3)	0.11348 (16)	0.0255 (5)
C2	0.3530 (2)	0.4544 (3)	0.09134 (15)	0.0243 (5)
C3	0.2690 (3)	0.3376 (3)	0.06233 (15)	0.0250 (5)
H3	0.1667	0.3424	0.0503	0.030*
C4	0.3415 (3)	0.2147 (3)	0.05198 (16)	0.0290 (5)
C5	0.4922 (3)	0.2047 (3)	0.06733 (18)	0.0340 (6)
H5	0.5372	0.1176	0.0593	0.041*
C6	0.5749 (3)	0.3209 (3)	0.09404 (18)	0.0348 (6)
H6	0.6772	0.3172	0.1033	0.042*
C7	0.5034 (3)	0.4422 (3)	0.10677 (17)	0.0283 (5)
C8	0.4561 (3)	0.6612 (3)	0.13951 (16)	0.0292 (5)
C9	0.5022 (3)	0.8028 (3)	0.17033 (19)	0.0376 (6)
H9A	0.6078	0.8069	0.1833	0.056*
H9B	0.4637	0.8250	0.2247	0.056*
H9C	0.4659	0.8711	0.1235	0.056*
C10	0.0670 (3)	0.5783 (3)	0.16509 (16)	0.0253 (5)
H10	0.0627	0.4807	0.1406	0.030*
C11	−0.0865 (3)	0.6359 (4)	0.16324 (19)	0.0395 (7)
H11A	−0.0923	0.7357	0.1451	0.047*	0.618 (11)
H11B	−0.1578	0.5818	0.1209	0.047*	0.618 (11)
H11C	−0.1601	0.5618	0.1472	0.047*	0.382 (11)
H11D	−0.1074	0.7143	0.1202	0.047*	0.382 (11)
C12A	−0.1140 (5)	0.6192 (9)	0.2584 (3)	0.0431 (17)	0.618 (11)
H12A	−0.1388	0.5213	0.2713	0.052*	0.618 (11)
H12B	−0.1909	0.6829	0.2711	0.052*	0.618 (11)
C13A	0.0344 (5)	0.6615 (8)	0.3103 (4)	0.0475 (18)	0.618 (11)
H13A	0.0502	0.7637	0.3060	0.057*	0.618 (11)
H13B	0.0446	0.6349	0.3742	0.057*	0.618 (11)
C12B	−0.0817 (14)	0.6861 (9)	0.2588 (3)	0.044 (3)	0.382 (11)
H12C	−0.1795	0.6854	0.2744	0.053*	0.382 (11)
H12D	−0.0426	0.7826	0.2663	0.053*	0.382 (11)
C13B	0.0173 (8)	0.5832 (11)	0.3181 (6)	0.040 (2)	0.382 (11)
H13C	0.0495	0.6203	0.3793	0.049*	0.382 (11)
H13D	−0.0283	0.4903	0.3213	0.049*	0.382 (11)
C14	0.1399 (3)	0.5790 (3)	0.26381 (18)	0.0381 (7)
H14A	0.1530	0.4823	0.2877	0.046*	0.618 (11)
H14B	0.2351	0.6259	0.2715	0.046*	0.618 (11)
H14C	0.1994	0.4937	0.2784	0.046*	0.382 (11)
H14D	0.2026	0.6624	0.2768	0.046*	0.382 (11)

	U11	U22	U33	U12	U13	U23
Br1	0.04047 (18)	0.03448 (17)	0.04127 (18)	0.00614 (12)	0.01135 (13)	−0.00446 (12)
S1	0.0221 (3)	0.0325 (3)	0.0328 (3)	0.0048 (2)	0.0086 (2)	0.0075 (3)
O1	0.0183 (8)	0.0479 (12)	0.0312 (10)	0.0003 (8)	0.0054 (7)	0.0023 (8)
O2	0.0290 (10)	0.0792 (16)	0.0320 (10)	0.0134 (10)	0.0054 (8)	0.0183 (11)
C1	0.0188 (11)	0.0333 (13)	0.0256 (12)	0.0028 (10)	0.0073 (9)	0.0053 (10)
C2	0.0192 (11)	0.0359 (13)	0.0187 (11)	0.0060 (9)	0.0056 (9)	0.0062 (9)
C3	0.0208 (11)	0.0350 (13)	0.0202 (11)	0.0050 (10)	0.0062 (9)	0.0037 (10)
C4	0.0308 (13)	0.0357 (14)	0.0218 (12)	0.0059 (11)	0.0084 (10)	0.0018 (10)
C5	0.0314 (13)	0.0419 (15)	0.0310 (13)	0.0167 (12)	0.0118 (11)	0.0057 (12)
C6	0.0201 (11)	0.0531 (17)	0.0328 (14)	0.0121 (11)	0.0090 (10)	0.0069 (13)
C7	0.0207 (11)	0.0419 (15)	0.0232 (12)	0.0026 (10)	0.0064 (9)	0.0055 (11)
C8	0.0242 (12)	0.0405 (14)	0.0238 (12)	−0.0006 (11)	0.0060 (10)	0.0036 (11)
C9	0.0325 (14)	0.0440 (16)	0.0367 (15)	−0.0079 (12)	0.0068 (12)	−0.0013 (13)
C10	0.0208 (11)	0.0301 (13)	0.0266 (12)	−0.0003 (9)	0.0081 (9)	−0.0013 (10)
C11	0.0199 (12)	0.068 (2)	0.0320 (14)	0.0022 (13)	0.0071 (11)	0.0020 (14)
C12A	0.028 (2)	0.071 (5)	0.033 (3)	0.011 (3)	0.0120 (19)	0.005 (3)
C13A	0.037 (3)	0.081 (5)	0.025 (2)	0.008 (3)	0.006 (2)	−0.009 (3)
C12B	0.054 (6)	0.049 (5)	0.035 (4)	0.022 (4)	0.027 (4)	0.006 (3)
C13B	0.044 (4)	0.048 (5)	0.034 (4)	0.004 (4)	0.019 (3)	0.007 (4)
C14	0.0281 (13)	0.0590 (19)	0.0271 (13)	0.0070 (13)	0.0049 (11)	0.0073 (13)

Br1—C4	1.900 (3)	C10—H10	1.0000
S1—O2	1.487 (2)	C11—C12A	1.519 (4)
S1—C1	1.761 (2)	C11—C12B	1.519 (4)
S1—C10	1.805 (2)	C11—H11A	0.9900
O1—C8	1.375 (3)	C11—H11B	0.9900
O1—C7	1.377 (3)	C11—H11C	0.9900
C1—C8	1.351 (4)	C11—H11D	0.9900
C1—C2	1.453 (4)	C12A—C13A	1.533 (6)
C2—C3	1.393 (4)	C12A—H12A	0.9900
C2—C7	1.399 (3)	C12A—H12B	0.9900
C3—C4	1.379 (3)	C13A—C14	1.532 (4)
C3—H3	0.9500	C13A—H13A	0.9900
C4—C5	1.400 (4)	C13A—H13B	0.9900
C5—C6	1.374 (4)	C12B—C13B	1.533 (6)
C5—H5	0.9500	C12B—H12C	0.9900
C6—C7	1.369 (4)	C12B—H12D	0.9900
C6—H6	0.9500	C13B—C14	1.531 (4)
C8—C9	1.471 (4)	C13B—H13C	0.9900
C9—H9A	0.9800	C13B—H13D	0.9900
C9—H9B	0.9800	C14—H14A	0.9900
C9—H9C	0.9800	C14—H14B	0.9900
C10—C14	1.535 (4)	C14—H14C	0.9900
C10—C11	1.541 (3)	C14—H14D	0.9900
O2—S1—C1	107.12 (12)	C10—C11—H11C	111.4
O2—S1—C10	107.95 (12)	H11A—C11—H11C	128.0
C1—S1—C10	98.47 (11)	C12A—C11—H11D	131.3
C8—O1—C7	106.76 (19)	C12B—C11—H11D	111.1
C8—C1—C2	107.5 (2)	C10—C11—H11D	111.0
C8—C1—S1	122.9 (2)	H11A—C11—H11D	25.2
C2—C1—S1	129.26 (19)	H11B—C11—H11D	86.0
C3—C2—C7	119.3 (2)	H11C—C11—H11D	109.1
C3—C2—C1	136.2 (2)	C11—C12A—C13A	99.7 (4)
C7—C2—C1	104.5 (2)	C11—C12A—H12A	111.8
C4—C3—C2	116.7 (2)	C13A—C12A—H12A	111.8
C4—C3—H3	121.6	C11—C12A—H12B	111.8
C2—C3—H3	121.6	C13A—C12A—H12B	111.8
C3—C4—C5	123.1 (3)	H12A—C12A—H12B	109.6
C3—C4—Br1	118.46 (19)	C14—C13A—C12A	103.6 (4)
C5—C4—Br1	118.4 (2)	C14—C13A—H13A	111.0
C6—C5—C4	120.0 (2)	C12A—C13A—H13A	111.0
C6—C5—H5	120.0	C14—C13A—H13B	111.0
C4—C5—H5	120.0	C12A—C13A—H13B	111.0
C7—C6—C5	117.1 (2)	H13A—C13A—H13B	109.0
C7—C6—H6	121.5	C11—C12B—C13B	105.8 (5)
C5—C6—H6	121.5	C11—C12B—H12C	110.6
C6—C7—O1	125.9 (2)	C13B—C12B—H12C	110.6
C6—C7—C2	123.7 (3)	C11—C12B—H12D	110.6
O1—C7—C2	110.4 (2)	C13B—C12B—H12D	110.6
C1—C8—O1	110.9 (2)	H12C—C12B—H12D	108.7
C1—C8—C9	134.2 (2)	C14—C13B—C12B	98.0 (5)
O1—C8—C9	115.0 (2)	C14—C13B—H13C	112.2
C8—C9—H9A	109.5	C12B—C13B—H13C	112.2
C8—C9—H9B	109.5	C14—C13B—H13D	112.2
H9A—C9—H9B	109.5	C12B—C13B—H13D	112.2
C8—C9—H9C	109.5	H13C—C13B—H13D	109.8
H9A—C9—H9C	109.5	C13B—C14—C10	105.9 (4)
H9B—C9—H9C	109.5	C13A—C14—C10	103.6 (3)
C14—C10—C11	106.0 (2)	C13B—C14—H14A	83.4
C14—C10—S1	110.42 (18)	C13A—C14—H14A	111.0
C11—C10—S1	109.34 (19)	C10—C14—H14A	111.0
C14—C10—H10	110.3	C13B—C14—H14B	132.5
C11—C10—H10	110.3	C13A—C14—H14B	111.0
S1—C10—H10	110.3	C10—C14—H14B	111.0
C12A—C11—C10	105.1 (3)	H14A—C14—H14B	109.0
C12B—C11—C10	102.9 (5)	C13B—C14—H14C	110.6
C12A—C11—H11A	110.7	C13A—C14—H14C	134.9
C12B—C11—H11A	87.3	C10—C14—H14C	110.8
C10—C11—H11A	110.7	H14B—C14—H14C	83.1
C12A—C11—H11B	110.7	C13B—C14—H14D	110.5
C12B—C11—H11B	133.5	C13A—C14—H14D	84.7
C10—C11—H11B	110.7	C10—C14—H14D	110.4
H11A—C11—H11B	108.8	H14A—C14—H14D	130.1
C12A—C11—H11C	86.0	H14C—C14—H14D	108.7
C12B—C11—H11C	111.2
O2—S1—C1—C8	118.2 (2)	S1—C1—C8—C9	6.3 (4)
C10—S1—C1—C8	−129.9 (2)	C7—O1—C8—C1	−0.2 (3)
O2—S1—C1—C2	−54.7 (2)	C7—O1—C8—C9	179.5 (2)
C10—S1—C1—C2	57.2 (2)	O2—S1—C10—C14	175.88 (18)
C8—C1—C2—C3	178.9 (3)	C1—S1—C10—C14	64.7 (2)
S1—C1—C2—C3	−7.3 (4)	O2—S1—C10—C11	−67.9 (2)
C8—C1—C2—C7	−0.1 (3)	C1—S1—C10—C11	−179.06 (19)
S1—C1—C2—C7	173.68 (19)	C14—C10—C11—C12A	−19.1 (4)
C7—C2—C3—C4	1.0 (3)	S1—C10—C11—C12A	−138.2 (4)
C1—C2—C3—C4	−177.9 (3)	C14—C10—C11—C12B	8.5 (5)
C2—C3—C4—C5	−1.4 (3)	S1—C10—C11—C12B	−110.5 (5)
C2—C3—C4—Br1	179.56 (17)	C12B—C11—C12A—C13A	−48.7 (8)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12A—C13A	40.2 (7)
Br1—C4—C5—C6	179.0 (2)	C11—C12A—C13A—C14	−46.9 (8)
C4—C5—C6—C7	1.7 (4)	C12A—C11—C12B—C13B	63.3 (8)
C5—C6—C7—O1	177.8 (2)	C10—C11—C12B—C13B	−34.7 (10)
C5—C6—C7—C2	−2.2 (4)	C11—C12B—C13B—C14	46.2 (11)
C8—O1—C7—C6	−179.9 (2)	C12B—C13B—C14—C13A	49.8 (6)
C8—O1—C7—C2	0.1 (3)	C12B—C13B—C14—C10	−39.8 (9)
C3—C2—C7—C6	0.8 (4)	C12A—C13A—C14—C13B	−62.9 (8)
C1—C2—C7—C6	180.0 (2)	C12A—C13A—C14—C10	35.4 (7)
C3—C2—C7—O1	−179.2 (2)	C11—C10—C14—C13B	20.3 (5)
C1—C2—C7—O1	0.0 (3)	S1—C10—C14—C13B	138.6 (5)
C2—C1—C8—O1	0.1 (3)	C11—C10—C14—C13A	−10.0 (4)
S1—C1—C8—O1	−174.09 (16)	S1—C10—C14—C13A	108.3 (4)
C2—C1—C8—C9	−179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.46	3.392 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.46	3.392 (3)	169

Symmetry code: (i) .