5-Chloro-3-cyclo-pentyl-sulfonyl-2-methyl-1-benzofuran.

In the title compound, C(14)H(15)ClO(3)S, the cyclo-penyl ring adopts an envelope conformation. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds into dual chains propagating in [100]. The dual chains arise from pairs of the same or different hydrogen bonds between adjacent molecules.

Related literature

For the pharmacological 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: Seo et al. (2011a ▶,b ▶).

Experimental

Crystal data

C14H15ClO3S

M = 298.77

Triclinic,

a = 7.4833 (8) Å

b = 8.7888 (9) Å

c = 10.9061 (10) Å

α = 66.919 (5)°

β = 82.848 (6)°

γ = 82.689 (6)°

V = 652.31 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.45 mm−1

T = 173 K

0.39 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.844, T max = 0.905

11884 measured reflections

3252 independent reflections

2721 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.143

S = 1.05

3252 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.73 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/S160053681103933X/cv5153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103933X/cv5153Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103933X/cv5153Isup3.cml

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

C14H15ClO3S	Z = 2
Mr = 298.77	F(000) = 312
Triclinic, P1	Dx = 1.521 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4833 (8) Å	Cell parameters from 5081 reflections
b = 8.7888 (9) Å	θ = 2.5–28.2°
c = 10.9061 (10) Å	µ = 0.45 mm−1
α = 66.919 (5)°	T = 173 K
β = 82.848 (6)°	Block, colourless
γ = 82.689 (6)°	0.39 × 0.27 × 0.22 mm
V = 652.31 (11) Å3

Bruker SMART APEXII CCD diffractometer	3252 independent reflections
Radiation source: rotating anode	2721 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.046
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.844, Tmax = 0.905	l = −14→14
11884 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.143	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3252 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.73 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
S1	0.01806 (6)	0.70534 (5)	0.73025 (4)	0.02070 (15)
Cl1	0.22626 (7)	0.92775 (6)	0.13290 (4)	0.03364 (17)
O1	0.26706 (18)	0.34648 (14)	0.62681 (11)	0.0261 (3)
O2	−0.07756 (18)	0.60437 (16)	0.85224 (11)	0.0291 (3)
O3	−0.08387 (17)	0.83205 (15)	0.62857 (11)	0.0257 (3)
C1	0.1369 (2)	0.5756 (2)	0.65566 (15)	0.0210 (3)
C2	0.1864 (2)	0.6199 (2)	0.51383 (15)	0.0209 (3)
C3	0.1721 (2)	0.7648 (2)	0.39920 (15)	0.0225 (4)
H3	0.1194	0.8673	0.4030	0.027*
C4	0.2388 (3)	0.7506 (2)	0.28003 (16)	0.0243 (4)
C5	0.3159 (3)	0.6020 (2)	0.27022 (17)	0.0276 (4)
H5	0.3586	0.5994	0.1853	0.033*
C6	0.3301 (3)	0.4594 (2)	0.38371 (17)	0.0274 (4)
H6	0.3818	0.3568	0.3797	0.033*
C7	0.2654 (2)	0.4727 (2)	0.50369 (15)	0.0221 (4)
C8	0.1883 (2)	0.4117 (2)	0.71738 (16)	0.0245 (4)
C9	0.1791 (3)	0.2926 (2)	0.85921 (17)	0.0321 (4)
H9A	0.1229	0.3503	0.9169	0.048*
H9B	0.3015	0.2468	0.8848	0.048*
H9C	0.1068	0.2023	0.8693	0.048*
C10	0.1818 (2)	0.8010 (2)	0.77215 (15)	0.0232 (4)
H10	0.1163	0.8755	0.8158	0.028*
C11	0.3143 (3)	0.6800 (2)	0.86896 (17)	0.0295 (4)
H11A	0.2577	0.6388	0.9618	0.035*
H11B	0.3568	0.5842	0.8436	0.035*
C12	0.4688 (3)	0.7835 (3)	0.85509 (18)	0.0328 (4)
H12A	0.5859	0.7157	0.8595	0.039*
H12B	0.4556	0.8253	0.9281	0.039*
C13	0.4615 (3)	0.9290 (2)	0.71898 (19)	0.0327 (4)
H13A	0.4423	1.0361	0.7310	0.039*
H13B	0.5758	0.9276	0.6629	0.039*
C14	0.3028 (3)	0.9064 (2)	0.65330 (16)	0.0278 (4)
H14A	0.2385	1.0147	0.6028	0.033*
H14B	0.3446	0.8483	0.5920	0.033*

	U11	U22	U33	U12	U13	U23
S1	0.0169 (3)	0.0228 (2)	0.0204 (2)	0.00049 (18)	−0.00042 (16)	−0.00706 (17)
Cl1	0.0423 (3)	0.0320 (3)	0.0211 (2)	−0.0046 (2)	−0.00045 (19)	−0.00445 (19)
O1	0.0293 (8)	0.0185 (6)	0.0285 (6)	0.0010 (5)	−0.0056 (5)	−0.0068 (5)
O2	0.0240 (7)	0.0365 (7)	0.0233 (6)	−0.0060 (6)	0.0040 (5)	−0.0084 (5)
O3	0.0214 (7)	0.0259 (6)	0.0272 (6)	0.0044 (5)	−0.0051 (5)	−0.0082 (5)
C1	0.0198 (9)	0.0212 (8)	0.0210 (7)	−0.0016 (7)	−0.0013 (6)	−0.0070 (6)
C2	0.0180 (9)	0.0215 (8)	0.0235 (7)	−0.0010 (7)	−0.0017 (6)	−0.0092 (6)
C3	0.0212 (9)	0.0217 (8)	0.0238 (7)	−0.0002 (7)	−0.0019 (6)	−0.0085 (6)
C4	0.0233 (10)	0.0263 (8)	0.0218 (7)	−0.0041 (7)	−0.0018 (6)	−0.0071 (6)
C5	0.0243 (10)	0.0352 (10)	0.0276 (8)	−0.0022 (8)	−0.0002 (7)	−0.0175 (8)
C6	0.0263 (10)	0.0258 (8)	0.0350 (9)	0.0027 (8)	−0.0045 (7)	−0.0176 (7)
C7	0.0209 (9)	0.0193 (7)	0.0250 (7)	−0.0007 (7)	−0.0041 (6)	−0.0070 (6)
C8	0.0221 (10)	0.0233 (8)	0.0272 (8)	−0.0024 (7)	−0.0039 (7)	−0.0079 (7)
C9	0.0375 (12)	0.0222 (8)	0.0295 (8)	−0.0025 (8)	−0.0084 (8)	−0.0007 (7)
C10	0.0202 (9)	0.0247 (8)	0.0245 (7)	0.0015 (7)	−0.0009 (6)	−0.0105 (7)
C11	0.0276 (11)	0.0326 (9)	0.0252 (8)	−0.0018 (8)	−0.0059 (7)	−0.0068 (7)
C12	0.0241 (11)	0.0447 (11)	0.0293 (9)	−0.0041 (9)	−0.0041 (7)	−0.0129 (8)
C13	0.0289 (12)	0.0274 (9)	0.0411 (10)	−0.0038 (8)	−0.0058 (8)	−0.0109 (8)
C14	0.0267 (11)	0.0265 (8)	0.0266 (8)	−0.0038 (8)	−0.0033 (7)	−0.0054 (7)

S1—O2	1.4382 (12)	C8—C9	1.488 (2)
S1—O3	1.4415 (11)	C9—H9A	0.9800
S1—C1	1.7441 (16)	C9—H9B	0.9800
S1—C10	1.7664 (18)	C9—H9C	0.9800
Cl1—C4	1.7463 (17)	C10—C14	1.529 (2)
O1—C8	1.365 (2)	C10—C11	1.530 (2)
O1—C7	1.3662 (18)	C10—H10	1.0000
C1—C8	1.356 (2)	C11—C12	1.517 (3)
C1—C2	1.450 (2)	C11—H11A	0.9900
C2—C7	1.392 (2)	C11—H11B	0.9900
C2—C3	1.395 (2)	C12—C13	1.535 (3)
C3—C4	1.380 (2)	C12—H12A	0.9900
C3—H3	0.9500	C12—H12B	0.9900
C4—C5	1.397 (3)	C13—C14	1.531 (3)
C5—C6	1.378 (2)	C13—H13A	0.9900
C5—H5	0.9500	C13—H13B	0.9900
C6—C7	1.381 (2)	C14—H14A	0.9900
C6—H6	0.9500	C14—H14B	0.9900
O2—S1—O3	118.65 (8)	C8—C9—H9C	109.5
O2—S1—C1	108.48 (8)	H9A—C9—H9C	109.5
O3—S1—C1	106.51 (7)	H9B—C9—H9C	109.5
O2—S1—C10	108.07 (8)	C14—C10—C11	104.30 (15)
O3—S1—C10	108.11 (8)	C14—C10—S1	114.73 (12)
C1—S1—C10	106.39 (8)	C11—C10—S1	114.46 (12)
C8—O1—C7	106.90 (12)	C14—C10—H10	107.7
C8—C1—C2	107.01 (14)	C11—C10—H10	107.7
C8—C1—S1	126.67 (12)	S1—C10—H10	107.7
C2—C1—S1	126.15 (12)	C12—C11—C10	103.74 (15)
C7—C2—C3	120.01 (14)	C12—C11—H11A	111.0
C7—C2—C1	104.43 (14)	C10—C11—H11A	111.0
C3—C2—C1	135.56 (15)	C12—C11—H11B	111.0
C4—C3—C2	116.08 (15)	C10—C11—H11B	111.0
C4—C3—H3	122.0	H11A—C11—H11B	109.0
C2—C3—H3	122.0	C11—C12—C13	107.18 (15)
C3—C4—C5	123.68 (16)	C11—C12—H12A	110.3
C3—C4—Cl1	118.36 (13)	C13—C12—H12A	110.3
C5—C4—Cl1	117.96 (13)	C11—C12—H12B	110.3
C6—C5—C4	120.02 (15)	C13—C12—H12B	110.3
C6—C5—H5	120.0	H12A—C12—H12B	108.5
C4—C5—H5	120.0	C14—C13—C12	106.39 (17)
C5—C6—C7	116.75 (15)	C14—C13—H13A	110.5
C5—C6—H6	121.6	C12—C13—H13A	110.5
C7—C6—H6	121.6	C14—C13—H13B	110.5
O1—C7—C6	125.78 (14)	C12—C13—H13B	110.5
O1—C7—C2	110.78 (13)	H13A—C13—H13B	108.6
C6—C7—C2	123.44 (15)	C10—C14—C13	103.38 (14)
C1—C8—O1	110.88 (14)	C10—C14—H14A	111.1
C1—C8—C9	134.00 (15)	C13—C14—H14A	111.1
O1—C8—C9	115.11 (14)	C10—C14—H14B	111.1
C8—C9—H9A	109.5	C13—C14—H14B	111.1
C8—C9—H9B	109.5	H14A—C14—H14B	109.1
H9A—C9—H9B	109.5
O2—S1—C1—C8	−22.22 (19)	C1—C2—C7—O1	−0.2 (2)
O3—S1—C1—C8	−151.00 (17)	C3—C2—C7—C6	−1.1 (3)
C10—S1—C1—C8	93.83 (18)	C1—C2—C7—C6	179.06 (17)
O2—S1—C1—C2	152.39 (16)	C2—C1—C8—O1	0.0 (2)
O3—S1—C1—C2	23.61 (18)	S1—C1—C8—O1	175.43 (13)
C10—S1—C1—C2	−91.55 (17)	C2—C1—C8—C9	179.0 (2)
C8—C1—C2—C7	0.1 (2)	S1—C1—C8—C9	−5.5 (3)
S1—C1—C2—C7	−175.35 (14)	C7—O1—C8—C1	−0.1 (2)
C8—C1—C2—C3	−179.7 (2)	C7—O1—C8—C9	−179.37 (15)
S1—C1—C2—C3	4.8 (3)	O2—S1—C10—C14	176.93 (11)
C7—C2—C3—C4	0.3 (3)	O3—S1—C10—C14	−53.47 (13)
C1—C2—C3—C4	−179.85 (19)	C1—S1—C10—C14	60.60 (13)
C2—C3—C4—C5	0.5 (3)	O2—S1—C10—C11	56.38 (14)
C2—C3—C4—Cl1	−179.62 (13)	O3—S1—C10—C11	−174.02 (12)
C3—C4—C5—C6	−0.6 (3)	C1—S1—C10—C11	−59.95 (13)
Cl1—C4—C5—C6	179.48 (15)	C14—C10—C11—C12	37.10 (17)
C4—C5—C6—C7	−0.1 (3)	S1—C10—C11—C12	163.27 (12)
C8—O1—C7—C6	−179.05 (19)	C10—C11—C12—C13	−22.06 (19)
C8—O1—C7—C2	0.2 (2)	C11—C12—C13—C14	−1.1 (2)
C5—C6—C7—O1	−179.91 (17)	C11—C10—C14—C13	−37.65 (17)
C5—C6—C7—C2	0.9 (3)	S1—C10—C14—C13	−163.66 (12)
C3—C2—C7—O1	179.66 (15)	C12—C13—C14—C10	23.73 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.95	2.51	3.420 (2)	160.
C12—H12A···O2ii	0.99	2.59	3.557 (2)	167.
C13—H13B···O3ii	0.99	2.61	3.516 (3)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.95	2.51	3.420 (2)	160
C12—H12A⋯O2ii	0.99	2.59	3.557 (2)	167
C13—H13B⋯O3ii	0.99	2.61	3.516 (3)	153

Symmetry codes: (i) ; (ii) .