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

In the title compound, C(15)H(17)ClO(3)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

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 structural studies of related 3-aryl­sulfonyl-5-chloro-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C15H17ClO3S

M = 312.80

Monoclinic,

a = 14.3135 (2) Å

b = 9.2829 (2) Å

c = 11.3433 (2) Å

β = 107.566 (1)°

V = 1436.91 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 173 K

0.29 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.891, T max = 0.954

13251 measured reflections

3287 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.07

3287 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.37 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/S1600536811008270/bh2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008270/bh2340Isup2.hkl

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

C15H17ClO3S	F(000) = 656
Mr = 312.80	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Melting point: 440 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.3135 (2) Å	Cell parameters from 5109 reflections
b = 9.2829 (2) Å	θ = 2.7–27.5°
c = 11.3433 (2) Å	µ = 0.42 mm−1
β = 107.566 (1)°	T = 173 K
V = 1436.91 (4) Å3	Block, colourless
Z = 4	0.29 × 0.18 × 0.11 mm

Bruker SMART APEXII CCD diffractometer	3287 independent reflections
Radiation source: rotating anode	2856 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→10
Tmin = 0.891, Tmax = 0.954	l = −14→14
13251 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.093	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.5583P] where P = (Fo2 + 2Fc2)/3
3287 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.36 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
S	0.31521 (3)	0.72877 (4)	0.40822 (3)	0.02105 (11)
Cl	0.18841 (3)	0.20832 (5)	0.64837 (4)	0.03919 (13)
O2	0.28307 (9)	0.73602 (12)	0.51704 (10)	0.0298 (3)
O1	0.43749 (7)	0.36827 (12)	0.34930 (10)	0.0255 (2)
O3	0.38824 (8)	0.82960 (12)	0.39699 (11)	0.0320 (3)
C1	0.35822 (10)	0.55463 (15)	0.40040 (13)	0.0208 (3)
C2	0.33118 (10)	0.42681 (15)	0.45538 (13)	0.0209 (3)
C3	0.27018 (10)	0.39605 (17)	0.52741 (14)	0.0242 (3)
H3	0.2347	0.4694	0.5537	0.029*
C4	0.26403 (11)	0.25316 (18)	0.55855 (15)	0.0266 (3)
C5	0.31494 (11)	0.14251 (17)	0.52184 (15)	0.0294 (3)
H5	0.3075	0.0459	0.5452	0.035*
C6	0.37639 (11)	0.17320 (17)	0.45146 (15)	0.0284 (3)
H6	0.4125	0.1000	0.4260	0.034*
C7	0.38230 (10)	0.31567 (16)	0.42022 (14)	0.0230 (3)
C8	0.42122 (10)	0.51346 (16)	0.33784 (13)	0.0226 (3)
C9	0.47360 (11)	0.59044 (18)	0.26251 (15)	0.0292 (3)
H9A	0.4262	0.6427	0.1956	0.044*
H9B	0.5091	0.5208	0.2272	0.044*
H9C	0.5201	0.6588	0.3148	0.044*
C10	0.21039 (10)	0.74609 (15)	0.27476 (13)	0.0208 (3)
H10	0.2316	0.7276	0.1998	0.025*
C11	0.13094 (11)	0.63719 (17)	0.27601 (15)	0.0285 (3)
H11A	0.1104	0.6511	0.3511	0.034*
H11B	0.1570	0.5382	0.2778	0.034*
C12	0.04281 (12)	0.6570 (2)	0.16061 (17)	0.0362 (4)
H12A	0.0626	0.6364	0.0859	0.043*
H12B	−0.0094	0.5880	0.1628	0.043*
C13	0.00340 (12)	0.8095 (2)	0.15363 (18)	0.0367 (4)
H13A	−0.0523	0.8209	0.0773	0.044*
H13B	−0.0209	0.8278	0.2253	0.044*
C14	0.08265 (12)	0.91795 (19)	0.15367 (16)	0.0338 (4)
H14A	0.0561	1.0166	0.1522	0.041*
H14B	0.1027	0.9049	0.0781	0.041*
C15	0.17212 (11)	0.90049 (16)	0.26764 (15)	0.0274 (3)
H15A	0.2241	0.9684	0.2627	0.033*
H15B	0.1539	0.9231	0.3431	0.033*

	U11	U22	U33	U12	U13	U23
S	0.02279 (18)	0.01684 (18)	0.02228 (19)	0.00067 (12)	0.00493 (14)	−0.00147 (13)
Cl	0.0382 (2)	0.0426 (3)	0.0397 (3)	−0.00341 (17)	0.01619 (19)	0.01558 (19)
O2	0.0390 (6)	0.0287 (6)	0.0215 (5)	0.0062 (5)	0.0088 (5)	−0.0033 (4)
O1	0.0275 (5)	0.0225 (5)	0.0282 (6)	0.0036 (4)	0.0111 (4)	−0.0011 (4)
O3	0.0265 (5)	0.0208 (5)	0.0445 (7)	−0.0038 (4)	0.0044 (5)	0.0007 (5)
C1	0.0219 (6)	0.0188 (7)	0.0213 (7)	0.0000 (5)	0.0057 (5)	0.0003 (5)
C2	0.0213 (6)	0.0183 (7)	0.0206 (7)	0.0006 (5)	0.0027 (5)	0.0004 (5)
C3	0.0239 (7)	0.0243 (7)	0.0241 (7)	0.0019 (6)	0.0068 (6)	0.0015 (6)
C4	0.0235 (7)	0.0300 (8)	0.0246 (7)	−0.0025 (6)	0.0047 (6)	0.0063 (6)
C5	0.0329 (8)	0.0203 (7)	0.0302 (8)	−0.0011 (6)	0.0025 (6)	0.0050 (6)
C6	0.0305 (8)	0.0197 (7)	0.0318 (8)	0.0037 (6)	0.0045 (6)	−0.0012 (6)
C7	0.0226 (7)	0.0221 (7)	0.0227 (7)	0.0011 (5)	0.0045 (5)	−0.0011 (6)
C8	0.0220 (6)	0.0221 (7)	0.0220 (7)	−0.0001 (5)	0.0039 (5)	−0.0005 (6)
C9	0.0282 (7)	0.0339 (9)	0.0274 (8)	−0.0029 (6)	0.0114 (6)	0.0012 (7)
C10	0.0214 (7)	0.0206 (7)	0.0196 (7)	0.0007 (5)	0.0052 (5)	0.0002 (5)
C11	0.0274 (7)	0.0225 (7)	0.0326 (8)	−0.0035 (6)	0.0047 (6)	0.0011 (6)
C12	0.0282 (8)	0.0351 (9)	0.0387 (10)	−0.0083 (7)	0.0000 (7)	−0.0002 (8)
C13	0.0231 (8)	0.0417 (10)	0.0403 (10)	0.0006 (7)	0.0022 (7)	0.0053 (8)
C14	0.0286 (8)	0.0321 (9)	0.0363 (9)	0.0039 (6)	0.0030 (7)	0.0096 (7)
C15	0.0264 (7)	0.0211 (7)	0.0319 (8)	0.0014 (6)	0.0046 (6)	0.0030 (6)

S—O3	1.4372 (11)	C9—H9B	0.9800
S—O2	1.4431 (12)	C9—H9C	0.9800
S—C1	1.7416 (15)	C10—C11	1.525 (2)
S—C10	1.7882 (14)	C10—C15	1.528 (2)
Cl—C4	1.7461 (16)	C10—H10	1.0000
O1—C8	1.3673 (18)	C11—C12	1.530 (2)
O1—C7	1.3760 (18)	C11—H11A	0.9900
C1—C8	1.360 (2)	C11—H11B	0.9900
C1—C2	1.447 (2)	C12—C13	1.517 (3)
C2—C7	1.391 (2)	C12—H12A	0.9900
C2—C3	1.393 (2)	C12—H12B	0.9900
C3—C4	1.382 (2)	C13—C14	1.516 (2)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.394 (2)	C13—H13B	0.9900
C5—C6	1.384 (2)	C14—C15	1.529 (2)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.378 (2)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C8—C9	1.480 (2)	C15—H15B	0.9900
C9—H9A	0.9800
O3—S—O2	118.27 (7)	C11—C10—C15	111.46 (12)
O3—S—C1	108.80 (7)	C11—C10—S	111.72 (10)
O2—S—C1	107.20 (7)	C15—C10—S	108.96 (10)
O3—S—C10	108.26 (7)	C11—C10—H10	108.2
O2—S—C10	108.50 (7)	C15—C10—H10	108.2
C1—S—C10	105.04 (7)	S—C10—H10	108.2
C8—O1—C7	107.10 (11)	C10—C11—C12	109.68 (13)
C8—C1—C2	107.48 (13)	C10—C11—H11A	109.7
C8—C1—S	126.00 (11)	C12—C11—H11A	109.7
C2—C1—S	126.49 (11)	C10—C11—H11B	109.7
C7—C2—C3	119.53 (13)	C12—C11—H11B	109.7
C7—C2—C1	104.62 (13)	H11A—C11—H11B	108.2
C3—C2—C1	135.84 (13)	C13—C12—C11	110.76 (14)
C4—C3—C2	116.49 (14)	C13—C12—H12A	109.5
C4—C3—H3	121.8	C11—C12—H12A	109.5
C2—C3—H3	121.8	C13—C12—H12B	109.5
C3—C4—C5	123.47 (15)	C11—C12—H12B	109.5
C3—C4—Cl	118.45 (13)	H12A—C12—H12B	108.1
C5—C4—Cl	118.08 (12)	C14—C13—C12	110.68 (14)
C6—C5—C4	120.08 (15)	C14—C13—H13A	109.5
C6—C5—H5	120.0	C12—C13—H13A	109.5
C4—C5—H5	120.0	C14—C13—H13B	109.5
C7—C6—C5	116.40 (14)	C12—C13—H13B	109.5
C7—C6—H6	121.8	H13A—C13—H13B	108.1
C5—C6—H6	121.8	C13—C14—C15	111.43 (14)
O1—C7—C6	125.55 (14)	C13—C14—H14A	109.3
O1—C7—C2	110.42 (13)	C15—C14—H14A	109.3
C6—C7—C2	124.03 (14)	C13—C14—H14B	109.3
C1—C8—O1	110.38 (13)	C15—C14—H14B	109.3
C1—C8—C9	134.19 (14)	H14A—C14—H14B	108.0
O1—C8—C9	115.43 (13)	C10—C15—C14	109.85 (13)
C8—C9—H9A	109.5	C10—C15—H15A	109.7
C8—C9—H9B	109.5	C14—C15—H15A	109.7
H9A—C9—H9B	109.5	C10—C15—H15B	109.7
C8—C9—H9C	109.5	C14—C15—H15B	109.7
H9A—C9—H9C	109.5	H15A—C15—H15B	108.2
H9B—C9—H9C	109.5
O3—S—C1—C8	−29.39 (15)	C3—C2—C7—C6	0.5 (2)
O2—S—C1—C8	−158.38 (13)	C1—C2—C7—C6	−178.90 (14)
C10—S—C1—C8	86.33 (14)	C2—C1—C8—O1	−0.51 (16)
O3—S—C1—C2	152.86 (12)	S—C1—C8—O1	−178.61 (10)
O2—S—C1—C2	23.87 (14)	C2—C1—C8—C9	179.31 (15)
C10—S—C1—C2	−91.41 (13)	S—C1—C8—C9	1.2 (3)
C8—C1—C2—C7	0.17 (16)	C7—O1—C8—C1	0.64 (16)
S—C1—C2—C7	178.26 (11)	C7—O1—C8—C9	−179.21 (12)
C8—C1—C2—C3	−179.09 (16)	O3—S—C10—C11	177.11 (11)
S—C1—C2—C3	−1.0 (2)	O2—S—C10—C11	−53.37 (12)
C7—C2—C3—C4	−0.6 (2)	C1—S—C10—C11	61.01 (12)
C1—C2—C3—C4	178.57 (15)	O3—S—C10—C15	−59.29 (12)
C2—C3—C4—C5	0.0 (2)	O2—S—C10—C15	70.23 (12)
C2—C3—C4—Cl	−179.83 (11)	C1—S—C10—C15	−175.40 (10)
C3—C4—C5—C6	0.7 (2)	C15—C10—C11—C12	57.47 (17)
Cl—C4—C5—C6	−179.44 (12)	S—C10—C11—C12	179.64 (12)
C4—C5—C6—C7	−0.8 (2)	C10—C11—C12—C13	−57.59 (19)
C8—O1—C7—C6	178.58 (14)	C11—C12—C13—C14	57.6 (2)
C8—O1—C7—C2	−0.52 (16)	C12—C13—C14—C15	−56.9 (2)
C5—C6—C7—O1	−178.78 (14)	C11—C10—C15—C14	−56.53 (17)
C5—C6—C7—C2	0.2 (2)	S—C10—C15—C14	179.73 (11)
C3—C2—C7—O1	179.63 (12)	C13—C14—C15—C10	55.92 (19)
C1—C2—C7—O1	0.21 (16)

Cg is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.54	3.2630 (19)	133
C10—H10···O2ii	1.00	2.42	3.3899 (19)	162
C9—H9C···Cgiii	0.98	2.69	3.577 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.95	2.54	3.2630 (19)	133
C10—H10⋯O2ii	1.00	2.42	3.3899 (19)	162
C9—H9C⋯Cgiii	0.98	2.69	3.577 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) .