3-(4-Chloro-phenyl-sulfon-yl)-5-isopropyl-2-methyl-1-benzofuran.

In the title mol-ecule, C(18)H(17)ClO(3)S, the 4-chloro-phenyl ring makes a dihedral angle of 77.03 (5)° with the mean plane of the benzofuran fragment. In the crystal structure, the mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

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

Experimental

Crystal data

C18H17ClO3S

M = 348.83

Monoclinic,

a = 11.4851 (4) Å

b = 11.3194 (4) Å

c = 13.0600 (4) Å

β = 101.475 (2)°

V = 1663.92 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.29 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.660, T max = 0.746

14572 measured reflections

3643 independent reflections

3109 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.08

3643 reflections

211 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.65 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/S1600536811014784/su2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014784/su2271Isup2.hkl

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

C18H17ClO3S	F(000) = 728
Mr = 348.83	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5946 reflections
a = 11.4851 (4) Å	θ = 2.4–28.3°
b = 11.3194 (4) Å	µ = 0.37 mm−1
c = 13.0600 (4) Å	T = 296 K
β = 101.475 (2)°	Block, colourless
V = 1663.92 (10) Å3	0.29 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3643 independent reflections
Radiation source: rotating anode	3109 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.040
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.660, Tmax = 0.746	l = −16→16
14572 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) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8346P] where P = (Fo2 + 2Fc2)/3
3643 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.67 e Å−3
1 restraint	Δρmin = −0.65 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
Cl1	0.26041 (5)	0.75171 (5)	−0.02985 (5)	0.04730 (19)
S1	0.05170 (4)	0.34612 (5)	0.20282 (4)	0.02918 (16)
O1	0.28084 (13)	0.32071 (12)	0.46858 (10)	0.0284 (3)
O2	−0.04776 (13)	0.39127 (15)	0.24196 (13)	0.0410 (4)
O3	0.03725 (14)	0.24367 (13)	0.13660 (12)	0.0364 (4)
C1	0.16557 (17)	0.31448 (17)	0.30843 (15)	0.0259 (4)
C2	0.26193 (16)	0.23122 (16)	0.30977 (14)	0.0234 (4)
C3	0.29613 (17)	0.15214 (17)	0.23947 (15)	0.0267 (4)
H3	0.2521	0.1454	0.1718	0.032*
C4	0.39669 (18)	0.08375 (18)	0.27190 (15)	0.0276 (4)
C5	0.46245 (17)	0.09257 (17)	0.37270 (14)	0.0290 (4)
H5	0.5292	0.0452	0.3930	0.035*
C6	0.42883 (17)	0.17475 (17)	0.44745 (14)	0.0279 (4)
H6	0.4720	0.1827	0.5153	0.033*
C7	0.32941 (17)	0.23906 (16)	0.41025 (14)	0.0242 (4)
C8	0.18122 (18)	0.36468 (18)	0.40469 (16)	0.0287 (4)
C9	0.4355 (2)	−0.0030 (2)	0.19646 (17)	0.0356 (5)
H9	0.3747	−0.0018	0.1321	0.043*
C10	0.5518 (3)	0.0338 (3)	0.1676 (3)	0.0635 (8)
H10A	0.5444	0.1124	0.1395	0.095*
H10B	0.5708	−0.0197	0.1163	0.095*
H10C	0.6140	0.0320	0.2288	0.095*
C11	0.4420 (3)	−0.1283 (2)	0.2381 (2)	0.0586 (8)
H11A	0.5058	−0.1344	0.2978	0.088*
H11B	0.4560	−0.1818	0.1848	0.088*
H11C	0.3684	−0.1482	0.2581	0.088*
C12	0.1135 (2)	0.4515 (2)	0.45385 (18)	0.0420 (6)
H12A	0.0530	0.4865	0.4013	0.063*
H12B	0.1662	0.5119	0.4874	0.063*
H12C	0.0772	0.4124	0.5048	0.063*
C13	0.10801 (17)	0.46178 (18)	0.13593 (16)	0.0289 (4)
C14	0.1036 (2)	0.5775 (2)	0.17029 (17)	0.0358 (5)
H14	0.0693	0.5944	0.2274	0.043*
C15	0.1502 (2)	0.6673 (2)	0.11922 (19)	0.0383 (5)
H15	0.1484	0.7450	0.1419	0.046*
C16	0.19963 (18)	0.6399 (2)	0.03376 (18)	0.0339 (5)
C17	0.2032 (2)	0.5257 (2)	−0.00179 (18)	0.0368 (5)
H17	0.2363	0.5092	−0.0597	0.044*
C18	0.15686 (19)	0.4358 (2)	0.04978 (16)	0.0336 (5)
H18	0.1585	0.3583	0.0267	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0377 (3)	0.0432 (4)	0.0619 (4)	−0.0010 (2)	0.0123 (3)	0.0175 (3)
S1	0.0243 (3)	0.0286 (3)	0.0343 (3)	0.00487 (19)	0.0049 (2)	0.0052 (2)
O1	0.0352 (7)	0.0273 (7)	0.0242 (7)	0.0024 (6)	0.0093 (6)	−0.0011 (5)
O2	0.0282 (8)	0.0458 (10)	0.0512 (9)	0.0108 (7)	0.0136 (7)	0.0117 (8)
O3	0.0346 (8)	0.0310 (8)	0.0399 (8)	0.0000 (6)	−0.0015 (7)	−0.0003 (6)
C1	0.0260 (9)	0.0242 (9)	0.0283 (9)	0.0041 (7)	0.0076 (7)	0.0036 (8)
C2	0.0235 (9)	0.0224 (9)	0.0247 (9)	0.0009 (7)	0.0057 (7)	0.0031 (7)
C3	0.0297 (10)	0.0274 (10)	0.0222 (9)	0.0030 (8)	0.0034 (8)	−0.0001 (7)
C4	0.0303 (10)	0.0250 (10)	0.0288 (9)	0.0043 (8)	0.0092 (8)	0.0019 (8)
C5	0.0251 (9)	0.0283 (11)	0.0336 (10)	0.0041 (8)	0.0056 (8)	0.0052 (8)
C6	0.0281 (9)	0.0292 (10)	0.0246 (9)	−0.0026 (8)	0.0012 (8)	0.0031 (8)
C7	0.0282 (9)	0.0221 (9)	0.0238 (9)	−0.0024 (7)	0.0090 (7)	0.0014 (7)
C8	0.0327 (10)	0.0245 (10)	0.0319 (10)	0.0034 (8)	0.0133 (8)	0.0041 (8)
C9	0.0426 (12)	0.0338 (12)	0.0312 (10)	0.0136 (9)	0.0095 (9)	−0.0016 (9)
C10	0.073 (2)	0.0551 (18)	0.077 (2)	0.0068 (14)	0.0497 (17)	−0.0074 (15)
C11	0.096 (2)	0.0326 (13)	0.0543 (16)	0.0061 (14)	0.0326 (16)	−0.0058 (11)
C12	0.0532 (14)	0.0375 (13)	0.0400 (12)	0.0143 (11)	0.0209 (11)	−0.0020 (10)
C13	0.0253 (9)	0.0287 (10)	0.0321 (10)	0.0072 (8)	0.0041 (8)	0.0051 (8)
C14	0.0398 (11)	0.0320 (12)	0.0373 (11)	0.0078 (9)	0.0117 (9)	0.0019 (9)
C15	0.0431 (12)	0.0269 (11)	0.0455 (12)	0.0044 (9)	0.0101 (10)	−0.0010 (9)
C16	0.0254 (10)	0.0342 (12)	0.0412 (12)	0.0041 (8)	0.0045 (8)	0.0100 (9)
C17	0.0351 (11)	0.0397 (13)	0.0384 (11)	0.0087 (9)	0.0141 (9)	0.0055 (9)
C18	0.0355 (11)	0.0306 (11)	0.0354 (11)	0.0091 (9)	0.0086 (9)	0.0017 (9)

Cl1—C16	1.735 (2)	C9—C10	1.517 (4)
S1—O2	1.4352 (15)	C9—H9	0.9800
S1—O3	1.4364 (16)	C10—H10A	0.9600
S1—C1	1.739 (2)	C10—H10B	0.9600
S1—C13	1.766 (2)	C10—H10C	0.9600
O1—C8	1.369 (2)	C11—H11A	0.9600
O1—C7	1.384 (2)	C11—H11B	0.9600
C1—C8	1.359 (3)	C11—H11C	0.9600
C1—C2	1.451 (3)	C12—H12A	0.9600
C2—C7	1.388 (3)	C12—H12B	0.9600
C2—C3	1.394 (3)	C12—H12C	0.9600
C3—C4	1.385 (3)	C13—C18	1.385 (3)
C3—H3	0.9300	C13—C14	1.388 (3)
C4—C5	1.385 (3)	C14—C15	1.381 (3)
C4—C9	1.519 (3)	C14—H14	0.9300
C5—C6	1.4551 (17)	C15—C16	1.384 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.360 (3)	C16—C17	1.377 (3)
C6—H6	0.9300	C17—C18	1.383 (3)
C8—C12	1.477 (3)	C17—H17	0.9300
C9—C11	1.516 (3)	C18—H18	0.9300
O2—S1—O3	119.81 (10)	C9—C10—H10A	109.5
O2—S1—C1	108.49 (9)	C9—C10—H10B	109.5
O3—S1—C1	106.86 (9)	H10A—C10—H10B	109.5
O2—S1—C13	107.93 (9)	C9—C10—H10C	109.5
O3—S1—C13	108.09 (10)	H10A—C10—H10C	109.5
C1—S1—C13	104.68 (9)	H10B—C10—H10C	109.5
C8—O1—C7	106.68 (15)	C9—C11—H11A	109.5
C8—C1—C2	107.47 (17)	C9—C11—H11B	109.5
C8—C1—S1	126.02 (15)	H11A—C11—H11B	109.5
C2—C1—S1	126.50 (15)	C9—C11—H11C	109.5
C7—C2—C3	119.10 (17)	H11A—C11—H11C	109.5
C7—C2—C1	104.54 (16)	H11B—C11—H11C	109.5
C3—C2—C1	136.35 (18)	C8—C12—H12A	109.5
C4—C3—C2	119.01 (18)	C8—C12—H12B	109.5
C4—C3—H3	120.5	H12A—C12—H12B	109.5
C2—C3—H3	120.5	C8—C12—H12C	109.5
C3—C4—C5	120.95 (17)	H12A—C12—H12C	109.5
C3—C4—C9	119.83 (18)	H12B—C12—H12C	109.5
C5—C4—C9	119.22 (17)	C18—C13—C14	120.6 (2)
C4—C5—C6	121.10 (17)	C18—C13—S1	119.47 (17)
C4—C5—H5	119.4	C14—C13—S1	119.90 (16)
C6—C5—H5	119.4	C15—C14—C13	119.7 (2)
C7—C6—C5	114.74 (17)	C15—C14—H14	120.1
C7—C6—H6	122.6	C13—C14—H14	120.1
C5—C6—H6	122.6	C14—C15—C16	119.0 (2)
C6—C7—O1	124.24 (17)	C14—C15—H15	120.5
C6—C7—C2	125.10 (17)	C16—C15—H15	120.5
O1—C7—C2	110.65 (16)	C17—C16—C15	121.8 (2)
C1—C8—O1	110.66 (17)	C17—C16—Cl1	118.80 (17)
C1—C8—C12	134.1 (2)	C15—C16—Cl1	119.43 (18)
O1—C8—C12	115.19 (18)	C16—C17—C18	119.1 (2)
C11—C9—C10	111.3 (2)	C16—C17—H17	120.5
C11—C9—C4	111.85 (18)	C18—C17—H17	120.5
C10—C9—C4	111.7 (2)	C17—C18—C13	119.8 (2)
C11—C9—H9	107.2	C17—C18—H18	120.1
C10—C9—H9	107.2	C13—C18—H18	120.1
C4—C9—H9	107.2
O2—S1—C1—C8	−24.7 (2)	S1—C1—C8—O1	−179.01 (14)
O3—S1—C1—C8	−155.17 (18)	C2—C1—C8—C12	−177.8 (2)
C13—S1—C1—C8	90.33 (19)	S1—C1—C8—C12	3.0 (4)
O2—S1—C1—C2	156.20 (17)	C7—O1—C8—C1	−0.3 (2)
O3—S1—C1—C2	25.73 (19)	C7—O1—C8—C12	178.10 (17)
C13—S1—C1—C2	−88.77 (18)	C3—C4—C9—C11	−122.0 (2)
C8—C1—C2—C7	0.0 (2)	C5—C4—C9—C11	57.6 (3)
S1—C1—C2—C7	179.20 (14)	C3—C4—C9—C10	112.5 (2)
C8—C1—C2—C3	178.7 (2)	C5—C4—C9—C10	−67.9 (3)
S1—C1—C2—C3	−2.0 (3)	O2—S1—C13—C18	−146.81 (17)
C7—C2—C3—C4	−0.1 (3)	O3—S1—C13—C18	−15.87 (19)
C1—C2—C3—C4	−178.8 (2)	C1—S1—C13—C18	97.77 (18)
C2—C3—C4—C5	0.4 (3)	O2—S1—C13—C14	33.5 (2)
C2—C3—C4—C9	−179.98 (18)	O3—S1—C13—C14	164.47 (17)
C3—C4—C5—C6	−0.6 (3)	C1—S1—C13—C14	−81.89 (18)
C9—C4—C5—C6	179.76 (18)	C18—C13—C14—C15	−1.2 (3)
C4—C5—C6—C7	0.5 (3)	S1—C13—C14—C15	178.50 (17)
C5—C6—C7—O1	178.91 (16)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—C2	−0.2 (3)	C14—C15—C16—C17	0.2 (3)
C8—O1—C7—C6	−178.93 (18)	C14—C15—C16—Cl1	−179.07 (17)
C8—O1—C7—C2	0.3 (2)	C15—C16—C17—C18	−0.5 (3)
C3—C2—C7—C6	0.0 (3)	Cl1—C16—C17—C18	178.81 (17)
C1—C2—C7—C6	179.07 (18)	C16—C17—C18—C13	−0.1 (3)
C3—C2—C7—O1	−179.21 (16)	C14—C13—C18—C17	0.9 (3)
C1—C2—C7—O1	−0.2 (2)	S1—C13—C18—C17	−178.76 (16)
C2—C1—C8—O1	0.2 (2)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O3i	0.96	2.57	3.489 (3)	160
C11—H11B···Cgii	0.96	2.81	3.562 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O3i	0.96	2.57	3.489 (3)	160
C11—H11B⋯Cgii	0.96	2.81	3.562 (3)	136

Symmetry codes: (i) ; (ii) .