3-(4-Chloro-phenyl-sulfon-yl)-2,5-dimethyl-1-benzofuran.

In the title compound, C(16)H(13)ClO(3)S, the 4-chloro-phenyl ring makes a dihedral angle of 79.96 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological 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 our previous structural studies of related 3-(4-chloro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C16H13ClO3S

M = 320.77

Monoclinic,

a = 15.3529 (3) Å

b = 12.1495 (2) Å

c = 8.2663 (2) Å

β = 105.363 (1)°

V = 1486.82 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 177 K

0.37 × 0.23 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.867, T max = 0.962

13864 measured reflections

3398 independent reflections

2655 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.06

3398 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 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/S1600536810044223/ng5054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044223/ng5054Isup2.hkl

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

C16H13ClO3S	F(000) = 664
Mr = 320.77	Dx = 1.433 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 4847 reflections
a = 15.3529 (3) Å	θ = 2.8–27.5°
b = 12.1495 (2) Å	µ = 0.40 mm−1
c = 8.2663 (2) Å	T = 177 K
β = 105.363 (1)°	Block, colourless
V = 1486.82 (5) Å3	0.37 × 0.23 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3398 independent reflections
Radiation source: rotating anode	2655 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.4°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→14
Tmin = 0.867, Tmax = 0.962	l = −10→10
13864 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.4243P] where P = (Fo2 + 2Fc2)/3
3398 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 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
Cl	0.48342 (4)	0.92660 (5)	0.73305 (10)	0.0705 (2)
S	0.17974 (3)	0.58289 (4)	0.44925 (5)	0.03028 (14)
O1	0.04560 (8)	0.56425 (10)	0.79164 (16)	0.0336 (3)
O2	0.11294 (8)	0.63535 (12)	0.31700 (15)	0.0417 (3)
O3	0.22166 (9)	0.48321 (11)	0.41515 (15)	0.0384 (3)
C1	0.13384 (11)	0.55688 (14)	0.6156 (2)	0.0282 (4)
C2	0.17212 (10)	0.48293 (14)	0.75339 (19)	0.0265 (4)
C3	0.24701 (11)	0.41325 (14)	0.7986 (2)	0.0286 (4)
H3	0.2872	0.4070	0.7293	0.034*
C4	0.26171 (11)	0.35337 (15)	0.9461 (2)	0.0305 (4)
C5	0.20127 (12)	0.36427 (16)	1.0465 (2)	0.0336 (4)
H5	0.2120	0.3226	1.1471	0.040*
C6	0.12720 (12)	0.43281 (15)	1.0054 (2)	0.0346 (4)
H6	0.0871	0.4400	1.0748	0.041*
C7	0.11476 (11)	0.49046 (15)	0.8570 (2)	0.0287 (4)
C8	0.05880 (11)	0.60332 (15)	0.6451 (2)	0.0312 (4)
C9	0.34169 (13)	0.27807 (18)	0.9993 (2)	0.0426 (5)
H9A	0.3251	0.2045	0.9527	0.064*
H9B	0.3608	0.2738	1.1220	0.064*
H9C	0.3914	0.3068	0.9579	0.064*
C10	−0.00891 (12)	0.68520 (16)	0.5565 (3)	0.0403 (5)
H10A	0.0030	0.7562	0.6145	0.060*
H10B	−0.0696	0.6598	0.5558	0.060*
H10C	−0.0048	0.6936	0.4409	0.060*
C11	0.26643 (11)	0.67929 (14)	0.5303 (2)	0.0285 (4)
C12	0.24350 (12)	0.78759 (16)	0.5522 (2)	0.0372 (4)
H12	0.1818	0.8092	0.5243	0.045*
C13	0.31025 (13)	0.86365 (16)	0.6145 (3)	0.0409 (5)
H13	0.2954	0.9381	0.6301	0.049*
C14	0.39885 (13)	0.83017 (17)	0.6538 (3)	0.0418 (5)
C15	0.42284 (13)	0.72285 (18)	0.6332 (3)	0.0527 (6)
H15	0.4846	0.7016	0.6616	0.063*
C16	0.35555 (12)	0.64652 (17)	0.5705 (3)	0.0435 (5)
H16	0.3706	0.5721	0.5552	0.052*

	U11	U22	U33	U12	U13	U23
Cl	0.0463 (3)	0.0523 (4)	0.1062 (6)	−0.0155 (3)	0.0085 (3)	−0.0142 (3)
S	0.0351 (2)	0.0300 (3)	0.0243 (2)	0.00103 (18)	0.00535 (17)	0.00088 (17)
O1	0.0275 (6)	0.0353 (7)	0.0396 (7)	−0.0011 (5)	0.0114 (5)	−0.0041 (6)
O2	0.0411 (7)	0.0475 (9)	0.0302 (7)	0.0000 (6)	−0.0013 (5)	0.0064 (6)
O3	0.0524 (8)	0.0333 (7)	0.0313 (6)	0.0023 (6)	0.0143 (6)	−0.0041 (6)
C1	0.0294 (8)	0.0253 (9)	0.0285 (8)	−0.0018 (7)	0.0050 (7)	−0.0015 (7)
C2	0.0294 (8)	0.0247 (9)	0.0251 (8)	−0.0053 (7)	0.0066 (6)	−0.0032 (7)
C3	0.0312 (8)	0.0280 (9)	0.0281 (8)	0.0004 (7)	0.0105 (7)	−0.0024 (7)
C4	0.0328 (9)	0.0276 (9)	0.0294 (8)	−0.0032 (7)	0.0050 (7)	−0.0005 (7)
C5	0.0402 (10)	0.0331 (10)	0.0276 (8)	−0.0092 (8)	0.0090 (7)	0.0012 (8)
C6	0.0358 (9)	0.0377 (11)	0.0340 (9)	−0.0083 (8)	0.0160 (8)	−0.0043 (8)
C7	0.0254 (8)	0.0279 (9)	0.0333 (9)	−0.0036 (7)	0.0086 (7)	−0.0050 (7)
C8	0.0288 (8)	0.0283 (9)	0.0338 (9)	−0.0042 (7)	0.0039 (7)	−0.0053 (8)
C9	0.0444 (11)	0.0420 (12)	0.0403 (10)	0.0056 (9)	0.0092 (9)	0.0095 (9)
C10	0.0325 (9)	0.0334 (11)	0.0498 (11)	0.0038 (8)	0.0016 (8)	−0.0051 (9)
C11	0.0325 (8)	0.0277 (9)	0.0254 (8)	0.0027 (7)	0.0076 (7)	0.0041 (7)
C12	0.0316 (9)	0.0315 (10)	0.0471 (11)	0.0065 (8)	0.0082 (8)	0.0035 (9)
C13	0.0429 (10)	0.0281 (10)	0.0522 (12)	0.0023 (8)	0.0134 (9)	0.0013 (9)
C14	0.0361 (10)	0.0380 (11)	0.0490 (11)	−0.0068 (8)	0.0074 (8)	−0.0018 (9)
C15	0.0299 (10)	0.0440 (13)	0.0790 (16)	0.0052 (9)	0.0055 (10)	−0.0068 (12)
C16	0.0358 (10)	0.0337 (11)	0.0591 (13)	0.0073 (8)	0.0092 (9)	−0.0028 (10)

Cl—C14	1.743 (2)	C6—H6	0.9500
S—O3	1.4339 (14)	C8—C10	1.484 (2)
S—O2	1.4350 (13)	C9—H9A	0.9800
S—C1	1.7319 (17)	C9—H9B	0.9800
S—C11	1.7664 (18)	C9—H9C	0.9800
O1—C8	1.366 (2)	C10—H10A	0.9800
O1—C7	1.385 (2)	C10—H10B	0.9800
C1—C8	1.362 (2)	C10—H10C	0.9800
C1—C2	1.448 (2)	C11—C16	1.378 (2)
C2—C7	1.384 (2)	C11—C12	1.386 (3)
C2—C3	1.397 (2)	C12—C13	1.375 (3)
C3—C4	1.386 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.374 (3)
C4—C5	1.406 (2)	C13—H13	0.9500
C4—C9	1.501 (2)	C14—C15	1.378 (3)
C5—C6	1.377 (3)	C15—C16	1.383 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.381 (3)	C16—H16	0.9500
O3—S—O2	119.53 (8)	C4—C9—H9A	109.5
O3—S—C1	107.47 (8)	C4—C9—H9B	109.5
O2—S—C1	109.07 (8)	H9A—C9—H9B	109.5
O3—S—C11	107.60 (8)	C4—C9—H9C	109.5
O2—S—C11	108.01 (8)	H9A—C9—H9C	109.5
C1—S—C11	104.12 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.00 (13)	C8—C10—H10A	109.5
C8—C1—C2	107.60 (15)	C8—C10—H10B	109.5
C8—C1—S	127.45 (14)	H10A—C10—H10B	109.5
C2—C1—S	124.91 (13)	C8—C10—H10C	109.5
C7—C2—C3	119.21 (15)	H10A—C10—H10C	109.5
C7—C2—C1	104.70 (15)	H10B—C10—H10C	109.5
C3—C2—C1	136.09 (15)	C16—C11—C12	120.86 (17)
C4—C3—C2	118.96 (15)	C16—C11—S	119.99 (14)
C4—C3—H3	120.5	C12—C11—S	119.15 (13)
C2—C3—H3	120.5	C13—C12—C11	119.80 (17)
C3—C4—C5	119.40 (16)	C13—C12—H12	120.1
C3—C4—C9	120.51 (16)	C11—C12—H12	120.1
C5—C4—C9	120.09 (16)	C14—C13—C12	118.87 (18)
C6—C5—C4	122.84 (16)	C14—C13—H13	120.6
C6—C5—H5	118.6	C12—C13—H13	120.6
C4—C5—H5	118.6	C13—C14—C15	122.10 (18)
C5—C6—C7	115.89 (16)	C13—C14—Cl	118.84 (16)
C5—C6—H6	122.1	C15—C14—Cl	119.06 (15)
C7—C6—H6	122.1	C14—C15—C16	118.91 (18)
C6—C7—C2	123.71 (16)	C14—C15—H15	120.5
C6—C7—O1	125.86 (15)	C16—C15—H15	120.5
C2—C7—O1	110.43 (15)	C11—C16—C15	119.46 (18)
C1—C8—O1	110.27 (15)	C11—C16—H16	120.3
C1—C8—C10	134.82 (17)	C15—C16—H16	120.3
O1—C8—C10	114.91 (15)
O3—S—C1—C8	−148.80 (16)	C8—O1—C7—C2	0.37 (18)
O2—S—C1—C8	−17.84 (19)	C2—C1—C8—O1	−0.30 (19)
C11—S—C1—C8	97.26 (17)	S—C1—C8—O1	−178.16 (12)
O3—S—C1—C2	33.69 (16)	C2—C1—C8—C10	178.95 (18)
O2—S—C1—C2	164.64 (14)	S—C1—C8—C10	1.1 (3)
C11—S—C1—C2	−80.26 (15)	C7—O1—C8—C1	−0.03 (18)
C8—C1—C2—C7	0.51 (18)	C7—O1—C8—C10	−179.45 (14)
S—C1—C2—C7	178.44 (13)	O3—S—C11—C16	−8.62 (18)
C8—C1—C2—C3	−179.35 (18)	O2—S—C11—C16	−138.91 (15)
S—C1—C2—C3	−1.4 (3)	C1—S—C11—C16	105.24 (16)
C7—C2—C3—C4	0.1 (2)	O3—S—C11—C12	171.21 (14)
C1—C2—C3—C4	179.94 (18)	O2—S—C11—C12	40.92 (17)
C2—C3—C4—C5	−0.1 (2)	C1—S—C11—C12	−74.93 (16)
C2—C3—C4—C9	−179.70 (16)	C16—C11—C12—C13	0.1 (3)
C3—C4—C5—C6	−0.2 (3)	S—C11—C12—C13	−179.71 (14)
C9—C4—C5—C6	179.34 (17)	C11—C12—C13—C14	0.0 (3)
C4—C5—C6—C7	0.6 (3)	C12—C13—C14—C15	−0.2 (3)
C5—C6—C7—C2	−0.6 (3)	C12—C13—C14—Cl	−179.91 (15)
C5—C6—C7—O1	−179.53 (16)	C13—C14—C15—C16	0.2 (4)
C3—C2—C7—C6	0.3 (3)	Cl—C14—C15—C16	179.91 (18)
C1—C2—C7—C6	−179.60 (16)	C12—C11—C16—C15	−0.1 (3)
C3—C2—C7—O1	179.35 (14)	S—C11—C16—C15	179.72 (17)
C1—C2—C7—O1	−0.54 (18)	C14—C15—C16—C11	0.0 (3)
C8—O1—C7—C6	179.41 (17)

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

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.56	3.495 (2)	167
C10—H10A···O2ii	0.98	2.43	3.279 (2)	145
C13—H13···Cgiii	0.95	2.74	3.411 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.56	3.495 (2)	167
C10—H10A⋯O2ii	0.98	2.43	3.279 (2)	145
C13—H13⋯Cgiii	0.95	2.74	3.411 (2)	128

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