5-Chloro-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C16H13ClO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.004 (2) Å] of the benzo-furan ring system and the 4-methyl-phenyl ring is 29.25 (8)°. In the crystal, inversion dimers linked by pairs of weak C-H⋯O interactions generate R 2 (2)(14) loops.

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: Choi et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C16H13ClO2S

M = 304.77

Triclinic,

a = 8.0694 (8) Å

b = 8.0763 (8) Å

c = 11.4208 (11) Å

α = 90.185 (6)°

β = 96.280 (6)°

γ = 111.701 (6)°

V = 686.63 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 173 K

0.35 × 0.34 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.865, T max = 0.958

12808 measured reflections

3423 independent reflections

3021 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

3423 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018400/nk2211sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018400/nk2211Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018400/nk2211Isup3.cml

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

C16H13ClO2S	Z = 2
Mr = 304.77	F(000) = 316
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Melting point = 459–460 K
a = 8.0694 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0763 (8) Å	Cell parameters from 4424 reflections
c = 11.4208 (11) Å	θ = 2.7–28.1°
α = 90.185 (6)°	µ = 0.43 mm−1
β = 96.280 (6)°	T = 173 K
γ = 111.701 (6)°	Block, colourless
V = 686.63 (12) Å3	0.35 × 0.34 × 0.10 mm

Bruker SMART APEXII CCD diffractometer	3423 independent reflections
Radiation source: rotating anode	3021 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.048
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.865, Tmax = 0.958	l = −15→15
12808 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.3137P] where P = (Fo2 + 2Fc2)/3
3423 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 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	0.21613 (6)	−0.06293 (6)	0.00434 (4)	0.03430 (13)
S1	0.79728 (5)	0.32171 (5)	0.40498 (4)	0.02612 (12)
O1	0.30621 (15)	0.15287 (15)	0.50057 (10)	0.0257 (2)
O2	0.82257 (18)	0.19866 (17)	0.31756 (13)	0.0401 (3)
C1	0.5655 (2)	0.2423 (2)	0.41897 (14)	0.0239 (3)
C2	0.4219 (2)	0.1456 (2)	0.32835 (14)	0.0236 (3)
C3	0.4092 (2)	0.0990 (2)	0.20888 (14)	0.0259 (3)
H3	0.5122	0.1328	0.1679	0.031*
C4	0.2396 (2)	0.0014 (2)	0.15325 (14)	0.0269 (3)
C5	0.0852 (2)	−0.0505 (2)	0.21040 (15)	0.0291 (3)
H5	−0.0284	−0.1179	0.1680	0.035*
C6	0.0970 (2)	−0.0040 (2)	0.32891 (15)	0.0282 (3)
H6	−0.0061	−0.0370	0.3698	0.034*
C7	0.2666 (2)	0.0929 (2)	0.38407 (14)	0.0241 (3)
C8	0.4897 (2)	0.2427 (2)	0.52001 (14)	0.0238 (3)
C9	0.5607 (2)	0.3179 (2)	0.63960 (14)	0.0238 (3)
C10	0.7141 (2)	0.4725 (2)	0.66158 (15)	0.0280 (3)
H10	0.7738	0.5314	0.5976	0.034*
C11	0.7804 (2)	0.5414 (2)	0.77602 (15)	0.0296 (4)
H11	0.8862	0.6458	0.7898	0.036*
C12	0.6930 (2)	0.4586 (2)	0.87084 (15)	0.0282 (3)
C13	0.5390 (2)	0.3061 (2)	0.84809 (15)	0.0281 (3)
H13	0.4780	0.2489	0.9121	0.034*
C14	0.4720 (2)	0.2353 (2)	0.73466 (14)	0.0256 (3)
H14	0.3661	0.1309	0.7213	0.031*
C15	0.7646 (3)	0.5323 (3)	0.99514 (16)	0.0390 (4)
H15A	0.6653	0.5005	1.0436	0.059*
H15B	0.8228	0.6624	0.9952	0.059*
H15C	0.8522	0.4818	1.0276	0.059*
C16	0.8112 (3)	0.5192 (2)	0.32875 (16)	0.0318 (4)
H16A	0.9311	0.5749	0.3036	0.048*
H16B	0.7896	0.6031	0.3815	0.048*
H16C	0.7206	0.4877	0.2595	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0365 (3)	0.0364 (2)	0.0259 (2)	0.01030 (19)	−0.00156 (17)	−0.00172 (16)
S1	0.0199 (2)	0.0253 (2)	0.0326 (2)	0.00772 (16)	0.00336 (15)	0.00359 (15)
O1	0.0207 (6)	0.0284 (6)	0.0265 (6)	0.0073 (5)	0.0031 (4)	−0.0001 (4)
O2	0.0316 (7)	0.0302 (6)	0.0614 (9)	0.0115 (6)	0.0178 (6)	−0.0034 (6)
C1	0.0214 (8)	0.0241 (7)	0.0262 (7)	0.0090 (6)	0.0017 (6)	0.0007 (6)
C2	0.0218 (8)	0.0215 (7)	0.0281 (8)	0.0091 (6)	0.0014 (6)	0.0021 (6)
C3	0.0257 (8)	0.0260 (7)	0.0269 (8)	0.0107 (6)	0.0035 (6)	0.0021 (6)
C4	0.0303 (9)	0.0243 (7)	0.0255 (7)	0.0106 (7)	−0.0008 (6)	0.0001 (6)
C5	0.0252 (8)	0.0272 (8)	0.0315 (8)	0.0076 (7)	−0.0026 (7)	0.0006 (6)
C6	0.0226 (8)	0.0287 (8)	0.0329 (8)	0.0089 (7)	0.0031 (6)	0.0024 (6)
C7	0.0238 (8)	0.0237 (7)	0.0256 (7)	0.0098 (6)	0.0021 (6)	0.0015 (6)
C8	0.0201 (8)	0.0218 (7)	0.0290 (8)	0.0073 (6)	0.0021 (6)	0.0021 (6)
C9	0.0241 (8)	0.0240 (7)	0.0258 (7)	0.0117 (6)	0.0034 (6)	0.0014 (6)
C10	0.0301 (9)	0.0248 (7)	0.0282 (8)	0.0081 (7)	0.0072 (7)	0.0031 (6)
C11	0.0297 (9)	0.0234 (7)	0.0329 (8)	0.0065 (7)	0.0046 (7)	−0.0028 (6)
C12	0.0311 (9)	0.0278 (8)	0.0275 (8)	0.0132 (7)	0.0030 (7)	−0.0024 (6)
C13	0.0298 (9)	0.0296 (8)	0.0270 (8)	0.0123 (7)	0.0075 (7)	0.0048 (6)
C14	0.0228 (8)	0.0236 (7)	0.0301 (8)	0.0081 (6)	0.0040 (6)	0.0027 (6)
C15	0.0417 (11)	0.0422 (10)	0.0295 (9)	0.0116 (9)	0.0035 (8)	−0.0084 (7)
C16	0.0342 (10)	0.0272 (8)	0.0355 (9)	0.0118 (7)	0.0087 (7)	0.0073 (7)

Cl1—C4	1.7462 (16)	C9—C10	1.393 (2)
S1—O2	1.4879 (13)	C9—C14	1.399 (2)
S1—C1	1.7648 (17)	C10—C11	1.388 (2)
S1—C16	1.7925 (17)	C10—H10	0.9500
O1—C7	1.3768 (18)	C11—C12	1.393 (2)
O1—C8	1.3790 (19)	C11—H11	0.9500
C1—C8	1.364 (2)	C12—C13	1.387 (2)
C1—C2	1.445 (2)	C12—C15	1.505 (2)
C2—C7	1.393 (2)	C13—C14	1.382 (2)
C2—C3	1.397 (2)	C13—H13	0.9500
C3—C4	1.381 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.396 (2)	C15—H15B	0.9800
C5—C6	1.387 (2)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.378 (2)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C8—C9	1.459 (2)
O2—S1—C1	106.64 (7)	C10—C9—C8	121.45 (14)
O2—S1—C16	106.07 (8)	C14—C9—C8	119.67 (15)
C1—S1—C16	97.73 (8)	C11—C10—C9	120.65 (15)
C7—O1—C8	106.62 (12)	C11—C10—H10	119.7
C8—C1—C2	107.24 (14)	C9—C10—H10	119.7
C8—C1—S1	126.49 (13)	C10—C11—C12	120.54 (16)
C2—C1—S1	125.89 (12)	C10—C11—H11	119.7
C7—C2—C3	119.27 (15)	C12—C11—H11	119.7
C7—C2—C1	105.00 (14)	C13—C12—C11	118.46 (15)
C3—C2—C1	135.73 (15)	C13—C12—C15	120.74 (16)
C4—C3—C2	116.75 (15)	C11—C12—C15	120.80 (16)
C4—C3—H3	121.6	C14—C13—C12	121.65 (16)
C2—C3—H3	121.6	C14—C13—H13	119.2
C3—C4—C5	123.29 (15)	C12—C13—H13	119.2
C3—C4—Cl1	118.71 (13)	C13—C14—C9	119.81 (15)
C5—C4—Cl1	118.00 (13)	C13—C14—H14	120.1
C6—C5—C4	120.20 (15)	C9—C14—H14	120.1
C6—C5—H5	119.9	C12—C15—H15A	109.5
C4—C5—H5	119.9	C12—C15—H15B	109.5
C7—C6—C5	116.26 (15)	H15A—C15—H15B	109.5
C7—C6—H6	121.9	C12—C15—H15C	109.5
C5—C6—H6	121.9	H15A—C15—H15C	109.5
O1—C7—C6	125.14 (14)	H15B—C15—H15C	109.5
O1—C7—C2	110.63 (14)	S1—C16—H16A	109.5
C6—C7—C2	124.23 (15)	S1—C16—H16B	109.5
C1—C8—O1	110.51 (14)	H16A—C16—H16B	109.5
C1—C8—C9	133.98 (15)	S1—C16—H16C	109.5
O1—C8—C9	115.51 (13)	H16A—C16—H16C	109.5
C10—C9—C14	118.87 (15)	H16B—C16—H16C	109.5
O2—S1—C1—C8	142.96 (15)	C1—C2—C7—C6	−179.96 (15)
C16—S1—C1—C8	−107.64 (15)	C2—C1—C8—O1	−0.17 (17)
O2—S1—C1—C2	−29.09 (16)	S1—C1—C8—O1	−173.43 (11)
C16—S1—C1—C2	80.31 (15)	C2—C1—C8—C9	−179.34 (16)
C8—C1—C2—C7	−0.40 (17)	S1—C1—C8—C9	7.4 (3)
S1—C1—C2—C7	172.92 (12)	C7—O1—C8—C1	0.68 (17)
C8—C1—C2—C3	179.75 (17)	C7—O1—C8—C9	−179.99 (12)
S1—C1—C2—C3	−6.9 (3)	C1—C8—C9—C10	29.6 (3)
C7—C2—C3—C4	−0.1 (2)	O1—C8—C9—C10	−149.54 (15)
C1—C2—C3—C4	179.69 (16)	C1—C8—C9—C14	−151.36 (18)
C2—C3—C4—C5	0.1 (2)	O1—C8—C9—C14	29.5 (2)
C2—C3—C4—Cl1	−179.18 (11)	C14—C9—C10—C11	1.5 (2)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−179.49 (15)
Cl1—C4—C5—C6	179.45 (12)	C9—C10—C11—C12	−1.0 (3)
C4—C5—C6—C7	−0.4 (2)	C10—C11—C12—C13	0.2 (2)
C8—O1—C7—C6	179.86 (15)	C10—C11—C12—C15	179.82 (16)
C8—O1—C7—C2	−0.94 (16)	C11—C12—C13—C14	0.3 (2)
C5—C6—C7—O1	179.43 (14)	C15—C12—C13—C14	−179.38 (16)
C5—C6—C7—C2	0.3 (2)	C12—C13—C14—C9	0.2 (2)
C3—C2—C7—O1	−179.29 (13)	C10—C9—C14—C13	−1.0 (2)
C1—C2—C7—O1	0.83 (17)	C8—C9—C14—C13	179.91 (14)
C3—C2—C7—C6	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.95	2.54	3.436 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.54	3.436 (2)	158

Symmetry code: (i) .