3-(4-Bromo-phenyl-sulfin-yl)-5-chloro-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)BrClO(2)S, the 4-bromo-phenyl ring makes a dihedral angle of 86.85 (6)° with the mean plane [mean deviation = 0.009 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by slipped π-π inter-actions between the benzene and the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.884 (2), inter-planar distance = 3.369 (2) and slippage = 1.945 (2) Å], and between the 4-bromo-phenyl rings of adjacent mol-ecules [centroid-centroid distance = 3.882 (2), inter-planar distance = 3.552 (2) and slippage = 1.566 (2) Å]. A Br⋯Br [3.6446 (4) Å] halogen inter-action is also observed.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C15H10BrClO2S

M = 369.65

Triclinic,

a = 6.4192 (1) Å

b = 9.9185 (2) Å

c = 11.7755 (2) Å

α = 100.681 (1)°

β = 92.113 (1)°

γ = 104.168 (1)°

V = 711.67 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.22 mm−1

T = 173 K

0.38 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.374, T max = 0.475

13131 measured reflections

3529 independent reflections

3236 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.12

3529 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.76 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) I. DOI: 10.1107/S1600536812025846/ds2198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025846/ds2198Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025846/ds2198Isup3.cml

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

C15H10BrClO2S	Z = 2
Mr = 369.65	F(000) = 368
Triclinic, P1	Dx = 1.725 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4192 (1) Å	Cell parameters from 7922 reflections
b = 9.9185 (2) Å	θ = 2.5–28.3°
c = 11.7755 (2) Å	µ = 3.22 mm−1
α = 100.681 (1)°	T = 173 K
β = 92.113 (1)°	Block, colourless
γ = 104.168 (1)°	0.38 × 0.31 × 0.27 mm
V = 711.67 (2) Å3

Bruker SMART APEXII CCD diffractometer	3529 independent reflections
Radiation source: rotating anode	3236 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.374, Tmax = 0.475	l = −15→15
13131 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F2) = 0.081	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.3308P] where P = (Fo2 + 2Fc2)/3
3529 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.76 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
Br1	0.73945 (4)	0.92053 (2)	0.917091 (18)	0.03412 (8)
Cl1	−0.34796 (9)	0.39254 (7)	0.44410 (7)	0.05267 (19)
S1	0.18432 (8)	0.27154 (5)	0.84285 (4)	0.02666 (11)
O1	0.3068 (2)	0.10245 (15)	0.53223 (12)	0.0280 (3)
O2	−0.0436 (3)	0.27377 (19)	0.86385 (15)	0.0408 (4)
C1	0.1970 (3)	0.21347 (19)	0.69398 (16)	0.0221 (3)
C2	0.0811 (3)	0.23994 (19)	0.59651 (16)	0.0218 (3)
C3	−0.0758 (3)	0.3123 (2)	0.58146 (19)	0.0273 (4)
H3	−0.1307	0.3616	0.6456	0.033*
C4	−0.1474 (3)	0.3084 (2)	0.4682 (2)	0.0329 (5)
C5	−0.0676 (4)	0.2384 (3)	0.3725 (2)	0.0381 (5)
H5	−0.1203	0.2402	0.2965	0.046*
C6	0.0869 (4)	0.1664 (3)	0.38686 (19)	0.0353 (5)
H6	0.1427	0.1179	0.3225	0.042*
C7	0.1560 (3)	0.1686 (2)	0.49963 (17)	0.0254 (4)
C8	0.3276 (3)	0.1306 (2)	0.65100 (18)	0.0253 (4)
C9	0.4833 (4)	0.0697 (2)	0.7071 (2)	0.0357 (5)
H9A	0.6304	0.1255	0.7026	0.054*
H9B	0.4668	−0.0287	0.6672	0.054*
H9C	0.4555	0.0720	0.7886	0.054*
C10	0.3331 (3)	0.4532 (2)	0.85442 (15)	0.0222 (3)
C11	0.2396 (3)	0.5607 (2)	0.89910 (18)	0.0283 (4)
H11	0.0936	0.5387	0.9172	0.034*
C12	0.3588 (3)	0.7010 (2)	0.91761 (18)	0.0296 (4)
H12	0.2961	0.7758	0.9486	0.036*
C13	0.5709 (3)	0.7301 (2)	0.89001 (16)	0.0247 (4)
C14	0.6662 (3)	0.6227 (2)	0.84636 (19)	0.0294 (4)
H14	0.8119	0.6448	0.8279	0.035*
C15	0.5474 (3)	0.4829 (2)	0.82977 (19)	0.0292 (4)
H15	0.6119	0.4080	0.8018	0.035*

	U11	U22	U33	U12	U13	U23
Br1	0.04322 (14)	0.02544 (12)	0.02911 (12)	0.00304 (9)	0.00126 (9)	0.00208 (8)
Cl1	0.0273 (3)	0.0545 (4)	0.0839 (5)	0.0083 (2)	−0.0072 (3)	0.0384 (4)
S1	0.0281 (2)	0.0293 (2)	0.0188 (2)	0.00123 (18)	0.00349 (17)	0.00343 (18)
O1	0.0258 (7)	0.0302 (7)	0.0268 (7)	0.0092 (6)	0.0044 (5)	−0.0010 (6)
O2	0.0277 (8)	0.0484 (9)	0.0358 (8)	−0.0032 (7)	0.0136 (6)	−0.0022 (7)
C1	0.0210 (8)	0.0223 (8)	0.0210 (8)	0.0032 (7)	0.0012 (7)	0.0024 (7)
C2	0.0194 (8)	0.0224 (8)	0.0214 (8)	0.0020 (7)	0.0022 (7)	0.0032 (7)
C3	0.0207 (9)	0.0270 (9)	0.0344 (10)	0.0038 (7)	0.0034 (7)	0.0090 (8)
C4	0.0203 (9)	0.0330 (10)	0.0460 (12)	0.0002 (8)	−0.0024 (8)	0.0195 (9)
C5	0.0302 (11)	0.0500 (13)	0.0286 (10)	−0.0052 (9)	−0.0063 (8)	0.0165 (10)
C6	0.0338 (11)	0.0448 (12)	0.0215 (9)	0.0014 (9)	0.0033 (8)	0.0035 (9)
C7	0.0208 (8)	0.0290 (9)	0.0233 (9)	0.0024 (7)	0.0026 (7)	0.0025 (7)
C8	0.0220 (9)	0.0233 (8)	0.0283 (9)	0.0030 (7)	0.0014 (7)	0.0032 (7)
C9	0.0286 (10)	0.0325 (11)	0.0471 (13)	0.0110 (8)	−0.0020 (9)	0.0075 (10)
C10	0.0216 (8)	0.0264 (9)	0.0160 (8)	0.0043 (7)	0.0001 (6)	0.0002 (7)
C11	0.0218 (9)	0.0363 (10)	0.0279 (10)	0.0105 (8)	0.0053 (7)	0.0042 (8)
C12	0.0308 (10)	0.0311 (10)	0.0290 (10)	0.0150 (8)	0.0053 (8)	0.0014 (8)
C13	0.0287 (9)	0.0246 (9)	0.0189 (8)	0.0057 (7)	−0.0013 (7)	0.0022 (7)
C14	0.0215 (9)	0.0316 (10)	0.0337 (10)	0.0067 (8)	0.0054 (8)	0.0026 (8)
C15	0.0251 (9)	0.0290 (10)	0.0323 (10)	0.0090 (8)	0.0087 (8)	−0.0005 (8)

Br1—C13	1.895 (2)	C5—H5	0.9500
Br1—Br1i	3.6446 (4)	C6—C7	1.379 (3)
Cl1—C4	1.738 (2)	C6—H6	0.9500
Cl1—Cl1ii	3.3576 (15)	C8—C9	1.482 (3)
S1—O2	1.4973 (16)	C9—H9A	0.9800
S1—C1	1.7522 (19)	C9—H9B	0.9800
S1—C10	1.798 (2)	C9—H9C	0.9800
O1—C8	1.369 (2)	C10—C11	1.380 (3)
O1—C7	1.375 (2)	C10—C15	1.388 (3)
C1—C8	1.360 (3)	C11—C12	1.387 (3)
C1—C2	1.444 (3)	C11—H11	0.9500
C2—C7	1.393 (3)	C12—C13	1.385 (3)
C2—C3	1.396 (3)	C12—H12	0.9500
C3—C4	1.386 (3)	C13—C14	1.383 (3)
C3—H3	0.9500	C14—C15	1.383 (3)
C4—C5	1.392 (3)	C14—H14	0.9500
C5—C6	1.378 (4)	C15—H15	0.9500
C13—Br1—Br1i	129.17 (6)	C1—C8—O1	110.68 (17)
C4—Cl1—Cl1ii	147.84 (10)	C1—C8—C9	132.7 (2)
O2—S1—C1	108.52 (9)	O1—C8—C9	116.58 (17)
O2—S1—C10	106.57 (9)	C8—C9—H9A	109.5
C1—S1—C10	98.01 (9)	C8—C9—H9B	109.5
C8—O1—C7	106.55 (14)	H9A—C9—H9B	109.5
C8—C1—C2	107.50 (16)	C8—C9—H9C	109.5
C8—C1—S1	123.01 (15)	H9A—C9—H9C	109.5
C2—C1—S1	129.49 (14)	H9B—C9—H9C	109.5
C7—C2—C3	119.56 (18)	C11—C10—C15	120.93 (18)
C7—C2—C1	104.41 (16)	C11—C10—S1	119.38 (15)
C3—C2—C1	136.02 (18)	C15—C10—S1	119.34 (15)
C4—C3—C2	116.62 (19)	C10—C11—C12	119.95 (18)
C4—C3—H3	121.7	C10—C11—H11	120.0
C2—C3—H3	121.7	C12—C11—H11	120.0
C3—C4—C5	122.8 (2)	C13—C12—C11	118.80 (18)
C3—C4—Cl1	118.67 (18)	C13—C12—H12	120.6
C5—C4—Cl1	118.47 (17)	C11—C12—H12	120.6
C6—C5—C4	120.8 (2)	C14—C13—C12	121.50 (19)
C6—C5—H5	119.6	C14—C13—Br1	118.71 (15)
C4—C5—H5	119.6	C12—C13—Br1	119.75 (15)
C5—C6—C7	116.4 (2)	C13—C14—C15	119.41 (18)
C5—C6—H6	121.8	C13—C14—H14	120.3
C7—C6—H6	121.8	C15—C14—H14	120.3
O1—C7—C6	125.35 (18)	C14—C15—C10	119.37 (18)
O1—C7—C2	110.85 (17)	C14—C15—H15	120.3
C6—C7—C2	123.8 (2)	C10—C15—H15	120.3
O2—S1—C1—C8	−144.10 (17)	C1—C2—C7—C6	−179.82 (19)
C10—S1—C1—C8	105.36 (17)	C2—C1—C8—O1	0.7 (2)
O2—S1—C1—C2	35.8 (2)	S1—C1—C8—O1	−179.37 (13)
C10—S1—C1—C2	−74.70 (18)	C2—C1—C8—C9	179.8 (2)
C8—C1—C2—C7	−0.4 (2)	S1—C1—C8—C9	−0.3 (3)
S1—C1—C2—C7	179.69 (15)	C7—O1—C8—C1	−0.7 (2)
C8—C1—C2—C3	178.4 (2)	C7—O1—C8—C9	−179.98 (17)
S1—C1—C2—C3	−1.6 (3)	O2—S1—C10—C11	11.79 (19)
C7—C2—C3—C4	−0.2 (3)	C1—S1—C10—C11	123.91 (16)
C1—C2—C3—C4	−178.8 (2)	O2—S1—C10—C15	−174.93 (16)
C2—C3—C4—C5	−0.9 (3)	C1—S1—C10—C15	−62.81 (18)
C2—C3—C4—Cl1	178.31 (14)	C15—C10—C11—C12	1.4 (3)
Cl1ii—Cl1—C4—C3	8.9 (3)	S1—C10—C11—C12	174.58 (16)
Cl1ii—Cl1—C4—C5	−171.87 (13)	C10—C11—C12—C13	0.3 (3)
C3—C4—C5—C6	1.1 (3)	C11—C12—C13—C14	−1.0 (3)
Cl1—C4—C5—C6	−178.09 (17)	C11—C12—C13—Br1	−178.79 (15)
C4—C5—C6—C7	−0.2 (3)	Br1i—Br1—C13—C14	−52.56 (18)
C8—O1—C7—C6	−179.8 (2)	Br1i—Br1—C13—C12	125.32 (15)
C8—O1—C7—C2	0.5 (2)	C12—C13—C14—C15	0.0 (3)
C5—C6—C7—O1	179.31 (19)	Br1—C13—C14—C15	177.84 (16)
C5—C6—C7—C2	−1.0 (3)	C13—C14—C15—C10	1.7 (3)
C3—C2—C7—O1	−179.05 (16)	C11—C10—C15—C14	−2.4 (3)
C1—C2—C7—O1	−0.1 (2)	S1—C10—C15—C14	−175.55 (16)
C3—C2—C7—C6	1.2 (3)