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

In the title compound, C(15)H(10)BrClO(3)S, the 4-bromo-substituted benzene ring forms a dihedral angle of 72.55 (6)° with the mean plane [mean deviation = 0.008 (2) Å] of the benzofuran ring system. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into chains along [001]. There are also π-π inter-actions between the furan and benzene rings of symmetry-related benzofuran systems [centroid-centroid distances = 3.549 (3) and 3.632 (3) Å].

Related literature

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

Experimental

Crystal data

C15H10BrClO3S

M = 385.65

Triclinic,

a = 7.1089 (2) Å

b = 10.4169 (3) Å

c = 11.0217 (3) Å

α = 69.659 (2)°

β = 89.526 (2)°

γ = 71.632 (1)°

V = 721.58 (4) Å3

Z = 2

Mo Kα radiation

μ = 3.18 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 = 0.448, T max = 0.746

13182 measured reflections

3570 independent reflections

3007 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.08

3570 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.43 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) global, I. DOI: 10.1107/S1600536812024592/lh5482sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024592/lh5482Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024592/lh5482Isup3.cml

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

C15H10BrClO3S	Z = 2
Mr = 385.65	F(000) = 384
Triclinic, P1	Dx = 1.775 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1089 (2) Å	Cell parameters from 7922 reflections
b = 10.4169 (3) Å	θ = 2.5–28.3°
c = 11.0217 (3) Å	µ = 3.18 mm−1
α = 69.659 (2)°	T = 173 K
β = 89.526 (2)°	Block, colourless
γ = 71.632 (1)°	0.38 × 0.31 × 0.27 mm
V = 721.58 (4) Å3

Bruker SMART APEXII CCD diffractometer	3570 independent reflections
Radiation source: rotating anode	3007 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.054
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.448, Tmax = 0.746	l = −14→14
13182 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0238P] where P = (Fo2 + 2Fc2)/3
3570 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.43 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	−0.05797 (4)	−0.23812 (2)	0.82146 (3)	0.03829 (11)
Cl1	0.31879 (13)	0.47313 (9)	0.12675 (7)	0.0514 (2)
S1	0.53111 (8)	0.13394 (6)	0.70691 (5)	0.02350 (14)
O1	0.1919 (2)	0.53895 (17)	0.62583 (18)	0.0320 (4)
O2	0.6309 (3)	0.10707 (19)	0.83068 (17)	0.0320 (4)
O3	0.6452 (2)	0.10389 (17)	0.60557 (16)	0.0282 (4)
C1	0.3820 (3)	0.3152 (2)	0.6417 (2)	0.0237 (4)
C2	0.3255 (3)	0.4018 (2)	0.5047 (2)	0.0242 (5)
C3	0.3615 (4)	0.3785 (3)	0.3887 (2)	0.0288 (5)
H3	0.4391	0.2863	0.3874	0.035*
C4	0.2782 (4)	0.4967 (3)	0.2754 (3)	0.0345 (6)
C5	0.1640 (4)	0.6333 (3)	0.2737 (3)	0.0406 (7)
H5	0.1098	0.7108	0.1929	0.049*
C6	0.1294 (4)	0.6564 (3)	0.3885 (3)	0.0378 (7)
H6	0.0539	0.7491	0.3898	0.045*
C7	0.2097 (4)	0.5387 (3)	0.5014 (3)	0.0293 (5)
C8	0.2974 (4)	0.4014 (3)	0.7101 (3)	0.0297 (5)
C9	0.2938 (4)	0.3784 (3)	0.8495 (3)	0.0400 (6)
H9A	0.1613	0.3780	0.8744	0.060*
H9B	0.3238	0.4568	0.8661	0.060*
H9C	0.3940	0.2850	0.9008	0.060*
C10	0.3644 (3)	0.0345 (2)	0.7367 (2)	0.0246 (5)
C11	0.2993 (4)	−0.0064 (3)	0.8589 (2)	0.0333 (6)
H11	0.3425	0.0202	0.9252	0.040*
C12	0.1709 (4)	−0.0863 (3)	0.8835 (3)	0.0364 (6)
H12	0.1249	−0.1146	0.9667	0.044*
C13	0.1106 (4)	−0.1243 (2)	0.7867 (3)	0.0291 (5)
C14	0.1743 (4)	−0.0834 (3)	0.6636 (2)	0.0305 (5)
H14	0.1313	−0.1105	0.5976	0.037*
C15	0.3008 (4)	−0.0028 (3)	0.6388 (2)	0.0286 (5)
H15	0.3444	0.0272	0.5550	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.03630 (17)	0.02806 (14)	0.0493 (2)	−0.01477 (11)	0.00645 (13)	−0.00910 (12)
Cl1	0.0655 (5)	0.0720 (5)	0.0242 (3)	−0.0428 (4)	0.0035 (3)	−0.0084 (3)
S1	0.0238 (3)	0.0256 (3)	0.0201 (3)	−0.0069 (2)	0.0006 (2)	−0.0082 (2)
O1	0.0265 (9)	0.0271 (8)	0.0463 (11)	−0.0081 (7)	0.0063 (8)	−0.0187 (8)
O2	0.0309 (9)	0.0384 (9)	0.0253 (9)	−0.0116 (7)	−0.0032 (7)	−0.0097 (7)
O3	0.0263 (9)	0.0290 (8)	0.0267 (9)	−0.0060 (7)	0.0046 (7)	−0.0101 (7)
C1	0.0205 (11)	0.0259 (10)	0.0255 (12)	−0.0089 (9)	0.0020 (9)	−0.0092 (9)
C2	0.0192 (11)	0.0253 (10)	0.0294 (12)	−0.0104 (9)	0.0007 (9)	−0.0088 (9)
C3	0.0286 (12)	0.0300 (11)	0.0274 (13)	−0.0130 (10)	0.0027 (10)	−0.0071 (10)
C4	0.0331 (14)	0.0455 (14)	0.0267 (13)	−0.0246 (11)	0.0010 (11)	−0.0051 (11)
C5	0.0333 (14)	0.0357 (13)	0.0408 (17)	−0.0189 (11)	−0.0064 (12)	0.0071 (12)
C6	0.0244 (13)	0.0228 (11)	0.0604 (19)	−0.0103 (9)	−0.0014 (12)	−0.0059 (12)
C7	0.0219 (11)	0.0290 (11)	0.0397 (14)	−0.0129 (9)	0.0030 (10)	−0.0116 (10)
C8	0.0235 (12)	0.0351 (12)	0.0354 (14)	−0.0120 (10)	0.0042 (10)	−0.0165 (11)
C9	0.0392 (15)	0.0550 (16)	0.0365 (15)	−0.0181 (13)	0.0100 (12)	−0.0274 (13)
C10	0.0260 (12)	0.0228 (10)	0.0225 (11)	−0.0069 (9)	0.0015 (9)	−0.0061 (9)
C11	0.0420 (15)	0.0394 (13)	0.0227 (12)	−0.0190 (11)	0.0048 (11)	−0.0114 (11)
C12	0.0431 (15)	0.0384 (13)	0.0251 (13)	−0.0182 (12)	0.0050 (11)	−0.0042 (11)
C13	0.0275 (12)	0.0215 (10)	0.0334 (13)	−0.0065 (9)	0.0051 (10)	−0.0059 (9)
C14	0.0316 (13)	0.0337 (12)	0.0297 (13)	−0.0111 (10)	0.0020 (11)	−0.0153 (10)
C15	0.0312 (13)	0.0307 (11)	0.0242 (12)	−0.0097 (10)	0.0057 (10)	−0.0108 (10)

Br1—C13	1.887 (2)	C6—C7	1.374 (4)
Cl1—C4	1.748 (3)	C6—H6	0.9500
S1—O2	1.4380 (18)	C8—C9	1.472 (4)
S1—O3	1.4392 (17)	C9—H9A	0.9800
S1—C1	1.735 (2)	C9—H9B	0.9800
S1—C10	1.765 (2)	C9—H9C	0.9800
O1—C8	1.374 (3)	C10—C11	1.387 (3)
O1—C7	1.378 (3)	C10—C15	1.389 (3)
C1—C8	1.364 (3)	C11—C12	1.385 (4)
C1—C2	1.446 (3)	C11—H11	0.9500
C2—C3	1.389 (3)	C12—C13	1.373 (4)
C2—C7	1.392 (3)	C12—H12	0.9500
C3—C4	1.383 (4)	C13—C14	1.393 (4)
C3—H3	0.9500	C14—C15	1.378 (4)
C4—C5	1.392 (4)	C14—H14	0.9500
C5—C6	1.375 (4)	C15—H15	0.9500
C5—H5	0.9500
O2—S1—O3	120.14 (11)	C1—C8—O1	110.0 (2)
O2—S1—C1	108.61 (11)	C1—C8—C9	134.5 (2)
O3—S1—C1	106.53 (10)	O1—C8—C9	115.6 (2)
O2—S1—C10	107.53 (11)	C8—C9—H9A	109.5
O3—S1—C10	107.70 (10)	C8—C9—H9B	109.5
C1—S1—C10	105.43 (11)	H9A—C9—H9B	109.5
C8—O1—C7	107.14 (17)	C8—C9—H9C	109.5
C8—C1—C2	107.8 (2)	H9A—C9—H9C	109.5
C8—C1—S1	126.30 (19)	H9B—C9—H9C	109.5
C2—C1—S1	125.94 (17)	C11—C10—C15	120.7 (2)
C3—C2—C7	119.6 (2)	C11—C10—S1	119.19 (19)
C3—C2—C1	135.8 (2)	C15—C10—S1	120.08 (18)
C7—C2—C1	104.6 (2)	C12—C11—C10	119.5 (2)
C4—C3—C2	116.4 (2)	C12—C11—H11	120.3
C4—C3—H3	121.8	C10—C11—H11	120.3
C2—C3—H3	121.8	C13—C12—C11	119.5 (2)
C3—C4—C5	123.4 (3)	C13—C12—H12	120.2
C3—C4—Cl1	118.2 (2)	C11—C12—H12	120.2
C5—C4—Cl1	118.4 (2)	C12—C13—C14	121.5 (2)
C6—C5—C4	120.2 (2)	C12—C13—Br1	119.62 (19)
C6—C5—H5	119.9	C14—C13—Br1	118.8 (2)
C4—C5—H5	119.9	C15—C14—C13	118.9 (2)
C7—C6—C5	116.6 (2)	C15—C14—H14	120.5
C7—C6—H6	121.7	C13—C14—H14	120.5
C5—C6—H6	121.7	C14—C15—C10	119.8 (2)
C6—C7—O1	125.6 (2)	C14—C15—H15	120.1
C6—C7—C2	123.9 (2)	C10—C15—H15	120.1
O1—C7—C2	110.5 (2)
O2—S1—C1—C8	−27.8 (2)	C1—C2—C7—O1	−0.6 (2)
O3—S1—C1—C8	−158.5 (2)	C2—C1—C8—O1	−0.8 (3)
C10—S1—C1—C8	87.2 (2)	S1—C1—C8—O1	179.12 (16)
O2—S1—C1—C2	152.06 (19)	C2—C1—C8—C9	178.4 (3)
O3—S1—C1—C2	21.3 (2)	S1—C1—C8—C9	−1.7 (4)
C10—S1—C1—C2	−92.9 (2)	C7—O1—C8—C1	0.4 (2)
C8—C1—C2—C3	−179.8 (3)	C7—O1—C8—C9	−179.0 (2)
S1—C1—C2—C3	0.3 (4)	O2—S1—C10—C11	22.3 (2)
C8—C1—C2—C7	0.8 (2)	O3—S1—C10—C11	153.12 (19)
S1—C1—C2—C7	−179.05 (17)	C1—S1—C10—C11	−93.4 (2)
C7—C2—C3—C4	0.4 (3)	O2—S1—C10—C15	−157.24 (19)
C1—C2—C3—C4	−178.8 (2)	O3—S1—C10—C15	−26.4 (2)
C2—C3—C4—C5	0.1 (4)	C1—S1—C10—C15	87.0 (2)
C2—C3—C4—Cl1	−179.96 (17)	C15—C10—C11—C12	0.5 (4)
C3—C4—C5—C6	0.3 (4)	S1—C10—C11—C12	−179.0 (2)
Cl1—C4—C5—C6	−179.7 (2)	C10—C11—C12—C13	0.3 (4)
C4—C5—C6—C7	−1.1 (4)	C11—C12—C13—C14	−0.5 (4)
C5—C6—C7—O1	−179.8 (2)	C11—C12—C13—Br1	178.11 (19)
C5—C6—C7—C2	1.7 (4)	C12—C13—C14—C15	0.0 (4)
C8—O1—C7—C6	−178.5 (2)	Br1—C13—C14—C15	−178.66 (18)
C8—O1—C7—C2	0.2 (2)	C13—C14—C15—C10	0.8 (4)
C3—C2—C7—C6	−1.4 (4)	C11—C10—C15—C14	−1.1 (4)
C1—C2—C7—C6	178.1 (2)	S1—C10—C15—C14	178.47 (18)
C3—C2—C7—O1	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.95	2.53	3.203 (3)	128
C15—H15···O3ii	0.95	2.57	3.195 (3)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.95	2.53	3.203 (3)	128
C15—H15⋯O3ii	0.95	2.57	3.195 (3)	124

Symmetry codes: (i) ; (ii) .