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

In the title compound, C(15)H(10)BrClO(2)S, the 4-chloro-phenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 89.55 (9)°]. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds and and a Br⋯Br contact [3.783 (3) Å].

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 the structures of related 3-(4-chloro­phenyl­sulfin­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C15H10BrClO2S

M = 369.65

Monoclinic,

a = 11.530 (6) Å

b = 5.834 (3) Å

c = 22.045 (13) Å

β = 100.602 (16)°

V = 1457.6 (15) Å3

Z = 4

Mo Kα radiation

μ = 3.14 mm−1

T = 173 K

0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.625, T max = 0.746

12344 measured reflections

3169 independent reflections

2505 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.125

S = 1.08

3169 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.61 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/S1600536810038870/hg2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038870/hg2719Isup2.hkl

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

C15H10BrClO2S	F(000) = 736
Mr = 369.65	Dx = 1.684 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4598 reflections
a = 11.530 (6) Å	θ = 2.4–27.8°
b = 5.834 (3) Å	µ = 3.14 mm−1
c = 22.045 (13) Å	T = 173 K
β = 100.602 (16)°	Block, colourless
V = 1457.6 (15) Å3	0.20 × 0.16 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3169 independent reflections
Radiation source: rotating anode	2505 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.054
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 = −7→7
Tmin = 0.625, Tmax = 0.746	l = −28→28
12344 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) = 0.125	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0713P)2] where P = (Fo2 + 2Fc2)/3
3169 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.61 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
Br	0.49545 (3)	1.26359 (6)	0.558213 (16)	0.05190 (16)
Cl	0.73989 (8)	0.5654 (2)	0.33164 (3)	0.0649 (3)
S	0.93528 (6)	0.61437 (15)	0.61528 (3)	0.0386 (2)
O1	0.69728 (19)	0.4763 (4)	0.71682 (8)	0.0423 (5)
O2	0.9809 (2)	0.8550 (5)	0.62575 (10)	0.0516 (6)
C1	0.8083 (3)	0.5913 (5)	0.64826 (12)	0.0345 (6)
C2	0.7048 (3)	0.7367 (5)	0.64045 (12)	0.0328 (6)
C3	0.6625 (2)	0.9187 (5)	0.60174 (12)	0.0344 (6)
H3	0.7039	0.9731	0.5711	0.041*
C4	0.5576 (3)	1.0161 (5)	0.61011 (12)	0.0371 (6)
C5	0.4941 (3)	0.9380 (6)	0.65489 (13)	0.0433 (7)
H5	0.4221	1.0104	0.6590	0.052*
C6	0.5362 (3)	0.7563 (6)	0.69289 (13)	0.0453 (8)
H6	0.4950	0.7011	0.7235	0.054*
C7	0.6407 (3)	0.6592 (6)	0.68429 (12)	0.0368 (6)
C8	0.7994 (3)	0.4395 (5)	0.69429 (12)	0.0371 (7)
C9	0.8777 (4)	0.2533 (6)	0.72349 (16)	0.0533 (9)
H9A	0.9466	0.2421	0.7035	0.080*
H9B	0.8346	0.1077	0.7189	0.080*
H9C	0.9037	0.2870	0.7674	0.080*
C10	0.8689 (2)	0.6021 (5)	0.53503 (12)	0.0300 (6)
C11	0.8105 (3)	0.4075 (5)	0.50999 (14)	0.0451 (8)
H11	0.7987	0.2828	0.5359	0.054*
C12	0.7695 (3)	0.3952 (6)	0.44718 (15)	0.0488 (8)
H12	0.7280	0.2639	0.4293	0.059*
C13	0.7902 (2)	0.5784 (6)	0.41089 (13)	0.0390 (7)
C14	0.8486 (3)	0.7708 (5)	0.43509 (15)	0.0434 (8)
H14	0.8616	0.8944	0.4091	0.052*
C15	0.8881 (3)	0.7822 (5)	0.49797 (14)	0.0395 (7)
H15	0.9286	0.9148	0.5157	0.047*

	U11	U22	U33	U12	U13	U23
Br	0.0453 (2)	0.0542 (3)	0.0552 (2)	0.01571 (15)	0.00677 (17)	0.00300 (14)
Cl	0.0517 (5)	0.1073 (8)	0.0349 (4)	0.0106 (5)	0.0053 (4)	−0.0076 (4)
S	0.0285 (4)	0.0529 (5)	0.0344 (4)	0.0028 (3)	0.0059 (3)	0.0022 (3)
O1	0.0496 (13)	0.0516 (13)	0.0274 (9)	−0.0036 (11)	0.0116 (9)	0.0057 (8)
O2	0.0441 (13)	0.0659 (15)	0.0450 (12)	−0.0217 (13)	0.0090 (10)	−0.0112 (11)
C1	0.0330 (15)	0.0442 (17)	0.0269 (12)	0.0012 (13)	0.0067 (11)	0.0009 (11)
C2	0.0307 (15)	0.0414 (17)	0.0263 (12)	−0.0052 (12)	0.0054 (11)	−0.0035 (10)
C3	0.0310 (14)	0.0427 (17)	0.0312 (13)	−0.0006 (13)	0.0099 (11)	0.0014 (11)
C4	0.0320 (14)	0.0464 (17)	0.0323 (13)	0.0004 (14)	0.0040 (12)	−0.0075 (12)
C5	0.0300 (15)	0.064 (2)	0.0374 (14)	0.0020 (15)	0.0105 (12)	−0.0127 (14)
C6	0.0412 (18)	0.068 (2)	0.0301 (15)	−0.0078 (15)	0.0159 (14)	−0.0050 (13)
C7	0.0394 (16)	0.0462 (17)	0.0252 (12)	−0.0063 (14)	0.0067 (12)	−0.0033 (12)
C8	0.0436 (16)	0.0414 (16)	0.0257 (12)	−0.0029 (14)	0.0046 (12)	−0.0003 (11)
C9	0.068 (3)	0.051 (2)	0.0385 (16)	0.0065 (16)	0.0032 (17)	0.0119 (13)
C10	0.0256 (13)	0.0325 (14)	0.0334 (13)	0.0047 (11)	0.0096 (11)	0.0010 (10)
C11	0.054 (2)	0.0348 (16)	0.0470 (16)	−0.0054 (15)	0.0095 (15)	0.0040 (13)
C12	0.052 (2)	0.0419 (18)	0.0496 (17)	−0.0068 (16)	0.0025 (15)	−0.0083 (14)
C13	0.0278 (14)	0.058 (2)	0.0336 (14)	0.0102 (14)	0.0110 (12)	−0.0027 (13)
C14	0.0409 (18)	0.052 (2)	0.0395 (15)	0.0005 (15)	0.0137 (14)	0.0109 (13)
C15	0.0374 (17)	0.0410 (17)	0.0424 (15)	−0.0088 (13)	0.0132 (14)	−0.0017 (12)

Br—C4	1.899 (3)	C6—C7	1.376 (5)
Br—Bri	3.7826 (17)	C6—H6	0.9500
Cl—C13	1.738 (3)	C8—C9	1.482 (4)
S—O2	1.502 (3)	C9—H9A	0.9800
S—C1	1.756 (3)	C9—H9B	0.9800
S—C10	1.795 (3)	C9—H9C	0.9800
O1—C8	1.376 (4)	C10—C15	1.373 (4)
O1—C7	1.381 (4)	C10—C11	1.382 (4)
C1—C8	1.365 (4)	C11—C12	1.380 (4)
C1—C2	1.448 (4)	C11—H11	0.9500
C2—C3	1.393 (4)	C12—C13	1.382 (5)
C2—C7	1.395 (4)	C12—H12	0.9500
C3—C4	1.379 (4)	C13—C14	1.366 (5)
C3—H3	0.9500	C14—C15	1.379 (4)
C4—C5	1.409 (4)	C14—H14	0.9500
C5—C6	1.383 (5)	C15—H15	0.9500
C5—H5	0.9500
C4—Br—Bri	155.35 (9)	C1—C8—C9	132.5 (3)
O2—S—C1	107.65 (14)	O1—C8—C9	116.8 (3)
O2—S—C10	105.22 (13)	C8—C9—H9A	109.5
C1—S—C10	99.69 (13)	C8—C9—H9B	109.5
C8—O1—C7	106.7 (2)	H9A—C9—H9B	109.5
C8—C1—C2	107.2 (3)	C8—C9—H9C	109.5
C8—C1—S	122.7 (2)	H9A—C9—H9C	109.5
C2—C1—S	129.6 (2)	H9B—C9—H9C	109.5
C3—C2—C7	120.1 (3)	C15—C10—C11	120.7 (3)
C3—C2—C1	135.0 (3)	C15—C10—S	118.0 (2)
C7—C2—C1	104.9 (2)	C11—C10—S	120.9 (2)
C4—C3—C2	116.6 (3)	C12—C11—C10	119.7 (3)
C4—C3—H3	121.7	C12—C11—H11	120.2
C2—C3—H3	121.7	C10—C11—H11	120.2
C3—C4—C5	122.9 (3)	C11—C12—C13	118.5 (3)
C3—C4—Br	118.4 (2)	C11—C12—H12	120.8
C5—C4—Br	118.7 (2)	C13—C12—H12	120.8
C6—C5—C4	120.1 (3)	C14—C13—C12	122.3 (3)
C6—C5—H5	119.9	C14—C13—Cl	118.5 (2)
C4—C5—H5	119.9	C12—C13—Cl	119.1 (2)
C7—C6—C5	116.8 (3)	C13—C14—C15	118.7 (3)
C7—C6—H6	121.6	C13—C14—H14	120.7
C5—C6—H6	121.6	C15—C14—H14	120.7
C6—C7—O1	126.1 (3)	C10—C15—C14	120.1 (3)
C6—C7—C2	123.4 (3)	C10—C15—H15	120.0
O1—C7—C2	110.5 (3)	C14—C15—H15	120.0
C1—C8—O1	110.7 (3)
O2—S—C1—C8	−120.0 (3)	C1—C2—C7—O1	−1.0 (3)
C10—S—C1—C8	130.5 (2)	C2—C1—C8—O1	0.0 (3)
O2—S—C1—C2	50.7 (3)	S—C1—C8—O1	172.54 (19)
C10—S—C1—C2	−58.8 (3)	C2—C1—C8—C9	−178.9 (3)
C8—C1—C2—C3	−179.5 (3)	S—C1—C8—C9	−6.4 (5)
S—C1—C2—C3	8.7 (5)	C7—O1—C8—C1	−0.7 (3)
C8—C1—C2—C7	0.6 (3)	C7—O1—C8—C9	178.4 (3)
S—C1—C2—C7	−171.2 (2)	O2—S—C10—C15	10.8 (3)
C7—C2—C3—C4	1.0 (4)	C1—S—C10—C15	122.2 (2)
C1—C2—C3—C4	−178.9 (3)	O2—S—C10—C11	−175.8 (2)
C2—C3—C4—C5	−0.4 (4)	C1—S—C10—C11	−64.3 (3)
C2—C3—C4—Br	−179.6 (2)	C15—C10—C11—C12	−0.9 (5)
C3—C4—C5—C6	0.0 (5)	S—C10—C11—C12	−174.2 (3)
Br—C4—C5—C6	179.2 (2)	C10—C11—C12—C13	1.1 (5)
C4—C5—C6—C7	−0.2 (4)	C11—C12—C13—C14	−0.7 (5)
C5—C6—C7—O1	−179.5 (3)	C11—C12—C13—Cl	179.7 (3)
C5—C6—C7—C2	0.8 (5)	C12—C13—C14—C15	0.0 (5)
C8—O1—C7—C6	−178.6 (3)	Cl—C13—C14—C15	179.7 (3)
C8—O1—C7—C2	1.1 (3)	C11—C10—C15—C14	0.3 (5)
C3—C2—C7—C6	−1.3 (4)	S—C10—C15—C14	173.8 (3)
C1—C2—C7—C6	178.7 (3)	C13—C14—C15—C10	0.2 (5)
C3—C2—C7—O1	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O2ii	0.98	2.51	3.473 (5)	166
C14—H14···O2iii	0.95	2.56	3.376 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O2i	0.98	2.51	3.473 (5)	166
C14—H14⋯O2ii	0.95	2.56	3.376 (4)	145

Symmetry codes: (i) ; (ii) .