3-(4-Bromo-phenyl-sulfin-yl)-5-chloro-2,7-dimethyl-1-benzo-furan.

In the title compound, C16H12BrClO2S, the 4-bromo-phenyl ring makes a dihedral angle of 88.84 (5)° with the mean plane [r.m.s. deviation = 0.009 (1) Å] of the benzo-furan fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-S⋯π [3.386 (2) Å] inter-actions, forming a chain perpendicular to the bc plane.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012a ▶,b ▶).

Experimental

Crystal data

C16H12BrClO2S

M = 383.68

Triclinic,

a = 6.1266 (3) Å

b = 10.0247 (5) Å

c = 12.6630 (7) Å

α = 84.749 (3)°

β = 79.235 (2)°

γ = 86.443 (3)°

V = 760.03 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.02 mm−1

T = 173 K

0.33 × 0.23 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.506, T max = 0.746

13853 measured reflections

3794 independent reflections

3209 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.05

3794 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.72 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300994X/aa2089sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300994X/aa2089Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300994X/aa2089Isup3.cml

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

C16H12BrClO2S	Z = 2
Mr = 383.68	F(000) = 384
Triclinic, P1	Dx = 1.677 Mg m−3
Hall symbol: -P 1	Melting point = 442–443 K
a = 6.1266 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0247 (5) Å	Cell parameters from 6958 reflections
c = 12.6630 (7) Å	θ = 2.5–28.5°
α = 84.749 (3)°	µ = 3.02 mm−1
β = 79.235 (2)°	T = 173 K
γ = 86.443 (3)°	Block, colourless
V = 760.03 (7) Å3	0.33 × 0.23 × 0.16 mm

Bruker SMART APEXII CCD diffractometer	3794 independent reflections
Radiation source: rotating anode	3209 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 28.5°, θmin = 1.6°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.506, Tmax = 0.746	l = −16→16
13853 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) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2147P] where P = (Fo2 + 2Fc2)/3
3794 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.72 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	0.60695 (4)	0.00462 (2)	0.662469 (16)	0.03820 (9)
Cl1	−0.07539 (9)	0.08106 (6)	0.16204 (5)	0.03950 (14)
S1	0.38584 (8)	0.50904 (4)	0.34160 (3)	0.02363 (11)
O1	0.7066 (2)	0.40065 (13)	0.06063 (10)	0.0251 (3)
O2	0.1390 (2)	0.52341 (15)	0.35333 (11)	0.0326 (3)
C1	0.4874 (3)	0.43659 (18)	0.21924 (14)	0.0226 (4)
C2	0.3886 (3)	0.33547 (18)	0.17248 (14)	0.0218 (4)
C3	0.1985 (3)	0.26119 (19)	0.20141 (15)	0.0253 (4)
H3	0.0981	0.2709	0.2674	0.030*
C4	0.1635 (3)	0.17304 (19)	0.12968 (16)	0.0266 (4)
C5	0.3103 (3)	0.15431 (19)	0.03288 (15)	0.0288 (4)
H5	0.2794	0.0908	−0.0130	0.035*
C6	0.5011 (3)	0.22733 (19)	0.00283 (14)	0.0266 (4)
C7	0.5301 (3)	0.31709 (18)	0.07481 (14)	0.0228 (4)
C8	0.6746 (3)	0.47297 (19)	0.14948 (14)	0.0235 (4)
C9	0.6643 (4)	0.2110 (2)	−0.10013 (16)	0.0366 (5)
H9A	0.6792	0.2976	−0.1429	0.055*
H9B	0.6108	0.1458	−0.1414	0.055*
H9C	0.8092	0.1791	−0.0832	0.055*
C10	0.8461 (3)	0.5696 (2)	0.15219 (16)	0.0301 (4)
H10A	0.7906	0.6308	0.2083	0.045*
H10B	0.8800	0.6211	0.0820	0.045*
H10C	0.9813	0.5208	0.1681	0.045*
C11	0.4447 (3)	0.36641 (18)	0.43057 (14)	0.0219 (4)
C12	0.2744 (3)	0.3133 (2)	0.50722 (15)	0.0258 (4)
H12	0.1267	0.3504	0.5121	0.031*
C13	0.3225 (3)	0.2049 (2)	0.57709 (15)	0.0290 (4)
H13	0.2075	0.1662	0.6297	0.035*
C14	0.5385 (4)	0.15413 (19)	0.56925 (15)	0.0267 (4)
C15	0.7110 (3)	0.2096 (2)	0.49468 (16)	0.0292 (4)
H15	0.8592	0.1738	0.4912	0.035*
C16	0.6637 (3)	0.3177 (2)	0.42569 (16)	0.0285 (4)
H16	0.7799	0.3585	0.3752	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.05595 (17)	0.03092 (13)	0.03054 (13)	−0.00131 (10)	−0.01697 (10)	0.00087 (8)
Cl1	0.0293 (3)	0.0376 (3)	0.0541 (3)	−0.0073 (2)	−0.0115 (2)	−0.0046 (2)
S1	0.0255 (2)	0.0252 (2)	0.0202 (2)	0.00279 (19)	−0.00371 (18)	−0.00560 (17)
O1	0.0249 (7)	0.0283 (7)	0.0209 (6)	−0.0009 (6)	−0.0012 (5)	−0.0026 (5)
O2	0.0245 (7)	0.0433 (8)	0.0296 (7)	0.0106 (6)	−0.0056 (6)	−0.0079 (6)
C1	0.0237 (9)	0.0257 (9)	0.0181 (8)	0.0025 (8)	−0.0034 (7)	−0.0038 (7)
C2	0.0227 (9)	0.0225 (8)	0.0201 (8)	0.0033 (7)	−0.0050 (7)	−0.0013 (7)
C3	0.0214 (9)	0.0266 (9)	0.0266 (9)	0.0029 (8)	−0.0026 (7)	−0.0012 (7)
C4	0.0249 (10)	0.0228 (9)	0.0336 (10)	−0.0008 (8)	−0.0105 (8)	−0.0002 (7)
C5	0.0364 (11)	0.0251 (9)	0.0278 (9)	0.0004 (8)	−0.0127 (8)	−0.0051 (7)
C6	0.0330 (11)	0.0259 (9)	0.0212 (9)	0.0044 (8)	−0.0069 (8)	−0.0029 (7)
C7	0.0229 (9)	0.0240 (9)	0.0211 (8)	0.0010 (7)	−0.0047 (7)	−0.0002 (7)
C8	0.0247 (9)	0.0253 (9)	0.0202 (8)	0.0013 (8)	−0.0045 (7)	−0.0014 (7)
C9	0.0482 (14)	0.0354 (11)	0.0245 (10)	−0.0002 (10)	0.0000 (9)	−0.0088 (8)
C10	0.0284 (10)	0.0311 (10)	0.0305 (10)	−0.0049 (9)	−0.0046 (8)	−0.0003 (8)
C11	0.0229 (9)	0.0257 (9)	0.0178 (8)	−0.0010 (7)	−0.0040 (7)	−0.0051 (7)
C12	0.0193 (9)	0.0328 (10)	0.0255 (9)	−0.0011 (8)	−0.0021 (7)	−0.0075 (8)
C13	0.0301 (11)	0.0334 (10)	0.0232 (9)	−0.0079 (9)	−0.0012 (8)	−0.0032 (8)
C14	0.0357 (11)	0.0247 (9)	0.0220 (9)	−0.0024 (8)	−0.0097 (8)	−0.0036 (7)
C15	0.0234 (10)	0.0351 (10)	0.0296 (10)	0.0038 (8)	−0.0073 (8)	−0.0044 (8)
C16	0.0218 (9)	0.0355 (11)	0.0263 (9)	0.0015 (8)	−0.0010 (8)	−0.0014 (8)

Br1—C14	1.8972 (19)	C8—C10	1.480 (3)
Cl1—C4	1.742 (2)	C9—H9A	0.9800
S1—O2	1.4907 (15)	C9—H9B	0.9800
S1—C1	1.7622 (17)	C9—H9C	0.9800
S1—C11	1.7990 (19)	C10—H10A	0.9800
O1—C8	1.371 (2)	C10—H10B	0.9800
O1—C7	1.384 (2)	C10—H10C	0.9800
C1—C8	1.358 (3)	C11—C12	1.382 (3)
C1—C2	1.437 (3)	C11—C16	1.392 (3)
C2—C7	1.392 (2)	C12—C13	1.390 (3)
C2—C3	1.394 (3)	C12—H12	0.9500
C3—C4	1.377 (3)	C13—C14	1.377 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.399 (3)	C14—C15	1.386 (3)
C5—C6	1.391 (3)	C15—C16	1.380 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (3)	C16—H16	0.9500
C6—C9	1.503 (3)
O2—S1—C1	107.21 (9)	C6—C9—H9B	109.5
O2—S1—C11	106.44 (9)	H9A—C9—H9B	109.5
C1—S1—C11	97.25 (8)	C6—C9—H9C	109.5
C8—O1—C7	106.52 (13)	H9A—C9—H9C	109.5
C8—C1—C2	107.65 (16)	H9B—C9—H9C	109.5
C8—C1—S1	124.42 (15)	C8—C10—H10A	109.5
C2—C1—S1	127.88 (14)	C8—C10—H10B	109.5
C7—C2—C3	119.18 (18)	H10A—C10—H10B	109.5
C7—C2—C1	104.93 (17)	C8—C10—H10C	109.5
C3—C2—C1	135.88 (17)	H10A—C10—H10C	109.5
C4—C3—C2	116.76 (17)	H10B—C10—H10C	109.5
C4—C3—H3	121.6	C12—C11—C16	121.24 (18)
C2—C3—H3	121.6	C12—C11—S1	119.47 (14)
C3—C4—C5	123.07 (18)	C16—C11—S1	119.13 (14)
C3—C4—Cl1	117.96 (15)	C11—C12—C13	119.01 (18)
C5—C4—Cl1	118.97 (16)	C11—C12—H12	120.5
C6—C5—C4	120.94 (18)	C13—C12—H12	120.5
C6—C5—H5	119.5	C14—C13—C12	119.35 (18)
C4—C5—H5	119.5	C14—C13—H13	120.3
C7—C6—C5	114.94 (16)	C12—C13—H13	120.3
C7—C6—C9	121.98 (19)	C13—C14—C15	121.87 (18)
C5—C6—C9	123.08 (18)	C13—C14—Br1	120.01 (15)
C6—C7—O1	124.64 (16)	C15—C14—Br1	118.11 (15)
C6—C7—C2	125.08 (19)	C16—C15—C14	118.83 (18)
O1—C7—C2	110.28 (16)	C16—C15—H15	120.6
C1—C8—O1	110.62 (17)	C14—C15—H15	120.6
C1—C8—C10	133.30 (17)	C15—C16—C11	119.59 (18)
O1—C8—C10	116.07 (16)	C15—C16—H16	120.2
C6—C9—H9A	109.5	C11—C16—H16	120.2
O2—S1—C1—C8	140.11 (16)	C1—C2—C7—C6	179.24 (18)
C11—S1—C1—C8	−110.13 (17)	C3—C2—C7—O1	179.36 (15)
O2—S1—C1—C2	−37.03 (19)	C1—C2—C7—O1	0.1 (2)
C11—S1—C1—C2	72.73 (18)	C2—C1—C8—O1	−0.9 (2)
C8—C1—C2—C7	0.5 (2)	S1—C1—C8—O1	−178.55 (13)
S1—C1—C2—C7	178.04 (14)	C2—C1—C8—C10	−179.3 (2)
C8—C1—C2—C3	−178.6 (2)	S1—C1—C8—C10	3.1 (3)
S1—C1—C2—C3	−1.1 (3)	C7—O1—C8—C1	0.9 (2)
C7—C2—C3—C4	−0.1 (3)	C7—O1—C8—C10	179.63 (16)
C1—C2—C3—C4	179.0 (2)	O2—S1—C11—C12	−13.18 (18)
C2—C3—C4—C5	1.3 (3)	C1—S1—C11—C12	−123.58 (16)
C2—C3—C4—Cl1	−178.72 (14)	O2—S1—C11—C16	171.25 (15)
C3—C4—C5—C6	−1.2 (3)	C1—S1—C11—C16	60.86 (17)
Cl1—C4—C5—C6	178.83 (14)	C16—C11—C12—C13	−3.2 (3)
C4—C5—C6—C7	−0.2 (3)	S1—C11—C12—C13	−178.65 (15)
C4—C5—C6—C9	179.95 (19)	C11—C12—C13—C14	0.8 (3)
C5—C6—C7—O1	−179.37 (16)	C12—C13—C14—C15	1.2 (3)
C9—C6—C7—O1	0.5 (3)	C12—C13—C14—Br1	−179.12 (15)
C5—C6—C7—C2	1.6 (3)	C13—C14—C15—C16	−0.8 (3)
C9—C6—C7—C2	−178.61 (18)	Br1—C14—C15—C16	179.46 (15)
C8—O1—C7—C6	−179.79 (18)	C14—C15—C16—C11	−1.5 (3)
C8—O1—C7—C2	−0.60 (19)	C12—C11—C16—C15	3.5 (3)
C3—C2—C7—C6	−1.5 (3)	S1—C11—C16—C15	179.03 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.50	3.249 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.50	3.249 (2)	136

Symmetry code: (i) .