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

In the title compound, C17H15BrO2S, both the benzo-furan and 2-bromo-phenyl rings are virtually planar, with r.m.s. deviations of 0.009 (2) and 0.006 (2) Å, respectively. The dihedral angle between these mean planes is 89.31 (7)°. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions into inversion dimers. These dimers are further linked by C-H⋯π inter-actions into supra-molecular chains running along the b axis. In addition, C-S⋯π inter-actions, with an S-to-ring-centroid distance of 3.50 (2) Å, are observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Triclinic,

a = 7.540 (3) Å

b = 8.415 (3) Å

c = 12.722 (4) Å

α = 98.933 (19)°

β = 105.001 (19)°

γ = 93.530 (18)°

V = 765.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.82 mm−1

T = 173 K

0.32 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.522, T max = 0.746

12648 measured reflections

3304 independent reflections

2857 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.12

3304 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.54 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/S1600536813019867/fj2637sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019867/fj2637Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019867/fj2637Isup3.cml

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

C17H15BrO2S	Z = 2
Mr = 363.26	F(000) = 368
Triclinic, P1	Dx = 1.575 Mg m−3
Hall symbol: -P 1	Melting point = 457–458 K
a = 7.540 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.415 (3) Å	Cell parameters from 6758 reflections
c = 12.722 (4) Å	θ = 2.7–28.3°
α = 98.933 (19)°	µ = 2.82 mm−1
β = 105.001 (19)°	T = 173 K
γ = 93.530 (18)°	Block, colourless
V = 765.9 (5) Å3	0.32 × 0.26 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	3304 independent reflections
Radiation source: rotating anode	2857 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
Tmin = 0.522, Tmax = 0.746	l = −16→16
12648 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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.085	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.4612P] where P = (Fo2 + 2Fc2)/3
3304 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.54 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	0.37567 (4)	0.55880 (4)	0.20521 (2)	0.03750 (11)
S1	0.60544 (9)	0.28866 (8)	0.08301 (5)	0.02716 (15)
O1	0.5429 (2)	0.1218 (2)	0.34388 (13)	0.0266 (4)
O2	0.7458 (3)	0.2104 (2)	0.03489 (15)	0.0389 (5)
C1	0.6293 (3)	0.2361 (3)	0.21447 (19)	0.0240 (5)
C2	0.7898 (3)	0.2554 (3)	0.30929 (19)	0.0241 (5)
C3	0.9721 (3)	0.3263 (3)	0.3373 (2)	0.0261 (5)
H3	1.0173	0.3768	0.2862	0.031*
C4	1.0854 (3)	0.3215 (3)	0.4414 (2)	0.0281 (5)
C5	1.0155 (4)	0.2476 (3)	0.5162 (2)	0.0310 (6)
H5	1.0956	0.2466	0.5872	0.037*
C6	0.8355 (4)	0.1761 (3)	0.4916 (2)	0.0291 (5)
C7	0.7280 (3)	0.1826 (3)	0.3862 (2)	0.0249 (5)
C8	0.4873 (3)	0.1568 (3)	0.2387 (2)	0.0258 (5)
C9	1.2833 (4)	0.3978 (4)	0.4766 (2)	0.0370 (6)
H9A	1.3071	0.4537	0.4187	0.056*
H9B	1.3667	0.3135	0.4883	0.056*
H9C	1.3043	0.4757	0.5455	0.056*
C10	0.7603 (4)	0.0990 (4)	0.5728 (2)	0.0387 (7)
H10A	0.6570	0.1553	0.5876	0.058*
H10B	0.8578	0.1065	0.6419	0.058*
H10C	0.7173	−0.0151	0.5416	0.058*
C11	0.2921 (3)	0.1021 (4)	0.1772 (2)	0.0347 (6)
H11A	0.2629	0.1425	0.1071	0.052*
H11B	0.2110	0.1442	0.2215	0.052*
H11C	0.2734	−0.0164	0.1622	0.052*
C12	0.6930 (3)	0.5004 (3)	0.12476 (18)	0.0244 (5)
C13	0.8517 (3)	0.5498 (3)	0.0974 (2)	0.0290 (5)
H13	0.9179	0.4712	0.0665	0.035*
C14	0.9149 (4)	0.7125 (3)	0.1146 (2)	0.0350 (6)
H14	1.0229	0.7453	0.0947	0.042*
C15	0.8198 (4)	0.8273 (3)	0.1610 (2)	0.0364 (6)
H15	0.8627	0.9389	0.1728	0.044*
C16	0.6626 (4)	0.7803 (3)	0.1903 (2)	0.0338 (6)
H16	0.5992	0.8590	0.2235	0.041*
C17	0.5983 (3)	0.6167 (3)	0.17078 (19)	0.0267 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.03110 (16)	0.04774 (19)	0.04011 (17)	0.01447 (12)	0.01611 (12)	0.01220 (13)
S1	0.0323 (3)	0.0273 (3)	0.0219 (3)	0.0011 (3)	0.0082 (3)	0.0035 (2)
O1	0.0258 (8)	0.0286 (9)	0.0269 (9)	0.0010 (7)	0.0092 (7)	0.0072 (7)
O2	0.0568 (12)	0.0300 (10)	0.0380 (10)	0.0081 (9)	0.0281 (9)	0.0033 (8)
C1	0.0269 (12)	0.0210 (12)	0.0247 (12)	0.0027 (9)	0.0074 (10)	0.0046 (9)
C2	0.0271 (12)	0.0218 (12)	0.0234 (12)	0.0027 (10)	0.0079 (10)	0.0024 (9)
C3	0.0280 (12)	0.0229 (12)	0.0298 (13)	0.0013 (10)	0.0106 (10)	0.0074 (10)
C4	0.0260 (12)	0.0253 (12)	0.0320 (13)	0.0019 (10)	0.0070 (10)	0.0038 (10)
C5	0.0332 (13)	0.0327 (14)	0.0263 (13)	0.0063 (11)	0.0049 (11)	0.0068 (11)
C6	0.0330 (13)	0.0290 (13)	0.0273 (13)	0.0053 (11)	0.0101 (11)	0.0073 (10)
C7	0.0254 (12)	0.0240 (12)	0.0273 (12)	0.0027 (10)	0.0103 (10)	0.0052 (10)
C8	0.0269 (12)	0.0233 (12)	0.0277 (12)	0.0033 (10)	0.0092 (10)	0.0030 (10)
C9	0.0273 (13)	0.0411 (16)	0.0398 (15)	0.0011 (12)	0.0051 (12)	0.0061 (12)
C10	0.0423 (16)	0.0457 (17)	0.0326 (15)	0.0035 (13)	0.0128 (13)	0.0163 (13)
C11	0.0268 (13)	0.0398 (16)	0.0361 (15)	−0.0018 (12)	0.0071 (11)	0.0072 (12)
C12	0.0269 (12)	0.0274 (12)	0.0191 (11)	0.0046 (10)	0.0039 (9)	0.0078 (9)
C13	0.0296 (13)	0.0300 (13)	0.0296 (13)	0.0062 (11)	0.0099 (11)	0.0077 (10)
C14	0.0291 (13)	0.0376 (15)	0.0368 (15)	0.0016 (12)	0.0046 (11)	0.0099 (12)
C15	0.0379 (15)	0.0276 (14)	0.0371 (15)	−0.0001 (12)	−0.0009 (12)	0.0060 (11)
C16	0.0391 (15)	0.0277 (14)	0.0305 (14)	0.0106 (11)	0.0027 (11)	0.0018 (11)
C17	0.0245 (12)	0.0334 (14)	0.0212 (11)	0.0076 (10)	0.0027 (10)	0.0064 (10)

Br1—C17	1.896 (3)	C9—H9A	0.9800
S1—O2	1.4913 (19)	C9—H9B	0.9800
S1—C1	1.763 (2)	C9—H9C	0.9800
S1—C12	1.809 (3)	C10—H10A	0.9800
O1—C8	1.378 (3)	C10—H10B	0.9800
O1—C7	1.392 (3)	C10—H10C	0.9800
C1—C8	1.354 (3)	C11—H11A	0.9800
C1—C2	1.451 (3)	C11—H11B	0.9800
C2—C7	1.392 (3)	C11—H11C	0.9800
C2—C3	1.397 (3)	C12—C13	1.388 (3)
C3—C4	1.386 (4)	C12—C17	1.391 (3)
C3—H3	0.9500	C13—C14	1.387 (4)
C4—C5	1.405 (4)	C13—H13	0.9500
C4—C9	1.512 (4)	C14—C15	1.387 (4)
C5—C6	1.387 (4)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.384 (4)
C6—C7	1.387 (4)	C15—H15	0.9500
C6—C10	1.509 (4)	C16—C17	1.393 (4)
C8—C11	1.483 (3)	C16—H16	0.9500
O2—S1—C1	107.88 (11)	H9A—C9—H9C	109.5
O2—S1—C12	105.17 (11)	H9B—C9—H9C	109.5
C1—S1—C12	99.38 (11)	C6—C10—H10A	109.5
C8—O1—C7	106.49 (18)	C6—C10—H10B	109.5
C8—C1—C2	108.3 (2)	H10A—C10—H10B	109.5
C8—C1—S1	121.31 (19)	C6—C10—H10C	109.5
C2—C1—S1	130.28 (18)	H10A—C10—H10C	109.5
C7—C2—C3	119.3 (2)	H10B—C10—H10C	109.5
C7—C2—C1	104.2 (2)	C8—C11—H11A	109.5
C3—C2—C1	136.5 (2)	C8—C11—H11B	109.5
C4—C3—C2	118.5 (2)	H11A—C11—H11B	109.5
C4—C3—H3	120.8	C8—C11—H11C	109.5
C2—C3—H3	120.8	H11A—C11—H11C	109.5
C3—C4—C5	119.9 (2)	H11B—C11—H11C	109.5
C3—C4—C9	120.8 (2)	C13—C12—C17	119.0 (2)
C5—C4—C9	119.3 (2)	C13—C12—S1	117.37 (18)
C6—C5—C4	123.4 (2)	C17—C12—S1	123.18 (19)
C6—C5—H5	118.3	C14—C13—C12	120.8 (2)
C4—C5—H5	118.3	C14—C13—H13	119.6
C7—C6—C5	114.6 (2)	C12—C13—H13	119.6
C7—C6—C10	122.2 (2)	C13—C14—C15	119.7 (3)
C5—C6—C10	123.2 (2)	C13—C14—H14	120.2
C6—C7—C2	124.4 (2)	C15—C14—H14	120.2
C6—C7—O1	124.9 (2)	C16—C15—C14	120.4 (3)
C2—C7—O1	110.7 (2)	C16—C15—H15	119.8
C1—C8—O1	110.3 (2)	C14—C15—H15	119.8
C1—C8—C11	133.8 (2)	C15—C16—C17	119.5 (2)
O1—C8—C11	115.9 (2)	C15—C16—H16	120.2
C4—C9—H9A	109.5	C17—C16—H16	120.2
C4—C9—H9B	109.5	C12—C17—C16	120.6 (2)
H9A—C9—H9B	109.5	C12—C17—Br1	121.3 (2)
C4—C9—H9C	109.5	C16—C17—Br1	118.05 (19)
O2—S1—C1—C8	−121.0 (2)	C8—O1—C7—C6	178.3 (2)
C12—S1—C1—C8	129.6 (2)	C8—O1—C7—C2	0.0 (2)
O2—S1—C1—C2	54.9 (3)	C2—C1—C8—O1	0.0 (3)
C12—S1—C1—C2	−54.5 (2)	S1—C1—C8—O1	176.70 (16)
C8—C1—C2—C7	0.0 (3)	C2—C1—C8—C11	−179.9 (3)
S1—C1—C2—C7	−176.30 (19)	S1—C1—C8—C11	−3.2 (4)
C8—C1—C2—C3	−178.6 (3)	C7—O1—C8—C1	0.0 (3)
S1—C1—C2—C3	5.1 (4)	C7—O1—C8—C11	179.9 (2)
C7—C2—C3—C4	0.1 (3)	O2—S1—C12—C13	5.5 (2)
C1—C2—C3—C4	178.5 (3)	C1—S1—C12—C13	117.0 (2)
C2—C3—C4—C5	−0.6 (4)	O2—S1—C12—C17	177.91 (19)
C2—C3—C4—C9	−179.4 (2)	C1—S1—C12—C17	−70.5 (2)
C3—C4—C5—C6	0.5 (4)	C17—C12—C13—C14	−0.5 (4)
C9—C4—C5—C6	179.3 (2)	S1—C12—C13—C14	172.26 (19)
C4—C5—C6—C7	0.1 (4)	C12—C13—C14—C15	0.8 (4)
C4—C5—C6—C10	−179.2 (3)	C13—C14—C15—C16	0.1 (4)
C5—C6—C7—C2	−0.7 (4)	C14—C15—C16—C17	−1.3 (4)
C10—C6—C7—C2	178.6 (2)	C13—C12—C17—C16	−0.7 (3)
C5—C6—C7—O1	−178.7 (2)	S1—C12—C17—C16	−173.02 (19)
C10—C6—C7—O1	0.6 (4)	C13—C12—C17—Br1	177.67 (18)
C3—C2—C7—C6	0.6 (4)	S1—C12—C17—Br1	5.3 (3)
C1—C2—C7—C6	−178.3 (2)	C15—C16—C17—C12	1.6 (4)
C3—C2—C7—O1	178.9 (2)	C15—C16—C17—Br1	−176.83 (19)
C1—C2—C7—O1	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cg1i	0.98	2.92	3.594 (3)	127
C16—H16···Cg2ii	0.95	2.78	3.551 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯Cg1i	0.98	2.92	3.594 (3)	127
C16—H16⋯Cg2ii	0.95	2.78	3.551 (3)	139

Symmetry codes: (i) ; (ii) .