5-Bromo-2-methyl-3-(3-methyl-phenyl-sulfin-yl)-1-benzo-furan.

In the title compound, C16H13BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzo-furan ring system and the 3-methyl-phenyl ring is 84.83 (4)°. In the crystal, mol-ecules are linked via pairs of Br⋯O [3.240 (1) Å] contacts, forming inversion dimers. These dimers are linked by C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H13BrO2S

M = 349.23

Triclinic,

a = 8.4209 (1) Å

b = 8.9042 (1) Å

c = 10.8628 (1) Å

α = 106.956 (1)°

β = 90.441 (1)°

γ = 108.900 (1)°

V = 732.38 (1) Å3

Z = 2

Mo Kα radiation

μ = 2.95 mm−1

T = 173 K

0.43 × 0.32 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.365, T max = 0.746

13736 measured reflections

3667 independent reflections

3391 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.066

S = 1.09

3667 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.36 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) I. DOI: 10.1107/S1600536814003365/su2700sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003365/su2700Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003365/su2700Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H13BrO2S	Z = 2
Mr = 349.23	F(000) = 352
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4209 (1) Å	Cell parameters from 8553 reflections
b = 8.9042 (1) Å	θ = 2.5–28.4°
c = 10.8628 (1) Å	µ = 2.95 mm−1
α = 106.956 (1)°	T = 173 K
β = 90.441 (1)°	Block, colourless
γ = 108.900 (1)°	0.43 × 0.32 × 0.09 mm
V = 732.38 (1) Å3

Bruker SMART APEXII CCD diffractometer	3667 independent reflections
Radiation source: rotating anode	3391 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.365, Tmax = 0.746	l = −14→14
13736 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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F2) = 0.066	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0306P)2 + 0.2396P] where P = (Fo2 + 2Fc2)/3
3667 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.36 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	0.04187 (2)	0.75979 (2)	0.479648 (15)	0.03138 (7)
S1	0.24413 (5)	0.49344 (5)	0.90916 (4)	0.02597 (9)
O1	0.23301 (15)	0.94970 (14)	1.04896 (11)	0.0283 (2)
O2	0.08675 (15)	0.36872 (15)	0.82700 (13)	0.0339 (3)
C1	0.23351 (19)	0.69433 (19)	0.93705 (15)	0.0230 (3)
C2	0.18550 (18)	0.76541 (18)	0.84534 (14)	0.0209 (3)
C3	0.14284 (19)	0.71368 (19)	0.71172 (15)	0.0224 (3)
H3	0.1423	0.6081	0.6579	0.027*
C4	0.10115 (19)	0.82404 (19)	0.66114 (15)	0.0235 (3)
C5	0.0980 (2)	0.9788 (2)	0.73792 (17)	0.0271 (3)
H5	0.0661	1.0488	0.6989	0.033*
C6	0.1413 (2)	1.03082 (19)	0.87084 (17)	0.0273 (3)
H6	0.1405	1.1358	0.9249	0.033*
C7	0.18532 (19)	0.92194 (19)	0.92009 (15)	0.0234 (3)
C8	0.2602 (2)	0.8082 (2)	1.05582 (16)	0.0266 (3)
C9	0.3152 (3)	0.8114 (3)	1.18646 (17)	0.0384 (4)
H9A	0.3161	0.7005	1.1833	0.058*
H9B	0.2369	0.8424	1.2469	0.058*
H9C	0.4291	0.8934	1.2159	0.058*
C10	0.40882 (18)	0.50755 (19)	0.80452 (15)	0.0234 (3)
C11	0.5604 (2)	0.6403 (2)	0.84122 (18)	0.0317 (3)
H11	0.5760	0.7300	0.9187	0.038*
C12	0.6883 (2)	0.6386 (2)	0.7623 (2)	0.0384 (4)
H12	0.7932	0.7281	0.7859	0.046*
C13	0.6648 (2)	0.5077 (2)	0.64917 (19)	0.0345 (4)
H13	0.7539	0.5090	0.5959	0.041*
C14	0.5133 (2)	0.3745 (2)	0.61235 (17)	0.0289 (3)
C15	0.3854 (2)	0.3760 (2)	0.69235 (16)	0.0266 (3)
H15	0.2810	0.2857	0.6697	0.032*
C16	0.4876 (3)	0.2305 (3)	0.4904 (2)	0.0424 (4)
H16A	0.5240	0.2737	0.4181	0.064*
H16B	0.3678	0.1614	0.4714	0.064*
H16C	0.5545	0.1629	0.5023	0.064*

	U11	U22	U33	U12	U13	U23
Br1	0.03812 (10)	0.03427 (10)	0.02629 (9)	0.01357 (7)	0.00008 (6)	0.01480 (7)
S1	0.02985 (19)	0.02419 (19)	0.0310 (2)	0.01154 (15)	0.00610 (15)	0.01633 (16)
O1	0.0335 (6)	0.0250 (6)	0.0242 (6)	0.0104 (5)	0.0017 (4)	0.0042 (5)
O2	0.0277 (6)	0.0229 (6)	0.0491 (8)	0.0053 (5)	0.0083 (5)	0.0119 (5)
C1	0.0248 (7)	0.0231 (7)	0.0238 (7)	0.0085 (6)	0.0040 (5)	0.0107 (6)
C2	0.0214 (6)	0.0196 (7)	0.0245 (7)	0.0077 (5)	0.0052 (5)	0.0099 (6)
C3	0.0259 (7)	0.0199 (7)	0.0233 (7)	0.0092 (5)	0.0032 (5)	0.0079 (6)
C4	0.0225 (7)	0.0249 (7)	0.0256 (7)	0.0075 (6)	0.0022 (5)	0.0121 (6)
C5	0.0260 (7)	0.0227 (7)	0.0373 (9)	0.0088 (6)	0.0034 (6)	0.0156 (7)
C6	0.0292 (8)	0.0184 (7)	0.0345 (8)	0.0093 (6)	0.0036 (6)	0.0070 (6)
C7	0.0241 (7)	0.0212 (7)	0.0237 (7)	0.0069 (5)	0.0031 (5)	0.0063 (6)
C8	0.0259 (7)	0.0286 (8)	0.0264 (8)	0.0080 (6)	0.0039 (6)	0.0113 (6)
C9	0.0439 (10)	0.0467 (11)	0.0243 (8)	0.0141 (8)	−0.0007 (7)	0.0124 (8)
C10	0.0219 (7)	0.0236 (7)	0.0296 (8)	0.0100 (6)	0.0012 (6)	0.0131 (6)
C11	0.0277 (8)	0.0259 (8)	0.0368 (9)	0.0069 (6)	0.0001 (7)	0.0057 (7)
C12	0.0253 (8)	0.0308 (9)	0.0524 (12)	0.0037 (7)	0.0050 (7)	0.0097 (8)
C13	0.0293 (8)	0.0335 (9)	0.0450 (10)	0.0131 (7)	0.0123 (7)	0.0157 (8)
C14	0.0315 (8)	0.0285 (8)	0.0316 (8)	0.0152 (6)	0.0026 (6)	0.0111 (7)
C15	0.0245 (7)	0.0225 (7)	0.0338 (8)	0.0081 (6)	−0.0015 (6)	0.0103 (6)
C16	0.0451 (10)	0.0391 (10)	0.0401 (10)	0.0190 (8)	0.0048 (8)	0.0027 (8)

Br1—C4	1.8988 (16)	C8—C9	1.479 (2)
Br1—O2i	3.2399 (14)	C9—H9A	0.9800
S1—O2	1.4954 (13)	C9—H9B	0.9800
S1—C1	1.7571 (16)	C9—H9C	0.9800
S1—C10	1.7960 (16)	C10—C15	1.382 (2)
O1—C8	1.373 (2)	C10—C11	1.387 (2)
O1—C7	1.3810 (19)	C11—C12	1.382 (3)
C1—C8	1.352 (2)	C11—H11	0.9500
C1—C2	1.444 (2)	C12—C13	1.386 (3)
C2—C3	1.394 (2)	C12—H12	0.9500
C2—C7	1.394 (2)	C13—C14	1.389 (2)
C3—C4	1.388 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.390 (2)
C4—C5	1.396 (2)	C14—C16	1.507 (3)
C5—C6	1.387 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.377 (2)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C4—Br1—O2i	175.63 (5)	C8—C9—H9B	109.5
O2—S1—C1	108.56 (7)	H9A—C9—H9B	109.5
O2—S1—C10	106.16 (7)	C8—C9—H9C	109.5
C1—S1—C10	98.49 (7)	H9A—C9—H9C	109.5
C8—O1—C7	106.43 (12)	H9B—C9—H9C	109.5
C8—C1—C2	107.45 (14)	C15—C10—C11	121.21 (15)
C8—C1—S1	123.80 (12)	C15—C10—S1	118.01 (12)
C2—C1—S1	128.62 (12)	C11—C10—S1	120.56 (13)
C3—C2—C7	119.50 (13)	C12—C11—C10	118.38 (17)
C3—C2—C1	135.70 (14)	C12—C11—H11	120.8
C7—C2—C1	104.80 (13)	C10—C11—H11	120.8
C4—C3—C2	116.72 (14)	C11—C12—C13	120.62 (16)
C4—C3—H3	121.6	C11—C12—H12	119.7
C2—C3—H3	121.6	C13—C12—H12	119.7
C3—C4—C5	122.96 (15)	C12—C13—C14	121.11 (17)
C3—C4—Br1	118.47 (12)	C12—C13—H13	119.4
C5—C4—Br1	118.57 (11)	C14—C13—H13	119.4
C6—C5—C4	120.40 (14)	C13—C14—C15	118.14 (16)
C6—C5—H5	119.8	C13—C14—C16	121.43 (17)
C4—C5—H5	119.8	C15—C14—C16	120.43 (16)
C7—C6—C5	116.32 (14)	C10—C15—C14	120.54 (15)
C7—C6—H6	121.8	C10—C15—H15	119.7
C5—C6—H6	121.8	C14—C15—H15	119.7
C6—C7—O1	125.57 (14)	C14—C16—H16A	109.5
C6—C7—C2	124.08 (15)	C14—C16—H16B	109.5
O1—C7—C2	110.35 (13)	H16A—C16—H16B	109.5
C1—C8—O1	110.95 (14)	C14—C16—H16C	109.5
C1—C8—C9	133.31 (16)	H16A—C16—H16C	109.5
O1—C8—C9	115.71 (15)	H16B—C16—H16C	109.5
C8—C9—H9A	109.5
O2—S1—C1—C8	129.11 (14)	C1—C2—C7—O1	1.19 (16)
C10—S1—C1—C8	−120.59 (14)	C2—C1—C8—O1	0.05 (18)
O2—S1—C1—C2	−46.22 (16)	S1—C1—C8—O1	−176.13 (11)
C10—S1—C1—C2	64.09 (15)	C2—C1—C8—C9	−178.18 (18)
C8—C1—C2—C3	179.77 (17)	S1—C1—C8—C9	5.6 (3)
S1—C1—C2—C3	−4.3 (3)	C7—O1—C8—C1	0.68 (17)
C8—C1—C2—C7	−0.75 (17)	C7—O1—C8—C9	179.25 (14)
S1—C1—C2—C7	175.18 (12)	O2—S1—C10—C15	−21.27 (13)
C7—C2—C3—C4	−0.4 (2)	C1—S1—C10—C15	−133.50 (12)
C1—C2—C3—C4	179.07 (16)	O2—S1—C10—C11	164.08 (13)
C2—C3—C4—C5	−1.1 (2)	C1—S1—C10—C11	51.85 (14)
C2—C3—C4—Br1	−179.96 (11)	C15—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	1.5 (2)	S1—C10—C11—C12	174.82 (14)
Br1—C4—C5—C6	−179.67 (12)	C10—C11—C12—C13	0.2 (3)
C4—C5—C6—C7	−0.3 (2)	C11—C12—C13—C14	−0.4 (3)
C5—C6—C7—O1	179.71 (14)	C12—C13—C14—C15	−0.1 (3)
C5—C6—C7—C2	−1.2 (2)	C12—C13—C14—C16	−179.16 (18)
C8—O1—C7—C6	178.02 (15)	C11—C10—C15—C14	−0.8 (2)
C8—O1—C7—C2	−1.18 (17)	S1—C10—C15—C14	−175.41 (12)
C3—C2—C7—C6	1.6 (2)	C13—C14—C15—C10	0.6 (2)
C1—C2—C7—C6	−178.02 (15)	C16—C14—C15—C10	179.75 (15)
C3—C2—C7—O1	−179.22 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ii	0.98	2.91	3.785 (2)	150
C12—H12···Cg2iii	0.95	2.79	3.674 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C10–C15 (3-methyl­phen­yl) and C2–C7 (benzene), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cg1i	0.98	2.91	3.785 (2)	150
C12—H12⋯Cg2ii	0.95	2.79	3.674 (2)	154

Symmetry codes: (i) ; (ii) .