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

In the title compound, C17H15BrO2S, the 4-methyl-benzene ring makes a dihedral angle of 89.01 (7)° with the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzo-furan fragment. In the crystal, mol-ecules are linked into supra-molecular layers that stack along [001] by weak C-H⋯O, C-H⋯π and C-S⋯π [3.364 (2) Å] inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Triclinic,

a = 6.1794 (6) Å

b = 10.057 (1) Å

c = 12.5793 (12) Å

α = 84.072 (6)°

β = 79.738 (6)°

γ = 85.471 (6)°

V = 763.67 (13) Å3

Z = 2

Mo Kα radiation

μ = 2.83 mm−1

T = 173 K

0.22 × 0.13 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.640, T max = 0.746

13108 measured reflections

3331 independent reflections

2180 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.089

S = 1.04

3331 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.52 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/S1600536813009756/tk5212sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009756/tk5212Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009756/tk5212Isup3.cml

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

C17H15BrO2S	Z = 2
Mr = 363.26	F(000) = 368
Triclinic, P1	Dx = 1.580 Mg m−3
Hall symbol: -P 1	Melting point = 406–407 K
a = 6.1794 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.057 (1) Å	Cell parameters from 3261 reflections
c = 12.5793 (12) Å	θ = 2.4–26.4°
α = 84.072 (6)°	µ = 2.83 mm−1
β = 79.738 (6)°	T = 173 K
γ = 85.471 (6)°	Block, colourless
V = 763.67 (13) Å3	0.22 × 0.13 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	3331 independent reflections
Radiation source: rotating anode	2180 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.075
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.0°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.640, Tmax = 0.746	l = −16→15
13108 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0171P)2 + 0.341P] where P = (Fo2 + 2Fc2)/3
3331 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.52 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	1.08078 (6)	0.92372 (4)	0.82890 (3)	0.04049 (15)
S1	0.60771 (14)	0.49101 (9)	0.65693 (6)	0.0281 (2)
O1	0.2942 (3)	0.5989 (2)	0.93938 (16)	0.0285 (6)
O2	0.8519 (3)	0.4747 (2)	0.64788 (17)	0.0355 (6)
C1	0.5062 (5)	0.5624 (3)	0.7794 (2)	0.0243 (8)
C2	0.6048 (5)	0.6623 (3)	0.8261 (2)	0.0237 (8)
C3	0.7900 (5)	0.7364 (3)	0.7958 (3)	0.0273 (8)
H3	0.8874	0.7271	0.7291	0.033*
C4	0.8251 (5)	0.8235 (3)	0.8669 (3)	0.0284 (8)
C5	0.6844 (5)	0.8414 (3)	0.9642 (3)	0.0303 (9)
H5	0.7164	0.9043	1.0098	0.036*
C6	0.4982 (5)	0.7692 (3)	0.9961 (2)	0.0273 (8)
C7	0.4681 (5)	0.6809 (3)	0.9246 (3)	0.0241 (8)
C8	0.3243 (5)	0.5271 (3)	0.8496 (3)	0.0271 (8)
C9	0.3398 (6)	0.7855 (4)	1.1002 (3)	0.0399 (10)
H9A	0.1935	0.8152	1.0838	0.060*
H9B	0.3911	0.8522	1.1399	0.060*
H9C	0.3315	0.6995	1.1447	0.060*
C10	0.1534 (6)	0.4332 (3)	0.8474 (3)	0.0335 (9)
H10A	0.0188	0.4838	0.8317	0.050*
H10B	0.1218	0.3813	0.9181	0.050*
H10C	0.2062	0.3723	0.7911	0.050*
C11	0.5490 (5)	0.6350 (3)	0.5679 (2)	0.0247 (8)
C12	0.7171 (5)	0.6888 (3)	0.4924 (3)	0.0290 (8)
H12	0.8642	0.6515	0.4883	0.035*
C13	0.6670 (6)	0.7983 (4)	0.4229 (3)	0.0340 (9)
H13	0.7823	0.8369	0.3716	0.041*
C14	0.4543 (6)	0.8527 (3)	0.4259 (3)	0.0304 (8)
C15	0.2879 (6)	0.7931 (4)	0.4998 (3)	0.0326 (9)
H15	0.1399	0.8279	0.5020	0.039*
C16	0.3330 (5)	0.6843 (3)	0.5699 (3)	0.0303 (8)
H16	0.2170	0.6435	0.6192	0.036*
C17	0.4004 (6)	0.9735 (4)	0.3523 (3)	0.0432 (10)
H17A	0.2433	0.9781	0.3477	0.065*
H17B	0.4880	0.9666	0.2798	0.065*
H17C	0.4348	1.0546	0.3814	0.065*

	U11	U22	U33	U12	U13	U23
Br1	0.0302 (2)	0.0392 (3)	0.0535 (3)	−0.00854 (17)	−0.00904 (17)	−0.00239 (19)
S1	0.0288 (5)	0.0298 (6)	0.0253 (5)	−0.0003 (4)	−0.0035 (4)	−0.0036 (4)
O1	0.0286 (14)	0.0304 (15)	0.0237 (13)	−0.0015 (11)	0.0017 (10)	−0.0003 (11)
O2	0.0250 (13)	0.0460 (17)	0.0343 (14)	0.0097 (11)	−0.0052 (10)	−0.0069 (12)
C1	0.0237 (19)	0.026 (2)	0.0219 (18)	0.0001 (15)	−0.0024 (14)	0.0001 (16)
C2	0.0204 (18)	0.027 (2)	0.0226 (18)	0.0015 (15)	−0.0032 (14)	−0.0007 (16)
C3	0.0243 (19)	0.031 (2)	0.0237 (18)	0.0013 (16)	−0.0006 (14)	0.0009 (17)
C4	0.026 (2)	0.026 (2)	0.034 (2)	−0.0021 (16)	−0.0092 (16)	0.0000 (17)
C5	0.036 (2)	0.028 (2)	0.028 (2)	0.0004 (17)	−0.0082 (16)	−0.0043 (17)
C6	0.035 (2)	0.026 (2)	0.0211 (18)	0.0019 (17)	−0.0076 (15)	0.0001 (16)
C7	0.0242 (19)	0.021 (2)	0.0242 (19)	−0.0022 (16)	−0.0014 (14)	0.0050 (16)
C8	0.028 (2)	0.026 (2)	0.0256 (19)	0.0013 (16)	−0.0066 (15)	0.0030 (17)
C9	0.048 (2)	0.043 (3)	0.027 (2)	−0.0022 (19)	0.0015 (17)	−0.0063 (18)
C10	0.032 (2)	0.033 (2)	0.035 (2)	−0.0082 (17)	−0.0044 (15)	0.0015 (18)
C11	0.0236 (19)	0.031 (2)	0.0201 (17)	−0.0027 (16)	−0.0042 (14)	−0.0040 (16)
C12	0.0238 (19)	0.033 (2)	0.031 (2)	−0.0040 (16)	−0.0046 (15)	−0.0064 (17)
C13	0.031 (2)	0.037 (2)	0.034 (2)	−0.0136 (18)	−0.0034 (16)	0.0002 (19)
C14	0.036 (2)	0.032 (2)	0.0258 (19)	−0.0061 (17)	−0.0085 (16)	−0.0029 (17)
C15	0.028 (2)	0.036 (2)	0.036 (2)	0.0038 (17)	−0.0113 (16)	−0.0051 (18)
C16	0.025 (2)	0.035 (2)	0.0296 (19)	−0.0075 (16)	−0.0008 (15)	0.0011 (17)
C17	0.052 (3)	0.039 (3)	0.041 (2)	−0.0099 (19)	−0.0174 (19)	0.0050 (19)

Br1—C4	1.904 (3)	C9—H9B	0.9800
S1—O2	1.490 (2)	C9—H9C	0.9800
S1—C1	1.760 (3)	C10—H10A	0.9800
S1—C11	1.792 (3)	C10—H10B	0.9800
O1—C8	1.380 (4)	C10—H10C	0.9800
O1—C7	1.381 (4)	C11—C12	1.380 (4)
C1—C8	1.347 (4)	C11—C16	1.383 (4)
C1—C2	1.439 (4)	C12—C13	1.385 (4)
C2—C3	1.390 (4)	C12—H12	0.9500
C2—C7	1.390 (4)	C13—C14	1.379 (4)
C3—C4	1.369 (4)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.387 (5)
C4—C5	1.389 (5)	C14—C17	1.503 (5)
C5—C6	1.385 (4)	C15—C16	1.375 (4)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.372 (4)	C16—H16	0.9500
C6—C9	1.504 (4)	C17—H17A	0.9800
C8—C10	1.477 (5)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800
O2—S1—C1	106.70 (14)	H9A—C9—H9C	109.5
O2—S1—C11	106.82 (14)	H9B—C9—H9C	109.5
C1—S1—C11	96.87 (15)	C8—C10—H10A	109.5
C8—O1—C7	106.4 (2)	C8—C10—H10B	109.5
C8—C1—C2	107.4 (3)	H10A—C10—H10B	109.5
C8—C1—S1	125.2 (3)	C8—C10—H10C	109.5
C2—C1—S1	127.3 (2)	H10A—C10—H10C	109.5
C3—C2—C7	118.9 (3)	H10B—C10—H10C	109.5
C3—C2—C1	135.8 (3)	C12—C11—C16	120.7 (3)
C7—C2—C1	105.3 (3)	C12—C11—S1	119.6 (2)
C4—C3—C2	116.7 (3)	C16—C11—S1	119.4 (2)
C4—C3—H3	121.7	C11—C12—C13	118.6 (3)
C2—C3—H3	121.7	C11—C12—H12	120.7
C3—C4—C5	123.3 (3)	C13—C12—H12	120.7
C3—C4—Br1	117.6 (3)	C14—C13—C12	121.8 (3)
C5—C4—Br1	119.1 (3)	C14—C13—H13	119.1
C6—C5—C4	121.2 (3)	C12—C13—H13	119.1
C6—C5—H5	119.4	C13—C14—C15	118.2 (3)
C4—C5—H5	119.4	C13—C14—C17	121.9 (3)
C7—C6—C5	114.6 (3)	C15—C14—C17	120.0 (3)
C7—C6—C9	122.1 (3)	C16—C15—C14	121.2 (3)
C5—C6—C9	123.3 (3)	C16—C15—H15	119.4
C6—C7—O1	124.7 (3)	C14—C15—H15	119.4
C6—C7—C2	125.3 (3)	C15—C16—C11	119.3 (3)
O1—C7—C2	110.0 (3)	C15—C16—H16	120.3
C1—C8—O1	110.8 (3)	C11—C16—H16	120.3
C1—C8—C10	133.4 (3)	C14—C17—H17A	109.5
O1—C8—C10	115.8 (3)	C14—C17—H17B	109.5
C6—C9—H9A	109.5	H17A—C17—H17B	109.5
C6—C9—H9B	109.5	C14—C17—H17C	109.5
H9A—C9—H9B	109.5	H17A—C17—H17C	109.5
C6—C9—H9C	109.5	H17B—C17—H17C	109.5
O2—S1—C1—C8	−139.0 (3)	C1—C2—C7—C6	−179.1 (3)
C11—S1—C1—C8	111.1 (3)	C3—C2—C7—O1	179.8 (3)
O2—S1—C1—C2	37.5 (3)	C1—C2—C7—O1	−0.1 (3)
C11—S1—C1—C2	−72.4 (3)	C2—C1—C8—O1	0.9 (3)
C8—C1—C2—C3	179.7 (3)	S1—C1—C8—O1	177.9 (2)
S1—C1—C2—C3	2.7 (5)	C2—C1—C8—C10	178.6 (3)
C8—C1—C2—C7	−0.4 (3)	S1—C1—C8—C10	−4.3 (5)
S1—C1—C2—C7	−177.4 (2)	C7—O1—C8—C1	−0.9 (3)
C7—C2—C3—C4	0.3 (4)	C7—O1—C8—C10	−179.1 (2)
C1—C2—C3—C4	−179.8 (3)	O2—S1—C11—C12	13.2 (3)
C2—C3—C4—C5	−1.1 (5)	C1—S1—C11—C12	123.1 (3)
C2—C3—C4—Br1	178.7 (2)	O2—S1—C11—C16	−171.8 (3)
C3—C4—C5—C6	0.9 (5)	C1—S1—C11—C16	−62.0 (3)
Br1—C4—C5—C6	−179.0 (2)	C16—C11—C12—C13	3.8 (5)
C4—C5—C6—C7	0.2 (4)	S1—C11—C12—C13	178.6 (2)
C4—C5—C6—C9	−179.6 (3)	C11—C12—C13—C14	−1.2 (5)
C5—C6—C7—O1	−179.9 (3)	C12—C13—C14—C15	−1.3 (5)
C9—C6—C7—O1	−0.1 (5)	C12—C13—C14—C17	178.5 (3)
C5—C6—C7—C2	−1.1 (5)	C13—C14—C15—C16	1.4 (5)
C9—C6—C7—C2	178.7 (3)	C17—C14—C15—C16	−178.5 (3)
C8—O1—C7—C6	179.6 (3)	C14—C15—C16—C11	1.1 (5)
C8—O1—C7—C2	0.6 (3)	C12—C11—C16—C15	−3.7 (5)
C3—C2—C7—C6	0.8 (5)	S1—C11—C16—C15	−178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.58	3.338 (4)	137
C17—H17C···Cgii	0.98	2.77	3.739 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 4-methyl­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.58	3.338 (4)	137
C17—H17C⋯Cg ii	0.98	2.77	3.739 (4)	169

Symmetry codes: (i) ; (ii) .