5-Bromo-2,4,6-trimethyl-3-(4-methyl-phenyl-sulfin-yl)-1-benzo-furan.

In the title compound, C18H17BrO2S, the dihedral angle between the methyl-phenyl ring and the mean plane of the benzo-furan rung system is 87.0 (2)°. In the crystal, mol-ecules related by inversion are paired into dimers via C-H⋯O and C-H⋯π inter-actions. These dimers are further linked by C-H⋯O hydrogen bonds and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.555 (5) Å], resulting in a three-dimensional supra-molecular network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2011 ▶).

Experimental

Crystal data

C18H17BrO2S

M = 377.29

Triclinic,

a = 8.793 (5) Å

b = 9.229 (5) Å

c = 10.861 (6) Å

α = 86.105 (16)°

β = 69.582 (17)°

γ = 80.550 (16)°

V = 814.7 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.66 mm−1

T = 173 K

0.42 × 0.35 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.402, T max = 0.580

10322 measured reflections

2857 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.177

S = 1.15

2857 reflections

203 parameters

H-atom parameters constrained

Δρmax = 1.44 e Å−3

Δρmin = −1.27 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/S1600536814004310/xu5773sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004310/xu5773Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004310/xu5773Isup3.cml

CCDC reference: 988674

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

C18H17BrO2S	Z = 2
Mr = 377.29	F(000) = 384
Triclinic, P1	Dx = 1.538 Mg m−3
Hall symbol: -P 1	Melting point = 470–471 K
a = 8.793 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.229 (5) Å	Cell parameters from 5866 reflections
c = 10.861 (6) Å	θ = 2.2–28.2°
α = 86.105 (16)°	µ = 2.66 mm−1
β = 69.582 (17)°	T = 173 K
γ = 80.550 (16)°	Block, colourless
V = 814.7 (8) Å3	0.42 × 0.35 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	2857 independent reflections
Radiation source: rotating anode	2420 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.067
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.402, Tmax = 0.580	l = −12→12
10322 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)] = 0.062	Hydrogen site location: difference Fourier map
wR(F2) = 0.177	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0949P)2 + 1.1374P] where P = (Fo2 + 2Fc2)/3
2857 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 1.44 e Å−3
0 restraints	Δρmin = −1.27 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	0.73930 (7)	0.37481 (6)	0.59473 (5)	0.0546 (3)
S1	0.14037 (13)	0.83306 (15)	0.96038 (13)	0.0394 (3)
O1	0.5385 (4)	0.7754 (3)	1.0502 (3)	0.0328 (7)
O2	0.0597 (5)	0.7075 (5)	0.9495 (4)	0.0571 (11)
C1	0.3381 (5)	0.7704 (5)	0.9688 (5)	0.0319 (10)
C2	0.4792 (5)	0.6678 (5)	0.8932 (4)	0.0276 (9)
C3	0.5165 (6)	0.5721 (5)	0.7880 (5)	0.0346 (10)
C4	0.6773 (6)	0.4989 (5)	0.7443 (5)	0.0346 (10)
C5	0.7984 (6)	0.5111 (5)	0.7983 (5)	0.0360 (11)
C6	0.7561 (5)	0.6025 (5)	0.9048 (5)	0.0346 (11)
H6	0.8326	0.6129	0.9463	0.042*
C7	0.5984 (5)	0.6779 (5)	0.9481 (4)	0.0278 (9)
C8	0.3796 (5)	0.8293 (5)	1.0595 (4)	0.0307 (10)
C9	0.3914 (7)	0.5491 (7)	0.7294 (6)	0.0503 (14)
H9A	0.4179	0.5943	0.6416	0.075*
H9B	0.2824	0.5945	0.7855	0.075*
H9C	0.3921	0.4436	0.7229	0.075*
C10	0.9707 (6)	0.4268 (7)	0.7463 (6)	0.0520 (14)
H10A	1.0319	0.4439	0.8028	0.078*
H10B	1.0265	0.4603	0.6566	0.078*
H10C	0.9653	0.3216	0.7459	0.078*
C11	0.2953 (7)	0.9413 (6)	1.1636 (5)	0.0447 (12)
H11A	0.3449	1.0314	1.1384	0.067*
H11B	0.3071	0.9033	1.2468	0.067*
H11C	0.1786	0.9629	1.1742	0.067*
C12	0.1975 (5)	0.9215 (5)	0.8030 (5)	0.0353 (11)
C13	0.1410 (6)	0.8845 (6)	0.7076 (6)	0.0413 (12)
H13	0.0813	0.8043	0.7215	0.050*
C14	0.1720 (7)	0.9653 (6)	0.5911 (5)	0.0450 (12)
H14	0.1340	0.9392	0.5250	0.054*
C15	0.2570 (7)	1.0826 (6)	0.5702 (5)	0.0459 (13)
C16	0.3127 (7)	1.1186 (6)	0.6677 (6)	0.0485 (14)
H16	0.3734	1.1980	0.6538	0.058*
C17	0.2810 (6)	1.0405 (6)	0.7841 (5)	0.0414 (12)
H17	0.3162	1.0681	0.8513	0.050*
C18	0.2899 (11)	1.1726 (8)	0.4462 (6)	0.075 (2)
H18A	0.3956	1.1316	0.3821	0.112*
H18B	0.2933	1.2741	0.4653	0.112*
H18C	0.2025	1.1711	0.4101	0.112*

	U11	U22	U33	U12	U13	U23
Br1	0.0716 (5)	0.0430 (4)	0.0419 (4)	−0.0002 (3)	−0.0117 (3)	−0.0140 (3)
S1	0.0234 (5)	0.0507 (7)	0.0420 (7)	−0.0043 (5)	−0.0094 (5)	0.0013 (6)
O1	0.0333 (16)	0.0353 (17)	0.0331 (18)	−0.0088 (13)	−0.0132 (13)	−0.0042 (14)
O2	0.0391 (19)	0.068 (3)	0.070 (3)	−0.0237 (18)	−0.0217 (19)	0.015 (2)
C1	0.026 (2)	0.031 (2)	0.037 (3)	−0.0052 (17)	−0.0097 (18)	0.0021 (19)
C2	0.026 (2)	0.028 (2)	0.033 (2)	−0.0085 (16)	−0.0128 (17)	0.0018 (18)
C3	0.042 (3)	0.029 (2)	0.036 (3)	−0.0090 (19)	−0.015 (2)	0.001 (2)
C4	0.046 (3)	0.028 (2)	0.028 (2)	−0.0071 (19)	−0.0085 (19)	−0.0049 (18)
C5	0.033 (2)	0.034 (2)	0.036 (3)	−0.0050 (19)	−0.0055 (19)	0.003 (2)
C6	0.024 (2)	0.039 (3)	0.044 (3)	−0.0084 (18)	−0.014 (2)	0.005 (2)
C7	0.031 (2)	0.031 (2)	0.026 (2)	−0.0122 (17)	−0.0111 (17)	−0.0006 (17)
C8	0.034 (2)	0.031 (2)	0.027 (2)	−0.0066 (18)	−0.0106 (18)	0.0022 (18)
C9	0.051 (3)	0.053 (3)	0.059 (4)	−0.006 (2)	−0.032 (3)	−0.018 (3)
C10	0.035 (3)	0.059 (3)	0.048 (3)	0.002 (2)	−0.001 (2)	−0.002 (3)
C11	0.046 (3)	0.044 (3)	0.037 (3)	−0.005 (2)	−0.003 (2)	−0.009 (2)
C12	0.027 (2)	0.034 (2)	0.041 (3)	0.0061 (18)	−0.0106 (19)	−0.005 (2)
C13	0.039 (3)	0.037 (3)	0.050 (3)	−0.004 (2)	−0.018 (2)	−0.006 (2)
C14	0.057 (3)	0.041 (3)	0.037 (3)	0.006 (2)	−0.020 (2)	−0.010 (2)
C15	0.056 (3)	0.032 (3)	0.038 (3)	0.006 (2)	−0.007 (2)	−0.010 (2)
C16	0.053 (3)	0.034 (3)	0.054 (4)	−0.009 (2)	−0.010 (3)	−0.001 (2)
C17	0.044 (3)	0.040 (3)	0.043 (3)	−0.008 (2)	−0.017 (2)	−0.006 (2)
C18	0.111 (6)	0.051 (4)	0.040 (4)	0.001 (4)	−0.006 (4)	0.002 (3)

Br1—C4	1.918 (5)	C10—H10A	0.9800
S1—O2	1.485 (4)	C10—H10B	0.9800
S1—C1	1.772 (5)	C10—H10C	0.9800
S1—C12	1.785 (5)	C11—H11A	0.9800
O1—C8	1.374 (6)	C11—H11B	0.9800
O1—C7	1.375 (6)	C11—H11C	0.9800
C1—C8	1.337 (7)	C12—C13	1.378 (8)
C1—C2	1.456 (6)	C12—C17	1.384 (7)
C2—C7	1.392 (6)	C13—C14	1.389 (8)
C2—C3	1.405 (7)	C13—H13	0.9500
C3—C4	1.393 (7)	C14—C15	1.378 (8)
C3—C9	1.497 (7)	C14—H14	0.9500
C4—C5	1.406 (7)	C15—C16	1.391 (9)
C5—C6	1.384 (7)	C15—C18	1.497 (8)
C5—C10	1.515 (7)	C16—C17	1.375 (8)
C6—C7	1.378 (6)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.490 (7)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800
O2—S1—C1	110.8 (2)	C5—C10—H10B	109.5
O2—S1—C12	106.7 (2)	H10A—C10—H10B	109.5
C1—S1—C12	99.4 (2)	C5—C10—H10C	109.5
C8—O1—C7	106.3 (3)	H10A—C10—H10C	109.5
C8—C1—C2	107.6 (4)	H10B—C10—H10C	109.5
C8—C1—S1	117.8 (4)	C8—C11—H11A	109.5
C2—C1—S1	134.5 (4)	C8—C11—H11B	109.5
C7—C2—C3	119.4 (4)	H11A—C11—H11B	109.5
C7—C2—C1	104.1 (4)	C8—C11—H11C	109.5
C3—C2—C1	136.6 (4)	H11A—C11—H11C	109.5
C4—C3—C2	114.9 (4)	H11B—C11—H11C	109.5
C4—C3—C9	122.9 (5)	C13—C12—C17	120.2 (5)
C2—C3—C9	122.2 (4)	C13—C12—S1	120.4 (4)
C3—C4—C5	125.7 (4)	C17—C12—S1	118.8 (4)
C3—C4—Br1	116.9 (4)	C12—C13—C14	119.5 (5)
C5—C4—Br1	117.4 (4)	C12—C13—H13	120.2
C6—C5—C4	118.0 (4)	C14—C13—H13	120.2
C6—C5—C10	119.3 (5)	C15—C14—C13	120.9 (5)
C4—C5—C10	122.7 (5)	C15—C14—H14	119.6
C7—C6—C5	117.2 (4)	C13—C14—H14	119.6
C7—C6—H6	121.4	C14—C15—C16	118.8 (5)
C5—C6—H6	121.4	C14—C15—C18	121.9 (6)
O1—C7—C6	124.4 (4)	C16—C15—C18	119.3 (6)
O1—C7—C2	110.8 (4)	C17—C16—C15	120.8 (5)
C6—C7—C2	124.8 (4)	C17—C16—H16	119.6
C1—C8—O1	111.2 (4)	C15—C16—H16	119.6
C1—C8—C11	134.7 (5)	C16—C17—C12	119.8 (5)
O1—C8—C11	114.0 (4)	C16—C17—H17	120.1
C3—C9—H9A	109.5	C12—C17—H17	120.1
C3—C9—H9B	109.5	C15—C18—H18A	109.5
H9A—C9—H9B	109.5	C15—C18—H18B	109.5
C3—C9—H9C	109.5	H18A—C18—H18B	109.5
H9A—C9—H9C	109.5	C15—C18—H18C	109.5
H9B—C9—H9C	109.5	H18A—C18—H18C	109.5
C5—C10—H10A	109.5	H18B—C18—H18C	109.5
O2—S1—C1—C8	−134.4 (4)	C5—C6—C7—C2	0.5 (7)
C12—S1—C1—C8	113.6 (4)	C3—C2—C7—O1	−179.3 (4)
O2—S1—C1—C2	48.7 (5)	C1—C2—C7—O1	1.0 (5)
C12—S1—C1—C2	−63.3 (5)	C3—C2—C7—C6	1.7 (7)
C8—C1—C2—C7	−0.9 (5)	C1—C2—C7—C6	−178.0 (4)
S1—C1—C2—C7	176.2 (4)	C2—C1—C8—O1	0.6 (5)
C8—C1—C2—C3	179.5 (5)	S1—C1—C8—O1	−177.1 (3)
S1—C1—C2—C3	−3.4 (8)	C2—C1—C8—C11	178.4 (5)
C7—C2—C3—C4	−2.6 (6)	S1—C1—C8—C11	0.7 (7)
C1—C2—C3—C4	177.0 (5)	C7—O1—C8—C1	0.0 (5)
C7—C2—C3—C9	176.4 (5)	C7—O1—C8—C11	−178.3 (4)
C1—C2—C3—C9	−4.1 (8)	O2—S1—C12—C13	10.6 (4)
C2—C3—C4—C5	1.6 (7)	C1—S1—C12—C13	125.8 (4)
C9—C3—C4—C5	−177.3 (5)	O2—S1—C12—C17	−177.8 (4)
C2—C3—C4—Br1	−176.7 (3)	C1—S1—C12—C17	−62.6 (4)
C9—C3—C4—Br1	4.4 (6)	C17—C12—C13—C14	1.6 (7)
C3—C4—C5—C6	0.5 (7)	S1—C12—C13—C14	173.0 (4)
Br1—C4—C5—C6	178.8 (3)	C12—C13—C14—C15	−0.6 (8)
C3—C4—C5—C10	179.4 (5)	C13—C14—C15—C16	0.4 (8)
Br1—C4—C5—C10	−2.3 (6)	C13—C14—C15—C18	−179.2 (5)
C4—C5—C6—C7	−1.5 (6)	C14—C15—C16—C17	−1.3 (8)
C10—C5—C6—C7	179.5 (4)	C18—C15—C16—C17	178.4 (5)
C8—O1—C7—C6	178.3 (4)	C15—C16—C17—C12	2.2 (8)
C8—O1—C7—C2	−0.7 (4)	C13—C12—C17—C16	−2.4 (7)
C5—C6—C7—O1	−178.3 (4)	S1—C12—C17—C16	−174.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.32	3.181 (6)	151
C17—H17···O1ii	0.95	2.58	3.456 (6)	154
C11—H11A···Cg2ii	0.98	2.83	3.794 (6)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.32	3.181 (6)	151
C17—H17⋯O1ii	0.95	2.58	3.456 (6)	154
C11—H11A⋯Cg2ii	0.98	2.83	3.794 (6)	167

Symmetry codes: (i) ; (ii) .