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

In the title compound, C18H17BrO2S, the dihedral angle between the mean plane of the benzo-furan ring system and the benzene ring is 68.58 (4)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds into inversion dimers. These dimers are linked by C-H⋯O hydrogen bonds and π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.783 (1) Å], forming a three-dimensional network. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [3.153 (1) Å] involving the sulfinyl groups.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2011 ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2013 ▶) and for a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C18H17BrO2S

M = 377.29

Triclinic,

a = 6.2336 (1) Å

b = 11.0353 (2) Å

c = 12.9149 (2) Å

α = 69.384 (1)°

β = 76.421 (1)°

γ = 76.799 (1)°

V = 797.84 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.71 mm−1

T = 173 K

0.35 × 0.34 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.462, T max = 0.746

14962 measured reflections

4023 independent reflections

3702 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.070

S = 1.06

4023 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.49 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/S1600536814005352/bx2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005352/bx2455Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005352/bx2455Isup3.cml

CCDC reference: 990682

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

C18H17BrO2S	Z = 2
Mr = 377.29	F(000) = 384
Triclinic, P1	Dx = 1.570 Mg m−3
Hall symbol: -P 1	Melting point = 469–470 K
a = 6.2336 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0353 (2) Å	Cell parameters from 8866 reflections
c = 12.9149 (2) Å	θ = 3.0–28.4°
α = 69.384 (1)°	µ = 2.71 mm−1
β = 76.421 (1)°	T = 173 K
γ = 76.799 (1)°	Block, colourless
V = 797.84 (2) Å3	0.35 × 0.34 × 0.28 mm

Bruker SMART APEXII CCD diffractometer	4023 independent reflections
Radiation source: rotating anode	3702 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.7°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.462, Tmax = 0.746	l = −17→17
14962 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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.070	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.3061P] where P = (Fo2 + 2Fc2)/3
4023 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.49 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	0.62873 (3)	0.900826 (16)	0.403993 (14)	0.03223 (7)
S1	0.75692 (6)	0.51077 (3)	0.11568 (3)	0.01987 (9)
O1	0.27755 (19)	0.45708 (11)	0.37436 (9)	0.0241 (2)
O2	0.99335 (19)	0.51170 (11)	0.12084 (10)	0.0265 (2)
C1	0.5810 (3)	0.51004 (14)	0.24439 (12)	0.0196 (3)
C2	0.5305 (2)	0.59855 (14)	0.31119 (12)	0.0190 (3)
C3	0.6265 (3)	0.69926 (14)	0.31564 (12)	0.0195 (3)
C4	0.5100 (3)	0.76127 (15)	0.39418 (13)	0.0219 (3)
C5	0.3111 (3)	0.72874 (16)	0.46735 (13)	0.0244 (3)
C6	0.2268 (3)	0.62354 (17)	0.46533 (13)	0.0252 (3)
H6	0.0964	0.5954	0.5154	0.030*
C7	0.3399 (3)	0.56176 (15)	0.38791 (12)	0.0214 (3)
C8	0.4262 (3)	0.42809 (15)	0.28649 (12)	0.0221 (3)
C9	0.8457 (3)	0.73299 (16)	0.24263 (14)	0.0242 (3)
H9A	0.8171	0.8110	0.1782	0.036*
H9B	0.9253	0.6592	0.2159	0.036*
H9C	0.9372	0.7506	0.2863	0.036*
C10	0.1860 (3)	0.80420 (19)	0.54665 (16)	0.0341 (4)
H10A	0.0587	0.7619	0.5938	0.051*
H10B	0.1318	0.8943	0.5033	0.051*
H10C	0.2863	0.8054	0.5943	0.051*
C11	0.3854 (3)	0.31944 (16)	0.25548 (14)	0.0270 (3)
H11A	0.2470	0.3462	0.2240	0.041*
H11B	0.3713	0.2422	0.3224	0.041*
H11C	0.5108	0.2979	0.1995	0.041*
C12	0.6482 (3)	0.67448 (14)	0.03546 (12)	0.0198 (3)
C13	0.7999 (3)	0.75067 (15)	−0.04158 (12)	0.0225 (3)
H13	0.9557	0.7183	−0.0474	0.027*
C14	0.7230 (3)	0.87472 (16)	−0.11039 (14)	0.0275 (3)
C15	0.4952 (3)	0.92001 (17)	−0.09772 (15)	0.0329 (4)
H15	0.4411	1.0057	−0.1425	0.039*
C16	0.3449 (3)	0.84324 (19)	−0.02136 (15)	0.0337 (4)
H16	0.1893	0.8765	−0.0144	0.040*
C17	0.4195 (3)	0.71802 (17)	0.04509 (14)	0.0272 (3)
H17	0.3168	0.6635	0.0959	0.033*
C18	0.8835 (4)	0.9564 (2)	−0.19860 (17)	0.0443 (5)
H18A	0.8480	0.9733	−0.2729	0.066*
H18B	1.0366	0.9092	−0.1953	0.066*
H18C	0.8703	1.0399	−0.1850	0.066*

	U11	U22	U33	U12	U13	U23
Br1	0.04364 (12)	0.02725 (10)	0.03175 (10)	−0.01115 (8)	−0.00252 (8)	−0.01557 (7)
S1	0.02068 (18)	0.01787 (17)	0.02010 (17)	−0.00149 (13)	−0.00020 (13)	−0.00790 (13)
O1	0.0248 (6)	0.0267 (6)	0.0223 (5)	−0.0103 (5)	0.0007 (4)	−0.0087 (4)
O2	0.0194 (5)	0.0287 (6)	0.0292 (6)	0.0009 (4)	−0.0019 (4)	−0.0109 (5)
C1	0.0212 (7)	0.0183 (6)	0.0185 (6)	−0.0026 (5)	−0.0023 (5)	−0.0058 (5)
C2	0.0199 (7)	0.0189 (7)	0.0174 (6)	−0.0019 (5)	−0.0029 (5)	−0.0054 (5)
C3	0.0205 (7)	0.0181 (6)	0.0187 (6)	−0.0028 (5)	−0.0033 (5)	−0.0047 (5)
C4	0.0260 (8)	0.0195 (7)	0.0216 (7)	−0.0031 (6)	−0.0054 (6)	−0.0076 (6)
C5	0.0247 (8)	0.0268 (8)	0.0220 (7)	0.0008 (6)	−0.0034 (6)	−0.0113 (6)
C6	0.0215 (7)	0.0319 (8)	0.0213 (7)	−0.0058 (6)	0.0009 (6)	−0.0093 (6)
C7	0.0226 (7)	0.0215 (7)	0.0199 (7)	−0.0058 (6)	−0.0030 (6)	−0.0054 (5)
C8	0.0253 (8)	0.0212 (7)	0.0190 (7)	−0.0041 (6)	−0.0039 (6)	−0.0052 (5)
C9	0.0231 (7)	0.0237 (7)	0.0269 (7)	−0.0071 (6)	0.0008 (6)	−0.0106 (6)
C10	0.0325 (9)	0.0390 (10)	0.0318 (9)	0.0002 (8)	0.0010 (7)	−0.0204 (8)
C11	0.0324 (9)	0.0236 (8)	0.0282 (8)	−0.0094 (7)	−0.0055 (7)	−0.0085 (6)
C12	0.0223 (7)	0.0191 (7)	0.0180 (6)	−0.0024 (6)	−0.0027 (5)	−0.0069 (5)
C13	0.0242 (8)	0.0235 (7)	0.0213 (7)	−0.0064 (6)	−0.0022 (6)	−0.0084 (6)
C14	0.0363 (9)	0.0243 (8)	0.0239 (7)	−0.0107 (7)	−0.0056 (7)	−0.0061 (6)
C15	0.0436 (11)	0.0230 (8)	0.0299 (8)	0.0011 (7)	−0.0140 (8)	−0.0047 (6)
C16	0.0266 (9)	0.0370 (10)	0.0324 (9)	0.0061 (7)	−0.0082 (7)	−0.0097 (7)
C17	0.0226 (8)	0.0304 (8)	0.0253 (8)	−0.0026 (6)	−0.0018 (6)	−0.0071 (6)
C18	0.0531 (13)	0.0348 (10)	0.0388 (10)	−0.0213 (9)	−0.0083 (9)	0.0051 (8)

Br1—C4	1.9073 (15)	C9—H9C	0.9800
S1—O2	1.4934 (12)	C10—H10A	0.9800
S1—C1	1.7619 (15)	C10—H10B	0.9800
S1—C12	1.8024 (15)	C10—H10C	0.9800
S1—O2i	3.1527 (12)	C11—H11A	0.9800
O1—C8	1.3694 (19)	C11—H11B	0.9800
O1—C7	1.3770 (18)	C11—H11C	0.9800
C1—C8	1.361 (2)	C12—C13	1.387 (2)
C1—C2	1.457 (2)	C12—C17	1.387 (2)
C2—C7	1.393 (2)	C13—C14	1.392 (2)
C2—C3	1.401 (2)	C13—H13	0.9500
C3—C4	1.393 (2)	C14—C15	1.385 (3)
C3—C9	1.508 (2)	C14—C18	1.505 (2)
C4—C5	1.405 (2)	C15—C16	1.381 (3)
C5—C6	1.390 (2)	C15—H15	0.9500
C5—C10	1.510 (2)	C16—C17	1.386 (2)
C6—C7	1.375 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.479 (2)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
O2—S1—C1	111.08 (7)	C5—C10—H10A	109.5
O2—S1—C12	106.70 (7)	C5—C10—H10B	109.5
C1—S1—C12	96.91 (7)	H10A—C10—H10B	109.5
O2—S1—O2i	78.25 (6)	C5—C10—H10C	109.5
C1—S1—O2i	169.73 (6)	H10A—C10—H10C	109.5
C12—S1—O2i	83.97 (5)	H10B—C10—H10C	109.5
C8—O1—C7	106.60 (12)	C8—C11—H11A	109.5
C8—C1—C2	107.12 (13)	C8—C11—H11B	109.5
C8—C1—S1	118.68 (12)	H11A—C11—H11B	109.5
C2—C1—S1	133.04 (11)	C8—C11—H11C	109.5
C7—C2—C3	119.45 (14)	H11A—C11—H11C	109.5
C7—C2—C1	104.27 (13)	H11B—C11—H11C	109.5
C3—C2—C1	136.25 (14)	C13—C12—C17	121.63 (14)
C4—C3—C2	115.39 (14)	C13—C12—S1	117.57 (12)
C4—C3—C9	123.20 (13)	C17—C12—S1	120.62 (12)
C2—C3—C9	121.37 (13)	C12—C13—C14	119.71 (15)
C3—C4—C5	125.00 (14)	C12—C13—H13	120.1
C3—C4—Br1	117.82 (11)	C14—C13—H13	120.1
C5—C4—Br1	117.18 (11)	C15—C14—C13	118.57 (16)
C6—C5—C4	118.23 (14)	C15—C14—C18	120.73 (16)
C6—C5—C10	119.23 (15)	C13—C14—C18	120.69 (17)
C4—C5—C10	122.54 (15)	C16—C15—C14	121.38 (16)
C7—C6—C5	117.29 (14)	C16—C15—H15	119.3
C7—C6—H6	121.4	C14—C15—H15	119.3
C5—C6—H6	121.4	C15—C16—C17	120.44 (17)
C6—C7—O1	124.56 (14)	C15—C16—H16	119.8
C6—C7—C2	124.45 (14)	C17—C16—H16	119.8
O1—C7—C2	110.98 (13)	C16—C17—C12	118.19 (16)
C1—C8—O1	110.99 (13)	C16—C17—H17	120.9
C1—C8—C11	133.49 (15)	C12—C17—H17	120.9
O1—C8—C11	115.50 (14)	C14—C18—H18A	109.5
C3—C9—H9A	109.5	C14—C18—H18B	109.5
C3—C9—H9B	109.5	H18A—C18—H18B	109.5
H9A—C9—H9B	109.5	C14—C18—H18C	109.5
C3—C9—H9C	109.5	H18A—C18—H18C	109.5
H9A—C9—H9C	109.5	H18B—C18—H18C	109.5
H9B—C9—H9C	109.5
O2—S1—C1—C8	−136.06 (12)	C8—O1—C7—C2	−1.35 (16)
C12—S1—C1—C8	113.02 (13)	C3—C2—C7—C6	4.5 (2)
O2—S1—C1—C2	58.06 (17)	C1—C2—C7—C6	−177.07 (15)
C12—S1—C1—C2	−52.85 (16)	C3—C2—C7—O1	−176.74 (13)
C8—C1—C2—C7	−1.46 (16)	C1—C2—C7—O1	1.73 (16)
S1—C1—C2—C7	165.60 (13)	C2—C1—C8—O1	0.71 (17)
C8—C1—C2—C3	176.62 (17)	S1—C1—C8—O1	−168.54 (10)
S1—C1—C2—C3	−16.3 (3)	C2—C1—C8—C11	179.18 (16)
C7—C2—C3—C4	−4.3 (2)	S1—C1—C8—C11	9.9 (2)
C1—C2—C3—C4	177.88 (16)	C7—O1—C8—C1	0.35 (17)
C7—C2—C3—C9	173.53 (14)	C7—O1—C8—C11	−178.42 (13)
C1—C2—C3—C9	−4.3 (3)	O2—S1—C12—C13	25.77 (14)
C2—C3—C4—C5	0.9 (2)	C1—S1—C12—C13	140.27 (12)
C9—C3—C4—C5	−176.88 (15)	O2—S1—C12—C17	−158.95 (13)
C2—C3—C4—Br1	−179.31 (10)	C1—S1—C12—C17	−44.45 (14)
C9—C3—C4—Br1	2.9 (2)	C17—C12—C13—C14	0.8 (2)
C3—C4—C5—C6	2.7 (2)	S1—C12—C13—C14	176.07 (12)
Br1—C4—C5—C6	−177.13 (12)	C12—C13—C14—C15	1.6 (2)
C3—C4—C5—C10	−176.77 (15)	C12—C13—C14—C18	−176.88 (16)
Br1—C4—C5—C10	3.4 (2)	C13—C14—C15—C16	−2.1 (3)
C4—C5—C6—C7	−2.7 (2)	C18—C14—C15—C16	176.39 (18)
C10—C5—C6—C7	176.80 (15)	C14—C15—C16—C17	0.1 (3)
C5—C6—C7—O1	−179.40 (14)	C15—C16—C17—C12	2.3 (3)
C5—C6—C7—C2	−0.8 (2)	C13—C12—C17—C16	−2.8 (2)
C8—O1—C7—C6	177.44 (15)	S1—C12—C17—C16	−177.85 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ii	0.95	2.50	3.4478 (19)	172
C11—H11A···O2iii	0.98	2.36	3.244 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.50	3.4478 (19)	172
C11—H11A⋯O2ii	0.98	2.36	3.244 (2)	150

Symmetry codes: (i) ; (ii) .