5-Bromo-3-ethyl-sulfinyl-7-methyl-2-(4-methyl-phen-yl)-1-benzo-furan.

In the title compound, C18H17BrO2S, the dihedral angle between the mean planes of the benzo-furan and 4-methyl-phenyl rings is 14.54 (5)°. In the crystal, mol-ecules are linked via pairs of π-π inter-actions between the benzene and 4-methyl-phenyl rings, with centroid-centroid distances of 3.811 (3) and 3.755 (3) Å. A similar inter-action is found between the furan and 4-methyl-phenyl rings, with a centroid-centroid distance of 3.866 (3) Å between neighbouring mol-ecules. The mol-ecules are stacked along the a-axis direction. In addition, a short Br⋯O contact distance of 3.128 (2) Å is observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶). For π–π stacking in metal complexes with aromatic nitro­gen ligands, see: Janiak (2000 ▶).

Experimental

Crystal data

C18H17BrO2S

M = 377.29

Triclinic,

a = 7.3921 (2) Å

b = 10.2909 (3) Å

c = 11.8701 (3) Å

α = 68.867 (1)°

β = 89.146 (1)°

γ = 71.361 (1)°

V = 792.91 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.73 mm−1

T = 173 K

0.37 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.535, T max = 0.746

13645 measured reflections

3457 independent reflections

3145 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.04

3457 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.47 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/S1600536814005844/fj2667sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005844/fj2667Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005844/fj2667Isup3.cml

CCDC reference: 992016

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

C18H17BrO2S	Z = 2
Mr = 377.29	F(000) = 384
Triclinic, P1	Dx = 1.580 Mg m−3
Hall symbol: -P 1	Melting point = 420–419 K
a = 7.3921 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2909 (3) Å	Cell parameters from 8443 reflections
c = 11.8701 (3) Å	θ = 2.3–28.3°
α = 68.867 (1)°	µ = 2.73 mm−1
β = 89.146 (1)°	T = 173 K
γ = 71.361 (1)°	Block, colourless
V = 792.91 (4) Å3	0.37 × 0.25 × 0.22 mm

Bruker SMART APEXII CCD diffractometer	3457 independent reflections
Radiation source: rotating anode	3145 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→13
Tmin = 0.535, Tmax = 0.746	l = −15→15
13645 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.3263P] where P = (Fo2 + 2Fc2)/3
3457 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.47 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	0.99213 (3)	0.28117 (2)	1.076443 (17)	0.03316 (9)
S1	0.64111 (7)	0.80626 (5)	0.58929 (4)	0.02572 (12)
O1	0.80567 (19)	0.41973 (14)	0.55125 (12)	0.0243 (3)
O2	0.7922 (2)	0.81341 (17)	0.66688 (15)	0.0380 (4)
C1	0.7074 (3)	0.6207 (2)	0.60113 (17)	0.0226 (4)
C2	0.7941 (3)	0.4927 (2)	0.71109 (17)	0.0232 (4)
C3	0.8306 (3)	0.4680 (2)	0.83342 (17)	0.0251 (4)
H3	0.7908	0.5463	0.8627	0.030*
C4	0.9278 (3)	0.3240 (2)	0.90957 (17)	0.0262 (4)
C5	0.9886 (3)	0.2066 (2)	0.86941 (18)	0.0269 (4)
H5	1.0556	0.1097	0.9262	0.032*
C6	0.9532 (3)	0.2284 (2)	0.74878 (18)	0.0252 (4)
C7	0.8532 (3)	0.3738 (2)	0.67370 (17)	0.0231 (4)
C8	0.7173 (3)	0.5711 (2)	0.50770 (17)	0.0231 (4)
C9	1.0208 (3)	0.1073 (2)	0.70051 (19)	0.0314 (4)
H9A	0.9108	0.0820	0.6816	0.047*
H9B	1.1140	0.0198	0.7618	0.047*
H9C	1.0816	0.1406	0.6266	0.047*
C10	0.6536 (3)	0.6380 (2)	0.37788 (17)	0.0236 (4)
C11	0.5193 (3)	0.7799 (2)	0.32352 (18)	0.0273 (4)
H11	0.4689	0.8370	0.3715	0.033*
C12	0.4589 (3)	0.8382 (2)	0.20024 (18)	0.0302 (4)
H12	0.3686	0.9355	0.1646	0.036*
C13	0.5276 (3)	0.7571 (2)	0.12746 (18)	0.0305 (4)
C14	0.6616 (3)	0.6152 (2)	0.18236 (19)	0.0309 (4)
H14	0.7102	0.5578	0.1345	0.037*
C15	0.7248 (3)	0.5567 (2)	0.30458 (18)	0.0273 (4)
H15	0.8175	0.4604	0.3395	0.033*
C16	0.4606 (3)	0.8183 (3)	−0.00608 (19)	0.0407 (5)
H16A	0.3793	0.7662	−0.0213	0.061*
H16B	0.5721	0.8047	−0.0517	0.061*
H16C	0.3865	0.9241	−0.0324	0.061*
C17	0.4326 (3)	0.8128 (2)	0.67180 (19)	0.0314 (5)
H17A	0.4619	0.7210	0.7452	0.038*
H17B	0.4015	0.8974	0.6986	0.038*
C18	0.2603 (3)	0.8292 (2)	0.5931 (2)	0.0336 (5)
H18A	0.2232	0.9248	0.5247	0.050*
H18B	0.1527	0.8241	0.6418	0.050*
H18C	0.2939	0.7492	0.5621	0.050*

	U11	U22	U33	U12	U13	U23
Br1	0.03870 (14)	0.03266 (13)	0.02694 (12)	−0.01276 (9)	−0.00261 (8)	−0.00897 (9)
S1	0.0267 (2)	0.0211 (2)	0.0298 (2)	−0.00751 (18)	0.00028 (19)	−0.01041 (18)
O1	0.0245 (7)	0.0218 (6)	0.0263 (6)	−0.0059 (5)	0.0029 (5)	−0.0104 (5)
O2	0.0368 (9)	0.0364 (8)	0.0449 (9)	−0.0163 (7)	−0.0060 (7)	−0.0162 (7)
C1	0.0182 (9)	0.0212 (9)	0.0288 (9)	−0.0062 (7)	0.0028 (7)	−0.0103 (7)
C2	0.0171 (9)	0.0233 (9)	0.0291 (9)	−0.0067 (7)	0.0035 (7)	−0.0098 (7)
C3	0.0231 (9)	0.0256 (9)	0.0287 (9)	−0.0088 (7)	0.0026 (7)	−0.0122 (8)
C4	0.0240 (10)	0.0307 (10)	0.0258 (9)	−0.0109 (8)	0.0015 (7)	−0.0111 (8)
C5	0.0211 (9)	0.0237 (9)	0.0331 (10)	−0.0070 (7)	0.0004 (8)	−0.0079 (8)
C6	0.0184 (9)	0.0244 (9)	0.0332 (10)	−0.0067 (7)	0.0031 (7)	−0.0118 (8)
C7	0.0194 (9)	0.0250 (9)	0.0273 (9)	−0.0083 (7)	0.0038 (7)	−0.0118 (7)
C8	0.0173 (9)	0.0212 (9)	0.0308 (9)	−0.0064 (7)	0.0045 (7)	−0.0101 (7)
C9	0.0299 (11)	0.0227 (9)	0.0382 (11)	−0.0026 (8)	0.0025 (8)	−0.0129 (8)
C10	0.0212 (9)	0.0274 (9)	0.0260 (9)	−0.0123 (7)	0.0048 (7)	−0.0107 (7)
C11	0.0239 (10)	0.0287 (10)	0.0299 (10)	−0.0085 (8)	0.0045 (8)	−0.0122 (8)
C12	0.0222 (10)	0.0313 (10)	0.0327 (10)	−0.0086 (8)	0.0020 (8)	−0.0076 (8)
C13	0.0260 (10)	0.0408 (12)	0.0272 (10)	−0.0178 (9)	0.0049 (8)	−0.0102 (8)
C14	0.0320 (11)	0.0383 (11)	0.0311 (10)	−0.0180 (9)	0.0102 (8)	−0.0176 (9)
C15	0.0279 (10)	0.0259 (9)	0.0310 (10)	−0.0118 (8)	0.0069 (8)	−0.0118 (8)
C16	0.0367 (12)	0.0562 (15)	0.0283 (10)	−0.0197 (11)	0.0034 (9)	−0.0112 (10)
C17	0.0298 (11)	0.0311 (10)	0.0316 (10)	−0.0036 (8)	0.0054 (8)	−0.0156 (8)
C18	0.0290 (11)	0.0328 (11)	0.0440 (12)	−0.0119 (9)	0.0085 (9)	−0.0189 (9)

Br1—C4	1.8996 (19)	C9—H9C	0.9800
Br1—O2i	3.1284 (15)	C10—C11	1.396 (3)
S1—O2	1.4943 (15)	C10—C15	1.401 (3)
S1—C1	1.7658 (19)	C11—C12	1.384 (3)
S1—C17	1.810 (2)	C11—H11	0.9500
O1—C7	1.369 (2)	C12—C13	1.392 (3)
O1—C8	1.378 (2)	C12—H12	0.9500
C1—C8	1.370 (3)	C13—C14	1.395 (3)
C1—C2	1.447 (3)	C13—C16	1.503 (3)
C2—C7	1.389 (3)	C14—C15	1.377 (3)
C2—C3	1.396 (3)	C14—H14	0.9500
C3—C4	1.379 (3)	C15—H15	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.397 (3)	C16—H16B	0.9800
C5—C6	1.382 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—C18	1.519 (3)
C6—C7	1.390 (3)	C17—H17A	0.9900
C6—C9	1.496 (3)	C17—H17B	0.9900
C8—C10	1.456 (3)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C4—Br1—O2i	164.97 (7)	C11—C10—C8	122.23 (17)
O2—S1—C1	106.64 (9)	C15—C10—C8	119.43 (17)
O2—S1—C17	106.82 (10)	C12—C11—C10	120.49 (18)
C1—S1—C17	98.32 (10)	C12—C11—H11	119.8
C7—O1—C8	107.13 (14)	C10—C11—H11	119.8
C8—C1—C2	107.24 (16)	C11—C12—C13	121.33 (19)
C8—C1—S1	127.11 (15)	C11—C12—H12	119.3
C2—C1—S1	124.84 (14)	C13—C12—H12	119.3
C7—C2—C3	119.30 (17)	C12—C13—C14	117.90 (18)
C7—C2—C1	104.87 (16)	C12—C13—C16	121.8 (2)
C3—C2—C1	135.80 (17)	C14—C13—C16	120.3 (2)
C4—C3—C2	116.46 (17)	C15—C14—C13	121.33 (19)
C4—C3—H3	121.8	C15—C14—H14	119.3
C2—C3—H3	121.8	C13—C14—H14	119.3
C3—C4—C5	123.18 (18)	C14—C15—C10	120.62 (18)
C3—C4—Br1	119.36 (15)	C14—C15—H15	119.7
C5—C4—Br1	117.42 (14)	C10—C15—H15	119.7
C6—C5—C4	121.36 (17)	C13—C16—H16A	109.5
C6—C5—H5	119.3	C13—C16—H16B	109.5
C4—C5—H5	119.3	H16A—C16—H16B	109.5
C5—C6—C7	114.64 (17)	C13—C16—H16C	109.5
C5—C6—C9	123.41 (17)	H16A—C16—H16C	109.5
C7—C6—C9	121.92 (18)	H16B—C16—H16C	109.5
O1—C7—C2	110.82 (16)	C18—C17—S1	111.08 (15)
O1—C7—C6	124.11 (16)	C18—C17—H17A	109.4
C2—C7—C6	125.04 (18)	S1—C17—H17A	109.4
C1—C8—O1	109.93 (16)	C18—C17—H17B	109.4
C1—C8—C10	135.84 (17)	S1—C17—H17B	109.4
O1—C8—C10	114.21 (16)	H17A—C17—H17B	108.0
C6—C9—H9A	109.5	C17—C18—H18A	109.5
C6—C9—H9B	109.5	C17—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C6—C9—H9C	109.5	C17—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C11—C10—C15	118.32 (17)
O2—S1—C1—C8	−130.72 (18)	C5—C6—C7—C2	1.6 (3)
C17—S1—C1—C8	118.85 (18)	C9—C6—C7—C2	−176.86 (19)
O2—S1—C1—C2	37.58 (19)	C2—C1—C8—O1	−0.3 (2)
C17—S1—C1—C2	−72.85 (18)	S1—C1—C8—O1	169.66 (13)
C8—C1—C2—C7	0.9 (2)	C2—C1—C8—C10	177.6 (2)
S1—C1—C2—C7	−169.35 (14)	S1—C1—C8—C10	−12.4 (3)
C8—C1—C2—C3	179.1 (2)	C7—O1—C8—C1	−0.4 (2)
S1—C1—C2—C3	8.8 (3)	C7—O1—C8—C10	−178.87 (16)
C7—C2—C3—C4	1.0 (3)	C1—C8—C10—C11	−15.2 (4)
C1—C2—C3—C4	−177.0 (2)	O1—C8—C10—C11	162.70 (17)
C2—C3—C4—C5	0.1 (3)	C1—C8—C10—C15	166.5 (2)
C2—C3—C4—Br1	177.69 (14)	O1—C8—C10—C15	−15.6 (3)
C3—C4—C5—C6	−0.4 (3)	C15—C10—C11—C12	−0.1 (3)
Br1—C4—C5—C6	−178.01 (15)	C8—C10—C11—C12	−178.39 (19)
C4—C5—C6—C7	−0.4 (3)	C10—C11—C12—C13	0.8 (3)
C4—C5—C6—C9	177.98 (19)	C11—C12—C13—C14	−0.7 (3)
C8—O1—C7—C2	1.0 (2)	C11—C12—C13—C16	179.0 (2)
C8—O1—C7—C6	−176.82 (18)	C12—C13—C14—C15	−0.2 (3)
C3—C2—C7—O1	−179.73 (16)	C16—C13—C14—C15	−179.9 (2)
C1—C2—C7—O1	−1.2 (2)	C13—C14—C15—C10	0.9 (3)
C3—C2—C7—C6	−1.9 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C2—C7—C6	176.64 (18)	C8—C10—C15—C14	177.56 (18)
C5—C6—C7—O1	179.12 (17)	O2—S1—C17—C18	171.58 (14)
C9—C6—C7—O1	0.7 (3)	C1—S1—C17—C18	−78.14 (16)