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

In the title compound, C17H15BrO2S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.004 (3) Å] and that of the 4-methyl-phenyl ring is 0.9 (2)°. In the crystal, mol-ecules are linked by C-H⋯O, C-H⋯π and Br⋯π [3.636 (2) Å] inter-actions, and by π-π inter-actions between the 4-methyl-phenyl and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.650 (2) Å], forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Monoclinic,

a = 5.0202 (3) Å

b = 25.0471 (12) Å

c = 12.2430 (6) Å

β = 100.340 (2)°

V = 1514.45 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.85 mm−1

T = 173 K

0.60 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.541, T max = 0.746

26373 measured reflections

3868 independent reflections

3104 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.06

3868 reflections

192 parameters

H-atom parameters constrained

Δρmax = 1.97 e Å−3

Δρmin = −0.83 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: SHELXS97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014470/ff2130sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014470/ff2130Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014470/ff2130Isup3.cml

CCDC reference: 1009166

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

C17H15BrO2S	F(000) = 736
Mr = 363.26	Dx = 1.593 Mg m−3
Monoclinic, P21/n	Melting point = 405–404 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.0202 (3) Å	Cell parameters from 7637 reflections
b = 25.0471 (12) Å	θ = 2.4–27.2°
c = 12.2430 (6) Å	µ = 2.85 mm−1
β = 100.340 (2)°	T = 173 K
V = 1514.45 (14) Å3	Block, colourless
Z = 4	0.60 × 0.14 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	3868 independent reflections
Radiation source: rotating anode	3104 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.058
Detector resolution: 10.0 pixels mm-1	θmax = 28.6°, θmin = 1.6°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −33→32
Tmin = 0.541, Tmax = 0.746	l = −16→16
26373 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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F2) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0648P)2 + 3.2187P] where P = (Fo2 + 2Fc2)/3
3868 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 1.97 e Å−3
0 restraints	Δρmin = −0.83 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	−0.00958 (8)	0.504511 (15)	0.82039 (3)	0.03501 (14)
S1	0.56805 (19)	0.35409 (3)	0.54542 (7)	0.0275 (2)
O1	0.8410 (5)	0.33583 (9)	0.86960 (18)	0.0242 (5)
O2	0.2710 (5)	0.36245 (11)	0.5189 (2)	0.0368 (6)
C1	0.6586 (7)	0.35476 (13)	0.6920 (3)	0.0229 (6)
C2	0.5277 (7)	0.38802 (13)	0.7630 (3)	0.0220 (6)
C3	0.3264 (7)	0.42681 (13)	0.7465 (3)	0.0258 (7)
H3	0.2391	0.4368	0.6740	0.031*
C4	0.2582 (7)	0.45033 (14)	0.8400 (3)	0.0266 (7)
C5	0.3796 (8)	0.43619 (15)	0.9476 (3)	0.0308 (8)
H5	0.3257	0.4532	1.0095	0.037*
C6	0.5790 (8)	0.39732 (15)	0.9641 (3)	0.0304 (8)
H6	0.6644	0.3869	1.0366	0.037*
C7	0.6481 (7)	0.37435 (13)	0.8707 (3)	0.0236 (7)
C8	0.8441 (7)	0.32375 (12)	0.7603 (2)	0.0208 (6)
C9	1.0400 (7)	0.28307 (13)	0.7429 (3)	0.0214 (6)
C10	1.0737 (7)	0.26723 (14)	0.6372 (3)	0.0253 (7)
H10	0.9656	0.2830	0.5738	0.030*
C11	1.2624 (7)	0.22877 (14)	0.6235 (3)	0.0272 (7)
H11	1.2815	0.2185	0.5505	0.033*
C12	1.4238 (7)	0.20489 (13)	0.7136 (3)	0.0250 (7)
C13	1.3907 (8)	0.22062 (15)	0.8188 (3)	0.0304 (8)
H13	1.4991	0.2045	0.8817	0.037*
C14	1.2043 (8)	0.25910 (14)	0.8346 (3)	0.0282 (7)
H14	1.1873	0.2694	0.9077	0.034*
C15	1.6299 (8)	0.16284 (15)	0.6982 (3)	0.0326 (8)
H15A	1.6346	0.1589	0.6189	0.049*
H15B	1.5796	0.1287	0.7280	0.049*
H15C	1.8091	0.1737	0.7376	0.049*
C16	0.7154 (8)	0.41740 (17)	0.5188 (3)	0.0343 (8)
H16A	0.6577	0.4453	0.5669	0.041*
H16B	0.9154	0.4149	0.5359	0.041*
C17	0.6247 (12)	0.4323 (2)	0.3983 (4)	0.0561 (13)
H17A	0.6821	0.4046	0.3510	0.084*
H17B	0.7062	0.4665	0.3835	0.084*
H17C	0.4270	0.4355	0.3822	0.084*

	U11	U22	U33	U12	U13	U23
Br1	0.0368 (2)	0.0297 (2)	0.0398 (2)	0.00835 (15)	0.01023 (16)	−0.00114 (15)
S1	0.0371 (5)	0.0267 (4)	0.0158 (4)	0.0048 (3)	−0.0031 (3)	−0.0012 (3)
O1	0.0324 (13)	0.0245 (12)	0.0153 (10)	0.0040 (9)	0.0033 (9)	−0.0006 (9)
O2	0.0348 (15)	0.0414 (16)	0.0300 (13)	−0.0066 (12)	−0.0056 (11)	0.0023 (12)
C1	0.0293 (17)	0.0211 (15)	0.0174 (14)	0.0008 (12)	0.0019 (12)	−0.0020 (12)
C2	0.0274 (16)	0.0197 (15)	0.0181 (14)	−0.0028 (12)	0.0021 (12)	−0.0032 (12)
C3	0.0268 (16)	0.0233 (16)	0.0257 (16)	−0.0008 (13)	0.0005 (13)	−0.0001 (13)
C4	0.0255 (16)	0.0254 (16)	0.0289 (17)	−0.0001 (13)	0.0051 (13)	−0.0010 (13)
C5	0.041 (2)	0.0293 (18)	0.0246 (17)	0.0030 (15)	0.0126 (15)	−0.0033 (14)
C6	0.040 (2)	0.0336 (19)	0.0170 (15)	0.0051 (15)	0.0032 (14)	−0.0002 (13)
C7	0.0298 (17)	0.0207 (15)	0.0195 (15)	0.0009 (13)	0.0022 (13)	−0.0016 (12)
C8	0.0287 (16)	0.0192 (14)	0.0134 (13)	−0.0034 (12)	0.0004 (11)	−0.0011 (11)
C9	0.0266 (16)	0.0194 (14)	0.0172 (14)	−0.0023 (12)	0.0015 (12)	0.0001 (11)
C10	0.0318 (17)	0.0253 (16)	0.0178 (15)	0.0022 (13)	0.0021 (13)	0.0045 (12)
C11	0.0346 (18)	0.0261 (17)	0.0215 (16)	−0.0004 (14)	0.0069 (13)	−0.0033 (13)
C12	0.0262 (16)	0.0223 (16)	0.0265 (17)	−0.0013 (13)	0.0048 (13)	−0.0014 (13)
C13	0.0362 (19)	0.0324 (19)	0.0203 (16)	0.0053 (15)	−0.0014 (14)	0.0046 (14)
C14	0.0377 (19)	0.0297 (18)	0.0164 (15)	0.0064 (14)	0.0024 (13)	−0.0010 (13)
C15	0.0338 (19)	0.0272 (18)	0.037 (2)	0.0016 (15)	0.0054 (15)	−0.0017 (15)
C16	0.0335 (19)	0.042 (2)	0.0271 (18)	−0.0040 (16)	0.0052 (15)	0.0024 (16)
C17	0.079 (4)	0.056 (3)	0.032 (2)	−0.011 (3)	0.004 (2)	0.016 (2)

Br1—C4	1.895 (4)	C9—C14	1.403 (4)
S1—O2	1.483 (3)	C10—C11	1.382 (5)
S1—C1	1.770 (3)	C10—H10	0.9500
S1—C16	1.804 (4)	C11—C12	1.383 (5)
O1—C7	1.369 (4)	C11—H11	0.9500
O1—C8	1.375 (4)	C12—C13	1.384 (5)
C1—C8	1.375 (4)	C12—C15	1.512 (5)
C1—C2	1.445 (4)	C13—C14	1.381 (5)
C2—C3	1.390 (5)	C13—H13	0.9500
C2—C7	1.391 (4)	C14—H14	0.9500
C3—C4	1.383 (5)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.395 (5)	C15—H15C	0.9800
C5—C6	1.385 (5)	C16—C17	1.511 (6)
C5—H5	0.9500	C16—H16A	0.9900
C6—C7	1.379 (5)	C16—H16B	0.9900
C6—H6	0.9500	C17—H17A	0.9800
C8—C9	1.458 (5)	C17—H17B	0.9800
C9—C10	1.392 (5)	C17—H17C	0.9800
O2—S1—C1	106.61 (16)	C11—C10—H10	119.6
O2—S1—C16	105.37 (17)	C9—C10—H10	119.6
C1—S1—C16	97.81 (17)	C10—C11—C12	121.4 (3)
C7—O1—C8	107.2 (2)	C10—C11—H11	119.3
C8—C1—C2	106.9 (3)	C12—C11—H11	119.3
C8—C1—S1	129.3 (3)	C11—C12—C13	117.9 (3)
C2—C1—S1	123.6 (2)	C11—C12—C15	121.2 (3)
C3—C2—C7	119.4 (3)	C13—C12—C15	120.9 (3)
C3—C2—C1	135.5 (3)	C14—C13—C12	121.8 (3)
C7—C2—C1	105.1 (3)	C14—C13—H13	119.1
C4—C3—C2	117.3 (3)	C12—C13—H13	119.1
C4—C3—H3	121.3	C13—C14—C9	120.1 (3)
C2—C3—H3	121.3	C13—C14—H14	119.9
C3—C4—C5	122.8 (3)	C9—C14—H14	119.9
C3—C4—Br1	118.4 (3)	C12—C15—H15A	109.5
C5—C4—Br1	118.7 (3)	C12—C15—H15B	109.5
C6—C5—C4	119.8 (3)	H15A—C15—H15B	109.5
C6—C5—H5	120.1	C12—C15—H15C	109.5
C4—C5—H5	120.1	H15A—C15—H15C	109.5
C7—C6—C5	117.1 (3)	H15B—C15—H15C	109.5
C7—C6—H6	121.5	C17—C16—S1	109.4 (3)
C5—C6—H6	121.5	C17—C16—H16A	109.8
O1—C7—C6	125.8 (3)	S1—C16—H16A	109.8
O1—C7—C2	110.6 (3)	C17—C16—H16B	109.8
C6—C7—C2	123.5 (3)	S1—C16—H16B	109.8
C1—C8—O1	110.1 (3)	H16A—C16—H16B	108.2
C1—C8—C9	135.0 (3)	C16—C17—H17A	109.5
O1—C8—C9	114.9 (3)	C16—C17—H17B	109.5
C10—C9—C14	118.0 (3)	H17A—C17—H17B	109.5
C10—C9—C8	122.2 (3)	C16—C17—H17C	109.5
C14—C9—C8	119.8 (3)	H17A—C17—H17C	109.5
C11—C10—C9	120.8 (3)	H17B—C17—H17C	109.5
O2—S1—C1—C8	141.1 (3)	C2—C1—C8—O1	−0.8 (4)
C16—S1—C1—C8	−110.3 (3)	S1—C1—C8—O1	−177.1 (2)
O2—S1—C1—C2	−34.7 (3)	C2—C1—C8—C9	−179.4 (3)
C16—S1—C1—C2	74.0 (3)	S1—C1—C8—C9	4.3 (6)
C8—C1—C2—C3	−179.6 (4)	C7—O1—C8—C1	1.0 (4)
S1—C1—C2—C3	−3.0 (6)	C7—O1—C8—C9	179.9 (3)
C8—C1—C2—C7	0.3 (4)	C1—C8—C9—C10	0.2 (6)
S1—C1—C2—C7	176.9 (3)	O1—C8—C9—C10	−178.3 (3)
C7—C2—C3—C4	0.6 (5)	C1—C8—C9—C14	179.4 (4)
C1—C2—C3—C4	−179.5 (4)	O1—C8—C9—C14	0.8 (4)
C2—C3—C4—C5	−0.9 (5)	C14—C9—C10—C11	0.4 (5)
C2—C3—C4—Br1	178.6 (2)	C8—C9—C10—C11	179.6 (3)
C3—C4—C5—C6	0.5 (6)	C9—C10—C11—C12	−0.1 (5)
Br1—C4—C5—C6	−179.0 (3)	C10—C11—C12—C13	0.1 (5)
C4—C5—C6—C7	0.2 (6)	C10—C11—C12—C15	180.0 (3)
C8—O1—C7—C6	179.5 (3)	C11—C12—C13—C14	−0.4 (6)
C8—O1—C7—C2	−0.8 (4)	C15—C12—C13—C14	179.8 (4)
C5—C6—C7—O1	179.3 (3)	C12—C13—C14—C9	0.7 (6)
C5—C6—C7—C2	−0.4 (6)	C10—C9—C14—C13	−0.7 (5)
C3—C2—C7—O1	−179.8 (3)	C8—C9—C14—C13	−179.9 (3)
C1—C2—C7—O1	0.3 (4)	O2—S1—C16—C17	−60.2 (4)
C3—C2—C7—C6	0.0 (5)	C1—S1—C16—C17	−169.9 (3)
C1—C2—C7—C6	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.58	3.507 (4)	164
C16—H16B···O2ii	0.99	2.26	3.110 (5)	144
C15—H15C···Cg1ii	0.99	2.78	3.607 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 4-methyl­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.58	3.507 (4)	164
C16—H16B⋯O2ii	0.99	2.26	3.110 (5)	144
C15—H15C⋯Cg1ii	0.99	2.78	3.607 (3)	143

Symmetry codes: (i) ; (ii) .