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

In the title compound, C17H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.003 (2) Å] of the benzo-furan ring system and the mean plane [r.m.s. deviation = 0.006 (2) Å] of the 4-bromo-phenyl ring is 83.09 (7)°. In the crystal, weak C-H⋯π inter-actions are observed.

Related literature

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

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Monoclinic,

a = 20.0084 (8) Å

b = 7.1890 (3) Å

c = 10.7804 (4) Å

β = 101.478 (2)°

V = 1519.65 (10) Å3

Z = 4

Mo Kα radiation

μ = 2.84 mm−1

T = 173 K

0.37 × 0.26 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.425, T max = 0.746

26485 measured reflections

3791 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.05

3791 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.86 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/S1600536813017753/nc2313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017753/nc2313Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017753/nc2313Isup3.cml

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

C17H15BrO2S	F(000) = 736
Mr = 363.26	Dx = 1.588 Mg m−3
Monoclinic, P21/c	Melting point = 446–447 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 20.0084 (8) Å	Cell parameters from 6275 reflections
b = 7.1890 (3) Å	θ = 3.1–27.2°
c = 10.7804 (4) Å	µ = 2.84 mm−1
β = 101.478 (2)°	T = 173 K
V = 1519.65 (10) Å3	Block, colourless
Z = 4	0.37 × 0.26 × 0.05 mm

Bruker SMART APEXII CCD diffractometer	3791 independent reflections
Radiation source: rotating anode	2928 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.071
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −7→9
Tmin = 0.425, Tmax = 0.746	l = −14→14
26485 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.8553P] where P = (Fo2 + 2Fc2)/3
3791 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.86 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	0.471187 (16)	0.90385 (6)	0.33352 (3)	0.06164 (16)
S1	0.30484 (3)	0.38470 (9)	0.64879 (6)	0.02963 (16)
O1	0.11729 (8)	0.5558 (2)	0.62907 (13)	0.0245 (4)
O2	0.30702 (10)	0.1917 (3)	0.5990 (2)	0.0456 (5)
C1	0.22159 (11)	0.4684 (3)	0.60389 (19)	0.0230 (5)
C2	0.17882 (11)	0.4857 (3)	0.47877 (19)	0.0218 (4)
C3	0.18654 (12)	0.4633 (3)	0.35339 (19)	0.0240 (5)
H3	0.2292	0.4267	0.3354	0.029*
C4	0.13130 (12)	0.4951 (3)	0.25574 (19)	0.0242 (5)
C5	0.06756 (12)	0.5501 (3)	0.28199 (19)	0.0230 (4)
C6	0.06000 (11)	0.5739 (3)	0.40622 (19)	0.0230 (5)
H6	0.0178	0.6124	0.4253	0.028*
C7	0.11582 (11)	0.5398 (3)	0.50083 (18)	0.0220 (4)
C8	0.18216 (12)	0.5111 (3)	0.68885 (19)	0.0245 (5)
C9	0.13935 (14)	0.4700 (4)	0.1205 (2)	0.0327 (6)
H9A	0.1875	0.4477	0.1187	0.049*
H9B	0.1238	0.5826	0.0720	0.049*
H9C	0.1120	0.3635	0.0831	0.049*
C10	0.00712 (13)	0.5824 (4)	0.1766 (2)	0.0302 (5)
H10A	−0.0325	0.6167	0.2123	0.045*
H10B	−0.0030	0.4683	0.1265	0.045*
H10C	0.0174	0.6831	0.1221	0.045*
C11	0.19543 (14)	0.5183 (4)	0.82940 (19)	0.0313 (5)
H11A	0.2425	0.4795	0.8633	0.047*
H11B	0.1639	0.4344	0.8607	0.047*
H11C	0.1887	0.6456	0.8569	0.047*
C12	0.34419 (11)	0.5327 (4)	0.5498 (2)	0.0270 (5)
C13	0.38253 (14)	0.4501 (4)	0.4718 (3)	0.0407 (7)
H13	0.3838	0.3186	0.4644	0.049*
C14	0.41911 (14)	0.5619 (5)	0.4046 (3)	0.0469 (8)
H14	0.4451	0.5078	0.3492	0.056*
C15	0.41750 (12)	0.7519 (5)	0.4186 (2)	0.0379 (7)
C16	0.37837 (13)	0.8355 (4)	0.4953 (2)	0.0354 (6)
H16	0.3768	0.9671	0.5022	0.042*
C17	0.34162 (12)	0.7238 (4)	0.5615 (2)	0.0302 (5)
H17	0.3146	0.7782	0.6151	0.036*

	U11	U22	U33	U12	U13	U23
Br1	0.04327 (19)	0.1047 (4)	0.03699 (18)	−0.03020 (17)	0.00810 (13)	0.01789 (15)
S1	0.0254 (3)	0.0305 (4)	0.0322 (3)	0.0010 (2)	0.0038 (2)	0.0074 (2)
O1	0.0278 (8)	0.0287 (10)	0.0182 (7)	0.0021 (7)	0.0074 (6)	0.0007 (6)
O2	0.0385 (10)	0.0257 (12)	0.0747 (14)	0.0058 (9)	0.0161 (9)	0.0068 (9)
C1	0.0266 (11)	0.0214 (13)	0.0213 (10)	−0.0025 (9)	0.0052 (8)	0.0014 (8)
C2	0.0257 (10)	0.0181 (12)	0.0222 (10)	−0.0018 (9)	0.0059 (8)	0.0016 (8)
C3	0.0291 (11)	0.0215 (13)	0.0231 (10)	0.0034 (10)	0.0094 (8)	0.0024 (8)
C4	0.0351 (12)	0.0189 (12)	0.0199 (9)	0.0002 (10)	0.0088 (8)	0.0002 (8)
C5	0.0286 (11)	0.0179 (12)	0.0220 (10)	−0.0026 (9)	0.0039 (8)	0.0016 (7)
C6	0.0242 (10)	0.0223 (13)	0.0234 (10)	−0.0005 (9)	0.0067 (8)	0.0009 (8)
C7	0.0294 (11)	0.0198 (13)	0.0188 (9)	−0.0017 (9)	0.0094 (8)	0.0007 (7)
C8	0.0299 (11)	0.0223 (13)	0.0208 (10)	−0.0014 (10)	0.0042 (8)	0.0004 (8)
C9	0.0476 (14)	0.0308 (15)	0.0208 (10)	0.0117 (12)	0.0095 (10)	0.0008 (9)
C10	0.0330 (12)	0.0322 (15)	0.0234 (11)	−0.0006 (11)	0.0006 (9)	0.0014 (9)
C11	0.0427 (14)	0.0321 (15)	0.0186 (10)	0.0015 (12)	0.0052 (9)	−0.0006 (8)
C12	0.0225 (10)	0.0335 (15)	0.0242 (10)	−0.0014 (10)	0.0030 (8)	−0.0001 (9)
C13	0.0395 (15)	0.0385 (18)	0.0480 (15)	0.0000 (13)	0.0185 (12)	−0.0072 (12)
C14	0.0393 (16)	0.063 (2)	0.0438 (16)	−0.0047 (14)	0.0222 (13)	−0.0116 (13)
C15	0.0257 (12)	0.059 (2)	0.0288 (12)	−0.0102 (12)	0.0057 (9)	0.0066 (11)
C16	0.0296 (12)	0.0378 (16)	0.0376 (13)	−0.0048 (12)	0.0040 (10)	0.0070 (11)
C17	0.0272 (11)	0.0325 (15)	0.0322 (11)	−0.0010 (10)	0.0086 (9)	0.0005 (9)

Br1—C15	1.892 (3)	C9—H9A	0.9800
S1—O2	1.492 (2)	C9—H9B	0.9800
S1—C1	1.746 (2)	C9—H9C	0.9800
S1—C12	1.796 (2)	C10—H10A	0.9800
O1—C8	1.368 (3)	C10—H10B	0.9800
O1—C7	1.382 (2)	C10—H10C	0.9800
C1—C8	1.358 (3)	C11—H11A	0.9800
C1—C2	1.452 (3)	C11—H11B	0.9800
C2—C7	1.384 (3)	C11—H11C	0.9800
C2—C3	1.400 (3)	C12—C13	1.380 (3)
C3—C4	1.385 (3)	C12—C17	1.382 (4)
C3—H3	0.9500	C13—C14	1.385 (4)
C4—C5	1.417 (3)	C13—H13	0.9500
C4—C9	1.509 (3)	C14—C15	1.375 (5)
C5—C6	1.388 (3)	C14—H14	0.9500
C5—C10	1.504 (3)	C15—C16	1.384 (4)
C6—C7	1.376 (3)	C16—C17	1.380 (3)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.486 (3)	C17—H17	0.9500
O2—S1—C1	108.38 (11)	H9A—C9—H9C	109.5
O2—S1—C12	106.81 (11)	H9B—C9—H9C	109.5
C1—S1—C12	97.93 (11)	C5—C10—H10A	109.5
C8—O1—C7	106.33 (16)	C5—C10—H10B	109.5
C8—C1—C2	107.05 (19)	H10A—C10—H10B	109.5
C8—C1—S1	122.76 (16)	C5—C10—H10C	109.5
C2—C1—S1	129.82 (16)	H10A—C10—H10C	109.5
C7—C2—C3	118.5 (2)	H10B—C10—H10C	109.5
C7—C2—C1	104.66 (18)	C8—C11—H11A	109.5
C3—C2—C1	136.8 (2)	C8—C11—H11B	109.5
C4—C3—C2	119.4 (2)	H11A—C11—H11B	109.5
C4—C3—H3	120.3	C8—C11—H11C	109.5
C2—C3—H3	120.3	H11A—C11—H11C	109.5
C3—C4—C5	120.54 (18)	H11B—C11—H11C	109.5
C3—C4—C9	119.5 (2)	C13—C12—C17	121.3 (2)
C5—C4—C9	120.0 (2)	C13—C12—S1	118.0 (2)
C6—C5—C4	120.2 (2)	C17—C12—S1	120.38 (17)
C6—C5—C10	119.0 (2)	C12—C13—C14	119.0 (3)
C4—C5—C10	120.84 (19)	C12—C13—H13	120.5
C7—C6—C5	117.7 (2)	C14—C13—H13	120.5
C7—C6—H6	121.1	C15—C14—C13	119.5 (2)
C5—C6—H6	121.1	C15—C14—H14	120.3
C6—C7—O1	125.39 (19)	C13—C14—H14	120.3
C6—C7—C2	123.72 (19)	C14—C15—C16	121.7 (2)
O1—C7—C2	110.88 (19)	C14—C15—Br1	119.5 (2)
C1—C8—O1	111.08 (18)	C16—C15—Br1	118.8 (2)
C1—C8—C11	133.3 (2)	C17—C16—C15	118.7 (3)
O1—C8—C11	115.63 (19)	C17—C16—H16	120.7
C4—C9—H9A	109.5	C15—C16—H16	120.7
C4—C9—H9B	109.5	C16—C17—C12	119.8 (2)
H9A—C9—H9B	109.5	C16—C17—H17	120.1
C4—C9—H9C	109.5	C12—C17—H17	120.1
O2—S1—C1—C8	115.6 (2)	C1—C2—C7—C6	179.3 (2)
C12—S1—C1—C8	−133.6 (2)	C3—C2—C7—O1	−179.8 (2)
O2—S1—C1—C2	−56.5 (3)	C1—C2—C7—O1	−0.2 (3)
C12—S1—C1—C2	54.3 (2)	C2—C1—C8—O1	−0.3 (3)
C8—C1—C2—C7	0.3 (3)	S1—C1—C8—O1	−174.01 (17)
S1—C1—C2—C7	173.37 (19)	C2—C1—C8—C11	179.6 (3)
C8—C1—C2—C3	179.8 (3)	S1—C1—C8—C11	6.0 (4)
S1—C1—C2—C3	−7.1 (4)	C7—O1—C8—C1	0.2 (3)
C7—C2—C3—C4	−0.2 (3)	C7—O1—C8—C11	−179.7 (2)
C1—C2—C3—C4	−179.7 (3)	O2—S1—C12—C13	−15.3 (2)
C2—C3—C4—C5	0.1 (4)	C1—S1—C12—C13	−127.3 (2)
C2—C3—C4—C9	−179.7 (2)	O2—S1—C12—C17	171.18 (18)
C3—C4—C5—C6	0.4 (4)	C1—S1—C12—C17	59.2 (2)
C9—C4—C5—C6	−179.8 (2)	C17—C12—C13—C14	0.1 (4)
C3—C4—C5—C10	−179.2 (2)	S1—C12—C13—C14	−173.3 (2)
C9—C4—C5—C10	0.6 (3)	C12—C13—C14—C15	1.2 (4)
C4—C5—C6—C7	−0.9 (3)	C13—C14—C15—C16	−2.2 (4)
C10—C5—C6—C7	178.7 (2)	C13—C14—C15—Br1	176.7 (2)
C5—C6—C7—O1	−179.7 (2)	C14—C15—C16—C17	1.7 (4)
C5—C6—C7—C2	0.8 (4)	Br1—C15—C16—C17	−177.17 (18)
C8—O1—C7—C6	−179.5 (2)	C15—C16—C17—C12	−0.4 (4)
C8—O1—C7—C2	0.0 (3)	C13—C12—C17—C16	−0.5 (4)
C3—C2—C7—C6	−0.3 (4)	S1—C12—C17—C16	172.77 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cg1i	0.98	2.89	3.537 (4)	124
C11—H11C···Cg2ii	0.98	2.78	3.714 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯Cg1i	0.98	2.89	3.537 (4)	124
C11—H11C⋯Cg2ii	0.98	2.78	3.714 (4)	159

Symmetry codes: (i) ; (ii) .