5-Bromo-2,7-dimethyl-3-(4-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C17H15BrO3S, the dihedral angle between the mean planes of the benzo-furan and 4-methyl-phenyl rings is 76.43 (5)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds into inversion dimers that are further linked by Br⋯Br [3.6517 (4) Å] contacts about inversion centers into supra-molecular sheets that lie parallel to (111).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶, 2013 ▶).

Experimental

Crystal data

C17H15BrO3S

M = 379.26

Triclinic,

a = 8.1554 (2) Å

b = 9.9790 (2) Å

c = 10.1260 (2) Å

α = 77.410 (1)°

β = 77.114 (1)°

γ = 76.009 (1)°

V = 767.68 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.82 mm−1

T = 173 K

0.34 × 0.32 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.543, T max = 0.746

14016 measured reflections

3812 independent reflections

3336 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.04

3812 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.42 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/S1600536814007181/gg2139sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007181/gg2139Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007181/gg2139Isup3.cml

CCDC reference: 994776

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

C17H15BrO3S	Z = 2
Mr = 379.26	F(000) = 384
Triclinic, P1	Dx = 1.641 Mg m−3
Hall symbol: -P 1	Melting point = 475–474 K
a = 8.1554 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9790 (2) Å	Cell parameters from 6793 reflections
c = 10.1260 (2) Å	θ = 2.7–28.3°
α = 77.410 (1)°	µ = 2.82 mm−1
β = 77.114 (1)°	T = 173 K
γ = 76.009 (1)°	Block, colourless
V = 767.68 (3) Å3	0.34 × 0.32 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	3812 independent reflections
Radiation source: rotating anode	3336 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.543, Tmax = 0.746	l = −13→13
14016 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0353P)2 + 0.3958P] where P = (Fo2 + 2Fc2)/3
3812 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.42 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	0.50946 (3)	0.81656 (2)	−0.00546 (2)	0.03262 (8)
S1	0.91173 (6)	0.31301 (5)	0.35042 (4)	0.02099 (10)
O1	0.93317 (17)	0.24115 (13)	−0.01983 (13)	0.0222 (3)
O2	0.88773 (18)	0.45707 (15)	0.36343 (14)	0.0274 (3)
O3	1.06161 (18)	0.21433 (15)	0.38771 (14)	0.0287 (3)
C1	0.9028 (2)	0.31299 (19)	0.18034 (17)	0.0199 (3)
C2	0.8119 (2)	0.42615 (19)	0.09103 (18)	0.0195 (3)
C3	0.7156 (2)	0.56082 (19)	0.10102 (19)	0.0225 (4)
H3	0.6982	0.6000	0.1818	0.027*
C4	0.6470 (2)	0.63398 (19)	−0.01324 (19)	0.0232 (4)
C5	0.6705 (3)	0.5809 (2)	−0.13421 (19)	0.0251 (4)
H5	0.6202	0.6369	−0.2094	0.030*
C6	0.7667 (2)	0.4471 (2)	−0.14618 (18)	0.0230 (4)
C7	0.8346 (2)	0.37528 (19)	−0.03066 (18)	0.0205 (3)
C8	0.9720 (2)	0.2055 (2)	0.10962 (18)	0.0217 (4)
C9	0.7931 (3)	0.3831 (2)	−0.2723 (2)	0.0308 (4)
H9A	0.9106	0.3284	−0.2890	0.046*
H9B	0.7745	0.4576	−0.3516	0.046*
H9C	0.7114	0.3215	−0.2585	0.046*
C10	1.0746 (3)	0.0626 (2)	0.1429 (2)	0.0284 (4)
H10A	1.0974	0.0473	0.2366	0.043*
H10B	1.1838	0.0523	0.0778	0.043*
H10C	1.0108	−0.0065	0.1363	0.043*
C11	0.7293 (2)	0.25019 (19)	0.44768 (18)	0.0206 (3)
C12	0.5677 (3)	0.3361 (2)	0.4457 (2)	0.0270 (4)
H12	0.5553	0.4269	0.3908	0.032*
C13	0.4250 (3)	0.2879 (2)	0.5248 (2)	0.0295 (4)
H13	0.3142	0.3461	0.5232	0.035*
C14	0.4410 (3)	0.1561 (2)	0.60634 (19)	0.0267 (4)
C15	0.6032 (3)	0.0716 (2)	0.6056 (2)	0.0303 (4)
H15	0.6155	−0.0193	0.6604	0.036*
C16	0.7476 (3)	0.1173 (2)	0.5263 (2)	0.0269 (4)
H16	0.8580	0.0580	0.5260	0.032*
C17	0.2839 (3)	0.1074 (3)	0.6937 (2)	0.0375 (5)
H17A	0.3131	0.0064	0.7278	0.056*
H17B	0.1937	0.1266	0.6384	0.056*
H17C	0.2427	0.1575	0.7718	0.056*

	U11	U22	U33	U12	U13	U23
Br1	0.03337 (12)	0.01974 (11)	0.03988 (13)	−0.00075 (8)	−0.00655 (9)	−0.00013 (8)
S1	0.0221 (2)	0.0245 (2)	0.0167 (2)	−0.00315 (17)	−0.00529 (16)	−0.00419 (16)
O1	0.0252 (7)	0.0221 (6)	0.0191 (6)	−0.0024 (5)	−0.0035 (5)	−0.0065 (5)
O2	0.0345 (8)	0.0283 (7)	0.0229 (7)	−0.0090 (6)	−0.0053 (6)	−0.0089 (6)
O3	0.0226 (7)	0.0357 (8)	0.0258 (7)	−0.0006 (6)	−0.0085 (5)	−0.0031 (6)
C1	0.0201 (8)	0.0221 (9)	0.0162 (8)	−0.0025 (7)	−0.0034 (6)	−0.0026 (7)
C2	0.0199 (8)	0.0211 (8)	0.0173 (8)	−0.0053 (7)	−0.0027 (6)	−0.0021 (7)
C3	0.0254 (9)	0.0224 (9)	0.0199 (8)	−0.0060 (7)	−0.0024 (7)	−0.0042 (7)
C4	0.0231 (9)	0.0184 (8)	0.0257 (9)	−0.0044 (7)	−0.0026 (7)	−0.0004 (7)
C5	0.0277 (10)	0.0266 (10)	0.0209 (9)	−0.0087 (8)	−0.0067 (7)	0.0020 (7)
C6	0.0252 (9)	0.0272 (10)	0.0182 (8)	−0.0094 (8)	−0.0044 (7)	−0.0023 (7)
C7	0.0216 (8)	0.0207 (8)	0.0190 (8)	−0.0054 (7)	−0.0023 (7)	−0.0031 (7)
C8	0.0206 (9)	0.0248 (9)	0.0196 (8)	−0.0044 (7)	−0.0036 (7)	−0.0037 (7)
C9	0.0392 (12)	0.0361 (11)	0.0195 (9)	−0.0089 (9)	−0.0079 (8)	−0.0057 (8)
C10	0.0274 (10)	0.0236 (9)	0.0318 (10)	0.0015 (8)	−0.0057 (8)	−0.0072 (8)
C11	0.0222 (9)	0.0242 (9)	0.0154 (8)	−0.0031 (7)	−0.0039 (7)	−0.0045 (7)
C12	0.0278 (10)	0.0226 (9)	0.0269 (10)	−0.0009 (8)	−0.0055 (8)	−0.0007 (8)
C13	0.0227 (9)	0.0318 (11)	0.0301 (10)	0.0014 (8)	−0.0038 (8)	−0.0058 (8)
C14	0.0278 (10)	0.0326 (10)	0.0192 (9)	−0.0059 (8)	−0.0020 (7)	−0.0060 (8)
C15	0.0316 (11)	0.0264 (10)	0.0273 (10)	−0.0037 (8)	−0.0049 (8)	0.0041 (8)
C16	0.0235 (9)	0.0274 (10)	0.0252 (9)	0.0011 (8)	−0.0054 (8)	−0.0005 (8)
C17	0.0312 (11)	0.0460 (13)	0.0328 (11)	−0.0127 (10)	0.0004 (9)	−0.0028 (10)

Br1—C4	1.9023 (19)	C9—H9A	0.9800
Br1—Br1i	3.6517 (4)	C9—H9B	0.9800
S1—O2	1.4343 (14)	C9—H9C	0.9800
S1—O3	1.4381 (14)	C10—H10A	0.9800
S1—C1	1.7400 (17)	C10—H10B	0.9800
S1—C11	1.7618 (19)	C10—H10C	0.9800
O1—C8	1.368 (2)	C11—C16	1.383 (3)
O1—C7	1.380 (2)	C11—C12	1.390 (3)
C1—C8	1.358 (3)	C12—C13	1.384 (3)
C1—C2	1.446 (2)	C12—H12	0.9500
C2—C7	1.391 (2)	C13—C14	1.385 (3)
C2—C3	1.395 (3)	C13—H13	0.9500
C3—C4	1.381 (3)	C14—C15	1.385 (3)
C3—H3	0.9500	C14—C17	1.507 (3)
C4—C5	1.395 (3)	C15—C16	1.385 (3)
C5—C6	1.391 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.386 (3)	C17—H17A	0.9800
C6—C9	1.500 (3)	C17—H17B	0.9800
C8—C10	1.479 (3)	C17—H17C	0.9800
C4—Br1—Br1i	147.64 (6)	H9A—C9—H9B	109.5
O2—S1—O3	119.77 (9)	C6—C9—H9C	109.5
O2—S1—C1	106.40 (8)	H9A—C9—H9C	109.5
O3—S1—C1	109.32 (9)	H9B—C9—H9C	109.5
O2—S1—C11	107.59 (9)	C8—C10—H10A	109.5
O3—S1—C11	107.93 (9)	C8—C10—H10B	109.5
C1—S1—C11	104.85 (8)	H10A—C10—H10B	109.5
C8—O1—C7	107.07 (14)	C8—C10—H10C	109.5
C8—C1—C2	107.66 (15)	H10A—C10—H10C	109.5
C8—C1—S1	126.61 (14)	H10B—C10—H10C	109.5
C2—C1—S1	125.66 (14)	C16—C11—C12	120.53 (18)
C7—C2—C3	119.23 (17)	C16—C11—S1	120.14 (14)
C7—C2—C1	104.64 (16)	C12—C11—S1	119.33 (15)
C3—C2—C1	136.13 (16)	C13—C12—C11	119.24 (19)
C4—C3—C2	116.18 (17)	C13—C12—H12	120.4
C4—C3—H3	121.9	C11—C12—H12	120.4
C2—C3—H3	121.9	C12—C13—C14	121.07 (19)
C3—C4—C5	123.76 (18)	C12—C13—H13	119.5
C3—C4—Br1	118.52 (14)	C14—C13—H13	119.5
C5—C4—Br1	117.71 (14)	C13—C14—C15	118.72 (18)
C6—C5—C4	120.83 (18)	C13—C14—C17	119.98 (19)
C6—C5—H5	119.6	C15—C14—C17	121.30 (19)
C4—C5—H5	119.6	C16—C15—C14	121.17 (19)
C7—C6—C5	114.64 (17)	C16—C15—H15	119.4
C7—C6—C9	122.07 (18)	C14—C15—H15	119.4
C5—C6—C9	123.28 (17)	C11—C16—C15	119.25 (18)
O1—C7—C6	124.36 (16)	C11—C16—H16	120.4
O1—C7—C2	110.27 (15)	C15—C16—H16	120.4
C6—C7—C2	125.36 (18)	C14—C17—H17A	109.5
C1—C8—O1	110.36 (16)	C14—C17—H17B	109.5
C1—C8—C10	134.25 (17)	H17A—C17—H17B	109.5
O1—C8—C10	115.38 (16)	C14—C17—H17C	109.5
C6—C9—H9A	109.5	H17A—C17—H17C	109.5
C6—C9—H9B	109.5	H17B—C17—H17C	109.5
O2—S1—C1—C8	156.87 (17)	C3—C2—C7—O1	179.91 (15)
O3—S1—C1—C8	26.20 (19)	C1—C2—C7—O1	−0.49 (19)
C11—S1—C1—C8	−89.30 (18)	C3—C2—C7—C6	−0.9 (3)
O2—S1—C1—C2	−26.54 (18)	C1—C2—C7—C6	178.71 (17)
O3—S1—C1—C2	−157.20 (15)	C2—C1—C8—O1	0.3 (2)
C11—S1—C1—C2	87.29 (17)	S1—C1—C8—O1	177.42 (13)
C8—C1—C2—C7	0.1 (2)	C2—C1—C8—C10	−178.7 (2)
S1—C1—C2—C7	−177.03 (14)	S1—C1—C8—C10	−1.6 (3)
C8—C1—C2—C3	179.6 (2)	C7—O1—C8—C1	−0.6 (2)
S1—C1—C2—C3	2.5 (3)	C7—O1—C8—C10	178.59 (16)
C7—C2—C3—C4	0.8 (3)	O2—S1—C11—C16	−139.02 (15)
C1—C2—C3—C4	−178.64 (19)	O3—S1—C11—C16	−8.47 (18)
C2—C3—C4—C5	−0.5 (3)	C1—S1—C11—C16	107.99 (16)
C2—C3—C4—Br1	178.49 (13)	O2—S1—C11—C12	40.21 (17)
Br1i—Br1—C4—C3	70.15 (19)	O3—S1—C11—C12	170.75 (15)
Br1i—Br1—C4—C5	−110.76 (15)	C1—S1—C11—C12	−72.78 (16)
C3—C4—C5—C6	0.3 (3)	C16—C11—C12—C13	0.8 (3)
Br1—C4—C5—C6	−178.75 (14)	S1—C11—C12—C13	−178.44 (16)
C4—C5—C6—C7	−0.3 (3)	C11—C12—C13—C14	0.5 (3)
C4—C5—C6—C9	178.51 (18)	C12—C13—C14—C15	−1.2 (3)
C8—O1—C7—C6	−178.52 (17)	C12—C13—C14—C17	178.7 (2)
C8—O1—C7—C2	0.69 (19)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—O1	179.69 (16)	C17—C14—C15—C16	−179.28 (19)
C9—C6—C7—O1	0.9 (3)	C12—C11—C16—C15	−1.3 (3)
C5—C6—C7—C2	0.6 (3)	S1—C11—C16—C15	177.89 (15)
C9—C6—C7—C2	−178.21 (18)	C14—C15—C16—C11	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ii	0.95	2.54	3.330 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.54	3.330 (2)	140

Symmetry code: (i) .