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

In the title compound, C17H15BrO3S, the dihedral angle between the mean planes of the benzo-furan and 3-methyl-phenyl rings is 77.37 (5)°. In the crystal, mol-ecules are linked via pairs of Br⋯O [Br⋯O = 3.335 (2) Å] contacts into inversion dimers. These dimers are further linked by C-H⋯O hydrogen bonds and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid separation = 3.884 (3) Å] into supra-molecular chains running along the a-axis direction.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶, 2013 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15BrO3S

M = 379.26

Monoclinic,

a = 8.8813 (3) Å

b = 6.5976 (2) Å

c = 26.5044 (8) Å

β = 97.635 (1)°

V = 1539.26 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.82 mm−1

T = 296 K

0.50 × 0.46 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.379, T max = 0.746

26392 measured reflections

3831 independent reflections

3188 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.07

3831 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.45 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/S1600536814008149/bh2497sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008149/bh2497Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008149/bh2497Isup3.cml

CCDC reference: 996711

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

C17H15BrO3S	F(000) = 768
Mr = 379.26	Dx = 1.637 Mg m−3
Monoclinic, P21/c	Melting point = 439–438 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8813 (3) Å	Cell parameters from 9774 reflections
b = 6.5976 (2) Å	θ = 2.3–28.2°
c = 26.5044 (8) Å	µ = 2.82 mm−1
β = 97.635 (1)°	T = 296 K
V = 1539.26 (8) Å3	Block, colourless
Z = 4	0.50 × 0.46 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	3831 independent reflections
Radiation source: rotating anode	3188 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.043
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.379, Tmax = 0.746	l = −35→35
26392 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F2) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0364P)2 + 0.7777P] where P = (Fo2 + 2Fc2)/3
3831 reflections	(Δ/σ)max = 0.002
202 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.46068 (3)	0.80654 (4)	0.428686 (8)	0.04118 (9)
S1	0.26202 (5)	0.72154 (8)	0.641971 (18)	0.02783 (11)
O1	0.09711 (16)	0.2852 (2)	0.55049 (5)	0.0314 (3)
O2	0.27849 (16)	0.9169 (2)	0.61959 (5)	0.0352 (3)
O3	0.16243 (16)	0.7009 (3)	0.68033 (6)	0.0380 (4)
C1	0.2041 (2)	0.5514 (3)	0.59334 (7)	0.0284 (4)
C2	0.2454 (2)	0.5613 (3)	0.54261 (7)	0.0277 (4)
C3	0.3313 (2)	0.6908 (3)	0.51640 (7)	0.0305 (4)
H3	0.3777	0.8062	0.5314	0.037*
C4	0.3435 (2)	0.6375 (4)	0.46673 (7)	0.0318 (4)
C5	0.2756 (2)	0.4660 (4)	0.44286 (7)	0.0347 (5)
H5	0.2888	0.4380	0.4093	0.042*
C6	0.1884 (2)	0.3360 (3)	0.46849 (8)	0.0325 (4)
C7	0.1763 (2)	0.3932 (3)	0.51806 (7)	0.0291 (4)
C8	0.1157 (2)	0.3850 (3)	0.59611 (7)	0.0302 (4)
C9	0.1153 (3)	0.1474 (4)	0.44553 (8)	0.0415 (5)
H9A	0.1709	0.0312	0.4596	0.062*
H9B	0.1157	0.1499	0.4093	0.062*
H9C	0.0125	0.1399	0.4529	0.062*
C10	0.0370 (3)	0.2911 (3)	0.63612 (9)	0.0368 (5)
H10A	0.0463	0.3777	0.6655	0.055*
H10B	0.0821	0.1619	0.6454	0.055*
H10C	−0.0685	0.2730	0.6235	0.055*
C11	0.4444 (2)	0.6401 (3)	0.66941 (7)	0.0283 (4)
C12	0.5609 (2)	0.7803 (3)	0.67428 (7)	0.0314 (4)
H12	0.5452	0.9090	0.6603	0.038*
C13	0.7026 (2)	0.7273 (4)	0.70039 (8)	0.0389 (5)
C14	0.7213 (3)	0.5329 (4)	0.71966 (8)	0.0461 (6)
H14	0.8152	0.4950	0.7369	0.055*
C15	0.6045 (3)	0.3937 (4)	0.71410 (8)	0.0444 (6)
H15	0.6208	0.2638	0.7274	0.053*
C16	0.4631 (2)	0.4458 (4)	0.68888 (8)	0.0367 (5)
H16	0.3834	0.3533	0.6852	0.044*
C17	0.8290 (2)	0.8819 (5)	0.70728 (10)	0.0535 (7)
H17A	0.8362	0.9388	0.7409	0.080*
H17B	0.8078	0.9877	0.6825	0.080*
H17C	0.9233	0.8176	0.7029	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.04301 (14)	0.04977 (17)	0.03230 (13)	0.01099 (10)	0.01067 (9)	0.00424 (9)
S1	0.0264 (2)	0.0325 (3)	0.0236 (2)	0.00823 (19)	−0.00028 (17)	−0.00524 (18)
O1	0.0345 (7)	0.0306 (8)	0.0276 (7)	0.0047 (6)	−0.0014 (6)	−0.0037 (6)
O2	0.0379 (7)	0.0294 (8)	0.0352 (8)	0.0090 (6)	−0.0061 (6)	−0.0033 (6)
O3	0.0309 (7)	0.0511 (11)	0.0329 (8)	0.0049 (7)	0.0072 (6)	−0.0131 (7)
C1	0.0293 (9)	0.0319 (11)	0.0229 (9)	0.0079 (8)	−0.0007 (7)	−0.0030 (7)
C2	0.0272 (9)	0.0315 (11)	0.0228 (9)	0.0105 (8)	−0.0028 (7)	−0.0035 (7)
C3	0.0295 (9)	0.0333 (12)	0.0276 (9)	0.0086 (8)	−0.0002 (7)	−0.0019 (8)
C4	0.0314 (9)	0.0382 (12)	0.0255 (9)	0.0132 (8)	0.0027 (7)	0.0025 (8)
C5	0.0359 (10)	0.0439 (13)	0.0230 (9)	0.0166 (9)	−0.0016 (8)	−0.0055 (8)
C6	0.0328 (10)	0.0336 (12)	0.0288 (10)	0.0137 (8)	−0.0049 (8)	−0.0061 (8)
C7	0.0295 (9)	0.0304 (11)	0.0253 (9)	0.0100 (8)	−0.0033 (7)	−0.0012 (8)
C8	0.0317 (9)	0.0304 (11)	0.0271 (9)	0.0100 (8)	−0.0012 (7)	−0.0028 (8)
C9	0.0484 (12)	0.0394 (13)	0.0332 (11)	0.0111 (10)	−0.0072 (9)	−0.0118 (9)
C10	0.0409 (11)	0.0353 (13)	0.0343 (11)	0.0029 (9)	0.0052 (9)	−0.0013 (9)
C11	0.0283 (9)	0.0390 (11)	0.0174 (8)	0.0115 (8)	0.0025 (7)	−0.0011 (7)
C12	0.0287 (9)	0.0419 (13)	0.0239 (9)	0.0067 (8)	0.0044 (7)	−0.0019 (8)
C13	0.0285 (10)	0.0651 (16)	0.0235 (9)	0.0108 (10)	0.0057 (8)	−0.0055 (10)
C14	0.0348 (11)	0.0774 (19)	0.0253 (10)	0.0247 (12)	0.0005 (8)	0.0031 (11)
C15	0.0542 (13)	0.0508 (15)	0.0275 (10)	0.0248 (12)	0.0033 (10)	0.0101 (10)
C16	0.0405 (11)	0.0430 (13)	0.0266 (9)	0.0113 (9)	0.0050 (8)	0.0036 (9)
C17	0.0263 (10)	0.086 (2)	0.0482 (14)	0.0016 (12)	0.0042 (9)	−0.0118 (14)

Br1—C4	1.903 (2)	C9—H9A	0.9600
Br1—O2i	3.3350 (16)	C9—H9B	0.9600
S1—O2	1.4341 (17)	C9—H9C	0.9600
S1—O3	1.4400 (15)	C10—H10A	0.9600
S1—C1	1.735 (2)	C10—H10B	0.9600
S1—C11	1.7687 (19)	C10—H10C	0.9600
O1—C8	1.368 (2)	C11—C12	1.381 (3)
O1—C7	1.379 (3)	C11—C16	1.383 (3)
C1—C8	1.358 (3)	C12—C13	1.398 (3)
C1—C2	1.441 (3)	C12—H12	0.9300
C2—C7	1.387 (3)	C13—C14	1.382 (4)
C2—C3	1.391 (3)	C13—C17	1.510 (4)
C3—C4	1.381 (3)	C14—C15	1.379 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.394 (3)	C15—C16	1.385 (3)
C5—C6	1.392 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.385 (3)	C17—H17A	0.9600
C6—C9	1.495 (3)	C17—H17B	0.9600
C8—C10	1.481 (3)	C17—H17C	0.9600
C4—Br1—O2i	168.67 (6)	H9A—C9—H9B	109.5
O2—S1—O3	118.89 (9)	C6—C9—H9C	109.5
O2—S1—C1	108.10 (9)	H9A—C9—H9C	109.5
O3—S1—C1	108.30 (10)	H9B—C9—H9C	109.5
O2—S1—C11	107.76 (10)	C8—C10—H10A	109.5
O3—S1—C11	107.20 (9)	C8—C10—H10B	109.5
C1—S1—C11	105.88 (9)	H10A—C10—H10B	109.5
C8—O1—C7	106.91 (16)	C8—C10—H10C	109.5
C8—C1—C2	107.93 (17)	H10A—C10—H10C	109.5
C8—C1—S1	126.84 (15)	H10B—C10—H10C	109.5
C2—C1—S1	125.22 (16)	C12—C11—C16	122.29 (19)
C7—C2—C3	119.64 (18)	C12—C11—S1	117.95 (16)
C7—C2—C1	104.47 (18)	C16—C11—S1	119.54 (17)
C3—C2—C1	135.88 (19)	C11—C12—C13	119.5 (2)
C4—C3—C2	115.9 (2)	C11—C12—H12	120.2
C4—C3—H3	122.0	C13—C12—H12	120.2
C2—C3—H3	122.0	C14—C13—C12	118.1 (2)
C3—C4—C5	123.7 (2)	C14—C13—C17	122.1 (2)
C3—C4—Br1	118.26 (17)	C12—C13—C17	119.8 (2)
C5—C4—Br1	117.99 (15)	C15—C14—C13	121.8 (2)
C6—C5—C4	120.94 (18)	C15—C14—H14	119.1
C6—C5—H5	119.5	C13—C14—H14	119.1
C4—C5—H5	119.5	C14—C15—C16	120.5 (2)
C7—C6—C5	114.4 (2)	C14—C15—H15	119.8
C7—C6—C9	122.0 (2)	C16—C15—H15	119.8
C5—C6—C9	123.63 (19)	C11—C16—C15	117.8 (2)
O1—C7—C6	124.08 (19)	C11—C16—H16	121.1
O1—C7—C2	110.57 (16)	C15—C16—H16	121.1
C6—C7—C2	125.3 (2)	C13—C17—H17A	109.5
C1—C8—O1	110.12 (17)	C13—C17—H17B	109.5
C1—C8—C10	135.10 (19)	H17A—C17—H17B	109.5
O1—C8—C10	114.78 (19)	C13—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	−149.32 (17)	C3—C2—C7—O1	179.96 (16)
O3—S1—C1—C8	−19.3 (2)	C1—C2—C7—O1	0.1 (2)
C11—S1—C1—C8	95.42 (18)	C3—C2—C7—C6	2.0 (3)
O2—S1—C1—C2	32.05 (18)	C1—C2—C7—C6	−177.80 (18)
O3—S1—C1—C2	162.10 (16)	C2—C1—C8—O1	0.2 (2)
C11—S1—C1—C2	−83.20 (18)	S1—C1—C8—O1	−178.57 (14)
C8—C1—C2—C7	−0.2 (2)	C2—C1—C8—C10	−179.5 (2)
S1—C1—C2—C7	178.62 (14)	S1—C1—C8—C10	1.7 (3)
C8—C1—C2—C3	180.0 (2)	C7—O1—C8—C1	−0.2 (2)
S1—C1—C2—C3	−1.2 (3)	C7—O1—C8—C10	179.60 (16)
C7—C2—C3—C4	−1.2 (3)	O2—S1—C11—C12	12.15 (17)
C1—C2—C3—C4	178.6 (2)	O3—S1—C11—C12	−116.91 (15)
C2—C3—C4—C5	0.1 (3)	C1—S1—C11—C12	127.64 (16)
C2—C3—C4—Br1	−179.53 (13)	O2—S1—C11—C16	−173.10 (15)
O2i—Br1—C4—C3	58.1 (4)	O3—S1—C11—C16	57.84 (18)
O2i—Br1—C4—C5	−121.5 (3)	C1—S1—C11—C16	−57.62 (18)
C3—C4—C5—C6	0.4 (3)	C16—C11—C12—C13	−1.1 (3)
Br1—C4—C5—C6	−179.97 (15)	S1—C11—C12—C13	173.54 (15)
C4—C5—C6—C7	0.2 (3)	C11—C12—C13—C14	1.2 (3)
C4—C5—C6—C9	−178.61 (19)	C11—C12—C13—C17	−178.06 (19)
C8—O1—C7—C6	177.97 (18)	C12—C13—C14—C15	−0.6 (3)
C8—O1—C7—C2	0.0 (2)	C17—C13—C14—C15	178.7 (2)
C5—C6—C7—O1	−179.12 (17)	C13—C14—C15—C16	−0.3 (3)
C9—C6—C7—O1	−0.3 (3)	C12—C11—C16—C15	0.2 (3)
C5—C6—C7—C2	−1.5 (3)	S1—C11—C16—C15	−174.34 (15)
C9—C6—C7—C2	177.39 (19)	C14—C15—C16—C11	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ii	0.96	2.54	3.338 (3)	141
C17—H17C···O3iii	0.96	2.41	3.357 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2i	0.96	2.54	3.338 (3)	141
C17—H17C⋯O3ii	0.96	2.41	3.357 (3)	170

Symmetry codes: (i) ; (ii) .