Crystal structure of 3-(2-bromo-phenyl-sulfon-yl)-2,5,7-trimethyl-1-benzo-furan.

In the title compound, C17H15BrO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.016 (2) Å] and the 2-bromo-phenyl ring is 82.93 (6)°. In the crystal, mol-ecules are linked via pairs of C-H⋯π hydrogen bonds and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.881 (2) Å] into inversion-related dimers along the b-axis direction. These dimers are further linked by short Br⋯O [3.185 (2) Å] contacts.

Related literature

For a related structure and background to benzo­furan derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15BrO3S

M = 379.26

Monoclinic,

a = 7.8969 (2) Å

b = 8.1489 (2) Å

c = 24.3146 (6) Å

β = 96.210 (1)°

V = 1555.49 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 173 K

0.31 × 0.27 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.479, T max = 0.713

27395 measured reflections

3867 independent reflections

3130 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.03

3867 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.34 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/S1600536814021850/mw2127sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021850/mw2127Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021850/mw2127Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814021850/mw2127fig1.tif

The mol­ecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.

x y z x y z x y z x y z . DOI: 10.1107/S1600536814021850/mw2127fig2.tif

A view of the C—H⋯π, π–π and Br⋯O inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 1, − y + 1, − z + 1; (ii) − x + , y − , − z + ; (iii) − x, − y + 1, − z + 1; (iv) − x + , y + , − z + .]

CCDC reference: 1027593

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

C17H15BrO3S	F(000) = 768
Mr = 379.26	Dx = 1.619 Mg m−3
Monoclinic, P21/n	Melting point = 454–453 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8969 (2) Å	Cell parameters from 7387 reflections
b = 8.1489 (2) Å	θ = 2.6–26.1°
c = 24.3146 (6) Å	µ = 2.79 mm−1
β = 96.210 (1)°	T = 173 K
V = 1555.49 (7) Å3	Block, colourless
Z = 4	0.31 × 0.27 × 0.13 mm

Bruker SMART APEXII CCD diffractometer	3867 independent reflections
Radiation source: rotating anode	3130 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.042
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.479, Tmax = 0.713	l = −31→32
27395 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) = 0.080	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.8758P] where P = (Fo2 + 2Fc2)/3
3867 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.49 (d, J = 6.12 Hz, 1H), 7.65 (d, J =6.84 Hz, 1H), 7.53-7.58 (m, 1H), 7.38-7.43 (m, 1H), 7.06 (s, 1H), 6.88 (s, 1H), 2.84 (s, 3H), 2.43 (s, 3H), 2.31 (s, 3H).

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	0.46256 (3)	0.42412 (3)	0.713662 (9)	0.03093 (9)
S1	0.12638 (7)	0.65915 (7)	0.65837 (2)	0.02299 (13)
O1	0.1202 (2)	0.22941 (18)	0.58642 (6)	0.0280 (4)
O2	0.0262 (2)	0.7852 (2)	0.62933 (7)	0.0320 (4)
O3	0.0830 (2)	0.6094 (2)	0.71169 (7)	0.0311 (4)
C1	0.1294 (3)	0.4896 (3)	0.61574 (9)	0.0222 (4)
C2	0.1822 (3)	0.4890 (3)	0.56071 (8)	0.0208 (4)
C3	0.2360 (3)	0.6058 (3)	0.52431 (9)	0.0241 (4)
H3	0.2402	0.7190	0.5337	0.029*
C4	0.2832 (3)	0.5521 (3)	0.47408 (9)	0.0257 (5)
C5	0.2767 (3)	0.3855 (3)	0.46099 (9)	0.0273 (5)
H5	0.3106	0.3521	0.4264	0.033*
C6	0.2235 (3)	0.2660 (3)	0.49579 (9)	0.0270 (5)
C7	0.1761 (3)	0.3251 (3)	0.54484 (9)	0.0229 (4)
C8	0.0946 (3)	0.3321 (3)	0.62932 (9)	0.0258 (5)
C9	0.3440 (3)	0.6725 (3)	0.43345 (10)	0.0350 (6)
H9A	0.2662	0.7664	0.4294	0.053*
H9B	0.3467	0.6188	0.3975	0.053*
H9C	0.4587	0.7105	0.4470	0.053*
C10	0.2218 (4)	0.0869 (3)	0.48191 (12)	0.0412 (6)
H10A	0.2464	0.0228	0.5159	0.062*
H10B	0.3084	0.0642	0.4570	0.062*
H10C	0.1093	0.0566	0.4638	0.062*
C11	0.0392 (3)	0.2511 (3)	0.67846 (10)	0.0378 (6)
H11A	0.1317	0.1821	0.6958	0.057*
H11B	−0.0608	0.1827	0.6674	0.057*
H11C	0.0099	0.3344	0.7049	0.057*
C12	0.3401 (3)	0.7318 (3)	0.66497 (8)	0.0220 (4)
C13	0.3630 (3)	0.8918 (3)	0.64809 (10)	0.0286 (5)
H13	0.2678	0.9543	0.6327	0.034*
C14	0.5241 (3)	0.9611 (3)	0.65352 (11)	0.0365 (6)
H14	0.5390	1.0714	0.6423	0.044*
C15	0.6626 (3)	0.8704 (3)	0.67508 (11)	0.0363 (6)
H15	0.7730	0.9181	0.6785	0.044*
C16	0.6417 (3)	0.7101 (3)	0.69174 (10)	0.0315 (5)
H16	0.7377	0.6476	0.7063	0.038*
C17	0.4809 (3)	0.6409 (3)	0.68725 (9)	0.0238 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.03549 (14)	0.02720 (13)	0.02903 (14)	0.00525 (10)	−0.00148 (9)	0.00300 (9)
S1	0.0223 (3)	0.0245 (3)	0.0227 (3)	0.0008 (2)	0.0050 (2)	−0.0029 (2)
O1	0.0390 (9)	0.0201 (7)	0.0247 (8)	−0.0047 (7)	0.0030 (7)	0.0020 (6)
O2	0.0277 (8)	0.0306 (9)	0.0366 (9)	0.0082 (7)	−0.0009 (7)	−0.0044 (7)
O3	0.0319 (8)	0.0388 (10)	0.0243 (8)	−0.0031 (7)	0.0113 (7)	−0.0042 (7)
C1	0.0231 (10)	0.0228 (10)	0.0209 (11)	−0.0007 (8)	0.0030 (8)	−0.0005 (8)
C2	0.0197 (10)	0.0225 (10)	0.0201 (10)	0.0011 (8)	0.0018 (8)	0.0005 (8)
C3	0.0275 (11)	0.0204 (10)	0.0244 (11)	−0.0008 (8)	0.0033 (9)	−0.0006 (8)
C4	0.0248 (11)	0.0295 (11)	0.0229 (11)	0.0006 (9)	0.0031 (9)	0.0018 (9)
C5	0.0304 (11)	0.0307 (12)	0.0214 (11)	0.0033 (9)	0.0052 (9)	−0.0048 (9)
C6	0.0299 (11)	0.0255 (11)	0.0248 (12)	0.0019 (9)	−0.0001 (9)	−0.0043 (9)
C7	0.0258 (11)	0.0208 (10)	0.0217 (11)	−0.0016 (8)	0.0012 (8)	0.0016 (8)
C8	0.0282 (11)	0.0258 (11)	0.0236 (11)	−0.0030 (9)	0.0031 (9)	−0.0012 (9)
C9	0.0391 (14)	0.0392 (14)	0.0283 (13)	−0.0014 (11)	0.0106 (11)	0.0039 (11)
C10	0.0618 (18)	0.0252 (12)	0.0368 (15)	0.0020 (12)	0.0065 (13)	−0.0082 (11)
C11	0.0508 (16)	0.0351 (13)	0.0288 (13)	−0.0102 (12)	0.0098 (11)	0.0050 (11)
C12	0.0242 (10)	0.0244 (11)	0.0180 (10)	−0.0011 (8)	0.0055 (8)	−0.0046 (8)
C13	0.0346 (12)	0.0241 (11)	0.0278 (12)	0.0005 (9)	0.0057 (10)	−0.0006 (9)
C14	0.0477 (15)	0.0286 (12)	0.0349 (14)	−0.0092 (11)	0.0124 (12)	−0.0037 (10)
C15	0.0308 (12)	0.0455 (15)	0.0339 (14)	−0.0116 (11)	0.0085 (11)	−0.0094 (12)
C16	0.0256 (11)	0.0428 (14)	0.0261 (12)	0.0003 (10)	0.0034 (9)	−0.0053 (10)
C17	0.0293 (11)	0.0262 (11)	0.0163 (10)	0.0023 (9)	0.0044 (8)	−0.0027 (8)

Br1—C17	1.890 (2)	C8—C11	1.472 (3)
Br1—O3i	22.6093 (17)	C9—H9A	0.9800
S1—O3	1.4345 (16)	C9—H9B	0.9800
S1—O2	1.4348 (17)	C9—H9C	0.9800
S1—C1	1.729 (2)	C10—H10A	0.9800
S1—C12	1.779 (2)	C10—H10B	0.9800
O1—C8	1.369 (3)	C10—H10C	0.9800
O1—C7	1.386 (3)	C11—H11A	0.9800
C1—C8	1.361 (3)	C11—H11B	0.9800
C1—C2	1.444 (3)	C11—H11C	0.9800
C2—C7	1.390 (3)	C12—C13	1.385 (3)
C2—C3	1.397 (3)	C12—C17	1.396 (3)
C3—C4	1.386 (3)	C13—C14	1.385 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.395 (3)	C14—C15	1.376 (4)
C4—C9	1.507 (3)	C14—H14	0.9500
C5—C6	1.385 (3)	C15—C16	1.383 (4)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.375 (3)	C16—C17	1.383 (3)
C6—C10	1.497 (3)	C16—H16	0.9500
C17—Br1—O3i	76.20 (6)	H9A—C9—H9B	109.5
O3—S1—O2	118.32 (10)	C4—C9—H9C	109.5
O3—S1—C1	109.64 (10)	H9A—C9—H9C	109.5
O2—S1—C1	108.65 (10)	H9B—C9—H9C	109.5
O3—S1—C12	109.22 (10)	C6—C10—H10A	109.5
O2—S1—C12	105.85 (10)	C6—C10—H10B	109.5
C1—S1—C12	104.19 (10)	H10A—C10—H10B	109.5
C8—O1—C7	107.27 (16)	C6—C10—H10C	109.5
C8—C1—C2	107.93 (19)	H10A—C10—H10C	109.5
C8—C1—S1	126.30 (17)	H10B—C10—H10C	109.5
C2—C1—S1	125.62 (16)	C8—C11—H11A	109.5
C7—C2—C3	118.87 (19)	C8—C11—H11B	109.5
C7—C2—C1	104.80 (18)	H11A—C11—H11B	109.5
C3—C2—C1	136.3 (2)	C8—C11—H11C	109.5
C4—C3—C2	118.2 (2)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C13—C12—C17	119.4 (2)
C3—C4—C5	120.1 (2)	C13—C12—S1	116.07 (17)
C3—C4—C9	120.5 (2)	C17—C12—S1	124.50 (17)
C5—C4—C9	119.4 (2)	C12—C13—C14	120.3 (2)
C6—C5—C4	123.5 (2)	C12—C13—H13	119.9
C6—C5—H5	118.3	C14—C13—H13	119.9
C4—C5—H5	118.3	C15—C14—C13	120.1 (2)
C7—C6—C5	114.4 (2)	C15—C14—H14	120.0
C7—C6—C10	122.7 (2)	C13—C14—H14	120.0
C5—C6—C10	122.9 (2)	C14—C15—C16	120.3 (2)
C6—C7—O1	125.00 (19)	C14—C15—H15	119.9
C6—C7—C2	124.9 (2)	C16—C15—H15	119.9
O1—C7—C2	110.03 (18)	C17—C16—C15	120.0 (2)
C1—C8—O1	109.95 (18)	C17—C16—H16	120.0
C1—C8—C11	134.9 (2)	C15—C16—H16	120.0
O1—C8—C11	115.2 (2)	C16—C17—C12	120.0 (2)
C4—C9—H9A	109.5	C16—C17—Br1	117.25 (18)
C4—C9—H9B	109.5	C12—C17—Br1	122.73 (17)
O3—S1—C1—C8	0.8 (2)	C1—C2—C7—O1	1.1 (2)
O2—S1—C1—C8	−129.9 (2)	C2—C1—C8—O1	−0.4 (2)
C12—S1—C1—C8	117.6 (2)	S1—C1—C8—O1	−176.16 (16)
O3—S1—C1—C2	−174.23 (18)	C2—C1—C8—C11	178.8 (3)
O2—S1—C1—C2	55.1 (2)	S1—C1—C8—C11	3.0 (4)
C12—S1—C1—C2	−57.4 (2)	C7—O1—C8—C1	1.1 (2)
C8—C1—C2—C7	−0.4 (2)	C7—O1—C8—C11	−178.3 (2)
S1—C1—C2—C7	175.34 (16)	O3—S1—C12—C13	−121.32 (17)
C8—C1—C2—C3	−178.9 (2)	O2—S1—C12—C13	7.10 (19)
S1—C1—C2—C3	−3.1 (4)	C1—S1—C12—C13	121.60 (18)
C7—C2—C3—C4	−0.8 (3)	O3—S1—C12—C17	56.5 (2)
C1—C2—C3—C4	177.4 (2)	O2—S1—C12—C17	−175.07 (17)
C2—C3—C4—C5	−0.1 (3)	C1—S1—C12—C17	−60.6 (2)
C2—C3—C4—C9	−179.4 (2)	C17—C12—C13—C14	−0.3 (3)
C3—C4—C5—C6	0.4 (4)	S1—C12—C13—C14	177.65 (18)
C9—C4—C5—C6	179.7 (2)	C12—C13—C14—C15	0.8 (4)
C4—C5—C6—C7	0.3 (3)	C13—C14—C15—C16	−0.4 (4)
C4—C5—C6—C10	−178.2 (2)	C14—C15—C16—C17	−0.6 (4)
C5—C6—C7—O1	−179.3 (2)	C15—C16—C17—C12	1.2 (3)
C10—C6—C7—O1	−0.8 (4)	C15—C16—C17—Br1	−177.56 (18)
C5—C6—C7—C2	−1.4 (3)	C13—C12—C17—C16	−0.7 (3)
C10—C6—C7—C2	177.2 (2)	S1—C12—C17—C16	−178.47 (17)
C8—O1—C7—C6	176.8 (2)	C13—C12—C17—Br1	177.95 (16)
C8—O1—C7—C2	−1.4 (2)	S1—C12—C17—Br1	0.2 (3)
C3—C2—C7—C6	1.7 (3)	O3i—Br1—C17—C16	−99.99 (17)
C1—C2—C7—C6	−177.1 (2)	O3i—Br1—C17—C12	81.32 (17)
C3—C2—C7—O1	179.89 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cg1ii	0.98	2.84	3.608 (2)	136

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C2C7 benzene ring.

DHA	DH	HA	D A	DHA
C9H9C Cg1i	0.98	2.84	3.608(2)	136

Symmetry code: (i) .