organic compounds
of 3-(2-bromophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr
In the title compound, C17H15BrO3S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.016 (2) Å] and the 2-bromophenyl ring is 82.93 (6)°. In the crystal, molecules are linked via pairs of C—H⋯π hydrogen bonds and π–π interactions between the benzene and furan rings of neighbouring molecules [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.
Keywords: crystal structure; benzofuran; 2-bromophenyl; C—H⋯π hydrogen bonds; π–π interactions; Br⋯O contact.
CCDC reference: 1027593
1. 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).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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.
Supporting information
CCDC reference: 1027593
10.1107/S1600536814021850/mw2127sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814021850/mw2127Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814021850/mw2127Isup3.cml
The starting material 3-(2-bromophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran was prepared by a literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 403 mg, 1.8 mmol) was added in small portions to a stirred solution of 3-(2-bromophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (278 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 10 ml) and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane-ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 72% (218 mg); m.p. 453–454 K; Rf = 0.51 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (21 mg) in acetone (15 ml) at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, and 0.98 Å for methyl H atoms, respectively. Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C)) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).Fig. 1. 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. Fig. 2. A view of the C—H···π, π–π and Br···O interactions (dotted lines) in the 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 + 1/2, y - 1/2, - z + 3/2 ; (iii) - x, - y + 1, - z + 1; (iv) - x + 1/2, y + 1/2, - z + 3/2.] |
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 |
C17H15BrO3S | V = 1555.49 (7) Å3 |
Mr = 379.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.8969 (2) Å | µ = 2.79 mm−1 |
b = 8.1489 (2) Å | T = 173 K |
c = 24.3146 (6) Å | 0.31 × 0.27 × 0.13 mm |
β = 96.210 (1)° |
Bruker SMART APEXII CCD diffractometer | 3867 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3130 reflections with I > 2σ(I) |
Tmin = 0.479, Tmax = 0.713 | Rint = 0.042 |
27395 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.51 e Å−3 |
3867 reflections | Δρmin = −0.34 e Å−3 |
202 parameters |
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) |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···Cg1ii | 0.98 | 2.84 | 3.608 (2) | 136 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···Cg1i | 0.98 | 2.84 | 3.608 (2) | 136.3 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The X-ray centre of Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.
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As a part of our continuing program for benzofuran derivatives (Choi & Lee, 2014), we report herein on the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (2) Å from the least-squares plane defined by the nine constituent atoms. The 2-bromophenyl ring is essentially planar, with a mean deviation of 0.004 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-bromophenyl ring is 82.93 (6)°. In the crystal structure (Fig. 2), molecules are linked via two different pairs of C—H···π hydrogen bonds (Table 1, Cg1 is the centroid of the C2–C7 benzene ring) and π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2iii distance of 3.881 (2) Å and an interplanar distance of 3.562 (2) Å resulting in a slippage of 1.541 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring), into inversion-related dimers along the b-axis direction. These dimers are further linked by halogen-bondings (Politzer et al. 2007) between the bromine and the O atom of the O═S═O unit [Br1..O3ii = 3.185 (2) Å, C17—Br1···O3ii = 164.49 (7)°, symmetry code: (ii) - x + 1/2, y - 1/2, - z + 3/2].