organic compounds
5-Bromo-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-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, C18H17BrO2S, the dihedral angle between the mean planes of the benzofuran and 4-methylphenyl rings is 14.54 (5)°. In the crystal, molecules are linked via pairs of π–π interactions between the benzene and 4-methylphenyl rings, with centroid–centroid distances of 3.811 (3) and 3.755 (3) Å. A similar interaction is found between the furan and 4-methylphenyl rings, with a centroid–centroid distance of 3.866 (3) Å between neighbouring molecules. The molecules are stacked along the a-axis direction. In addition, a short Br⋯O contact distance of 3.128 (2) Å is observed between inversion-related dimers.
CCDC reference: 992016
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007). For π–π stacking in metal complexes with aromatic nitrogen ligands, see: Janiak (2000).
Experimental
Crystal data
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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: 992016
10.1107/S1600536814005844/fj2667sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005844/fj2667Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005844/fj2667Isup3.cml
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-ethylsulfanyl-7-methyl-2-(4-methylphenyl)-1-benzofuran (361 mg, 0.9 mmol) in dichloromethane (25 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 419–420 K; Rf = 0.51 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso (H) = 1.2Ueq (C) for aryl and methylene, 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).C18H17BrO2S | Z = 2 |
Mr = 377.29 | F(000) = 384 |
Triclinic, P1 | Dx = 1.580 Mg m−3 |
Hall symbol: -P 1 | Melting point = 420–419 K |
a = 7.3921 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2909 (3) Å | Cell parameters from 8443 reflections |
c = 11.8701 (3) Å | θ = 2.3–28.3° |
α = 68.867 (1)° | µ = 2.73 mm−1 |
β = 89.146 (1)° | T = 173 K |
γ = 71.361 (1)° | Block, colourless |
V = 792.91 (4) Å3 | 0.37 × 0.25 × 0.22 mm |
Bruker SMART APEXII CCD diffractometer | 3457 independent reflections |
Radiation source: rotating anode | 3145 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.035 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ϕ and ω scans | h = −8→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −11→13 |
Tmin = 0.535, Tmax = 0.746 | l = −15→15 |
13645 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)] = 0.029 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.3263P] where P = (Fo2 + 2Fc2)/3 |
3457 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C18H17BrO2S | γ = 71.361 (1)° |
Mr = 377.29 | V = 792.91 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3921 (2) Å | Mo Kα radiation |
b = 10.2909 (3) Å | µ = 2.73 mm−1 |
c = 11.8701 (3) Å | T = 173 K |
α = 68.867 (1)° | 0.37 × 0.25 × 0.22 mm |
β = 89.146 (1)° |
Bruker SMART APEXII CCD diffractometer | 3457 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3145 reflections with I > 2σ(I) |
Tmin = 0.535, Tmax = 0.746 | Rint = 0.035 |
13645 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.66 e Å−3 |
3457 reflections | Δρmin = −0.47 e Å−3 |
202 parameters |
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 | 0.99213 (3) | 0.28117 (2) | 1.076443 (17) | 0.03316 (9) | |
S1 | 0.64111 (7) | 0.80626 (5) | 0.58929 (4) | 0.02572 (12) | |
O1 | 0.80567 (19) | 0.41973 (14) | 0.55125 (12) | 0.0243 (3) | |
O2 | 0.7922 (2) | 0.81341 (17) | 0.66688 (15) | 0.0380 (4) | |
C1 | 0.7074 (3) | 0.6207 (2) | 0.60113 (17) | 0.0226 (4) | |
C2 | 0.7941 (3) | 0.4927 (2) | 0.71109 (17) | 0.0232 (4) | |
C3 | 0.8306 (3) | 0.4680 (2) | 0.83342 (17) | 0.0251 (4) | |
H3 | 0.7908 | 0.5463 | 0.8627 | 0.030* | |
C4 | 0.9278 (3) | 0.3240 (2) | 0.90957 (17) | 0.0262 (4) | |
C5 | 0.9886 (3) | 0.2066 (2) | 0.86941 (18) | 0.0269 (4) | |
H5 | 1.0556 | 0.1097 | 0.9262 | 0.032* | |
C6 | 0.9532 (3) | 0.2284 (2) | 0.74878 (18) | 0.0252 (4) | |
C7 | 0.8532 (3) | 0.3738 (2) | 0.67370 (17) | 0.0231 (4) | |
C8 | 0.7173 (3) | 0.5711 (2) | 0.50770 (17) | 0.0231 (4) | |
C9 | 1.0208 (3) | 0.1073 (2) | 0.70051 (19) | 0.0314 (4) | |
H9A | 0.9108 | 0.0820 | 0.6816 | 0.047* | |
H9B | 1.1140 | 0.0198 | 0.7618 | 0.047* | |
H9C | 1.0816 | 0.1406 | 0.6266 | 0.047* | |
C10 | 0.6536 (3) | 0.6380 (2) | 0.37788 (17) | 0.0236 (4) | |
C11 | 0.5193 (3) | 0.7799 (2) | 0.32352 (18) | 0.0273 (4) | |
H11 | 0.4689 | 0.8370 | 0.3715 | 0.033* | |
C12 | 0.4589 (3) | 0.8382 (2) | 0.20024 (18) | 0.0302 (4) | |
H12 | 0.3686 | 0.9355 | 0.1646 | 0.036* | |
C13 | 0.5276 (3) | 0.7571 (2) | 0.12746 (18) | 0.0305 (4) | |
C14 | 0.6616 (3) | 0.6152 (2) | 0.18236 (19) | 0.0309 (4) | |
H14 | 0.7102 | 0.5578 | 0.1345 | 0.037* | |
C15 | 0.7248 (3) | 0.5567 (2) | 0.30458 (18) | 0.0273 (4) | |
H15 | 0.8175 | 0.4604 | 0.3395 | 0.033* | |
C16 | 0.4606 (3) | 0.8183 (3) | −0.00608 (19) | 0.0407 (5) | |
H16A | 0.3793 | 0.7662 | −0.0213 | 0.061* | |
H16B | 0.5721 | 0.8047 | −0.0517 | 0.061* | |
H16C | 0.3865 | 0.9241 | −0.0324 | 0.061* | |
C17 | 0.4326 (3) | 0.8128 (2) | 0.67180 (19) | 0.0314 (5) | |
H17A | 0.4619 | 0.7210 | 0.7452 | 0.038* | |
H17B | 0.4015 | 0.8974 | 0.6986 | 0.038* | |
C18 | 0.2603 (3) | 0.8292 (2) | 0.5931 (2) | 0.0336 (5) | |
H18A | 0.2232 | 0.9248 | 0.5247 | 0.050* | |
H18B | 0.1527 | 0.8241 | 0.6418 | 0.050* | |
H18C | 0.2939 | 0.7492 | 0.5621 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03870 (14) | 0.03266 (13) | 0.02694 (12) | −0.01276 (9) | −0.00261 (8) | −0.00897 (9) |
S1 | 0.0267 (2) | 0.0211 (2) | 0.0298 (2) | −0.00751 (18) | 0.00028 (19) | −0.01041 (18) |
O1 | 0.0245 (7) | 0.0218 (6) | 0.0263 (6) | −0.0059 (5) | 0.0029 (5) | −0.0104 (5) |
O2 | 0.0368 (9) | 0.0364 (8) | 0.0449 (9) | −0.0163 (7) | −0.0060 (7) | −0.0162 (7) |
C1 | 0.0182 (9) | 0.0212 (9) | 0.0288 (9) | −0.0062 (7) | 0.0028 (7) | −0.0103 (7) |
C2 | 0.0171 (9) | 0.0233 (9) | 0.0291 (9) | −0.0067 (7) | 0.0035 (7) | −0.0098 (7) |
C3 | 0.0231 (9) | 0.0256 (9) | 0.0287 (9) | −0.0088 (7) | 0.0026 (7) | −0.0122 (8) |
C4 | 0.0240 (10) | 0.0307 (10) | 0.0258 (9) | −0.0109 (8) | 0.0015 (7) | −0.0111 (8) |
C5 | 0.0211 (9) | 0.0237 (9) | 0.0331 (10) | −0.0070 (7) | 0.0004 (8) | −0.0079 (8) |
C6 | 0.0184 (9) | 0.0244 (9) | 0.0332 (10) | −0.0067 (7) | 0.0031 (7) | −0.0118 (8) |
C7 | 0.0194 (9) | 0.0250 (9) | 0.0273 (9) | −0.0083 (7) | 0.0038 (7) | −0.0118 (7) |
C8 | 0.0173 (9) | 0.0212 (9) | 0.0308 (9) | −0.0064 (7) | 0.0045 (7) | −0.0101 (7) |
C9 | 0.0299 (11) | 0.0227 (9) | 0.0382 (11) | −0.0026 (8) | 0.0025 (8) | −0.0129 (8) |
C10 | 0.0212 (9) | 0.0274 (9) | 0.0260 (9) | −0.0123 (7) | 0.0048 (7) | −0.0107 (7) |
C11 | 0.0239 (10) | 0.0287 (10) | 0.0299 (10) | −0.0085 (8) | 0.0045 (8) | −0.0122 (8) |
C12 | 0.0222 (10) | 0.0313 (10) | 0.0327 (10) | −0.0086 (8) | 0.0020 (8) | −0.0076 (8) |
C13 | 0.0260 (10) | 0.0408 (12) | 0.0272 (10) | −0.0178 (9) | 0.0049 (8) | −0.0102 (8) |
C14 | 0.0320 (11) | 0.0383 (11) | 0.0311 (10) | −0.0180 (9) | 0.0102 (8) | −0.0176 (9) |
C15 | 0.0279 (10) | 0.0259 (9) | 0.0310 (10) | −0.0118 (8) | 0.0069 (8) | −0.0118 (8) |
C16 | 0.0367 (12) | 0.0562 (15) | 0.0283 (10) | −0.0197 (11) | 0.0034 (9) | −0.0112 (10) |
C17 | 0.0298 (11) | 0.0311 (10) | 0.0316 (10) | −0.0036 (8) | 0.0054 (8) | −0.0156 (8) |
C18 | 0.0290 (11) | 0.0328 (11) | 0.0440 (12) | −0.0119 (9) | 0.0085 (9) | −0.0189 (9) |
Br1—C4 | 1.8996 (19) | C9—H9C | 0.9800 |
Br1—O2i | 3.1284 (15) | C10—C11 | 1.396 (3) |
S1—O2 | 1.4943 (15) | C10—C15 | 1.401 (3) |
S1—C1 | 1.7658 (19) | C11—C12 | 1.384 (3) |
S1—C17 | 1.810 (2) | C11—H11 | 0.9500 |
O1—C7 | 1.369 (2) | C12—C13 | 1.392 (3) |
O1—C8 | 1.378 (2) | C12—H12 | 0.9500 |
C1—C8 | 1.370 (3) | C13—C14 | 1.395 (3) |
C1—C2 | 1.447 (3) | C13—C16 | 1.503 (3) |
C2—C7 | 1.389 (3) | C14—C15 | 1.377 (3) |
C2—C3 | 1.396 (3) | C14—H14 | 0.9500 |
C3—C4 | 1.379 (3) | C15—H15 | 0.9500 |
C3—H3 | 0.9500 | C16—H16A | 0.9800 |
C4—C5 | 1.397 (3) | C16—H16B | 0.9800 |
C5—C6 | 1.382 (3) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | C17—C18 | 1.519 (3) |
C6—C7 | 1.390 (3) | C17—H17A | 0.9900 |
C6—C9 | 1.496 (3) | C17—H17B | 0.9900 |
C8—C10 | 1.456 (3) | C18—H18A | 0.9800 |
C9—H9A | 0.9800 | C18—H18B | 0.9800 |
C9—H9B | 0.9800 | C18—H18C | 0.9800 |
C4—Br1—O2i | 164.97 (7) | C11—C10—C8 | 122.23 (17) |
O2—S1—C1 | 106.64 (9) | C15—C10—C8 | 119.43 (17) |
O2—S1—C17 | 106.82 (10) | C12—C11—C10 | 120.49 (18) |
C1—S1—C17 | 98.32 (10) | C12—C11—H11 | 119.8 |
C7—O1—C8 | 107.13 (14) | C10—C11—H11 | 119.8 |
C8—C1—C2 | 107.24 (16) | C11—C12—C13 | 121.33 (19) |
C8—C1—S1 | 127.11 (15) | C11—C12—H12 | 119.3 |
C2—C1—S1 | 124.84 (14) | C13—C12—H12 | 119.3 |
C7—C2—C3 | 119.30 (17) | C12—C13—C14 | 117.90 (18) |
C7—C2—C1 | 104.87 (16) | C12—C13—C16 | 121.8 (2) |
C3—C2—C1 | 135.80 (17) | C14—C13—C16 | 120.3 (2) |
C4—C3—C2 | 116.46 (17) | C15—C14—C13 | 121.33 (19) |
C4—C3—H3 | 121.8 | C15—C14—H14 | 119.3 |
C2—C3—H3 | 121.8 | C13—C14—H14 | 119.3 |
C3—C4—C5 | 123.18 (18) | C14—C15—C10 | 120.62 (18) |
C3—C4—Br1 | 119.36 (15) | C14—C15—H15 | 119.7 |
C5—C4—Br1 | 117.42 (14) | C10—C15—H15 | 119.7 |
C6—C5—C4 | 121.36 (17) | C13—C16—H16A | 109.5 |
C6—C5—H5 | 119.3 | C13—C16—H16B | 109.5 |
C4—C5—H5 | 119.3 | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 114.64 (17) | C13—C16—H16C | 109.5 |
C5—C6—C9 | 123.41 (17) | H16A—C16—H16C | 109.5 |
C7—C6—C9 | 121.92 (18) | H16B—C16—H16C | 109.5 |
O1—C7—C2 | 110.82 (16) | C18—C17—S1 | 111.08 (15) |
O1—C7—C6 | 124.11 (16) | C18—C17—H17A | 109.4 |
C2—C7—C6 | 125.04 (18) | S1—C17—H17A | 109.4 |
C1—C8—O1 | 109.93 (16) | C18—C17—H17B | 109.4 |
C1—C8—C10 | 135.84 (17) | S1—C17—H17B | 109.4 |
O1—C8—C10 | 114.21 (16) | H17A—C17—H17B | 108.0 |
C6—C9—H9A | 109.5 | C17—C18—H18A | 109.5 |
C6—C9—H9B | 109.5 | C17—C18—H18B | 109.5 |
H9A—C9—H9B | 109.5 | H18A—C18—H18B | 109.5 |
C6—C9—H9C | 109.5 | C17—C18—H18C | 109.5 |
H9A—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | H18B—C18—H18C | 109.5 |
C11—C10—C15 | 118.32 (17) | ||
O2—S1—C1—C8 | −130.72 (18) | C5—C6—C7—C2 | 1.6 (3) |
C17—S1—C1—C8 | 118.85 (18) | C9—C6—C7—C2 | −176.86 (19) |
O2—S1—C1—C2 | 37.58 (19) | C2—C1—C8—O1 | −0.3 (2) |
C17—S1—C1—C2 | −72.85 (18) | S1—C1—C8—O1 | 169.66 (13) |
C8—C1—C2—C7 | 0.9 (2) | C2—C1—C8—C10 | 177.6 (2) |
S1—C1—C2—C7 | −169.35 (14) | S1—C1—C8—C10 | −12.4 (3) |
C8—C1—C2—C3 | 179.1 (2) | C7—O1—C8—C1 | −0.4 (2) |
S1—C1—C2—C3 | 8.8 (3) | C7—O1—C8—C10 | −178.87 (16) |
C7—C2—C3—C4 | 1.0 (3) | C1—C8—C10—C11 | −15.2 (4) |
C1—C2—C3—C4 | −177.0 (2) | O1—C8—C10—C11 | 162.70 (17) |
C2—C3—C4—C5 | 0.1 (3) | C1—C8—C10—C15 | 166.5 (2) |
C2—C3—C4—Br1 | 177.69 (14) | O1—C8—C10—C15 | −15.6 (3) |
C3—C4—C5—C6 | −0.4 (3) | C15—C10—C11—C12 | −0.1 (3) |
Br1—C4—C5—C6 | −178.01 (15) | C8—C10—C11—C12 | −178.39 (19) |
C4—C5—C6—C7 | −0.4 (3) | C10—C11—C12—C13 | 0.8 (3) |
C4—C5—C6—C9 | 177.98 (19) | C11—C12—C13—C14 | −0.7 (3) |
C8—O1—C7—C2 | 1.0 (2) | C11—C12—C13—C16 | 179.0 (2) |
C8—O1—C7—C6 | −176.82 (18) | C12—C13—C14—C15 | −0.2 (3) |
C3—C2—C7—O1 | −179.73 (16) | C16—C13—C14—C15 | −179.9 (2) |
C1—C2—C7—O1 | −1.2 (2) | C13—C14—C15—C10 | 0.9 (3) |
C3—C2—C7—C6 | −1.9 (3) | C11—C10—C15—C14 | −0.8 (3) |
C1—C2—C7—C6 | 176.64 (18) | C8—C10—C15—C14 | 177.56 (18) |
C5—C6—C7—O1 | 179.12 (17) | O2—S1—C17—C18 | 171.58 (14) |
C9—C6—C7—O1 | 0.7 (3) | C1—S1—C17—C18 | −78.14 (16) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H17BrO2S |
Mr | 377.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 7.3921 (2), 10.2909 (3), 11.8701 (3) |
α, β, γ (°) | 68.867 (1), 89.146 (1), 71.361 (1) |
V (Å3) | 792.91 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.73 |
Crystal size (mm) | 0.37 × 0.25 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.535, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13645, 3457, 3145 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.076, 1.04 |
No. of reflections | 3457 |
No. of parameters | 202 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.47 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).
References
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Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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As a part of our continuing study of 5-bromo-3-ethylsulfinyl-7-methyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010a) and 4-chlorophenyl (Choi et al., 2010b) substituents in 2-position, we report here on the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 14.54 (5)°.
In the crystal structure (Fig. 2), the molecules are linked via π–π interactions between the benzene and 4-methylphenyl rings, and the furan and 4-methylphenyl rings of neighbouring molecules. The molecules stack along the a-axis direction. The relevant centroid names of π–π stacking interactions are Cg1 for the benzene ring (C2–C7), Cg2 for the furan ring (C1/C2/C7/O1/O8) and Cg3 for the 4-methylphenyl ring (C10–C15). The centroid–centroid separations of Cg1···Cg3ii, Cg1···Cg3iii and Cg2···Cg3ii are 3.811 (2), 3.755 (2) and 3.866 (2) Å, respectively. The symmetry codes are:(ii) -x + 1, -y + 1, -z + 1; (iii)-x + 2, -y + 1, -z + 1. Both interplanar angles between the rings (C2–C7) and (C10–C15)ii as well as (C2–C7) and (C10–C15)iii, and (C1/C2/C7/O1/C8) and (C10–C15)ii equal to 13.90 (5)° and 15.66 (5)°, respectively. This angle is quite large for rings being in π-electron···π-electron interactions as it follows from the study by Janiak (2000) who investigated π–π stacking in metal complexes with aromatic nitrogen ligands. According to Fig. 8 of Janiak's study, the interplanar angles between the rings that are involved in π-electron···π-electron interactions are less than 10° in overwhelming majority of cases. In addition, Br···O halogen-bondings (Politzer et al., 2007) between the bromine atom and the oxygen atom of the S═O unit [Br1···O2i = 3.128 (2) Å C4—Br1···O2i = 164.97 (7)°, (symmetry code :(i) - x + 2, - y + 1, - z + 2)] are observed between inversion-related dimers.