organic compounds
of 5-bromo-2,4,6-trimethyl-3-[(2-methylphenyl)sulfinyl]-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 [r.m.s. deviation = 0.025 (2) Å] and the 2-methylbenzene rings is 87.87 (5)°. In the crystal, molecules are linked into supramolecular layers parallel to (0-11) by C—H⋯O hydrogen bonds and Br⋯Br [3.4521 (5) Å] contacts. These are connected into a three-dimensional architecture via C—H⋯π interactions, which link inversion-related molecules into dimers, and π–π interactions between the benzene and furan rings [centroid–centroid distance = 3.573 (2) Å].
Keywords: crystal structure; benzofuran; π–π interactions; C—H⋯π interactions; C—H⋯O hydrogen bonds; Br⋯Br contacts.
CCDC reference: 1413623
1. Related literature
For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab Khan et al. (2005); Ono et al. (2002). For a related structure, see: Choi et al. (2014). For synthetic details, see: Choi et al. (1999).
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: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,1998); software used to prepare material for publication: SHELXL2014.
Supporting information
CCDC reference: 1413623
https://doi.org/10.1107/S2056989015013687/tk5377sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013687/tk5377Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013687/tk5377Isup3.cml
The starting material 5-bromo-2,4,6-trimethyl-3-(2-methylphenylsulfanyl)-1-benzofuran was prepared by the literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-2,4,6-trimethyl-3-(2-methylphenylsulfanyl)-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (25 ml) at 273 K. After being stirred at room temperature for 8 h, the mixture was washed with a saturated sodium bicarbonate solution (2 x 10 ml). 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 colourless solid [yield 68% (226 mg); m.p.: 466–467 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 (21 mg) in ethyl acetate (20 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 A for methyl H atoms, Uiso(H) = 1.2Ueq (C) for aryl and 1.5Ueq (C) for methyl H atoms.
Many compounds involving a benzofuran skeleton show interesting pharmacological properties such as anti-bacterial, anti-fungal, anti-tumour and anti-viral activities (Aslam et al., 2009; Galal et al., 2009; Wahab Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999; Ono et al., 2002). As a part of our continuing project on benzofuran derivatives (Choi et al., 2014), we report herein the of the title compound. In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.025 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-methylbenzene ring is 87.87 (5) Å. In the (Fig. 2), molecules are linked by C—H···O hydrogen bonds (Table 1) and Br1···Br1iv [3.4521 (5) Å] contacts in the (0 -1 1) plane. Further, inversion-related molecules are paired into dimers via C—H···π interactions (Fig. 3, Table 1, Cg1 is the centroid of the C2–C7 benzene ring). These dimers are further linked by π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.573 (1) Å and an interplanar distance of 3.488 (2) Å resulting in a slippage of 0.775 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).
For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab Khan et al. (2005); Ono et al. (2002). For a related structure, see: Choi et al. (2014). For synthetic details, see: Choi et al. (1999).
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: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,1998); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).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···O and Br···Br 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, z; (iv) - x, - y + 2, - z + 1; (v) x - 1, y, z.] | |
Fig. 3. A view of the C—H···π and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (ii) - x + 1, - y + 2, - z; (iii) - x + 1, - y + 1, - z + 1.] |
C18H17BrO2S | Z = 2 |
Mr = 377.29 | F(000) = 384 |
Triclinic, P1 | Dx = 1.566 Mg m−3 |
a = 7.4011 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6609 (2) Å | Cell parameters from 7576 reflections |
c = 11.1857 (2) Å | θ = 2.8–28.3° |
α = 67.265 (1)° | µ = 2.70 mm−1 |
β = 86.593 (1)° | T = 173 K |
γ = 79.384 (1)° | Block, colourless |
V = 800.00 (3) Å3 | 0.60 × 0.54 × 0.48 mm |
Bruker SMART APEXII CCD diffractometer | 3982 independent reflections |
Radiation source: rotating anode | 3297 reflections with I > 2σ(I) |
Detector resolution: 10.0 pixels mm-1 | Rint = 0.046 |
φ and ω scans | θmax = 28.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.269, Tmax = 0.746 | k = −14→14 |
14745 measured reflections | l = −14→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.3816P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3982 reflections | Δρmax = 0.48 e Å−3 |
204 parameters | Δρmin = −0.79 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.040 (2) |
C18H17BrO2S | γ = 79.384 (1)° |
Mr = 377.29 | V = 800.00 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4011 (2) Å | Mo Kα radiation |
b = 10.6609 (2) Å | µ = 2.70 mm−1 |
c = 11.1857 (2) Å | T = 173 K |
α = 67.265 (1)° | 0.60 × 0.54 × 0.48 mm |
β = 86.593 (1)° |
Bruker SMART APEXII CCD diffractometer | 3982 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3297 reflections with I > 2σ(I) |
Tmin = 0.269, Tmax = 0.746 | Rint = 0.046 |
14745 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.48 e Å−3 |
3982 reflections | Δρmin = −0.79 e Å−3 |
204 parameters |
Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.01 (d, J = 7.52 Hz, 1H), 7.35-7.44 (m, 2H), 7.15-7.23 (m, 2H), 2.64 (s, 3H), 2.53 (s, 3H), 2.50 (s, 3H), 2.15 (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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.18479 (4) | 0.88031 (3) | 0.48841 (3) | 0.04996 (12) | |
S1 | 0.47494 (6) | 0.56515 (5) | 0.10695 (5) | 0.02289 (12) | |
O1 | 0.82901 (18) | 0.52534 (15) | 0.36828 (13) | 0.0255 (3) | |
O2 | 0.29324 (19) | 0.52076 (15) | 0.14556 (15) | 0.0318 (3) | |
C1 | 0.5830 (2) | 0.5705 (2) | 0.24007 (18) | 0.0215 (4) | |
C2 | 0.5307 (2) | 0.63609 (19) | 0.33233 (18) | 0.0212 (4) | |
C3 | 0.3713 (3) | 0.7126 (2) | 0.36069 (19) | 0.0252 (4) | |
C4 | 0.3916 (3) | 0.7625 (2) | 0.4560 (2) | 0.0305 (5) | |
C5 | 0.5531 (3) | 0.7344 (2) | 0.5293 (2) | 0.0320 (5) | |
C6 | 0.7045 (3) | 0.6511 (2) | 0.5047 (2) | 0.0292 (4) | |
H6 | 0.8151 | 0.6258 | 0.5538 | 0.035* | |
C7 | 0.6896 (3) | 0.6060 (2) | 0.40654 (18) | 0.0232 (4) | |
C8 | 0.7605 (3) | 0.5054 (2) | 0.26755 (19) | 0.0230 (4) | |
C9 | 0.1912 (3) | 0.7347 (2) | 0.2948 (2) | 0.0353 (5) | |
H9A | 0.0923 | 0.7254 | 0.3583 | 0.053* | |
H9B | 0.1951 | 0.6658 | 0.2564 | 0.053* | |
H9C | 0.1682 | 0.8275 | 0.2265 | 0.053* | |
C10 | 0.5626 (4) | 0.7902 (3) | 0.6331 (2) | 0.0456 (6) | |
H10A | 0.6826 | 0.7532 | 0.6771 | 0.068* | |
H10B | 0.4653 | 0.7624 | 0.6961 | 0.068* | |
H10C | 0.5460 | 0.8912 | 0.5936 | 0.068* | |
C11 | 0.8919 (3) | 0.4230 (2) | 0.2093 (2) | 0.0315 (5) | |
H11A | 0.8326 | 0.4174 | 0.1360 | 0.047* | |
H11B | 0.9303 | 0.3298 | 0.2745 | 0.047* | |
H11C | 0.9999 | 0.4674 | 0.1790 | 0.047* | |
C12 | 0.4240 (3) | 0.7459 (2) | 0.00352 (18) | 0.0237 (4) | |
C13 | 0.2409 (3) | 0.8030 (2) | −0.0253 (2) | 0.0354 (5) | |
H13 | 0.1482 | 0.7498 | 0.0148 | 0.042* | |
C14 | 0.1930 (3) | 0.9375 (3) | −0.1124 (3) | 0.0458 (6) | |
H14 | 0.0671 | 0.9775 | −0.1315 | 0.055* | |
C15 | 0.3276 (4) | 1.0137 (3) | −0.1718 (2) | 0.0425 (6) | |
H15 | 0.2950 | 1.1065 | −0.2312 | 0.051* | |
C16 | 0.5101 (3) | 0.9544 (2) | −0.1444 (2) | 0.0356 (5) | |
H16 | 0.6019 | 1.0078 | −0.1858 | 0.043* | |
C17 | 0.5636 (3) | 0.8195 (2) | −0.05849 (19) | 0.0266 (4) | |
C18 | 0.7640 (3) | 0.7562 (3) | −0.0369 (2) | 0.0373 (5) | |
H18A | 0.8362 | 0.8142 | −0.1052 | 0.056* | |
H18B | 0.7826 | 0.6637 | −0.0391 | 0.056* | |
H18C | 0.8037 | 0.7494 | 0.0478 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.05418 (19) | 0.03685 (17) | 0.05438 (19) | 0.00746 (11) | 0.01541 (12) | −0.02160 (13) |
S1 | 0.0205 (2) | 0.0245 (3) | 0.0253 (2) | −0.00667 (18) | −0.00178 (17) | −0.0098 (2) |
O1 | 0.0211 (7) | 0.0289 (8) | 0.0257 (7) | −0.0014 (5) | −0.0027 (5) | −0.0104 (6) |
O2 | 0.0237 (7) | 0.0313 (8) | 0.0385 (8) | −0.0127 (6) | −0.0026 (6) | −0.0074 (7) |
C1 | 0.0181 (8) | 0.0234 (10) | 0.0229 (9) | −0.0051 (7) | 0.0006 (7) | −0.0081 (8) |
C2 | 0.0211 (9) | 0.0195 (9) | 0.0206 (9) | −0.0045 (7) | 0.0020 (7) | −0.0047 (7) |
C3 | 0.0254 (9) | 0.0205 (10) | 0.0240 (10) | −0.0038 (7) | 0.0041 (7) | −0.0028 (8) |
C4 | 0.0375 (11) | 0.0194 (10) | 0.0291 (11) | −0.0006 (8) | 0.0082 (8) | −0.0062 (8) |
C5 | 0.0500 (13) | 0.0205 (10) | 0.0221 (10) | −0.0050 (9) | 0.0016 (9) | −0.0051 (8) |
C6 | 0.0370 (11) | 0.0247 (11) | 0.0234 (10) | −0.0047 (8) | −0.0046 (8) | −0.0059 (8) |
C7 | 0.0245 (9) | 0.0200 (10) | 0.0220 (9) | −0.0033 (7) | 0.0003 (7) | −0.0047 (8) |
C8 | 0.0208 (9) | 0.0244 (10) | 0.0241 (10) | −0.0058 (7) | 0.0003 (7) | −0.0089 (8) |
C9 | 0.0229 (10) | 0.0347 (12) | 0.0435 (13) | 0.0015 (8) | 0.0022 (9) | −0.0128 (10) |
C10 | 0.0743 (18) | 0.0328 (13) | 0.0322 (13) | −0.0039 (12) | −0.0018 (12) | −0.0173 (11) |
C11 | 0.0218 (9) | 0.0345 (12) | 0.0386 (12) | 0.0011 (8) | 0.0011 (8) | −0.0172 (10) |
C12 | 0.0271 (9) | 0.0242 (10) | 0.0205 (9) | −0.0055 (8) | −0.0020 (7) | −0.0086 (8) |
C13 | 0.0252 (10) | 0.0353 (12) | 0.0372 (12) | −0.0051 (9) | −0.0058 (9) | −0.0040 (10) |
C14 | 0.0367 (13) | 0.0393 (14) | 0.0466 (15) | 0.0009 (10) | −0.0116 (11) | −0.0022 (11) |
C15 | 0.0552 (15) | 0.0263 (12) | 0.0369 (13) | −0.0047 (11) | −0.0060 (11) | −0.0022 (10) |
C16 | 0.0467 (13) | 0.0309 (12) | 0.0300 (11) | −0.0169 (10) | 0.0021 (9) | −0.0082 (9) |
C17 | 0.0299 (10) | 0.0317 (11) | 0.0232 (10) | −0.0108 (8) | 0.0013 (8) | −0.0136 (9) |
C18 | 0.0287 (11) | 0.0438 (14) | 0.0376 (12) | −0.0146 (10) | 0.0073 (9) | −0.0110 (10) |
Br1—C4 | 1.905 (2) | C9—H9C | 0.9800 |
Br1—Br1i | 3.4521 (5) | C10—H10A | 0.9800 |
S1—O2 | 1.4921 (14) | C10—H10B | 0.9800 |
S1—C1 | 1.7561 (19) | C10—H10C | 0.9800 |
S1—C12 | 1.805 (2) | C11—H11A | 0.9800 |
O1—C8 | 1.366 (2) | C11—H11B | 0.9800 |
O1—C7 | 1.376 (2) | C11—H11C | 0.9800 |
C1—C8 | 1.360 (3) | C12—C13 | 1.381 (3) |
C1—C2 | 1.454 (3) | C12—C17 | 1.399 (3) |
C2—C7 | 1.395 (3) | C13—C14 | 1.381 (3) |
C2—C3 | 1.399 (3) | C13—H13 | 0.9500 |
C3—C4 | 1.389 (3) | C14—C15 | 1.377 (4) |
C3—C9 | 1.498 (3) | C14—H14 | 0.9500 |
C4—C5 | 1.409 (3) | C15—C16 | 1.379 (4) |
C5—C6 | 1.381 (3) | C15—H15 | 0.9500 |
C5—C10 | 1.505 (3) | C16—C17 | 1.384 (3) |
C6—C7 | 1.375 (3) | C16—H16 | 0.9500 |
C6—H6 | 0.9500 | C17—C18 | 1.504 (3) |
C8—C11 | 1.481 (3) | C18—H18A | 0.9800 |
C9—H9A | 0.9800 | C18—H18B | 0.9800 |
C9—H9B | 0.9800 | C18—H18C | 0.9800 |
C4—Br1—Br1i | 173.50 (6) | C5—C10—H10B | 109.5 |
O2—S1—C1 | 110.19 (9) | H10A—C10—H10B | 109.5 |
O2—S1—C12 | 105.80 (9) | C5—C10—H10C | 109.5 |
C1—S1—C12 | 101.64 (9) | H10A—C10—H10C | 109.5 |
C8—O1—C7 | 106.53 (14) | H10B—C10—H10C | 109.5 |
C8—C1—C2 | 106.98 (16) | C8—C11—H11A | 109.5 |
C8—C1—S1 | 117.93 (15) | C8—C11—H11B | 109.5 |
C2—C1—S1 | 135.02 (15) | H11A—C11—H11B | 109.5 |
C7—C2—C3 | 119.21 (18) | C8—C11—H11C | 109.5 |
C7—C2—C1 | 104.32 (16) | H11A—C11—H11C | 109.5 |
C3—C2—C1 | 136.46 (18) | H11B—C11—H11C | 109.5 |
C4—C3—C2 | 115.32 (18) | C13—C12—C17 | 121.35 (19) |
C4—C3—C9 | 122.90 (19) | C13—C12—S1 | 116.73 (15) |
C2—C3—C9 | 121.76 (19) | C17—C12—S1 | 121.36 (15) |
C3—C4—C5 | 125.3 (2) | C14—C13—C12 | 119.8 (2) |
C3—C4—Br1 | 117.17 (16) | C14—C13—H13 | 120.1 |
C5—C4—Br1 | 117.52 (16) | C12—C13—H13 | 120.1 |
C6—C5—C4 | 117.8 (2) | C15—C14—C13 | 120.0 (2) |
C6—C5—C10 | 120.1 (2) | C15—C14—H14 | 120.0 |
C4—C5—C10 | 122.0 (2) | C13—C14—H14 | 120.0 |
C7—C6—C5 | 117.64 (19) | C14—C15—C16 | 119.6 (2) |
C7—C6—H6 | 121.2 | C14—C15—H15 | 120.2 |
C5—C6—H6 | 121.2 | C16—C15—H15 | 120.2 |
C6—C7—O1 | 124.63 (17) | C15—C16—C17 | 122.1 (2) |
C6—C7—C2 | 124.46 (19) | C15—C16—H16 | 119.0 |
O1—C7—C2 | 110.91 (16) | C17—C16—H16 | 119.0 |
C1—C8—O1 | 111.23 (17) | C16—C17—C12 | 117.10 (19) |
C1—C8—C11 | 133.54 (19) | C16—C17—C18 | 120.40 (19) |
O1—C8—C11 | 115.20 (16) | C12—C17—C18 | 122.48 (19) |
C3—C9—H9A | 109.5 | C17—C18—H18A | 109.5 |
C3—C9—H9B | 109.5 | C17—C18—H18B | 109.5 |
H9A—C9—H9B | 109.5 | H18A—C18—H18B | 109.5 |
C3—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 |
C5—C10—H10A | 109.5 | ||
O2—S1—C1—C8 | 130.07 (16) | C3—C2—C7—C6 | −2.7 (3) |
C12—S1—C1—C8 | −118.10 (16) | C1—C2—C7—C6 | 178.32 (19) |
O2—S1—C1—C2 | −53.3 (2) | C3—C2—C7—O1 | 177.36 (16) |
C12—S1—C1—C2 | 58.6 (2) | C1—C2—C7—O1 | −1.6 (2) |
C8—C1—C2—C7 | 1.7 (2) | C2—C1—C8—O1 | −1.1 (2) |
S1—C1—C2—C7 | −175.25 (16) | S1—C1—C8—O1 | 176.39 (13) |
C8—C1—C2—C3 | −177.1 (2) | C2—C1—C8—C11 | −179.1 (2) |
S1—C1—C2—C3 | 6.0 (4) | S1—C1—C8—C11 | −1.6 (3) |
C7—C2—C3—C4 | 5.3 (3) | C7—O1—C8—C1 | 0.1 (2) |
C1—C2—C3—C4 | −176.1 (2) | C7—O1—C8—C11 | 178.51 (17) |
C7—C2—C3—C9 | −173.01 (18) | O2—S1—C12—C13 | −3.79 (19) |
C1—C2—C3—C9 | 5.6 (3) | C1—S1—C12—C13 | −118.91 (17) |
C2—C3—C4—C5 | −4.3 (3) | O2—S1—C12—C17 | −175.31 (16) |
C9—C3—C4—C5 | 174.0 (2) | C1—S1—C12—C17 | 69.58 (17) |
C2—C3—C4—Br1 | 174.84 (13) | C17—C12—C13—C14 | −3.1 (3) |
C9—C3—C4—Br1 | −6.9 (3) | S1—C12—C13—C14 | −174.6 (2) |
C3—C4—C5—C6 | 0.3 (3) | C12—C13—C14—C15 | 1.0 (4) |
Br1—C4—C5—C6 | −178.87 (15) | C13—C14—C15—C16 | 0.5 (4) |
C3—C4—C5—C10 | −178.6 (2) | C14—C15—C16—C17 | 0.0 (4) |
Br1—C4—C5—C10 | 2.2 (3) | C15—C16—C17—C12 | −2.0 (3) |
C4—C5—C6—C7 | 2.7 (3) | C15—C16—C17—C18 | 176.6 (2) |
C10—C5—C6—C7 | −178.4 (2) | C13—C12—C17—C16 | 3.5 (3) |
C5—C6—C7—O1 | 178.41 (18) | S1—C12—C17—C16 | 174.66 (16) |
C5—C6—C7—C2 | −1.5 (3) | C13—C12—C17—C18 | −175.1 (2) |
C8—O1—C7—C6 | −178.95 (19) | S1—C12—C17—C18 | −3.9 (3) |
C8—O1—C7—C2 | 1.0 (2) |
Symmetry code: (i) −x, −y+2, −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—H9B···O2 | 0.98 | 2.33 | 3.274 (3) | 162 |
C11—H11C···O2ii | 0.98 | 2.32 | 3.276 (2) | 166 |
C15—H15···Cg1iii | 0.95 | 2.88 | 3.659 (3) | 140 |
Symmetry codes: (ii) x+1, y, z; (iii) −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—H9B···O2 | 0.98 | 2.33 | 3.274 (3) | 162 |
C11—H11C···O2i | 0.98 | 2.32 | 3.276 (2) | 166 |
C15—H15···Cg1ii | 0.95 | 2.88 | 3.659 (3) | 140 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.
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Many compounds involving a benzofuran skeleton show interesting pharmacological properties such as anti-bacterial, anti-fungal, anti-tumour and anti-viral activities (Aslam et al., 2009; Galal et al., 2009; Wahab Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999; Ono et al., 2002). As a part of our continuing project on benzofuran derivatives (Choi et al., 2014), we report herein the crystal structure of the title compound. In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.025 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-methylbenzene ring is 87.87 (5) Å. In the crystal structure (Fig. 2), molecules are linked by C—H···O hydrogen bonds (Table 1) and Br1···Br1iv [3.4521 (5) Å] contacts in the (0 -1 1) plane. Further, inversion-related molecules are paired into dimers via C—H···π interactions (Fig. 3, Table 1, Cg1 is the centroid of the C2–C7 benzene ring). These dimers are further linked by π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.573 (1) Å and an interplanar distance of 3.488 (2) Å resulting in a slippage of 0.775 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).