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organic compounds
3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-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 molecule, C16H13ClO3S, the 3-chlorophenyl ring makes a dihedral angle of 76.30 (5)° with the mean plane of the benzofuran fragment. In the crystal, pairs of intermolecular C—H⋯π interactions link the molecules into inversion dimers.
Related literature
For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009
); Khan et al. (2005
). For natural products with benzofuran rings, see: Akgul & Anil (2003
); Soekamto et al. (2003
). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010
, 2011
).
Experimental
Crystal data
|
Refinement
|
|
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 (Farrugia, 1997
) and DIAMOND (Brandenburg, 1998
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536811035720/qm2026sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035720/qm2026Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811035720/qm2026Isup3.cml
77% 3-chloroperoxybenzoic acid (514 mg, 2.3 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,5-dimethyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 396–397 K; Rf = 0.75 (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 in acetone at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.99 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms.
Recently, many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 76.30 (5)° . The crystal packing (Fig.2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C9—H9C···Cgi, Cg is the centroid of the C2–C7 benzene ring).
For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).
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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C16H13ClO3S | Z = 2 |
Mr = 320.77 | F(000) = 332 |
Triclinic, P1 | Dx = 1.476 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1000 (4) Å | Cell parameters from 5186 reflections |
b = 8.8622 (5) Å | θ = 2.4–27.9° |
c = 10.6898 (6) Å | µ = 0.42 mm−1 |
α = 84.023 (3)° | T = 173 K |
β = 81.514 (3)° | Block, colourless |
γ = 72.378 (3)° | 0.28 × 0.27 × 0.19 mm |
V = 721.90 (7) Å3 |
Bruker SMART APEXII CCD diffractometer | 3622 independent reflections |
Radiation source: rotating anode | 2951 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.051 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.4°, θmin = 1.9° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −11→11 |
Tmin = 0.579, Tmax = 0.746 | l = −14→14 |
13538 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)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.243P] where P = (Fo2 + 2Fc2)/3 |
3622 reflections | (Δ/σ)max < 0.001 |
192 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C16H13ClO3S | γ = 72.378 (3)° |
Mr = 320.77 | V = 721.90 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1000 (4) Å | Mo Kα radiation |
b = 8.8622 (5) Å | µ = 0.42 mm−1 |
c = 10.6898 (6) Å | T = 173 K |
α = 84.023 (3)° | 0.28 × 0.27 × 0.19 mm |
β = 81.514 (3)° |
Bruker SMART APEXII CCD diffractometer | 3622 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2951 reflections with I > 2σ(I) |
Tmin = 0.579, Tmax = 0.746 | Rint = 0.051 |
13538 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.39 e Å−3 |
3622 reflections | Δρmin = −0.40 e Å−3 |
192 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 | ||
S1 | 0.33167 (5) | 0.43504 (5) | 0.29715 (4) | 0.02475 (13) | |
Cl1 | −0.08568 (7) | 0.78553 (6) | −0.04210 (5) | 0.04248 (16) | |
O1 | 0.49244 (16) | −0.00637 (14) | 0.20581 (12) | 0.0310 (3) | |
O2 | 0.45023 (15) | 0.49763 (14) | 0.20924 (13) | 0.0328 (3) | |
O3 | 0.31247 (17) | 0.46293 (15) | 0.42888 (12) | 0.0324 (3) | |
C1 | 0.3859 (2) | 0.23236 (19) | 0.28520 (16) | 0.0239 (3) | |
C2 | 0.3302 (2) | 0.12036 (19) | 0.37751 (16) | 0.0242 (3) | |
C3 | 0.2342 (2) | 0.1260 (2) | 0.49708 (16) | 0.0272 (4) | |
H3 | 0.1872 | 0.2233 | 0.5372 | 0.033* | |
C4 | 0.2087 (2) | −0.0133 (2) | 0.55658 (17) | 0.0298 (4) | |
C5 | 0.2811 (2) | −0.1561 (2) | 0.49675 (19) | 0.0342 (4) | |
H5 | 0.2626 | −0.2505 | 0.5389 | 0.041* | |
C6 | 0.3782 (2) | −0.1647 (2) | 0.3793 (2) | 0.0341 (4) | |
H6 | 0.4273 | −0.2621 | 0.3395 | 0.041* | |
C7 | 0.3998 (2) | −0.0244 (2) | 0.32300 (17) | 0.0274 (4) | |
C8 | 0.4815 (2) | 0.1509 (2) | 0.18512 (17) | 0.0273 (4) | |
C9 | 0.1031 (3) | −0.0119 (3) | 0.68477 (19) | 0.0404 (5) | |
H9A | 0.1140 | 0.0730 | 0.7319 | 0.061* | |
H9B | 0.1462 | −0.1143 | 0.7316 | 0.061* | |
H9C | −0.0198 | 0.0063 | 0.6744 | 0.061* | |
C10 | 0.5727 (2) | 0.1939 (2) | 0.06278 (18) | 0.0367 (4) | |
H10A | 0.5343 | 0.3093 | 0.0459 | 0.055* | |
H10B | 0.5455 | 0.1426 | −0.0052 | 0.055* | |
H10C | 0.6989 | 0.1584 | 0.0665 | 0.055* | |
C11 | 0.1232 (2) | 0.51080 (19) | 0.24554 (15) | 0.0241 (3) | |
C12 | −0.0193 (2) | 0.4771 (2) | 0.31850 (17) | 0.0287 (4) | |
H12 | −0.0056 | 0.4149 | 0.3963 | 0.034* | |
C13 | −0.1810 (2) | 0.5353 (2) | 0.27665 (18) | 0.0326 (4) | |
H13 | −0.2789 | 0.5109 | 0.3250 | 0.039* | |
C14 | −0.2017 (2) | 0.6286 (2) | 0.16502 (17) | 0.0313 (4) | |
H14 | −0.3133 | 0.6683 | 0.1362 | 0.038* | |
C15 | −0.0585 (2) | 0.6636 (2) | 0.09564 (17) | 0.0290 (4) | |
C16 | 0.1054 (2) | 0.6038 (2) | 0.13328 (16) | 0.0277 (4) | |
H16 | 0.2037 | 0.6259 | 0.0835 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0225 (2) | 0.0215 (2) | 0.0316 (2) | −0.00858 (15) | −0.00493 (16) | 0.00078 (16) |
Cl1 | 0.0428 (3) | 0.0451 (3) | 0.0349 (3) | −0.0092 (2) | −0.0093 (2) | 0.0141 (2) |
O1 | 0.0274 (6) | 0.0253 (6) | 0.0376 (7) | −0.0053 (5) | 0.0013 (5) | −0.0050 (5) |
O2 | 0.0245 (6) | 0.0294 (7) | 0.0460 (8) | −0.0130 (5) | −0.0032 (5) | 0.0051 (5) |
O3 | 0.0383 (7) | 0.0286 (6) | 0.0335 (7) | −0.0114 (5) | −0.0106 (5) | −0.0027 (5) |
C1 | 0.0210 (7) | 0.0221 (7) | 0.0294 (8) | −0.0071 (6) | −0.0048 (6) | 0.0008 (6) |
C2 | 0.0198 (7) | 0.0225 (8) | 0.0315 (9) | −0.0071 (6) | −0.0072 (6) | 0.0010 (6) |
C3 | 0.0259 (8) | 0.0260 (8) | 0.0300 (9) | −0.0075 (6) | −0.0059 (7) | 0.0003 (7) |
C4 | 0.0257 (8) | 0.0330 (9) | 0.0325 (9) | −0.0115 (7) | −0.0093 (7) | 0.0067 (7) |
C5 | 0.0314 (9) | 0.0254 (9) | 0.0469 (11) | −0.0114 (7) | −0.0093 (8) | 0.0083 (8) |
C6 | 0.0310 (9) | 0.0222 (8) | 0.0495 (12) | −0.0075 (7) | −0.0062 (8) | −0.0024 (8) |
C7 | 0.0219 (8) | 0.0256 (8) | 0.0343 (9) | −0.0062 (6) | −0.0040 (7) | −0.0008 (7) |
C8 | 0.0218 (8) | 0.0256 (8) | 0.0339 (9) | −0.0059 (6) | −0.0053 (7) | 0.0001 (7) |
C9 | 0.0420 (11) | 0.0465 (11) | 0.0343 (10) | −0.0199 (9) | −0.0036 (8) | 0.0096 (9) |
C10 | 0.0323 (9) | 0.0402 (10) | 0.0331 (10) | −0.0079 (8) | 0.0025 (8) | 0.0003 (8) |
C11 | 0.0222 (8) | 0.0223 (8) | 0.0273 (8) | −0.0061 (6) | −0.0024 (6) | −0.0010 (6) |
C12 | 0.0264 (8) | 0.0293 (9) | 0.0288 (9) | −0.0083 (7) | −0.0019 (7) | 0.0047 (7) |
C13 | 0.0237 (8) | 0.0375 (10) | 0.0349 (10) | −0.0095 (7) | 0.0001 (7) | 0.0023 (8) |
C14 | 0.0241 (8) | 0.0338 (9) | 0.0330 (9) | −0.0034 (7) | −0.0054 (7) | −0.0011 (7) |
C15 | 0.0307 (9) | 0.0263 (8) | 0.0270 (9) | −0.0046 (7) | −0.0045 (7) | 0.0016 (7) |
C16 | 0.0264 (8) | 0.0257 (8) | 0.0298 (9) | −0.0079 (7) | −0.0008 (7) | 0.0012 (7) |
S1—O3 | 1.4328 (13) | C6—H6 | 0.9500 |
S1—O2 | 1.4355 (12) | C8—C10 | 1.478 (2) |
S1—C1 | 1.7289 (17) | C9—H9A | 0.9800 |
S1—C11 | 1.7659 (17) | C9—H9B | 0.9800 |
Cl1—C15 | 1.7334 (18) | C9—H9C | 0.9800 |
O1—C8 | 1.366 (2) | C10—H10A | 0.9800 |
O1—C7 | 1.383 (2) | C10—H10B | 0.9800 |
C1—C8 | 1.357 (2) | C10—H10C | 0.9800 |
C1—C2 | 1.449 (2) | C11—C16 | 1.383 (2) |
C2—C7 | 1.387 (2) | C11—C12 | 1.387 (2) |
C2—C3 | 1.392 (2) | C12—C13 | 1.377 (3) |
C3—C4 | 1.386 (2) | C12—H12 | 0.9500 |
C3—H3 | 0.9500 | C13—C14 | 1.380 (3) |
C4—C5 | 1.401 (3) | C13—H13 | 0.9500 |
C4—C9 | 1.504 (3) | C14—C15 | 1.381 (2) |
C5—C6 | 1.376 (3) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—C16 | 1.376 (2) |
C6—C7 | 1.373 (3) | C16—H16 | 0.9500 |
O3—S1—O2 | 119.46 (8) | C4—C9—H9A | 109.5 |
O3—S1—C1 | 107.56 (8) | C4—C9—H9B | 109.5 |
O2—S1—C1 | 109.13 (8) | H9A—C9—H9B | 109.5 |
O3—S1—C11 | 107.49 (8) | C4—C9—H9C | 109.5 |
O2—S1—C11 | 107.47 (8) | H9A—C9—H9C | 109.5 |
C1—S1—C11 | 104.80 (8) | H9B—C9—H9C | 109.5 |
C8—O1—C7 | 106.97 (13) | C8—C10—H10A | 109.5 |
C8—C1—C2 | 107.83 (15) | C8—C10—H10B | 109.5 |
C8—C1—S1 | 126.08 (13) | H10A—C10—H10B | 109.5 |
C2—C1—S1 | 126.02 (12) | C8—C10—H10C | 109.5 |
C7—C2—C3 | 119.05 (16) | H10A—C10—H10C | 109.5 |
C7—C2—C1 | 104.37 (15) | H10B—C10—H10C | 109.5 |
C3—C2—C1 | 136.58 (16) | C16—C11—C12 | 121.36 (16) |
C4—C3—C2 | 118.71 (16) | C16—C11—S1 | 119.09 (12) |
C4—C3—H3 | 120.6 | C12—C11—S1 | 119.55 (13) |
C2—C3—H3 | 120.6 | C13—C12—C11 | 119.07 (16) |
C3—C4—C5 | 119.84 (16) | C13—C12—H12 | 120.5 |
C3—C4—C9 | 120.42 (17) | C11—C12—H12 | 120.5 |
C5—C4—C9 | 119.74 (17) | C12—C13—C14 | 120.52 (16) |
C6—C5—C4 | 122.43 (17) | C12—C13—H13 | 119.7 |
C6—C5—H5 | 118.8 | C14—C13—H13 | 119.7 |
C4—C5—H5 | 118.8 | C13—C14—C15 | 119.29 (17) |
C7—C6—C5 | 116.06 (17) | C13—C14—H14 | 120.4 |
C7—C6—H6 | 122.0 | C15—C14—H14 | 120.4 |
C5—C6—H6 | 122.0 | C16—C15—C14 | 121.53 (16) |
C6—C7—O1 | 125.54 (16) | C16—C15—Cl1 | 119.16 (14) |
C6—C7—C2 | 123.90 (16) | C14—C15—Cl1 | 119.31 (14) |
O1—C7—C2 | 110.56 (15) | C15—C16—C11 | 118.19 (16) |
C1—C8—O1 | 110.26 (15) | C15—C16—H16 | 120.9 |
C1—C8—C10 | 134.82 (17) | C11—C16—H16 | 120.9 |
O1—C8—C10 | 114.92 (15) | ||
O3—S1—C1—C8 | −151.41 (16) | C1—C2—C7—O1 | 0.08 (19) |
O2—S1—C1—C8 | −20.43 (19) | C2—C1—C8—O1 | −0.2 (2) |
C11—S1—C1—C8 | 94.41 (17) | S1—C1—C8—O1 | −177.39 (12) |
O3—S1—C1—C2 | 31.89 (17) | C2—C1—C8—C10 | 179.7 (2) |
O2—S1—C1—C2 | 162.86 (14) | S1—C1—C8—C10 | 2.5 (3) |
C11—S1—C1—C2 | −82.29 (16) | C7—O1—C8—C1 | 0.2 (2) |
C8—C1—C2—C7 | 0.06 (19) | C7—O1—C8—C10 | −179.65 (15) |
S1—C1—C2—C7 | 177.27 (13) | O3—S1—C11—C16 | 133.45 (14) |
C8—C1—C2—C3 | 179.0 (2) | O2—S1—C11—C16 | 3.68 (16) |
S1—C1—C2—C3 | −3.8 (3) | C1—S1—C11—C16 | −112.32 (14) |
C7—C2—C3—C4 | −1.3 (3) | O3—S1—C11—C12 | −46.03 (16) |
C1—C2—C3—C4 | 179.93 (18) | O2—S1—C11—C12 | −175.80 (14) |
C2—C3—C4—C5 | 0.9 (3) | C1—S1—C11—C12 | 68.19 (16) |
C2—C3—C4—C9 | −178.90 (17) | C16—C11—C12—C13 | 1.3 (3) |
C3—C4—C5—C6 | −0.1 (3) | S1—C11—C12—C13 | −179.25 (14) |
C9—C4—C5—C6 | 179.68 (18) | C11—C12—C13—C14 | −1.4 (3) |
C4—C5—C6—C7 | −0.3 (3) | C12—C13—C14—C15 | −0.2 (3) |
C5—C6—C7—O1 | 179.85 (17) | C13—C14—C15—C16 | 1.9 (3) |
C5—C6—C7—C2 | −0.1 (3) | C13—C14—C15—Cl1 | −178.12 (15) |
C8—O1—C7—C6 | 179.81 (18) | C14—C15—C16—C11 | −2.0 (3) |
C8—O1—C7—C2 | −0.20 (19) | Cl1—C15—C16—C11 | 178.02 (13) |
C3—C2—C7—C6 | 0.9 (3) | C12—C11—C16—C15 | 0.4 (3) |
C1—C2—C7—C6 | −179.93 (17) | S1—C11—C16—C15 | −179.09 (13) |
C3—C2—C7—O1 | −179.07 (15) |
Cg is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···Cgi | 0.98 | 2.73 | 3.663 (2) | 159 |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClO3S |
Mr | 320.77 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.1000 (4), 8.8622 (5), 10.6898 (6) |
α, β, γ (°) | 84.023 (3), 81.514 (3), 72.378 (3) |
V (Å3) | 721.90 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.28 × 0.27 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.579, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13538, 3622, 2951 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.110, 1.05 |
No. of reflections | 3622 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
Cg is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···Cgi | 0.98 | 2.73 | 3.663 (2) | 159.1 |
Symmetry code: (i) −x, −y, −z+1. |
References
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Recently, many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 76.30 (5)° . The crystal packing (Fig.2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C9—H9C···Cgi, Cg is the centroid of the C2–C7 benzene ring).