organic compounds
5-Chloro-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, C18H17ClO2S, the dihedral angle between the mean planes of the benzofuran ring system and the methylphenyl ring is 14.50 (4)°. The centroid–centroid distances between the benzene and the methylphenyl rings are 3.827 (2) and 3.741 (2) Å, while the centroid–centroid distance between the furan and methylphenyl rings is 3.843 (2) Å. These distances indicate π–π interactions; on the other hand, the interplanar angles between the benzene and methylphenyl rings, and between the furan and methylphenyl rings are 13.89 (4) and 15.53 (4)°, respectively. In the crystal, the molecules stack along the a-axis direction.
CCDC reference: 991267
Related literature
For background information about related compounds and their crystal structures, see Choi et al. (2010a,b). 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: 991267
10.1107/S1600536814005601/fb2296sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005601/fb2296Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005601/fb2296Isup3.cml
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to the stirred solution of 5-chloro-3-ethylsulfanyl-7-methyl-2-(4-methylphenyl)-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. The mixture was washed with saturated sodium hydrogen carbonate solution after having been stirred at room temperature for 4h. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure.
The residue was purified by
(hexane–ethyl acetate, 1:1v/v) to afford the title compound as a colourless solid [yield 71%, m.p. 392–393 K; Rf = 0.56 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the 5% solution of the title compound in acetone at room temperature. The average crystal size was approximately 1.1 × 1.3 × 0.8 mm. (The measured crystal was cut from a large one.) The crystals are soluble in polar solvents.All the hydrogen atoms were observed in the difference
However, they were situated into the idealized positions and refined using a riding-model approximation. The used constraints: C—H = 0.95 Å for aryl, 0.98 Å for methyl and for 0.99 Å for methylene H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene, while 1.5Ueq(C) for the 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).C18H17ClO2S | Z = 2 |
Mr = 332.83 | F(000) = 348 |
Triclinic, P1 | Dx = 1.408 Mg m−3 |
Hall symbol: -P 1 | Melting point = 392–393 K |
a = 7.3638 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2524 (6) Å | Cell parameters from 8286 reflections |
c = 11.8335 (7) Å | θ = 2.3–28.4° |
α = 68.949 (3)° | µ = 0.38 mm−1 |
β = 89.362 (3)° | T = 173 K |
γ = 71.460 (3)° | Block, colourless |
V = 785.11 (8) Å3 | 0.46 × 0.37 × 0.33 mm |
Bruker SMART APEXII CCD diffractometer | 3759 independent reflections |
Radiation source: rotating anode | 3348 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.031 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.0°, θmin = 2.3° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −13→13 |
Tmin = 0.691, Tmax = 0.746 | l = −15→15 |
13937 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2412P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3759 reflections | Δρmax = 0.31 e Å−3 |
203 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.006 (2) |
C18H17ClO2S | γ = 71.460 (3)° |
Mr = 332.83 | V = 785.11 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3638 (5) Å | Mo Kα radiation |
b = 10.2524 (6) Å | µ = 0.38 mm−1 |
c = 11.8335 (7) Å | T = 173 K |
α = 68.949 (3)° | 0.46 × 0.37 × 0.33 mm |
β = 89.362 (3)° |
Bruker SMART APEXII CCD diffractometer | 3759 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3348 reflections with I > 2σ(I) |
Tmin = 0.691, Tmax = 0.746 | Rint = 0.031 |
13937 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.31 e Å−3 |
3759 reflections | Δρmin = −0.29 e Å−3 |
203 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 | ||
Cl1 | 0.02297 (6) | 0.70926 (4) | −0.07104 (3) | 0.03932 (13) | |
S1 | 0.36271 (5) | 0.19161 (4) | 0.40911 (3) | 0.02784 (11) | |
O1 | 0.19351 (14) | 0.58273 (10) | 0.44275 (8) | 0.0265 (2) | |
O2 | 0.21419 (17) | 0.18248 (12) | 0.32973 (11) | 0.0411 (3) | |
C1 | 0.29375 (19) | 0.37881 (14) | 0.39556 (12) | 0.0251 (3) | |
C2 | 0.20899 (19) | 0.50599 (14) | 0.28375 (12) | 0.0248 (3) | |
C3 | 0.1735 (2) | 0.52797 (15) | 0.16126 (13) | 0.0279 (3) | |
H3 | 0.2128 | 0.4481 | 0.1335 | 0.033* | |
C4 | 0.0781 (2) | 0.67216 (16) | 0.08294 (13) | 0.0290 (3) | |
C5 | 0.0153 (2) | 0.79189 (15) | 0.12135 (13) | 0.0298 (3) | |
H5 | −0.0515 | 0.8884 | 0.0634 | 0.036* | |
C7 | 0.14795 (19) | 0.62695 (15) | 0.31933 (12) | 0.0251 (3) | |
C6 | 0.0489 (2) | 0.77201 (15) | 0.24256 (13) | 0.0273 (3) | |
C8 | 0.28210 (19) | 0.43087 (14) | 0.48790 (12) | 0.0249 (3) | |
C9 | −0.0186 (2) | 0.89610 (16) | 0.28858 (15) | 0.0343 (3) | |
H9A | −0.1057 | 0.9849 | 0.2243 | 0.052* | |
H9B | 0.0929 | 0.9177 | 0.3116 | 0.052* | |
H9C | −0.0870 | 0.8668 | 0.3599 | 0.052* | |
C10 | 0.3426 (2) | 0.36521 (15) | 0.61893 (12) | 0.0262 (3) | |
C11 | 0.2685 (2) | 0.44896 (16) | 0.69082 (13) | 0.0299 (3) | |
H11 | 0.1763 | 0.5457 | 0.6543 | 0.036* | |
C12 | 0.3291 (2) | 0.39130 (18) | 0.81450 (14) | 0.0343 (3) | |
H12 | 0.2787 | 0.4499 | 0.8615 | 0.041* | |
C13 | 0.4619 (2) | 0.24959 (18) | 0.87129 (13) | 0.0339 (3) | |
C14 | 0.5333 (2) | 0.16600 (17) | 0.80041 (14) | 0.0338 (3) | |
H14 | 0.6229 | 0.0683 | 0.8379 | 0.041* | |
C15 | 0.4761 (2) | 0.22262 (16) | 0.67607 (13) | 0.0297 (3) | |
H15 | 0.5282 | 0.1639 | 0.6294 | 0.036* | |
C16 | 0.5257 (3) | 0.1898 (2) | 1.00639 (14) | 0.0458 (4) | |
H16A | 0.6069 | 0.0852 | 1.0331 | 0.069* | |
H16B | 0.4121 | 0.1986 | 1.0509 | 0.069* | |
H16C | 0.5994 | 0.2468 | 1.0229 | 0.069* | |
C17 | 0.5744 (2) | 0.18473 (17) | 0.32871 (14) | 0.0336 (3) | |
H17A | 0.6062 | 0.1004 | 0.3012 | 0.040* | |
H17B | 0.5467 | 0.2772 | 0.2556 | 0.040* | |
C18 | 0.7460 (2) | 0.16692 (17) | 0.40993 (15) | 0.0363 (3) | |
H18A | 0.7127 | 0.2480 | 0.4401 | 0.054* | |
H18B | 0.8561 | 0.1696 | 0.3630 | 0.054* | |
H18C | 0.7798 | 0.0717 | 0.4791 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0511 (3) | 0.0362 (2) | 0.02820 (19) | −0.01466 (18) | −0.00402 (16) | −0.00909 (15) |
S1 | 0.0307 (2) | 0.02136 (17) | 0.03107 (19) | −0.00773 (14) | 0.00090 (14) | −0.01020 (13) |
O1 | 0.0277 (5) | 0.0223 (5) | 0.0278 (5) | −0.0054 (4) | 0.0023 (4) | −0.0101 (4) |
O2 | 0.0422 (7) | 0.0359 (6) | 0.0484 (7) | −0.0158 (5) | −0.0071 (5) | −0.0166 (5) |
C1 | 0.0235 (6) | 0.0218 (6) | 0.0280 (6) | −0.0057 (5) | 0.0031 (5) | −0.0089 (5) |
C2 | 0.0210 (6) | 0.0230 (6) | 0.0296 (7) | −0.0065 (5) | 0.0029 (5) | −0.0098 (5) |
C3 | 0.0274 (7) | 0.0263 (6) | 0.0304 (7) | −0.0080 (5) | 0.0016 (5) | −0.0119 (5) |
C4 | 0.0283 (7) | 0.0304 (7) | 0.0275 (7) | −0.0106 (6) | −0.0006 (5) | −0.0092 (5) |
C5 | 0.0274 (7) | 0.0240 (6) | 0.0334 (7) | −0.0067 (5) | −0.0010 (6) | −0.0070 (5) |
C7 | 0.0225 (6) | 0.0241 (6) | 0.0280 (6) | −0.0068 (5) | 0.0017 (5) | −0.0100 (5) |
C6 | 0.0226 (6) | 0.0236 (6) | 0.0338 (7) | −0.0059 (5) | 0.0019 (5) | −0.0103 (5) |
C8 | 0.0222 (6) | 0.0216 (6) | 0.0304 (7) | −0.0068 (5) | 0.0041 (5) | −0.0098 (5) |
C9 | 0.0339 (8) | 0.0237 (7) | 0.0410 (8) | −0.0028 (6) | 0.0020 (6) | −0.0130 (6) |
C10 | 0.0258 (7) | 0.0275 (6) | 0.0275 (6) | −0.0121 (5) | 0.0056 (5) | −0.0102 (5) |
C11 | 0.0320 (7) | 0.0292 (7) | 0.0318 (7) | −0.0132 (6) | 0.0080 (6) | −0.0129 (6) |
C12 | 0.0398 (8) | 0.0396 (8) | 0.0318 (7) | −0.0199 (7) | 0.0115 (6) | −0.0173 (6) |
C13 | 0.0327 (8) | 0.0441 (8) | 0.0278 (7) | −0.0205 (7) | 0.0064 (6) | −0.0104 (6) |
C14 | 0.0294 (7) | 0.0340 (7) | 0.0315 (7) | −0.0097 (6) | 0.0021 (6) | −0.0058 (6) |
C15 | 0.0270 (7) | 0.0313 (7) | 0.0304 (7) | −0.0088 (6) | 0.0042 (5) | −0.0121 (6) |
C16 | 0.0473 (10) | 0.0616 (11) | 0.0283 (8) | −0.0238 (9) | 0.0054 (7) | −0.0117 (7) |
C17 | 0.0341 (8) | 0.0309 (7) | 0.0331 (7) | −0.0029 (6) | 0.0056 (6) | −0.0160 (6) |
C18 | 0.0332 (8) | 0.0325 (7) | 0.0451 (9) | −0.0107 (6) | 0.0082 (6) | −0.0172 (7) |
Cl1—C4 | 1.7465 (15) | C10—C15 | 1.397 (2) |
S1—O2 | 1.4962 (12) | C10—C11 | 1.4054 (19) |
S1—C1 | 1.7686 (13) | C11—C12 | 1.384 (2) |
S1—C17 | 1.8129 (16) | C11—H11 | 0.9500 |
O1—C7 | 1.3746 (16) | C12—C13 | 1.389 (2) |
O1—C8 | 1.3782 (15) | C12—H12 | 0.9500 |
C1—C8 | 1.3689 (19) | C13—C14 | 1.391 (2) |
C1—C2 | 1.4498 (18) | C13—C16 | 1.510 (2) |
C2—C7 | 1.3905 (18) | C14—C15 | 1.387 (2) |
C2—C3 | 1.3988 (19) | C14—H14 | 0.9500 |
C3—C4 | 1.3811 (19) | C15—H15 | 0.9500 |
C3—H3 | 0.9500 | C16—H16A | 0.9800 |
C4—C5 | 1.401 (2) | C16—H16B | 0.9800 |
C5—C6 | 1.388 (2) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | C17—C18 | 1.519 (2) |
C7—C6 | 1.3868 (18) | C17—H17A | 0.9900 |
C6—C9 | 1.5006 (19) | C17—H17B | 0.9900 |
C8—C10 | 1.4597 (19) | C18—H18A | 0.9800 |
C9—H9A | 0.9800 | C18—H18B | 0.9800 |
C9—H9B | 0.9800 | C18—H18C | 0.9800 |
C9—H9C | 0.9800 | ||
O2—S1—C1 | 106.72 (6) | C15—C10—C8 | 122.50 (13) |
O2—S1—C17 | 106.62 (7) | C11—C10—C8 | 119.29 (12) |
C1—S1—C17 | 98.27 (7) | C12—C11—C10 | 120.40 (14) |
C7—O1—C8 | 107.00 (10) | C12—C11—H11 | 119.8 |
C8—C1—C2 | 107.17 (12) | C10—C11—H11 | 119.8 |
C8—C1—S1 | 127.41 (10) | C11—C12—C13 | 121.40 (14) |
C2—C1—S1 | 124.75 (10) | C11—C12—H12 | 119.3 |
C7—C2—C3 | 119.38 (12) | C13—C12—H12 | 119.3 |
C7—C2—C1 | 104.93 (12) | C12—C13—C14 | 118.17 (14) |
C3—C2—C1 | 135.63 (13) | C12—C13—C16 | 120.22 (15) |
C4—C3—C2 | 116.30 (13) | C14—C13—C16 | 121.61 (15) |
C4—C3—H3 | 121.8 | C15—C14—C13 | 121.24 (14) |
C2—C3—H3 | 121.8 | C15—C14—H14 | 119.4 |
C3—C4—C5 | 123.25 (13) | C13—C14—H14 | 119.4 |
C3—C4—Cl1 | 119.41 (11) | C14—C15—C10 | 120.58 (14) |
C5—C4—Cl1 | 117.29 (11) | C14—C15—H15 | 119.7 |
C6—C5—C4 | 121.19 (13) | C10—C15—H15 | 119.7 |
C6—C5—H5 | 119.4 | C13—C16—H16A | 109.5 |
C4—C5—H5 | 119.4 | C13—C16—H16B | 109.5 |
O1—C7—C6 | 124.11 (12) | H16A—C16—H16B | 109.5 |
O1—C7—C2 | 110.69 (11) | C13—C16—H16C | 109.5 |
C6—C7—C2 | 125.17 (13) | H16A—C16—H16C | 109.5 |
C7—C6—C5 | 114.68 (12) | H16B—C16—H16C | 109.5 |
C7—C6—C9 | 122.11 (13) | C18—C17—S1 | 111.08 (10) |
C5—C6—C9 | 123.20 (13) | C18—C17—H17A | 109.4 |
C1—C8—O1 | 110.19 (12) | S1—C17—H17A | 109.4 |
C1—C8—C10 | 135.60 (12) | C18—C17—H17B | 109.4 |
O1—C8—C10 | 114.20 (11) | S1—C17—H17B | 109.4 |
C6—C9—H9A | 109.5 | H17A—C17—H17B | 108.0 |
C6—C9—H9B | 109.5 | C17—C18—H18A | 109.5 |
H9A—C9—H9B | 109.5 | C17—C18—H18B | 109.5 |
C6—C9—H9C | 109.5 | H18A—C18—H18B | 109.5 |
H9A—C9—H9C | 109.5 | C17—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
C15—C10—C11 | 118.19 (13) | H18B—C18—H18C | 109.5 |
O2—S1—C1—C8 | 131.72 (13) | C4—C5—C6—C7 | 0.2 (2) |
C17—S1—C1—C8 | −118.07 (13) | C4—C5—C6—C9 | −178.83 (14) |
O2—S1—C1—C2 | −37.66 (13) | C2—C1—C8—O1 | 0.68 (15) |
C17—S1—C1—C2 | 72.54 (13) | S1—C1—C8—O1 | −170.20 (10) |
C8—C1—C2—C7 | −1.27 (15) | C2—C1—C8—C10 | −178.15 (15) |
S1—C1—C2—C7 | 169.92 (10) | S1—C1—C8—C10 | 11.0 (2) |
C8—C1—C2—C3 | −178.44 (15) | C7—O1—C8—C1 | 0.20 (14) |
S1—C1—C2—C3 | −7.3 (2) | C7—O1—C8—C10 | 179.30 (11) |
C7—C2—C3—C4 | 0.1 (2) | C1—C8—C10—C15 | 15.7 (2) |
C1—C2—C3—C4 | 176.96 (15) | O1—C8—C10—C15 | −163.06 (12) |
C2—C3—C4—C5 | −1.2 (2) | C1—C8—C10—C11 | −165.94 (15) |
C2—C3—C4—Cl1 | −178.57 (10) | O1—C8—C10—C11 | 15.27 (18) |
C3—C4—C5—C6 | 1.0 (2) | C15—C10—C11—C12 | 0.8 (2) |
Cl1—C4—C5—C6 | 178.51 (11) | C8—C10—C11—C12 | −177.59 (13) |
C8—O1—C7—C6 | 176.97 (13) | C10—C11—C12—C13 | −0.8 (2) |
C8—O1—C7—C2 | −1.06 (14) | C11—C12—C13—C14 | 0.0 (2) |
C3—C2—C7—O1 | 179.17 (11) | C11—C12—C13—C16 | 179.84 (14) |
C1—C2—C7—O1 | 1.44 (15) | C12—C13—C14—C15 | 0.9 (2) |
C3—C2—C7—C6 | 1.2 (2) | C16—C13—C14—C15 | −179.02 (14) |
C1—C2—C7—C6 | −176.57 (13) | C13—C14—C15—C10 | −0.8 (2) |
O1—C7—C6—C5 | −179.01 (12) | C11—C10—C15—C14 | 0.0 (2) |
C2—C7—C6—C5 | −1.3 (2) | C8—C10—C15—C14 | 178.34 (13) |
O1—C7—C6—C9 | 0.0 (2) | O2—S1—C17—C18 | −170.38 (10) |
C2—C7—C6—C9 | 177.75 (13) | C1—S1—C17—C18 | 79.34 (11) |
Experimental details
Crystal data | |
Chemical formula | C18H17ClO2S |
Mr | 332.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 7.3638 (5), 10.2524 (6), 11.8335 (7) |
α, β, γ (°) | 68.949 (3), 89.362 (3), 71.460 (3) |
V (Å3) | 785.11 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.46 × 0.37 × 0.33 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.691, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13937, 3759, 3348 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.100, 1.06 |
No. of reflections | 3759 |
No. of parameters | 203 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.29 |
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
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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As a part of our ongoing study of 5-chloro-3-ethylsulfinyl-7-methyl-1-benzofuran derivatives which contain 4-fluorophenyl and 4 iodophenyl substituents in the 2-position (Choi et al. (2010a,b) for the F and I-compound, respectively), we report the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with the mean deviation from the least-squares plane defined by the nine constituent atoms which equals to 0.016 (1) Å. The 4-methylphenyl ring is also essentially planar, with the mean deviation of 0.004 (1) Å from the least-squares plane defined by the six core-ring atoms. The dihedral angle between the benzofuran ring system and the core of the 4-methylphenyl rings is 14.50 (4)°.
Let the centroid names Cg1, Cg2 and Cg3 be assigned to the benzene ring (C2–C7), the furan ring (C1/C2/C7/O1/C8) and the core of 4-methylphenyl ring (C10–C15), respectively: The centroid–centroid separations of Cg1···Cg3i, Cg1···Cg3ii and Cg2···Cg3i are 3.827 (2), 3.741 (2) and 3.843 (2) Å, respectively. (The symmetry codes are: (i) -x + 1, -y + 1, -z + 1; (ii) -x, -y + 1, -z + 1.)
The interplanar angles between the benzene and the core of 4-methylphenyl ring and between the furan and the core of 4-methylphenyl ring equal to 13.89 (4) and 15.53 (4)°, respectively. These angles are quite large for the 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.