5-Cyclo­pentyl-2-methyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S160053681400868X

. 2014 Apr 26;70(Pt 5):o592. doi: 10.1107/S160053681400868X

5-Cyclopentyl-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran

Hong Dae Choi ^a, Pil Ja Seo ^a, Uk Lee ^b,^*

PMCID: PMC4011272 PMID: 24860390

Abstract

In the title compound, C₂₁H₂₂O₃S, the cyclopentyl ring adopts a twist conformation. The dihedral angle between the mean planes of the benzofuran and 4-methylphenyl rings is 72.38 (6)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯π interactions, forming a three-dimensional supramolecular network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012 ▶, 2014 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₂₁H₂₂O₃S
M _r = 354.45
Monoclinic,
a = 10.5452 (7) Å
b = 6.3093 (4) Å
c = 13.7813 (9) Å
β = 91.626 (4)°
V = 916.54 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.42 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.636, T _max = 0.746
13479 measured reflections
4144 independent reflections
3276 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.106
S = 1.02
4144 reflections
228 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 2111 Friedel pairs
Absolute structure parameter: 0.02 (6)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400868X/bt6977sup1.cif

e-70-0o592-sup1.cif^{(27.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400868X/bt6977Isup2.hkl

e-70-0o592-Isup2.hkl^{(203.1KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supporting information file. DOI: 10.1107/S160053681400868X/bt6977Isup3.cml

CCDC reference: 997753

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.44	3.279 (3)	148
C20—H20⋯O2ⁱⁱ	0.95	2.54	3.244 (3)	131
C9—H9⋯Cg1ⁱⁱⁱ	1.0	2.89	3.680 (3)	136
C12—H12B⋯Cg1^iv	0.99	2.88	3.591 (3)	129
C14—H14C⋯Cg2ⁱⁱ	0.98	2.94	3.826 (3)	151

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

1. Comment

As a part of our ongoing study of 5-cylcopentyl-2-methyl-1-benzofuran derivatives containing phenylsulfonyl (Seo et al., 2011), 4-bromophenylsulfonyl (Choi et al., 2012) and 3-methylphenylsulfonyl (Choi et al., 2014) substituents in the 3-position, we report here on the crystal structure of the title compound.

The title compound crystallizes in the non-centrosymmetric space group P_n.

In the title molecule (Fig. 1), the benzofuran ring is essentially planar, with a mean deviation of 0.011 (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 (2) Å from the least-squares plane defined by the six constituent atoms. The cyclopentyl ring has a twist conformation. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 72.38 (6)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively), resulting in a three-dimensional supramolecular network.

2. Experimental

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (290 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, 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 column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 398–399 K; R_f = 0.51 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation of a solution of the title compound in ethyl acetate at room temperature.