Crystal structure of 2,5-dimethyl-3-(2-methyl­phenyl­sulfon­yl)-1-benzo­furan

Hong Dae Choi; Uk Lee

doi:10.1107/S1600536814022788

. 2014 Oct 24;70(Pt 11):o1181–o1182. doi: 10.1107/S1600536814022788

Crystal structure of 2,5-dimethyl-3-(2-methylphenylsulfonyl)-1-benzofuran

Hong Dae Choi ^a, Uk Lee ^b,^*

PMCID: PMC4257330 PMID: 25484818

Abstract

The title compound, C₁₇H₁₆O₃S, crystallized with two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the benzofuran ring system [r.m.s. deviation of 0.013 (1) for A and 0.009 (1) Å for B] and the 2-methylphenyl ring is 83.88 (5) for A and 86.94 (5)° for B. In the crystal, the B molecules are linked into a chain along the b-axis direction by C—H⋯O hydrogen bonds. The A molecules are connected on either side of this chain by further C—H⋯O hydrogen bonds. These chains are linked via C—H⋯π interactions, forming sheets parallel to (100). There are also very weak π–π interactions present [centroid–centroid distance = 3.925 (11) Å] involvingthe 2-methylphenyl rings of neighbouring A and B molecules.

Keywords: crystal structure, benzofuran, 2-methylphenyl, sulfonyl, C—H⋯O hydrogen bonds, C—H⋯π interactions, π–π interactions

Related literature

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C₁₇H₁₆O₃S
M _r = 300.36
Monoclinic,
a = 16.7338 (4) Å
b = 8.0646 (2) Å
c = 21.8195 (6) Å
β = 95.296 (1)°
V = 2932.00 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.58 × 0.37 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.879, T _max = 0.950
27259 measured reflections
6773 independent reflections
5313 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.04
6773 reflections
385 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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/S1600536814022788/su5004sup1.cif

e-70-o1181-sup1.cif^{(837.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022788/su5004Isup2.hkl

e-70-o1181-Isup2.hkl^{(331.5KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814022788/su5004Isup3.cml

Click here for additional data file.^{(480.8KB, tif)}

. DOI: 10.1107/S1600536814022788/su5004fig1.tif

The molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(443.1KB, tif)}

x y z x y z x y z x y z . DOI: 10.1107/S1600536814022788/su5004fig2.tif

A view of the C—H⋯O interactions (dashed lines) in the crystal structure of the title compound - see Table 1 for details. H atoms not involved in hydrogen bonding have been omitted for clarity [Symmetry codes: (i) −x, y + Inline graphic , −z + ; (ii) x, y + 1, z; (iii) −x, y − , −z + ; (iv) x, y − 1, z].

Click here for additional data file.^{(554.3KB, tif)}

x y z x y z . DOI: 10.1107/S1600536814022788/su5004fig3.tif

A view of the C—H⋯π and π–π interactions (dashed lines) in the crystal structure of the title compound - see Table 1 for details. H atoms non-participating in hydrogen-bonding have been omitted for clarity [Symmetry codes: (i) x, −y + Inline graphic , z − ; (ii) x, −y + , z + ].

CCDC reference: 1029621

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

Table 1. Hydrogen-bond geometry (, ).

Cg1 and Cg2 are the centroids of benzene rings C2C7 and C19C24, respectively.

DHA	DH	HA	D A	DHA
C23H23O5ⁱ	0.95	2.52	3.431(3)	162
C34H34BO2ⁱⁱ	0.98	2.43	3.137(2)	129
C31H31Cg1ⁱⁱ	0.95	2.93	3.773(3)	148
C14H14Cg2ⁱ	0.95	3.00	3.876(3)	154

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

Acknowledgments

The X-ray centre of Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

supplementary crystallographic information

S1. Comment

As part of our continuing program on benzofuran derivatives (Choi & Lee, 2014), we report herein on the crystal structure of the title compound which crystallizes with two symmetrically independent molecules (A and B) in the asymmetric unit.

In the title molecules (A and B; Fig. 1), the benzofuran units are essentially planar, with mean deviations of 0.013 (1) and 0.009 (1) Å for A and B, respectively, from the mean planes defined by the nine constituent non-H atoms. The dihedral angles formed by the benzofuran ring systems and the 2-methylphenyl rings are 83.88 (5) and 86.94 (5)° for A and B, respectively.

In the crystal, the B molecules are linked into a chain along the b axis direction by C—H···O hydrogen bonds (Table 1 and Fig. 2). The A molecules are connected on either side of this chain by further C-H···O hydrogen bonds (Table 1). These chains are linked via C—H···π interactions forming sheets parallel to (100); see Table 1. There are also very weak π···π interactions present (Fig. 3) involving 2-methylphenyl rings of neighbouring A and B molecules [Cg3···Cg7ⁱ = 3.925 (11) Å, where Cg3 and Cg7 are the centroids of rings C11-C16 and C28-C33; symmetry code: (i) = x, -y+3/2, z+1/2].

S2. Experimental

The starting material 2,5-dimethyl-3-(2-methylphenylsulfanyl)-1-benzofuran was prepared by the literature method (Choi et al., 1999). 3-chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 2,5-dimethyl-3-(2-methylphenylsulfanyl)-1-benzofuran (295 mg, 1.1 mmol) in dichloromethane (35 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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 colourless solid [yield 71%; 222 mg; m.p. 385–386 K; R_f = 0.54 (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 (23 mg) in ethyl acetate (20 ml) at room temperature.