1-(1-Benzofuran-2-yl)-2-(phenyl­sulfon­yl)ethanone

Hatem A Abdel-Aziz; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811037366

. 2011 Sep 17;67(Pt 10):o2675. doi: 10.1107/S1600536811037366

1-(1-Benzofuran-2-yl)-2-(phenylsulfonyl)ethanone

Hatem A Abdel-Aziz ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3201267 PMID: 22058784

Abstract

The overall molecular conformation of the title compound, C₁₆H₁₂O₄S, is elongated, the dihedral angle formed between the benzofuran (r.m.s. deviation = 0.018 Å) and benzene rings being 24.81 (6)°. Both sulfonyl O atoms lie to one side of the S-bound benzene ring, and the carbonyl and furan O atoms are syn to each other. Supramolecular arrays parallel to (101) sustained by C—H⋯O contacts feature in the crystal packing.

Related literature

For the biological activity of sulfones, see: Garuti et al. (2002 ▶), and of benzofuran, see: Abdel-Aziz & Mekawey (2009 ▶). For previous work on the chemistry and biological activity of benzofurans, see: Abdel-Wahab et al. (2009 ▶); Abdel-Aziz et al. (2009 ▶, 2011 ▶). For the synthesis, see: Takahashi et al. (1986 ▶).

Experimental

Crystal data

C₁₆H₁₂O₄S
M _r = 300.32
Monoclinic,
a = 10.7560 (2) Å
b = 4.7855 (1) Å
c = 26.1838 (5) Å
β = 91.024 (2)°
V = 1347.54 (5) Å³
Z = 4
Cu Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.598, T _max = 1.000
4617 measured reflections
2650 independent reflections
2495 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.086
S = 1.04
2650 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037366/pk2346sup1.cif

e-67-o2675-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037366/pk2346Isup2.hkl

e-67-o2675-Isup2.hkl^{(130.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037366/pk2346Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.55	3.1808 (19)	124
C7—H7a⋯O2ⁱⁱ	0.99	2.57	3.5383 (17)	165
C7—H7b⋯O1ⁱ	0.99	2.47	3.3746 (17)	152
C15—H15⋯O3ⁱⁱⁱ	0.95	2.47	3.2742 (17)	142

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

Acknowledgments

The authors thank King Saud University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The investigation of the title compound, (I), a composite of sulphone and benzofuran groups, was motivated by the known biological activity of each component (Garuti et al., 2002; Abdel-Aziz & Mekawey, 2009) and represents a continuation of on-going biological and structural studies in this area (Abdel-Wahab et al., 2009; Abdel-Aziz et al., 2009; Abdel-Aziz et al., 2011).

With respect to the S-bound benzene ring in (I), Fig. 1, the two sulfonyl-O atoms lie to one side and the methylene group to the other. The benzofuran group is planar (r.m.s. deviation = 0.018 Å) and is splayed out with respect to the rest of the molecule. The dihedral angle between the S-bound benzene and benzofuran rings is 24.81 (6) ° so that overall the molecule has a flattened shape. The carbonyl- and benzofuran-O atoms are syn to each other.

The crystal packing is dominated by C—H···O interactions, Table 1, involving all but the benzofuran-O4 atom. These lead to the formation of supramolecular arrays parallel to (101), Fig. 2. There are no specific interactions between the layers, Fig. 3.

Experimental

The title compound was prepared according to the reported method (Takahashi et al., 1986). The yellow crystals were isolated from a mixture of EtOH/DMF (v/v = 3/1) by slow evaporation at room temperature.