2-(2-Meth­oxy­phen­yl)-1-benzofuran

Michaela Pojarová; Michal Dušek; Andrej Jančařík; Emanuel Makrlík; Zdeňka Sedláková

doi:10.1107/S1600536811017168

. 2011 May 14;67(Pt 6):o1427. doi: 10.1107/S1600536811017168

2-(2-Methoxyphenyl)-1-benzofuran

Michaela Pojarová ^a,^*, Michal Dušek ^a, Andrej Jančařík ^b, Emanuel Makrlík ^c, Zdeňka Sedláková ^d

PMCID: PMC3120470 PMID: 21754807

Abstract

In the title compound, C₁₅H₁₂O₂, the dihedral angle between the aromatic ring systems is 16.67 (6)°. The methyl C atom is almost coplanar with its attached benzene ring [displacement = 0.020 (2) Å]. In the crystal, the molecules are connected by weak C—H⋯O bonds and face-to-edge C—H⋯π interactions between the 2-methoxyphenyl rings.

Related literature

For the biological activity of related compounds, see: Akgul & Anil (2003 ▶); Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶); Soekamto et al. (2003 ▶). For the synthesis, see: Takeda et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₂O₂
M _r = 224.25
Orthorhombic,
a = 6.9419 (1) Å
b = 11.4409 (2) Å
c = 14.1703 (3) Å
V = 1125.43 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 120 K
0.27 × 0.25 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.683, T _max = 1.000
11347 measured reflections
2006 independent reflections
1955 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.088
S = 1.09
2006 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ▶), 822 Friedel pairs
Flack parameter: −0.2 (2)

Data collection: CrysAlis PRO (Oxford Diffraction, 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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017168/hb5866sup1.cif

e-67-o1427-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017168/hb5866Isup2.hkl

e-67-o1427-Isup2.hkl^{(98.7KB, hkl)}

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

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

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2ⁱ	0.96	2.57	3.272 (2)	131
C3—H3⋯Cg1ⁱⁱ	0.93	2.78	3.604 (2)	149

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

Acknowledgments

This work was supported by the Institutional research plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Sciences of the Czech Republic and the Czech Ministry of Education, Youth and Sports, project MSM 4977751303.

supplementary crystallographic information

Comment

A wide range of natural products with diverse pharmaceutical properties, such as antifungal, antitumor, antiviral, and antimicrobial (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005), contain a benzofuran ring (Akgul & Anil, 2003; Soekamto et al., 2003). In this paper, we present a crystal structure of the title compound, (I).

The benzofuran unit is essentially planar, with a mean deviation of 0.019 (2)Å from the least-square plane defined by the nine atoms in benzofuran ring. The methoxy group forms intermolecular hydrogen bond to the oxygen in benzofuran ring (Table 1). Another weak interactions found in the crystal is the C—H···π interaction between the 2-methoxyphenyl rings [C3—H3···Cg1 (C2 → C7)] which is responsible for their edge-to-face orientation (Fig. 2).

Experimental

2-(2'-methoxyphenyl]-benzo[b]furan was synthesized by the method described by Takeda (Takeda et al., 2007). Crystals were prepared by slow evaporation from acetonitrile.