3-(2-Meth­oxy­naphthalen-1-yl)-2-benzofuran-1(3H)-one

V Silambarasan; S Sundaramoorthy; R Sivasakthikumaran; A K Mohanakrishnan; D Velmurugan

doi:10.1107/S1600536811026596

. 2011 Jul 9;67(Pt 8):o1973. doi: 10.1107/S1600536811026596

3-(2-Methoxynaphthalen-1-yl)-2-benzofuran-1(3H)-one

V Silambarasan ^a, S Sundaramoorthy ^a, R Sivasakthikumaran ^b, A K Mohanakrishnan ^b, D Velmurugan ^a,^*

PMCID: PMC3213432 PMID: 22091011

Abstract

The asymmetric unit of the title compound, C₁₉H₁₄O₃, contains two crystallographically independent molecules in which the dihedral angles between the naphthalene and benzofuran ring systems are 76.49 (7) and 86.17 (7)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen-bonding interactions into chains running parallel to the a axis. In addition, the crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Aslam et al. (2006 ▶); Galal et al. (2009 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶). For related structures see: Thenmozhi et al. (2010 ▶); Valerga et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₁₄O₃
M _r = 290.30
Monoclinic,
a = 13.2572 (5) Å
b = 11.8560 (4) Å
c = 18.6160 (7) Å
β = 91.657 (2)°
V = 2924.79 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.979, T _max = 0.982
27565 measured reflections
7292 independent reflections
4519 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.122
S = 1.00
7292 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026596/sj5168sup1.cif

e-67-o1973-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026596/sj5168Isup2.hkl

e-67-o1973-Isup2.hkl^{(349.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026596/sj5168Isup3.cml

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

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

Cg2, Cg4 and Cg8 are the centroids of C1–C6, C13–C18 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O6ⁱ	0.93	2.45	3.238 (2)	142
C14—H14⋯O6ⁱⁱ	0.93	2.51	3.435 (2)	175
C12—H12⋯Cg4ⁱⁱ	0.98	2.93	3.755 (2)	143
C15—H15⋯Cg2ⁱⁱⁱ	0.93	2.88	3.800 (2)	169
C16—H16⋯Cg8^iv	0.93	2.81	3.553 (2)	137
C30—H30C⋯Cg8^v	0.96	2.89	3.687 (2)	141

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

Acknowledgments

SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

supplementary crystallographic information

Comment

Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Galal et al., 2009). Compounds with the benzofuran skeleton (Akgul & Anil, 2003) show significant pharmacological activities such as fungicidal (Aslam et al., 2006), antitumor and antiviral activities (Galal et al., 2009). In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Fig. 1 shows the asymmetric unit consisting of two molecules of the title compound. The naphthalene ring system is itself planar and the benzofuran ring system is also planar with a maximum deviation of 0.039 (1), 0.008 (1) Å, respectively in one molecule and 0.022 (2), 0.033 (1) Å in the other. The dihedral angles between the naphthalene ring systems and the benzofuran ring systems are 76.49 (7) and 86.17 (7)° in the two molecules. The C7—C8—O1—C11 [179.12 (15)°] and C29—C28—O4—C30 [179.87 (140)°] torsional angles that indicate the methoxy substitutions are essentially coplanar with the attached ring.

Hydrogen bond interactions are shown in Table 1 and the C—H···π interactions (Cg2, Cg4 and Cg8 are centriods of the rings containing the atoms C1—C6, C13—C18 and C20—C25 respectively). In the crystal structure, molecules are linked by intermolecular C—H···O hydrogen-bonding interactions into chains running parallel to the a axis.

Experimental

A mixture of 2-hydrazinopyridine and tolualdehyde were refluxed in ethanol with a catalytic quantity of conc. HCl or gl. AcOH. After the reaction is over, the contents were cooled down and the resulting product was filtered off. Diffraction quality crystals were obtained upon recrystallization in ethanol.