Cinnamyl 2-oxo-2H-chromene-3-carboxyl­ate

Cui-Lian Xu; Nan Yang; Guo-Yu Yang; Su-Fang Fan; Cao-Yuan Niu

doi:10.1107/S1600536809045644

. 2009 Nov 4;65(Pt 12):o2991. doi: 10.1107/S1600536809045644

Cinnamyl 2-oxo-2H-chromene-3-carboxylate

Cui-Lian Xu ^a,^*, Nan Yang ^b, Guo-Yu Yang ^a, Su-Fang Fan ^a, Cao-Yuan Niu ^a

PMCID: PMC2972065 PMID: 21578731

Abstract

The title compound, C₁₉H₁₄O₄, was prepared by the reaction of 2-oxo-2H-chromene-3-acyl chloride with cinnamic alcohol. The whole molecule is not planar, the dihedral angle between the planes of coumarin and benzene rings being 13.94 (4)°, but the plane of the coumarin ring and that of the ester group are almost coplanar, making a dihedral angle of 2.9 (1)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link two molecules into dimers, and π–π stacking interactions between inversion-related rings of the coumarin groups [centroid–centroid distance 3.8380 (15) Å with a slippage of 1.535 Å], which connect the dimers into columns extending along [010].

Related literature

For the medicinal and biological activity of coumarins and their derivatives, see: Borges et al. (2005 ▶); Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Gursoy & Karali (2003 ▶). For the development of coumarin derivatives as anti-HIV agents, see: Yu et al. (2003 ▶, 2007 ▶). For the structure of menthyl 2-oxo-2H-chromene-3-carboxylate, see: Xu et al. (2009 ▶). graphic file with name e-65-o2991-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₄O₄
M _r = 306.30
Monoclinic,
a = 5.7026 (11) Å
b = 8.2969 (17) Å
c = 31.693 (6) Å
β = 92.96 (3)°
V = 1497.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 K
0.20 × 0.18 × 0.18 mm

Data collection

Rigaku R-AXIS-IV diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.981, T _max = 0.983
4266 measured reflections
2485 independent reflections
2002 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.147
S = 1.08
2485 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: R-AXIS (Rigaku, 1997 ▶); cell refinement: R-AXIS data reduction: R-AXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation & Rigaku, 2000 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045644/si2212sup1.cif

e-65-o2991-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045644/si2212Isup2.hkl

e-65-o2991-Isup2.hkl^{(122.1KB, hkl)}

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
C5—H5A⋯O3ⁱ	0.93	2.54	3.344 (3)	145
C7—H7A⋯O3ⁱ	0.93	2.46	3.292 (3)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Foundation of Henan Province (No. 2009A150012).

supplementary crystallographic information

Comment

The coumarins and derivatives display a wide range of biological activities, such as antiviral effect (Borges et al., 2005), anti-inflammatories (Kontogiorgis & Hadjipavlou-Litina, 2005), anti-bacterials (Gursoy & Karali, 2003), and anti-proliferative properties. (Yu et al., 2003; Yu et al., 2007), as well as being a kind of basic flavor compounds. As part of work, we have synthesized the title compound (I) and report its crystal structure here.

The molecular structure of (I) is shown in Fig. 1. It crystallizes in the E conformation, with an C11—C12—C13—C14 torsion angle of -19.6 (3)°. The plane of the coumarin ring and that of the ester group are almost co-planar, with a small dihedral angle of 2.9 (1) °, but the coumarin ring is not coplanar with the C14-benzene ring, forming a dihedral angle of 13.94 (4)°.

There are weak intermolecular C—H···O hydrogen bonds (Table 1) that link two molecules into a dimer (Fig. 2), and π-π stackings between two parallel rings [Cg1:O1, C1, C6, C7, C8, C9 and Cg2:C1ⁱ - C6ⁱ. Symmetry code:(i) -x, 1 - y, -z] with a slippage of 1.535 Å and Cg1···Cg2 distance of 3.8380 (15) Å that helps to connect dimers into columns along the b axis (Fig. 3). The perpendicular distance between the stacked coumarin rings is 3.518 Å.

Experimental

Compound (I) was synthesized as reported by Xu et al. (2009), starting from 2-oxo-2H-chromene-3-acyl chloride and cinnamic alcohol in equimolar amounts. Single crystals of the title compound suitable for X-ray diffractions were obtained by slow evaporation of a mixed solvent (ethyl acetate: petroleum ether = 1: 3, 7 ml) solution of the title compound (0.030 g).