4-Chloro­phenyl 2-oxo-2H-chromene-3-carboxyl­ate

Xiao-Qiang Guo; Jun Yan; Ya Gan; Qin Song; Xiao-Jun Gou

doi:10.1107/S1600536812003376

. 2012 Feb 4;68(Pt 3):o574. doi: 10.1107/S1600536812003376

4-Chlorophenyl 2-oxo-2H-chromene-3-carboxylate

Xiao-Qiang Guo ^a, Jun Yan ^a, Ya Gan ^a, Qin Song ^a, Xiao-Jun Gou ^a,^*

PMCID: PMC3297301 PMID: 22412491

Abstract

In title compound, C₁₆H₉ClO₄, the coumarin ring system is approximately planar [maximum deviation = 0.056 (1) Å] and is oriented with respect to the benzene ring at an angle of 22.60 (7)°. Intermolecular C—H⋯O hydrogen bonding is present in the crystal.

Related literature

For the biochemical properties of related compounds, see: Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Finn et al. (2002 ▶); Gursoy & Karali (2003 ▶); Borges et al. (2005 ▶). For the synthesis, see: Zhou et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₉ClO₄
M _r = 300.68
Monoclinic,
a = 15.7586 (6) Å
b = 7.0694 (2) Å
c = 12.7167 (6) Å
β = 113.037 (5)°
V = 1303.70 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 135 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.99, T _max = 1.00
5907 measured reflections
2662 independent reflections
2059 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.092
S = 1.04
2662 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003376/xu5453sup1.cif

e-68-0o574-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003376/xu5453Isup2.hkl

e-68-0o574-Isup2.hkl^{(130.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812003376/xu5453Isup3.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⋯O2ⁱ	0.95	2.34	3.061 (2)	133

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Applied Basic Research Program of Sichuan Provincial Science and Technology Department, China (grant No. 2009JY0113). The authors thank Mr Z.–H. Mao and Mr D.–B. Luo of the Analytical and Testing Center, Sichuan University, for assistance with the data collection.

supplementary crystallographic information

Comment

The coumarins and derivatives have demonstrated an ever-increasing variety of uses, including platelet anti-aggregating activity, anti-inflammatory activity (Kontogiorgis & Hadjipavlou-Litina, 2005), anti-tumor activity (Finn et al., 2002), anti-bacterials (Gursoy & Karali, 2003), and antiviral effect (Borges et al., 2005). So the title compound was synthesized according to the published method (Zhou et al., 2008). We report here the crystal structure of the title compound. In the title compound (Fig. 1), the dihedral angle between the planes of coumarin and benzene ring is 22.60 (7)°. The packing view of the title compound is shown in Fig. 2, weak intermolecular C—H···O hydrogen bonding is present in the crystal (Table 1).

Experimental

2-Oxo-2H-chromene-3-carboxylic acid (0.02 mol) was added to 10 ml sulfurous oxychloride. The mixture was refluxed for 3 h, and then the resultant was removed with simple distillation to give 2-oxo-2H-chromene-3-carbonyl chloride (3.95 g). The compound can be used directly without purification. The solution of 4-chlorophenol (0.0165 mol) dissolved in dried methyl dichloride (15 ml) was added dropwise to a solution of 2-oxo-2H-chromene-3-acyl chloride (0.015 mol) dissolved in methyl dichloride (20 ml) and triethylamine (2.5 ml) at room temperature. The reaction mixture was refluxed for 6 h, (mornitored by TLC). The mixture was then neutralized with 5% HCl and washed with saturated NaHCO₃ and brine respectively. The organic phase was dried over Na₂SO₄ and evaporated under the reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate: petroleum ether) to give the pure compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a mixed solvent (methyl dichloride: methanol) at room temperature.