Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 4 (April 2007)

organic compounds

su3001 scheme

Acta Cryst. (2007). C63, o239-o242 [ doi:10.1107/S0108270107008712 ]

Carbonyl-carbonyl, carbonyl- and carbonyl-halogen dipolar interactions as the directing motifs of the supramolecular structure of ethyl 6-chloro-2-oxo-2H-chromene-3-carboxylate and ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate

R. J. Santos-Contreras, F. J. Martínez-Martínez, E. V. García-Báez, I. I. Padilla-Martínez, A. L. Peraza and H. Höpfl

Abstract: The title compounds, C₁₂H₉ClO₄, (I), and C₁₂H₉BrO₄, (II), are isomorphous and crystallize in the monoclinic space group P2₁/c. Both compounds present an anti conformation between the 3-carboxy and the lactone carbonyl groups. Both carbonyl groups are out of the plane defined by the remaining chromene atoms, by 8.37 (6) and 17.57 (6)° for (I), and by 9.07 (8) and 18.96 (18)° for (II), owing to their involvement in intermolecular interactions. In both compounds, layers of centrosymmetric hydrogen-bonded dimers are developed in the [ $\overline{5}$ $\overline{2}$ 22] plane through C-HO interactions, involving both carbonyl groups as acceptors. Two families of dimers stack through C=OC=O, C=O [pi] and C-XC=O (X = Cl and Br) dipolar interactions, as well as a C-H [pi] interaction, developing the three-dimensional structure along the c axis.

Formula: C₁₂H₉ClO₄ and C₁₂H₉BrO₄


	Structure factor file (CIF format) (125.8 kbytes) [ doi:10.1107/S0108270107008712/su3001Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (132.5 kbytes) [ doi:10.1107/S0108270107008712/su3001IIsup3.hkl ] Contains datablock II

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