Carbonyl-carbonyl, carbonyl-pi 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. 2007

Rocio J Santos-Contreras, and Francisco J Martínez-Martínez, and Efrén V García-Báez, and Itzia I Padilla-Martínez, and Ana L Peraza, and Herbert Höpfl
Facultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán, Colima 28400, Mexico.

The title compounds, C(12)H(9)ClO(4), (I), and C(12)H(9)BrO(4), (II), are isomorphous and crystallize in the monoclinic space group P2(1)/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) degrees for (I), and by 9.07 (8) and 18.96 (18) degrees for (II), owing to their involvement in intermolecular interactions. In both compounds, layers of centrosymmetric hydrogen-bonded dimers are developed in the [-5 -2 22] plane through C-H...O interactions, involving both carbonyl groups as acceptors. Two families of dimers stack through C=O...C=O, C=O...pi and C-X...C=O (X = Cl and Br) dipolar interactions, as well as a C-H...pi interaction, developing the three-dimensional structure along the c axis.

UI MeSH Term Description Entries
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D006574 Heterocyclic Compounds, 2-Ring A class of heterocyclic compounds that include a two-ring fused structure. Both aromatic and non-aromatic ring structures are included in this category. Fused Heterocyclic Compounds, Two-Ring,Two Ring Heterocyclic Compounds,2-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Two Ring,Heterocyclic Compounds, 2 Ring
D006842 Hydrocarbons, Brominated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with BROMINE. Brominated Hydrocarbons
D006843 Hydrocarbons, Chlorinated Hydrocarbon compounds with one or more of the hydrogens replaced by CHLORINE. Chlorinated Hydrocarbon,Chlorinated Hydrocarbons,Organochlorine Compound,Chlorine Compounds, Organic,Organochlorine Compounds,Compound, Organochlorine,Compounds, Organic Chlorine,Compounds, Organochlorine,Hydrocarbon, Chlorinated,Organic Chlorine Compounds

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