title: Hydrogen bonding due to regioisomerism and its effect on the supramolecular architecture of diethyl 2-[(2/4-hydroxyanilino)methylidene]malonates.
abstract: Diethyl 2-[(2-hydroxyanilino)methylidene]malonate, (I), and diethyl 2-[(4-hydroxyanilino)methylidene]malonate, (II), both C(14)H(17)NO(5), crystallize in centrosymmetric orthorhombic and monoclinic crystal systems, respectively. Compound (I) resides on a crystallographic mirror plane and displays bifurcated intramolecular hydrogen bonding, as well as intermolecular hydrogen bonding due to the position of the hydroxy group. Compound (II) has a single intramolecular N-H...O hydrogen bond. Infinite one-dimensional head-to-tail chains formed by O-H...O hydrogen bonding are present in both structures. The molecular packing is mainly influenced by the intermolecular O-H...O interactions. Additionally, C-H...O interactions crosslinking the chains are found in (II).
authors.affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India. ilangovanbdu@yahoo.com
authors.forename: Andivelu
authors.initials: A
authors.lastname: Ilangovan
authors.forename: Perumal
authors.initials: P
authors.lastname: Venkatesan
authors.forename: Rajendran
authors.initials: R
authors.lastname: Ganesh Kumar
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D008314:Malonates; C579177:diethyl 2-((2-hydroxyanilino)methylidene)malonate; C579178:diethyl 2-((4-hydroxyanilino)methylidene)malonate