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Influence of ortho ‐substituent on the molecular and crystal structures of 2‐( N ‐arylimino)coumarin‐3‐carboxamide: isotypic and polymorphic structures
Author(s) -
Shishkina Svitlana V.,
Konovalova Irina S.,
Kovalenko Sergiy M.,
Trostianko Pavlo V.,
Geleverya Anna O.,
Nikolayeva Lyudmila L.,
Bunyatyan Natalya D.
Publication year - 2019
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520619010485
Subject(s) - crystal structure , chemistry , substituent , carboxamide , halogen , coumarin , stereochemistry , group (periodic table) , aryl , crystal (programming language) , derivative (finance) , molecule , crystallography , organic chemistry , alkyl , computer science , financial economics , programming language , economics
During a comprehensive study of a series of 2‐( N ‐arylimino)coumarin‐3‐carboxamides with the aryl group substituted in the ortho ‐position by either a halogen atom, a methyl group or a methoxy group, the existence of three groups of isotypic crystal structures has been revealed. The similarity of crystal structures belonging to the same groups was confirmed by the analysis based on the comparison of pairwise interactions energies obtained from quantum chemical calculations. Group I includes unsubstituted, methyl‐substituted and polymorphic modification 1 of fluoro‐substituted 2‐( N ‐arylimino)coumarin‐3‐carboxamide. Structures of polymorphic modification 2 of fluoro‐substituted derivative, chloro‐substituted and polymorphic modification 1 of bromo‐substituted 2‐( N ‐arylimino)coumarin‐3‐carboxamide may represent group II. Group III contains structures of polymorphic modification 2 of bromo‐substituted derivative, iodine‐ and methoxy‐substituted 2‐( N ‐arylimino)coumarin‐3‐carboxamides. Structures of the same type group have extremely close parameters of the unit cell as well as those of molecular and crystal structures. But they are not identical. Polymorphic modifications of fluoro‐ and bromo‐substituted 2‐( N ‐arylimino)coumarin‐3‐carboxamides belong to different crystal types mainly due to different arrangement of basic structural motifs separated out using quantum chemical calculations.