Intermolecular Interactions of Trichloromethyl Group in the Crystal State, the Case of 2‑Trichloromethyl‑3H‑4-quinazoline Polymorphs and 1‑Methyl-2-trichloroacetylpyrrole–Hirshfeld Surface Analysis of Chlorine Halogen Bonding

Intermolecular interactions in the crystal state, a possible source of the observed polymorphism, are investigated with the use of the combined crystallographic methods, theoretical computations, and a modern approach of Hirshfeld surface analysis. Special attention is paid to a trichloromethyl grou...

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Bibliographic Details
Published inCrystal growth & design Vol. 13; no. 9; pp. 3913 - 3924
Main Authors Rybarczyk-Pirek, Agnieszka J, Chęcińska, Lilianna, Małecka, Magdalena, Wojtulewski, Sławomir
Format Journal Article
LanguageEnglish
Published Washington,DC American Chemical Society 04.09.2013
Subjects
Condensed matter: structure, mechanical and thermal properties
Crystalline state (including molecular motions in solids)
Crystallographic aspects of phase transformations; pressure effects
Exact sciences and technology
Physics
Structure of solids and liquids; crystallography
Structure of specific crystalline solids
Intermolecular interaction
Stacking sequence
Chlorine
Experimental design
Digital simulation
Computerized simulation
Surface analysis
Van der Waals radius
Conformation
Polymorphism
Crystal structure
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Summary:Intermolecular interactions in the crystal state, a possible source of the observed polymorphism, are investigated with the use of the combined crystallographic methods, theoretical computations, and a modern approach of Hirshfeld surface analysis. Special attention is paid to a trichloromethyl group, a potential donor of halogen bonding. It is demonstrated that due to packing effects and stacking interactions, its conformation does not have to correspond to the lowest energy structure of an isolated molecule, leading to formation of different polymorphs. The analysis of Hirshfeld surfaces, in contrast to standard geometrical criterion of sum of van der Waals radii, indicates the dominant role of various chlorine intermolecular contacts into the overall molecular packing and reveals the characteristic features of the obtained fingerprint plots. These interactions, a subject of our special interest, are discussed in details in order to provide their comprehensive description by means of Hirshfeld surface analysis tools.
ISSN:1528-7483
1528-7505
DOI:10.1021/cg400584w