Qu-anti-tative analysis of weak non-covalent inter-actions in (Z)-3-(4-chloro-phen-yl)-2-phenyl-acrylo-nitrile: insights from PIXEL and Hirshfeld surface analysis

Mani Udayakumar; Margarita Cerón; Paulina Ceballos; Judith Percino; Subbiah Thamotharan

doi:10.1107/S2056989019003694

Qu-anti-tative analysis of weak non-covalent inter-actions in (Z)-3-(4-chloro-phen-yl)-2-phenyl-acrylo-nitrile: insights from PIXEL and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2019 Mar 26;75(Pt 4):499-505. doi: 10.1107/S2056989019003694. eCollection 2019 Apr 1.

Authors

Mani Udayakumar¹, Margarita Cerón², Paulina Ceballos², Judith Percino², Subbiah Thamotharan¹

Affiliations

¹ Biomolecular Crystallography Laboratory, Department of Bioinformatics, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur 613 401, India.
² Unidad de Polímeros y Electrónica Orgánica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Val3-Ecocampus Valsequillo, Independencia O2 Sur 50, San Pedro Zacachimalpa, Puebla, CP 72960, Mexico.

Abstract

In the solid state, the title compound, C₁₅H₁₀ClN, is disordered over two orientations with a refined occupancy ratio of 0.86 (2):0.14 (2). The crystal structure is mainly stabilized by inter-molecular C-H⋯N and C-H⋯Cl hydrogen bonds, and C-H⋯π inter-actions. The mol-ecules pack in columns and adjacent columns are linked by weak C-H⋯Cl inter-actions. The PIXEL energy analysis suggests that the inter-molecular C-H⋯π inter-actions form a strong dimer in the major component. Hirshfeld analysis reveals that H⋯C, H⋯H, H⋯Cl and H⋯N contacts are the most important contributors to the crystal packing.

Keywords: C—H⋯π interactions; Hirshfeld surface; PIXEL; acrylonitrile; conjugation; crystal structure; hydrogen bonding; two-dimensional fingerprint plots..