Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemi-hydrate and 1,6-di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile

Farid N Naghiyev; Victor N Khrustalev; Nikolai U Venskovsky; Tatiana A Tereshina; Ali N Khalilov; Mehmet Akkurt; Ajaya Bhattarai; İbrahim G Mamedov

doi:10.1107/S2056989022007356

Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemi-hydrate and 1,6-di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile

Acta Crystallogr E Crystallogr Commun. 2022 Jul 26;78(Pt 8):833-839. doi: 10.1107/S2056989022007356. eCollection 2022 Aug 1.

Authors

Farid N Naghiyev¹, Victor N Khrustalev^{2

3}, Nikolai U Venskovsky², Tatiana A Tereshina³, Ali N Khalilov^{4

1}, Mehmet Akkurt⁵, Ajaya Bhattarai⁶, İbrahim G Mamedov¹

Affiliations

¹ Department of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan.
² Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198, Russian Federation.
³ N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation.
⁴ "Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan.
⁵ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁶ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

In 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemihydrate, C₁₈H₁₄BrN₃O·0.5H₂O, (I), pairs of mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming dimers with an R ² ₂(12) ring motif. The dimers are connected by N-H⋯Br and O-H⋯O hydrogen bonds, and C-Br⋯π inter-actions, forming layers parallel to the (010) plane. 1,6-Di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile, C₁₃H₉N₅O, (II), crystallizes in the triclinic space group P with two independent mol-ecules (IIA and IIB) in the asymmetric unit. In the crystal of (II), mol-ecules IIA and IIB are linked by inter-molecular N-H⋯N and N-H⋯O hydrogen bonds into layers parallel to (001). These layers are connected along the c-axis direction by weak C-H⋯N contacts. C-H⋯π and C-N⋯π inter-actions connect adjacent mol-ecules, forming chains along the a-axis direction. In (I) and (II), the stability of the packing is ensured by van der Waals inter-actions between the layers. In (I), Hirshfeld surface analysis showed that the most important contributions to the crystal packing are from H⋯H (37.9%), C⋯H/H⋯C (18.4%), Br⋯H/H⋯Br (13.3%), N⋯H/H⋯N (11.5%) and O⋯H/H⋯O (10.0%) inter-actions, while in (II), H⋯H inter-actions are the most significant contributors to the crystal packing (27.6% for mol-ecule IIA and 23.1% for mol-ecule IIB).

Keywords: Hirshfeld surface analysis; crystal structure; dimers; disorder; hydrogen bonds; van der Waals interactions.

Grants and funding

This paper was supported by Baku State University and the Ministry of Science and Higher Education of the Russian Federation [award No. 075–03–2020-223 (0770–2020–0017)].