Crystal structure and Hirshfeld surface analyses, inter-molecular inter-action energies and energy frameworks of methyl 6-amino-5-cyano-2-(2-meth-oxy-2-oxoeth-yl)-4-(4-nitro-phen-yl)-4 H-pyran-3-carboxyl-ate

Farid N Naghiyev; Tuncer Hökelek; Victor N Khrustalev; Huseyn M Mamedov; Alebel N Belay; Jamshid Ashurov; Ibrahim G Mamedov

doi:10.1107/S2056989025001276

Crystal structure and Hirshfeld surface analyses, inter-molecular inter-action energies and energy frameworks of methyl 6-amino-5-cyano-2-(2-meth-oxy-2-oxoeth-yl)-4-(4-nitro-phen-yl)-4 H-pyran-3-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2025 Mar 11;81(Pt 4):296-302. doi: 10.1107/S2056989025001276. eCollection 2025 Apr 1.

Authors

Farid N Naghiyev¹, Tuncer Hökelek², Victor N Khrustalev^{3

4}, Huseyn M Mamedov⁵, Alebel N Belay⁶, Jamshid Ashurov⁷, Ibrahim G Mamedov¹

Affiliations

¹ Department of Chemistry, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan.
² Hacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye.
³ Peoples' Friendship University of Russia (RUDN University) Miklukho-Maklay St 6 Moscow 117198 Russian Federation.
⁴ N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow 119991, Russian Federation.
⁵ Faculty of Physics, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan.
⁶ Department of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia.
⁷ Institute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek St. 83, Tashkent, 100125, Uzbekistan.

Abstract

The title compound, C₁₇H₁₅N₃O₇, contains pyran and phenyl rings, with the pyran ring exhibiting a flattened-boat conformation. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming R ² ₂(12) ring motifs. These dimers are linked through N-H⋯O hydrogen bonds into a three-dimensional architecture. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯O/O⋯H (29.7%), H⋯H (28.7%), H⋯C/C⋯H (16.0%) and H⋯N/N⋯H (12.9%) inter-actions. In addition to van der Waals inter-actions and N-H⋯N and N-H⋯O hydrogen bonds, halogen bonds, tetrel bonds and pnictogen bonds also play an important role in the cohesion of the crystal structure.

Keywords: carboxylate; crystal structure; hydrogen bond.