Synthesis, crystal structure and Hirshfeld surface analysis of N-(6-acetyl-1-nitro-naphthalen-2-yl)acetamide

Xin-Wei Shi; Shao-Jun Zheng; Qiang-Qiang Lu; Gen Li; Ya-Fu Zhou

doi:10.1107/S2056989024001609

Synthesis, crystal structure and Hirshfeld surface analysis of N-(6-acetyl-1-nitro-naphthalen-2-yl)acetamide

Acta Crystallogr E Crystallogr Commun. 2024 Mar 6;80(Pt 4):347-350. doi: 10.1107/S2056989024001609. eCollection 2024 Mar 1.

Authors

Xin-Wei Shi¹, Shao-Jun Zheng², Qiang-Qiang Lu¹, Gen Li¹, Ya-Fu Zhou¹

Affiliations

¹ Xi'an Botanical Garden of Shaanxi Province (Institute of Botany of Shaanxi Province), Shaanxi Engineering Research Centre for Conservation and Utilization of Botanical Resources, Xi'an 710061, People's Republic of China.
² School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, Jiangsu, People's Republic of China.

Abstract

The title compound, C₁₄H₁₂N₂O₄, was obtained from 2-acetyl-6-amino-naphthalene through two-step reactions of acetyl-ation and nitration. The mol-ecule comprises the naphthalene ring system consisting of functional systems bearing a acetyl group (C-2), a nitro group (C-5), and an acetyl-amino group (C-6). In the crystal, the mol-ecules are assembled into two-dimensional sheet-like structures by inter-molecular N-H⋯O and C-H⋯O hydrogen-bonding inter-actions. Hirshfeld surface analysis illustrates that the most important contributions to the crystal packing are from O⋯H/H⋯O (43.7%), H⋯H (31.0%), and C⋯H/H⋯C (8.5%) contacts.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bonding; naphthalene ring.

Grants and funding

Funding for this research was provided by: the Xi’an Science and Technology Plan Project (grant No. 20NYYF0043); the Key Research and Development Program of Shaanxi (grant No. 2023-YBNY-248 and 2023-YBNY-100); the Key Research and Development Program of China (grant No. 2021YFD1600400); the National Natural Science Foundation of China (grant No. 42301053).