Crystal structure and Hirshfeld surface analysis of 2,2,2-tri-chloro- N, N-bis-{[(1 RS,4 SR)-1,4-di-hydro-1,4-ep-oxy-naphthalen-1-yl]meth-yl}acetamide

Zeliha Atioğlu; Mehmet Akkurt; Gunay Z Mammadova; Ajaya Bhattarai

doi:10.1107/S2056989021009907

Crystal structure and Hirshfeld surface analysis of 2,2,2-tri-chloro- N, N-bis-{[(1 RS,4 SR)-1,4-di-hydro-1,4-ep-oxy-naphthalen-1-yl]meth-yl}acetamide

Acta Crystallogr E Crystallogr Commun. 2021 Sep 28;77(Pt 10):1048-1053. doi: 10.1107/S2056989021009907. eCollection 2021 Oct 1.

Authors

Zeliha Atioğlu¹, Mehmet Akkurt², Gunay Z Mammadova³, Ajaya Bhattarai⁴

Affiliations

¹ Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Turkey.
² Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
³ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
⁴ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

In the title compound, C₂₄H₁₈Cl₃NO₃, the tetra-hydro-furan rings adopt envelope conformations. In the crystal, C-H⋯O hydrogen bonds connect mol-ecules, generating layers parallel to the (001) plane. These layers are connected along the c-axis direction by C-H⋯π inter-actions. The packing is further stabilized by inter-layer van der Waals and inter-halogen inter-actions. The most important contributions to the surface contacts are from H⋯H (36.8%), Cl⋯H/H⋯Cl (26.6%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (11.3%) inter-actions, as concluded from a Hirshfeld surface analysis.

Keywords: C—H⋯O hydrogen bonds; C—H⋯π interactions; Diels–Alder reaction; Hirshfeld surface analysis; IMDAF reaction; crystal structure; tetrahydrofuran rings.