Crystal structure and Hirshfeld surface analysis of (3aR,4S,7S,7aS)-4,5,6,7,8,8-hexa-chloro-2-{6-[(3aR,4R,7R,7aS)-4,5,6,7,8,8-hexa-chloro-1,3-dioxo-1,3,3a,4,7,7a-hexa-hydro-2H-4,7-methano-isoindol-2-yl]hex-yl}-3a,4,7,7a-tetra-hydro-1H-4,7-methano-iso-indole-1,3(2H)-dione.

Aygun I Alikhanova,Sixberth Mlowe,Zeliha Atioğlu,Mehmet Akkurt

doi:10.1107/s2056989021006952

Abstract

The mol-ecule of the title compound, C24H16Cl12N2O4, is generated by a crystallographic inversion centre at the midpoint of the central C-C bond. A kink in the mol-ecule is defined by a torsion angle of -169.86 (15)° about this central bond of the alkyl bridge. The pyrrolidine ring is essentially planar [max. deviation = 0.014 (1) Å]. The cyclo-hexane ring has a boat conformation, while both cyclo-pentane rings adopt an envelope conformation. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯O, C-H⋯Cl and C-Cl⋯π inter-actions, and short inter-molecular Cl⋯O and Cl⋯Cl contacts, forming a three-dimensional network.

Highlights

The molecule of the title compound, C24H16Cl12N2O4, is generated by a crystallographic inversion centre at the midpoint of the central C—C bond
Molecules are linked by intermolecular C—HÁ Á ÁO, C—HÁ Á ÁCl and C—ClÁ Á Á interactions, and short intermolecular ClÁ Á ÁO and ClÁ Á ÁCl contacts, forming a three-dimensional network
N-heterocycles or N-ligands can be used as precursors in the synthesis of coordination compounds (Ma et al, 2020, 2021; Mahmudov et al, 2013), and as building blocks in the construction of supramolecular structures as they have both hydrogen-bond donor and acceptor capabilities (Gurbanov et al, 2020a; Kopylovich et al, 2011a,b; Asgarova et al, 2019)

Summary

Chemical context

N-heterocyclic compounds are of interest in the fields of synthetic organic chemistry, coordination chemistry and medicinal chemistry because of their important biological properties (Mahmoudi et al, 2016, 2017a,b,c, 2018a,b; 2019; Viswanathan et al, 2019). For this reason, many approaches have been developed for their efficient and versatile synthesis (Gurbanov et al, 2017, 2018a,b; Ma et al, 2017a,b). Intermolecular halogen bonds and other types of non-covalent interactions in halogenated N-heterocyclic compounds can improve their solubility and other functional properties. Symmetry codes: (i) Àx þ 2; y À 12; Àz þ 12; (ii) Àx þ 2; Ày; Àz; (iii) Àx þ 2; y þ 12; Àz þ 12

Structural commentary

Supramolecular features and Hirshfeld surface analysis

Database survey

Synthesis and crystallization

Findings

Refinement