Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

Abstract

In the title compound, C25H12Cl6O4, the two carbonyl groups are oriented in a same direction with respect to the naphthalene ring system and are situated roughly parallel to each other, while the two 2,4,6-trichlorobenzene rings are orientated in opposite directions with respect to the naphthalene ring system: the carbonyl C—(C=O)—C planes subtend dihedral angles of 45.54 (15) and 30.02 (15)° to the naphthalene ring system are. The dihedral angles formed by the carbonyl groups and the benzene rings show larger differences, the C=O vectors being inclined to the benzene rings by 46.39 (16) and 79.78 (16)°. An intramolecular O—H...O=C hydrogen bond forms an S(6) ring motif. In the crystal, no effective intermolecular hydrogen bonds are found; instead, O...Cl and C...Cl close contacts are observed along the 21 helical-axis direction. The Hirshfeld surface analysis reveals several weak interactions, the major contributor being Cl...H/H...Cl contacts.

Weak interaction based interpretation of crystal packing characteristics of aromatic rings accumulating molecules: Hirshfeld surface analyses reinforced X-ray crystal study on 1,8-dibenzoyl-7-ethoxynaphthalen-2- ol and its 2-ethoxylated homologue

“…Furthermore, the authors have been investigating the relationship between the crystalline packing structure and the inter-/intramolecular interaction through crystal structural study occasionally with the help of Hirshfeld surface analyses [23,24]. This reinforced crystal analysis protocol has afforded several successful results to reveal the governing schemes for the crystal packings with standpoint of the roles of rather powerless intermolecular interactions, which are weaker than classical hydrogen bonding for example … stackings and nonclassical hydrogen bondings [25,26].…”