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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-tri-chloro-benzene 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 intra-molecular O-H⋯O=C hydrogen bond forms an S(6) ring motif. In the crystal, no effective inter-molecular 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.
Highlights
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)
Since the discovery of an effective method for diaroylation at the 1,8(peri)-positions of the naphthalene ring core and the related reactions (Okamoto & Yonezawa, 2009; Okamoto et al, 2011; Okamoto, Mitsui et al, 2012), we have reported on the spatial organization of 1,8-diaroylated naphthalenes and homologous compounds in both the solid state and solution (Okamoto, Watanabe et al, 2012; Yoshiwaka et al, 2015; Okamoto et al, 2015; Ohisa et al, 2018)
Summary
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) and the associated two-dimensional fingerprint plots (McKinnon et al, 2007) were performed with CrystalExplorer (Turner et al, 2017). The Hirshfeld surfaces are colour-mapped with the normalized contact distance, dnorm, from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The two-dimensional fingerprint plots from the Hirshfeld surface analysis are shown, revealing the intermolecular contacts and their percentage distributions on the Hirshfeld surface. (3.9%), CÁ Á ÁC (3.0%) and OÁ Á ÁC/CÁ Á ÁO (1.3%) contacts make significant contributions to the Hirshfeld surface
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Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
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