Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of <i>C</i>,<i>C</i>,<i>N</i>-Triaryl Substituted Imines

Abstract

The X-ray crystal structures of C,C,N-triaryl-substituted imine compounds, which have methoxy or hydroxy group adjacent to the imino moiety, are reported and discussed in comparison with those of the precursor ketone compounds, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene and 1-(4-chlorobenzoyl)-2-hydroxy-7-methoxynaphthalene. In crystals, three aromatic rings in a molecule of the methyl ether-retained imine compound are positioned almost perpendicularly to each other by giving non-coplanar spatial organization of the single molecular structure [dihedral angles: 85.32(18)˚ for Clinked phenyl ring and naphthalene ring; 79.27(17)˚ for N-linked phenyl ring and naphthalene ring; 84.78(17)˚ for Clinked phenyl ring and N-linked phenyl ring]. Spatial organization of the analogous methyl ether-cleaved imine compound has essentially same topology [dihedral angles 80.39(6)˚ for the Clinked phenyl ring and naphthalene ring; 82.35(6)˚ for the N-linked phenyl ring and naphthalene ring; 87.09(7)˚ for C-and N-linked phenyl rings]. These structural features of triarylimines apparently differ from those of the precursor ketones. Two aromatic rings in the methyl ether-cleaved ketone compound make smaller dihedral angle [58.10(6)˚] by intramolecular hydrogen bond between ketonic carbonyl group and hydroxy group [2.5573(16) Å] than that of the methyl ether-retained ketone [72.06(7)˚]. In molecular packing, the methyl ether-retained imine forms tubular molecular alignments composed of R-S dimeric molecular pairs, whereas the methyl ether-retained ketone affords consecutively stacks of one configurated molecules.

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“…Coordination complexes have many medicinal, industrial and other pharmacological applications, such as anti-cholesterol, anti-HIV, antibacterial, antifungal, analgesic, antitubercular, and anticancer activities. These references [1][2][3][4][5][6][7][8][9][10] provide their synthetic history. Soriano-García et al (2007) synthesized 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-En-6,20-dione and used it in the treatment of androgen-dependent diseases [11].…”

Crystal structure of 7-methoxy-1-{[(E)-2,6-dimethylphenylimino] (phenyl)methyl}-2-naphthol: Clarification of non-covalent bonding interactions on the basis of spatial organization of single molecular structure and the molecular alignments

“…In order to accomplish the purpose, the authors have planned introduction of additional aromatic ring planes to the core of the aroylnaphthalene molecules to realize more crowded inner spatial situation in aromatic-rings accumulating molecule. As one of the molecular transformation approaches to obtain such spatial organization, the authors designed conversion of ketonic carbonyl group in 1-monoaroylnaphthalene to imino moiety by the reaction with aromatic amines [17,18]. Herein, the authors report crystal structure of novel triarylimine molecule, and discuss correlation among spatial structure of single molecule, non-covalent bonding interactions, and molecular accumulation structure by comparison with the precursor 1-monoaroylnaphthalene [19].…”