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

• 作者: Akiko Okamoto Atsushi Nagasawa Noriyuki Yonezawa Siqingaowa
• 来源期刊: 晶体结构理论与应用(英文)
• 学科: 化学
• 关键词: Non-Coplanarly Accumulated Aromatic Rings Spatial Organization Triarylimine
• 年，卷（期）: 2013,（4）
• 页码范围: 139-147
• 页数: 9页
• 分类号: O6

摘要

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 C-linked phenyl ring and naphthalene ring;79.27(17)° for N-linked phenyl ring and naphthalene ring;84.78(17)° for C-linked 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 C-linked 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) A] 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.