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

Akiko Okamoto, Atsushi Nagasawa, Siqingaowa, Noriyuki Yonezawa
2013 Crystal Structure Theory and Applications  
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
more » ... ng 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) 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.
doi:10.4236/csta.2013.24019 fatcat:kzooqiz3vzhrffbl3t5ejzg4rq