1,8-Bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene

Atsushi Nagasawa,Noriyuki Yonezawa,Akiko Okamoto,Kotaro Kataoka,Takahiro Nishijima

doi:10.1107/s1600536810041346

Abstract

The title compound {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C26H22O4N2, possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the molecules interact through intermolecular N—H⋯O hydrogen bonds between the amino and methoxy groups on the naphthalene ring systems and N—H⋯π interactions between the amino groups and the naphthalene rings. Furthermore, weak C—H⋯O hydrogen bonds and π–π stacking interactions between the benzene rings are observed. The centroid–centroid and interplanar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent molecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5)°. The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C—C—C—O torsion angle = 175.91 (10)°].

Highlights

The title compound {systematic name: [8-(4-aminobenzoyl)2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C26H22O4N2, possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis
The molecules interact through intermolecular N—
H atoms treated by a mixture of independent and constrained refinement max = 0.24 e Å3

Summary

Data collection

R factor = 0.043; wR factor = 0.114; data-to-parameter ratio = 10.6. H O hydrogen bonds between the amino and methoxy groups on the naphthalene ring systems and N—H interactions between the amino groups and the naphthalene rings. Weak C—H O hydrogen bonds and – stacking interactions between the benzene rings are observed. The centroid–centroid and interplanar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent molecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5). The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C—C—C—O torsion angle =

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The authors express their gratitude to Professor Keiichi

Special details