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1-[2-(Carboxy-meth-oxy)phen-yl]-N-(4-chloro-phen-yl)methanimine oxide.


ABSTRACT: In the title resonance conformer, C(15)H(12)ClNO(4), the central C-N bond [1.297?(2)?Å] has considerable double-bond character and the N-O bond [1.3215?(18)?Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the mol-ecule, with both benzene rings twisted out of the central C-C-N-C plane [the dihedral angle formed between the rings = 81.99?(8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of the benzene ring to which it is connected [C-C-O-C torsion angle = -78.42?(17)°]. The most prominent inter-molecular inter-actions involve the carboxylic acid the N(+)-O(-) residues with the O-H?O hydrogen bonds leading to helical supra-molecular chains along the b axis. These chains are connected into layers via C-H?O(carbon-yl) inter-actions and the layers are consolidated into the crystal structure by C-H?Cl contacts.

SUBMITTER: Skakle JM 

PROVIDER: S-EPMC2980074 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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1-[2-(Carboxy-meth-oxy)phen-yl]-N-(4-chloro-phen-yl)methanimine oxide.

Skakle Janet M S JM   Tiekink Edward R T ER   Wardell James L JL   Wardell Solange M S V SM  

Acta crystallographica. Section E, Structure reports online 20091204 Pt 1


In the title resonance conformer, C(15)H(12)ClNO(4), the central C-N bond [1.297 (2) Å] has considerable double-bond character and the N-O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the mol-ecule, with both benzene rings twisted out of the central C-C-N-C plane [the dihedral angle formed between the rings = 81.99 (8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of t  ...[more]

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