1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide
In the title resonance conformer, C(15)H(12)ClNO(4), the central C-N bond [1.297 (2) angstrom] has considerable double-bond character and the N-O bond [1.3215 (18) angstrom] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the molecule, wi...
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| Format: | Article |
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International Union of Crystallography
2010
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| _version_ | 1825720663605772288 |
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| author | Skakle, J.M.S. Tiekink, E.R.T. Wardell, J.L. Wardell, S.M.S.V. |
| author_facet | Skakle, J.M.S. Tiekink, E.R.T. Wardell, J.L. Wardell, S.M.S.V. |
| author_sort | Skakle, J.M.S. |
| collection | UM |
| description | In the title resonance conformer, C(15)H(12)ClNO(4), the central C-N bond [1.297 (2) angstrom] has considerable double-bond character and the N-O bond [1.3215 (18) angstrom] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the molecule, with both benzene rings twisted out of the central C-C-N-C plane [the dihedral angle formed between the rings = 81.99 (8)degrees]. 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)degrees]. The most prominent intermolecular interactions involve the carboxylic acid the N(+)-O(-) residues with the O-H center dot center dot center dot O hydrogen bonds leading to helical supramolecular chains along the b axis. These chains are connected into layers via C-H center dot center dot center dot O(carbonyl) interactions and the layers are consolidated into the crystal structure by C-H center dot center dot center dot Cl contacts. |
| first_indexed | 2024-03-06T05:38:33Z |
| format | Article |
| id | um.eprints-15308 |
| institution | Universiti Malaya |
| last_indexed | 2024-03-06T05:38:33Z |
| publishDate | 2010 |
| publisher | International Union of Crystallography |
| record_format | dspace |
| spelling | um.eprints-153082019-01-30T09:15:36Z http://eprints.um.edu.my/15308/ 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide Skakle, J.M.S. Tiekink, E.R.T. Wardell, J.L. Wardell, S.M.S.V. Q Science (General) In the title resonance conformer, C(15)H(12)ClNO(4), the central C-N bond [1.297 (2) angstrom] has considerable double-bond character and the N-O bond [1.3215 (18) angstrom] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the molecule, with both benzene rings twisted out of the central C-C-N-C plane [the dihedral angle formed between the rings = 81.99 (8)degrees]. 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)degrees]. The most prominent intermolecular interactions involve the carboxylic acid the N(+)-O(-) residues with the O-H center dot center dot center dot O hydrogen bonds leading to helical supramolecular chains along the b axis. These chains are connected into layers via C-H center dot center dot center dot O(carbonyl) interactions and the layers are consolidated into the crystal structure by C-H center dot center dot center dot Cl contacts. International Union of Crystallography 2010 Article PeerReviewed Skakle, J.M.S. and Tiekink, E.R.T. and Wardell, J.L. and Wardell, S.M.S.V. (2010) 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide. Acta Crystallographica Section E: Structure Reports Online, 66 (1). O45-U1478. ISSN 1600-5368, |
| spellingShingle | Q Science (General) Skakle, J.M.S. Tiekink, E.R.T. Wardell, J.L. Wardell, S.M.S.V. 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title | 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title_full | 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title_fullStr | 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title_full_unstemmed | 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title_short | 1-[2-(Carboxymethoxy)phenyl]-N-(4-chlorophenyl)methanimine oxide |
| title_sort | 1 2 carboxymethoxy phenyl n 4 chlorophenyl methanimine oxide |
| topic | Q Science (General) |
| work_keys_str_mv | AT skaklejms 12carboxymethoxyphenyln4chlorophenylmethanimineoxide AT tiekinkert 12carboxymethoxyphenyln4chlorophenylmethanimineoxide AT wardelljl 12carboxymethoxyphenyln4chlorophenylmethanimineoxide AT wardellsmsv 12carboxymethoxyphenyln4chlorophenylmethanimineoxide |