( E )-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]-4-nitrophenolate
- Morgan State Univ., Baltimore, MD (United States). Dept. of Chemsitry
- Howard Univ., Washington, DC (United States). Dept. of Chemistry
- Keene State College, Keene, NH (United States). Dept. of Chemistry
The title molecule, C13H9N3O6, consists of a 2-hydroxy-5- nitrophenyliminio group and a 4-nitrophenolate group bonded to a methylene C atom with both of the planar six membered rings nearly in the plane of the molecule [dihedral angle = 1.3 (4)°]. Each of the nitro O atoms is twisted slightly out of the plane of the molecule. The amine group forms an intramolecular hydrogen bond with both nearby O atoms, each of which has partial occupancy of attached H atoms [0.36 (3) and 0.64 (3)]. An extended -delocalization throughout the entire molecule exists producing a zwitterionic effect in this region of the molecule. The shortened phenolate C-O bond [1.2749 (19) ], in concert with the slightly longer phenol C-O bond [1.3316 (19) Å ], provides evidence for this effect. The crystal packing is influenced by extensive strong intermolecular O-HO hydrogen bonding between the depicted phenolate and hydroxy O atoms and their respective H atoms within the -delocalized region of the molecule. As a result, molecules are linked into an infinite polymeric chain diagonally along the [110] plane of the unit cell in an alternate inverted pattern. A MOPAC AM1 calculation provides support for these observations.
- Research Organization:
- Morgan State Univ., Baltimore, MD (United States)
- Sponsoring Organization:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
- Grant/Contract Number:
- FG02-03ER63580
- OSTI ID:
- 1625728
- Journal Information:
- Acta Crystallographica. Section E, Vol. 65, Issue 2; ISSN 1600-5368
- Publisher:
- International Union of CrystallographyCopyright Statement
- Country of Publication:
- United States
- Language:
- English
( E )-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]phenolate
|
journal | February 2009 |
2-{( E )-[(4-Methylphenyl)imino]methyl}-4-nitrophenol–2-{( E )-[(4-methylphenyl)iminio]methyl}-4-nitrophenolate (0.60/0.40)
|
journal | August 2011 |
5-Hydroxy-2-{( E )-[(3-nitrophenyl)iminio]methyl}phenolate
|
journal | August 2012 |
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