( E )-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]-4-nitrophenolate

Journal Article · Wed Jan 14 00:00:00 EST 2009 · Acta Crystallographica. Section E

DOI:https://doi.org/10.1107/s1600536809000543· OSTI ID:1625728

Hijji, Yousef M. ^[1]; Barare, Belygona ^[1]; Butcher, Ray J. ^[2]; Jasinski, Jerry P. ^[3]

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1. Morgan State Univ., Baltimore, MD (United States). Dept. of Chemsitry
2. Howard Univ., Washington, DC (United States). Dept. of Chemistry
3. 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 Crystallography
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Crystallography