Received 23 December 2008
aDepartment of Chemistry, Morgan State University, Baltimore, MD 21251, USA,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, and cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: firstname.lastname@example.org
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  plane of the unit cell in an alternate inverted pattern. A MOPAC AM1 calculation provides support for these observations.
For related structures, see: Butcher et al. (2007); Ersanli et al. (2003); Gül et al. (2007); Hijji et al. (2008); Odabasoglu et al. (2006); Jasinski et al. (2007). For related literature, see: Schmidt & Polik (2007).
Data collection: CrysAlisPro (Oxford Diffraction, 2007); cell refinement: CrysAlisPro; data reduction: CrysAlisPro program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2463 ).
Support to YMH and BB was provided by DOE-CETBR grant No. DE-FG02-03ER63580 and NSF-RISE Award No. HRD-0627276. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Vijesh, A. M. & Narayana, B. (2007). Acta Cryst. E63, o3748.
Ersanli, C. C., Albayrak, Ç., Odabasoglu, M. & Erdönmez, A. (2003). Acta Cryst. C59, o601-o602.
Gül, Z. S., Agar, A. A. & Isik, S. (2007). Acta Cryst. E63, o4564.
Hijji, Y. M., Barare, B., Kennedy, A. P. & Butcher, R. (2008). Sensors and Actuators B: Che., doi:10.1016/j.SnB.2008.11.045.
Jasinski, J. P., Butcher, R. J., Narayana, B., Swamy, M. T. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4566-o4567.
Odabasoglu, M., Albayrak, C. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1094-o1096.
Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA; URL: http://www.webmo.net.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.