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Volume 65 
Part 2 
Pages o291-o292  
February 2009  

Received 23 December 2008
Accepted 6 January 2009
Online 14 January 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.129
Data-to-parameter ratio = 12.4
Details
Open access

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

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: rbutcher99@yahoo.com

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 [pi]-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-H...O hydrogen bonding between the depicted phenolate and hydroxy O atoms and their respective H atoms within the [pi]-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.

Related literature

For related structures, see: Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Vijesh, A. M. & Narayana, B. (2007). Acta Cryst. E63, o3748.]); Ersanli et al. (2003[Ersanli, C. C., Albayrak, Ç., Odabasoglu, M. & Erdönmez, A. (2003). Acta Cryst. C59, o601-o602.]); Gül et al. (2007[Gül, Z. S., Agar, A. A. & Isik, S. (2007). Acta Cryst. E63, o4564.]); Hijji et al. (2008[Hijji, Y. M., Barare, B., Kennedy, A. P. & Butcher, R. (2008). Sensors and Actuators B: Che., doi:10.1016/j.SnB.2008.11.045.]); Odabasoglu et al. (2006[Odabasoglu, M., Albayrak, C. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1094-o1096.]); Jasinski et al. (2007[Jasinski, J. P., Butcher, R. J., Narayana, B., Swamy, M. T. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4566-o4567.]). For related literature, see: Schmidt & Polik (2007[Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA; URL: http://www.webmo.net.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9N3O6

  • Mr = 303.23

  • Monoclinic, P 21 /c

  • a = 7.9649 (1) Å

  • b = 8.6110 (1) Å

  • c = 19.1190 (3) Å

  • [beta] = 98.433 (2)°

  • V = 1297.11 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 296 (2) K

  • 0.37 × 0.27 × 0.18 mm

Data collection
  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.954, Tmax = 0.978

  • 6432 measured reflections

  • 2495 independent reflections

  • 1819 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.129

  • S = 1.05

  • 2495 reflections

  • 202 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O2i 0.82 1.77 2.5570 (16) 161
O2-H2O...O1ii 0.82 1.75 2.5570 (16) 166
N1-H1N...O1 0.86 1.90 2.6001 (19) 138
C3-H3A...O3iii 0.93 2.56 3.295 (2) 137
C7-H7A...O4iv 0.93 2.67 3.289 (2) 125
C7-H7A...O5v 0.93 2.44 3.312 (2) 156
C10-H10A...O4vi 0.93 2.53 3.321 (2) 143
C13-H13A...O4iv 0.93 2.64 3.195 (2) 119
C13-H13A...O5v 0.93 2.63 3.512 (2) 160
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x, -y+2, -z; (iv) -x+1, -y+1, -z; (v) -x+1, -y, -z; (vi) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlisPro (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlisPro; data reduction: CrysAlisPro program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2463 ).


Acknowledgements

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.

References

Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Vijesh, A. M. & Narayana, B. (2007). Acta Cryst. E63, o3748.  [CSD] [CrossRef] [details]
Ersanli, C. C., Albayrak, Ç., Odabasoglu, M. & Erdönmez, A. (2003). Acta Cryst. C59, o601-o602.  [CrossRef] [details]
Gül, Z. S., Agar, A. A. & Isik, S. (2007). Acta Cryst. E63, o4564.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
Odabasoglu, M., Albayrak, C. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1094-o1096.  [CrossRef] [details]
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.  [CrossRef] [details]


Acta Cryst (2009). E65, o291-o292   [ doi:10.1107/S1600536809000543 ]

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