Received 9 December 2011
aYoung Researchers Club, Tabriz Branch, Islamic Azad University, Tabriz, Iran,bDepartment of Chemistry, University of Zanjan 45195-313, Zanjan, Iran,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: email@example.com
The molecule of the title compound, C15H14N4O3, is completed by the application of crystallographic twofold symmetry, with the carbonyl group lying on the rotation axis. The molecule is close to planar: the greatest deviation of a torsion angle from 0° is 7.3 (2)° about the bond linking the phenol ring to the rest of the molecule. An intramolecular O-HN(imine) hydrogen bond is formed in each half of the molecule. The carbonyl O atom is anti with respect to the amine H atoms and this allows for the formation of N-HO(hydroxyl) hydrogen bonds in the crystal, which results in supramolecular layers lying parallel to (100).
Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6561 ).
The authors are grateful to the Islamic Azad University (Tabriz Branch), the University of Zanjan and the University of Malaya for support of this study.
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bikas, R., Hosseini Monfared, H., Bijanzad, K., Koroglu, A. & Kazak, C. (2010a). Acta Cryst. E66, o2073.
Bikas, R., Hosseini Monfared, H., Kazak, C., Arslan, N. B. & Bijanzad, K. (2010b). Acta Cryst. E66, o2015.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.