Received 20 June 2010
The condensation of 2-carboxybenzaldehyde with 1,2-phenylenediamine unexpectedly yielded the title compound, C22H14N2O4·CH4O. The benzimidazole ring system is almost perpendicular to the phthalazine ring system, making a dihedral angle of 88.4 (5)°. Intermolecular O-HN and O-HO hydrogen-bonding interactions stabilize the crystal structure.
For hydrogen bonding, see: Scheiner (1997). For the role of hydrogen bonding between solvent molecules and heterocyclic compounds in the formation of supramolecules, see: Amaya & Rebek (2004); Roesky & Andruh (2003). Nelson et al. (1982) have reported that reaction of 2,6-diacetylpyridine and 1,2-phenylenediamine can form benzimidazole groups via oxidative dehydrogenation and Li et al. (2002) have isolated a benzimidazole derivate by the reaction of 5-bromo-2-hydroxybenzaldehyde and 1,2-phenylenediamine in the presence of anhydrous ethanol solution. For a related structure, see: Zhang et al. (2009).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: JH2172 ).
The authors acknowledge South China Normal University for supporting this work.
Amaya, T. & Rebek, J. (2004). J. Am. Chem. Soc. 126, 14149-14156.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, J., Zhang, F. X. & Shi, Q. Z. (2002). Chin. J. Inorg. Chem. 6, 643-645.
Nelson, S. M., Esho, F. S. & Drew, M. G. B. (1982). J. Chem. Soc. Dalton Trans. pp. 407-415.
Roesky, H. W. & Andruh, M. (2003). Coord. Chem. Rev. 236, 91-119.
Scheiner (1997). Please give full reference.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, Y.-L., Wu, Y.-J., Peng, G. & Deng, H. (2009). Acta Cryst. E65, o974.