Received 25 August 2009
The asymmetric unit of the title compound, C14H8N2O8·2C3H7NO or L·2DMF (DMF = N,N-dimethylformamide), contains one half of the centrosymmetric molecule L and one solvent molecule, which is disordered between two orientations in a 0.555 (4):0.445 (4) ratio. Intermolecular O-HO hydrogen bonds link one L and two DMF molecules into a centrosymmetric hydrogen-bonded cluster. The crystal packing is further stabilized by weak intermolecular C-HO hydrogen bonds.
For recent developments in the chemistry of naphthalene diimides, see Bhosale et al. (2008). For pyromellitic diimides, see: Gabriel & Iverson (2002); Ghosh & Ramakrishnan (2005); Kimizuka et al. (1995). For details of the synthesis, see Barooah et al. (2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2607 ).
This work was supported by the Project for Innovation Teams of Liaoning Province, China (No. 2007 T052), the Project for Provincial Key Laboratories of Liaoning Province, China (No. 2008S104) and the Doctoral Startup Project, Liaoning University.
Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608-615.
Bhosale, S. V., Jani, C. H. & Langford, S. J. (2008). Chem. Soc. Rev. 37, 331-342.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gabriel, G. J. & Iverson, B. L. (2002). J. Am. Chem. Soc. 124, 15174-15175.
Ghosh, S. & Ramakrishnan, S. (2005). Angew. Chem. Int. Ed. 44, 5441-5447.
Kimizuka, N., Kawasaki, T., Hirata, K. & Kunitake, T. (1995). J. Am. Chem. Soc. 117, 6360-6361.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.