Received 5 December 2011
The title compound, C12H11BrN2O2, was prepared by an intra-cyclization reaction of (S)-1-(5-bromo-2-nitrobenzyl)-5-oxopyrrolidine-2-carboxylic acid methyl ester in the presence of EtOH/Fe. The five-membered pyrrolidinone ring adopts an approximate envelope conformation, while the seven-membered diazepanone ring displays a twisted boat conformation. Intermolecular classical N-HO hydrogen bonds and weak C-HO interactions help to stabilize the crystal structure.
For applications of pyrrolo[2,1-c][1,4]benzodiazepines, see: Bose et al. (1992); Hu et al. (2001); Jitendra et al. (2007); Kamal et al. (2002); Thurston & Bose (1994). For a related structure, see: Cheng et al. (2007).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5404 ).
The work was supported by grants from the National Natural Science Foundation of China (No. 30973613) and the National Science Foundation for Post-doctoral Scientists of China (No. 2011M500578).
Bose, D. S., Jones, G. B. & Thurston, D. E. (1992). Tetrahedron, 48, 751-758.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, M.-S., Ma, C., Liu, J.-H., Sha, Y. & Wang, Q.-H. (2007). Acta Cryst. E63, o4605.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hu, W.-P., Wang, J.-J., Lin, F.-L., Lin, Y.-C., Lin, S.-R. & Hsu, M.-H. (2001). J. Org. Chem. 66, 2881-2883.
Jitendra, K. M., Puja, G., Preeti, D., Ashutosh, K., Mohammad, I. S., Madhur, R. & Gautam, P. (2007). Bioorg. Med. Chem. Lett. 17, 1326-1331.
Kamal, A., Rao, M. V., Laxman, N., Ramesh, G. & Reddy, G. S. K. (2002). Curr. Med. Chem. Anti-Cancer Agent. 2, 215-254.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Thurston, D. E. & Bose, D. S. (1994). Chem. Rev. 94, 433-465.