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Volume 68 
Part 1 
Page o126  
January 2012  

Received 5 December 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 185 K
Mean [sigma](C-C) = 0.003 Å
R = 0.022
wR = 0.057
Data-to-parameter ratio = 14.6
Details
Open access

(11aS)-7-Bromo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-3,11-dione

aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China, and bJiangsu Kanion Pharmaceutical Co. Ltd, Lianyungang 222001, People's Republic of China
Correspondence e-mail: machao@syphu.edu.cn

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-H...O hydrogen bonds and weak C-H...O interactions help to stabilize the crystal structure.

Related literature

For applications of pyrrolo[2,1-c][1,4]benzodiazepines, see: Bose et al. (1992[Bose, D. S., Jones, G. B. & Thurston, D. E. (1992). Tetrahedron, 48, 751-758.]); Hu et al. (2001[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 et al. (2007[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 et al. (2002[Kamal, A., Rao, M. V., Laxman, N., Ramesh, G. & Reddy, G. S. K. (2002). Curr. Med. Chem. Anti-Cancer Agent. 2, 215-254.]); Thurston & Bose (1994[Thurston, D. E. & Bose, D. S. (1994). Chem. Rev. 94, 433-465.]). For a related structure, see: Cheng et al. (2007[Cheng, M.-S., Ma, C., Liu, J.-H., Sha, Y. & Wang, Q.-H. (2007). Acta Cryst. E63, o4605.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11BrN2O2

  • Mr = 295.14

  • Orthorhombic, P 21 21 21

  • a = 4.3880 (4) Å

  • b = 13.1210 (11) Å

  • c = 19.8722 (16) Å

  • V = 1144.14 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.58 mm-1

  • T = 185 K

  • 0.22 × 0.18 × 0.07 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.506, Tmax = 0.788

  • 7012 measured reflections

  • 2244 independent reflections

  • 2074 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.057

  • S = 1.02

  • 2244 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 884 Friedel pairs

  • Flack parameter: -0.007 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.88 2.00 2.864 (2) 169
C5-H5A...O2ii 0.99 2.38 3.328 (3) 160
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 ).


Acknowledgements

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).

References

Bose, D. S., Jones, G. B. & Thurston, D. E. (1992). Tetrahedron, 48, 751-758.  [CrossRef]
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.  [CSD] [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Jitendra, K. M., Puja, G., Preeti, D., Ashutosh, K., Mohammad, I. S., Madhur, R. & Gautam, P. (2007). Bioorg. Med. Chem. Lett. 17, 1326-1331.  [PubMed]
Kamal, A., Rao, M. V., Laxman, N., Ramesh, G. & Reddy, G. S. K. (2002). Curr. Med. Chem. Anti-Cancer Agent. 2, 215-254.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Thurston, D. E. & Bose, D. S. (1994). Chem. Rev. 94, 433-465.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, o126  [ doi:10.1107/S1600536811052962 ]

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