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

Ma, C.; Wang, Z.-Z.; Pan, L.; Tian, Y.; Xiao, W.

doi:10.1107/S1600536811052962

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 (C-C) = 0.003 Å
R = 0.022
wR = 0.057
Data-to-parameter ratio = 14.6
Details

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

Chao Ma,^a Zhen-Zhong Wang,^b Li Pan,^a Yu Tian ^a and Wei Xiao ^b ^*

^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-HO hydrogen bonds and weak C-HO interactions help to stabilize the crystal structure.

Related literature

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).

Experimental

Crystal data

C₁₂H₁₁BrN₂O₂
M_r = 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 radiation
= 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) T_min = 0.506, T_max = 0.788
7012 measured reflections
2244 independent reflections
2074 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.022
wR(F²) = 0.057
S = 1.02
2244 reflections
154 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.21 e Å^-3
Absolute structure: Flack (1983), 884 Friedel pairs
Flack parameter: -0.007 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.88	2.00	2.864 (2)	169
C5-H5AO2ⁱⁱ	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); 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 ).

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.
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.

organic compounds