Pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dithione

Ourahou, S.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810021410

Volume 66
Part 7
Page o1653
July 2010

Received 31 May 2010
Accepted 4 June 2010
Online 16 June 2010

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.107
Data-to-parameter ratio = 15.6
Details

Pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dithione

Sarah Ourahou,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The seven-membered fused-ring in the title compound, C₁₂H₁₂N₂S₂, adopts a boat conformation (with the two phenylene C atoms representing the stern and the methine C atom the prow). This methine C atom and the tertiary N atom also belong to a five-membered ring, which has an envelope conformation. In the crystal structure, molecules are linked about a center of inversion by pairs of N-HS hydrogen bonds.

Related literature

For background to pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione, see: Antonow et al. (2007); Kamal et al. (2007). For a related structure, Neidle et al. (1991).

Experimental

Crystal data

C₁₂H₁₂N₂S₂
M_r = 248.36
Monoclinic, P 2₁ /c
a = 13.9831 (5) Å
b = 10.0134 (3) Å
c = 8.2670 (3) Å
= 97.089 (1)°
V = 1148.68 (7) Å³
Z = 4
Mo K radiation
= 0.44 mm^-1
T = 200 K
0.12 × 0.10 × 0.07 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.950, T_max = 0.970
14013 measured reflections
3017 independent reflections
2117 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.107
S = 1.01
3017 reflections
193 parameters
12 restraints
All H-atom parameters refined
_max = 0.39 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S1ⁱ	0.86 (1)	2.58 (1)	3.411 (2)	166 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2774 ).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Antonow, D., Jenkins, T. C., Howard, P. W. & Thurston, D. E. (2007). Bioorg. Med. Chem. 15, 3041-3053.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kamal, A., Reddy, K. L., Devaiah, V., Shankaraiah, N., Reddy, G. S. K. & Raghavan, S. (2007). J. Comb. Chem. 9, 29-42.
Neidle, S., Webster, G. D., Jones, G. B. & Thurston, D. E. (1991). Acta Cryst. C47, 2678-2680.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.

organic compounds