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

Volume 64
Part 3
Page o587
March 2008

Received 29 January 2008
Accepted 8 February 2008
Online 13 February 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.122
Data-to-parameter ratio = 16.8
Details

7-Chloro-11a-phenyl-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

Rafael Tamazyan,^a ^* Armen Ayvazyan,^a Ashot Martirosyan,^b Gohar Harutyunyan ^b and Vahan Martirosyan ^b

^aMolecular Structure Research Center, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia, and ^bInstitute of Fine Organic Chemistry, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia
Correspondence e-mail: rafael@msrc.am

The title compound, C₁₈H₁₅ClN₂O₂, is a potential human immunodeficiency virus type-1 (HIV-1) non-nucleoside reverse transcriptase inhibitor. The pyrrolidine ring adopts an envelope and the diazepine ring a boat conformation. In the crystal structure, two isomers (R and S) form centrosymmetric dimers via N-HO hydrogen bonds.

Related literature

For details of the pharmacological properties of this family of compounds, see: De Clercq (1996). For the crystal structures of some analogues of the title compound, see: Karapetyan et al. (2002); Tamazyan et al. (2002, 2007). For reference structural data, see Allen et al. (1987).

Experimental

Crystal data

C₁₈H₁₅ClN₂O₂
M_r = 326.77
Triclinic, $[P \overline 1]$
a = 8.9749 (18) Å
b = 9.2184 (18) Å
c = 9.912 (2) Å
= 86.90 (3)°
= 71.35 (3)°
= 88.27 (3)°
V = 775.8 (3) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 293 (2) K
0.35 × 0.32 × 0.28 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
7347 measured reflections
4514 independent reflections
3148 reflections with I > 2(I)
R_int = 0.035
3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
4514 reflections
268 parameters
All H-atom parameters refined
_max = 0.27 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4O12ⁱ	0.85 (2)	2.35 (2)	2.997 (2)	133 (2)
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: DATCOL in CAD-4 (Enraf-Nonius, 1988); cell refinement: LS in CAD-4; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2462 ).

Acknowledgements

This research was carried out under the framework of the Armenian Science and Education Foundation (ANSEF grant No. PS-chemorg-907). The authors express their thanks to ANSEF.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
De Clercq, E. (1996). Rev. Med. Virol. 6, 97-117.
Enraf-Nonius (1988). CAD-4 Manual. Version 5.0. Enraf-Nonius, Delft, The Netherlands.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Karapetyan, H., Tamazyan, R., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o399-o401.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (1997). HELENA. University of Utrecht, The Netherlands.
Tamazyan, R., Ayvazyan, A., Martirosyan, A., Martirosyan, V. & Schinazi, R. (2007). Acta Cryst. E63, o3967.
Tamazyan, R., Karapetyan, H., Martirosyan, A., Hovhannesyan, V. & Gasparyan, S. (2002). Acta Cryst. C58, o386-o388.

organic compounds