3-(6-Bromo­hex­yl)-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Dardouri, R.; Ouazzani Chahdi, F.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810040122

Volume 66
Part 11
Page o2804
November 2010

Received 6 October 2010
Accepted 7 October 2010
Online 13 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.153
Data-to-parameter ratio = 24.4
Details

3-(6-Bromohexyl)-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rchida Dardouri,^a Fouad Ouazzani Chahdi,^a Natalie Saffon,^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,^bService Commun Rayons-X FR2599, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The seven-membered ring in the title compound, C₁₇H₂₃BrN₂O₂, adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The bromohexyl substituent occupies an equatorial position, with the hexyl chain exhibiting an extended conformation. Weak intermolecular C-HO hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005).

Experimental

Crystal data

C₁₇H₂₃BrN₂O₂
M_r = 367.28
Monoclinic, P 2₁ /n
a = 7.5214 (1) Å
b = 9.3693 (2) Å
c = 23.8686 (5) Å
= 91.750 (1)°
V = 1681.24 (6) Å³
Z = 4
Mo K radiation
= 2.45 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.526, T_max = 0.791
25590 measured reflections
4897 independent reflections
3478 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.153
S = 1.01
4897 reflections
201 parameters
H-atom parameters constrained
_max = 1.92 e Å^-3
_min = -0.68 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BO1ⁱ	0.96	2.58	3.430 (3)	147
C7-H7CO2ⁱⁱ	0.96	2.51	3.471 (3)	174
C11-H11BO1ⁱⁱ	0.96	2.60	3.551 (3)	173
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: XU5049 ).

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Mondieig, M., Négrier, Ph., Léger, J. M., Benali, B., Lazar, Z., Elassyry, A., Jarmouni, C., Lakhrissi, B. & Massoui, M. (2005). Anal. Sci. X-Ray Struct. Anal. Online, 21, x145-x146.
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, 920-925.

organic compounds