3-Hy­droxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

Rida, M.; Mamari, K.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811054456

Volume 68
Part 1
Page o238
January 2012

Received 17 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.052
wR = 0.153
Data-to-parameter ratio = 18.5
Details

3-Hydroxy-4-phenyl-1-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Mohamed Rida,^a Khalil Mamari,^a El Mokhtar Essassi ^a and Seik Weng Ng ^b,^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

The asymmetric unit of the title compound, C₁₈H₁₈N₂O₂, contains three independent molecules. In each, the seven-membered diazepine ring adopts a boat conformation with the hydroxy-substituted C atom at the prow and fused-ring C atoms at the stern. In the crystal, the molecules are linked by O-HO and N-HO hydrogen bonds. The allyl group of one molecule is equally disordered over two positions.

Related literature

For a related structure, see: Rida et al. (2011).

Experimental

Crystal data

C₁₈H₁₈N₂O₂
M_r = 294.34
Monoclinic, C 2/c
a = 51.6665 (8) Å
b = 14.5766 (2) Å
c = 11.9316 (2) Å
= 90.965 (2)°
V = 8984.7 (2) Å³
Z = 24
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.21 × 0.15 × 0.13 mm

Data collection

Bruker APEX DUO diffractometer
98635 measured reflections
11182 independent reflections
8815 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.153
S = 1.01
11182 reflections
604 parameters
16 restraints
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.74 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oO2ⁱ	0.84	1.96	2.786 (2)	167
O5-H5oO6ⁱⁱ	0.84	2.30	3.022 (2)	145
N1-H1nO3	0.88	2.58	3.142 (2)	123
N3-H3nO4ⁱⁱⁱ	0.88	2.40	2.900 (2)	116
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); 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: XU5411 ).

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 (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Rida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945-o946.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds