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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 [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.052
wR = 0.153
Data-to-parameter ratio = 18.5
Details
Open access

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

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-H...O and N-H...O 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[Rida, M., Essassi, E. M., Massip, S., Lazar, S. & Zouihri, H. (2011). Acta Cryst. E67, o945-o946.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N2O2

  • Mr = 294.34

  • Monoclinic, C 2/c

  • a = 51.6665 (8) Å

  • b = 14.5766 (2) Å

  • c = 11.9316 (2) Å

  • [beta] = 90.965 (2)°

  • V = 8984.7 (2) Å3

  • Z = 24

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.153

  • S = 1.01

  • 11182 reflections

  • 604 parameters

  • 16 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.74 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1o...O2i 0.84 1.96 2.786 (2) 167
O5-H5o...O6ii 0.84 2.30 3.022 (2) 145
N1-H1n...O3 0.88 2.58 3.142 (2) 123
N3-H3n...O4iii 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o238  [ doi:10.1107/S1600536811054456 ]

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