[Journal logo]

Volume 68 
Part 12 
Page o3356  
December 2012  

Received 4 November 2012
Accepted 10 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.140
Data-to-parameter ratio = 15.5
Details
Open access

4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,cDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt,dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, and eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt
Correspondence e-mail: akkurt@erciyes.edu.tr, a.r.Kennedy@strath.ac.uk

In the title compound, C15H12N2O, the phenyl ring makes a dihedral angle of 32.45 (9)° with the benzene ring of the 1,5-benzodiazepin-2-one unit. The seven-membered ring adopts a boat conformation with the methylene group as the prow and the fused benzene-ring C atoms as the stern. In the crystal, inversion dimers linked by pairs of N-H...O hydrogen bonds generate R22(8) loops. The dimers are further linked by C-H...O hydrogen bonds, so forming a column along the a-axis direction.

Related literature

For background to benzodiazepine compounds, see: McKernan (2000[McKernan, R. M. (2000). Nat. Neurosci. 3, 587-592.]); Thakur et al. (2003[Thakur, A., Thakur, M. & Khadikar, P. V. (2003). Bioorg. Med. Chem. 11, 5203-5207.]). For related structures, see: Benelbaghdadi et al. (2003[Benelbaghdadi, R., Hasnaoui, R. A., Lavergne, J. P., Ait Itto, M. & Pierrot, M. (2003). Acta Cryst. E59, o143-o144.]); Visnjevac et al. (2002[Visnjevac, A., Avdagic, A. & Kojic-Prodic, B. (2002). Acta Cryst. E58, o148-o150.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O

  • Mr = 236.27

  • Triclinic, [P \overline 1]

  • a = 4.6894 (5) Å

  • b = 10.8353 (13) Å

  • c = 11.7540 (13) Å

  • [alpha] = 77.721 (10)°

  • [beta] = 83.805 (9)°

  • [gamma] = 82.112 (10)°

  • V = 576.13 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 123 K

  • 0.35 × 0.09 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur Eos CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.928, Tmax = 1.000

  • 4335 measured reflections

  • 2584 independent reflections

  • 1830 reflections with I > 2[sigma]I

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.140

  • S = 1.02

  • 2584 reflections

  • 167 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.91 (2) 1.99 (2) 2.900 (2) 175 (2)
C1-H1B...O1ii 0.99 2.56 3.468 (2) 153
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6983 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

References

Benelbaghdadi, R., Hasnaoui, R. A., Lavergne, J. P., Ait Itto, M. & Pierrot, M. (2003). Acta Cryst. E59, o143-o144.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
McKernan, R. M. (2000). Nat. Neurosci. 3, 587-592.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thakur, A., Thakur, M. & Khadikar, P. V. (2003). Bioorg. Med. Chem. 11, 5203-5207.  [CrossRef] [PubMed] [ChemPort]
Visnjevac, A., Avdagic, A. & Kojic-Prodic, B. (2002). Acta Cryst. E58, o148-o150.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3356  [ doi:10.1107/S160053681204651X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.