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

Akkurt, M.; Kennedy, A.R.; Younes, S.H.H.; Mohamed, S.K.; Abdelhamid, A.A.

doi:10.1107/S160053681204651X

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 (C-C) = 0.003 Å
R = 0.053
wR = 0.140
Data-to-parameter ratio = 15.5
Details

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

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b ^* Sabry H. H. Younes,^c Shaaban K. Mohamed ^d,^e and Antar A. Abdelhamid ^d

^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-HO hydrogen bonds generate R₂²(8) loops. The dimers are further linked by C-HO hydrogen bonds, so forming a column along the a-axis direction.

Related literature

For background to benzodiazepine compounds, see: McKernan (2000); Thakur et al. (2003). For related structures, see: Benelbaghdadi et al. (2003); Visnjevac et al. (2002).

Experimental

Crystal data

C₁₅H₁₂N₂O
M_r = 236.27
Triclinic, $[P \overline 1]$
a = 4.6894 (5) Å
b = 10.8353 (13) Å
c = 11.7540 (13) Å
= 77.721 (10)°
= 83.805 (9)°
= 82.112 (10)°
V = 576.13 (12) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.928, T_max = 1.000
4335 measured reflections
2584 independent reflections
1830 reflections with I > 2I
R_int = 0.034

Refinement

R[F² > 2(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
_max = 0.24 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.91 (2)	1.99 (2)	2.900 (2)	175 (2)
C1-H1BO1ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
McKernan, R. M. (2000). Nat. Neurosci. 3, 587-592.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thakur, A., Thakur, M. & Khadikar, P. V. (2003). Bioorg. Med. Chem. 11, 5203-5207.
Visnjevac, A., Avdagic, A. & Kojic-Prodic, B. (2002). Acta Cryst. E58, o148-o150.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References