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Volume 69 
Part 6 
Page o874  
June 2013  

Received 1 April 2013
Accepted 6 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.120
Data-to-parameter ratio = 21.4
Details
Open access

2-Chloro-1-(2,4,4-trimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)ethanone

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C14H19ClN2O, the diazepine ring adopts a boat conformation. The Cl atom of the chloroacetyl group is trans to the N atom of the diazepine ring. In the crystal, the molecules form chains running along the diagonal of the ac plane through N-H...O hydrogen bonds.

Related literature

For the biological activity of benzodiazepine derivatives, see: Ponnuswamy et al. (2006[Ponnuswamy, S., Murugadoss, R., Jeyaraman, R., Thiruvalluvar, A. & Parthasarathi, V. (2006). Indian J. Chem. Sect. B, 45, 2059-2070.]); Rahbaek et al. (1999[Rahbaek, L., Breinholt, J., Frisvad, J. C. & Christophersen, C. (1999). J. Org. Chem. 64, 1689-1692.]). For related structures see: Thiruvalluvar & Ponnuswamy (2007[Thiruvalluvar, A. & Ponnuswamy, S. (2007). Acta Cryst. E63, o4264.]); Kavitha et al. (2012[Kavitha, T., Ponnuswamy, S., Suguna, S., Sakthivel, P. & Ponnuswamy, M. N. (2012). Mol. Cryst. Liq. Cryst. 557, 18-27.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. 1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H19ClN2O

  • Mr = 266.76

  • Monoclinic, P 21 /n

  • a = 10.3971 (3) Å

  • b = 12.2589 (3) Å

  • c = 11.0994 (3) Å

  • [beta] = 93.953 (1)°

  • V = 1411.33 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 293 K

  • 0.23 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.949

  • 13339 measured reflections

  • 3568 independent reflections

  • 2767 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.120

  • S = 1.07

  • 3568 reflections

  • 167 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.835 (19) 2.276 (19) 3.1049 (16) 171.5 (17)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6901 ).


Acknowledgements

SP thanks the UGC, New Delhi, for financial assistance in the form of a major research project.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. 1-19.
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kavitha, T., Ponnuswamy, S., Suguna, S., Sakthivel, P. & Ponnuswamy, M. N. (2012). Mol. Cryst. Liq. Cryst. 557, 18-27.  [CSD] [CrossRef] [ChemPort]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Ponnuswamy, S., Murugadoss, R., Jeyaraman, R., Thiruvalluvar, A. & Parthasarathi, V. (2006). Indian J. Chem. Sect. B, 45, 2059-2070.
Rahbaek, L., Breinholt, J., Frisvad, J. C. & Christophersen, C. (1999). J. Org. Chem. 64, 1689-1692.  [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Thiruvalluvar, A. & Ponnuswamy, S. (2007). Acta Cryst. E63, o4264.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o874  [ doi:10.1107/S1600536813012324 ]

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