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Volume 69 
Part 6 
Page o971  
June 2013  

Received 16 March 2013
Accepted 20 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.075
wR = 0.162
Data-to-parameter ratio = 18.8
Details
Open access

1-(4-Chlorophenyl)-2-(1,3-diazepan-2-ylidene)ethanone

aCollege of Chemistry and Chemical Engineering, Jiang Xi Normal University, Nanchang, Jiang Xi 330022, People's Republic of China, and bBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
Correspondence e-mail: yucy@iccas.ac.cn

In the title compound, C13H15ClN2O, there are two crystallographically independent but conformationally similar (E)-molecules in the asymmetric unit [dihedral angles between the phenyl ring and a common planar fragment of the 1,3-diazepane moiety = 47.34 (16) and 48.00 (16)°]. The seven-membered ring system adopts a chair conformation in both molecules. In the crystal, N-H...O hydrogen bonds lead to chains extending along the b-axis direction.

Related literature

Heterocyclic ketene aminals are a useful synthon for the synthesis of fused heterocycles, see: Huang & Wang (1994[Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.]). For their bioactivity and potential applications as pesticides and in medicine, see: Kondo et al. (1990[Kondo, H., Taguchi, M., Inoue, Y., Sakamoto, F. & Tsukamoto, G. (1990). J. Med. Chem. 33, 2012-2015.]); Jordan et al. (2002[Jordan, A. D., Vaidya, A. H., Rosenthal, D. I., Dubinsky, B., Kordik, C. P., Sanfilippo, P. J., Wu, W.-N. & Reitz, A. B. (2002). Bioorg. Med. Chem. Lett. 12, 2381-2386.]). For the synthesis, see: Huang & Liu (1989[Huang, Z.-T. & Liu, Z.-R. (1989). Synth. Commun. 19, 943-958.]). For a similar structure, see: Yu et al. (2006[Yu, C.-Y., Yan, S.-J. & Huang, Z.-T. (2006). Acta Cryst. E62, o2655-o2656.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15ClN2O

  • Mr = 250.72

  • Triclinic, [P \overline 1]

  • a = 10.779 (4) Å

  • b = 10.815 (3) Å

  • c = 12.158 (4) Å

  • [alpha] = 96.091 (4)°

  • [beta] = 110.710 (4)°

  • [gamma] = 101.244 (4)°

  • V = 1276.4 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 173 K

  • 0.25 × 0.15 × 0.14 mm

Data collection
  • Rigaku Saturn724+ CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.606, Tmax = 1.000

  • 11344 measured reflections

  • 5780 independent reflections

  • 4854 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.162

  • S = 1.12

  • 5780 reflections

  • 307 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2 0.88 2.07 2.834 (3) 145
N3-H3...O1i 0.88 2.09 2.878 (3) 149
Symmetry code: (i) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2253 ).


Acknowledgements

We thank Tongling Liang at the Chinese Academy of Sciences for the X-ray crystallographic determination.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Huang, Z.-T. & Liu, Z.-R. (1989). Synth. Commun. 19, 943-958.  [CrossRef] [ChemPort] [ISI]
Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.  [CrossRef] [ChemPort]
Jordan, A. D., Vaidya, A. H., Rosenthal, D. I., Dubinsky, B., Kordik, C. P., Sanfilippo, P. J., Wu, W.-N. & Reitz, A. B. (2002). Bioorg. Med. Chem. Lett. 12, 2381-2386.  [CrossRef] [PubMed] [ChemPort]
Kondo, H., Taguchi, M., Inoue, Y., Sakamoto, F. & Tsukamoto, G. (1990). J. Med. Chem. 33, 2012-2015.  [CrossRef] [ChemPort] [PubMed] [ISI]
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yu, C.-Y., Yan, S.-J. & Huang, Z.-T. (2006). Acta Cryst. E62, o2655-o2656.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o971  [ doi:10.1107/S1600536813013858 ]

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