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Volume 69 
Part 12 
Page o1837  
December 2013  

Received 25 October 2013
Accepted 22 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.177
Data-to-parameter ratio = 15.6
Details
Open access

N-(2-Oxo-2,3,4,5,6,7-hexa­hydro-1H-azepin-3-yl)cyclo­hexa­necarboxamide

aSuzhou University Experimental Material Supply Center, Suzhou 215123, People's Republic of China, and bCollege of Pharmacy, China Pharmaceutical University, Tongjiaxiang No. 24 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: yzcpu@163.com

In the title compound, C13H22N2O2, both the six-membered ring and the seven-membered lactam ring adopt chair conformations. In the crystal, mol­ecules are linked by pairs of N-H...O hydrogen bonds between inversion-related lactam rings into centrosymmetric dimers with an R22(8) graph-set motif. Further N-H...O hydrogen bonds link the molecules into [100] chains.

Related literature

For background information on 3-(acyl­amino)­azepan-2-ones, see: Fox et al. (2009[Fox, D. J., Reckless, J., Lingard, H., Warren, S. & Grainger, D. J. (2009). J. Med. Chem. 52, 3591-3595.]); Grainger & Fox (2006[Grainger, D. J. & Fox, D. J. (2006). Patent WO 2006016152A1.]). For a related crystal structure, see: Zhu et al. (2007[Zhu, N., Tran, P., Bell, N. & Stevens, C. L. K. (2007). J. Chem. Crystallogr. 37, 670-683.]).

[Scheme 1]

Experimental

Crystal data
  • C13H22N2O2

  • Mr = 238.33

  • Triclinic, [P \overline 1]

  • a = 5.007 (1) Å

  • b = 11.642 (2) Å

  • c = 12.739 (3) Å

  • [alpha] = 63.66 (3)°

  • [beta] = 82.69 (3)°

  • [gamma] = 82.75 (3)°

  • V = 658.0 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.976, Tmax = 0.992

  • 2700 measured reflections

  • 2400 independent reflections

  • 1581 reflections with I > 2[sigma](I)

  • Rint = 0.073

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.177

  • S = 1.01

  • 2400 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.37 3.158 (3) 152
N2-H2A...O2ii 0.86 2.09 2.927 (3) 165
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: 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: PK2501 ).


References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Fox, D. J., Reckless, J., Lingard, H., Warren, S. & Grainger, D. J. (2009). J. Med. Chem. 52, 3591-3595.  [CrossRef] [PubMed] [ChemPort]
Grainger, D. J. & Fox, D. J. (2006). Patent WO 2006016152A1.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhu, N., Tran, P., Bell, N. & Stevens, C. L. K. (2007). J. Chem. Crystallogr. 37, 670-683.  [Web of Science] [CSD] [CrossRef]


Acta Cryst (2013). E69, o1837  [ doi:10.1107/S1600536813031863 ]

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