3-Chloro­azepan-2-one

Wang, D.-C.; Fan, D.-M.; Liu, H.-Q.; Ou-yang, P.-K.

doi:10.1107/S1600536810002060

Volume 66
Part 2
Page o438
February 2010

Received 6 October 2009
Accepted 16 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.148
Data-to-parameter ratio = 16.4
Details

3-Chloroazepan-2-one

De-Cai Wang,^a ^* Dong-Mei Fan,^a Hua-Quan Liu ^a and Ping-Kai Ou-yang ^a

^aState Key Laboratory of Materials-Oriented Chemcial Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: dcwang@njut.edu.cn

In the title compound, C₆H₁₀ClNO, an intermediate for the production of lysine, there are intramolecular C-HCl hydrogen bonds.

Related literature

For the preparation of the title compound, see: Wineman et al. (1958). For puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₆H₁₀ClNO
M_r = 147.60
Monoclinic, C 2/c
a = 18.776 (4) Å
b = 7.3440 (15) Å
c = 11.109 (2) Å
= 103.65 (3)°
V = 1488.6 (5) Å³
Z = 8
Mo K radiation
= 0.43 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.881, T_max = 0.918
2654 measured reflections
1345 independent reflections
1107 reflections with I > 2(I)
R_int = 0.020
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.148
S = 1.01
1345 reflections
82 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1BCl	0.97	2.82	3.215 (3)	105
C3-H3BCl	0.97	2.80	3.374 (3)	119

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2071 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wineman, R. J., Hsu, E.-P. T. & Anagnostopoulos, C. E. (1958). J. Am. Chem. Soc. 80, 6233-6237.

organic compounds