1-Benzoyl-3-chloro­azepan-2-one

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

doi:10.1107/S1600536809033510

Volume 65
Part 10
Page o2383
October 2009

Received 8 August 2009
Accepted 22 August 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R = 0.040
wR = 0.109
Data-to-parameter ratio = 7.9
Details

1-Benzoyl-3-chloroazepan-2-one

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

^aState Key Laboratory of Materials-Oriented Chemical 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 crystal structure of the title compound, C₁₃H₁₄ClNO₂, intermolecular C-HO interactions link the molecules into a two-dimensional network.

Related literature

For related structures, see: Tull et al. (1964); Largman et al. (1979). For ring-puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₁₄ClNO₂
M_r = 251.70
Orthorhombic, P n a 2₁
a = 19.564 (4) Å
b = 7.6500 (15) Å
c = 8.4050 (17) Å
V = 1257.9 (4) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.917, T_max = 0.971
2413 measured reflections
1229 independent reflections
968 reflections with I > 2(I)
R_int = 0.027
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.109
S = 1.01
1229 reflections
155 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1184 Friedel pairs
Flack parameter: 0.07 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5AO1ⁱ	0.93	2.43	3.335 (6)	163
C12-H12AO2ⁱⁱ	0.98	2.56	3.319 (5)	134
Symmetry codes: (i) x, y+1, z; (ii) $[-x, -y+1, z-{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2754 ).

Acknowledgements

The authors thank the Innovation Fund for Doctoral Theses (BSCX200811), Nanjing University of Technology, 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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Largman, T., Sifniades, S. & Schmehl, L. J. (1979). Synth. Commun. 9, 255-259.
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.
Tull, R., O'Neill, R. C., McCarthy, E. P., Pappas, J. J. & Chemerda, J. M. (1964). J. Org. Chem. 29, 2425-2426.

organic compounds