N-[2-(1,3-Benzodioxol-5-yl)eth­yl]-2-chloro­acetamide

Dong, H.-C.

doi:10.1107/S1600536808014232

Volume 64
Part 6
Page o1118
June 2008

Received 6 May 2008
Accepted 12 May 2008
Online 21 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.035
wR = 0.110
Data-to-parameter ratio = 13.6
Details

N-[2-(1,3-Benzodioxol-5-yl)ethyl]-2-chloroacetamide

Hui-Chao Dong ^a ^*

^aHenan Provincial Key Laboratory of Surface & Interface Science, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
Correspondence e-mail: donghuichao6503@yahoo.cn

The title compound, C₁₁H₁₂ClNO₃, crystallizes with two independent molecules in the asymmetric unit. Intermolecular N-HO hydrogen bonds link the molecules related by translation along the b axis into two independent hydrogen-bonded chains. The crystal studied exhibited inversion twinning.

Related literature

For the crystal structures of related compounds, see: Kuehne et al. (1988). For details of the aplication of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide, see: Bernhard & Snieckus (1971); Ma et al. (2006). For bond-length data, see Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₂ClNO₃
M_r = 241.67
Orthorhombic, P c a 2₁
a = 14.429 (3) Å
b = 5.1258 (10) Å
c = 30.679 (6) Å
V = 2269.1 (8) Å³
Z = 8
Mo K radiation
= 0.33 mm^-1
T = 293 (2) K
0.20 × 0.12 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.937, T_max = 0.971
15836 measured reflections
3949 independent reflections
2946 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.110
S = 1.13
3949 reflections
290 parameters
1 restraint
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.34 e Å^-3
Absolute structure: Flack (1983), 1304 Friedel pairs
Flack parameter: 0.47 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO3ⁱ	0.86	2.18	2.894 (4)	140
N2-H2BO6ⁱⁱ	0.86	2.18	2.894 (4)	140
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2412 ).

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.
Bernhard, H. O. & Snieckus, V. (1971). Tetrahedron, 27, 2091-2100.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kuehne, M. E., Bornmann, W. G., Parsons, W. H., Spitzer, T. D., Blount, J. F. & Zubieta, J. (1988). J. Org. Chem. 53, 3439-3450.
Ma, C., Liu, S., Xin, L., Zhang, Q., Ding, K., Falck, J. R. & Shin, D. (2006). Chem. Lett. 35, 1010-1011.
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Takyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds