(IUCr) 2-Chloro-N-(2,5-dichlorophenyl)acetamide

Volume 65
Part 6
Page o1445
June 2009

Received 15 May 2009
Accepted 25 May 2009
Online 29 May 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R = 0.040
wR = 0.098
Data-to-parameter ratio = 15.7
Details

2-Chloro-N-(2,5-dichlorophenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
Correspondence e-mail: gowdabt@yahoo.com

The conformation of the N-H bond in the structure of the title compound, C₈H₆Cl₃NO, is anti to the C=O bond. The N-H H atom shows close intramolecular N-HCl hydrogen bonds with both the ring Cl atom in the ortho position and the side-chain Cl atom. The molecules crystallize in planes parallel to (221).

Related literature

For the preparation, see: Shilpa & Gowda (2007); Pies et al. (1971). For our work on the effect of ring and side-chain substitutions on the solid-state geometries of aromatic amides, see: Gowda Foro & Fuess (2008); Gowda, Kozísek et al. (2008); Gowda et al. (2009).

Experimental

Crystal data

C₈H₆Cl₃NO
M_r = 238.49
Triclinic, $[P \overline 1]$
a = 7.492 (2) Å
b = 8.496 (2) Å
c = 8.988 (2) Å
= 69.68 (2)°
= 67.54 (2)°
= 66.67 (2)°
V = 472.4 (2) Å³
Z = 2
Mo K radiation
= 0.92 mm^-1
T = 299 K
0.38 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.720, T_max = 0.823
2735 measured reflections
1914 independent reflections
1359 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.098
S = 1.02
1914 reflections
122 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NCl3	0.82 (3)	2.43 (3)	2.922 (2)	120 (2)
N1-H1NCl1	0.82 (3)	2.45 (3)	2.933 (2)	119 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2962 ).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany for an extension of his research fellowship.

References

Gowda, B. T., Foro, S. & Fuess, H. (2008). Acta Cryst. E64, o419.
Gowda, B. T., Foro, S., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o949.
Gowda, B. T., Kozísek, J., Tokarcík, M. & Fuess, H. (2008). Acta Cryst. E64, o987.
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.
Pies, W., Rager, H. & Weiss, A. (1971). Org. Magn. Reson. 3, 147-176.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shilpa & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62, 84-90.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds