2-(4-Chloro­benzamido)­acetic acid

Khan, I.U.; Khan, M.H.; Arshad, M.N.; Akkurt, M.

doi:10.1107/S1600536811009536

Volume 67
Part 4
Page o916
April 2011

Received 11 March 2011
Accepted 13 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 17.8
Details

2-(4-Chlorobenzamido)acetic acid

Islam Ullah Khan,^a ^* Muneeb Hayat Khan,^a Muhammad Nadeem Arshad ^a and Mehmet Akkurt ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: iukhan@gcu.edu.pk, akkurt@erciyes.edu.tr

In the crystal structure of the title molecule, C₉H₈ClNO₃, adjacent molecules are arranged into centrosymmetric dimers through pairs of intermolecular O-HO interactions. Intermolecular N-HO hydrogen bonds link the dimers into a layer parallel to the bc plane. In the layer, molecules are packed in a face-to-face [pi] -stacked arrangment, showing [pi] - [pi] stacking interactions between the benzene rings with a centroid-centroid distance of 3.6884 (8) Å.

Related literature

For crystallographic studies of benzamide derivatives, see: Donnelly et al. (2008); Mugnoli et al. (1991); Stensland et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₉H₈ClNO₃
M_r = 213.61
Monoclinic, P 2₁ /c
a = 10.5035 (2) Å
b = 13.2105 (4) Å
c = 7.1226 (2) Å
= 102.203 (1)°
V = 965.98 (4) Å³
Z = 4
Mo K radiation
= 0.37 mm^-1
T = 296 K
0.36 × 0.21 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
9027 measured reflections
2365 independent reflections
1627 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.098
S = 1.02
2365 reflections
133 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.83 (2)	2.06 (2)	2.8491 (19)	160 (2)
O3-H1OO1ⁱⁱ	0.83 (1)	1.85 (2)	2.6613 (16)	165 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2688 ).

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University, Lahore.

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.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Donnelly, K., Gallagher, J. F. & Lough, A. J. (2008). Acta Cryst. C64, o335-o340.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Mugnoli, A., Carnasciali, M. M., Sancassan, F., Novi, M. & Petrillo, G. (1991). Acta Cryst. C47, 1916-1919.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stensland, B., Csöregh, I. & Högberg, T. (1995). Acta Cryst. B51, 847-856.

organic compounds