(IUCr) 3-(3,5-Dichloroanilinocarbonyl)propionic acid

Volume 64
Part 5
Page o787
May 2008

Received 30 March 2008
Accepted 31 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 17.3
Details

3-(3,5-Dichloroanilinocarbonyl)propionic acid

Farooq Ali Shah,^a M. Nawaz Tahir,^b ^* Saqib Ali ^a and Muhammad Akram Kashmiri ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan,^bUniversity of Sargodha, Department of Physics, Sagrodha, Pakistan, and ^cGovernment College University, Department of Chemistry, Lahore, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The crystal structure of the title compound, C₁₀H₉Cl₂NO₃, consists of dimers due to intermolecular O-HO hydrogen bonding forming an R₂²(8) ring through the carboxyl groups. These dimers are linked to each other by intermolecular hydrogen bonds between the amine group and the adjacent carbonyl O atom. A single C-Cl [pi] interaction is also observed between the chloro-substituted aromatic rings.

Related literature

For related literature, see: Nath et al. (2001); Wardell et al. (2006).

Experimental

Crystal data

C₁₀H₉Cl₂NO₃
M_r = 262.08
Triclinic, $[P \overline 1]$
a = 4.8568 (2) Å
b = 8.6677 (4) Å
c = 13.9038 (8) Å
= 74.467 (3)°
= 80.495 (2)°
= 82.712 (3)°
V = 554.09 (5) Å³
Z = 2
Mo K radiation
= 0.57 mm^-1
T = 296 (2) K
0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.870, T_max = 0.945
12157 measured reflections
2971 independent reflections
2065 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.125
S = 1.07
2971 reflections
172 parameters
Only H-atom coordinates refined
_max = 0.27 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO3ⁱ	0.84 (3)	2.07 (3)	2.904 (2)	175 (2)
O1-H1O2ⁱⁱ	0.92 (4)	1.74 (4)	2.658 (3)	175 (4)
C7-Cl1Cgⁱⁱⁱ	1.74 (1)	3.54 (1)	4.033 (2)	93 (1)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z; (iii) x-1, y, z. Cg is the centroid of atoms C5-C10.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2109 ).

Acknowledgements

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer. Dr Saqib Ali is also grateful to the PSF for financial support under project No. PSF/R&D/C-QU/Chem(270).

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Nath, M., Pokharia, S. & Yadav, R. (2001). Coord. Chem. Rev. 215, 99-149.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o45-o46.

organic compounds