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Volume 68 
Part 1 
Page o221  
January 2012  

Received 1 December 2011
Accepted 19 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.128
Data-to-parameter ratio = 15.3
Details
Open access

N-(2-Chloro-5-methylphenyl)succinamic acid

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C11H12ClNO3, the conformation of the N-H bond in the amide segment is syn with respect to the ortho-Cl atom. The amide and carboxyl C=O groups are syn to each other. Furthermore, the C=O and O-H bonds of the carboxyl group are in syn positions with respect to each other. The dihedral angle between the benzene ring and the amide group is 47.8 (2)°. In the crystal, molecules are connected by pairs of O-H...O hydrogen bonds, forming inversion dimers. The dimers are further linked by N-H...O hydrogen bonds into double chains along the b-axis direction.

Related literature

For our previous studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.]); Saraswathi et al. (2011[Saraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2093.]), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]) and on N-chloroarylamides, see: Gowda et al. (1996[Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.]). For modes of hydrogen bonding in the structures of carboxylic acids, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). For the centrosymmetrical dimeric hydrogen-bonding association of carboxylic groups, see: Jagannathan et al. (1994[Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12ClNO3

  • Mr = 241.67

  • Monoclinic, C 2/c

  • a = 23.780 (5) Å

  • b = 4.7784 (7) Å

  • c = 23.892 (5) Å

  • [beta] = 121.20 (1)°

  • V = 2322.2 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 293 K

  • 0.42 × 0.10 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.877, Tmax = 0.975

  • 4399 measured reflections

  • 2322 independent reflections

  • 1680 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.128

  • S = 1.19

  • 2322 reflections

  • 152 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3O...O2i 0.83 (2) 1.83 (2) 2.652 (4) 172 (5)
N1-H1N...O1ii 0.86 (2) 2.08 (2) 2.910 (4) 163 (3)
Symmetry codes: (i) [-x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2035 ).


Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.

References

Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.  [ChemPort]
Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.  [ChemPort]
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.  [ChemPort]
Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.  [CrossRef] [ChemPort] [ISI]
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.  [ChemPort]
Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.  [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Saraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2093.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o221  [ doi:10.1107/S1600536811054638 ]

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