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Volume 66 
Part 8 
Page o1945  
August 2010  

Received 28 May 2010
Accepted 23 June 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.137
Data-to-parameter ratio = 15.3
Details
Open access

2-Aminoanilinium 2-chloroacetate

aSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, India
Correspondence e-mail: skdsc@uohyd.ernet.in

In the crystal structure of the title compound, C6H9N2+·ClCH2COO-, prepared by the reaction of OPDA (orthophenelynediamine) with chloroacetic acid, N-H...O hydrogen bonds generate ladder-like chains and very weak intermolecular C-H...Cl hydrogen-bonding interactions between the anions and cations lead to a supramolecular network. C-H...O interactions also occur.

Related literature

For hydrogen bonding with chlorine, see: Brammer et al. (2008[Brammer, L., Espellargas, G. M. & Libri, S. (2008). CrystEngComm, 10, 1712-1727.]); Metrangolo et al. (2006[Metrangolo, P., Pilati, T. & Resnati, G. (2006). CrystEngComm, 8, 946-947.], 2009[Metrangolo, P., Pilati, T., Terraneo, G., Biella, S. & Resnati, G. (2009). CrystEngComm, 11, 1187-1196.]). For ladder-like networks, see: Kinbara, Hashimoto et al. (1996[Kinbara, K., Hashimoto, Y., Sukegawa, Y., Nohira, H. & Saigo, A. (1996). J. Am. Chem. Soc. 118, 3441-3449.]); Kinbara, Kai et al. (1996[Kinbara, K., Kai, A., Maekawa, Y., Hashimoto, Y., Naruse, S., Hasegawa, M. & Saigo, K. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 247-253.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C2H2ClO2-

  • Mr = 202.64

  • Monoclinic, P 21 /c

  • a = 11.371 (3) Å

  • b = 4.4852 (11) Å

  • c = 20.115 (4) Å

  • [beta] = 110.439 (12)°

  • V = 961.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 298 K

  • 0.36 × 0.20 × 0.16 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.879, Tmax = 0.944

  • 9366 measured reflections

  • 1922 independent reflections

  • 1651 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.137

  • S = 1.09

  • 1922 reflections

  • 126 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1C...O2i 0.90 1.88 2.777 (2) 173
N1-H1B...O2ii 0.94 1.82 2.763 (2) 173
N2-H2B...O1 0.87 2.16 3.004 (3) 163
C4-H4...O1iii 0.93 2.66 3.527 (3) 156
C3-H3...Cl1iv 0.93 3.24 3.985 (3) 138
N2-H2A...N2iii 0.81 2.77 3.587 (4) 179
C8-H8A...Cl1v 0.90 (3) 3.10 (3) 3.878 (3) 146 (3)
C8-H8B...O1vi 0.99 (4) 2.71 (4) 3.491 (4) 136 (3)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) -x+2, -y, -z+2; (vi) x, y-1, z.

Data collection: SMART (Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2035 ).


Acknowledgements

We thank the Department of Science and Technology, Government of India, for the National X-ray Diffractometer facility at the University of Hyderabad. We acknowledge the Department of Science and Technology, Government of India, for financial support (project No. SR/S1/IC-23/2007). ASR and RK are grateful to the CSIR, Government of India, and BKT thanks the UGC, Government of India, for their fellowships. We also thank Dr A. R. Bijju, School of Chemistry, University of Hyderabad, for helpful discussions.

References

Brammer, L., Espellargas, G. M. & Libri, S. (2008). CrystEngComm, 10, 1712-1727.  [ISI] [CrossRef] [ChemPort]
Bruker (2003). SADABS, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Kinbara, K., Hashimoto, Y., Sukegawa, Y., Nohira, H. & Saigo, A. (1996). J. Am. Chem. Soc. 118, 3441-3449.  [CrossRef] [ChemPort] [ISI]
Kinbara, K., Kai, A., Maekawa, Y., Hashimoto, Y., Naruse, S., Hasegawa, M. & Saigo, K. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 247-253.
Metrangolo, P., Pilati, T. & Resnati, G. (2006). CrystEngComm, 8, 946-947.  [ISI] [CrossRef] [ChemPort]
Metrangolo, P., Pilati, T., Terraneo, G., Biella, S. & Resnati, G. (2009). CrystEngComm, 11, 1187-1196.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o1945  [ doi:10.1107/S1600536810024554 ]

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