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Volume 68 
Part 11 
Page o3187  
November 2012  

Received 1 October 2012
Accepted 16 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.112
Data-to-parameter ratio = 17.2
Details
Open access

2-Amino-5-chloropyridinium 4-aminobenzoate

aDepartment of Physics, M.A.M. School of Engineering, Siruganur, Tiruchirappalli 621 105, India,bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Physics, Anna University, BIT Campus, Tiruchirappalli 620 024, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title molecular salt, C5H6ClN2+·C7H6NO2-, the cations and anions are connected by cation-to-anion and anion-to-anion N-H...O hydrogen bonds into a three-dimensional network. The dihedral angle between the ring and the CO2 group in the anion is 7.14 (7)°.

Related literature

For general background to chloropyridinium derivatives, see: Brahadeeswaran et al. (2006[Brahadeeswaran, S., Onduka, S., Takagi, M., Takahashi, Y., Adachi, H., Yoshimura, M., Mori, Y. & Sasaki, T. (2006). J. Cryst. Growth, 292, 441-444.]); Tomaru et al. (1991[Tomaru, S., Matsumoto, S., Kurihara, T., Suzuki, H., Oobara, N. & Kaino, T. (1991). Appl. Phys. Lett. 58, 2583-2585.]). For N-H...O hydrogen bonds, see: Blessing (1986[Blessing, R. H. (1986). Acta Cryst. B42, 613-621.]); Brown (1976[Brown, I. D. (1976). Acta Cryst. A32, 24-31.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6ClN2+·C7H6NO2-

  • Mr = 265.70

  • Monoclinic, P 21 /n

  • a = 6.9879 (4) Å

  • b = 22.0074 (13) Å

  • c = 8.0554 (5) Å

  • [beta] = 92.796 (1)°

  • V = 1237.33 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 293 K

  • 0.20 × 0.19 × 0.18 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.946

  • 12108 measured reflections

  • 3086 independent reflections

  • 2642 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.112

  • S = 1.04

  • 3086 reflections

  • 179 parameters

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.86 1.76 2.6135 (15) 175
N2-H2A...O1i 0.89 (2) 1.94 (2) 2.8216 (18) 172.1 (19)
N2-H2B...O1ii 0.86 (2) 2.10 (2) 2.8776 (17) 150.3 (19)
N3-H3A...O1iii 0.862 (19) 2.19 (2) 3.0357 (18) 167.4 (17)
N3-H3B...O2iv 0.86 (2) 2.08 (2) 2.9291 (18) 171 (2)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6844 ).


Acknowledgements

The authors thank the TBI Consultancy, University of Madras, India, for the data collection.

References

Blessing, R. H. (1986). Acta Cryst. B42, 613-621.  [CrossRef] [ISI] [details]
Brahadeeswaran, S., Onduka, S., Takagi, M., Takahashi, Y., Adachi, H., Yoshimura, M., Mori, Y. & Sasaki, T. (2006). J. Cryst. Growth, 292, 441-444.  [ISI] [CrossRef] [ChemPort]
Brown, I. D. (1976). Acta Cryst. A32, 24-31.  [CrossRef] [details]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [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]
Tomaru, S., Matsumoto, S., Kurihara, T., Suzuki, H., Oobara, N. & Kaino, T. (1991). Appl. Phys. Lett. 58, 2583-2585.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, o3187  [ doi:10.1107/S1600536812043085 ]

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