2-Amino-5-chloro­pyridinium 4-amino­benzoate

Kannan, V.; Sugumar, P.; Brahadeeswaran, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536812043085

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.112
Data-to-parameter ratio = 17.2
Details

2-Amino-5-chloropyridinium 4-aminobenzoate

V. Kannan,^a P. Sugumar,^b S. Brahadeeswaran ^c and M. N. Ponnuswamy ^b ^*

^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-HO 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); Tomaru et al. (1991). For N-HO hydrogen bonds, see: Blessing (1986); Brown (1976).

Experimental

Crystal data

C₅H₆ClN₂⁺·C₇H₆NO₂^-
M_r = 265.70
Monoclinic, P 2₁ /n
a = 6.9879 (4) Å
b = 22.0074 (13) Å
c = 8.0554 (5) Å
= 92.796 (1)°
V = 1237.33 (13) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.941, T_max = 0.946
12108 measured reflections
3086 independent reflections
2642 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(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
_max = 0.20 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	1.76	2.6135 (15)	175
N2-H2AO1ⁱ	0.89 (2)	1.94 (2)	2.8216 (18)	172.1 (19)
N2-H2BO1ⁱⁱ	0.86 (2)	2.10 (2)	2.8776 (17)	150.3 (19)
N3-H3AO1ⁱⁱⁱ	0.862 (19)	2.19 (2)	3.0357 (18)	167.4 (17)
N3-H3BO2^iv	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); cell refinement: SAINT (Bruker, 2008); 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Brahadeeswaran, S., Onduka, S., Takagi, M., Takahashi, Y., Adachi, H., Yoshimura, M., Mori, Y. & Sasaki, T. (2006). J. Cryst. Growth, 292, 441-444.
Brown, I. D. (1976). Acta Cryst. A32, 24-31.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tomaru, S., Matsumoto, S., Kurihara, T., Suzuki, H., Oobara, N. & Kaino, T. (1991). Appl. Phys. Lett. 58, 2583-2585.

organic compounds