2-Amino-5-chloro­pyridinium 2-carb­oxy­acetate

Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810019677

Volume 66
Part 6
Pages o1496-o1497
June 2010

Received 25 May 2010
Accepted 25 May 2010
Online 29 May 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.097
Data-to-parameter ratio = 16.9
Details

2-Amino-5-chloropyridinium 2-carboxyacetate

Madhukar Hemamalini ^a and Hoong-Kun Fun ^a ^*⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The title salt, C₅H₆ClN₂⁺·C₃H₃O₄^-, contains two cations and two anions in the asymmetric unit. Both 2-amino-5-chloropyridinium ions are protonated at their pyridine N atoms and both hydrogen malonate ions feature an intramolecular O-HO hydrogen bond, which generates an S(6) ring motif and results in a folded conformation. In the crystal structure, the cations and anions are linked via N-HO, O-HO and C-HO hydrogen bonds, forming chains propagating in [010], which are cross-linked by further C-HO interactions.

Related literature

For background to the chemistry of substituted pyridines, see: Amr et al. (2006); Bart et al. (2001); Shinkai et al. (2000); Klimesôva et al. (1999). For related structures, see: Pourayoubi et al. (2007); Janczak & Perpétuo (2009); Akriche & Rzaigui (2005). For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₆ClN₂⁺·C₃H₃O₄^-
M_r = 232.62
Monoclinic, P 2₁ /c
a = 15.6971 (19) Å
b = 16.866 (2) Å
c = 7.4662 (10) Å
= 94.518 (3)°
V = 1970.5 (4) Å³
Z = 8
Mo K radiation
= 0.38 mm^-1
T = 100 K
0.22 × 0.14 × 0.07 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.921, T_max = 0.973
22474 measured reflections
5811 independent reflections
4314 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.097
S = 1.01
5811 reflections
343 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.37 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1NAO1A	0.93 (2)	1.68 (2)	2.5982 (17)	171 (2)
N2A-H2NAO2A	0.95 (2)	2.01 (2)	2.9518 (19)	169.1 (18)
N2A-H3NAO3Bⁱ	0.87 (2)	2.07 (2)	2.9333 (18)	178 (2)
N1B-H1NBO1B	0.92 (2)	1.69 (2)	2.5980 (17)	169 (2)
N2B-H2NBO2B	0.88 (2)	2.08 (2)	2.9538 (19)	175 (2)
N2B-H3NBO3Aⁱⁱ	0.93 (2)	2.04 (2)	2.9598 (19)	175 (2)
O4A-H1OAO2A	0.94 (2)	1.58 (2)	2.4835 (16)	158 (2)
O4B-H1OBO2B	0.93 (3)	1.57 (3)	2.4752 (16)	162 (3)
C1A-H1AO3Bⁱⁱⁱ	0.960 (18)	2.458 (18)	3.374 (2)	159.6 (14)
C1B-H1BO3Aⁱⁱⁱ	0.98 (2)	2.46 (2)	3.417 (2)	166.1 (18)
C7A-H7ABO1Bⁱⁱⁱ	0.97 (2)	2.31 (2)	3.2509 (19)	162.6 (18)
C7B-H7BBO4A^iv	0.96 (2)	2.55 (2)	3.440 (2)	155.7 (16)
C4A-H4AO4Bⁱ	0.95 (2)	2.32 (2)	3.264 (2)	171.6 (18)
C4B-H4BO4Aⁱⁱ	0.94 (2)	2.30 (2)	3.237 (2)	177.4 (17)
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+2; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5466 ).

Acknowledgements

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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organic compounds