Ammonium 2-amino­pyrazine-3-carboxyl­ate

Lutz, M.; Jakobi, A.J.

doi:10.1107/S1600536811010865

Volume 67
Part 4
Page o984
April 2011

Received 18 March 2011
Accepted 23 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.026
wR = 0.072
Data-to-parameter ratio = 6.4
Details

Ammonium 2-aminopyrazine-3-carboxylate

Martin Lutz ^a ^* and Arjen J. Jakobi ^a

^aBijvoet Center for Biomolecular Research, Crystal and Structural Chemistry, Faculty of Science, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands
Correspondence e-mail: m.lutz@uu.nl

The title compound NH₄⁺·C₅H₄N₃O₂^- crystallizes with two formula units in the asymmetric unit. In each anion, the carboxylate is deprotonated and the planar amino group [angle sums of 359 (3) and 355 (3)° at N] remains protonated. In the crystal, the cations and anions are bridged by N-HO and N-HN hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structure of the free acid, see: Dobson & Gerkin (1996); Ptasiewicz-Bak & Leciejewicz (1997). For the metal complex with nickel, see: Ptasiewicz-Bak & Leciejewicz (1999). For the coordination chemistry of 2-pyrazinecarboxylic acid, see: Ptasiewicz-Bak et al. (1995); Ellsworth & zur Loye (2008). In the present study a half-normal probability plot (Abrahams & Keve, 1971), a quaternion fit (Mackay, 1984) and rigid-body analysis (Schomaker & Trueblood, 1998) have been used.

Experimental

Crystal data

NH₄⁺·C₅H₄N₃O₂^-
M_r = 156.15
Orthorhombic, P c a 2₁
a = 12.5066 (6) Å
b = 3.8833 (2) Å
c = 27.9659 (14) Å
V = 1358.22 (12) Å³
Z = 8
Mo K radiation
= 0.12 mm^-1
T = 150 K
0.40 × 0.19 × 0.09 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) T_min = 0.70, T_max = 0.75
16898 measured reflections
1580 independent reflections
1540 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.072
S = 1.05
1580 reflections
247 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N31-H31AN22ⁱ	0.92 (3)	2.20 (3)	3.103 (2)	169 (2)
N31-H31BO21	0.90 (3)	2.07 (3)	2.726 (2)	129 (2)
N32-H32AN21ⁱⁱ	0.88 (3)	2.23 (3)	3.100 (2)	168 (2)
N32-H32BO22	0.86 (3)	2.06 (3)	2.686 (2)	129 (2)
N3-H3BO21	0.93 (3)	1.97 (3)	2.849 (2)	157 (2)
N3-H3CO11ⁱⁱⁱ	0.96 (3)	2.58 (3)	3.287 (2)	131 (2)
N3-H3CN11ⁱⁱⁱ	0.96 (3)	2.00 (3)	2.909 (2)	159 (2)
N3-H3DO11^iv	0.89 (3)	2.13 (3)	2.944 (2)	152 (2)
N4-H4AO12	0.86 (3)	2.13 (3)	2.897 (2)	148 (3)
N4-H4AN12	0.86 (3)	2.23 (3)	2.912 (2)	135 (3)
N4-H4BO11	0.95 (4)	1.86 (4)	2.793 (2)	166 (3)
N4-H4CO11^v	0.84 (3)	2.01 (4)	2.839 (2)	170 (3)
N4-H4DO22^vi	0.87 (3)	1.87 (3)	2.742 (2)	176 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iv) $[x-{\script{1\over 2}}, -y+2, z]$ ; (v) x, y-1, z; (vi) $[x+{\script{1\over 2}}, -y+1, z]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: manual editing of SHELXL cif file.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2357 ).

References

Abrahams, S. C. & Keve, E. T. (1971). Acta Cryst. A27, 157-165.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dobson, A. J. & Gerkin, R. E. (1996). Acta Cryst. C52, 1512-1514.
Ellsworth, J. M. & zur Loye, H.-C. (2008). Dalton Trans. pp. 5823-5835.
Mackay, A. L. (1984). Acta Cryst. A40, 165-166.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Ptasiewicz-Bak, H. & Leciejewicz, J. (1997). Pol. J. Chem. 71, 1350-1358.
Ptasiewicz-Bak, H. & Leciejewicz, J. (1999). Pol. J. Chem. 73, 717-725.
Ptasiewicz-Bak, H., Leciejewicz, J. & Zachara, J. (1995). J. Coord. Chem. 36, 317-326.
Schomaker, V. & Trueblood, K. N. (1998). Acta Cryst. B54, 507-514.
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds