2-(3-Amino­pyridinium-1-yl)-3-carb­oxy­propano­ate monohydrate

Millán Corrales, G.; Morales-Morales, D.; Hernández-Ortega, S.; Campos-Gaxiola, J.J.; Cruz Enríquez, A.

doi:10.1107/S1600536812006897

Volume 68
Part 3
Page o853
March 2012

Received 31 January 2012
Accepted 15 February 2012
Online 24 February 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.058
Data-to-parameter ratio = 11.7
Details

2-(3-Aminopyridinium-1-yl)-3-carboxypropanoate monohydrate

Guadalupe Millán Corrales,^a David Morales-Morales,^b Simón Hernández-Ortega,^b José J. Campos-Gaxiola ^a and Adriana Cruz Enríquez ^a ^*

^aFacultad de Ingeniería Mochis, Universidad Autónoma de Sinaloa, Fuente de Poseidón y Prol. Angel Flores, CP 81223, Los Mochis, Sinaloa, Mexico, and ^bInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacan, CP 04510, México, DF, Mexico
Correspondence e-mail: cenriqueza@yahoo.com.mx

The title compound, C₉H₁₀N₂O₄·H₂O, was obtained as a zwitterion derived from the nucleophilic attack of 3-aminopyridine on the fumaric [alpha] , [beta] -system. Within the molecule, the aminopyridine moiety and the carboxylate and carboxylic acid fragments form dihedral angles of 68.6 (2) and 62.8 (2)°, respectively. The geometry adopted by the molecule does not allow the formation of centrosymmetric dimeric hydrogen-bonded units; instead chains along the a axis are linked by COO-HOOC motifs. These chains are interconnected by N-HO and O-HO hydrogen bonds involving the carboxylic acid and carboxylate units and the solvent water molecules.

Related literature

For background to the synthesis, see: Kavuru et al. (2010). For structures and applications of zwitterion derivatives, see: Bis & Zaworotko (2005); Hill et al. (2001); Sarma et al. (2009). For fundamental hydrogen-bond interactions, see: Desiraju (1995); Etter (1990, 1991).

Experimental

Crystal data

C₉H₁₀N₂O₄·H₂O
M_r = 228.21
Orthorhombic, P n a 2₁
a = 7.4939 (8) Å
b = 19.446 (2) Å
c = 7.0227 (7) Å
V = 1023.39 (19) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 298 K
0.30 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
10663 measured reflections
1868 independent reflections
1642 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.058
S = 0.96
1868 reflections
160 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.11 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2ⁱ	0.87 (1)	1.60 (1)	2.4681 (15)	177 (2)
O5-H5AO4ⁱⁱ	0.85 (1)	2.04 (1)	2.8879 (18)	174 (2)
O5-H5BO1ⁱⁱⁱ	0.86 (1)	1.94 (1)	2.7968 (19)	173 (2)
N2-H2AO5^iv	0.91 (1)	2.02 (1)	2.920 (2)	168 (2)
N2-H2BO4^iv	0.91 (1)	2.08 (1)	2.987 (2)	173 (2)
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y, z-1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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) and SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2513 ).

Acknowledgements

This work was supported by the Secretaria de Educación Pública (PROMEP, PTC-035) and Universidad Autónoma de Sinaloa (DGIP, PROFAPI-048). Support of this research by CONACyT (grant No. 154732) is gratefully acknowledged.

References

Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Etter, M. C. (1991). J. Phys. Chem. 9, 4601-4610.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hill, L. W., Rondan, N. & Schmidt, D. (2001). Macromolecules, 34, 372-375.
Kavuru, P., Aboarayes, D., Arora, K. K., Clarke, H. D., Kennedy, A., Marshall, L., Ong, T. T., Perman, J., Pujari, T., Wojtas, L. & Zaworotko, M. J. (2010). Cryst. Growth Des. 10, 3568-3584.
Sarma, B. N., Balakrishna, K. N., Bhogala, N. & Nangia, A. (2009). Cryst. Growth Des. 9, 1546-1557.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds