Imidazole–imidazolium picrate monohydrate

Moreno-Fuquen, R.; De Almeida Santos, R.; Aguirre, L.

doi:10.1107/S160053681005169X

Volume 67
Part 1
Page o139
January 2011

Received 22 November 2010
Accepted 9 December 2010
Online 15 December 2010

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.109
Data-to-parameter ratio = 8.9
Details

Imidazole-imidazolium picrate monohydrate

Rodolfo Moreno-Fuquen,^a ^* Regina De Almeida Santos ^b and Lina Aguirre ^c

^aDepartamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,^bInstituto de Química,IFSC, Universidade de São Paulo, São Carlos, Brazil, and ^cUniversidad Menendez Pelayo, Casa de la Ciencia, Pabellón del Perú, Avda Maria Luisa, s/n 41013, Sevilla, Spain
Correspondence e-mail: rodimo26@yahoo.es

The asymmetric unit of the title compound, C₃H₅N₂⁺·C₆H₂N₃O₇^-·C₃H₄N₂·H₂O or H(C₃H₄N₂)₂⁺·C₆H₂N₃O₇^-·H₂O, contains a diimidazolium cationic unit, one picrate anion and one molecule of water. In the crystal, the components are connected by N-HO, N-HN and O-HO hydrogen bonds, forming a two-dimensional network parallel to (001). In addition, weak intermolecular C-HO hydrogen bonds lead to the formation of a three-dimensional network featuring R₅⁵(19) rings.

Related literature

For background to imidazolium salts see: Moreno-Fuquen et al. (2009a,b ). For imidazole as an antifungal agent, see: Miranda et al. (1998); Rodriguez & Acosta (1997). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond geometries, see: Emsley (1984); Etter (1990); Nardelli (1995).

Experimental

Crystal data

C₃H₅N₂⁺·C₆H₂N₃O₇^-·C₃H₄N₂·H₂O
M_r = 383.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 3.8180 (1) Å
b = 20.8160 (8) Å
c = 21.4420 (8) Å
V = 1704.11 (10) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 291 K
0.53 × 0.21 × 0.14 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
12017 measured reflections
2207 independent reflections
1723 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.109
S = 1.06
2207 reflections
248 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N5-H5N6	0.86	1.81	2.666 (3)	180
N4-H401O5	0.94	1.78	2.714 (3)	176
O5-H501O1	0.91	1.90	2.801 (3)	179
O5-H502O1ⁱ	0.99	1.82	2.782 (3)	163
N7-H701O1ⁱⁱ	0.88	2.01	2.876 (2)	167
C10-H101O6ⁱⁱⁱ	0.93	2.51	3.352 (4)	151
C9-H91O8^iv	0.93	2.58	3.481 (3)	162
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5175 ).

Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002). RMF also thanks the Universidad del Valle, Colombia, and the Instituto de Química de São Carlos, USP, Brazil, for partial financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Emsley, J. (1984). Complex Chemistry, Structure and Bonding. Vol. 57, pp. 147-191. Berlin: Springer-Verlag.
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Miranda, C. L., Henderson, M. C. & Buhler, D. R. (1998). Toxicol. Appl. Pharmacol. 148, 237-244.
Moreno-Fuquen, R., Ellena, J. & Theodoro, J. E. (2009a). Acta Cryst. E65, o2717.
Moreno-Fuquen, R., Kennedy, A. R., Gilmour, D., De Almeida Santos, R. H. & Viana, R. B. (2009b). Acta Cryst. E65, o3044-o3045.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307-326. New York: Academic Press.
Rodriguez, R. J. & Acosta, D. Jr (1997). Toxicology, 117, 123-131.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds