A second monoclinic polymorph of ethyl­enediammonium bis­(hydrogen squarate) monohydrate

Zenkhri, L.; Bataille, T.; Audebrand, N.

doi:10.1107/S1600536811009019

Volume 67
Part 5
Page o1118
May 2011

Received 24 February 2011
Accepted 9 March 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 15.6
Details

A second monoclinic polymorph of ethylenediammonium bis(hydrogen squarate) monohydrate

Louiza Zenkhri,^a ^* Thierry Bataille ^b and Nathalie Audebrand ^b

^aFaculté des Sciences et Technologie et Sciences de la Matière, Université Kasdi Merbah Ouargla, Route Gardaia, Ourgla, Algeria, and ^bLaboratoire Sciences Chimiques de Rennes (CNRS, UMR 6226), Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes Cedex, France
Correspondence e-mail: louizazenkhri@yahoo.fr

The title compound, C₂H₁₀N₂²⁺·2HC₄O₄^-·H₂O, a new polymorph of ethylenediammonium bis(hydrogen squarate) monohydrate, was synthesized by slow evaporation of an acid solution. The asymetric unit contains two hydrogen squarate anions, two half-molecules of protonated ethylenediamine arranged around a twofold axis and one water molecule. In the crystal, N-HO and O-HO hydrogen bonds between the hydrogen squarate anions, protonated N atoms from the amine group and water molecules lead to a three-dimensional framework. In particular, the cohesion between the squarate groups is ensured by very short intermolecular hydrogen bonds bonds. The title compound crystallized together with the previously reported polymorph [Mathew et al. (2002). J. Mol. Struct. 641, 263-279].

Related literature

For the previously reported polymorph, see: Mathew et al. (2002).

Experimental

Crystal data

C₂H₁₀N₂²⁺·2C₄HO₄^-·H₂O
M_r = 306.23
Monoclinic, P 2/c
a = 14.1907 (3) Å
b = 9.0224 (2) Å
c = 10.9412 (2) Å
= 111.789 (1)°
V = 1300.77 (5) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 293 K
0.45 × 0.44 × 0.37 mm

Data collection

Nonius KappaCCD diffractometer
16099 measured reflections
2957 independent reflections
2101 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.116
S = 1.06
2957 reflections
190 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO5ⁱ	0.89	2.14	2.9205 (17)	146
N1-H1BO1Wⁱⁱ	0.88	1.99	2.8482 (18)	163
N1-H1CO8	0.88	1.90	2.7717 (18)	169
N2-H2AO2	0.88	1.97	2.8222 (17)	162
N2-H2BO1Wⁱⁱⁱ	0.90	1.94	2.8279 (18)	171
N2-H2CO1ⁱ	0.90	1.92	2.8071 (17)	168
O4-H4O3^iv	1.05	1.42	2.4675 (15)	179
O7-H7O6ⁱⁱⁱ	1.06	1.41	2.4645 (14)	178
O1W-H1WO6	0.92	2.10	2.8724 (17)	140
O1W-H1WO8^iv	0.92	2.40	3.0489 (18)	128
O1W-H2WO3	0.93	1.88	2.8035 (19)	171
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x, -y, z+{\script{1\over 2}}]$ ; (iv) $[x, -y, z-{\script{1\over 2}}]$ .

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); 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: DN2662 ).

Acknowledgements

Grateful thanks are expressed to Dr T. Roisnel (Centre de Diffractomtétrie X, UMR CNRS 6226) for his assistance with the single-crystal data collection.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Mathew, S., Paul, G., Shivasankar, K., Choudhury, A. & Rao, C. N. R. (2002). J. Mol. Struct. 641, 263-279.
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 & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds