1,1-Dimethyl­biguanidium(2+) dinitrate

Fridrichová, M.; Císařová, I.; Němec, I.

doi:10.1107/S1600536811051105

Volume 68
Part 1
Pages o18-o19
January 2012

Received 18 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (N-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 12.5
Details

1,1-Dimethylbiguanidium(2+) dinitrate

Michaela Fridrichová,^a ^* Ivana Císarová ^a and Ivan Nemec ^a

^aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 12843 Prague 2, Czech Republic
Correspondence e-mail: fantom.ag@seznam.cz

In the crystal structure of the title compound, C₄H₁₃N₅²⁺·2NO₃^-, the main intermolecular interactions are the N-HO hydrogen bonds between the cationic amino groups and the O atoms of the nitrate ions. All amino H atoms and nitrate O atoms are involved in the three-dimensional hydrogen-bond network. There are two graph-set motifs R₂²(8), which include the amino groups connected to the N atoms in the biguanide 3-, 4- and 5-positions, and the O atoms of a nitrate ion. They are extended along the a axis. An O atom of the second nitrate ion is involved in a graph-set motif C(4) that is a part of a helix-like N-HOH-N-HO chain oriented along the b axis. There are also two weak C-HO interactions in the crystal structure.

Related literature

For uses of biguanide derivatives in medicine, see: Watkins et al. (1987). For applications of 1,1-dimethylbiguanide, see: Bell & Hadden (1997); Hopker (1961); Wiernsperger (2000). For 1,1-dimethylbiguanide in metal complexes, see: Gheorghiu (1969); Marchi et al. (1999); Spacu & Gheorghiu (1968, 1969); Viossat et al. (1995); Zhu et al. (2002). For related structures of monocation salts, see: Hariharan et al. (1989); He et al. (2002); Huang et al. (2008); Lu et al. (2004a); Zhu et al. (2003). For related structures of dication salts, see: Lemoine et al. (1994); Lu et al. (2004b). For related salt materials, see: Fridrichová et al. (2010); Matulková et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990). For details of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₄H₁₃N₅²⁺·2NO₃^-
M_r = 255.21
Monoclinic, P 2₁ /c
a = 7.7850 (2) Å
b = 5.7313 (2) Å
c = 26.5321 (7) Å
= 101.6020 (15)°
V = 1159.63 (6) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 150 K
0.4 × 0.3 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer
13222 measured reflections
2228 independent reflections
1913 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.113
S = 1.08
2228 reflections
178 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H12O2	0.89 (1)	2.06 (2)	2.9158 (17)	160 (2)
N1-H12O1	0.89 (1)	2.57 (2)	3.3151 (17)	142 (1)
N1-H11O5	0.88 (1)	2.09 (2)	2.9463 (16)	164 (2)
N1-H11O4	0.88 (1)	2.57 (2)	3.2920 (17)	140 (1)
N2-H21O4	0.84 (1)	2.15 (2)	2.9571 (18)	161 (2)
N2-H21O4ⁱ	0.84 (1)	2.56 (2)	3.0833 (17)	122 (2)
N2-H22O6ⁱⁱ	0.87 (1)	2.15 (2)	2.9674 (18)	157 (2)
N2-H22O6ⁱ	0.87 (1)	2.64 (2)	3.2503 (18)	128 (2)
N3-H3O5ⁱⁱ	0.85 (1)	2.05 (2)	2.8479 (16)	157 (2)
N3-H3O6ⁱⁱ	0.85 (1)	2.59 (2)	3.2947 (17)	142 (2)
N4-H42O3ⁱⁱⁱ	0.85 (1)	2.17 (2)	2.9300 (18)	149 (2)
N4-H42O1ⁱⁱⁱ	0.85 (1)	2.34 (2)	3.1164 (18)	153 (2)
N4-H41O3^iv	0.89 (1)	1.97 (2)	2.8487 (17)	170 (2)
C3-H3BO2ⁱⁱ	0.98	2.42	3.255 (2)	143
C4-H4AO6^v	0.98	2.55	3.519 (2)	170
Symmetry codes: (i) -x+1, -y, -z; (ii) x-1, y, z; (iii) x, y-1, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z.

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2139 ).

Acknowledgements

This work was supported by the Grant Agency of Charles University in Prague (grant No. 58608), the Czech Science Foundation (grant No. 203/09/0878) and it is a part of the long term Research Plan of the Ministry of Education of the Czech Republic (No. MSM0021620857). We would like to thank Dr Jan Fábry for his careful supervision and inspiring critique.

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organic compounds