Ethylenediammonium chloride thiocyanate

In the ethylenediammonium dication of the title salt, C2H10N2 2+·Cl−·SCN−, the N—C—C—N torsion angle is 72.09 (12)°. In the crystal, an extensive three-dimensional hydrogen-bonding network, formed by N—H⋯Cl and N—H⋯N hydrogen bonds, holds all the ions together.

In the ethylenediammonium dication of the title salt, C 2 H 10 N 2 2+ ÁCl À ÁSCN À , the N-C-C-N torsion angle is 72.09 (12) . In the crystal, an extensive three-dimensional hydrogen-bonding network, formed by N-HÁ Á ÁCl and N-HÁ Á ÁN hydrogen bonds, holds all the ions together.
In (I) (Fig. 1), the asymmetric unit consists of one diprotonated ethylenediammonium cation, one Cland one SCNanions. In this atomic arrangement, the organic group has no internal symmetry. In fact, the mean length of the C-N bonds: 1.4816 (14) Å is lower than that of the C-C bonds:1.5054 (15) Å. The [C 2 H 10 N 2 ] 2+ dication shows an eclipsed conformation with a N-C-C-N torsion angle of 72.09 (12)°. The main geometrical features of this group are similar to that reported for others ethylenediammonium halides (Chen, 2009) and phosphates (Kamoun et al.,1989). The thiocyanate ion, present as a monodentate ligand, is almost linear with an angle of 178.48 (11)° and an average C-S and C-N bond lengths of 1.6358 (12) Å and 1.1573 (16) Å, respectively.
In the crystal structure, the ethylenediammonium cations are linked to the chloride and thiocyanate anions by means of five medium N-H···Cl and two weak N-H···N(CS) intermolecular hydrogen bonds (Table 1) to form a threedimensional network (Fig. 2). The N···Cl and N···N(CS) distances range from 3.1982 (9) to 3.3543 (10) Å and 2.8533 (14) Å to 3.1106 (17) Å, respectively. The sum of Van der Waal's radii of N and Cl, and N and O are 3.3 Å and 2.9 Å, respectively.

Experimental
The title compound has been obtained as crystalline solid in the reaction of ethylenediamine with an aqueous acidic mixture of hydrochloric acid and thiocyanic acid (1/1 ratio). Thiocyanic acid was prepared using the published procedure (Bartlett et al., 1969). After a slow solvent evaporation yellow crystals suitable for X-ray analysis were obtained.They were washed with diethyl ether and dried over P 2 O 5 .

Refinement
The H atoms were positioned geometrically (the C-H and N-H bonds were respectively fixed at 0.96 and 0.89), and allowed to ride on their parent atoms, with U iso (H) = 1.2 U eq (C, N).

Computing details
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg et al., 1999) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.40 e Å −3 Δρ min = −0.25 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.294 (15) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq