Ethyl-enedi-ammonium chloride thio-cyanate.

In the ethyl-enedi-ammonium 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.

Related literature

For the crystal structures of related compounds, see: Kamoun et al. (1989 ▶); Chen (2009 ▶). For details of the synthesis of thio­cyanic acid, see: Bartlett et al. (1969 ▶). For protonic conductivity and dielectric relaxation in ethyl­endi­ammonium salts, see: Karoui et al. (2013 ▶).

Experimental

Crystal data

C2H10N2 2+·Cl−·n class="Chemical">SCN−

M = 155.65

Triclinic,

a = 6.2726 (2) Å

b = 6.3462 (2) Å

c = 9.1745 (3) Å

α = 92.436 (3)°

β = 92.193 (3)°

γ = 94.341 (3)°

V = 363.52 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.72 mm−1

T = 293 K

0.50 × 0.42 × 0.17 mm

Data collection

Agilent Xcalibur (Sapphire2) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T min = 0.737, T max = 0.887

6396 measured reflections

2189 independent reflections

1947 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.072

S = 1.08

2189 reflections

74 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008830/cv5396sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008830/cv5396Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008830/cv5396Isup3.cdx

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C2H10N22+·Cl−·SCN−	F(000) = 164
Mr = 155.65	Cell parameters from 3445 reflections
Triclinic, P1	Dx = 1.422 Mg m−3Dm = 1.398 Mg m−3Dm measured by flotation
Hall symbol: -P 1	Melting point: 443 K
a = 6.2726 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 6.3462 (2) Å	Cell parameters from 5534 reflections
c = 9.1745 (3) Å	θ = 3.2–44.7°
α = 92.436 (3)°	µ = 0.72 mm−1
β = 92.193 (3)°	T = 293 K
γ = 94.341 (3)°	Parallelipipedic, light yellow
V = 363.52 (2) Å3	0.50 × 0.42 × 0.17 mm
Z = 2

Agilent Xcalibur (Sapphire2) diffractometer	2189 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1947 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.3622 pixels mm-1	θmax = 30.5°, θmin = 3.2°
ω scans	h = −5→8
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −9→9
Tmin = 0.737, Tmax = 0.887	l = −13→13
6396 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.0716P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2189 reflections	Δρmax = 0.40 e Å−3
74 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.294 (15)
Primary atom site location: structure-invariant direct methods

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.19093 (4)	0.72470 (4)	0.47679 (3)	0.02934 (10)
S1	0.68519 (5)	0.78130 (5)	0.20850 (3)	0.03649 (10)
C1	0.45634 (19)	0.73609 (17)	0.11677 (11)	0.0294 (2)
N1	0.2924 (2)	0.7024 (2)	0.05464 (13)	0.0458 (3)
N2	0.31015 (15)	0.22026 (15)	0.43178 (10)	0.0305 (2)
H2A	0.4348	0.2481	0.4811	0.046*
H2B	0.2590	0.0888	0.4473	0.046*
H2C	0.2178	0.3109	0.4619	0.046*
C2	0.34163 (16)	0.24184 (17)	0.27393 (12)	0.0288 (2)
H2D	0.4449	0.1449	0.2424	0.035*
H2E	0.4007	0.3844	0.2582	0.035*
C3	0.13799 (19)	0.19753 (19)	0.18191 (12)	0.0322 (2)
H3E	0.1733	0.1811	0.0803	0.039*
H3D	0.0665	0.0651	0.2095	0.039*
N3	−0.01089 (16)	0.36715 (17)	0.19736 (11)	0.0345 (2)
H3A	−0.1283	0.3334	0.1412	0.052*
H3B	0.0525	0.4885	0.1701	0.052*
H3C	−0.0462	0.3812	0.2901	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.02482 (13)	0.02877 (14)	0.03390 (15)	−0.00093 (8)	0.00252 (9)	−0.00075 (9)
S1	0.02975 (16)	0.04342 (18)	0.03524 (17)	−0.00037 (11)	−0.00273 (11)	−0.00101 (12)
C1	0.0356 (5)	0.0265 (5)	0.0262 (5)	0.0033 (4)	−0.0003 (4)	0.0020 (3)
N1	0.0446 (6)	0.0482 (6)	0.0434 (6)	0.0040 (5)	−0.0144 (5)	0.0008 (5)
N2	0.0269 (4)	0.0339 (5)	0.0312 (4)	0.0058 (3)	−0.0035 (3)	0.0048 (3)
C2	0.0229 (4)	0.0312 (5)	0.0329 (5)	0.0040 (4)	0.0042 (4)	0.0030 (4)
C3	0.0337 (5)	0.0347 (5)	0.0275 (5)	0.0027 (4)	−0.0009 (4)	−0.0066 (4)
N3	0.0291 (4)	0.0447 (5)	0.0296 (5)	0.0075 (4)	−0.0064 (3)	0.0002 (4)

S1—C1	1.6358 (12)	C2—H2E	0.9700
C1—N1	1.1573 (16)	C3—N3	1.4834 (15)
N2—C2	1.4798 (14)	C3—H3E	0.9700
N2—H2A	0.8900	C3—H3D	0.9700
N2—H2B	0.8900	N3—H3A	0.8900
N2—H2C	0.8900	N3—H3B	0.8900
C2—C3	1.5054 (15)	N3—H3C	0.8900
C2—H2D	0.9700
N1—C1—S1	178.48 (11)	N3—C3—C2	112.98 (9)
C2—N2—H2A	109.5	N3—C3—H3E	109.0
C2—N2—H2B	109.5	C2—C3—H3E	109.0
H2A—N2—H2B	109.5	N3—C3—H3D	109.0
C2—N2—H2C	109.5	C2—C3—H3D	109.0
H2A—N2—H2C	109.5	H3E—C3—H3D	107.8
H2B—N2—H2C	109.5	C3—N3—H3A	109.5
N2—C2—C3	113.06 (9)	C3—N3—H3B	109.5
N2—C2—H2D	109.0	H3A—N3—H3B	109.5
C3—C2—H2D	109.0	C3—N3—H3C	109.5
N2—C2—H2E	109.0	H3A—N3—H3C	109.5
C3—C2—H2E	109.0	H3B—N3—H3C	109.5
H2D—C2—H2E	107.8
N2—C2—C3—N3	72.09 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1i	0.89	2.36	3.1982 (9)	158
N2—H2B···Cl1ii	0.89	2.35	3.2246 (10)	169
N2—H2C···Cl1iii	0.89	2.64	3.3237 (10)	134
N3—H3C···Cl1iii	0.89	2.46	3.2953 (11)	158
N3—H3A···N1iv	0.89	2.03	2.8533 (14)	153
N2—H2C···Cl1	0.89	2.64	3.3543 (10)	138
N3—H3B···N1	0.89	2.27	3.1106 (17)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1i	0.89	2.36	3.1982 (9)	158
N2—H2B⋯Cl1ii	0.89	2.35	3.2246 (10)	169
N2—H2C⋯Cl1iii	0.89	2.64	3.3237 (10)	134
N3—H3C⋯Cl1iii	0.89	2.46	3.2953 (11)	158
N3—H3A⋯N1iv	0.89	2.03	2.8533 (14)	153
N2—H2C⋯Cl1	0.89	2.64	3.3543 (10)	138
N3—H3B⋯N1	0.89	2.27	3.1106 (17)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .