Ethyl-enediaminium hemioxalate thio-cyanate.

In the title compound, C(2)H(10)N(2) (2+)·0.5(C(2)O(4))(2-)·NCS(-), the ethyl-enediaminium dication adopts a (+)-synclinal conformation with an N-C-C-N torsion angle of 62.64 (15)°. The oxalate dianion lies across an inversion centre. In the crystal structure, the ions are linked through N-H⋯N, N-H⋯O and C-H⋯S hydrogen bonds, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Barnes et al. (1998 ▶); Smith et al. (2006 ▶); Seidel et al. (2008 ▶); Tang et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C2H10N2 2+·0.5C2O4 2−·NCS−

M = 164.21

Triclinic,

a = 6.4044 (19) Å

b = 6.6199 (19) Å

c = 9.377 (3) Å

α = 80.799 (5)°

β = 81.179 (5)°

γ = 74.452 (5)°

V = 375.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.43 × 0.41 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.854, T max = 0.879

5091 measured reflections

1867 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.06

1867 reflections

94 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005994/ci5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005994/ci5031Isup2.hkl

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

C2H10N22+·0.5C2O42−·NCS−	Z = 2
Mr = 164.21	F(000) = 174
Triclinic, P1	Dx = 1.452 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4044 (19) Å	Cell parameters from 3525 reflections
b = 6.6199 (19) Å	θ = 2.2–28.3°
c = 9.377 (3) Å	µ = 0.38 mm−1
α = 80.799 (5)°	T = 298 K
β = 81.179 (5)°	Block, colourless
γ = 74.452 (5)°	0.43 × 0.41 × 0.35 mm
V = 375.5 (2) Å3

Bruker SMART APEX CCD area-detector diffractometer	1867 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 83.66 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scan	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.854, Tmax = 0.879	l = −12→12
5091 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1426P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1867 reflections	Δρmax = 0.51 e Å−3
94 parameters	Δρmin = −0.52 e Å−3
0 restraints	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.41 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.23176 (14)	0.09074 (15)	0.45456 (11)	0.0325 (2)
O2	0.41295 (15)	0.23958 (14)	0.57426 (10)	0.0309 (2)
C1	0.39758 (18)	0.09557 (17)	0.50846 (12)	0.0232 (2)
S1	0.76420 (7)	0.30131 (6)	0.20864 (5)	0.04886 (18)
N1	0.7143 (2)	0.7005 (2)	0.04926 (17)	0.0521 (4)
C2	0.7374 (2)	0.5334 (2)	0.11335 (15)	0.0362 (3)
N2	0.2850 (2)	0.94792 (18)	0.17891 (12)	0.0346 (3)
H2A	0.2477	1.0605	0.1135	0.041*
H2B	0.4190	0.8736	0.1513	0.041*
H2C	0.2819	0.9898	0.2650	0.041*
N3	0.18949 (17)	0.64628 (17)	0.44290 (12)	0.0287 (2)
H3A	0.2241	0.5223	0.4981	0.034*
H3B	0.0574	0.7188	0.4760	0.034*
H3C	0.2868	0.7191	0.4460	0.034*
C3	0.1898 (2)	0.6105 (2)	0.29020 (15)	0.0316 (3)
H3D	0.0877	0.5264	0.2881	0.038*
H3E	0.3340	0.5311	0.2548	0.038*
C4	0.1284 (2)	0.8139 (2)	0.19058 (15)	0.0356 (3)
H4A	0.1213	0.7813	0.0945	0.043*
H4B	−0.0157	0.8932	0.2262	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0227 (4)	0.0324 (5)	0.0425 (5)	−0.0015 (3)	−0.0087 (4)	−0.0100 (4)
O2	0.0302 (5)	0.0241 (4)	0.0388 (5)	−0.0025 (3)	−0.0072 (4)	−0.0091 (4)
C1	0.0220 (5)	0.0207 (5)	0.0251 (5)	−0.0035 (4)	−0.0018 (4)	−0.0013 (4)
S1	0.0510 (3)	0.0346 (2)	0.0483 (3)	0.00328 (17)	0.00029 (18)	0.00231 (16)
N1	0.0485 (8)	0.0464 (8)	0.0511 (8)	−0.0062 (6)	−0.0010 (6)	0.0098 (6)
C2	0.0303 (6)	0.0399 (7)	0.0327 (7)	−0.0011 (5)	−0.0009 (5)	−0.0037 (5)
N2	0.0409 (6)	0.0288 (5)	0.0300 (5)	−0.0051 (5)	−0.0044 (4)	0.0023 (4)
N3	0.0267 (5)	0.0258 (5)	0.0341 (6)	−0.0077 (4)	−0.0060 (4)	−0.0002 (4)
C3	0.0323 (6)	0.0261 (6)	0.0353 (7)	−0.0050 (5)	−0.0018 (5)	−0.0067 (5)
C4	0.0396 (7)	0.0336 (7)	0.0332 (7)	−0.0053 (5)	−0.0116 (5)	−0.0031 (5)

O1—C1	1.2539 (15)	N3—C3	1.4879 (18)
O2—C1	1.2474 (15)	N3—H3A	0.89
C1—C1i	1.568 (2)	N3—H3B	0.89
S1—C2	1.6295 (16)	N3—H3C	0.89
N1—C2	1.155 (2)	C3—C4	1.5054 (19)
N2—C4	1.4890 (19)	C3—H3D	0.97
N2—H2A	0.89	C3—H3E	0.97
N2—H2B	0.89	C4—H4A	0.97
N2—H2C	0.89	C4—H4B	0.97
O2—C1—O1	125.46 (11)	H3A—N3—H3C	109.5
O2—C1—C1i	117.42 (13)	H3B—N3—H3C	109.5
O1—C1—C1i	117.12 (13)	N3—C3—C4	112.50 (11)
N1—C2—S1	177.95 (14)	N3—C3—H3D	109.1
C4—N2—H2A	109.5	C4—C3—H3D	109.1
C4—N2—H2B	109.5	N3—C3—H3E	109.1
H2A—N2—H2B	109.5	C4—C3—H3E	109.1
C4—N2—H2C	109.5	H3D—C3—H3E	107.8
H2A—N2—H2C	109.5	N2—C4—C3	113.05 (11)
H2B—N2—H2C	109.5	N2—C4—H4A	109.0
C3—N3—H3A	109.5	C3—C4—H4A	109.0
C3—N3—H3B	109.5	N2—C4—H4B	109.0
H3A—N3—H3B	109.5	C3—C4—H4B	109.0
C3—N3—H3C	109.5	H4A—C4—H4B	107.8
N3—C3—C4—N2	62.64 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.89	2.11	2.986 (2)	169
N3—H3A···O2	0.89	2.02	2.8685 (17)	158
C3—H3E···S1	0.97	2.77	3.7294 (18)	169
N2—H2A···N1ii	0.89	2.05	2.899 (2)	159
N2—H2C···O1iii	0.89	1.95	2.8337 (18)	172
N3—H3B···O1iv	0.89	2.02	2.9078 (17)	174
N3—H3C···O1iii	0.89	2.40	3.0465 (18)	129
N3—H3C···O2v	0.89	1.99	2.8189 (18)	154
C4—H4B···S1vi	0.97	2.68	3.4495 (18)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1	0.89	2.11	2.986 (2)	169
N3—H3A⋯O2	0.89	2.02	2.8685 (17)	158
C3—H3E⋯S1	0.97	2.77	3.7294 (18)	169
N2—H2A⋯N1i	0.89	2.05	2.899 (2)	159
N2—H2C⋯O1ii	0.89	1.95	2.8337 (18)	172
N3—H3B⋯O1iii	0.89	2.02	2.9078 (17)	174
N3—H3C⋯O1ii	0.89	2.40	3.0465 (18)	129
N3—H3C⋯O2iv	0.89	1.99	2.8189 (18)	154
C4—H4B⋯S1v	0.97	2.68	3.4495 (18)	136

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