Ethyl-enediammonium dichloro-iodide chloride.

The asymmetric unit of the crystal structure of the title compound, C(2)H(10)N(2) (2+)·Cl(2)I(-)·Cl(-), contains two ethyl-ene-diammonium cations, two [ICl(2)](-) anions and two Cl(-) anions, of which one cation, one [ICl(2)](-) anion and one Cl(-) anion have site symmetry 2, with the mid-point of the C-C bond of the cation, the I atom of [ICl(2)](-) anion and the Cl(-) anion located on the twofold rotation axes. The two independent cations show different conformations, the N-C-C-N torsion angles being 160.1 (2) and -73.1 (4)°. The crystal structure is stabilized by extensive inter-molecular N-H⋯Cl hydrogen bonding.

Related literature

For general background to combining protonated aromatic nitro­gen bases with halide or polyhalide ions, see: Tucker & Kroon (1973 ▶); Bandoli et al. (1978 ▶). For Cl—I bond lengths and Cl–I–Cl bond angles, see: Lang et al. (2000 ▶); Wang et al. (1999a ▶,b ▶).

Experimental

Crystal data

C2H10N2 2+·Cl2I−·Cl−

M = 295.37

Monoclinic,

a = 8.565 (2) Å

b = 16.2186 (15) Å

c = 19.9631 (16) Å

β = 101.164 (16)°

V = 2720.8 (7) Å3

Z = 12

Mo Kα radiation

μ = 4.34 mm−1

T = 293 K

0.36 × 0.30 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.230, T max = 0.301

13418 measured reflections

3106 independent reflections

2821 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.056

S = 1.10

3106 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039038/xu2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039038/xu2588Isup2.hkl

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

C2H10N22+·Cl2I−·Cl−	F(000) = 1680
Mr = 295.37	Dx = 2.163 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2821 reflections
a = 8.565 (2) Å	θ = 2.5–27.5°
b = 16.2186 (15) Å	µ = 4.34 mm−1
c = 19.9631 (16) Å	T = 293 K
β = 101.164 (16)°	Block, yellow
V = 2720.8 (7) Å3	0.36 × 0.30 × 0.28 mm
Z = 12

Rigaku SCXmini diffractometer	3106 independent reflections
Radiation source: fine-focus sealed tube	2821 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.230, Tmax = 0.301	l = −25→25
13418 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)] = 0.023	H-atom parameters constrained
wR(F2) = 0.056	w = 1/[σ2(Fo2) + (0.0271P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3106 reflections	Δρmax = 0.92 e Å−3
114 parameters	Δρmin = −0.65 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00017 (4)

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
C1	0.9115 (3)	0.1716 (2)	0.24029 (15)	0.0472 (8)
H1D	0.8758	0.2243	0.2199	0.057*
H1E	0.8778	0.1289	0.2065	0.057*
C2	1.0658 (4)	0.8169 (2)	0.43343 (16)	0.0412 (7)
H2D	1.0988	0.8492	0.4747	0.049*
H2E	1.1129	0.7626	0.4416	0.049*
C3	0.8881 (4)	0.80844 (18)	0.41979 (16)	0.0415 (7)
H3D	0.8539	0.7849	0.3747	0.050*
H3E	0.8592	0.7700	0.4526	0.050*
Cl1	0.30378 (10)	0.45106 (5)	0.26597 (4)	0.04654 (19)
Cl2	1.16812 (9)	0.58195 (6)	0.42064 (4)	0.04530 (19)
Cl3	0.57256 (8)	0.54598 (5)	0.41952 (3)	0.03576 (16)
Cl4	0.5000	0.23483 (7)	0.2500	0.0401 (2)
Cl5	0.47720 (9)	0.79063 (5)	0.40942 (4)	0.04283 (18)
I1	0.0000	0.450435 (17)	0.2500	0.03375 (8)
I2	0.88263 (2)	0.564990 (11)	0.418170 (9)	0.02956 (7)
N1	0.8379 (3)	0.15711 (16)	0.29954 (12)	0.0395 (6)
H1A	0.8485	0.1042	0.3114	0.059*
H1B	0.7351	0.1700	0.2890	0.059*
H1C	0.8855	0.1883	0.3342	0.059*
N2	1.1282 (3)	0.85669 (15)	0.37681 (12)	0.0384 (6)
H2A	1.0820	0.8342	0.3372	0.058*
H2B	1.2330	0.8492	0.3832	0.058*
H2C	1.1069	0.9104	0.3762	0.058*
N3	0.8007 (3)	0.88669 (15)	0.42352 (12)	0.0382 (6)
H3A	0.8401	0.9123	0.4626	0.057*
H3B	0.6981	0.8759	0.4216	0.057*
H3C	0.8115	0.9189	0.3886	0.057*

	U11	U22	U33	U12	U13	U23
C1	0.0272 (16)	0.084 (3)	0.0303 (15)	−0.0052 (16)	0.0042 (13)	0.0027 (16)
C2	0.0345 (17)	0.0478 (18)	0.0391 (16)	0.0067 (13)	0.0013 (13)	0.0026 (14)
C3	0.0399 (18)	0.0322 (16)	0.0529 (19)	−0.0026 (12)	0.0100 (15)	0.0020 (14)
Cl1	0.0356 (4)	0.0628 (5)	0.0405 (4)	0.0103 (4)	0.0056 (3)	0.0010 (4)
Cl2	0.0291 (4)	0.0586 (5)	0.0487 (4)	−0.0054 (3)	0.0089 (3)	0.0000 (4)
Cl3	0.0263 (3)	0.0409 (4)	0.0391 (4)	0.0016 (3)	0.0038 (3)	−0.0005 (3)
Cl4	0.0340 (5)	0.0407 (6)	0.0420 (6)	0.000	−0.0016 (4)	0.000
Cl5	0.0300 (4)	0.0488 (4)	0.0488 (4)	−0.0043 (3)	0.0055 (3)	−0.0040 (3)
I1	0.03698 (16)	0.03827 (15)	0.02565 (13)	0.000	0.00517 (11)	0.000
I2	0.02793 (11)	0.03197 (11)	0.02788 (10)	0.00081 (7)	0.00317 (7)	−0.00044 (7)
N1	0.0337 (13)	0.0450 (15)	0.0410 (14)	0.0042 (11)	0.0099 (11)	0.0038 (11)
N2	0.0295 (13)	0.0401 (14)	0.0463 (14)	0.0023 (10)	0.0090 (11)	−0.0025 (11)
N3	0.0310 (13)	0.0435 (14)	0.0413 (14)	−0.0039 (11)	0.0103 (11)	−0.0044 (11)

C1—N1	1.463 (4)	Cl2—I2	2.4518 (10)
C1—C1i	1.491 (6)	Cl3—I2	2.6790 (9)
C1—H1D	0.9700	I1—Cl1ii	2.5595 (10)
C1—H1E	0.9700	N1—H1A	0.8900
C2—N2	1.488 (4)	N1—H1B	0.8900
C2—C3	1.499 (4)	N1—H1C	0.8900
C2—H2D	0.9700	N2—H2A	0.8900
C2—H2E	0.9700	N2—H2B	0.8900
C3—N3	1.483 (4)	N2—H2C	0.8900
C3—H3D	0.9700	N3—H3A	0.8900
C3—H3E	0.9700	N3—H3B	0.8900
Cl1—I1	2.5595 (10)	N3—H3C	0.8900
N1—C1—C1i	111.4 (3)	Cl2—I2—Cl3	178.30 (3)
N1—C1—H1D	109.3	C1—N1—H1A	109.5
C1i—C1—H1D	109.3	C1—N1—H1B	109.5
N1—C1—H1E	109.3	H1A—N1—H1B	109.5
C1i—C1—H1E	109.3	C1—N1—H1C	109.5
H1D—C1—H1E	108.0	H1A—N1—H1C	109.5
N2—C2—C3	113.8 (3)	H1B—N1—H1C	109.5
N2—C2—H2D	108.8	C2—N2—H2A	109.5
C3—C2—H2D	108.8	C2—N2—H2B	109.5
N2—C2—H2E	108.8	H2A—N2—H2B	109.5
C3—C2—H2E	108.8	C2—N2—H2C	109.5
H2D—C2—H2E	107.7	H2A—N2—H2C	109.5
N3—C3—C2	114.7 (3)	H2B—N2—H2C	109.5
N3—C3—H3D	108.6	C3—N3—H3A	109.5
C2—C3—H3D	108.6	C3—N3—H3B	109.5
N3—C3—H3E	108.6	H3A—N3—H3B	109.5
C2—C3—H3E	108.6	C3—N3—H3C	109.5
H3D—C3—H3E	107.6	H3A—N3—H3C	109.5
Cl1—I1—Cl1ii	179.55 (4)	H3B—N3—H3C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1iii	0.89	2.65	3.410 (3)	144
N1—H1A···Cl3iii	0.89	2.76	3.341 (3)	124
N1—H1B···Cl4	0.89	2.27	3.136 (2)	164
N1—H1C···Cl5iii	0.89	2.27	3.148 (3)	168
N2—H2A···Cl4iv	0.89	2.38	3.232 (3)	161
N2—H2B···Cl5v	0.89	2.26	3.123 (3)	162
N2—H2C···Cl3iv	0.89	2.40	3.246 (3)	159
N3—H3A···Cl3vi	0.89	2.42	3.297 (2)	167
N3—H3B···Cl5	0.89	2.32	3.144 (3)	154
N3—H3C···Cl1iv	0.89	2.49	3.319 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.89	2.65	3.410 (3)	144
N1—H1A⋯Cl3i	0.89	2.76	3.341 (3)	124
N1—H1B⋯Cl4	0.89	2.27	3.136 (2)	164
N1—H1C⋯Cl5i	0.89	2.27	3.148 (3)	168
N2—H2A⋯Cl4ii	0.89	2.38	3.232 (3)	161
N2—H2B⋯Cl5iii	0.89	2.26	3.123 (3)	162
N2—H2C⋯Cl3ii	0.89	2.40	3.246 (3)	159
N3—H3A⋯Cl3iv	0.89	2.42	3.297 (2)	167
N3—H3B⋯Cl5	0.89	2.32	3.144 (3)	154
N3—H3C⋯Cl1ii	0.89	2.49	3.319 (2)	155

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