Ethyl-enediammonium dichloride.

The title ionic compound, C(2)H(10)N(2) (2+)·2Cl(-), crystallizes with a center of symmetry within the cation. Each of the positively charged ammonium ends of the mol-ecule is trigonally hydrogen bonded to three different chloride counter-ions, while each of the chloride ions is trigonally hydrogen bonded to three different ethyl-enediammonium cations. The hydrogen-bonding network leads to stabilization of the structure.

Related literature

For the applications of ethyl­enediamine, see: Kotti et al. (2006 ▶); Warner (1912 ▶).

Experimental

Crystal data

C2H10N2 2+·2Cl−

M = 133.02

Monoclinic,

a = 4.3807 (3) Å

b = 6.8569 (4) Å

c = 9.9464 (5) Å

β = 91.192 (2)°

V = 298.71 (3) Å3

Z = 2

Cu Kα radiation

μ = 8.71 mm−1

T = 100 K

0.45 × 0.30 × 0.29 mm

Data collection

Bruker SMART CCD APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.085, T max = 0.090

1654 measured reflections

521 independent reflections

520 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.070

S = 1.15

521 reflections

44 parameters

Only H-atom coordinates refined

Δρmax = 0.41 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018327/lh2823sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018327/lh2823Isup2.hkl

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

C2H10N22+·2Cl−	F(000) = 140
Mr = 133.02	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1684 reflections
a = 4.3807 (3) Å	θ = 4.5–67.4°
b = 6.8569 (4) Å	µ = 8.71 mm−1
c = 9.9464 (5) Å	T = 100 K
β = 91.192 (2)°	Parallelepiped, colourless
V = 298.71 (3) Å3	0.45 × 0.30 × 0.29 mm
Z = 2

Bruker SMART CCD APEXII area-detector diffractometer	521 independent reflections
Radiation source: fine-focus sealed tube	520 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 67.8°, θmin = 7.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −5→4
Tmin = 0.085, Tmax = 0.090	k = −8→8
1654 measured reflections	l = −11→11

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)] = 0.028	Only H-atom coordinates refined
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.1865P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
521 reflections	Δρmax = 0.41 e Å−3
44 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.066 (5)

Experimental. crystal mounted on cryoloop using Paratone-N

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	0.91302 (8)	0.07997 (5)	0.67014 (3)	0.0043 (3)
C1	0.3856 (4)	0.0762 (2)	0.97532 (18)	0.0037 (4)
H1A	0.254 (5)	0.019 (3)	0.903 (2)	0.004*
H1B	0.269 (5)	0.131 (3)	1.047 (2)	0.004*
N1	0.5508 (3)	0.2442 (2)	0.91610 (14)	0.0044 (4)
H1C	0.660 (5)	0.305 (3)	0.983 (2)	0.007*
H1D	0.444 (5)	0.328 (4)	0.885 (2)	0.007*
H1E	0.654 (5)	0.206 (3)	0.845 (2)	0.007*

	U11	U22	U33	U12	U13	U23
Cl1	0.0057 (3)	0.0048 (3)	0.0023 (3)	−0.00036 (11)	−0.00138 (18)	−0.00050 (11)
C1	0.0017 (8)	0.0051 (9)	0.0041 (8)	−0.0003 (6)	−0.0013 (7)	0.0001 (5)
N1	0.0067 (7)	0.0032 (7)	0.0031 (7)	0.0013 (6)	−0.0015 (6)	0.0009 (5)

C1—N1	1.488 (2)	N1—H1C	0.91 (2)
C1—C1i	1.522 (3)	N1—H1D	0.80 (3)
C1—H1A	0.99 (2)	N1—H1E	0.89 (2)
C1—H1B	0.96 (2)
N1—C1—C1i	109.68 (18)	C1—N1—H1C	108.8 (13)
N1—C1—H1A	107.3 (12)	C1—N1—H1D	114.8 (16)
C1i—C1—H1A	109.4 (13)	H1C—N1—H1D	104 (2)
N1—C1—H1B	105.1 (13)	C1—N1—H1E	110.4 (15)
C1i—C1—H1B	112.8 (13)	H1C—N1—H1E	116 (2)
H1A—C1—H1B	112.3 (17)	H1D—N1—H1E	102 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1E···Cl1	0.89 (2)	2.27 (2)	3.1514 (15)	175 (2)
N1—H1D···Cl1ii	0.80 (3)	2.39 (3)	3.1770 (15)	170 (2)
N1—H1C···Cl1iii	0.91 (2)	2.29 (2)	3.1922 (15)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1E⋯Cl1	0.89 (2)	2.27 (2)	3.1514 (15)	175 (2)
N1—H1D⋯Cl1i	0.80 (3)	2.39 (3)	3.1770 (15)	170 (2)
N1—H1C⋯Cl1ii	0.91 (2)	2.29 (2)	3.1922 (15)	171 (2)

Symmetry codes: (i) ; (ii) .