2-Amino-ethanaminium iodide.

The title salt, [NH(3)CH(2)CH(2)NH(2)](+)·I(-), has an array structure based on strong inter-molecular N-H⋯N hydrogen bonding formed between the ammonium and amine groups of adjacent cations. This inter-action gives a helical chain of cations that runs parallel to the b axis. The four remaining NH group H atoms all form hydrogen bonds to the iodide anion, and these iodide anions lie in channels parallel to the cation-cation chains.

Related literature

For syntheses and structures of salt forms of the related ethyl­ene-1,2-diammonium, see: Chen (2009 ▶); Saidi et al. (2011 ▶). For a structural example of a complex of ethyl­ene-1,2-diammonium, see: Zhang et al. (2006 ▶). For the synthesis that gave the title compound as a by-product, see: Kennedy et al. (2011 ▶). For C–N bond length changes in another monoprotonated symmetrical diamine, see: Craig et al. (2012 ▶).

Experimental

Crystal data

C2H9N2 +·I−

M = 188.01

Orthorhombic,

a = 8.1380 (2) Å

b = 8.6259 (2) Å

c = 16.7854 (6) Å

V = 1178.29 (6) Å3

Z = 8

Mo Kα radiation

μ = 5.29 mm−1

T = 123 K

0.28 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Gemini S diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.405, T max = 0.805

13735 measured reflections

1675 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.035

S = 1.08

1675 reflections

83 parameters

All H-atom parameters refined

Δρmax = 0.58 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202065X/br2201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202065X/br2201Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202065X/br2201Isup3.cml

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

C2H9N2+·I−	F(000) = 704
Mr = 188.01	Dx = 2.120 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7738 reflections
a = 8.1380 (2) Å	θ = 3.4–30.4°
b = 8.6259 (2) Å	µ = 5.29 mm−1
c = 16.7854 (6) Å	T = 123 K
V = 1178.29 (6) Å3	Cut needle, colourless
Z = 8	0.28 × 0.08 × 0.04 mm

Oxford Diffraction Gemini S diffractometer	1675 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 30.5°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −11→11
Tmin = 0.405, Tmax = 0.805	k = −12→12
13735 measured reflections	l = −23→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.016	All H-atom parameters refined
wR(F2) = 0.035	w = 1/[σ2(Fo2) + (0.0188P)2 + 0.0175P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.003
1675 reflections	Δρmax = 0.58 e Å−3
83 parameters	Δρmin = −0.39 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: 0.00618 (17)

Experimental. Absorption correction: CrysAlis PRO (Oxford Diffraction, 2010). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
I1	0.153737 (12)	0.243717 (9)	0.639779 (7)	0.01478 (5)
N1	0.57239 (17)	0.09977 (16)	0.66467 (10)	0.0152 (3)
N2	0.91366 (18)	−0.12957 (16)	0.57234 (10)	0.0166 (3)
C1	0.72638 (19)	0.00806 (18)	0.65975 (11)	0.0156 (3)
C2	0.7645 (2)	−0.03399 (18)	0.57391 (10)	0.0164 (3)
H1	0.720 (2)	−0.083 (2)	0.6923 (11)	0.022 (5)*
H2	0.812 (2)	0.073 (2)	0.6768 (12)	0.025 (5)*
H3	0.677 (2)	−0.0965 (19)	0.5534 (11)	0.020 (5)*
H4	0.771 (2)	0.0590 (19)	0.5396 (11)	0.018 (4)*
H1N	0.573 (3)	0.206 (3)	0.6334 (13)	0.030 (5)*
H2N	0.487 (2)	0.042 (2)	0.6523 (12)	0.027 (5)*
H3N	0.561 (2)	0.131 (2)	0.7119 (12)	0.028 (6)*
H4N	0.932 (2)	−0.161 (2)	0.5259 (13)	0.029 (5)*
H5N	0.998 (2)	−0.073 (2)	0.5848 (13)	0.029 (6)*

	U11	U22	U33	U12	U13	U23
I1	0.01452 (7)	0.01487 (7)	0.01494 (8)	0.00109 (3)	−0.00020 (4)	−0.00022 (4)
N1	0.0146 (7)	0.0161 (7)	0.0150 (8)	−0.0014 (5)	0.0018 (6)	−0.0016 (5)
N2	0.0151 (7)	0.0194 (7)	0.0152 (8)	0.0000 (5)	0.0019 (6)	−0.0009 (6)
C1	0.0140 (8)	0.0188 (8)	0.0141 (8)	−0.0001 (6)	−0.0006 (6)	0.0007 (6)
C2	0.0164 (8)	0.0191 (7)	0.0136 (8)	0.0010 (6)	0.0007 (7)	0.0010 (6)

N1—C1	1.484 (2)	N2—H5N	0.866 (19)
N1—H1N	1.06 (2)	C1—C2	1.518 (2)
N1—H2N	0.882 (19)	C1—H1	0.959 (18)
N1—H3N	0.84 (2)	C1—H2	0.937 (19)
N2—C2	1.467 (2)	C2—H3	0.959 (17)
N2—H4N	0.84 (2)	C2—H4	0.989 (18)
C1—N1—H1N	115.5 (12)	C2—C1—H1	110.8 (11)
C1—N1—H2N	110.4 (12)	N1—C1—H2	107.0 (11)
H1N—N1—H2N	112.4 (17)	C2—C1—H2	106.3 (13)
C1—N1—H3N	108.5 (13)	H1—C1—H2	110.7 (18)
H1N—N1—H3N	100.7 (16)	N2—C2—C1	108.70 (14)
H2N—N1—H3N	108.6 (17)	N2—C2—H3	107.1 (10)
C2—N2—H4N	110.2 (13)	C1—C2—H3	108.8 (11)
C2—N2—H5N	109.6 (12)	N2—C2—H4	113.8 (10)
H4N—N2—H5N	105.2 (18)	C1—C2—H4	111.7 (11)
N1—C1—C2	110.67 (14)	H3—C2—H4	106.6 (15)
N1—C1—H1	111.2 (11)
N1—C1—C2—N2	−177.75 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	1.06 (2)	1.75 (2)	2.805 (2)	173.0 (19)
N1—H2N···I1	0.882 (19)	3.231 (18)	3.6502 (14)	111.6 (13)
N1—H2N···I1ii	0.882 (19)	2.820 (19)	3.6047 (14)	148.9 (15)
N1—H3N···I1iii	0.84 (2)	2.78 (2)	3.5713 (16)	157.9 (16)
N2—H4N···I1iv	0.84 (2)	2.96 (2)	3.7346 (16)	155.5 (16)
N2—H5N···I1v	0.866 (19)	3.152 (19)	3.9328 (15)	151.2 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	1.06 (2)	1.75 (2)	2.805 (2)	173.0 (19)
N1—H2N⋯I1	0.882 (19)	3.231 (18)	3.6502 (14)	111.6 (13)
N1—H2N⋯I1ii	0.882 (19)	2.820 (19)	3.6047 (14)	148.9 (15)
N1—H3N⋯I1iii	0.84 (2)	2.78 (2)	3.5713 (16)	157.9 (16)
N2—H4N⋯I1iv	0.84 (2)	2.96 (2)	3.7346 (16)	155.5 (16)
N2—H5N⋯I1v	0.866 (19)	3.152 (19)	3.9328 (15)	151.2 (14)

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