2-Hy-droxy-ethyl-ammonium iodide.

In the crystal structure of the title salt, C2H8NO(+)·I(-), N-H⋯O, N-H⋯I and O-H⋯I hydrogen bonds lead to the formation of layers staggered along the c axis.

Related literature

A variety of compounds are known in the literature involving the cation [NH3CH2CH2OH]+. A WebCSD search (Release April 2014) yielded 85 examples (Thomas et al., 2010 ▶), see for example: Koo et al. (1974 ▶) for 2-hy­droxy­ethyl­ammonium bromide, or Koo et al. (1972 ▶) for 2-hy­droxy­ethyl­ammonium chloride.

Experimental

Crystal data

C2H8NO+·I−

M = 188.99

Triclinic,

a = 4.6557 (4) Å

b = 7.5432 (6) Å

c = 8.1787 (7) Å

α = 85.235 (2)°

β = 78.091 (2)°

γ = 77.544 (2)°

V = 274.21 (4) Å3

Z = 2

Mo Kα radiation

μ = 5.70 mm−1

T = 150 K

0.34 × 0.12 × 0.03 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.672, T max = 0.843

4884 measured reflections

1319 independent reflections

1254 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.032

S = 1.08

1319 reflections

48 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814009581/zl2586sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009581/zl2586Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009581/zl2586Isup3.cml

CCDC reference: 999797

Additional supporting information: crystallographic information; 3D view; checkCIF report

C2H8NO+·I−	Z = 2
Mr = 188.99	F(000) = 176
Triclinic, P1	Dx = 2.289 Mg m−3
a = 4.6557 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5432 (6) Å	Cell parameters from 3767 reflections
c = 8.1787 (7) Å	θ = 2.8–29.0°
α = 85.235 (2)°	µ = 5.70 mm−1
β = 78.091 (2)°	T = 150 K
γ = 77.544 (2)°	Plate, colorless
V = 274.21 (4) Å3	0.34 × 0.12 × 0.03 mm

Bruker Kappa APEXII DUO diffractometer	1319 independent reflections
Radiation source: fine-focus sealed tube	1254 reflections with I > 2σ(I)
Curved graphite monochromator	Rint = 0.021
Detector resolution: 8.3333 pixels mm-1	θmax = 28.0°, θmin = 2.6°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −9→9
Tmin = 0.672, Tmax = 0.843	l = −10→10
4884 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.032	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0163P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3
1319 reflections	(Δ/σ)max = 0.002
48 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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
I1	0.63581 (3)	0.752733 (16)	0.669449 (16)	0.01732 (5)
O1	1.1624 (3)	0.3874 (2)	0.79532 (19)	0.0204 (3)
H1D	1.0844	0.4856	0.7510	0.031*
N1	0.7519 (4)	0.2059 (2)	0.6780 (2)	0.0182 (4)
H1A	0.5779	0.2898	0.7009	0.027*
H1B	0.7164	0.1061	0.6366	0.027*
H1C	0.8882	0.2542	0.6011	0.027*
C1	0.9351 (5)	0.3140 (3)	0.9069 (3)	0.0189 (4)
H1E	0.7493	0.4085	0.9290	0.023*
H1F	1.0004	0.2765	1.0146	0.023*
C2	0.8719 (5)	0.1527 (3)	0.8344 (3)	0.0182 (4)
H2A	1.0590	0.0596	0.8098	0.022*
H2B	0.7245	0.0988	0.9174	0.022*

	U11	U22	U33	U12	U13	U23
I1	0.01634 (8)	0.01767 (8)	0.01768 (8)	−0.00360 (5)	−0.00336 (5)	0.00129 (5)
O1	0.0182 (7)	0.0167 (7)	0.0249 (8)	−0.0035 (6)	−0.0021 (6)	0.0012 (6)
N1	0.0164 (9)	0.0213 (9)	0.0175 (9)	−0.0048 (7)	−0.0027 (7)	−0.0022 (7)
C1	0.0218 (11)	0.0203 (11)	0.0139 (10)	−0.0046 (8)	−0.0020 (8)	0.0000 (8)
C2	0.0188 (10)	0.0176 (11)	0.0182 (10)	−0.0023 (8)	−0.0058 (8)	0.0018 (8)

O1—C1	1.425 (3)	C1—C2	1.505 (3)
O1—H1D	0.8400	C1—H1E	0.9900
N1—C2	1.490 (3)	C1—H1F	0.9900
N1—H1A	0.9100	C2—H2A	0.9900
N1—H1B	0.9100	C2—H2B	0.9900
N1—H1C	0.9100
C1—O1—H1D	109.5	O1—C1—H1F	109.5
C2—N1—H1A	109.5	C2—C1—H1F	109.5
C2—N1—H1B	109.5	H1E—C1—H1F	108.0
H1A—N1—H1B	109.5	N1—C2—C1	111.23 (16)
C2—N1—H1C	109.5	N1—C2—H2A	109.4
H1A—N1—H1C	109.5	C1—C2—H2A	109.4
H1B—N1—H1C	109.5	N1—C2—H2B	109.4
O1—C1—C2	110.92 (17)	C1—C2—H2B	109.4
O1—C1—H1E	109.5	H2A—C2—H2B	108.0
C2—C1—H1E	109.5
O1—C1—C2—N1	−63.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.91	1.93	2.800 (2)	158
N1—H1B···I1ii	0.91	2.75	3.5825 (18)	152
N1—H1C···I1iii	0.91	2.78	3.6322 (18)	155
O1—H1D···I1	0.84	2.72	3.5100 (15)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.91	1.93	2.800 (2)	158
N1—H1B⋯I1ii	0.91	2.75	3.5825 (18)	152
N1—H1C⋯I1iii	0.91	2.78	3.6322 (18)	155
O1—H1D⋯I1	0.84	2.72	3.5100 (15)	157

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