2-Hy­droxy­ethyl­ammonium iodide

Kohrt, C.; Spannenberg, A.; Werner, T.

doi:10.1107/S1600536814009581

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o628

doi:10.1107/S1600536814009581

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2-Hydroxyethylammonium iodide

Christina Kohrt,^a Anke Spannenberg ^a and Thomas Werner ^a ^*

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: thomas.werner@catalysis.de

(Received 17 April 2014; accepted 28 April 2014; online 3 May 2014)

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.

CCDC reference: 999797

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_r = 188.99
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.014
wR(F²) = 0.032
S = 1.08
1319 reflections
48 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.46 e Å⁻³

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) x-1, y, z; (ii) x, y-1, z; (iii) -x+2, -y+1, -z+1.

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.

Supporting information

CCDC reference: 999797

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814009581/zl2586sup1.cif

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

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

checkCIF report

Comment top

Recently we were interested in the synthesis of perfluorinated organocatalysts. In this context we tried to alkylate 2-aminoethanol with 1H,1H,2H,2H-perfluorooctyliodide. Unfortunately we did not obtain the desired product under the chosen reaction conditions. However, instead we were able to isolate the title compound in excellent yield. The molecular structure of the ammonium iodide shows a nitrogen atom carrying three protons and one 2-hydroxyethyl-group and the iodide as anion (Fig. 1). The cations are aggregated through N—H···O hydrogen bonds in a linear arrangement parallel to the a axis. These chains are extended by N—H···I and O—H···I hydrogen bonds into layers staggered along the c axis (Fig. 2).

A variety of compounds involving the same cation had been reported in the literature. A WebCSD search (Release April 2014, Thomas et al. (2010)) yielded 85 examples of hydroxyethylammonium salts; for the bromide and chloride salts most closely related to the iodide title compound, please see Koo et al. (1974) and Koo et al. (1972), respectively.

Related literature top

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 top

2-Aminoethanol (4.09 mmol, 250 mg, 1 eq) was added to 1H,1H,2H,2H-perfluorooctyliodide (12.3 mmol, 5.80 g, 3 eq) in a pressure pipe under argon. The solution was stirred at 80°C for 24 h. Afterwards the resulting yellow solution was layered with 2,2,2-trifluoroethanol and crystals precipitated directly from the mixture. 84% (3.43 mmol, 649 mg) of the title compound were obtained as colorless crystals. ¹H NMR (CF₃—CD₂—OD): δ 3.59–3.48 (br m, 2H); 2.78–2.67 (br m, 2H) ppm. ¹³C NMR (CF₃—CD₂—OD): δ 62.47 (s, CH₂); 44.03 (s, CH₂) ppm. Elemental analysis calculated (%) for C₂H₈INO: C 12.71, H 4.27, N 7.41; found: C 12.97, H 4.10, N 7.48.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound in the crystal. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing plot; hydrogen bonds are shown as dashed lines.

2-Hydroxyethylammonium iodide top

Crystal data top

C₂H₈NO⁺·I⁻	Z = 2
M_r = 188.99	F(000) = 176
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0163P)² + 0.0136P] where P = (F_o² + 2F_c²)/3
1319 reflections	(Δ/σ)_max = 0.002
48 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂H₈NO⁺·I⁻	γ = 77.544 (2)°
M_r = 188.99	V = 274.21 (4) Å³
Triclinic, P1	Z = 2
a = 4.6557 (4) Å	Mo Kα radiation
b = 7.5432 (6) Å	µ = 5.70 mm⁻¹
c = 8.1787 (7) Å	T = 150 K
α = 85.235 (2)°	0.34 × 0.12 × 0.03 mm
β = 78.091 (2)°

Data collection top

Bruker Kappa APEXII DUO diffractometer	1319 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1254 reflections with I > 2σ(I)
T_min = 0.672, T_max = 0.843	R_int = 0.021
4884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.014	0 restraints
wR(F²) = 0.032	H-atom parameters constrained
S = 1.08	Δρ_max = 0.58 e Å⁻³
1319 reflections	Δρ_min = −0.46 e Å⁻³
48 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.91	1.93	2.800 (2)	158.1
N1—H1B···I1ⁱⁱ	0.91	2.75	3.5825 (18)	151.8
N1—H1C···I1ⁱⁱⁱ	0.91	2.78	3.6322 (18)	155.4
O1—H1D···I1	0.84	2.72	3.5100 (15)	157.1

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1.

Acknowledgements

We wish to thank the Federal Ministry of Research and Education (BMBF) for financial support (Chemische Prozesse und stoffliche Nutzung von CO₂: Technologien für Nachhaltigkeit und Klimaschutz, grant 01 RC 1004A).

References

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