organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-Hy­dr­oxy­ethyl­ammonium iodide

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.

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[Thomas, I. R., Bruno, I. J., Cole, J. C., Macrae, C. F., Pidcock, E. & Wood, P. A. (2010). J. Appl. Cryst. 43, 362-366.]), see for example: Koo et al. (1974[Koo, C. H., Choe, C., Roe, T. S. & Kim, H. S. (1974). J. Korean Chem. Soc. 18, 25-30.]) for 2-hy­droxy­ethyl­ammonium bromide, or Koo et al. (1972[Koo, C. H., Lee, O. & Shin, H. S. (1972). J. Korean Chem. Soc. 16, 6-12.]) for 2-hy­droxy­ethyl­ammonium chloride.

[Scheme 1]

Experimental

Crystal data
  • C2H8NO+·I

  • Mr = 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[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.672, Tmax = 0.843

  • 4884 measured reflections

  • 1319 independent reflections

  • 1254 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.014

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H1A - H1D were clearly identified in difference Fourier maps. All H atoms were placed in idealized positions with d(O—H) = 0.84, d(N—H) = 0.91, d(C—H) = 0.99 Å and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) and 1.5 Ueq(N, O)

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
[Figure 1] Fig. 1. The molecular structure of the title compound in the crystal. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing plot; hydrogen bonds are shown as dashed lines.
2-Hydroxyethylammonium iodide top
Crystal data top
C2H8NO+·IZ = 2
Mr = 188.99F(000) = 176
Triclinic, P1Dx = 2.289 Mg m3
a = 4.6557 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.5432 (6) ÅCell parameters from 3767 reflections
c = 8.1787 (7) Åθ = 2.8–29.0°
α = 85.235 (2)°µ = 5.70 mm1
β = 78.091 (2)°T = 150 K
γ = 77.544 (2)°Plate, colorless
V = 274.21 (4) Å30.34 × 0.12 × 0.03 mm
Data collection top
Bruker Kappa APEXII DUO
diffractometer
1319 independent reflections
Radiation source: fine-focus sealed tube1254 reflections with I > 2σ(I)
Curved graphite monochromatorRint = 0.021
Detector resolution: 8.3333 pixels mm-1θmax = 28.0°, θmin = 2.6°
ϕ and ω scansh = 66
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 99
Tmin = 0.672, Tmax = 0.843l = 1010
4884 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.014Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.032H-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 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C2H8NO+·Iγ = 77.544 (2)°
Mr = 188.99V = 274.21 (4) Å3
Triclinic, P1Z = 2
a = 4.6557 (4) ÅMo Kα radiation
b = 7.5432 (6) ŵ = 5.70 mm1
c = 8.1787 (7) ÅT = 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)
Tmin = 0.672, Tmax = 0.843Rint = 0.021
4884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0140 restraints
wR(F2) = 0.032H-atom parameters constrained
S = 1.08Δρmax = 0.58 e Å3
1319 reflectionsΔρmin = 0.46 e Å3
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
xyzUiso*/Ueq
I10.63581 (3)0.752733 (16)0.669449 (16)0.01732 (5)
O11.1624 (3)0.3874 (2)0.79532 (19)0.0204 (3)
H1D1.08440.48560.75100.031*
N10.7519 (4)0.2059 (2)0.6780 (2)0.0182 (4)
H1A0.57790.28980.70090.027*
H1B0.71640.10610.63660.027*
H1C0.88820.25420.60110.027*
C10.9351 (5)0.3140 (3)0.9069 (3)0.0189 (4)
H1E0.74930.40850.92900.023*
H1F1.00040.27651.01460.023*
C20.8719 (5)0.1527 (3)0.8344 (3)0.0182 (4)
H2A1.05900.05960.80980.022*
H2B0.72450.09880.91740.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01634 (8)0.01767 (8)0.01768 (8)0.00360 (5)0.00336 (5)0.00129 (5)
O10.0182 (7)0.0167 (7)0.0249 (8)0.0035 (6)0.0021 (6)0.0012 (6)
N10.0164 (9)0.0213 (9)0.0175 (9)0.0048 (7)0.0027 (7)0.0022 (7)
C10.0218 (11)0.0203 (11)0.0139 (10)0.0046 (8)0.0020 (8)0.0000 (8)
C20.0188 (10)0.0176 (11)0.0182 (10)0.0023 (8)0.0058 (8)0.0018 (8)
Geometric parameters (Å, º) top
O1—C11.425 (3)C1—C21.505 (3)
O1—H1D0.8400C1—H1E0.9900
N1—C21.490 (3)C1—H1F0.9900
N1—H1A0.9100C2—H2A0.9900
N1—H1B0.9100C2—H2B0.9900
N1—H1C0.9100
C1—O1—H1D109.5O1—C1—H1F109.5
C2—N1—H1A109.5C2—C1—H1F109.5
C2—N1—H1B109.5H1E—C1—H1F108.0
H1A—N1—H1B109.5N1—C2—C1111.23 (16)
C2—N1—H1C109.5N1—C2—H2A109.4
H1A—N1—H1C109.5C1—C2—H2A109.4
H1B—N1—H1C109.5N1—C2—H2B109.4
O1—C1—C2110.92 (17)C1—C2—H2B109.4
O1—C1—H1E109.5H2A—C2—H2B108.0
C2—C1—H1E109.5
O1—C1—C2—N163.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.911.932.800 (2)158
N1—H1B···I1ii0.912.753.5825 (18)152
N1—H1C···I1iii0.912.783.6322 (18)155
O1—H1D···I10.842.723.5100 (15)157
Symmetry codes: (i) x1, y, z; (ii) x, y1, z; (iii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.911.932.800 (2)158.1
N1—H1B···I1ii0.912.753.5825 (18)151.8
N1—H1C···I1iii0.912.783.6322 (18)155.4
O1—H1D···I10.842.723.5100 (15)157.1
Symmetry codes: (i) x1, y, z; (ii) x, y1, 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

First citationBruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKoo, C. H., Choe, C., Roe, T. S. & Kim, H. S. (1974). J. Korean Chem. Soc. 18, 25–30.  CAS Google Scholar
First citationKoo, C. H., Lee, O. & Shin, H. S. (1972). J. Korean Chem. Soc. 16, 6–12.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationThomas, I. R., Bruno, I. J., Cole, J. C., Macrae, C. F., Pidcock, E. & Wood, P. A. (2010). J. Appl. Cryst. 43, 362–366.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds