In the crystal structure of the title salt, C2H 8NO+·I-, N-H⋯O, N-H⋯I and O-H⋯I hydrogen bonds lead to the formation of layers staggered along the c axis

Kohrt, C.

Spannenberg, A.

Werner, T.

English

Repositorium für Naturwissenschaften und Technik  (TIB Hannover)

2-Hydroxyethylammonium iodideChristina Kohrt, Anke Spannenberg and Thomas Werner*Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse29a, 18059 Rostock, GermanyCorrespondence e-mail: thomas.werner@catalysis.deReceived 17 April 2014; accepted 28 April 2014Key indicators: single-crystal X-ray study; T = 150 K; mean (C–C) = 0.003 Å;R factor = 0.014; wR factor = 0.032; data-to-parameter ratio = 27.5.In the crystal structure of the title salt, C2H8NO+I, N—H  O, N—H  I and O—H  I hydrogen bonds lead to theformation of layers staggered along the c axis.Related literatureA variety of compounds are known in the literature involvingthe cation [NH3CH2CH2OH]+. A WebCSD search (ReleaseApril 2014) yielded 85 examples (Thomas et al., 2010), see forexample: Koo et al. (1974) for 2-hydroxyethylammoniumbromide, or Koo et al. (1972) for 2-hydroxyethylammoniumchloride.ExperimentalCrystal dataC2H8NO+IMr = 188.99Triclinic, P1a = 4.6557 (4) Åb = 7.5432 (6) Åc = 8.1787 (7) Å = 85.235 (2) = 78.091 (2) = 77.544 (2)V = 274.21 (4) Å3Z = 2Mo K radiation = 5.70 mm1T = 150 K0.34  0.12  0.03 mmData collectionBruker Kappa APEXII DUOdiffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2008)Tmin = 0.672, Tmax = 0.8434884 measured reflections1319 independent reflections1254 reflections with I > 2(I)Rint = 0.021RefinementR[F 2 > 2(F 2)] = 0.014wR(F 2) = 0.032S = 1.081319 reflections48 parametersH-atom parameters constrainedmax = 0.58 e Å3min = 0.46 e Å3Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AN1—H1A  O1i 0.91 1.93 2.800 (2) 158N1—H1B  I1ii 0.91 2.75 3.5825 (18) 152N1—H1C  I1iii 0.91 2.78 3.6322 (18) 155O1—H1D  I1 0.84 2.72 3.5100 (15) 157Symmetry codes: (i) x  1; y; z; (ii) x; y 1; z; (iii) xþ 2;yþ 1;zþ 1.Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT(Bruker, 2009); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP inSHELXTL (Sheldrick, 2008); software used to prepare material forpublication: SHELXTL.We wish to thank the Federal Ministry of Research andEducation (BMBF) for financial support (Chemische Prozesseund stoffliche Nutzung von CO2: Technologien für Nach-haltigkeit und Klimaschutz, grant 01 RC 1004A).Supporting information for this paper is available from the IUCrelectronic archives (Reference: ZL2586).ReferencesBruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.Koo, C. H., Choe, C., Roe, T. S. & Kim, H. S. (1974). J. Korean Chem. Soc. 18,25–30.Koo, C. H., Lee, O. & Shin, H. S. (1972). J. Korean Chem. Soc. 16, 6–12.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Thomas, I. R., Bruno, I. J., Cole, J. C., Macrae, C. F., Pidcock, E. & Wood, P. A.(2010). J. Appl. Cryst. 43, 362–366.organic compoundso628 Kohrt et al. doi:10.1107/S1600536814009581 Acta Cryst. (2014). E70, o628Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2014). E70, o628    supporting informationActa Cryst. (2014). E70, o628    [doi:10.1107/S1600536814009581]2-Hydroxyethylammonium iodideChristina Kohrt, Anke Spannenberg and Thomas WernerS1. Comment 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.S2. Experimental 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.S3. Refinement 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)supporting informationsup-2Acta Cryst. (2014). E70, o628    Figure 1The molecular structure of the title compound in the crystal. Displacement ellipsoids are drawn at the 50% probability level. supporting informationsup-3Acta Cryst. (2014). E70, o628    Figure 2Packing plot; hydrogen bonds are shown as dashed lines. 2-Hydroxyethylammonium iodide Crystal data C2H8NO+·I−Mr = 188.99Triclinic, P1a = 4.6557 (4) Åb = 7.5432 (6) Åc = 8.1787 (7) Åα = 85.235 (2)°β = 78.091 (2)°γ = 77.544 (2)°V = 274.21 (4) Å3Z = 2F(000) = 176Dx = 2.289 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 3767 reflectionsθ = 2.8–29.0°µ = 5.70 mm−1T = 150 KPlate, colorless0.34 × 0.12 × 0.03 mmData collection Bruker Kappa APEXII DUO diffractometerRadiation source: fine-focus sealed tubeCurved graphite monochromatorDetector resolution: 8.3333 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2008)Tmin = 0.672, Tmax = 0.8434884 measured reflections1319 independent reflections1254 reflections with I > 2σ(I)Rint = 0.021θmax = 28.0°, θmin = 2.6°h = −6→6k = −9→9l = −10→10Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.014wR(F2) = 0.032S = 1.081319 reflections48 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0163P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.002Δρmax = 0.58 e Å−3Δρmin = −0.46 e Å−3Special details 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) x y z Uiso*/UeqI1 0.63581 (3) 0.752733 (16) 0.669449 (16) 0.01732 (5)supporting informationsup-4Acta Cryst. (2014). E70, o628    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) U11 U22 U33 U12 U13 U23I1 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) O1—C1 1.425 (3) C1—C2 1.505 (3)O1—H1D 0.8400 C1—H1E 0.9900N1—C2 1.490 (3) C1—H1F 0.9900N1—H1A 0.9100 C2—H2A 0.9900N1—H1B 0.9100 C2—H2B 0.9900N1—H1C 0.9100C1—O1—H1D 109.5 O1—C1—H1F 109.5C2—N1—H1A 109.5 C2—C1—H1F 109.5C2—N1—H1B 109.5 H1E—C1—H1F 108.0H1A—N1—H1B 109.5 N1—C2—C1 111.23 (16)C2—N1—H1C 109.5 N1—C2—H2A 109.4H1A—N1—H1C 109.5 C1—C2—H2A 109.4H1B—N1—H1C 109.5 N1—C2—H2B 109.4O1—C1—C2 110.92 (17) C1—C2—H2B 109.4O1—C1—H1E 109.5 H2A—C2—H2B 108.0C2—C1—H1E 109.5O1—C1—C2—N1 −63.2 (2)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN1—H1A···O1i 0.91 1.93 2.800 (2) 158supporting informationsup-5Acta Cryst. (2014). E70, o628    N1—H1B···I1ii 0.91 2.75 3.5825 (18) 152N1—H1C···I1iii 0.91 2.78 3.6322 (18) 155O1—H1D···I1 0.84 2.72 3.5100 (15) 157Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1.

2-hydroxyethylammonium iodide

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2-hydroxyethylammonium iodide

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