organic compounds
H-imidazol-3-ium-4-yl)ethanaminium dichloride, a re-determination
of 2-(1aLaboratoire de Chimie Inorganique et Environnement, Universite de Tlemcen, BP119, 13000, Tlemcen, Algeria, and bCentre de Diffractometrie X, UMR 6226 CNRS, Unite Sciences Chimiques de Rennes, Universite de Rennes I, 263 Avenue du General Leclerc, 35042 Rennes, France
*Correspondence e-mail: l_bouklihacene@mail.univ-tlemcen.dz, lilibou25@yahoo.fr
The 5H11N3+·2Cl−, was redetermined. In comparison with the previous study [Bonnet et al. (1975). Bull. Soc. Fr. Mineral. Crist. 98, 208–213.], the positions of some H atoms were corrected, allowing a more accurate description of the hydrogen-bonding scheme. In addition, the was also determined. The maximum differences in terms of bond lengths and angles between the two determinations are 0.022 Å and 1.43°, respectively. The organic cation display a anti conformation of the protonated amine function and the imidazolium ring. The dihedral angle between the imidazolium plane and the plane through the C—C—N side chain is 29.58 (3)°. In the crystal, the organic cations and Cl− anions are stacked alternatively into layers parallel to (100). N—H⋯Cl hydrogen bonds between all H atoms of the ammonium group and both N—H groups of the imidazolium ring and the Cl− acceptor anions lead to the linkage of organic and inorganic layers into a three-dimensional network.
of the title molecular salt, CKeywords: crystal structure; histamine; redetermination; hydrogen bonding.
CCDC reference: 1051848
1. Related literature
Histamine [2-(1H-imidazol-4-yl)ethanamine] is a biogenic amine present in essentially all mammalian tissues and involved in several defense mechanisms of the body. It plays a role in various physiological processes, such as control of gastric acid secretion, neurotransmission, regulation of the microcirculation, and modulation of inflammatory (Cooper et al., 1990; Barnes, 2001) and immunological reactions (Schwartz et al., 1991; Bachert et al., 1998; Emanuel et al., 1999). The contribution of histamine in these physiological and pathological processes and the use in pharmacology make it an interesting substance in biochemistry (Leurs et al., 1995; Galoppin & Ponvert, 1997; O'Mahony et al., 2011; Jadidi-Niaragh & Mirshafiey, 2010; Gustiananda et al., 2012). The structure of the title compound has been determined previously by Bonnet et al. (1975) who reported lattice parameters of a =7.596 (6), b = 12.706 (8), c = 4.457 (4) Å, β = 91.64 (5)° at room temperature. For the structure of the histamine copper(II) chloride complex and its study, see: Belfilali et al. (2015a), and for the structure of monopronated histamine with Cl− as counter-anion, see: Belfilali et al. (2015b).
2. Experimental
2.1. Crystal data
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1051848
https://doi.org/10.1107/S2056989015018848/wm5220sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018848/wm5220Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015018848/wm5220Isup3.cml
A stoichiometric mixture of histamine dihydrochloride (1.0 mmol) and 3-ethoxy-4-hydroxybenzaldehyde was irradiated in a microwave oven at 200 Watt for 10 minutes. The reaction mixture was then allowed to attain room temperature and the obtained crystals were separated by filtration.
Hydrogen atoms linked to nitrogen atoms were found from Fourier difference maps and were refined with distance restraints in the range 0.84 (3) - 0.95 (3) Å and with a common Uiso parameter of 0.05 Å2. C-bound hydrogen atoms were refined with calculated positions, with C—H = 0.95 and U(H)iso = 1.2Ueq(C) for aromatic H atoms and with C—H = 0.99 and U(H)iso = 1.2Ueq(C) for methylene H atoms.
Histamine [2-(1H-imidazol-4-yl)ethanamine] is a biogenic amine present in essentially all mammalian tissues and involved in several defense mechanisms of the body. It plays a role in various physiological processes, such as control of gastric acid secretion, neurotransmission, regulation of the microcirculation, and modulation of inflammatory (Cooper et al., 1990; Barnes et al., 2001) and immunological reactions (Schwartz et al., 1991; Bachert et al., 1998; Emanuel et al., 1999). The contribution of histamine in these physiological and pathological processes and the use in pharmacology make it an interesting substance in biochemistry (Leurs et al., 1995; Galoppin & Ponvert, 1997; O'Mahony et al., 2011; Jadidi-Niaragh & Mirshafiey, 2010; Gustiananda et al., 2012). The structure of the title compound has been determined previously by Bonnet et al. (1975) who reported lattice parameters of a =7.596 (6), b = 12.706 (8), c = 4.457 (4) Å, β = 91.64 (5)° at room temperature. For the structure of the histamine copper(II) chloride complex and its study, see: Belfilali et al. (2015a), and for the structure of monopronated histamine with Cl- as counter-anion, see: Belfilali et al. (2015b).
A stoichiometric mixture of histamine dihydrochloride (1.0 mmol) and 3-ethoxy-4-hydroxybenzaldehyde was irradiated in a microwave oven at 200 Watt for 10 minutes. The reaction mixture was then allowed to attain room temperature and the obtained crystals were separated by filtration.
detailsHydrogen atoms linked to nitrogen atoms were found from Fourier difference maps and were refined with distance restraints in the range 0.84 (3) - 0.95 (3) Å and with a common Uiso parameter of 0.05 Å2. C-bound hydrogen atoms were refined with calculated positions, with C—H = 0.95 and U(H)iso = 1.2Ueq(C) for aromatic H atoms and with C—H = 0.99 and U(H)iso = 1.2Ueq(C) for methylene H atoms.
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. Tautomeric forms of histamine. | |
Fig. 2. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 3. Part of the crystal structure with hydrogen bonds shown as dashed lines. |
C5H11N3+·2Cl− | F(000) = 192 |
Mr = 184.07 | Dx = 1.445 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2786 reflections |
a = 4.4358 (2) Å | θ = 2.7–27.5° |
b = 12.6281 (4) Å | µ = 0.70 mm−1 |
c = 7.5588 (3) Å | T = 150 K |
β = 91.910 (1)° | Prism, colourless |
V = 423.18 (3) Å3 | 0.43 × 0.32 × 0.09 mm |
Z = 2 |
Bruker APEXII CCD, diffractometer | 1815 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | h = −5→5 |
Tmin = 0.825, Tmax = 0.939 | k = −16→13 |
3729 measured reflections | l = −9→9 |
1855 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.058 | w = 1/[σ2(Fo2) + (0.0327P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1855 reflections | Δρmax = 0.22 e Å−3 |
106 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 841 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (5) |
C5H11N3+·2Cl− | V = 423.18 (3) Å3 |
Mr = 184.07 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.4358 (2) Å | µ = 0.70 mm−1 |
b = 12.6281 (4) Å | T = 150 K |
c = 7.5588 (3) Å | 0.43 × 0.32 × 0.09 mm |
β = 91.910 (1)° |
Bruker APEXII CCD, diffractometer | 1855 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | 1815 reflections with I > 2σ(I) |
Tmin = 0.825, Tmax = 0.939 | Rint = 0.024 |
3729 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.058 | Δρmax = 0.22 e Å−3 |
S = 1.08 | Δρmin = −0.17 e Å−3 |
1855 reflections | Absolute structure: Flack (1983), 841 Friedel pairs |
106 parameters | Absolute structure parameter: 0.06 (5) |
1 restraint |
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 | ||
N1 | 0.9759 (4) | 0.18301 (13) | 0.4308 (2) | 0.0201 (3) | |
H1A | 1.115 (6) | 0.232 (2) | 0.472 (3) | 0.05* | |
H1B | 0.787 (6) | 0.217 (2) | 0.441 (3) | 0.05* | |
H1C | 1.015 (6) | 0.179 (2) | 0.316 (4) | 0.05* | |
C2 | 0.9990 (5) | 0.07908 (15) | 0.5236 (2) | 0.0209 (4) | |
H2A | 1.2044 | 0.0497 | 0.5125 | 0.025* | |
H2B | 0.853 | 0.0285 | 0.469 | 0.025* | |
C3 | 0.9317 (4) | 0.09457 (15) | 0.7190 (2) | 0.0214 (4) | |
H3A | 1.053 | 0.1545 | 0.7669 | 0.026* | |
H3B | 0.716 | 0.1127 | 0.7299 | 0.026* | |
C4 | 1.0019 (4) | −0.00243 (13) | 0.8252 (2) | 0.0160 (3) | |
C5 | 1.1983 (4) | −0.08313 (15) | 0.8024 (2) | 0.0189 (3) | |
H5 | 1.3185 | −0.0945 | 0.7025 | 0.023* | |
N6 | 1.1904 (3) | −0.14577 (12) | 0.95191 (19) | 0.0206 (3) | |
H6 | 1.284 (6) | −0.206 (2) | 0.964 (3) | 0.05* | |
C7 | 0.9952 (4) | −0.10582 (15) | 1.0615 (2) | 0.0211 (4) | |
H7 | 0.9475 | −0.1342 | 1.1736 | 0.025* | |
N8 | 0.8764 (3) | −0.01892 (12) | 0.98803 (17) | 0.0168 (3) | |
H8 | 0.745 (6) | 0.021 (2) | 1.031 (4) | 0.05* | |
Cl1 | 0.47163 (8) | 0.32961 (3) | 0.59693 (5) | 0.02068 (11) | |
Cl2 | 0.43148 (9) | 0.15270 (3) | 0.11930 (5) | 0.01937 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0192 (7) | 0.0233 (9) | 0.0178 (7) | −0.0004 (6) | 0.0021 (6) | 0.0025 (6) |
C2 | 0.0264 (9) | 0.0187 (9) | 0.0175 (9) | −0.0022 (7) | 0.0010 (7) | −0.0001 (7) |
C3 | 0.0267 (9) | 0.0202 (9) | 0.0174 (8) | 0.0047 (8) | 0.0036 (7) | 0.0012 (7) |
C4 | 0.0168 (7) | 0.0158 (8) | 0.0155 (7) | −0.0017 (7) | 0.0002 (6) | −0.0027 (6) |
C5 | 0.0208 (8) | 0.0177 (8) | 0.0183 (8) | 0.0006 (7) | 0.0026 (6) | −0.0036 (7) |
N6 | 0.0214 (7) | 0.0173 (8) | 0.0233 (7) | 0.0014 (6) | 0.0018 (6) | 0.0014 (6) |
C7 | 0.0225 (9) | 0.0215 (9) | 0.0195 (7) | −0.0013 (7) | 0.0008 (7) | 0.0033 (7) |
N8 | 0.0167 (7) | 0.0168 (7) | 0.0173 (7) | −0.0009 (6) | 0.0032 (5) | −0.0017 (5) |
Cl1 | 0.01948 (19) | 0.0235 (2) | 0.01936 (17) | −0.00067 (18) | 0.00474 (13) | −0.00219 (16) |
Cl2 | 0.01775 (18) | 0.0187 (2) | 0.02194 (18) | −0.00186 (17) | 0.00442 (13) | −0.00354 (15) |
N1—C2 | 1.490 (2) | C4—C5 | 1.355 (3) |
N1—H1A | 0.92 (3) | C4—N8 | 1.383 (2) |
N1—H1B | 0.95 (3) | C5—N6 | 1.381 (2) |
N1—H1C | 0.89 (3) | C5—H5 | 0.95 |
C2—C3 | 1.530 (2) | N6—C7 | 1.319 (2) |
C2—H2A | 0.99 | N6—H6 | 0.88 (3) |
C2—H2B | 0.99 | C7—N8 | 1.331 (2) |
C3—C4 | 1.492 (2) | C7—H7 | 0.95 |
C3—H3A | 0.99 | N8—H8 | 0.84 (3) |
C3—H3B | 0.99 | ||
C2—N1—H1A | 113.7 (15) | H3A—C3—H3B | 107.9 |
C2—N1—H1B | 113.9 (15) | C5—C4—N8 | 106.22 (14) |
H1A—N1—H1B | 105 (2) | C5—C4—C3 | 132.25 (16) |
C2—N1—H1C | 112.9 (18) | N8—C4—C3 | 121.30 (14) |
H1A—N1—H1C | 103 (2) | C4—C5—N6 | 107.03 (15) |
H1B—N1—H1C | 108 (2) | C4—C5—H5 | 126.5 |
N1—C2—C3 | 109.22 (15) | N6—C5—H5 | 126.5 |
N1—C2—H2A | 109.8 | C7—N6—C5 | 109.26 (15) |
C3—C2—H2A | 109.8 | C7—N6—H6 | 126.0 (18) |
N1—C2—H2B | 109.8 | C5—N6—H6 | 124.3 (17) |
C3—C2—H2B | 109.8 | N6—C7—N8 | 108.21 (15) |
H2A—C2—H2B | 108.3 | N6—C7—H7 | 125.9 |
C4—C3—C2 | 111.78 (14) | N8—C7—H7 | 125.9 |
C4—C3—H3A | 109.3 | C7—N8—C4 | 109.27 (14) |
C2—C3—H3A | 109.3 | C7—N8—H8 | 126.6 (18) |
C4—C3—H3B | 109.3 | C4—N8—H8 | 124.2 (18) |
C2—C3—H3B | 109.3 | ||
N1—C2—C3—C4 | −170.28 (15) | C4—C5—N6—C7 | 0.6 (2) |
C2—C3—C4—C5 | 26.5 (3) | C5—N6—C7—N8 | −0.2 (2) |
C2—C3—C4—N8 | −159.79 (15) | N6—C7—N8—C4 | −0.27 (19) |
N8—C4—C5—N6 | −0.70 (17) | C5—C4—N8—C7 | 0.61 (17) |
C3—C4—C5—N6 | 173.73 (18) | C3—C4—N8—C7 | −174.57 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1i | 0.92 (3) | 2.19 (3) | 3.1071 (17) | 171 (2) |
N1—H1B···Cl1 | 0.95 (3) | 2.34 (3) | 3.1930 (17) | 150 (2) |
N1—H1C···Cl2i | 0.89 (3) | 2.44 (3) | 3.1768 (16) | 141 (2) |
N6—H6···Cl2ii | 0.88 (3) | 2.28 (3) | 3.1046 (16) | 157 (2) |
N8—H8···Cl2iii | 0.84 (3) | 2.28 (3) | 3.1157 (15) | 169 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1; (iii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1i | 0.92 (3) | 2.19 (3) | 3.1071 (17) | 171 (2) |
N1—H1B···Cl1 | 0.95 (3) | 2.34 (3) | 3.1930 (17) | 150 (2) |
N1—H1C···Cl2i | 0.89 (3) | 2.44 (3) | 3.1768 (16) | 141 (2) |
N6—H6···Cl2ii | 0.88 (3) | 2.28 (3) | 3.1046 (16) | 157 (2) |
N8—H8···Cl2iii | 0.84 (3) | 2.28 (3) | 3.1157 (15) | 169 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1; (iii) x, y, z+1. |
Acknowledgements
The authors gratefully acknowledge the support of the Algerian Ministry of Higher Education and Scientific Research and thank Frédéric Atil from the Club de Minéralogie de Chamonix, du Mont-Blanc et des Alpes du Nord.
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