Crystal structure of 2-(1H-imidazol-4-yl)ethanaminium chloride.

The title mol-ecular salt, C5H10N3 (+)·Cl(-), was obtained as by-product in the attempted synthesis of a histamine derivative. The terminal amino group of the starting material is protonated. The Cimidazole-C-C-N(H3)(+) group in the cation is in an anti conformation with a torsion angle of 176.22 (10)°. In the crystal, cations and anions are linked via N-H⋯N and N-H-Cl hydrogen bonds, forming a two-dimensional network parallel to (10-1). A single weak C-H⋯Cl hydrogen bond completes a three-dimensional network.

Related literature

For the biological and pharmacological applications of histamine derivatives, see: Barnes et al. (2001 ▸); Schwartz et al. (1991 ▸); Bachert et al. (1998 ▸); Emanuel et al. (1999 ▸); Apáti et al. (2012 ▸). For a study of a histamine copper(II) chloride complex, see: Belfilali et al. (2015 ▸). For the general chemistry of transition metal ions with histamine, see: Mikulski et al. (2012 ▸); Kowalik-Jankowska et al. (2010 ▸); Selmeczi et al. (2012 ▸). For a related structure, see: Prout et al. (1974 ▸).

Experimental

Crystal data

C5H10N3 +·Cl−

M = 147.61

Monoclinic,

a = 4.5840 (2) Å

b = 9.1614 (3) Å

c = 17.3114 (5) Å

β = 91.682 (1)°

V = 726.69 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 150 K

0.41 × 0.13 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▸)’ T min = 0.868, T max = 0.965

5568 measured reflections

1645 independent reflections

1494 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.08

1645 reflections

86 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2006 ▸); cell refinement: 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 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▸) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006866/lh5756sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006866/lh5756Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006866/lh5756Isup3.docx

Click here for additional data file.

. DOI: 10.1107/S2056989015006866/lh5756fig1.tif

The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015006866/lh5756fig2.tif

Part of the crystal structure with hydrogen bonds shown as dashed lines.

CCDC reference: 1051527

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

C5H10N3+·Cl−	F(000) = 312
Mr = 147.61	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2978 reflections
a = 4.5840 (2) Å	θ = 4.6–27.5°
b = 9.1614 (3) Å	µ = 0.44 mm−1
c = 17.3114 (5) Å	T = 150 K
β = 91.682 (1)°	Prism, colourless
V = 726.69 (4) Å3	0.41 × 0.13 × 0.08 mm
Z = 4

Bruker APEXII diffractometer	1494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2006)'	h = −5→5
Tmin = 0.868, Tmax = 0.965	k = −11→11
5568 measured reflections	l = −19→22
1645 independent 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0331P)2 + 0.246P] where P = (Fo2 + 2Fc2)/3
1645 reflections	(Δ/σ)max = 0.001
86 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.21 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
N1	0.4106 (2)	0.80020 (12)	−0.01832 (6)	0.0174 (2)
H1A	0.3108	0.7313	−0.0462	0.026*
H1B	0.5029	0.8614	−0.051	0.026*
H1C	0.2838	0.8521	0.0104	0.026*
C2	0.6308 (3)	0.72762 (15)	0.03395 (7)	0.0174 (3)
H2A	0.7497	0.8028	0.0613	0.021*
H2B	0.7631	0.6675	0.0029	0.021*
C3	0.4835 (3)	0.63146 (15)	0.09277 (8)	0.0192 (3)
H3A	0.3615	0.6926	0.1262	0.023*
H3B	0.3543	0.5605	0.0655	0.023*
C4	0.7051 (3)	0.55095 (15)	0.14180 (7)	0.0169 (3)
N5	0.8253 (2)	0.41984 (12)	0.11844 (6)	0.0184 (2)
C6	1.0162 (3)	0.38371 (15)	0.17436 (7)	0.0197 (3)
H6	1.1334	0.2982	0.1741	0.024*
N7	1.0229 (3)	0.48288 (14)	0.23111 (7)	0.0223 (3)
H7	1.124 (5)	0.481 (2)	0.2682 (14)	0.05*
C8	0.8270 (3)	0.58985 (16)	0.21139 (8)	0.0229 (3)
H8	0.7842	0.6747	0.2405	0.027*
Cl1	0.13058 (7)	0.01456 (3)	0.108958 (17)	0.01841 (12)

	U11	U22	U33	U12	U13	U23
N1	0.0185 (5)	0.0155 (6)	0.0180 (5)	−0.0019 (4)	−0.0008 (4)	−0.0004 (4)
C2	0.0152 (6)	0.0180 (6)	0.0190 (6)	−0.0021 (5)	−0.0022 (5)	−0.0002 (5)
C3	0.0156 (6)	0.0200 (7)	0.0220 (7)	−0.0008 (5)	0.0007 (5)	0.0009 (5)
C4	0.0160 (6)	0.0180 (6)	0.0169 (6)	−0.0017 (5)	0.0031 (5)	0.0006 (5)
N5	0.0206 (5)	0.0155 (5)	0.0189 (5)	−0.0016 (4)	−0.0018 (4)	−0.0006 (5)
C6	0.0218 (6)	0.0176 (6)	0.0197 (6)	−0.0007 (5)	−0.0012 (5)	0.0015 (5)
N7	0.0238 (6)	0.0268 (6)	0.0161 (6)	0.0001 (5)	−0.0041 (5)	−0.0009 (5)
C8	0.0252 (7)	0.0233 (7)	0.0202 (7)	0.0034 (6)	0.0008 (5)	−0.0046 (6)
Cl1	0.02061 (18)	0.01856 (18)	0.01589 (19)	−0.00105 (12)	−0.00236 (12)	−0.00087 (11)

N1—C2	1.4920 (16)	C3—H3B	0.99
N1—H1A	0.91	C4—C8	1.3604 (18)
N1—H1B	0.91	C4—N5	1.3866 (17)
N1—H1C	0.91	N5—C6	1.3277 (16)
C2—C3	1.5196 (18)	C6—N7	1.3379 (18)
C2—H2A	0.99	C6—H6	0.95
C2—H2B	0.99	N7—C8	1.3658 (18)
C3—C4	1.4985 (18)	N7—H7	0.78 (2)
C3—H3A	0.99	C8—H8	0.95
C2—N1—H1A	109.5	C2—C3—H3B	109.4
C2—N1—H1B	109.5	H3A—C3—H3B	108
H1A—N1—H1B	109.5	C8—C4—N5	109.20 (11)
C2—N1—H1C	109.5	C8—C4—C3	128.79 (13)
H1A—N1—H1C	109.5	N5—C4—C3	121.99 (11)
H1B—N1—H1C	109.5	C6—N5—C4	105.21 (11)
N1—C2—C3	111.03 (10)	N5—C6—N7	111.50 (12)
N1—C2—H2A	109.4	N5—C6—H6	124.2
C3—C2—H2A	109.4	N7—C6—H6	124.2
N1—C2—H2B	109.4	C6—N7—C8	107.63 (11)
C3—C2—H2B	109.4	C6—N7—H7	126.3 (16)
H2A—C2—H2B	108	C8—N7—H7	126.1 (16)
C4—C3—C2	110.96 (10)	C4—C8—N7	106.46 (12)
C4—C3—H3A	109.4	C4—C8—H8	126.8
C2—C3—H3A	109.4	N7—C8—H8	126.8
C4—C3—H3B	109.4
N1—C2—C3—C4	176.22 (10)	C4—N5—C6—N7	0.21 (15)
C2—C3—C4—C8	93.03 (17)	N5—C6—N7—C8	−0.18 (16)
C2—C3—C4—N5	−84.87 (15)	N5—C4—C8—N7	0.06 (15)
C8—C4—N5—C6	−0.16 (15)	C3—C4—C8—N7	−178.06 (12)
C3—C4—N5—C6	178.11 (12)	C6—N7—C8—C4	0.07 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N5i	0.91	1.96	2.8508 (15)	168
N1—H1B···Cl1i	0.91	2.28	3.1557 (11)	160
N1—H1C···Cl1ii	0.91	2.39	3.2443 (11)	157
N7—H7···Cl1iii	0.78 (2)	2.40 (2)	3.1645 (12)	168 (2)
C2—H2A···Cl1iv	0.99	2.72	3.6974 (14)	168

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AN5i	0.91	1.96	2.8508(15)	168
N1H1BCl1i	0.91	2.28	3.1557(11)	160
N1H1CCl1ii	0.91	2.39	3.2443(11)	157
N7H7Cl1iii	0.78(2)	2.40(2)	3.1645(12)	168(2)
C2H2ACl1iv	0.99	2.72	3.6974(14)	168

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