2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium chloride.

In the crystal structure of the title compound, C(4)H(8)N(3)O(+)·Cl(-), N-H⋯Cl hydrogen bonds link the components into chains along [010]. In addition, weak C-H⋯Cl hydrogen bonds link the chains into a two-dimensional network perpendicular to (001).

Related literature

For creatinine (2-amino-1-methyl-5H-imidazol-4-one), which is used in the synthesis of some 1:1 proton-transfer compounds, see; Moghimi et al. (2004 ▶); Soleimannejad et al. (2005 ▶). For related structures, see: Tabatabaee et al. (2007 ▶); Bujak & Zaleski (2002 ▶); Tabatabaee, Abbasi et al. (2011 ▶); Tabatabaee, Tahriri et al. (2011 ▶, 2012 ▶); Tabatabaee, Adineh et al. (2012 ▶). For background information on weak C—H⋯Cl hydrogen bonds, see: Freytag & Jones (2000 ▶); Taylor & Kennard (1982 ▶).

Experimental

Crystal data

C4H8N3O+·Cl−

M = 149.58

Monoclinic,

a = 8.4617 (2) Å

b = 7.7073 (2) Å

c = 10.2215 (3) Å

β = 98.369 (2)°

V = 659.52 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.51 mm−1

T = 120 K

0.57 × 0.35 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.509, T max = 1.000

5373 measured reflections

1167 independent reflections

1158 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.074

S = 1.08

1167 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027080/lh5487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027080/lh5487Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027080/lh5487Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H8N3O+·Cl−	F(000) = 312
Mr = 149.58	Dx = 1.507 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 5086 reflections
a = 8.4617 (2) Å	θ = 4.4–66.9°
b = 7.7073 (2) Å	µ = 4.51 mm−1
c = 10.2215 (3) Å	T = 120 K
β = 98.369 (2)°	Plate, colourless
V = 659.52 (3) Å3	0.57 × 0.35 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1167 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1158 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.3784 pixels mm-1	θmax = 67.0°, θmin = 6.4°
Rotation method data acquisition using ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.509, Tmax = 1.000	l = −12→11
5373 measured 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.1996P] where P = (Fo2 + 2Fc2)/3
1167 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.18 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. The H atoms were all located in a difference map, but those attached to carbon atoms and the nitrogen atom in amino group were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, N—H in the range 0.86–0.89 N—H to 0.86 O—H = 0.82 Å) and Uiso(H) (in the range 1.2 times Ueq of the parent atom). The distance between hydrogen atom H3 and N2 was left unrestrained.

	x	y	z	Uiso*/Ueq
Cl1	0.86814 (3)	0.71590 (4)	0.45236 (3)	0.02046 (16)
O1	0.43618 (13)	0.57647 (13)	0.32081 (12)	0.0358 (3)
N1	0.79940 (13)	0.13245 (15)	0.41934 (11)	0.0238 (3)
H1	0.8035	0.0210	0.4217	0.029*
H2	0.8847	0.1923	0.4421	0.029*
N2	0.64629 (13)	0.38708 (14)	0.37714 (11)	0.0217 (3)
H3	0.7227	0.4646	0.4031	0.026*
C1	0.48933 (16)	0.43236 (18)	0.33205 (13)	0.0234 (3)
C2	0.40103 (16)	0.26312 (17)	0.30246 (14)	0.0211 (3)
H4	0.3128	0.2525	0.3529	0.025*
H5	0.3606	0.2526	0.2090	0.025*
N3	0.52395 (13)	0.13463 (14)	0.34360 (11)	0.0189 (3)
C3	0.66330 (16)	0.21100 (17)	0.38107 (13)	0.0184 (3)
C4	0.49578 (15)	−0.04876 (17)	0.31667 (13)	0.0222 (3)
H6	0.4772	−0.0674	0.2228	0.027*
H7	0.4040	−0.0858	0.3545	0.027*
H8	0.5876	−0.1142	0.3549	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0170 (2)	0.0197 (2)	0.0238 (2)	−0.00117 (10)	0.00001 (14)	−0.00029 (10)
O1	0.0308 (6)	0.0202 (6)	0.0562 (7)	0.0037 (4)	0.0058 (5)	0.0023 (5)
N1	0.0176 (6)	0.0207 (6)	0.0312 (6)	−0.0022 (4)	−0.0029 (5)	−0.0001 (5)
N2	0.0203 (6)	0.0182 (6)	0.0262 (6)	−0.0030 (4)	0.0019 (5)	−0.0020 (4)
C1	0.0225 (7)	0.0205 (7)	0.0279 (7)	0.0009 (5)	0.0055 (5)	0.0006 (5)
C2	0.0162 (7)	0.0191 (6)	0.0276 (7)	0.0028 (5)	0.0021 (5)	0.0011 (6)
N3	0.0166 (5)	0.0163 (6)	0.0233 (6)	−0.0002 (4)	0.0007 (4)	0.0001 (4)
C3	0.0203 (7)	0.0188 (7)	0.0163 (6)	−0.0019 (5)	0.0032 (5)	−0.0007 (4)
C4	0.0195 (7)	0.0175 (6)	0.0285 (7)	−0.0017 (5)	0.0002 (5)	−0.0008 (5)

O1—C1	1.1976 (18)	C2—N3	1.4533 (16)
N1—C3	1.3094 (18)	C2—H4	0.9700
N1—H1	0.8600	C2—H5	0.9700
N1—H2	0.8600	N3—C3	1.3237 (18)
N2—C3	1.3647 (17)	N3—C4	1.4530 (17)
N2—C1	1.3856 (17)	C4—H6	0.9600
N2—H3	0.8921	C4—H7	0.9600
C1—C2	1.5118 (19)	C4—H8	0.9600
C3—N1—H1	120.0	H4—C2—H5	109.2
C3—N1—H2	120.0	C3—N3—C4	127.01 (11)
H1—N1—H2	120.0	C3—N3—C2	110.53 (11)
C3—N2—C1	110.62 (11)	C4—N3—C2	121.15 (10)
C3—N2—H3	126.1	N1—C3—N3	126.05 (12)
C1—N2—H3	123.3	N1—C3—N2	123.57 (12)
O1—C1—N2	126.44 (13)	N3—C3—N2	110.36 (11)
O1—C1—C2	127.82 (12)	N3—C4—H6	109.5
N2—C1—C2	105.73 (11)	N3—C4—H7	109.5
N3—C2—C1	102.59 (11)	H6—C4—H7	109.5
N3—C2—H4	111.2	N3—C4—H8	109.5
C1—C2—H4	111.2	H6—C4—H8	109.5
N3—C2—H5	111.2	H7—C4—H8	109.5
C1—C2—H5	111.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.86	2.42	3.2714 (12)	169
N1—H2···Cl1ii	0.86	2.32	3.1506 (12)	163
N2—H3···Cl1	0.89	2.31	3.1808 (11)	165
C2—H4···Cl1iii	0.97	2.69	3.6271 (14)	162
C4—H8···Cl1i	0.96	2.77	3.7241 (13)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.86	2.42	3.2714 (12)	169
N1—H2⋯Cl1ii	0.86	2.32	3.1506 (12)	163
N2—H3⋯Cl1	0.89	2.31	3.1808 (11)	165
C2—H4⋯Cl1iii	0.97	2.69	3.6271 (14)	162
C4—H8⋯Cl1i	0.96	2.77	3.7241 (13)	175

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