2-Hy-droxy-methyl-1,3-dimethyl-1H-imidazol-3-ium triiodide.

The crystal packing of the title salt, C6H11N2O(+)·I3 (-), can be described as consisting of alternating layers of cations and anions parallel to the (100) plane along the a-axis direction. The components are linked by O-H⋯I, C-H⋯I and C-H⋯O interactions, generating a three-dimensional network. The O atom deviates from the imidazol ring by 0.896 (2) Å.

Related literature

For the importance of heterocyclic compounds and their applications, see: Pandey et al. (2009 ▶); Nasser (2000 ▶). For the biological activity of imidazole and imidazolium derivatives, see: Ucucu et al. (2001 ▶); Dominianni et al. (1989 ▶); Ozkay et al. (2010 ▶). For our previous work on imidazole derivatives, see: Bahnous et al. (2012 ▶); Zama et al. (2013 ▶); Chelghoum et al. (2011 ▶).

Experimental

Crystal data

C6H11N2O+·I3 −

M = 507.87

Monoclinic,

a = 7.1647 (8) Å

b = 15.5586 (19) Å

c = 11.3201 (13) Å

β = 96.026 (7)°

V = 1254.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 7.44 mm−1

T = 150 K

0.24 × 0.03 × 0.02 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.781, T max = 1.000

7061 measured reflections

2222 independent reflections

2104 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.034

S = 1.15

2222 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SMART (Bruker, 2006 ▶); data reduction: SMART; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012) ▶ and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813020266/hg5333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020266/hg5333Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020266/hg5333Isup3.cml

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

C6H11N2O+·I3−	F(000) = 912
Mr = 507.87	Dx = 2.688 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5058 reflections
a = 7.1647 (8) Å	θ = 2.2–25.1°
b = 15.5586 (19) Å	µ = 7.44 mm−1
c = 11.3201 (13) Å	T = 150 K
β = 96.026 (7)°	Stick, brown
V = 1254.9 (3) Å3	0.24 × 0.03 × 0.02 mm
Z = 4

Bruker APEXII diffractometer	2104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
CCD rotation images, thin slices scans	θmax = 25.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.781, Tmax = 1.000	k = −18→18
7061 measured reflections	l = −13→13
2222 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)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.034	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + 1.5935P] where P = (Fo2 + 2Fc2)/3
2222 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.47 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
I2	0.23583 (2)	0.148350 (12)	0.326494 (15)	0.01269 (6)
I1	0.19816 (3)	−0.006510 (12)	0.171029 (17)	0.01684 (6)
I3	0.25836 (3)	0.297933 (14)	0.474053 (18)	0.02126 (6)
N2	0.7383 (3)	0.17050 (16)	0.3419 (2)	0.0144 (5)
O1	0.8099 (3)	0.15052 (14)	0.09130 (18)	0.0177 (5)
H1	0.9119	0.1286	0.0833	0.027*
N1	0.7438 (3)	0.03209 (16)	0.3568 (2)	0.0141 (5)
C2	0.7275 (4)	0.09763 (19)	0.2795 (3)	0.0132 (6)
C5	0.7344 (4)	−0.0598 (2)	0.3266 (3)	0.0209 (7)
H5A	0.61	−0.0738	0.292	0.031*
H5B	0.7643	−0.0933	0.3972	0.031*
H5C	0.8227	−0.0723	0.2707	0.031*
C6	0.7239 (4)	0.2584 (2)	0.2943 (3)	0.0196 (7)
H6A	0.8421	0.2751	0.2686	0.029*
H6B	0.6918	0.2971	0.3551	0.029*
H6C	0.6285	0.2605	0.2282	0.029*
C3	0.7663 (4)	0.0651 (2)	0.4703 (3)	0.0195 (7)
H3	0.7811	0.0336	0.5405	0.023*
C4	0.7630 (4)	0.1512 (2)	0.4610 (3)	0.0171 (7)
H4	0.7751	0.1904	0.5234	0.021*
C1	0.6972 (4)	0.0911 (2)	0.1468 (3)	0.0160 (6)
H1A	0.7269	0.0332	0.1228	0.019*
H1B	0.566	0.1018	0.1204	0.019*

	U11	U22	U33	U12	U13	U23
I2	0.01199 (10)	0.01601 (11)	0.01018 (10)	−0.00047 (7)	0.00176 (7)	0.00073 (7)
I1	0.02125 (11)	0.01258 (11)	0.01685 (11)	−0.00009 (8)	0.00283 (8)	−0.00207 (8)
I3	0.02175 (11)	0.02351 (12)	0.01884 (12)	−0.00312 (8)	0.00360 (8)	−0.00943 (8)
N2	0.0138 (12)	0.0121 (13)	0.0176 (14)	0.0021 (10)	0.0039 (10)	0.0011 (11)
O1	0.0196 (10)	0.0200 (12)	0.0144 (11)	−0.0001 (9)	0.0058 (8)	0.0043 (9)
N1	0.0139 (12)	0.0159 (13)	0.0122 (12)	−0.0006 (10)	0.0008 (9)	0.0034 (11)
C2	0.0075 (13)	0.0149 (15)	0.0172 (15)	0.0021 (11)	0.0017 (11)	0.0017 (12)
C5	0.0276 (17)	0.0114 (16)	0.0234 (17)	0.0011 (13)	0.0022 (13)	0.0032 (13)
C6	0.0235 (16)	0.0124 (16)	0.0239 (17)	0.0016 (13)	0.0075 (13)	0.0029 (13)
C3	0.0193 (15)	0.0275 (19)	0.0117 (15)	0.0002 (13)	0.0021 (12)	0.0025 (13)
C4	0.0182 (15)	0.0213 (17)	0.0127 (15)	−0.0006 (13)	0.0054 (12)	−0.0039 (13)
C1	0.0158 (14)	0.0176 (16)	0.0141 (15)	−0.0007 (12)	−0.0004 (11)	0.0042 (13)

I2—I3	2.8594 (4)	C5—H5A	0.96
I2—I1	2.9792 (4)	C5—H5B	0.96
N2—C2	1.334 (4)	C5—H5C	0.96
N2—C4	1.374 (4)	C6—H6A	0.96
N2—C6	1.470 (4)	C6—H6B	0.96
O1—C1	1.417 (3)	C6—H6C	0.96
O1—H1	0.82	C3—C4	1.344 (5)
N1—C2	1.341 (4)	C3—H3	0.93
N1—C3	1.377 (4)	C4—H4	0.93
N1—C5	1.470 (4)	C1—H1A	0.97
C2—C1	1.499 (4)	C1—H1B	0.97
I3—I2—I1	178.026 (8)	N2—C6—H6B	109.5
C2—N2—C4	109.2 (3)	H6A—C6—H6B	109.5
C2—N2—C6	126.8 (3)	N2—C6—H6C	109.5
C4—N2—C6	124.0 (3)	H6A—C6—H6C	109.5
C1—O1—H1	109.5	H6B—C6—H6C	109.5
C2—N1—C3	108.6 (3)	C4—C3—N1	107.4 (3)
C2—N1—C5	126.1 (3)	C4—C3—H3	126.3
C3—N1—C5	125.3 (3)	N1—C3—H3	126.3
N2—C2—N1	107.7 (3)	C3—C4—N2	107.1 (3)
N2—C2—C1	125.7 (3)	C3—C4—H4	126.4
N1—C2—C1	126.6 (3)	N2—C4—H4	126.4
N1—C5—H5A	109.5	O1—C1—C2	111.7 (2)
N1—C5—H5B	109.5	O1—C1—H1A	109.3
H5A—C5—H5B	109.5	C2—C1—H1A	109.3
N1—C5—H5C	109.5	O1—C1—H1B	109.3
H5A—C5—H5C	109.5	C2—C1—H1B	109.3
H5B—C5—H5C	109.5	H1A—C1—H1B	107.9
N2—C6—H6A	109.5
C4—N2—C2—N1	0.4 (3)	C2—N1—C3—C4	0.2 (3)
C6—N2—C2—N1	−178.8 (2)	C5—N1—C3—C4	−178.4 (3)
C4—N2—C2—C1	178.8 (3)	N1—C3—C4—N2	0.1 (3)
C6—N2—C2—C1	−0.4 (4)	C2—N2—C4—C3	−0.3 (3)
C3—N1—C2—N2	−0.4 (3)	C6—N2—C4—C3	179.0 (3)
C5—N1—C2—N2	178.2 (2)	N2—C2—C1—O1	44.3 (4)
C3—N1—C2—C1	−178.7 (3)	N1—C2—C1—O1	−137.6 (3)
C5—N1—C2—C1	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···I1i	0.82	3.03	3.741 (2)	146
C1—H1B···I3ii	0.97	3.05	3.924 (3)	151
C4—H4···O1iii	0.93	2.60	3.421 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯I1i	0.82	3.03	3.741 (2)	146
C1—H1B⋯I3ii	0.97	3.05	3.924 (3)	151
C4—H4⋯O1iii	0.93	2.60	3.421 (4)	148

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