2-Hy-droxy-methyl-1,3-dimethyl-imidazolium iodide.

The crystal packing of the title compound, C(6)H(11)N(2)O(+)·I(-), can be described as inter-calated layers lying parallel to (010), with the iodide ions located between the cations. A weak intra-molecular C-H⋯O hydrogen bond occurs within the cation. In the crystal, inter-molecular O-H⋯I hydrogen bonds result in the formation of a three-dimensional network and reinforce the cohesion of the ionic structure.

Related literature

For related ionic liquids, see: Welton (1999 ▶); Kubisa (2004 ▶); Corma & Garcia (2003 ▶); Sheldon (2001 ▶); Wasserscheid & Kerm (2000 ▶). For synthetic appilications of ionic liquids, see: Varma & Namboodiri (2001 ▶).

Experimental

Crystal data

C6H11N2O+·I−

M = 254.07

Monoclinic,

a = 7.3428 (3) Å

b = 7.2186 (3) Å

c = 16.8870 (8) Å

β = 93.093 (2)°

V = 893.79 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.53 mm−1

T = 150 K

0.3 × 0.13 × 0.01 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.718, T max = 0.965

4200 measured reflections

2035 independent reflections

1463 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.063

S = 1.03

2035 reflections

94 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025700/hg5062sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025700/hg5062Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025700/hg5062Isup3.cml

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

C6H11N2O+·I−	F(000) = 488
Mr = 254.07	Dx = 1.888 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1935 reflections
a = 7.3428 (3) Å	θ = 2.4–27.4°
b = 7.2186 (3) Å	µ = 3.53 mm−1
c = 16.8870 (8) Å	T = 150 K
β = 93.093 (2)°	Prism, colourless
V = 893.79 (7) Å3	0.3 × 0.13 × 0.01 mm
Z = 4

Bruker APEXII diffractometer	1463 reflections with I > 2σ(I)
graphite	Rint = 0.019
CCD rotation images, thin slices scans	θmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −5→9
Tmin = 0.718, Tmax = 0.965	k = −6→9
4200 measured reflections	l = −21→21
2035 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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0289P)2 + 0.3175P] where P = (Fo2 + 2Fc2)/3
2035 reflections	(Δ/σ)max = 0.001
94 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.54 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
I1	0.80624 (2)	0.74882 (2)	0.413580 (10)	0.02430 (8)
C1	0.6996 (5)	0.2724 (3)	0.20049 (17)	0.0284 (6)
H1A	0.8326	0.2864	0.2033	0.043*
H1B	0.6438	0.3775	0.1716	0.043*
H1C	0.6663	0.157	0.1728	0.043*
N2	0.6343 (3)	0.2668 (2)	0.28084 (14)	0.0204 (5)
C3	0.4551 (4)	0.2855 (3)	0.29967 (18)	0.0251 (6)
H3	0.3528	0.3011	0.2634	0.03*
C4	0.4528 (4)	0.2773 (3)	0.37988 (17)	0.0232 (6)
H4	0.3482	0.2865	0.4104	0.028*
N5	0.6304 (3)	0.2533 (2)	0.40871 (13)	0.0195 (5)
C6	0.6882 (4)	0.2431 (3)	0.49319 (18)	0.0271 (6)
H6A	0.7534	0.1265	0.5038	0.041*
H6B	0.5807	0.2483	0.5251	0.041*
H6C	0.7689	0.3475	0.5071	0.041*
C7	0.7404 (4)	0.2472 (3)	0.34775 (16)	0.0192 (5)
C8	0.9437 (4)	0.2288 (3)	0.35238 (19)	0.0254 (6)
H8A	0.9867	0.2055	0.4081	0.03*
H8B	0.9789	0.1212	0.3202	0.03*
O9	1.0295 (3)	0.3905 (2)	0.32453 (12)	0.0305 (4)
H9	0.9902	0.4838	0.348	0.046*

	U11	U22	U33	U12	U13	U23
I1	0.01963 (12)	0.02953 (13)	0.02391 (12)	0.00057 (7)	0.00275 (8)	−0.00027 (6)
C1	0.0296 (16)	0.0386 (16)	0.0173 (14)	−0.0004 (12)	0.0043 (12)	−0.0005 (11)
N2	0.0192 (11)	0.0243 (11)	0.0179 (11)	0.0006 (8)	0.0020 (9)	−0.0003 (8)
C3	0.0170 (14)	0.0308 (15)	0.0277 (15)	0.0020 (11)	0.0027 (11)	0.0000 (11)
C4	0.0147 (13)	0.0310 (14)	0.0242 (14)	0.0011 (10)	0.0029 (11)	0.0007 (10)
N5	0.0154 (11)	0.0256 (11)	0.0176 (11)	0.0004 (8)	0.0017 (9)	−0.0005 (8)
C6	0.0209 (14)	0.0408 (17)	0.0196 (14)	0.0001 (11)	0.0011 (11)	0.0017 (10)
C7	0.0161 (12)	0.0217 (13)	0.0200 (13)	−0.0007 (10)	0.0026 (10)	0.0003 (9)
C8	0.0172 (14)	0.0315 (15)	0.0276 (15)	0.0006 (11)	0.0026 (12)	0.0005 (11)
O9	0.0217 (10)	0.0301 (10)	0.0410 (11)	−0.0052 (9)	0.0133 (8)	−0.0041 (9)

C1—N2	1.464 (4)	N5—C7	1.343 (3)
C1—H1A	0.98	N5—C6	1.468 (4)
C1—H1B	0.98	C6—H6A	0.98
C1—H1C	0.98	C6—H6B	0.98
N2—C7	1.345 (3)	C6—H6C	0.98
N2—C3	1.376 (4)	C7—C8	1.497 (4)
C3—C4	1.357 (4)	C8—O9	1.419 (3)
C3—H3	0.95	C8—H8A	0.99
C4—N5	1.379 (4)	C8—H8B	0.99
C4—H4	0.95	O9—H9	0.84
N2—C1—H1A	109.5	C4—N5—C6	124.6 (2)
N2—C1—H1B	109.5	N5—C6—H6A	109.5
H1A—C1—H1B	109.5	N5—C6—H6B	109.5
N2—C1—H1C	109.5	H6A—C6—H6B	109.5
H1A—C1—H1C	109.5	N5—C6—H6C	109.5
H1B—C1—H1C	109.5	H6A—C6—H6C	109.5
C7—N2—C3	109.5 (2)	H6B—C6—H6C	109.5
C7—N2—C1	125.3 (3)	N5—C7—N2	107.2 (3)
C3—N2—C1	125.2 (3)	N5—C7—C8	127.0 (3)
C4—C3—N2	106.9 (3)	N2—C7—C8	125.7 (3)
C4—C3—H3	126.6	O9—C8—C7	111.6 (2)
N2—C3—H3	126.6	O9—C8—H8A	109.3
C3—C4—N5	107.2 (3)	C7—C8—H8A	109.3
C3—C4—H4	126.4	O9—C8—H8B	109.3
N5—C4—H4	126.4	C7—C8—H8B	109.3
C7—N5—C4	109.3 (2)	H8A—C8—H8B	108
C7—N5—C6	126.1 (3)	C8—O9—H9	109.5
C7—N2—C3—C4	0.1 (3)	C6—N5—C7—C8	0.1 (3)
C1—N2—C3—C4	−178.4 (2)	C3—N2—C7—N5	0.0 (2)
N2—C3—C4—N5	−0.2 (3)	C1—N2—C7—N5	178.48 (18)
C3—C4—N5—C7	0.2 (2)	C3—N2—C7—C8	−178.1 (2)
C3—C4—N5—C6	178.15 (19)	C1—N2—C7—C8	0.3 (3)
C4—N5—C7—N2	−0.1 (2)	N5—C7—C8—O9	−113.9 (3)
C6—N5—C7—N2	−178.06 (18)	N2—C7—C8—O9	63.8 (3)
C4—N5—C7—C8	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···I1	0.84	2.62	3.4504 (18)	169
C1—H1A···O9	0.98	2.55	3.230 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯I1	0.84	2.62	3.4504 (18)	169
C1—H1A⋯O9	0.98	2.55	3.230 (4)	126