2-Hy-droxy-methyl-1,3-dimethyl-1H-benzimidazol-3-ium iodide.

In the cation of the title compound, C10H13N2O(+)·I(-), all non-H atoms, with the exception of the O atom, are essentially coplanar, with a maximum deviation of 0.04 (1) Å. In the crystal, the cations and anions are arranged in layers parallel to (100). The cations are connected to the anions via an O-H⋯I hydrogen bond and there are significant π-π stacking inter-actions between cation layers, with centroid-centroid distances in the range 3.606 (5)-3.630 (5) Å. A weak intra-molecular C-H⋯O hydrogen bond is also observed. The crystal studied was an inversion twin with refined components of 0.52 (5) and 0.48 (5).

Related literature

For applications of this class of compounds, see: Tonelli et al. (2010 ▶); Preston (1974 ▶); Hazelton et al. (1995 ▶); Kucukguzel et al. (2001 ▶); Islam et al. (1991 ▶); Li et al. (2003 ▶); Abboud et al. (2006 ▶). For our previous work on imidazole derivatives, see: Bahnous et al. (2012 ▶); Zama et al. (2013 ▶); Chelghoum et al. (2011 ▶).

Experimental

Crystal data

C10H13N2O+·I−

M = 304.12

Orthorhombic,

a = 6.5690 (7) Å

b = 10.1342 (10) Å

c = 16.9357 (19) Å

V = 1127.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.81 mm−1

T = 150 K

0.14 × 0.13 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.647, T max = 0.747

10018 measured reflections

4002 independent reflections

3243 reflections with I > 2σ(I)

R int = 0.02

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.068

S = 1.05

4002 reflections

131 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −0.72 e Å−3

Absolute structure: Flack (1983 ▶), 1518 Friedel pairs

Absolute structure parameter: 0.48 (5)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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, 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/S1600536813022307/lh5638sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022307/lh5638Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022307/lh5638Isup3.cml

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

C10H13N2O+·I−	F(000) = 592
Mr = 304.12	Dx = 1.792 Mg m−3
Orthorhombic, P21nb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2bc 2a	Cell parameters from 4274 reflections
a = 6.5690 (7) Å	θ = 2.4–34.0°
b = 10.1342 (10) Å	µ = 2.81 mm−1
c = 16.9357 (19) Å	T = 150 K
V = 1127.4 (2) Å3	Cube, colorless
Z = 4	0.14 × 0.13 × 0.12 mm

Bruker APEXII CCD diffractometer	3243 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.02
CCD rotation images, thin slices scans	θmax = 34.2°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→10
Tmin = 0.647, Tmax = 0.747	k = −16→15
10018 measured reflections	l = −26→19
4002 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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0263P)2 + 1.1204P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
4002 reflections	Δρmax = 1.34 e Å−3
131 parameters	Δρmin = −0.72 e Å−3
1 restraint	Absolute structure: Flack (1983), 1518 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.48 (5)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	1.0638 (4)	0.0386 (3)	0.05918 (17)	0.0303 (8)
N1	0.9055 (15)	0.3459 (2)	0.11990 (13)	0.0203 (5)
N2	0.9033 (12)	0.2982 (2)	−0.00606 (12)	0.0168 (5)
C1	0.893 (2)	0.1018 (3)	0.0837 (2)	0.0284 (9)
C2	0.9025 (18)	0.2473 (2)	0.06700 (14)	0.0192 (5)
C3	0.9014 (18)	0.4343 (2)	−0.00046 (14)	0.0165 (5)
C4	0.9022 (15)	0.4649 (2)	0.07953 (15)	0.0179 (6)
C5	0.9046 (16)	0.2214 (3)	−0.07961 (15)	0.0226 (7)
C6	0.893 (2)	0.3340 (3)	0.20631 (18)	0.0326 (11)
C7	0.901 (2)	0.5947 (2)	0.10657 (18)	0.0239 (6)
C8	0.9001 (18)	0.6923 (2)	0.0495 (2)	0.0277 (7)
C9	0.9004 (16)	0.6620 (3)	−0.03096 (19)	0.0255 (7)
C10	0.9028 (14)	0.5327 (2)	−0.05820 (16)	0.0218 (6)
I1	0.3999 (3)	0.08238 (2)	0.21526 (1)	0.0330 (1)
H1	1.15370	0.04750	0.09236	0.0454*
H1A	0.77590	0.06427	0.05712	0.0341*
H1B	0.87606	0.08812	0.13999	0.0341*
H5A	0.98363	0.14266	−0.07223	0.0339*
H5B	0.76764	0.19799	−0.09352	0.0339*
H5C	0.96352	0.27334	−0.12114	0.0339*
H6A	0.83795	0.24932	0.21993	0.0487*
H6B	1.02677	0.34281	0.22861	0.0487*
H6C	0.80648	0.40223	0.22679	0.0487*
H7	0.90136	0.61465	0.16017	0.0287*
H8	0.89907	0.78024	0.06512	0.0333*
H9	0.89902	0.73060	−0.06745	0.0306*
H10	0.90517	0.51273	−0.11180	0.0262*

	U11	U22	U33	U12	U13	U23
O1	0.0335 (14)	0.0250 (11)	0.0324 (14)	0.0107 (11)	−0.0066 (12)	−0.0073 (10)
N1	0.0282 (11)	0.0161 (8)	0.0166 (9)	−0.002 (3)	0.000 (4)	−0.0013 (7)
N2	0.0179 (9)	0.0168 (8)	0.0158 (9)	−0.011 (2)	0.001 (3)	−0.0022 (7)
C1	0.045 (2)	0.0144 (10)	0.0258 (13)	0.009 (3)	0.004 (4)	0.0015 (9)
C2	0.0215 (10)	0.0150 (8)	0.0210 (10)	0.003 (3)	0.003 (5)	−0.0004 (8)
C3	0.0142 (8)	0.0155 (9)	0.0197 (10)	−0.001 (3)	0.001 (5)	−0.0004 (7)
C4	0.0179 (10)	0.0152 (9)	0.0206 (11)	0.006 (3)	−0.003 (4)	−0.0020 (8)
C5	0.0248 (13)	0.0236 (11)	0.0194 (11)	−0.010 (3)	−0.003 (4)	−0.0061 (9)
C6	0.053 (3)	0.0289 (12)	0.0158 (12)	0.003 (4)	−0.001 (4)	−0.0010 (9)
C7	0.0250 (11)	0.0174 (9)	0.0292 (13)	0.005 (4)	0.001 (6)	−0.0065 (9)
C8	0.0222 (11)	0.0130 (9)	0.0480 (17)	0.000 (4)	−0.001 (6)	−0.0015 (10)
C9	0.0183 (11)	0.0205 (10)	0.0377 (15)	−0.008 (3)	−0.003 (5)	0.0089 (10)
C10	0.0188 (10)	0.0226 (10)	0.0240 (12)	0.002 (4)	−0.001 (5)	0.0059 (9)
I1	0.0493 (1)	0.0319 (1)	0.0177 (1)	−0.0001 (3)	−0.0001 (4)	−0.0009 (1)

O1—C1	1.357 (11)	C9—C10	1.389 (4)
O1—H1	0.8200	C1—H1A	0.9700
N1—C4	1.387 (3)	C1—H1B	0.9700
N1—C6	1.471 (4)	C5—H5A	0.9600
N1—C2	1.342 (3)	C5—H5B	0.9600
N2—C3	1.383 (3)	C5—H5C	0.9600
N2—C5	1.469 (3)	C6—H6A	0.9600
N2—C2	1.341 (3)	C6—H6B	0.9600
C1—C2	1.503 (4)	C6—H6C	0.9600
C3—C10	1.397 (3)	C7—H7	0.9300
C3—C4	1.390 (3)	C8—H8	0.9300
C4—C7	1.393 (3)	C9—H9	0.9300
C7—C8	1.383 (4)	C10—H10	0.9300
C8—C9	1.397 (5)
C1—O1—H1	109.00	C2—C1—H1A	109.00
C2—N1—C4	108.6 (2)	C2—C1—H1B	109.00
C2—N1—C6	127.0 (2)	H1A—C1—H1B	108.00
C4—N1—C6	124.1 (2)	N2—C5—H5A	109.00
C2—N2—C3	108.69 (19)	N2—C5—H5B	109.00
C2—N2—C5	125.4 (2)	N2—C5—H5C	109.00
C3—N2—C5	125.9 (2)	H5A—C5—H5B	109.00
O1—C1—C2	111.8 (8)	H5A—C5—H5C	109.00
N1—C2—C1	127.3 (2)	H5B—C5—H5C	109.00
N2—C2—C1	123.5 (2)	N1—C6—H6A	109.00
N1—C2—N2	109.24 (19)	N1—C6—H6B	109.00
N2—C3—C10	131.6 (2)	N1—C6—H6C	109.00
C4—C3—C10	121.5 (2)	H6A—C6—H6B	109.00
N2—C3—C4	106.82 (19)	H6A—C6—H6C	110.00
N1—C4—C7	131.3 (2)	H6B—C6—H6C	109.00
C3—C4—C7	122.1 (2)	C4—C7—H7	122.00
N1—C4—C3	106.66 (19)	C8—C7—H7	122.00
C4—C7—C8	116.5 (3)	C7—C8—H8	119.00
C7—C8—C9	121.6 (2)	C9—C8—H8	119.00
C8—C9—C10	122.1 (3)	C8—C9—H9	119.00
C3—C10—C9	116.2 (2)	C10—C9—H9	119.00
O1—C1—H1A	109.00	C3—C10—H10	122.00
O1—C1—H1B	109.00	C9—C10—H10	122.00
C2—N1—C4—C7	179.2 (12)	C3—N2—C2—C1	176.7 (11)
C6—N1—C4—C7	4.8 (19)	O1—C1—C2—N2	66.5 (13)
C4—N1—C2—N2	1.8 (13)	O1—C1—C2—N1	−115.6 (11)
C6—N1—C2—N2	175.9 (10)	N2—C3—C10—C9	−179.9 (11)
C4—N1—C2—C1	−176.4 (11)	C4—C3—C10—C9	−1.4 (15)
C6—N1—C2—C1	−2 (2)	C10—C3—C4—C7	1.1 (17)
C6—N1—C4—C3	−175.6 (10)	N2—C3—C4—N1	0.3 (12)
C2—N1—C4—C3	−1.2 (12)	N2—C3—C4—C7	179.9 (10)
C5—N2—C2—N1	178.8 (9)	C10—C3—C4—N1	−178.6 (10)
C5—N2—C2—C1	−3.0 (17)	N1—C4—C7—C8	179.2 (11)
C3—N2—C2—N1	−1.6 (13)	C3—C4—C7—C8	−0.4 (17)
C5—N2—C3—C4	−179.6 (9)	C4—C7—C8—C9	0.0 (18)
C2—N2—C3—C10	179.5 (12)	C7—C8—C9—C10	−0.4 (18)
C2—N2—C3—C4	0.8 (12)	C8—C9—C10—C3	1.1 (15)
C5—N2—C3—C10	−0.9 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···I1i	0.8200	2.6600	3.473 (3)	171.00
C5—H5A···O1	0.9600	2.5200	3.170 (5)	125.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯I1i	0.82	2.66	3.473 (3)	171
C5—H5A⋯O1	0.96	2.52	3.170 (5)	125

Symmetry code: (i) .