2-Methyl-5,6-dinitro-benzimidazolium chloride.

In the title compound, C(8)H(7)N(4)O(4) (+)·Cl(-), the cation possesses twofold symmetry, with the twofold axis bis-ecting the 2-methyl-5,6-dinitro-benzimidazolium cation. The methyl H atoms are disordered about this twofold axis and were assigned equal half-occupancies. The chloride anion also lies on a twofold axis. In the crystal, N-H⋯Cl and C-H⋯O hydrogen bonds link the ions to form a three-dimensional network.

Related literature

For literature on the anti­tumour, anthelmintic, anti­bacterial, virucidal and fungicidal properties of benzimidazole derivatives, see: Refaat (2010 ▶); Laryea et al. (2010 ▶); Horton et al. (2003 ▶); Spasov et al. (1999 ▶); Soula & Luu-Duc (1986 ▶). For literature on the coordination and corrosion inhibitor abilities of the benzimidazoles, see: Kuznetsov & Kaza­nsky (2008 ▶); Subramanyam & Mayanna (1985 ▶). For literature on the use of benzimidazole derivatives as photographic materials and dyes, see: Hoffmann et al. (2011 ▶); Alamgir et al. (2007 ▶). For a related structure, see: Hökelek et al. (2002 ▶).

Experimental

Crystal data

C8H7N4O4 +·Cl−

M = 258.63

Orthorhombic,

a = 4.9453 (1) Å

b = 20.4691 (4) Å

c = 10.4543 (3) Å

V = 1058.25 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 100 K

0.46 × 0.40 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.848, T max = 0.929

3043 measured reflections

1302 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.11

1302 reflections

83 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 517 Friedel pairs

Flack parameter: 0.10 (6)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008105/su2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008105/su2261Isup2.hkl

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

C8H7N4O4+·Cl−	F(000) = 528
Mr = 258.63	Dx = 1.623 Mg m−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 2425 reflections
a = 4.9453 (1) Å	θ = 2.8–28.2°
b = 20.4691 (4) Å	µ = 0.37 mm−1
c = 10.4543 (3) Å	T = 100 K
V = 1058.25 (4) Å3	Block, yellow
Z = 4	0.46 × 0.40 × 0.20 mm

Bruker Kappa APEXII CCD area-detector diffractometer	1302 independent reflections
Radiation source: fine-focus sealed tube	1264 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.848, Tmax = 0.929	k = −20→26
3043 measured reflections	l = −13→13

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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.4282P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1302 reflections	Δρmax = 0.27 e Å−3
83 parameters	Δρmin = −0.16 e Å−3
0 restraints	Absolute structure: Flack (1983), 517 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (6)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cl1	0.38240 (8)	0.0000	0.5000	0.02165 (12)
O1	0.9799 (2)	0.31462 (5)	0.62135 (10)	0.0235 (2)
O2	0.5726 (2)	0.27552 (5)	0.60594 (10)	0.0234 (2)
N1	0.8093 (2)	0.27227 (6)	0.64031 (11)	0.0174 (2)
N2	0.8329 (2)	0.03251 (5)	0.68250 (10)	0.0133 (2)
H2A	0.712 (4)	0.0200 (10)	0.628 (2)	0.035 (6)*
C1	0.8975 (3)	0.21173 (6)	0.70323 (11)	0.0143 (2)
C2	0.7865 (3)	0.15455 (7)	0.65679 (12)	0.0146 (3)
H2	0.6486	0.1545	0.5963	0.018*
C3	0.8933 (3)	0.09724 (6)	0.70596 (11)	0.0124 (2)
C4	1.0000	−0.00475 (10)	0.7500	0.0143 (3)
C5	1.0000	−0.07722 (10)	0.7500	0.0207 (4)
H5A	0.8609	−0.0929	0.6937	0.031*	0.50
H5B	0.9666	−0.0929	0.8351	0.031*	0.50
H5C	1.1726	−0.0929	0.7211	0.031*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.01317 (19)	0.0379 (3)	0.01385 (18)	0.000	0.000	−0.00422 (19)
O1	0.0284 (5)	0.0159 (5)	0.0261 (5)	−0.0007 (4)	0.0058 (4)	0.0042 (4)
O2	0.0231 (5)	0.0213 (5)	0.0259 (5)	0.0069 (4)	−0.0046 (4)	0.0017 (4)
N1	0.0222 (6)	0.0145 (5)	0.0156 (5)	0.0036 (5)	0.0015 (4)	0.0010 (4)
N2	0.0137 (5)	0.0129 (5)	0.0133 (5)	−0.0011 (4)	0.0006 (4)	−0.0010 (4)
C1	0.0145 (6)	0.0127 (6)	0.0157 (5)	0.0026 (5)	0.0030 (5)	0.0019 (4)
C2	0.0133 (5)	0.0169 (6)	0.0137 (5)	0.0015 (5)	0.0000 (4)	0.0009 (5)
C3	0.0129 (5)	0.0125 (6)	0.0117 (5)	−0.0009 (5)	0.0026 (5)	−0.0007 (4)
C4	0.0145 (7)	0.0154 (9)	0.0131 (7)	0.000	0.0035 (6)	0.000
C5	0.0250 (10)	0.0110 (9)	0.0261 (10)	0.000	0.0025 (8)	0.000

N1—O1	1.2259 (16)	C2—H2	0.9300
N1—O2	1.2260 (16)	C3—C3i	1.401 (3)
N1—C1	1.4692 (17)	C4—N2	1.3275 (16)
N2—C3	1.3801 (16)	C4—N2i	1.3275 (16)
N2—H2A	0.86 (2)	C4—C5	1.483 (3)
C1—C1i	1.409 (3)	C5—H5A	0.9600
C2—C1	1.3808 (18)	C5—H5B	0.9600
C2—C3	1.3855 (18)	C5—H5C	0.9600
O1—N1—O2	124.84 (12)	N2—C3—C2	131.66 (12)
O1—N1—C1	117.67 (11)	N2—C3—C3i	106.24 (7)
O2—N1—C1	117.41 (11)	C2—C3—C3i	122.08 (8)
C3—N2—H2A	123.5 (14)	N2i—C4—N2	109.87 (17)
C4—N2—C3	108.82 (12)	N2i—C4—C5	125.07 (9)
C4—N2—H2A	127.6 (14)	N2—C4—C5	125.07 (9)
C1i—C1—N1	121.63 (7)	C4—C5—H5A	109.5
C2—C1—N1	116.07 (11)	C4—C5—H5B	109.5
C2—C1—C1i	122.02 (8)	C4—C5—H5C	109.5
C1—C2—C3	115.83 (12)	H5A—C5—H5B	109.5
C1—C2—H2	122.1	H5A—C5—H5C	109.5
C3—C2—H2	122.1	H5B—C5—H5C	109.5
O1—N1—C1—C1i	33.8 (2)	C3—C2—C1—N1	172.73 (11)
O1—N1—C1—C2	−140.30 (13)	C3—C2—C1—C1i	−1.3 (2)
O2—N1—C1—C1i	−149.18 (15)	C1—C2—C3—N2	179.82 (13)
O2—N1—C1—C2	36.76 (17)	C1—C2—C3—C3i	−2.1 (2)
C4—N2—C3—C2	177.52 (13)	N2i—C4—N2—C3	0.32 (6)
C4—N2—C3—C3i	−0.81 (16)	C5—C4—N2—C3	−179.68 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86 (2)	2.15 (2)	3.008 (1)	172.5 (18)
C2—H2···O1ii	0.93	2.51	3.339 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.86 (2)	2.15 (2)	3.008 (1)	172.5 (18)
C2—H2⋯O1i	0.93	2.51	3.339 (2)	150

Symmetry code: (i) .