2-Methyl-benzimidazolium nitrate.

In the title compound, C(8)H(9)N(2) (+)·NO(3) (-), inter-molecular N-H⋯O hydrogen bonds join the mol-ecules into a chain extending along the b axis.

Related literature

For the applications of related benzimidazole compounds, see: Wright (1951 ▶); El-masry et al. (2000 ▶); Gümüş et al. (2003 ▶).

Experimental

Crystal data

C8H9N2 +·NO3 −

M = 195.18

Monoclinic,

a = 7.711 (4) Å

b = 15.127 (7) Å

c = 8.270 (4) Å

β = 99.398 (7)°

V = 951.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.981, T max = 0.987

4774 measured reflections

1685 independent reflections

1319 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.07

1685 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008615/gk2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008615/gk2255Isup2.hkl

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

C8H9N2+·NO3−	F(000) = 408
Mr = 195.18	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2174 reflections
a = 7.711 (4) Å	θ = 2.5–25.5°
b = 15.127 (7) Å	µ = 0.11 mm−1
c = 8.270 (4) Å	T = 298 K
β = 99.398 (7)°	Block, colorless
V = 951.7 (8) Å3	0.18 × 0.16 × 0.12 mm
Z = 4

Bruker SMART APEX diffractometer	1685 independent reflections
Radiation source: fine-focus sealed tube	1319 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.981, Tmax = 0.987	k = −11→18
4774 measured reflections	l = −9→9

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3
1685 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > 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	0.3641 (2)	0.06287 (10)	0.78462 (18)	0.0735 (5)
O2	0.33057 (19)	0.15524 (9)	0.97555 (17)	0.0643 (4)
O3	0.2248 (3)	0.02349 (11)	0.9773 (2)	0.0915 (6)
N1	0.3063 (2)	0.07987 (10)	0.9136 (2)	0.0538 (4)
N2	0.6679 (2)	0.12445 (11)	0.25067 (19)	0.0600 (5)
H2	0.6828	0.0687	0.2374	0.072*
N3	0.5577 (2)	0.24731 (11)	0.31726 (19)	0.0576 (5)
H3	0.4889	0.2842	0.3542	0.069*
C1	0.3941 (3)	0.11166 (15)	0.3743 (3)	0.0727 (6)
H1A	0.3921	0.0516	0.3368	0.109*
H1B	0.2839	0.1395	0.3331	0.109*
H1C	0.4132	0.1126	0.4920	0.109*
C2	0.5376 (3)	0.15990 (13)	0.3145 (2)	0.0569 (5)
C3	0.7769 (3)	0.19049 (13)	0.2083 (2)	0.0561 (5)
C4	0.7057 (3)	0.26993 (13)	0.2519 (2)	0.0542 (5)
C5	0.7834 (3)	0.35057 (14)	0.2303 (3)	0.0677 (6)
H5	0.7356	0.4035	0.2595	0.081*
C6	0.9355 (3)	0.34816 (19)	0.1630 (3)	0.0805 (7)
H6	0.9920	0.4009	0.1463	0.097*
C7	1.0070 (3)	0.2684 (2)	0.1191 (3)	0.0802 (7)
H7	1.1095	0.2695	0.0734	0.096*
C8	0.9302 (3)	0.18829 (18)	0.1416 (3)	0.0715 (7)
H8	0.9787	0.1353	0.1134	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.1006 (12)	0.0560 (9)	0.0718 (10)	0.0061 (8)	0.0370 (9)	−0.0048 (7)
O2	0.0865 (10)	0.0434 (8)	0.0651 (9)	−0.0085 (7)	0.0188 (7)	−0.0067 (6)
O3	0.1307 (16)	0.0554 (10)	0.0990 (13)	−0.0287 (10)	0.0499 (12)	0.0017 (8)
N1	0.0628 (10)	0.0406 (9)	0.0590 (10)	0.0020 (7)	0.0127 (8)	0.0042 (7)
N2	0.0735 (11)	0.0464 (9)	0.0564 (10)	0.0153 (8)	−0.0006 (8)	−0.0086 (7)
N3	0.0710 (11)	0.0476 (10)	0.0521 (9)	0.0150 (8)	0.0038 (8)	−0.0094 (7)
C1	0.0902 (16)	0.0612 (14)	0.0673 (13)	0.0017 (12)	0.0145 (12)	−0.0006 (11)
C2	0.0728 (13)	0.0487 (12)	0.0462 (10)	0.0126 (10)	0.0004 (9)	−0.0052 (8)
C3	0.0621 (12)	0.0575 (12)	0.0440 (10)	0.0131 (10)	−0.0051 (8)	−0.0086 (9)
C4	0.0619 (11)	0.0536 (11)	0.0433 (10)	0.0096 (9)	−0.0024 (8)	−0.0058 (8)
C5	0.0810 (15)	0.0539 (13)	0.0631 (13)	0.0037 (11)	−0.0033 (11)	−0.0019 (10)
C6	0.0806 (16)	0.0842 (18)	0.0716 (15)	−0.0133 (14)	−0.0030 (12)	0.0061 (13)
C7	0.0679 (14)	0.105 (2)	0.0662 (14)	0.0061 (14)	0.0070 (11)	−0.0032 (14)
C8	0.0685 (14)	0.0831 (17)	0.0593 (13)	0.0169 (13)	−0.0007 (11)	−0.0124 (11)

O1—N1	1.248 (2)	C1—H1C	0.9600
O2—N1	1.252 (2)	C3—C8	1.384 (3)
O3—N1	1.228 (2)	C3—C4	1.393 (3)
N2—C2	1.322 (3)	C4—C5	1.383 (3)
N2—C3	1.387 (3)	C5—C6	1.378 (4)
N2—H2	0.8600	C5—H5	0.9300
N3—C2	1.331 (3)	C6—C7	1.399 (4)
N3—C4	1.383 (3)	C6—H6	0.9300
N3—H3	0.8600	C7—C8	1.374 (4)
C1—C2	1.476 (3)	C7—H7	0.9300
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600
O3—N1—O1	120.19 (17)	C8—C3—N2	132.5 (2)
O3—N1—O2	120.66 (17)	C8—C3—C4	121.5 (2)
O1—N1—O2	119.14 (16)	N2—C3—C4	105.96 (18)
C2—N2—C3	109.90 (17)	C5—C4—N3	132.13 (19)
C2—N2—H2	125.1	C5—C4—C3	122.0 (2)
C3—N2—H2	125.1	N3—C4—C3	105.85 (18)
C2—N3—C4	109.90 (16)	C6—C5—C4	116.3 (2)
C2—N3—H3	125.1	C6—C5—H5	121.8
C4—N3—H3	125.1	C4—C5—H5	121.8
C2—C1—H1A	109.5	C5—C6—C7	121.7 (2)
C2—C1—H1B	109.5	C5—C6—H6	119.2
H1A—C1—H1B	109.5	C7—C6—H6	119.2
C2—C1—H1C	109.5	C8—C7—C6	121.9 (2)
H1A—C1—H1C	109.5	C8—C7—H7	119.1
H1B—C1—H1C	109.5	C6—C7—H7	119.1
N2—C2—N3	108.40 (19)	C7—C8—C3	116.6 (2)
N2—C2—C1	126.37 (19)	C7—C8—H8	121.7
N3—C2—C1	125.23 (19)	C3—C8—H8	121.7
C3—N2—C2—N3	−0.6 (2)	C8—C3—C4—N3	−178.53 (17)
C3—N2—C2—C1	179.86 (19)	N2—C3—C4—N3	−0.24 (19)
C4—N3—C2—N2	0.4 (2)	N3—C4—C5—C6	178.52 (19)
C4—N3—C2—C1	179.99 (19)	C3—C4—C5—C6	0.0 (3)
C2—N2—C3—C8	178.5 (2)	C4—C5—C6—C7	0.0 (3)
C2—N2—C3—C4	0.5 (2)	C5—C6—C7—C8	−0.4 (4)
C2—N3—C4—C5	−178.8 (2)	C6—C7—C8—C3	0.7 (3)
C2—N3—C4—C3	−0.1 (2)	N2—C3—C8—C7	−178.4 (2)
C8—C3—C4—C5	0.3 (3)	C4—C3—C8—C7	−0.7 (3)
N2—C3—C4—C5	178.59 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.03	2.855 (3)	162
N3—H3···O2ii	0.86	1.93	2.775 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.03	2.855 (3)	162
N3—H3⋯O2ii	0.86	1.93	2.775 (2)	166

Symmetry codes: (i) ; (ii) .