5,6-Dimethyl-1H-benzimidazol-3-ium nitrate.

The title salt, C9H11N2 (+)·NO3 (-), features a planar cation (r.m.s. for 11 non-H atoms = 0.016 Å). In the crystal, N-H⋯O hydrogen bonds link nitrate and benzimidazole ions into a three-dimensional network.

Related literature

For background to benzimidazole, see: Roderick et al. (1972 ▶). For related crystal structures, see: Lee & Scheidt (1986 ▶), Liu (2012 ▶), Cui et al. (2009 ▶).

Experimental

Crystal data

C9H11N2 +·NO3 −

M = 209.21

Monoclinic,

a = 6.938 (4) Å

b = 14.694 (8) Å

c = 10.379 (6) Å

β = 108.598 (9)°

V = 1002.8 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.29 × 0.27 × 0.22 mm

Data collection

Rigaku R-AXIS Spider diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi 1995 ▶) T min = 0.970, T max = 0.977

5401 measured reflections

1973 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.05

1973 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027578/hg5349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027578/hg5349Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027578/hg5349Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027578/hg5349Isup4.cml

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

C9H11N2+·NO3−	F(000) = 440
Mr = 209.21	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3271 reflections
a = 6.938 (4) Å	θ = 2.5–26.6°
b = 14.694 (8) Å	µ = 0.11 mm−1
c = 10.379 (6) Å	T = 296 K
β = 108.598 (9)°	Block, yellow
V = 1002.8 (10) Å3	0.29 × 0.27 × 0.22 mm
Z = 4

Rigaku R-AXIS Spider diffractometer	1617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	k = −17→18
Tmin = 0.970, Tmax = 0.977	l = −8→12
5401 measured reflections	13 standard reflections every 0 reflections
1973 independent reflections	intensity decay: none

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.1519P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1973 reflections	Δρmax = 0.18 e Å−3
145 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.102 (10)

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
C6	0.3017 (3)	0.52774 (14)	0.13819 (18)	0.0638 (5)
H6A	0.3096	0.5767	0.1965	0.077*
C3	0.2734 (3)	0.38091 (11)	−0.03709 (17)	0.0545 (4)
H3A	0.2625	0.3319	−0.0956	0.065*
N3	0.9477 (2)	0.33163 (9)	0.55623 (14)	0.0615 (4)
C4	0.2174 (2)	0.46728 (10)	−0.08774 (14)	0.0451 (4)
C1	0.4099 (4)	0.27501 (17)	0.1557 (2)	0.0936 (8)
H1A	0.3917	0.2333	0.0816	0.140*
H1B	0.3287	0.2558	0.2102	0.140*
H1C	0.5506	0.2761	0.2104	0.140*
C2	0.3452 (3)	0.36885 (13)	0.10052 (19)	0.0613 (5)
C8	0.4308 (4)	0.4293 (2)	0.3399 (2)	0.1049 (9)
H8A	0.4287	0.4865	0.3839	0.157*
H8B	0.5670	0.4058	0.3678	0.157*
H8C	0.3432	0.3870	0.3647	0.157*
C7	0.3576 (3)	0.44249 (15)	0.18821 (18)	0.0645 (5)
C5	0.2327 (2)	0.53977 (10)	−0.00159 (17)	0.0493 (4)
N2	0.1683 (2)	0.61491 (10)	−0.08221 (17)	0.0609 (4)
C9	0.1169 (3)	0.58998 (12)	−0.20846 (19)	0.0602 (5)
H9A	0.0678	0.6289	−0.2824	0.072*
N1	0.1439 (2)	0.50169 (10)	−0.21736 (13)	0.0519 (4)
O1	0.9388 (3)	0.31136 (10)	0.66814 (13)	0.0858 (5)
O2	1.0253 (3)	0.40438 (9)	0.53833 (14)	0.0857 (5)
O3	0.8828 (3)	0.27846 (9)	0.45932 (13)	0.0829 (5)
H1	0.108 (3)	0.4713 (15)	−0.297 (2)	0.082 (7)*
H2	0.156 (4)	0.6760 (18)	−0.053 (2)	0.097 (7)*

	U11	U22	U33	U12	U13	U23
C6	0.0503 (9)	0.0868 (13)	0.0550 (10)	−0.0109 (9)	0.0176 (7)	−0.0263 (9)
C3	0.0557 (9)	0.0498 (9)	0.0583 (9)	−0.0039 (7)	0.0187 (7)	−0.0015 (7)
N3	0.0792 (10)	0.0433 (7)	0.0533 (8)	0.0036 (7)	0.0090 (7)	0.0041 (6)
C4	0.0417 (8)	0.0517 (8)	0.0436 (7)	−0.0050 (6)	0.0161 (6)	−0.0024 (6)
C1	0.0874 (16)	0.0854 (15)	0.0949 (16)	−0.0108 (12)	0.0109 (12)	0.0373 (12)
C2	0.0511 (9)	0.0712 (11)	0.0599 (10)	−0.0090 (8)	0.0155 (7)	0.0135 (8)
C8	0.0874 (16)	0.175 (3)	0.0469 (11)	−0.0045 (17)	0.0142 (10)	0.0111 (14)
C7	0.0479 (9)	0.0968 (14)	0.0472 (9)	−0.0077 (9)	0.0128 (7)	0.0073 (9)
C5	0.0413 (8)	0.0518 (9)	0.0559 (9)	−0.0042 (6)	0.0172 (6)	−0.0079 (7)
N2	0.0529 (8)	0.0488 (8)	0.0779 (10)	0.0012 (6)	0.0163 (7)	−0.0064 (7)
C9	0.0499 (9)	0.0584 (10)	0.0699 (11)	0.0022 (7)	0.0156 (8)	0.0138 (8)
N1	0.0517 (8)	0.0601 (9)	0.0442 (7)	−0.0023 (6)	0.0157 (6)	−0.0004 (6)
O1	0.1216 (13)	0.0780 (9)	0.0593 (8)	−0.0232 (8)	0.0309 (8)	−0.0002 (7)
O2	0.1434 (14)	0.0470 (7)	0.0653 (9)	−0.0202 (7)	0.0315 (9)	0.0006 (6)
O3	0.1287 (13)	0.0498 (7)	0.0549 (7)	−0.0080 (7)	0.0078 (7)	−0.0012 (6)

C6—C7	1.364 (3)	C1—H1B	0.9600
C6—C5	1.386 (3)	C1—H1C	0.9600
C6—H6A	0.9300	C2—C7	1.399 (3)
C3—C2	1.366 (3)	C8—C7	1.505 (3)
C3—C4	1.381 (2)	C8—H8A	0.9600
C3—H3A	0.9300	C8—H8B	0.9600
N3—O1	1.2197 (19)	C8—H8C	0.9600
N3—O2	1.237 (2)	C5—N2	1.371 (2)
N3—O3	1.2393 (19)	N2—C9	1.296 (2)
C4—C5	1.373 (2)	N2—H2	0.96 (3)
C4—N1	1.374 (2)	C9—N1	1.318 (2)
C1—C2	1.505 (3)	C9—H9A	0.9300
C1—H1A	0.9600	N1—H1	0.90 (2)
C7—C6—C5	118.47 (16)	C7—C8—H8A	109.5
C7—C6—H6A	120.8	C7—C8—H8B	109.5
C5—C6—H6A	120.8	H8A—C8—H8B	109.5
C2—C3—C4	118.80 (16)	C7—C8—H8C	109.5
C2—C3—H3A	120.6	H8A—C8—H8C	109.5
C4—C3—H3A	120.6	H8B—C8—H8C	109.5
O1—N3—O2	120.70 (15)	C6—C7—C2	120.78 (17)
O1—N3—O3	120.23 (15)	C6—C7—C8	118.5 (2)
O2—N3—O3	119.06 (15)	C2—C7—C8	120.7 (2)
C5—C4—N1	106.25 (15)	N2—C5—C4	106.54 (15)
C5—C4—C3	120.73 (15)	N2—C5—C6	132.67 (16)
N1—C4—C3	133.01 (14)	C4—C5—C6	120.79 (16)
C2—C1—H1A	109.5	C9—N2—C5	108.69 (15)
C2—C1—H1B	109.5	C9—N2—H2	124.2 (14)
H1A—C1—H1B	109.5	C5—N2—H2	127.1 (14)
C2—C1—H1C	109.5	N2—C9—N1	110.46 (16)
H1A—C1—H1C	109.5	N2—C9—H9A	124.8
H1B—C1—H1C	109.5	N1—C9—H9A	124.8
C3—C2—C7	120.41 (18)	C9—N1—C4	108.06 (14)
C3—C2—C1	118.79 (19)	C9—N1—H1	123.2 (14)
C7—C2—C1	120.80 (18)	C4—N1—H1	128.6 (14)
C2—C3—C4—C5	−0.2 (2)	C3—C4—C5—N2	179.37 (14)
C2—C3—C4—N1	179.02 (15)	N1—C4—C5—C6	179.55 (13)
C4—C3—C2—C7	1.3 (2)	C3—C4—C5—C6	−1.0 (2)
C4—C3—C2—C1	−178.89 (16)	C7—C6—C5—N2	−179.34 (16)
C5—C6—C7—C2	−0.1 (3)	C7—C6—C5—C4	1.2 (2)
C5—C6—C7—C8	−179.48 (16)	C4—C5—N2—C9	0.16 (18)
C3—C2—C7—C6	−1.1 (3)	C6—C5—N2—C9	−179.36 (17)
C1—C2—C7—C6	179.06 (18)	C5—N2—C9—N1	−0.22 (19)
C3—C2—C7—C8	178.23 (17)	N2—C9—N1—C4	0.19 (18)
C1—C2—C7—C8	−1.6 (3)	C5—C4—N1—C9	−0.09 (16)
N1—C4—C5—N2	−0.04 (16)	C3—C4—N1—C9	−179.40 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.96 (3)	2.31 (3)	3.043 (3)	133.0 (15)
N2—H2···O3i	0.96 (3)	1.86 (3)	2.797 (3)	165 (2)
N1—H1···O1ii	0.90 (3)	2.60 (2)	3.191 (3)	123.8 (17)
N1—H1···O2ii	0.90 (3)	1.89 (2)	2.797 (3)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.96 (3)	2.31 (3)	3.043 (3)	133.0 (15)
N2—H2⋯O3i	0.96 (3)	1.86 (3)	2.797 (3)	165 (2)
N1—H1⋯O1ii	0.90 (3)	2.60 (2)	3.191 (3)	123.8 (17)
N1—H1⋯O2ii	0.90 (3)	1.89 (2)	2.797 (3)	178 (2)

Symmetry codes: (i) ; (ii) .