2-Amino-benzimidazolium hydrogen sulfate.

In the title salt, C(7)H(8)N(3) (+)·HSO(4) (-), the benzimdazole ring system is planar [mean deviation 0.0086 (1) Å]. In the crystal, N-H⋯O and O-H⋯O hydrogen-bond inter-actions give rise to a layer motif.

Related literature

For related compounds, see: El-Medania et al. (2003 ▶); Yeşilel et al. (2008 ▶).

Experimental

Crystal data

C7H8N3 +·HSO4 −

M = 231.23

Monoclinic,

a = 10.855 (6) Å

b = 13.049 (7) Å

c = 7.082 (4) Å

β = 99.025 (7)°

V = 990.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 291 (2) K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.950, T max = 0.968

5083 measured reflections

1841 independent reflections

1408 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 0.96

1841 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041706/ng2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041706/ng2522Isup2.hkl

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

C7H8N3+·HSO4−	F(000) = 480
Mr = 231.23	Dx = 1.550 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1841 reflections
a = 10.855 (6) Å	θ = 1.0–1.0°
b = 13.049 (7) Å	µ = 0.33 mm−1
c = 7.082 (4) Å	T = 291 K
β = 99.025 (7)°	Block, colourless
V = 990.7 (9) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker SMART diffractometer	1841 independent reflections
Radiation source: fine-focus sealed tube	1408 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.950, Tmax = 0.968	k = −11→15
5083 measured reflections	l = −8→8

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0593P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
1841 reflections	Δρmax = 0.23 e Å−3
136 parameters	Δρmin = −0.35 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
C1	0.61393 (19)	0.67017 (16)	0.3926 (3)	0.0400 (5)
C2	0.80252 (18)	0.71967 (16)	0.5357 (3)	0.0387 (5)
C3	0.9247 (2)	0.72581 (18)	0.6229 (3)	0.0483 (6)
H3	0.9725	0.6674	0.6557	0.058*
C4	0.9730 (2)	0.82273 (19)	0.6594 (3)	0.0533 (6)
H4	1.0555	0.8296	0.7178	0.064*
C5	0.9026 (2)	0.91056 (19)	0.6120 (3)	0.0563 (6)
H5	0.9382	0.9746	0.6407	0.068*
C6	0.7787 (2)	0.90386 (17)	0.5216 (3)	0.0497 (6)
H6	0.7310	0.9620	0.4866	0.060*
C7	0.73133 (18)	0.80702 (16)	0.4872 (3)	0.0385 (5)
N1	0.72523 (15)	0.63593 (13)	0.4769 (2)	0.0410 (4)
H1A	0.7460	0.5725	0.4925	0.049*
N2	0.61415 (15)	0.77282 (13)	0.3989 (2)	0.0429 (5)
H2A	0.5521	0.8116	0.3555	0.051*
N3	0.51968 (16)	0.61327 (14)	0.3154 (3)	0.0534 (5)
H3A	0.5265	0.5476	0.3163	0.064*
H3B	0.4511	0.6416	0.2639	0.064*
O1	0.21109 (12)	0.84704 (11)	0.3128 (2)	0.0508 (4)
H1B	0.2450	0.8155	0.4069	0.076*
O2	0.32882 (14)	0.75437 (11)	0.1058 (2)	0.0533 (5)
O3	0.41587 (12)	0.90419 (10)	0.2672 (2)	0.0494 (4)
O4	0.23730 (14)	0.91989 (11)	0.0168 (2)	0.0539 (4)
S1	0.30277 (5)	0.85757 (4)	0.16657 (8)	0.0404 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (11)	0.0385 (12)	0.0414 (12)	0.0044 (9)	0.0057 (10)	−0.0029 (9)
C2	0.0419 (12)	0.0400 (12)	0.0344 (11)	0.0037 (9)	0.0069 (9)	−0.0013 (9)
C3	0.0444 (12)	0.0581 (15)	0.0420 (13)	0.0089 (11)	0.0057 (10)	0.0033 (11)
C4	0.0416 (13)	0.0658 (17)	0.0518 (15)	−0.0066 (11)	0.0051 (11)	−0.0039 (12)
C5	0.0584 (15)	0.0548 (16)	0.0577 (15)	−0.0130 (12)	0.0151 (12)	−0.0092 (12)
C6	0.0537 (14)	0.0407 (13)	0.0552 (15)	0.0009 (10)	0.0103 (12)	−0.0020 (11)
C7	0.0401 (11)	0.0386 (12)	0.0371 (12)	0.0045 (9)	0.0073 (9)	−0.0016 (9)
N1	0.0438 (10)	0.0322 (10)	0.0453 (11)	0.0091 (7)	0.0017 (8)	−0.0001 (7)
N2	0.0404 (10)	0.0343 (10)	0.0520 (12)	0.0109 (7)	0.0013 (8)	−0.0010 (8)
N3	0.0447 (10)	0.0400 (11)	0.0719 (14)	0.0050 (8)	−0.0019 (10)	−0.0067 (10)
O1	0.0408 (8)	0.0495 (10)	0.0611 (10)	0.0055 (7)	0.0047 (8)	0.0063 (7)
O2	0.0640 (10)	0.0331 (9)	0.0582 (10)	0.0091 (7)	−0.0047 (8)	−0.0073 (7)
O3	0.0387 (8)	0.0372 (9)	0.0669 (10)	−0.0035 (6)	−0.0086 (7)	0.0032 (7)
O4	0.0609 (9)	0.0381 (9)	0.0548 (10)	0.0046 (7)	−0.0153 (8)	0.0072 (7)
S1	0.0402 (3)	0.0288 (3)	0.0484 (4)	0.0019 (2)	−0.0045 (2)	0.0007 (2)

C1—N3	1.312 (3)	C6—C7	1.372 (3)
C1—N1	1.338 (2)	C6—H6	0.9300
C1—N2	1.340 (3)	C7—N2	1.400 (2)
C2—C3	1.375 (3)	N1—H1A	0.8600
C2—C7	1.390 (3)	N2—H2A	0.8600
C2—N1	1.401 (3)	N3—H3A	0.8600
C3—C4	1.378 (3)	N3—H3B	0.8600
C3—H3	0.9300	O1—S1	1.5510 (18)
C4—C5	1.389 (3)	O1—H1B	0.8200
C4—H4	0.9300	O2—S1	1.4549 (16)
C5—C6	1.398 (3)	O3—S1	1.4528 (14)
C5—H5	0.9300	O4—S1	1.4336 (15)
N3—C1—N1	126.0 (2)	C6—C7—N2	131.49 (19)
N3—C1—N2	125.21 (19)	C2—C7—N2	106.26 (18)
N1—C1—N2	108.79 (18)	C1—N1—C2	109.21 (17)
C3—C2—C7	121.5 (2)	C1—N1—H1A	125.4
C3—C2—N1	132.04 (19)	C2—N1—H1A	125.4
C7—C2—N1	106.42 (17)	C1—N2—C7	109.28 (16)
C2—C3—C4	116.7 (2)	C1—N2—H2A	125.4
C2—C3—H3	121.7	C7—N2—H2A	125.4
C4—C3—H3	121.7	C1—N3—H3A	120.0
C3—C4—C5	122.2 (2)	C1—N3—H3B	120.0
C3—C4—H4	118.9	H3A—N3—H3B	120.0
C5—C4—H4	118.9	S1—O1—H1B	109.5
C4—C5—C6	120.8 (2)	O4—S1—O3	114.09 (9)
C4—C5—H5	119.6	O4—S1—O2	113.76 (10)
C6—C5—H5	119.6	O3—S1—O2	110.13 (9)
C7—C6—C5	116.5 (2)	O4—S1—O1	104.41 (10)
C7—C6—H6	121.8	O3—S1—O1	106.91 (10)
C5—C6—H6	121.8	O2—S1—O1	106.88 (10)
C6—C7—C2	122.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.86	2.00	2.848 (3)	167
O1—H1B···O2ii	0.82	1.80	2.619 (2)	176
N2—H2A···O3	0.86	1.94	2.795 (2)	177
N3—H3A···O3i	0.86	2.09	2.899 (3)	157
N3—H3B···O2	0.86	2.17	2.987 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.86	2.00	2.848 (3)	167
O1—H1B⋯O2ii	0.82	1.80	2.619 (2)	176
N2—H2A⋯O3	0.86	1.94	2.795 (2)	177
N3—H3A⋯O3i	0.86	2.09	2.899 (3)	157
N3—H3B⋯O2	0.86	2.17	2.987 (2)	158

Symmetry codes: (i) ; (ii) .