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ISSN: 2056-9890

2-Amino­benzimidazolium hydrogen sulfate

aCollege of Sciences, Nanjing University of Technology, Nanjing, 210009, People's Republic of China, and bState Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
*Correspondence e-mail: whuang@nju.edu.cn

(Received 3 December 2008; accepted 9 December 2008; online 13 December 2008)

In the title salt, C7H8N3+·HSO4, the benzimdazole ring system is planar [mean deviation 0.0086 (1) Å]. In the crystal, N—H⋯O and O—H⋯O hydrogen-bond inter­actions give rise to a layer motif.

Related literature

For related compounds, see: El-Medania et al. (2003[El-Medania, S. M., Youssef, T. A. & Ramadan, R. M. (2003). J. Mol. Struct. 644, 77-87.]); Yeşilel et al. (2008[Yeşilel, O. Z., Odabaşoğlu, M. & Büyükgüngör, O. (2008). J. Mol. Struct. 874, 151-158.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N3+·HSO4

  • Mr = 231.23

  • Monoclinic, P 21 /c

  • 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.968

  • 5083 measured reflections

  • 1841 independent reflections

  • 1408 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Several ion-pair adducts of 2-aminobenzimidazole with different organic acids such as picric acid (El-Medania et al., 2003) and squaric acid (YeŞilel et al., 2008) have been reported. Herein, we present a hydrogen sulfate of 2-aminobenzimidazole.

The atom-numbering scheme of the title compound is shown in Fig. 1, while selected bond distances and bond angles are given in Table 1. The benzimidazole skeleton of the title compound is planar and the proton is delocalized within the imidazole ring although it is added to one of the nitrogen atoms. With regard to the hydrogen sulfate anion, the hydrogen atom is added to the O1 atom of SO4 group due to the obviously longer O1–S1 bond length. In the crystal packing, typical π-π stacking can be found between neighbouring aromatic rings with the centroid-to-centroid separation of 3.452 (2) Å. Furthermore, N—H···O and O—H···O hydrogen bonding interactions are found between adjacent molecules to form a three-dimensional network (Fig. 2).

Related literature top

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

Experimental top

The treatment of 2-aminobenzimidazole dissolved in methanol with an excess of hydrochloric acid yields the title compound. Single crystal suitable for X-ray diffraction measurement was obtained after 3 days' slow evaporation of the mother liquid at room temperature in air. Anal. Calcd. For C~7~H~9Ñ~3Õ~4~S: C, 36.36; H, 3.92; O, 27.68%. Found: C, 36.17; H, 4.03; N, 27.74%. Main FT—IR absorptions (KBr pellets, cm-1): 3385 (s), 3194 (m), 1687 (s), 1476 (m), 1286 (m), 1206(s), 1175 (vs), 1070 (m), 1026 (m), 888 (s), and 577 (w).

Refinement top

The non-hydrogen atoms were refined anisotropically, whereas the H atoms bonded with carbon, nitrogen and oxygen atoms were placed in geometrically idealized positions (C—H = 0.93 Å, N—H = 0.86 Å and O—H = 0.82 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(C) and 1.2U~eq~(N) and Uĩso~(H) = 1.5U~eq~(O).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP drawing of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A perspective view of the packing structure of the title compound. Symmetry codes: (i) -x + 1, y - 1/2, -z + 1/2; (ii) x, -y + 3/2, z + 1/2.
2-Aminobenzimidazolium hydrogen sulfate top
Crystal data top
C7H8N3+·HSO4F(000) = 480
Mr = 231.23Dx = 1.550 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1841 reflections
a = 10.855 (6) Åθ = 1.0–1.0°
b = 13.049 (7) ŵ = 0.33 mm1
c = 7.082 (4) ÅT = 291 K
β = 99.025 (7)°Block, colourless
V = 990.7 (9) Å30.16 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART
diffractometer
1841 independent reflections
Radiation source: fine-focus sealed tube1408 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1313
Tmin = 0.950, Tmax = 0.968k = 1115
5083 measured reflectionsl = 88
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-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 reflectionsΔρmax = 0.23 e Å3
136 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0
Crystal data top
C7H8N3+·HSO4V = 990.7 (9) Å3
Mr = 231.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.855 (6) ŵ = 0.33 mm1
b = 13.049 (7) ÅT = 291 K
c = 7.082 (4) Å0.16 × 0.12 × 0.10 mm
β = 99.025 (7)°
Data collection top
Bruker SMART
diffractometer
1841 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1408 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.968Rint = 0.057
5083 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 0.96Δρmax = 0.23 e Å3
1841 reflectionsΔρmin = 0.35 e Å3
136 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.61393 (19)0.67017 (16)0.3926 (3)0.0400 (5)
C20.80252 (18)0.71967 (16)0.5357 (3)0.0387 (5)
C30.9247 (2)0.72581 (18)0.6229 (3)0.0483 (6)
H30.97250.66740.65570.058*
C40.9730 (2)0.82273 (19)0.6594 (3)0.0533 (6)
H41.05550.82960.71780.064*
C50.9026 (2)0.91056 (19)0.6120 (3)0.0563 (6)
H50.93820.97460.64070.068*
C60.7787 (2)0.90386 (17)0.5216 (3)0.0497 (6)
H60.73100.96200.48660.060*
C70.73133 (18)0.80702 (16)0.4872 (3)0.0385 (5)
N10.72523 (15)0.63593 (13)0.4769 (2)0.0410 (4)
H1A0.74600.57250.49250.049*
N20.61415 (15)0.77282 (13)0.3989 (2)0.0429 (5)
H2A0.55210.81160.35550.051*
N30.51968 (16)0.61327 (14)0.3154 (3)0.0534 (5)
H3A0.52650.54760.31630.064*
H3B0.45110.64160.26390.064*
O10.21109 (12)0.84704 (11)0.3128 (2)0.0508 (4)
H1B0.24500.81550.40690.076*
O20.32882 (14)0.75437 (11)0.1058 (2)0.0533 (5)
O30.41587 (12)0.90419 (10)0.2672 (2)0.0494 (4)
O40.23730 (14)0.91989 (11)0.0168 (2)0.0539 (4)
S10.30277 (5)0.85757 (4)0.16657 (8)0.0404 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0399 (11)0.0385 (12)0.0414 (12)0.0044 (9)0.0057 (10)0.0029 (9)
C20.0419 (12)0.0400 (12)0.0344 (11)0.0037 (9)0.0069 (9)0.0013 (9)
C30.0444 (12)0.0581 (15)0.0420 (13)0.0089 (11)0.0057 (10)0.0033 (11)
C40.0416 (13)0.0658 (17)0.0518 (15)0.0066 (11)0.0051 (11)0.0039 (12)
C50.0584 (15)0.0548 (16)0.0577 (15)0.0130 (12)0.0151 (12)0.0092 (12)
C60.0537 (14)0.0407 (13)0.0552 (15)0.0009 (10)0.0103 (12)0.0020 (11)
C70.0401 (11)0.0386 (12)0.0371 (12)0.0045 (9)0.0073 (9)0.0016 (9)
N10.0438 (10)0.0322 (10)0.0453 (11)0.0091 (7)0.0017 (8)0.0001 (7)
N20.0404 (10)0.0343 (10)0.0520 (12)0.0109 (7)0.0013 (8)0.0010 (8)
N30.0447 (10)0.0400 (11)0.0719 (14)0.0050 (8)0.0019 (10)0.0067 (10)
O10.0408 (8)0.0495 (10)0.0611 (10)0.0055 (7)0.0047 (8)0.0063 (7)
O20.0640 (10)0.0331 (9)0.0582 (10)0.0091 (7)0.0047 (8)0.0073 (7)
O30.0387 (8)0.0372 (9)0.0669 (10)0.0035 (6)0.0086 (7)0.0032 (7)
O40.0609 (9)0.0381 (9)0.0548 (10)0.0046 (7)0.0153 (8)0.0072 (7)
S10.0402 (3)0.0288 (3)0.0484 (4)0.0019 (2)0.0045 (2)0.0007 (2)
Geometric parameters (Å, º) top
C1—N31.312 (3)C6—C71.372 (3)
C1—N11.338 (2)C6—H60.9300
C1—N21.340 (3)C7—N21.400 (2)
C2—C31.375 (3)N1—H1A0.8600
C2—C71.390 (3)N2—H2A0.8600
C2—N11.401 (3)N3—H3A0.8600
C3—C41.378 (3)N3—H3B0.8600
C3—H30.9300O1—S11.5510 (18)
C4—C51.389 (3)O1—H1B0.8200
C4—H40.9300O2—S11.4549 (16)
C5—C61.398 (3)O3—S11.4528 (14)
C5—H50.9300O4—S11.4336 (15)
N3—C1—N1126.0 (2)C6—C7—N2131.49 (19)
N3—C1—N2125.21 (19)C2—C7—N2106.26 (18)
N1—C1—N2108.79 (18)C1—N1—C2109.21 (17)
C3—C2—C7121.5 (2)C1—N1—H1A125.4
C3—C2—N1132.04 (19)C2—N1—H1A125.4
C7—C2—N1106.42 (17)C1—N2—C7109.28 (16)
C2—C3—C4116.7 (2)C1—N2—H2A125.4
C2—C3—H3121.7C7—N2—H2A125.4
C4—C3—H3121.7C1—N3—H3A120.0
C3—C4—C5122.2 (2)C1—N3—H3B120.0
C3—C4—H4118.9H3A—N3—H3B120.0
C5—C4—H4118.9S1—O1—H1B109.5
C4—C5—C6120.8 (2)O4—S1—O3114.09 (9)
C4—C5—H5119.6O4—S1—O2113.76 (10)
C6—C5—H5119.6O3—S1—O2110.13 (9)
C7—C6—C5116.5 (2)O4—S1—O1104.41 (10)
C7—C6—H6121.8O3—S1—O1106.91 (10)
C5—C6—H6121.8O2—S1—O1106.88 (10)
C6—C7—C2122.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.862.002.848 (3)167
O1—H1B···O2ii0.821.802.619 (2)176
N2—H2A···O30.861.942.795 (2)177
N3—H3A···O3i0.862.092.899 (3)157
N3—H3B···O20.862.172.987 (2)158
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC7H8N3+·HSO4
Mr231.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)10.855 (6), 13.049 (7), 7.082 (4)
β (°) 99.025 (7)
V3)990.7 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.16 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.950, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
5083, 1841, 1408
Rint0.057
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.103, 0.96
No. of reflections1841
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.35

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.862.002.848 (3)167
O1—H1B···O2ii0.821.802.619 (2)176
N2—H2A···O30.861.942.795 (2)177
N3—H3A···O3i0.862.092.899 (3)157
N3—H3B···O20.862.172.987 (2)158
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+3/2, z+1/2.
 

Footnotes

Additional correspondence author.

Acknowledgements

WH acknowledges the National Natural Science Foundation of China (No. 20871065) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, for financial aid.

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEl-Medania, S. M., Youssef, T. A. & Ramadan, R. M. (2003). J. Mol. Struct. 644, 77–87.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYeşilel, O. Z., Odabaşoğlu, M. & Büyükgüngör, O. (2008). J. Mol. Struct. 874, 151–158.  Google Scholar

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