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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2913.
Published online 2010 October 23. doi:  10.1107/S1600536810042145
PMCID: PMC3009281

2-Methyl­benzimidazolium thio­cyanate

Abstract

In the crystal structure of the title compound, C8H9N2 +·SCN, the nearly planar 2-methyl­benzimidazolium cation [r.m.s. deviation = 0.0123 (4) Å] is perpendicular to a mirror plane and the methyl H atoms are disordered about the mirror plane with equal occupancies. The thio­cyanate anion also lies on a mirror plane. N—H(...)N hydrogen bonds link the components into an infinite chain along the b axis.

Related literature

For related structures, see: Bhattacharya et al. (2004 [triangle]); Ding et al. (2004 [triangle]); Shaker et al. (2010 [triangle]); Huang et al. (2006 [triangle]). For the application of benzimidazole derivatives in crystal engineering, see: Cai et al. (2002 [triangle]). For the biological properties of benzimidazole derivatives, see: Refaat (2010 [triangle]); Ansari & Lal (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2913-scheme1.jpg

Experimental

Crystal data

  • C8H9N2 +·SCN
  • M r = 191.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2913-efi2.jpg
  • a = 9.879 (2) Å
  • b = 7.2157 (15) Å
  • c = 12.890 (3) Å
  • V = 918.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 100 K
  • 0.40 × 0.29 × 0.15 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.888, T max = 0.956
  • 10495 measured reflections
  • 1133 independent reflections
  • 1000 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.090
  • S = 1.01
  • 1133 reflections
  • 71 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042145/is2616sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042145/is2616Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (UMRG grant RG024/09BIO).

supplementary crystallographic information

Comment

Benzimidazoles are a class of compounds with a wide variety of biological properties (Refaat, 2010; Ansari & Lal, 2009) and applications in crystal-engineering (Cai et al., 2002). During our studies on coordination behavior of 2-methylbenzimidazole, the title crystal was obtained unexpectedly as a by-product. The structures of several compounds similar to present structure have been reported (Bhattacharya et al., 2004; Ding et al., 2004; Shaker et al., 2010; Huang et al., 2006).

The asymmetric unit of the title compound, contains one-half molecule of each component. The nearly planar 2-methylbenzimidazolium moiety (r.m.s = 0.0123 Å) is perpendicular to, and the thiocyanate ion lies on a mirror plane. In the crystal structure, an N—H···N hydrogen bond links the molecules into an infinite chain along the b axis.

Experimental

An ethanolic solution (12 ml) of 2-methylbenzimidazole (5 mmol, 0.78 g) was added to an aqueous solution (10 ml) of CuCl2. 2H2O (0.5 g, 2 mmol) followed by addition of an aqueous solution (10 ml) of KSCN (5 mmol).The resulting precipitates were filtered off. The colorless crystals of the title compound were obtained from the filtrate.

Refinement

The C-bound hydrogen atoms were placed at calculated positions (C—H 0.95 or 0.98 Å) and were treated as riding on their parent atoms, with Uiso(H) set to 1.2 or 1.5 Ueq(C). The N-bound hydrogen atom was located in a difference Fourier map and refined with a distance restraint of N—H 0.88 (2) Å.

Figures

Fig. 1.
Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabelled atoms are generated by the symmetry operation (x, –y + 3/2, z).

Crystal data

C8H9N2+·SCNF(000) = 400
Mr = 191.25Dx = 1.382 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 4285 reflections
a = 9.879 (2) Åθ = 2.6–30.3°
b = 7.2157 (15) ŵ = 0.31 mm1
c = 12.890 (3) ÅT = 100 K
V = 918.9 (3) Å3Block, colorless
Z = 40.40 × 0.29 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer1133 independent reflections
Radiation source: fine-focus sealed tube1000 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.888, Tmax = 0.956k = −9→9
10495 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0395P)2 + 0.9286P] where P = (Fo2 + 2Fc2)/3
1133 reflections(Δ/σ)max < 0.001
71 parametersΔρmax = 0.39 e Å3
1 restraintΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
S1−0.11964 (6)0.25000.31732 (5)0.02094 (18)
N10.15210 (19)0.25000.37930 (15)0.0193 (4)
C10.0383 (2)0.25000.35335 (17)0.0162 (4)
H20.2584 (17)0.485 (2)0.3813 (13)0.019*
N20.28838 (12)0.60009 (17)0.38143 (10)0.0155 (3)
C20.0609 (2)0.75000.38575 (17)0.0191 (5)
H2A0.02770.87790.38250.029*0.50
H2B0.02990.69220.45030.029*0.50
H2BA0.02580.68000.32640.029*0.50
C30.2103 (2)0.75000.38283 (15)0.0156 (4)
C40.42343 (15)0.6534 (2)0.37939 (11)0.0148 (3)
C50.54317 (15)0.5525 (2)0.37848 (11)0.0179 (3)
H50.54320.42090.37740.022*
C60.66199 (15)0.6529 (2)0.37921 (11)0.0189 (3)
H60.74600.58870.37970.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0159 (3)0.0182 (3)0.0287 (3)0.000−0.0020 (2)0.000
N10.0179 (9)0.0140 (9)0.0260 (10)0.0000.0024 (7)0.000
C10.0200 (10)0.0105 (9)0.0182 (10)0.0000.0034 (8)0.000
N20.0169 (6)0.0104 (6)0.0191 (6)−0.0018 (5)0.0000 (5)0.0004 (5)
C20.0170 (10)0.0192 (11)0.0211 (11)0.0000.0015 (8)0.000
C30.0193 (10)0.0151 (10)0.0126 (9)0.000−0.0012 (8)0.000
C40.0168 (7)0.0141 (7)0.0135 (6)−0.0007 (6)−0.0004 (5)0.0004 (5)
C50.0215 (7)0.0126 (7)0.0197 (7)0.0023 (6)−0.0015 (6)−0.0003 (6)
C60.0175 (7)0.0200 (8)0.0193 (7)0.0026 (6)−0.0007 (6)0.0001 (6)

Geometric parameters (Å, °)

S1—C11.628 (2)C2—H2BA0.9800
N1—C11.173 (3)C4—C51.389 (2)
N2—C31.3289 (18)C4—C4i1.394 (3)
N2—C41.3888 (19)C5—C61.379 (2)
N2—H20.881 (15)C5—H50.9500
C2—C31.477 (3)C6—C6i1.401 (3)
C2—H2A0.9800C6—H60.9500
C2—H2B0.9800
N1—C1—S1180.0 (2)N2—C3—C2125.52 (9)
C3—N2—C4109.44 (13)N2—C4—C5132.32 (14)
C3—N2—H2124.8 (12)N2—C4—C4i106.08 (8)
C4—N2—H2125.7 (12)C5—C4—C4i121.60 (9)
C3—C2—H2A109.5C6—C5—C4116.72 (15)
C3—C2—H2B109.5C6—C5—H5121.6
H2A—C2—H2B109.5C4—C5—H5121.6
C3—C2—H2BA109.5C5—C6—C6i121.67 (9)
H2A—C2—H2BA109.5C5—C6—H6119.2
H2B—C2—H2BA109.5C6i—C6—H6119.2
N2—C3—N2i108.97 (18)

Symmetry codes: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N10.88 (2)2.00 (2)2.8627 (16)168 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2616).

References

  • Ansari, K. F. & Lal, C. (2009). J. Chem. Sci.121, 1017–1025.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bhattacharya, R., Chanda, S., Bocelli, G., Cantoni, A. & Ghosh, A. (2004). J. Chem. Crystallogr.34, 393–400.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cai, C.-X., Tian, Y.-Q., Li, Y.-Z. & You, X.-Z. (2002). Acta Cryst. C58, m459–m460. [PubMed]
  • Ding, C.-F., Zhang, S.-S., Li, X.-M., Xu, H. & Ouyang, P.-K. (2004). Acta Cryst. E60, o2441–o2443.
  • Refaat, H. M. (2010). Eur. J. Med. Chem.45, 2949–2956. [PubMed]
  • A. Shaker, S., Khaledi, H. & Mohd Ali, H. (2010). Acta Cryst. E66, o2291. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Huang, X., Liu, J.-G. & Xu, D.-J. (2006). Acta Cryst. E62, o1833–o1835.

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