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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m674.
Published online 2009 May 23. doi:  10.1107/S1600536809018935
PMCID: PMC2969637

2-(3-Pyridinio)benzimidazolium penta­chloridoanti­monate(III) monohydrate

Abstract

In the title compound, (C12H11N3)[SbCl5]·H2O, the SbIII centre is surrounded by five Cl atoms and displays a distorted square-pyramidal coordination geometry. The dihedral angle formed by the plane of the imidazole ring system with the pyridine ring is 4.380 (15)°. The crystal structure is stabilized by N—H(...)Cl, O—H(...)Cl and N—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For the pharmacologic activity of benzimidazole derivatives, see: Minoura et al. (2004 [triangle]); Pawar et al. (2004 [triangle]); Demirayak et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m674-scheme1.jpg

Experimental

Crystal data

  • (C12H11N3)[SbCl5]·H2O
  • M r = 514.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m674-efi1.jpg
  • a = 9.2619 (19) Å
  • b = 13.425 (3) Å
  • c = 14.380 (3) Å
  • β = 102.27 (3)°
  • V = 1747.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.35 mm−1
  • T = 293 K
  • 0.25 × 0.22 × 0.19 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.892, T max = 0.964 (expected range = 0.592–0.640)
  • 15623 measured reflections
  • 3410 independent reflections
  • 3037 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.068
  • S = 0.93
  • 3410 reflections
  • 199 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018935/rz2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018935/rz2324Isup2.hkl

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

Acknowledgments

HJX acknowledges a start-up grant from Southeast University, China.

supplementary crystallographic information

Comment

Benzimidazole and its derivatives have received great attention owing to their pharmacologic activities, such as antidiabetic (Minoura et al., 2004), antifungal (Pawar et al.,2004), and anticancer (Demirayak et al., 2002) activities. In this paper, the crystal structure of the title compound is reported.

The asymmetric unit of the title compound (Fig. 1) contains a 2-(3'-pyridinio)benzimidazolium dication, a pentachloroantimonate dianion and a water molecule. In the anion, the antimony(III) atom is coordinated by five chloride anions in a distorted square-pyramidal geometry. The Sb—Cl distances are in the range 2.3687 (10)- 2.7522 (11) Å. In the cation, the pyridine ring and the imidazole ring system are nearly coplanar, the dihedral angle they form being 4.360 (15)°. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O, N—H···C and O—H···Cl hydrogen bonds (Table 1), resulting in the formation of a three-dimensional network.

Experimental

To a mixture of 2-(3'-pyridyl)benzimidazole (0.1 mmol) and water (7 ml), concentrated hydrochloric acid (12 M) was added dropwise till complete dissolution of the solid phase. Concentrated hydrochloric acid was similarly added dropwise to dissolve the solid phase persisting in a mixture of antimony trichloride (0.3 mmol) and water (7 ml). The two solutions were then mixed and stirred for 20 minutes. The resulting precipitate was filtered off and dissolved in hydrochloric acid. Colourless crystals suitable for X-ray analysis were formed after several weeks on slow evaporation of the solvent at room temperature.

Refinement

H atoms bound to C and N atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å, N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C, N). Water H atoms were located in a difference Fourier map and refined with O—H = 0.85 Å and with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Packing diagram of the title compound, showing the structure along the c axis. Intermolecular H bonds are shown as dashed lines.

Crystal data

(C12H11N3)[SbCl5]·H2OF(000) = 1000
Mr = 514.25Dx = 1.955 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1647 reflections
a = 9.2619 (19) Åθ = 3.0–27.6°
b = 13.425 (3) ŵ = 2.35 mm1
c = 14.380 (3) ÅT = 293 K
β = 102.27 (3)°Prism, colourless
V = 1747.2 (7) Å30.25 × 0.22 × 0.19 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3410 independent reflections
Radiation source: fine-focus sealed tube3037 reflections with I > 2σ(I)
graphiteRint = 0.043
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −16→16
Tmin = 0.892, Tmax = 0.964l = −17→17
15623 measured reflections

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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 0.93w = 1/[σ2(Fo2) + (0.0319P)2 + 2.5497P] where P = (Fo2 + 2Fc2)/3
3410 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.32 e Å3
6 restraintsΔρmin = −0.47 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*/Ueq
Sb10.98691 (2)0.410246 (16)0.112742 (15)0.02964 (9)
Cl10.98813 (10)0.24807 (7)0.17778 (7)0.0451 (2)
Cl21.06091 (10)0.48665 (7)0.29163 (6)0.0446 (2)
Cl30.93983 (10)0.34774 (8)−0.06139 (6)0.0445 (2)
Cl41.25689 (10)0.38926 (8)0.11321 (8)0.0516 (3)
Cl50.68651 (10)0.39170 (8)0.09585 (6)0.0434 (2)
C10.5091 (3)0.3717 (2)0.4685 (2)0.0280 (7)
C20.4622 (4)0.3711 (3)0.3703 (2)0.0346 (7)
H2A0.36310.36420.34090.042*
C30.5715 (4)0.3813 (3)0.3187 (3)0.0412 (9)
H3A0.54570.38040.25260.049*
C40.7199 (4)0.3929 (3)0.3638 (3)0.0463 (10)
H4A0.79010.39890.32650.056*
C50.7658 (4)0.3958 (3)0.4611 (3)0.0433 (9)
H5A0.86460.40460.49050.052*
C60.6566 (4)0.3849 (2)0.5131 (2)0.0304 (7)
C70.5252 (3)0.3714 (2)0.6244 (2)0.0280 (7)
C80.4838 (4)0.3694 (2)0.7169 (2)0.0289 (7)
C90.5913 (4)0.3773 (3)0.7992 (2)0.0376 (8)
H9A0.69060.38120.79630.045*
N30.5509 (4)0.3794 (2)0.8830 (2)0.0421 (7)
H3B0.61900.38410.93380.051*
C110.4115 (5)0.3745 (3)0.8920 (3)0.0417 (9)
H11A0.38910.37760.95200.050*
C120.3373 (4)0.3627 (3)0.7250 (2)0.0364 (8)
H12A0.26300.35660.67050.044*
N10.4320 (3)0.3631 (2)0.54084 (18)0.0285 (6)
H1A0.33830.35380.53280.034*
N20.6611 (3)0.3840 (2)0.6097 (2)0.0335 (6)
H2B0.73960.39050.65360.040*
C100.3011 (4)0.3649 (3)0.8128 (3)0.0407 (8)
H10A0.20310.35990.81820.049*
O1W0.1429 (3)0.3470 (2)0.4754 (2)0.0636 (9)
H1WA0.12600.38920.43030.076*
H1WB0.09510.29250.46760.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sb10.02958 (13)0.02996 (14)0.02782 (13)−0.00150 (9)0.00262 (9)0.00183 (9)
Cl10.0391 (5)0.0362 (5)0.0563 (6)−0.0002 (4)0.0014 (4)0.0136 (4)
Cl20.0442 (5)0.0505 (5)0.0366 (5)−0.0094 (4)0.0033 (4)−0.0069 (4)
Cl30.0465 (5)0.0524 (6)0.0302 (4)0.0073 (4)−0.0016 (4)−0.0029 (4)
Cl40.0338 (5)0.0687 (7)0.0536 (6)−0.0061 (4)0.0121 (4)−0.0013 (5)
Cl50.0362 (5)0.0638 (6)0.0294 (4)0.0076 (4)0.0051 (4)−0.0009 (4)
C10.0268 (16)0.0268 (16)0.0303 (17)−0.0023 (13)0.0056 (13)0.0006 (13)
C20.0346 (18)0.0373 (19)0.0307 (17)−0.0029 (15)0.0042 (14)0.0015 (15)
C30.050 (2)0.041 (2)0.0347 (19)0.0018 (17)0.0125 (17)0.0028 (16)
C40.043 (2)0.052 (2)0.050 (2)0.0057 (18)0.0234 (19)0.0063 (18)
C50.0252 (18)0.054 (2)0.052 (2)0.0025 (16)0.0107 (16)−0.0012 (18)
C60.0258 (16)0.0304 (17)0.0345 (18)0.0018 (13)0.0051 (14)0.0005 (14)
C70.0243 (16)0.0278 (16)0.0296 (17)−0.0012 (13)0.0003 (13)0.0004 (13)
C80.0297 (16)0.0262 (16)0.0284 (16)−0.0001 (13)0.0011 (13)0.0001 (13)
C90.0345 (19)0.042 (2)0.0316 (18)−0.0054 (15)−0.0032 (15)−0.0015 (15)
N30.0470 (19)0.0465 (19)0.0260 (15)−0.0043 (14)−0.0073 (13)−0.0020 (13)
C110.056 (2)0.039 (2)0.0301 (19)−0.0013 (17)0.0093 (17)−0.0027 (16)
C120.0316 (18)0.043 (2)0.0312 (18)−0.0028 (15)−0.0005 (14)0.0018 (15)
N10.0199 (13)0.0392 (16)0.0252 (13)−0.0065 (11)0.0026 (10)0.0025 (12)
N20.0215 (13)0.0430 (17)0.0331 (15)−0.0011 (12)−0.0008 (11)−0.0007 (13)
C100.039 (2)0.048 (2)0.0365 (19)−0.0003 (17)0.0103 (16)−0.0029 (17)
O1W0.0352 (15)0.074 (2)0.073 (2)−0.0205 (14)−0.0072 (14)0.0269 (17)

Geometric parameters (Å, °)

Sb1—Cl12.3687 (10)C7—N11.327 (4)
Sb1—Cl42.5149 (11)C7—C81.461 (4)
Sb1—Cl32.5885 (10)C8—C91.379 (5)
Sb1—Cl22.7184 (11)C8—C121.389 (5)
Sb1—Cl52.7522 (11)C9—N31.336 (5)
C1—C21.386 (5)C9—H9A0.9300
C1—N11.387 (4)N3—C111.327 (5)
C1—C61.391 (4)N3—H3B0.8600
C2—C31.383 (5)C11—C101.365 (5)
C2—H2A0.9300C11—H11A0.9300
C3—C41.398 (6)C12—C101.374 (5)
C3—H3A0.9300C12—H12A0.9300
C4—C51.374 (6)N1—H1A0.8600
C4—H4A0.9300N2—H2B0.8600
C5—C61.388 (5)C10—H10A0.9300
C5—H5A0.9300O1W—H1WA0.8501
C6—N21.381 (4)O1W—H1WB0.8499
C7—N21.331 (4)
Cl1—Sb1—Cl488.55 (4)N2—C7—N1108.8 (3)
Cl1—Sb1—Cl393.99 (4)N2—C7—C8126.0 (3)
Cl4—Sb1—Cl385.94 (4)N1—C7—C8125.2 (3)
Cl1—Sb1—Cl289.66 (4)C9—C8—C12118.3 (3)
Cl4—Sb1—Cl289.38 (4)C9—C8—C7119.8 (3)
Cl3—Sb1—Cl2173.98 (3)C12—C8—C7121.8 (3)
Cl1—Sb1—Cl582.62 (3)N3—C9—C8119.0 (3)
Cl4—Sb1—Cl5167.42 (4)N3—C9—H9A120.5
Cl3—Sb1—Cl585.76 (4)C8—C9—H9A120.5
Cl2—Sb1—Cl599.46 (4)C11—N3—C9123.5 (3)
C2—C1—N1131.6 (3)C11—N3—H3B118.2
C2—C1—C6122.4 (3)C9—N3—H3B118.2
N1—C1—C6106.0 (3)N3—C11—C10119.7 (3)
C3—C2—C1116.0 (3)N3—C11—H11A120.2
C3—C2—H2A122.0C10—C11—H11A120.2
C1—C2—H2A122.0C10—C12—C8120.6 (3)
C2—C3—C4121.5 (4)C10—C12—H12A119.7
C2—C3—H3A119.3C8—C12—H12A119.7
C4—C3—H3A119.3C7—N1—C1109.4 (3)
C5—C4—C3122.4 (4)C7—N1—H1A125.3
C5—C4—H4A118.8C1—N1—H1A125.3
C3—C4—H4A118.8C7—N2—C6109.5 (3)
C4—C5—C6116.2 (3)C7—N2—H2B125.3
C4—C5—H5A121.9C6—N2—H2B125.3
C6—C5—H5A121.9C11—C10—C12118.9 (4)
N2—C6—C5132.3 (3)C11—C10—H10A120.5
N2—C6—C1106.3 (3)C12—C10—H10A120.5
C5—C6—C1121.4 (3)H1WA—O1W—H1WB117.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1W0.861.822.652 (4)161
N3—H3B···Cl5i0.862.283.056 (3)150
N2—H2B···Cl2ii0.862.483.179 (3)139
O1W—H1WA···Cl2iii0.852.353.197 (3)172
O1W—H1WB···Cl3iv0.852.353.198 (3)174

Symmetry codes: (i) x, y, z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x−1, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2324).

References

  • Demirayak, S., Abu Mohsen, U. & Karaburun, A. C. (2002). Eur. J. Med. Chem.37, 255–260. [PubMed]
  • Minoura, H., Takeshita, S., Ita, M., Hirosumi, J., Mabuchi, M., Kawamura, I., Nakajima, S., Nakayama, O., Kayakiri, H., Oku, T., Ohkubo-Suzuki, A., Fukagawa, M., Kojo, H., Hanioka, K., Yamasaki, N., Imoto, T., Kobayashi, Y. & Mutoh, S. (2004). Eur. J. Pharmacol.494, 273–281. [PubMed]
  • Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharmacol. Sci.21, 115–118. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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