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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Page m674
doi:10.1107/S1600536809018935

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

Li-Jing Cui,a Hai-Jun Xua* and Ke-Ji Pana

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
*Correspondence e-mail: xuhj@seu.edu.cn

(Received 12 May 2009; accepted 19 May 2009; online 23 May 2009)

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[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.]); Pawar et al. (2004[Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharmacol. Sci. 21, 115-118.]); Demirayak et al. (2002[Demirayak, S., Abu Mohsen, U. & Karaburun, A. C. (2002). Eur. J. Med. Chem. 37, 255-260.]).

[Scheme 1]

Experimental

Crystal data

  • (C12H11N3)[SbCl5]·H2O

  • Mr = 514.25

  • Monoclinic, P 21 /c

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.892, Tmax = 0.964 (expected range = 0.592–0.640)

  • 15623 measured reflections

  • 3410 independent reflections

  • 3037 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1W 0.86 1.82 2.652 (4) 161
N3—H3B⋯Cl5i 0.86 2.28 3.056 (3) 150
N2—H2B⋯Cl2ii 0.86 2.48 3.179 (3) 139
O1W—H1WA⋯Cl2iii 0.85 2.35 3.197 (3) 172
O1W—H1WB⋯Cl3iv 0.85 2.35 3.198 (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+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information

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

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

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound, showing the structure along the c axis. Intermolecular H bonds are shown as dashed lines.
2-(3-Pyridinio)benzimidazolium pentachloridoantimonate(III) monohydrate top
Crystal data top
(C12H11N3)[SbCl5]·H2OF(000) = 1000
Mr = 514.25Dx = 1.955 Mg m−3
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 mm−1
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 top
Rigaku SCXmini
diffractometer		3410 independent reflections
Radiation source: fine-focus sealed tube3037 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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 = 0.93 w = 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 Å−3
6 restraintsΔρmin = −0.48 e Å−3
Crystal data top
(C12H11N3)[SbCl5]·H2OV = 1747.2 (7) Å3
Mr = 514.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2619 (19) ŵ = 2.35 mm−1
b = 13.425 (3) ÅT = 293 K
c = 14.380 (3) Å0.25 × 0.22 × 0.19 mm
β = 102.27 (3)°
Data collection top
Rigaku SCXmini
diffractometer		3410 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		3037 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.964Rint = 0.043
15623 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0286 restraints
wR(F2) = 0.068H-atom parameters constrained
S = 0.93Δρmax = 0.32 e Å−3
3410 reflectionsΔρmin = −0.48 e Å−3
199 parameters
Special details top

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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formula(C12H11N3)[SbCl5]·H2O
Mr514.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.2619 (19), 13.425 (3), 14.380 (3)
β (°) 102.27 (3)
V (Å3)1747.2 (7)
Z4
Radiation typeMo Kα
µ (mm−1)2.35
Crystal size (mm)0.25 × 0.22 × 0.19
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.892, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections		15623, 3410, 3037
Rint0.043
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.068, 0.93
No. of reflections3410
No. of parameters199
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.48

Computer programs: CrystalClear (Rigaku, 2005), 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···O1W0.861.822.652 (4)160.7
N3—H3B···Cl5i0.862.283.056 (3)149.7
N2—H2B···Cl2ii0.862.483.179 (3)139.4
O1W—H1WA···Cl2iii0.852.353.197 (3)171.5
O1W—H1WB···Cl3iv0.852.353.198 (3)173.7
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.
 

Acknowledgements

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

References

First citationDemirayak, S., Abu Mohsen, U. & Karaburun, A. C. (2002). Eur. J. Med. Chem. 37, 255–260.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMinoura, 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.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationPawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharmacol. Sci. 21, 115–118.  Web of Science CrossRef CAS Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Page m674
doi:10.1107/S1600536809018935
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