metal-organic compounds
2-(3-Pyridinio)benzimidazolium pentachloridoantimonate(III) monohydrate
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
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 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); Pawar et al. (2004); Demirayak et al. (2002).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
10.1107/S1600536809018935/rz2324sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018935/rz2324Isup2.hkl
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.
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).
Data collection: CrystalClear (Rigaku, 2005); cell
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).(C12H11N3)[SbCl5]·H2O | F(000) = 1000 |
Mr = 514.25 | Dx = 1.955 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1647 reflections |
a = 9.2619 (19) Å | θ = 3.0–27.6° |
b = 13.425 (3) Å | µ = 2.35 mm−1 |
c = 14.380 (3) Å | T = 293 K |
β = 102.27 (3)° | Prism, colourless |
V = 1747.2 (7) Å3 | 0.25 × 0.22 × 0.19 mm |
Z = 4 |
Rigaku SCXmini diffractometer | 3410 independent reflections |
Radiation source: fine-focus sealed tube | 3037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 3.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −16→16 |
Tmin = 0.892, Tmax = 0.964 | l = −17→17 |
15623 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | H-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 parameters | Δρmax = 0.32 e Å−3 |
6 restraints | Δρmin = −0.48 e Å−3 |
(C12H11N3)[SbCl5]·H2O | V = 1747.2 (7) Å3 |
Mr = 514.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.2619 (19) Å | µ = 2.35 mm−1 |
b = 13.425 (3) Å | T = 293 K |
c = 14.380 (3) Å | 0.25 × 0.22 × 0.19 mm |
β = 102.27 (3)° |
Rigaku SCXmini diffractometer | 3410 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 3037 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.964 | Rint = 0.043 |
15623 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 6 restraints |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.32 e Å−3 |
3410 reflections | Δρmin = −0.48 e Å−3 |
199 parameters |
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 | ||
Sb1 | 0.98691 (2) | 0.410246 (16) | 0.112742 (15) | 0.02964 (9) | |
Cl1 | 0.98813 (10) | 0.24807 (7) | 0.17778 (7) | 0.0451 (2) | |
Cl2 | 1.06091 (10) | 0.48665 (7) | 0.29163 (6) | 0.0446 (2) | |
Cl3 | 0.93983 (10) | 0.34774 (8) | −0.06139 (6) | 0.0445 (2) | |
Cl4 | 1.25689 (10) | 0.38926 (8) | 0.11321 (8) | 0.0516 (3) | |
Cl5 | 0.68651 (10) | 0.39170 (8) | 0.09585 (6) | 0.0434 (2) | |
C1 | 0.5091 (3) | 0.3717 (2) | 0.4685 (2) | 0.0280 (7) | |
C2 | 0.4622 (4) | 0.3711 (3) | 0.3703 (2) | 0.0346 (7) | |
H2A | 0.3631 | 0.3642 | 0.3409 | 0.042* | |
C3 | 0.5715 (4) | 0.3813 (3) | 0.3187 (3) | 0.0412 (9) | |
H3A | 0.5457 | 0.3804 | 0.2526 | 0.049* | |
C4 | 0.7199 (4) | 0.3929 (3) | 0.3638 (3) | 0.0463 (10) | |
H4A | 0.7901 | 0.3989 | 0.3265 | 0.056* | |
C5 | 0.7658 (4) | 0.3958 (3) | 0.4611 (3) | 0.0433 (9) | |
H5A | 0.8646 | 0.4046 | 0.4905 | 0.052* | |
C6 | 0.6566 (4) | 0.3849 (2) | 0.5131 (2) | 0.0304 (7) | |
C7 | 0.5252 (3) | 0.3714 (2) | 0.6244 (2) | 0.0280 (7) | |
C8 | 0.4838 (4) | 0.3694 (2) | 0.7169 (2) | 0.0289 (7) | |
C9 | 0.5913 (4) | 0.3773 (3) | 0.7992 (2) | 0.0376 (8) | |
H9A | 0.6906 | 0.3812 | 0.7963 | 0.045* | |
N3 | 0.5509 (4) | 0.3794 (2) | 0.8830 (2) | 0.0421 (7) | |
H3B | 0.6190 | 0.3841 | 0.9338 | 0.051* | |
C11 | 0.4115 (5) | 0.3745 (3) | 0.8920 (3) | 0.0417 (9) | |
H11A | 0.3891 | 0.3776 | 0.9520 | 0.050* | |
C12 | 0.3373 (4) | 0.3627 (3) | 0.7250 (2) | 0.0364 (8) | |
H12A | 0.2630 | 0.3566 | 0.6705 | 0.044* | |
N1 | 0.4320 (3) | 0.3631 (2) | 0.54084 (18) | 0.0285 (6) | |
H1A | 0.3383 | 0.3538 | 0.5328 | 0.034* | |
N2 | 0.6611 (3) | 0.3840 (2) | 0.6097 (2) | 0.0335 (6) | |
H2B | 0.7396 | 0.3905 | 0.6536 | 0.040* | |
C10 | 0.3011 (4) | 0.3649 (3) | 0.8128 (3) | 0.0407 (8) | |
H10A | 0.2031 | 0.3599 | 0.8182 | 0.049* | |
O1W | 0.1429 (3) | 0.3470 (2) | 0.4754 (2) | 0.0636 (9) | |
H1WA | 0.1260 | 0.3892 | 0.4303 | 0.076* | |
H1WB | 0.0951 | 0.2925 | 0.4676 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sb1 | 0.02958 (13) | 0.02996 (14) | 0.02782 (13) | −0.00150 (9) | 0.00262 (9) | 0.00183 (9) |
Cl1 | 0.0391 (5) | 0.0362 (5) | 0.0563 (6) | −0.0002 (4) | 0.0014 (4) | 0.0136 (4) |
Cl2 | 0.0442 (5) | 0.0505 (5) | 0.0366 (5) | −0.0094 (4) | 0.0033 (4) | −0.0069 (4) |
Cl3 | 0.0465 (5) | 0.0524 (6) | 0.0302 (4) | 0.0073 (4) | −0.0016 (4) | −0.0029 (4) |
Cl4 | 0.0338 (5) | 0.0687 (7) | 0.0536 (6) | −0.0061 (4) | 0.0121 (4) | −0.0013 (5) |
Cl5 | 0.0362 (5) | 0.0638 (6) | 0.0294 (4) | 0.0076 (4) | 0.0051 (4) | −0.0009 (4) |
C1 | 0.0268 (16) | 0.0268 (16) | 0.0303 (17) | −0.0023 (13) | 0.0056 (13) | 0.0006 (13) |
C2 | 0.0346 (18) | 0.0373 (19) | 0.0307 (17) | −0.0029 (15) | 0.0042 (14) | 0.0015 (15) |
C3 | 0.050 (2) | 0.041 (2) | 0.0347 (19) | 0.0018 (17) | 0.0125 (17) | 0.0028 (16) |
C4 | 0.043 (2) | 0.052 (2) | 0.050 (2) | 0.0057 (18) | 0.0234 (19) | 0.0063 (18) |
C5 | 0.0252 (18) | 0.054 (2) | 0.052 (2) | 0.0025 (16) | 0.0107 (16) | −0.0012 (18) |
C6 | 0.0258 (16) | 0.0304 (17) | 0.0345 (18) | 0.0018 (13) | 0.0051 (14) | 0.0005 (14) |
C7 | 0.0243 (16) | 0.0278 (16) | 0.0296 (17) | −0.0012 (13) | 0.0003 (13) | 0.0004 (13) |
C8 | 0.0297 (16) | 0.0262 (16) | 0.0284 (16) | −0.0001 (13) | 0.0011 (13) | 0.0001 (13) |
C9 | 0.0345 (19) | 0.042 (2) | 0.0316 (18) | −0.0054 (15) | −0.0032 (15) | −0.0015 (15) |
N3 | 0.0470 (19) | 0.0465 (19) | 0.0260 (15) | −0.0043 (14) | −0.0073 (13) | −0.0020 (13) |
C11 | 0.056 (2) | 0.039 (2) | 0.0301 (19) | −0.0013 (17) | 0.0093 (17) | −0.0027 (16) |
C12 | 0.0316 (18) | 0.043 (2) | 0.0312 (18) | −0.0028 (15) | −0.0005 (14) | 0.0018 (15) |
N1 | 0.0199 (13) | 0.0392 (16) | 0.0252 (13) | −0.0065 (11) | 0.0026 (10) | 0.0025 (12) |
N2 | 0.0215 (13) | 0.0430 (17) | 0.0331 (15) | −0.0011 (12) | −0.0008 (11) | −0.0007 (13) |
C10 | 0.039 (2) | 0.048 (2) | 0.0365 (19) | −0.0003 (17) | 0.0103 (16) | −0.0029 (17) |
O1W | 0.0352 (15) | 0.074 (2) | 0.073 (2) | −0.0205 (14) | −0.0072 (14) | 0.0269 (17) |
Sb1—Cl1 | 2.3687 (10) | C7—N1 | 1.327 (4) |
Sb1—Cl4 | 2.5149 (11) | C7—C8 | 1.461 (4) |
Sb1—Cl3 | 2.5885 (10) | C8—C9 | 1.379 (5) |
Sb1—Cl2 | 2.7184 (11) | C8—C12 | 1.389 (5) |
Sb1—Cl5 | 2.7522 (11) | C9—N3 | 1.336 (5) |
C1—C2 | 1.386 (5) | C9—H9A | 0.9300 |
C1—N1 | 1.387 (4) | N3—C11 | 1.327 (5) |
C1—C6 | 1.391 (4) | N3—H3B | 0.8600 |
C2—C3 | 1.383 (5) | C11—C10 | 1.365 (5) |
C2—H2A | 0.9300 | C11—H11A | 0.9300 |
C3—C4 | 1.398 (6) | C12—C10 | 1.374 (5) |
C3—H3A | 0.9300 | C12—H12A | 0.9300 |
C4—C5 | 1.374 (6) | N1—H1A | 0.8600 |
C4—H4A | 0.9300 | N2—H2B | 0.8600 |
C5—C6 | 1.388 (5) | C10—H10A | 0.9300 |
C5—H5A | 0.9300 | O1W—H1WA | 0.8501 |
C6—N2 | 1.381 (4) | O1W—H1WB | 0.8499 |
C7—N2 | 1.331 (4) | ||
Cl1—Sb1—Cl4 | 88.55 (4) | N2—C7—N1 | 108.8 (3) |
Cl1—Sb1—Cl3 | 93.99 (4) | N2—C7—C8 | 126.0 (3) |
Cl4—Sb1—Cl3 | 85.94 (4) | N1—C7—C8 | 125.2 (3) |
Cl1—Sb1—Cl2 | 89.66 (4) | C9—C8—C12 | 118.3 (3) |
Cl4—Sb1—Cl2 | 89.38 (4) | C9—C8—C7 | 119.8 (3) |
Cl3—Sb1—Cl2 | 173.98 (3) | C12—C8—C7 | 121.8 (3) |
Cl1—Sb1—Cl5 | 82.62 (3) | N3—C9—C8 | 119.0 (3) |
Cl4—Sb1—Cl5 | 167.42 (4) | N3—C9—H9A | 120.5 |
Cl3—Sb1—Cl5 | 85.76 (4) | C8—C9—H9A | 120.5 |
Cl2—Sb1—Cl5 | 99.46 (4) | C11—N3—C9 | 123.5 (3) |
C2—C1—N1 | 131.6 (3) | C11—N3—H3B | 118.2 |
C2—C1—C6 | 122.4 (3) | C9—N3—H3B | 118.2 |
N1—C1—C6 | 106.0 (3) | N3—C11—C10 | 119.7 (3) |
C3—C2—C1 | 116.0 (3) | N3—C11—H11A | 120.2 |
C3—C2—H2A | 122.0 | C10—C11—H11A | 120.2 |
C1—C2—H2A | 122.0 | C10—C12—C8 | 120.6 (3) |
C2—C3—C4 | 121.5 (4) | C10—C12—H12A | 119.7 |
C2—C3—H3A | 119.3 | C8—C12—H12A | 119.7 |
C4—C3—H3A | 119.3 | C7—N1—C1 | 109.4 (3) |
C5—C4—C3 | 122.4 (4) | C7—N1—H1A | 125.3 |
C5—C4—H4A | 118.8 | C1—N1—H1A | 125.3 |
C3—C4—H4A | 118.8 | C7—N2—C6 | 109.5 (3) |
C4—C5—C6 | 116.2 (3) | C7—N2—H2B | 125.3 |
C4—C5—H5A | 121.9 | C6—N2—H2B | 125.3 |
C6—C5—H5A | 121.9 | C11—C10—C12 | 118.9 (4) |
N2—C6—C5 | 132.3 (3) | C11—C10—H10A | 120.5 |
N2—C6—C1 | 106.3 (3) | C12—C10—H10A | 120.5 |
C5—C6—C1 | 121.4 (3) | H1WA—O1W—H1WB | 117.8 |
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+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C12H11N3)[SbCl5]·H2O |
Mr | 514.25 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.35 |
Crystal size (mm) | 0.25 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Rigaku SCXmini diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.892, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15623, 3410, 3037 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.068, 0.93 |
No. of reflections | 3410 |
No. of parameters | 199 |
No. of restraints | 6 |
H-atom treatment | H-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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1W | 0.86 | 1.82 | 2.652 (4) | 160.7 |
N3—H3B···Cl5i | 0.86 | 2.28 | 3.056 (3) | 149.7 |
N2—H2B···Cl2ii | 0.86 | 2.48 | 3.179 (3) | 139.4 |
O1W—H1WA···Cl2iii | 0.85 | 2.35 | 3.197 (3) | 171.5 |
O1W—H1WB···Cl3iv | 0.85 | 2.35 | 3.198 (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
Demirayak, S., Abu Mohsen, U. & Karaburun, A. C. (2002). Eur. J. Med. Chem. 37, 255–260. Web of Science CrossRef PubMed CAS Google Scholar
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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.
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.