Literature DB >> 21579271

Aqua-bis(1H-benzimidazole-2-carboxyl-ato-κO,N)zinc(II).

Li Li Di1, Yue Wang, Guo Wu Lin, Tao Lu.   

Abstract

In the title compound, [Zn(C(8)H(5)N(2)O(2))(2)(H(2)O)], the Zn(II) ion is coordinated in each case by a carboxyl-ate O atom and an imidazole N atom from two different benzimidazole-2-carboxyl-ate (BIC) ligands and one water O atom in a trigonal-bipyramidal geometry. In the complex mol-ecule, the two benzimidazole planes are twisted, making a dihedral angle of 55.93 (11)°. The three-dimensional framework is organized by inter-molecular N-H⋯O hydrogen bonding and O-H⋯O inter-actions and π-π inter-actions between adjacent benzimidazole rings [centroid-centroid distance = 3.586 (3) Å].

Entities:  

Year:  2010        PMID： 21579271      PMCID： PMC2979547          DOI： 10.1107/S1600536810015631

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activity of zinc complexes, see: Yoshikawa et al. (2001 ▶); Adachi et al. (2004 ▶). For the biological activity of benzimidazole derivatives, see: Shingalapur et al. (2009 ▶). For zinc N-heterocyclic or their carboxyl­ate complexes, see: He (2006 ▶); Li et al. (2007 ▶); Gao et al. (2005 ▶). For the structural index τ, see: Addison et al. (1984 ▶). For related structures, see: Liu et al. (2004 ▶); Lin (2006 ▶); Zhong et al. (2006 ▶).

Experimental

Crystal data

[Zn(C8H5N2O2)2(H2O)] M = 405.67 Monoclinic, a = 25.9702 (15) Å b = 10.0870 (6) Å c = 16.7885 (10) Å β = 129.21 (3)° V = 3407.8 (14) Å3 Z = 8 Mo Kα radiation μ = 1.48 mm−1 T = 293 K 0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan (ABSCOR; Higashi, 1995 ▶) T min = 0.757, T max = 0.866 6178 measured reflections 3097 independent reflections 2368 reflections with I > 2σ(I) R int = 0.039 3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.101 S = 0.99 3097 reflections 235 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.56 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: CrystalStructure (Rigaku, 2002 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015631/kp2256sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015631/kp2256Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C8H5N2O2)2(H2O)]F(000) = 1648
Mr = 405.67Dx = 1.581 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 25.9702 (15) Åθ = 10–13°
b = 10.0870 (6) ŵ = 1.48 mm−1
c = 16.7885 (10) ÅT = 293 K
β = 129.21 (3)°Block, colourless
V = 3407.8 (14) Å30.20 × 0.10 × 0.10 mm
Z = 8
Enraf–Nonius CAD-4 diffractometer2368 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = −31→31
Absorption correction: ψ scan (ABSCOR; Higashi, 1995)k = 0→12
Tmin = 0.757, Tmax = 0.866l = −20→20
6178 measured reflections3 standard reflections every 120 min
3097 independent reflections intensity decay: 1%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3
3097 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
xyzUiso*/Ueq
Zn10.569627 (17)0.05468 (4)0.69627 (3)0.02900 (14)
O10.50351 (16)0.3274 (3)0.4673 (2)0.0650 (9)
O20.54498 (12)0.1385 (2)0.55532 (17)0.0374 (6)
O30.67653 (12)−0.1506 (2)0.97193 (17)0.0413 (6)
O40.60004 (11)−0.0175 (2)0.84308 (17)0.0364 (6)
O50.48517 (12)−0.0394 (3)0.61712 (19)0.0544 (8)
H5A0.4577−0.03250.55200.065*
H5B0.4758−0.08720.64810.065*
N10.56695 (13)0.2485 (3)0.7205 (2)0.0330 (6)
N20.54861 (16)0.4515 (3)0.6583 (2)0.0433 (8)
H2A0.53750.51460.61560.052*
N30.64903 (12)−0.0562 (3)0.74399 (19)0.0299 (6)
N40.72922 (13)−0.1867 (3)0.8647 (2)0.0392 (7)
H4A0.7536−0.23200.92060.047*
C10.6165 (2)0.4261 (5)0.9534 (3)0.0632 (12)
H1A0.63230.41531.02040.076*
C20.6052 (2)0.5536 (5)0.9134 (3)0.0622 (12)
H2B0.61350.62540.95470.075*
C30.5824 (2)0.5773 (4)0.8158 (3)0.0567 (11)
H3A0.57500.66280.79000.068*
C40.57069 (19)0.4657 (3)0.7569 (3)0.0422 (9)
C50.58192 (16)0.3372 (4)0.7962 (3)0.0353 (8)
C60.60498 (19)0.3157 (4)0.8957 (3)0.0466 (9)
H6A0.61230.23050.92220.056*
C70.54749 (17)0.3217 (3)0.6408 (3)0.0351 (8)
C80.52981 (18)0.2603 (4)0.5450 (3)0.0377 (8)
C90.64989 (16)−0.0943 (3)0.8895 (2)0.0309 (7)
C100.67732 (15)−0.1125 (3)0.8339 (2)0.0295 (7)
C110.68567 (15)−0.0954 (4)0.7139 (2)0.0318 (8)
C120.67916 (17)−0.0663 (4)0.6270 (3)0.0415 (9)
H12A0.6452−0.01200.57530.050*
C130.72500 (19)−0.1208 (4)0.6205 (3)0.0514 (11)
H13A0.7224−0.10140.56400.062*
C140.7749 (2)−0.2041 (5)0.6966 (3)0.0587 (12)
H14A0.8042−0.24100.68850.070*
C150.78262 (19)−0.2338 (4)0.7829 (3)0.0547 (11)
H15A0.8167−0.28860.83410.066*
C160.73686 (17)−0.1779 (4)0.7905 (3)0.0378 (8)
U11U22U33U12U13U23
Zn10.0261 (2)0.0311 (2)0.0279 (2)0.00695 (17)0.01612 (17)0.00661 (17)
O10.110 (3)0.0434 (17)0.0441 (16)0.0153 (17)0.0498 (18)0.0146 (14)
O20.0499 (14)0.0327 (14)0.0329 (13)0.0076 (11)0.0277 (12)0.0067 (11)
O30.0463 (14)0.0491 (16)0.0300 (13)0.0162 (12)0.0248 (12)0.0143 (12)
O40.0365 (13)0.0456 (15)0.0319 (12)0.0156 (11)0.0238 (11)0.0129 (11)
O50.0410 (14)0.089 (2)0.0384 (15)−0.0239 (15)0.0277 (13)−0.0217 (14)
N10.0356 (15)0.0309 (15)0.0288 (15)0.0036 (12)0.0187 (13)0.0037 (12)
N20.0580 (19)0.0310 (17)0.0414 (17)0.0026 (15)0.0316 (16)0.0080 (14)
N30.0272 (14)0.0362 (15)0.0250 (14)0.0105 (12)0.0159 (12)0.0095 (12)
N40.0362 (16)0.0500 (19)0.0305 (15)0.0204 (14)0.0206 (14)0.0189 (14)
C10.068 (3)0.075 (3)0.044 (2)−0.011 (3)0.034 (2)−0.014 (2)
C20.074 (3)0.054 (3)0.056 (3)−0.014 (2)0.041 (3)−0.025 (2)
C30.070 (3)0.038 (2)0.063 (3)−0.007 (2)0.042 (3)−0.011 (2)
C40.047 (2)0.035 (2)0.045 (2)−0.0039 (16)0.0293 (19)−0.0041 (17)
C50.0328 (18)0.039 (2)0.0334 (19)0.0000 (16)0.0204 (16)−0.0015 (16)
C60.052 (2)0.048 (2)0.034 (2)0.0009 (19)0.0247 (19)0.0001 (18)
C70.041 (2)0.0280 (19)0.036 (2)0.0033 (15)0.0245 (17)0.0047 (16)
C80.045 (2)0.037 (2)0.0331 (19)0.0056 (17)0.0257 (17)0.0087 (16)
C90.0310 (18)0.0343 (18)0.0245 (17)0.0022 (15)0.0161 (15)0.0026 (15)
C100.0247 (16)0.0313 (17)0.0285 (17)0.0064 (14)0.0149 (14)0.0045 (15)
C110.0259 (16)0.0411 (19)0.0263 (17)0.0038 (14)0.0156 (15)0.0011 (15)
C120.0363 (19)0.054 (2)0.0334 (19)0.0130 (18)0.0216 (17)0.0142 (18)
C130.046 (2)0.074 (3)0.042 (2)0.014 (2)0.032 (2)0.013 (2)
C140.046 (2)0.086 (3)0.059 (3)0.026 (2)0.040 (2)0.017 (2)
C150.042 (2)0.076 (3)0.049 (2)0.031 (2)0.031 (2)0.024 (2)
C160.0327 (18)0.047 (2)0.0341 (19)0.0130 (16)0.0212 (16)0.0104 (17)
Zn1—O51.947 (3)C1—C21.393 (6)
Zn1—N12.007 (3)C1—H1A0.9300
Zn1—N32.014 (2)C2—C31.365 (6)
Zn1—O42.184 (2)C2—H2B0.9300
Zn1—O22.193 (2)C3—C41.400 (5)
O1—C81.224 (4)C3—H3A0.9300
O2—C81.268 (4)C4—C51.398 (5)
O3—C91.227 (4)C5—C61.390 (5)
O4—C91.268 (4)C6—H6A0.9300
O5—H5A0.8500C7—C81.500 (5)
O5—H5B0.8500C9—C101.502 (4)
N1—C71.318 (4)C11—C121.389 (5)
N1—C51.394 (4)C11—C161.397 (5)
N2—C71.338 (4)C12—C131.377 (5)
N2—C41.375 (5)C12—H12A0.9300
N2—H2A0.8600C13—C141.387 (5)
N3—C101.318 (4)C13—H13A0.9300
N3—C111.387 (4)C14—C151.366 (5)
N4—C101.328 (4)C14—H14A0.9300
N4—C161.383 (4)C15—C161.391 (5)
N4—H4A0.8600C15—H15A0.9300
C1—C61.379 (6)
O5—Zn1—N1116.39 (12)C3—C4—C5121.7 (4)
O5—Zn1—N3115.42 (12)N1—C5—C6131.0 (3)
N1—Zn1—N3128.19 (11)N1—C5—C4108.1 (3)
O5—Zn1—O493.18 (11)C6—C5—C4120.9 (3)
N1—Zn1—O497.49 (10)C1—C6—C5117.1 (4)
N3—Zn1—O479.46 (9)C1—C6—H6A121.5
O5—Zn1—O290.98 (11)C5—C6—H6A121.5
N1—Zn1—O279.56 (10)N1—C7—N2112.6 (3)
N3—Zn1—O299.82 (10)N1—C7—C8121.2 (3)
O4—Zn1—O2175.67 (9)N2—C7—C8126.1 (3)
C8—O2—Zn1112.0 (2)O1—C8—O2126.7 (3)
C9—O4—Zn1113.4 (2)O1—C8—C7120.0 (3)
Zn1—O5—H5A120.4O2—C8—C7113.3 (3)
Zn1—O5—H5B119.6O3—C9—O4127.2 (3)
H5A—O5—H5B120.0O3—C9—C10119.6 (3)
C7—N1—C5105.8 (3)O4—C9—C10113.2 (3)
C7—N1—Zn1112.4 (2)N3—C10—N4112.5 (3)
C5—N1—Zn1141.7 (2)N3—C10—C9121.3 (3)
C7—N2—C4107.5 (3)N4—C10—C9126.2 (3)
C7—N2—H2A126.3C12—C11—N3131.7 (3)
C4—N2—H2A126.3C12—C11—C16120.3 (3)
C10—N3—C11106.3 (3)N3—C11—C16107.9 (3)
C10—N3—Zn1112.6 (2)C13—C12—C11117.5 (3)
C11—N3—Zn1141.2 (2)C13—C12—H12A121.3
C10—N4—C16107.5 (3)C11—C12—H12A121.3
C10—N4—H4A126.2C12—C13—C14121.4 (4)
C16—N4—H4A126.2C12—C13—H13A119.3
C6—C1—C2121.4 (4)C14—C13—H13A119.3
C6—C1—H1A119.3C15—C14—C13122.3 (4)
C2—C1—H1A119.3C15—C14—H14A118.9
C3—C2—C1122.6 (4)C13—C14—H14A118.9
C3—C2—H2B118.7C14—C15—C16116.6 (3)
C1—C2—H2B118.7C14—C15—H15A121.7
C2—C3—C4116.3 (4)C16—C15—H15A121.7
C2—C3—H3A121.9N4—C16—C15132.3 (3)
C4—C3—H3A121.9N4—C16—C11105.8 (3)
N2—C4—C3132.3 (4)C15—C16—C11121.9 (3)
N2—C4—C5106.0 (3)
O5—Zn1—O2—C8105.9 (2)Zn1—N1—C7—N2−177.1 (2)
N1—Zn1—O2—C8−10.8 (2)C5—N1—C7—C8177.4 (3)
N3—Zn1—O2—C8−138.1 (2)Zn1—N1—C7—C80.2 (4)
O5—Zn1—O4—C9113.9 (2)C4—N2—C7—N10.3 (4)
N1—Zn1—O4—C9−128.9 (2)C4—N2—C7—C8−176.9 (3)
N3—Zn1—O4—C9−1.3 (2)Zn1—O2—C8—O1−166.9 (3)
O5—Zn1—N1—C7−80.8 (3)Zn1—O2—C8—C713.2 (4)
N3—Zn1—N1—C799.4 (2)N1—C7—C8—O1170.2 (3)
O4—Zn1—N1—C7−178.1 (2)N2—C7—C8—O1−12.9 (6)
O2—Zn1—N1—C75.1 (2)N1—C7—C8—O2−9.9 (5)
O5—Zn1—N1—C5103.6 (4)N2—C7—C8—O2167.0 (3)
N3—Zn1—N1—C5−76.2 (4)Zn1—O4—C9—O3−178.6 (3)
O4—Zn1—N1—C56.3 (4)Zn1—O4—C9—C102.2 (4)
O2—Zn1—N1—C5−170.5 (4)C11—N3—C10—N4−0.7 (4)
O5—Zn1—N3—C10−88.5 (2)Zn1—N3—C10—N4179.3 (2)
N1—Zn1—N3—C1091.3 (3)C11—N3—C10—C9−178.7 (3)
O4—Zn1—N3—C100.0 (2)Zn1—N3—C10—C91.3 (4)
O2—Zn1—N3—C10175.6 (2)C16—N4—C10—N30.9 (4)
O5—Zn1—N3—C1191.5 (4)C16—N4—C10—C9178.9 (3)
N1—Zn1—N3—C11−88.7 (4)O3—C9—C10—N3178.3 (3)
O4—Zn1—N3—C11180.0 (4)O4—C9—C10—N3−2.5 (5)
O2—Zn1—N3—C11−4.4 (4)O3—C9—C10—N40.5 (5)
C6—C1—C2—C3−0.2 (7)O4—C9—C10—N4179.8 (3)
C1—C2—C3—C40.1 (7)C10—N3—C11—C12−179.6 (4)
C7—N2—C4—C3179.0 (4)Zn1—N3—C11—C120.4 (7)
C7—N2—C4—C5−0.5 (4)C10—N3—C11—C160.1 (4)
C2—C3—C4—N2−179.5 (4)Zn1—N3—C11—C16−179.8 (3)
C2—C3—C4—C5−0.1 (6)N3—C11—C12—C13179.3 (4)
C7—N1—C5—C6−179.6 (4)C16—C11—C12—C13−0.4 (5)
Zn1—N1—C5—C6−3.8 (6)C11—C12—C13—C141.4 (6)
C7—N1—C5—C4−0.4 (4)C12—C13—C14—C15−1.8 (7)
Zn1—N1—C5—C4175.3 (3)C13—C14—C15—C161.1 (7)
N2—C4—C5—N10.6 (4)C10—N4—C16—C15179.6 (4)
C3—C4—C5—N1−179.0 (3)C10—N4—C16—C11−0.8 (4)
N2—C4—C5—C6179.9 (3)C14—C15—C16—N4179.4 (4)
C3—C4—C5—C60.3 (6)C14—C15—C16—C11−0.1 (6)
C2—C1—C6—C50.4 (6)C12—C11—C16—N4−179.9 (3)
N1—C5—C6—C1178.6 (4)N3—C11—C16—N40.4 (4)
C4—C5—C6—C1−0.5 (6)C12—C11—C16—C15−0.2 (6)
C5—N1—C7—N20.1 (4)N3—C11—C16—C15−180.0 (4)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.861.932.765 (4)162
N4—H4A···O3ii0.861.952.778 (4)161
O5—H5A···O2iii0.852.062.670 (4)128
O5—H5B···O4iv0.852.182.695 (5)119
Zn1—O51.947 (3)
Zn1—N12.007 (3)
Zn1—N32.014 (2)
Zn1—O42.184 (2)
Zn1—O22.193 (2)
O5—Zn1—N1116.39 (12)
O5—Zn1—N3115.42 (12)
N1—Zn1—N3128.19 (11)
O5—Zn1—O493.18 (11)
N1—Zn1—O497.49 (10)
N3—Zn1—O479.46 (9)
O5—Zn1—O290.98 (11)
N1—Zn1—O279.56 (10)
N3—Zn1—O299.82 (10)
O4—Zn1—O2175.67 (9)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O1i0.861.932.765 (4)162
N4—H4A⋯O3ii0.861.952.778 (4)161
O5—H5A⋯O2iii0.852.062.670 (4)128
O5—H5B⋯O4iv0.852.182.695 (5)119

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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