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The Zn atom in the title complex, [Zn(C4H4O6)(C3H4N2)2]n, is in an octa­hedral environment comprising two N atoms fom the imidazole ligands and four O atoms from the tartrate ligands. The imino groups participate in intra­molecular N—H...O hydrogen bonds, as do the O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002127/ng2195sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002127/ng2195Isup2.hkl
Contains datablock I

CCDC reference: 295084

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.027
  • wR factor = 0.076
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.97 From the CIF: _reflns_number_total 3070 Count of symmetry unique reflns 1732 Completeness (_total/calc) 177.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1338 Fraction of Friedel pairs measured 0.773 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

catena-Poly[[bis(imidazole-κN)zinc(II)]-µ-L-(+)-tartrato-κ4O,O':O'',O'''] top
Crystal data top
[Zn(C4H6O6)(C3H4N2)2]F(000) = 1424
Mr = 349.61Dx = 1.655 Mg m3
Orthorhombic, C2221Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c2Cell parameters from 25 reflections
a = 8.949 (9) Åθ = 11–15°
b = 14.175 (5) ŵ = 1.78 mm1
c = 22.128 (5) ÅT = 293 K
V = 2807 (3) Å3Prism, colorless
Z = 80.6 × 0.4 × 0.3 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2935 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.0°, θmin = 2.7°
ω–2θ scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 018
Tmin = 0.425, Tmax = 0.580l = 2828
3374 measured reflections3 standard reflections every 60 min
3070 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters not refined
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0387P)2 + 2.8362P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.022
3070 reflectionsΔρmax = 0.35 e Å3
190 parametersΔρmin = 0.38 e Å3
0 restraintsAbsolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (13)
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
Zn10.30350 (3)0.28478 (2)0.647839 (13)0.02312 (9)
O10.1010 (2)0.20955 (14)0.65160 (9)0.0286 (4)
O20.5600 (2)0.04144 (14)0.65063 (14)0.0336 (5)
O30.3524 (2)0.21229 (15)0.73428 (8)0.0269 (4)
H110.28780.20700.76030.040*
O40.1456 (2)0.37794 (13)0.69717 (10)0.0283 (4)
H120.12760.42560.67750.042*
O50.4306 (2)0.16785 (14)0.62348 (9)0.0301 (4)
O60.1197 (2)0.18912 (17)0.69568 (11)0.0391 (5)
N10.5915 (4)0.51620 (19)0.6452 (2)0.0493 (8)
H10.60660.57610.64610.059*
N20.4779 (3)0.37854 (18)0.65577 (14)0.0357 (6)
N30.2554 (3)0.3262 (2)0.55915 (12)0.0363 (6)
N40.1339 (5)0.3514 (3)0.47467 (16)0.0643 (11)
H20.06130.35490.44930.077*
C10.4793 (3)0.11075 (18)0.66274 (12)0.0221 (5)
C20.4311 (3)0.12631 (18)0.72882 (12)0.0213 (5)
H30.36470.07460.74080.026*
C30.0044 (3)0.23603 (19)0.68570 (13)0.0257 (6)
C40.0077 (3)0.33402 (19)0.71498 (13)0.0240 (5)
H40.07390.37260.69880.029*
C50.4649 (4)0.4715 (2)0.66228 (18)0.0431 (9)
H50.37980.50170.67670.052*
C60.6904 (4)0.4500 (3)0.6266 (2)0.0522 (9)
H60.78650.46040.61220.063*
C70.6205 (4)0.3647 (3)0.6334 (2)0.0479 (10)
H70.66260.30630.62440.057*
C80.1262 (5)0.3201 (4)0.53159 (19)0.0630 (13)
H80.03960.29690.54950.076*
C90.3494 (6)0.3597 (6)0.5169 (2)0.093 (2)
H90.45110.37030.52250.112*
C100.2733 (7)0.3758 (5)0.4647 (2)0.093 (2)
H100.31250.39960.42890.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02148 (14)0.02156 (14)0.02631 (15)0.00026 (12)0.00030 (12)0.00357 (13)
O10.0268 (9)0.0277 (9)0.0315 (9)0.0037 (8)0.0057 (8)0.0046 (10)
O20.0456 (12)0.0252 (9)0.0302 (11)0.0102 (8)0.0048 (11)0.0004 (9)
O30.0232 (8)0.0290 (9)0.0284 (9)0.0074 (8)0.0046 (7)0.0016 (9)
O40.0287 (10)0.0178 (9)0.0382 (11)0.0015 (7)0.0070 (8)0.0071 (8)
O50.0383 (12)0.0282 (10)0.0237 (9)0.0074 (9)0.0035 (9)0.0037 (8)
O60.0286 (11)0.0429 (13)0.0460 (13)0.0129 (9)0.0120 (10)0.0127 (10)
N10.0511 (17)0.0273 (13)0.070 (2)0.0112 (12)0.004 (2)0.0021 (17)
N20.0325 (13)0.0269 (12)0.0478 (17)0.0042 (10)0.0045 (13)0.0010 (12)
N30.0376 (13)0.0423 (15)0.0289 (13)0.0028 (11)0.0067 (11)0.0079 (11)
N40.070 (2)0.089 (3)0.0339 (17)0.012 (2)0.0169 (17)0.0096 (18)
C10.0217 (12)0.0197 (11)0.0248 (14)0.0033 (9)0.0008 (10)0.0011 (9)
C20.0201 (12)0.0206 (12)0.0232 (13)0.0020 (10)0.0001 (10)0.0019 (10)
C30.0234 (13)0.0285 (14)0.0251 (13)0.0021 (10)0.0005 (10)0.0017 (10)
C40.0204 (12)0.0228 (12)0.0289 (14)0.0006 (10)0.0001 (10)0.0024 (10)
C50.0448 (19)0.0322 (16)0.052 (2)0.0049 (14)0.0000 (16)0.0046 (15)
C60.0340 (17)0.0462 (19)0.076 (3)0.0132 (17)0.0076 (19)0.0009 (18)
C70.0318 (17)0.0339 (16)0.078 (3)0.0005 (13)0.0055 (16)0.0019 (17)
C80.049 (2)0.101 (4)0.040 (2)0.000 (2)0.0080 (18)0.011 (2)
C90.065 (3)0.160 (6)0.054 (3)0.042 (4)0.012 (2)0.052 (3)
C100.108 (5)0.135 (5)0.037 (2)0.053 (4)0.018 (3)0.040 (3)
Geometric parameters (Å, º) top
Zn1—N22.057 (3)N3—C81.310 (5)
Zn1—O52.081 (2)N3—C91.345 (5)
Zn1—N32.093 (3)N4—C101.313 (7)
Zn1—O12.104 (2)N4—C81.337 (5)
Zn1—O32.215 (2)N4—H20.8600
Zn1—O42.221 (2)C1—C21.540 (4)
O1—C31.265 (3)C2—C2i1.549 (5)
O2—C11.248 (3)C2—H30.9800
O3—C21.413 (3)C3—C41.536 (4)
O3—H110.8200C4—C4ii1.556 (6)
O4—C41.438 (3)C4—H40.9800
O4—H120.8200C5—H50.9300
O5—C11.265 (3)C6—C71.370 (5)
O6—C31.247 (4)C6—H60.9300
N1—C51.352 (5)C7—H70.9300
N1—C61.354 (5)C8—H80.9300
N1—H10.8600C9—C101.359 (7)
N2—C51.330 (4)C9—H90.9300
N2—C71.383 (5)C10—H100.9300
N2—Zn1—O597.02 (11)O2—C1—C2118.6 (3)
N2—Zn1—N393.14 (12)O5—C1—C2117.6 (2)
O5—Zn1—N395.33 (10)O3—C2—C1110.1 (2)
N2—Zn1—O1167.75 (10)O3—C2—C2i110.19 (16)
O5—Zn1—O194.43 (10)C1—C2—C2i110.6 (3)
N3—Zn1—O190.12 (10)O3—C2—H3108.6
N2—Zn1—O394.37 (10)C1—C2—H3108.6
O5—Zn1—O375.30 (8)C2i—C2—H3108.6
N3—Zn1—O3168.64 (10)O6—C3—O1124.3 (3)
O1—Zn1—O384.31 (8)O6—C3—C4117.7 (2)
N2—Zn1—O493.24 (11)O1—C3—C4117.9 (2)
O5—Zn1—O4161.54 (8)O4—C4—C3109.6 (2)
N3—Zn1—O499.40 (10)O4—C4—C4ii110.4 (3)
O1—Zn1—O474.57 (9)C3—C4—C4ii114.45 (14)
O3—Zn1—O488.68 (8)O4—C4—H4107.3
C3—O1—Zn1121.02 (18)C3—C4—H4107.3
C2—O3—Zn1115.13 (15)C4ii—C4—H4107.3
C2—O3—H11109.5N2—C5—N1111.2 (3)
Zn1—O3—H11120.7N2—C5—H5124.4
C4—O4—Zn1115.06 (16)N1—C5—H5124.4
C4—O4—H12109.5N1—C6—C7106.3 (3)
Zn1—O4—H12110.7N1—C6—H6126.9
C1—O5—Zn1121.35 (18)C7—C6—H6126.9
C5—N1—C6107.9 (3)C6—C7—N2109.6 (3)
C5—N1—H1126.0C6—C7—H7125.2
C6—N1—H1126.0N2—C7—H7125.2
C5—N2—C7105.1 (3)N3—C8—N4111.8 (4)
C5—N2—Zn1125.6 (2)N3—C8—H8124.1
C7—N2—Zn1125.3 (2)N4—C8—H8124.1
C8—N3—C9104.6 (3)N3—C9—C10109.7 (5)
C8—N3—Zn1126.8 (3)N3—C9—H9125.2
C9—N3—Zn1128.5 (3)C10—C9—H9125.2
C10—N4—C8107.1 (4)N4—C10—C9106.8 (4)
C10—N4—H2126.4N4—C10—H10126.6
C8—N4—H2126.4C9—C10—H10126.6
O2—C1—O5123.8 (3)
N2—Zn1—O1—C36.5 (6)N2—Zn1—N3—C929.8 (5)
O5—Zn1—O1—C3152.6 (2)O5—Zn1—N3—C967.5 (5)
N3—Zn1—O1—C3112.1 (2)O1—Zn1—N3—C9162.0 (5)
O3—Zn1—O1—C377.9 (2)O3—Zn1—N3—C9101.5 (7)
O4—Zn1—O1—C312.3 (2)O4—Zn1—N3—C9123.7 (5)
N2—Zn1—O3—C299.82 (18)Zn1—O5—C1—O2177.5 (2)
O5—Zn1—O3—C23.69 (16)Zn1—O5—C1—C24.7 (3)
N3—Zn1—O3—C231.4 (5)Zn1—O3—C2—C16.6 (2)
O1—Zn1—O3—C292.41 (17)Zn1—O3—C2—C2i128.9 (2)
O4—Zn1—O3—C2167.04 (16)O2—C1—C2—O3174.7 (2)
N2—Zn1—O4—C4167.73 (19)O5—C1—C2—O37.4 (3)
O5—Zn1—O4—C443.9 (4)O2—C1—C2—C2i52.7 (3)
N3—Zn1—O4—C498.54 (19)O5—C1—C2—C2i129.5 (2)
O1—Zn1—O4—C411.03 (17)Zn1—O1—C3—O6171.0 (2)
O3—Zn1—O4—C473.43 (18)Zn1—O1—C3—C411.3 (3)
N2—Zn1—O5—C192.0 (2)Zn1—O4—C4—C39.0 (3)
N3—Zn1—O5—C1174.2 (2)Zn1—O4—C4—C4ii117.96 (14)
O1—Zn1—O5—C183.6 (2)O6—C3—C4—O4178.6 (3)
O3—Zn1—O5—C10.7 (2)O1—C3—C4—O40.7 (3)
O4—Zn1—O5—C131.3 (4)O6—C3—C4—C4ii56.7 (4)
O5—Zn1—N2—C5169.6 (3)O1—C3—C4—C4ii125.4 (3)
N3—Zn1—N2—C573.8 (3)C7—N2—C5—N10.0 (5)
O1—Zn1—N2—C531.4 (7)Zn1—N2—C5—N1158.4 (3)
O3—Zn1—N2—C5114.7 (3)C6—N1—C5—N20.3 (5)
O4—Zn1—N2—C525.8 (3)C5—N1—C6—C70.5 (5)
O5—Zn1—N2—C715.4 (3)N1—C6—C7—N20.5 (5)
N3—Zn1—N2—C780.3 (3)C5—N2—C7—C60.3 (5)
O1—Zn1—N2—C7174.4 (4)Zn1—N2—C7—C6158.1 (3)
O3—Zn1—N2—C791.1 (3)C9—N3—C8—N42.1 (6)
O4—Zn1—N2—C7179.9 (3)Zn1—N3—C8—N4179.0 (3)
N2—Zn1—N3—C8154.1 (4)C10—N4—C8—N31.8 (7)
O5—Zn1—N3—C8108.6 (4)C8—N3—C9—C101.7 (8)
O1—Zn1—N3—C814.1 (4)Zn1—N3—C9—C10178.5 (5)
O3—Zn1—N3—C874.6 (6)C8—N4—C10—C90.7 (8)
O4—Zn1—N3—C860.3 (4)N3—C9—C10—N40.7 (9)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1iii0.861.902.746 (4)169
N4—H2···O5iv0.862.022.846 (5)162
O3—H11···O6ii0.821.812.617 (4)168
O4—H12···O2v0.821.852.649 (4)165
Symmetry codes: (ii) x, y, z+3/2; (iii) x+1/2, y+1/2, z; (iv) x1/2, y+1/2, z+1; (v) x1/2, y+1/2, z.
 

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