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In the title ZnII complex, [Zn(C5H3N2O4)2(H2O)2]·C10H8N2, the ZnII atom is octa­hedrally surrounded by two chelating monodeprotonated 5-carb­oxy-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules. Inter­molecular O—H...O hydrogen-bonding inter­actions link the mol­ecules in the crystal structure, forming two-dimensional layers. These layers self-assemble into a three-dimensional network through inter­molecular N—H...N hydrogen-bond inter­actions between imidazole N—H and pyridyl N atoms. The Zn atom and the mid-point of the central C—C bond of the bipyridine are located on inversion centers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039705/dn2064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039705/dn2064Isup2.hkl
Contains datablock I

CCDC reference: 627482

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.066
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.82 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N1 .. 5.43 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C20 H18 N6 O10 Zn1 Atom count from _chemical_formula_moiety:C30 H26 N8 O10 Zn1 ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.824 Tmax scaled 0.824 Tmin scaled 0.814 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT (Bruker, 1998; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Diaquabis(5-carboxy-1H-imidazole-4-carboxylato-κ2N,O)zinc(II) 4,4'-bipyridine solvate top
Crystal data top
[Zn(C5H3N2O4)2(H2O)2]·C10H8N2Z = 1
Mr = 567.78F(000) = 290
Triclinic, P1Dx = 1.741 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0195 (5) ÅCell parameters from 1052 reflections
b = 6.6503 (7) Åθ = 2.9–28.0°
c = 17.0480 (17) ŵ = 1.21 mm1
α = 86.317 (2)°T = 293 K
β = 86.687 (2)°Block, colorless
γ = 72.588 (2)°0.22 × 0.18 × 0.16 mm
V = 541.44 (10) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2096 independent reflections
Radiation source: fine-focus sealed tube2055 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
φ and ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 66
Tmin = 0.988, Tmax = 1.000k = 78
2982 measured reflectionsl = 1420
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.037P)2 + 0.2715P]
where P = (Fo2 + 2Fc2)/3
2096 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.31 e Å3
3 restraintsΔρmin = 0.39 e Å3
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
Zn10.00000.50000.00000.01828 (10)
C10.0660 (3)0.2391 (2)0.14291 (9)0.0173 (3)
C20.1683 (3)0.1837 (2)0.21691 (9)0.0184 (3)
C30.2999 (3)0.4505 (2)0.16625 (9)0.0193 (3)
H30.38360.55820.16080.023*
C40.1119 (3)0.1550 (2)0.09515 (9)0.0181 (3)
C50.1486 (4)0.0173 (3)0.27743 (10)0.0236 (3)
C60.6585 (4)0.2559 (3)0.42332 (10)0.0266 (4)
H60.58710.14210.43230.032*
C70.8091 (4)0.3014 (3)0.48157 (10)0.0247 (3)
H70.83680.21970.52840.030*
C80.9192 (3)0.4704 (3)0.46967 (9)0.0208 (3)
C90.8697 (4)0.5856 (3)0.39810 (10)0.0269 (4)
H90.93970.69950.38720.032*
C100.7160 (4)0.5293 (3)0.34337 (10)0.0275 (4)
H100.68440.60860.29600.033*
N10.1504 (3)0.4066 (2)0.11185 (8)0.0185 (3)
N20.3153 (3)0.3200 (2)0.23021 (8)0.0195 (3)
H20.40210.32180.27210.023*
N30.6102 (3)0.3671 (2)0.35478 (8)0.0251 (3)
O10.1944 (3)0.00447 (18)0.12403 (7)0.0247 (3)
O20.1707 (2)0.24418 (17)0.02826 (7)0.0203 (2)
O30.0048 (3)0.1086 (2)0.25900 (8)0.0353 (3)
H3A0.06390.06930.21610.053*
O40.2596 (3)0.0011 (2)0.33940 (7)0.0324 (3)
O1W0.3645 (2)0.71321 (18)0.05378 (7)0.0216 (2)
H1WA0.330 (4)0.816 (2)0.0697 (11)0.026*
H1WB0.508 (3)0.748 (3)0.0291 (11)0.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02199 (15)0.02082 (15)0.01564 (15)0.01142 (10)0.00674 (10)0.00237 (9)
C10.0188 (7)0.0178 (7)0.0173 (7)0.0085 (6)0.0020 (6)0.0004 (6)
C20.0200 (7)0.0198 (7)0.0169 (8)0.0080 (6)0.0017 (6)0.0020 (6)
C30.0211 (7)0.0223 (8)0.0179 (8)0.0108 (6)0.0042 (6)0.0013 (6)
C40.0175 (7)0.0181 (7)0.0202 (8)0.0069 (6)0.0014 (6)0.0035 (6)
C50.0295 (8)0.0224 (8)0.0187 (8)0.0077 (7)0.0008 (6)0.0015 (6)
C60.0300 (9)0.0292 (9)0.0243 (9)0.0136 (7)0.0055 (7)0.0013 (7)
C70.0297 (8)0.0274 (8)0.0191 (8)0.0114 (7)0.0061 (7)0.0022 (6)
C80.0195 (7)0.0251 (8)0.0179 (8)0.0062 (6)0.0027 (6)0.0020 (6)
C90.0343 (9)0.0305 (9)0.0209 (8)0.0168 (7)0.0077 (7)0.0039 (7)
C100.0330 (9)0.0325 (9)0.0187 (8)0.0118 (7)0.0089 (7)0.0029 (7)
N10.0211 (6)0.0198 (6)0.0178 (7)0.0106 (5)0.0041 (5)0.0004 (5)
N20.0218 (6)0.0241 (7)0.0152 (6)0.0099 (5)0.0058 (5)0.0007 (5)
N30.0248 (7)0.0306 (8)0.0214 (7)0.0089 (6)0.0067 (5)0.0037 (6)
O10.0337 (6)0.0244 (6)0.0231 (6)0.0189 (5)0.0031 (5)0.0009 (5)
O20.0223 (6)0.0233 (6)0.0194 (6)0.0120 (5)0.0065 (4)0.0006 (4)
O30.0572 (9)0.0319 (7)0.0257 (7)0.0275 (7)0.0084 (6)0.0086 (5)
O40.0424 (7)0.0356 (7)0.0202 (6)0.0131 (6)0.0090 (5)0.0072 (5)
O1W0.0214 (6)0.0225 (6)0.0250 (6)0.0113 (5)0.0079 (5)0.0022 (5)
Geometric parameters (Å, º) top
Zn1—N1i2.0798 (13)C5—O31.320 (2)
Zn1—N12.0798 (13)C6—N31.336 (2)
Zn1—O22.1400 (11)C6—C71.383 (2)
Zn1—O2i2.1400 (11)C6—H60.9300
Zn1—O1Wi2.1491 (12)C7—C81.392 (2)
Zn1—O1W2.1491 (12)C7—H70.9300
C1—N11.3713 (19)C8—C91.392 (2)
C1—C21.376 (2)C8—C8ii1.491 (3)
C1—C41.488 (2)C9—C101.381 (2)
C2—N21.365 (2)C9—H90.9300
C2—C51.485 (2)C10—N31.337 (2)
C3—N11.325 (2)C10—H100.9300
C3—N21.340 (2)N2—H20.8600
C3—H30.9300O3—H3A0.8200
C4—O11.2559 (19)O1W—H1WA0.815 (9)
C4—O21.260 (2)O1W—H1WB0.818 (9)
C5—O41.205 (2)
N1i—Zn1—N1180.00 (9)O3—C5—C2116.11 (15)
N1i—Zn1—O2100.39 (4)N3—C6—C7123.30 (16)
N1—Zn1—O279.61 (4)N3—C6—H6118.4
N1i—Zn1—O2i79.61 (4)C7—C6—H6118.4
N1—Zn1—O2i100.39 (4)C6—C7—C8119.62 (16)
O2—Zn1—O2i180.00 (6)C6—C7—H7120.2
N1i—Zn1—O1Wi88.44 (5)C8—C7—H7120.2
N1—Zn1—O1Wi91.56 (5)C7—C8—C9117.02 (15)
O2—Zn1—O1Wi90.15 (4)C7—C8—C8ii122.38 (19)
O2i—Zn1—O1Wi89.85 (4)C9—C8—C8ii120.59 (19)
N1i—Zn1—O1W91.56 (5)C10—C9—C8119.45 (16)
N1—Zn1—O1W88.44 (5)C10—C9—H9120.3
O2—Zn1—O1W89.85 (4)C8—C9—H9120.3
O2i—Zn1—O1W90.15 (4)N3—C10—C9123.55 (16)
O1Wi—Zn1—O1W180.00 (6)N3—C10—H10118.2
N1—C1—C2109.16 (13)C9—C10—H10118.2
N1—C1—C4118.39 (13)C3—N1—C1105.83 (13)
C2—C1—C4132.43 (14)C3—N1—Zn1143.05 (11)
N2—C2—C1105.96 (13)C1—N1—Zn1111.12 (10)
N2—C2—C5120.42 (14)C3—N2—C2107.67 (13)
C1—C2—C5133.62 (15)C3—N2—H2126.2
N1—C3—N2111.38 (14)C2—N2—H2126.2
N1—C3—H3124.3C6—N3—C10117.06 (15)
N2—C3—H3124.3C4—O2—Zn1114.46 (9)
O1—C4—O2124.99 (14)C5—O3—H3A109.5
O1—C4—C1118.59 (14)Zn1—O1W—H1WA111.6 (14)
O2—C4—C1116.42 (13)Zn1—O1W—H1WB117.3 (14)
O4—C5—O3122.45 (15)H1WA—O1W—H1WB111.5 (17)
O4—C5—C2121.44 (16)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N30.861.892.7435 (19)170
O3—H3A···O10.821.722.5403 (18)177
O1W—H1WA···O1iii0.82 (1)1.91 (1)2.7058 (16)166 (2)
O1W—H1WB···O2iv0.82 (1)1.92 (1)2.7224 (15)166 (2)
Symmetry codes: (iii) x, y+1, z; (iv) x1, y+1, z.
 

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