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The title ZnII complex, [Zn(C4H4O5)(C6H6N4S2)(H2O)]·2H2O, with ligands consisting of an oxydi­acetate dianion (ODA), a di­amino­bi­thia­zole (DABT) mol­ecule and a water mol­ecule, displays a distorted octahedral coordination geometry. The tridentate ODA chelates to the ZnII in a meridional configuration, with the Zn—O(ether) distance of 2.216 (5) Å, much longer than the Zn—O(carboxyl) distances of 2.051 (5) and 2.071 (5) Å. The overlapped arrangement of parallel DABT ligands, with a separation of 3.509 (9) Å between neighboring DABT rings, suggests π–π stacking between neighboring mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015630/wn6171sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015630/wn6171Isup2.hkl
Contains datablock I

CCDC reference: 221640

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.012 Å
  • H-atom completeness 88%
  • Disorder in solvent or counterion
  • R factor = 0.054
  • wR factor = 0.189
  • Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ......................... 33.00 Perc. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C10 H16 N4 O8 S2 Zn1 Atom count from the _atom_site data: C10 H14 N4 O8 S2 Zn1 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C10 H16 N4 O8 S2 Zn TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 40.00 40.00 0.00 H 64.00 56.00 8.00 N 16.00 16.00 0.00 O 32.00 32.00 0.00 S 8.00 8.00 0.00 Zn 4.00 4.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Zn(C4H4O5)(C6H6N4S2)(H2O)]·2H2OF(000) = 920
Mr = 449.76Dx = 1.680 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 20 reflections
a = 16.682 (4) Åθ = 4.8–10.2°
b = 10.083 (3) ŵ = 1.66 mm1
c = 11.1718 (17) ÅT = 298 K
β = 108.907 (2)°Prism, colorless
V = 1777.8 (7) Å30.30 × 0.25 × 0.14 mm
Z = 4
Data collection top
Rigaku AFC-7S
diffractometer
1589 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 26.0°, θmin = 2.4°
ω/2θ scansh = 2019
Absorption correction: ψ scan
(North et al., 1968)
k = 120
Tmin = 0.602, Tmax = 0.790l = 013
3688 measured reflections3 standard reflections every 150 reflections
3496 independent reflections intensity decay: 1.5%
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0885P)2]
where P = (Fo2 + 2Fc2)/3
3496 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.53 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*/UeqOcc. (<1)
Zn0.16865 (5)0.47670 (8)0.39044 (8)0.0474 (3)
S10.08453 (15)0.2469 (3)0.2390 (3)0.0928 (9)
S1'0.1527 (2)0.4055 (3)0.7957 (3)0.0993 (9)
O10.1536 (3)0.6785 (4)0.3935 (5)0.0544 (12)
O20.2093 (3)0.8742 (5)0.3714 (5)0.0619 (14)
O30.2991 (3)0.5579 (4)0.4571 (4)0.0486 (12)
O40.2467 (3)0.3152 (4)0.3984 (4)0.0484 (11)
O50.3757 (3)0.2401 (5)0.4146 (5)0.0652 (14)
O60.1693 (3)0.5030 (4)0.1936 (4)0.0520 (12)
O70.3232 (5)0.5881 (7)0.9924 (6)0.104 (2)
O8a0.5082 (13)0.369 (2)0.329 (2)0.158 (7)*0.50
O8b0.4800 (15)0.437 (2)0.232 (2)0.177 (8)*0.50
N20.0097 (5)0.3649 (8)0.1134 (7)0.088 (2)
H210.05250.40990.10920.106*
H220.02760.33680.04520.106*
N2'0.2726 (5)0.5297 (8)0.7243 (6)0.086 (2)
H230.29470.55650.66900.103*
H240.29800.54450.80340.103*
N30.0545 (4)0.3766 (6)0.3369 (6)0.0575 (16)
N3'0.1559 (4)0.4386 (6)0.5704 (6)0.0613 (17)
C20.0012 (4)0.3389 (9)0.2238 (9)0.069 (2)
C2'0.1973 (6)0.4640 (8)0.6867 (8)0.069 (2)
C40.0266 (5)0.3331 (8)0.4356 (9)0.064 (2)
C4'0.0810 (5)0.3685 (7)0.5605 (9)0.068 (2)
C50.0460 (6)0.2658 (9)0.3976 (11)0.091 (3)
H50.07270.23270.45270.109*
C5'0.0698 (7)0.3445 (9)0.6734 (9)0.088 (3)
H5'0.02330.30060.68320.106*
C110.2135 (5)0.7506 (7)0.3905 (7)0.0513 (17)
C120.3004 (4)0.6911 (6)0.4123 (6)0.0465 (16)
H12A0.31380.69070.33410.056*
H12B0.34300.74280.47440.056*
C130.3615 (4)0.4687 (7)0.4385 (7)0.0563 (18)
H13A0.41210.46980.51230.068*
H13B0.37690.49650.36580.068*
C140.3243 (5)0.3301 (7)0.4174 (7)0.0506 (17)
H610.20770.45960.16460.100*
H620.15270.57760.15380.100*
H710.37200.56421.06780.100*
H720.26920.56051.00260.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0496 (5)0.0406 (4)0.0537 (5)0.0020 (4)0.0192 (4)0.0033 (4)
S10.0612 (14)0.0932 (18)0.127 (2)0.0263 (13)0.0345 (15)0.0023 (17)
S1'0.163 (3)0.0791 (17)0.0775 (17)0.0015 (17)0.0690 (18)0.0122 (13)
O10.061 (3)0.041 (3)0.067 (3)0.008 (2)0.029 (3)0.005 (2)
O20.076 (4)0.043 (3)0.074 (4)0.002 (3)0.034 (3)0.002 (3)
O30.051 (3)0.042 (3)0.051 (3)0.001 (2)0.013 (2)0.001 (2)
O40.045 (3)0.040 (3)0.057 (3)0.002 (2)0.012 (2)0.002 (2)
O50.054 (3)0.050 (3)0.078 (4)0.010 (2)0.002 (3)0.012 (3)
O60.057 (3)0.050 (3)0.051 (3)0.003 (2)0.020 (2)0.003 (2)
O70.159 (7)0.087 (5)0.080 (4)0.032 (5)0.056 (5)0.005 (4)
N20.079 (5)0.115 (6)0.068 (5)0.039 (5)0.021 (4)0.004 (5)
N2'0.119 (7)0.093 (5)0.045 (4)0.005 (5)0.024 (4)0.005 (4)
N30.055 (4)0.049 (3)0.073 (4)0.006 (3)0.028 (4)0.000 (3)
N3'0.087 (5)0.054 (4)0.047 (4)0.001 (3)0.028 (4)0.005 (3)
C20.034 (4)0.078 (6)0.088 (7)0.014 (4)0.013 (4)0.007 (5)
C2'0.095 (7)0.050 (5)0.068 (6)0.006 (5)0.034 (5)0.005 (4)
C40.068 (5)0.052 (4)0.082 (6)0.000 (4)0.039 (5)0.001 (4)
C4'0.089 (6)0.043 (4)0.100 (7)0.004 (4)0.068 (6)0.003 (4)
C50.078 (6)0.069 (6)0.154 (10)0.015 (5)0.076 (7)0.004 (6)
C5'0.130 (8)0.072 (6)0.086 (7)0.023 (6)0.066 (7)0.012 (5)
C110.070 (5)0.042 (4)0.049 (4)0.000 (4)0.028 (4)0.008 (3)
C120.055 (4)0.037 (4)0.046 (4)0.011 (3)0.014 (3)0.010 (3)
C130.045 (4)0.056 (4)0.064 (5)0.000 (4)0.012 (3)0.007 (4)
C140.054 (5)0.044 (4)0.045 (4)0.007 (3)0.003 (4)0.002 (3)
Geometric parameters (Å, º) top
Zn—O12.051 (5)N2—H210.860
Zn—N32.066 (6)N2—H220.860
Zn—O42.069 (4)N2'—C2'1.360 (11)
Zn—N3'2.124 (6)N2'—H230.860
Zn—O32.216 (5)N2'—H240.860
Zn—O62.219 (4)N3—C21.342 (10)
S1—C51.689 (11)N3—C41.399 (10)
S1—C21.759 (8)N3'—C2'1.285 (10)
S1'—C5'1.712 (11)N3'—C4'1.409 (10)
S1'—C2'1.723 (9)C4—C51.334 (12)
O1—C111.245 (8)C4—C4'1.440 (12)
O2—C111.263 (8)C4'—C5'1.355 (11)
O3—C121.436 (8)C5—H50.930
O3—C131.440 (8)C5'—H5'0.930
O4—C141.251 (8)C11—C121.513 (10)
O5—C141.256 (8)C12—H12A0.970
O6—H610.917C12—H12B0.970
O6—H620.872C13—C141.517 (10)
O7—H710.993C13—H13A0.970
O7—H720.985C13—H13B0.970
N2—C21.313 (11)
O1—Zn—N3112.6 (2)C4'—N3'—Zn112.0 (5)
O1—Zn—O4149.13 (19)N2—C2—N3126.0 (7)
N3—Zn—O497.8 (2)N2—C2—S1122.3 (7)
O1—Zn—N3'96.5 (2)N3—C2—S1111.7 (7)
N3—Zn—N3'79.6 (3)N3'—C2'—N2'123.3 (8)
O4—Zn—N3'94.1 (2)N3'—C2'—S1'115.7 (7)
O1—Zn—O374.93 (17)N2'—C2'—S1'121.0 (7)
N3—Zn—O3172.3 (2)C5—C4—N3114.1 (9)
O4—Zn—O374.95 (17)C5—C4—C4'131.0 (8)
N3'—Zn—O397.9 (2)N3—C4—C4'114.9 (7)
O1—Zn—O686.44 (17)C5'—C4'—N3'113.7 (9)
N3—Zn—O694.1 (2)C5'—C4'—C4128.6 (8)
O4—Zn—O686.05 (17)N3'—C4'—C4117.7 (7)
N3'—Zn—O6173.7 (2)C4—C5—S1112.9 (7)
O3—Zn—O688.23 (16)C4—C5—H5123.6
C5—S1—C289.8 (4)S1—C5—H5123.6
C5'—S1'—C2'88.9 (4)C4'—C5'—S1'111.1 (7)
C11—O1—Zn118.4 (4)C4'—C5'—H5'124.4
C12—O3—C13116.1 (5)S1'—C5'—H5'124.4
C12—O3—Zn110.6 (4)O1—C11—O2125.4 (7)
C13—O3—Zn113.5 (4)O1—C11—C12119.9 (6)
C14—O4—Zn121.0 (4)O2—C11—C12114.7 (7)
Zn—O6—H61121.5O3—C12—C11107.8 (5)
Zn—O6—H62120.3O3—C12—H12A110.1
H61—O6—H62112.0C11—C12—H12A110.1
H71—O7—H72111.2O3—C12—H12B110.1
C2—N2—H21120.0C11—C12—H12B110.1
C2—N2—H22120.0H12A—C12—H12B108.5
H21—N2—H22120.0O3—C13—C14108.6 (6)
C2'—N2'—H23120.0O3—C13—H13A110.0
C2'—N2'—H24120.0C14—C13—H13A110.0
H23—N2'—H24120.0O3—C13—H13B110.0
C2—N3—C4111.5 (7)C14—C13—H13B110.0
C2—N3—Zn132.7 (5)H13A—C13—H13B108.3
C4—N3—Zn115.8 (5)O4—C14—O5125.9 (7)
C2'—N3'—C4'110.6 (7)O4—C14—C13119.0 (6)
C2'—N3'—Zn137.4 (6)O5—C14—C13115.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O60.862.092.878 (10)152
N2—H22···O5i0.861.952.799 (10)168
N2—H23···O30.862.393.169 (8)151
N2—H24···O70.862.062.897 (9)163
O6—H61···O2ii0.921.782.696 (7)173
O6—H62···O5iii0.871.812.674 (7)174
O7—H71···O8biv0.992.473.43 (2)163
O7—H72···O2v0.982.312.792 (9)110
C5—H5···O8avi0.932.433.14 (2)133
C13—H13A···O8avii0.972.463.24 (2)138
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x, y, z+1; (v) x+1/2, y1/2, z+3/2; (vi) x1/2, y+1/2, z+1/2; (vii) x+1, y+1, z+1.
 

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