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Acta Cryst. (2007). E63, m2178-m2179    [ doi:10.1107/S160053680703454X ]

Bis([mu]-pyridine-2,3-dicarboxylato)bis[aqua(2,2'-diamino-4,4'-bi-1,3-thiazole)cobalt(II)] decahydrate

Y.-Y. Lin, G.-H. Chen, Y.-P. Yu and B.-X. Liu

Abstract top

In the centrosymmetric title dimeric CoII complex, [Co2(C7H3NO4)2(C6H6N4OS2)2(H2O)2].10H2O, each CoII cation has a distorted octahedral coordination geometry formed by a diaminobithiazole (DABT) ligand, two pyridine-2,3-dicarboxylate anions and a coordinated water molecule. With its two carboxylate groups, the pyridine-2,3-dicarboxylate anion bridges two CoII ions to form the dimeric complex. Within the chelating DABT ligand, the two thiazole rings are twisted with respect to each other [dihedral angle = 3.29 (19)°]. Extensive N-H...O, O-H...O and O-H...N hydrogen bonding helps to stabilize the crystal structure.

Comment top

Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown biological activities such as the effective inhibitors of DNA synthesis of the tumor cells (Waring, 1981; Fisher et al., 1985). As part of serial structural investigation of metal complexes with DABT (Liu & Xu, 2004), the title CoII complex was recently prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The complex of CoII has a distorted octahedral coordination geometry (Table 1) formed by one of DABT ligand, one of pyridine-2,3-dicarboxylate anion, one of coordinated water and one of adjacent pyridine-2,3-dicarboxylate anion.

Within the complex, the DABT molecule shows approximately coplanar configuration with the dihedral angle of 3.29 (19)° between thiazole rings defined by C1, C2, C3, S1, N1 and C4, C5, C6, S2, N3. This is compare to 4.57 (7)° found in [Mn(DABT)(oxydiacetate)] (Luo et al., 2004) and 6.52 (9)° found in [Cu(DABT)(oxydiacetato)] (Wu et al., 2003), but different from the 17.23 (7)° found in [Cr(C4H5NO4)(C6H6N4S2)(H2O)]Cl (Liu et al., 2004) and 20.02 (8)° in [Ni(DABT)(iminodiacetate)] (Liu & Xu, 2005). Bond lengths C6—N4 [1.334 (4) Å] and C3—N2 [1.326 (4) Å] imply the existence of electron delocalization between thiazole rings and amino groups.

Within the pyridine-2,3-dicarboxylate anion, one oxygen atom (O11) of one carboxyl group of the pyridine-2,3-dicarboxylate anion and the nitrogen atom (N11) of pyridine ring chelate to CoII atom and one oxygen atom (O13) of another carboxyl group of the pyridine-2,3-dicarboxylate anion chelates to another neighboring CoII atom to form the dimeric complex across an inversion centre. The dihedral angles between the pyridine ring and two carboxyl group plans are 5.84 (7) and 84.82 (11)° for the plan formed by C11, C16, O11, O12 and the plan formed by C12, C17, O13, O14 respectively. Otherwise, another uncoordinated oxygen atom (O12 and O14) hydrogen bonded to the lattice water within the complex (Fig. 1 and Table 2), which helps to stabilize the crystal structure.

Related literature top

For general background, see: Waring (1981); Fisher et al. (1985). For related structures, see: Liu & Xu (2004); Liu et al. (2004); Liu & Xu (2005); Luo et al. (2004); Wu et al. (2003).

Experimental top

An aqua solution (20 ml) containing DABT (0.20 g, 1 mmol) and CoCl2.6H2O (0.23 g, 1 mmol) was mixed with an aqueous solution (10 ml) of pyridine-2,3-dicarboxylic acid (0.17 g, 1 mmol) and NaOH (0.08 g, 2 mmol). The mixture was refluxed for 6 h. After cooling to room temperature the solution was filtered. Single crystals of the title compound were obtained from the filtrate after 3 d.

Refinement top

H atoms on carbon atoms were placed in calculated positions with C—H distances = 0.93 Å (aromatic), and were included in the final cycles of refinement in riding mode with Uiso(H) = 1.2Ueq(C). H atoms of amino groups and coordinated water molecule were located in a difference Fourier map and included in the structure factor calculations in riding mode with Uiso(H) = 1.2Ueq(N,O). H atoms of lattice water molecules were located in a difference Fourier map and refined as riding in their as-found relative positions, Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed lines showing the hydrogen bonding [symmetry code: (ii) 1 - x,2 - y,1 - z].
Bis(µ-pyridine-2,3-dicarboxylato)bis[aqua(2,2'-diamino-4,4'-bi-1,3-\ thiazole)cobalt(II)] decahydrate top
Crystal data top
[Co2(C7H3NO4)2(C6H6N4OS2)2(H2O)2]·10H2OZ = 1
Mr = 1060.80F(000) = 546
Triclinic, P1Dx = 1.674 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1415 (12) ÅCell parameters from 3550 reflections
b = 11.2685 (17) Åθ = 2.2–25.0°
c = 12.0084 (18) ŵ = 1.08 mm−1
α = 74.269 (2)°T = 295 K
β = 82.864 (2)°Prism, red
γ = 87.713 (2)°0.20 × 0.18 × 0.15 mm
V = 1052.2 (3) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		3653 independent reflections
Radiation source: fine-focus sealed tube2911 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 2.2°
ω scansh = −9→9
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −12→13
Tmin = 0.785, Tmax = 0.850l = −10→14
5510 measured reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0371P)2 + 0.1585P]
where P = (Fo2 + 2Fc2)/3
3653 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Co2(C7H3NO4)2(C6H6N4OS2)2(H2O)2]·10H2Oγ = 87.713 (2)°
Mr = 1060.80V = 1052.2 (3) Å3
Triclinic, P1Z = 1
a = 8.1415 (12) ÅMo Kα radiation
b = 11.2685 (17) ŵ = 1.08 mm−1
c = 12.0084 (18) ÅT = 295 K
α = 74.269 (2)°0.20 × 0.18 × 0.15 mm
β = 82.864 (2)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		3653 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2911 reflections with I > 2σ(I)
Tmin = 0.785, Tmax = 0.850Rint = 0.024
5510 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.35 e Å−3
S = 1.06Δρmin = −0.35 e Å−3
3653 reflectionsAbsolute structure: ?
280 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Co0.60678 (5)0.75306 (4)0.67792 (3)0.02432 (14)
O10.8327 (3)0.7076 (2)0.74704 (18)0.0352 (6)
H1A0.86720.73440.80510.042*
H1B0.85110.62020.75390.042*
O110.7251 (2)0.84018 (19)0.51418 (18)0.0283 (5)
O120.6872 (3)0.9176 (2)0.32782 (19)0.0430 (7)
O130.4141 (3)1.10459 (19)0.23638 (17)0.0310 (5)
O140.3918 (3)0.9300 (2)0.18751 (18)0.0346 (6)
O1W0.9293 (3)0.9688 (3)0.1480 (2)0.0643 (8)
H1WA0.87660.95450.21560.096*
H1WB0.86310.96210.10360.096*
O2W0.6777 (3)0.9173 (3)0.0296 (2)0.0668 (9)
H2WA0.60100.91360.08510.100*
H2WB0.64040.9555−0.03170.100*
O3W0.1478 (3)0.7661 (3)0.1589 (2)0.0578 (8)
H3WA0.06580.81440.15030.087*
H3WB0.21640.79970.18450.087*
O4W0.9238 (4)0.7896 (3)0.9211 (2)0.0692 (9)
H4WA0.83130.80990.95350.104*
H4WB0.97650.85430.89050.104*
O5W0.9981 (3)0.4713 (3)0.7438 (2)0.0580 (8)
H5WA1.08170.47150.77580.087*
H5WB0.94980.40130.77580.087*
N10.4475 (3)0.6361 (2)0.8125 (2)0.0277 (6)
N20.3392 (4)0.7576 (3)0.9341 (3)0.0496 (9)
H2A0.40100.82000.89670.060*
H2B0.27180.76460.99120.060*
N30.6356 (3)0.5797 (2)0.6344 (2)0.0292 (6)
N40.8368 (4)0.6102 (3)0.4712 (3)0.0466 (8)
H4A0.86280.68490.46600.056*
H4B0.89180.57620.42060.056*
N110.4028 (3)0.8234 (2)0.5804 (2)0.0244 (6)
S10.24658 (13)0.52066 (9)0.98787 (8)0.0504 (3)
S20.69105 (13)0.38950 (9)0.55697 (9)0.0494 (3)
C10.4354 (4)0.5161 (3)0.8048 (3)0.0318 (8)
C20.3348 (4)0.4416 (3)0.8901 (3)0.0461 (10)
H20.31530.35930.89580.055*
C30.3536 (4)0.6516 (3)0.9056 (3)0.0343 (8)
C40.5369 (4)0.4850 (3)0.7072 (3)0.0315 (8)
C50.5490 (5)0.3779 (3)0.6782 (3)0.0451 (10)
H50.48920.30730.71790.054*
C60.7259 (4)0.5416 (3)0.5516 (3)0.0347 (8)
C110.4513 (4)0.8779 (3)0.4665 (2)0.0219 (7)
C120.3387 (4)0.9247 (3)0.3874 (3)0.0225 (7)
C130.1700 (4)0.9115 (3)0.4278 (3)0.0287 (7)
H130.09120.94000.37680.034*
C140.1218 (4)0.8561 (3)0.5432 (3)0.0292 (8)
H140.01010.84660.57150.035*
C150.2420 (4)0.8144 (3)0.6168 (3)0.0294 (8)
H150.20860.77850.69530.035*
C160.6369 (4)0.8799 (3)0.4317 (3)0.0251 (7)
C170.3888 (4)0.9916 (3)0.2608 (3)0.0267 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co0.0253 (2)0.0238 (3)0.0231 (2)−0.00139 (18)−0.00092 (17)−0.00574 (18)
O10.0353 (13)0.0335 (14)0.0382 (14)−0.0013 (10)−0.0107 (10)−0.0090 (11)
O110.0217 (12)0.0335 (13)0.0282 (12)−0.0005 (10)−0.0003 (9)−0.0071 (10)
O120.0309 (14)0.0640 (18)0.0259 (13)0.0036 (12)0.0064 (10)−0.0032 (12)
O130.0436 (14)0.0247 (13)0.0244 (12)−0.0022 (10)−0.0013 (10)−0.0070 (10)
O140.0486 (15)0.0332 (14)0.0252 (12)−0.0035 (11)−0.0032 (10)−0.0132 (10)
O1W0.0445 (17)0.096 (2)0.0495 (18)−0.0068 (16)0.0110 (13)−0.0213 (16)
O2W0.0565 (18)0.104 (3)0.0370 (16)0.0172 (17)−0.0063 (13)−0.0152 (16)
O3W0.0556 (18)0.068 (2)0.0555 (18)0.0012 (15)−0.0085 (14)−0.0250 (15)
O4W0.064 (2)0.079 (2)0.078 (2)0.0005 (17)−0.0182 (16)−0.0410 (18)
O5W0.0528 (18)0.070 (2)0.0552 (18)0.0086 (15)−0.0105 (14)−0.0224 (15)
N10.0281 (15)0.0266 (15)0.0251 (15)0.0004 (12)−0.0002 (12)−0.0030 (12)
N20.057 (2)0.045 (2)0.0430 (19)−0.0086 (16)0.0228 (16)−0.0177 (16)
N30.0276 (15)0.0267 (15)0.0347 (16)0.0009 (12)−0.0036 (12)−0.0107 (13)
N40.050 (2)0.0421 (19)0.048 (2)−0.0006 (15)0.0140 (16)−0.0209 (16)
N110.0244 (14)0.0229 (14)0.0249 (14)−0.0020 (11)0.0007 (11)−0.0057 (11)
S10.0504 (6)0.0504 (6)0.0390 (6)−0.0131 (5)0.0117 (5)0.0015 (5)
S20.0630 (7)0.0339 (6)0.0588 (7)0.0044 (5)−0.0069 (5)−0.0261 (5)
C10.0314 (19)0.0279 (19)0.0337 (19)−0.0034 (15)−0.0088 (15)−0.0013 (15)
C20.049 (2)0.033 (2)0.051 (2)−0.0106 (18)−0.0011 (19)−0.0032 (18)
C30.0319 (19)0.037 (2)0.0279 (19)0.0003 (16)0.0003 (15)−0.0006 (16)
C40.036 (2)0.0237 (18)0.036 (2)0.0004 (15)−0.0118 (15)−0.0067 (15)
C50.056 (3)0.028 (2)0.053 (2)−0.0035 (18)−0.0084 (19)−0.0115 (18)
C60.038 (2)0.030 (2)0.042 (2)0.0078 (16)−0.0081 (16)−0.0182 (16)
C110.0256 (17)0.0191 (16)0.0233 (17)−0.0011 (13)−0.0037 (13)−0.0090 (13)
C120.0271 (17)0.0187 (16)0.0241 (17)0.0005 (13)−0.0022 (13)−0.0103 (13)
C130.0276 (18)0.0292 (19)0.0326 (19)0.0040 (14)−0.0079 (14)−0.0124 (15)
C140.0216 (17)0.0306 (19)0.0352 (19)−0.0021 (14)0.0032 (14)−0.0111 (15)
C150.0287 (18)0.0311 (19)0.0267 (18)−0.0028 (14)0.0026 (14)−0.0073 (14)
C160.0267 (17)0.0217 (17)0.0282 (19)−0.0007 (13)0.0004 (14)−0.0101 (14)
C170.0240 (17)0.030 (2)0.0266 (18)0.0013 (14)−0.0055 (13)−0.0071 (15)
Geometric parameters (Å, °) top
Co—O12.100 (2)N2—H2B0.8421
Co—O112.077 (2)N3—C61.319 (4)
Co—O13i2.119 (2)N3—C41.392 (4)
Co—N12.119 (2)N4—C61.334 (4)
Co—N32.151 (3)N4—H4A0.8603
Co—N112.152 (3)N4—H4B0.8727
O1—H1A0.9091N11—C151.326 (4)
O1—H1B0.9730N11—C111.354 (4)
O11—C161.268 (4)S1—C21.730 (4)
O12—C161.226 (4)S1—C31.735 (3)
O13—C171.246 (4)S2—C51.721 (4)
O13—Coi2.119 (2)S2—C61.731 (3)
O14—C171.258 (4)C1—C21.344 (4)
O1W—H1WA0.8476C1—C41.462 (4)
O1W—H1WB0.8222C2—H20.9300
O2W—H2WA0.8481C4—C51.342 (5)
O2W—H2WB0.8324C5—H50.9300
O3W—H3WA0.8428C11—C121.388 (4)
O3W—H3WB0.8205C11—C161.517 (4)
O4W—H4WA0.8557C12—C131.398 (4)
O4W—H4WB0.8309C12—C171.515 (4)
O5W—H5WA0.8221C13—C141.371 (4)
O5W—H5WB0.8637C13—H130.9300
N1—C31.322 (4)C14—C151.383 (4)
N1—C11.388 (4)C14—H140.9300
N2—C31.326 (4)C15—H150.9300
N2—H2A0.8659
O11—Co—O192.19 (8)C5—S2—C689.78 (17)
O11—Co—O13i102.79 (8)C2—C1—N1115.8 (3)
O1—Co—O13i86.43 (9)C2—C1—C4127.8 (3)
O11—Co—N1161.66 (10)N1—C1—C4116.3 (3)
O1—Co—N199.38 (9)C1—C2—S1110.3 (3)
O13i—Co—N192.16 (9)C1—C2—H2124.9
O11—Co—N389.33 (9)S1—C2—H2124.9
O1—Co—N385.08 (9)N1—C3—N2123.7 (3)
O13i—Co—N3165.46 (9)N1—C3—S1114.1 (3)
N1—Co—N377.62 (10)N2—C3—S1122.2 (3)
O11—Co—N1177.37 (8)C5—C4—N3115.4 (3)
O1—Co—N11169.15 (9)C5—C4—C1129.1 (3)
O13i—Co—N1192.97 (9)N3—C4—C1115.5 (3)
N1—Co—N1191.47 (9)C4—C5—S2110.4 (3)
N3—Co—N1197.56 (10)C4—C5—H5124.8
Co—O1—H1A125.8S2—C5—H5124.8
Co—O1—H1B106.3N3—C6—N4124.8 (3)
H1A—O1—H1B114.7N3—C6—S2113.6 (3)
C16—O11—Co118.08 (19)N4—C6—S2121.6 (3)
C17—O13—Coi138.2 (2)N11—C11—C12122.3 (3)
H1WA—O1W—H1WB107.0N11—C11—C16114.9 (3)
H2WA—O2W—H2WB107.4C12—C11—C16122.8 (3)
H3WA—O3W—H3WB106.3C11—C12—C13118.0 (3)
H4WA—O4W—H4WB107.1C11—C12—C17123.6 (3)
H5WA—O5W—H5WB107.3C13—C12—C17118.5 (3)
C3—N1—C1110.5 (3)C14—C13—C12119.5 (3)
C3—N1—Co133.9 (2)C14—C13—H13120.3
C1—N1—Co115.6 (2)C12—C13—H13120.3
C3—N2—H2A121.2C13—C14—C15118.9 (3)
C3—N2—H2B120.2C13—C14—H14120.6
H2A—N2—H2B118.5C15—C14—H14120.6
C6—N3—C4110.9 (3)N11—C15—C14122.9 (3)
C6—N3—Co134.3 (2)N11—C15—H15118.5
C4—N3—Co114.8 (2)C14—C15—H15118.5
C6—N4—H4A125.9O12—C16—O11126.4 (3)
C6—N4—H4B118.0O12—C16—C11117.7 (3)
H4A—N4—H4B116.0O11—C16—C11115.9 (3)
C15—N11—C11118.4 (3)O13—C17—O14124.9 (3)
C15—N11—Co128.4 (2)O13—C17—C12117.7 (3)
C11—N11—Co113.05 (19)O14—C17—C12117.2 (3)
C2—S1—C389.32 (17)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O4W0.911.792.694 (4)177
O1—H1B···O5W0.972.042.943 (4)153
N2—H2A···O13i0.872.082.853 (4)149
N2—H2B···O3Wii0.842.142.968 (4)167
N4—H4A···O110.862.212.869 (4)133
N4—H4B···O5Wiii0.872.253.105 (4)165
O1W—H1WA···O120.851.902.690 (3)156
O1W—H1WB···O2W0.821.992.796 (4)166
O2W—H2WA···O140.852.012.839 (3)167
O2W—H2WB···O14iv0.832.012.817 (3)165
O3W—H3WA···O1Wv0.842.022.823 (4)158
O3W—H3WB···O140.822.102.878 (4)159
O4W—H4WA···O2Wii0.862.012.814 (4)155
O4W—H4WB···O1Wvi0.832.082.884 (5)164
O5W—H5WB···O3Wvii0.861.992.854 (4)175
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) x−1, y, z; (vi) −x+2, −y+2, −z+1; (vii) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Co—O12.100 (2)Co—N12.119 (2)
Co—O112.077 (2)Co—N32.151 (3)
Co—O13i2.119 (2)Co—N112.152 (3)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O4W0.911.792.694 (4)177
O1—H1B···O5W0.972.042.943 (4)153
N2—H2A···O13i0.872.082.853 (4)149
N2—H2B···O3Wii0.842.142.968 (4)167
N4—H4A···O110.862.212.869 (4)133
N4—H4B···O5Wiii0.872.253.105 (4)165
O1W—H1WA···O120.851.902.690 (3)156
O1W—H1WB···O2W0.821.992.796 (4)166
O2W—H2WA···O140.852.012.839 (3)167
O2W—H2WB···O14iv0.832.012.817 (3)165
O3W—H3WA···O1Wv0.842.022.823 (4)158
O3W—H3WB···O140.822.102.878 (4)159
O4W—H4WA···O2Wii0.862.012.814 (4)155
O4W—H4WB···O1Wvi0.832.082.884 (5)164
O5W—H5WB···O3Wvii0.861.992.854 (4)175
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) x−1, y, z; (vi) −x+2, −y+2, −z+1; (vii) −x+1, −y+1, −z+1.
Acknowledgements top

This project was supported by the Educational Development Foundation of Shanghai Educational Committee, China (grant No. AB0448).

references
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