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Acta Cryst. (2010). E66, m569    [ doi:10.1107/S1600536810014522 ]

Bis([mu]-5-hydroxy-2-{[2-(N-phenylthiocarbamoyl)hydrazin-1-ylidene]methyl}phenolato)bis[chloridozinc(II)] N,N-dimethylformamide tetrasolvate

K. W. Tan, C. H. Ng, M. J. Maah and S. W. Ng

Abstract top

In the dinuclear title compound, [Zn2(C14H12N3O2S)2Cl2]·4C3H7NO, the two monodeprotonated Schiff base ligands N,O,S:O-chelate to Zn atoms. The formally negatively charged O atom involved in chelation also serves as a bridge. The O, O', N and S atoms comprise a square, and the Cl atom the apex of a square pyramid surrounding each metal atom. The solvate dimethylformamide molecules, one of which is disordered over two positions in a 3:1 ratio, are hydrogen bonded to the dinuclear molecule.

Related literature top

For related zinc complexes, see: Tan et al. (2009a,b).

Experimental top

Zinc chloride (0.14 g, 1 mmol) and 2,4-dihydroxybenzaldehyde 4-phenyl thiosemicarbazone (0.29 g, 1 mmol) were heated in ethanol (20 ml) for 3 hours. The compound that separated on cooling the solution was recrystallized from a mixture of ethanol and DMF.

Refinement top

Carbon-, nitrogen- and oxygen-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98, N–H 0.86, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C,N,O).

One of the four DMF molecules is disordered over two positions; as the disorder refined to a near 3:1 ratio, this is fixed as exactly 3:1. Pairs of distances were restrained to within 0.01 Å of each other. Each component was restrained to be nearly flat. The anisotropic temperature factors were restrained to be nearly isotropic.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Zn2Cl2(C14H12N3O2S)2.4DMF at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the four DMF molecules is not shown.
Bis(µ-5-hydroxy-2-{[2-(N-phenylthiocarbamoyl)hydrazin-1- ylidene]methyl}phenolato)bis[chloridozinc(II)] N,N-dimethylformamide tetrasolvate top
Crystal data top
[Zn2(C14H12N3O2S)2Cl2]·4C3H7NOZ = 2
Mr = 1066.68F(000) = 1104
Triclinic, P1Dx = 1.527 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1913 (4) ÅCell parameters from 1271 reflections
b = 17.6402 (7) Åθ = 2.3–19.6°
c = 17.9597 (7) ŵ = 1.30 mm−1
α = 64.941 (3)°T = 100 K
β = 81.213 (3)°Prism, yellow
γ = 89.103 (3)°0.12 × 0.08 × 0.04 mm
V = 2319.76 (17) Å3
Data collection top
Bruker SMART APEX
diffractometer		8106 independent reflections
Radiation source: fine-focus sealed tube4918 reflections with I > 2σ(I)
graphiteRint = 0.071
ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.860, Tmax = 0.950k = −20→20
15848 measured reflectionsl = −20→21
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0745P)2]
where P = (Fo2 + 2Fc2)/3
8106 reflections(Δ/σ)max = 0.001
634 parametersΔρmax = 0.59 e Å−3
68 restraintsΔρmin = −0.70 e Å−3
Crystal data top
[Zn2(C14H12N3O2S)2Cl2]·4C3H7NOγ = 89.103 (3)°
Mr = 1066.68V = 2319.76 (17) Å3
Triclinic, P1Z = 2
a = 8.1913 (4) ÅMo Kα radiation
b = 17.6402 (7) ŵ = 1.30 mm−1
c = 17.9597 (7) ÅT = 100 K
α = 64.941 (3)°0.12 × 0.08 × 0.04 mm
β = 81.213 (3)°
Data collection top
Bruker SMART APEX
diffractometer		8106 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4918 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.950Rint = 0.071
15848 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.161Δρmax = 0.59 e Å−3
S = 0.97Δρmin = −0.70 e Å−3
8106 reflectionsAbsolute structure: ?
634 parametersFlack parameter: ?
68 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.41630 (9)0.73410 (4)0.85750 (4)0.0238 (2)
Zn20.50793 (9)0.77020 (4)0.66356 (4)0.0224 (2)
Cl10.16292 (19)0.66906 (9)0.92067 (9)0.0294 (4)
Cl20.2909 (2)0.78623 (10)0.59478 (10)0.0332 (4)
S10.4684 (2)0.81633 (9)0.93413 (9)0.0273 (4)
S20.7294 (2)0.71361 (9)0.60021 (10)0.0292 (4)
O10.4913 (5)0.6764 (2)0.7795 (2)0.0245 (10)
O20.5357 (6)0.4359 (3)0.7225 (3)0.0408 (12)
H2o0.50360.46940.67850.061*
O30.4394 (5)0.8279 (2)0.7412 (2)0.0239 (9)
O40.1114 (5)1.0395 (2)0.7781 (3)0.0294 (10)
H4o0.08491.00100.82620.044*
O60.0090 (6)0.9223 (3)0.9310 (3)0.0423 (12)
O70.8112 (5)0.5952 (3)1.1131 (3)0.0360 (11)
O81.0048 (5)0.9906 (2)0.4063 (2)0.0288 (10)
N10.5986 (6)0.6606 (3)0.9244 (3)0.0260 (12)
N20.6490 (6)0.6813 (3)0.9837 (3)0.0293 (13)
H20.72040.65061.01430.035*
N30.6376 (7)0.7521 (3)1.0620 (3)0.0319 (13)
H30.69760.71431.08850.038*
N40.6596 (6)0.8812 (3)0.5933 (3)0.0196 (11)
N50.7916 (6)0.8787 (3)0.5369 (3)0.0231 (12)
H50.85010.92510.50240.028*
N60.9575 (6)0.8135 (3)0.4732 (3)0.0244 (12)
H61.00630.86120.44720.029*
N80.0525 (7)0.8249 (3)1.0570 (3)0.0289 (13)
N90.9143 (6)0.4839 (3)1.2119 (3)0.0286 (12)
N101.0845 (6)1.1074 (3)0.2867 (3)0.0319 (13)
C10.5341 (7)0.5977 (3)0.8007 (4)0.0225 (14)
C20.5085 (7)0.5574 (3)0.7506 (4)0.0268 (15)
H2A0.45780.58590.70270.032*
C30.5561 (8)0.4766 (4)0.7704 (4)0.0313 (16)
C40.6296 (8)0.4348 (4)0.8402 (4)0.0350 (17)
H4A0.66380.37960.85310.042*
C50.6531 (8)0.4718 (4)0.8898 (4)0.0337 (16)
H5A0.70160.44150.93820.040*
C60.6075 (7)0.5545 (4)0.8720 (4)0.0268 (15)
C70.6436 (8)0.5892 (4)0.9270 (4)0.0277 (15)
H7A0.70620.55690.96910.033*
C80.5905 (8)0.7475 (4)0.9951 (4)0.0263 (15)
C90.5975 (8)0.8134 (4)1.0929 (4)0.0300 (15)
C100.5199 (10)0.7877 (4)1.1740 (4)0.045 (2)
H100.49010.73011.20820.054*
C110.4855 (11)0.8470 (5)1.2053 (5)0.056 (2)
H110.43200.82961.26120.067*
C120.5281 (9)0.9301 (5)1.1565 (4)0.0412 (18)
H120.50370.97001.17870.049*
C130.6059 (9)0.9564 (4)1.0753 (5)0.0412 (18)
H130.63551.01411.04160.049*
C140.6406 (8)0.8978 (4)1.0435 (4)0.0339 (16)
H140.69410.91550.98750.041*
C150.3996 (7)0.9082 (3)0.7144 (3)0.0207 (13)
C160.2762 (7)0.9312 (3)0.7617 (3)0.0203 (13)
H160.21960.88990.81280.024*
C170.2344 (7)1.0147 (4)0.7347 (4)0.0239 (14)
C180.3160 (8)1.0763 (4)0.6607 (4)0.0261 (15)
H180.28711.13300.64270.031*
C190.4385 (7)1.0544 (3)0.6138 (4)0.0240 (14)
H190.49521.09690.56350.029*
C200.4839 (7)0.9705 (3)0.6375 (3)0.0207 (13)
C210.6179 (7)0.9557 (4)0.5841 (4)0.0250 (14)
H210.67891.00270.53980.030*
C220.8311 (7)0.8049 (4)0.5348 (4)0.0231 (14)
C231.0165 (7)0.7507 (4)0.4479 (4)0.0273 (15)
C241.0604 (8)0.7757 (4)0.3625 (4)0.0389 (18)
H241.04910.83190.32430.047*
C251.1209 (10)0.7171 (5)0.3341 (5)0.058 (2)
H251.15170.73420.27590.069*
C261.1372 (10)0.6363 (5)0.3869 (5)0.054 (2)
H261.17890.59720.36620.065*
C271.0927 (10)0.6124 (5)0.4704 (5)0.055 (2)
H271.10140.55560.50790.066*
C281.0351 (9)0.6691 (4)0.5015 (4)0.045 (2)
H281.00850.65150.56000.054*
C320.0373 (8)0.8497 (4)0.9781 (4)0.0338 (16)
H320.04870.80940.95580.041*
C330.0466 (10)0.8813 (4)1.0970 (4)0.0449 (19)
H33A0.02830.93801.05690.067*
H33B0.15160.88151.11680.067*
H33C−0.04410.86241.14430.067*
C340.0917 (10)0.7388 (4)1.1072 (4)0.045 (2)
H34A0.19970.73891.12420.067*
H34B0.09490.70641.07420.067*
H34C0.00670.71351.15670.067*
C350.8629 (8)0.5233 (4)1.1402 (4)0.0337 (16)
H350.86530.49441.10580.040*
C360.9132 (11)0.5215 (4)1.2697 (4)0.054 (2)
H36A0.87040.57761.24590.081*
H36B1.02610.52581.27990.081*
H36C0.84230.48661.32230.081*
C370.9689 (9)0.3989 (4)1.2394 (4)0.0415 (18)
H37A0.97970.38251.19320.062*
H37B0.88770.36061.28580.062*
H37C1.07630.39631.25790.062*
C380.9962 (8)1.0668 (4)0.3608 (4)0.0267 (15)
H380.92061.09750.38140.032*
C391.1953 (8)1.0671 (5)0.2467 (4)0.0430 (19)
H39A1.30791.09160.23560.065*
H39B1.16081.07510.19410.065*
H39C1.19291.00700.28310.065*
C401.0718 (10)1.1982 (4)0.2402 (5)0.055 (2)
H40A0.98871.21810.27210.083*
H40B1.03891.20980.18630.083*
H40C1.17921.22700.23110.083*
O50.4714 (11)0.5477 (6)0.5814 (5)0.060 (2)0.75
N70.5710 (9)0.6399 (6)0.4550 (7)0.039 (2)0.75
C290.5636 (14)0.5685 (8)0.5180 (8)0.071 (4)0.75
H290.63910.52880.51330.085*0.75
C300.4685 (14)0.7083 (6)0.4500 (7)0.057 (3)0.75
H30A0.38660.69070.50090.086*0.75
H30B0.41150.72460.40170.086*0.75
H30C0.53760.75600.44400.086*0.75
C310.6916 (14)0.6569 (8)0.3799 (7)0.069 (3)0.75
H31A0.76730.61120.39110.103*0.75
H31B0.75480.70970.36380.103*0.75
H31C0.63350.66120.33460.103*0.75
O5'0.379 (3)0.5363 (15)0.5975 (14)0.053 (7)0.25
N7'0.554 (3)0.613 (2)0.493 (2)0.085 (18)0.25
C29'0.412 (3)0.6011 (14)0.5386 (14)0.043 (7)0.25
H29'0.33450.64340.52530.052*0.25
C30'0.591 (5)0.693 (2)0.422 (2)0.075 (13)0.25
H30D0.57220.68680.37190.112*0.25
H30E0.70660.71070.41550.112*0.25
H30F0.51860.73440.42970.112*0.25
C31'0.699 (4)0.5632 (18)0.4958 (19)0.050 (8)0.25
H31D0.69130.51650.55120.074*0.25
H31E0.79930.59830.48400.074*0.25
H31F0.70240.54100.45390.074*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0287 (4)0.0219 (4)0.0169 (4)0.0053 (3)−0.0028 (3)−0.0048 (3)
Zn20.0261 (4)0.0203 (4)0.0175 (4)0.0028 (3)−0.0025 (3)−0.0051 (3)
Cl10.0299 (9)0.0307 (9)0.0230 (8)0.0019 (7)−0.0032 (7)−0.0074 (7)
Cl20.0311 (9)0.0346 (9)0.0289 (9)0.0010 (7)−0.0090 (7)−0.0072 (7)
S10.0324 (9)0.0255 (9)0.0215 (8)0.0047 (7)−0.0063 (7)−0.0071 (7)
S20.0323 (9)0.0212 (8)0.0273 (9)0.0030 (7)0.0017 (7)−0.0061 (7)
O10.034 (3)0.017 (2)0.017 (2)0.0053 (18)−0.0033 (19)−0.0023 (18)
O20.058 (3)0.024 (3)0.042 (3)0.010 (2)−0.013 (3)−0.014 (2)
O30.030 (2)0.019 (2)0.018 (2)0.0033 (18)−0.0009 (19)−0.0038 (18)
O40.030 (2)0.031 (3)0.026 (2)0.009 (2)0.003 (2)−0.014 (2)
O60.052 (3)0.042 (3)0.025 (3)0.016 (2)−0.004 (2)−0.008 (2)
O70.045 (3)0.025 (3)0.026 (2)0.006 (2)−0.010 (2)0.001 (2)
O80.031 (3)0.024 (2)0.026 (2)0.0010 (18)−0.001 (2)−0.006 (2)
N10.031 (3)0.025 (3)0.017 (3)0.004 (2)−0.006 (2)−0.003 (2)
N20.033 (3)0.030 (3)0.025 (3)0.009 (2)−0.011 (3)−0.010 (3)
N30.046 (4)0.026 (3)0.024 (3)0.008 (3)−0.015 (3)−0.008 (2)
N40.020 (3)0.022 (3)0.013 (2)0.006 (2)−0.001 (2)−0.005 (2)
N50.024 (3)0.025 (3)0.016 (3)0.001 (2)0.004 (2)−0.006 (2)
N60.027 (3)0.018 (3)0.022 (3)0.001 (2)0.005 (2)−0.006 (2)
N80.043 (3)0.023 (3)0.019 (3)0.007 (2)−0.002 (3)−0.009 (2)
N90.031 (3)0.029 (3)0.025 (3)0.004 (2)−0.012 (3)−0.008 (3)
N100.028 (3)0.030 (3)0.024 (3)−0.005 (2)−0.004 (3)0.001 (3)
C10.024 (3)0.012 (3)0.023 (3)0.005 (2)0.003 (3)−0.002 (3)
C20.029 (4)0.016 (3)0.026 (3)0.003 (3)0.000 (3)−0.001 (3)
C30.033 (4)0.028 (4)0.035 (4)0.005 (3)0.002 (3)−0.017 (3)
C40.042 (4)0.015 (3)0.037 (4)0.008 (3)−0.004 (3)−0.001 (3)
C50.038 (4)0.024 (4)0.028 (4)0.001 (3)0.001 (3)−0.002 (3)
C60.028 (4)0.019 (3)0.023 (3)0.001 (3)0.001 (3)0.000 (3)
C70.031 (4)0.025 (4)0.023 (3)0.011 (3)−0.005 (3)−0.006 (3)
C80.030 (4)0.022 (3)0.020 (3)−0.001 (3)−0.005 (3)−0.002 (3)
C90.037 (4)0.029 (4)0.025 (4)0.001 (3)−0.017 (3)−0.009 (3)
C100.074 (6)0.030 (4)0.030 (4)−0.007 (4)−0.013 (4)−0.009 (3)
C110.089 (7)0.051 (5)0.031 (4)−0.014 (5)−0.008 (4)−0.021 (4)
C120.048 (5)0.043 (5)0.038 (4)0.001 (4)−0.016 (4)−0.020 (4)
C130.041 (4)0.031 (4)0.051 (5)0.003 (3)−0.015 (4)−0.014 (4)
C140.039 (4)0.028 (4)0.032 (4)0.003 (3)−0.008 (3)−0.010 (3)
C150.025 (3)0.024 (3)0.017 (3)0.005 (3)−0.011 (3)−0.011 (3)
C160.022 (3)0.022 (3)0.015 (3)0.000 (2)−0.003 (3)−0.007 (3)
C170.017 (3)0.033 (4)0.027 (3)0.010 (3)−0.010 (3)−0.017 (3)
C180.037 (4)0.022 (3)0.021 (3)0.012 (3)−0.012 (3)−0.009 (3)
C190.027 (3)0.019 (3)0.019 (3)0.003 (3)−0.006 (3)0.000 (3)
C200.021 (3)0.025 (3)0.013 (3)0.005 (2)−0.004 (3)−0.006 (3)
C210.024 (3)0.029 (4)0.018 (3)−0.001 (3)−0.005 (3)−0.005 (3)
C220.024 (3)0.026 (3)0.021 (3)0.005 (3)−0.010 (3)−0.009 (3)
C230.026 (4)0.029 (4)0.026 (4)0.004 (3)−0.004 (3)−0.012 (3)
C240.044 (4)0.042 (4)0.030 (4)0.014 (3)−0.007 (3)−0.015 (3)
C250.071 (6)0.072 (6)0.034 (4)0.018 (5)−0.001 (4)−0.030 (5)
C260.055 (5)0.048 (5)0.067 (6)0.012 (4)0.001 (5)−0.037 (5)
C270.072 (6)0.035 (4)0.050 (5)0.012 (4)0.012 (4)−0.018 (4)
C280.059 (5)0.038 (4)0.032 (4)0.019 (4)0.002 (4)−0.013 (4)
C320.030 (4)0.035 (4)0.033 (4)0.009 (3)0.002 (3)−0.014 (3)
C330.069 (5)0.032 (4)0.035 (4)0.016 (4)−0.013 (4)−0.015 (3)
C340.073 (6)0.023 (4)0.035 (4)0.009 (4)−0.009 (4)−0.011 (3)
C350.027 (4)0.039 (4)0.029 (4)0.000 (3)−0.009 (3)−0.007 (3)
C360.089 (7)0.039 (5)0.034 (4)0.013 (4)−0.024 (4)−0.010 (4)
C370.046 (5)0.029 (4)0.038 (4)0.009 (3)−0.012 (4)−0.002 (3)
C380.028 (4)0.027 (4)0.026 (4)−0.001 (3)−0.006 (3)−0.012 (3)
C390.038 (4)0.064 (5)0.025 (4)−0.007 (4)−0.009 (3)−0.015 (4)
C400.051 (5)0.042 (5)0.047 (5)−0.003 (4)−0.020 (4)0.010 (4)
O50.067 (6)0.074 (5)0.037 (4)−0.003 (5)−0.010 (4)−0.021 (4)
N70.047 (5)0.028 (5)0.044 (5)−0.004 (4)−0.020 (4)−0.012 (4)
C290.084 (8)0.065 (8)0.077 (8)0.002 (6)−0.018 (6)−0.041 (6)
C300.059 (6)0.058 (6)0.060 (6)0.021 (5)−0.009 (5)−0.031 (5)
C310.076 (7)0.084 (7)0.060 (6)−0.002 (6)−0.013 (6)−0.043 (6)
O5'0.054 (11)0.057 (10)0.051 (11)0.001 (8)−0.020 (8)−0.020 (8)
N7'0.10 (2)0.08 (2)0.09 (2)−0.016 (9)−0.018 (10)−0.046 (12)
C29'0.053 (11)0.041 (11)0.045 (11)0.008 (8)−0.008 (9)−0.027 (8)
C30'0.070 (15)0.081 (15)0.077 (15)0.001 (10)−0.012 (9)−0.035 (10)
C31'0.049 (11)0.049 (11)0.052 (11)0.002 (9)−0.012 (9)−0.022 (9)
Geometric parameters (Å, °) top
Zn1—N12.127 (5)C15—C161.388 (7)
Zn1—O12.073 (4)C15—C201.427 (8)
Zn1—O32.024 (4)C16—C171.396 (8)
Zn1—S12.464 (2)C16—H160.9500
Zn1—Cl12.272 (2)C17—C181.387 (8)
Zn2—O12.024 (4)C18—C191.369 (8)
Zn2—O32.061 (4)C18—H180.9500
Zn2—N42.116 (5)C19—C201.416 (8)
Zn2—S22.420 (2)C19—H190.9500
Zn2—Cl22.264 (2)C20—C211.441 (8)
S1—C81.686 (6)C21—H210.9500
S2—C221.675 (6)C23—C281.375 (9)
O1—C11.332 (6)C23—C241.394 (9)
O2—C31.360 (7)C24—C251.387 (9)
O2—H2o0.8400C24—H240.9500
O3—C151.341 (6)C25—C261.356 (10)
O4—C171.359 (7)C25—H250.9500
O4—H4o0.8400C26—C271.363 (10)
O6—C321.241 (7)C26—H260.9500
O7—C351.245 (7)C27—C281.383 (9)
O8—C381.250 (7)C27—H270.9500
N1—C71.290 (7)C28—H280.9500
N1—N21.380 (7)C32—H320.9500
N2—C81.339 (7)C33—H33A0.9800
N2—H20.8800C33—H33B0.9800
N3—C81.352 (8)C33—H33C0.9800
N3—C91.423 (8)C34—H34A0.9800
N3—H30.8400C34—H34B0.9800
N4—C211.299 (7)C34—H34C0.9800
N4—N51.377 (6)C35—H350.9500
N5—C221.351 (7)C36—H36A0.9800
N5—H50.8800C36—H36B0.9800
N6—C221.354 (7)C36—H36C0.9800
N6—C231.417 (7)C37—H37A0.9800
N6—H60.8400C37—H37B0.9800
N8—C321.320 (8)C37—H37C0.9800
N8—C331.450 (8)C38—H380.9500
N8—C341.461 (7)C39—H39A0.9800
N9—C351.311 (8)C39—H39B0.9800
N9—C361.449 (8)C39—H39C0.9800
N9—C371.452 (7)C40—H40A0.9800
N10—C381.313 (7)C40—H40B0.9800
N10—C391.434 (8)C40—H40C0.9800
N10—C401.470 (8)O5—C291.180 (14)
C1—C21.400 (8)N7—C291.282 (18)
C1—C61.406 (8)N7—C301.437 (11)
C2—C31.381 (8)N7—C311.465 (14)
C2—H2A0.9500C29—H290.9500
C3—C41.382 (9)C30—H30A0.9800
C4—C51.344 (9)C30—H30B0.9800
C4—H4A0.9500C30—H30C0.9800
C5—C61.413 (8)C31—H31A0.9800
C5—H5A0.9500C31—H31B0.9800
C6—C71.431 (9)C31—H31C0.9800
C7—H7A0.9500O5'—C29'1.182 (16)
C9—C101.378 (9)N7'—C29'1.27 (2)
C9—C141.391 (8)N7'—C30'1.437 (15)
C10—C111.388 (9)N7'—C31'1.464 (16)
C10—H100.9500C29'—H29'0.9500
C11—C121.369 (10)C30'—H30D0.9800
C11—H110.9500C30'—H30E0.9800
C12—C131.378 (10)C30'—H30F0.9800
C12—H120.9500C31'—H31D0.9800
C13—C141.385 (9)C31'—H31E0.9800
C13—H130.9500C31'—H31F0.9800
C14—H140.9500
O3—Zn1—O175.50 (14)O4—C17—C18116.8 (5)
O3—Zn1—N1130.41 (17)O4—C17—C16122.4 (5)
O1—Zn1—N182.67 (17)C18—C17—C16120.8 (5)
O3—Zn1—Cl1118.76 (12)C19—C18—C17119.1 (5)
O1—Zn1—Cl1101.42 (12)C19—C18—H18120.4
N1—Zn1—Cl1108.86 (14)C17—C18—H18120.4
O3—Zn1—S199.12 (12)C18—C19—C20122.3 (5)
O1—Zn1—S1152.95 (13)C18—C19—H19118.8
N1—Zn1—S181.11 (14)C20—C19—H19118.8
Cl1—Zn1—S1104.25 (6)C19—C20—C15117.6 (5)
O1—Zn2—O375.80 (15)C19—C20—C21117.1 (5)
O1—Zn2—N4135.26 (17)C15—C20—C21125.2 (5)
O3—Zn2—N483.09 (16)N4—C21—C20123.3 (5)
O1—Zn2—Cl2118.39 (13)N4—C21—H21118.3
O3—Zn2—Cl2103.72 (12)C20—C21—H21118.3
N4—Zn2—Cl2104.65 (13)N5—C22—N6112.7 (5)
O1—Zn2—S295.77 (11)N5—C22—S2123.0 (4)
O3—Zn2—S2146.98 (13)N6—C22—S2124.3 (4)
N4—Zn2—S281.05 (12)C28—C23—C24119.1 (6)
Cl2—Zn2—S2108.23 (6)C28—C23—N6124.6 (6)
C8—S1—Zn196.0 (2)C24—C23—N6116.4 (5)
C22—S2—Zn297.4 (2)C25—C24—C23118.9 (7)
C1—O1—Zn2127.7 (4)C25—C24—H24120.5
C1—O1—Zn1127.9 (4)C23—C24—H24120.5
Zn2—O1—Zn1104.11 (16)C26—C25—C24122.0 (7)
C3—O2—H2o109.5C26—C25—H25119.0
C15—O3—Zn1131.1 (3)C24—C25—H25119.0
C15—O3—Zn2123.7 (3)C25—C26—C27118.6 (7)
Zn1—O3—Zn2104.55 (16)C25—C26—H26120.7
C17—O4—H4o109.5C27—C26—H26120.7
C7—N1—N2115.3 (5)C26—C27—C28121.4 (7)
C7—N1—Zn1126.0 (4)C26—C27—H27119.3
N2—N1—Zn1117.2 (4)C28—C27—H27119.3
C8—N2—N1120.7 (5)C23—C28—C27120.0 (7)
C8—N2—H2119.6C23—C28—H28120.0
N1—N2—H2119.6C27—C28—H28120.0
C8—N3—C9127.7 (5)O6—C32—N8124.4 (6)
C8—N3—H3116.2O6—C32—H32117.8
C9—N3—H3116.2N8—C32—H32117.8
C21—N4—N5115.5 (5)N8—C33—H33A109.5
C21—N4—Zn2124.8 (4)N8—C33—H33B109.5
N5—N4—Zn2117.6 (3)H33A—C33—H33B109.5
C22—N5—N4119.8 (5)N8—C33—H33C109.5
C22—N5—H5120.1H33A—C33—H33C109.5
N4—N5—H5120.1H33B—C33—H33C109.5
C22—N6—C23127.0 (5)N8—C34—H34A109.5
C22—N6—H6116.5N8—C34—H34B109.5
C23—N6—H6116.5H34A—C34—H34B109.5
C32—N8—C33123.1 (5)N8—C34—H34C109.5
C32—N8—C34120.8 (5)H34A—C34—H34C109.5
C33—N8—C34115.9 (5)H34B—C34—H34C109.5
C35—N9—C36121.6 (6)O7—C35—N9125.8 (7)
C35—N9—C37122.0 (6)O7—C35—H35117.1
C36—N9—C37116.3 (5)N9—C35—H35117.1
C38—N10—C39123.0 (6)N9—C36—H36A109.5
C38—N10—C40120.2 (6)N9—C36—H36B109.5
C39—N10—C40116.7 (6)H36A—C36—H36B109.5
O1—C1—C2119.8 (5)N9—C36—H36C109.5
O1—C1—C6121.0 (5)H36A—C36—H36C109.5
C2—C1—C6119.2 (5)H36B—C36—H36C109.5
C3—C2—C1120.6 (6)N9—C37—H37A109.5
C3—C2—H2A119.7N9—C37—H37B109.5
C1—C2—H2A119.7H37A—C37—H37B109.5
O2—C3—C2122.2 (6)N9—C37—H37C109.5
O2—C3—C4117.8 (6)H37A—C37—H37C109.5
C2—C3—C4119.9 (6)H37B—C37—H37C109.5
C5—C4—C3120.6 (6)O8—C38—N10124.5 (6)
C5—C4—H4A119.7O8—C38—H38117.7
C3—C4—H4A119.7N10—C38—H38117.7
C4—C5—C6121.7 (6)N10—C39—H39A109.5
C4—C5—H5A119.2N10—C39—H39B109.5
C6—C5—H5A119.2H39A—C39—H39B109.5
C1—C6—C5118.1 (6)N10—C39—H39C109.5
C1—C6—C7124.6 (5)H39A—C39—H39C109.5
C5—C6—C7117.3 (6)H39B—C39—H39C109.5
N1—C7—C6125.6 (6)N10—C40—H40A109.5
N1—C7—H7A117.2N10—C40—H40B109.5
C6—C7—H7A117.2H40A—C40—H40B109.5
N2—C8—N3112.3 (5)N10—C40—H40C109.5
N2—C8—S1123.9 (5)H40A—C40—H40C109.5
N3—C8—S1123.7 (5)H40B—C40—H40C109.5
C10—C9—C14119.9 (6)C29—N7—C30125.6 (12)
C10—C9—N3119.1 (6)C29—N7—C31119.9 (10)
C14—C9—N3120.9 (6)C30—N7—C31114.5 (11)
C9—C10—C11119.3 (6)O5—C29—N7125.9 (14)
C9—C10—H10120.3O5—C29—H29117.1
C11—C10—H10120.3N7—C29—H29117.1
C12—C11—C10120.7 (7)C29'—N7'—C30'118 (3)
C12—C11—H11119.7C29'—N7'—C31'134 (4)
C10—C11—H11119.7C30'—N7'—C31'108 (3)
C11—C12—C13120.5 (7)O5'—C29'—N7'119 (3)
C11—C12—H12119.8O5'—C29'—H29'120.5
C13—C12—H12119.8N7'—C29'—H29'120.5
C12—C13—C14119.4 (7)N7'—C30'—H30D109.5
C12—C13—H13120.3N7'—C30'—H30E109.5
C14—C13—H13120.3H30D—C30'—H30E109.5
C13—C14—C9120.3 (6)N7'—C30'—H30F109.5
C13—C14—H14119.9H30D—C30'—H30F109.5
C9—C14—H14119.9H30E—C30'—H30F109.5
O3—C15—C16119.9 (5)N7'—C31'—H31D109.5
O3—C15—C20120.5 (5)N7'—C31'—H31E109.5
C16—C15—C20119.5 (5)H31D—C31'—H31E109.5
C15—C16—C17120.5 (5)N7'—C31'—H31F109.5
C15—C16—H16119.7H31D—C31'—H31F109.5
C17—C16—H16119.7H31E—C31'—H31F109.5
O3—Zn1—S1—C8−137.6 (2)C2—C1—C6—C50.2 (9)
O1—Zn1—S1—C8−61.6 (3)O1—C1—C6—C7−0.3 (9)
N1—Zn1—S1—C8−7.8 (2)C2—C1—C6—C7178.6 (6)
Cl1—Zn1—S1—C899.5 (2)C4—C5—C6—C10.8 (9)
O1—Zn2—S2—C22−143.0 (2)C4—C5—C6—C7−177.7 (6)
O3—Zn2—S2—C22−70.3 (3)N2—N1—C7—C6−179.5 (5)
N4—Zn2—S2—C22−8.0 (2)Zn1—N1—C7—C614.6 (9)
Cl2—Zn2—S2—C2294.6 (2)C1—C6—C7—N17.9 (10)
O3—Zn2—O1—C1−172.8 (5)C5—C6—C7—N1−173.8 (6)
N4—Zn2—O1—C1−108.4 (5)N1—N2—C8—N3172.5 (5)
Cl2—Zn2—O1—C189.1 (5)N1—N2—C8—S1−6.3 (8)
S2—Zn2—O1—C1−25.3 (5)C9—N3—C8—N2−179.5 (6)
O3—Zn2—O1—Zn11.46 (16)C9—N3—C8—S1−0.7 (9)
N4—Zn2—O1—Zn165.9 (3)Zn1—S1—C8—N210.1 (5)
Cl2—Zn2—O1—Zn1−96.67 (16)Zn1—S1—C8—N3−168.5 (5)
S2—Zn2—O1—Zn1148.99 (14)C8—N3—C9—C10123.0 (7)
O3—Zn1—O1—C1172.8 (5)C8—N3—C9—C14−59.2 (9)
N1—Zn1—O1—C137.7 (5)C14—C9—C10—C110.0 (11)
Cl1—Zn1—O1—C1−70.2 (5)N3—C9—C10—C11177.9 (7)
S1—Zn1—O1—C191.2 (5)C9—C10—C11—C120.0 (12)
O3—Zn1—O1—Zn2−1.48 (17)C10—C11—C12—C13−0.1 (12)
N1—Zn1—O1—Zn2−136.6 (2)C11—C12—C13—C140.1 (11)
Cl1—Zn1—O1—Zn2115.56 (14)C12—C13—C14—C9−0.1 (10)
S1—Zn1—O1—Zn2−83.1 (3)C10—C9—C14—C130.0 (10)
O1—Zn1—O3—C15172.6 (5)N3—C9—C14—C13−177.8 (6)
N1—Zn1—O3—C15−120.5 (5)Zn1—O3—C15—C16−25.5 (8)
Cl1—Zn1—O3—C1577.4 (5)Zn2—O3—C15—C16144.2 (4)
S1—Zn1—O3—C15−34.5 (5)Zn1—O3—C15—C20154.2 (4)
O1—Zn1—O3—Zn21.46 (16)Zn2—O3—C15—C20−36.1 (7)
N1—Zn1—O3—Zn268.3 (3)O3—C15—C16—C17179.5 (5)
Cl1—Zn1—O3—Zn2−93.78 (16)C20—C15—C16—C17−0.2 (9)
S1—Zn1—O3—Zn2154.36 (14)C15—C16—C17—O4178.2 (5)
O1—Zn2—O3—C15−173.5 (5)C15—C16—C17—C18−0.5 (9)
N4—Zn2—O3—C1546.3 (4)O4—C17—C18—C19−178.7 (5)
Cl2—Zn2—O3—C15−57.2 (4)C16—C17—C18—C190.1 (9)
S2—Zn2—O3—C15108.0 (4)C17—C18—C19—C200.9 (9)
O1—Zn2—O3—Zn1−1.49 (17)C18—C19—C20—C15−1.6 (9)
N4—Zn2—O3—Zn1−141.7 (2)C18—C19—C20—C21−178.4 (6)
Cl2—Zn2—O3—Zn1114.81 (14)O3—C15—C20—C19−178.5 (5)
S2—Zn2—O3—Zn1−80.0 (2)C16—C15—C20—C191.1 (8)
O3—Zn1—N1—C7−92.8 (5)O3—C15—C20—C21−2.0 (9)
O1—Zn1—N1—C7−29.0 (5)C16—C15—C20—C21177.7 (6)
Cl1—Zn1—N1—C770.6 (5)N5—N4—C21—C20−179.5 (5)
S1—Zn1—N1—C7172.7 (5)Zn2—N4—C21—C2017.4 (8)
O3—Zn1—N1—N2101.5 (4)C19—C20—C21—N4−172.0 (6)
O1—Zn1—N1—N2165.4 (4)C15—C20—C21—N411.5 (9)
Cl1—Zn1—N1—N2−95.0 (4)N4—N5—C22—N6176.6 (5)
S1—Zn1—N1—N27.1 (4)N4—N5—C22—S2−1.8 (8)
C7—N1—N2—C8−170.3 (5)C23—N6—C22—N5−172.2 (5)
Zn1—N1—N2—C8−3.2 (7)C23—N6—C22—S26.2 (9)
O1—Zn2—N4—C21−98.7 (5)Zn2—S2—C22—N58.0 (5)
O3—Zn2—N4—C21−37.0 (5)Zn2—S2—C22—N6−170.2 (5)
Cl2—Zn2—N4—C2165.5 (5)C22—N6—C23—C28−41.3 (10)
S2—Zn2—N4—C21172.1 (5)C22—N6—C23—C24139.9 (6)
O1—Zn2—N4—N598.5 (4)C28—C23—C24—C250.3 (10)
O3—Zn2—N4—N5160.2 (4)N6—C23—C24—C25179.2 (6)
Cl2—Zn2—N4—N5−97.3 (4)C23—C24—C25—C260.5 (12)
S2—Zn2—N4—N59.3 (3)C24—C25—C26—C270.0 (13)
C21—N4—N5—C22−171.8 (5)C25—C26—C27—C28−1.4 (13)
Zn2—N4—N5—C22−7.4 (6)C24—C23—C28—C27−1.7 (11)
Zn2—O1—C1—C2−36.4 (8)N6—C23—C28—C27179.5 (7)
Zn1—O1—C1—C2150.7 (4)C26—C27—C28—C232.2 (13)
Zn2—O1—C1—C6142.5 (5)C33—N8—C32—O6−3.4 (11)
Zn1—O1—C1—C6−30.5 (8)C34—N8—C32—O6−177.8 (6)
O1—C1—C2—C3178.2 (5)C36—N9—C35—O71.1 (10)
C6—C1—C2—C3−0.7 (9)C37—N9—C35—O7178.5 (6)
C1—C2—C3—O2−178.9 (6)C39—N10—C38—O84.0 (10)
C1—C2—C3—C40.1 (9)C40—N10—C38—O8−176.6 (6)
O2—C3—C4—C5180.0 (6)C30—N7—C29—O50.3 (4)
C2—C3—C4—C50.9 (10)C31—N7—C29—O5−179.6 (4)
C3—C4—C5—C6−1.4 (10)C30'—N7'—C29'—O5'179.9 (4)
O1—C1—C6—C5−178.7 (5)C31'—N7'—C29'—O5'0.0 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O50.841.762.595 (9)170
O4—H4o···O60.841.822.657 (6)175
N2—H2···O70.881.892.713 (6)156
N3—H3···O70.842.182.940 (6)151
N5—H5···O80.881.902.717 (6)154
N6—H6···O80.842.082.841 (6)150
Table 1
Selected geometric parameters (Å) top
Zn1—N12.127 (5)Zn2—O12.024 (4)
Zn1—O12.073 (4)Zn2—O32.061 (4)
Zn1—O32.024 (4)Zn2—N42.116 (5)
Zn1—S12.464 (2)Zn2—S22.420 (2)
Zn1—Cl12.272 (2)Zn2—Cl22.264 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O50.841.762.595 (9)170
O4—H4o···O60.841.822.657 (6)175
N2—H2···O70.881.892.713 (6)156
N3—H3···O70.842.182.940 (6)151
N5—H5···O80.881.902.717 (6)154
N6—H6···O80.842.082.841 (6)150
Acknowledgements top

We thank MOHE (FRGS -FP001/2009) and the Ministry of Science and Technology (grant No. Esc 02-02-11-SF0033) for supporting this study. KWT also thanks the Ministry of Higher Education for an SLAI scholarship.

references
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