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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): m569.
Published online 2010 April 24. doi:  10.1107/S1600536810014522
PMCID: PMC2979048

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

Abstract

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

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0m569-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C14H12N3O2S)2Cl2]·4C3H7NO
  • M r = 1066.68
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m569-efi1.jpg
  • a = 8.1913 (4) Å
  • b = 17.6402 (7) Å
  • c = 17.9597 (7) Å
  • α = 64.941 (3)°
  • β = 81.213 (3)°
  • γ = 89.103 (3)°
  • V = 2319.76 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.30 mm−1
  • T = 100 K
  • 0.12 × 0.08 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.860, T max = 0.950
  • 15848 measured reflections
  • 8106 independent reflections
  • 4918 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.161
  • S = 0.97
  • 8106 reflections
  • 634 parameters
  • 68 restraints
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.71 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014522/hg2675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014522/hg2675Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

[Zn2(C14H12N3O2S)2Cl2]·4C3H7NOZ = 2
Mr = 1066.68F(000) = 1104
Triclinic, P1Dx = 1.527 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer8106 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

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 = 0.97w = 1/[σ2(Fo2) + (0.0745P)2] where P = (Fo2 + 2Fc2)/3
8106 reflections(Δ/σ)max = 0.001
634 parametersΔρmax = 0.59 e Å3
68 restraintsΔρmin = −0.70 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2675).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2009a). Acta Cryst. E65, m61–m62. [PMC free article] [PubMed]
  • Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2009b). Acta Cryst. E65, m549. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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