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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1340.
Published online 2010 September 30. doi:  10.1107/S1600536810038614
PMCID: PMC2983178

Bis(pyridine-2-carbaldehyde thio­semi­carbazone)zinc(II) dinitrate dihydrate

Abstract

The asymmetric unit of the title compound, [Zn(C7H8N4S)2](NO3)2·2H2O, contains two Zn(pht)2 cations (pht is pyridine-2-carbaldehyde thio­semicarbazone), four nitrate anions and four water mol­ecules. In the cations, each ZnII ion adopts a distorted octa­hedral coordination geometry, being chelated by two tridentate pht ligands. In the crystal, the cations, anions and water mol­ecules are connected via O—H(...)O and N—H(...)O hydrogen bonds into a three-dimensional network.

Related literature

For related structures, see: Antholine et al. (1977 [triangle]); Ainscough et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1340-scheme1.jpg

Experimental

Crystal data

  • [Zn(C7H8N4S)2](NO3)2·2H2O
  • M r = 585.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1340-efi1.jpg
  • a = 21.4623 (14) Å
  • b = 16.6324 (12) Å
  • c = 13.2764 (10) Å
  • β = 102.876 (2)°
  • V = 4620.1 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.31 mm−1
  • T = 120 K
  • 0.25 × 0.22 × 0.20 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a [triangle]) T min = 0.736, T max = 0.780
  • 22904 measured reflections
  • 8732 independent reflections
  • 5113 reflections with I > 2σ(I)
  • R int = 0.077

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.123
  • S = 1.02
  • 8732 reflections
  • 631 parameters
  • H-atom parameters constrained
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038614/bt5358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038614/bt5358Isup2.hkl

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

Acknowledgments

The authors thank the Program for Young Excellent Talents in Southeast University for financial support.

supplementary crystallographic information

Comment

The examination of the antitumor properties of N-heterocyclic carboxaldehyde thiosemicarbazones has been extended to the consideration of some of their first-row transition metal complexes (Antholine et al. 1977, Ainscough et al. 1998). Meanwhile, zinc plays an important role in various biological systems and is a vital component an essential cofactor, critical for numerous cellular processes and may be a major regulatory ion in the metabolism of cells. Herein, we report a ZnII complex, Zn(pht)2.2NO3.2H2O (pht= 2-(pyridine-2-carbaldehyde)hydrazinecarbothioamide).

The asymmetric unit of the title compound, contains two Zn(pht)2 cations (pht = 2-(pyridine-2-carbaldehyde)hydrazinecarbothioamide), which have the similar structure, four nitrates and four free water molecules. In the Zn(pht)2 cations, each ZnII ions adopts a distorted octahedral coordination geometry, being chelated by two tridentate pht ligands. In a pht, all the atoms are approximatively coplanar, and the distances of the C=N bond are 1.269 (6)–1.283 (6) Å, which are shorter than those of C—N bond (1.303 (7)–1.369 (6) Å), being considered to have full double-bond character. In packing, All the Zn(pht)2 cations, nitrates and water molecules are linked each other via O—H···O and N—H···O hydrogen bonds into a three-dimensional supramolecular network.

Experimental

A mixture of pht (0.036 g, 0.2 mmol), Zn(NO3)2.6H2O (0.029 g, 0.1 mmol), and water (8 ml) were heated ina 15 ml Teflon-lined vessel at 120 ° for 3 days, followed by slow cooling (5 ° h-1) to room temperature. After filtration, colorless block crystals were collected and dried in air (0.018 g, yield ca 30.7% based on pht).

Refinement

All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C—H = 0.93 Å and N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(C or N). H atoms of water molecules were located in difference Fourier maps and included in the subsequent refinement with O—H= 0.85Å with Uiso(H) = 1.2 Ueq(O).

Figures

Fig. 1.
View of the asymmetric unit of the title compoundcompound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

Crystal data

[Zn(C7H8N4S)2](NO3)2·2H2OF(000) = 2400
Mr = 585.89Dx = 1.685 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 785 reflections
a = 21.4623 (14) Åθ = 2.4–28.0°
b = 16.6324 (12) ŵ = 1.31 mm1
c = 13.2764 (10) ÅT = 120 K
β = 102.876 (2)°Block, colorless
V = 4620.1 (6) Å30.25 × 0.22 × 0.20 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer8732 independent reflections
Radiation source: fine-focus sealed tube5113 reflections with I > 2σ(I)
graphiteRint = 0.077
[var phi] and ω scanθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)h = −25→21
Tmin = 0.736, Tmax = 0.780k = −20→12
22904 measured reflectionsl = −16→16

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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
8732 reflections(Δ/σ)max = 0.029
631 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = −0.43 e Å3

Special details

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)

xyzUiso*/Ueq
Zn10.25244 (3)0.23919 (3)0.57658 (4)0.02381 (17)
Zn20.22452 (3)0.75501 (3)0.82766 (4)0.02208 (17)
S10.18156 (7)0.30117 (8)0.42437 (10)0.0301 (4)
S20.32904 (7)0.17217 (8)0.48824 (11)0.0330 (4)
S30.14317 (7)0.65650 (8)0.85347 (10)0.0280 (3)
S40.30520 (7)0.65526 (8)0.80976 (10)0.0280 (4)
C10.3251 (3)0.1529 (3)0.7846 (4)0.0339 (15)
H1A0.35820.18870.78310.041*
C20.3318 (3)0.0998 (3)0.8668 (4)0.0378 (16)
H2A0.36840.10040.91950.045*
C30.2829 (3)0.0460 (3)0.8692 (4)0.0386 (16)
H3A0.28630.00940.92310.046*
C40.2294 (3)0.0477 (3)0.7902 (4)0.0332 (15)
H4A0.19590.01230.79000.040*
C50.2258 (3)0.1028 (3)0.7106 (4)0.0266 (13)
C60.1702 (3)0.1088 (3)0.6264 (4)0.0277 (13)
H6A0.13620.07310.62020.033*
C80.1178 (2)0.2397 (3)0.4168 (4)0.0223 (12)
C90.1696 (3)0.3390 (3)0.7026 (4)0.0270 (13)
H9A0.13680.30330.67520.032*
C100.1577 (3)0.4020 (3)0.7660 (4)0.0285 (14)
H10A0.11730.40860.77970.034*
C110.2065 (3)0.4540 (3)0.8076 (4)0.0330 (15)
H11A0.19960.49610.84990.040*
C120.2655 (3)0.4431 (3)0.7859 (4)0.0298 (14)
H12A0.29920.47730.81370.036*
C130.2735 (3)0.3807 (3)0.7222 (3)0.0200 (12)
C140.3341 (3)0.3668 (3)0.6934 (4)0.0256 (13)
H14A0.37010.39730.72140.031*
C160.3920 (3)0.2337 (3)0.5309 (4)0.0288 (13)
C170.3197 (3)0.8776 (3)0.7546 (4)0.0286 (14)
H17A0.34790.86390.81610.034*
C180.3399 (3)0.9322 (3)0.6897 (4)0.0300 (14)
H18A0.38120.95300.70590.036*
C190.2978 (3)0.9545 (3)0.6017 (4)0.0334 (15)
H19A0.30970.99220.55770.040*
C200.2369 (3)0.9208 (3)0.5776 (4)0.0291 (14)
H20A0.20730.93590.51820.035*
C210.2214 (2)0.8643 (3)0.6445 (4)0.0207 (12)
C220.1609 (3)0.8202 (3)0.6203 (4)0.0256 (13)
H22A0.12920.83200.56210.031*
C240.0965 (3)0.6578 (3)0.7329 (4)0.0232 (13)
C250.1337 (3)0.8917 (3)0.8776 (4)0.0278 (13)
H25A0.10750.87820.81410.033*
C260.1147 (3)0.9538 (3)0.9340 (4)0.0285 (14)
H26A0.07710.98190.90770.034*
C270.1520 (3)0.9729 (3)1.0289 (4)0.0320 (14)
H27A0.13981.01351.06860.038*
C280.2086 (3)0.9305 (3)1.0648 (4)0.0320 (14)
H28A0.23500.94271.12860.038*
C290.2246 (3)0.8702 (3)1.0038 (4)0.0235 (13)
C300.2841 (3)0.8244 (3)1.0344 (4)0.0258 (13)
H30A0.31320.83431.09630.031*
C320.3575 (3)0.6699 (3)0.9239 (4)0.0242 (13)
N10.2738 (2)0.1546 (2)0.7083 (3)0.0270 (11)
N20.1698 (2)0.1650 (2)0.5611 (3)0.0234 (10)
N30.1180 (2)0.1775 (2)0.4824 (3)0.0273 (11)
H3B0.08550.14600.47450.033*
N40.06559 (19)0.2474 (2)0.3439 (3)0.0275 (11)
H4B0.03460.21400.34050.033*
H4C0.06240.28580.29970.033*
N50.2263 (2)0.3291 (2)0.6810 (3)0.0225 (10)
N60.3358 (2)0.3111 (2)0.6284 (3)0.0243 (11)
N70.3911 (2)0.2952 (2)0.5973 (3)0.0287 (11)
H7A0.42470.32390.61950.034*
N80.4457 (2)0.2266 (3)0.4975 (4)0.0427 (13)
H8A0.47660.25980.51830.051*
H8B0.44950.18880.45520.051*
N90.2622 (2)0.8438 (2)0.7334 (3)0.0231 (10)
N100.15389 (19)0.7643 (2)0.6836 (3)0.0195 (10)
N110.1020 (2)0.7152 (2)0.6629 (3)0.0244 (11)
H11B0.07320.72040.60670.029*
N120.0521 (2)0.6028 (2)0.7020 (3)0.0316 (12)
H12B0.02860.60470.64040.038*
H12C0.04660.56500.74330.038*
N130.1877 (2)0.8507 (2)0.9102 (3)0.0229 (10)
N140.2938 (2)0.7703 (2)0.9722 (3)0.0212 (10)
N150.3479 (2)0.7262 (2)0.9943 (3)0.0256 (11)
H15A0.37570.73331.05110.031*
N160.4098 (2)0.6278 (2)0.9496 (3)0.0328 (12)
H16A0.43600.63621.00790.039*
H16B0.41820.59160.90830.039*
N170.5277 (3)0.4141 (3)0.5916 (4)0.0421 (13)
N180.5183 (2)0.9676 (3)0.6417 (3)0.0291 (11)
N19−0.0127 (3)0.0485 (3)0.3698 (4)0.0358 (12)
N20−0.0031 (2)0.6531 (3)0.4316 (4)0.0358 (12)
O10.4955 (2)0.4005 (3)0.6560 (3)0.0628 (14)
O20.5329 (2)0.3626 (3)0.5256 (4)0.0677 (15)
O30.5557 (2)0.4799 (3)0.5909 (3)0.0544 (13)
O40.57090 (17)0.9985 (2)0.6837 (3)0.0329 (10)
O50.46998 (18)1.0110 (2)0.6105 (3)0.0406 (11)
O60.51370 (17)0.8926 (2)0.6304 (3)0.0335 (10)
O7−0.01433 (19)0.1186 (2)0.4029 (3)0.0448 (11)
O80.0395 (2)0.0142 (3)0.3794 (3)0.0516 (12)
O9−0.0623 (2)0.0145 (3)0.3268 (3)0.0648 (15)
O100.02421 (18)0.7177 (2)0.4717 (3)0.0395 (11)
O11−0.01805 (19)0.6012 (2)0.4904 (3)0.0430 (11)
O12−0.01414 (18)0.6431 (2)0.3370 (3)0.0441 (11)
O1W0.62343 (19)0.4712 (3)0.4129 (3)0.0608 (13)
H1WA0.61120.45620.35040.073*
H1WB0.60570.44440.45330.073*
O2W0.52013 (19)0.6250 (3)0.7187 (3)0.0588 (13)
H2WA0.50640.61750.77330.071*
H2WB0.54960.59950.69900.071*
O3W0.04209 (17)0.3374 (2)0.1575 (3)0.0400 (10)
H3WA0.01520.33250.10010.048*
H3WB0.03370.38470.17460.048*
O4W0.43806 (18)0.7533 (2)0.6735 (3)0.0542 (12)
H4WA0.46790.72660.65640.065*
H4WB0.45450.78970.71610.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0256 (4)0.0197 (3)0.0261 (3)−0.0050 (3)0.0059 (3)−0.0023 (3)
Zn20.0243 (4)0.0183 (3)0.0222 (3)0.0012 (3)0.0023 (3)−0.0007 (3)
S10.0311 (10)0.0296 (8)0.0283 (7)−0.0100 (7)0.0039 (7)0.0025 (6)
S20.0338 (10)0.0279 (8)0.0388 (8)−0.0050 (7)0.0116 (7)−0.0111 (6)
S30.0340 (10)0.0228 (7)0.0260 (7)−0.0015 (7)0.0038 (6)0.0007 (6)
S40.0302 (9)0.0229 (7)0.0279 (7)0.0048 (7)0.0005 (6)−0.0041 (6)
C10.040 (4)0.024 (3)0.034 (3)−0.002 (3)0.001 (3)−0.003 (3)
C20.059 (5)0.025 (3)0.028 (3)0.016 (3)0.006 (3)−0.005 (3)
C30.065 (5)0.021 (3)0.036 (3)0.007 (3)0.025 (3)0.004 (3)
C40.045 (4)0.021 (3)0.038 (3)0.008 (3)0.019 (3)0.003 (3)
C50.035 (4)0.017 (3)0.034 (3)0.004 (3)0.019 (3)0.001 (2)
C60.029 (4)0.015 (3)0.043 (3)−0.005 (3)0.015 (3)−0.001 (3)
C80.023 (3)0.020 (3)0.025 (3)0.002 (3)0.008 (2)−0.006 (2)
C90.038 (4)0.018 (3)0.025 (3)−0.004 (3)0.008 (3)0.004 (2)
C100.032 (4)0.031 (3)0.026 (3)0.010 (3)0.012 (3)0.012 (2)
C110.055 (5)0.018 (3)0.025 (3)0.007 (3)0.005 (3)0.000 (2)
C120.041 (4)0.019 (3)0.028 (3)−0.002 (3)0.004 (3)−0.003 (2)
C130.023 (4)0.019 (3)0.017 (3)0.002 (3)0.004 (2)0.003 (2)
C140.030 (4)0.021 (3)0.023 (3)−0.005 (3)0.001 (3)0.002 (2)
C160.029 (4)0.024 (3)0.034 (3)0.002 (3)0.009 (3)−0.001 (2)
C170.027 (4)0.022 (3)0.035 (3)0.005 (3)0.004 (3)−0.005 (3)
C180.025 (4)0.023 (3)0.044 (3)−0.003 (3)0.012 (3)−0.005 (3)
C190.051 (4)0.021 (3)0.034 (3)−0.013 (3)0.022 (3)−0.006 (3)
C200.040 (4)0.026 (3)0.023 (3)−0.005 (3)0.013 (3)0.000 (2)
C210.023 (3)0.014 (3)0.027 (3)0.002 (2)0.008 (2)−0.003 (2)
C220.031 (4)0.024 (3)0.022 (3)0.002 (3)0.006 (3)0.001 (2)
C240.030 (4)0.016 (3)0.027 (3)0.002 (3)0.012 (3)−0.004 (2)
C250.025 (4)0.026 (3)0.033 (3)−0.002 (3)0.007 (3)0.003 (3)
C260.024 (4)0.024 (3)0.039 (3)0.006 (3)0.011 (3)0.002 (3)
C270.034 (4)0.022 (3)0.043 (3)0.001 (3)0.015 (3)−0.009 (3)
C280.037 (4)0.022 (3)0.038 (3)−0.005 (3)0.010 (3)−0.011 (3)
C290.028 (4)0.017 (3)0.028 (3)0.002 (3)0.012 (3)0.001 (2)
C300.033 (4)0.024 (3)0.021 (3)0.000 (3)0.007 (3)−0.005 (2)
C320.019 (3)0.020 (3)0.035 (3)0.000 (3)0.010 (3)0.001 (2)
N10.030 (3)0.019 (2)0.034 (3)0.003 (2)0.011 (2)0.000 (2)
N20.027 (3)0.016 (2)0.029 (2)−0.002 (2)0.009 (2)0.0015 (19)
N30.025 (3)0.020 (2)0.036 (3)−0.009 (2)0.005 (2)−0.003 (2)
N40.021 (3)0.025 (3)0.034 (2)−0.004 (2)0.001 (2)0.001 (2)
N50.024 (3)0.019 (2)0.025 (2)0.001 (2)0.007 (2)−0.0008 (19)
N60.026 (3)0.021 (2)0.028 (2)0.001 (2)0.011 (2)0.003 (2)
N70.023 (3)0.028 (3)0.035 (3)−0.005 (2)0.005 (2)−0.006 (2)
N80.032 (3)0.042 (3)0.057 (3)−0.006 (3)0.017 (3)−0.016 (3)
N90.020 (3)0.019 (2)0.031 (2)−0.002 (2)0.007 (2)−0.0047 (19)
N100.020 (3)0.017 (2)0.022 (2)−0.001 (2)0.0064 (19)−0.0004 (18)
N110.022 (3)0.026 (3)0.023 (2)−0.010 (2)0.000 (2)0.0038 (19)
N120.030 (3)0.026 (3)0.039 (3)−0.011 (2)0.007 (2)0.002 (2)
N130.023 (3)0.018 (2)0.029 (2)0.001 (2)0.009 (2)−0.0018 (19)
N140.017 (3)0.021 (2)0.025 (2)0.002 (2)0.0043 (19)−0.0006 (19)
N150.028 (3)0.023 (2)0.021 (2)0.001 (2)−0.004 (2)−0.0029 (18)
N160.031 (3)0.028 (3)0.036 (3)0.007 (2)0.000 (2)−0.010 (2)
N170.041 (4)0.041 (3)0.042 (3)−0.006 (3)0.006 (3)−0.006 (3)
N180.026 (3)0.031 (3)0.028 (3)−0.003 (3)0.002 (2)0.004 (2)
N190.037 (4)0.031 (3)0.039 (3)−0.005 (3)0.009 (3)0.007 (2)
N200.032 (3)0.031 (3)0.041 (3)0.010 (3)0.000 (3)−0.001 (2)
O10.063 (3)0.077 (4)0.059 (3)−0.036 (3)0.038 (3)−0.026 (3)
O20.081 (4)0.059 (3)0.075 (3)−0.013 (3)0.042 (3)−0.022 (3)
O30.053 (3)0.046 (3)0.061 (3)−0.020 (3)0.006 (2)−0.003 (2)
O40.023 (2)0.030 (2)0.043 (2)−0.0044 (19)0.0008 (19)0.0046 (18)
O50.028 (3)0.033 (2)0.054 (3)0.005 (2)−0.005 (2)0.001 (2)
O60.038 (3)0.019 (2)0.045 (2)−0.0062 (19)0.012 (2)−0.0087 (18)
O70.051 (3)0.021 (2)0.072 (3)−0.004 (2)0.036 (2)−0.008 (2)
O80.049 (3)0.047 (3)0.058 (3)0.019 (3)0.011 (2)0.006 (2)
O90.065 (3)0.059 (3)0.058 (3)−0.045 (3)−0.014 (3)0.015 (2)
O100.047 (3)0.027 (2)0.037 (2)−0.004 (2)−0.007 (2)0.0000 (18)
O110.046 (3)0.037 (2)0.046 (3)−0.008 (2)0.010 (2)0.007 (2)
O120.046 (3)0.046 (3)0.033 (2)0.008 (2)−0.006 (2)−0.005 (2)
O1W0.066 (3)0.076 (3)0.040 (3)−0.008 (3)0.010 (2)0.004 (2)
O2W0.048 (3)0.070 (3)0.061 (3)0.002 (3)0.018 (2)0.005 (2)
O3W0.046 (3)0.034 (2)0.040 (2)−0.001 (2)0.012 (2)−0.0074 (19)
O4W0.046 (3)0.053 (3)0.055 (3)−0.010 (2)−0.008 (2)0.004 (2)

Geometric parameters (Å, °)

Zn1—N62.133 (4)C21—C221.463 (7)
Zn1—N22.133 (4)C22—N101.283 (6)
Zn1—N52.196 (4)C22—H22A0.9300
Zn1—N12.211 (4)C24—N121.319 (6)
Zn1—S12.4678 (15)C24—N111.356 (6)
Zn1—S22.4860 (16)C25—N131.331 (6)
Zn2—N102.165 (4)C25—C261.389 (7)
Zn2—N142.165 (4)C25—H25A0.9300
Zn2—N132.178 (4)C26—C271.372 (7)
Zn2—N92.203 (4)C26—H26A0.9300
Zn2—S42.4475 (15)C27—C281.393 (7)
Zn2—S32.4733 (15)C27—H27A0.9300
S1—C81.692 (5)C28—C291.380 (7)
S2—C161.689 (6)C28—H28A0.9300
S3—C241.688 (5)C29—N131.356 (6)
S4—C321.690 (5)C29—C301.464 (7)
C1—N11.319 (6)C30—N141.270 (6)
C1—C21.386 (7)C30—H30A0.9300
C1—H1A0.9300C32—N161.304 (6)
C2—C31.385 (7)C32—N151.369 (6)
C2—H2A0.9300N2—N31.361 (5)
C3—C41.372 (7)N3—H3B0.8600
C3—H3A0.9300N4—H4B0.8600
C4—C51.388 (7)N4—H4C0.8600
C4—H4A0.9300N6—N71.367 (5)
C5—N11.349 (6)N7—H7A0.8600
C5—C61.445 (7)N8—H8A0.8600
C6—N21.273 (6)N8—H8B0.8600
C6—H6A0.9300N10—N111.359 (5)
C8—N41.314 (6)N11—H11B0.8600
C8—N31.353 (6)N12—H12B0.8600
C9—N51.322 (6)N12—H12C0.8600
C9—C101.404 (7)N14—N151.348 (5)
C9—H9A0.9300N15—H15A0.8600
C10—C111.375 (7)N16—H16A0.8600
C10—H10A0.9300N16—H16B0.8600
C11—C121.371 (7)N17—O11.233 (6)
C11—H11A0.9300N17—O21.249 (6)
C12—C131.375 (6)N17—O31.250 (6)
C12—H12A0.9300N18—O41.252 (5)
C13—N51.347 (6)N18—O51.256 (5)
C13—C141.452 (7)N18—O61.258 (5)
C14—N61.273 (6)N19—O91.229 (5)
C14—H14A0.9300N19—O81.238 (5)
C16—N81.329 (6)N19—O71.249 (5)
C16—N71.354 (6)N20—O121.236 (5)
C17—N91.328 (6)N20—O111.252 (5)
C17—C181.387 (7)N20—O101.281 (5)
C17—H17A0.9300O1W—H1WA0.8500
C18—C191.359 (7)O1W—H1WB0.8501
C18—H18A0.9300O2W—H2WA0.8499
C19—C201.394 (7)O2W—H2WB0.8500
C19—H19A0.9300O3W—H3WA0.8502
C20—C211.383 (6)O3W—H3WB0.8500
C20—H20A0.9300O4W—H4WA0.8500
C21—N91.347 (6)O4W—H4WB0.8502
N6—Zn1—N2167.04 (16)N10—C22—C21116.6 (5)
N6—Zn1—N574.23 (16)N10—C22—H22A121.7
N2—Zn1—N597.52 (16)C21—C22—H22A121.7
N6—Zn1—N195.16 (16)N12—C24—N11116.2 (5)
N2—Zn1—N174.32 (16)N12—C24—S3121.4 (4)
N5—Zn1—N188.34 (15)N11—C24—S3122.4 (4)
N6—Zn1—S1110.45 (11)N13—C25—C26123.0 (5)
N2—Zn1—S179.34 (12)N13—C25—H25A118.5
N5—Zn1—S191.99 (11)C26—C25—H25A118.5
N1—Zn1—S1153.47 (13)C27—C26—C25119.1 (5)
N6—Zn1—S278.96 (12)C27—C26—H26A120.5
N2—Zn1—S2108.58 (11)C25—C26—H26A120.5
N5—Zn1—S2153.14 (12)C26—C27—C28118.9 (5)
N1—Zn1—S292.62 (11)C26—C27—H27A120.6
S1—Zn1—S298.79 (5)C28—C27—H27A120.6
N10—Zn2—N14169.14 (15)C29—C28—C27118.6 (5)
N10—Zn2—N1397.54 (15)C29—C28—H28A120.7
N14—Zn2—N1373.92 (16)C27—C28—H28A120.7
N10—Zn2—N973.97 (15)N13—C29—C28122.7 (5)
N14—Zn2—N999.09 (15)N13—C29—C30115.1 (4)
N13—Zn2—N990.90 (15)C28—C29—C30122.1 (5)
N10—Zn2—S4109.51 (11)N14—C30—C29116.6 (5)
N14—Zn2—S478.71 (11)N14—C30—H30A121.7
N13—Zn2—S4152.61 (12)C29—C30—H30A121.7
N9—Zn2—S492.42 (11)N16—C32—N15116.1 (5)
N10—Zn2—S378.04 (11)N16—C32—S4121.2 (4)
N14—Zn2—S3108.77 (11)N15—C32—S4122.7 (4)
N13—Zn2—S393.90 (11)C1—N1—C5118.7 (5)
N9—Zn2—S3151.99 (12)C1—N1—Zn1127.7 (4)
S4—Zn2—S395.80 (5)C5—N1—Zn1113.5 (3)
C8—S1—Zn197.99 (18)C6—N2—N3121.0 (4)
C16—S2—Zn197.7 (2)C6—N2—Zn1118.6 (4)
C24—S3—Zn298.53 (19)N3—N2—Zn1120.4 (3)
C32—S4—Zn299.06 (19)C8—N3—N2119.7 (4)
N1—C1—C2122.7 (6)C8—N3—H3B120.2
N1—C1—H1A118.6N2—N3—H3B120.2
C2—C1—H1A118.6C8—N4—H4B120.0
C3—C2—C1119.0 (6)C8—N4—H4C120.0
C3—C2—H2A120.5H4B—N4—H4C120.0
C1—C2—H2A120.5C9—N5—C13118.6 (4)
C4—C3—C2118.5 (5)C9—N5—Zn1126.8 (3)
C4—C3—H3A120.7C13—N5—Zn1114.6 (3)
C2—C3—H3A120.7C14—N6—N7120.2 (5)
C3—C4—C5119.4 (6)C14—N6—Zn1118.6 (4)
C3—C4—H4A120.3N7—N6—Zn1121.1 (3)
C5—C4—H4A120.3C16—N7—N6118.8 (4)
N1—C5—C4121.7 (5)C16—N7—H7A120.6
N1—C5—C6116.2 (5)N6—N7—H7A120.6
C4—C5—C6122.1 (5)C16—N8—H8A120.0
N2—C6—C5117.2 (5)C16—N8—H8B120.0
N2—C6—H6A121.4H8A—N8—H8B120.0
C5—C6—H6A121.4C17—N9—C21118.1 (4)
N4—C8—N3115.3 (5)C17—N9—Zn2127.2 (3)
N4—C8—S1122.1 (4)C21—N9—Zn2114.7 (3)
N3—C8—S1122.6 (4)C22—N10—N11120.9 (4)
N5—C9—C10121.5 (5)C22—N10—Zn2117.9 (4)
N5—C9—H9A119.3N11—N10—Zn2121.1 (3)
C10—C9—H9A119.3C24—N11—N10118.5 (4)
C11—C10—C9119.1 (5)C24—N11—H11B120.7
C11—C10—H10A120.5N10—N11—H11B120.7
C9—C10—H10A120.5C24—N12—H12B120.0
C12—C11—C10119.3 (5)C24—N12—H12C120.0
C12—C11—H11A120.4H12B—N12—H12C120.0
C10—C11—H11A120.4C25—N13—C29117.7 (4)
C11—C12—C13118.5 (5)C25—N13—Zn2126.7 (3)
C11—C12—H12A120.7C29—N13—Zn2115.6 (3)
C13—C12—H12A120.7C30—N14—N15120.2 (4)
N5—C13—C12123.0 (5)C30—N14—Zn2118.6 (4)
N5—C13—C14115.3 (4)N15—N14—Zn2121.1 (3)
C12—C13—C14121.7 (5)N14—N15—C32118.4 (4)
N6—C14—C13117.2 (5)N14—N15—H15A120.8
N6—C14—H14A121.4C32—N15—H15A120.8
C13—C14—H14A121.4C32—N16—H16A120.0
N8—C16—N7115.1 (5)C32—N16—H16B120.0
N8—C16—S2121.5 (4)H16A—N16—H16B120.0
N7—C16—S2123.3 (4)O1—N17—O2120.8 (5)
N9—C17—C18123.4 (5)O1—N17—O3120.7 (5)
N9—C17—H17A118.3O2—N17—O3118.5 (6)
C18—C17—H17A118.3O4—N18—O5120.5 (4)
C19—C18—C17118.2 (5)O4—N18—O6120.0 (5)
C19—C18—H18A120.9O5—N18—O6119.5 (5)
C17—C18—H18A120.9O9—N19—O8120.5 (5)
C18—C19—C20119.8 (5)O9—N19—O7120.2 (6)
C18—C19—H19A120.1O8—N19—O7119.3 (5)
C20—C19—H19A120.1O12—N20—O11121.5 (5)
C21—C20—C19118.3 (5)O12—N20—O10120.1 (5)
C21—C20—H20A120.9O11—N20—O10118.4 (5)
C19—C20—H20A120.9H1WA—O1W—H1WB112.2
N9—C21—C20122.1 (5)H2WA—O2W—H2WB127.8
N9—C21—C22115.9 (4)H3WA—O3W—H3WB100.8
C20—C21—C22121.9 (5)H4WA—O4W—H4WB108.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3B···O70.862.192.966 (6)150
N4—H4B···O70.862.172.957 (6)153
N4—H4C···O3W0.862.032.840 (5)157
N7—H7A···O10.861.962.813 (6)172
N8—H8A···O20.862.082.906 (6)160
N8—H8B···O6i0.862.042.870 (6)163
N11—H11B···O100.861.872.710 (5)167
N12—H12B···O110.862.022.876 (6)173
N12—H12C···O8ii0.862.273.114 (6)168
N15—H15A···O4Wiii0.861.872.733 (5)178
N16—H16A···O6iii0.862.112.909 (6)155
N16—H16B···O4iv0.862.022.873 (5)173
O1W—H1WA···O4v0.852.323.042 (5)144
O1W—H1WB···O30.852.393.041 (6)134
O2W—H2WA···O5iv0.852.332.927 (6)128
O2W—H2WB···O30.852.473.141 (6)136
O3W—H3WA···O10vi0.852.222.800 (5)126
O3W—H3WB···O9vii0.852.242.978 (6)145
O4W—H4WA···O2W0.852.092.746 (6)133
O4W—H4WB···O60.852.552.958 (5)111

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+3/2, z−1/2; (vi) −x, y−1/2, −z+1/2; (vii) −x, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5358).

References

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  • Antholine, W. E., Knight, J. M. & Petering, D. H. (1977). Inorg. Chem.16, 569–574.
  • Bruker (2000). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Sheldrick, G. M. (2008a). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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