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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): m489.
Published online 2008 February 20. doi:  10.1107/S160053680800442X
PMCID: PMC2960845

Tetrakis[(benzene-18-crown-6)potassium]bis[tris(thiocyanato)copper(I)]

Abstract

The title complex, bis­(μ-benzene-18-crown-6)-3κ6 O:4κO;4κ6 O:3κO-bis­(benzene-18-crown-6)-1κ6 O,6κ6 O-tetra-μ-thiocyanato-1:2κ2 S:N;2:3κ2 N:S;4:5κ2 S:N;5:6κ2 N:S-dithio­cyanato-2κN,5κN-2,5-dicopper(I)-1,3,4,6-tetra­potassium(I), [K4Cu2(NCS)6(C16H24O6)4] or {[K(C16H24O6)]4[Cu(NCS)3]2}, consists of four [K(benzene-18-crown-6)]+ cations and two [Cu(NCS)3]2− anions, forming a dimeric structure with site symmetry An external file that holds a picture, illustration, etc.
Object name is e-64-0m489-efi1.jpg. In each [Cu(NCS)3]2− anion, the CuI atom is coordinated by three N atoms of thio­cyanate ligands in a trigonal–planar coordination geometry. Each [Cu(NCS)3]2− anion bridges two [K(benzene-18-crown-6)]+ cations, with K—S distances of 3.317 (3) and 3.198 (3) Å, and two [K(benzene-18-crown-6)]+ cations are linked across a crystallographic centre of inversion, with K—O distances of 2.903 (5) Å.

Related literature

For structures incorporating [Cu(NCS)3]2− anions, see: Rusanova et al. (2000 [triangle]); Wang et al. (1987 [triangle]). For polymeric structures incorporating crown ethers, see: Desai et al. (2001 [triangle]); Bastos et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m489-scheme1.jpg

Experimental

Crystal data

  • [K4Cu2(NCS)6(C16H24O6)4]
  • M r = 1881.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m489-efi2.jpg
  • a = 9.702 (3) Å
  • b = 13.119 (4) Å
  • c = 17.968 (6) Å
  • α = 91.015 (6)°
  • β = 97.167 (6)°
  • γ = 105.558 (6)°
  • V = 2182.9 (12) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.89 mm−1
  • T = 273 (2) K
  • 0.49 × 0.21 × 0.16 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.668, T max = 0.870
  • 11606 measured reflections
  • 7633 independent reflections
  • 2441 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.160
  • S = 0.85
  • 7633 reflections
  • 505 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800442X/bi2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800442X/bi2279Isup2.hkl

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

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (No. X051040).

supplementary crystallographic information

Comment

Much interest has been focused on crown ethers and their metal cations, because they can act as modules to form polymeric supramolecular structures (Desai et al., 2001; Bastos et al., 2000).

The title complex consists of four [K(benzene-18-crown-6)]+ cations and two [Cu(NCS)3]2- anions. The CuI atom is coordinated by three N atoms in a trigonal-planar geometry (Table 1). The K+ ions are coordinated by six O atoms, and lie approximately in the plane of the crown ether. The K—O bond lengths vary from 2.683 (5)–2.903 (5) Å for K1 and 2.729 (5)–2.819 (5) Å for K2. In addition, K+ is coordinated by one S atom from [Cu(NCS)3]2-, with K1—S1 = 3.317 (3) Å and K2—S2 = 3.198 (3) Å.

Experimental

Cu(NCS) (0.1853 g, 1.5 mmol) and K(NCS) (0.1448 g, 1.5 mmol) in 15 ml absolute alcohol were refluxed for 4 h, then benzene-18-crown-6 (0.4675 g, 1.5 mmol) was added slowly and the mixture was refluxed for a further 4 h. After cooling to room temperature, the mixture was filtered and the solid recrystallized from diethyl ether. Elemental analysis: calculated C 44.69, H 5.14, N 4.47%; found: C 44.76, H 5.17, N 4.51%.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The title complex (H atoms omitted) showing the numbering scheme for Cu, K, N and S atoms. Displacement ellipsoids are drawn at the 30% probability level. Atoms with the suffix A are generated by the symmetry operator 1 - x, -y, 1 - z.

Crystal data

[K4Cu2(NCS)6(C16H24O6)4]Z = 1
Mr = 1881.36F000 = 980
Triclinic, P1Dx = 1.431 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.702 (3) ÅCell parameters from 1026 reflections
b = 13.119 (4) Åθ = 2.3–19.0º
c = 17.968 (6) ŵ = 0.89 mm1
α = 91.015 (6)ºT = 273 (2) K
β = 97.167 (6)ºBlock, green
γ = 105.558 (6)º0.49 × 0.21 × 0.16 mm
V = 2182.9 (12) Å3

Data collection

Bruker SMART CCD diffractometer7633 independent reflections
Radiation source: fine-focus sealed tube2441 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 273(2) Kθmax = 25.0º
ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.669, Tmax = 0.870k = −11→15
11606 measured reflectionsl = −21→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.160  w = 1/[σ2(Fo2) + (0.0464P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
7633 reflectionsΔρmax = 0.41 e Å3
505 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cu1−0.10846 (12)−0.10295 (8)0.25933 (6)0.0631 (4)
K10.35951 (18)−0.15952 (12)0.48793 (9)0.0492 (5)
K2−0.03041 (19)0.27283 (12)0.09562 (10)0.0566 (5)
N1−0.0459 (8)−0.1929 (6)0.3274 (4)0.072 (2)
N20.0190 (8)0.0283 (5)0.2376 (4)0.066 (2)
N3−0.2976 (8)−0.1432 (5)0.2030 (4)0.065 (2)
O10.4114 (6)−0.3250 (4)0.5657 (3)0.0529 (14)
O20.4960 (5)−0.2967 (4)0.4361 (3)0.0490 (14)
O30.4511 (5)−0.1319 (4)0.3487 (3)0.0501 (14)
O40.3773 (5)0.0397 (4)0.4201 (3)0.0502 (14)
O50.1858 (5)−0.0452 (4)0.5271 (3)0.0542 (14)
O60.2402 (5)−0.2078 (4)0.6189 (3)0.0523 (14)
O7−0.2852 (5)0.2777 (4)0.1540 (3)0.0526 (15)
O8−0.0563 (6)0.4250 (4)0.1980 (3)0.0598 (15)
O90.1587 (6)0.4733 (4)0.1018 (3)0.0632 (16)
O100.1230 (6)0.3411 (4)−0.0244 (3)0.0571 (15)
O11−0.0473 (6)0.1308 (4)−0.0203 (3)0.0626 (16)
O12−0.2782 (6)0.1135 (4)0.0589 (3)0.0632 (16)
S10.0692 (3)−0.34102 (19)0.40627 (13)0.0706 (7)
S20.2182 (3)0.21181 (19)0.20496 (16)0.0946 (9)
S3−0.5419 (3)−0.21268 (18)0.09955 (14)0.0814 (8)
C10.5322 (8)−0.3583 (6)0.5560 (5)0.043 (2)
C20.6081 (10)−0.4018 (6)0.6090 (5)0.064 (2)
H20.5798−0.41090.65660.077*
C30.7264 (10)−0.4328 (7)0.5929 (6)0.075 (3)
H30.7771−0.46320.62940.090*
C40.7697 (10)−0.4188 (7)0.5231 (6)0.075 (3)
H40.8489−0.44030.51170.090*
C50.6951 (9)−0.3726 (6)0.4703 (5)0.058 (2)
H50.7252−0.36170.42320.069*
C60.5774 (9)−0.3425 (6)0.4857 (5)0.045 (2)
C70.5258 (9)−0.2889 (6)0.3594 (4)0.057 (2)
H7A0.5144−0.35880.33670.069*
H7B0.6241−0.24670.35770.069*
C80.4219 (9)−0.2380 (6)0.3185 (4)0.058 (2)
H8A0.4317−0.23780.26540.070*
H8B0.3239−0.27710.32400.070*
C90.3642 (8)−0.0726 (6)0.3085 (4)0.057 (2)
H9A0.2627−0.10460.31160.069*
H9B0.3783−0.07110.25600.069*
C100.4111 (8)0.0383 (6)0.3445 (5)0.062 (2)
H10A0.51440.06690.34500.075*
H10B0.36320.08320.31500.075*
C110.2444 (8)0.0633 (6)0.4253 (5)0.058 (2)
H11A0.16660.01180.39450.069*
H11B0.24820.13290.40680.069*
C120.2161 (9)0.0610 (6)0.5048 (5)0.062 (2)
H12A0.29990.10460.53680.074*
H12B0.13460.08900.50990.074*
C130.1522 (8)−0.0568 (6)0.6012 (5)0.062 (2)
H13A0.0718−0.02800.60700.074*
H13B0.2346−0.01820.63630.074*
C140.1140 (8)−0.1704 (6)0.6171 (4)0.061 (2)
H14A0.0774−0.18000.66510.073*
H14B0.0392−0.21050.57850.073*
C150.2126 (9)−0.3179 (6)0.6263 (4)0.062 (2)
H15A0.1494−0.35540.58250.075*
H15B0.1647−0.33780.67020.075*
C160.3524 (9)−0.3477 (6)0.6340 (4)0.057 (2)
H16A0.4185−0.30720.67580.068*
H16B0.3357−0.42250.64290.068*
C17−0.3083 (9)0.3740 (6)0.1718 (4)0.041 (2)
C18−0.4398 (9)0.3943 (6)0.1667 (4)0.053 (2)
H18−0.52300.34110.14920.063*
C19−0.4496 (10)0.4936 (8)0.1874 (4)0.062 (2)
H19−0.53920.50720.18500.074*
C20−0.3253 (11)0.5724 (6)0.2114 (4)0.063 (3)
H20−0.33190.63940.22520.075*
C21−0.1925 (9)0.5539 (6)0.2154 (4)0.055 (2)
H21−0.10960.60820.23160.066*
C22−0.1822 (8)0.4550 (6)0.1955 (4)0.041 (2)
C230.0801 (9)0.5023 (7)0.2165 (5)0.073 (3)
H23A0.15020.46860.24050.087*
H23B0.07050.55610.25170.087*
C240.1317 (9)0.5524 (6)0.1490 (5)0.078 (3)
H24A0.05960.58250.12280.093*
H24B0.21970.60890.16290.093*
C250.2142 (9)0.5112 (6)0.0356 (5)0.072 (3)
H25A0.30080.56940.04790.086*
H25B0.14360.53670.00370.086*
C260.2478 (9)0.4232 (7)−0.0036 (4)0.069 (3)
H26A0.29120.4483−0.04790.083*
H26B0.31670.39730.02920.083*
C270.1488 (10)0.2524 (6)−0.0615 (5)0.086 (3)
H27A0.21140.2218−0.02790.104*
H27B0.19610.2747−0.10530.104*
C280.0099 (11)0.1736 (6)−0.0844 (5)0.077 (3)
H28A−0.05670.2067−0.11270.093*
H28B0.02340.1176−0.11630.093*
C29−0.1779 (10)0.0482 (6)−0.0361 (5)0.071 (3)
H29A−0.1581−0.0139−0.05760.085*
H29B−0.24480.0707−0.07250.085*
C30−0.2434 (9)0.0212 (6)0.0333 (5)0.075 (3)
H30A−0.3298−0.03760.02320.089*
H30B−0.17590.00140.07100.089*
C31−0.3593 (9)0.0944 (6)0.1204 (5)0.072 (3)
H31A−0.29960.08220.16490.087*
H31B−0.44140.03270.10880.087*
C32−0.4091 (9)0.1910 (5)0.1331 (5)0.073 (3)
H32A−0.46440.20520.08750.088*
H32B−0.47040.18020.17260.088*
C330.0053 (8)−0.2538 (7)0.3610 (4)0.050 (2)
C340.1016 (9)0.1047 (7)0.2239 (4)0.055 (2)
C35−0.3980 (10)−0.1725 (6)0.1608 (5)0.054 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0681 (8)0.0618 (7)0.0576 (7)0.0144 (6)0.0103 (6)−0.0051 (6)
K10.0542 (12)0.0595 (12)0.0424 (11)0.0270 (10)0.0131 (9)0.0074 (9)
K20.0580 (13)0.0523 (11)0.0607 (13)0.0137 (10)0.0162 (10)−0.0039 (10)
N10.070 (6)0.076 (6)0.067 (6)0.023 (4)−0.005 (4)0.010 (4)
N20.069 (6)0.059 (5)0.064 (5)0.005 (4)0.013 (4)−0.002 (4)
N30.063 (6)0.067 (5)0.062 (6)0.014 (4)0.009 (4)0.000 (4)
O10.065 (4)0.060 (3)0.047 (4)0.030 (3)0.026 (3)0.023 (3)
O20.061 (4)0.063 (4)0.035 (3)0.032 (3)0.016 (3)0.005 (3)
O30.053 (4)0.058 (4)0.043 (3)0.023 (3)0.002 (3)0.007 (3)
O40.041 (4)0.060 (4)0.052 (4)0.021 (3)0.000 (3)0.006 (3)
O50.052 (4)0.059 (4)0.056 (4)0.023 (3)0.009 (3)−0.005 (3)
O60.060 (4)0.054 (4)0.051 (4)0.024 (3)0.017 (3)0.000 (3)
O70.050 (4)0.034 (3)0.072 (4)0.006 (3)0.018 (3)−0.003 (3)
O80.047 (4)0.062 (4)0.064 (4)0.008 (3)0.003 (3)−0.018 (3)
O90.075 (4)0.059 (4)0.054 (4)0.007 (3)0.026 (3)0.000 (3)
O100.066 (4)0.045 (3)0.066 (4)0.017 (3)0.024 (3)0.004 (3)
O110.079 (5)0.054 (4)0.060 (4)0.022 (3)0.019 (4)0.006 (3)
O120.071 (4)0.044 (3)0.082 (4)0.020 (3)0.027 (4)0.001 (3)
S10.0656 (17)0.0853 (17)0.0639 (17)0.0266 (14)0.0065 (13)0.0060 (14)
S20.0675 (19)0.0794 (18)0.124 (2)0.0000 (15)0.0018 (17)0.0385 (17)
S30.0670 (17)0.0811 (18)0.0795 (19)−0.0015 (14)−0.0045 (15)0.0047 (14)
C10.041 (5)0.042 (5)0.048 (6)0.020 (4)−0.003 (5)−0.007 (4)
C20.071 (7)0.072 (6)0.052 (6)0.031 (5)−0.011 (5)0.000 (5)
C30.056 (7)0.079 (7)0.095 (9)0.037 (6)−0.018 (6)0.001 (6)
C40.055 (7)0.079 (7)0.097 (9)0.034 (6)0.004 (7)−0.007 (7)
C50.053 (6)0.055 (6)0.069 (7)0.020 (5)0.011 (5)−0.003 (5)
C60.044 (6)0.039 (5)0.049 (6)0.010 (4)−0.001 (5)0.001 (4)
C70.066 (6)0.061 (6)0.046 (6)0.017 (5)0.019 (5)−0.012 (4)
C80.068 (7)0.069 (6)0.040 (5)0.017 (5)0.019 (5)0.003 (5)
C90.049 (6)0.090 (7)0.036 (5)0.027 (5)−0.003 (4)0.013 (5)
C100.052 (6)0.071 (6)0.069 (7)0.030 (5)−0.001 (5)0.020 (5)
C110.042 (6)0.064 (6)0.068 (7)0.022 (5)−0.006 (5)0.012 (5)
C120.073 (7)0.055 (6)0.065 (7)0.035 (5)−0.003 (5)−0.009 (5)
C130.056 (6)0.076 (7)0.069 (7)0.041 (5)0.018 (5)−0.004 (5)
C140.052 (6)0.075 (6)0.069 (6)0.033 (5)0.027 (5)0.004 (5)
C150.081 (7)0.067 (6)0.047 (6)0.023 (6)0.032 (5)0.021 (5)
C160.071 (7)0.056 (5)0.056 (6)0.029 (5)0.027 (5)0.030 (4)
C170.045 (6)0.055 (6)0.027 (5)0.015 (5)0.015 (4)0.013 (4)
C180.057 (6)0.050 (6)0.053 (6)0.017 (5)0.008 (5)0.000 (4)
C190.066 (7)0.091 (7)0.048 (6)0.045 (6)0.028 (5)0.010 (5)
C200.092 (8)0.053 (6)0.061 (6)0.043 (6)0.027 (6)0.010 (5)
C210.070 (7)0.055 (6)0.040 (5)0.015 (5)0.014 (5)−0.009 (4)
C220.041 (5)0.050 (5)0.038 (5)0.019 (5)0.012 (4)0.002 (4)
C230.057 (7)0.086 (7)0.060 (7)0.001 (5)−0.001 (5)−0.023 (5)
C240.075 (7)0.058 (6)0.082 (8)−0.012 (5)0.013 (6)−0.021 (6)
C250.081 (7)0.062 (6)0.063 (7)−0.004 (5)0.026 (6)0.005 (5)
C260.080 (8)0.087 (7)0.046 (6)0.020 (6)0.026 (5)0.013 (5)
C270.120 (10)0.059 (6)0.099 (8)0.033 (6)0.069 (8)0.010 (6)
C280.136 (10)0.057 (6)0.049 (6)0.037 (6)0.028 (7)−0.003 (5)
C290.079 (7)0.045 (6)0.087 (8)0.014 (5)0.016 (6)−0.016 (5)
C300.085 (7)0.058 (6)0.090 (8)0.025 (5)0.032 (6)−0.004 (6)
C310.082 (7)0.035 (5)0.097 (8)0.001 (5)0.035 (6)0.006 (5)
C320.062 (6)0.035 (5)0.117 (8)−0.004 (5)0.030 (6)−0.008 (5)
C330.039 (5)0.066 (6)0.040 (5)0.009 (5)0.000 (4)−0.012 (5)
C340.052 (6)0.067 (6)0.043 (6)0.022 (5)−0.014 (5)−0.002 (5)
C350.062 (7)0.045 (5)0.055 (6)0.014 (5)0.015 (5)0.002 (5)

Geometric parameters (Å, °)

Cu1—N11.873 (8)C7—H7A0.970
Cu1—N21.910 (7)C7—H7B0.970
Cu1—N31.915 (7)C8—H8A0.970
K1—O52.683 (5)C8—H8B0.970
K1—O22.718 (5)C9—C101.510 (9)
K1—O12.727 (5)C9—H9A0.970
K1—O32.756 (5)C9—H9B0.970
K1—O62.761 (5)C10—H10A0.970
K1—O42.875 (5)C10—H10B0.970
K1—O4i2.903 (5)C11—C121.489 (9)
K1—S13.317 (3)C11—H11A0.970
K2—O122.729 (5)C11—H11B0.970
K2—O112.730 (5)C12—H12A0.970
K2—O92.765 (5)C12—H12B0.970
K2—O82.773 (5)C13—C141.479 (9)
K2—O102.797 (5)C13—H13A0.970
K2—O72.819 (5)C13—H13B0.970
K2—S23.198 (3)C14—H14A0.970
N1—C331.185 (9)C14—H14B0.970
N2—C341.155 (8)C15—C161.501 (9)
N3—C351.129 (9)C15—H15A0.970
O1—C11.384 (8)C15—H15B0.970
O1—C161.421 (7)C16—H16A0.970
O2—C61.370 (8)C16—H16B0.970
O2—C71.443 (7)C17—C181.364 (9)
O3—C81.426 (7)C17—C221.402 (9)
O3—C91.435 (8)C18—C191.379 (9)
O4—C111.419 (8)C18—H180.930
O4—C101.437 (8)C19—C201.376 (10)
O4—K1i2.903 (5)C19—H190.930
O5—C131.411 (8)C20—C211.367 (10)
O5—C121.420 (8)C20—H200.930
O6—C151.408 (7)C21—C221.373 (9)
O6—C141.433 (8)C21—H210.930
O7—C171.379 (8)C23—C241.468 (10)
O7—C321.421 (8)C23—H23A0.970
O8—C221.376 (8)C23—H23B0.970
O8—C231.431 (8)C24—H24A0.970
O9—C251.411 (8)C24—H24B0.970
O9—C241.427 (8)C25—C261.470 (9)
O10—C261.392 (8)C25—H25A0.970
O10—C271.425 (8)C25—H25B0.970
O11—C281.400 (8)C26—H26A0.970
O11—C291.422 (8)C26—H26B0.970
O12—C311.423 (8)C27—C281.468 (11)
O12—C301.425 (7)C27—H27A0.970
S1—C331.626 (9)C27—H27B0.970
S2—C341.622 (9)C28—H28A0.970
S3—C351.625 (9)C28—H28B0.970
C1—C21.359 (10)C29—C301.476 (10)
C1—C61.388 (9)C29—H29A0.970
C2—C31.377 (10)C29—H29B0.970
C2—H20.930C30—H30A0.970
C3—C41.372 (11)C30—H30B0.970
C3—H30.930C31—C321.495 (9)
C4—C51.369 (10)C31—H31A0.970
C4—H40.930C31—H31B0.970
C5—C61.361 (9)C32—H32A0.970
C5—H50.930C32—H32B0.970
C7—C81.483 (9)
N1—Cu1—N2121.2 (3)C10—C9—H9A110.3
N1—Cu1—N3121.5 (3)O3—C9—H9B110.3
N2—Cu1—N3117.1 (3)C10—C9—H9B110.3
O5—K1—O2170.74 (16)H9A—C9—H9B108.6
O5—K1—O1123.77 (17)O4—C10—C9111.5 (6)
O2—K1—O156.17 (15)O4—C10—H10A109.3
O5—K1—O3117.82 (17)C9—C10—H10A109.3
O2—K1—O361.31 (15)O4—C10—H10B109.3
O1—K1—O3117.47 (16)C9—C10—H10B109.3
O5—K1—O662.87 (16)H10A—C10—H10B108.0
O2—K1—O6116.73 (16)O4—C11—C12109.8 (6)
O1—K1—O660.98 (15)O4—C11—H11A109.7
O3—K1—O6172.87 (16)C12—C11—H11A109.7
O5—K1—O462.10 (16)O4—C11—H11B109.7
O2—K1—O4120.45 (16)C12—C11—H11B109.7
O1—K1—O4165.95 (16)H11A—C11—H11B108.2
O3—K1—O461.15 (15)O5—C12—C11109.1 (6)
O6—K1—O4122.24 (16)O5—C12—H12A109.9
O5—K1—O4i97.66 (15)C11—C12—H12A109.9
O2—K1—O4i91.54 (15)O5—C12—H12B109.9
O1—K1—O4i83.25 (14)C11—C12—H12B109.9
O3—K1—O4i98.96 (15)H12A—C12—H12B108.3
O6—K1—O4i87.85 (15)O5—C13—C14109.4 (6)
O4—K1—O4i83.24 (15)O5—C13—H13A109.8
O5—K1—S188.66 (12)C14—C13—H13A109.8
O2—K1—S182.11 (12)O5—C13—H13B109.8
O1—K1—S183.85 (12)C14—C13—H13B109.8
O3—K1—S187.91 (12)H13A—C13—H13B108.2
O6—K1—S185.01 (12)O6—C14—C13109.0 (6)
O4—K1—S1109.70 (12)O6—C14—H14A109.9
O4i—K1—S1167.06 (11)C13—C14—H14A109.9
O12—K2—O1160.81 (17)O6—C14—H14B109.9
O12—K2—O9158.87 (17)C13—C14—H14B109.9
O11—K2—O9120.39 (18)H14A—C14—H14B108.3
O12—K2—O8113.47 (17)O6—C15—C16109.4 (6)
O11—K2—O8169.50 (18)O6—C15—H15A109.8
O9—K2—O861.31 (15)C16—C15—H15A109.8
O12—K2—O10114.86 (17)O6—C15—H15B109.8
O11—K2—O1061.28 (16)C16—C15—H15B109.8
O9—K2—O1059.47 (15)H15A—C15—H15B108.2
O8—K2—O10118.10 (16)O1—C16—C15107.2 (6)
O12—K2—O759.33 (15)O1—C16—H16A110.3
O11—K2—O7118.88 (17)C15—C16—H16A110.3
O9—K2—O7111.00 (15)O1—C16—H16B110.3
O8—K2—O754.23 (15)C15—C16—H16B110.3
O10—K2—O7141.73 (16)H16A—C16—H16B108.5
O12—K2—S2115.35 (13)C18—C17—O7125.4 (7)
O11—K2—S297.40 (13)C18—C17—C22120.1 (7)
O9—K2—S285.75 (13)O7—C17—C22114.5 (7)
O8—K2—S293.05 (14)C17—C18—C19120.2 (8)
O10—K2—S299.01 (13)C17—C18—H18119.9
O7—K2—S2117.94 (13)C19—C18—H18119.9
C33—N1—Cu1168.9 (7)C20—C19—C18119.3 (8)
C34—N2—Cu1176.3 (7)C20—C19—H19120.3
C35—N3—Cu1168.5 (8)C18—C19—H19120.3
C1—O1—C16117.6 (6)C21—C20—C19121.3 (8)
C1—O1—K1119.3 (4)C21—C20—H20119.4
C16—O1—K1118.6 (4)C19—C20—H20119.4
C6—O2—C7118.6 (6)C20—C21—C22119.7 (8)
C6—O2—K1119.9 (4)C20—C21—H21120.2
C7—O2—K1117.4 (4)C22—C21—H21120.2
C8—O3—C9113.0 (6)C21—C22—O8125.8 (7)
C8—O3—K1102.9 (4)C21—C22—C17119.5 (7)
C9—O3—K1106.0 (4)O8—C22—C17114.7 (7)
C11—O4—C10113.2 (6)O8—C23—C24111.1 (7)
C11—O4—K1106.6 (4)O8—C23—H23A109.4
C10—O4—K1112.5 (4)C24—C23—H23A109.4
C11—O4—K1i120.6 (4)O8—C23—H23B109.4
C10—O4—K1i106.1 (4)C24—C23—H23B109.4
K1—O4—K1i96.76 (15)H23A—C23—H23B108.0
C13—O5—C12113.7 (6)O9—C24—C23108.1 (7)
C13—O5—K1114.9 (4)O9—C24—H24A110.1
C12—O5—K1116.6 (4)C23—C24—H24A110.1
C15—O6—C14113.6 (6)O9—C24—H24B110.1
C15—O6—K1108.0 (4)C23—C24—H24B110.1
C14—O6—K1109.3 (4)H24A—C24—H24B108.4
C17—O7—C32117.2 (6)O9—C25—C26107.9 (7)
C17—O7—K2119.5 (4)O9—C25—H25A110.1
C32—O7—K2117.2 (4)C26—C25—H25A110.1
C22—O8—C23119.9 (6)O9—C25—H25B110.1
C22—O8—K2120.9 (4)C26—C25—H25B110.1
C23—O8—K2109.5 (4)H25A—C25—H25B108.4
C25—O9—C24114.4 (6)O10—C26—C25110.6 (7)
C25—O9—K2118.5 (4)O10—C26—H26A109.5
C24—O9—K2116.9 (4)C25—C26—H26A109.5
C26—O10—C27113.3 (6)O10—C26—H26B109.5
C26—O10—K2113.1 (4)C25—C26—H26B109.5
C27—O10—K2109.5 (4)H26A—C26—H26B108.1
C28—O11—C29114.1 (7)O10—C27—C28108.6 (7)
C28—O11—K2115.8 (4)O10—C27—H27A110.0
C29—O11—K2116.8 (4)C28—C27—H27A110.0
C31—O12—C30112.4 (6)O10—C27—H27B110.0
C31—O12—K2110.9 (4)C28—C27—H27B110.0
C30—O12—K2109.4 (4)H27A—C27—H27B108.3
C33—S1—K193.0 (3)O11—C28—C27109.4 (8)
C34—S2—K289.6 (3)O11—C28—H28A109.8
C2—C1—O1125.6 (8)C27—C28—H28A109.8
C2—C1—C6119.3 (8)O11—C28—H28B109.8
O1—C1—C6115.1 (7)C27—C28—H28B109.8
C1—C2—C3120.6 (9)H28A—C28—H28B108.3
C1—C2—H2119.7O11—C29—C30110.3 (7)
C3—C2—H2119.7O11—C29—H29A109.6
C4—C3—C2120.1 (9)C30—C29—H29A109.6
C4—C3—H3120.0O11—C29—H29B109.6
C2—C3—H3120.0C30—C29—H29B109.6
C5—C4—C3119.2 (9)H29A—C29—H29B108.1
C5—C4—H4120.4O12—C30—C29106.5 (7)
C3—C4—H4120.4O12—C30—H30A110.4
C6—C5—C4121.0 (9)C29—C30—H30A110.4
C6—C5—H5119.5O12—C30—H30B110.4
C4—C5—H5119.5C29—C30—H30B110.4
C5—C6—O2124.8 (8)H30A—C30—H30B108.6
C5—C6—C1119.8 (8)O12—C31—C32106.8 (6)
O2—C6—C1115.4 (7)O12—C31—H31A110.4
O2—C7—C8107.3 (6)C32—C31—H31A110.4
O2—C7—H7A110.2O12—C31—H31B110.4
C8—C7—H7A110.2C32—C31—H31B110.4
O2—C7—H7B110.2H31A—C31—H31B108.6
C8—C7—H7B110.2O7—C32—C31108.1 (7)
H7A—C7—H7B108.5O7—C32—H32A110.1
O3—C8—C7108.7 (7)C31—C32—H32A110.1
O3—C8—H8A110.0O7—C32—H32B110.1
C7—C8—H8A110.0C31—C32—H32B110.1
O3—C8—H8B110.0H32A—C32—H32B108.4
C7—C8—H8B110.0N1—C33—S1177.6 (8)
H8A—C8—H8B108.3N2—C34—S2179.7 (10)
O3—C9—C10107.0 (6)N3—C35—S3179.0 (9)
O3—C9—H9A110.3

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2279).

References

  • Bastos, M. B. R., Moreira, J. C. & Farias, P. A. M. (2000). Anal. Chim. Acta, 408, 83–88.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun.1, 83–90.
  • Rusanova, J. A., Domasevitch, K. V., Vassilyeva, O. Yu., Kokozay, V. N. & Rusanov, E. B. (2000). J. Chem. Soc. Dalton Trans. pp. 2175–2182.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, M., Zheng, P.-J., Zhang, J.-Z., Chen, Z., Shen, J.-M. & Yang, Y.-H. (1987). Acta Cryst. C43, 1544–1546.

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