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Acta Cryst. (2009). E65, m641    [ doi:10.1107/S1600536809017073 ]

Tris(phenyl 2-pyridyl ketone oxime-[kappa]2N,N')cadmium(II) dinitrate

J. Yan and G.-X. Liu

Abstract top

The Cd atom in the title compound, [Cd(C12H10N2O)3](NO3)2, adopts a distorted octahedral geometry, being ligated by six N atoms from three different phenyl-2-pyridyl ketone oxime ligands. In the crystal structure, intermolecular O-H...O and C-H...O hydrogen bonds link the molecules into a chain structure propagating along [100]. The chains are further linked into a three-dimensional supramolecular structure via van der Waals forces.

Comment top

Pyridine-2-carbaldehyde oxime ligands usually bind to metals in a bidentate fashion, either chelating one metal center or bridging two metals. Their complexes find application in diverse areas such as functional supramolecular design, magnetic materials and catalysis (Korpi et al., 2005; Pearse et al., 1989; Afrati et al., 2005; Stamatatos et al., 2006). The title compound is a new cadmium complex from the reaction of Cd(NO3)2.4H2O with phenyl-2-pyridyl ketone oxime (ppo). The compound consists of three N,N-chelating ligands and two nitrate anion. The three ppo ligands are coordinated to nickel to form three five-membered CdC2N2 rings.

The central cadmium atom adopts a distorted octahedral geometry (Fig. 1), which are ligated by six N atoms from three different phenyl-2-pyridyl ketone oxime ligands. The bond distances Cd—N, are in the expected ranges of 2.320 (3)–2.402 (3) Å, and the coordination angles around Ni atom are in the range 68.00 (11)–172.80 (12)°. In the crystal structure, intermolecular C—H···O hydrogen bonds link the molecules into one-dimensional chain structure, which are further linker into three-dimensional supramolecular structure via van der Waals forces.

Related literature top

For related structures, see: Korpi et al. (2005); Pearse et al. (1989); Afrati et al. (2005); Stamatatos et al. (2006). For related literature, see: Papatriantafyllopoulou et al. (2007).

Experimental top

A colourless solution of phenyl-2-pyridyl ketone oxime (0.394 g, 2.00 mmol) in MeOH (10 ml) was slowly added to a solution of Cd(NO3)2.4H2O (0.308 g, 1.00 mmol) in MeOH (10 ml) and the resulting colourless solution was stirred for 1 h at room temperature. A small quantity of undissolved material was removed by filtration. The filtrate was allowed to stand undisturbed in a closed flask for a period of 7–8 d. Colourless block crystals appeared which were collected by filtration, washed with cold MeOH (1 ml) and ice-cold Et2O (2 ml), and dried in air [yield: 70%].

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 Å and O—H = 0.82 Å, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for hydroxyl H and x = 1.2 for aromatic H atoms. The deepest hole is located 1.01Å from atom Cd1.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
Tris(phenyl 2-pyridyl ketone oxime-k2N,N')cadmium(II) dinitrate top
Crystal data top
[Cd(C12H10N2O)3](NO3)2Z = 2
Mr = 831.08F000 = 844
Triclinic, P1Dx = 1.556 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.618 (3) ÅCell parameters from 3787 reflections
b = 11.687 (4) Åθ = 2.4–24.4º
c = 15.279 (5) ŵ = 0.68 mm−1
α = 101.263 (4)ºT = 293 K
β = 100.166 (4)ºBlock, colourless
γ = 101.807 (4)º0.24 × 0.22 × 0.18 mm
V = 1773.3 (10) Å3
Data collection top
Bruker SMART Apex CCD area-detector
diffractometer		6526 independent reflections
Radiation source: sealed tube4387 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 293 Kθmax = 25.5º
phi and ω scansθmin = 1.4º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −12→12
Tmin = 0.853, Tmax = 0.887k = −13→14
13329 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.077  w = 1/[σ2(Fo2) + (0.010P)2 + 0.9209P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
6526 reflectionsΔρmax = 0.45 e Å−3
490 parametersΔρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cd(C12H10N2O)3](NO3)2γ = 101.807 (4)º
Mr = 831.08V = 1773.3 (10) Å3
Triclinic, P1Z = 2
a = 10.618 (3) ÅMo Kα
b = 11.687 (4) ŵ = 0.68 mm−1
c = 15.279 (5) ÅT = 293 K
α = 101.263 (4)º0.24 × 0.22 × 0.18 mm
β = 100.166 (4)º
Data collection top
Bruker SMART Apex CCD area-detector
diffractometer		6526 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4387 reflections with I > 2σ(I)
Tmin = 0.853, Tmax = 0.887Rint = 0.041
13329 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046490 parameters
wR(F2) = 0.077H-atom parameters constrained
S = 1.08Δρmax = 0.45 e Å−3
6526 reflectionsΔρmin = −0.54 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.39932 (3)0.31776 (3)0.24172 (2)0.04876 (12)
N10.6295 (3)0.3685 (3)0.2886 (2)0.0444 (9)
N20.5000 (3)0.2396 (3)0.1219 (2)0.0427 (8)
N30.4239 (3)0.4973 (3)0.1957 (2)0.0421 (8)
N40.3093 (3)0.4563 (3)0.3321 (2)0.0421 (8)
N50.3952 (3)0.1499 (3)0.3045 (2)0.0426 (9)
N60.1810 (3)0.1985 (3)0.2194 (2)0.0424 (8)
N70.1902 (3)0.3451 (4)0.0246 (3)0.0670 (12)
N80.3849 (5)0.2736 (4)0.5251 (3)0.0751 (13)
O10.4373 (3)0.1901 (3)0.02985 (19)0.0568 (8)
H10.36080.19640.02150.085*
O20.2339 (3)0.4255 (3)0.39257 (19)0.0524 (8)
H20.26880.38540.42320.079*
O30.0693 (3)0.2320 (3)0.1822 (2)0.0615 (8)
H30.08860.27820.14980.092*
O40.1362 (3)0.3998 (3)0.0776 (2)0.0938 (12)
O50.2140 (4)0.3763 (4)−0.0428 (3)0.1087 (14)
O60.2210 (3)0.2537 (4)0.0439 (3)0.0946 (12)
O70.4502 (5)0.3435 (4)0.4894 (3)0.1285 (17)
O80.2671 (4)0.2615 (4)0.5008 (3)0.1301 (18)
O90.4367 (5)0.2216 (4)0.5717 (3)0.1331 (18)
C10.6938 (4)0.4314 (4)0.3723 (3)0.0514 (11)
H1A0.64690.46850.41030.062*
C20.8274 (4)0.4444 (4)0.4061 (3)0.0586 (13)
H2A0.87000.49080.46460.070*
C30.8948 (4)0.3864 (4)0.3503 (3)0.0625 (14)
H3A0.98360.39020.37150.075*
C40.8300 (4)0.3226 (4)0.2628 (3)0.0484 (11)
H40.87510.28390.22420.058*
C50.6979 (4)0.3163 (3)0.2325 (3)0.0376 (10)
C60.6255 (4)0.2552 (3)0.1382 (3)0.0374 (10)
C70.7001 (4)0.2251 (4)0.0665 (3)0.0426 (10)
C80.6898 (4)0.1069 (4)0.0231 (3)0.0631 (13)
H80.63570.04410.03850.076*
C90.7599 (5)0.0828 (5)−0.0427 (4)0.0842 (17)
H90.75270.0034−0.07200.101*
C100.8401 (5)0.1739 (6)−0.0658 (4)0.0833 (17)
H100.88770.1564−0.11010.100*
C110.8501 (4)0.2905 (5)−0.0238 (3)0.0689 (14)
H110.90360.3525−0.04040.083*
C120.7816 (4)0.3176 (4)0.0431 (3)0.0532 (12)
H120.79010.39740.07230.064*
C130.5020 (4)0.5307 (4)0.1411 (3)0.0591 (13)
H130.54720.47640.11680.071*
C140.5201 (4)0.6396 (4)0.1186 (3)0.0596 (13)
H140.57650.65910.08060.071*
C150.4529 (4)0.7188 (4)0.1534 (3)0.0515 (12)
H150.46140.79310.13850.062*
C160.3725 (4)0.6877 (3)0.2106 (3)0.0492 (11)
H160.32620.74080.23490.059*
C170.3608 (3)0.5765 (3)0.2320 (2)0.0350 (9)
C180.2810 (3)0.5415 (3)0.2966 (2)0.0352 (9)
C190.1797 (4)0.6062 (3)0.3191 (3)0.0396 (10)
C200.0747 (4)0.6039 (4)0.2504 (3)0.0551 (12)
H200.06910.56410.19030.066*
C21−0.0220 (5)0.6609 (5)0.2712 (4)0.0768 (16)
H21−0.09210.65960.22460.092*
C22−0.0163 (6)0.7188 (5)0.3584 (5)0.086 (2)
H22−0.08280.75530.37200.103*
C230.0890 (6)0.7224 (4)0.4261 (4)0.0761 (16)
H230.09400.76270.48590.091*
C240.1879 (4)0.6674 (3)0.4070 (3)0.0553 (12)
H240.25950.67190.45360.066*
C250.5031 (4)0.1182 (4)0.3414 (3)0.0510 (12)
H250.58520.16620.34240.061*
C260.5001 (4)0.0196 (4)0.3777 (3)0.0570 (12)
H260.5775−0.00010.40140.068*
C270.3793 (4)−0.0487 (4)0.3776 (3)0.0508 (11)
H270.3735−0.11580.40240.061*
C280.2668 (4)−0.0187 (3)0.3412 (3)0.0498 (11)
H280.1843−0.06540.34050.060*
C290.2771 (4)0.0812 (3)0.3057 (2)0.0342 (9)
C300.1588 (4)0.1179 (3)0.2634 (3)0.0370 (9)
C310.0258 (4)0.0574 (3)0.2733 (3)0.0404 (10)
C32−0.0003 (4)0.0635 (4)0.3599 (3)0.0518 (11)
H320.06350.10830.41180.062*
C33−0.1227 (4)0.0021 (4)0.3680 (4)0.0642 (14)
H33−0.14160.00740.42560.077*
C34−0.2156 (4)−0.0661 (4)0.2919 (4)0.0690 (15)
H34−0.2964−0.10860.29820.083*
C35−0.1901 (4)−0.0721 (4)0.2063 (4)0.0726 (15)
H35−0.2538−0.11820.15470.087*
C36−0.0694 (4)−0.0095 (4)0.1965 (3)0.0597 (13)
H36−0.0527−0.01250.13850.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03717 (17)0.04326 (19)0.0802 (3)0.01777 (14)0.02862 (17)0.02601 (17)
N10.041 (2)0.036 (2)0.057 (3)0.0085 (16)0.0198 (19)0.0055 (19)
N20.040 (2)0.043 (2)0.041 (2)0.0079 (17)0.0013 (18)0.0117 (18)
N30.0376 (19)0.043 (2)0.054 (2)0.0149 (16)0.0173 (17)0.0192 (18)
N40.051 (2)0.046 (2)0.038 (2)0.0164 (17)0.0197 (17)0.0167 (18)
N50.0320 (19)0.045 (2)0.059 (2)0.0132 (16)0.0172 (17)0.0218 (18)
N60.0314 (18)0.051 (2)0.048 (2)0.0167 (17)0.0053 (17)0.0173 (19)
N70.034 (2)0.087 (4)0.074 (3)0.015 (2)0.007 (2)0.010 (3)
N80.086 (4)0.054 (3)0.077 (4)0.034 (3)−0.007 (3)0.003 (3)
O10.0427 (18)0.064 (2)0.052 (2)0.0047 (17)−0.0019 (16)0.0074 (17)
O20.070 (2)0.060 (2)0.0440 (19)0.0276 (16)0.0248 (17)0.0282 (16)
O30.0425 (17)0.078 (2)0.080 (2)0.0250 (16)0.0141 (16)0.0456 (19)
O40.062 (2)0.109 (3)0.093 (3)0.022 (2)0.018 (2)−0.016 (2)
O50.132 (4)0.123 (3)0.101 (3)0.045 (3)0.053 (3)0.058 (3)
O60.078 (3)0.104 (3)0.129 (4)0.041 (2)0.043 (2)0.054 (3)
O70.152 (4)0.094 (3)0.141 (4)0.023 (3)0.040 (3)0.032 (3)
O80.074 (3)0.107 (3)0.177 (5)0.026 (3)−0.015 (3)−0.005 (3)
O90.183 (5)0.126 (4)0.120 (4)0.095 (4)0.011 (3)0.059 (3)
C10.054 (3)0.049 (3)0.047 (3)0.009 (2)0.017 (2)0.002 (2)
C20.052 (3)0.070 (3)0.040 (3)−0.005 (3)0.005 (2)0.007 (3)
C30.031 (2)0.100 (4)0.055 (3)0.008 (3)0.007 (2)0.026 (3)
C40.037 (2)0.075 (3)0.036 (3)0.019 (2)0.009 (2)0.012 (2)
C50.034 (2)0.036 (2)0.044 (3)0.0074 (19)0.015 (2)0.010 (2)
C60.031 (2)0.032 (2)0.048 (3)0.0077 (18)0.009 (2)0.008 (2)
C70.037 (2)0.050 (3)0.042 (3)0.015 (2)0.009 (2)0.010 (2)
C80.075 (3)0.054 (3)0.068 (3)0.024 (3)0.029 (3)0.012 (3)
C90.100 (4)0.075 (4)0.079 (4)0.033 (3)0.038 (4)−0.005 (3)
C100.076 (4)0.115 (5)0.071 (4)0.041 (4)0.040 (3)0.014 (4)
C110.053 (3)0.105 (4)0.056 (3)0.016 (3)0.020 (3)0.033 (3)
C120.048 (3)0.065 (3)0.044 (3)0.014 (2)0.008 (2)0.010 (2)
C130.057 (3)0.054 (3)0.085 (4)0.020 (2)0.043 (3)0.031 (3)
C140.055 (3)0.061 (3)0.076 (4)0.012 (2)0.034 (3)0.034 (3)
C150.055 (3)0.041 (3)0.058 (3)0.002 (2)0.010 (2)0.022 (2)
C160.059 (3)0.035 (2)0.056 (3)0.011 (2)0.018 (2)0.014 (2)
C170.029 (2)0.037 (2)0.036 (2)0.0046 (18)0.0019 (19)0.008 (2)
C180.037 (2)0.036 (2)0.030 (2)0.0083 (19)0.0039 (19)0.007 (2)
C190.049 (3)0.039 (2)0.039 (3)0.018 (2)0.015 (2)0.015 (2)
C200.061 (3)0.071 (3)0.045 (3)0.031 (3)0.014 (2)0.024 (3)
C210.063 (3)0.089 (4)0.109 (5)0.045 (3)0.032 (3)0.058 (4)
C220.104 (5)0.071 (4)0.134 (6)0.056 (4)0.082 (5)0.056 (4)
C230.117 (5)0.056 (3)0.083 (4)0.042 (3)0.062 (4)0.026 (3)
C240.074 (3)0.042 (3)0.060 (3)0.018 (2)0.032 (3)0.017 (2)
C250.030 (2)0.054 (3)0.073 (3)0.010 (2)0.008 (2)0.029 (3)
C260.051 (3)0.055 (3)0.073 (4)0.020 (2)0.018 (3)0.024 (3)
C270.060 (3)0.041 (3)0.056 (3)0.018 (2)0.014 (3)0.019 (2)
C280.049 (3)0.039 (3)0.068 (3)0.011 (2)0.022 (2)0.019 (2)
C290.038 (2)0.035 (2)0.031 (2)0.0114 (19)0.0088 (19)0.0081 (19)
C300.035 (2)0.036 (2)0.039 (3)0.0088 (19)0.010 (2)0.005 (2)
C310.032 (2)0.042 (3)0.049 (3)0.010 (2)0.012 (2)0.012 (2)
C320.046 (3)0.051 (3)0.055 (3)0.005 (2)0.016 (2)0.009 (2)
C330.054 (3)0.063 (3)0.082 (4)0.011 (3)0.040 (3)0.012 (3)
C340.040 (3)0.061 (3)0.100 (5)0.002 (3)0.023 (3)0.009 (3)
C350.039 (3)0.082 (4)0.075 (4)−0.008 (3)0.003 (3)−0.001 (3)
C360.043 (3)0.066 (3)0.064 (3)0.005 (2)0.016 (3)0.007 (3)
Geometric parameters (Å, °) top
Cd1—N32.320 (3)C11—C121.380 (5)
Cd1—N12.337 (3)C11—H110.9300
Cd1—N52.342 (3)C12—H120.9300
Cd1—N62.376 (3)C13—C141.368 (5)
Cd1—N42.380 (3)C13—H130.9300
Cd1—N22.402 (3)C14—C151.364 (5)
N1—C11.327 (5)C14—H140.9300
N1—C51.353 (4)C15—C161.374 (5)
N2—C61.279 (4)C15—H150.9300
N2—O11.396 (4)C16—C171.387 (5)
N3—C131.332 (4)C16—H160.9300
N3—C171.341 (4)C17—C181.474 (5)
N4—C181.285 (4)C18—C191.486 (5)
N4—O21.378 (3)C19—C241.372 (5)
N5—C251.340 (4)C19—C201.382 (5)
N5—C291.349 (4)C20—C211.382 (5)
N6—C301.269 (4)C20—H200.9300
N6—O31.386 (3)C21—C221.356 (7)
N7—O51.208 (5)C21—H210.9300
N7—O41.227 (4)C22—C231.370 (7)
N7—O61.252 (5)C22—H220.9300
N8—O91.161 (5)C23—C241.382 (6)
N8—O81.210 (5)C23—H230.9300
N8—O71.234 (5)C24—H240.9300
O1—H10.8200C25—C261.371 (5)
O2—H20.8200C25—H250.9300
O3—H30.8200C26—C271.365 (5)
C1—C21.388 (5)C26—H260.9300
C1—H1A0.9300C27—C281.369 (5)
C2—C31.373 (5)C27—H270.9300
C2—H2A0.9300C28—C291.373 (5)
C3—C41.375 (5)C28—H280.9300
C3—H3A0.9300C29—C301.490 (5)
C4—C51.380 (5)C30—C311.491 (5)
C4—H40.9300C31—C361.382 (5)
C5—C61.470 (5)C31—C321.391 (5)
C6—C71.490 (5)C32—C331.389 (5)
C7—C81.384 (5)C32—H320.9300
C7—C121.387 (5)C33—C341.368 (6)
C8—C91.373 (6)C33—H330.9300
C8—H80.9300C34—C351.374 (6)
C9—C101.366 (6)C34—H340.9300
C9—H90.9300C35—C361.387 (5)
C10—C111.362 (6)C35—H350.9300
C10—H100.9300C36—H360.9300
N3—Cd1—N186.23 (10)C11—C12—C7119.5 (4)
N3—Cd1—N5172.80 (12)C11—C12—H12120.2
N1—Cd1—N588.33 (10)C7—C12—H12120.2
N3—Cd1—N6117.48 (10)N3—C13—C14124.2 (4)
N1—Cd1—N6156.28 (10)N3—C13—H13117.9
N5—Cd1—N668.00 (11)C14—C13—H13117.9
N3—Cd1—N469.06 (11)C15—C14—C13118.0 (4)
N1—Cd1—N4110.42 (11)C15—C14—H14121.0
N5—Cd1—N4108.62 (11)C13—C14—H14121.0
N6—Cd1—N480.07 (11)C14—C15—C16119.2 (4)
N3—Cd1—N289.14 (10)C14—C15—H15120.4
N1—Cd1—N268.22 (12)C16—C15—H15120.4
N5—Cd1—N293.23 (10)C15—C16—C17119.7 (4)
N6—Cd1—N2110.04 (11)C15—C16—H16120.2
N4—Cd1—N2158.13 (10)C17—C16—H16120.2
C1—N1—C5118.6 (3)N3—C17—C16121.0 (3)
C1—N1—Cd1122.8 (3)N3—C17—C18117.3 (3)
C5—N1—Cd1117.9 (3)C16—C17—C18121.6 (3)
C6—N2—O1113.9 (3)N4—C18—C17115.1 (3)
C6—N2—Cd1119.3 (3)N4—C18—C19124.6 (3)
O1—N2—Cd1126.3 (2)C17—C18—C19120.2 (3)
C13—N3—C17117.8 (3)C24—C19—C20119.3 (4)
C13—N3—Cd1125.2 (3)C24—C19—C18121.3 (4)
C17—N3—Cd1116.9 (2)C20—C19—C18119.4 (4)
C18—N4—O2114.0 (3)C21—C20—C19119.8 (4)
C18—N4—Cd1115.8 (2)C21—C20—H20120.1
O2—N4—Cd1123.5 (2)C19—C20—H20120.1
C25—N5—C29117.2 (3)C22—C21—C20121.1 (5)
C25—N5—Cd1124.3 (3)C22—C21—H21119.5
C29—N5—Cd1118.5 (2)C20—C21—H21119.5
C30—N6—O3114.2 (3)C21—C22—C23118.9 (5)
C30—N6—Cd1119.8 (3)C21—C22—H22120.6
O3—N6—Cd1123.4 (2)C23—C22—H22120.6
O5—N7—O4122.9 (5)C22—C23—C24121.2 (5)
O5—N7—O6120.6 (5)C22—C23—H23119.4
O4—N7—O6116.5 (5)C24—C23—H23119.4
O9—N8—O8126.6 (6)C19—C24—C23119.6 (5)
O9—N8—O7120.3 (6)C19—C24—H24120.2
O8—N8—O7112.9 (5)C23—C24—H24120.2
N2—O1—H1109.5N5—C25—C26124.1 (4)
N4—O2—H2109.5N5—C25—H25118.0
N6—O3—H3109.5C26—C25—H25118.0
N1—C1—C2123.3 (4)C27—C26—C25117.6 (4)
N1—C1—H1A118.4C27—C26—H26121.2
C2—C1—H1A118.4C25—C26—H26121.2
C3—C2—C1117.8 (4)C26—C27—C28120.1 (4)
C3—C2—H2A121.1C26—C27—H27120.0
C1—C2—H2A121.1C28—C27—H27120.0
C2—C3—C4119.5 (4)C27—C28—C29119.3 (4)
C2—C3—H3A120.2C27—C28—H28120.4
C4—C3—H3A120.2C29—C28—H28120.4
C3—C4—C5119.7 (4)N5—C29—C28121.8 (3)
C3—C4—H4120.1N5—C29—C30116.0 (3)
C5—C4—H4120.1C28—C29—C30122.2 (3)
N1—C5—C4121.0 (4)N6—C30—C29115.6 (3)
N1—C5—C6116.9 (3)N6—C30—C31125.1 (3)
C4—C5—C6122.0 (3)C29—C30—C31119.2 (3)
N2—C6—C5116.2 (3)C36—C31—C32120.0 (4)
N2—C6—C7123.9 (4)C36—C31—C30119.9 (4)
C5—C6—C7119.6 (3)C32—C31—C30120.0 (4)
C8—C7—C12119.5 (4)C33—C32—C31119.3 (4)
C8—C7—C6121.3 (4)C33—C32—H32120.4
C12—C7—C6119.2 (4)C31—C32—H32120.4
C9—C8—C7119.6 (4)C34—C33—C32120.5 (4)
C9—C8—H8120.2C34—C33—H33119.8
C7—C8—H8120.2C32—C33—H33119.8
C10—C9—C8120.9 (5)C33—C34—C35120.3 (4)
C10—C9—H9119.5C33—C34—H34119.8
C8—C9—H9119.5C35—C34—H34119.8
C11—C10—C9119.8 (5)C34—C35—C36120.1 (5)
C11—C10—H10120.1C34—C35—H35119.9
C9—C10—H10120.1C36—C35—H35119.9
C10—C11—C12120.6 (5)C31—C36—C35119.8 (4)
C10—C11—H11119.7C31—C36—H36120.1
C12—C11—H11119.7C35—C36—H36120.1
N3—Cd1—N1—C190.4 (3)N2—C6—C7—C8−69.3 (5)
N5—Cd1—N1—C1−84.8 (3)C5—C6—C7—C8116.4 (4)
N6—Cd1—N1—C1−88.5 (4)N2—C6—C7—C12110.8 (5)
N4—Cd1—N1—C124.4 (3)C5—C6—C7—C12−63.5 (5)
N2—Cd1—N1—C1−179.0 (3)C12—C7—C8—C9−0.3 (7)
N3—Cd1—N1—C5−99.7 (3)C6—C7—C8—C9179.8 (4)
N5—Cd1—N1—C585.0 (3)C7—C8—C9—C100.2 (8)
N6—Cd1—N1—C581.4 (4)C8—C9—C10—C11−0.6 (9)
N4—Cd1—N1—C5−165.7 (2)C9—C10—C11—C121.1 (8)
N2—Cd1—N1—C5−9.1 (2)C10—C11—C12—C7−1.1 (7)
N3—Cd1—N2—C689.4 (3)C8—C7—C12—C110.7 (6)
N1—Cd1—N2—C63.1 (3)C6—C7—C12—C11−179.4 (4)
N5—Cd1—N2—C6−83.8 (3)C17—N3—C13—C14−1.2 (7)
N6—Cd1—N2—C6−151.5 (3)Cd1—N3—C13—C14−176.6 (3)
N4—Cd1—N2—C693.9 (4)N3—C13—C14—C15−0.7 (7)
N3—Cd1—N2—O1−81.9 (3)C13—C14—C15—C161.3 (7)
N1—Cd1—N2—O1−168.2 (3)C14—C15—C16—C17−0.1 (6)
N5—Cd1—N2—O1104.9 (3)C13—N3—C17—C162.4 (6)
N6—Cd1—N2—O137.2 (3)Cd1—N3—C17—C16178.2 (3)
N4—Cd1—N2—O1−77.4 (4)C13—N3—C17—C18−176.4 (4)
N1—Cd1—N3—C1352.5 (3)Cd1—N3—C17—C18−0.6 (4)
N6—Cd1—N3—C13−128.0 (3)C15—C16—C17—N3−1.8 (6)
N4—Cd1—N3—C13166.1 (4)C15—C16—C17—C18177.0 (4)
N2—Cd1—N3—C13−15.7 (3)O2—N4—C18—C17179.7 (3)
N1—Cd1—N3—C17−122.9 (3)Cd1—N4—C18—C17−27.8 (4)
N6—Cd1—N3—C1756.6 (3)O2—N4—C18—C191.9 (5)
N4—Cd1—N3—C17−9.3 (3)Cd1—N4—C18—C19154.4 (3)
N2—Cd1—N3—C17168.9 (3)N3—C17—C18—N419.4 (5)
N3—Cd1—N4—C1820.4 (3)C16—C17—C18—N4−159.4 (4)
N1—Cd1—N4—C1897.8 (3)N3—C17—C18—C19−162.7 (3)
N5—Cd1—N4—C18−166.9 (3)C16—C17—C18—C1918.5 (6)
N6—Cd1—N4—C18−104.3 (3)N4—C18—C19—C2458.9 (6)
N2—Cd1—N4—C1815.6 (5)C17—C18—C19—C24−118.8 (4)
N3—Cd1—N4—O2170.0 (3)N4—C18—C19—C20−120.5 (4)
N1—Cd1—N4—O2−112.6 (3)C17—C18—C19—C2061.8 (5)
N5—Cd1—N4—O2−17.3 (3)C24—C19—C20—C21−1.3 (6)
N6—Cd1—N4—O245.3 (3)C18—C19—C20—C21178.1 (4)
N2—Cd1—N4—O2165.2 (3)C19—C20—C21—C22−0.5 (7)
N1—Cd1—N5—C25−4.0 (3)C20—C21—C22—C231.5 (8)
N6—Cd1—N5—C25174.4 (3)C21—C22—C23—C24−0.7 (8)
N4—Cd1—N5—C25−115.1 (3)C20—C19—C24—C232.1 (6)
N2—Cd1—N5—C2564.0 (3)C18—C19—C24—C23−177.3 (4)
N1—Cd1—N5—C29174.6 (3)C22—C23—C24—C19−1.1 (7)
N6—Cd1—N5—C29−7.0 (3)C29—N5—C25—C261.7 (6)
N4—Cd1—N5—C2963.5 (3)Cd1—N5—C25—C26−179.7 (3)
N2—Cd1—N5—C29−117.4 (3)N5—C25—C26—C27−1.4 (7)
N3—Cd1—N6—C30−161.7 (3)C25—C26—C27—C280.8 (6)
N1—Cd1—N6—C3017.1 (5)C26—C27—C28—C29−0.6 (6)
N5—Cd1—N6—C3013.1 (3)C25—N5—C29—C28−1.4 (5)
N4—Cd1—N6—C30−101.7 (3)Cd1—N5—C29—C28179.9 (3)
N2—Cd1—N6—C3098.4 (3)C25—N5—C29—C30−179.4 (3)
N3—Cd1—N6—O3−1.1 (3)Cd1—N5—C29—C301.9 (4)
N1—Cd1—N6—O3177.7 (3)C27—C28—C29—N51.0 (6)
N5—Cd1—N6—O3173.7 (3)C27—C28—C29—C30178.8 (4)
N4—Cd1—N6—O358.9 (3)O3—N6—C30—C29−179.0 (3)
N2—Cd1—N6—O3−101.0 (3)Cd1—N6—C30—C29−16.7 (4)
C5—N1—C1—C2−1.3 (6)O3—N6—C30—C312.5 (5)
Cd1—N1—C1—C2168.5 (3)Cd1—N6—C30—C31164.8 (3)
N1—C1—C2—C3−1.7 (6)N5—C29—C30—N69.7 (5)
C1—C2—C3—C42.7 (6)C28—C29—C30—N6−168.2 (4)
C2—C3—C4—C5−0.8 (6)N5—C29—C30—C31−171.7 (3)
C1—N1—C5—C43.4 (5)C28—C29—C30—C3110.4 (5)
Cd1—N1—C5—C4−167.0 (3)N6—C30—C31—C3661.6 (5)
C1—N1—C5—C6−175.6 (3)C29—C30—C31—C36−116.9 (4)
Cd1—N1—C5—C614.1 (4)N6—C30—C31—C32−121.4 (4)
C3—C4—C5—N1−2.3 (6)C29—C30—C31—C3260.1 (5)
C3—C4—C5—C6176.5 (4)C36—C31—C32—C33−0.1 (6)
O1—N2—C6—C5175.1 (3)C30—C31—C32—C33−177.1 (4)
Cd1—N2—C6—C52.7 (4)C31—C32—C33—C341.6 (7)
O1—N2—C6—C70.6 (5)C32—C33—C34—C35−1.7 (7)
Cd1—N2—C6—C7−171.7 (3)C33—C34—C35—C360.4 (8)
N1—C5—C6—N2−11.1 (5)C32—C31—C36—C35−1.2 (6)
C4—C5—C6—N2170.0 (4)C30—C31—C36—C35175.8 (4)
N1—C5—C6—C7163.6 (3)C34—C35—C36—C311.0 (7)
C4—C5—C6—C7−15.3 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C32—H32···O80.932.483.355 (6)157
C27—H27···O9i0.932.583.191 (6)123
C14—H14···O5ii0.932.493.261 (6)141
C4—H4···O3iii0.932.423.285 (5)155
C3—H3A···O2iii0.932.563.461 (5)164
O3—H3···O60.822.342.892 (4)126
O3—H3···O40.822.002.820 (5)176
O2—H2···O80.822.042.800 (5)154
O2—H2···O70.822.212.939 (6)149
O1—H1···O60.821.812.585 (4)158
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C32—H32···O80.932.483.355 (6)157
C27—H27···O9i0.932.583.191 (6)123
C14—H14···O5ii0.932.493.261 (6)141
C4—H4···O3iii0.932.423.285 (5)155
C3—H3A···O2iii0.932.563.461 (5)164
O3—H3···O60.822.342.892 (4)126
O3—H3···O40.822.002.820 (5)176
O2—H2···O80.822.042.800 (5)154
O2—H2···O70.822.212.939 (6)149
O1—H1···O60.821.812.585 (4)158
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (No. 20731004), the Natural Science Foundation for Outstanding Scholars of Anhui Province, China (grant No. 044-J-04011) and the Natural Science Foundation of Education Commission of Anhui Province, China (No. KJ2008B004).

references
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