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Acta Cryst. (2007). E63, m2618    [ doi:10.1107/S1600536807046272 ]

Bis([mu]-N,2-di-3-pyridylisoindoline-1-imine-[kappa]2N,N')bis[aqua(perchlorato-[kappa]O)cadmium(II)] bis(perchlorate) methanol disolvate

L.-N. Zhu, S. Gao and S. W. Ng

Abstract top

The dinuclear dication in the title compound, [Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4O, lies on a twofold rotation axis as the two N,2-di-3-pyridylisoindoline-1-imine N-heterocycles function in [mu]2-bridging modes. Aside from the four N atoms, the Cd atom is also linked to the water and perchlorate O atoms, the O atoms being cis to each other in an octahedral geometry. The charge is balanced by two perchlorate ions; these interact weakly with the coordinated water and uncoordinated methanol molecules.

Comment top

The N-[2,3-dihydro-2-(4-pyridinyl)-1H-isoindol-1-ylidene]-4-pyridinamine N-heterocycle forms an ethanol-coordinated adduct with cadmium dinitrate; the compound exists as a linear chain as the ligand functions as a bridge through its pyridyl N-atoms (Mulyana et al., 2005). N-[2,3-Dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine forms a 2:1 adduct with cadmium perchlorate, but the position of the donor pyridyl N-atoms restricts the formation of a chain structure.

The dinuclear dication in [Cd2(C17H14N4)4(H2O)2(ClO4)2] 2[ClO4].2(CH3OH) lies about a twofold rotation axis. Aside from the four N atoms, the Cd is also linked to the water and perchlorate O atoms, the O atoms being cis to each other in the octahedral geometry (Table 1). The charge is balanced by two perchlorate ions; these interact weakly with the coordinated water and free methanol molecules (Table 2).

Related literature top

For the only reference in the literature to N-[2,3-dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine, see Vanden Eynde et al. (1992). The title compound was synthesized using the same procedure as for the 4-pyridyl analogue (Mulyana et al., 2005); Mulyana et al. (2005) also report the crystal structure of the ethanol-coordinated Cd(NO3)2 adduct.

Experimental top

The ligand was synthesized from o-phthalaldehyde and 3-aminopyridine (in place of 4-aminopyridine) according to the procedure described by Mulyana et al. (2005). An aqueous solution (5 ml) of cadmium perchlorate hexahydrate (0.210 g, 0.5 mmol) was added dropwise to an methanol solution (15 ml) containing N-[2,3-dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine (0.286 g, 1 mmol). The resulting mixture was heated for 0.5 h. Colorless prismatic crystals were obtained from the solution after several days.

Refinement top

The Cl–O distance in the free perchlorate was refined with a distance restraint of Cl–O = 1.440±0.005 Å and the C–O distance in the methanol molecule was restrained to 1.450±0.005 Å (somewhat tight restraints were used). The anisotropic displacement parameters of the methanol atoms were restrained to be nearly isotropic.

The carbon-bound H atoms were generated geometrically (C–H 0.93 – 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The water and methanolic H atoms were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined; U(H) was set to 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the dinuclear dication (the free perchlorate and methanol are omitted). Displacement ellipsoids are drawn at the 30% probability level, and H atoms are drawn as spheres of arbitrary radii. Symmetry code i = 1 − x, y, 3/2 − z.
Bis(µ-N,2-di-3-pyridylisoindoline-1-imine-κ2N,N')bis[aqua(perchlorato-\ κO)cadmium(II)] bis(perchlorate) methanol disolvate top
Crystal data top
[Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4OF000 = 3792
Mr = 1868.04Dx = 1.618 Mg m−3
Orthorhombic, PbcnMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 36081 reflections
a = 21.0869 (6) Åθ = 3.0–27.5º
b = 14.8065 (4) ŵ = 0.78 mm−1
c = 24.5650 (6) ÅT = 295 (2) K
V = 7669.8 (4) Å3Prism, colorless
Z = 40.31 × 0.26 × 0.23 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		8748 independent reflections
Radiation source: fine-focus sealed tube4867 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 295(2) Kθmax = 27.5º
ω scansθmin = 3.0º
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −27→27
Tmin = 0.399, Tmax = 0.842k = −19→17
70672 measured reflectionsl = −31→31
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.181  w = 1/[σ2(Fo2) + (0.0926P)2 + 0.6395P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
8748 reflectionsΔρmax = 0.82 e Å−3
525 parametersΔρmin = −0.92 e Å−3
17 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0010 (2)
Crystal data top
[Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4OV = 7669.8 (4) Å3
Mr = 1868.04Z = 4
Orthorhombic, PbcnMo Kα
a = 21.0869 (6) ŵ = 0.78 mm−1
b = 14.8065 (4) ÅT = 295 (2) K
c = 24.5650 (6) Å0.31 × 0.26 × 0.23 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		8748 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4867 reflections with I > 2σ(I)
Tmin = 0.399, Tmax = 0.842Rint = 0.077
70672 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05617 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.09Δρmax = 0.82 e Å−3
8748 reflectionsΔρmin = −0.92 e Å−3
525 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.635902 (17)0.65940 (2)0.627490 (13)0.05385 (17)
Cl10.74313 (8)0.47014 (11)0.60565 (7)0.0835 (4)
Cl20.53500 (9)0.81815 (11)0.36251 (6)0.0824 (4)
O10.7036 (2)0.5440 (3)0.58675 (14)0.0824 (12)
O20.7426 (3)0.4662 (4)0.66334 (17)0.1157 (17)
O30.7203 (3)0.3871 (3)0.5849 (2)0.1266 (19)
O40.8058 (3)0.4856 (4)0.5878 (3)0.157 (3)
O50.5253 (4)0.8874 (4)0.4008 (3)0.166 (3)
O60.5543 (4)0.8587 (5)0.3128 (2)0.163 (3)
O70.4781 (3)0.7685 (6)0.3600 (3)0.203 (4)
O80.5853 (3)0.7629 (4)0.3823 (3)0.161 (3)
O90.5898 (4)0.8544 (4)0.5059 (3)0.153 (3)
H9o0.59330.84950.47150.229*
O1w0.67378 (17)0.7619 (2)0.56473 (13)0.0669 (9)
H1w10.70500.79400.57540.100*
H1w20.64610.79630.55020.100*
N10.5972 (2)0.5502 (3)0.68868 (15)0.0577 (10)
N20.5722 (2)0.5292 (3)0.83597 (15)0.0610 (11)
N30.60584 (19)0.5596 (3)0.92480 (15)0.0568 (10)
N40.4370 (2)0.6175 (3)0.93989 (15)0.0571 (10)
N50.56585 (18)0.7712 (3)0.66228 (15)0.0519 (9)
N60.39646 (18)0.7952 (3)0.69501 (15)0.0555 (10)
N70.29018 (18)0.7710 (3)0.67160 (15)0.0543 (10)
N80.2817 (2)0.7036 (3)0.81592 (16)0.0630 (11)
C10.5938 (3)0.4629 (3)0.6737 (2)0.0652 (13)
H10.59830.44860.63710.078*
C20.5841 (3)0.3945 (4)0.7100 (2)0.0740 (15)
H20.58080.33510.69810.089*
C30.5791 (3)0.4154 (4)0.7651 (2)0.0703 (15)
H30.57330.36970.79060.084*
C40.5828 (2)0.5038 (3)0.78171 (18)0.0546 (11)
C50.5907 (2)0.5696 (3)0.74220 (18)0.0545 (11)
H50.59160.62980.75290.065*
C60.6173 (3)0.5363 (3)0.87058 (19)0.0557 (12)
C70.6870 (2)0.5257 (3)0.8650 (2)0.0593 (12)
C80.7249 (3)0.5074 (4)0.8197 (2)0.0717 (15)
H80.70720.49780.78550.086*
C90.7896 (3)0.5042 (4)0.8275 (3)0.0794 (17)
H90.81580.49150.79800.095*
C100.8163 (3)0.5192 (4)0.8776 (3)0.093 (2)
H100.86020.51740.88130.112*
C110.7794 (3)0.5368 (4)0.9225 (3)0.0842 (18)
H110.79760.54600.95650.101*
C120.7141 (3)0.5403 (3)0.9154 (2)0.0671 (14)
C130.6648 (3)0.5607 (4)0.9568 (2)0.0672 (14)
H130.66410.51510.98520.081*
H13B0.67180.61940.97330.081*
C140.5484 (2)0.5836 (3)0.94858 (18)0.0533 (11)
C150.5449 (3)0.6060 (3)1.00350 (19)0.0643 (13)
H150.58110.60411.02520.077*
C160.4877 (3)0.6309 (3)1.0255 (2)0.0665 (14)
H160.48450.64311.06250.080*
C170.4347 (3)0.6380 (3)0.9925 (2)0.0651 (14)
H170.39660.65751.00750.078*
C180.4921 (2)0.5902 (3)0.91875 (18)0.0538 (11)
H180.49300.57460.88210.065*
C190.5831 (2)0.8585 (3)0.6609 (2)0.0601 (13)
H190.62500.87270.65290.072*
C200.5412 (3)0.9274 (4)0.6710 (2)0.0672 (14)
H200.55520.98690.67090.081*
C210.4790 (2)0.9087 (3)0.68110 (19)0.0600 (12)
H210.45030.95520.68730.072*
C220.4592 (2)0.8191 (3)0.68203 (16)0.0502 (11)
C230.5045 (2)0.7530 (3)0.67357 (17)0.0507 (11)
H230.49210.69280.67580.061*
C240.3530 (2)0.7902 (3)0.65882 (18)0.0521 (11)
C250.3553 (2)0.8023 (3)0.59882 (18)0.0566 (12)
C260.4052 (3)0.8169 (4)0.5640 (2)0.0687 (14)
H260.44650.82060.57720.082*
C270.3930 (4)0.8260 (4)0.5089 (2)0.0832 (18)
H270.42620.83560.48470.100*
C280.3314 (4)0.8208 (4)0.4899 (2)0.097 (2)
H280.32390.82720.45280.116*
C290.2814 (4)0.8065 (4)0.5238 (2)0.0857 (19)
H290.24020.80470.51040.103*
C300.2936 (3)0.7948 (3)0.5790 (2)0.0650 (14)
C310.2486 (3)0.7760 (4)0.62388 (18)0.0658 (14)
H310.21780.82420.62760.079*
H31B0.22640.71940.61810.079*
C320.2651 (2)0.7455 (3)0.72242 (19)0.0552 (11)
C330.2017 (2)0.7243 (4)0.7285 (2)0.0661 (13)
H330.17400.73080.69930.079*
C340.1797 (3)0.6936 (4)0.7776 (3)0.0788 (16)
H340.13690.68000.78190.095*
C350.2207 (3)0.6831 (4)0.8204 (2)0.0742 (15)
H350.20540.66100.85330.089*
C360.3031 (2)0.7365 (3)0.76821 (18)0.0558 (11)
H360.34540.75410.76580.067*
C370.5692 (4)0.9435 (5)0.5193 (3)0.136 (3)
H37A0.52370.94470.52130.203*
H37B0.58320.98490.49170.203*
H37C0.58670.96090.55380.203*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0483 (2)0.0615 (3)0.0518 (2)0.00206 (16)0.00526 (15)−0.00315 (15)
Cl10.0760 (10)0.0842 (11)0.0903 (10)0.0239 (9)0.0060 (8)0.0004 (8)
Cl20.0913 (12)0.0785 (10)0.0773 (9)−0.0042 (9)0.0064 (8)−0.0024 (7)
O10.090 (3)0.083 (3)0.074 (2)0.048 (2)0.003 (2)−0.0037 (19)
O20.126 (4)0.143 (4)0.078 (3)0.018 (3)−0.019 (3)0.010 (3)
O30.154 (5)0.081 (3)0.145 (4)0.017 (3)−0.030 (4)−0.029 (3)
O40.087 (4)0.156 (5)0.229 (7)0.043 (4)0.061 (4)0.057 (5)
O50.188 (7)0.143 (5)0.165 (6)0.017 (5)0.012 (5)−0.068 (5)
O60.189 (7)0.193 (7)0.108 (4)0.027 (5)0.022 (5)0.048 (4)
O70.175 (7)0.217 (9)0.218 (7)−0.110 (7)−0.058 (6)0.009 (6)
O80.125 (5)0.157 (6)0.200 (6)0.055 (4)0.045 (4)0.088 (5)
O90.195 (6)0.112 (4)0.151 (5)−0.011 (4)−0.085 (4)0.014 (3)
O1w0.064 (2)0.069 (2)0.067 (2)−0.0084 (18)0.0102 (17)0.0027 (17)
N10.060 (3)0.058 (2)0.055 (2)0.006 (2)0.0026 (19)0.0016 (18)
N20.055 (3)0.071 (3)0.057 (2)0.010 (2)−0.0024 (19)0.0027 (19)
N30.049 (2)0.067 (3)0.055 (2)−0.003 (2)−0.0071 (18)0.0079 (18)
N40.061 (3)0.054 (2)0.056 (2)0.004 (2)0.0051 (19)0.0052 (18)
N50.043 (2)0.053 (2)0.060 (2)0.0064 (18)0.0048 (17)−0.0044 (17)
N60.041 (2)0.073 (3)0.053 (2)0.002 (2)−0.0021 (17)0.0018 (18)
N70.043 (2)0.060 (2)0.060 (2)0.0029 (18)−0.0110 (17)−0.0008 (18)
N80.049 (3)0.078 (3)0.062 (2)0.003 (2)0.0024 (19)0.004 (2)
C10.071 (4)0.060 (3)0.065 (3)0.001 (3)0.009 (3)−0.008 (2)
C20.076 (4)0.058 (3)0.087 (4)0.002 (3)0.003 (3)−0.011 (3)
C30.071 (4)0.061 (3)0.080 (4)0.010 (3)0.004 (3)0.012 (3)
C40.048 (3)0.063 (3)0.052 (2)0.002 (2)−0.001 (2)0.002 (2)
C50.050 (3)0.056 (3)0.058 (3)0.003 (2)0.006 (2)−0.003 (2)
C60.054 (3)0.052 (3)0.061 (3)0.004 (2)0.000 (2)0.016 (2)
C70.048 (3)0.046 (3)0.083 (3)0.003 (2)−0.002 (2)0.010 (2)
C80.062 (4)0.065 (4)0.088 (4)0.005 (3)0.007 (3)0.011 (3)
C90.055 (4)0.065 (4)0.118 (5)0.013 (3)0.015 (3)0.018 (3)
C100.053 (4)0.067 (4)0.159 (7)0.002 (3)−0.005 (4)0.020 (4)
C110.059 (4)0.071 (4)0.123 (5)0.001 (3)−0.023 (4)−0.001 (3)
C120.054 (3)0.054 (3)0.093 (4)0.004 (2)−0.009 (3)0.010 (3)
C130.058 (3)0.070 (3)0.073 (3)−0.002 (3)−0.019 (3)0.006 (3)
C140.058 (3)0.048 (3)0.054 (3)−0.003 (2)−0.003 (2)0.009 (2)
C150.075 (4)0.058 (3)0.060 (3)−0.002 (3)−0.011 (3)0.005 (2)
C160.088 (4)0.060 (3)0.052 (3)0.008 (3)0.000 (3)0.001 (2)
C170.077 (4)0.059 (3)0.059 (3)0.009 (3)0.008 (3)0.004 (2)
C180.052 (3)0.059 (3)0.051 (2)0.002 (2)0.004 (2)0.007 (2)
C190.049 (3)0.056 (3)0.076 (3)0.001 (2)0.005 (2)0.000 (2)
C200.068 (4)0.057 (3)0.077 (3)0.002 (3)0.006 (3)0.003 (2)
C210.052 (3)0.056 (3)0.072 (3)0.007 (2)0.004 (2)0.003 (2)
C220.047 (3)0.062 (3)0.041 (2)0.003 (2)−0.0047 (19)0.0064 (19)
C230.044 (3)0.056 (3)0.052 (2)0.003 (2)0.0015 (19)0.002 (2)
C240.052 (3)0.050 (3)0.054 (3)0.005 (2)−0.008 (2)0.000 (2)
C250.072 (4)0.050 (3)0.048 (2)0.004 (2)−0.012 (2)0.001 (2)
C260.084 (4)0.066 (3)0.057 (3)−0.001 (3)−0.006 (3)0.003 (2)
C270.114 (5)0.080 (4)0.055 (3)−0.001 (4)−0.003 (3)0.005 (3)
C280.145 (7)0.095 (5)0.051 (3)−0.002 (5)−0.029 (4)0.007 (3)
C290.105 (5)0.085 (4)0.067 (4)−0.006 (4)−0.036 (4)0.003 (3)
C300.079 (4)0.054 (3)0.062 (3)0.003 (3)−0.024 (3)−0.004 (2)
C310.061 (3)0.065 (3)0.071 (3)0.006 (3)−0.027 (3)−0.006 (2)
C320.048 (3)0.048 (3)0.069 (3)0.006 (2)−0.003 (2)−0.004 (2)
C330.047 (3)0.073 (4)0.078 (3)0.003 (3)−0.013 (3)−0.001 (3)
C340.048 (3)0.084 (4)0.105 (5)−0.003 (3)0.007 (3)0.000 (3)
C350.050 (3)0.089 (4)0.083 (4)−0.004 (3)0.009 (3)0.006 (3)
C360.046 (3)0.065 (3)0.057 (3)0.001 (2)−0.005 (2)0.003 (2)
C370.123 (6)0.141 (6)0.143 (6)0.005 (5)−0.011 (5)0.021 (5)
Geometric parameters (Å, °) top
Cd1—O12.442 (3)C9—C101.373 (8)
Cd1—O1w2.306 (3)C9—H90.9300
Cd1—N12.354 (4)C10—C111.374 (9)
Cd1—N4i2.343 (4)C10—H100.9300
Cd1—N52.378 (4)C11—C121.389 (8)
Cd1—N8i2.319 (4)C11—H110.9300
Cl1—O41.410 (6)C12—C131.485 (8)
Cl1—O31.415 (5)C13—H130.9700
Cl1—O21.418 (4)C13—H13B0.9700
Cl1—O11.450 (4)C14—C151.391 (6)
Cl2—O51.406 (4)C14—C181.399 (7)
Cl2—O71.408 (4)C15—C161.373 (7)
Cl2—O61.419 (4)C15—H150.9300
Cl2—O81.425 (4)C16—C171.383 (7)
O9—C371.428 (5)C16—H160.9300
O9—H9o0.85C17—H170.9300
O1w—H1w10.85C18—H180.9300
O1w—H1w20.85C19—C201.372 (7)
N1—C11.344 (6)C19—H190.9300
N1—C51.353 (5)C20—C211.362 (7)
N2—C61.280 (6)C20—H200.9300
N2—C41.403 (6)C21—C221.392 (7)
N3—C141.391 (6)C21—H210.9300
N3—C61.397 (6)C22—C231.385 (6)
N3—C131.472 (6)C23—H230.9300
N4—C171.329 (6)C24—C251.485 (7)
N4—C181.334 (6)C25—C261.372 (7)
N4—Cd1i2.343 (4)C25—C301.394 (7)
N5—C191.342 (6)C26—C271.385 (7)
N5—C231.350 (6)C26—H260.9300
N6—C241.279 (6)C27—C281.382 (11)
N6—C221.405 (6)C27—H270.9300
N7—C241.391 (6)C28—C291.360 (10)
N7—C321.407 (6)C28—H280.9300
N7—C311.466 (5)C29—C301.393 (7)
N8—C351.327 (7)C29—H290.9300
N8—C361.347 (6)C30—C311.481 (7)
N8—Cd1i2.319 (4)C31—H310.9700
C1—C21.364 (7)C31—H31B0.9700
C1—H10.9300C32—C331.381 (7)
C2—C31.393 (7)C32—C361.387 (6)
C2—H20.9300C33—C341.371 (8)
C3—C41.373 (7)C33—H330.9300
C3—H30.9300C34—C351.370 (8)
C4—C51.385 (6)C34—H340.9300
C5—H50.9300C35—H350.9300
C6—C71.484 (7)C36—H360.9300
C7—C121.381 (7)C37—H37A0.9600
C7—C81.397 (7)C37—H37B0.9600
C8—C91.378 (8)C37—H37C0.9600
C8—H80.9300
O1w—Cd1—N8i87.44 (14)C7—C12—C13110.9 (5)
O1w—Cd1—N4i85.96 (13)C11—C12—C13128.0 (6)
N8i—Cd1—N4i171.83 (14)N3—C13—C12102.9 (4)
O1w—Cd1—N1177.61 (12)N3—C13—H13111.2
N8i—Cd1—N194.06 (15)C12—C13—H13111.2
N4i—Cd1—N192.38 (14)N3—C13—H13B111.2
O1w—Cd1—N589.83 (13)C12—C13—H13B111.2
N8i—Cd1—N593.05 (14)H13—C13—H13B109.1
N4i—Cd1—N591.76 (14)N3—C14—C15121.0 (4)
N1—Cd1—N591.94 (14)N3—C14—C18122.5 (4)
O1w—Cd1—O189.10 (13)C15—C14—C18116.5 (5)
N8i—Cd1—O190.30 (15)C16—C15—C14119.5 (5)
N4i—Cd1—O184.78 (14)C16—C15—H15120.3
N1—Cd1—O189.04 (14)C14—C15—H15120.3
N5—Cd1—O1176.44 (13)C15—C16—C17120.0 (5)
O4—Cl1—O3110.3 (4)C15—C16—H16120.0
O4—Cl1—O2109.0 (4)C17—C16—H16120.0
O3—Cl1—O2108.7 (3)N4—C17—C16121.5 (5)
O4—Cl1—O1108.4 (3)N4—C17—H17119.2
O3—Cl1—O1110.1 (3)C16—C17—H17119.2
O2—Cl1—O1110.2 (3)N4—C18—C14123.8 (4)
O5—Cl2—O7106.6 (5)N4—C18—H18118.1
O5—Cl2—O6107.9 (5)C14—C18—H18118.1
O7—Cl2—O6115.3 (5)N5—C19—C20122.5 (5)
O5—Cl2—O8107.4 (5)N5—C19—H19118.7
O7—Cl2—O8110.4 (5)C20—C19—H19118.7
O6—Cl2—O8108.8 (4)C21—C20—C19120.1 (5)
Cl1—O1—Cd1137.1 (2)C21—C20—H20120.0
C37—O9—H9o109.4C19—C20—H20120.0
Cd1—O1w—H1w1115.3C20—C21—C22119.1 (5)
Cd1—O1w—H1w2115.9C20—C21—H21120.5
H1w1—O1w—H1w2109.0C22—C21—H21120.5
C1—N1—C5117.7 (4)C23—C22—C21117.7 (4)
C1—N1—Cd1120.3 (3)C23—C22—N6120.4 (4)
C5—N1—Cd1120.6 (3)C21—C22—N6121.8 (4)
C6—N2—C4122.3 (4)N5—C23—C22123.4 (4)
C14—N3—C6127.9 (4)N5—C23—H23118.3
C14—N3—C13120.6 (4)C22—C23—H23118.3
C6—N3—C13111.5 (4)N6—C24—N7122.5 (4)
C17—N4—C18118.7 (4)N6—C24—C25131.2 (5)
C17—N4—Cd1i127.0 (4)N7—C24—C25106.3 (4)
C18—N4—Cd1i112.1 (3)C26—C25—C30120.8 (5)
C19—N5—C23117.2 (4)C26—C25—C24131.5 (5)
C19—N5—Cd1119.6 (3)C30—C25—C24107.8 (4)
C23—N5—Cd1122.0 (3)C25—C26—C27118.8 (6)
C24—N6—C22122.1 (4)C25—C26—H26120.6
C24—N7—C32127.8 (4)C27—C26—H26120.6
C24—N7—C31112.3 (4)C28—C27—C26120.0 (7)
C32—N7—C31119.9 (4)C28—C27—H27120.0
C35—N8—C36118.7 (5)C26—C27—H27120.0
C35—N8—Cd1i127.7 (4)C29—C28—C27122.0 (6)
C36—N8—Cd1i111.9 (3)C29—C28—H28119.0
N1—C1—C2122.9 (5)C27—C28—H28119.0
N1—C1—H1118.6C28—C29—C30118.2 (6)
C2—C1—H1118.6C28—C29—H29120.9
C1—C2—C3118.8 (5)C30—C29—H29120.9
C1—C2—H2120.6C29—C30—C25120.2 (6)
C3—C2—H2120.6C29—C30—C31129.0 (5)
C4—C3—C2119.7 (5)C25—C30—C31110.8 (4)
C4—C3—H3120.1N7—C31—C30102.7 (4)
C2—C3—H3120.1N7—C31—H31111.2
C3—C4—C5118.0 (4)C30—C31—H31111.2
C3—C4—N2121.9 (4)N7—C31—H31B111.2
C5—C4—N2119.8 (5)C30—C31—H31B111.2
N1—C5—C4122.9 (4)H31—C31—H31B109.1
N1—C5—H5118.5C33—C32—C36116.7 (5)
C4—C5—H5118.5C33—C32—N7121.3 (4)
N2—C6—N3121.6 (5)C36—C32—N7121.9 (4)
N2—C6—C7131.8 (5)C34—C33—C32119.9 (5)
N3—C6—C7106.6 (4)C34—C33—H33120.0
C12—C7—C8120.6 (5)C32—C33—H33120.0
C12—C7—C6108.1 (4)C35—C34—C33119.9 (5)
C8—C7—C6131.3 (5)C35—C34—H34120.0
C9—C8—C7117.5 (6)C33—C34—H34120.0
C9—C8—H8121.2N8—C35—C34121.5 (5)
C7—C8—H8121.2N8—C35—H35119.2
C10—C9—C8121.8 (6)C34—C35—H35119.2
C10—C9—H9119.1N8—C36—C32123.1 (5)
C8—C9—H9119.1N8—C36—H36118.4
C9—C10—C11121.1 (6)C32—C36—H36118.4
C9—C10—H10119.5O9—C37—H37A109.5
C11—C10—H10119.5O9—C37—H37B109.5
C10—C11—C12118.0 (6)H37A—C37—H37B109.5
C10—C11—H11121.0O9—C37—H37C109.5
C12—C11—H11121.0H37A—C37—H37C109.5
C7—C12—C11121.0 (6)H37B—C37—H37C109.5
O4—Cl1—O1—Cd1−120.7 (5)C13—N3—C14—C18175.0 (4)
O3—Cl1—O1—Cd1118.4 (4)N3—C14—C15—C16178.8 (5)
O2—Cl1—O1—Cd1−1.5 (5)C18—C14—C15—C161.4 (7)
O1w—Cd1—O1—Cl1140.1 (4)C14—C15—C16—C17−3.2 (8)
N8i—Cd1—O1—Cl152.7 (4)C18—N4—C17—C16−0.5 (7)
N4i—Cd1—O1—Cl1−133.8 (4)Cd1i—N4—C17—C16−162.4 (4)
N1—Cd1—O1—Cl1−41.4 (4)C15—C16—C17—N42.8 (8)
N8i—Cd1—N1—C1−120.6 (4)C17—N4—C18—C14−1.4 (7)
N4i—Cd1—N1—C154.3 (4)Cd1i—N4—C18—C14163.0 (4)
N5—Cd1—N1—C1146.2 (4)N3—C14—C18—N4−176.4 (4)
O1—Cd1—N1—C1−30.4 (4)C15—C14—C18—N41.0 (7)
N8i—Cd1—N1—C545.4 (4)C23—N5—C19—C200.6 (7)
N4i—Cd1—N1—C5−139.6 (4)Cd1—N5—C19—C20167.9 (4)
N5—Cd1—N1—C5−47.8 (4)N5—C19—C20—C21−2.2 (8)
O1—Cd1—N1—C5135.6 (4)C19—C20—C21—C221.2 (8)
O1w—Cd1—N5—C19−31.4 (4)C20—C21—C22—C231.3 (7)
N8i—Cd1—N5—C1956.0 (4)C20—C21—C22—N6176.6 (4)
N4i—Cd1—N5—C19−117.4 (4)C24—N6—C22—C23−96.3 (5)
N1—Cd1—N5—C19150.2 (4)C24—N6—C22—C2188.4 (6)
O1w—Cd1—N5—C23135.2 (3)C19—N5—C23—C222.0 (6)
N8i—Cd1—N5—C23−137.3 (3)Cd1—N5—C23—C22−165.0 (3)
N4i—Cd1—N5—C2349.3 (3)C21—C22—C23—N5−2.9 (6)
N1—Cd1—N5—C23−43.2 (3)N6—C22—C23—N5−178.4 (4)
C5—N1—C1—C20.1 (8)C22—N6—C24—N7−176.8 (4)
Cd1—N1—C1—C2166.6 (4)C22—N6—C24—C252.9 (8)
N1—C1—C2—C3−1.8 (9)C32—N7—C24—N6−7.1 (8)
C1—C2—C3—C41.2 (8)C31—N7—C24—N6175.5 (5)
C2—C3—C4—C50.8 (8)C32—N7—C24—C25173.2 (4)
C2—C3—C4—N2174.0 (5)C31—N7—C24—C25−4.3 (5)
C6—N2—C4—C392.8 (6)N6—C24—C25—C264.6 (9)
C6—N2—C4—C5−94.2 (6)N7—C24—C25—C26−175.7 (5)
C1—N1—C5—C42.1 (7)N6—C24—C25—C30−176.5 (5)
Cd1—N1—C5—C4−164.3 (4)N7—C24—C25—C303.2 (5)
C3—C4—C5—N1−2.5 (7)C30—C25—C26—C271.4 (8)
N2—C4—C5—N1−175.8 (4)C24—C25—C26—C27−179.8 (5)
C4—N2—C6—N3−178.5 (4)C25—C26—C27—C280.3 (9)
C4—N2—C6—C73.1 (9)C26—C27—C28—C29−0.2 (10)
C14—N3—C6—N2−4.5 (8)C27—C28—C29—C30−1.6 (10)
C13—N3—C6—N2178.3 (5)C28—C29—C30—C253.2 (9)
C14—N3—C6—C7174.3 (4)C28—C29—C30—C31−178.1 (6)
C13—N3—C6—C7−2.9 (5)C26—C25—C30—C29−3.2 (8)
N2—C6—C7—C12−179.7 (5)C24—C25—C30—C29177.8 (5)
N3—C6—C7—C121.6 (5)C26—C25—C30—C31178.0 (5)
N2—C6—C7—C82.2 (10)C24—C25—C30—C31−1.1 (6)
N3—C6—C7—C8−176.4 (5)C24—N7—C31—C303.5 (5)
C12—C7—C8—C90.3 (8)C32—N7—C31—C30−174.1 (4)
C6—C7—C8—C9178.2 (5)C29—C30—C31—N7179.9 (5)
C7—C8—C9—C10−0.7 (9)C25—C30—C31—N7−1.4 (6)
C8—C9—C10—C111.0 (10)C24—N7—C32—C33−176.9 (5)
C9—C10—C11—C12−1.0 (9)C31—N7—C32—C330.4 (7)
C8—C7—C12—C11−0.3 (8)C24—N7—C32—C360.2 (7)
C6—C7—C12—C11−178.6 (5)C31—N7—C32—C36177.5 (4)
C8—C7—C12—C13178.5 (5)C36—C32—C33—C34−1.8 (8)
C6—C7—C12—C130.2 (6)N7—C32—C33—C34175.5 (5)
C10—C11—C12—C70.6 (9)C32—C33—C34—C35−0.8 (9)
C10—C11—C12—C13−178.0 (5)C36—N8—C35—C340.8 (9)
C14—N3—C13—C12−174.5 (4)Cd1i—N8—C35—C34−163.1 (4)
C6—N3—C13—C122.9 (5)C33—C34—C35—N81.4 (9)
C7—C12—C13—N3−1.8 (6)C35—N8—C36—C32−3.6 (8)
C11—C12—C13—N3176.9 (5)Cd1i—N8—C36—C32162.7 (4)
C6—N3—C14—C15−179.3 (5)C33—C32—C36—N84.1 (7)
C13—N3—C14—C15−2.3 (7)N7—C32—C36—N8−173.2 (4)
C6—N3—C14—C18−2.0 (7)
Symmetry codes: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O3ii0.852.112.945 (6)167
O1w—H1w2···O90.851.832.665 (7)167
O9—H9o···O50.852.322.959 (9)132
Symmetry codes: (ii) −x+3/2, y+1/2, z.
Table 1
Selected geometric parameters (Å) top
Cd1—O12.442 (3)Cd1—N4i2.343 (4)
Cd1—O1w2.306 (3)Cd1—N52.378 (4)
Cd1—N12.354 (4)Cd1—N8i2.319 (4)
Symmetry codes: (i) −x+1, y, −z+3/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O3ii0.852.112.945 (6)167
O1w—H1w2···O90.851.832.665 (7)167
O9—H9o···O50.852.322.959 (9)132
Symmetry codes: (ii) −x+3/2, y+1/2, z.
Acknowledgements top

The authors thank the Heilongjiang Province Natural Science Foundation (grant No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (grant No. 1054 G036) and the University of Malaya for supporting this study.

references
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