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Acta Cryst. (2008). E64, m1427-m1428    [ doi:10.1107/S1600536808033138 ]

(Benzene-1,3-dicarboxylato-[kappa]2O1,O1')(1,12,15,26-tetraaza-5,8,19,22-tetraoxa-3,4:9,10:17,18:23,24-tetrabenzocyclooctacosane-[kappa]4N1,N12,N15,N26)cadmium(II) benzene-1,3-dicarboxylic acid solvate

Z.-F. Jia, J.-F. Ma and L.-P. Zhang

Abstract top

In the title compound, [Cd(C8H4O4)(C36H44N4O4)]·C8H6O4, the CdII atom is six-coordinated by four N atoms from the macrocyclic ligand and two O atoms from a benzene-1,3-dicarboxylate ligand. The complex molecules are linked by N-H...O hydrogen bonds, forming a one-dimensional chain structure along the b axis. The chains are further connected through N-H...O and O-H...O hydrogen bonds between the complex molecule and an uncoordinated benzene-1,3-dicarboxylic acid molecule, resulting in a two-dimensional supramolecular network.

Comment top

As part of an investigation of the supramolecular chemistry of crown ether systems, we present here the crystal structure of the title compound.

In the title compound, the CdII atom displays a psudo-square-pyramidal coordination geometry, defined by four N atoms from the macrocyclic ligand in the basal plane and two O atoms of the carboxylate group of a benzene-1,3-dicarboxylate ligand (Fig. 1). The bond distances (Cd—N, Cd—O) and angles (N—Cd—N, N—Cd—O) are normal (Table 1) (Banerjee et al., 2005; Liu et al., 2005). The complex molecules are linked by N—H···O hydrogen bonds, forming a one-dimensional chain structure along the b-axis (Table 2). The uncoordinated benzene-1,3-dicarboxylic acid molecules are located on both sides of the chain. The adjacent chains are further connected through N—H···O and O—H···O hydrogen bonds between the complex molecule and the benzene-1,3-dicarboxylic acid, resulting in a two-dimensional supramolecular network (Fig. 2) (Sarkar et al., 2008).

Related literature top

For related literature, see: Banerjee et al. (2005); Liu et al. (2005); Sarkar et al. (2008). [From the Section Editors: It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···." etc. Please revise this section as indicated.]

Experimental top

A mixture of Cd(OH)2 (0.146 g, 1 mmol), benzene-1,3-dicarboxylic acid (0.162 g, 1 mmol) and 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza-5,8,19,22- tetraoxacyclooctacosane (0.596 g, 1 mmol) in EtOH (10 ml) was placed in a 20 ml Teflon-lined reactor and heated at 393 K for 3 d. After the reactor was gradually cooled to room temperature at a rate of 10 K h-1, colorless crystals were obtained.

Refinement top

H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH) and 0.97 Å (CH2) and with Uiso(H) = 1.2Ueq(C). H atoms bound to N and O atoms were located in a difference Fourier map and refined with restraints of N—H = 0.84 (2) and O—H = 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N) or Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. View of the two-dimensional supramolecular structure of the title compound. Hydrogen bonds are shown as dashed lines.
(Benzene-1,3-dicarboxylato-κ2O1,O1')(1,12,15,26-tetraaza- 5,8,19,22-tetraoxa-3,4:9,10:17,18:23,24-tetrabenzocyclooctacosane- κ4N1,N12,N15,N26)cadmium(II) benzene-1,3-dicarboxylic acid solvate top
Crystal data top
[Cd(C8H4O4)(C36H44N4O4)]·C8H6O4F(000) = 2152
Mr = 1039.39Dx = 1.464 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10582 reflections
a = 12.912 (3) Åθ = 3.1–27.5°
b = 23.330 (5) ŵ = 0.53 mm−1
c = 16.086 (3) ÅT = 293 K
β = 103.37 (3)°Block, colourless
V = 4714.4 (18) Å30.34 × 0.29 × 0.21 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		10582 independent reflections
Radiation source: 18 kW rotation anode4951 reflections with I > 2σ(I)
graphiteRint = 0.158
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −16→15
Tmin = 0.842, Tmax = 0.913k = −30→30
43452 measured reflectionsl = −20→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0557P)2 + 6.3548P]
where P = (Fo2 + 2Fc2)/3
10582 reflections(Δ/σ)max = 0.001
640 parametersΔρmax = 0.68 e Å−3
9 restraintsΔρmin = −0.71 e Å−3
Crystal data top
[Cd(C8H4O4)(C36H44N4O4)]·C8H6O4V = 4714.4 (18) Å3
Mr = 1039.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.912 (3) ŵ = 0.53 mm−1
b = 23.330 (5) ÅT = 293 K
c = 16.086 (3) Å0.34 × 0.29 × 0.21 mm
β = 103.37 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		10582 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4951 reflections with I > 2σ(I)
Tmin = 0.842, Tmax = 0.913Rint = 0.158
43452 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.085H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.185Δρmax = 0.68 e Å−3
S = 1.02Δρmin = −0.71 e Å−3
10582 reflectionsAbsolute structure: ?
640 parametersFlack parameter: ?
9 restraintsRogers parameter: ?
Special details top

Refinement. The crystal quality is not fine and weakly diffracting, so that the value of R(int) is greater than 0.15.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.82429 (4)0.70844 (2)0.68005 (3)0.04757 (17)
C10.7605 (6)0.6571 (3)0.9444 (4)0.060 (2)
C20.6668 (8)0.6673 (4)0.9702 (6)0.090 (3)
H20.62280.69750.94630.108*
C30.6387 (9)0.6330 (7)1.0308 (7)0.126 (5)
H30.57690.64061.04920.151*
C40.7012 (12)0.5884 (6)1.0634 (6)0.122 (5)
H40.67940.56391.10160.147*
C50.7954 (11)0.5784 (5)1.0419 (6)0.109 (4)
H50.84020.54901.06750.131*
C60.8223 (8)0.6133 (4)0.9807 (5)0.074 (2)
C71.0047 (8)0.5921 (5)1.0100 (6)0.116 (4)
H7A0.99590.55611.03780.140*
H7B1.01770.62171.05350.140*
C81.1002 (8)0.5876 (5)0.9714 (7)0.116 (4)
H8A1.16460.58531.01650.140*
H8B1.09510.55320.93700.140*
C91.1934 (7)0.6434 (4)0.8896 (6)0.088 (3)
C101.2900 (8)0.6155 (5)0.9199 (6)0.115 (4)
H101.29770.58870.96360.138*
C111.3740 (9)0.6284 (6)0.8837 (9)0.125 (5)
H111.43890.60990.90300.150*
C121.3626 (8)0.6679 (5)0.8201 (9)0.118 (4)
H121.41980.67700.79640.142*
C131.2657 (7)0.6944 (4)0.7910 (6)0.090 (3)
H131.25870.72130.74740.108*
C141.1804 (6)0.6827 (3)0.8234 (5)0.068 (2)
C151.0722 (5)0.7088 (3)0.7890 (4)0.0609 (18)
H15A1.04600.72420.83630.073*
H15B1.07930.74050.75160.073*
C161.0233 (7)0.6366 (4)0.6768 (5)0.112 (4)
H16A0.99340.59840.67630.134*
H16B1.10020.63260.69170.134*
C170.9913 (7)0.6604 (5)0.5876 (5)0.109 (4)
H17A1.03140.69520.58450.131*
H17B1.00970.63290.54800.131*
C180.8618 (6)0.7140 (3)0.4908 (4)0.0618 (19)
H18A0.91040.74590.50700.074*
H18B0.78990.72890.48090.074*
C190.8784 (6)0.6886 (3)0.4090 (4)0.060 (2)
C200.9703 (7)0.6970 (4)0.3810 (5)0.078 (2)
H201.02520.71750.41610.094*
C210.9863 (8)0.6769 (4)0.3043 (6)0.088 (3)
H211.05010.68300.28820.106*
C220.9040 (9)0.6474 (4)0.2527 (5)0.089 (3)
H220.91150.63370.20010.107*
C230.8087 (8)0.6377 (4)0.2782 (5)0.079 (3)
H230.75310.61800.24260.095*
C240.7984 (6)0.6576 (3)0.3560 (4)0.061 (2)
C250.6174 (6)0.6254 (3)0.3339 (5)0.069 (2)
H25A0.63260.58850.31150.083*
H25B0.59300.65130.28620.083*
C260.5341 (6)0.6190 (3)0.3835 (5)0.071 (2)
H26A0.46840.60560.34630.085*
H26B0.55670.59100.42860.085*
C270.4366 (6)0.6752 (3)0.4613 (5)0.062 (2)
C280.3364 (6)0.6499 (3)0.4314 (5)0.071 (2)
H280.32220.62790.38190.086*
C290.2600 (6)0.6585 (4)0.4766 (7)0.088 (3)
H290.19430.64060.45830.105*
C300.2770 (7)0.6917 (4)0.5464 (7)0.095 (3)
H300.22290.69790.57470.115*
C310.3760 (7)0.7167 (4)0.5760 (5)0.080 (3)
H310.38760.73990.62420.096*
C320.4574 (6)0.7078 (3)0.5354 (4)0.0611 (19)
C330.5690 (5)0.7290 (3)0.5729 (4)0.061 (2)
H33A0.59430.74990.52930.073*
H33B0.56740.75540.61910.073*
C340.6087 (6)0.6435 (3)0.6662 (4)0.064 (2)
H34A0.64000.60590.66450.077*
H34B0.53190.63940.64920.077*
C350.6395 (5)0.6666 (3)0.7562 (4)0.0595 (19)
H35A0.61050.70490.75740.071*
H35B0.60900.64250.79340.071*
C360.7893 (6)0.6938 (3)0.8745 (4)0.060 (2)
H36A0.75620.73110.87440.072*
H36B0.86580.69950.88780.072*
C380.7114 (7)0.5151 (4)0.5534 (5)0.071 (2)
C390.7151 (6)0.4983 (3)0.4656 (5)0.0593 (19)
C400.6242 (6)0.4738 (3)0.4124 (5)0.072 (2)
H400.56290.46770.43220.086*
C410.6280 (8)0.4590 (4)0.3298 (5)0.086 (3)
H410.56880.44220.29410.104*
C420.7189 (8)0.4687 (3)0.2990 (6)0.081 (2)
H420.71950.45900.24300.097*
C430.8081 (6)0.4928 (3)0.3516 (5)0.067 (2)
C440.8058 (6)0.5070 (3)0.4330 (5)0.065 (2)
H440.86620.52300.46830.078*
C450.9072 (7)0.5032 (4)0.3212 (7)0.078 (2)
C460.6529 (6)1.0083 (3)0.7105 (5)0.066 (2)
C470.7441 (6)0.9768 (3)0.6899 (4)0.0484 (16)
C480.7501 (6)0.9177 (3)0.6919 (4)0.0528 (17)
H480.69590.89670.70690.063*
C490.8341 (6)0.8891 (3)0.6723 (4)0.058 (2)
C500.9124 (6)0.9191 (3)0.6491 (4)0.063 (2)
H500.96920.89960.63570.075*
C510.9097 (7)0.9778 (3)0.6448 (5)0.073 (2)
H510.96340.99810.62810.088*
C520.8253 (6)1.0064 (3)0.6661 (4)0.067 (2)
H520.82331.04620.66420.080*
C530.8379 (8)0.8241 (3)0.6773 (5)0.065 (2)
O10.5169 (4)0.6717 (2)0.4188 (3)0.0736 (15)
O20.7106 (4)0.6477 (2)0.3893 (3)0.0721 (15)
O30.9132 (6)0.6043 (3)0.9519 (4)0.114 (2)
O41.1044 (6)0.6339 (3)0.9226 (4)0.117 (2)
O60.9880 (5)0.5205 (3)0.3692 (5)0.108 (2)
O70.6451 (5)0.4982 (3)0.5886 (4)0.105 (2)
O90.6665 (4)1.0564 (2)0.7453 (3)0.0647 (13)
O100.5626 (5)0.9828 (3)0.6893 (4)0.100 (2)
O110.7628 (5)0.7989 (2)0.6994 (4)0.0899 (19)
O120.9136 (5)0.7986 (2)0.6586 (4)0.0844 (17)
N10.6446 (5)0.6817 (3)0.6058 (4)0.0567 (16)
H1N0.654 (6)0.660 (3)0.566 (3)0.068*
N20.7561 (4)0.6687 (2)0.7885 (3)0.0499 (14)
H2N0.776 (5)0.6348 (12)0.789 (4)0.060*
N30.8784 (5)0.6731 (3)0.5614 (4)0.0558 (15)
H3N0.843 (5)0.6439 (19)0.547 (4)0.067*
N40.9934 (5)0.6679 (3)0.7413 (4)0.0573 (16)
H4N0.981 (6)0.649 (3)0.783 (3)0.069*
O50.8952 (6)0.4924 (3)0.2400 (5)0.108 (2)
H5O0.953 (5)0.503 (5)0.228 (7)0.162*
O80.7893 (5)0.5506 (3)0.5885 (3)0.0796 (16)
H8O0.795 (7)0.549 (4)0.6431 (17)0.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0465 (3)0.0453 (3)0.0494 (3)0.0013 (3)0.0079 (2)0.0025 (3)
C10.066 (5)0.064 (5)0.046 (4)−0.005 (4)0.005 (4)−0.009 (4)
C20.081 (7)0.116 (8)0.074 (6)0.007 (6)0.017 (5)0.011 (6)
C30.091 (8)0.215 (15)0.070 (7)−0.046 (9)0.015 (6)0.017 (8)
C40.150 (12)0.157 (13)0.057 (6)−0.067 (10)0.017 (8)0.009 (7)
C50.169 (12)0.087 (8)0.061 (6)0.002 (8)0.002 (7)0.015 (5)
C60.103 (7)0.067 (6)0.045 (4)0.013 (5)0.004 (5)0.004 (4)
C70.119 (9)0.145 (10)0.079 (6)0.001 (8)0.009 (7)0.043 (7)
C80.128 (10)0.103 (9)0.108 (8)0.035 (7)0.008 (7)0.030 (7)
C90.063 (6)0.114 (8)0.075 (6)0.021 (5)−0.007 (5)−0.012 (6)
C100.087 (7)0.150 (10)0.082 (6)0.051 (7)−0.033 (6)−0.036 (6)
C110.057 (6)0.150 (12)0.145 (11)0.031 (8)−0.020 (7)−0.052 (9)
C120.060 (7)0.126 (10)0.164 (12)−0.006 (7)0.015 (8)−0.066 (9)
C130.057 (5)0.084 (7)0.122 (8)−0.018 (5)0.007 (5)−0.029 (5)
C140.050 (4)0.072 (5)0.072 (5)0.000 (4)−0.006 (4)−0.017 (5)
C150.057 (4)0.056 (4)0.065 (4)0.000 (4)0.005 (4)−0.009 (4)
C160.082 (7)0.139 (9)0.098 (7)0.050 (6)−0.015 (6)−0.042 (7)
C170.079 (6)0.175 (11)0.076 (6)0.056 (7)0.024 (5)0.019 (6)
C180.074 (5)0.049 (4)0.059 (4)−0.010 (4)0.009 (4)−0.001 (4)
C190.066 (5)0.062 (5)0.053 (4)−0.004 (4)0.016 (4)0.007 (3)
C200.085 (6)0.086 (7)0.065 (5)−0.010 (5)0.019 (5)0.004 (4)
C210.090 (7)0.096 (7)0.084 (6)−0.007 (6)0.032 (6)0.012 (5)
C220.125 (8)0.094 (7)0.059 (5)−0.002 (6)0.041 (6)−0.002 (5)
C230.103 (7)0.085 (6)0.048 (4)−0.014 (5)0.015 (5)−0.013 (4)
C240.068 (5)0.062 (5)0.054 (4)−0.001 (4)0.013 (4)0.005 (4)
C250.070 (5)0.062 (5)0.065 (5)−0.007 (4)−0.005 (4)−0.013 (4)
C260.072 (5)0.062 (5)0.078 (5)−0.006 (4)0.015 (5)−0.009 (4)
C270.055 (5)0.064 (5)0.063 (5)0.001 (4)0.007 (4)0.013 (4)
C280.064 (5)0.067 (6)0.076 (5)−0.002 (4)0.001 (5)0.007 (4)
C290.044 (5)0.091 (7)0.119 (8)0.011 (5)0.000 (5)0.023 (6)
C300.060 (6)0.117 (9)0.111 (8)0.011 (5)0.022 (6)−0.001 (6)
C310.066 (5)0.105 (7)0.067 (5)0.024 (5)0.010 (4)0.004 (5)
C320.062 (5)0.066 (5)0.051 (4)0.013 (4)0.003 (4)0.009 (4)
C330.059 (4)0.057 (5)0.060 (4)0.004 (4)0.004 (4)0.001 (3)
C340.059 (5)0.051 (5)0.074 (5)−0.009 (4)0.002 (4)0.008 (4)
C350.055 (4)0.061 (5)0.064 (5)0.007 (4)0.017 (4)0.008 (4)
C360.063 (5)0.058 (5)0.057 (4)−0.003 (4)0.006 (4)−0.005 (3)
C380.077 (6)0.071 (6)0.070 (5)−0.010 (5)0.023 (5)0.003 (4)
C390.060 (5)0.053 (5)0.071 (5)−0.001 (4)0.026 (4)0.010 (4)
C400.068 (5)0.070 (6)0.085 (6)−0.017 (4)0.031 (5)−0.008 (4)
C410.093 (7)0.087 (7)0.076 (6)−0.025 (5)0.015 (5)−0.015 (5)
C420.102 (7)0.065 (6)0.082 (6)−0.009 (5)0.039 (6)−0.007 (4)
C430.078 (6)0.063 (5)0.069 (5)−0.001 (4)0.032 (5)−0.002 (4)
C440.063 (5)0.052 (5)0.087 (6)0.003 (4)0.032 (4)0.006 (4)
C450.085 (7)0.071 (6)0.094 (7)0.010 (5)0.054 (6)0.010 (5)
C460.068 (5)0.056 (5)0.081 (5)−0.006 (4)0.032 (4)0.003 (4)
C470.060 (4)0.046 (4)0.044 (4)0.000 (3)0.021 (3)−0.008 (3)
C480.063 (5)0.050 (5)0.049 (4)−0.009 (4)0.020 (4)−0.003 (3)
C490.073 (5)0.045 (4)0.047 (4)−0.002 (4)−0.005 (4)−0.002 (3)
C500.063 (5)0.061 (5)0.065 (5)0.013 (4)0.018 (4)−0.010 (4)
C510.085 (6)0.057 (6)0.084 (6)−0.003 (5)0.034 (5)0.008 (4)
C520.078 (5)0.049 (4)0.076 (5)0.002 (4)0.024 (5)0.005 (4)
C530.080 (6)0.050 (5)0.055 (4)0.009 (5)−0.008 (4)−0.006 (4)
O10.074 (4)0.073 (4)0.079 (4)−0.007 (3)0.027 (3)−0.011 (3)
O20.066 (3)0.091 (4)0.058 (3)−0.013 (3)0.011 (3)−0.011 (3)
O30.112 (5)0.157 (7)0.067 (4)0.064 (5)0.007 (4)0.019 (4)
O40.104 (5)0.155 (7)0.093 (5)0.046 (5)0.027 (4)0.050 (5)
O60.072 (4)0.138 (6)0.123 (5)−0.005 (4)0.038 (4)0.008 (5)
O70.107 (5)0.130 (6)0.093 (4)−0.040 (4)0.054 (4)−0.021 (4)
O90.084 (4)0.043 (3)0.074 (3)−0.004 (3)0.033 (3)−0.012 (2)
O100.083 (4)0.093 (5)0.138 (5)−0.019 (4)0.052 (4)−0.039 (4)
O110.110 (5)0.050 (4)0.104 (4)0.001 (3)0.013 (4)−0.003 (3)
O120.090 (4)0.054 (4)0.104 (4)0.018 (3)0.013 (3)−0.008 (3)
N10.050 (3)0.063 (4)0.051 (4)0.005 (3)−0.002 (3)−0.010 (3)
N20.047 (3)0.047 (3)0.053 (3)−0.001 (3)0.006 (3)−0.004 (3)
N30.049 (4)0.068 (4)0.050 (3)0.006 (3)0.010 (3)0.008 (3)
N40.050 (3)0.057 (4)0.058 (4)0.006 (3)−0.001 (3)0.000 (3)
O50.130 (6)0.102 (5)0.116 (5)−0.012 (5)0.075 (5)−0.006 (4)
O80.090 (4)0.077 (4)0.068 (3)−0.022 (3)0.012 (3)0.003 (3)
Geometric parameters (Å, °) top
Cd1—N12.433 (6)C26—O11.392 (8)
Cd1—N22.321 (6)C26—H26A0.9700
Cd1—N32.329 (6)C26—H26B0.9700
Cd1—N42.374 (6)C27—O11.370 (9)
Cd1—O112.302 (6)C27—C321.387 (10)
Cd1—O122.462 (6)C27—C281.401 (10)
Cd1—C532.706 (8)C28—C291.369 (11)
C1—C61.344 (10)C28—H280.9300
C1—C21.388 (11)C29—C301.341 (12)
C1—C361.526 (10)C29—H290.9300
C2—C31.373 (13)C30—C311.384 (12)
C2—H20.9300C30—H300.9300
C3—C41.346 (16)C31—C321.376 (10)
C3—H30.9300C31—H310.9300
C4—C51.360 (15)C32—C331.510 (9)
C4—H40.9300C33—N11.487 (8)
C5—C61.383 (13)C33—H33A0.9700
C5—H50.9300C33—H33B0.9700
C6—O31.375 (10)C34—N11.471 (9)
C7—O31.357 (10)C34—C351.509 (9)
C7—C81.507 (8)C34—H34A0.9700
C7—H7A0.9700C34—H34B0.9700
C7—H7B0.9700C35—N21.475 (8)
C8—O41.343 (11)C35—H35A0.9700
C8—H8A0.9700C35—H35B0.9700
C8—H8B0.9700C36—N21.471 (8)
C9—C141.385 (12)C36—H36A0.9700
C9—O41.391 (11)C36—H36B0.9700
C9—C101.392 (12)C38—O71.197 (9)
C10—C111.376 (15)C38—O81.325 (9)
C10—H100.9300C38—C391.478 (10)
C11—C121.361 (16)C39—C441.403 (10)
C11—H110.9300C39—C401.404 (10)
C12—C131.376 (13)C40—C411.386 (10)
C12—H120.9300C40—H400.9300
C13—C141.351 (11)C41—C421.394 (11)
C13—H130.9300C41—H410.9300
C14—C151.507 (10)C42—C431.380 (10)
C15—N41.475 (9)C42—H420.9300
C15—H15A0.9700C43—C441.358 (10)
C15—H15B0.9700C43—C451.492 (8)
C16—N41.394 (10)C44—H440.9300
C16—C171.506 (8)C45—O61.214 (10)
C16—H16A0.9700C45—O51.304 (11)
C16—H16B0.9700C46—O91.246 (8)
C17—N31.452 (10)C46—O101.283 (9)
C17—H17A0.9700C46—C471.490 (10)
C17—H17B0.9700C47—C521.381 (9)
C18—N31.461 (8)C47—C481.382 (9)
C18—C191.503 (10)C48—C491.370 (10)
C18—H18A0.9700C48—H480.9300
C18—H18B0.9700C49—C501.351 (10)
C19—C201.376 (10)C49—C531.518 (10)
C19—C241.382 (10)C50—C511.372 (10)
C20—C211.379 (11)C50—H500.9300
C20—H200.9300C51—C521.385 (10)
C21—C221.372 (12)C51—H510.9300
C21—H210.9300C52—H520.9300
C22—C231.402 (12)C53—O121.239 (9)
C22—H220.9300C53—O111.253 (10)
C23—C241.371 (10)N1—H1N0.85 (6)
C23—H230.9300N2—H2N0.83 (2)
C24—O21.380 (9)N3—H3N0.82 (5)
C25—O21.420 (8)N4—H4N0.85 (6)
C25—C261.489 (10)O5—H5O0.85 (8)
C25—H25A0.9700O8—H8O0.87 (2)
C25—H25B0.9700
O11—Cd1—N293.5 (2)C29—C28—H28120.7
O11—Cd1—N3127.9 (2)C27—C28—H28120.7
N2—Cd1—N3135.4 (2)C30—C29—C28122.0 (9)
O11—Cd1—N4128.5 (2)C30—C29—H29119.0
N2—Cd1—N490.1 (2)C28—C29—H29119.0
N3—Cd1—N477.1 (2)C29—C30—C31119.4 (9)
O11—Cd1—N188.9 (2)C29—C30—H30120.3
N2—Cd1—N177.4 (2)C31—C30—H30120.3
N3—Cd1—N186.6 (2)C32—C31—C30121.3 (8)
N4—Cd1—N1141.5 (2)C32—C31—H31119.3
O11—Cd1—O1254.7 (2)C30—C31—H31119.3
N2—Cd1—O12135.87 (19)C31—C32—C27118.2 (7)
N3—Cd1—O1287.1 (2)C31—C32—C33121.7 (7)
N4—Cd1—O1289.0 (2)C27—C32—C33120.0 (7)
N1—Cd1—O12125.1 (2)N1—C33—C32112.7 (6)
C6—C1—C2118.1 (9)N1—C33—H33A109.0
C6—C1—C36121.7 (8)C32—C33—H33A109.0
C2—C1—C36120.1 (7)N1—C33—H33B109.0
C3—C2—C1120.2 (10)C32—C33—H33B109.0
C3—C2—H2119.9H33A—C33—H33B107.8
C1—C2—H2119.9N1—C34—C35111.3 (6)
C4—C3—C2119.6 (12)N1—C34—H34A109.4
C4—C3—H3120.2C35—C34—H34A109.4
C2—C3—H3120.2N1—C34—H34B109.4
C3—C4—C5121.7 (12)C35—C34—H34B109.4
C3—C4—H4119.2H34A—C34—H34B108.0
C5—C4—H4119.2N2—C35—C34111.8 (6)
C4—C5—C6117.8 (11)N2—C35—H35A109.3
C4—C5—H5121.1C34—C35—H35A109.3
C6—C5—H5121.1N2—C35—H35B109.3
C1—C6—O3115.9 (8)C34—C35—H35B109.3
C1—C6—C5122.4 (10)H35A—C35—H35B107.9
O3—C6—C5121.7 (9)N2—C36—C1113.7 (6)
O3—C7—C8113.3 (8)N2—C36—H36A108.8
O3—C7—H7A108.9C1—C36—H36A108.8
C8—C7—H7A108.9N2—C36—H36B108.8
O3—C7—H7B108.9C1—C36—H36B108.8
C8—C7—H7B108.9H36A—C36—H36B107.7
H7A—C7—H7B107.7O7—C38—O8124.1 (8)
O4—C8—C7109.5 (8)O7—C38—C39123.4 (8)
O4—C8—H8A109.8O8—C38—C39112.6 (8)
C7—C8—H8A109.8C44—C39—C40119.0 (7)
O4—C8—H8B109.8C44—C39—C38122.2 (7)
C7—C8—H8B109.8C40—C39—C38118.8 (7)
H8A—C8—H8B108.2C41—C40—C39118.4 (8)
C14—C9—O4115.9 (8)C41—C40—H40120.8
C14—C9—C10121.2 (11)C39—C40—H40120.8
O4—C9—C10123.0 (10)C40—C41—C42121.3 (8)
C11—C10—C9118.7 (12)C40—C41—H41119.3
C11—C10—H10120.7C42—C41—H41119.3
C9—C10—H10120.7C43—C42—C41120.0 (8)
C12—C11—C10120.5 (11)C43—C42—H42120.0
C12—C11—H11119.7C41—C42—H42120.0
C10—C11—H11119.7C44—C43—C42119.4 (8)
C11—C12—C13119.4 (12)C44—C43—C45119.2 (8)
C11—C12—H12120.3C42—C43—C45121.4 (8)
C13—C12—H12120.3C43—C44—C39122.0 (7)
C14—C13—C12122.4 (11)C43—C44—H44119.0
C14—C13—H13118.8C39—C44—H44119.0
C12—C13—H13118.8O6—C45—O5125.9 (8)
C13—C14—C9117.8 (8)O6—C45—C43121.5 (9)
C13—C14—C15123.1 (8)O5—C45—C43112.7 (9)
C9—C14—C15119.1 (8)O9—C46—O10124.3 (8)
N4—C15—C14113.5 (6)O9—C46—C47120.4 (7)
N4—C15—H15A108.9O10—C46—C47115.3 (7)
C14—C15—H15A108.9C52—C47—C48117.6 (7)
N4—C15—H15B108.9C52—C47—C46120.3 (7)
C14—C15—H15B108.9C48—C47—C46122.1 (7)
H15A—C15—H15B107.7C49—C48—C47121.5 (7)
N4—C16—C17117.0 (7)C49—C48—H48119.2
N4—C16—H16A108.1C47—C48—H48119.2
C17—C16—H16A108.1C50—C49—C48119.6 (7)
N4—C16—H16B108.1C50—C49—C53121.0 (8)
C17—C16—H16B108.1C48—C49—C53119.3 (8)
H16A—C16—H16B107.3C49—C50—C51121.2 (7)
N3—C17—C16112.8 (7)C49—C50—H50119.4
N3—C17—H17A109.0C51—C50—H50119.4
C16—C17—H17A109.0C50—C51—C52118.7 (8)
N3—C17—H17B109.0C50—C51—H51120.6
C16—C17—H17B109.0C52—C51—H51120.6
H17A—C17—H17B107.8C47—C52—C51121.3 (7)
N3—C18—C19113.5 (6)C47—C52—H52119.4
N3—C18—H18A108.9C51—C52—H52119.4
C19—C18—H18A108.9O12—C53—O11123.3 (8)
N3—C18—H18B108.9O12—C53—C49118.9 (9)
C19—C18—H18B108.9O11—C53—C49117.8 (8)
H18A—C18—H18B107.7O12—C53—Cd165.3 (4)
C20—C19—C24116.8 (7)O11—C53—Cd158.0 (4)
C20—C19—C18122.7 (7)C49—C53—Cd1174.5 (6)
C24—C19—C18120.5 (7)C27—O1—C26117.8 (6)
C19—C20—C21124.3 (8)C24—O2—C25118.1 (6)
C19—C20—H20117.8C7—O3—C6118.3 (7)
C21—C20—H20117.8C8—O4—C9120.1 (8)
C22—C21—C20117.1 (9)C53—O11—Cd194.5 (5)
C22—C21—H21121.4C53—O12—Cd187.4 (5)
C20—C21—H21121.4C34—N1—C33113.8 (6)
C21—C22—C23120.9 (8)C34—N1—Cd1104.0 (4)
C21—C22—H22119.6C33—N1—Cd1117.3 (4)
C23—C22—H22119.6C34—N1—H1N105 (5)
C24—C23—C22119.3 (8)C33—N1—H1N112 (5)
C24—C23—H23120.3Cd1—N1—H1N104 (5)
C22—C23—H23120.3C36—N2—C35113.3 (6)
C23—C24—O2124.0 (7)C36—N2—Cd1118.0 (4)
C23—C24—C19121.6 (8)C35—N2—Cd1106.4 (4)
O2—C24—C19114.4 (7)C36—N2—H2N110 (5)
O2—C25—C26108.2 (6)C35—N2—H2N105 (5)
O2—C25—H25A110.1Cd1—N2—H2N103 (5)
C26—C25—H25A110.1C17—N3—C18108.4 (6)
O2—C25—H25B110.1C17—N3—Cd1107.8 (5)
C26—C25—H25B110.1C18—N3—Cd1112.8 (4)
H25A—C25—H25B108.4C17—N3—H3N112 (5)
O1—C26—C25109.5 (7)C18—N3—H3N110 (5)
O1—C26—H26A109.8Cd1—N3—H3N106 (5)
C25—C26—H26A109.8C16—N4—C15116.7 (7)
O1—C26—H26B109.8C16—N4—Cd1106.7 (4)
C25—C26—H26B109.8C15—N4—Cd1114.6 (4)
H26A—C26—H26B108.2C16—N4—H4N116 (5)
O1—C27—C32116.3 (7)C15—N4—H4N99 (5)
O1—C27—C28123.2 (7)Cd1—N4—H4N102 (5)
C32—C27—C28120.4 (8)C45—O5—H5O105 (8)
C29—C28—C27118.5 (8)C38—O8—H8O107 (7)
C6—C1—C2—C3−0.4 (13)N1—Cd1—C53—O12−134.0 (4)
C36—C1—C2—C3177.5 (8)N2—Cd1—C53—O11−35.7 (5)
C1—C2—C3—C4−1.8 (16)N3—Cd1—C53—O11140.9 (5)
C2—C3—C4—C54.2 (18)N4—Cd1—C53—O11−136.5 (5)
C3—C4—C5—C6−4.2 (17)N1—Cd1—C53—O1148.8 (5)
C2—C1—C6—O3178.8 (7)O12—Cd1—C53—O11−177.2 (8)
C36—C1—C6—O30.9 (11)C32—C27—O1—C26140.3 (7)
C2—C1—C6—C50.3 (12)C28—C27—O1—C26−42.5 (10)
C36—C1—C6—C5−177.6 (7)C25—C26—O1—C27175.0 (6)
C4—C5—C6—C11.9 (14)C23—C24—O2—C25−12.8 (11)
C4—C5—C6—O3−176.5 (9)C19—C24—O2—C25168.9 (6)
O3—C7—C8—O449.9 (13)C26—C25—O2—C24−179.4 (6)
C14—C9—C10—C111.2 (15)C8—C7—O3—C6−175.5 (9)
O4—C9—C10—C11−179.2 (9)C1—C6—O3—C7137.9 (9)
C9—C10—C11—C120.4 (17)C5—C6—O3—C7−43.6 (13)
C10—C11—C12—C13−1.1 (18)C7—C8—O4—C9171.2 (8)
C11—C12—C13—C140.1 (15)C14—C9—O4—C8163.9 (9)
C12—C13—C14—C91.5 (13)C10—C9—O4—C8−15.7 (14)
C12—C13—C14—C15−176.5 (8)O12—C53—O11—Cd1−3.1 (8)
O4—C9—C14—C13178.3 (7)C49—C53—O11—Cd1176.0 (5)
C10—C9—C14—C13−2.2 (13)N2—Cd1—O11—C53148.4 (5)
O4—C9—C14—C15−3.6 (11)N3—Cd1—O11—C53−49.4 (6)
C10—C9—C14—C15175.9 (8)N4—Cd1—O11—C5355.5 (6)
C13—C14—C15—N4108.1 (9)N1—Cd1—O11—C53−134.2 (5)
C9—C14—C15—N4−69.9 (9)O12—Cd1—O11—C531.6 (4)
N4—C16—C17—N3−52.6 (13)O11—C53—O12—Cd12.9 (8)
N3—C18—C19—C20−101.1 (8)C49—C53—O12—Cd1−176.2 (6)
N3—C18—C19—C2481.9 (9)O11—Cd1—O12—C53−1.6 (4)
C24—C19—C20—C210.5 (12)N2—Cd1—O12—C53−53.2 (5)
C18—C19—C20—C21−176.6 (8)N3—Cd1—O12—C53140.5 (5)
C19—C20—C21—C220.9 (13)N4—Cd1—O12—C53−142.4 (5)
C20—C21—C22—C23−0.9 (14)N1—Cd1—O12—C5356.7 (5)
C21—C22—C23—C24−0.5 (13)C35—C34—N1—C33−85.7 (7)
C22—C23—C24—O2−176.2 (7)C35—C34—N1—Cd143.0 (6)
C22—C23—C24—C192.1 (12)C32—C33—N1—C34−53.0 (8)
C20—C19—C24—C23−2.0 (11)C32—C33—N1—Cd1−174.6 (5)
C18—C19—C24—C23175.1 (7)O11—Cd1—N1—C34−108.0 (5)
C20—C19—C24—O2176.4 (6)N2—Cd1—N1—C34−14.1 (4)
C18—C19—C24—O2−6.5 (10)N3—Cd1—N1—C34124.0 (4)
O2—C25—C26—O156.7 (8)N4—Cd1—N1—C3459.7 (6)
O1—C27—C28—C29−176.8 (7)O12—Cd1—N1—C34−152.0 (4)
C32—C27—C28—C290.3 (11)C53—Cd1—N1—C34−128.3 (5)
C27—C28—C29—C302.4 (13)O11—Cd1—N1—C3318.6 (5)
C28—C29—C30—C31−2.4 (15)N2—Cd1—N1—C33112.5 (5)
C29—C30—C31—C32−0.3 (14)N3—Cd1—N1—C33−109.4 (5)
C30—C31—C32—C272.9 (12)N4—Cd1—N1—C33−173.7 (4)
C30—C31—C32—C33−172.6 (8)O12—Cd1—N1—C33−25.4 (6)
O1—C27—C32—C31174.4 (7)C53—Cd1—N1—C33−1.7 (6)
C28—C27—C32—C31−2.9 (11)C1—C36—N2—C3567.6 (8)
O1—C27—C32—C33−10.0 (10)C1—C36—N2—Cd1−167.2 (5)
C28—C27—C32—C33172.7 (6)C34—C35—N2—C36177.0 (6)
C31—C32—C33—N1108.6 (8)C34—C35—N2—Cd145.8 (6)
C27—C32—C33—N1−66.9 (9)O11—Cd1—N2—C36−56.5 (5)
N1—C34—C35—N2−64.3 (8)N3—Cd1—N2—C36143.7 (4)
C6—C1—C36—N283.3 (8)N4—Cd1—N2—C3672.0 (5)
C2—C1—C36—N2−94.5 (8)N1—Cd1—N2—C36−144.6 (5)
O7—C38—C39—C44−164.4 (8)O12—Cd1—N2—C36−16.7 (6)
O8—C38—C39—C4415.6 (11)C53—Cd1—N2—C36−40.9 (5)
O7—C38—C39—C4016.9 (13)O11—Cd1—N2—C3572.1 (4)
O8—C38—C39—C40−163.2 (7)N3—Cd1—N2—C35−87.7 (5)
C44—C39—C40—C410.2 (11)N4—Cd1—N2—C35−159.4 (4)
C38—C39—C40—C41179.1 (8)N1—Cd1—N2—C35−16.0 (4)
C39—C40—C41—C42−0.9 (13)O12—Cd1—N2—C35111.9 (4)
C40—C41—C42—C431.0 (13)C53—Cd1—N2—C3587.7 (4)
C41—C42—C43—C44−0.4 (12)C16—C17—N3—C18159.4 (8)
C41—C42—C43—C45179.3 (8)C16—C17—N3—Cd137.0 (10)
C42—C43—C44—C39−0.4 (12)C19—C18—N3—C1770.6 (8)
C45—C43—C44—C39180.0 (7)C19—C18—N3—Cd1−170.1 (5)
C40—C39—C44—C430.4 (11)O11—Cd1—N3—C17114.7 (6)
C38—C39—C44—C43−178.4 (7)N2—Cd1—N3—C17−91.1 (6)
C44—C43—C45—O65.1 (13)N4—Cd1—N3—C17−14.4 (6)
C42—C43—C45—O6−174.6 (9)N1—Cd1—N3—C17−159.3 (6)
C44—C43—C45—O5−174.3 (8)O12—Cd1—N3—C1775.3 (6)
C42—C43—C45—O56.0 (11)C53—Cd1—N3—C1793.1 (6)
O9—C46—C47—C52−33.8 (10)O11—Cd1—N3—C18−4.9 (6)
O10—C46—C47—C52145.5 (7)N2—Cd1—N3—C18149.3 (4)
O9—C46—C47—C48147.6 (7)N4—Cd1—N3—C18−134.0 (5)
O10—C46—C47—C48−33.0 (10)N1—Cd1—N3—C1881.1 (5)
C52—C47—C48—C491.0 (10)O12—Cd1—N3—C18−44.3 (4)
C46—C47—C48—C49179.6 (6)C53—Cd1—N3—C18−26.5 (5)
C47—C48—C49—C50−1.1 (10)C17—C16—N4—C15−94.1 (9)
C47—C48—C49—C53178.7 (6)C17—C16—N4—Cd135.4 (10)
C48—C49—C50—C510.1 (11)C14—C15—N4—C16−51.4 (9)
C53—C49—C50—C51−179.7 (7)C14—C15—N4—Cd1−177.1 (5)
C49—C50—C51—C520.9 (11)O11—Cd1—N4—C16−139.1 (6)
C48—C47—C52—C510.0 (10)N2—Cd1—N4—C16126.3 (6)
C46—C47—C52—C51−178.6 (7)N3—Cd1—N4—C16−10.5 (6)
C50—C51—C52—C47−1.0 (11)N1—Cd1—N4—C1656.7 (7)
C50—C49—C53—O12−1.0 (10)O12—Cd1—N4—C16−97.8 (6)
C48—C49—C53—O12179.2 (6)C53—Cd1—N4—C16−115.1 (6)
C50—C49—C53—O11179.9 (7)O11—Cd1—N4—C15−8.3 (6)
C48—C49—C53—O110.1 (10)N2—Cd1—N4—C15−102.9 (5)
O11—Cd1—C53—O12177.2 (8)N3—Cd1—N4—C15120.2 (5)
N2—Cd1—C53—O12141.4 (4)N1—Cd1—N4—C15−172.5 (4)
N3—Cd1—C53—O12−41.9 (5)O12—Cd1—N4—C1533.0 (5)
N4—Cd1—C53—O1240.6 (5)C53—Cd1—N4—C1515.7 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O80.82 (5)2.42 (4)3.148 (8)147 (6)
N4—H4N···O40.85 (6)2.46 (6)3.043 (8)127 (6)
N2—H2N···O9i0.83 (2)2.10 (3)2.901 (7)163 (6)
O8—H8O···O9i0.87 (2)1.76 (3)2.605 (7)166 (9)
O5—H5O···O10ii0.85 (8)1.71 (8)2.548 (9)170 (12)
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Cd1—N12.433 (6)Cd1—N42.374 (6)
Cd1—N22.321 (6)Cd1—O112.302 (6)
Cd1—N32.329 (6)Cd1—O122.462 (6)
O11—Cd1—N293.5 (2)N3—Cd1—N186.6 (2)
O11—Cd1—N3127.9 (2)N4—Cd1—N1141.5 (2)
N2—Cd1—N3135.4 (2)O11—Cd1—O1254.7 (2)
O11—Cd1—N4128.5 (2)N2—Cd1—O12135.87 (19)
N2—Cd1—N490.1 (2)N3—Cd1—O1287.1 (2)
N3—Cd1—N477.1 (2)N4—Cd1—O1289.0 (2)
O11—Cd1—N188.9 (2)N1—Cd1—O12125.1 (2)
N2—Cd1—N177.4 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O80.82 (5)2.42 (4)3.148 (8)147 (6)
N4—H4N···O40.85 (6)2.46 (6)3.043 (8)127 (6)
N2—H2N···O9i0.83 (2)2.10 (3)2.901 (7)163 (6)
O8—H8O···O9i0.87 (2)1.76 (3)2.605 (7)166 (9)
O5—H5O···O10ii0.85 (8)1.71 (8)2.548 (9)170 (12)
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, z−1/2.
Acknowledgements top

We thank the National Natural Science Foundation of China (grant No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05-0320) and the Analysis and Testing Foundation of Northeast Normal University for support.

references
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