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Acta Cryst. (2007). E63, m1654-m1655    [ doi:10.1107/S1600536807022416 ]

catena-Poly[[[bis(2-methyl-1H-imidazole-[kappa]N3)cadmium(II)]-[mu]-cyclohexane-1,4-dicarboxylato] dihydrate]

Y.-J. Li

Abstract top

In the title compound, {[Cd(C8H10O2)(C4H6N2)2]·2H2O}n, each CdII atom is six-coordinated by two N atoms from two 2-methyl-1H-imidazole (mi) molecules and four O atoms from two cyclohexane-1,4-dicarboxylate (1,4-chdc) ligands in a distorted octahedral environment. The asymmetric unit consists of two independent mononuclear complex units and two solvent water molecules. Each 1,4-chdc acts as a bis-chelating ligand that binds two CdII atoms, thus forming two unique helical chains. These chains are decorated with mi ligands alternately on the two sides. Furthermore, O-H...O and N-H...O hydrogen bonds link the chains together, forming a three-dimensional supramolecular structure. There are weak [pi]-[pi] interactions between mi ligands in neighbouring chains at (x, y, z) and (-x, -y, 2 - z), with an interplanar distance of 3.62 (2) Å.

Comment top

Helical structures have received much attention in coordination chemistry and materials chemistry (Lehn, 1990). So far, many helical complexes have been generated by self-assembly processes (Chen & Liu, 2002). An appropriate flexible bidentate organic acid bridge could be useful in the formation of helical chains in the presence of secondary ligands, such as 2,2'-bipyridine (bipy) and 1,10-phenanthroline (phen) (Li et al., 2002). The N atoms from the secondary ligand may occupy two coordination positions of metal ions. The rest of the coordination positions are available for other carboxylate ligands to allow the formation of a helix. We selected cyclohexane-1,4-dicarboxylic acid (1,4-chdcH2) as a bridging ligand and 2-methyl-1H-imidazole (mi) as a secondary ligand, generating a new helical chain coordination polymer, [Cd(1,4-chdc)(mi)2].2H2O, (I), which is reported here.

In compound (I), the asymmetric unit contains two crystallographically nonequivalent CdII atoms (Cd1 and Cd2), two 1,4-chdc anions, four mi ligands, and four free water molecules (Fig. 1). Each CdII atom is six-coordinated by two N atoms from two mi molecules, and four O atoms from two 1,4-chdc ligands in a distorted octahedral environment (Fig. 1). The Cd—O distances range from 2.279 (5) to 2.457 (4) Å, and the Cd—N distances vary from 2.235 (5) to 2.269 (4) Å (Table 1). As shown in Fig. 2, each 1,4-chdc moiety acts as a bis-chelating ligand that binds two CdII atoms, forming two unique helical chains. These chains are decorated with mi ligands alternately at two sides. Furthermore, the O—H···O and N—H···O hydrogen bonds (Table 2) link the chains together, forming a three-dimensional supramolecular structure of (I). There are weak π—π interactions between 2-methyl- 1H-imidazole ligands in neighboring chains at (x, y, z) and (-x, -y, 2 - z), with the interplanar distance of 3.62 (2) Å.

Related literature top

Two related helical coordination polymers with mixed ligands, [Co2(phen)2(1,4-chdc)2(H2O)2]n and [Ni2(phen)2(1,4-chdc)2(H2O)2]n, have been prepared under hydrothermal conditions. The most attractive structural feature of the two isomorphic compounds is that they both exhibit an infinite helical chainlike structure with 21 helices. Moreover, the adjacent chains are linked via hydrogen bonds and π-π interactions into three-dimensional supramolecular structures (Qi et al., 2003).

For related literature, see: Chen & Liu (2002); Lehn (1990); Li et al. (2002).

Experimental top

A mixture of CdCl2.2H2O (0.5 mmol), 1,4-chdc acid (0.5 mmol), mi (0.5 mmol), and H2O (500 mmol) was adjusted to pH = 7 by addition of aqueous NaOH solution, and heated at 453 K for 6 days. After the mixture was slowly cooled to room temperature, colourless crystals of (I) were yielded (37% yield).

Refinement top

All H atoms on C and N atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93 Å) and refined as riding, with Uiso(H) =1.2Ueq(carrier). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O—H = 0.85 Å; their temperature factors were tied to those of parent atoms by a factor of 1.2.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. (H atoms have been omitted). Symmetry code: (i) x + 1/2, y, 1.5 - z; (ii) 0.5 - x, 1/2 + y, z.
[Figure 2] Fig. 2. View of the chain structure in (I). H atoms have been omitted.
catena-Poly[[[bis(2-methyl-1H-imidazole-κN3)cadmium(II)]-µ- cyclohexane-1,4-dicarboxylato] dihydrate] top
Crystal data top
[Cd(C8H10O2)(C4H6N2)2]·2H2OF(000) = 3936
Mr = 482.81Dx = 1.496 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 51297 reflections
a = 17.593 (4) Åθ = 3.2–27.5°
b = 16.005 (3) ŵ = 1.06 mm−1
c = 30.446 (6) ÅT = 292 K
V = 8573 (3) Å3Block, colourless
Z = 160.33 × 0.31 × 0.28 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9751 independent reflections
Radiation source: rotating anode6833 reflections with I > 2σ(I)
graphiteRint = 0.074
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −22→22
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −20→20
Tmin = 0.698, Tmax = 0.742l = −39→38
71497 measured reflections
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0421P)2 + 26.2686P]
where P = (Fo2 + 2Fc2)/3
9751 reflections(Δ/σ)max = 0.002
515 parametersΔρmax = 1.41 e Å−3
24 restraintsΔρmin = −1.01 e Å−3
Crystal data top
[Cd(C8H10O2)(C4H6N2)2]·2H2OV = 8573 (3) Å3
Mr = 482.81Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 17.593 (4) ŵ = 1.06 mm−1
b = 16.005 (3) ÅT = 292 K
c = 30.446 (6) Å0.33 × 0.31 × 0.28 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9751 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		6833 reflections with I > 2σ(I)
Tmin = 0.698, Tmax = 0.742Rint = 0.074
71497 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0421P)2 + 26.2686P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127Δρmax = 1.41 e Å−3
S = 1.01Δρmin = −1.01 e Å−3
9751 reflectionsAbsolute structure: ?
515 parametersFlack parameter: ?
24 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
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
C10.3487 (4)0.0299 (4)0.8365 (2)0.0655 (16)
C20.3969 (4)0.0552 (5)0.8728 (2)0.084 (2)
H2A0.40820.00750.89080.125*
H2B0.37100.09660.89000.125*
H2C0.44330.07830.86150.125*
C30.2583 (6)−0.0328 (6)0.8009 (3)0.117 (4)
H30.2163−0.06580.79430.140*
C40.2962 (5)0.0120 (5)0.7727 (2)0.093 (3)
H40.28620.01650.74280.111*
C50.4929 (5)−0.0180 (4)0.6884 (2)0.086 (2)
H50.46820.00880.66540.104*
C60.5290 (5)−0.0929 (5)0.6857 (2)0.091 (3)
H60.5335−0.12680.66100.109*
C70.5378 (3)−0.0443 (4)0.75212 (19)0.0567 (14)
C80.5594 (5)−0.0398 (6)0.7991 (2)0.114 (3)
H8A0.5626−0.09530.81100.171*
H8B0.5218−0.00850.81500.171*
H8C0.6079−0.01280.80180.171*
C90.3491 (3)0.2185 (3)0.70464 (16)0.0418 (11)
C100.3014 (3)0.2702 (3)0.67294 (15)0.0425 (11)
H100.33730.30100.65440.051*
C110.2531 (3)0.3359 (3)0.69652 (18)0.0471 (12)
H11A0.23520.37670.67530.057*
H11B0.28420.36490.71790.057*
C120.1844 (3)0.2963 (3)0.71987 (16)0.0464 (12)
H12A0.20220.25920.74290.056*
H12B0.15410.33990.73340.056*
C130.1358 (3)0.2479 (3)0.68804 (15)0.0407 (11)
H130.11870.28660.66520.049*
C140.1845 (3)0.1795 (3)0.66569 (16)0.0451 (12)
H14A0.20190.14000.68760.054*
H14B0.15360.14930.64460.054*
C150.2530 (3)0.2179 (4)0.64228 (15)0.0500 (13)
H15A0.28390.17360.62990.060*
H15B0.23530.25270.61830.060*
C160.0660 (3)0.2092 (3)0.70850 (15)0.0421 (11)
C170.0291 (5)0.2609 (8)0.8744 (3)0.140 (4)
H17A0.01820.30130.85190.210*
H17B0.02540.28680.90270.210*
H17C−0.00670.21580.87250.210*
C180.1073 (4)0.2279 (4)0.86811 (18)0.0582 (15)
C190.2189 (5)0.1846 (8)0.8780 (2)0.132 (4)
H190.26370.16740.89150.158*
C200.2070 (6)0.1864 (7)0.8342 (3)0.125 (3)
H200.24140.17220.81220.150*
C21−0.0350 (4)0.1632 (5)0.9842 (3)0.088 (2)
H21−0.04510.21141.00020.106*
C22−0.0868 (5)0.1091 (6)0.9702 (3)0.117 (3)
H22−0.13900.11200.97460.140*
C230.0253 (4)0.0665 (4)0.9494 (2)0.0644 (16)
C240.0853 (5)0.0148 (5)0.9297 (3)0.116 (3)
H24A0.12990.01700.94780.174*
H24B0.09720.03540.90090.174*
H24C0.0680−0.04200.92760.174*
C250.2703 (3)0.1530 (3)1.01604 (16)0.0446 (12)
C260.3384 (3)0.1297 (3)1.04391 (17)0.0487 (12)
H260.35310.18021.06010.058*
C270.4074 (3)0.1047 (3)1.01558 (18)0.0489 (13)
H27A0.41410.14540.99230.059*
H27B0.45290.10521.03360.059*
C280.3971 (3)0.0188 (3)0.99572 (16)0.0440 (11)
H28A0.44150.00480.97840.053*
H28B0.35340.01930.97630.053*
C290.3855 (3)−0.0475 (3)1.03110 (15)0.0414 (11)
H290.4294−0.04611.05080.050*
C300.3793 (3)−0.1346 (3)1.01204 (17)0.0466 (12)
C320.3221 (4)0.0625 (4)1.07818 (16)0.0561 (15)
H32A0.36270.06191.09970.067*
H32B0.27520.07601.09340.067*
C330.3150 (3)−0.0239 (3)1.05761 (16)0.0500 (13)
H33A0.2708−0.02501.03850.060*
H33B0.3072−0.06491.08060.060*
N10.3556 (3)0.0527 (3)0.79580 (16)0.0665 (14)
N20.2897 (3)−0.0240 (4)0.84165 (18)0.0800 (17)
H20.2751−0.04770.86560.096*
N30.4986 (3)0.0114 (3)0.73007 (15)0.0572 (12)
N40.5567 (3)−0.1078 (3)0.72553 (18)0.0638 (13)
H4A0.5826−0.15110.73310.077*
N50.1569 (3)0.2111 (3)0.89909 (14)0.0599 (13)
N60.1345 (3)0.2130 (4)0.82889 (16)0.0862 (19)
H6A0.11090.21910.80440.103*
N70.0366 (3)0.1368 (3)0.97121 (16)0.0603 (12)
N8−0.0480 (4)0.0483 (4)0.9479 (2)0.0862 (19)
H8−0.06790.00560.93520.103*
O10.2783 (2)0.1910 (3)0.98117 (14)0.0797 (14)
O20.2054 (2)0.1357 (3)1.02861 (14)0.0738 (13)
O1W0.1019 (3)0.0996 (3)1.09298 (15)0.0737 (13)
HW110.139 (2)0.113 (4)1.0753 (18)0.088*
HW120.067 (3)0.138 (3)1.090 (2)0.088*
O30.3518 (4)−0.1455 (3)0.97550 (18)0.112 (2)
O2W0.4907 (3)−0.2497 (3)1.09893 (13)0.0690 (12)
HW210.464 (3)−0.218 (3)1.0825 (15)0.083*
HW220.491 (4)−0.232 (4)1.1251 (8)0.083*
O40.4037 (3)−0.1952 (3)1.03138 (15)0.0824 (15)
O3W0.2434 (3)−0.0813 (4)0.92112 (18)0.0933 (16)
HW310.209 (3)−0.120 (4)0.924 (2)0.112*
HW320.277 (3)−0.090 (5)0.941 (2)0.112*
O50.3690 (2)0.2477 (2)0.74102 (13)0.0610 (11)
O4W0.3630 (3)0.2924 (4)0.9246 (2)0.1069 (19)
HW410.344 (4)0.252 (4)0.940 (3)0.128*
HW420.407 (3)0.275 (5)0.915 (3)0.128*
O60.3704 (3)0.1473 (3)0.69354 (13)0.0691 (12)
O70.0579 (2)0.2059 (3)0.74928 (11)0.0602 (11)
O80.0155 (2)0.1791 (3)0.68348 (11)0.0533 (9)
Cd10.44158 (2)0.12656 (2)0.758212 (12)0.04416 (11)
Cd20.14412 (2)0.21222 (2)0.973230 (11)0.04324 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.060 (4)0.071 (4)0.065 (4)−0.002 (3)0.006 (3)0.001 (3)
C20.068 (5)0.123 (6)0.060 (4)−0.019 (4)0.000 (3)0.019 (4)
C30.127 (8)0.136 (8)0.087 (5)−0.081 (7)0.001 (5)−0.013 (5)
C40.113 (7)0.100 (6)0.065 (4)−0.048 (5)0.006 (4)−0.005 (4)
C50.123 (7)0.066 (4)0.070 (4)0.030 (4)−0.038 (4)−0.010 (3)
C60.116 (7)0.074 (5)0.081 (5)0.032 (5)−0.031 (5)−0.030 (4)
C70.048 (3)0.057 (3)0.064 (3)0.014 (3)0.005 (3)0.008 (3)
C80.133 (8)0.131 (8)0.077 (5)0.072 (6)−0.019 (5)0.013 (5)
C90.031 (2)0.051 (3)0.044 (3)−0.007 (2)−0.001 (2)0.006 (2)
C100.029 (2)0.058 (3)0.040 (2)−0.002 (2)0.0027 (19)0.010 (2)
C110.036 (3)0.045 (3)0.061 (3)0.000 (2)0.002 (2)0.009 (2)
C120.038 (3)0.055 (3)0.046 (3)−0.006 (2)0.006 (2)−0.008 (2)
C130.031 (3)0.053 (3)0.038 (2)0.001 (2)−0.0010 (19)0.007 (2)
C140.032 (3)0.061 (3)0.042 (3)−0.005 (2)−0.001 (2)−0.008 (2)
C150.035 (3)0.078 (4)0.036 (2)0.002 (3)0.000 (2)−0.002 (3)
C160.032 (3)0.055 (3)0.039 (2)0.003 (2)0.000 (2)0.003 (2)
C170.096 (7)0.233 (13)0.091 (6)0.073 (8)−0.003 (5)0.037 (7)
C180.059 (4)0.068 (4)0.047 (3)0.002 (3)−0.006 (3)0.003 (3)
C190.084 (6)0.256 (13)0.054 (4)0.081 (7)−0.015 (4)−0.039 (6)
C200.114 (6)0.188 (8)0.072 (5)0.056 (6)0.000 (4)−0.028 (5)
C210.077 (5)0.077 (5)0.110 (6)−0.019 (4)0.022 (4)−0.024 (4)
C220.066 (5)0.133 (8)0.152 (8)−0.030 (5)0.025 (5)−0.053 (7)
C230.084 (5)0.046 (3)0.064 (4)−0.004 (3)−0.010 (3)0.001 (3)
C240.121 (8)0.065 (5)0.163 (9)0.012 (5)0.004 (7)−0.037 (5)
C250.052 (3)0.037 (3)0.044 (3)0.005 (2)−0.003 (2)−0.006 (2)
C260.056 (3)0.042 (3)0.048 (3)0.001 (3)−0.011 (2)−0.009 (2)
C270.038 (3)0.041 (3)0.068 (3)−0.001 (2)−0.008 (2)0.001 (2)
C280.036 (3)0.049 (3)0.048 (3)0.001 (2)0.006 (2)−0.003 (2)
C290.041 (3)0.042 (3)0.041 (2)0.006 (2)−0.009 (2)−0.003 (2)
C300.048 (3)0.048 (3)0.044 (3)0.000 (3)−0.006 (2)−0.003 (2)
C320.071 (4)0.062 (4)0.035 (3)0.018 (3)−0.005 (2)−0.006 (2)
C330.060 (4)0.051 (3)0.039 (3)0.004 (3)0.004 (2)0.011 (2)
N10.072 (4)0.065 (3)0.062 (3)−0.016 (3)−0.002 (3)0.003 (3)
N20.087 (4)0.088 (4)0.065 (3)−0.039 (3)0.003 (3)0.010 (3)
N30.060 (3)0.052 (3)0.059 (3)0.007 (2)−0.007 (2)0.002 (2)
N40.064 (3)0.046 (3)0.081 (3)0.012 (2)−0.009 (3)0.000 (2)
N50.053 (3)0.083 (4)0.043 (2)0.003 (3)−0.007 (2)−0.014 (2)
N60.077 (4)0.137 (6)0.044 (3)0.022 (4)−0.017 (3)−0.008 (3)
N70.067 (3)0.052 (3)0.061 (3)−0.010 (2)−0.006 (2)−0.002 (2)
N80.088 (5)0.077 (4)0.093 (4)−0.040 (4)−0.017 (4)−0.006 (3)
O10.056 (3)0.111 (4)0.072 (3)0.000 (3)−0.006 (2)0.040 (3)
O20.049 (3)0.101 (4)0.071 (3)0.014 (2)0.007 (2)0.028 (2)
O1W0.081 (3)0.073 (3)0.066 (3)−0.024 (3)0.014 (2)−0.004 (2)
O30.175 (5)0.058 (3)0.102 (4)0.009 (3)−0.076 (4)−0.016 (3)
O2W0.069 (3)0.088 (3)0.049 (2)0.014 (3)0.001 (2)−0.004 (2)
O40.124 (4)0.045 (2)0.078 (3)0.015 (3)−0.038 (3)−0.005 (2)
O3W0.074 (4)0.115 (4)0.091 (4)−0.005 (3)−0.004 (3)0.042 (3)
O50.071 (3)0.055 (2)0.058 (2)−0.012 (2)−0.031 (2)0.0038 (18)
O4W0.072 (4)0.112 (5)0.136 (5)0.011 (3)0.014 (3)0.041 (4)
O60.078 (3)0.067 (3)0.062 (2)0.030 (2)−0.017 (2)−0.012 (2)
O70.045 (2)0.099 (3)0.0366 (18)−0.019 (2)0.0004 (16)0.0044 (19)
O80.040 (2)0.080 (3)0.0404 (18)−0.0171 (19)−0.0017 (15)−0.0007 (18)
Cd10.03687 (19)0.0486 (2)0.0470 (2)0.00164 (17)−0.01030 (16)0.00212 (17)
Cd20.0455 (2)0.0431 (2)0.04110 (19)0.00382 (17)−0.00389 (16)−0.00270 (16)
Geometric parameters (Å, °) top
C1—N11.298 (8)C21—N71.386 (9)
C1—N21.360 (8)C21—H210.9300
C1—C21.449 (9)C22—N81.368 (10)
C2—H2A0.9600C22—H220.9300
C2—H2B0.9600C23—N81.323 (8)
C2—H2C0.9600C23—N71.322 (7)
C3—C41.303 (10)C23—C241.468 (10)
C3—N21.364 (9)C24—H24A0.9600
C3—H30.9300C24—H24B0.9600
C4—N11.416 (9)C24—H24C0.9600
C4—H40.9300C25—O11.232 (6)
C5—C61.359 (9)C25—O21.234 (7)
C5—N31.356 (7)C25—C261.516 (7)
C5—H50.9300C26—C321.527 (8)
C6—N41.329 (8)C26—C271.542 (8)
C6—H60.9300C26—H260.9800
C7—N31.313 (7)C27—C281.513 (7)
C7—N41.342 (7)C27—H27A0.9700
C7—C81.482 (9)C27—H27B0.9700
C8—H8A0.9600C28—C291.525 (7)
C8—H8B0.9600C28—H28A0.9700
C8—H8C0.9600C28—H28B0.9700
C9—O61.246 (6)C29—C301.515 (7)
C9—O51.252 (6)C29—C331.527 (7)
C9—C101.523 (7)C29—H290.9800
C10—C151.516 (7)C30—O41.214 (6)
C10—C111.531 (7)C30—O31.226 (6)
C10—H100.9800C32—C331.523 (8)
C11—C121.538 (7)C32—H32A0.9700
C11—H11A0.9700C32—H32B0.9700
C11—H11B0.9700C33—H33A0.9700
C12—C131.508 (7)C33—H33B0.9700
C12—H12A0.9700Cd1—N12.235 (5)
C12—H12B0.9700N2—H20.8600
C13—C161.509 (7)Cd1—N32.266 (5)
C13—C141.547 (7)N4—H4A0.8600
C13—H130.9800Cd2—N52.269 (4)
C14—C151.530 (7)N6—H6A0.8600
C14—H14A0.9700Cd2—N72.244 (5)
C14—H14B0.9700N8—H80.8600
C15—H15A0.9700Cd2—O12.397 (4)
C15—H15B0.9700Cd2—O22.347 (4)
C16—O71.251 (6)O1W—HW110.87 (5)
C16—O81.266 (6)O1W—HW120.87 (5)
C17—C181.485 (10)O2W—HW210.85 (5)
C17—H17A0.9600O2W—HW220.844 (19)
C17—H17B0.9600O3W—HW310.87 (6)
C17—H17C0.9600O3W—HW320.86 (6)
C18—N61.308 (7)O4W—HW410.87 (7)
C18—N51.313 (7)O4W—HW420.87 (6)
C19—N51.335 (8)Cd1—O52.380 (4)
C19—C201.352 (10)Cd1—O62.357 (4)
C19—H190.9300Cd1—O8i2.355 (3)
C20—N61.354 (10)Cd1—O7i2.419 (4)
C20—H200.9300Cd2—O3ii2.279 (5)
C21—C221.327 (10)Cd2—O4ii2.457 (4)
N1—C1—N2111.0 (6)C25—C26—C32114.0 (5)
N1—C1—C2126.5 (6)C25—C26—C27111.9 (4)
N2—C1—C2122.5 (6)C32—C26—C27110.3 (4)
C1—C2—H2A109.5C25—C26—H26106.7
C1—C2—H2B109.5C32—C26—H26106.7
H2A—C2—H2B109.5C27—C26—H26106.7
C1—C2—H2C109.5C28—C27—C26111.4 (4)
H2A—C2—H2C109.5C28—C27—H27A109.3
H2B—C2—H2C109.5C26—C27—H27A109.3
C4—C3—N2109.6 (7)C28—C27—H27B109.3
C4—C3—H3125.2C26—C27—H27B109.3
N2—C3—H3125.2H27A—C27—H27B108.0
C3—C4—N1107.7 (7)C27—C28—C29111.5 (4)
C3—C4—H4126.1C27—C28—H28A109.3
N1—C4—H4126.1C29—C28—H28A109.3
C6—C5—N3109.3 (6)C27—C28—H28B109.3
C6—C5—H5125.4C29—C28—H28B109.3
N3—C5—H5125.4H28A—C28—H28B108.0
N4—C6—C5105.9 (6)C30—C29—C28112.3 (4)
N4—C6—H6127.1C30—C29—C33111.9 (4)
C5—C6—H6127.1C28—C29—C33108.1 (4)
N3—C7—N4109.7 (5)C30—C29—H29108.2
N3—C7—C8126.6 (6)C28—C29—H29108.2
N4—C7—C8123.7 (6)C33—C29—H29108.2
C7—C8—H8A109.5O4—C30—O3117.8 (5)
C7—C8—H8B109.5O4—C30—C29121.7 (5)
H8A—C8—H8B109.5O3—C30—C29120.5 (5)
C7—C8—H8C109.5O4—C30—Cd2iii63.2 (3)
H8A—C8—H8C109.5O3—C30—Cd2iii54.8 (3)
H8B—C8—H8C109.5C29—C30—Cd2iii174.5 (4)
O6—C9—O5119.8 (5)C33—C32—C26112.0 (4)
O6—C9—C10119.4 (4)C33—C32—H32A109.2
O5—C9—C10120.8 (5)C26—C32—H32A109.2
C15—C10—C9113.5 (4)C33—C32—H32B109.2
C15—C10—C11110.8 (4)C26—C32—H32B109.2
C9—C10—C11112.4 (4)H32A—C32—H32B107.9
C15—C10—H10106.5C32—C33—C29112.0 (5)
C9—C10—H10106.5C32—C33—H33A109.2
C11—C10—H10106.5C29—C33—H33A109.2
C10—C11—C12111.8 (4)C32—C33—H33B109.2
C10—C11—H11A109.3C29—C33—H33B109.2
C12—C11—H11A109.3H33A—C33—H33B107.9
C10—C11—H11B109.3C1—N1—C4106.0 (6)
C12—C11—H11B109.3C1—N1—Cd1134.5 (4)
H11A—C11—H11B107.9C4—N1—Cd1119.2 (4)
C13—C12—C11111.1 (4)C1—N2—C3105.7 (6)
C13—C12—H12A109.4C1—N2—H2127.2
C11—C12—H12A109.4C3—N2—H2127.2
C13—C12—H12B109.4C7—N3—C5106.3 (5)
C11—C12—H12B109.4C7—N3—Cd1126.3 (4)
H12A—C12—H12B108.0C5—N3—Cd1127.1 (4)
C12—C13—C16114.0 (4)C6—N4—C7108.9 (5)
C12—C13—C14109.4 (4)C6—N4—H4A125.6
C16—C13—C14110.0 (4)C7—N4—H4A125.6
C12—C13—H13107.7C18—N5—C19105.3 (5)
C16—C13—H13107.7C18—N5—Cd2130.3 (4)
C14—C13—H13107.7C19—N5—Cd2124.2 (4)
C15—C14—C13110.9 (4)C18—N6—C20107.1 (6)
C15—C14—H14A109.5C18—N6—H6A126.4
C13—C14—H14A109.5C20—N6—H6A126.4
C15—C14—H14B109.5C23—N7—C21105.4 (6)
C13—C14—H14B109.5C23—N7—Cd2126.7 (5)
H14A—C14—H14B108.0C21—N7—Cd2126.5 (4)
C10—C15—C14112.2 (4)C23—N8—C22108.3 (6)
C10—C15—H15A109.2C23—N8—H8125.9
C14—C15—H15A109.2C22—N8—H8125.9
C10—C15—H15B109.2C25—O1—Cd292.5 (4)
C14—C15—H15B109.2C25—O2—Cd294.9 (3)
H15A—C15—H15B107.9HW11—O1W—HW12107 (3)
O7—C16—O8120.0 (4)C30—O3—Cd2iii99.1 (4)
O7—C16—C13121.4 (4)HW21—O2W—HW22111 (3)
O8—C16—C13118.6 (4)C30—O4—Cd2iii90.6 (3)
C18—C17—H17A109.5HW31—O3W—HW32108 (3)
C18—C17—H17B109.5C9—O5—Cd192.3 (3)
H17A—C17—H17B109.5HW41—O4W—HW42107 (7)
C18—C17—H17C109.5C9—O6—Cd193.5 (3)
H17A—C17—H17C109.5C16—O7—Cd1iv91.5 (3)
H17B—C17—H17C109.5C16—O8—Cd1iv94.0 (3)
N6—C18—N5112.0 (6)N1—Cd1—N393.62 (19)
N6—C18—C17121.4 (6)N1—Cd1—O8i100.17 (15)
N5—C18—C17126.6 (6)N3—Cd1—O8i109.32 (16)
N5—C19—C20110.0 (7)N1—Cd1—O698.18 (18)
N5—C19—H19125.0N3—Cd1—O691.94 (15)
C20—C19—H19125.0O8i—Cd1—O6150.77 (15)
N6—C20—C19105.6 (7)N1—Cd1—O5100.37 (18)
N6—C20—H20127.2N3—Cd1—O5144.75 (15)
C19—C20—H20127.2O8i—Cd1—O599.87 (13)
C22—C21—N7109.5 (7)O6—Cd1—O554.29 (13)
C22—C21—H21125.2N1—Cd1—O7i153.96 (16)
N7—C21—H21125.2N3—Cd1—O7i90.96 (17)
C21—C22—N8106.3 (7)O8i—Cd1—O7i54.33 (11)
C21—C22—H22126.9O6—Cd1—O7i107.27 (15)
N8—C22—H22126.9O5—Cd1—O7i90.33 (15)
N8—C23—N7110.5 (6)N7—Cd2—N592.99 (18)
N8—C23—C24124.3 (7)N7—Cd2—O3ii124.4 (2)
N7—C23—C24125.2 (7)N5—Cd2—O3ii91.99 (19)
C23—C24—H24A109.5N7—Cd2—O297.27 (17)
C23—C24—H24B109.5N5—Cd2—O2131.71 (17)
H24A—C24—H24B109.5O3ii—Cd2—O2119.0 (2)
C23—C24—H24C109.5N7—Cd2—O1139.16 (18)
H24A—C24—H24C109.5N5—Cd2—O190.09 (16)
H24B—C24—H24C109.5O3ii—Cd2—O196.1 (2)
O1—C25—O2119.0 (5)O2—Cd2—O153.20 (14)
O1—C25—C26120.9 (5)N7—Cd2—O4ii93.16 (18)
O2—C25—C26120.1 (5)N5—Cd2—O4ii139.08 (18)
O1—C25—Cd260.8 (3)O3ii—Cd2—O4ii52.18 (15)
O2—C25—Cd258.5 (3)O2—Cd2—O4ii87.38 (17)
C26—C25—Cd2172.4 (3)O1—Cd2—O4ii110.49 (19)
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, y, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—HW11···O20.87 (5)1.88 (5)2.737 (6)169 (7)
O2W—HW21···O40.85 (5)1.92 (3)2.708 (6)153 (6)
O2W—HW22···O8v0.84 (2)1.97 (2)2.814 (5)173 (5)
O3W—HW32···O30.86 (6)1.90 (4)2.727 (7)160 (8)
O3W—HW31···O4Wiii0.87 (6)1.89 (6)2.758 (8)176 (9)
O4W—HW41···O10.87 (7)1.97 (8)2.797 (7)160 (7)
O4W—HW42···O2Wvi0.87 (6)1.90 (3)2.756 (7)170 (9)
N2—H2···O3W0.861.862.712 (7)171
N4—H4A···O5vii0.861.992.845 (6)171
N6—H6A···O70.861.932.776 (6)167
N8—H8···O1Wviii0.861.982.839 (7)173
Symmetry codes: (v) −x+1/2, −y, z+1/2; (iii) −x+1/2, y−1/2, z; (vi) −x+1, −y, −z+2; (vii) −x+1, y−1/2, −z+3/2; (viii) −x, −y, −z+2.
Table 1
Selected geometric parameters (Å, °) top
Cd1—N12.235 (5)Cd1—O52.380 (4)
Cd1—N32.266 (5)Cd1—O62.357 (4)
Cd2—N52.269 (4)Cd1—O8i2.355 (3)
Cd2—N72.244 (5)Cd1—O7i2.419 (4)
Cd2—O12.397 (4)Cd2—O3ii2.279 (5)
Cd2—O22.347 (4)Cd2—O4ii2.457 (4)
N1—Cd1—N393.62 (19)N7—Cd2—N592.99 (18)
N1—Cd1—O8i100.17 (15)N7—Cd2—O3ii124.4 (2)
N3—Cd1—O8i109.32 (16)N5—Cd2—O3ii91.99 (19)
N1—Cd1—O698.18 (18)N7—Cd2—O297.27 (17)
N3—Cd1—O691.94 (15)N5—Cd2—O2131.71 (17)
O8i—Cd1—O6150.77 (15)O3ii—Cd2—O2119.0 (2)
N1—Cd1—O5100.37 (18)N7—Cd2—O1139.16 (18)
N3—Cd1—O5144.75 (15)N5—Cd2—O190.09 (16)
O8i—Cd1—O599.87 (13)O3ii—Cd2—O196.1 (2)
O6—Cd1—O554.29 (13)O2—Cd2—O153.20 (14)
N1—Cd1—O7i153.96 (16)N7—Cd2—O4ii93.16 (18)
N3—Cd1—O7i90.96 (17)N5—Cd2—O4ii139.08 (18)
O8i—Cd1—O7i54.33 (11)O3ii—Cd2—O4ii52.18 (15)
O6—Cd1—O7i107.27 (15)O2—Cd2—O4ii87.38 (17)
O5—Cd1—O7i90.33 (15)O1—Cd2—O4ii110.49 (19)
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, y+1/2, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—HW11···O20.87 (5)1.88 (5)2.737 (6)169 (7)
O2W—HW21···O40.85 (5)1.92 (3)2.708 (6)153 (6)
O2W—HW22···O8iii0.84 (2)1.97 (2)2.814 (5)173 (5)
O3W—HW32···O30.86 (6)1.90 (4)2.727 (7)160 (8)
O3W—HW31···O4Wiv0.87 (6)1.89 (6)2.758 (8)176 (9)
O4W—HW41···O10.87 (7)1.97 (8)2.797 (7)160 (7)
O4W—HW42···O2Wv0.87 (6)1.90 (3)2.756 (7)170 (9)
N2—H2···O3W0.861.862.712 (7)171
N4—H4A···O5vi0.861.992.845 (6)171
N6—H6A···O70.861.932.776 (6)167
N8—H8···O1Wvii0.861.982.839 (7)173
Symmetry codes: (iii) −x+1/2, −y, z+1/2; (iv) −x+1/2, y−1/2, z; (v) −x+1, −y, −z+2; (vi) −x+1, y−1/2, −z+3/2; (vii) −x, −y, −z+2.
Acknowledgements top

The authors thank Beihua University for supporting this work.

references
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