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Acta Cryst. (2008). E64, m1458    [ doi:10.1107/S1600536808033886 ]

Bis([mu]-2-hydroxybenozato)-[kappa]3O,O':O';[kappa]3O:O,O'-bis[(2-hydroxybenozato-[kappa]2O,O')(1,10-phenanthroline-[kappa]2N,N')cadmium(II)]

Q.-Y. Shi, Z.-C. Li, Z.-S. Cheng, J.-B. Tan and J.-L. Liu

Abstract top

The dinuclear title compound, [Cd2(C7H5O3)4(C12H8N2)2], is located on a crystallographic rotation twofold axis. The two CdII ions are connected by two tridentate bridging 2-hydroxybenzoate anions. Each CdII ion is seven-coordinated by five O atoms from three 2-hydroxybenzoate ligands and two N atoms from 1,10-phenanthroline. The 2-hydroxybenzoate molecules adopt two kinds of coordination mode, bidentate chelating and tridentate bridging-chelating. Intramolecular hydrogen bonds between hydroxy and carboxylate groups from 2-hydroxybenzoate groups and [pi]-[pi] stacking interactions between parallel 1,10-phenanthroline ligands [centroid-centroid distances = 3.707 (3) and 3.842 (3) Å] are observed. Furthermore, adjacent benzene rings from 2-hydroxybenzoate ligands are involved in [pi]-[pi] interactions with interplanar distances of 3.642 (3) Å, thereby forming a chain along the a axis direction.

Comment top

Transition metal complexes with substituted benzoate ligands have attracted wide attention in past decades, owing to their variable high-dimensional architectures and potential applications for gas absorption and separation, and catalysis, etc [Du et al., 2007; Horike et al., 2007; Humphrey et al., 2007; Pan et al., 2006; Sudik et al., 2005; Tomas et al., 2006; Zhang et al., 2008]. Herein, we report the synthesis and crystal structure of the title compound, obtained by the reaction of Sm(NO3)3, Cd(CH3COO)2, 1,10-phenanthroline and 2-hydroxybenzoic acid. No samarium was however incorporated in the crystals isolated and the title compound is a dinuclear CdII complex of 2-hydroxybenzoic acid and 1,10-phenanthroline. A perspective view of the complex, showing the atomic numbering scheme, is depicted in Fig. 1. Each CdII is seven-coordinated by five oxygen atoms from three 2-hydroxybenzoate ligands, and two nitrogen atoms from 1,10-phenanthroline, and the coordination geometry around the CdII ion may be described as a distorted mono-capped trigonal prism. Two adjacent CdII units are connected by two bridging 2-hydroxybenzoate anions to generate a dinuclear complex. The 2-hydroxybenzoate molecules adopt two kinds of coordination modes, bidentate chelating and tridentate bridging-chelating. The inequivalence between the mono and bidentate bridging oxygen atoms is evident from the Cd—O bond distances: the Cd—O distances of the bridging oxygen atoms are longer than those of the monodentate oxygen atoms: Cd1—O5 is 2.421 (2) Å and Cd1—O5i is 2.491 (2) Å, while Cd1—O1, Cd—O2 and Cd—O4 are 2.399 (2), 2.327 (2) and 2.363 (2) Å, respectively (symmetry code: (i): -x, y, 1/2 - z).

Intramolecular hydrogen bonds between hydroxyl and carboxylate groups from the 2-hydroxybenzoates [O6···O4 = 2.579 (3) Å and O3···O2 = 2.576 (2) Å, Table 1] and π-π stacking attractions between parallel 1,10-phenanthroline ligands [centroid to centroid distances: 3.707 (3) and 3.842 (3) Å] are clearly observed in this complex, which may contribute to its stability.

Furthermore, adjacent phenyl rings from 2-hydroxybenzoate ligands are also involved in π-π stacking interactions by partial overlap of π-electron densities (Tong et al., 1999). The centroid-centroid separation between rings A (atoms C14—C19) and Bj [atoms C21—C26; symmetry code: (j): 1/2 + x, 1/2 - y, 1/2 + z] is 3.642 (3) Å. Considering these π-π intermolecular attractions, they imply the formation of a one-dimensional chain along the direction of the a-axis. (Fig. 2).

Related literature top

For general background, see: Horike et al. (2007); Humphrey et al. (2007); Sudik et al. (2005); Zhang et al. (2008). For related structures, see: Du et al. (2007); Pan et al. (2006); Tomas et al. (2006). For related literature, see: Tong et al. (1999).

Experimental top

A sample of Sm(NO3)3.6H2O (0.090 g, 0.20 mmol), Cd(CH3COO)2.2H2O (0.052 g, 0.20 mmol), 2-hydroxybenzoic acid (0.070 g, 0.50 mmol), 1,10-phenanthroline (0.036 g, 0.20 mmol) and distilled water (8 ml) were mixed in a 15 ml Teflon-lined stainless steel vessel and the pH value was adjusted to about 5 with NaOH. Then, the mixture was heated to 393 K under autogenous pressure for 48 h, and cooled slowly to room temperature. Colorless block-like crystals suitable for X-ray single-crystal diffraction analysis were obtained by filtration and washed with distilled water and ethanol.

Refinement top

All H atoms were placed in calculated positions and were allowed to ride on their parent atoms; C—H = 0.93 (aromatic C—H) and O—H = 0.82 (hydroxyl) Å; Uiso(H) = 1.2 Ueq (C) and Uiso (H) = 1.5 Ueq (O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP-3 (Farrugia, 1997) plot of the title compound with displacement ellipsoids at the 30% probability level. All H atoms are omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of the title compound, showing a one-dimensional chain-like structure generated by the intermolecular π-π interactions. All H atoms are omitted for clarity. [Symmetry codes: (j): 1/2 + x, 1/2 - y, 1/2 + z].
Bis(µ-2-hydroxybenozato)- κ3O,O':O';κ3O:O,O'- bis[(2-hydroxybenozato-κ2O,O')(1,10-phenanthroline- κ2N,N')cadmium(II)] top
Crystal data top
[Cd2(C7H5O3)4(C12H8N2)2]F(000) = 2272
Mr = 1133.65Dx = 1.687 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4082 reflections
a = 27.9391 (19) Åθ = 1.9–27.4°
b = 10.3078 (7) ŵ = 1.03 mm−1
c = 20.468 (2) ÅT = 298 K
β = 130.770 (1)°Block, colorless
V = 4464.2 (6) Å30.30 × 0.25 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		4390 independent reflections
Radiation source: fine-focus sealed tube3671 reflections with I > 2σ(I)
graphiteRint = 0.027
φ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −34→23
Tmin = 0.748, Tmax = 0.837k = −12→12
11963 measured reflectionsl = −18→25
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0314P)2 + 1.2193P]
where P = (Fo2 + 2Fc2)/3
4390 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[Cd2(C7H5O3)4(C12H8N2)2]V = 4464.2 (6) Å3
Mr = 1133.65Z = 4
Monoclinic, C2/cMo Kα radiation
a = 27.9391 (19) ŵ = 1.03 mm−1
b = 10.3078 (7) ÅT = 298 K
c = 20.468 (2) Å0.30 × 0.25 × 0.18 mm
β = 130.770 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		4390 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3671 reflections with I > 2σ(I)
Tmin = 0.748, Tmax = 0.837Rint = 0.027
11963 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.067Δρmax = 0.25 e Å−3
S = 1.06Δρmin = −0.36 e Å−3
4390 reflectionsAbsolute structure: ?
316 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.13185 (12)0.5408 (3)0.40308 (16)0.0477 (6)
H10.14360.46250.43260.057*
C20.15571 (15)0.6556 (3)0.4506 (2)0.0609 (8)
H20.18320.65340.51050.073*
C30.13835 (14)0.7702 (3)0.40838 (19)0.0644 (8)
H30.15360.84740.43940.077*
C40.09731 (13)0.7733 (3)0.31771 (18)0.0491 (7)
C50.07771 (16)0.8903 (3)0.2685 (2)0.0652 (9)
H50.09200.96970.29710.078*
C60.03932 (15)0.8881 (3)0.1826 (2)0.0604 (8)
H60.02780.96570.15240.072*
C70.01567 (12)0.7686 (2)0.13628 (17)0.0448 (6)
C8−0.02500 (12)0.7611 (3)0.04561 (18)0.0517 (7)
H8−0.03790.83670.01310.062*
C9−0.04538 (13)0.6440 (3)0.00554 (18)0.0510 (7)
H9−0.07190.6383−0.05420.061*
C10−0.02569 (11)0.5324 (3)0.05582 (16)0.0438 (6)
H10−0.03990.45240.02810.053*
C110.03313 (11)0.6513 (2)0.18132 (16)0.0352 (5)
C120.07583 (11)0.6531 (2)0.27488 (16)0.0362 (5)
C130.16216 (11)0.2707 (2)0.25844 (15)0.0393 (6)
C140.22134 (11)0.2278 (2)0.27919 (16)0.0407 (6)
C150.26018 (13)0.1335 (3)0.34283 (19)0.0518 (7)
C160.31708 (14)0.1016 (3)0.3645 (2)0.0701 (9)
H160.34310.04000.40710.084*
C170.33538 (17)0.1594 (4)0.3243 (3)0.0817 (12)
H170.37370.13620.33950.098*
C180.29839 (16)0.2517 (4)0.2617 (3)0.0750 (10)
H180.31140.29080.23460.090*
C190.24122 (14)0.2856 (3)0.2392 (2)0.0558 (7)
H190.21590.34800.19690.067*
C20−0.05515 (11)0.2173 (2)0.10588 (15)0.0382 (5)
C21−0.11314 (11)0.1442 (2)0.03654 (15)0.0361 (5)
C22−0.11635 (12)0.0730 (2)−0.02440 (15)0.0432 (6)
C23−0.17163 (14)0.0033 (3)−0.08804 (16)0.0565 (8)
H23−0.1743−0.0454−0.12850.068*
C24−0.22170 (13)0.0073 (3)−0.09029 (18)0.0607 (8)
H24−0.2581−0.0396−0.13240.073*
C25−0.21937 (13)0.0784 (3)−0.03221 (18)0.0576 (8)
H25−0.25410.0811−0.03530.069*
C26−0.16526 (12)0.1463 (2)0.03120 (17)0.0451 (6)
H26−0.16360.19440.07110.054*
Cd10.057575 (8)0.350425 (15)0.231588 (11)0.03562 (7)
N10.09300 (9)0.53845 (19)0.31732 (12)0.0372 (4)
N20.01241 (8)0.53497 (18)0.14148 (12)0.0361 (4)
O10.13009 (8)0.36071 (17)0.20625 (12)0.0517 (5)
O20.14511 (8)0.21631 (18)0.29634 (11)0.0497 (5)
O30.24496 (10)0.0733 (2)0.38541 (14)0.0733 (6)
H3A0.20830.09070.36250.110*
O4−0.00846 (8)0.21515 (17)0.10927 (12)0.0527 (5)
O50.05244 (8)0.28218 (18)0.34009 (12)0.0516 (5)
O6−0.06878 (9)0.06944 (18)−0.02577 (12)0.0582 (5)
H6A−0.03970.11570.01280.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0451 (14)0.0544 (16)0.0402 (15)0.0009 (12)0.0264 (12)0.0023 (12)
C20.0598 (19)0.074 (2)0.0388 (15)−0.0100 (15)0.0276 (14)−0.0083 (14)
C30.075 (2)0.0561 (19)0.0585 (19)−0.0184 (16)0.0419 (17)−0.0227 (15)
C40.0547 (16)0.0434 (15)0.0540 (17)−0.0046 (12)0.0375 (14)−0.0069 (12)
C50.083 (2)0.0347 (15)0.079 (2)−0.0069 (15)0.0531 (19)−0.0092 (15)
C60.081 (2)0.0320 (14)0.074 (2)0.0066 (14)0.0534 (19)0.0109 (14)
C70.0488 (14)0.0373 (14)0.0556 (16)0.0067 (11)0.0373 (13)0.0082 (12)
C80.0521 (16)0.0519 (17)0.0555 (17)0.0147 (13)0.0370 (14)0.0210 (14)
C90.0466 (15)0.0615 (19)0.0398 (15)0.0083 (13)0.0260 (13)0.0099 (13)
C100.0407 (13)0.0445 (14)0.0398 (14)0.0001 (11)0.0235 (12)0.0003 (11)
C110.0358 (12)0.0347 (13)0.0438 (14)0.0014 (9)0.0298 (12)0.0025 (10)
C120.0361 (12)0.0362 (13)0.0426 (14)−0.0019 (10)0.0284 (11)−0.0020 (10)
C130.0359 (13)0.0407 (14)0.0367 (13)−0.0027 (10)0.0217 (11)−0.0052 (11)
C140.0380 (13)0.0415 (14)0.0453 (14)−0.0039 (10)0.0284 (12)−0.0091 (11)
C150.0413 (15)0.0504 (17)0.0551 (17)0.0027 (12)0.0277 (14)−0.0097 (13)
C160.0430 (16)0.072 (2)0.079 (2)0.0128 (15)0.0329 (17)−0.0067 (18)
C170.052 (2)0.089 (3)0.110 (3)−0.0032 (18)0.055 (2)−0.035 (2)
C180.080 (2)0.082 (2)0.106 (3)−0.026 (2)0.079 (2)−0.032 (2)
C190.0632 (18)0.0562 (18)0.0655 (19)−0.0087 (14)0.0498 (16)−0.0096 (14)
C200.0415 (13)0.0274 (12)0.0391 (13)−0.0002 (10)0.0233 (11)0.0027 (10)
C210.0396 (13)0.0301 (12)0.0340 (12)−0.0005 (9)0.0219 (11)0.0025 (9)
C220.0543 (15)0.0336 (14)0.0392 (14)0.0038 (11)0.0295 (12)0.0044 (11)
C230.0702 (19)0.0434 (16)0.0355 (15)−0.0025 (13)0.0256 (14)−0.0060 (12)
C240.0474 (17)0.0550 (18)0.0412 (16)−0.0091 (13)0.0121 (13)−0.0018 (13)
C250.0417 (15)0.0582 (18)0.0542 (18)−0.0056 (13)0.0231 (14)0.0044 (14)
C260.0446 (14)0.0438 (15)0.0421 (14)0.0004 (11)0.0261 (12)0.0022 (11)
Cd10.03456 (11)0.03147 (11)0.03994 (12)0.00079 (7)0.02394 (9)0.00196 (7)
N10.0367 (10)0.0370 (11)0.0375 (11)0.0005 (8)0.0240 (9)0.0023 (9)
N20.0336 (10)0.0365 (11)0.0373 (11)0.0004 (8)0.0228 (9)0.0009 (8)
O10.0432 (10)0.0568 (12)0.0545 (11)0.0086 (8)0.0316 (9)0.0137 (9)
O20.0457 (10)0.0594 (12)0.0537 (11)0.0101 (9)0.0367 (9)0.0135 (9)
O30.0634 (13)0.0808 (16)0.0761 (15)0.0276 (11)0.0457 (12)0.0327 (13)
O40.0434 (10)0.0479 (11)0.0676 (13)−0.0064 (8)0.0367 (10)−0.0098 (9)
O50.0585 (11)0.0506 (11)0.0498 (11)0.0123 (9)0.0373 (10)0.0157 (9)
O60.0736 (13)0.0545 (12)0.0648 (13)−0.0001 (10)0.0532 (11)−0.0074 (10)
Geometric parameters (Å, °) top
C1—N11.331 (3)C16—H160.9300
C1—C21.394 (4)C17—C181.373 (5)
C1—H10.9300C17—H170.9300
C2—C31.353 (4)C18—C191.388 (4)
C2—H20.9300C18—H180.9300
C3—C41.407 (4)C19—H190.9300
C3—H30.9300C20—O5i1.252 (3)
C4—C121.406 (3)C20—O41.260 (3)
C4—C51.432 (4)C20—C211.484 (3)
C5—C61.335 (5)C21—C261.388 (4)
C5—H50.9300C21—C221.399 (3)
C6—C71.426 (4)C22—O61.348 (3)
C6—H60.9300C22—C231.404 (4)
C7—C111.401 (3)C23—C241.370 (4)
C7—C81.410 (4)C23—H230.9300
C8—C91.358 (4)C24—C251.362 (4)
C8—H80.9300C24—H240.9300
C9—C101.395 (3)C25—C261.378 (4)
C9—H90.9300C25—H250.9300
C10—N21.331 (3)C26—H260.9300
C10—H100.9300Cd1—O22.3271 (16)
C11—N21.349 (3)Cd1—N12.355 (2)
C11—C121.451 (4)Cd1—N22.3606 (19)
C12—N11.355 (3)Cd1—O42.3630 (18)
C13—O11.247 (3)Cd1—O12.3993 (19)
C13—O21.275 (3)Cd1—O52.4214 (18)
C13—C141.480 (3)Cd1—O5i2.4911 (18)
C14—C191.388 (4)O3—H3A0.8199
C14—C151.405 (4)O5—C20i1.252 (3)
C15—O31.345 (4)O5—Cd1i2.4911 (18)
C15—C161.382 (4)O6—H6A0.8200
C16—C171.357 (6)
N1—C1—C2122.8 (3)O5i—C20—O4119.8 (2)
N1—C1—H1118.6O5i—C20—C21121.0 (2)
C2—C1—H1118.6O4—C20—C21119.2 (2)
C3—C2—C1119.1 (3)C26—C21—C22119.0 (2)
C3—C2—H2120.4C26—C21—C20120.1 (2)
C1—C2—H2120.4C22—C21—C20120.9 (2)
C2—C3—C4120.4 (3)O6—C22—C21122.9 (2)
C2—C3—H3119.8O6—C22—C23118.0 (2)
C4—C3—H3119.8C21—C22—C23119.1 (3)
C12—C4—C3116.8 (3)C24—C23—C22119.8 (3)
C12—C4—C5119.5 (3)C24—C23—H23120.1
C3—C4—C5123.7 (3)C22—C23—H23120.1
C6—C5—C4121.4 (3)C25—C24—C23121.4 (3)
C6—C5—H5119.3C25—C24—H24119.3
C4—C5—H5119.3C23—C24—H24119.3
C5—C6—C7121.0 (3)C24—C25—C26119.6 (3)
C5—C6—H6119.5C24—C25—H25120.2
C7—C6—H6119.5C26—C25—H25120.2
C11—C7—C8117.0 (2)C25—C26—C21121.1 (3)
C11—C7—C6119.8 (3)C25—C26—H26119.5
C8—C7—C6123.2 (2)C21—C26—H26119.5
C9—C8—C7120.2 (2)O2—Cd1—N1106.89 (7)
C9—C8—H8119.9O2—Cd1—N2138.63 (6)
C7—C8—H8119.9N1—Cd1—N270.68 (7)
C8—C9—C10118.7 (3)O2—Cd1—O493.20 (6)
C8—C9—H9120.7N1—Cd1—O4158.83 (6)
C10—C9—H9120.7N2—Cd1—O489.92 (6)
N2—C10—C9123.1 (2)O2—Cd1—O155.09 (6)
N2—C10—H10118.4N1—Cd1—O196.97 (7)
C9—C10—H10118.4N2—Cd1—O183.78 (6)
N2—C11—C7122.8 (2)O4—Cd1—O188.99 (7)
N2—C11—C12117.8 (2)O2—Cd1—O588.55 (6)
C7—C11—C12119.4 (2)N1—Cd1—O578.67 (7)
N1—C12—C4122.7 (2)N2—Cd1—O5128.98 (6)
N1—C12—C11118.5 (2)O4—Cd1—O5109.11 (7)
C4—C12—C11118.8 (2)O1—Cd1—O5140.82 (6)
O1—C13—O2120.2 (2)O2—Cd1—O5i126.96 (6)
O1—C13—C14120.7 (2)N1—Cd1—O5i115.33 (6)
O2—C13—C14119.0 (2)N2—Cd1—O5i86.73 (6)
C19—C14—C15118.7 (3)O4—Cd1—O5i53.13 (6)
C19—C14—C13120.3 (2)O1—Cd1—O5i140.94 (6)
C15—C14—C13120.9 (2)O5—Cd1—O5i70.66 (7)
O3—C15—C16117.8 (3)C1—N1—C12118.2 (2)
O3—C15—C14122.7 (2)C1—N1—Cd1125.56 (17)
C16—C15—C14119.5 (3)C12—N1—Cd1116.05 (15)
C17—C16—C15120.7 (3)C10—N2—C11118.2 (2)
C17—C16—H16119.6C10—N2—Cd1124.98 (16)
C15—C16—H16119.6C11—N2—Cd1116.38 (15)
C16—C17—C18121.2 (3)C13—O1—Cd191.02 (15)
C16—C17—H17119.4C13—O2—Cd193.65 (15)
C18—C17—H17119.4C15—O3—H3A109.4
C17—C18—C19119.0 (3)C20—O4—Cd196.43 (15)
C17—C18—H18120.5C20i—O5—Cd1163.72 (17)
C19—C18—H18120.5C20i—O5—Cd1i90.61 (15)
C14—C19—C18120.9 (3)Cd1—O5—Cd1i99.62 (6)
C14—C19—H19119.5C22—O6—H6A109.5
C18—C19—H19119.5
N1—C1—C2—C30.8 (5)O1—Cd1—N1—C1−99.78 (19)
C1—C2—C3—C4−0.7 (5)O5—Cd1—N1—C140.75 (19)
C2—C3—C4—C120.3 (4)O5i—Cd1—N1—C1102.81 (19)
C2—C3—C4—C5−178.8 (3)O2—Cd1—N1—C12130.28 (16)
C12—C4—C5—C60.1 (5)N2—Cd1—N1—C12−6.16 (15)
C3—C4—C5—C6179.1 (3)O4—Cd1—N1—C12−30.7 (3)
C4—C5—C6—C70.8 (5)O1—Cd1—N1—C1274.72 (16)
C5—C6—C7—C11−0.4 (4)O5—Cd1—N1—C12−144.75 (17)
C5—C6—C7—C8179.9 (3)O5i—Cd1—N1—C12−82.69 (17)
C11—C7—C8—C9−0.2 (4)C9—C10—N2—C11−0.4 (4)
C6—C7—C8—C9179.4 (3)C9—C10—N2—Cd1−172.1 (2)
C7—C8—C9—C100.5 (4)C7—C11—N2—C100.7 (3)
C8—C9—C10—N2−0.2 (4)C12—C11—N2—C10−178.6 (2)
C8—C7—C11—N2−0.4 (4)C7—C11—N2—Cd1173.18 (18)
C6—C7—C11—N2179.9 (2)C12—C11—N2—Cd1−6.2 (3)
C8—C7—C11—C12178.9 (2)O2—Cd1—N2—C1084.4 (2)
C6—C7—C11—C12−0.7 (4)N1—Cd1—N2—C10178.3 (2)
C3—C4—C12—N10.1 (4)O4—Cd1—N2—C10−10.32 (19)
C5—C4—C12—N1179.3 (2)O1—Cd1—N2—C1078.67 (19)
C3—C4—C12—C11179.7 (2)O5—Cd1—N2—C10−125.16 (18)
C5—C4—C12—C11−1.2 (4)O5i—Cd1—N2—C10−63.38 (18)
N2—C11—C12—N10.4 (3)O2—Cd1—N2—C11−87.44 (18)
C7—C11—C12—N1−178.9 (2)N1—Cd1—N2—C116.44 (15)
N2—C11—C12—C4−179.1 (2)O4—Cd1—N2—C11177.81 (16)
C7—C11—C12—C41.5 (4)O1—Cd1—N2—C11−93.21 (16)
O1—C13—C14—C19−1.4 (4)O5—Cd1—N2—C1162.97 (18)
O2—C13—C14—C19−179.7 (2)O5i—Cd1—N2—C11124.74 (16)
O1—C13—C14—C15175.0 (2)O2—C13—O1—Cd11.5 (2)
O2—C13—C14—C15−3.3 (3)C14—C13—O1—Cd1−176.72 (19)
C19—C14—C15—O3179.4 (3)O2—Cd1—O1—C13−0.88 (14)
C13—C14—C15—O32.9 (4)N1—Cd1—O1—C13104.88 (15)
C19—C14—C15—C160.6 (4)N2—Cd1—O1—C13174.48 (15)
C13—C14—C15—C16−175.9 (2)O4—Cd1—O1—C13−95.49 (15)
O3—C15—C16—C17−179.6 (3)O5—Cd1—O1—C1324.28 (19)
C14—C15—C16—C17−0.8 (5)O5i—Cd1—O1—C13−108.56 (16)
C15—C16—C17—C180.5 (5)O1—C13—O2—Cd1−1.6 (2)
C16—C17—C18—C19−0.1 (5)C14—C13—O2—Cd1176.70 (18)
C15—C14—C19—C18−0.2 (4)N1—Cd1—O2—C13−85.86 (15)
C13—C14—C19—C18176.3 (2)N2—Cd1—O2—C13−6.14 (19)
C17—C18—C19—C140.0 (5)O4—Cd1—O2—C1387.38 (15)
O5i—C20—C21—C26−0.5 (3)O1—Cd1—O2—C130.86 (13)
O4—C20—C21—C26−179.4 (2)O5—Cd1—O2—C13−163.56 (15)
O5i—C20—C21—C22179.2 (2)O5i—Cd1—O2—C13132.15 (14)
O4—C20—C21—C220.3 (3)O5i—C20—O4—Cd10.7 (2)
C26—C21—C22—O6177.6 (2)C21—C20—O4—Cd1179.66 (17)
C20—C21—C22—O6−2.1 (3)O2—Cd1—O4—C20134.91 (14)
C26—C21—C22—C23−1.4 (3)N1—Cd1—O4—C20−63.3 (2)
C20—C21—C22—C23178.9 (2)N2—Cd1—O4—C20−86.37 (15)
O6—C22—C23—C24−178.3 (2)O1—Cd1—O4—C20−170.14 (15)
C21—C22—C23—C240.8 (4)O5—Cd1—O4—C2045.33 (15)
C22—C23—C24—C250.4 (4)O5i—Cd1—O4—C20−0.40 (13)
C23—C24—C25—C26−1.1 (4)O2—Cd1—O5—C20i−34.5 (6)
C24—C25—C26—C210.4 (4)N1—Cd1—O5—C20i−142.0 (6)
C22—C21—C26—C250.8 (4)N2—Cd1—O5—C20i164.6 (6)
C20—C21—C26—C25−179.5 (2)O4—Cd1—O5—C20i58.4 (6)
C2—C1—N1—C12−0.4 (4)O1—Cd1—O5—C20i−54.9 (6)
C2—C1—N1—Cd1174.0 (2)O5i—Cd1—O5—C20i95.8 (6)
C4—C12—N1—C1−0.1 (4)O2—Cd1—O5—Cd1i−162.70 (7)
C11—C12—N1—C1−179.6 (2)N1—Cd1—O5—Cd1i89.75 (7)
C4—C12—N1—Cd1−174.99 (19)N2—Cd1—O5—Cd1i36.35 (10)
C11—C12—N1—Cd15.5 (3)O4—Cd1—O5—Cd1i−69.82 (8)
O2—Cd1—N1—C1−44.2 (2)O1—Cd1—O5—Cd1i176.89 (7)
N2—Cd1—N1—C1179.3 (2)O5i—Cd1—O5—Cd1i−32.44 (8)
O4—Cd1—N1—C1154.77 (19)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O40.821.862.579 (3)146
O3—H3A···O20.821.872.576 (2)143
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O40.821.862.579 (3)146
O3—H3A···O20.821.872.576 (2)143
Acknowledgements top

The authors gratefully acknowledge financial support from the Scientific Research Project for Comprehensive Talent Cultivation of South China Normal University (2008–2009).

references
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