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Acta Cryst. (2009). E65, m664-m665    [ doi:10.1107/S160053680901811X ]

Aquabis(4-nitrobenzoato)-[kappa]2O,O';[kappa]O-(piperidinium-4-carboxylato-[kappa]2O,O')cadmium(II)

R.-W. Zhang, L.-L. Wang and X.-J. Zhao

Abstract top

In the mixed ligand title compound, [Cd(C6H11NO2)(C7H4NO4)2(H2O)], which exhibits a discrete mononuclear structure, the CdII atom is in a distorted octahedral geometry, surrounded by five carboxylate O atoms and one coordinated water molecule. The piperdinium ring adopts a chair conformation and the two 4-nitrobenzoate rings are oriented at a dihedral angle of 75.8 (1)°. Intermolecular O-H...O and N-H...O hydrogen bonds link the mononuclear entities into a three-dimensional supramolecular network.

Comment top

Recently, the rational design and skillful construction of the coordination complexes with mixed ligands have aroused great interest due to their intriguing framework topologies and potential applications in ino-exchange (Muthu et al., 2002), catalysis (Fujita et al., 1994), luminescence (Zheng et al., 2004), and gas storage (Rosi et al., 2003). Bearing two potential binding sites (–NH– and –COOH) capable of coordination with transition metal atoms, 4-piperidinecarboxylic acid exists as a zwitterion with the amino group protonated and the carboxylic group deprotonated in aqueous solution (Mora et al., 2002). Thus, by carefully control the degree of the protonation/deprotonation of carboxylic and/or amino groups, it can selectively act as a bridge ligand linking different metal atoms into an infinite high-dimensional framework or as a terminal ligand forming a discrete complex (Inomata et al., 2002). However, to the best of our knowledge, only a few examples involved in 4-piperidinecarboxylic acid have been reported by far (Adams et al., 2006a,b; Podesta et al., 2002). Thus, to continue to explore the coordination behavior of 4-piperidinecarboxylic acid, herein, we report the crystal structure of a CdII complex with 4-piperidinecarboxylate and 4-nitrobenzoxylate anion.

As shown in Fig. 1, the mononuclear structure of the title complex, (I), consists of one crystallographic independent CdII atom, two separate 4-nitrobenzoxylate anions, one zwitterionic 4-piperidinecarboxylate molecule, and one coordinated water molecule. The sole CdII center is six-coordinated by one coordinated water molecule (O11), and five carboxylate O atoms from two independent 4-nitrobenzoxylate (O1, O2 and O5) and one 4-piperidinecarboxylate molecule (O9 and O10), exhibiting a distorted octahedral geometry (Table 1.). The Cd–O bond distances are in the range of 2.1914 (16)–2.3684 (17)Å, which are comparable to those previously reported values (Inomata et al., 2004; Wang et al., 2008). The carboxylate group of 4-nitrobenzoxylate anion presents two different coordination modes: monodentate and asymmetric chelating bidentate fashions. In contrast, the carboxylate group of 4-piperidinecarboxylate only adopts an asymmetric chelating bidentate coordination mode. Additionally, the N atom of piperidine ring does not coordinate to a metal atom, and the protonated piperidine ring of 4-piperdinecarboxylate is in a chair conformation significantly resulted from the relatively lower energy (Delgado et al., 2001).

As shown in Fig. 2, the adjacent mononuclear entities are linked in to a two-dimensional (2-D) layer by threefold hydrogen bonding interactions between the protonated –NH2+/coordinated water molecule and the carboxylate group of 4-piperdinecarboxylate /4-nitrobenzoxylate anion (Table 2.). The neighbour 2-D layers are further assembled into a 3-D supramolecular network (Fig. 3) also by the hydrogen bonding interaction between the coordinated water molecule and the carboxylate group of 4-nitrobenzoxylate anion (O11–H11A···O3). Thus, the abundant hydrogen bonds interactions significantly dominate the formation of 3-D supramolecular network of the title complex.

Related literature top

For the framework topologies and potential applications in ino-exchange of coordination complexes with mixed ligands, see: Muthu et al. (2002); Fujita et al. (1994); Zheng et al. (2004); Rosi et al. (2003). 4-piperidinecarboxylic acid exists as a zwitterion with the amino group protonated and the carboxylic group deprotonated in aqueous solution (Mora et al., 2002). It can selectively act as a bridge ligand linking different metal atoms into an infinite high-dimensional framework or as a terminal ligand forming a discrete complex (Inomata et al., 2002). For related structures, see: Adams et al. (2006a,b); Podesta et al. (2002); Delgado et al. (2001). For Cd—O bond lengths, see: Inomata et al. (2004); Wang et al. (2008).

Experimental top

To an aqueous solution (5 ml) of CdCl2. 2.5H2O (45.7 mg, 0.2 mmol) was slowly added a methanol solution (5 ml) containing 4-piperidinecarboxylic acid (12.9 mg, 0.1 mmol) and 4-nitrobenzoic acid (16.7 mg, 0.1 mmol) with constant stirring. And the pH value of the mixture was adjusted to 6 by NaOH solution (0.1 M). The resulting colorless solution was further stirred for half an hour and filtered. The filtrate was allowed to evaporate at room temperature. Pale-yellow block-shaped crystals were obtained within two weeks (yield 70% based on CdII salt).

Refinement top

The H atoms of the water molecule were located in the final difference Fourier map, their positions were refined and their isotropic displacement parameters were set to 1.5 times the equivalent displacement parameter of the O atom. H atoms of the NH2+ and the piperidine ring were placed in geometrically calculated positions and their isotropic displacement parameters were set to 1.2 times the equivalent displacement parameter of their parent atoms.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The 2-D layer of (I) formed by hydrogen bonding interactions. Only H atoms involved in hydrogen bonds are included.
[Figure 3] Fig. 3. The 3-D network of (I) formed by hydrogen bond interactions. Only H atoms involved in hydrogen bonds are included.
Aquabis(4-nitrobenzoato)-κ2O,O';κO-(piperidinium-4- carboxylato-κ2O,O')cadmium(II) top
Crystal data top
[Cd(C6H11NO2)(C7H4NO4)2(H2O)]F000 = 1192
Mr = 591.80Dx = 1.745 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8249 reflections
a = 22.7135 (7) Åθ = 2.9–27.8º
b = 6.6294 (2) ŵ = 1.04 mm−1
c = 14.9658 (5) ÅT = 296 K
β = 91.3400 (10)ºBlock, pale-yellow
V = 2252.89 (12) Å30.32 × 0.28 × 0.22 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3950 independent reflections
Radiation source: fine-focus sealed tube3615 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 296 Kθmax = 25.0º
φ and ω scansθmin = 0.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −18→26
Tmin = 0.733, Tmax = 0.804k = −7→7
10944 measured reflectionsl = −17→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.056  w = 1/[σ2(Fo2) + (0.0248P)2 + 1.8541P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3950 reflectionsΔρmax = 0.37 e Å−3
316 parametersΔρmin = −0.32 e Å−3
18 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cd(C6H11NO2)(C7H4NO4)2(H2O)]V = 2252.89 (12) Å3
Mr = 591.80Z = 4
Monoclinic, P21/cMo Kα
a = 22.7135 (7) ŵ = 1.04 mm−1
b = 6.6294 (2) ÅT = 296 K
c = 14.9658 (5) Å0.32 × 0.28 × 0.22 mm
β = 91.3400 (10)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3950 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3615 reflections with I > 2σ(I)
Tmin = 0.733, Tmax = 0.804Rint = 0.014
10944 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02018 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.05Δρmax = 0.37 e Å−3
3950 reflectionsΔρmin = −0.32 e Å−3
316 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.219460 (8)0.68670 (3)0.490995 (11)0.03129 (7)
O10.11917 (8)0.7419 (3)0.45149 (12)0.0458 (5)
O20.18499 (8)0.7480 (3)0.34618 (12)0.0372 (4)
O3−0.10379 (9)0.7684 (4)0.13243 (15)0.0595 (6)
O4−0.04142 (11)0.7829 (5)0.02901 (15)0.0822 (9)
O50.30087 (8)0.5260 (3)0.46044 (13)0.0450 (5)
O60.34464 (10)0.7998 (3)0.40672 (16)0.0563 (6)
O70.59387 (12)0.2162 (5)0.3509 (3)0.1201 (13)
O80.54181 (11)−0.0455 (4)0.3661 (2)0.0759 (7)
O90.24780 (8)0.7579 (3)0.63847 (11)0.0371 (4)
O100.23667 (10)1.0130 (3)0.54773 (12)0.0506 (5)
O110.18002 (9)0.3782 (3)0.52820 (14)0.0490 (5)
H11A0.14860.36920.49630.073*
H11B0.20070.27200.53420.073*
N1−0.05315 (11)0.7738 (4)0.10707 (16)0.0432 (6)
N20.54786 (12)0.1355 (4)0.3662 (2)0.0637 (8)
N30.28125 (9)1.4822 (3)0.78005 (14)0.0354 (5)
H3A0.26041.56100.74200.043*
H3B0.29461.56030.82530.043*
C10.08383 (11)0.7676 (4)0.30125 (16)0.0297 (5)
C20.02551 (11)0.7688 (4)0.32711 (17)0.0326 (5)
H20.01690.76750.38750.039*
C3−0.01979 (11)0.7717 (4)0.26380 (17)0.0342 (6)
H3−0.05890.77300.28060.041*
C4−0.00508 (11)0.7727 (4)0.17489 (17)0.0331 (6)
C50.05237 (12)0.7745 (4)0.14668 (17)0.0384 (6)
H50.06080.77790.08620.046*
C60.09691 (11)0.7712 (4)0.21095 (17)0.0354 (6)
H60.13600.77130.19370.043*
C70.13244 (11)0.7537 (4)0.37115 (17)0.0309 (5)
C80.39914 (11)0.4942 (4)0.41654 (17)0.0356 (6)
C90.44834 (14)0.5789 (5)0.3783 (2)0.0549 (8)
H90.44800.71440.36230.066*
C100.49774 (14)0.4642 (5)0.3638 (3)0.0622 (9)
H100.53120.52170.33980.075*
C110.49655 (12)0.2628 (5)0.3857 (2)0.0445 (7)
C120.44856 (12)0.1744 (4)0.42363 (18)0.0402 (6)
H120.44880.03770.43770.048*
C130.39998 (12)0.2921 (4)0.44039 (17)0.0367 (6)
H130.36760.23560.46790.044*
C140.34426 (12)0.6197 (4)0.42904 (17)0.0372 (6)
C150.27278 (11)1.0862 (4)0.69599 (15)0.0306 (5)
H150.29541.00780.74040.037*
C160.31251 (11)1.2505 (4)0.66016 (17)0.0349 (6)
H16A0.34691.18890.63420.042*
H16B0.29151.32420.61330.042*
C170.33216 (12)1.3960 (4)0.73289 (18)0.0399 (6)
H17A0.35771.32620.77560.048*
H17B0.35461.50450.70670.048*
C180.24177 (13)1.3237 (4)0.81621 (17)0.0370 (6)
H18A0.20811.38700.84340.044*
H18B0.26291.24720.86200.044*
C190.22071 (11)1.1830 (4)0.74276 (17)0.0341 (6)
H19A0.19691.25760.69940.041*
H19B0.19631.07830.76790.041*
C200.25127 (11)0.9437 (4)0.62321 (16)0.0326 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03884 (12)0.02632 (11)0.02842 (11)0.00414 (8)−0.00520 (7)−0.00244 (7)
O10.0443 (11)0.0636 (13)0.0294 (10)0.0109 (10)−0.0012 (8)0.0033 (9)
O20.0321 (10)0.0429 (10)0.0364 (10)0.0004 (8)−0.0041 (8)0.0006 (8)
O30.0341 (12)0.0792 (16)0.0646 (14)0.0025 (11)−0.0104 (10)0.0013 (12)
O40.0595 (15)0.149 (3)0.0372 (13)0.0001 (16)−0.0105 (11)0.0044 (15)
O50.0403 (11)0.0396 (11)0.0552 (12)0.0066 (9)0.0049 (9)−0.0040 (9)
O60.0592 (13)0.0369 (12)0.0725 (15)0.0100 (10)−0.0061 (11)0.0148 (10)
O70.0492 (15)0.0736 (19)0.240 (4)0.0041 (14)0.053 (2)0.026 (2)
O80.0572 (14)0.0516 (15)0.120 (2)0.0142 (12)0.0266 (14)0.0137 (14)
O90.0543 (11)0.0239 (9)0.0331 (9)−0.0009 (8)−0.0006 (8)−0.0017 (7)
O100.0843 (14)0.0275 (9)0.0388 (10)0.0071 (9)−0.0225 (10)−0.0030 (8)
O110.0479 (11)0.0328 (10)0.0650 (13)−0.0032 (9)−0.0228 (10)0.0083 (9)
N10.0420 (14)0.0409 (13)0.0462 (15)0.0022 (11)−0.0101 (11)0.0018 (11)
N20.0408 (14)0.0533 (16)0.098 (2)0.0069 (12)0.0211 (14)0.0190 (15)
N30.0487 (13)0.0225 (10)0.0348 (11)−0.0030 (9)−0.0047 (9)−0.0030 (9)
C10.0331 (13)0.0233 (12)0.0325 (13)0.0020 (10)−0.0009 (10)0.0021 (10)
C20.0384 (14)0.0297 (13)0.0299 (13)0.0030 (11)0.0027 (11)0.0025 (10)
C30.0301 (13)0.0307 (13)0.0418 (14)0.0015 (10)0.0034 (11)0.0024 (11)
C40.0350 (14)0.0280 (13)0.0359 (14)0.0012 (10)−0.0067 (11)0.0015 (10)
C50.0400 (15)0.0461 (16)0.0290 (13)0.0027 (12)0.0021 (11)0.0029 (12)
C60.0306 (13)0.0420 (15)0.0338 (13)0.0004 (11)0.0028 (11)0.0013 (11)
C70.0365 (14)0.0211 (12)0.0348 (14)0.0027 (10)−0.0035 (11)0.0000 (10)
C80.0371 (14)0.0330 (14)0.0364 (13)0.0006 (11)−0.0047 (11)0.0007 (11)
C90.0538 (19)0.0326 (16)0.079 (2)−0.0024 (14)0.0086 (16)0.0141 (15)
C100.0452 (18)0.0460 (19)0.096 (3)−0.0031 (15)0.0208 (17)0.0118 (18)
C110.0355 (15)0.0420 (16)0.0563 (18)0.0032 (12)0.0044 (13)0.0059 (14)
C120.0409 (15)0.0327 (14)0.0469 (16)0.0016 (12)0.0012 (12)0.0075 (12)
C130.0357 (14)0.0367 (15)0.0376 (14)−0.0008 (11)0.0015 (11)0.0052 (11)
C140.0428 (15)0.0368 (15)0.0316 (13)0.0036 (12)−0.0089 (11)−0.0015 (11)
C150.0397 (14)0.0226 (12)0.0293 (12)0.0040 (10)−0.0045 (10)0.0004 (10)
C160.0326 (13)0.0373 (14)0.0348 (13)0.0010 (11)0.0039 (11)−0.0015 (11)
C170.0365 (14)0.0382 (15)0.0447 (15)−0.0071 (12)−0.0039 (12)0.0011 (12)
C180.0517 (16)0.0265 (13)0.0332 (13)−0.0015 (11)0.0082 (12)−0.0019 (10)
C190.0386 (14)0.0273 (13)0.0367 (14)−0.0066 (11)0.0064 (11)−0.0020 (11)
C200.0410 (13)0.0248 (12)0.0318 (12)0.0055 (10)−0.0035 (10)−0.0039 (10)
Geometric parameters (Å, °) top
Cd1—O52.1917 (18)C3—C41.379 (4)
Cd1—O112.3061 (19)C3—H30.9300
Cd1—O22.3229 (17)C4—C51.381 (4)
Cd1—O92.3327 (17)C5—C61.380 (4)
Cd1—O102.3534 (18)C5—H50.9300
Cd1—O12.3684 (19)C6—H60.9300
Cd1—C72.675 (2)C8—C91.386 (4)
Cd1—C202.697 (2)C8—C131.387 (4)
O1—C71.249 (3)C8—C141.514 (4)
O2—C71.260 (3)C9—C101.377 (4)
O3—N11.220 (3)C9—H90.9300
O4—N11.206 (3)C10—C111.375 (4)
O5—C141.265 (3)C10—H100.9300
O6—C141.240 (3)C11—C121.372 (4)
O7—N21.201 (4)C12—C131.379 (4)
O8—N21.207 (4)C12—H120.9300
O9—C201.256 (3)C13—H130.9300
O10—C201.257 (3)C15—C201.514 (3)
O11—H11A0.8504C15—C161.520 (4)
O11—H11B0.8500C15—C191.529 (3)
N1—C41.473 (3)C15—H150.9800
N2—C111.474 (4)C16—C171.514 (4)
N3—C171.483 (3)C16—H16A0.9700
N3—C181.491 (3)C16—H16B0.9700
N3—H3A0.9000C17—H17A0.9700
N3—H3B0.9000C17—H17B0.9700
C1—C21.389 (4)C18—C191.511 (3)
C1—C61.391 (3)C18—H18A0.9700
C1—C71.506 (3)C18—H18B0.9700
C2—C31.382 (4)C19—H19A0.9700
C2—H20.9300C19—H19B0.9700
O5—Cd1—O1187.34 (7)C1—C6—H6119.7
O5—Cd1—O299.09 (7)O1—C7—O2122.4 (2)
O11—Cd1—O2104.84 (7)O1—C7—C1118.9 (2)
O5—Cd1—O994.60 (7)O2—C7—C1118.7 (2)
O11—Cd1—O992.93 (7)O1—C7—Cd162.30 (13)
O2—Cd1—O9157.95 (7)O2—C7—Cd160.23 (12)
O5—Cd1—O10112.86 (8)C1—C7—Cd1173.83 (17)
O11—Cd1—O10142.21 (7)C9—C8—C13119.4 (3)
O2—Cd1—O10103.02 (6)C9—C8—C14120.2 (2)
O9—Cd1—O1055.45 (6)C13—C8—C14120.4 (2)
O5—Cd1—O1146.54 (7)C10—C9—C8120.6 (3)
O11—Cd1—O179.66 (7)C10—C9—H9119.7
O2—Cd1—O155.86 (6)C8—C9—H9119.7
O9—Cd1—O1116.58 (6)C11—C10—C9118.6 (3)
O10—Cd1—O195.67 (7)C11—C10—H10120.7
O5—Cd1—C7123.68 (7)C9—C10—H10120.7
O11—Cd1—C791.37 (7)C12—C11—C10122.3 (3)
O2—Cd1—C728.08 (7)C12—C11—N2118.4 (3)
O9—Cd1—C7141.64 (7)C10—C11—N2119.3 (3)
O10—Cd1—C7101.72 (7)C11—C12—C13118.7 (3)
O1—Cd1—C727.83 (7)C11—C12—H12120.7
O5—Cd1—C20104.32 (7)C13—C12—H12120.7
O11—Cd1—C20118.82 (7)C12—C13—C8120.4 (3)
O2—Cd1—C20130.75 (7)C12—C13—H13119.8
O9—Cd1—C2027.72 (7)C8—C13—H13119.8
O10—Cd1—C2027.77 (7)O6—C14—O5125.7 (3)
O1—Cd1—C20108.98 (7)O6—C14—C8119.0 (3)
C7—Cd1—C20124.63 (7)O5—C14—C8115.3 (2)
C7—O1—Cd189.86 (15)C20—C15—C16112.2 (2)
C7—O2—Cd191.69 (15)C20—C15—C19110.6 (2)
C14—O5—Cd1120.47 (17)C16—C15—C19109.4 (2)
C20—O9—Cd192.50 (14)C20—C15—H15108.2
C20—O10—Cd191.50 (15)C16—C15—H15108.2
Cd1—O11—H11A104.6C19—C15—H15108.2
Cd1—O11—H11B122.9C17—C16—C15111.8 (2)
H11A—O11—H11B117.1C17—C16—H16A109.3
O4—N1—O3122.3 (2)C15—C16—H16A109.3
O4—N1—C4119.4 (2)C17—C16—H16B109.3
O3—N1—C4118.3 (2)C15—C16—H16B109.3
O7—N2—O8122.8 (3)H16A—C16—H16B107.9
O7—N2—C11118.6 (3)N3—C17—C16111.6 (2)
O8—N2—C11118.6 (3)N3—C17—H17A109.3
C17—N3—C18112.6 (2)C16—C17—H17A109.3
C17—N3—H3A109.1N3—C17—H17B109.3
C18—N3—H3A109.1C16—C17—H17B109.3
C17—N3—H3B109.1H17A—C17—H17B108.0
C18—N3—H3B109.1N3—C18—C19110.7 (2)
H3A—N3—H3B107.8N3—C18—H18A109.5
C2—C1—C6119.8 (2)C19—C18—H18A109.5
C2—C1—C7119.7 (2)N3—C18—H18B109.5
C6—C1—C7120.4 (2)C19—C18—H18B109.5
C3—C2—C1120.6 (2)H18A—C18—H18B108.1
C3—C2—H2119.7C18—C19—C15110.9 (2)
C1—C2—H2119.7C18—C19—H19A109.5
C4—C3—C2117.9 (2)C15—C19—H19A109.5
C4—C3—H3121.0C18—C19—H19B109.5
C2—C3—H3121.0C15—C19—H19B109.5
C3—C4—C5123.1 (2)H19A—C19—H19B108.0
C3—C4—N1118.2 (2)O9—C20—O10120.4 (2)
C5—C4—N1118.7 (2)O9—C20—C15120.1 (2)
C6—C5—C4118.0 (2)O10—C20—C15119.5 (2)
C6—C5—H5121.0O9—C20—Cd159.78 (12)
C4—C5—H5121.0O10—C20—Cd160.73 (13)
C5—C6—C1120.5 (2)C15—C20—Cd1176.71 (18)
C5—C6—H6119.7
O5—Cd1—O1—C7−44.7 (2)C20—Cd1—C7—O2113.00 (15)
O11—Cd1—O1—C7−113.45 (16)O5—Cd1—C7—C149.5 (17)
O2—Cd1—O1—C72.54 (14)O11—Cd1—C7—C1−38.2 (17)
O9—Cd1—O1—C7158.45 (14)O2—Cd1—C7—C181.7 (17)
O10—Cd1—O1—C7104.44 (16)O9—Cd1—C7—C1−134.7 (17)
C20—Cd1—O1—C7129.46 (15)O10—Cd1—C7—C1177.4 (17)
O5—Cd1—O2—C7153.29 (15)O1—Cd1—C7—C1−102.8 (17)
O11—Cd1—O2—C763.65 (15)C20—Cd1—C7—C1−165.3 (17)
O9—Cd1—O2—C7−79.0 (2)C13—C8—C9—C100.1 (5)
O10—Cd1—O2—C7−90.55 (15)C14—C8—C9—C10−177.8 (3)
O1—Cd1—O2—C7−2.52 (14)C8—C9—C10—C111.8 (5)
C20—Cd1—O2—C7−88.77 (16)C9—C10—C11—C12−1.9 (5)
O11—Cd1—O5—C14176.52 (19)C9—C10—C11—N2176.8 (3)
O2—Cd1—O5—C1471.91 (19)O7—N2—C11—C12−164.7 (4)
O9—Cd1—O5—C14−90.75 (19)O8—N2—C11—C1215.5 (5)
O10—Cd1—O5—C14−36.4 (2)O7—N2—C11—C1016.6 (5)
O1—Cd1—O5—C14109.9 (2)O8—N2—C11—C10−163.1 (4)
C7—Cd1—O5—C1486.6 (2)C10—C11—C12—C13−0.1 (5)
C20—Cd1—O5—C14−64.4 (2)N2—C11—C12—C13−178.8 (3)
O5—Cd1—O9—C20112.35 (16)C11—C12—C13—C82.1 (4)
O11—Cd1—O9—C20−160.08 (16)C9—C8—C13—C12−2.1 (4)
O2—Cd1—O9—C20−16.0 (3)C14—C8—C13—C12175.7 (2)
O10—Cd1—O9—C20−2.34 (15)Cd1—O5—C14—O6−5.4 (4)
O1—Cd1—O9—C20−80.19 (16)Cd1—O5—C14—C8176.17 (15)
C7—Cd1—O9—C20−64.15 (19)C9—C8—C14—O6−1.8 (4)
O5—Cd1—O10—C20−77.03 (17)C13—C8—C14—O6−179.6 (3)
O11—Cd1—O10—C2040.4 (2)C9—C8—C14—O5176.7 (3)
O2—Cd1—O10—C20177.09 (16)C13—C8—C14—O5−1.1 (4)
O9—Cd1—O10—C202.33 (15)C20—C15—C16—C17178.2 (2)
O1—Cd1—O10—C20120.86 (16)C19—C15—C16—C1755.1 (3)
C7—Cd1—O10—C20148.36 (16)C18—N3—C17—C1654.5 (3)
C6—C1—C2—C30.6 (4)C15—C16—C17—N3−54.3 (3)
C7—C1—C2—C3−176.9 (2)C17—N3—C18—C19−56.0 (3)
C1—C2—C3—C40.2 (4)N3—C18—C19—C1557.1 (3)
C2—C3—C4—C5−1.2 (4)C20—C15—C19—C18179.4 (2)
C2—C3—C4—N1179.4 (2)C16—C15—C19—C18−56.6 (3)
O4—N1—C4—C3177.0 (3)Cd1—O9—C20—O104.2 (3)
O3—N1—C4—C3−1.9 (4)Cd1—O9—C20—C15−176.2 (2)
O4—N1—C4—C5−2.4 (4)Cd1—O10—C20—O9−4.1 (3)
O3—N1—C4—C5178.7 (3)Cd1—O10—C20—C15176.2 (2)
C3—C4—C5—C61.3 (4)C16—C15—C20—O9140.5 (2)
N1—C4—C5—C6−179.3 (2)C19—C15—C20—O9−97.1 (3)
C4—C5—C6—C1−0.5 (4)C16—C15—C20—O10−39.9 (3)
C2—C1—C6—C5−0.4 (4)C19—C15—C20—O1082.6 (3)
C7—C1—C6—C5177.0 (2)C16—C15—C20—Cd153 (3)
Cd1—O1—C7—O2−4.6 (3)C19—C15—C20—Cd1175 (3)
Cd1—O1—C7—C1173.1 (2)O5—Cd1—C20—O9−72.07 (16)
Cd1—O2—C7—O14.7 (3)O11—Cd1—C20—O922.85 (18)
Cd1—O2—C7—C1−173.03 (19)O2—Cd1—C20—O9172.13 (13)
C2—C1—C7—O10.5 (4)O10—Cd1—C20—O9175.9 (3)
C6—C1—C7—O1−176.9 (2)O1—Cd1—C20—O9111.27 (15)
C2—C1—C7—O2178.3 (2)C7—Cd1—C20—O9137.25 (15)
C6—C1—C7—O20.9 (4)O5—Cd1—C20—O10112.06 (16)
C2—C1—C7—Cd1100.0 (17)O11—Cd1—C20—O10−153.02 (15)
C6—C1—C7—Cd1−77.4 (17)O2—Cd1—C20—O10−3.7 (2)
O5—Cd1—C7—O1152.24 (15)O9—Cd1—C20—O10−175.9 (3)
O11—Cd1—C7—O164.52 (16)O1—Cd1—C20—O10−64.60 (17)
O2—Cd1—C7—O1−175.5 (2)C7—Cd1—C20—O10−38.62 (19)
O9—Cd1—C7—O1−31.9 (2)O5—Cd1—C20—C1517 (3)
O10—Cd1—C7—O1−79.80 (16)O11—Cd1—C20—C15112 (3)
C20—Cd1—C7—O1−62.53 (18)O2—Cd1—C20—C15−99 (3)
O5—Cd1—C7—O2−32.23 (17)O9—Cd1—C20—C1589 (3)
O11—Cd1—C7—O2−119.95 (15)O10—Cd1—C20—C15−95 (3)
O9—Cd1—C7—O2143.58 (14)O1—Cd1—C20—C15−159 (3)
O10—Cd1—C7—O295.73 (15)C7—Cd1—C20—C15−133 (3)
O1—Cd1—C7—O2175.5 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O11—H11A···O3i0.852.263.019 (3)149
O11—H11B···O10ii0.851.912.754 (3)172
N3—H3A···O9iii0.902.042.887 (3)156
N3—H3B···O6iv0.901.892.762 (3)163
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+5/2, z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Cd1—O52.1917 (18)Cd1—O92.3327 (17)
Cd1—O112.3061 (19)Cd1—O102.3534 (18)
Cd1—O22.3229 (17)Cd1—O12.3684 (19)
O5—Cd1—O1187.34 (7)O5—Cd1—C20104.32 (7)
O5—Cd1—C7123.68 (7)O11—Cd1—C20118.82 (7)
O11—Cd1—C791.37 (7)C7—Cd1—C20124.63 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O11—H11A···O3i0.852.263.019 (3)149
O11—H11B···O10ii0.851.912.754 (3)172
N3—H3A···O9iii0.902.042.887 (3)156
N3—H3B···O6iv0.901.892.762 (3)163
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+5/2, z+1/2.
Acknowledgements top

The authors gratefully acknowledge financial support from Tianjin Education Committee (2006ZD07).

references
References top

Adams, C. J., Angeloni, A., Orpen, A. G., Podesta, T. J. & Shore, B. (2006a). Cryst. Growth Des. 6, 411–422.

Adams, C. J., Crawford, P. C., Orpen, A. G. & Podesta, T. J. (2006b). Dalton Trans. pp. 4078–4092.

Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2003). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Delgado, G., Mora, A. J. & Bahsas, A. (2001). Acta Cryst. C57, 965–967.

Fujita, M., Kwon, Y. J., Washizu, S. & Ogura, K. (1994). J. Am. Chem. Soc. 116, 1151–1152.

Inomata, Y., Ando, M. & Howell, F. S. (2002). J. Mol. Struct. 616, 201–212.

Inomata, Y., Arai, Y., Yamakoshi, T. & Howell, F. S. (2004). J. Inorg. Biochem. 98, 2149–2159.

Mora, A. J., Delgado, G., Ramírez, B. M., Rincón, L., Almeida, R., Cuervo, J. & Bahsas, A. (2002). J. Mol. Struct. 615, 201–208.

Muthu, S., Yip, J. H. K. & Vittal, J. J. (2002). J. Chem. Soc. Dalton Trans. pp. 4561–4568.

Podesta, T. J. & Orpen, A. G. (2002). CrystEngComm, 4, 336–342.

Rosi, N. L., Eckert, J., Eddaoudi, M., Vodak, D. T., Kim, J., ÖKeeffe, M. & Yaghi, O. M. (2003). Science, 300, 1127–1129.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, X. G., Li, J., Ding, B., Yang, E. C. & Zhao, X. J. (2008). J. Mol. Struct. 876, 268–277.

Zheng, X. J., Sun, C. Y., Lu, S. Z., Liao, F. H., Gao, S. & Jin, L. P. (2004). Eur. J. Inorg. Chem. pp. 3262–3268.