catena-Poly[[bis­(dimethyl­ammonium) [cadmate(II)-bis­(μ-1,1′:4′,1′′-terphenyl-3,3′′-dicarboxyl­ato)]] dimethyl­formamide disolvate]

Park, S.-W.; Gu, J.-M.; Kim, Y.; Huh, S.

doi:10.1107/S1600536810051366

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m71

https://doi.org/10.1107/S1600536810051366

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catena-Poly[[bis(dimethylammonium) [cadmate(II)-bis(μ-1,1′:4′,1′′-terphenyl-3,3′′-dicarboxylato)]] dimethylformamide disolvate]

Sang-Wook Park,^a Ja-Min Gu,^a Youngmee Kim ^b and Seong Huh ^a ^*

^aDepartment of Chemistry and Protein Research Center for Bio-Industry, Hankuk University of Foreign Studies, Yongin 449-791, Republic of Korea, and ^bDepartment of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
^*Correspondence e-mail: shuh@hufs.ac.kr

(Received 29 November 2010; accepted 7 December 2010; online 11 December 2010)

In the title compound, {(C₂H₈N)₂[Cd(C₂₀H₁₂O₄)₂]·2C₃H₇NO}_n, the Cd^II ion lies on a twofold rotation axis and is in a distorted octahedral CdO₆ environment, defined by four O atoms of two μ²-coordinated 1,1′:4′,1′′-terphenyl-3,3′′-dicarboxylate (DCT) ligands and two O atoms of two μ¹-coordinated DCT ligands. Both types of DCT ligands act as bridging, forming a one-dimensional polymeric structure propagating parallel to [10 $[\overline1]$ ].

Related literature

For background information on metal-organic frameworks (MOFs), see: Li & Zhou (2009 ); Huh et al. (2009 , 2010 ); Youm et al. (2004 ); Gu et al. (2010 ).

Experimental

Crystal data

(C₂H₈N)₂[Cd(C₂₀H₁₂O₄)₂]·2C₃H₇NO
M_r = 983.37
Monoclinic, C 2/c
a = 28.525 (4) Å
b = 9.3267 (13) Å
c = 20.580 (3) Å
β = 114.752 (2)°
V = 4972.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.08 × 0.08 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
13515 measured reflections
4888 independent reflections
2861 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.116
S = 0.90
4888 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 1.47 e Å⁻³
Δρ_min = −0.76 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051366/lh5182sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051366/lh5182Isup2.hkl

checkCIF report

Comment top

The role of bridging ligands in the formation of structurally interesting metal-organic frameworks (MOFs) is of significant importance for the design of multi-functional MOFs and coordination polymers (Li & Zhou, 2009; Huh et al., 2010; Huh et al., 2009; Youm et al., 2004). For instance, the reaction between a Zn(II) ion and a new C_{2 h}-symmetric bridging ligand, 3,3"-dicarboxy-1,1':4',1"-terphenyl (DCT), in the presence of 1,4-diazacyclo[2,2,2]octane (DABCO) afforded a new nanoporous Zn-MOF containing DABCO ligands with an uncoordinated nitrogen atom towards one-dimensional channels. The resulting DABCO-functionalized Zn-MOF showed a better adsorption of CO₂ over H₂ and N₂ with an exceptionally high CO₂ adsorption enthalpy (Gu et al., 2010).

To prepare new functional MOFs and coordination polymers, a reaction between Cd(NO₃)₂.H₂O and the DCT ligand was investigated. A new one-dimensional coordination polymer, [H₂N(CH₃)₂]₂[Cd(DCT)₂].2DMF (I), was obtained as colorless crystals and the crystal structure of (I) is reported herein. In the crystal structure of the title compound the Cd atom is coordinated by four oxygen atoms of two µ²-coordinated DCT ligands and two oxygen atoms of two µ¹-coordinated DCT ligands (Fig. 1). Two DCT ligands bridging two Cd atoms and the title compound forms an extended one-dimensional coordination polymer (Fig. 2). The overall coordination environment of a Cd atom is a distorted octahedral geometry. The title compound possesses periodically arranged Cd^II ions with two negative charges per Cd center because of the charge mismatching between Cd^II ions and the DCT ligands. Therefore two dimethylammonium cations are required for charge balancing. In addtion there are two dimethylformamide solvent molecules in the formula unit.

Related literature top

For background information on metal-organic frameworks (MOFs), see: Li & Zhou (2009); Huh et al. (2009, 2010); Youm et al. (2004); Gu et al. (2010).

Experimental top

The reaction mixture of Cd(NO₃)₂.H₂O (30.8 mg, 0.1 mmol) and 3,3"-dicarboxy-1,1':4',1"-terphenyl (DCT, 32 mg, 0.1 mmol) in 10 ml of DMF was heated at 130 °C for 4 d. The resulting clear solution was storedat room temperature for few days gave colorless crystals.

Structure description top

For background information on metal-organic frameworks (MOFs), see: Li & Zhou (2009); Huh et al. (2009, 2010); Youm et al. (2004); Gu et al. (2010).

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound's anion with labeling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. One-dimensional chain of the title compound. The dimethylammonium cations and DMF solvent molecules are omitted for clarity.

catena-Poly[[bis(dimethylammonium) [cadmate(II)-bis(µ-1,1':4',1''-terphenyl-3,3''-dicarboxylato)]] dimethylformamide disolvate] top

Crystal data top

(C₂H₈N)₂[Cd(C₂₀H₁₂O₄)₂]·2C₃H₇NO	F(000) = 2040
M_r = 983.37	D_x = 1.314 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2049 reflections
a = 28.525 (4) Å	θ = 2.3–27.0°
b = 9.3267 (13) Å	µ = 0.50 mm⁻¹
c = 20.580 (3) Å	T = 293 K
β = 114.752 (2)°	Block, colorless
V = 4972.1 (11) Å³	0.08 × 0.08 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
φ and ω scans	h = −35→32
13515 measured reflections	k = −8→11
4888 independent reflections	l = −25→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
4888 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 1.47 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

(C₂H₈N)₂[Cd(C₂₀H₁₂O₄)₂]·2C₃H₇NO	V = 4972.1 (11) Å³
M_r = 983.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.525 (4) Å	µ = 0.50 mm⁻¹
b = 9.3267 (13) Å	T = 293 K
c = 20.580 (3) Å	0.08 × 0.08 × 0.05 mm
β = 114.752 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2861 reflections with I > 2σ(I)
13515 measured reflections	R_int = 0.068
4888 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.90	Δρ_max = 1.47 e Å⁻³
4888 reflections	Δρ_min = −0.76 e Å⁻³
298 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

	x	y	z	U_iso*/U_eq
Cd1	1.0000	0.22586 (5)	0.7500	0.03992 (17)
O1	1.08028 (11)	0.3209 (3)	0.77314 (16)	0.0572 (9)
O2	1.01785 (11)	0.4040 (3)	0.67570 (16)	0.0621 (9)
O3	0.95903 (10)	0.0827 (3)	0.65658 (14)	0.0505 (8)
O4	1.03902 (12)	0.0114 (4)	0.68232 (16)	0.0719 (10)
C1	1.06411 (17)	0.4007 (5)	0.7194 (2)	0.0449 (11)
C2	1.10258 (15)	0.4955 (4)	0.7074 (2)	0.0389 (10)
C3	1.15225 (14)	0.5095 (4)	0.7608 (2)	0.0390 (10)
H3	1.1610	0.4619	0.8040	0.047*
C4	1.18932 (14)	0.5936 (4)	0.7510 (2)	0.0382 (10)
C5	1.17464 (16)	0.6611 (5)	0.6854 (2)	0.0482 (12)
H5	1.1987	0.7164	0.6770	0.058*
C6	1.12548 (16)	0.6485 (5)	0.6323 (2)	0.0534 (12)
H6	1.1167	0.6951	0.5888	0.064*
C7	1.08924 (16)	0.5672 (5)	0.6433 (2)	0.0471 (11)
H7	1.0558	0.5605	0.6077	0.056*
C8	0.74239 (14)	−0.1084 (4)	0.3083 (2)	0.0377 (10)
C9	0.76565 (15)	0.0007 (5)	0.3571 (2)	0.0452 (11)
H9	0.7467	0.0827	0.3560	0.054*
C10	0.81649 (16)	−0.0094 (5)	0.4076 (2)	0.0465 (11)
H10	0.8308	0.0657	0.4395	0.056*
C11	0.84628 (15)	−0.1288 (5)	0.4114 (2)	0.0379 (10)
C12	0.82222 (15)	−0.2418 (5)	0.3648 (2)	0.0443 (11)
H12	0.8404	−0.3260	0.3677	0.053*
C13	0.77171 (15)	−0.2300 (5)	0.3145 (2)	0.0463 (11)
H13	0.7569	−0.3066	0.2837	0.056*
C14	0.90158 (15)	−0.1368 (4)	0.4619 (2)	0.0385 (10)
C15	0.92021 (15)	−0.0652 (4)	0.5273 (2)	0.0408 (10)
H15	0.8975	−0.0131	0.5400	0.049*
C16	0.97212 (15)	−0.0706 (4)	0.5738 (2)	0.0396 (10)
C17	1.00572 (16)	−0.1481 (5)	0.5552 (2)	0.0506 (12)
H17	1.0406	−0.1523	0.5861	0.061*
C18	0.98748 (16)	−0.2195 (5)	0.4906 (2)	0.0541 (12)
H18	1.0102	−0.2724	0.4782	0.065*
C19	0.93633 (16)	−0.2132 (5)	0.4445 (2)	0.0480 (11)
H19	0.9248	−0.2609	0.4009	0.058*
C20	0.99169 (17)	0.0116 (5)	0.6434 (2)	0.0473 (11)
N21	0.1478 (2)	0.4189 (6)	0.9596 (2)	0.0814 (14)
O21	0.16600 (16)	0.1981 (4)	0.9324 (2)	0.0925 (13)
C21	0.1350 (2)	0.2929 (7)	0.9302 (3)	0.0737 (16)
H21	0.1000	0.2727	0.9057	0.088*
C22	0.2015 (3)	0.4610 (9)	0.9988 (4)	0.146 (3)
H22A	0.2235	0.3826	0.9996	0.220*
H22B	0.2077	0.4863	1.0469	0.220*
H22C	0.2088	0.5420	0.9757	0.220*
C23	0.1082 (3)	0.5226 (8)	0.9496 (3)	0.126 (3)
H23A	0.1143	0.6068	0.9275	0.189*
H23B	0.1088	0.5475	0.9952	0.189*
H23C	0.0752	0.4828	0.9196	0.189*
N31	0.12647 (13)	1.0202 (4)	0.80646 (18)	0.0537 (10)
H31A	0.1302	1.0770	0.8436	0.064*
H31B	0.0943	1.0331	0.7724	0.064*
C31	0.16355 (19)	1.0657 (7)	0.7781 (3)	0.0912 (19)
H31C	0.1980	1.0579	0.8149	0.137*
H31D	0.1568	1.1634	0.7623	0.137*
H31E	0.1601	1.0055	0.7385	0.137*
C32	0.1320 (2)	0.8719 (6)	0.8299 (3)	0.101 (2)
H32A	0.1310	0.8107	0.7919	0.152*
H32B	0.1042	0.8471	0.8426	0.152*
H32C	0.1643	0.8599	0.8708	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0305 (2)	0.0450 (3)	0.0417 (3)	0.000	0.01258 (19)	0.000
O1	0.0486 (19)	0.058 (2)	0.060 (2)	−0.0061 (16)	0.0182 (16)	0.0137 (17)
O2	0.0367 (18)	0.067 (2)	0.072 (2)	−0.0066 (16)	0.0126 (17)	0.0110 (17)
O3	0.0426 (18)	0.061 (2)	0.0476 (18)	0.0010 (15)	0.0182 (15)	−0.0085 (15)
O4	0.0410 (19)	0.101 (3)	0.055 (2)	0.0050 (19)	0.0016 (16)	−0.0156 (19)
C1	0.042 (3)	0.041 (3)	0.051 (3)	0.002 (2)	0.019 (2)	−0.003 (2)
C2	0.037 (2)	0.035 (3)	0.047 (3)	0.0023 (19)	0.020 (2)	0.002 (2)
C3	0.038 (2)	0.038 (3)	0.040 (2)	0.005 (2)	0.015 (2)	0.0036 (19)
C4	0.033 (2)	0.037 (3)	0.044 (3)	0.0013 (19)	0.015 (2)	0.000 (2)
C5	0.040 (3)	0.053 (3)	0.053 (3)	−0.004 (2)	0.020 (2)	0.014 (2)
C6	0.043 (3)	0.064 (3)	0.048 (3)	0.002 (2)	0.014 (2)	0.016 (2)
C7	0.035 (2)	0.048 (3)	0.051 (3)	0.004 (2)	0.011 (2)	0.007 (2)
C8	0.035 (2)	0.036 (3)	0.042 (2)	0.000 (2)	0.016 (2)	0.001 (2)
C9	0.041 (3)	0.041 (3)	0.052 (3)	0.006 (2)	0.017 (2)	−0.006 (2)
C10	0.046 (3)	0.042 (3)	0.045 (3)	−0.002 (2)	0.013 (2)	−0.006 (2)
C11	0.039 (2)	0.042 (3)	0.034 (2)	0.002 (2)	0.0158 (19)	0.002 (2)
C12	0.044 (2)	0.040 (3)	0.048 (3)	0.006 (2)	0.018 (2)	−0.002 (2)
C13	0.045 (2)	0.040 (3)	0.052 (3)	−0.003 (2)	0.018 (2)	−0.011 (2)
C14	0.040 (2)	0.040 (3)	0.034 (2)	0.001 (2)	0.014 (2)	0.001 (2)
C15	0.037 (2)	0.042 (3)	0.044 (3)	0.001 (2)	0.018 (2)	0.002 (2)
C16	0.038 (2)	0.040 (3)	0.038 (2)	0.002 (2)	0.012 (2)	−0.001 (2)
C17	0.038 (3)	0.057 (3)	0.051 (3)	0.009 (2)	0.012 (2)	−0.001 (2)
C18	0.048 (3)	0.056 (3)	0.060 (3)	0.010 (2)	0.024 (2)	−0.008 (3)
C19	0.045 (3)	0.051 (3)	0.045 (3)	0.002 (2)	0.015 (2)	−0.010 (2)
C20	0.047 (3)	0.046 (3)	0.045 (3)	−0.002 (2)	0.015 (2)	0.003 (2)
N21	0.092 (4)	0.076 (4)	0.074 (3)	−0.010 (3)	0.034 (3)	−0.021 (3)
O21	0.095 (3)	0.086 (3)	0.078 (3)	0.011 (2)	0.018 (2)	−0.011 (2)
C21	0.090 (4)	0.067 (4)	0.054 (3)	−0.016 (4)	0.020 (3)	−0.010 (3)
C22	0.108 (6)	0.159 (8)	0.171 (7)	−0.055 (5)	0.057 (5)	−0.080 (6)
C23	0.151 (7)	0.092 (6)	0.130 (6)	0.007 (5)	0.054 (5)	−0.012 (4)
N31	0.046 (2)	0.060 (3)	0.049 (2)	0.010 (2)	0.0142 (19)	−0.0055 (19)
C31	0.069 (4)	0.108 (5)	0.113 (5)	0.000 (3)	0.055 (4)	−0.002 (4)
C32	0.134 (6)	0.064 (4)	0.127 (5)	0.021 (4)	0.075 (5)	0.014 (4)

Geometric parameters (Å, º) top

Cd1—O3	2.228 (3)	C12—H12	0.9300
Cd1—O3ⁱ	2.228 (3)	C13—H13	0.9300
Cd1—O1	2.312 (3)	C14—C19	1.383 (5)
Cd1—O1ⁱ	2.312 (3)	C14—C15	1.394 (5)
Cd1—O2	2.451 (3)	C15—C16	1.387 (5)
Cd1—O2ⁱ	2.451 (3)	C15—H15	0.9300
Cd1—C1ⁱ	2.714 (4)	C16—C17	1.376 (5)
Cd1—C1	2.714 (4)	C16—C20	1.510 (6)
O1—C1	1.250 (5)	C17—C18	1.380 (6)
O2—C1	1.248 (4)	C17—H17	0.9300
O3—C20	1.262 (5)	C18—C19	1.369 (5)
O4—C20	1.249 (5)	C18—H18	0.9300
C1—C2	1.508 (6)	C19—H19	0.9300
C2—C7	1.383 (5)	N21—C21	1.302 (6)
C2—C3	1.389 (5)	N21—C23	1.434 (7)
C3—C4	1.397 (5)	N21—C22	1.455 (7)
C3—H3	0.9300	O21—C21	1.238 (6)
C4—C5	1.386 (5)	C21—H21	0.9300
C4—C8ⁱⁱ	1.485 (5)	C22—H22A	0.9600
C5—C6	1.375 (5)	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—C7	1.375 (5)	C23—H23A	0.9600
C6—H6	0.9300	C23—H23B	0.9600
C7—H7	0.9300	C23—H23C	0.9600
C8—C13	1.383 (5)	N31—C32	1.452 (6)
C8—C9	1.388 (5)	N31—C31	1.469 (6)
C8—C4ⁱⁱⁱ	1.485 (5)	N31—H31A	0.9000
C9—C10	1.389 (5)	N31—H31B	0.9000
C9—H9	0.9300	C31—H31C	0.9600
C10—C11	1.383 (5)	C31—H31D	0.9600
C10—H10	0.9300	C31—H31E	0.9600
C11—C12	1.396 (5)	C32—H32A	0.9600
C11—C14	1.484 (5)	C32—H32B	0.9600
C12—C13	1.383 (5)	C32—H32C	0.9600

O3—Cd1—O3ⁱ	106.36 (15)	C10—C11—C14	121.9 (4)
O3—Cd1—O1	121.60 (10)	C12—C11—C14	121.0 (4)
O3ⁱ—Cd1—O1	86.31 (11)	C13—C12—C11	120.9 (4)
O3—Cd1—O1ⁱ	86.31 (11)	C13—C12—H12	119.6
O3ⁱ—Cd1—O1ⁱ	121.60 (10)	C11—C12—H12	119.6
O1—Cd1—O1ⁱ	134.91 (16)	C12—C13—C8	122.3 (4)
O3—Cd1—O2	92.22 (10)	C12—C13—H13	118.9
O3ⁱ—Cd1—O2	140.68 (10)	C8—C13—H13	118.9
O1—Cd1—O2	54.70 (10)	C19—C14—C15	118.1 (4)
O1ⁱ—Cd1—O2	93.34 (10)	C19—C14—C11	120.8 (4)
O3—Cd1—O2ⁱ	140.68 (10)	C15—C14—C11	121.0 (4)
O3ⁱ—Cd1—O2ⁱ	92.22 (10)	C16—C15—C14	121.0 (4)
O1—Cd1—O2ⁱ	93.34 (11)	C16—C15—H15	119.5
O1ⁱ—Cd1—O2ⁱ	54.69 (10)	C14—C15—H15	119.5
O2—Cd1—O2ⁱ	94.67 (15)	C17—C16—C15	119.6 (4)
O3—Cd1—C1ⁱ	113.54 (12)	C17—C16—C20	120.4 (4)
O3ⁱ—Cd1—C1ⁱ	108.72 (12)	C15—C16—C20	120.0 (4)
O1—Cd1—C1ⁱ	115.31 (12)	C16—C17—C18	119.7 (4)
O1ⁱ—Cd1—C1ⁱ	27.33 (10)	C16—C17—H17	120.1
O2—Cd1—C1ⁱ	94.22 (11)	C18—C17—H17	120.1
O2ⁱ—Cd1—C1ⁱ	27.36 (10)	C19—C18—C17	120.6 (4)
O3—Cd1—C1	108.72 (12)	C19—C18—H18	119.7
O3ⁱ—Cd1—C1	113.54 (12)	C17—C18—H18	119.7
O1—Cd1—C1	27.34 (10)	C18—C19—C14	121.0 (4)
O1ⁱ—Cd1—C1	115.31 (12)	C18—C19—H19	119.5
O2—Cd1—C1	27.36 (10)	C14—C19—H19	119.5
O2ⁱ—Cd1—C1	94.22 (11)	O4—C20—O3	124.1 (4)
C1ⁱ—Cd1—C1	106.12 (18)	O4—C20—C16	118.6 (4)
C1—O1—Cd1	94.5 (3)	O3—C20—C16	117.2 (4)
C1—O2—Cd1	88.1 (3)	C21—N21—C23	119.5 (6)
C20—O3—Cd1	109.4 (3)	C21—N21—C22	121.7 (6)
O2—C1—O1	122.7 (4)	C23—N21—C22	118.7 (6)
O2—C1—C2	119.3 (4)	O21—C21—N21	124.9 (6)
O1—C1—C2	118.0 (4)	O21—C21—H21	117.5
O2—C1—Cd1	64.5 (2)	N21—C21—H21	117.5
O1—C1—Cd1	58.1 (2)	N21—C22—H22A	109.5
C2—C1—Cd1	176.1 (3)	N21—C22—H22B	109.5
C7—C2—C3	119.4 (4)	H22A—C22—H22B	109.5
C7—C2—C1	120.8 (4)	N21—C22—H22C	109.5
C3—C2—C1	119.8 (4)	H22A—C22—H22C	109.5
C2—C3—C4	121.4 (4)	H22B—C22—H22C	109.5
C2—C3—H3	119.3	N21—C23—H23A	109.5
C4—C3—H3	119.3	N21—C23—H23B	109.5
C5—C4—C3	117.2 (4)	H23A—C23—H23B	109.5
C5—C4—C8ⁱⁱ	121.5 (4)	N21—C23—H23C	109.5
C3—C4—C8ⁱⁱ	121.3 (4)	H23A—C23—H23C	109.5
C6—C5—C4	121.8 (4)	H23B—C23—H23C	109.5
C6—C5—H5	119.1	C32—N31—C31	114.3 (4)
C4—C5—H5	119.1	C32—N31—H31A	108.7
C7—C6—C5	120.2 (4)	C31—N31—H31A	108.7
C7—C6—H6	119.9	C32—N31—H31B	108.7
C5—C6—H6	119.9	C31—N31—H31B	108.7
C6—C7—C2	119.9 (4)	H31A—N31—H31B	107.6
C6—C7—H7	120.1	N31—C31—H31C	109.5
C2—C7—H7	120.1	N31—C31—H31D	109.5
C13—C8—C9	116.6 (4)	H31C—C31—H31D	109.5
C13—C8—C4ⁱⁱⁱ	121.7 (4)	N31—C31—H31E	109.5
C9—C8—C4ⁱⁱⁱ	121.7 (4)	H31C—C31—H31E	109.5
C8—C9—C10	121.6 (4)	H31D—C31—H31E	109.5
C8—C9—H9	119.2	N31—C32—H32A	109.5
C10—C9—H9	119.2	N31—C32—H32B	109.5
C11—C10—C9	121.5 (4)	H32A—C32—H32B	109.5
C11—C10—H10	119.3	N31—C32—H32C	109.5
C9—C10—H10	119.3	H32A—C32—H32C	109.5
C10—C11—C12	117.0 (4)	H32B—C32—H32C	109.5

O3—Cd1—O1—C1	68.3 (3)	C2—C3—C4—C5	−0.8 (6)
O3ⁱ—Cd1—O1—C1	175.3 (3)	C2—C3—C4—C8ⁱⁱ	180.0 (4)
O1ⁱ—Cd1—O1—C1	−52.1 (2)	C3—C4—C5—C6	1.1 (6)
O2—Cd1—O1—C1	0.6 (2)	C8ⁱⁱ—C4—C5—C6	−179.6 (4)
O2ⁱ—Cd1—O1—C1	−92.7 (3)	C4—C5—C6—C7	0.0 (7)
C1ⁱ—Cd1—O1—C1	−75.8 (3)	C5—C6—C7—C2	−1.4 (7)
O3—Cd1—O2—C1	−128.6 (3)	C3—C2—C7—C6	1.7 (6)
O3ⁱ—Cd1—O2—C1	−9.1 (3)	C1—C2—C7—C6	−177.4 (4)
O1—Cd1—O2—C1	−0.6 (2)	C13—C8—C9—C10	2.6 (6)
O1ⁱ—Cd1—O2—C1	145.0 (3)	C4ⁱⁱⁱ—C8—C9—C10	−175.6 (4)
O2ⁱ—Cd1—O2—C1	90.1 (3)	C8—C9—C10—C11	0.1 (6)
C1ⁱ—Cd1—O2—C1	117.6 (3)	C9—C10—C11—C12	−3.3 (6)
O3ⁱ—Cd1—O3—C20	−64.4 (3)	C9—C10—C11—C14	175.9 (4)
O1—Cd1—O3—C20	31.4 (3)	C10—C11—C12—C13	3.7 (6)
O1ⁱ—Cd1—O3—C20	173.7 (3)	C14—C11—C12—C13	−175.5 (4)
O2—Cd1—O3—C20	80.5 (3)	C11—C12—C13—C8	−1.0 (6)
O2ⁱ—Cd1—O3—C20	−179.4 (2)	C9—C8—C13—C12	−2.2 (6)
C1ⁱ—Cd1—O3—C20	176.1 (3)	C4ⁱⁱⁱ—C8—C13—C12	176.1 (4)
C1—Cd1—O3—C20	58.2 (3)	C10—C11—C14—C19	−148.1 (4)
Cd1—O2—C1—O1	1.1 (4)	C12—C11—C14—C19	31.1 (6)
Cd1—O2—C1—C2	−179.3 (3)	C10—C11—C14—C15	30.5 (6)
Cd1—O1—C1—O2	−1.2 (5)	C12—C11—C14—C15	−150.4 (4)
Cd1—O1—C1—C2	179.2 (3)	C19—C14—C15—C16	−0.1 (6)
O3—Cd1—C1—O2	55.5 (3)	C11—C14—C15—C16	−178.7 (4)
O3ⁱ—Cd1—C1—O2	173.7 (2)	C14—C15—C16—C17	−0.2 (6)
O1—Cd1—C1—O2	178.9 (4)	C14—C15—C16—C20	178.1 (4)
O1ⁱ—Cd1—C1—O2	−39.3 (3)	C15—C16—C17—C18	0.0 (7)
O2ⁱ—Cd1—C1—O2	−92.0 (3)	C20—C16—C17—C18	−178.3 (4)
C1ⁱ—Cd1—C1—O2	−66.9 (2)	C16—C17—C18—C19	0.5 (7)
O3—Cd1—C1—O1	−123.3 (3)	C17—C18—C19—C14	−0.8 (7)
O3ⁱ—Cd1—C1—O1	−5.2 (3)	C15—C14—C19—C18	0.6 (6)
O1ⁱ—Cd1—C1—O1	141.8 (2)	C11—C14—C19—C18	179.2 (4)
O2—Cd1—C1—O1	−178.9 (4)	Cd1—O3—C20—O4	7.4 (5)
O2ⁱ—Cd1—C1—O1	89.1 (3)	Cd1—O3—C20—C16	−168.7 (3)
C1ⁱ—Cd1—C1—O1	114.2 (3)	C17—C16—C20—O4	2.3 (6)
O2—C1—C2—C7	−10.8 (6)	C15—C16—C20—O4	−176.0 (4)
O1—C1—C2—C7	168.7 (4)	C17—C16—C20—O3	178.6 (4)
O2—C1—C2—C3	170.1 (4)	C15—C16—C20—O3	0.4 (6)
O1—C1—C2—C3	−10.3 (6)	C23—N21—C21—O21	176.3 (6)
C7—C2—C3—C4	−0.6 (6)	C22—N21—C21—O21	0.3 (9)
C1—C2—C3—C4	178.5 (4)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	(C₂H₈N)₂[Cd(C₂₀H₁₂O₄)₂]·2C₃H₇NO
M_r	983.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.525 (4), 9.3267 (13), 20.580 (3)
β (°)	114.752 (2)
V (Å³)	4972.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.08 × 0.08 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13515, 4888, 2861
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.116, 0.90
No. of reflections	4888
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.47, −0.76

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD, Basic ResearchPromotion Fund) (KRF-2008–331-C00149).

References

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