Poly[(μ3-biphenyl-3,3′-dicarboxyl­ato)(1,10-phenanthroline)cadmium]

Qiu, Y.-E.

doi:10.1107/S1600536811042085

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1557

doi:10.1107/S1600536811042085

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Poly[(μ₃-biphenyl-3,3′-dicarboxylato)(1,10-phenanthroline)cadmium]

Yu-E Qiu ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou, Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzyeqiu@126.com

(Received 19 September 2011; accepted 12 October 2011; online 22 October 2011)

In the title compound, [Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]_n, the Cd^II ion is seven-coordinated in a distorted pentagonal–bipyramidal coordination geometry by five O atoms from bridging biphenyl-3,3′-dicarboylate (dpda) ligands and two N atoms from a 1,10-phenanthroline (1,10-phen) ligand. In the crystal, dinuclear units with a Cd⋯Cd separation of 3.8208 (7) Å are observed. Each of these dinuclear units is bridged via 3,3′-bpda in a chelating/chelating and bridging fashion, generating a zigzag chain along the c axis. Neighboring chains are further packed via weak π–π interactions between interchain parallel 1,10-phen rings [centroid–centroid distance = 3.5197 (9) Å] into a three-dimensional supramolecular architecture.

Related literature

For the use of biphenyldicarboxylato ligands in supramolecular chemistry, see: Furukawa et al. (2008 ); Qu (2007 ); Zhu (2010 ).

Experimental

Crystal data

[Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]
M_r = 532.81
Monoclinic, C 2/c
a = 26.1947 (17) Å
b = 9.7258 (5) Å
c = 21.2247 (14) Å
β = 127.411 (1)°
V = 4295.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 296 K
0.22 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.804, T_max = 0.887
12984 measured reflections
4902 independent reflections
3799 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.075
S = 1.04
4902 reflections
298 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811042085/im2322sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042085/im2322Isup2.hkl

checkCIF report

Comment top

Polycarboxylate ligands have been widely used to construct coordination polymers due to their versatile coordination modes. The use of biphenyldicarboxylic acid and its derivatives have been reported in literature (Qu, 2007; Furukawa et al., 2008; Zhu, 2010). The title coordination polymer [Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]_n, (I), was obtained under hydrothermal conditions and herein its crystal structure is reported.

There is one Cd^II cation, one 3,3'-biphenyl-dicarboxylate anion (3,3'-bpda) and one 1,10-phenanthroline (1,10-phen) ligand observed in the asymmetric unit of (I). The Cd^II ion is seven coordinated in a distorted pentagonal bipyramidal coordination geometry by five O atoms (O1ⁱⁱ, O2ⁱ, O2ⁱⁱ, O3, O4) from bridging 3,3'-bpda with Cd—O bond lengths in the range of 2.258 (2)–2.515 (3) Å, two N atoms (N1, N2) from two 1,10-phen ligands with Cd—N bond lengths of 2.336 (3) and 2.368 (3) Å (Fig. 1). In the crystal structure of (I), dinuclear units with a Cd···Cd separation of 3.8208 (7) Å are observed. Each of these dinuclear units is bridged via 3,3'-bpda in a µ₁ η¹:η¹/µ₂ η¹:η² coordination mode into one dimensional zigzag chains. Parallel 1, 10-phen ligands are attached to the outside of the zigzag chain with centroid distances of 3.5197 (9) Å indicating weak π-π stacking interactions (Fig. 2). Neighboring chains are further packed via weak π-π interactions between interchain parallel 1,10-phen rings into the resulting three dimensional supramolecular architecture.

Related literature top

For the use of biphenyldicarboxylato ligands in supramolecular chemistry, see: Furukawa et al. (2008); Qu (2007); Zhu (2010).

Experimental top

To a 16 ml Teflon-lined stainless steel vessel was loaded 3,3'-biphenyl-dicarboxylic acid (0.0242 g, 0.1 mmol), 1,10-phenanthroline (0.0198 g, 0.1 mmol), NaOH (0.0080 g, 0.2 mmol) and Cd(NO₃)₂ × 4H₂O (0.0308 g, 0.1 mmol), then it was sealed and heated to 160 °C for 72 h. After being cooled down to room temperature at a rate of -5 °C/h, colorless block shaped crystals are obtained after filtration. Yield: 0.025 g (47% based on Cd).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot of (I) at the 50% probability level. H atoms are represented by circles of arbitrary size. Symmetry code: (i)-x + 1, -y + 2, -z + 1; (ii)x, -y + 2, z - 1/2.
	Fig. 2. The one–dimensional zigzag chain structure of (I).

Poly[(µ₃-biphenyl-3,3'-dicarboxylato)(1,10-phenanthroline)cadmium] top

Crystal data top

[Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]	F(000) = 2128
M_r = 532.81	D_x = 1.648 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4252 reflections
a = 26.1947 (17) Å	θ = 2.3–26.6°
b = 9.7258 (5) Å	µ = 1.05 mm⁻¹
c = 21.2247 (14) Å	T = 296 K
β = 127.411 (1)°	Block, colorless
V = 4295.0 (5) Å³	0.22 × 0.16 × 0.12 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	4902 independent reflections
Radiation source: fine-focus sealed tube	3799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −33→34
T_min = 0.804, T_max = 0.887	k = −12→12
12984 measured reflections	l = −22→27

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0264P)² + 5.2631P] where P = (F_o² + 2F_c²)/3
4902 reflections	(Δ/σ)_max = 0.002
298 parameters	Δρ_max = 0.68 e Å⁻³
20 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]	V = 4295.0 (5) Å³
M_r = 532.81	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.1947 (17) Å	µ = 1.05 mm⁻¹
b = 9.7258 (5) Å	T = 296 K
c = 21.2247 (14) Å	0.22 × 0.16 × 0.12 mm
β = 127.411 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4902 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3799 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.887	R_int = 0.029
12984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	20 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.04	Δρ_max = 0.68 e Å⁻³
4902 reflections	Δρ_min = −0.39 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	0.576743 (12)	0.54986 (2)	0.356955 (13)	0.03981 (9)
O4	0.58387 (13)	0.7247 (2)	0.43196 (14)	0.0562 (6)
O2	0.53633 (12)	1.4416 (2)	0.71597 (14)	0.0510 (6)
N1	0.55605 (13)	0.3153 (3)	0.35361 (14)	0.0391 (6)
N2	0.66457 (14)	0.4227 (3)	0.38232 (16)	0.0462 (7)
O1	0.60664 (16)	1.2882 (2)	0.80000 (16)	0.0743 (9)
O3	0.63552 (15)	0.5452 (3)	0.50456 (15)	0.0715 (8)
C8	0.63079 (16)	0.9542 (3)	0.62890 (18)	0.0419 (7)
C22	0.7643 (2)	0.2526 (5)	0.4166 (2)	0.0690 (11)
H22	0.7980	0.1969	0.4287	0.083*
C15	0.50313 (17)	0.2623 (4)	0.33813 (19)	0.0493 (8)
H15	0.4707	0.3218	0.3267	0.059*
C9	0.61051 (15)	0.8739 (3)	0.56284 (18)	0.0384 (7)
H9	0.5779	0.9068	0.5125	0.046*
C6	0.60253 (15)	1.1531 (3)	0.67908 (18)	0.0378 (7)
H6	0.6193	1.1044	0.7256	0.045*
C25	0.66020 (16)	0.2840 (3)	0.38477 (18)	0.0429 (8)
C7	0.57685 (16)	1.2827 (3)	0.66989 (18)	0.0398 (7)
C5	0.60382 (15)	1.0940 (3)	0.62004 (18)	0.0372 (7)
C21	0.70931 (19)	0.1938 (4)	0.4015 (2)	0.0540 (9)
C26	0.60325 (16)	0.2285 (3)	0.37016 (17)	0.0410 (7)
C24	0.71735 (19)	0.4739 (4)	0.3960 (2)	0.0607 (10)
H24	0.7207	0.5686	0.3937	0.073*
C14	0.61750 (17)	0.6662 (3)	0.4976 (2)	0.0462 (8)
C10	0.63737 (18)	0.7474 (4)	0.5699 (2)	0.0510 (9)
C23	0.7685 (2)	0.3906 (5)	0.4137 (2)	0.0713 (12)
H23	0.8049	0.4303	0.4234	0.086*
C2	0.5534 (2)	1.3575 (4)	0.6021 (2)	0.0577 (10)
H2	0.5363	1.4447	0.5957	0.069*
C1	0.57283 (18)	1.3394 (3)	0.7327 (2)	0.0475 (8)
C3	0.5556 (2)	1.3028 (4)	0.5438 (2)	0.0668 (12)
H3	0.5407	1.3539	0.4986	0.080*
C17	0.5397 (2)	0.0336 (4)	0.3544 (2)	0.0605 (11)
H17	0.5336	−0.0606	0.3544	0.073*
C4	0.57985 (18)	1.1717 (4)	0.5526 (2)	0.0513 (9)
H4	0.5801	1.1351	0.5123	0.062*
C16	0.4936 (2)	0.1214 (4)	0.3381 (2)	0.0600 (10)
H16	0.4555	0.0885	0.3270	0.072*
C19	0.6478 (2)	−0.0034 (4)	0.3886 (2)	0.0646 (11)
H19	0.6439	−0.0982	0.3901	0.078*
C11	0.6841 (3)	0.6979 (5)	0.6435 (3)	0.0999 (17)
H11	0.7014	0.6111	0.6491	0.120*
C18	0.59693 (19)	0.0839 (3)	0.37142 (19)	0.0505 (9)
C13	0.6786 (2)	0.9026 (5)	0.7021 (2)	0.0867 (16)
H13	0.6926	0.9536	0.7470	0.104*
C12	0.7065 (3)	0.7767 (6)	0.7108 (3)	0.118 (2)
H12	0.7399	0.7446	0.7610	0.142*
C20	0.7008 (2)	0.0496 (4)	0.4026 (2)	0.0659 (11)
H20	0.7332	−0.0095	0.4135	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.05906 (17)	0.02976 (12)	0.03860 (14)	−0.00476 (11)	0.03382 (12)	−0.00224 (10)
O4	0.0822 (18)	0.0413 (13)	0.0422 (14)	0.0027 (13)	0.0362 (14)	−0.0058 (11)
O2	0.0564 (15)	0.0473 (13)	0.0569 (15)	0.0043 (12)	0.0383 (13)	−0.0115 (11)
N1	0.0439 (15)	0.0375 (14)	0.0341 (14)	−0.0049 (12)	0.0227 (12)	0.0023 (11)
N2	0.0523 (17)	0.0492 (17)	0.0444 (16)	−0.0107 (14)	0.0332 (14)	−0.0059 (13)
O1	0.145 (3)	0.0429 (14)	0.0609 (17)	0.0272 (16)	0.0757 (19)	0.0103 (12)
O3	0.107 (2)	0.0565 (13)	0.0489 (9)	0.0251 (13)	0.0461 (13)	0.0007 (11)
C8	0.0485 (19)	0.0465 (18)	0.0372 (17)	0.0058 (16)	0.0295 (15)	−0.0008 (15)
C22	0.066 (3)	0.094 (3)	0.058 (2)	0.010 (3)	0.043 (2)	−0.002 (2)
C15	0.055 (2)	0.049 (2)	0.046 (2)	−0.0103 (17)	0.0320 (18)	0.0016 (16)
C9	0.0429 (18)	0.0410 (17)	0.0334 (16)	0.0023 (14)	0.0243 (14)	−0.0009 (13)
C6	0.0468 (18)	0.0352 (15)	0.0384 (17)	−0.0041 (14)	0.0295 (15)	−0.0034 (13)
C25	0.052 (2)	0.0461 (19)	0.0315 (17)	−0.0015 (16)	0.0260 (16)	−0.0051 (14)
C7	0.0506 (19)	0.0361 (16)	0.0413 (17)	−0.0006 (14)	0.0324 (16)	−0.0045 (14)
C5	0.0402 (17)	0.0390 (16)	0.0388 (17)	−0.0025 (13)	0.0273 (15)	−0.0064 (13)
C21	0.061 (2)	0.067 (2)	0.0387 (19)	0.0051 (19)	0.0325 (18)	−0.0048 (17)
C26	0.054 (2)	0.0372 (17)	0.0282 (16)	−0.0054 (15)	0.0231 (15)	−0.0034 (13)
C24	0.065 (3)	0.066 (3)	0.061 (2)	−0.016 (2)	0.044 (2)	−0.0065 (19)
C14	0.061 (2)	0.0433 (14)	0.0453 (19)	0.0021 (16)	0.0380 (18)	−0.0038 (15)
C10	0.068 (2)	0.0494 (19)	0.0386 (18)	0.0156 (18)	0.0343 (18)	0.0033 (15)
C23	0.056 (3)	0.103 (4)	0.070 (3)	−0.008 (2)	0.046 (2)	−0.003 (3)
C2	0.086 (3)	0.0426 (19)	0.056 (2)	0.0179 (19)	0.049 (2)	0.0063 (17)
C1	0.074 (2)	0.0332 (17)	0.053 (2)	−0.0027 (17)	0.048 (2)	−0.0059 (16)
C3	0.107 (3)	0.057 (2)	0.053 (2)	0.024 (2)	0.057 (2)	0.0156 (18)
C17	0.083 (3)	0.039 (2)	0.048 (2)	−0.019 (2)	0.034 (2)	−0.0024 (16)
C4	0.071 (2)	0.053 (2)	0.0431 (19)	0.0113 (18)	0.0417 (19)	−0.0005 (16)
C16	0.071 (3)	0.055 (2)	0.050 (2)	−0.024 (2)	0.035 (2)	−0.0018 (18)
C19	0.093 (3)	0.0386 (19)	0.055 (2)	0.006 (2)	0.041 (2)	−0.0048 (17)
C11	0.136 (4)	0.084 (3)	0.060 (3)	0.060 (3)	0.050 (3)	0.004 (2)
C18	0.072 (3)	0.0370 (17)	0.0343 (18)	−0.0015 (17)	0.0277 (18)	−0.0024 (14)
C13	0.112 (4)	0.089 (3)	0.037 (2)	0.051 (3)	0.034 (2)	−0.002 (2)
C12	0.150 (4)	0.109 (3)	0.056 (3)	0.073 (3)	0.042 (3)	0.006 (2)
C20	0.088 (3)	0.056 (2)	0.054 (2)	0.023 (2)	0.043 (2)	−0.0011 (19)

Geometric parameters (Å, º) top

Cd1—O4	2.258 (2)	C6—H6	0.9300
Cd1—N1	2.336 (3)	C25—C21	1.413 (5)
Cd1—N2	2.368 (3)	C25—C26	1.432 (4)
Cd1—O2ⁱ	2.368 (2)	C7—C2	1.380 (4)
Cd1—O1ⁱⁱ	2.388 (2)	C7—C1	1.505 (4)
Cd1—O2ⁱⁱ	2.497 (2)	C5—C4	1.387 (4)
Cd1—O3	2.515 (3)	C21—C20	1.423 (5)
Cd1—C14	2.731 (3)	C26—C18	1.419 (4)
O4—C14	1.245 (4)	C24—C23	1.406 (6)
O2—C1	1.271 (4)	C24—H24	0.9300
O2—Cd1ⁱ	2.368 (2)	C14—C10	1.509 (4)
O2—Cd1ⁱⁱⁱ	2.497 (2)	C10—C11	1.360 (5)
N1—C15	1.320 (4)	C23—H23	0.9300
N1—C26	1.355 (4)	C2—C3	1.378 (5)
N2—C24	1.325 (4)	C2—H2	0.9300
N2—C25	1.358 (4)	C3—C4	1.386 (5)
O1—C1	1.238 (4)	C3—H3	0.9300
O1—Cd1ⁱⁱⁱ	2.388 (2)	C17—C16	1.341 (6)
O3—C14	1.243 (4)	C17—C18	1.401 (6)
C8—C13	1.367 (5)	C17—H17	0.9300
C8—C9	1.397 (4)	C4—H4	0.9300
C8—C5	1.491 (4)	C16—H16	0.9300
C22—C23	1.352 (6)	C19—C20	1.336 (6)
C22—C21	1.393 (5)	C19—C18	1.428 (6)
C22—H22	0.9300	C19—H19	0.9300
C15—C16	1.393 (5)	C11—C12	1.398 (6)
C15—H15	0.9300	C11—H11	0.9300
C9—C10	1.380 (4)	C13—C12	1.380 (6)
C9—H9	0.9300	C13—H13	0.9300
C6—C7	1.385 (4)	C12—H12	0.9300
C6—C5	1.398 (4)	C20—H20	0.9300

O4—Cd1—N1	132.46 (9)	C4—C5—C6	117.3 (3)
O4—Cd1—N2	125.46 (10)	C4—C5—C8	120.7 (3)
N1—Cd1—N2	70.87 (9)	C6—C5—C8	122.0 (3)
O4—Cd1—O2ⁱ	88.24 (9)	C22—C21—C25	117.3 (4)
N1—Cd1—O2ⁱ	80.75 (9)	C22—C21—C20	123.4 (4)
N2—Cd1—O2ⁱ	145.46 (8)	C25—C21—C20	119.3 (4)
O4—Cd1—O1ⁱⁱ	87.04 (9)	N1—C26—C18	121.6 (3)
N1—Cd1—O1ⁱⁱ	140.34 (9)	N1—C26—C25	119.2 (3)
N2—Cd1—O1ⁱⁱ	83.53 (10)	C18—C26—C25	119.2 (3)
O2ⁱ—Cd1—O1ⁱⁱ	108.10 (10)	N2—C24—C23	122.6 (4)
O4—Cd1—O2ⁱⁱ	127.82 (8)	N2—C24—H24	118.7
N1—Cd1—O2ⁱⁱ	94.27 (8)	C23—C24—H24	118.7
N2—Cd1—O2ⁱⁱ	86.32 (8)	O3—C14—O4	121.7 (3)
O2ⁱ—Cd1—O2ⁱⁱ	76.36 (8)	O3—C14—C10	120.2 (3)
O1ⁱⁱ—Cd1—O2ⁱⁱ	53.28 (8)	O4—C14—C10	118.1 (3)
O4—Cd1—O3	53.83 (8)	O3—C14—Cd1	66.77 (18)
N1—Cd1—O3	88.58 (8)	O4—C14—Cd1	54.92 (16)
N2—Cd1—O3	86.12 (9)	C10—C14—Cd1	172.8 (2)
O2ⁱ—Cd1—O3	113.01 (9)	C11—C10—C9	118.9 (3)
O1ⁱⁱ—Cd1—O3	120.11 (10)	C11—C10—C14	119.8 (3)
O2ⁱⁱ—Cd1—O3	170.56 (9)	C9—C10—C14	121.2 (3)
O4—Cd1—C14	26.82 (9)	C22—C23—C24	119.6 (4)
N1—Cd1—C14	111.54 (9)	C22—C23—H23	120.2
N2—Cd1—C14	106.69 (10)	C24—C23—H23	120.2
O2ⁱ—Cd1—C14	101.72 (9)	C3—C2—C7	119.8 (3)
O1ⁱⁱ—Cd1—C14	104.46 (9)	C3—C2—H2	120.1
O2ⁱⁱ—Cd1—C14	153.63 (9)	C7—C2—H2	120.1
O3—Cd1—C14	27.01 (9)	O1—C1—O2	121.8 (3)
C14—O4—Cd1	98.26 (19)	O1—C1—C7	119.2 (3)
C1—O2—Cd1ⁱ	129.8 (2)	O2—C1—C7	119.0 (3)
C1—O2—Cd1ⁱⁱⁱ	89.51 (19)	C2—C3—C4	120.0 (3)
Cd1ⁱ—O2—Cd1ⁱⁱⁱ	103.50 (8)	C2—C3—H3	120.0
C15—N1—C26	118.5 (3)	C4—C3—H3	120.0
C15—N1—Cd1	125.3 (2)	C16—C17—C18	120.0 (3)
C26—N1—Cd1	116.2 (2)	C16—C17—H17	120.0
C24—N2—C25	117.8 (3)	C18—C17—H17	120.0
C24—N2—Cd1	126.5 (3)	C3—C4—C5	121.5 (3)
C25—N2—Cd1	115.8 (2)	C3—C4—H4	119.2
C1—O1—Cd1ⁱⁱⁱ	95.4 (2)	C5—C4—H4	119.2
C14—O3—Cd1	86.2 (2)	C17—C16—C15	119.5 (4)
C13—C8—C9	117.5 (3)	C17—C16—H16	120.2
C13—C8—C5	121.0 (3)	C15—C16—H16	120.2
C9—C8—C5	121.4 (3)	C20—C19—C18	120.7 (4)
C23—C22—C21	119.9 (4)	C20—C19—H19	119.7
C23—C22—H22	120.1	C18—C19—H19	119.7
C21—C22—H22	120.1	C10—C11—C12	120.4 (4)
N1—C15—C16	123.1 (4)	C10—C11—H11	119.8
N1—C15—H15	118.5	C12—C11—H11	119.8
C16—C15—H15	118.5	C17—C18—C26	117.4 (4)
C10—C9—C8	122.1 (3)	C17—C18—C19	123.1 (4)
C10—C9—H9	118.9	C26—C18—C19	119.5 (4)
C8—C9—H9	118.9	C8—C13—C12	121.6 (4)
C7—C6—C5	121.5 (3)	C8—C13—H13	119.2
C7—C6—H6	119.3	C12—C13—H13	119.2
C5—C6—H6	119.3	C13—C12—C11	119.3 (4)
N2—C25—C21	122.8 (3)	C13—C12—H12	120.3
N2—C25—C26	117.9 (3)	C11—C12—H12	120.3
C21—C25—C26	119.4 (3)	C19—C20—C21	121.9 (4)
C2—C7—C6	119.8 (3)	C19—C20—H20	119.0
C2—C7—C1	120.3 (3)	C21—C20—H20	119.0
C6—C7—C1	119.9 (3)

N1—Cd1—O4—C14	45.0 (3)	Cd1—N2—C24—C23	177.4 (3)
N2—Cd1—O4—C14	−51.1 (2)	Cd1—O3—C14—O4	0.5 (4)
O2ⁱ—Cd1—O4—C14	120.7 (2)	Cd1—O3—C14—C10	−178.2 (3)
O1ⁱⁱ—Cd1—O4—C14	−131.0 (2)	Cd1—O4—C14—O3	−0.5 (4)
O2ⁱⁱ—Cd1—O4—C14	−168.08 (19)	Cd1—O4—C14—C10	178.2 (3)
O3—Cd1—O4—C14	0.3 (2)	O4—Cd1—C14—O3	179.5 (4)
O4—Cd1—N1—C15	60.5 (3)	N1—Cd1—C14—O3	33.6 (3)
N2—Cd1—N1—C15	−178.5 (3)	N2—Cd1—C14—O3	−41.9 (2)
O2ⁱ—Cd1—N1—C15	−18.5 (2)	O2ⁱ—Cd1—C14—O3	118.2 (2)
O1ⁱⁱ—Cd1—N1—C15	−125.7 (3)	O1ⁱⁱ—Cd1—C14—O3	−129.4 (2)
O2ⁱⁱ—Cd1—N1—C15	−93.9 (2)	O2ⁱⁱ—Cd1—C14—O3	−158.9 (2)
O3—Cd1—N1—C15	95.1 (2)	N1—Cd1—C14—O4	−145.9 (2)
O4—Cd1—N1—C26	−118.5 (2)	N2—Cd1—C14—O4	138.5 (2)
N2—Cd1—N1—C26	2.46 (19)	O2ⁱ—Cd1—C14—O4	−61.3 (2)
O2ⁱ—Cd1—N1—C26	162.5 (2)	O1ⁱⁱ—Cd1—C14—O4	51.1 (2)
O1ⁱⁱ—Cd1—N1—C26	55.2 (3)	O2ⁱⁱ—Cd1—C14—O4	21.6 (3)
O2ⁱⁱ—Cd1—N1—C26	87.1 (2)	O3—Cd1—C14—O4	−179.5 (4)
O3—Cd1—N1—C26	−83.9 (2)	O4—Cd1—C14—C10	−12.9 (19)
O4—Cd1—N2—C24	−51.3 (3)	N1—Cd1—C14—C10	−158.8 (19)
N1—Cd1—N2—C24	179.7 (3)	N2—Cd1—C14—C10	126 (2)
O2ⁱ—Cd1—N2—C24	143.2 (3)	O2ⁱ—Cd1—C14—C10	−74 (2)
O1ⁱⁱ—Cd1—N2—C24	30.4 (3)	O1ⁱⁱ—Cd1—C14—C10	38 (2)
O2ⁱⁱ—Cd1—N2—C24	83.9 (3)	O2ⁱⁱ—Cd1—C14—C10	9 (2)
O3—Cd1—N2—C24	−90.5 (3)	O3—Cd1—C14—C10	168 (2)
O4—Cd1—N2—C25	127.0 (2)	C8—C9—C10—C11	1.4 (6)
N1—Cd1—N2—C25	−2.0 (2)	C8—C9—C10—C14	−176.3 (3)
O2ⁱ—Cd1—N2—C25	−38.5 (3)	O3—C14—C10—C11	12.1 (6)
O1ⁱⁱ—Cd1—N2—C25	−151.3 (2)	O4—C14—C10—C11	−166.7 (4)
O2ⁱⁱ—Cd1—N2—C25	−97.8 (2)	O3—C14—C10—C9	−170.2 (4)
O3—Cd1—N2—C25	87.8 (2)	O4—C14—C10—C9	11.0 (5)
O4—Cd1—O3—C14	−0.3 (2)	C21—C22—C23—C24	0.5 (6)
N1—Cd1—O3—C14	−149.0 (2)	N2—C24—C23—C22	0.5 (6)
N2—Cd1—O3—C14	140.1 (2)	C6—C7—C2—C3	0.2 (6)
O2ⁱ—Cd1—O3—C14	−69.7 (2)	C1—C7—C2—C3	−178.0 (4)
O1ⁱⁱ—Cd1—O3—C14	59.9 (3)	Cd1ⁱⁱⁱ—O1—C1—O2	−2.7 (4)
O2ⁱⁱ—Cd1—O3—C14	103.3 (5)	Cd1ⁱⁱⁱ—O1—C1—C7	174.9 (3)
C26—N1—C15—C16	0.1 (5)	Cd1ⁱ—O2—C1—O1	−104.7 (4)
Cd1—N1—C15—C16	−178.9 (2)	Cd1ⁱⁱⁱ—O2—C1—O1	2.6 (4)
C13—C8—C9—C10	−0.4 (5)	Cd1ⁱ—O2—C1—C7	77.7 (4)
C5—C8—C9—C10	176.5 (3)	Cd1ⁱⁱⁱ—O2—C1—C7	−175.0 (3)
C24—N2—C25—C21	0.3 (5)	C2—C7—C1—O1	−163.1 (4)
Cd1—N2—C25—C21	−178.1 (2)	C6—C7—C1—O1	18.7 (5)
C24—N2—C25—C26	179.9 (3)	C2—C7—C1—O2	14.6 (5)
Cd1—N2—C25—C26	1.5 (3)	C6—C7—C1—O2	−163.6 (3)
C5—C6—C7—C2	−1.8 (5)	C7—C2—C3—C4	1.4 (6)
C5—C6—C7—C1	176.4 (3)	C2—C3—C4—C5	−1.5 (6)
C7—C6—C5—C4	1.6 (5)	C6—C5—C4—C3	0.0 (5)
C7—C6—C5—C8	−179.4 (3)	C8—C5—C4—C3	−178.9 (4)
C13—C8—C5—C4	149.9 (4)	C18—C17—C16—C15	0.2 (5)
C9—C8—C5—C4	−26.9 (5)	N1—C15—C16—C17	−0.1 (5)
C13—C8—C5—C6	−29.0 (5)	C9—C10—C11—C12	−2.7 (8)
C9—C8—C5—C6	154.2 (3)	C14—C10—C11—C12	175.1 (5)
C23—C22—C21—C25	−1.0 (5)	C16—C17—C18—C26	−0.3 (5)
C23—C22—C21—C20	179.4 (4)	C16—C17—C18—C19	−179.5 (3)
N2—C25—C21—C22	0.6 (5)	N1—C26—C18—C17	0.4 (5)
C26—C25—C21—C22	−179.0 (3)	C25—C26—C18—C17	−178.1 (3)
N2—C25—C21—C20	−179.8 (3)	N1—C26—C18—C19	179.6 (3)
C26—C25—C21—C20	0.6 (5)	C25—C26—C18—C19	1.1 (5)
C15—N1—C26—C18	−0.3 (4)	C20—C19—C18—C17	178.4 (4)
Cd1—N1—C26—C18	178.9 (2)	C20—C19—C18—C26	−0.7 (5)
C15—N1—C26—C25	178.2 (3)	C9—C8—C13—C12	0.7 (7)
Cd1—N1—C26—C25	−2.7 (3)	C5—C8—C13—C12	−176.2 (5)
N2—C25—C26—N1	0.8 (4)	C8—C13—C12—C11	−2.0 (10)
C21—C25—C26—N1	−179.6 (3)	C10—C11—C12—C13	3.0 (10)
N2—C25—C26—C18	179.3 (3)	C18—C19—C20—C21	0.3 (6)
C21—C25—C26—C18	−1.1 (4)	C22—C21—C20—C19	179.3 (4)
C25—N2—C24—C23	−0.9 (5)	C25—C21—C20—C19	−0.2 (6)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₄H₈O₄)(C₁₂H₈N₂)]
M_r	532.81
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	26.1947 (17), 9.7258 (5), 21.2247 (14)
β (°)	127.411 (1)
V (Å³)	4295.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.22 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.804, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	12984, 4902, 3799
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.075, 1.04
No. of reflections	4902
No. of parameters	298
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

This work was supported financially by the project of Shandong Province Higher Educational Science and Technology Program (grant No. J11LB56).

References

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