Poly[(μ2-quinoline-3-carboxyl­ato-κ2N:O)(μ2-quinoline-3-carboxyl­ato-κ3N:O,O′)cadmium]

Wang, X.; Yan, Y.-S.; Sun, H.-Y.; Wang, S.-T.; Liu, C.-B.

doi:10.1107/S1600536812001031

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m163

doi:10.1107/S1600536812001031

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Poly[(μ₂-quinoline-3-carboxylato-κ²N:O)(μ₂-quinoline-3-carboxylato-κ³N:O,O′)cadmium]

Xing Wang,^a Yong-Sheng Yan,^a He-Yi Sun,^a Shen-Tang Wang ^a and Chun-Bo Liu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: guangbocheujs@yahoo.com.cn

(Received 5 January 2012; accepted 10 January 2012; online 18 January 2012)

In the title compound, [Cd(C₁₀H₆NO₂)₂]_n, the Cd^II atom is coordinated by three O atoms and two N atoms from four quinoline-3-carboxylate (L⁻) ligands, leading to a distorted trigonal–bipyramidal geometry. The L⁻ ligands link the Cd^II atoms into a plane parallel to (100), with one ligand being tridentate, coordinating via the N atom and chelating a second Cd atom, and the other being bidentate, bridging two Cd atoms via the N and one O atom.. This two-dimensional network extends into a double-layer network by π–π interactions, with centroid–centroid distances of 3.680 (2) and 3.752 (2) Å. Another type of π–π interaction between pyridine rings [centroid–centroid distance = 3.527 (2) Å] leads to a three-dimensional supramolecular architecture.

Related literature

For background to the applications of cadmium coordination polymers and nicotinic acids, see: Niu et al. (2006 ); Song et al. (2006 ), Chen (2003); Chi et al. (2007 ); Lu et al. (2007 ). For a closely related structure, see: Hu et al. (2007 ).

Experimental

Crystal data

[Cd(C₁₀H₆NO₂)₂]
M_r = 456.72
Monoclinic, C 2/c
a = 28.5458 (19) Å
b = 8.2274 (5) Å
c = 15.381 (1) Å
β = 112.708 (1)°
V = 3332.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 153 K
0.13 × 0.11 × 0.10 mm

Data collection

Rigaku Saturn 724+ CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.845, T_max = 0.910
7361 measured reflections
3014 independent reflections
2659 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.051
S = 1.10
3014 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1ⁱ	2.3410 (16)
Cd1—N2	2.3188 (17)
Cd1—O1	2.1625 (15)
Cd1—O3ⁱⁱ	2.3858 (15)
Cd1—O4ⁱⁱ	2.2770 (15)
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalClear (Rigaku, 2007) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001031/vn2029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001031/vn2029Isup2.hkl

checkCIF report

Comment top

To date, much effort has been made on the construction of cadmium coordination polymers with a wide variety of topological structures which may possess promising perspectives toward molecular luminescent materials (Chi et al., 2007; Niu et al., 2006; Song et al., 2006; Lu et al., 2007). It is well known that nicotinic acid has been proved to be effective for constructing coordination polymers due to the versatile coordination fashion (Chen et al., 2003; Song et al., 2006). Compared with nicotinic acid, the structurally similar quinoline-3-carboxylic acid (HL) have been chosen to construct a new coordination polymer. Here, we report on the crystal structure of the title compound.

There is one cadmium (II) atom and two independent L^- ligands in the asymmetric unit. The Cd (II) atom is five-coordinated by two N atoms [Cd1—N1ⁱⁱ=2.341 (2) Å, Cd1—N2=2.319 (2) Å] and three O atoms [Cd1—O1=2.163 (2) Å, Cd—O3ⁱ=2.386 (2) Å, Cd—O4ⁱ=2.277 (2) Å] from four L^- ligands, showing a distorted trigonal bipyramidal coordination geometry (Fig. 1). The L^- ligand containing the N1 atom, acts as bis-monodentate mode toward cadmium centers with pyridine nitrogen atoms linking the cadmium atom and the carboxylate group linking the cadmium atom in a monodentate fashion, leading to the formation of a 1D chain structure along the the b axis. The 1D chains are linked into a 2D layer network by bis-chelating L^- ligand containing the N2 atom, There is in addition a 2D double-layer structure (black bond and green bond) which is connected by π–π interactions with the centroid to centroid distances of 3.680 (2) and 3.752 (2) Å, respectively (Fig. 2). The 2D double-layers are parallel to the (100) plane, and linked to each other by another type of π–π interaction between pyridine rings [centroid-to-centroid 3.527 (2) Å], resulting in a 3D supramolecular architecture.

There is a reported isostructural Zn analogue (Hu et al., 2007) which has a tetrahedral environment with L^- in a bis-monodentate mode, while the title compound shows a distorted trigonal bipyramidal coordination geometry with L^- in bis-monodentate and bis-chelating modes, respectively (Fig. 3). This comparison reveals the influence of different metal ion on the coordination mode of the ligand.

Related literature top

For background to the applications of cadmium coordination polymers and nicotinic acids, see: Niu et al. (2006); Song et al. (2006), Chen (2003); Chi et al. (2007); Lu et al. (2007). For a closely related structure, see: Hu et al. (2007).

Experimental top

Quinoline-3-carboxylic acid (HL) was purchased commercially and used without further purification. A mixture of CdCl₂ (18.400 mg, 0.1 mmol), and HL (17.300 mg, 0.1 mmol) was dissolved in a 10 mL of water with a pH = 6. The resulting mixture was heated in a 15 mL autoclave with Teflon-liner at 438 K for three days. Then the autoclave was slowly cooled to room temperature, and colourless block-shaped crystals were obtained with a yield of 50 %.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalClear (Rigaku, 2007) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound showing displacement ellipsoids (drawn at a 30% probability level) and labeling. H atoms are drawn as a small spheres of arbitrary radius. [symmetry codes: (i) x, - y, z + 1/2; (ii) x, y - 1, z.]
	Fig. 2. 2D double-layer structure and π-π stacking interactions between different 2D layers. All hydrogen atoms were omitted for clarity.
	Fig. 3. The comparision of the metal coordination environment between a reported isostructural Zn analogue and the title compound.

Poly[(µ₂-quinoline-3-carboxylato-κ²N:O)(µ₂-quinoline- 3-carboxylato-κ³N:O,O')cadmium] top

Crystal data top

[Cd(C₁₀H₆NO₂)₂]	F(000) = 1808
M_r = 456.72	D_x = 1.821 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6971 reflections
a = 28.5458 (19) Å	θ = 2.8–29.2°
b = 8.2274 (5) Å	µ = 1.34 mm⁻¹
c = 15.381 (1) Å	T = 153 K
β = 112.708 (1)°	Prism, colourless
V = 3332.3 (4) Å³	0.13 × 0.11 × 0.10 mm
Z = 8

Data collection top

Rigaku Saturn 724+ CCD area-detector diffractometer	3014 independent reflections
Radiation source: fine-focus sealed tube	2659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.3°, θ_min = 3.1°
ω scans	h = −34→34
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −9→9
T_min = 0.845, T_max = 0.910	l = −12→18
7361 measured reflections

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0291P)² + 0.9823P] where P = (F_o² + 2F_c²)/3
3014 reflections	(Δ/σ)_max = 0.002
244 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Cd(C₁₀H₆NO₂)₂]	V = 3332.3 (4) Å³
M_r = 456.72	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.5458 (19) Å	µ = 1.34 mm⁻¹
b = 8.2274 (5) Å	T = 153 K
c = 15.381 (1) Å	0.13 × 0.11 × 0.10 mm
β = 112.708 (1)°

Data collection top

Rigaku Saturn 724+ CCD area-detector diffractometer	3014 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	2659 reflections with I > 2σ(I)
T_min = 0.845, T_max = 0.910	R_int = 0.015
7361 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.10	Δρ_max = 0.33 e Å⁻³
3014 reflections	Δρ_min = −0.25 e Å⁻³
244 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.34654 (8)	0.4503 (3)	0.04346 (16)	0.0215 (5)
C2	0.32133 (8)	0.6060 (2)	−0.00212 (15)	0.0175 (4)
C3	0.34221 (7)	0.7571 (2)	0.03538 (14)	0.0179 (4)
H3	0.3719	0.7577	0.0895	0.021*
C4	0.27770 (8)	0.8986 (2)	−0.08096 (14)	0.0171 (4)
C5	0.25472 (8)	0.7512 (2)	−0.12288 (15)	0.0184 (4)
C6	0.27767 (8)	0.6043 (2)	−0.08109 (15)	0.0196 (5)
H6	0.2630	0.5057	−0.1074	0.023*
C7	0.25462 (8)	1.0467 (3)	−0.12039 (16)	0.0229 (5)
H7	0.2697	1.1447	−0.0939	0.028*
C8	0.20978 (9)	1.0464 (3)	−0.19802 (16)	0.0285 (5)
H8	0.1940	1.1444	−0.2227	0.034*
C9	0.18757 (9)	0.9000 (3)	−0.24036 (17)	0.0305 (6)
H9	0.1577	0.9019	−0.2941	0.037*
C10	0.20908 (8)	0.7552 (3)	−0.20397 (16)	0.0251 (5)
H10	0.1938	0.6587	−0.2324	0.030*
C11	0.40746 (8)	0.0031 (2)	−0.24972 (14)	0.0197 (5)
C12	0.43039 (8)	0.0798 (2)	−0.15411 (14)	0.0176 (4)
C13	0.40592 (8)	0.0688 (2)	−0.09095 (14)	0.0186 (4)
H13	0.3751	0.0139	−0.1106	0.022*
C14	0.47532 (8)	0.1623 (3)	−0.12613 (15)	0.0203 (5)
H14	0.4921	0.1728	−0.1671	0.024*
C15	0.49631 (8)	0.2315 (2)	−0.03555 (14)	0.0191 (5)
C16	0.46983 (8)	0.2114 (2)	0.02540 (14)	0.0175 (4)
C17	0.49105 (8)	0.2735 (2)	0.11748 (15)	0.0223 (5)
H17	0.4741	0.2599	0.1579	0.027*
C18	0.53653 (9)	0.3542 (3)	0.14796 (16)	0.0273 (5)
H18	0.5507	0.3935	0.2094	0.033*
C19	0.56197 (9)	0.3778 (3)	0.08655 (18)	0.0305 (6)
H19	0.5925	0.4344	0.1074	0.037*
C20	0.54238 (8)	0.3188 (3)	−0.00257 (17)	0.0275 (5)
H20	0.5595	0.3361	−0.0424	0.033*
N1	0.32245 (6)	0.89871 (19)	−0.00119 (12)	0.0168 (4)
N2	0.42383 (6)	0.13141 (19)	−0.00532 (12)	0.0174 (4)
O1	0.32218 (6)	0.32240 (18)	0.00681 (12)	0.0311 (4)
O2	0.38802 (6)	0.45193 (19)	0.11082 (12)	0.0291 (4)
O3	0.36675 (6)	−0.07521 (18)	−0.27266 (10)	0.0245 (3)
O4	0.43035 (6)	0.02228 (19)	−0.30471 (10)	0.0268 (4)
Cd1	0.371129 (5)	0.122196 (17)	0.077597 (10)	0.01700 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0258 (12)	0.0175 (11)	0.0264 (12)	0.0042 (10)	0.0158 (10)	0.0032 (9)
C2	0.0195 (11)	0.0155 (10)	0.0209 (11)	0.0021 (9)	0.0117 (9)	0.0024 (8)
C3	0.0165 (11)	0.0186 (11)	0.0186 (11)	0.0012 (9)	0.0068 (9)	0.0008 (9)
C4	0.0174 (10)	0.0187 (11)	0.0170 (11)	0.0003 (9)	0.0086 (9)	0.0014 (8)
C5	0.0182 (10)	0.0185 (10)	0.0200 (11)	0.0000 (9)	0.0091 (9)	0.0000 (9)
C6	0.0230 (11)	0.0142 (10)	0.0232 (12)	−0.0025 (9)	0.0108 (10)	−0.0027 (8)
C7	0.0253 (12)	0.0172 (11)	0.0256 (12)	0.0001 (10)	0.0092 (10)	0.0016 (9)
C8	0.0295 (13)	0.0254 (12)	0.0281 (13)	0.0087 (11)	0.0084 (11)	0.0100 (10)
C9	0.0237 (12)	0.0371 (14)	0.0228 (13)	0.0031 (11)	0.0003 (10)	0.0048 (10)
C10	0.0222 (12)	0.0255 (12)	0.0233 (12)	−0.0031 (10)	0.0040 (10)	−0.0016 (10)
C11	0.0226 (12)	0.0175 (10)	0.0163 (11)	0.0082 (10)	0.0044 (9)	0.0018 (8)
C12	0.0197 (11)	0.0166 (10)	0.0143 (11)	0.0043 (9)	0.0042 (9)	−0.0002 (8)
C13	0.0194 (11)	0.0176 (10)	0.0178 (11)	−0.0007 (9)	0.0060 (9)	0.0002 (8)
C14	0.0208 (11)	0.0224 (11)	0.0188 (11)	0.0031 (9)	0.0090 (9)	0.0018 (9)
C15	0.0172 (11)	0.0183 (10)	0.0195 (12)	0.0028 (9)	0.0046 (9)	0.0004 (9)
C16	0.0201 (11)	0.0128 (10)	0.0182 (11)	0.0026 (9)	0.0057 (9)	0.0012 (8)
C17	0.0266 (12)	0.0218 (11)	0.0176 (11)	−0.0006 (10)	0.0076 (9)	−0.0023 (9)
C18	0.0303 (13)	0.0255 (12)	0.0196 (12)	−0.0020 (11)	0.0024 (10)	−0.0051 (9)
C19	0.0218 (12)	0.0324 (14)	0.0328 (14)	−0.0109 (11)	0.0058 (10)	−0.0083 (10)
C20	0.0232 (12)	0.0304 (12)	0.0309 (14)	−0.0061 (10)	0.0126 (11)	−0.0029 (10)
N1	0.0178 (9)	0.0149 (9)	0.0176 (9)	0.0008 (7)	0.0067 (7)	0.0006 (7)
N2	0.0206 (9)	0.0171 (9)	0.0145 (9)	−0.0007 (7)	0.0067 (7)	0.0002 (7)
O1	0.0345 (9)	0.0137 (7)	0.0371 (10)	0.0016 (7)	0.0048 (8)	0.0015 (7)
O2	0.0267 (9)	0.0256 (9)	0.0300 (9)	0.0065 (7)	0.0054 (7)	0.0070 (7)
O3	0.0273 (9)	0.0259 (8)	0.0190 (8)	−0.0054 (7)	0.0075 (7)	−0.0051 (6)
O4	0.0263 (8)	0.0382 (9)	0.0167 (8)	−0.0031 (7)	0.0090 (7)	−0.0073 (7)
Cd1	0.02126 (10)	0.01480 (10)	0.01451 (10)	0.00057 (6)	0.00642 (7)	0.00132 (6)

Geometric parameters (Å, º) top

C1—O2	1.236 (3)	C12—C13	1.401 (3)
C1—O1	1.267 (3)	C13—N2	1.320 (3)
C1—C2	1.504 (3)	C13—H13	0.9300
C2—C6	1.364 (3)	C14—C15	1.407 (3)
C2—C3	1.403 (3)	C14—H14	0.9300
C3—N1	1.322 (3)	C15—C20	1.410 (3)
C3—H3	0.9300	C15—C16	1.423 (3)
C4—N1	1.388 (3)	C16—N2	1.379 (3)
C4—C7	1.407 (3)	C16—C17	1.404 (3)
C4—C5	1.411 (3)	C17—C18	1.370 (3)
C5—C6	1.406 (3)	C17—H17	0.9300
C5—C10	1.414 (3)	C18—C19	1.410 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.373 (3)	C19—C20	1.355 (3)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.399 (3)	C20—H20	0.9300
C8—H8	0.9300	N1—Cd1ⁱⁱ	2.3410 (16)
C9—C10	1.358 (3)	O3—Cd1ⁱ	2.3858 (15)
C9—H9	0.9300	O4—Cd1ⁱ	2.2770 (15)
C10—H10	0.9300	Cd1—N1ⁱⁱⁱ	2.3410 (16)
C11—O3	1.255 (3)	Cd1—N2	2.3188 (17)
C11—O4	1.262 (2)	Cd1—O1	2.1625 (15)
C11—C12	1.499 (3)	Cd1—O3^iv	2.3858 (15)
C11—Cd1ⁱ	2.658 (2)	Cd1—O4^iv	2.2770 (15)
C12—C14	1.366 (3)	Cd1—C11^iv	2.658 (2)

O2—C1—O1	124.4 (2)	C15—C14—H14	119.9
O2—C1—C2	120.84 (19)	C14—C15—C20	123.0 (2)
O1—C1—C2	114.72 (19)	C14—C15—C16	118.29 (19)
C6—C2—C3	118.19 (18)	C20—C15—C16	118.76 (19)
C6—C2—C1	120.99 (19)	N2—C16—C17	120.15 (18)
C3—C2—C1	120.81 (19)	N2—C16—C15	120.50 (18)
N1—C3—C2	124.21 (19)	C17—C16—C15	119.35 (19)
N1—C3—H3	117.9	C18—C17—C16	120.3 (2)
C2—C3—H3	117.9	C18—C17—H17	119.9
N1—C4—C7	119.89 (18)	C16—C17—H17	119.9
N1—C4—C5	120.76 (18)	C17—C18—C19	120.2 (2)
C7—C4—C5	119.35 (19)	C17—C18—H18	119.9
C6—C5—C4	118.53 (19)	C19—C18—H18	119.9
C6—C5—C10	122.08 (19)	C20—C19—C18	120.7 (2)
C4—C5—C10	119.38 (19)	C20—C19—H19	119.6
C2—C6—C5	120.16 (19)	C18—C19—H19	119.6
C2—C6—H6	119.9	C19—C20—C15	120.7 (2)
C5—C6—H6	119.9	C19—C20—H20	119.7
C8—C7—C4	119.8 (2)	C15—C20—H20	119.7
C8—C7—H7	120.1	C3—N1—C4	118.13 (17)
C4—C7—H7	120.1	C3—N1—Cd1ⁱⁱ	113.66 (13)
C7—C8—C9	120.6 (2)	C4—N1—Cd1ⁱⁱ	128.17 (13)
C7—C8—H8	119.7	C13—N2—C16	118.63 (17)
C9—C8—H8	119.7	C13—N2—Cd1	116.90 (14)
C10—C9—C8	120.8 (2)	C16—N2—Cd1	124.15 (13)
C10—C9—H9	119.6	C1—O1—Cd1	105.75 (14)
C8—C9—H9	119.6	C11—O3—Cd1ⁱ	88.09 (12)
C9—C10—C5	120.0 (2)	C11—O4—Cd1ⁱ	92.87 (13)
C9—C10—H10	120.0	O1—Cd1—O4^iv	159.22 (6)
C5—C10—H10	120.0	O1—Cd1—N2	97.38 (6)
O3—C11—O4	122.58 (19)	O4^iv—Cd1—N2	90.81 (5)
O3—C11—C12	119.90 (19)	O1—Cd1—N1ⁱⁱⁱ	101.45 (6)
O4—C11—C12	117.52 (19)	O4^iv—Cd1—N1ⁱⁱⁱ	96.41 (6)
O3—C11—Cd1ⁱ	63.76 (11)	N2—Cd1—N1ⁱⁱⁱ	97.04 (6)
O4—C11—Cd1ⁱ	58.81 (11)	O1—Cd1—O3^iv	110.18 (6)
C12—C11—Cd1ⁱ	176.28 (16)	O4^iv—Cd1—O3^iv	56.46 (5)
C14—C12—C13	118.20 (19)	N2—Cd1—O3^iv	145.40 (6)
C14—C12—C11	121.32 (19)	N1ⁱⁱⁱ—Cd1—O3^iv	97.50 (6)
C13—C12—C11	120.49 (19)	O1—Cd1—C11^iv	136.51 (7)
N2—C13—C12	124.2 (2)	O4^iv—Cd1—C11^iv	28.31 (6)
N2—C13—H13	117.9	N2—Cd1—C11^iv	118.46 (6)
C12—C13—H13	117.9	N1ⁱⁱⁱ—Cd1—C11^iv	97.88 (6)
C12—C14—C15	120.2 (2)	O3^iv—Cd1—C11^iv	28.14 (6)
C12—C14—H14	119.9

O2—C1—C2—C6	174.6 (2)	C17—C18—C19—C20	−1.2 (4)
O1—C1—C2—C6	−4.8 (3)	C18—C19—C20—C15	−0.5 (4)
O2—C1—C2—C3	−5.2 (3)	C14—C15—C20—C19	−177.5 (2)
O1—C1—C2—C3	175.38 (19)	C16—C15—C20—C19	2.2 (3)
C6—C2—C3—N1	−0.4 (3)	C2—C3—N1—C4	1.1 (3)
C1—C2—C3—N1	179.44 (18)	C2—C3—N1—Cd1ⁱⁱ	−176.85 (15)
N1—C4—C5—C6	1.1 (3)	C7—C4—N1—C3	178.10 (19)
C7—C4—C5—C6	−178.4 (2)	C5—C4—N1—C3	−1.4 (3)
N1—C4—C5—C10	179.84 (19)	C7—C4—N1—Cd1ⁱⁱ	−4.3 (3)
C7—C4—C5—C10	0.3 (3)	C5—C4—N1—Cd1ⁱⁱ	176.15 (14)
C3—C2—C6—C5	0.0 (3)	C12—C13—N2—C16	−0.8 (3)
C1—C2—C6—C5	−179.81 (18)	C12—C13—N2—Cd1	172.89 (16)
C4—C5—C6—C2	−0.4 (3)	C17—C16—N2—C13	−177.34 (19)
C10—C5—C6—C2	−179.1 (2)	C15—C16—N2—C13	2.5 (3)
N1—C4—C7—C8	−178.5 (2)	C17—C16—N2—Cd1	9.4 (3)
C5—C4—C7—C8	1.0 (3)	C15—C16—N2—Cd1	−170.71 (14)
C4—C7—C8—C9	−2.1 (4)	O2—C1—O1—Cd1	−5.0 (3)
C7—C8—C9—C10	1.9 (4)	C2—C1—O1—Cd1	174.42 (14)
C8—C9—C10—C5	−0.6 (4)	O4—C11—O3—Cd1ⁱ	−0.1 (2)
C6—C5—C10—C9	178.2 (2)	C12—C11—O3—Cd1ⁱ	179.26 (17)
C4—C5—C10—C9	−0.5 (3)	O3—C11—O4—Cd1ⁱ	0.1 (2)
O3—C11—C12—C14	178.30 (19)	C12—C11—O4—Cd1ⁱ	−179.27 (15)
O4—C11—C12—C14	−2.3 (3)	C1—O1—Cd1—O4^iv	33.2 (2)
O3—C11—C12—C13	−1.9 (3)	C1—O1—Cd1—N2	−79.22 (14)
O4—C11—C12—C13	177.47 (19)	C1—O1—Cd1—N1ⁱⁱⁱ	−177.98 (13)
C14—C12—C13—N2	−0.9 (3)	C1—O1—Cd1—O3^iv	79.52 (14)
C11—C12—C13—N2	179.27 (18)	C1—O1—Cd1—C11^iv	67.38 (17)
C13—C12—C14—C15	1.0 (3)	C13—N2—Cd1—O1	−77.63 (15)
C11—C12—C14—C15	−179.23 (19)	C16—N2—Cd1—O1	95.72 (15)
C12—C14—C15—C20	−179.7 (2)	C13—N2—Cd1—O4^iv	121.51 (15)
C12—C14—C15—C16	0.7 (3)	C16—N2—Cd1—O4^iv	−65.14 (15)
C14—C15—C16—N2	−2.5 (3)	C13—N2—Cd1—N1ⁱⁱⁱ	24.95 (15)
C20—C15—C16—N2	177.84 (19)	C16—N2—Cd1—N1ⁱⁱⁱ	−161.70 (15)
C14—C15—C16—C17	177.42 (19)	C13—N2—Cd1—O3^iv	139.20 (14)
C20—C15—C16—C17	−2.3 (3)	C16—N2—Cd1—O3^iv	−47.45 (19)
N2—C16—C17—C18	−179.46 (19)	C13—N2—Cd1—C11^iv	127.90 (14)
C15—C16—C17—C18	0.7 (3)	C16—N2—Cd1—C11^iv	−58.75 (16)
C16—C17—C18—C19	1.1 (3)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₆NO₂)₂]
M_r	456.72
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	153
a, b, c (Å)	28.5458 (19), 8.2274 (5), 15.381 (1)
β (°)	112.708 (1)
V (Å³)	3332.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.13 × 0.11 × 0.10

Data collection
Diffractometer	Rigaku Saturn 724+ CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.845, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	7361, 3014, 2659
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.051, 1.10
No. of reflections	3014
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: , SHELXL97 (Sheldrick, 2008), CrystalClear (Rigaku, 2007) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N1ⁱ	2.3410 (16)	Cd1—O3ⁱⁱ	2.3858 (15)
Cd1—N2	2.3188 (17)	Cd1—O4ⁱⁱ	2.2770 (15)
Cd1—O1	2.1625 (15)

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

Acknowledgements

The authors are thankful to Jiangsu University for support of this research.

References

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