Poly[(2,2′-bipyridine-κ2N,N′)(μ3-2,4,6-trimethyl­isophthalato-κ5O1,O1′:O1:O3,O3′)cadmium]

Hou, S.-G.; Jin, M.-F.

doi:10.1107/S1600536811054183

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages m84-m85

doi:10.1107/S1600536811054183

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Poly[(2,2′-bipyridine-κ²N,N′)(μ₃-2,4,6-trimethylisophthalato-κ⁵O¹,O^1′:O¹:O³,O^3′)cadmium]

Shao-Gang Hou ^a and Mei-Fang Jin ^a ^*

^aCollege of Chemical and Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
^*Correspondence e-mail: aymeifangjin@163.com

(Received 23 November 2011; accepted 16 December 2011; online 23 December 2011)

In the crystal structure of the polymeric title complex, [Cd(C₁₁H₁₀O₄)(C₁₀H₈N₂)]_n, the Cd^II cation is chelated by one 2,2-bipyridine ligand and two carboxyl groups from two trimethylisophthalate (TMIPA) anions, and is further coordinated by one carboxylate O atom from a third TMIPA anion, forming a distorted pentagonal–bipyramidal geometry. Each TMIPA anion bridges three Cd^II cations, forming polymeric complex sheets parallel to (001). Weak C—H⋯O hydrogen bonding occurs between adjacent sheets.

Related literature

For applications of functional metal-organic frameworks, see: Evans & Lin (2002 ); Chen et al. (2010 ); Leong & Vittal (2011 ); Sun et al. (2011 ). For related structures, see: Ma et al. (2008 ); Zhang et al. (2008 ); Zhou et al. (2003 ); Zhang et al. (2003 ); He et al. (2010 ); Liu et al. (2008 ). For our previous work, see: Dai et al. (2008 , 2009 ); Zhao et al. (2009 ).

Experimental

Crystal data

[Cd(C₁₁H₁₀O₄)(C₁₀H₈N₂)]
M_r = 474.77
Orthorhombic, P b c a
a = 13.1985 (8) Å
b = 15.5714 (9) Å
c = 18.1926 (11) Å
V = 3738.9 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 298 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.841, T_max = 0.890
14349 measured reflections
4299 independent reflections
2454 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.098
S = 0.99
4299 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.393 (4)
Cd1—N2	2.334 (4)
Cd1—O1	2.607 (3)
Cd1—O2ⁱ	2.317 (3)
Cd1—O2	2.372 (3)
Cd1—O3ⁱⁱ	2.347 (3)
Cd1—O4ⁱⁱ	2.396 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1ⁱⁱⁱ	0.93	2.32	3.240 (6)	169
C8—H8A⋯O3ⁱⁱⁱ	0.93	2.39	3.251 (6)	155
Symmetry code: (iii) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054183/xu5394sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054183/xu5394Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054183/xu5394Isup3.mol

checkCIF report

Comment top

The rational design and synthesis of functional metal-organic frameworks (MOFs) is a more and more fascinating field in recent years due to their interesting topologies and potential applications in gas adsorption, nonlinear optics, magnetism, molecular recognition, etc (Evans & Lin, 2002; Chen, et al., 2010; Leong & Vittal, 2011; Sun et al., 2011). As we know, the construction of MOFs mainly depends on the coordination geometry of metal ions and the nature of ligands. Besides, some secondary interactions, such as aromatic π···π interactions, classical hydrogen bonds (such as O-H···O and N-H···O hydrogen bonds), and non-classical hydrogen bonds (such as C-H···O hydrogen bond) often influence the packing of molecules from discrete subunits or low-dimentional entities to high-dimentional supramolecular frameworks. One of the most effective strategies to assemble MOFs is to use carboxylates as linkers because of their diverse conformations and coordination modes observed in the coordination process (Ma et al., 2008; Zhang et al., 2008). In spite of isophthalate-based MOFs (Zhou et al., 2003; Zhang et al., 2003) have been widely reported, to the best of our knowledge, only one MOF based on 2,4,6,-trimethylisophthalic acid (H₂TMIPA) has been documented until now (He et al., 2010). Based on our previous work (Dai et al., 2008; Dai et al., 2009; Zhao et al., 2009) and consideration the steric hindrance effects of additional three methyl groups on isophthalate, herein, we choose the H₂TMIPA as a bridging ligand to construct a novel Cd^II coordination polymer (I), which is a 2D (4,4) net incorporating [Cd₂(COO)₄N₂] SBUs.

The asymmetric unit of (I) contains one crystallographically independent Cd^II center, one TMIPA ligand and one bpy ligand. The Cd^II ion is in a slightly distorted pentagonal bipyramidal geometry, completed by five O atoms from three different TMIPA ligands and two N atoms from the same bpy ligand (Fig. 1). The equatorial plane of pentagonal bipyramid is defined by O2ⁱ, O3ⁱⁱ, O4ⁱⁱ, N2 atoms, while the axial positions are occupied N1, O1 atoms. [symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+3/2, y+1/2, z]. Two carboxyl groups on TMIPA ligand adopt two different coordination patterns, µ₁-η¹: η¹ chelating and µ₂-η²: η¹ bridging, respectively. The Cd-N bond lengths are 2.393 (4) and 2.334 (4) Å, while the Cd-O bond lengths vary from 2.317 (3) to 2.607 (3) Å (Table). The average Cd-N and Cd-O distances in (I) are comparable with those reported for Cd-based MOFs (Liu et al., 2008). Two crystallographically equivalent Cd^II anions are bridged by two tridentate bridging carboxyl groups to form a binuclear SBU with a Cd···Cd contact of 3.7886 (6) Å. Because of the steric hindrance between the methyl and the carboxyl groups, the two carboxyl groups of H₂TMIPA are not coplanar with the central benzene ring, generating two dihedral angles of 55.1 (2) and 85.3 (2)^o, respectively. The [Cd₂(COO)₄N₂] SBUs are joined by TMIPA ligands to form an infinite 1D zigzag chain. Furthermore, TMIPA ligands connect the zigzag chain to a 2D layer (Fig. 2) which is consolidated by the intrasheet weak face-to-face π···π interaction between bpy and TMIPA with Cg1···Cg2ⁱ separation of 3.725 (3) Å (Cg1 and Cg2 are the centroids of the N1/C1–C5 and C12–C17 rings, respectively; symmetry code: (i) -x+1, -y+1, -z+1). The bpy ligand acts as a terminal group to occupy the remaining coordinate sites, which prevents the structure from higher dimensionalities. The adjacent 2D layers are further extended to a 3D supramolecular framework by virtue of non-classical C-H···O hydrogen bonds (Table 2).

Related literature top

For applications of functional metal-organic frameworks, see: Evans & Lin (2002); Chen et al. (2010); Leong & Vittal (2011); Sun et al. (2011). For related structures, see: Ma et al. (2008); Zhang et al. (2008); Zhou et al. (2003); Zhang et al. (2003); He et al. (2010); Liu et al. (2008). For our previous work, see: Dai et al. (2008, 2009); Zhao et al. (2009).

Experimental top

A mixture of Cd(NO₃)₂.6H₂O (30 mg, 0.12 mmol), 2,4,6,-trimethylisophthalic acid (H₂TMIPA) (20 mg, 0.12 mmol) and bipyridine (10 mg, 0.06 mmol) was suspended in 15 mL mixed solvents of N,N'-dimethylformamide, ethanol and H₂O (v/v = 1:1:1), and heated in a Teflon-lined steel bomb at 373 K for 4 days. After cooling to room temperature, colorless crystals were collected, washed with ethanol several times, and dried in the air (yield: 47%, based on H₂TMIPA).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme and the coordination environment around the Cd^IIcentre. Displacement ellipsoids are drawn at 50% probability level and H atoms are shown as small spheres of arbitrary radii. (symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+3/2, y+1/2, z)
	Fig. 2. A ball-and-stick perspective view of the 2D sheet incorporating weak face-to-face π···π interaction (green dashed lines). Hydrogen atoms are omitted for clarity.

Poly[(2,2'-bipyridine-κ²N,N')(µ₃-2,4,6- trimethylisophthalato- κ⁵O¹,O^1':O¹:O³,O^3')cadmium] top

Crystal data top

[Cd(C₁₁H₁₀O₄)(C₁₀H₈N₂)]	F(000) = 1904
M_r = 474.77	D_x = 1.687 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5089 reflections
a = 13.1985 (8) Å	θ = 2.2–27.8°
b = 15.5714 (9) Å	µ = 1.20 mm⁻¹
c = 18.1926 (11) Å	T = 298 K
V = 3738.9 (4) Å³	Block, colorless
Z = 8	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4299 independent reflections
Radiation source: fine-focus sealed tube	2454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω and ϕ scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→11
T_min = 0.841, T_max = 0.890	k = −17→20
14349 measured reflections	l = −15→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
4299 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Cd(C₁₁H₁₀O₄)(C₁₀H₈N₂)]	V = 3738.9 (4) Å³
M_r = 474.77	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.1985 (8) Å	µ = 1.20 mm⁻¹
b = 15.5714 (9) Å	T = 298 K
c = 18.1926 (11) Å	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4299 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2454 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.890	R_int = 0.054
14349 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 0.99	Δρ_max = 0.51 e Å⁻³
4299 reflections	Δρ_min = −0.63 e Å⁻³
253 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
Cd1	0.50573 (2)	0.584163 (18)	0.575068 (16)	0.03177 (11)
C1	0.3060 (4)	0.7000 (3)	0.6257 (3)	0.0496 (14)
H1A	0.3218	0.7291	0.5826	0.060*
C2	0.2259 (4)	0.7293 (3)	0.6667 (3)	0.0569 (15)
H2A	0.1873	0.7758	0.6512	0.068*
C3	0.2046 (4)	0.6877 (3)	0.7314 (3)	0.0634 (16)
H3A	0.1518	0.7064	0.7613	0.076*
C4	0.2620 (4)	0.6187 (3)	0.7511 (3)	0.0586 (15)
H4A	0.2489	0.5903	0.7951	0.070*
C5	0.3391 (3)	0.5909 (3)	0.7063 (2)	0.0385 (11)
C6	0.4024 (4)	0.5140 (3)	0.7238 (2)	0.0396 (11)
C7	0.3857 (4)	0.4630 (3)	0.7852 (3)	0.0471 (13)
H7A	0.3346	0.4768	0.8183	0.057*
C8	0.4453 (4)	0.3916 (3)	0.7965 (3)	0.0541 (15)
H8A	0.4352	0.3573	0.8377	0.065*
C9	0.5189 (4)	0.3718 (3)	0.7472 (3)	0.0622 (16)
H9A	0.5590	0.3232	0.7533	0.075*
C10	0.5323 (5)	0.4249 (4)	0.6888 (3)	0.082 (2)
H10A	0.5835	0.4116	0.6555	0.098*
C11	0.6847 (3)	0.4899 (3)	0.5399 (2)	0.0311 (10)
C12	0.7761 (3)	0.4466 (3)	0.5081 (2)	0.0335 (11)
C13	0.8065 (3)	0.3639 (3)	0.5314 (2)	0.0344 (11)
C14	0.8932 (3)	0.3269 (3)	0.5012 (3)	0.0387 (12)
C15	0.9490 (4)	0.3712 (3)	0.4471 (3)	0.0581 (16)
C16	0.9164 (4)	0.4521 (3)	0.4247 (3)	0.0699 (18)
H16A	0.9529	0.4813	0.3888	0.084*
C17	0.8299 (4)	0.4907 (3)	0.4549 (3)	0.0543 (15)
C18	0.7974 (5)	0.5776 (3)	0.4262 (3)	0.078 (2)
H18A	0.7381	0.5964	0.4522	0.117*
H18B	0.7823	0.5733	0.3747	0.117*
H18C	0.8511	0.6183	0.4334	0.117*
C19	0.7417 (4)	0.3160 (3)	0.5853 (3)	0.0456 (13)
H19A	0.7717	0.2611	0.5955	0.068*
H19B	0.6753	0.3078	0.5648	0.068*
H19C	0.7365	0.3483	0.6301	0.068*
C20	0.9284 (3)	0.2395 (3)	0.5264 (3)	0.0417 (12)
C21	1.0421 (5)	0.3344 (4)	0.4112 (4)	0.097 (3)
H21A	1.0683	0.3748	0.3761	0.146*
H21B	1.0249	0.2819	0.3866	0.146*
H21C	1.0926	0.3232	0.4479	0.146*
N1	0.3624 (3)	0.6324 (2)	0.64418 (19)	0.0367 (9)
N2	0.4764 (3)	0.4950 (3)	0.6760 (2)	0.0532 (12)
O1	0.6951 (3)	0.5405 (2)	0.59115 (17)	0.0536 (9)
O2	0.5988 (2)	0.47532 (18)	0.51372 (16)	0.0412 (8)
O3	0.9433 (3)	0.2269 (2)	0.5937 (2)	0.0580 (10)
O4	0.9409 (3)	0.18136 (19)	0.48063 (19)	0.0618 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0381 (2)	0.02748 (17)	0.02972 (17)	−0.00141 (17)	0.00347 (18)	−0.00099 (13)
C1	0.059 (4)	0.047 (3)	0.043 (3)	0.003 (3)	0.007 (3)	0.009 (2)
C2	0.056 (4)	0.048 (3)	0.067 (4)	0.008 (3)	0.011 (3)	0.005 (3)
C3	0.061 (4)	0.063 (4)	0.066 (4)	0.016 (3)	0.021 (3)	0.002 (3)
C4	0.063 (4)	0.059 (3)	0.054 (3)	0.017 (3)	0.019 (3)	0.017 (3)
C5	0.040 (3)	0.041 (3)	0.035 (3)	−0.001 (3)	0.006 (2)	−0.001 (2)
C6	0.044 (3)	0.038 (3)	0.038 (3)	−0.001 (2)	0.002 (2)	0.002 (2)
C7	0.051 (3)	0.047 (3)	0.044 (3)	0.004 (3)	0.015 (3)	0.011 (2)
C8	0.060 (4)	0.047 (3)	0.054 (4)	−0.011 (3)	0.002 (3)	0.021 (3)
C9	0.068 (4)	0.048 (3)	0.070 (4)	0.019 (3)	0.009 (3)	0.022 (3)
C10	0.098 (5)	0.065 (4)	0.082 (5)	0.040 (4)	0.044 (4)	0.033 (3)
C11	0.029 (3)	0.026 (2)	0.038 (3)	0.004 (2)	0.002 (2)	0.007 (2)
C12	0.033 (3)	0.027 (2)	0.040 (3)	0.000 (2)	−0.003 (2)	0.005 (2)
C13	0.025 (3)	0.031 (2)	0.047 (3)	−0.004 (2)	−0.006 (2)	0.001 (2)
C14	0.026 (3)	0.030 (2)	0.061 (3)	0.003 (2)	0.003 (2)	0.001 (2)
C15	0.041 (3)	0.044 (3)	0.089 (4)	0.010 (3)	0.021 (3)	0.010 (3)
C16	0.055 (4)	0.048 (3)	0.106 (5)	0.014 (3)	0.040 (4)	0.034 (3)
C17	0.045 (3)	0.039 (3)	0.079 (4)	0.014 (3)	0.015 (3)	0.009 (3)
C18	0.084 (5)	0.049 (3)	0.102 (5)	0.020 (3)	0.036 (4)	0.029 (3)
C19	0.035 (3)	0.038 (3)	0.064 (3)	0.000 (2)	0.000 (3)	0.008 (2)
C20	0.034 (3)	0.027 (3)	0.064 (4)	0.002 (2)	−0.002 (3)	0.004 (3)
C21	0.069 (4)	0.071 (4)	0.152 (7)	0.034 (4)	0.063 (5)	0.032 (4)
N1	0.044 (3)	0.030 (2)	0.036 (2)	−0.002 (2)	0.0083 (19)	0.0022 (17)
N2	0.065 (3)	0.046 (2)	0.048 (3)	0.019 (2)	0.022 (2)	0.016 (2)
O1	0.049 (2)	0.061 (2)	0.051 (2)	0.0074 (19)	−0.0078 (18)	−0.0182 (18)
O2	0.0239 (18)	0.0478 (19)	0.052 (2)	0.0033 (16)	−0.0045 (16)	−0.0085 (15)
O3	0.072 (3)	0.038 (2)	0.064 (3)	0.0192 (19)	−0.023 (2)	−0.0055 (17)
O4	0.092 (3)	0.0328 (19)	0.061 (2)	0.017 (2)	0.010 (2)	−0.0006 (17)

Geometric parameters (Å, º) top

Cd1—N1	2.393 (4)	C11—O2	1.250 (5)
Cd1—N2	2.334 (4)	C11—C12	1.499 (6)
Cd1—O1	2.607 (3)	C12—C17	1.382 (6)
Cd1—O2ⁱ	2.317 (3)	C12—C13	1.414 (5)
Cd1—O2	2.372 (3)	C13—C14	1.394 (6)
Cd1—O3ⁱⁱ	2.347 (3)	C13—C19	1.500 (6)
Cd1—O4ⁱⁱ	2.396 (3)	C14—C15	1.409 (6)
C1—N1	1.333 (5)	C14—C20	1.510 (6)
C1—C2	1.371 (6)	C15—C16	1.392 (7)
C1—H1A	0.9300	C15—C21	1.505 (7)
C2—C3	1.372 (6)	C16—C17	1.402 (7)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.363 (7)	C17—C18	1.514 (6)
C3—H3A	0.9300	C18—H18A	0.9600
C4—C5	1.374 (6)	C18—H18B	0.9600
C4—H4A	0.9300	C18—H18C	0.9600
C5—N1	1.338 (5)	C19—H19A	0.9600
C5—C6	1.494 (6)	C19—H19B	0.9600
C6—N2	1.341 (5)	C19—H19C	0.9600
C6—C7	1.388 (6)	C20—O4	1.241 (5)
C7—C8	1.377 (6)	C20—O3	1.255 (5)
C7—H7A	0.9300	C20—Cd1ⁱⁱⁱ	2.718 (4)
C8—C9	1.357 (7)	C21—H21A	0.9600
C8—H8A	0.9300	C21—H21B	0.9600
C9—C10	1.359 (7)	C21—H21C	0.9600
C9—H9A	0.9300	O2—Cd1ⁱ	2.317 (3)
C10—N2	1.339 (6)	O3—Cd1ⁱⁱⁱ	2.347 (3)
C10—H10A	0.9300	O4—Cd1ⁱⁱⁱ	2.396 (3)
C11—O1	1.228 (5)

O2ⁱ—Cd1—N2	102.23 (14)	O1—C11—O2	120.5 (4)
O2ⁱ—Cd1—O3ⁱⁱ	130.54 (12)	O1—C11—C12	119.5 (4)
N2—Cd1—O3ⁱⁱ	119.81 (14)	O2—C11—C12	120.0 (4)
O2ⁱ—Cd1—O2	72.22 (12)	C17—C12—C13	121.1 (4)
N2—Cd1—O2	91.79 (12)	C17—C12—C11	117.4 (4)
O3ⁱⁱ—Cd1—O2	126.60 (12)	C13—C12—C11	121.5 (4)
O2ⁱ—Cd1—N1	91.21 (11)	C14—C13—C12	119.4 (4)
N2—Cd1—N1	69.02 (13)	C14—C13—C19	121.4 (4)
O3ⁱⁱ—Cd1—N1	81.58 (12)	C12—C13—C19	119.1 (4)
O2—Cd1—N1	151.76 (11)	C13—C14—C15	120.2 (4)
O2ⁱ—Cd1—O4ⁱⁱ	85.85 (11)	C13—C14—C20	120.3 (4)
N2—Cd1—O4ⁱⁱ	171.39 (14)	C15—C14—C20	119.5 (4)
O3ⁱⁱ—Cd1—O4ⁱⁱ	54.62 (11)	C16—C15—C14	119.0 (5)
O2—Cd1—O4ⁱⁱ	87.81 (12)	C16—C15—C21	118.0 (5)
N1—Cd1—O4ⁱⁱ	114.27 (12)	C14—C15—C21	123.0 (5)
O2ⁱ—Cd1—O1	123.00 (10)	C15—C16—C17	121.6 (5)
N2—Cd1—O1	85.17 (13)	C15—C16—H16A	119.2
O3ⁱⁱ—Cd1—O1	87.47 (12)	C17—C16—H16A	119.2
O2—Cd1—O1	50.95 (10)	C12—C17—C16	118.7 (4)
N1—Cd1—O1	141.36 (11)	C12—C17—C18	122.7 (4)
O4ⁱⁱ—Cd1—O1	87.91 (12)	C16—C17—C18	118.6 (5)
O2ⁱ—Cd1—C20ⁱⁱ	108.60 (14)	C17—C18—H18A	109.5
N2—Cd1—C20ⁱⁱ	146.97 (16)	C17—C18—H18B	109.5
O3ⁱⁱ—Cd1—C20ⁱⁱ	27.47 (12)	H18A—C18—H18B	109.5
O2—Cd1—C20ⁱⁱ	108.48 (13)	C17—C18—H18C	109.5
N1—Cd1—C20ⁱⁱ	98.32 (13)	H18A—C18—H18C	109.5
O4ⁱⁱ—Cd1—C20ⁱⁱ	27.16 (12)	H18B—C18—H18C	109.5
O1—Cd1—C20ⁱⁱ	87.82 (12)	C13—C19—H19A	109.5
N1—C1—C2	123.8 (4)	C13—C19—H19B	109.5
N1—C1—H1A	118.1	H19A—C19—H19B	109.5
C2—C1—H1A	118.1	C13—C19—H19C	109.5
C1—C2—C3	117.9 (5)	H19A—C19—H19C	109.5
C1—C2—H2A	121.1	H19B—C19—H19C	109.5
C3—C2—H2A	121.1	O4—C20—O3	121.3 (4)
C4—C3—C2	118.9 (5)	O4—C20—C14	119.6 (5)
C4—C3—H3A	120.5	O3—C20—C14	119.0 (4)
C2—C3—H3A	120.5	O4—C20—Cd1ⁱⁱⁱ	61.8 (2)
C3—C4—C5	120.3 (5)	O3—C20—Cd1ⁱⁱⁱ	59.6 (2)
C3—C4—H4A	119.9	C14—C20—Cd1ⁱⁱⁱ	178.4 (4)
C5—C4—H4A	119.9	C15—C21—H21A	109.5
N1—C5—C4	121.2 (4)	C15—C21—H21B	109.5
N1—C5—C6	116.1 (4)	H21A—C21—H21B	109.5
C4—C5—C6	122.7 (4)	C15—C21—H21C	109.5
N2—C6—C7	120.8 (4)	H21A—C21—H21C	109.5
N2—C6—C5	116.4 (4)	H21B—C21—H21C	109.5
C7—C6—C5	122.8 (4)	C1—N1—C5	117.8 (4)
C8—C7—C6	119.4 (5)	C1—N1—Cd1	123.9 (3)
C8—C7—H7A	120.3	C5—N1—Cd1	118.3 (3)
C6—C7—H7A	120.3	C10—N2—C6	117.9 (4)
C9—C8—C7	119.6 (5)	C10—N2—Cd1	122.0 (3)
C9—C8—H8A	120.2	C6—N2—Cd1	120.0 (3)
C7—C8—H8A	120.2	C11—O1—Cd1	88.5 (3)
C10—C9—C8	118.1 (5)	C11—O2—Cd1ⁱ	151.4 (3)
C10—C9—H9A	120.9	C11—O2—Cd1	99.2 (3)
C8—C9—H9A	120.9	Cd1ⁱ—O2—Cd1	107.78 (12)
N2—C10—C9	124.1 (5)	C20—O3—Cd1ⁱⁱⁱ	93.0 (3)
N2—C10—H10A	118.0	C20—O4—Cd1ⁱⁱⁱ	91.1 (3)
C9—C10—H10A	118.0

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1^iv	0.93	2.32	3.240 (6)	169
C8—H8A···O3^iv	0.93	2.39	3.251 (6)	155

Symmetry code: (iv) x−1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₁H₁₀O₄)(C₁₀H₈N₂)]
M_r	474.77
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.1985 (8), 15.5714 (9), 18.1926 (11)
V (Å³)	3738.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.841, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	14349, 4299, 2454
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.098, 0.99
No. of reflections	4299
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.63

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cd1—N1	2.393 (4)	Cd1—O2	2.372 (3)
Cd1—N2	2.334 (4)	Cd1—O3ⁱⁱ	2.347 (3)
Cd1—O1	2.607 (3)	Cd1—O4ⁱⁱ	2.396 (3)
Cd1—O2ⁱ	2.317 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱⁱⁱ	0.93	2.32	3.240 (6)	169
C8—H8A···O3ⁱⁱⁱ	0.93	2.39	3.251 (6)	155

Symmetry code: (iii) x−1/2, y, −z+3/2.

Acknowledgements

This work was supported financially by Anyang Institute of Technology, China.

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