Poly[(μ2-1,3-di-4-pyridyl­propane)(μ3-1,3-phenyl­enediacetato)­cadmium]

Liu, D.; Li, N.-Y.

doi:10.1107/S1600536811041432

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1540

doi:10.1107/S1600536811041432

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Poly[(μ₂-1,3-di-4-pyridylpropane)(μ₃-1,3-phenylenediacetato)cadmium]

Dong Liu ^a ^* and Ni-Ya Li ^a

^aCollege of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, Anhui, People's Republic of China
^*Correspondence e-mail: dongliu@chnu.edu.cn

(Received 12 September 2011; accepted 8 October 2011; online 12 October 2011)

In the title compound, [Cd(C₁₀H₈O₄)(C₁₃H₁₄N₂)]_n, two symmetry-related Cd atoms are bridged by two carboxylate O atoms into a binuclear Cd₂ subunit around an inversion center. The Cd atom has a distorted pentagonal–bipyramidal environment, defined by five O atoms from three different 1,3-phenylendiacetate (1,3-pda) ligands and two N atoms from two 1,3-di-4-pyridylpropane (bpp) ligands. Each Cd₂ subunit is linked to four different Cd₂ subunits by four 1,3-pda ligands and four bpp ligands, forming a two-dimensional network with rhombic grids (12.50 × 12.50 Å²) extending along the ab plane.

Related literature

For a coordination polymer with a similar structure, see: Nagaraja et al. (2010 ). For another compound synthesized from the same components as the title compound, see: Zhang et al. (2009 ). For Cd—O and Cd—N bond lengths in related structures, see: Clegg et al. (1995 ); Tao et al. (2000 ).

Experimental

Crystal data

[Cd(C₁₀H₈O₄)(C₁₃H₁₄N₂)]
M_r = 502.84
Orthorhombic, P b c n
a = 22.573 (5) Å
b = 10.729 (2) Å
c = 17.024 (3) Å
V = 4123.0 (14) Å³
Z = 8
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 223 K
0.25 × 0.25 × 0.20 mm

Data collection

Rigaku MercuryCCD area-detector diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.772, T_max = 0.811
13963 measured reflections
4693 independent reflections
3718 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.108
S = 1.19
4693 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: CrystalClear (Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041432/aa2028sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041432/aa2028Isup2.hkl

checkCIF report

Comment top

In view of progress of crystal engineering, the appropriate choice of metal ions and organic building blocks is the most effective and facile method to assemble metal-organic compounds with various structures (Clegg et al., 1995; Nagaraja et al., 2010; Tao et al., 2000). In the past decade, rigid dicaboxylate and dipyridyl ligands have been widely employed as organic linkers to afford coordination polymers (Tao et al., 2000). Recently, flexible dicaboxylate and dipyridyl ligands have also been used to bond with metal ions (Nagaraja et al., 2010). And the complexes assembled by flexible ligands usually exhibit different structures with those of the complexes assembled by rigid ligands. In this work, we employed Cd(NO₃)₂ and two flexible ligands (1,3-phenylendiacetic acid, 1,3-pda, and 1,3-di-4-pyridylpropane, bpp) as our system and obtained the title compound.

As shown in Fig. 1, the symmetry-unique Cd atom is located in a pentagonal-bipyramidal environment, coordinated by five O atoms from three different 1,3-pda ligands at the equatorial sites and two N atoms from two bpp ligands at the axial sites. The Cd1–O [2.302 (3)–2.662 (3) Å] and Cd–N [2.319 (4)–2.320 (4) Å] distances are consistent with those previously observed in the related reported complexes (Clegg et al., 1995; Tao et al., 2000). Two symmetry related Cd atoms (Cd1 and Cd1ⁱ; symmetry code: (i) -x + 1, -y, -z) are bridged by two carboxylate O atoms into a binuclear Cd₂ subunit around an inversion center. Each Cd₂ subunit is linked to four different Cd₂ subunits by four 1,3-pda ligands and four bpp ligands forming a two-dimensional (4,4) network with rhombic grids (12.50 × 12.50 Å²) extending along the ab plane (Fig. 2).

It should be noted that the complex [Cd₂(1,3-pda)₂(bpp)₃]_n (Zhang et al., 2009) was synthesized from the same components as the title compound. However, its structure is completely different.

Related literature top

For a coordination polymer with the similar structure, see: Nagaraja et al. (2010). For another compound synthesized from the same components as the title compound, see: Zhang et al. (2009). For Cd—O and Cd—N bond lengths in related structures, see: Clegg et al. (1995); Tao et al. (2000).

Experimental top

Cd(NO₃)₂^.4H₂O (31 mg, 0.1 mmol), 1,3-phenylenediacetic acid (19 mg, 0.1 mmol), 1,3-di-4-pyridylpropane (20 mg, 0.1 mmol), 1.5 ml of H₂O and 1.5 mL of EtOH were loaded to a 10 mL Pyrex glass tube. The tube was sealed and heated in an oven to 438 K for three days, and then cooled to ambient temperature at a rate of 5 K/h to form colourless blocks of the title compound, which were washed with ethanol and dried in air. Yield: 39 mg (78% yield based on Cd). Anal. calcd. for C₂₃H₂₂CdN₂O₄: C, 54.94; H, 4.41; N, 5.57. Found: C, 55.06; H, 4.22; N, 5.61. IR (KBr, cm^-1): 1606 (s), 1558 (s), 1540 (s), 1418 (m), 1395 (s), 1323 (m), 1217 (m), 1108 (m), 1068 (w), 1016 (m), 960 (s), 879 (m), 834 (s), 782 (s), 724 (s), 610 (m), 556 (s).

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Coordination environment of Cd(II) in the title compound with nonhydrogen atoms represented by thermal ellipsoids at 30% probability level, hydrogen atoms are drawn as spheres of arbitrary radius. [Symmetry codes: (i) x + 1/2, - y + 1/2, - z; (ii) - x + 1/2, y - 1/2, z; (iii) x - 1/2, - y + 1/2, - z.]
	Fig. 2. View of the two-dimensional network of the title compound extending along the ab plane.

Poly[(µ₂-1,3-di-4-pyridylpropane)(µ₃-1,3-phenylenediacetato)cadmium] top

Crystal data top

[Cd(C₁₀H₈O₄)(C₁₃H₁₄N₂)]	F(000) = 2032
M_r = 502.84	D_x = 1.620 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9088 reflections
a = 22.573 (5) Å	θ = 3.1–27.5°
b = 10.729 (2) Å	µ = 1.09 mm⁻¹
c = 17.024 (3) Å	T = 223 K
V = 4123.0 (14) Å³	Block, colourless
Z = 8	0.25 × 0.25 × 0.20 mm

Data collection top

Rigaku MercuryCCD area-detector diffractometer	4693 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −25→29
T_min = 0.772, T_max = 0.811	k = −13→12
13963 measured reflections	l = −12→22

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0287P)² + 4.0115P] where P = (F_o² + 2F_c²)/3
4693 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cd(C₁₀H₈O₄)(C₁₃H₁₄N₂)]	V = 4123.0 (14) Å³
M_r = 502.84	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 22.573 (5) Å	µ = 1.09 mm⁻¹
b = 10.729 (2) Å	T = 223 K
c = 17.024 (3) Å	0.25 × 0.25 × 0.20 mm

Data collection top

Rigaku MercuryCCD area-detector diffractometer	4693 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	3718 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.811	R_int = 0.044
13963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.19	Δρ_max = 0.65 e Å⁻³
4693 reflections	Δρ_min = −0.51 e Å⁻³
271 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	0.434747 (13)	0.10920 (3)	0.01591 (2)	0.03461 (12)
N1	0.49203 (16)	0.2373 (3)	0.0952 (3)	0.0393 (10)
N2	0.86922 (15)	0.4861 (3)	0.0701 (2)	0.0377 (9)
O1	0.36029 (14)	0.1141 (3)	0.1164 (2)	0.0498 (9)
O2	0.35892 (13)	0.2637 (3)	0.0268 (2)	0.0445 (9)
O3	0.01992 (13)	0.4305 (3)	0.0605 (2)	0.0441 (9)
O4	−0.02352 (13)	0.2645 (3)	0.1068 (2)	0.0525 (10)
C1	0.5298 (2)	0.1956 (4)	0.1497 (3)	0.0451 (13)
H1	0.5315	0.1093	0.1589	0.054*
C2	0.5662 (2)	0.2722 (4)	0.1930 (3)	0.0436 (12)
H2	0.5921	0.2383	0.2306	0.052*
C3	0.56421 (18)	0.4001 (4)	0.1806 (3)	0.0401 (11)
C4	0.5244 (2)	0.4433 (4)	0.1251 (4)	0.0511 (14)
H4	0.5209	0.5293	0.1158	0.061*
C5	0.4898 (2)	0.3602 (4)	0.0834 (4)	0.0509 (14)
H5	0.4637	0.3915	0.0452	0.061*
C6	0.60680 (19)	0.4873 (4)	0.2199 (3)	0.0451 (13)
H6A	0.6153	0.4588	0.2734	0.054*
H6B	0.5898	0.5712	0.2227	0.054*
C7	0.6637 (2)	0.4890 (5)	0.1712 (4)	0.0548 (15)
H7A	0.6791	0.4038	0.1682	0.066*
H7B	0.6537	0.5153	0.1177	0.066*
C8	0.71221 (19)	0.5728 (5)	0.2018 (3)	0.0478 (13)
H8A	0.7004	0.6602	0.1959	0.057*
H8B	0.7187	0.5563	0.2577	0.057*
C9	0.76871 (19)	0.5497 (4)	0.1569 (3)	0.0403 (11)
C10	0.8003 (2)	0.4414 (5)	0.1711 (3)	0.0580 (15)
H10	0.7879	0.3871	0.2112	0.070*
C11	0.8494 (2)	0.4124 (5)	0.1272 (4)	0.0554 (15)
H11	0.8697	0.3378	0.1378	0.066*
C12	0.8391 (2)	0.5898 (4)	0.0562 (3)	0.0453 (13)
H12	0.8527	0.6436	0.0164	0.054*
C13	0.7890 (2)	0.6227 (4)	0.0970 (4)	0.0520 (14)
H13	0.7686	0.6959	0.0835	0.062*
C14	0.22719 (18)	0.2311 (4)	0.1101 (3)	0.0332 (10)
C15	0.21730 (19)	0.1230 (4)	0.0675 (3)	0.0370 (11)
H15	0.2495	0.0778	0.0472	0.044*
C16	0.16009 (19)	0.0817 (4)	0.0549 (3)	0.0405 (11)
H16	0.1536	0.0089	0.0255	0.049*
C17	0.1124 (2)	0.1464 (4)	0.0851 (3)	0.0419 (12)
H17	0.0738	0.1167	0.0764	0.050*
C18	0.12081 (18)	0.2547 (4)	0.1281 (3)	0.0353 (10)
C19	0.17839 (18)	0.2964 (4)	0.1378 (3)	0.0352 (10)
H19	0.1847	0.3721	0.1643	0.042*
C20	0.28893 (18)	0.2752 (4)	0.1328 (3)	0.0438 (12)
H20A	0.2946	0.2599	0.1891	0.053*
H20B	0.2911	0.3654	0.1244	0.053*
C21	0.33970 (19)	0.2138 (4)	0.0882 (4)	0.0428 (13)
C22	0.06922 (18)	0.3252 (5)	0.1653 (3)	0.0408 (11)
H22A	0.0556	0.2802	0.2121	0.049*
H22B	0.0827	0.4080	0.1819	0.049*
C23	0.01800 (18)	0.3392 (4)	0.1080 (3)	0.0356 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02357 (18)	0.03206 (18)	0.0482 (2)	0.00165 (13)	0.00060 (14)	−0.00333 (15)
N1	0.033 (2)	0.0329 (19)	0.052 (3)	0.0006 (17)	−0.0019 (18)	−0.0084 (18)
N2	0.0289 (18)	0.039 (2)	0.045 (3)	−0.0011 (17)	0.0029 (17)	−0.0001 (18)
O1	0.0412 (18)	0.0419 (18)	0.066 (3)	0.0078 (16)	0.0093 (17)	0.0030 (17)
O2	0.0383 (18)	0.0419 (18)	0.053 (3)	0.0065 (15)	0.0058 (16)	−0.0010 (17)
O3	0.0397 (18)	0.0367 (16)	0.056 (3)	−0.0065 (14)	−0.0099 (16)	0.0124 (16)
O4	0.0305 (17)	0.0446 (18)	0.082 (3)	−0.0066 (15)	−0.0007 (17)	0.0119 (18)
C1	0.038 (3)	0.042 (3)	0.055 (4)	0.001 (2)	−0.002 (2)	−0.002 (2)
C2	0.035 (2)	0.048 (3)	0.048 (3)	0.000 (2)	−0.005 (2)	−0.005 (2)
C3	0.029 (2)	0.045 (3)	0.046 (3)	0.000 (2)	0.007 (2)	−0.013 (2)
C4	0.045 (3)	0.032 (2)	0.077 (5)	0.001 (2)	−0.007 (3)	−0.005 (3)
C5	0.039 (3)	0.045 (3)	0.069 (4)	0.002 (2)	−0.011 (3)	−0.001 (3)
C6	0.038 (3)	0.048 (3)	0.049 (4)	−0.007 (2)	0.002 (2)	−0.014 (2)
C7	0.040 (3)	0.061 (3)	0.064 (4)	−0.008 (3)	0.011 (3)	−0.021 (3)
C8	0.040 (3)	0.052 (3)	0.052 (4)	−0.006 (2)	0.008 (2)	−0.012 (2)
C9	0.036 (2)	0.042 (3)	0.042 (3)	−0.008 (2)	0.002 (2)	−0.006 (2)
C10	0.067 (3)	0.061 (3)	0.046 (4)	0.012 (3)	0.016 (3)	0.025 (3)
C11	0.051 (3)	0.057 (3)	0.059 (4)	0.013 (3)	0.009 (3)	0.017 (3)
C12	0.049 (3)	0.035 (2)	0.051 (4)	0.003 (2)	0.018 (2)	0.007 (2)
C13	0.051 (3)	0.039 (3)	0.066 (4)	0.011 (2)	0.015 (3)	0.010 (3)
C14	0.030 (2)	0.038 (2)	0.032 (3)	0.0020 (19)	0.0026 (19)	0.0021 (19)
C15	0.036 (2)	0.032 (2)	0.042 (3)	0.0040 (19)	0.003 (2)	−0.004 (2)
C16	0.040 (3)	0.036 (2)	0.045 (3)	−0.004 (2)	0.000 (2)	−0.005 (2)
C17	0.029 (2)	0.046 (3)	0.051 (4)	−0.001 (2)	−0.002 (2)	0.007 (2)
C18	0.031 (2)	0.042 (2)	0.033 (3)	0.008 (2)	0.001 (2)	0.008 (2)
C19	0.034 (2)	0.036 (2)	0.036 (3)	0.0040 (19)	−0.002 (2)	−0.0005 (19)
C20	0.030 (2)	0.046 (3)	0.056 (4)	0.002 (2)	0.005 (2)	−0.014 (2)
C21	0.028 (2)	0.040 (3)	0.061 (4)	−0.001 (2)	0.001 (2)	−0.012 (2)
C22	0.029 (2)	0.055 (3)	0.038 (3)	0.012 (2)	0.003 (2)	0.005 (2)
C23	0.026 (2)	0.038 (2)	0.043 (3)	0.007 (2)	0.002 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Cd1—O3ⁱ	2.302 (3)	C7—H7B	0.9800
Cd1—N2ⁱⁱ	2.319 (4)	C8—C9	1.507 (6)
Cd1—N1	2.320 (4)	C8—H8A	0.9800
Cd1—O3ⁱⁱⁱ	2.360 (3)	C8—H8B	0.9800
Cd1—O2	2.390 (3)	C9—C13	1.365 (7)
Cd1—O1	2.399 (3)	C9—C10	1.384 (7)
N1—C5	1.334 (6)	C10—C11	1.372 (7)
N1—C1	1.337 (6)	C10—H10	0.9400
N2—C12	1.325 (6)	C11—H11	0.9400
N2—C11	1.331 (6)	C12—C13	1.373 (7)
N2—Cd1ⁱⁱⁱ	2.319 (4)	C12—H12	0.9400
O1—C21	1.260 (6)	C13—H13	0.9400
O2—C21	1.252 (6)	C14—C15	1.385 (6)
O3—C23	1.272 (5)	C14—C19	1.388 (6)
O3—Cd1^iv	2.302 (3)	C14—C20	1.522 (6)
O3—Cd1ⁱⁱ	2.360 (3)	C15—C16	1.382 (6)
O4—C23	1.233 (5)	C15—H15	0.9400
C1—C2	1.376 (6)	C16—C17	1.379 (6)
C1—H1	0.9400	C16—H16	0.9400
C2—C3	1.389 (6)	C17—C18	1.387 (7)
C2—H2	0.9400	C17—H17	0.9400
C3—C4	1.383 (7)	C18—C19	1.384 (6)
C3—C6	1.499 (6)	C18—C22	1.526 (6)
C4—C5	1.381 (7)	C19—H19	0.9400
C4—H4	0.9400	C20—C21	1.524 (6)
C5—H5	0.9400	C20—H20A	0.9800
C6—C7	1.528 (7)	C20—H20B	0.9800
C6—H6A	0.9800	C22—C23	1.520 (6)
C6—H6B	0.9800	C22—H22A	0.9800
C7—C8	1.510 (6)	C22—H22B	0.9800
C7—H7A	0.9800

O3ⁱ—Cd1—N2ⁱⁱ	97.16 (12)	C7—C8—H8B	109.7
O3ⁱ—Cd1—N1	93.09 (13)	H8A—C8—H8B	108.2
N2ⁱⁱ—Cd1—N1	169.74 (13)	C13—C9—C10	116.0 (4)
O3ⁱ—Cd1—O3ⁱⁱⁱ	70.69 (13)	C13—C9—C8	124.7 (5)
N2ⁱⁱ—Cd1—O3ⁱⁱⁱ	95.28 (13)	C10—C9—C8	119.0 (5)
N1—Cd1—O3ⁱⁱⁱ	88.49 (13)	C11—C10—C9	120.8 (5)
O3ⁱ—Cd1—O2	150.50 (12)	C11—C10—H10	119.6
N2ⁱⁱ—Cd1—O2	84.15 (12)	C9—C10—H10	119.6
N1—Cd1—O2	86.72 (12)	N2—C11—C10	122.3 (5)
O3ⁱⁱⁱ—Cd1—O2	138.71 (11)	N2—C11—H11	118.8
O3ⁱ—Cd1—O1	95.43 (11)	C10—C11—H11	118.8
N2ⁱⁱ—Cd1—O1	90.74 (13)	N2—C12—C13	123.2 (5)
N1—Cd1—O1	87.86 (13)	N2—C12—H12	118.4
O3ⁱⁱⁱ—Cd1—O1	165.43 (12)	C13—C12—H12	118.4
O2—Cd1—O1	55.08 (12)	C9—C13—C12	120.5 (5)
C5—N1—C1	117.3 (4)	C9—C13—H13	119.7
C5—N1—Cd1	118.5 (3)	C12—C13—H13	119.7
C1—N1—Cd1	124.1 (3)	C15—C14—C19	118.2 (4)
C12—N2—C11	117.2 (4)	C15—C14—C20	122.7 (4)
C12—N2—Cd1ⁱⁱⁱ	125.8 (3)	C19—C14—C20	118.9 (4)
C11—N2—Cd1ⁱⁱⁱ	114.4 (3)	C16—C15—C14	120.0 (4)
C21—O1—Cd1	90.3 (3)	C16—C15—H15	120.0
C21—O2—Cd1	90.9 (3)	C14—C15—H15	120.0
C23—O3—Cd1^iv	150.1 (3)	C17—C16—C15	120.6 (4)
C23—O3—Cd1ⁱⁱ	100.6 (3)	C17—C16—H16	119.7
Cd1^iv—O3—Cd1ⁱⁱ	109.31 (13)	C15—C16—H16	119.7
N1—C1—C2	123.6 (4)	C16—C17—C18	120.8 (4)
N1—C1—H1	118.2	C16—C17—H17	119.6
C2—C1—H1	118.2	C18—C17—H17	119.6
C1—C2—C3	119.2 (5)	C19—C18—C17	117.5 (4)
C1—C2—H2	120.4	C19—C18—C22	120.5 (4)
C3—C2—H2	120.4	C17—C18—C22	122.0 (4)
C4—C3—C2	117.1 (4)	C18—C19—C14	122.8 (4)
C4—C3—C6	120.8 (4)	C18—C19—H19	118.6
C2—C3—C6	121.9 (5)	C14—C19—H19	118.6
C5—C4—C3	120.1 (4)	C14—C20—C21	115.3 (4)
C5—C4—H4	119.9	C14—C20—H20A	108.4
C3—C4—H4	119.9	C21—C20—H20A	108.4
N1—C5—C4	122.6 (5)	C14—C20—H20B	108.4
N1—C5—H5	118.7	C21—C20—H20B	108.4
C4—C5—H5	118.7	H20A—C20—H20B	107.5
C3—C6—C7	107.7 (4)	O2—C21—O1	123.6 (4)
C3—C6—H6A	110.2	O2—C21—C20	119.4 (4)
C7—C6—H6A	110.2	O1—C21—C20	117.0 (5)
C3—C6—H6B	110.2	O2—C21—Cd1	61.6 (2)
C7—C6—H6B	110.2	O1—C21—Cd1	62.0 (2)
H6A—C6—H6B	108.5	C20—C21—Cd1	176.5 (4)
C8—C7—C6	115.5 (4)	C23—C22—C18	111.3 (4)
C8—C7—H7A	108.4	C23—C22—H22A	109.4
C6—C7—H7A	108.4	C18—C22—H22A	109.4
C8—C7—H7B	108.4	C23—C22—H22B	109.4
C6—C7—H7B	108.4	C18—C22—H22B	109.4
H7A—C7—H7B	107.5	H22A—C22—H22B	108.0
C9—C8—C7	110.0 (4)	O4—C23—O3	121.1 (4)
C9—C8—H8A	109.7	O4—C23—C22	121.7 (4)
C7—C8—H8A	109.7	O3—C23—C22	117.3 (4)
C9—C8—H8B	109.7

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₈O₄)(C₁₃H₁₄N₂)]
M_r	502.84
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	223
a, b, c (Å)	22.573 (5), 10.729 (2), 17.024 (3)
V (Å³)	4123.0 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku MercuryCCD area-detector diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.772, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	13963, 4693, 3718
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.108, 1.19
No. of reflections	4693
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.51

Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

This work was supported by the Research Start-Up Fund for New Staff of Huaibei Normal University (600581).

References

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