Poly[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)(μ3-5-hy­droxy­isophthalato-κ4O1:O3,O3′:O3′)cadmium]

Hu, X.-Y.; Zhai, W.-H.; Ma, N.; Yang, G.-R.

doi:10.1107/S1600536811035975

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1352

https://doi.org/10.1107/S1600536811035975

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Poly[(5,5′-dimethyl-2,2′-bipyridine-κ²N,N′)(μ₃-5-hydroxyisophthalato-κ⁴O¹:O³,O^3′:O^3′)cadmium]

Xi-Ying Hu,^a ^* Wen-Hang Zhai,^a Ning Ma ^a and Guang-Rui Yang ^a

^aNorth China University of Water Conservancy and Electric Power, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: hbsyhxy@163.com

(Received 27 August 2011; accepted 3 September 2011; online 14 September 2011)

In the title compound, [Cd(C₈H₄O₅)(C₁₂H₁₂N₂)], the Cd^II cation is coordinated by three 5-hydroxyisophthalate anions and one 5,5′-bimethyl-2,2′-bipyridine ligand in a distorted CdO₄N₂ octahedral geometry. The 5-hydroxyisophthalate anions bridge the Cd cations, forming a two-dimensional polymeric complex parallel to (100). In the complex, the hydroxy group is linked to the uncoordinated carboxy-O atom via an O—H⋯O hydrogen bond. Weak C—H⋯O hydrogen bonds are also present in the crystal structure. One of the methyl groups is disordered over two positions in a 0.536 (11):0.464 (11) ratio.

Related literature

For background to network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ); Ockwig et al. (2005 ); Zang et al. (2011 ).

Experimental

Crystal data

[Cd(C₈H₄O₅)(C₁₂H₁₂N₂)]
M_r = 476.75
Monoclinic, P 2₁ /c
a = 10.7650 (2) Å
b = 13.0111 (3) Å
c = 16.5272 (4) Å
β = 125.235 (2)°
V = 1890.77 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.788, T_max = 0.806
7327 measured reflections
3315 independent reflections
2963 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.03
3315 reflections
261 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.1884 (19)
Cd1—O3ⁱ	2.4015 (19)
Cd1—O4ⁱ	2.3209 (18)
Cd1—O4ⁱⁱ	2.3922 (19)
Cd1—N1	2.329 (2)
Cd1—N2	2.340 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱⁱⁱ	0.82	1.86	2.680 (3)	174
C6—H6⋯O1^iv	0.93	2.31	3.229 (3)	169
C17—H17⋯O3^v	0.93	2.53	3.355 (5)	147
Symmetry codes: (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035975/xu5315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035975/xu5315Isup2.hkl

checkCIF report

Comment top

In recent years, supramolecular coordination assemblies have received much attention due to their variety of architectures and the potential applications as functional materials (Maspoch et al., 2007; Ockwig et al., 2005). A great number of isophthalic acid and its derivatives have been successfully employed in the generation of many novel structures (Zang et al., 2011). To further explore various factors that influence the properties and construction of coordination compounds, we undertake synthetic and structural studies on one novel Cd(II) complex based on 5-hydroxyisophthalic acid (H₂hip) and 5,5'-bimethyl-2,2'-bipyridine(bmbpy): Cd(hip)(bmbpy) (1).

As shown in Fig. 1, the asymmetric unit consists of one Cd^II atom, one hip^2- anion and one dmbpy ligand. The Cd^II atom is six-coordinated by four O atoms from three 5-hydroxyisophthalate ligands and two N atoms from a chelating 5,5'-bimethyl-2,2'-bipyridine ligand. Each hip^2- ligand acts as a µ₃-bridge linking three Cd^II atoms with one carboxylate groups in monodentate fashion and the other one in chelating/bridging mode. As depicted in Fig. 2, pair of metal atoms are linked together through two carboxylate oxygen atoms to form a tetratomic ring Cd₂O₂. Adjacent rings are further connected by hip^2- ligands to result in a layer structure in bc plane with the N-donor ligands hanging from it. A better understanding of this structure can be achieved via topological considerations. If the hip^2- ligand are considered as connecters, and the Cd₂O₂ Units are considered as four-connected nodes (connecting to four other such units via hip^2- ligands), the layer structure of 1 can be described as a (4,4)-net.

Related literature top

For background to network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011).

Experimental top

Compound 1 was synthesized hydrothermally in a Teflon-lined stainless steel container by heating a mixture of 5-hydroxyisophthalic acid (H₂hip) (0.0091 g, 0.05 mmol), 5,5'-bimethyl-2,2'-bipyridine(bmbpy) (0.0092 g, 0.05 mmol), Cd(NO₃)₂.4H₂O (0.0154 g, 0.05 mmol) and NaOH (0.0040 g, 0.1 mmol) in 7 ml of distilled water at 120°C for 3 days, and then cooled to room temperature. Colorless block crystals of 1 were obtained in 69% yield based on cadmium.

Structure description top

For background to network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Metal coordination and atom labeling in title compound (thermal ellipsoids at 50% probability level). Irrespective hydrogen atoms are omitted for clarity.
	Fig. 2. A view of the layer in compound 1. Dotted lines represent the topological view of the layer structure. The bmbpy ligands are omitted for clarity.

Poly[(5,5'-dimethyl-2,2'-bipyridine-κ²N,N')(µ₃-5- hydroxyisophthalato- κ⁴O¹:O³,O^3':O^3')cadmium] top

Crystal data top

[Cd(C₈H₄O₅)(C₁₂H₁₂N₂)]	F(000) = 952
M_r = 476.75	D_x = 1.675 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4955 reflections
a = 10.7650 (2) Å	θ = 3.0–29.2°
b = 13.0111 (3) Å	µ = 1.19 mm⁻¹
c = 16.5272 (4) Å	T = 296 K
β = 125.235 (2)°	Block, colourless
V = 1890.77 (7) Å³	0.21 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area detector diffractometer	3315 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.788, T_max = 0.806	k = −13→15
7327 measured reflections	l = −18→19

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0329P)² + 0.440P] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max = 0.002
261 parameters	Δρ_max = 0.44 e Å⁻³
19 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Cd(C₈H₄O₅)(C₁₂H₁₂N₂)]	V = 1890.77 (7) Å³
M_r = 476.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7650 (2) Å	µ = 1.19 mm⁻¹
b = 13.0111 (3) Å	T = 296 K
c = 16.5272 (4) Å	0.21 × 0.20 × 0.19 mm
β = 125.235 (2)°

Data collection top

Bruker APEXII CCD area detector diffractometer	3315 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2963 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.806	R_int = 0.022
7327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	19 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
3315 reflections	Δρ_min = −0.49 e Å⁻³
261 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	Occ. (<1)
Cd1	0.33624 (2)	0.908899 (14)	0.465227 (14)	0.02455 (9)
O1	0.4236 (3)	0.79166 (15)	0.58085 (15)	0.0445 (5)
O2	0.4437 (3)	0.68188 (19)	0.48809 (18)	0.0605 (7)
O3	0.3021 (2)	0.63401 (16)	0.81224 (15)	0.0398 (5)
O4	0.4714 (2)	0.51992 (16)	0.90921 (14)	0.0380 (5)
O5	0.5449 (3)	0.34087 (16)	0.66869 (17)	0.0482 (6)
H5	0.5532	0.3368	0.6225	0.072*
N1	0.0946 (3)	0.8445 (2)	0.4020 (2)	0.0447 (7)
N2	0.1680 (3)	1.0450 (2)	0.42515 (19)	0.0387 (6)
C1	0.4423 (3)	0.7026 (2)	0.5600 (2)	0.0311 (6)
C2	0.4028 (3)	0.5714 (2)	0.83066 (19)	0.0234 (6)
C3	0.4561 (3)	0.6172 (2)	0.62673 (19)	0.0268 (6)
C4	0.4971 (3)	0.5188 (2)	0.6169 (2)	0.0331 (7)
H4	0.5166	0.5067	0.5697	0.040*
C5	0.5091 (3)	0.4393 (2)	0.6761 (2)	0.0310 (6)
C6	0.4842 (3)	0.4582 (2)	0.74822 (19)	0.0269 (6)
H6	0.4975	0.4059	0.7909	0.032*
C7	0.4394 (3)	0.5551 (2)	0.75669 (18)	0.0224 (5)
C8	0.4245 (3)	0.6349 (2)	0.69598 (19)	0.0251 (6)
H8	0.3936	0.6997	0.7016	0.030*
C9	0.0650 (4)	0.7438 (3)	0.3945 (3)	0.0666 (12)
H9	0.1411	0.6988	0.4064	0.080*
C10	−0.0689 (4)	0.7022 (3)	0.3704 (4)	0.0818 (15)
C11	−0.0818 (12)	0.5869 (7)	0.3935 (10)	0.0662 (17)	0.464 (11)
H11A	−0.0717	0.5426	0.3511	0.099*	0.464 (11)
H11B	−0.1789	0.5758	0.3820	0.099*	0.464 (11)
H11C	−0.0024	0.5720	0.4614	0.099*	0.464 (11)
C11'	−0.0983 (10)	0.5886 (6)	0.3397 (9)	0.0662 (17)	0.536 (11)
H11D	−0.1467	0.5832	0.2697	0.099*	0.536 (11)
H11E	−0.1632	0.5594	0.3560	0.099*	0.536 (11)
H11F	−0.0034	0.5521	0.3744	0.099*	0.536 (11)
C12	−0.1789 (4)	0.7708 (3)	0.3531 (3)	0.0741 (13)
H12	−0.2718	0.7465	0.3372	0.089*
C13	−0.1532 (4)	0.8742 (3)	0.3590 (3)	0.0603 (11)
H13	−0.2283	0.9202	0.3470	0.072*
C14	−0.0139 (3)	0.9107 (2)	0.3832 (2)	0.0395 (8)
C15	0.0231 (3)	1.0213 (3)	0.3885 (2)	0.0399 (7)
C16	−0.0843 (4)	1.0982 (3)	0.3547 (3)	0.0659 (12)
H16	−0.1840	1.0817	0.3308	0.079*
C17	−0.0446 (4)	1.1988 (3)	0.3560 (3)	0.0726 (13)
H17	−0.1181	1.2500	0.3316	0.087*
C18	0.1026 (4)	1.2240 (3)	0.3932 (3)	0.0629 (11)
C19	0.1526 (5)	1.3337 (3)	0.3959 (4)	0.0828 (13)
H19A	0.0711	1.3708	0.3399	0.124*
H19B	0.2396	1.3334	0.3935	0.124*
H19C	0.1787	1.3663	0.4559	0.124*
C20	0.2049 (4)	1.1434 (3)	0.4275 (3)	0.0523 (9)
H20	0.3059	1.1587	0.4539	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03011 (13)	0.02303 (13)	0.02889 (13)	0.00030 (8)	0.02186 (10)	0.00374 (8)
O1	0.0808 (15)	0.0212 (11)	0.0346 (12)	0.0003 (10)	0.0351 (11)	0.0044 (9)
O2	0.115 (2)	0.0487 (15)	0.0543 (15)	0.0187 (14)	0.0701 (16)	0.0163 (12)
O3	0.0564 (13)	0.0369 (12)	0.0468 (13)	0.0183 (10)	0.0417 (11)	0.0115 (10)
O4	0.0502 (12)	0.0473 (13)	0.0265 (10)	0.0206 (10)	0.0279 (9)	0.0125 (10)
O5	0.0970 (17)	0.0237 (11)	0.0525 (14)	0.0176 (11)	0.0596 (14)	0.0079 (10)
N1	0.0337 (13)	0.0348 (15)	0.0647 (18)	−0.0030 (12)	0.0279 (13)	−0.0001 (14)
N2	0.0351 (13)	0.0308 (14)	0.0513 (16)	0.0056 (11)	0.0256 (12)	0.0057 (13)
C1	0.0402 (15)	0.0273 (16)	0.0303 (15)	0.0009 (12)	0.0228 (13)	0.0032 (13)
C2	0.0282 (13)	0.0213 (14)	0.0248 (14)	−0.0052 (11)	0.0177 (12)	−0.0029 (12)
C3	0.0359 (14)	0.0242 (14)	0.0236 (14)	−0.0002 (12)	0.0190 (12)	0.0036 (12)
C4	0.0559 (18)	0.0275 (15)	0.0313 (15)	0.0052 (13)	0.0340 (14)	0.0012 (13)
C5	0.0469 (17)	0.0227 (14)	0.0334 (16)	0.0050 (12)	0.0290 (14)	0.0008 (13)
C6	0.0375 (15)	0.0238 (15)	0.0251 (14)	0.0015 (12)	0.0214 (12)	0.0055 (12)
C7	0.0256 (13)	0.0228 (13)	0.0214 (13)	−0.0001 (11)	0.0150 (11)	0.0001 (11)
C8	0.0328 (14)	0.0183 (13)	0.0268 (14)	0.0019 (11)	0.0187 (12)	−0.0003 (12)
C9	0.0417 (19)	0.041 (2)	0.107 (3)	−0.0020 (16)	0.037 (2)	−0.005 (2)
C10	0.042 (2)	0.044 (2)	0.130 (4)	−0.0106 (18)	0.033 (2)	0.003 (3)
C11	0.0641 (19)	0.061 (2)	0.069 (2)	−0.0056 (12)	0.0358 (15)	0.0007 (15)
C11'	0.0641 (19)	0.061 (2)	0.069 (2)	−0.0056 (12)	0.0358 (15)	0.0007 (15)
C12	0.0377 (19)	0.059 (3)	0.113 (4)	−0.0105 (18)	0.037 (2)	0.007 (3)
C13	0.0345 (18)	0.060 (2)	0.083 (3)	0.0047 (17)	0.0316 (19)	0.006 (2)
C14	0.0296 (15)	0.0428 (19)	0.0448 (19)	0.0010 (13)	0.0208 (14)	0.0018 (15)
C15	0.0307 (15)	0.0424 (19)	0.0438 (18)	0.0052 (14)	0.0199 (14)	0.0050 (15)
C16	0.0374 (19)	0.050 (2)	0.093 (3)	0.0121 (16)	0.028 (2)	0.009 (2)
C17	0.050 (2)	0.052 (3)	0.097 (3)	0.0230 (19)	0.032 (2)	0.013 (2)
C18	0.053 (2)	0.0414 (18)	0.081 (3)	0.0153 (16)	0.031 (2)	0.011 (2)
C19	0.0794 (19)	0.0575 (17)	0.096 (2)	0.0031 (14)	0.0418 (15)	0.0074 (16)
C20	0.0410 (18)	0.0338 (19)	0.076 (3)	0.0032 (15)	0.0304 (18)	0.0059 (19)

Geometric parameters (Å, º) top

Cd1—O1	2.1884 (19)	C7—C8	1.387 (4)
Cd1—O3ⁱ	2.4015 (19)	C8—H8	0.9300
Cd1—O4ⁱ	2.3209 (18)	C9—C10	1.367 (5)
Cd1—O4ⁱⁱ	2.3922 (19)	C9—H9	0.9300
Cd1—N1	2.329 (2)	C10—C12	1.374 (6)
Cd1—N2	2.340 (2)	C10—C11'	1.536 (9)
O1—C1	1.257 (3)	C10—C11	1.574 (10)
O2—C1	1.229 (3)	C11—H11A	0.9600
O3—C2	1.246 (3)	C11—H11B	0.9600
O3—Cd1ⁱⁱⁱ	2.4015 (19)	C11—H11C	0.9600
O4—C2	1.254 (3)	C11'—H11D	0.9600
O4—Cd1ⁱⁱⁱ	2.3209 (18)	C11'—H11E	0.9600
O4—Cd1^iv	2.3922 (18)	C11'—H11F	0.9600
O5—C5	1.363 (3)	C12—C13	1.367 (6)
O5—H5	0.8200	C12—H12	0.9300
N1—C9	1.337 (4)	C13—C14	1.394 (5)
N1—C14	1.335 (4)	C13—H13	0.9300
N2—C20	1.333 (4)	C14—C15	1.482 (4)
N2—C15	1.343 (4)	C15—C16	1.380 (5)
C1—C3	1.511 (4)	C16—C17	1.373 (5)
C2—C7	1.500 (3)	C16—H16	0.9300
C2—Cd1ⁱⁱⁱ	2.714 (3)	C17—C18	1.368 (5)
C3—C8	1.389 (4)	C17—H17	0.9300
C3—C4	1.394 (4)	C18—C20	1.384 (5)
C4—C5	1.379 (4)	C18—C19	1.517 (6)
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.386 (4)	C19—H19B	0.9600
C6—C7	1.386 (4)	C19—H19C	0.9600
C6—H6	0.9300	C20—H20	0.9300

O1—Cd1—O4ⁱ	125.02 (8)	C6—C7—C8	120.6 (2)
O1—Cd1—N1	86.97 (9)	C6—C7—C2	118.8 (2)
O4ⁱ—Cd1—N1	139.44 (9)	C8—C7—C2	120.6 (2)
O1—Cd1—N2	130.36 (9)	C7—C8—C3	119.4 (2)
O4ⁱ—Cd1—N2	98.40 (8)	C7—C8—H8	120.3
N1—Cd1—N2	70.33 (9)	C3—C8—H8	120.3
O1—Cd1—O4ⁱⁱ	86.70 (7)	N1—C9—C10	124.7 (3)
O4ⁱ—Cd1—O4ⁱⁱ	71.16 (7)	N1—C9—H9	117.7
N1—Cd1—O4ⁱⁱ	142.19 (8)	C10—C9—H9	117.7
N2—Cd1—O4ⁱⁱ	85.97 (8)	C9—C10—C12	116.2 (4)
O1—Cd1—O3ⁱ	119.01 (8)	C9—C10—C11'	117.3 (5)
O4ⁱ—Cd1—O3ⁱ	54.77 (6)	C12—C10—C11'	124.6 (4)
N1—Cd1—O3ⁱ	89.50 (8)	C9—C10—C11	122.1 (5)
N2—Cd1—O3ⁱ	104.75 (8)	C12—C10—C11	118.9 (5)
O4ⁱⁱ—Cd1—O3ⁱ	125.72 (6)	C10—C11—H11A	109.5
O1—Cd1—C2ⁱ	126.71 (8)	C10—C11—H11B	109.5
O4ⁱ—Cd1—C2ⁱ	27.45 (7)	C10—C11—H11C	109.5
N1—Cd1—C2ⁱ	114.91 (9)	C10—C11'—H11D	109.5
N2—Cd1—C2ⁱ	102.94 (8)	C10—C11'—H11E	109.5
O4ⁱⁱ—Cd1—C2ⁱ	98.53 (7)	H11D—C11'—H11E	109.5
O3ⁱ—Cd1—C2ⁱ	27.32 (7)	C10—C11'—H11F	109.5
C1—O1—Cd1	117.35 (18)	H11D—C11'—H11F	109.5
C2—O3—Cd1ⁱⁱⁱ	90.45 (16)	H11E—C11'—H11F	109.5
C2—O4—Cd1ⁱⁱⁱ	93.99 (15)	C13—C12—C10	120.6 (3)
C2—O4—Cd1^iv	156.69 (17)	C13—C12—H12	119.7
Cd1ⁱⁱⁱ—O4—Cd1^iv	108.84 (7)	C10—C12—H12	119.7
C5—O5—H5	109.5	C12—C13—C14	119.7 (3)
C9—N1—C14	118.8 (3)	C12—C13—H13	120.1
C9—N1—Cd1	122.6 (2)	C14—C13—H13	120.1
C14—N1—Cd1	118.2 (2)	N1—C14—C13	119.9 (3)
C20—N2—C15	118.9 (3)	N1—C14—C15	116.3 (3)
C20—N2—Cd1	123.3 (2)	C13—C14—C15	123.7 (3)
C15—N2—Cd1	117.5 (2)	N2—C15—C16	120.0 (3)
O2—C1—O1	124.1 (3)	N2—C15—C14	116.9 (3)
O2—C1—C3	119.6 (3)	C16—C15—C14	123.1 (3)
O1—C1—C3	116.3 (2)	C17—C16—C15	120.3 (3)
O3—C2—O4	120.8 (2)	C17—C16—H16	119.9
O3—C2—C7	119.6 (2)	C15—C16—H16	119.9
O4—C2—C7	119.6 (2)	C18—C17—C16	120.3 (3)
O3—C2—Cd1ⁱⁱⁱ	62.23 (14)	C18—C17—H17	119.8
O4—C2—Cd1ⁱⁱⁱ	58.55 (13)	C16—C17—H17	119.8
C7—C2—Cd1ⁱⁱⁱ	177.30 (18)	C17—C18—C20	116.4 (4)
C8—C3—C4	119.5 (2)	C17—C18—C19	122.6 (3)
C8—C3—C1	120.8 (2)	C20—C18—C19	121.1 (3)
C4—C3—C1	119.7 (2)	C18—C19—H19A	109.5
C5—C4—C3	120.8 (2)	C18—C19—H19B	109.5
C5—C4—H4	119.6	H19A—C19—H19B	109.5
C3—C4—H4	119.6	C18—C19—H19C	109.5
O5—C5—C4	123.8 (2)	H19A—C19—H19C	109.5
O5—C5—C6	116.7 (2)	H19B—C19—H19C	109.5
C4—C5—C6	119.5 (3)	N2—C20—C18	124.2 (3)
C5—C6—C7	120.0 (2)	N2—C20—H20	117.9
C5—C6—H6	120.0	C18—C20—H20	117.9
C7—C6—H6	120.0

O4ⁱ—Cd1—O1—C1	−70.7 (2)	C3—C4—C5—C6	−1.8 (4)
N1—Cd1—O1—C1	82.4 (2)	O5—C5—C6—C7	−176.5 (3)
N2—Cd1—O1—C1	143.3 (2)	C4—C5—C6—C7	3.6 (4)
O4ⁱⁱ—Cd1—O1—C1	−134.8 (2)	C5—C6—C7—C8	−2.4 (4)
O3ⁱ—Cd1—O1—C1	−5.3 (2)	C5—C6—C7—C2	175.8 (2)
C2ⁱ—Cd1—O1—C1	−36.7 (2)	O3—C2—C7—C6	−146.8 (3)
O1—Cd1—N1—C9	−43.2 (3)	O4—C2—C7—C6	31.5 (4)
O4ⁱ—Cd1—N1—C9	102.1 (3)	O3—C2—C7—C8	31.5 (4)
N2—Cd1—N1—C9	−178.2 (3)	O4—C2—C7—C8	−150.3 (3)
O4ⁱⁱ—Cd1—N1—C9	−123.8 (3)	C6—C7—C8—C3	−0.5 (4)
O3ⁱ—Cd1—N1—C9	75.9 (3)	C2—C7—C8—C3	−178.7 (2)
C2ⁱ—Cd1—N1—C9	86.3 (3)	C4—C3—C8—C7	2.2 (4)
O1—Cd1—N1—C14	129.2 (3)	C1—C3—C8—C7	−179.5 (2)
O4ⁱ—Cd1—N1—C14	−85.5 (3)	C14—N1—C9—C10	−1.4 (7)
N2—Cd1—N1—C14	−5.9 (2)	Cd1—N1—C9—C10	170.9 (4)
O4ⁱⁱ—Cd1—N1—C14	48.5 (3)	N1—C9—C10—C12	0.0 (8)
O3ⁱ—Cd1—N1—C14	−111.7 (2)	N1—C9—C10—C11'	165.1 (6)
C2ⁱ—Cd1—N1—C14	−101.4 (2)	N1—C9—C10—C11	−161.0 (7)
O1—Cd1—N2—C20	119.8 (3)	C9—C10—C12—C13	0.7 (8)
O4ⁱ—Cd1—N2—C20	−32.6 (3)	C11'—C10—C12—C13	−163.1 (7)
N1—Cd1—N2—C20	−172.3 (3)	C11—C10—C12—C13	162.4 (7)
O4ⁱⁱ—Cd1—N2—C20	37.6 (3)	C10—C12—C13—C14	−0.2 (7)
O3ⁱ—Cd1—N2—C20	−88.3 (3)	C9—N1—C14—C13	1.9 (5)
C2ⁱ—Cd1—N2—C20	−60.2 (3)	Cd1—N1—C14—C13	−170.8 (3)
O1—Cd1—N2—C15	−67.1 (3)	C9—N1—C14—C15	−177.4 (3)
O4ⁱ—Cd1—N2—C15	140.4 (2)	Cd1—N1—C14—C15	9.9 (4)
N1—Cd1—N2—C15	0.7 (2)	C12—C13—C14—N1	−1.1 (6)
O4ⁱⁱ—Cd1—N2—C15	−149.3 (2)	C12—C13—C14—C15	178.1 (4)
O3ⁱ—Cd1—N2—C15	84.8 (2)	C20—N2—C15—C16	−0.4 (5)
C2ⁱ—Cd1—N2—C15	112.8 (2)	Cd1—N2—C15—C16	−173.7 (3)
Cd1—O1—C1—O2	14.9 (4)	C20—N2—C15—C14	177.3 (3)
Cd1—O1—C1—C3	−162.18 (18)	Cd1—N2—C15—C14	3.9 (4)
Cd1ⁱⁱⁱ—O3—C2—O4	−0.4 (3)	N1—C14—C15—N2	−9.2 (5)
Cd1ⁱⁱⁱ—O3—C2—C7	177.8 (2)	C13—C14—C15—N2	171.6 (3)
Cd1ⁱⁱⁱ—O4—C2—O3	0.5 (3)	N1—C14—C15—C16	168.4 (4)
Cd1^iv—O4—C2—O3	−168.2 (3)	C13—C14—C15—C16	−10.9 (6)
Cd1ⁱⁱⁱ—O4—C2—C7	−177.7 (2)	N2—C15—C16—C17	1.6 (7)
Cd1^iv—O4—C2—C7	13.6 (6)	C14—C15—C16—C17	−175.9 (4)
Cd1^iv—O4—C2—Cd1ⁱⁱⁱ	−168.7 (5)	C15—C16—C17—C18	−1.6 (8)
O2—C1—C3—C8	−167.0 (3)	C16—C17—C18—C20	0.5 (7)
O1—C1—C3—C8	10.3 (4)	C16—C17—C18—C19	179.5 (5)
O2—C1—C3—C4	11.3 (4)	C15—N2—C20—C18	−0.8 (6)
O1—C1—C3—C4	−171.5 (3)	Cd1—N2—C20—C18	172.2 (3)
C8—C3—C4—C5	−1.1 (4)	C17—C18—C20—N2	0.7 (6)
C1—C3—C4—C5	−179.3 (3)	C19—C18—C20—N2	−178.3 (4)
C3—C4—C5—O5	178.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2^v	0.82	1.86	2.680 (3)	174
C6—H6···O1^iv	0.93	2.31	3.229 (3)	169
C17—H17···O3^vi	0.93	2.53	3.355 (5)	147

Symmetry codes: (iv) −x+1, y−1/2, −z+3/2; (v) −x+1, −y+1, −z+1; (vi) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₄O₅)(C₁₂H₁₂N₂)]
M_r	476.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.7650 (2), 13.0111 (3), 16.5272 (4)
β (°)	125.235 (2)
V (Å³)	1890.77 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.21 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.788, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	7327, 3315, 2963
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.03
No. of reflections	3315
No. of parameters	261
No. of restraints	19
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.49

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—O1	2.1884 (19)	Cd1—O4ⁱⁱ	2.3922 (19)
Cd1—O3ⁱ	2.4015 (19)	Cd1—N1	2.329 (2)
Cd1—O4ⁱ	2.3209 (18)	Cd1—N2	2.340 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱⁱⁱ	0.82	1.86	2.680 (3)	174
C6—H6···O1^iv	0.93	2.31	3.229 (3)	169
C17—H17···O3^v	0.93	2.53	3.355 (5)	147

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

Acknowledgements

This work was supported financially by the North China University of Water Conservancy and Electric Power, China.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Zang, S.-Q., Fan, Y.-J., Li, J.-B., Hou, H.-W. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 3395–3405. Web of Science CSD CrossRef CAS Google Scholar

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