Poly[bis­(1H-imidazole)(μ3-7-oxabicyclo­[2.2.1]heptane-2,3-dicarboxyl­ato)cadmium(II)]

Wang, N.; Wang, Y.-J.; Lin, Q.-Y.

doi:10.1107/S1600536809021801

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m782

doi:10.1107/S1600536809021801

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Poly[bis(1H-imidazole)(μ₃-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato)cadmium(II)]

Na Wang,^a Yan-Jun Wang ^a and Qiu-Yue Lin ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 31 May 2009; accepted 9 June 2009; online 17 June 2009)

The title compound, [Cd(C₈H₈O₅)(C₃H₄N₂)₂]_n, was synthesized by the reaction of 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, cadmium acetate and imidazole. The Cd^II atom is seven-coordinated in a distorted pentagonal-bipyramidal configuration by five O atoms from carboxylate groups of three 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate ligands and two N atoms from two imidazole ligands. The crystal structure is stabilized by N—H⋯O and C—H⋯O hydrogen-bonding and C—H⋯π interactions.

Related literature

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) is a lower toxicity anticancer drug, see: Shimi et al. (1982 ). For cobalt complexes of norcantharidin, see: Wang et al. (1988 ) and of imidazole, see: Furenlid et al. (1986 ); Zhu et al. (2003 ).

Experimental

Crystal data

[Cd(C₈H₈O₅)(C₃H₄N₂)₂]
M_r = 432.71
Monoclinic, P 2₁ /c
a = 12.5374 (16) Å
b = 9.6596 (13) Å
c = 14.1635 (17) Å
β = 112.761 (7)°
V = 1581.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 296 K
0.12 × 0.06 × 0.05 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.900, T_max = 0.932
10791 measured reflections
2777 independent reflections
2310 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.216
S = 1.05
2777 reflections
217 parameters
234 restraints
H-atom parameters constrained
Δρ_max = 2.92 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.86	2.09	2.830 (12)	144
N4—H4B⋯O1ⁱⁱ	0.86	2.44	3.012 (17)	125
N4—H4B⋯O2ⁱⁱ	0.86	2.05	2.818 (13)	149
C6—H6A⋯O4	0.98	2.56	2.92 (2)	101
C11—H11A⋯O5	0.93	2.34	3.239 (15)	164
C14—H14A⋯O2ⁱⁱⁱ	0.93	2.55	3.358 (15)	145
C12—H12A⋯Cg5^iv	0.93	2.76	3.565 (14)	145
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z+1. Cg5 is the centroid of the N3/N4/C9–C11 ring.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021801/at2804sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021801/at2804Isup2.hkl

checkCIF report

Comment top

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) derived from cantharidin is a lower toxicity anticancer drug (Shimi et al., 1982). Imidazole is reputed as biocatalyst and biological ligand. Several cobalt complexes of norcantharidin (Wang et al., 1988) and of imidazole (Furenlid et al., 1986; Zhu et al., 2003) have been reported.

In the title compound, (I), (Fig. 1), the cadmium atom is seven-coordinated in a distorted pentagonal bipyramidal configuration, defined by five oxygen atoms (O2, O3, O3A, O4B, O5B) from carboxylate groups of three 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and two nitrogen atoms (N1, N3) from two imidazoles. Each 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride acts as a four-coordinared bridging linker that connects two cadmium centers.

The crystal structure is stabilized by N—H···O, C—H···O hydrogen bonding and C—H···π interactions (Table 1).

Related literature top

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (norcantharidin) is a lower toxicity anticancer drug, see: Shimi et al. (1982). For cobalt complexes of norcantharidin, see: Wang et al. (1988) and of imidazole, see: Furenlid et al. (1986); Zhu et al. (2003). Cg5 is the centroid of the N3/N4/C9–C11 ring.

Experimental top

7-Oxabicyclo[2.2.1] heptane-2,3-dicarboxylic anhydride, cadmium acetate and imidazole were dissolved in 15 mL distilled water. The mixture was sealed in a 25 mL Teflon-lined stainless vessel and heated at 443 K for 3 d, then cooled slowly to room temperature. A crystal suitable for X-ray diffraction was obtained.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability.

Poly[bis(1H-imidazole)(µ₃-7-oxabicyclo[2.2.1]heptane-2,3- dicarboxylato)cadmium(II)] top

Crystal data top

[Cd(C₈H₈O₅)(C₃H₄N₂)₂]	F(000) = 864
M_r = 432.71	D_x = 1.817 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3164 reflections
a = 12.5374 (16) Å	θ = 1.8–25.0°
b = 9.6596 (13) Å	µ = 1.41 mm⁻¹
c = 14.1635 (17) Å	T = 296 K
β = 112.761 (7)°	Block, colourless
V = 1581.7 (3) Å³	0.12 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2777 independent reflections
Radiation source: fine-focus sealed tube	2310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.900, T_max = 0.932	k = −9→11
10791 measured reflections	l = −16→16

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.216	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1141P)² + 20.9278P] where P = (F_o² + 2F_c²)/3
2777 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 2.92 e Å⁻³
234 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

[Cd(C₈H₈O₅)(C₃H₄N₂)₂]	V = 1581.7 (3) Å³
M_r = 432.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5374 (16) Å	µ = 1.41 mm⁻¹
b = 9.6596 (13) Å	T = 296 K
c = 14.1635 (17) Å	0.12 × 0.06 × 0.05 mm
β = 112.761 (7)°

Data collection top

Bruker APEXII area-detector diffractometer	2777 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2310 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.932	R_int = 0.035
10791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	234 restraints
wR(F²) = 0.216	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1141P)² + 20.9278P] where P = (F_o² + 2F_c²)/3
2777 reflections	Δρ_max = 2.92 e Å⁻³
217 parameters	Δρ_min = −1.26 e Å⁻³

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	0.56124 (6)	0.12069 (7)	0.41461 (5)	0.0343 (3)
C1	0.3497 (10)	−0.0468 (14)	0.3258 (10)	0.054 (2)
C2	0.2845 (10)	−0.2300 (14)	0.1484 (11)	0.057 (2)
C3	0.2272 (12)	−0.0995 (16)	0.2847 (13)	0.072 (2)
H3A	0.2224	−0.1610	0.3380	0.086*
C4	0.1928 (11)	−0.1894 (18)	0.1877 (12)	0.073 (2)
H4A	0.1672	−0.2772	0.2066	0.088*
C5	0.1415 (13)	−0.0051 (18)	0.2677 (13)	0.083 (3)
H5A	0.1617	0.0762	0.3126	0.099*
C6	0.0917 (13)	−0.1236 (17)	0.1263 (14)	0.080 (3)
H6A	0.0743	−0.1363	0.0532	0.096*
C7	0.0267 (13)	−0.0946 (18)	0.2649 (14)	0.083 (3)
H7A	0.0478	−0.1647	0.3180	0.100*
H7B	−0.0321	−0.0346	0.2715	0.100*
C8	−0.0141 (13)	−0.1606 (19)	0.1553 (13)	0.081 (3)
H8A	−0.0851	−0.1187	0.1084	0.097*
H8B	−0.0246	−0.2599	0.1573	0.097*
C9	0.7916 (10)	−0.0684 (14)	0.4431 (9)	0.054 (3)
H9A	0.8443	−0.0022	0.4815	0.064*
C10	0.8193 (11)	−0.1875 (15)	0.4113 (10)	0.060 (3)
H10A	0.8935	−0.2187	0.4231	0.072*
C11	0.6339 (10)	−0.1723 (13)	0.3608 (9)	0.051 (2)
H11A	0.5560	−0.1953	0.3299	0.061*
C12	0.3507 (10)	0.3209 (13)	0.4170 (9)	0.050 (2)
H12A	0.3139	0.2518	0.4388	0.060*
C13	0.3119 (11)	0.4481 (13)	0.3898 (10)	0.055 (3)
H13A	0.2432	0.4845	0.3897	0.066*
C14	0.4742 (10)	0.4295 (13)	0.3745 (9)	0.050 (2)
H14A	0.5396	0.4509	0.3616	0.060*
N1	0.4556 (8)	0.3092 (9)	0.4073 (6)	0.0389 (19)
N2	0.3900 (9)	0.5160 (10)	0.3620 (8)	0.055 (3)
H2A	0.3849	0.5999	0.3404	0.066*
N3	0.6737 (7)	−0.0577 (9)	0.4109 (6)	0.0385 (19)
N4	0.7219 (10)	−0.2529 (10)	0.3601 (8)	0.058 (3)
H4B	0.7153	−0.3326	0.3313	0.070*
O1	0.1232 (10)	0.0205 (13)	0.1600 (10)	0.102 (3)
O2	0.3853 (6)	0.0273 (8)	0.2739 (6)	0.0493 (16)
O3	0.4150 (8)	−0.0683 (11)	0.4176 (6)	0.064 (2)
O4	0.2664 (7)	−0.2321 (9)	0.0572 (7)	0.0558 (18)
O5	0.3769 (6)	−0.2772 (8)	0.2164 (5)	0.0425 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0361 (5)	0.0323 (5)	0.0371 (5)	0.0007 (3)	0.0170 (3)	0.0026 (3)
C1	0.042 (4)	0.063 (4)	0.067 (4)	−0.001 (3)	0.032 (3)	−0.023 (4)
C2	0.039 (4)	0.064 (5)	0.076 (5)	−0.007 (4)	0.032 (4)	−0.028 (4)
C3	0.049 (4)	0.082 (5)	0.089 (5)	−0.006 (4)	0.031 (4)	−0.034 (4)
C4	0.048 (4)	0.083 (5)	0.091 (5)	−0.003 (4)	0.029 (4)	−0.035 (4)
C5	0.059 (4)	0.087 (5)	0.095 (5)	−0.004 (4)	0.023 (4)	−0.029 (4)
C6	0.054 (4)	0.085 (5)	0.094 (5)	−0.004 (4)	0.021 (4)	−0.030 (4)
C7	0.055 (5)	0.097 (5)	0.097 (5)	−0.004 (4)	0.029 (4)	−0.030 (5)
C8	0.055 (4)	0.091 (5)	0.096 (5)	−0.003 (4)	0.028 (4)	−0.032 (5)
C9	0.041 (5)	0.056 (6)	0.060 (5)	0.011 (5)	0.014 (4)	0.002 (5)
C10	0.047 (5)	0.064 (6)	0.067 (6)	0.016 (5)	0.018 (5)	0.001 (5)
C11	0.043 (4)	0.052 (5)	0.057 (5)	0.006 (4)	0.020 (4)	−0.001 (4)
C12	0.044 (5)	0.053 (5)	0.064 (5)	0.003 (4)	0.033 (4)	0.000 (4)
C13	0.051 (5)	0.052 (5)	0.068 (6)	0.007 (5)	0.029 (5)	0.003 (5)
C14	0.050 (5)	0.050 (5)	0.057 (5)	−0.002 (5)	0.029 (4)	0.001 (5)
N1	0.049 (5)	0.030 (4)	0.041 (4)	−0.001 (4)	0.021 (4)	−0.003 (4)
N2	0.071 (7)	0.032 (5)	0.065 (6)	0.014 (5)	0.031 (5)	0.013 (4)
N3	0.037 (5)	0.037 (5)	0.041 (5)	0.003 (4)	0.015 (4)	0.001 (4)
N4	0.087 (8)	0.038 (5)	0.054 (6)	0.017 (5)	0.031 (5)	−0.007 (4)
O1	0.081 (5)	0.090 (6)	0.109 (6)	0.012 (5)	0.006 (5)	0.000 (5)
O2	0.046 (3)	0.050 (4)	0.060 (4)	0.001 (3)	0.029 (3)	0.006 (3)
O3	0.066 (5)	0.086 (5)	0.046 (4)	0.018 (4)	0.028 (3)	0.004 (4)
O4	0.050 (4)	0.055 (4)	0.060 (4)	0.011 (3)	0.019 (3)	−0.002 (3)
O5	0.045 (3)	0.042 (4)	0.046 (3)	0.003 (3)	0.024 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Cd1—N1	2.230 (9)	C7—H7A	0.9700
Cd1—N3	2.240 (9)	C7—H7B	0.9700
Cd1—O3ⁱ	2.333 (8)	C8—H8A	0.9700
Cd1—O5ⁱⁱ	2.476 (7)	C8—H8B	0.9700
Cd1—O4ⁱⁱ	2.487 (8)	C9—C10	1.329 (18)
Cd1—O2	2.500 (8)	C9—N3	1.372 (14)
Cd1—O3	2.599 (10)	C9—H9A	0.9300
C1—O2	1.226 (15)	C10—N4	1.316 (17)
C1—O3	1.258 (15)	C10—H10A	0.9300
C1—C3	1.506 (17)	C11—N3	1.305 (15)
C2—O4	1.222 (15)	C11—N4	1.354 (15)
C2—O5	1.271 (15)	C11—H11A	0.9300
C2—C4	1.510 (17)	C12—C13	1.323 (18)
C3—C5	1.36 (2)	C12—N1	1.379 (14)
C3—C4	1.540 (19)	C12—H12A	0.9300
C3—H3A	0.9800	C13—N2	1.357 (16)
C4—C6	1.38 (2)	C13—H13A	0.9300
C4—H4A	0.9800	C14—N1	1.306 (15)
C5—O1	1.47 (2)	C14—N2	1.304 (15)
C5—C7	1.67 (2)	C14—H14A	0.9300
C5—H5A	0.9800	N2—H2A	0.8600
C6—O1	1.476 (18)	N4—H4B	0.8600
C6—C8	1.57 (2)	O3—Cd1ⁱ	2.333 (8)
C6—H6A	0.9800	O4—Cd1ⁱⁱⁱ	2.487 (8)
C7—C8	1.57 (2)	O5—Cd1ⁱⁱⁱ	2.476 (7)

N1—Cd1—N3	174.2 (3)	C8—C6—H6A	112.5
N1—Cd1—O3ⁱ	93.7 (3)	C8—C7—C5	100.5 (13)
N3—Cd1—O3ⁱ	91.4 (3)	C8—C7—H7A	111.7
N1—Cd1—O5ⁱⁱ	89.6 (3)	C5—C7—H7A	111.7
N3—Cd1—O5ⁱⁱ	84.6 (3)	C8—C7—H7B	111.7
O3ⁱ—Cd1—O5ⁱⁱ	153.7 (3)	C5—C7—H7B	111.7
N1—Cd1—O4ⁱⁱ	90.2 (3)	H7A—C7—H7B	109.4
N3—Cd1—O4ⁱⁱ	85.8 (3)	C7—C8—C6	100.4 (12)
O3ⁱ—Cd1—O4ⁱⁱ	101.5 (3)	C7—C8—H8A	111.7
O5ⁱⁱ—Cd1—O4ⁱⁱ	52.3 (3)	C6—C8—H8A	111.7
N1—Cd1—O2	86.1 (3)	C7—C8—H8B	111.7
N3—Cd1—O2	94.2 (3)	C6—C8—H8B	111.7
O3ⁱ—Cd1—O2	117.3 (3)	H8A—C8—H8B	109.5
O5ⁱⁱ—Cd1—O2	89.0 (2)	C10—C9—N3	110.0 (12)
O4ⁱⁱ—Cd1—O2	141.1 (3)	C10—C9—H9A	125.0
N1—Cd1—O3	99.5 (3)	N3—C9—H9A	125.0
N3—Cd1—O3	85.1 (3)	N4—C10—C9	107.1 (11)
O3ⁱ—Cd1—O3	69.1 (4)	N4—C10—H10A	126.5
O5ⁱⁱ—Cd1—O3	136.0 (3)	C9—C10—H10A	126.5
O4ⁱⁱ—Cd1—O3	166.8 (3)	N3—C11—N4	110.6 (11)
O2—Cd1—O3	49.4 (3)	N3—C11—H11A	124.7
O2—C1—O3	118.3 (11)	N4—C11—H11A	124.7
O2—C1—C3	121.3 (13)	C13—C12—N1	107.8 (11)
O3—C1—C3	120.1 (13)	C13—C12—H12A	126.1
O4—C2—O5	122.5 (10)	N1—C12—H12A	126.1
O4—C2—C4	122.5 (13)	C12—C13—N2	107.9 (11)
O5—C2—C4	114.5 (12)	C12—C13—H13A	126.1
C5—C3—C1	117.4 (13)	N2—C13—H13A	126.1
C5—C3—C4	106.9 (13)	N1—C14—N2	111.8 (10)
C1—C3—C4	115.3 (11)	N1—C14—H14A	124.1
C5—C3—H3A	105.4	N2—C14—H14A	124.1
C1—C3—H3A	105.4	C14—N1—C12	105.7 (10)
C4—C3—H3A	105.4	C14—N1—Cd1	124.0 (7)
C6—C4—C2	122.0 (16)	C12—N1—Cd1	129.4 (8)
C6—C4—C3	100.0 (12)	C14—N2—C13	106.8 (10)
C2—C4—C3	119.0 (11)	C14—N2—H2A	126.6
C6—C4—H4A	104.6	C13—N2—H2A	126.6
C2—C4—H4A	104.6	C11—N3—C9	104.6 (10)
C3—C4—H4A	104.6	C11—N3—Cd1	123.6 (7)
C3—C5—O1	95.3 (13)	C9—N3—Cd1	131.1 (8)
C3—C5—C7	105.8 (14)	C10—N4—C11	107.7 (10)
O1—C5—C7	106.0 (12)	C10—N4—H4B	126.1
C3—C5—H5A	115.8	C11—N4—H4B	126.1
O1—C5—H5A	115.8	C6—O1—C5	95.3 (13)
C7—C5—H5A	115.8	C1—O2—Cd1	98.4 (7)
C4—C6—O1	99.4 (12)	C1—O3—Cd1ⁱ	149.9 (8)
C4—C6—C8	113.0 (16)	C1—O3—Cd1	92.7 (8)
O1—C6—C8	106.1 (13)	Cd1ⁱ—O3—Cd1	110.9 (4)
C4—C6—H6A	112.5	C2—O4—Cd1ⁱⁱⁱ	92.6 (7)
O1—C6—H6A	112.5	C2—O5—Cd1ⁱⁱⁱ	91.9 (6)

O2—C1—C3—C5	−67.4 (19)	C10—C9—N3—Cd1	−170.3 (9)
O3—C1—C3—C5	106.4 (18)	N1—Cd1—N3—C11	−105 (3)
O2—C1—C3—C4	60.1 (19)	O3ⁱ—Cd1—N3—C11	105.9 (9)
O3—C1—C3—C4	−126.2 (15)	O5ⁱⁱ—Cd1—N3—C11	−100.2 (9)
O4—C2—C4—C6	−15 (2)	O4ⁱⁱ—Cd1—N3—C11	−152.6 (9)
O5—C2—C4—C6	173.5 (13)	O2—Cd1—N3—C11	−11.6 (9)
O4—C2—C4—C3	−140.1 (15)	O3—Cd1—N3—C11	37.0 (9)
O5—C2—C4—C3	48 (2)	N1—Cd1—N3—C9	64 (3)
C5—C3—C4—C6	3.3 (19)	O3ⁱ—Cd1—N3—C9	−84.9 (10)
C1—C3—C4—C6	−129.2 (15)	O5ⁱⁱ—Cd1—N3—C9	69.0 (10)
C5—C3—C4—C2	138.9 (16)	O4ⁱⁱ—Cd1—N3—C9	16.6 (10)
C1—C3—C4—C2	6 (2)	O2—Cd1—N3—C9	157.6 (10)
C1—C3—C5—O1	91.7 (15)	O3—Cd1—N3—C9	−153.8 (10)
C4—C3—C5—O1	−39.6 (16)	C9—C10—N4—C11	0.0 (15)
C1—C3—C5—C7	−160.0 (14)	N3—C11—N4—C10	0.2 (14)
C4—C3—C5—C7	68.7 (17)	C4—C6—O1—C5	−60.7 (15)
C2—C4—C6—O1	−99.0 (17)	C8—C6—O1—C5	56.7 (14)
C3—C4—C6—O1	34.8 (16)	C3—C5—O1—C6	60.4 (13)
C2—C4—C6—C8	149.0 (14)	C7—C5—O1—C6	−47.8 (13)
C3—C4—C6—C8	−77.2 (16)	O3—C1—O2—Cd1	−11.1 (12)
C3—C5—C7—C8	−76.9 (17)	C3—C1—O2—Cd1	162.8 (10)
O1—C5—C7—C8	23.5 (16)	N1—Cd1—O2—C1	−99.8 (7)
C5—C7—C8—C6	10.1 (16)	N3—Cd1—O2—C1	86.1 (7)
C4—C6—C8—C7	65.5 (17)	O3ⁱ—Cd1—O2—C1	−7.6 (8)
O1—C6—C8—C7	−42.4 (17)	O5ⁱⁱ—Cd1—O2—C1	170.6 (7)
N3—C9—C10—N4	−0.3 (15)	O4ⁱⁱ—Cd1—O2—C1	174.6 (7)
N1—C12—C13—N2	0.7 (14)	O3—Cd1—O2—C1	6.2 (7)
N2—C14—N1—C12	−0.4 (13)	O2—C1—O3—Cd1ⁱ	153.0 (13)
N2—C14—N1—Cd1	169.4 (8)	C3—C1—O3—Cd1ⁱ	−21 (2)
C13—C12—N1—C14	−0.2 (13)	O2—C1—O3—Cd1	10.5 (11)
C13—C12—N1—Cd1	−169.3 (8)	C3—C1—O3—Cd1	−163.4 (10)
N3—Cd1—N1—C14	−18 (3)	N1—Cd1—O3—C1	70.6 (7)
O3ⁱ—Cd1—N1—C14	131.6 (9)	N3—Cd1—O3—C1	−105.8 (7)
O5ⁱⁱ—Cd1—N1—C14	−22.2 (9)	O3ⁱ—Cd1—O3—C1	160.9 (9)
O4ⁱⁱ—Cd1—N1—C14	30.1 (9)	O5ⁱⁱ—Cd1—O3—C1	−28.7 (8)
O2—Cd1—N1—C14	−111.2 (9)	O4ⁱⁱ—Cd1—O3—C1	−152.6 (11)
O3—Cd1—N1—C14	−158.9 (9)	O2—Cd1—O3—C1	−6.0 (6)
N3—Cd1—N1—C12	150 (3)	N1—Cd1—O3—Cd1ⁱ	−90.3 (4)
O3ⁱ—Cd1—N1—C12	−61.1 (10)	N3—Cd1—O3—Cd1ⁱ	93.3 (4)
O5ⁱⁱ—Cd1—N1—C12	145.1 (9)	O3ⁱ—Cd1—O3—Cd1ⁱ	0.0
O4ⁱⁱ—Cd1—N1—C12	−162.7 (9)	O5ⁱⁱ—Cd1—O3—Cd1ⁱ	170.4 (3)
O2—Cd1—N1—C12	56.1 (9)	O4ⁱⁱ—Cd1—O3—Cd1ⁱ	46.5 (14)
O3—Cd1—N1—C12	8.4 (10)	O2—Cd1—O3—Cd1ⁱ	−166.9 (5)
N1—C14—N2—C13	0.8 (14)	O5—C2—O4—Cd1ⁱⁱⁱ	9.0 (13)
C12—C13—N2—C14	−0.9 (14)	C4—C2—O4—Cd1ⁱⁱⁱ	−162.4 (13)
N4—C11—N3—C9	−0.4 (13)	O4—C2—O5—Cd1ⁱⁱⁱ	−9.0 (13)
N4—C11—N3—Cd1	171.2 (7)	C4—C2—O5—Cd1ⁱⁱⁱ	163.0 (11)
C10—C9—N3—C11	0.4 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5^iv	0.86	2.09	2.830 (12)	144
N4—H4B···O1ⁱⁱⁱ	0.86	2.44	3.012 (17)	125
N4—H4B···O2ⁱⁱⁱ	0.86	2.05	2.818 (13)	149
C6—H6A···O4	0.98	2.56	2.92 (2)	101
C11—H11A···O5	0.93	2.34	3.239 (15)	164
C14—H14A···O2ⁱⁱ	0.93	2.55	3.358 (15)	145
C12—H12A···Cg5ⁱ	0.93	2.76	3.565 (14)	145

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

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₈O₅)(C₃H₄N₂)₂]
M_r	432.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.5374 (16), 9.6596 (13), 14.1635 (17)
β (°)	112.761 (7)
V (Å³)	1581.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.12 × 0.06 × 0.05

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.900, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	10791, 2777, 2310
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.216, 1.05
No. of reflections	2777
No. of parameters	217
No. of restraints	234
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1141P)² + 20.9278P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.92, −1.26

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.8600	2.0900	2.830 (12)	144.00
N4—H4B···O1ⁱⁱ	0.8600	2.4400	3.012 (17)	125.00
N4—H4B···O2ⁱⁱ	0.8600	2.0500	2.818 (13)	149.00
C6—H6A···O4	0.9800	2.5600	2.92 (2)	101.00
C11—H11A···O5	0.9300	2.3400	3.239 (15)	164.00
C14—H14A···O2ⁱⁱⁱ	0.9300	2.5500	3.358 (15)	145.00
C12—H12A···Cg5^iv	0.93	2.76	3.565 (14)	145

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

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China (grant No. Y407301) for financial support.

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