Diaqua­bis­(5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2N3,O4)cadmium(II) 3.5-hydrate

Li, S.-J.; Dong, J.-J.; Song, W.-D.; Yan, J.-B.; Li, S.-H.

doi:10.1107/S1600536810031466

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1175-m1176

https://doi.org/10.1107/S1600536810031466

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Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-κ²N³,O⁴)cadmium(II) 3.5-hydrate

Shi-Jie Li,^a Jing-Jing Dong,^a Wen-Dong Song,^b ^* Jian-Bin Yan ^a and Shi-Hong Li ^c

^aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cCollege of Medical Laboratory, Hebei North University, Zhangjiakou 075000, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 13 July 2010; accepted 5 August 2010; online 28 August 2010)

In the title complex, [Cd(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O, the Cd^II is coordinated by two water molecules and N,O-chelated by two 5-carboxy-2-propyl-1H-imidazole-4-carboxylate anions in a distorted octahedral geometry. The two imidazole rings are oriented to each other with a dihedral angle of 75.1 (2)°. Strong O—H⋯O hydrogen bonds between protonated and deprotonated carboxylate groups occur in the molecular structure. In the crystal structure extensive O—H⋯O and N—H⋯O hydrogen bonds help to stabilize the three-dimensional supramolecular framework. The propyl groups of anions are disordered over two sites with refined occupancies of 0.768 (6):0.232 (6) and 0.642 (8):0.358 (8).

Related literature

For the potential uses and diverse structural types of metal complexes with the imidazole-4,5-dicarboxylate ligand, see: Zou et al. (2006 ); Li et al. (2006 ); Liu et al. (2004 ); Sun et al. (2005 ). For related structures, see: Yan et al. (2010 ); Li et al. (2010 ); Song et al. (2010 ); He et al. (2010 ); Fan et al. (2010 ).

Experimental

Crystal data

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O
M_r = 605.83
Triclinic, $[P \overline 1]$
a = 10.6228 (12) Å
b = 10.7000 (12) Å
c = 11.3694 (13) Å
α = 83.690 (1)°
β = 81.701 (1)°
γ = 87.441 (1)°
V = 1270.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 296 K
0.29 × 0.24 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.775, T_max = 0.829
6589 measured reflections
4494 independent reflections
3730 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.05
4494 reflections
346 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4W	0.86	1.89	2.747 (5)	172
N4—H4⋯O6W	0.86	1.90	2.729 (5)	161
O1—H1⋯O4	0.82 (3)	1.67 (3)	2.490 (5)	172 (7)
O7—H7⋯O6	0.82 (4)	1.63 (4)	2.440 (5)	171 (8)
O1W—H1W⋯O5Wⁱ	0.85	2.27	2.654 (5)	108
O1W—H2W⋯O8ⁱⁱ	0.85	1.90	2.737 (5)	168
O2W—H3W⋯O8ⁱⁱⁱ	0.84	2.08	2.852 (5)	152
O2W—H4W⋯O2^iv	0.86	1.99	2.818 (5)	163
O3W—H5W⋯O3^iv	0.85	2.19	2.794 (7)	128
O3W—H6W⋯O3^v	0.85	1.96	2.770 (6)	160
O4W—H7W⋯O3W	0.85	1.78	2.620 (8)	169
O4W—H8W⋯O7^vi	0.85	2.05	2.904 (6)	180
O5W—H9W⋯O5^vi	0.87	2.01	2.841 (5)	159
O5W—H10W⋯O4^vii	0.85	1.95	2.778 (5)	163
O6W—H11W⋯O3W^vii	0.85	1.87	2.679 (8)	160
O6W—H12W⋯O5W^viii	0.85	2.22	2.850 (5)	130
Symmetry codes: (i) x+1, y, z-1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+2, -y, -z+1; (v) x, y, z+1; (vi) -x+1, -y+1, -z+1; (vii) -x+1, -y, -z+1; (viii) x, y, z-1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810031466/xu5001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031466/xu5001Isup2.hkl

checkCIF report

Comment top

Imidazole-4,5-dicarboxylic acid (H₃IDC) has been widely used to coordinate with metal salts to obtain a series of MOFs with different structures and useful properties(Zou et al., 2006; Li et al., 2006; Liu et al., 2004; Sun et al., 2005), 2-propyl-1H-imidazole-4,5-carboxylate(H₃pimda) ligand as one derivative of H₃IDC with efficient N,O-donors has been used to obtain new metal-organic complexes by our research group, such as poly[diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- k³ N³,O⁴,O⁵)calcium(II)] (Song et al., 2010), [diaquabis (5-carboxy-2-propyl-1H-imidazole-4-carboxylato-k²N³,O⁴) manganese(II)]N,N-dimethylformamide (Yan et al., 2010), [Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-k² N³,O⁴)nickle(II)]N,N-dimethylformamide disolvate(Li et al., 2010), Diaquabis(4-carboxy-2-propyl-1H-imidazole-5-carboxylato- k²N³,O⁴)copper(II) N,N-dimethylformamide disolvate (He et al., 2010) and Diaquabis(5-carboxy-2-propyl-1H-imidazole- 4-carboxylato-k²N³,O⁴)nickle(II) tetrahedrate (Fan et al., 2010). In this paper, we report the structure of a new Cd(II) complex obtained under hydrothermal conditions.

As illustrated in figure 1, the title complex molecule is similar to diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ²N,O)nickle(II) tetrahedrate (Fan et al. 2010), contains one Cd^II ion, two mono-deprotonated H₂pimda^- anions, two coordinated water molecules and 3.5 solvent water molecules. The Cd^II is six-coordinated by two N,O-bidentate H₃pimda anions and two water molecules in a distorted octahedral geometry. the dihedral angle between the two imidazole rings is 75.0 (1) %A. In the crystal structure, the three-dimensional supramolecular framework is stabilized by extensive O—H···O and N—H···O hydrogen bonds involving the free water molecules, the coordinated water molecules, the carboxy O atoms and the protonated N atoms of H₃pimda. The propyl groups of H₃pimda are disordered over two sets of sites with refined occupiencies of 0.772 (6):0.228 (6) and 0.642 (8):0.358 (8).

Related literature top

For the potential uses and diverse structural types of metal complexes with the imidazole-4,5-dicarboxylate ligand, see: Zou et al. (2006); Li et al. (2006); Liu et al. (2004); Sun et al. (2005). For related structures, see: Yan et al. (2010); Li et al. (2010); Song et al.(2010); He et al. (2010); Fan et al. (2010).

Experimental top

A mixture of CdCl₂ (0.5 mmol, 0.09 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml water was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 433 K for 4 days. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Structure description top

For the potential uses and diverse structural types of metal complexes with the imidazole-4,5-dicarboxylate ligand, see: Zou et al. (2006); Li et al. (2006); Liu et al. (2004); Sun et al. (2005). For related structures, see: Yan et al. (2010); Li et al. (2010); Song et al.(2010); He et al. (2010); Fan et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing the atomic-numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids.

Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ²N³,O⁴)cadmium(II) 3.5-hydrate top

Crystal data top

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O	Z = 2
M_r = 605.83	F(000) = 618
Triclinic, P1	D_x = 1.584 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6228 (12) Å	Cell parameters from 3600 reflections
b = 10.7000 (12) Å	θ = 1.4–25.0°
c = 11.3694 (13) Å	µ = 0.93 mm⁻¹
α = 83.690 (1)°	T = 296 K
β = 81.701 (1)°	Block, colorless
γ = 87.441 (1)°	0.29 × 0.24 × 0.21 mm
V = 1270.5 (2) Å³

Data collection top

Bruker APEXII area-detector diffractometer	4494 independent reflections
Radiation source: fine-focus sealed tube	3730 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scan	θ_max = 25.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.775, T_max = 0.829	k = −12→8
6589 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0505P)² + 0.1685P] where P = (F_o² + 2F_c²)/3
4494 reflections	(Δ/σ)_max = 0.001
346 parameters	Δρ_max = 0.46 e Å⁻³
7 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O	γ = 87.441 (1)°
M_r = 605.83	V = 1270.5 (2) Å³
Triclinic, P1	Z = 2
a = 10.6228 (12) Å	Mo Kα radiation
b = 10.7000 (12) Å	µ = 0.93 mm⁻¹
c = 11.3694 (13) Å	T = 296 K
α = 83.690 (1)°	0.29 × 0.24 × 0.21 mm
β = 81.701 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	4494 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3730 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.829	R_int = 0.034
6589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	7 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.46 e Å⁻³
4494 reflections	Δρ_min = −0.59 e Å⁻³
346 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	0.84023 (3)	0.29169 (3)	0.19976 (2)	0.04816 (13)
O1	0.8778 (4)	−0.1913 (3)	0.5186 (3)	0.0698 (9)
O2	0.8413 (3)	−0.1136 (3)	0.6913 (3)	0.0701 (9)
O3	0.8810 (3)	0.0754 (3)	0.1940 (2)	0.0565 (7)
O4	0.8944 (3)	−0.1083 (3)	0.3037 (3)	0.0656 (8)
O5	0.7595 (3)	0.5000 (3)	0.2111 (3)	0.0553 (7)
O6	0.5964 (3)	0.6304 (3)	0.1835 (3)	0.0660 (8)
O7	0.3809 (3)	0.6208 (3)	0.1350 (3)	0.0604 (8)
O8	0.2516 (3)	0.4784 (3)	0.0948 (3)	0.0606 (8)
N1	0.8262 (3)	0.2015 (3)	0.3933 (3)	0.0454 (7)
N2	0.8116 (3)	0.1310 (3)	0.5823 (3)	0.0550 (9)
H2	0.8009	0.1302	0.6588	0.066*
N3	0.6294 (3)	0.2956 (3)	0.1734 (3)	0.0438 (7)
N4	0.4358 (3)	0.2862 (3)	0.1287 (3)	0.0479 (8)
H4	0.3681	0.2556	0.1112	0.058*
C1	0.8362 (3)	0.0280 (4)	0.5209 (3)	0.0447 (9)
C2	0.8454 (3)	0.0742 (3)	0.4021 (3)	0.0395 (8)
C3	0.8069 (5)	0.2337 (4)	0.5040 (4)	0.0591 (11)
C4	0.8760 (4)	0.0090 (4)	0.2913 (3)	0.0473 (9)
C5	0.8512 (4)	−0.0992 (4)	0.5834 (4)	0.0517 (10)
C6A	0.7979 (9)	0.3683 (10)	0.5325 (10)	0.085 (3)	0.772 (6)
H6A	0.8215	0.3717	0.6114	0.102*	0.772 (6)
H6B	0.8579	0.4174	0.4753	0.102*	0.772 (6)
C7A	0.6674 (9)	0.4249 (7)	0.5292 (8)	0.107 (3)	0.772 (6)
H7A	0.6091	0.3854	0.5949	0.128*	0.772 (6)
H7B	0.6379	0.4108	0.4550	0.128*	0.772 (6)
C8A	0.6699 (11)	0.5651 (7)	0.5390 (9)	0.129 (4)	0.772 (6)
H8A	0.5848	0.5970	0.5604	0.193*	0.772 (6)
H8B	0.7059	0.6073	0.4635	0.193*	0.772 (6)
H8C	0.7207	0.5796	0.5992	0.193*	0.772 (6)
C6B	0.740 (4)	0.350 (4)	0.549 (4)	0.085 (3)	0.228 (6)
H6C	0.6751	0.3816	0.5002	0.102*	0.228 (6)
H6D	0.6998	0.3328	0.6313	0.102*	0.228 (6)
C7B	0.844 (3)	0.442 (3)	0.540 (3)	0.107 (3)	0.228 (6)
H7C	0.8078	0.5259	0.5500	0.128*	0.228 (6)
H7D	0.8951	0.4445	0.4616	0.128*	0.228 (6)
C8B	0.924 (3)	0.399 (3)	0.637 (3)	0.129 (4)	0.228 (6)
H8D	0.9722	0.4679	0.6515	0.193*	0.228 (6)
H8E	0.9808	0.3317	0.6117	0.193*	0.228 (6)
H8F	0.8695	0.3699	0.7086	0.193*	0.228 (6)
C9	0.5736 (3)	0.4138 (3)	0.1688 (3)	0.0397 (8)
C10	0.4529 (3)	0.4099 (4)	0.1405 (3)	0.0413 (8)
C11	0.5431 (4)	0.2209 (4)	0.1490 (4)	0.0509 (10)
C12	0.6485 (4)	0.5201 (4)	0.1898 (3)	0.0470 (9)
C13	0.3529 (4)	0.5090 (4)	0.1221 (3)	0.0481 (9)
C14A	0.5509 (17)	0.0797 (5)	0.1655 (9)	0.061 (3)	0.642 (8)
H14A	0.6361	0.0508	0.1353	0.073*	0.642 (8)
H14B	0.4918	0.0464	0.1201	0.073*	0.642 (8)
C15A	0.5189 (11)	0.0302 (8)	0.2979 (9)	0.081 (3)	0.642 (8)
H15A	0.5740	0.0680	0.3443	0.098*	0.642 (8)
H15B	0.4315	0.0537	0.3267	0.098*	0.642 (8)
C16A	0.5361 (10)	−0.1097 (8)	0.3138 (11)	0.108 (4)	0.642 (8)
H16A	0.5605	−0.1354	0.3912	0.161*	0.642 (8)
H16B	0.6013	−0.1358	0.2531	0.161*	0.642 (8)
H16C	0.4576	−0.1479	0.3075	0.161*	0.642 (8)
C14B	0.572 (3)	0.0878 (9)	0.119 (2)	0.061 (3)	0.358 (8)
H14C	0.6611	0.0664	0.1216	0.073*	0.358 (8)
H14D	0.5526	0.0790	0.0400	0.073*	0.358 (8)
C15B	0.4893 (14)	0.0002 (15)	0.2123 (14)	0.081 (3)	0.358 (8)
H15C	0.4005	0.0244	0.2101	0.098*	0.358 (8)
H15D	0.5017	−0.0851	0.1905	0.098*	0.358 (8)
C16B	0.518 (3)	0.002 (2)	0.3363 (17)	0.108 (4)	0.358 (8)
H16D	0.4796	−0.0688	0.3859	0.161*	0.358 (8)
H16E	0.4832	0.0784	0.3669	0.161*	0.358 (8)
H16F	0.6080	−0.0025	0.3363	0.161*	0.358 (8)
O1W	0.8927 (3)	0.3292 (4)	0.0015 (3)	0.0955 (13)
H1W	0.9095	0.2617	−0.0314	0.143*
H2W	0.8569	0.3905	−0.0363	0.143*
O2W	1.0419 (3)	0.3400 (4)	0.2218 (3)	0.0897 (12)
H3W	1.0847	0.4010	0.1869	0.135*
H4W	1.0911	0.2778	0.2405	0.135*
O3W	0.9149 (6)	0.0145 (6)	0.9607 (5)	0.0625 (15)	0.50
H5W	0.9951	0.0020	0.9528	0.094*	0.50
H6W	0.9090	0.0145	1.0360	0.094*	0.50
O4W	0.7737 (5)	0.1534 (4)	0.8233 (3)	0.1211 (17)
H7W	0.8269	0.1083	0.8598	0.182*
H8W	0.7288	0.2197	0.8353	0.182*
O5W	0.1097 (3)	0.2735 (3)	0.8678 (3)	0.0718 (9)
H9W	0.1608	0.3312	0.8299	0.108*
H10W	0.1151	0.2123	0.8255	0.108*
O6W	0.2598 (4)	0.1582 (4)	0.0406 (4)	0.1044 (13)
H11W	0.2130	0.0949	0.0534	0.157*
H12W	0.2045	0.2161	0.0283	0.157*
H1	0.876 (8)	−0.162 (7)	0.449 (2)	0.157*
H7	0.453 (3)	0.632 (7)	0.149 (7)	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04170 (18)	0.0518 (2)	0.0479 (2)	0.00347 (13)	−0.00891 (12)	0.01025 (13)
O1	0.091 (2)	0.0495 (19)	0.067 (2)	−0.0007 (16)	−0.0173 (19)	0.0084 (16)
O2	0.070 (2)	0.079 (2)	0.0510 (19)	0.0116 (17)	−0.0047 (15)	0.0254 (15)
O3	0.0718 (19)	0.0587 (18)	0.0362 (15)	0.0191 (14)	−0.0077 (13)	−0.0008 (13)
O4	0.096 (2)	0.0453 (18)	0.0579 (18)	0.0127 (16)	−0.0199 (16)	−0.0092 (14)
O5	0.0471 (16)	0.0495 (17)	0.0723 (19)	−0.0052 (13)	−0.0187 (14)	−0.0049 (14)
O6	0.0647 (19)	0.0398 (17)	0.096 (2)	0.0045 (14)	−0.0164 (17)	−0.0127 (16)
O7	0.0518 (17)	0.0510 (18)	0.077 (2)	0.0153 (14)	−0.0098 (15)	−0.0072 (15)
O8	0.0370 (15)	0.069 (2)	0.071 (2)	0.0022 (13)	−0.0108 (13)	0.0172 (15)
N1	0.0490 (18)	0.0434 (19)	0.0429 (18)	0.0051 (14)	−0.0080 (14)	−0.0005 (14)
N2	0.063 (2)	0.064 (2)	0.0355 (17)	0.0098 (17)	−0.0058 (15)	−0.0041 (16)
N3	0.0387 (17)	0.0403 (18)	0.0517 (19)	0.0014 (14)	−0.0099 (14)	0.0012 (14)
N4	0.0384 (17)	0.050 (2)	0.055 (2)	−0.0057 (14)	−0.0133 (14)	0.0032 (15)
C1	0.038 (2)	0.049 (2)	0.044 (2)	0.0000 (16)	−0.0035 (16)	0.0043 (18)
C2	0.0334 (18)	0.044 (2)	0.041 (2)	0.0010 (15)	−0.0074 (15)	−0.0007 (16)
C3	0.076 (3)	0.053 (3)	0.050 (3)	0.009 (2)	−0.014 (2)	−0.006 (2)
C4	0.047 (2)	0.050 (2)	0.045 (2)	0.0074 (17)	−0.0120 (17)	−0.0020 (18)
C5	0.043 (2)	0.061 (3)	0.047 (2)	0.0004 (18)	−0.0083 (18)	0.014 (2)
C6A	0.109 (9)	0.068 (5)	0.078 (5)	0.011 (6)	−0.009 (6)	−0.021 (4)
C7A	0.133 (8)	0.069 (5)	0.115 (7)	0.011 (5)	−0.004 (5)	−0.017 (5)
C8A	0.174 (10)	0.067 (5)	0.136 (8)	0.020 (5)	0.006 (7)	−0.012 (5)
C6B	0.109 (9)	0.068 (5)	0.078 (5)	0.011 (6)	−0.009 (6)	−0.021 (4)
C7B	0.133 (8)	0.069 (5)	0.115 (7)	0.011 (5)	−0.004 (5)	−0.017 (5)
C8B	0.174 (10)	0.067 (5)	0.136 (8)	0.020 (5)	0.006 (7)	−0.012 (5)
C9	0.0391 (19)	0.039 (2)	0.0383 (19)	0.0003 (15)	−0.0029 (15)	0.0024 (15)
C10	0.039 (2)	0.044 (2)	0.0378 (19)	−0.0004 (16)	0.0002 (15)	0.0032 (16)
C11	0.048 (2)	0.043 (2)	0.061 (3)	−0.0025 (18)	−0.0127 (19)	0.0029 (19)
C12	0.048 (2)	0.046 (2)	0.047 (2)	0.0007 (18)	−0.0077 (17)	−0.0012 (17)
C13	0.041 (2)	0.056 (3)	0.040 (2)	0.0088 (18)	0.0033 (16)	0.0075 (18)
C14A	0.061 (7)	0.036 (3)	0.087 (9)	−0.006 (3)	−0.022 (7)	0.007 (4)
C15A	0.062 (5)	0.058 (5)	0.121 (8)	−0.003 (4)	−0.028 (5)	0.023 (5)
C16A	0.101 (7)	0.059 (5)	0.157 (10)	−0.007 (5)	−0.023 (6)	0.023 (6)
C14B	0.061 (7)	0.036 (3)	0.087 (9)	−0.006 (3)	−0.022 (7)	0.007 (4)
C15B	0.062 (5)	0.058 (5)	0.121 (8)	−0.003 (4)	−0.028 (5)	0.023 (5)
C16B	0.101 (7)	0.059 (5)	0.157 (10)	−0.007 (5)	−0.023 (6)	0.023 (6)
O1W	0.085 (3)	0.121 (3)	0.059 (2)	0.052 (2)	0.0107 (18)	0.035 (2)
O2W	0.0499 (19)	0.100 (3)	0.110 (3)	−0.0224 (18)	−0.0251 (18)	0.057 (2)
O3W	0.065 (4)	0.075 (4)	0.048 (3)	0.008 (3)	−0.007 (3)	−0.013 (3)
O4W	0.156 (4)	0.142 (4)	0.072 (2)	0.058 (3)	−0.030 (3)	−0.048 (3)
O5W	0.0623 (19)	0.069 (2)	0.084 (2)	−0.0175 (16)	0.0083 (16)	−0.0255 (17)
O6W	0.101 (3)	0.098 (3)	0.131 (4)	−0.001 (2)	−0.064 (3)	−0.025 (3)

Geometric parameters (Å, º) top

Cd1—O1W	2.238 (3)	C6B—H6D	0.9700
Cd1—O2W	2.281 (3)	C7B—C8B	1.512 (14)
Cd1—N1	2.290 (3)	C7B—H7C	0.9700
Cd1—N3	2.300 (3)	C7B—H7D	0.9700
Cd1—O3	2.341 (3)	C8B—H8D	0.9600
Cd1—O5	2.362 (3)	C8B—H8E	0.9600
O1—C5	1.291 (5)	C8B—H8F	0.9600
O1—H1	0.82 (3)	C9—C10	1.370 (5)
O2—C5	1.209 (5)	C9—C12	1.476 (5)
O3—C4	1.243 (5)	C10—C13	1.487 (5)
O4—C4	1.257 (5)	C11—C14A	1.502 (7)
O5—C12	1.243 (5)	C11—C14B	1.507 (9)
O6—C12	1.280 (5)	C14A—C15A	1.534 (12)
O7—C13	1.275 (5)	C14A—H14A	0.9700
O7—H7	0.82 (4)	C14A—H14B	0.9700
O8—C13	1.229 (5)	C15A—C16A	1.495 (10)
N1—C3	1.327 (5)	C15A—H15A	0.9700
N1—C2	1.363 (5)	C15A—H15B	0.9700
N2—C3	1.341 (5)	C16A—H16A	0.9600
N2—C1	1.364 (5)	C16A—H16B	0.9600
N2—H2	0.8600	C16A—H16C	0.9600
N3—C11	1.320 (5)	C14B—C15B	1.532 (14)
N3—C9	1.371 (5)	C14B—H14C	0.9700
N4—C11	1.346 (5)	C14B—H14D	0.9700
N4—C10	1.368 (5)	C15B—C16B	1.486 (13)
N4—H4	0.8600	C15B—H15C	0.9700
C1—C2	1.377 (5)	C15B—H15D	0.9700
C1—C5	1.478 (6)	C16B—H16D	0.9600
C2—C4	1.495 (5)	C16B—H16E	0.9600
C3—C6A	1.506 (11)	C16B—H16F	0.9600
C3—C6B	1.51 (4)	O1W—H1W	0.8499
C6A—C7A	1.492 (12)	O1W—H2W	0.8500
C6A—H6A	0.9700	O2W—H3W	0.8405
C6A—H6B	0.9700	O2W—H4W	0.8547
C7A—C8A	1.518 (10)	O3W—H5W	0.8500
C7A—H7A	0.9700	O3W—H6W	0.8501
C7A—H7B	0.9700	O4W—H7W	0.8503
C8A—H8A	0.9600	O4W—H8W	0.8498
C8A—H8B	0.9600	O5W—H9W	0.8741
C8A—H8C	0.9600	O5W—H10W	0.8500
C6B—C7B	1.498 (15)	O6W—H11W	0.8452
C6B—H6C	0.9700	O6W—H12W	0.8490

O1W—Cd1—O2W	88.94 (14)	C8B—C7B—H7C	110.3
O1W—Cd1—N1	162.70 (12)	C6B—C7B—H7D	110.3
O2W—Cd1—N1	85.50 (12)	C8B—C7B—H7D	110.3
O1W—Cd1—N3	89.03 (13)	H7C—C7B—H7D	108.5
O2W—Cd1—N3	165.95 (12)	C7B—C8B—H8D	109.5
N1—Cd1—N3	100.21 (11)	C7B—C8B—H8E	109.5
O1W—Cd1—O3	91.83 (12)	H8D—C8B—H8E	109.5
O2W—Cd1—O3	96.11 (12)	C7B—C8B—H8F	109.5
N1—Cd1—O3	72.55 (10)	H8D—C8B—H8F	109.5
N3—Cd1—O3	97.85 (10)	H8E—C8B—H8F	109.5
O1W—Cd1—O5	90.99 (12)	C10—C9—N3	110.1 (3)
O2W—Cd1—O5	94.05 (12)	C10—C9—C12	131.2 (3)
N1—Cd1—O5	105.72 (10)	N3—C9—C12	118.6 (3)
N3—Cd1—O5	72.08 (10)	N4—C10—C9	105.1 (3)
O3—Cd1—O5	169.50 (10)	N4—C10—C13	122.2 (3)
C5—O1—H1	107 (6)	C9—C10—C13	132.6 (4)
C4—O3—Cd1	117.3 (2)	N3—C11—N4	111.0 (3)
C12—O5—Cd1	115.9 (2)	N3—C11—C14A	125.1 (8)
C13—O7—H7	118 (6)	N4—C11—C14A	122.8 (8)
C3—N1—C2	106.7 (3)	N3—C11—C14B	123.8 (15)
C3—N1—Cd1	140.1 (3)	N4—C11—C14B	123.8 (16)
C2—N1—Cd1	113.2 (2)	O5—C12—O6	122.5 (4)
C3—N2—C1	108.9 (3)	O5—C12—C9	119.3 (3)
C3—N2—H2	125.6	O6—C12—C9	118.2 (4)
C1—N2—H2	125.6	O8—C13—O7	125.1 (4)
C11—N3—C9	105.6 (3)	O8—C13—C10	118.7 (4)
C11—N3—Cd1	140.3 (3)	O7—C13—C10	116.2 (4)
C9—N3—Cd1	113.7 (2)	C11—C14A—C15A	110.9 (6)
C11—N4—C10	108.1 (3)	C11—C14A—H14A	109.5
C11—N4—H4	125.9	C15A—C14A—H14A	109.5
C10—N4—H4	125.9	C11—C14A—H14B	109.5
N2—C1—C2	105.1 (3)	C15A—C14A—H14B	109.5
N2—C1—C5	121.4 (4)	H14A—C14A—H14B	108.0
C2—C1—C5	133.4 (4)	C16A—C15A—C14A	110.3 (8)
N1—C2—C1	109.3 (3)	C16A—C15A—H15A	109.6
N1—C2—C4	119.8 (3)	C14A—C15A—H15A	109.6
C1—C2—C4	130.8 (4)	C16A—C15A—H15B	109.6
N1—C3—N2	110.0 (4)	C14A—C15A—H15B	109.6
N1—C3—C6A	123.2 (6)	H15A—C15A—H15B	108.1
N2—C3—C6A	126.4 (6)	C11—C14B—C15B	108.1 (13)
N1—C3—C6B	129 (2)	C11—C14B—H14C	110.1
N2—C3—C6B	117.6 (18)	C15B—C14B—H14C	110.1
O3—C4—O4	125.2 (4)	C11—C14B—H14D	110.1
O3—C4—C2	117.2 (4)	C15B—C14B—H14D	110.1
O4—C4—C2	117.6 (3)	H14C—C14B—H14D	108.4
O2—C5—O1	122.4 (4)	C16B—C15B—C14B	113.8 (19)
O2—C5—C1	119.9 (4)	C16B—C15B—H15C	108.8
O1—C5—C1	117.6 (4)	C14B—C15B—H15C	108.8
C7A—C6A—C3	112.3 (8)	C16B—C15B—H15D	108.8
C7A—C6A—H6A	109.2	C14B—C15B—H15D	108.8
C3—C6A—H6A	109.2	H15C—C15B—H15D	107.7
C7A—C6A—H6B	109.2	C15B—C16B—H16D	109.5
C3—C6A—H6B	109.2	C15B—C16B—H16E	109.5
H6A—C6A—H6B	107.9	H16D—C16B—H16E	109.5
C6A—C7A—C8A	109.4 (8)	C15B—C16B—H16F	109.5
C6A—C7A—H7A	109.8	H16D—C16B—H16F	109.5
C8A—C7A—H7A	109.8	H16E—C16B—H16F	109.5
C6A—C7A—H7B	109.8	Cd1—O1W—H1W	112.0
C8A—C7A—H7B	109.8	Cd1—O1W—H2W	119.5
H7A—C7A—H7B	108.2	H1W—O1W—H2W	118.7
C7B—C6B—C3	104 (3)	Cd1—O2W—H3W	127.7
C7B—C6B—H6C	111.0	Cd1—O2W—H4W	116.0
C3—C6B—H6C	111.0	H3W—O2W—H4W	110.5
C7B—C6B—H6D	111.0	H5W—O3W—H6W	92.8
C3—C6B—H6D	111.0	H7W—O4W—H8W	136.0
H6C—C6B—H6D	109.0	H9W—O5W—H10W	107.5
C6B—C7B—C8B	107 (3)	H11W—O6W—H12W	100.2
C6B—C7B—H7C	110.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4W	0.86	1.89	2.747 (5)	172
N4—H4···O6W	0.86	1.90	2.729 (5)	161
O1—H1···O4	0.82 (3)	1.67 (3)	2.490 (5)	172 (7)
O7—H7···O6	0.82 (4)	1.63 (4)	2.440 (5)	171 (8)
O1W—H1W···O5Wⁱ	0.85	2.27	2.654 (5)	108
O1W—H2W···O8ⁱⁱ	0.85	1.90	2.737 (5)	168
O2W—H3W···O8ⁱⁱⁱ	0.84	2.08	2.852 (5)	152
O2W—H4W···O2^iv	0.86	1.99	2.818 (5)	163
O3W—H5W···O3^iv	0.85	2.19	2.794 (7)	128
O3W—H6W···O3^v	0.85	1.96	2.770 (6)	160
O4W—H7W···O3W	0.85	1.78	2.620 (8)	169
O4W—H8W···O7^vi	0.85	2.05	2.904 (6)	180
O5W—H9W···O5^vi	0.87	2.01	2.841 (5)	159
O5W—H10W···O4^vii	0.85	1.95	2.778 (5)	163
O6W—H11W···O3W^vii	0.85	1.87	2.679 (8)	160
O6W—H12W···O5W^viii	0.85	2.22	2.850 (5)	130

Symmetry codes: (i) x+1, y, z−1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+2, −y, −z+1; (v) x, y, z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z+1; (viii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·3.5H₂O
M_r	605.83
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.6228 (12), 10.7000 (12), 11.3694 (13)
α, β, γ (°)	83.690 (1), 81.701 (1), 87.441 (1)
V (Å³)	1270.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.29 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.775, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	6589, 4494, 3730
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.05
No. of reflections	4494
No. of parameters	346
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.59

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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—H2···O4W	0.86	1.89	2.747 (5)	172
N4—H4···O6W	0.86	1.90	2.729 (5)	161
O1—H1···O4	0.82 (3)	1.67 (3)	2.490 (5)	172 (7)
O7—H7···O6	0.82 (4)	1.63 (4)	2.440 (5)	171 (8)
O1W—H1W···O5Wⁱ	0.85	2.27	2.654 (5)	108
O1W—H2W···O8ⁱⁱ	0.85	1.90	2.737 (5)	168
O2W—H3W···O8ⁱⁱⁱ	0.84	2.08	2.852 (5)	152
O2W—H4W···O2^iv	0.86	1.99	2.818 (5)	163
O3W—H5W···O3^iv	0.85	2.19	2.794 (7)	128
O3W—H6W···O3^v	0.85	1.96	2.770 (6)	160
O4W—H7W···O3W	0.85	1.78	2.620 (8)	169
O4W—H8W···O7^vi	0.85	2.05	2.904 (6)	180
O5W—H9W···O5^vi	0.87	2.01	2.841 (5)	159
O5W—H10W···O4^vii	0.85	1.95	2.778 (5)	163
O6W—H11W···O3W^vii	0.85	1.87	2.679 (8)	160
O6W—H12W···O5W^viii	0.85	2.22	2.850 (5)	130

Symmetry codes: (i) x+1, y, z−1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+2, −y, −z+1; (v) x, y, z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y, −z+1; (viii) x, y, z−1.

Acknowledgements

This work was supported by the Nonprofit Industry Foundation of the National Ocean Administration of China (grant No. 2000905021), Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003-018(c)] and Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, R.-Z., Li, S.-J., Song, W.-D., Miao, D.-L. & Hu, S.-W. (2010). Acta Cryst. E66, m897–m898. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
He, L.-Z., Li, S.-J., Song, W.-D. & Miao, D.-L. (2010). Acta Cryst. E66, m896. Web of Science CrossRef IUCr Journals Google Scholar
Li, C.-J., Hu, S., Li, W., Lam, C. K., Zheng, Y.-Z. & Tong, M.-L. (2006). Eur. J. Inorg. Chem. pp. 1931–1935. Web of Science CSD CrossRef Google Scholar
Li, S.-J., Yan, J.-B., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m280. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, Y.-L., Kravtsov, V., Walsh, R. D., Poddar, P., Srikanth, H. & Eddaoudi, M. (2004). Chem. Commun. pp. 2806–2807. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sun, Y.-Q., Zhang, J., Chen, Y.-M. & Yang, G.-Y. (2005). Angew. Chem. Int. Ed. 44, 5814–5817. Web of Science CSD CrossRef CAS Google Scholar
Yan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zou, R.-Q., Sakurai, H. & Xu, Q. (2006). Angew. Chem. Int. Ed. 45, 2542–2546. Web of Science CSD CrossRef CAS Google Scholar

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