Diaqua­bis­(5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2N3,O4)cadmium N,N-dimethyl­formamide disolvate

Tong, S.-W.; Li, S.-J.; Song, W.-D.; Miao, D.-L.; An, J.-B.

doi:10.1107/S1600536811050264

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1870-m1871

https://doi.org/10.1107/S1600536811050264

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Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-κ²N³,O⁴)cadmium N,N-dimethylformamide disolvate

Shao-Wei Tong,^a Shi-Jie Li,^b Wen-Dong Song,^c ^* Dong-Liang Miao ^a and Jing-Bo An ^a

^aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, ^bSchool of Enviroment Science and Engineering, Donghua University, Shanghai 200051, People's Republic of China, and ^cCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 21 November 2011; accepted 23 November 2011; online 30 November 2011)

In the title complex, [Cd(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the six-coordinate Cd^II ion is in a slightly distorted octahedral environment, defined by two O atoms from two coordinated water molecules and two carboxylate O atoms and two N atoms from two N,O-bidentate 5-carboxy-2-propyl-1H-imidazole-4-carboxylate ligands. In the crystal, complex molecules and dimethylformamide solvent molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds into a two-dimensional supramolecular structure. The propyl groups of the ligands are disordered over two conformations with refined occupancies of 0.680 (7) and 0.320 (7).

Related literature

For our past work based on the H₃PIDC (2-propyl-imidazol-4,5-dicarboxylic acid) ligand, see: Fan et al. (2010 ); Li, Song, Miao, Tong et al. (2011 ); Li, Miao et al. (2010 ); Li, Yan et al. (2010 ); Song et al. (2010 ); He et al. (2010 ); Yan et al. (2010 ). For our past work based on the H₃EIDC (2-ethyl-1H-imidazol-4,5-dicarboxylic acid) ligand, see: Li, Ma et al. (2011 ); Li, Song, Miao, Hu et al. (2011 ).

Experimental

Crystal data

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r = 688.97
Orthorhombic, P n a 2₁
a = 16.6040 (14) Å
b = 9.8516 (8) Å
c = 18.4154 (16) Å
V = 3012.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 295 K
0.27 × 0.24 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.815, T_max = 0.851
16187 measured reflections
4421 independent reflections
3111 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.079
S = 1.00
4421 reflections
444 parameters
233 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1285 Friedel pairs
Flack parameter: −0.04 (4)

Table 1
Selected bond lengths (Å)

Cd1—N4	2.262 (4)
Cd1—N2	2.262 (4)
Cd1—O2W	2.325 (6)
Cd1—O1W	2.322 (5)
Cd1—O4	2.356 (5)
Cd1—O8	2.357 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.69	2.460 (6)	155
O6—H6⋯O7	0.82	1.64	2.453 (6)	174
O1W—H1W⋯O10	0.83 (2)	1.94 (2)	2.763 (6)	175 (9)
O1W—H2W⋯O5ⁱ	0.82 (2)	2.00 (4)	2.771 (6)	158 (9)
O2W—H3W⋯O1ⁱⁱ	0.80 (2)	2.02 (3)	2.787 (6)	161 (7)
O2W—H4W⋯O9	0.80 (2)	2.02 (3)	2.791 (6)	162 (8)
N1—H1A⋯O10ⁱⁱⁱ	0.86	1.91	2.761 (6)	170
N3—H3A⋯O9^iv	0.86	1.94	2.792 (6)	171
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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/S1600536811050264/pk2369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050264/pk2369Isup2.hkl

checkCIF report

Comment top

In recent years, structures containing metals and N-heterocyclic carboxylic acids have drawn increasing attention due to their fascinating structures and potential applications in many fields. For instance, N-heterocyclic carboxylic acids H₃IDC (imidazole-4,5-dicarboxylic acid) which can be deprotonated to form H₂IDC^-, HIDC^2- and IDC^3- anions under various pH conditions, have been broadly used to obtain a variety of metal-organic frameworks with novel structures and exceptional properties. In our previous research, efforts have been focused on the design and synthesis of interesting metal organic complexes with derivatives of H₃IDC, such as H₃PIDC (2-propyl-imidazole-4,5-dicarboxylic acid) (Fan et al., 2010; Li, Miao et al., 2010; Li, Yan et al., 2010; Li, Song, Miao, Tong et al., 2011; He et al., 2010; Song et al., 2010; Yan et al., 2010) and H₃EIDC (2-ethyl-1H-imidazole-4,5-dicarboxylic acid) (Li, Song, Miao, Hu et al., 2011; Li, Ma et al., 2011). To continue our studies, we report the synthesis and structure of a new Cd(II) complex obtained from the H₃PIDC ligand and cadmiun nitrate under hydrothermal conditions.

As shown in the Fig. 1, the title complex consists of one Cd^II ion, two mono-deprotonated H₂PIDC ligands, two coordinated water molecules and two dimethylformamide solvent molecules. The Cd^II atom is six-coordinate in a slightly distorted octahedral geometry, connected with two N,O-bidentate ligands [Cd—O = 2.321 (5) Å and Cd—N = 2.262 (4) Å] and two coordinated water molecules [Cd—O = 2.356 (5) Å]. It is noted that the two imidazole rings are nearly coplanar. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are connected via hydrogen bonds (Table 1) into a two-dimensional supramolecular structure. The propyl groups of H₂PIDC^- are disordered over conformations with refined occupancies of 0.679 (7):0.321 (7).

Related literature top

For our past work based on the H₃PIDC (2-propyl-imidazole-4,5-dicarboxylic acid ) ligand, see: Fan et al. (2010); Li, Song, Miao, Tong et al. (2011); Li, Miao et al. (2010); Li, Yan et al. (2010); Song et al. (2010); He et al. (2010); Yan et al. (2010). For our past work based on the H₃EIDC (2-ethyl-1H-imidazole-4,5-dicarboxylic acid) ligand, see: Li, Ma et al. (2011); Li, Song, Miao, Hu et al. (2011).

Experimental top

A mixture of Cd(CH₃COO)₂ (0.2 mmol, 0.046 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.2 mmol, 0.39 g) in 15 ml DMF was sealed in an autoclave equipped with a Teflon liner (25 ml) and then heated at 413 K for 3 days. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Structure description top

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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, non-H atoms are shown with 30% probability displacement ellipsoids.

Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ²N³,O⁴)cadmium N,N-dimethylformamide disolvate top

Crystal data top

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	F(000) = 1416
M_r = 688.97	D_x = 1.519 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3600 reflections
a = 16.6040 (14) Å	θ = 1.4–28°
b = 9.8516 (8) Å	µ = 0.79 mm⁻¹
c = 18.4154 (16) Å	T = 295 K
V = 3012.3 (4) Å³	Block, colourless
Z = 4	0.27 × 0.24 × 0.21 mm

Data collection top

Rigaku/MSC Mercury CCD diffractometer	4421 independent reflections
Radiation source: fine-focus sealed tube	3111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 26.3°, θ_min = 2.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −20→20
T_min = 0.815, T_max = 0.851	k = −11→12
16187 measured reflections	l = −22→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.020P)² + 3.2P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
4421 reflections	Δρ_max = 0.41 e Å⁻³
444 parameters	Δρ_min = −0.39 e Å⁻³
233 restraints	Absolute structure: Flack (1983), 1285 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (4)

Crystal data top

[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO	V = 3012.3 (4) Å³
M_r = 688.97	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.6040 (14) Å	µ = 0.79 mm⁻¹
b = 9.8516 (8) Å	T = 295 K
c = 18.4154 (16) Å	0.27 × 0.24 × 0.21 mm

Data collection top

Rigaku/MSC Mercury CCD diffractometer	4421 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	3111 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.851	R_int = 0.046
16187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.41 e Å⁻³
S = 1.00	Δρ_min = −0.39 e Å⁻³
4421 reflections	Absolute structure: Flack (1983), 1285 Friedel pairs
444 parameters	Absolute structure parameter: −0.04 (4)
233 restraints

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	0.61035 (2)	0.49830 (5)	0.52305 (9)	0.04966 (12)
O1	0.4830 (3)	1.1346 (4)	0.5670 (3)	0.0656 (16)
O2	0.5807 (3)	1.0620 (5)	0.6382 (3)	0.0668 (14)
H2	0.5962	0.9882	0.6534	0.080*
O3	0.6581 (3)	0.8521 (5)	0.6574 (3)	0.0677 (14)
O4	0.6630 (3)	0.6406 (4)	0.6142 (3)	0.0614 (13)
O5	0.7407 (3)	−0.1351 (4)	0.4749 (3)	0.0665 (16)
O6	0.6439 (3)	−0.0594 (5)	0.4016 (3)	0.0674 (14)
H6	0.6161	0.0092	0.3987	0.081*
O7	0.5653 (3)	0.1490 (4)	0.3846 (3)	0.0614 (13)
O8	0.5579 (2)	0.3569 (4)	0.4313 (3)	0.0572 (13)
O1W	0.7047 (3)	0.5956 (4)	0.4459 (4)	0.0730 (16)
H1W	0.748 (3)	0.554 (6)	0.440 (5)	0.110*
H2W	0.718 (4)	0.675 (3)	0.442 (5)	0.110*
O2W	0.5174 (3)	0.4033 (4)	0.6026 (3)	0.0662 (15)
H3W	0.519 (4)	0.325 (3)	0.590 (4)	0.099*
H4W	0.473 (2)	0.434 (6)	0.596 (5)	0.099*
N1	0.4706 (3)	0.8811 (4)	0.4998 (3)	0.0429 (15)
H1A	0.4358	0.9371	0.4826	0.051*
N2	0.5401 (2)	0.6945 (4)	0.5161 (4)	0.0391 (11)
N3	0.7518 (3)	0.1189 (5)	0.5425 (3)	0.0483 (17)
H3A	0.7873	0.0636	0.5592	0.058*
N4	0.6815 (2)	0.3026 (4)	0.5273 (4)	0.0418 (11)
C1	0.5241 (3)	0.9076 (5)	0.5542 (3)	0.0398 (14)
C2	0.5677 (3)	0.7909 (5)	0.5641 (3)	0.0396 (14)
C3	0.5277 (4)	1.0437 (6)	0.5882 (4)	0.0517 (18)
C4	0.6343 (4)	0.7584 (6)	0.6152 (4)	0.0527 (17)
C5	0.4819 (3)	0.7508 (5)	0.4775 (3)	0.0414 (14)
C6A	0.4334 (10)	0.686 (2)	0.4188 (5)	0.059 (3)	0.680 (7)
H6A	0.3842	0.7379	0.4119	0.071*	0.680 (7)
H6B	0.4183	0.5953	0.4338	0.071*	0.680 (7)
C7A	0.4787 (7)	0.6779 (11)	0.3461 (6)	0.076 (3)	0.680 (7)
H7A	0.5335	0.6477	0.3544	0.091*	0.680 (7)
H7B	0.4525	0.6126	0.3145	0.091*	0.680 (7)
C8A	0.4793 (9)	0.8133 (12)	0.3110 (7)	0.105 (4)	0.680 (7)
H8A	0.4993	0.8050	0.2623	0.158*	0.680 (7)
H8B	0.5134	0.8735	0.3380	0.158*	0.680 (7)
H8C	0.4255	0.8491	0.3098	0.158*	0.680 (7)
C6B	0.439 (2)	0.676 (4)	0.4189 (8)	0.065 (4)	0.320 (7)
H6C	0.3824	0.6690	0.4324	0.077*	0.320 (7)
H6D	0.4603	0.5846	0.4167	0.077*	0.320 (7)
C7B	0.4436 (13)	0.738 (3)	0.3427 (13)	0.080 (3)	0.320 (7)
H7C	0.4013	0.7008	0.3124	0.096*	0.320 (7)
H7D	0.4354	0.8358	0.3458	0.096*	0.320 (7)
C8B	0.5227 (14)	0.710 (3)	0.3096 (14)	0.105 (6)	0.320 (7)
H8D	0.5154	0.6838	0.2598	0.157*	0.320 (7)
H8E	0.5487	0.6379	0.3357	0.157*	0.320 (7)
H8F	0.5556	0.7902	0.3118	0.157*	0.320 (7)
C9	0.6991 (3)	0.0907 (5)	0.4879 (3)	0.0409 (15)
C10	0.6547 (3)	0.2079 (5)	0.4781 (3)	0.0399 (14)
C11	0.7400 (3)	0.2446 (5)	0.5661 (3)	0.0434 (15)
C12	0.6953 (4)	−0.0449 (6)	0.4524 (4)	0.0501 (17)
C13	0.5881 (4)	0.2408 (6)	0.4287 (4)	0.0467 (16)
C14A	0.7785 (8)	0.3070 (14)	0.6317 (5)	0.075 (3)	0.680 (7)
H14A	0.7634	0.4018	0.6353	0.091*	0.680 (7)
H14B	0.8367	0.3017	0.6276	0.091*	0.680 (7)
C15A	0.7501 (10)	0.2293 (14)	0.7006 (7)	0.108 (3)	0.680 (7)
H15A	0.6917	0.2293	0.7027	0.129*	0.680 (7)
H15B	0.7682	0.1358	0.6982	0.129*	0.680 (7)
C16A	0.7827 (10)	0.2939 (17)	0.7661 (6)	0.132 (4)	0.680 (7)
H16A	0.7636	0.2465	0.8083	0.199*	0.680 (7)
H16B	0.7653	0.3867	0.7681	0.199*	0.680 (7)
H16C	0.8404	0.2906	0.7648	0.199*	0.680 (7)
C14B	0.7994 (14)	0.320 (3)	0.6113 (10)	0.068 (4)	0.320 (7)
H14C	0.7917	0.4168	0.6047	0.081*	0.320 (7)
H14D	0.8536	0.2976	0.5955	0.081*	0.320 (7)
C15B	0.7901 (14)	0.284 (3)	0.6922 (12)	0.093 (4)	0.320 (7)
H15C	0.7966	0.1874	0.6990	0.112*	0.320 (7)
H15D	0.8312	0.3305	0.7203	0.112*	0.320 (7)
C16B	0.7095 (15)	0.327 (3)	0.7171 (14)	0.113 (6)	0.320 (7)
H16D	0.7064	0.3180	0.7689	0.169*	0.320 (7)
H16E	0.6693	0.2702	0.6949	0.169*	0.320 (7)
H16F	0.7003	0.4196	0.7037	0.169*	0.320 (7)
O9	0.3702 (2)	0.5396 (4)	0.6089 (3)	0.0675 (14)
N5	0.3911 (3)	0.7234 (5)	0.6798 (3)	0.0514 (13)
C17	0.3557 (3)	0.6572 (5)	0.6270 (3)	0.0559 (19)
H17A	0.3162	0.7031	0.6009	0.067*
C18	0.3685 (3)	0.8631 (5)	0.6949 (3)	0.080 (2)
H18A	0.3248	0.8892	0.6637	0.119*
H18B	0.4138	0.9215	0.6864	0.119*
H18C	0.3519	0.8709	0.7447	0.119*
C19	0.4499 (5)	0.6607 (9)	0.7254 (5)	0.087 (3)
H19A	0.4500	0.5645	0.7170	0.131*
H19B	0.4371	0.6784	0.7753	0.131*
H19C	0.5022	0.6971	0.7145	0.131*
O10	0.8514 (2)	0.4647 (4)	0.4356 (3)	0.0676 (15)
N6	0.8302 (3)	0.2882 (5)	0.3600 (3)	0.0548 (14)
C20	0.8676 (4)	0.3505 (7)	0.4120 (4)	0.060 (2)
H20A	0.9104	0.3050	0.4336	0.072*
C21	0.7640 (4)	0.3522 (8)	0.3232 (5)	0.075 (2)
H21A	0.7836	0.4272	0.2951	0.112*
H21B	0.7258	0.3843	0.3583	0.112*
H21C	0.7384	0.2876	0.2917	0.112*
C22	0.8521 (5)	0.1525 (7)	0.3359 (5)	0.084 (3)
H22A	0.8067	0.0929	0.3416	0.126*
H22B	0.8962	0.1196	0.3646	0.126*
H22C	0.8676	0.1553	0.2857	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04830 (18)	0.02748 (15)	0.0732 (3)	0.00652 (16)	−0.0012 (3)	−0.0011 (2)
O1	0.060 (3)	0.033 (2)	0.104 (5)	0.009 (2)	0.004 (3)	−0.005 (2)
O2	0.079 (4)	0.040 (3)	0.082 (4)	0.000 (3)	0.002 (3)	−0.019 (3)
O3	0.080 (4)	0.054 (3)	0.069 (4)	0.003 (2)	−0.028 (3)	−0.015 (3)
O4	0.062 (3)	0.047 (3)	0.075 (4)	0.005 (2)	−0.024 (3)	0.003 (3)
O5	0.063 (3)	0.031 (2)	0.105 (5)	0.011 (2)	0.008 (3)	−0.005 (3)
O6	0.075 (4)	0.039 (3)	0.088 (4)	0.004 (3)	−0.011 (3)	−0.019 (3)
O7	0.070 (3)	0.048 (3)	0.067 (3)	−0.003 (2)	−0.015 (3)	−0.008 (2)
O8	0.060 (3)	0.038 (2)	0.074 (4)	0.010 (2)	−0.015 (3)	0.002 (2)
O1W	0.066 (3)	0.040 (3)	0.113 (5)	−0.001 (2)	0.022 (4)	−0.002 (3)
O2W	0.064 (3)	0.037 (2)	0.098 (4)	0.001 (2)	0.017 (3)	−0.005 (3)
N1	0.038 (3)	0.033 (2)	0.059 (4)	0.008 (2)	−0.001 (3)	0.008 (2)
N2	0.040 (2)	0.030 (2)	0.047 (3)	0.0019 (17)	−0.008 (3)	−0.007 (3)
N3	0.037 (3)	0.036 (2)	0.072 (5)	0.007 (2)	−0.002 (3)	0.012 (3)
N4	0.038 (2)	0.0281 (19)	0.059 (3)	0.0001 (17)	0.003 (3)	0.008 (3)
C1	0.037 (3)	0.031 (3)	0.052 (4)	0.002 (2)	0.004 (3)	0.000 (3)
C2	0.043 (3)	0.031 (3)	0.045 (4)	0.001 (2)	0.002 (3)	0.004 (3)
C3	0.047 (4)	0.035 (3)	0.073 (5)	−0.005 (3)	0.016 (4)	−0.007 (3)
C4	0.052 (4)	0.048 (4)	0.057 (5)	0.000 (3)	−0.010 (4)	0.008 (4)
C5	0.036 (3)	0.035 (3)	0.053 (4)	0.001 (3)	0.001 (3)	0.002 (3)
C6A	0.056 (4)	0.056 (4)	0.064 (5)	0.001 (4)	−0.011 (4)	−0.006 (4)
C7A	0.068 (5)	0.081 (5)	0.079 (5)	0.004 (4)	−0.009 (4)	−0.006 (4)
C8A	0.112 (7)	0.109 (6)	0.095 (7)	−0.021 (6)	0.006 (6)	0.017 (6)
C6B	0.061 (6)	0.064 (6)	0.069 (6)	0.002 (5)	−0.010 (5)	−0.005 (5)
C7B	0.079 (6)	0.081 (6)	0.080 (6)	−0.002 (5)	−0.007 (5)	−0.004 (5)
C8B	0.106 (9)	0.104 (9)	0.103 (9)	−0.006 (7)	−0.006 (8)	0.001 (8)
C9	0.045 (3)	0.025 (3)	0.053 (4)	−0.004 (2)	0.012 (3)	0.003 (3)
C10	0.043 (3)	0.033 (3)	0.044 (4)	0.004 (2)	0.004 (3)	0.002 (3)
C11	0.045 (4)	0.036 (3)	0.050 (4)	−0.001 (3)	0.003 (3)	−0.002 (3)
C12	0.045 (4)	0.034 (3)	0.071 (5)	−0.007 (3)	0.018 (4)	−0.007 (3)
C13	0.053 (4)	0.033 (3)	0.054 (5)	−0.002 (3)	0.005 (4)	−0.003 (3)
C14A	0.075 (5)	0.070 (5)	0.082 (5)	−0.004 (4)	−0.018 (5)	−0.009 (5)
C15A	0.108 (6)	0.119 (6)	0.097 (5)	−0.025 (5)	−0.002 (5)	−0.011 (5)
C16A	0.150 (8)	0.152 (8)	0.095 (5)	−0.016 (7)	−0.017 (6)	−0.010 (6)
C14B	0.068 (7)	0.067 (6)	0.067 (7)	−0.011 (6)	−0.012 (6)	−0.004 (6)
C15B	0.098 (6)	0.097 (6)	0.084 (6)	−0.022 (5)	−0.012 (6)	−0.008 (6)
C16B	0.122 (9)	0.114 (9)	0.102 (9)	−0.010 (8)	−0.011 (8)	−0.008 (8)
O9	0.052 (3)	0.053 (3)	0.098 (4)	−0.003 (2)	−0.003 (3)	−0.012 (3)
N5	0.045 (3)	0.050 (3)	0.059 (4)	−0.002 (3)	0.005 (3)	−0.002 (3)
C17	0.043 (4)	0.045 (4)	0.080 (6)	0.004 (3)	0.002 (4)	−0.006 (4)
C18	0.108 (6)	0.046 (4)	0.084 (6)	0.000 (4)	0.012 (5)	−0.013 (4)
C19	0.090 (6)	0.092 (6)	0.080 (7)	0.018 (5)	−0.010 (6)	−0.008 (5)
O10	0.049 (3)	0.053 (3)	0.101 (4)	−0.002 (2)	−0.013 (3)	−0.026 (3)
N6	0.056 (3)	0.051 (3)	0.058 (4)	−0.006 (3)	0.005 (3)	−0.011 (3)
C20	0.039 (3)	0.058 (4)	0.082 (6)	−0.001 (3)	−0.006 (4)	0.001 (4)
C21	0.058 (5)	0.090 (6)	0.076 (6)	0.017 (4)	−0.007 (4)	−0.019 (5)
C22	0.110 (7)	0.051 (4)	0.092 (7)	0.001 (4)	0.029 (6)	−0.011 (4)

Geometric parameters (Å, º) top

Cd1—N4	2.262 (4)	C7B—H7D	0.9700
Cd1—N2	2.262 (4)	C8B—H8D	0.9600
Cd1—O2W	2.325 (6)	C8B—H8E	0.9600
Cd1—O1W	2.322 (5)	C8B—H8F	0.9600
Cd1—O4	2.356 (5)	C9—C10	1.381 (7)
Cd1—O8	2.357 (5)	C9—C12	1.489 (8)
O1—C3	1.227 (7)	C10—C13	1.468 (9)
O2—C3	1.287 (8)	C11—C14B	1.490 (9)
O2—H2	0.8200	C11—C14A	1.499 (8)
O3—C4	1.269 (8)	C14A—C15A	1.555 (11)
O4—C4	1.255 (7)	C14A—H14A	0.9700
O5—C12	1.236 (7)	C14A—H14B	0.9700
O6—C12	1.275 (8)	C15A—C16A	1.467 (11)
O6—H6	0.8200	C15A—H15A	0.9700
O7—C13	1.274 (7)	C15A—H15B	0.9700
O8—C13	1.251 (6)	C16A—H16A	0.9600
O1W—H1W	0.83 (2)	C16A—H16B	0.9600
O1W—H2W	0.82 (2)	C16A—H16C	0.9600
O2W—H3W	0.80 (2)	C14B—C15B	1.537 (12)
O2W—H4W	0.80 (2)	C14B—H14C	0.9700
N1—C5	1.360 (7)	C14B—H14D	0.9700
N1—C1	1.363 (7)	C15B—C16B	1.475 (12)
N1—H1A	0.8600	C15B—H15C	0.9700
N2—C5	1.321 (7)	C15B—H15D	0.9700
N2—C2	1.376 (7)	C16B—H16D	0.9600
N3—C11	1.327 (7)	C16B—H16E	0.9600
N3—C9	1.363 (7)	C16B—H16F	0.9600
N3—H3A	0.8600	O9—C17	1.229 (6)
N4—C11	1.334 (7)	N5—C17	1.311 (7)
N4—C10	1.375 (8)	N5—C19	1.429 (9)
C1—C2	1.372 (7)	N5—C18	1.454 (6)
C1—C3	1.480 (8)	C17—H17A	0.9300
C2—C4	1.486 (9)	C18—H18A	0.9600
C5—C6B	1.490 (9)	C18—H18B	0.9600
C5—C6A	1.492 (7)	C18—H18C	0.9600
C6A—C7A	1.537 (11)	C19—H19A	0.9600
C6A—H6A	0.9700	C19—H19B	0.9600
C6A—H6B	0.9700	C19—H19C	0.9600
C7A—C8A	1.483 (10)	O10—C20	1.235 (7)
C7A—H7A	0.9700	N6—C20	1.296 (8)
C7A—H7B	0.9700	N6—C21	1.436 (9)
C8A—H8A	0.9600	N6—C22	1.455 (8)
C8A—H8B	0.9600	C20—H20A	0.9300
C8A—H8C	0.9600	C21—H21A	0.9600
C6B—C7B	1.534 (12)	C21—H21B	0.9600
C6B—H6C	0.9700	C21—H21C	0.9600
C6B—H6D	0.9700	C22—H22A	0.9600
C7B—C8B	1.476 (12)	C22—H22B	0.9600
C7B—H7C	0.9700	C22—H22C	0.9600

N4—Cd1—N2	178.7 (3)	N3—C9—C10	105.6 (5)
N4—Cd1—O2W	88.96 (17)	N3—C9—C12	122.3 (5)
N2—Cd1—O2W	92.14 (18)	C10—C9—C12	132.1 (6)
N4—Cd1—O1W	91.17 (18)	N4—C10—C9	108.0 (5)
N2—Cd1—O1W	87.75 (17)	N4—C10—C13	120.1 (5)
O2W—Cd1—O1W	178.6 (2)	C9—C10—C13	131.8 (6)
N4—Cd1—O4	106.78 (19)	N3—C11—N4	109.4 (5)
N2—Cd1—O4	73.93 (18)	N3—C11—C14B	123.4 (14)
O2W—Cd1—O4	92.1 (2)	N4—C11—C14B	124.6 (14)
O1W—Cd1—O4	86.57 (18)	N3—C11—C14A	125.7 (8)
N4—Cd1—O8	73.39 (19)	N4—C11—C14A	124.5 (8)
N2—Cd1—O8	105.90 (17)	O5—C12—O6	125.0 (6)
O2W—Cd1—O8	88.21 (17)	O5—C12—C9	118.2 (7)
O1W—Cd1—O8	93.1 (2)	O6—C12—C9	116.8 (6)
O4—Cd1—O8	179.7 (2)	O8—C13—O7	123.6 (6)
C3—O2—H2	109.5	O8—C13—C10	118.8 (6)
C4—O4—Cd1	114.8 (4)	O7—C13—C10	117.6 (5)
C12—O6—H6	109.5	C11—C14A—C15A	109.1 (8)
C13—O8—Cd1	114.8 (4)	C11—C14A—H14A	109.9
Cd1—O1W—H1W	117 (6)	C15A—C14A—H14A	109.9
Cd1—O1W—H2W	129 (6)	C11—C14A—H14B	109.9
H1W—O1W—H2W	104 (4)	C15A—C14A—H14B	109.9
Cd1—O2W—H3W	101 (6)	H14A—C14A—H14B	108.3
Cd1—O2W—H4W	111 (6)	C16A—C15A—C14A	110.3 (10)
H3W—O2W—H4W	109 (4)	C16A—C15A—H15A	109.6
C5—N1—C1	108.2 (4)	C14A—C15A—H15A	109.6
C5—N1—H1A	125.9	C16A—C15A—H15B	109.6
C1—N1—H1A	125.9	C14A—C15A—H15B	109.6
C5—N2—C2	107.5 (4)	H15A—C15A—H15B	108.1
C5—N2—Cd1	140.0 (4)	C11—C14B—C15B	111.2 (16)
C2—N2—Cd1	112.4 (4)	C11—C14B—H14C	109.4
C11—N3—C9	109.7 (5)	C15B—C14B—H14C	109.4
C11—N3—H3A	125.2	C11—C14B—H14D	109.4
C9—N3—H3A	125.2	C15B—C14B—H14D	109.4
C11—N4—C10	107.3 (4)	H14C—C14B—H14D	108.0
C11—N4—Cd1	139.8 (5)	C16B—C15B—C14B	109.2 (11)
C10—N4—Cd1	112.8 (4)	C16B—C15B—H15C	109.8
N1—C1—C2	106.3 (5)	C14B—C15B—H15C	109.8
N1—C1—C3	120.7 (5)	C16B—C15B—H15D	109.8
C2—C1—C3	132.9 (6)	C14B—C15B—H15D	109.8
C1—C2—N2	108.4 (5)	H15C—C15B—H15D	108.3
C1—C2—C4	131.1 (6)	C15B—C16B—H16D	109.5
N2—C2—C4	120.5 (5)	C15B—C16B—H16E	109.5
O1—C3—O2	122.6 (6)	H16D—C16B—H16E	109.5
O1—C3—C1	120.1 (7)	C15B—C16B—H16F	109.5
O2—C3—C1	117.3 (6)	H16D—C16B—H16F	109.5
O4—C4—O3	124.2 (6)	H16E—C16B—H16F	109.5
O4—C4—C2	118.2 (6)	C17—N5—C19	121.9 (6)
O3—C4—C2	117.6 (5)	C17—N5—C18	119.9 (6)
N2—C5—N1	109.5 (5)	C19—N5—C18	118.2 (6)
N2—C5—C6B	122 (2)	O9—C17—N5	125.6 (5)
N1—C5—C6B	128 (2)	O9—C17—H17A	117.2
N2—C5—C6A	127.3 (10)	N5—C17—H17A	117.2
N1—C5—C6A	123.2 (10)	N5—C18—H18A	109.5
C5—C6A—C7A	113.0 (9)	N5—C18—H18B	109.5
C5—C6A—H6A	109.0	H18A—C18—H18B	109.5
C7A—C6A—H6A	109.0	N5—C18—H18C	109.5
C5—C6A—H6B	109.0	H18A—C18—H18C	109.5
C7A—C6A—H6B	109.0	H18B—C18—H18C	109.5
H6A—C6A—H6B	107.8	N5—C19—H19A	109.5
C8A—C7A—C6A	109.6 (10)	N5—C19—H19B	109.5
C8A—C7A—H7A	109.8	H19A—C19—H19B	109.5
C6A—C7A—H7A	109.8	N5—C19—H19C	109.5
C8A—C7A—H7B	109.8	H19A—C19—H19C	109.5
C6A—C7A—H7B	109.8	H19B—C19—H19C	109.5
H7A—C7A—H7B	108.2	C20—N6—C21	120.5 (6)
C5—C6B—C7B	116 (2)	C20—N6—C22	122.7 (7)
C5—C6B—H6C	108.3	C21—N6—C22	116.8 (6)
C7B—C6B—H6C	108.3	O10—C20—N6	125.9 (6)
C5—C6B—H6D	108.3	O10—C20—H20A	117.0
C7B—C6B—H6D	108.3	N6—C20—H20A	117.0
H6C—C6B—H6D	107.4	N6—C21—H21A	109.5
C8B—C7B—C6B	110.4 (12)	N6—C21—H21B	109.5
C8B—C7B—H7C	109.6	H21A—C21—H21B	109.5
C6B—C7B—H7C	109.6	N6—C21—H21C	109.5
C8B—C7B—H7D	109.6	H21A—C21—H21C	109.5
C6B—C7B—H7D	109.6	H21B—C21—H21C	109.5
H7C—C7B—H7D	108.1	N6—C22—H22A	109.5
C7B—C8B—H8D	109.5	N6—C22—H22B	109.5
C7B—C8B—H8E	109.5	H22A—C22—H22B	109.5
H8D—C8B—H8E	109.5	N6—C22—H22C	109.5
C7B—C8B—H8F	109.5	H22A—C22—H22C	109.5
H8D—C8B—H8F	109.5	H22B—C22—H22C	109.5
H8E—C8B—H8F	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.69	2.460 (6)	155
O6—H6···O7	0.82	1.64	2.453 (6)	174
O1W—H1W···O10	0.83 (2)	1.94 (2)	2.763 (6)	175 (9)
O1W—H2W···O5ⁱ	0.82 (2)	2.00 (4)	2.771 (6)	158 (9)
O2W—H3W···O1ⁱⁱ	0.80 (2)	2.02 (3)	2.787 (6)	161 (7)
O2W—H4W···O9	0.80 (2)	2.02 (3)	2.791 (6)	162 (8)
N1—H1A···O10ⁱⁱⁱ	0.86	1.91	2.761 (6)	170
N3—H3A···O9^iv	0.86	1.94	2.792 (6)	171

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

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M_r	688.97
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	16.6040 (14), 9.8516 (8), 18.4154 (16)
V (Å³)	3012.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.27 × 0.24 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.815, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	16187, 4421, 3111
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.079, 1.00
No. of reflections	4421
No. of parameters	444
No. of restraints	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.39
Absolute structure	Flack (1983), 1285 Friedel pairs
Absolute structure parameter	−0.04 (4)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—N4	2.262 (4)	Cd1—O1W	2.322 (5)
Cd1—N2	2.262 (4)	Cd1—O4	2.356 (5)
Cd1—O2W	2.325 (6)	Cd1—O8	2.357 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.69	2.460 (6)	155.2
O6—H6···O7	0.82	1.64	2.453 (6)	173.9
O1W—H1W···O10	0.83 (2)	1.94 (2)	2.763 (6)	175 (9)
O1W—H2W···O5ⁱ	0.82 (2)	2.00 (4)	2.771 (6)	158 (9)
O2W—H3W···O1ⁱⁱ	0.80 (2)	2.02 (3)	2.787 (6)	161 (7)
O2W—H4W···O9	0.80 (2)	2.02 (3)	2.791 (6)	162 (8)
N1—H1A···O10ⁱⁱⁱ	0.86	1.91	2.761 (6)	170.3
N3—H3A···O9^iv	0.86	1.94	2.792 (6)	170.8

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

Acknowledgements

The work was supported by the Nonprofit Industry Foundation of the National Ocean Administration of China (grant No. 2000905021), the Guangdong Oceanic Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121), the Guangdong Province Key Project in the Field of Social Development (grant No. A2009011–007(c)), the Science and Technology Department of Guangdong Province Project (grant No. 00087061110314018) and the Guangdong Natural Science Fundation (No. 9252408801000002).

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