Diaqua­bis­{1-[(1H-benzimidazol-2-yl)meth­yl]-1H-1,2,4-triazole-κN4}bis­(2,4,5-tricarb­oxy­benzoato-κO1)cadmium dihydrate

Zhao, L.; Liu, B.; Jin, G.; Meng, X.

doi:10.1107/S1600536812000384

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m139-m140

doi:10.1107/S1600536812000384

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Diaquabis{1-[(1H-benzimidazol-2-yl)methyl]-1H-1,2,4-triazole-κN⁴}bis(2,4,5-tricarboxybenzoato-κO¹)cadmium dihydrate

Lei Zhao,^a Bingtao Liu,^b Guanghua Jin ^c and Xiangru Meng ^c ^*

^aSchool of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, People's Republic of China, ^bSchool of Environmental and Municipal Engineering, North China Institute of Water Conservancy and Hydroelectric Power, Zhengzhou 450011, People's Republic of China, and ^cDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: mxr@zzu.edu.cn

(Received 22 December 2011; accepted 4 January 2012; online 11 January 2012)

In the title complex, [Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂]·2H₂O, the Cd^II ion lies on an inversion center and is coordinated by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)methyl]-1H-1,2,4-triazole ligands and two O atoms from two monodeprotonated 2,4,5-tricarboxybenzoate anions in equatorial positions and by two water O atoms in axial positions, leading to a distorted octahedral environment. In the crystal, complex molecules and solvent water molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds into a three-dimensional network. Intramolecular O—H⋯O hydrogen bonds are also present.

Related literature

For background information on complexes constructed from N-heterocyclic ligands and aromatic polycarboxylate anions, see: Braverman et al. (2007 ); Liu et al. (2010 ); Prajapati et al. (2009 ).

Experimental

Crystal data

[Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂]·2H₂O
M_r = 1089.19
Triclinic, $[P \overline 1]$
a = 7.7005 (15) Å
b = 8.6131 (17) Å
c = 17.460 (3) Å
α = 75.98 (3)°
β = 82.55 (3)°
γ = 70.60 (3)°
V = 1058.2 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 293 K
0.19 × 0.18 × 0.15 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ) T_min = 0.892, T_max = 0.913
12522 measured reflections
4987 independent reflections
4758 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.05
4987 reflections
322 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.2933 (15)
Cd1—O9	2.3155 (17)
Cd1—N1	2.358 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.85	2.19	3.001 (3)	160
O5—H5⋯O6ⁱ	0.85	1.77	2.611 (3)	168
O7—H7⋯O4ⁱⁱ	0.85	1.66	2.465 (2)	156
O9—H9A⋯O8ⁱⁱⁱ	0.85	2.01	2.844 (2)	167
O9—H9B⋯O2	0.85	1.94	2.688 (2)	147
O10—H10A⋯O8^iv	0.85	2.05	2.887 (3)	169
O10—H10B⋯N4	0.85	2.21	2.704 (3)	117
N5—H5A⋯O8^v	0.86	2.13	2.922 (3)	153
Symmetry codes: (i) -x, -y+3, -z+1; (ii) x-1, y+1, z; (iii) -x, -y+3, -z; (iv) x, y-1, z; (v) x+1, y-2, z.

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000384/wm2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000384/wm2579Isup2.hkl

checkCIF report

Comment top

A large number of Cd^II complexes constructed from N-heterocyclic and aromatic polycarboxylate ligands have been synthesized since Cd^II is able to coordinate simultaneously to both oxygen-containing and nitrogen-containing ligands. Some of the final products exhibit useful functional properties (Braverman et al., 2007; Liu et al., 2010; Prajapati et al., 2009). In order to further explore such compounds with new structures, we selected 1-((1H-benzimidazol-1-yl)methyl)-1H-1,2,4-triazole and 1,2,4,5-benzenetetracarboxylic acid as educts to self-assemble with Cd(NO₃)₂ and obtained the title complex, {[Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂] (H₂O)₂}, the crystal structure of which is reported herein.

The Cd^II ion lies on an inversion center and displays a slightly distorted octahedral geometry defined by atoms O1, O1A, N1, N1A from two 1-((1H-benzimidazol-1-yl)methyl)-1H-1,2,4-triazole ligands and two monodeprotonated 1,2,4,5-benzenetetracarboxylic acid anions in equatorial positions, and by atoms O9, O9A from water molecules in axial positions (Fig. 1). Intramolecular O—H···O hydrogen bonds between the carboxyl/carboxylate groups and between coordinating water molecules and carboxylate O atoms stabilize the molecular configuration, whereas O—H···O, O—H···N and N—H···O hydrogen bonds between carboxyl/carboxylate groups, between coordinating water molecules and carboxylate O atoms, between solvent water molecules and carboxylate O atoms, between imidazole groups and carboxylate O atoms and between solvent water molecules and imidazole N atoms of adjacent molecules consolidate the crystal packing (Fig. 2).

Related literature top

For background information on complexes constructed from N-heterocyclic ligands and aromatic polycarboxylate anions, see: Braverman et al. (2007); Liu et al. (2010); Prajapati et al. (2009).

Experimental top

A mixture of Cd(NO₃)₂ (0.05 mmol), 1-((1H-benzimidazol-1-yl)methyl)-1H-1,2,4-triazole (0.05 mmol) 1,2,4,5-benzenetetracarboxylic acid (0.05 mmol), methanol (2 ml) and water (8 ml) was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 393 K for 72 h, then cooled to room temperature. Colourless crystals were obtained from the evaporated filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the molecular struicture of the title complex showing the atom labelling with displacement ellipsoids drawn at the 30% probability level. [Symmetry code A) -x, -y + 2, -z.]
	Fig. 2. View of the crystal packing of the title complex, showing the three-dimensional structure stabilized by numerous hydrogen bonds.

Diaquabis{1-[(1H-benzimidazol-2-yl)methyl]-1H-1,2,4-triazole- κN⁴}bis(2,4,5-tricarboxybenzoato-κO¹)cadmium dihydrate top

Crystal data top

[Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂]·2H₂O	Z = 1
M_r = 1089.19	F(000) = 554
Triclinic, P1	D_x = 1.709 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7005 (15) Å	Cell parameters from 3785 reflections
b = 8.6131 (17) Å	θ = 2.4–27.9°
c = 17.460 (3) Å	µ = 0.62 mm⁻¹
α = 75.98 (3)°	T = 293 K
β = 82.55 (3)°	Prism, colourless
γ = 70.60 (3)°	0.19 × 0.18 × 0.15 mm
V = 1058.2 (3) Å³

Data collection top

Rigaku Saturn CCD diffractometer	4987 independent reflections
Radiation source: fine-focus sealed tube	4758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −11→11
T_min = 0.892, T_max = 0.913	l = −22→21
12522 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0457P)² + 0.6556P] where P = (F_o² + 2F_c²)/3
4987 reflections	(Δ/σ)_max < 0.001
322 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂]·2H₂O	γ = 70.60 (3)°
M_r = 1089.19	V = 1058.2 (3) Å³
Triclinic, P1	Z = 1
a = 7.7005 (15) Å	Mo Kα radiation
b = 8.6131 (17) Å	µ = 0.62 mm⁻¹
c = 17.460 (3) Å	T = 293 K
α = 75.98 (3)°	0.19 × 0.18 × 0.15 mm
β = 82.55 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	4987 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	4758 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.913	R_int = 0.023
12522 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	Δρ_max = 0.66 e Å⁻³
4987 reflections	Δρ_min = −0.65 e Å⁻³
322 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cd1	0.0000	1.0000	0.0000	0.01995 (7)
N1	0.2410 (2)	0.7537 (2)	0.04738 (11)	0.0250 (4)
N2	0.5217 (3)	0.6030 (2)	0.09222 (12)	0.0295 (4)
N3	0.4177 (2)	0.5005 (2)	0.09340 (11)	0.0238 (4)
N4	0.4526 (3)	0.3824 (2)	0.25900 (11)	0.0269 (4)
N5	0.6329 (3)	0.1335 (2)	0.24746 (12)	0.0321 (4)
H5A	0.6930	0.0485	0.2268	0.038*
O1	−0.0272 (2)	1.1045 (2)	0.11147 (9)	0.0285 (3)
O2	0.1184 (3)	1.2920 (2)	0.05454 (10)	0.0385 (4)
O3	0.3379 (3)	0.9741 (2)	0.18617 (10)	0.0397 (4)
H3	0.2496	0.9980	0.1563	0.048*
O4	0.3395 (3)	0.9197 (2)	0.31666 (10)	0.0389 (4)
O5	0.0260 (4)	1.3218 (2)	0.46604 (11)	0.0573 (6)
H5	0.0324	1.3638	0.5046	0.069*
O6	−0.0760 (3)	1.5906 (2)	0.40745 (11)	0.0558 (6)
O7	−0.3986 (2)	1.6650 (2)	0.30619 (11)	0.0410 (4)
H7	−0.4707	1.7657	0.3002	0.049*
O8	−0.2047 (2)	1.78648 (19)	0.22713 (10)	0.0308 (3)
O9	0.2285 (2)	1.1153 (2)	−0.06019 (9)	0.0309 (4)
H9A	0.2325	1.1543	−0.1098	0.037*
H9B	0.2115	1.1975	−0.0383	0.037*
O10	0.1906 (3)	0.6873 (2)	0.23452 (12)	0.0431 (4)
H10A	0.0737	0.7278	0.2353	0.052*
H10B	0.1948	0.5903	0.2295	0.052*
C1	0.0434 (3)	1.2165 (3)	0.11195 (12)	0.0216 (4)
C2	0.2772 (3)	1.0108 (3)	0.24903 (13)	0.0231 (4)
C3	−0.0278 (3)	1.4403 (3)	0.40573 (13)	0.0293 (5)
C4	−0.2513 (3)	1.6628 (3)	0.26677 (12)	0.0233 (4)
C5	0.0265 (3)	1.2716 (2)	0.18958 (11)	0.0189 (4)
C6	0.1271 (3)	1.1709 (2)	0.25503 (12)	0.0200 (4)
C7	0.0996 (3)	1.2271 (3)	0.32503 (12)	0.0230 (4)
H7A	0.1636	1.1578	0.3688	0.028*
C8	−0.0216 (3)	1.3844 (3)	0.33102 (12)	0.0219 (4)
C9	−0.1177 (3)	1.4889 (2)	0.26518 (12)	0.0201 (4)
C10	−0.0942 (3)	1.4299 (3)	0.19571 (12)	0.0205 (4)
H10	−0.1609	1.4980	0.1524	0.025*
C11	0.4094 (3)	0.7527 (3)	0.06434 (13)	0.0274 (4)
H11	0.4418	0.8504	0.0567	0.033*
C12	0.2522 (3)	0.5920 (3)	0.06641 (13)	0.0248 (4)
H12	0.1590	0.5491	0.0616	0.030*
C13	0.4912 (3)	0.3198 (3)	0.12359 (13)	0.0265 (4)
H13A	0.6060	0.2753	0.0944	0.032*
H13B	0.4048	0.2659	0.1153	0.032*
C14	0.5248 (3)	0.2790 (3)	0.20956 (13)	0.0243 (4)
C15	0.5184 (4)	0.2989 (3)	0.33352 (14)	0.0320 (5)
C16	0.4865 (5)	0.3505 (4)	0.40519 (16)	0.0488 (7)
H16	0.4082	0.4564	0.4104	0.059*
C17	0.5784 (7)	0.2342 (5)	0.46774 (18)	0.0706 (11)
H17	0.5617	0.2624	0.5169	0.085*
C18	0.6953 (7)	0.0761 (5)	0.4597 (2)	0.0862 (15)
H18	0.7548	0.0026	0.5038	0.103*
C19	0.7268 (6)	0.0237 (4)	0.3894 (2)	0.0657 (10)
H19	0.8050	−0.0824	0.3845	0.079*
C20	0.6336 (4)	0.1404 (3)	0.32615 (15)	0.0368 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02136 (11)	0.02025 (12)	0.01892 (11)	−0.00516 (8)	−0.00346 (7)	−0.00608 (8)
N1	0.0255 (9)	0.0240 (9)	0.0242 (9)	−0.0046 (7)	−0.0072 (7)	−0.0039 (7)
N2	0.0256 (9)	0.0314 (10)	0.0325 (10)	−0.0098 (8)	−0.0068 (8)	−0.0045 (8)
N3	0.0241 (9)	0.0229 (9)	0.0233 (9)	−0.0048 (7)	−0.0042 (7)	−0.0049 (7)
N4	0.0312 (10)	0.0244 (9)	0.0232 (9)	−0.0056 (8)	−0.0024 (7)	−0.0054 (7)
N5	0.0381 (11)	0.0205 (9)	0.0326 (10)	0.0016 (8)	−0.0093 (9)	−0.0078 (8)
O1	0.0361 (8)	0.0321 (8)	0.0249 (8)	−0.0147 (7)	−0.0028 (6)	−0.0138 (7)
O2	0.0639 (12)	0.0396 (10)	0.0224 (8)	−0.0281 (9)	0.0055 (8)	−0.0134 (7)
O3	0.0416 (10)	0.0385 (10)	0.0295 (9)	0.0115 (8)	−0.0087 (7)	−0.0199 (8)
O4	0.0429 (10)	0.0274 (9)	0.0284 (9)	0.0143 (7)	−0.0057 (7)	−0.0062 (7)
O5	0.1076 (18)	0.0305 (10)	0.0227 (9)	0.0044 (11)	−0.0244 (10)	−0.0108 (8)
O6	0.1015 (18)	0.0260 (9)	0.0304 (9)	0.0067 (10)	−0.0248 (11)	−0.0153 (8)
O7	0.0338 (9)	0.0192 (8)	0.0515 (11)	0.0072 (7)	0.0105 (8)	−0.0020 (8)
O8	0.0371 (9)	0.0181 (7)	0.0327 (8)	−0.0030 (7)	−0.0017 (7)	−0.0049 (6)
O9	0.0377 (9)	0.0342 (9)	0.0268 (8)	−0.0191 (7)	0.0033 (7)	−0.0087 (7)
O10	0.0361 (10)	0.0288 (9)	0.0634 (13)	−0.0049 (8)	−0.0022 (9)	−0.0154 (9)
C1	0.0242 (10)	0.0206 (10)	0.0198 (9)	−0.0014 (8)	−0.0067 (8)	−0.0086 (8)
C2	0.0209 (9)	0.0193 (10)	0.0287 (11)	0.0001 (8)	−0.0045 (8)	−0.0116 (8)
C3	0.0406 (13)	0.0221 (10)	0.0194 (10)	0.0029 (9)	−0.0063 (9)	−0.0089 (8)
C4	0.0281 (10)	0.0173 (10)	0.0191 (9)	0.0024 (8)	−0.0060 (8)	−0.0051 (8)
C5	0.0202 (9)	0.0196 (9)	0.0186 (9)	−0.0050 (8)	−0.0025 (7)	−0.0081 (8)
C6	0.0209 (9)	0.0171 (9)	0.0214 (9)	−0.0013 (8)	−0.0038 (7)	−0.0078 (8)
C7	0.0269 (10)	0.0188 (10)	0.0190 (9)	0.0018 (8)	−0.0075 (8)	−0.0056 (8)
C8	0.0271 (10)	0.0173 (9)	0.0181 (9)	0.0006 (8)	−0.0046 (8)	−0.0067 (8)
C9	0.0205 (9)	0.0166 (9)	0.0209 (9)	−0.0003 (7)	−0.0026 (7)	−0.0065 (8)
C10	0.0217 (9)	0.0186 (9)	0.0190 (9)	−0.0009 (8)	−0.0075 (7)	−0.0040 (8)
C11	0.0275 (11)	0.0282 (11)	0.0282 (11)	−0.0101 (9)	−0.0066 (9)	−0.0045 (9)
C12	0.0246 (10)	0.0254 (10)	0.0246 (10)	−0.0064 (8)	−0.0057 (8)	−0.0055 (8)
C13	0.0280 (11)	0.0212 (10)	0.0263 (11)	−0.0009 (8)	−0.0046 (8)	−0.0060 (8)
C14	0.0248 (10)	0.0207 (10)	0.0258 (10)	−0.0041 (8)	−0.0039 (8)	−0.0050 (8)
C15	0.0439 (14)	0.0280 (12)	0.0247 (11)	−0.0144 (10)	−0.0037 (10)	−0.0015 (9)
C16	0.080 (2)	0.0409 (15)	0.0287 (13)	−0.0232 (15)	0.0006 (13)	−0.0085 (12)
C17	0.132 (4)	0.061 (2)	0.0241 (14)	−0.038 (2)	−0.0179 (18)	−0.0009 (14)
C18	0.154 (4)	0.055 (2)	0.0416 (19)	−0.024 (3)	−0.048 (2)	0.0148 (16)
C19	0.102 (3)	0.0344 (16)	0.0494 (18)	−0.0056 (17)	−0.0356 (19)	0.0053 (14)
C20	0.0507 (15)	0.0271 (12)	0.0311 (12)	−0.0107 (11)	−0.0137 (11)	0.0008 (10)

Geometric parameters (Å, º) top

Cd1—O1ⁱ	2.2933 (15)	O10—H10A	0.8500
Cd1—O1	2.2933 (15)	O10—H10B	0.8500
Cd1—O9ⁱ	2.3154 (17)	C1—C5	1.518 (3)
Cd1—O9	2.3155 (17)	C2—C6	1.493 (3)
Cd1—N1ⁱ	2.358 (2)	C3—C8	1.486 (3)
Cd1—N1	2.358 (2)	C4—C9	1.514 (3)
N1—C12	1.327 (3)	C5—C10	1.392 (3)
N1—C11	1.364 (3)	C5—C6	1.400 (3)
N2—C11	1.308 (3)	C6—C7	1.387 (3)
N2—N3	1.371 (3)	C7—C8	1.386 (3)
N3—C12	1.332 (3)	C7—H7A	0.9300
N3—C13	1.454 (3)	C8—C9	1.399 (3)
N4—C14	1.329 (3)	C9—C10	1.394 (3)
N4—C15	1.394 (3)	C10—H10	0.9300
N5—C14	1.323 (3)	C11—H11	0.9300
N5—C20	1.390 (3)	C12—H12	0.9300
N5—H5A	0.8600	C13—C14	1.493 (3)
O1—C1	1.257 (3)	C13—H13A	0.9700
O2—C1	1.243 (3)	C13—H13B	0.9700
O3—C2	1.208 (3)	C15—C20	1.385 (4)
O3—H3	0.8501	C15—C16	1.393 (4)
O4—C2	1.299 (3)	C16—C17	1.377 (4)
O5—C3	1.278 (3)	C16—H16	0.9300
O5—H5	0.8504	C17—C18	1.389 (6)
O6—C3	1.229 (3)	C17—H17	0.9300
O7—C4	1.245 (3)	C18—C19	1.374 (5)
O7—H7	0.8500	C18—H18	0.9300
O8—C4	1.255 (3)	C19—C20	1.390 (4)
O9—H9A	0.8501	C19—H19	0.9300
O9—H9B	0.8499

O1ⁱ—Cd1—O1	180.0	C7—C6—C5	119.85 (18)
O1ⁱ—Cd1—O9ⁱ	93.80 (6)	C7—C6—C2	118.63 (18)
O1—Cd1—O9ⁱ	86.20 (6)	C5—C6—C2	121.27 (18)
O1ⁱ—Cd1—O9	86.20 (6)	C8—C7—C6	121.30 (19)
O1—Cd1—O9	93.80 (6)	C8—C7—H7A	119.3
O9ⁱ—Cd1—O9	180.000 (1)	C6—C7—H7A	119.4
O1ⁱ—Cd1—N1ⁱ	93.81 (7)	C7—C8—C9	119.42 (18)
O1—Cd1—N1ⁱ	86.19 (7)	C7—C8—C3	117.30 (18)
O9ⁱ—Cd1—N1ⁱ	86.47 (7)	C9—C8—C3	122.97 (18)
O9—Cd1—N1ⁱ	93.53 (7)	C10—C9—C8	119.14 (18)
O1ⁱ—Cd1—N1	86.19 (7)	C10—C9—C4	118.22 (18)
O1—Cd1—N1	93.81 (7)	C8—C9—C4	122.62 (18)
O9ⁱ—Cd1—N1	93.53 (7)	C5—C10—C9	121.59 (18)
O9—Cd1—N1	86.47 (7)	C5—C10—H10	119.2
N1ⁱ—Cd1—N1	180.00 (9)	C9—C10—H10	119.2
C12—N1—C11	103.37 (18)	N2—C11—N1	114.5 (2)
C12—N1—Cd1	132.41 (15)	N2—C11—H11	122.7
C11—N1—Cd1	124.19 (15)	N1—C11—H11	122.7
C11—N2—N3	102.43 (17)	N1—C12—N3	109.49 (19)
C12—N3—N2	110.17 (18)	N1—C12—H12	125.3
C12—N3—C13	129.49 (19)	N3—C12—H12	125.3
N2—N3—C13	120.31 (17)	N3—C13—C14	111.69 (18)
C14—N4—C15	108.15 (19)	N3—C13—H13A	109.3
C14—N5—C20	108.8 (2)	C14—C13—H13A	109.3
C14—N5—H5A	125.6	N3—C13—H13B	109.3
C20—N5—H5A	125.6	C14—C13—H13B	109.3
C1—O1—Cd1	120.44 (14)	H13A—C13—H13B	107.9
C2—O3—H3	109.5	N5—C14—N4	110.1 (2)
C3—O5—H5	109.4	N5—C14—C13	124.4 (2)
C4—O7—H7	109.5	N4—C14—C13	125.46 (19)
Cd1—O9—H9A	120.9	C20—C15—C16	122.0 (2)
Cd1—O9—H9B	103.5	C20—C15—N4	106.7 (2)
H9A—O9—H9B	106.5	C16—C15—N4	131.3 (2)
H10A—O10—H10B	95.5	C17—C16—C15	115.6 (3)
O2—C1—O1	126.63 (19)	C17—C16—H16	122.2
O2—C1—C5	116.63 (18)	C15—C16—H16	122.2
O1—C1—C5	116.65 (18)	C16—C17—C18	122.1 (3)
O3—C2—O4	123.89 (19)	C16—C17—H17	118.9
O3—C2—C6	122.1 (2)	C18—C17—H17	118.9
O4—C2—C6	113.95 (18)	C19—C18—C17	122.8 (3)
O6—C3—O5	123.4 (2)	C19—C18—H18	118.6
O6—C3—C8	121.3 (2)	C17—C18—H18	118.6
O5—C3—C8	115.20 (19)	C18—C19—C20	115.4 (3)
O7—C4—O8	127.6 (2)	C18—C19—H19	122.3
O7—C4—C9	115.04 (19)	C20—C19—H19	122.3
O8—C4—C9	117.30 (19)	C15—C20—N5	106.2 (2)
C10—C5—C6	118.63 (18)	C15—C20—C19	122.2 (3)
C10—C5—C1	118.31 (17)	N5—C20—C19	131.6 (3)
C6—C5—C1	123.07 (17)

O1ⁱ—Cd1—N1—C12	−65.3 (2)	C7—C8—C9—C4	−179.5 (2)
O1—Cd1—N1—C12	114.7 (2)	C3—C8—C9—C4	−6.1 (3)
O9ⁱ—Cd1—N1—C12	28.3 (2)	O7—C4—C9—C10	107.0 (2)
O9—Cd1—N1—C12	−151.7 (2)	O8—C4—C9—C10	−71.0 (3)
N1ⁱ—Cd1—N1—C12	147 (100)	O7—C4—C9—C8	−71.2 (3)
O1ⁱ—Cd1—N1—C11	117.24 (18)	O8—C4—C9—C8	110.8 (2)
O1—Cd1—N1—C11	−62.76 (18)	C6—C5—C10—C9	−0.5 (3)
O9ⁱ—Cd1—N1—C11	−149.18 (17)	C1—C5—C10—C9	179.71 (19)
O9—Cd1—N1—C11	30.82 (17)	C8—C9—C10—C5	−1.9 (3)
N1ⁱ—Cd1—N1—C11	−30 (100)	C4—C9—C10—C5	179.80 (19)
C11—N2—N3—C12	0.3 (2)	N3—N2—C11—N1	−0.1 (3)
C11—N2—N3—C13	−177.99 (19)	C12—N1—C11—N2	−0.1 (3)
O1ⁱ—Cd1—O1—C1	44 (100)	Cd1—N1—C11—N2	178.02 (15)
O9ⁱ—Cd1—O1—C1	−166.06 (16)	C11—N1—C12—N3	0.2 (2)
O9—Cd1—O1—C1	13.94 (16)	Cd1—N1—C12—N3	−177.62 (14)
N1ⁱ—Cd1—O1—C1	−79.36 (16)	N2—N3—C12—N1	−0.3 (3)
N1—Cd1—O1—C1	100.64 (16)	C13—N3—C12—N1	177.7 (2)
Cd1—O1—C1—O2	6.3 (3)	C12—N3—C13—C14	−113.5 (2)
Cd1—O1—C1—C5	−177.03 (12)	N2—N3—C13—C14	64.4 (3)
O2—C1—C5—C10	69.1 (3)	C20—N5—C14—N4	−0.3 (3)
O1—C1—C5—C10	−107.8 (2)	C20—N5—C14—C13	179.3 (2)
O2—C1—C5—C6	−110.6 (2)	C15—N4—C14—N5	0.2 (3)
O1—C1—C5—C6	72.4 (3)	C15—N4—C14—C13	−179.4 (2)
C10—C5—C6—C7	2.6 (3)	N3—C13—C14—N5	−161.6 (2)
C1—C5—C6—C7	−177.66 (19)	N3—C13—C14—N4	18.0 (3)
C10—C5—C6—C2	−171.46 (18)	C14—N4—C15—C20	0.0 (3)
C1—C5—C6—C2	8.3 (3)	C14—N4—C15—C16	179.6 (3)
O3—C2—C6—C7	−162.3 (2)	C20—C15—C16—C17	0.6 (4)
O4—C2—C6—C7	15.3 (3)	N4—C15—C16—C17	−178.9 (3)
O3—C2—C6—C5	11.8 (3)	C15—C16—C17—C18	0.1 (6)
O4—C2—C6—C5	−170.64 (19)	C16—C17—C18—C19	−0.5 (7)
C5—C6—C7—C8	−2.3 (3)	C17—C18—C19—C20	0.2 (7)
C2—C6—C7—C8	171.9 (2)	C16—C15—C20—N5	−179.8 (2)
C6—C7—C8—C9	−0.2 (3)	N4—C15—C20—N5	−0.2 (3)
C6—C7—C8—C3	−174.0 (2)	C16—C15—C20—C19	−1.0 (5)
O6—C3—C8—C7	154.1 (3)	N4—C15—C20—C19	178.6 (3)
O5—C3—C8—C7	−23.7 (3)	C14—N5—C20—C15	0.3 (3)
O6—C3—C8—C9	−19.5 (4)	C14—N5—C20—C19	−178.4 (3)
O5—C3—C8—C9	162.7 (2)	C18—C19—C20—C15	0.5 (5)
C7—C8—C9—C10	2.2 (3)	C18—C19—C20—N5	179.1 (4)
C3—C8—C9—C10	175.7 (2)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.85	2.19	3.001 (3)	160
O5—H5···O6ⁱⁱ	0.85	1.77	2.611 (3)	168
O7—H7···O4ⁱⁱⁱ	0.85	1.66	2.465 (2)	156
O9—H9A···O8^iv	0.85	2.01	2.844 (2)	167
O9—H9B···O2	0.85	1.94	2.688 (2)	147
O10—H10A···O8^v	0.85	2.05	2.887 (3)	169
O10—H10B···N4	0.85	2.21	2.704 (3)	117
N5—H5A···O8^vi	0.86	2.13	2.922 (3)	153

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₅O₈)₂(C₁₀H₉N₅)₂(H₂O)₂]·2H₂O
M_r	1089.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7005 (15), 8.6131 (17), 17.460 (3)
α, β, γ (°)	75.98 (3), 82.55 (3), 70.60 (3)
V (Å³)	1058.2 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.19 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2004)
T_min, T_max	0.892, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	12522, 4987, 4758
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.05
No. of reflections	4987
No. of parameters	322
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.65

Computer programs: CrystalClear (Rigaku/MSC, 2004), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cd1—O1	2.2933 (15)	Cd1—N1	2.358 (2)
Cd1—O9	2.3155 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.85	2.19	3.001 (3)	160.3
O5—H5···O6ⁱ	0.85	1.77	2.611 (3)	168.3
O7—H7···O4ⁱⁱ	0.85	1.66	2.465 (2)	156.0
O9—H9A···O8ⁱⁱⁱ	0.85	2.01	2.844 (2)	166.6
O9—H9B···O2	0.85	1.94	2.688 (2)	146.7
O10—H10A···O8^iv	0.85	2.05	2.887 (3)	168.5
O10—H10B···N4	0.85	2.21	2.704 (3)	117.3
N5—H5A···O8^v	0.86	2.13	2.922 (3)	153.4

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

Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. J0830412).

References

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