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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812000384/wm2579sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812000384/wm2579Isup2.hkl Contains datablock I

CCDC reference: 867964

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.033
wR factor = 0.084
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        4.6 Ratio

Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..        4.1 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         58
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT975_ALERT_2_C Positive Residual Density at 0.84A from O10    .       0.63 eA-3
PLAT975_ALERT_2_C Positive Residual Density at 0.76A from N4     .       0.59 eA-3
PLAT976_ALERT_2_C Negative Residual Density at 1.09A from O10    .      -0.63 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          8
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.03000 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N1  -CD1 -N1  -C12    15.00  0.00   2.575   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -CD1 -N1  -C11     3.00  0.00   2.575   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            O1  -CD1 -O1  -C1      4.00  0.00   2.575   1.555   1.555   1.555

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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)