Hexa­aqua­bis(μ-pyridine-2,6-di­carboxyl­ato-O,N,O′:O)dicadmium(II)-pyridine-2,6-di­carboxyl­ic acid (1/2)

Odoko, M.; Kusano, A.; Okabe, N.

doi:10.1107/S1600536801020888

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Hexaaquabis(μ-pyridine-2,6-dicarboxylato-O,N,O′:O)dicadmium(II)-pyridine-2,6-dicarboxylic acid (1/2)

M. Odoko, A. Kusano and N. Okabe

In the structure of the title compound, [Cd₂(C₇H₃NO₄)₂(H₂O)₆]·2C₇H₅NO₄, a centrosymmetric dinuclear Cd^II complex and free pyridine-2,6-dicarboxylic acid are present in a 1:2 ratio. Within the dinuclear complex, two Cd²⁺ ions are bridged by two carboxylate O atoms. Each Cd²⁺ ion is coordinated by one N and three O atoms of the pyridine-2,6-dicarboxylato ligands and three water O atoms, resulting in a distorted pentagonal bipyramidal coordination. The crystal structure is stabilized by hydrogen bonds involving all the H atoms of the water ligands.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020888/ob6098sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020888/ob6098Isup2.hkl Contains datablock I

CCDC reference: 180520

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R factor = 0.037
wR factor = 0.124
Data-to-parameter ratio = 10.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_707  Alert A D...A   Calc    3.275(6), Rep    3.117(5), Dev.     26.33 Sigma
                     O10  -O4      1.555   1.555

PLAT_707  Alert A D...A   Calc    3.117(6), Rep    2.956(5), Dev.     26.83 Sigma
                     O11  -O4      1.555   1.555

PLAT_725  Alert A D-H     Calc     0.95685, Rep     1.05000, Dev.      0.09 Ang.
                     O4   -H5      1.555   1.555


 Alert Level C:



PLAT_354  Alert C Short O-H Bond (0.82A)     O(9)   -   H(10)  =       0.70 Ang.


 3 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Pyridine-2,6-dicarboxylic acid (dipicolinic acid) is present in large amounts in bacterial spores (Powell, 1953; Church & Halvorson, 1959). It has been considered that it contributes to the high heat resistance of bacterial spores, in which it forms a metal complex with divalent metal ions, especially with the Ca²⁺ ion. Many crystal structures of chelate compounds of pyridine-2,6-dicarboxylic acid with divalent ions, such as Ca²⁺ (Strahs & Dickerson, 1968), Ag²⁺ (Drew et al., 1970), Ti²⁺ (Schwarzenbach, 1970), Sr²⁺ (Palmer et al., 1972), Ni²⁺ (Quaglieri et al., 1972), Fe²⁺ (Lainé, Gourdon & Launay, 1995; Lainé, Gourdon, Launay & Tuchagues, 1995), Cu²⁺, Zn²⁺ (Okabe & Oya, 2000a) and Mn²⁺ (Okabe & Oya, 2000b) have been determined. In order to clarify the coordination mode of chelate compounds of pyridine-2,6-dicarboxylic acid with divalent metal ions, we have analyzed the crystal structure of the title compound, (I).

Crystals of (I) were obtained as a 1:2 mixture of the dinuclear metal complex and free pyridine-2,6-dicarboxylic acid. Cd²⁺ ions are related by center of symmetry to each other. Each Cd²⁺ ion is coordinated by two O atoms and one N atom of the one ligand molecule, by one carboxylate O atom of the second ligand molecule and by three water O atoms. In the dinuclear complex, the carboxylate group and the N atom form a five-membered chelate ring with the Cd²⁺ ion (N2/C12/C14/O8/Cd and N2/C8/C13/O6/Cd), and the two Cd²⁺ ions are bridged by two bifurcated coordination bonds of two carboxylate O atoms [O6 and O6ⁱ; symmetry code: (i) -x, -y, 1 - z]. Each Cd²⁺ ion has seven coordinate bonds, forming a distorted pentagonal bipyramid, in which the N2, O6, O6ⁱ, O10 and O8 atoms form the distorted pentagonal plane. The pentagonal bipyramidal coordination of the d³sp³ hybrid orbital of the Cd²⁺ ion seems to be rare; it usually forms an octahedral d²sp³ hybrid orbital consisting of six coordination bonds. The planar conformation of the free ligand molecules co-crystallized with the chelate complex in (I) resembles the crystal structure of pyridine-2,6-dicarboxylic acid itself (Takusagawa et al., 1973).

Up until now, many crystal structure of chelate compounds of pyridine-2,6-dicarboxylic acid with various metal ions have been determined. In the crystal structure of Ag²⁺ (Drew et al., 1970), Sr²⁺ (Palmer et al., 1972), Ni²⁺ (Quaglieri et al., 1972), Cu²⁺ and Zn²⁺ (Okabe & Oya, 2000a), the pyridine-2,6-dicarboxylic acid ligand is coordinated to a mononuclear metal ion and acts as a terdentate ligand, in which the central metal ion is bonded to two N and four O atoms of two ligand molecules. But the Ti²⁺, Fe²⁺, Ca²⁺ and Mn²⁺ complexes are dinuclear, and the Sr²⁺ complex is polynuclear. Among these, the structures of Fe²⁺ (Lainé, Gourdon, Launay & Tuchagues, 1995) and Mn²⁺ (Okabe & Oya, 2000b) complexes are isomorphous with the Cd²⁺ complex, which are constituted of the dinuclear metal complex and free ligand molecules in 1:2 ratio. Not only do these structures have the same geometry, but they also have the same space group and similar cell constants. Each metal has three bonds to one ligand molecule, one to the second ligand molecule and three to water molecules. In the crystal structure of the title compound, the complex molecules and free ligand molecules are connected by hydrogen bonds involving all the H atoms of the water ligands.

Experimental top

Colorless plate-shaped crystals of (I) were obtained by slow evaporation from a 70% methanol-water solution of pyridine-2,6-dicarboxylic acid and cadmium chloride in a 1:4 molar ratio at room temperature.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

Figures top

Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Ellipsoids for non-H atoms correspond to 50% probability.

(I) top

Crystal data top

[Cd₂(C₇H₃NO₄)₂(H₂O)₆]·2C₇H₅NO₄	F(000) = 992.0
M_r = 997.36	D_x = 2.005 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 9.222 (3) Å	Cell parameters from 25 reflections
b = 14.768 (3) Å	θ = 14.6–15.0°
c = 12.239 (3) Å	µ = 1.39 mm⁻¹
β = 97.70 (2)°	T = 296 K
V = 1651.8 (7) Å³	Plate, colorless
Z = 2	0.20 × 0.20 × 0.05 mm

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.026
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→11
T_min = 0.784, T_max = 0.933	k = 0→19
4175 measured reflections	l = −15→15
3788 independent reflections	3 standard reflections every 150 reflections
2684 reflections with I > 2σ(I)	intensity decay: 1.4%

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.124	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.84 e Å⁻³
2684 reflections	Δρ_min = −1.39 e Å⁻³
253 parameters

Crystal data top

[Cd₂(C₇H₃NO₄)₂(H₂O)₆]·2C₇H₅NO₄	V = 1651.8 (7) Å³
M_r = 997.36	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.222 (3) Å	µ = 1.39 mm⁻¹
b = 14.768 (3) Å	T = 296 K
c = 12.239 (3) Å	0.20 × 0.20 × 0.05 mm
β = 97.70 (2)°

Data collection top

Rigaku AFC-5R diffractometer	2684 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.784, T_max = 0.933	3 standard reflections every 150 reflections
4175 measured reflections	intensity decay: 1.4%
3788 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	253 parameters
wR(F²) = 0.124	H-atom parameters not refined
S = 1.08	Δρ_max = 0.84 e Å⁻³
2684 reflections	Δρ_min = −1.39 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cd	0.08361 (4)	0.08439 (2)	0.90199 (3)	0.0248 (1)
O1	0.2982 (5)	0.4260 (2)	1.0909 (4)	0.051 (1)
O2	0.3019 (5)	0.2790 (2)	1.1255 (4)	0.047 (1)
O3	0.6280 (5)	0.1053 (3)	0.7794 (4)	0.058 (1)
O4	0.5744 (4)	0.0750 (3)	0.9485 (4)	0.0434 (10)
O5	−0.2018 (4)	0.1432 (2)	1.1556 (3)	0.0350 (9)
O6	−0.0775 (4)	0.0686 (2)	1.0389 (3)	0.0265 (7)
O7	0.1386 (4)	0.3552 (2)	0.7438 (3)	0.0325 (8)
O8	0.1488 (4)	0.2076 (2)	0.7800 (3)	0.0327 (8)
O9	−0.0975 (4)	0.0371 (2)	0.7650 (3)	0.0341 (8)
O10	0.2573 (4)	0.0281 (2)	0.8055 (3)	0.0380 (9)
O11	0.2849 (4)	0.0946 (2)	1.0519 (3)	0.0328 (8)
N1	0.4560 (4)	0.2408 (3)	0.9631 (4)	0.0295 (8)
N2	−0.0157 (4)	0.2228 (2)	0.9407 (3)	0.0220 (8)
C1	0.4146 (5)	0.3278 (3)	0.9752 (4)	0.029 (1)
C2	0.4455 (6)	0.3972 (3)	0.9052 (5)	0.036 (1)
C3	0.5179 (6)	0.3772 (4)	0.8177 (5)	0.043 (1)
C4	0.5607 (6)	0.2891 (4)	0.8035 (5)	0.040 (1)
C5	0.5286 (5)	0.2235 (3)	0.8773 (5)	0.031 (1)
C6	0.3327 (5)	0.3493 (3)	1.0713 (4)	0.029 (1)
C7	0.5803 (5)	0.1272 (4)	0.8636 (5)	0.037 (1)
C8	−0.0987 (5)	0.2277 (3)	1.0229 (4)	0.0218 (9)
C9	−0.1544 (6)	0.3097 (3)	1.0537 (4)	0.030 (1)
C10	−0.1267 (6)	0.3873 (3)	0.9991 (5)	0.035 (1)
C11	−0.0432 (6)	0.3823 (3)	0.9143 (5)	0.032 (1)
C12	0.0120 (5)	0.2991 (3)	0.8874 (4)	0.0237 (9)
C13	−0.1290 (5)	0.1394 (3)	1.0788 (4)	0.0235 (9)
C14	0.1073 (5)	0.2878 (3)	0.7967 (4)	0.0246 (9)
H1	0.4164	0.4584	0.9181	0.0436*
H2	0.5388	0.4246	0.7683	0.0513*
H3	0.6101	0.2741	0.7424	0.0478*
H4	0.2561	0.2853	1.1942	0.0463*
H5	0.6363	0.0231	0.9474	0.0463*
H6	−0.2129	0.3126	1.1123	0.0354*
H7	−0.1633	0.4447	1.0196	0.0410*
H8	−0.0245	0.4356	0.8746	0.0383*
H9	−0.1743	0.0591	0.7633	0.0463*
H10	−0.1054	−0.0099	0.7641	0.0463*
H11	0.2219	−0.0278	0.7729	0.0463*
H12	0.3362	0.0140	0.8790	0.0463*
H13	0.3419	0.1265	1.0248	0.0463*
H14	0.2340	0.1111	1.1168	0.0463*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.0334 (2)	0.0146 (2)	0.0294 (2)	0.0022 (1)	0.0153 (1)	0.0017 (1)
O1	0.085 (3)	0.023 (2)	0.051 (3)	0.011 (2)	0.035 (2)	0.001 (2)
O2	0.073 (3)	0.026 (2)	0.052 (3)	0.006 (2)	0.043 (2)	−0.001 (2)
O3	0.067 (3)	0.059 (3)	0.055 (3)	0.022 (2)	0.027 (2)	−0.010 (2)
O4	0.048 (2)	0.034 (2)	0.052 (3)	0.012 (2)	0.017 (2)	−0.002 (2)
O5	0.051 (2)	0.018 (2)	0.042 (2)	0.005 (1)	0.031 (2)	0.003 (1)
O6	0.041 (2)	0.011 (1)	0.032 (2)	0.005 (1)	0.022 (1)	0.004 (1)
O7	0.043 (2)	0.018 (2)	0.040 (2)	0.001 (1)	0.019 (2)	0.009 (1)
O8	0.050 (2)	0.014 (1)	0.040 (2)	0.003 (1)	0.029 (2)	0.004 (1)
O9	0.043 (2)	0.018 (2)	0.043 (2)	0.005 (1)	0.008 (2)	0.000 (1)
O10	0.050 (2)	0.024 (2)	0.046 (2)	0.006 (2)	0.026 (2)	0.005 (2)
O11	0.037 (2)	0.028 (2)	0.036 (2)	−0.004 (1)	0.014 (2)	−0.002 (2)
N1	0.028 (2)	0.028 (2)	0.033 (2)	0.001 (2)	0.010 (2)	−0.004 (2)
N2	0.028 (2)	0.016 (2)	0.024 (2)	0.001 (1)	0.011 (2)	−0.001 (1)
C1	0.029 (2)	0.027 (2)	0.031 (3)	−0.001 (2)	0.012 (2)	0.000 (2)
C2	0.046 (3)	0.025 (2)	0.040 (3)	−0.005 (2)	0.012 (2)	0.003 (2)
C3	0.043 (3)	0.048 (3)	0.042 (3)	−0.010 (3)	0.018 (3)	0.007 (3)
C4	0.038 (3)	0.047 (3)	0.037 (3)	−0.005 (2)	0.016 (2)	−0.007 (3)
C5	0.026 (2)	0.034 (3)	0.035 (3)	−0.001 (2)	0.010 (2)	−0.004 (2)
C6	0.034 (2)	0.026 (2)	0.028 (3)	0.001 (2)	0.010 (2)	0.000 (2)
C7	0.028 (2)	0.042 (3)	0.042 (3)	0.008 (2)	0.006 (2)	−0.009 (3)
C8	0.027 (2)	0.013 (2)	0.026 (2)	0.002 (2)	0.010 (2)	0.000 (2)
C9	0.045 (3)	0.019 (2)	0.029 (3)	0.003 (2)	0.018 (2)	0.000 (2)
C10	0.054 (3)	0.014 (2)	0.039 (3)	0.010 (2)	0.020 (2)	0.001 (2)
C11	0.048 (3)	0.014 (2)	0.036 (3)	0.003 (2)	0.015 (2)	0.005 (2)
C12	0.030 (2)	0.018 (2)	0.024 (2)	0.002 (2)	0.007 (2)	0.002 (2)
C13	0.031 (2)	0.018 (2)	0.024 (2)	0.001 (2)	0.010 (2)	0.003 (2)
C14	0.031 (2)	0.019 (2)	0.026 (2)	−0.001 (2)	0.010 (2)	0.002 (2)

Geometric parameters (Å, º) top

CD—O6	2.396 (4)	N1—C1	1.354 (6)
CD—O6ⁱ	2.376 (3)	N1—C5	1.343 (7)
CD—O8	2.478 (4)	N2—C8	1.345 (6)
CD—O9	2.310 (4)	N2—C12	1.342 (6)
CD—O10	2.271 (4)	C1—C2	1.390 (7)
CD—O11	2.434 (3)	C1—C6	1.514 (8)
CD—N2	2.315 (4)	C2—C3	1.368 (9)
O1—C6	1.209 (6)	C2—H1	0.961
O2—C6	1.284 (6)	C3—C4	1.378 (9)
O2—H4	0.994	C3—H2	0.961
O3—C7	1.216 (8)	C4—C5	1.384 (8)
O4—C7	1.301 (7)	C4—H3	0.951
O4—H5	0.958	C5—C7	1.516 (8)
O5—C13	1.227 (6)	C8—C9	1.388 (6)
O6—C13	1.271 (5)	C8—C13	1.516 (6)
O7—C14	1.242 (6)	C9—C10	1.368 (7)
O8—C14	1.271 (5)	C9—H6	0.954
O9—H9	0.777	C10—C11	1.374 (8)
O9—H10	0.698	C10—H7	0.957
O10—H11	0.955	C11—C12	1.387 (7)
O10—H12	1.099	C11—H8	0.954
O11—H13	0.810	C12—C14	1.515 (7)
O11—H14	1.005

O1···O10ⁱⁱ	2.787 (6)	O5···C11ⁱⁱ	3.327 (6)
O1···C10ⁱⁱⁱ	3.293 (6)	O5···C12ⁱⁱ	3.342 (6)
O1···O8ⁱⁱ	3.464 (6)	O5···C3^viii	3.477 (7)
O1···C3^iv	3.474 (7)	O6···O7ⁱⁱ	3.191 (5)
O1···C2^iv	3.518 (7)	O7···O9^ix	2.713 (5)
O1···O3ⁱⁱ	3.593 (6)	O7···O11^vi	2.955 (5)
O2···O8ⁱⁱ	2.514 (6)	O7···C13^vi	2.973 (5)
O2···O11	2.867 (5)	O7···C2	3.286 (6)
O2···O7ⁱⁱ	2.980 (6)	O7···C8^vi	3.466 (5)
O2···C14ⁱⁱ	3.097 (7)	O7···C3	3.509 (7)
O2···C4ⁱⁱ	3.172 (7)	O7···C1	3.568 (6)
O2···C5ⁱⁱ	3.485 (7)	O8···C6^vi	3.357 (7)
O2···N2	3.551 (5)	O8···N1	3.404 (5)
O3···O9^v	2.752 (6)	O8···C5	3.553 (6)
O3···C6^vi	3.535 (7)	O9···C10^vi	3.417 (7)
O4···O11^vii	2.821 (5)	O9···C9^vi	3.423 (6)
O4···O4^vii	2.974 (8)	O9···C11^x	3.535 (7)
O4···O11	3.117 (6)	O10···C7	3.310 (6)
O4···C13^v	3.124 (6)	O10···C3^xi	3.518 (7)
O4···O5^v	3.209 (5)	O10···C6^vi	3.538 (7)
O4···O6^v	3.254 (5)	O11···N1	2.965 (5)
O4···O10	3.275 (5)	C1···C14	3.390 (6)
O4···O10^vii	3.541 (6)	C6···C12	3.546 (6)
O5···O7ⁱⁱ	3.180 (5)	C7···C13^v	3.502 (7)
O5···C4^viii	3.183 (7)	C13···C14ⁱⁱ	3.385 (6)
O5···C14ⁱⁱ	3.290 (6)

O6—CD—O6ⁱ	69.7 (1)	N1—C1—C6	117.5 (4)
O6—CD—O8	135.7 (1)	C2—C1—C6	119.3 (4)
O6—CD—O9	91.3 (1)	C1—C2—C3	119.0 (5)
O6—CD—O10	151.1 (1)	C1—C2—H1	120.5
O6—CD—O11	87.7 (1)	C3—C2—H1	120.5
O6—CD—N2	69.1 (1)	C2—C3—C4	118.8 (6)
O6ⁱ—CD—O8	154.1 (1)	C2—C3—H2	119.7
O6ⁱ—CD—O9	83.6 (1)	C4—C3—H2	121.6
O6ⁱ—CD—O10	81.8 (1)	C3—C4—C5	119.2 (6)
O6ⁱ—CD—O11	82.9 (1)	C3—C4—H3	119.6
O6ⁱ—CD—N2	138.7 (1)	C5—C4—H3	121.2
O8—CD—O9	89.7 (1)	N1—C5—C4	123.4 (5)
O8—CD—O10	73.2 (1)	N1—C5—C7	117.6 (5)
O8—CD—O11	100.8 (1)	C4—C5—C7	119.0 (5)
O8—CD—N2	67.0 (1)	O1—C6—O2	124.9 (5)
O9—CD—O10	90.2 (1)	O1—C6—C1	121.5 (5)
O9—CD—O11	165.9 (1)	O2—C6—C1	113.6 (4)
O9—CD—N2	98.5 (1)	O3—C7—O4	125.3 (6)
O10—CD—O11	84.0 (1)	O3—C7—C5	119.9 (5)
O10—CD—N2	139.1 (1)	O4—C7—C5	114.8 (5)
O11—CD—N2	94.2 (1)	N2—C8—C9	121.2 (4)
C6—O2—H4	120.7	N2—C8—C13	116.7 (4)
C7—O4—H5	112.0	C9—C8—C13	122.1 (4)
CD—O6—CDⁱ	110.3 (1)	C8—C9—C10	119.9 (5)
CD—O6—C13	119.1 (3)	C8—C9—H6	120.7
CDⁱ—O6—C13	129.8 (3)	C10—C9—H6	119.4
CD—O8—C14	119.1 (3)	C9—C10—C11	118.9 (5)
CD—O9—H9	117.5	C9—C10—H7	121.1
CD—O9—H10	112.1	C11—C10—H7	119.9
H9—O9—H10	108.8	C10—C11—C12	119.2 (5)
CD—O10—H11	108.0	C10—C11—H8	119.9
CD—O10—H12	94.5	C12—C11—H8	120.9
H11—O10—H12	109.2	N2—C12—C11	121.9 (5)
CD—O11—H13	101.4	N2—C12—C14	115.5 (4)
CD—O11—H14	102.7	C11—C12—C14	122.6 (4)
H13—O11—H14	125.5	O5—C13—O6	127.0 (4)
C1—N1—C5	116.3 (4)	O5—C13—C8	117.3 (4)
CD—N2—C8	118.7 (3)	O6—C13—C8	115.7 (4)
CD—N2—C12	122.3 (3)	O7—C14—O8	124.6 (5)
C8—N2—C12	118.9 (4)	O7—C14—C12	119.5 (4)
N1—C1—C2	123.3 (5)	O8—C14—C12	115.9 (4)

CD—O6—CDⁱ—O6ⁱ	0.0000 (2)	O9—CD—O10—H12	−151.0
CD—O6—CDⁱ—O8ⁱ	169.8 (2)	O9—CD—O11—H13	123.7
CD—O6—CDⁱ—O9ⁱ	93.7 (1)	O9—CD—O11—H14	−105.6
CD—O6—CDⁱ—O10ⁱ	−175.1 (2)	O9—CD—N2—C8	93.9 (3)
CD—O6—CDⁱ—O11ⁱ	−90.2 (1)	O9—CD—N2—C12	−89.2 (3)
CD—O6—CDⁱ—N2ⁱ	−1.9 (2)	O10—CD—O6—C13	161.0 (3)
CD—O6—C13—O5	−173.1 (4)	O10—CD—O6ⁱ—C13ⁱ	−15.1 (4)
CD—O6—C13—C8	8.2 (5)	O10—CD—O8—C14	−166.7 (3)
CD—O6ⁱ—CDⁱ—O6	0.0000 (1)	O10—CD—O9—H9	−161.4
CD—O6ⁱ—CDⁱ—O8ⁱ	−173.6 (1)	O10—CD—O9—H10	71.4
CD—O6ⁱ—CDⁱ—O9ⁱ	−82.7 (1)	O10—CD—O11—H13	57.7
CD—O6ⁱ—CDⁱ—O10ⁱ	10.0 (3)	O10—CD—O11—H14	−171.6
CD—O6ⁱ—CDⁱ—O11ⁱ	83.2 (1)	O10—CD—N2—C8	−165.8 (3)
CD—O6ⁱ—CDⁱ—N2ⁱ	178.7 (2)	O10—CD—N2—C12	11.1 (4)
CD—O6ⁱ—C13ⁱ—O5ⁱ	4.1 (7)	O11—CD—O6—C13	87.7 (3)
CD—O6ⁱ—C13ⁱ—C8ⁱ	−177.2 (3)	O11—CD—O6ⁱ—C13ⁱ	−100.0 (4)
CD—O8—C14—O7	176.9 (3)	O11—CD—O8—C14	−86.4 (3)
CD—O8—C14—C12	−3.7 (5)	O11—CD—O9—H9	133.3
CD—N2—C8—C9	176.5 (3)	O11—CD—O9—H10	6.1
CD—N2—C8—C13	−4.1 (5)	O11—CD—O10—H11	128.1
CD—N2—C12—C11	−177.3 (3)	O11—CD—O10—H12	16.2
CD—N2—C12—C14	2.6 (5)	O11—CD—N2—C8	−80.1 (3)
O1—C6—O2—H4	−7.3	O11—CD—N2—C12	96.8 (3)
O1—C6—C1—N1	176.4 (5)	N1—C1—C2—C3	1.8 (8)
O1—C6—C1—C2	−2.7 (7)	N1—C1—C2—H1	−178.2
O2—C6—C1—N1	−5.4 (6)	N1—C5—C4—C3	0.5 (8)
O2—C6—C1—C2	175.6 (4)	N1—C5—C4—H3	−178.3
O3—C7—O4—H5	16.8	N2—CD—O6—C13	−7.7 (3)
O3—C7—C5—N1	169.7 (5)	N2—CD—O6ⁱ—C13ⁱ	171.7 (3)
O3—C7—C5—C4	−11.8 (7)	N2—CD—O8—C14	3.6 (3)
O4—C7—C5—N1	−13.0 (6)	N2—CD—O9—H9	−21.6
O4—C7—C5—C4	165.6 (5)	N2—CD—O9—H10	−148.7
O5—C13—C8—N2	178.4 (4)	N2—CD—O10—H11	−142.4
O5—C13—C8—C9	−2.2 (6)	N2—CD—O10—H12	105.7
O6—CD—O6ⁱ—CDⁱ	−0.02 (18)	N2—CD—O11—H13	−81.2
O6—CD—O6ⁱ—C13ⁱ	169.7 (4)	N2—CD—O11—H14	49.5
O6—CD—O8—C14	11.5 (4)	N2—C8—C9—C10	0.8 (7)
O6—CD—O9—H9	47.5	N2—C8—C9—H6	−179.8
O6—CD—O9—H10	−79.6	N2—C12—C11—C10	1.1 (7)
O6—CD—O10—H11	54.0	N2—C12—C11—H8	−178.5
O6—CD—O10—H12	−57.9	C1—N1—C5—C4	−0.3 (7)
O6—CD—O11—H13	−150.1	C1—N1—C5—C7	178.2 (4)
O6—CD—O11—H14	−19.3	C1—C2—C3—C4	−1.5 (8)
O6—CD—N2—C8	5.8 (3)	C1—C2—C3—H2	179.3
O6—CD—N2—C12	−177.3 (4)	C1—C6—O2—H4	174.5
O6—CDⁱ—O6ⁱ—CD	0.0000 (1)	C2—C1—N1—C5	−0.9 (7)
O6—CDⁱ—O6ⁱ—C13ⁱ	−171.0 (4)	C2—C3—C4—C5	0.5 (8)
O6—CDⁱ—O8ⁱ—C14ⁱ	−177.7 (3)	C2—C3—C4—H3	179.2
O6—CDⁱ—O9ⁱ—H9ⁱ	−116.9	C3—C2—C1—C6	−179.2 (5)
O6—CDⁱ—O9ⁱ—H10ⁱ	10.3	C3—C4—C5—C7	−178.0 (5)
O6—CDⁱ—O10ⁱ—H11ⁱ	−44.5	C4—C3—C2—H1	178.5
O6—CDⁱ—O10ⁱ—H12ⁱ	67.4	C5—N1—C1—C6	−179.9 (4)
O6—CDⁱ—O11ⁱ—H13ⁱ	−140.1	C5—C4—C3—H2	179.7
O6—CDⁱ—O11ⁱ—H14ⁱ	89.1	C5—C7—O4—H5	−160.4
O6—CDⁱ—N2ⁱ—C8ⁱ	−3.9 (4)	C6—C1—C2—H1	0.8
O6—CDⁱ—N2ⁱ—C12ⁱ	179.2 (3)	C7—C5—C4—H3	3.3
O6—C13—C8—N2	−2.8 (6)	C8—N2—C12—C11	−0.4 (6)
O6—C13—C8—C9	176.6 (4)	C8—N2—C12—C14	179.5 (4)
O7—C14—C12—N2	−179.7 (4)	C8—C9—C10—C11	−0.2 (7)
O7—C14—C12—C11	0.2 (7)	C8—C9—C10—H7	−179.4
O8—CD—O6—C13	−15.4 (4)	C9—C8—N2—C12	−0.6 (6)
O8—CD—O6ⁱ—C13ⁱ	0.0 (5)	C9—C10—C11—C12	−0.8 (7)
O8—CD—O9—H9	−88.3	C9—C10—C11—H8	178.8
O8—CD—O9—H10	144.6	C10—C9—C8—C13	−178.5 (4)
O8—CD—O10—H11	−128.7	C10—C11—C12—C14	−178.8 (4)
O8—CD—O10—H12	119.4	C11—C10—C9—H6	−179.5
O8—CD—O11—H13	−13.8	C12—N2—C8—C13	178.8 (4)
O8—CD—O11—H14	116.9	C12—C11—C10—H7	178.4
O8—CD—N2—C8	180.0 (3)	C13—C8—C9—H6	0.8
O8—CD—N2—C12	−3.1 (3)	C14—C12—C11—H8	1.6
O8—C14—C12—N2	0.9 (6)	H1—C2—C3—H2	−0.7
O8—C14—C12—C11	−179.2 (4)	H2—C3—C4—H3	−1.6
O9—CD—O6—C13	−106.3 (3)	H6—C9—C10—H7	1.3
O9—CD—O6ⁱ—C13ⁱ	76.0 (4)	H7—C10—C11—H8	−2.0
O9—CD—O8—C14	103.0 (3)	H7—C10—C11—H8	−2.0
O9—CD—O10—H11	−39.1

Symmetry codes: (i) −x, −y, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x, −y+1, −z+2; (iv) −x+1, −y+1, −z+2; (v) x+1, y, z; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y, −z+2; (viii) x−1, −y+1/2, z+1/2; (ix) −x, y+1/2, −z+3/2; (x) −x, y−1/2, −z+3/2; (xi) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4···O8ⁱⁱ	0.99	1.54	2.515 (6)	165
O4—H5···O11^vii	1.05	1.88	2.821 (5)	166
O9—H9···O3^xii	0.78	1.98	2.752 (6)	172
O9—H10···O7^x	0.70	2.02	2.713 (5)	177
O10—H11···O5ⁱ	0.96	1.94	2.638 (5)	128
O10—H12···O4	1.10	2.42	3.117 (5)	133
O11—H13···O4	0.81	2.57	2.956 (5)	127
O11—H14···O7ⁱⁱ	1.01	1.95	2.956 (6)	179

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

Experimental details

Crystal data
Chemical formula	[Cd₂(C₇H₃NO₄)₂(H₂O)₆]·2C₇H₅NO₄
M_r	997.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.222 (3), 14.768 (3), 12.239 (3)
β (°)	97.70 (2)
V (Å³)	1651.8 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.784, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	4175, 3788, 2684
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.124, 1.08
No. of reflections	2684
No. of parameters	253
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.84, −1.39

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 2000), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), TEXSAN.

Selected geometric parameters (Å, º) top

CD—O6	2.396 (4)	CD—O10	2.271 (4)
CD—O6ⁱ	2.376 (3)	CD—O11	2.434 (3)
CD—O8	2.478 (4)	CD—N2	2.315 (4)
CD—O9	2.310 (4)

O6—CD—O6ⁱ	69.7 (1)	O8—CD—O11	100.8 (1)
O6—CD—O8	135.7 (1)	O8—CD—N2	67.0 (1)
O6—CD—O9	91.3 (1)	O9—CD—O10	90.2 (1)
O6—CD—O10	151.1 (1)	O9—CD—O11	165.9 (1)
O6—CD—O11	87.7 (1)	O9—CD—N2	98.5 (1)
O6—CD—N2	69.1 (1)	O10—CD—O11	84.0 (1)
O8—CD—O9	89.7 (1)	O10—CD—N2	139.1 (1)
O8—CD—O10	73.2 (1)	O11—CD—N2	94.2 (1)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4···O8ⁱⁱ	0.99	1.54	2.515 (6)	165
O4—H5···O11ⁱⁱⁱ	1.05	1.88	2.821 (5)	166
O9—H9···O3^iv	0.78	1.98	2.752 (6)	172
O9—H10···O7^v	0.70	2.02	2.713 (5)	177
O10—H11···O5ⁱ	0.96	1.94	2.638 (5)	128
O10—H12···O4	1.10	2.42	3.117 (5)	133
O11—H13···O4	0.81	2.57	2.956 (5)	127
O11—H14···O7ⁱⁱ	1.01	1.95	2.956 (6)	179

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

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