Poly[[(2,2′-bipyridine)(μ3-7-oxabicyclo­[2.2.1]heptane-2,3-dicarboxyl­ato)cadmium] monohydrate]

Zhang, L.-L.; Li, S.-K.; Feng, J.; Lin, Q.-Y.

doi:10.1107/S1600536811036634

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1390-m1391

https://doi.org/10.1107/S1600536811036634

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Poly[[(2,2′-bipyridine)(μ₃-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato)cadmium] monohydrate]

Ling-Ling Zhang,^a Shi-Kun Li,^a,^b Jie Feng ^a and Qiu-Yue Lin ^a,^b ^*

^aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky51@zjnu.cn

(Received 21 April 2011; accepted 8 September 2011; online 14 September 2011)

The title compound, {[Cd(C₈H₈O₅)(C₁₀H₈N₂)]·H₂O}_n, was obtained by the reaction of cadmium acetate with 2,2′-bipyridine and 7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride. The Cd^II atom is seven-coordinated in a distorted pentagonal–bipyramidal configuration, defined by five O atoms from the carboxylate groups of three 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylato ligands and two N atoms from the 2,2′-bipyridine ligand. Two O atoms link two Cd^II atoms, forming a dinuclear center: the Cd—O—Cd bridging angle is 110.19 (6)°. The polymeric structure extends along [100] and is linked by intermolecular O—H⋯O hydrogen bonds involving the solvent water molecule. Extensive π–π stacking exists between 2,2-bypiridine ligands along [010] with centroid-centroid distance of 3.650 (2) Å

Related literature

For background to the applications of norcantharidin [systematic name: 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride], see: Wang et al. (1989 ). F or related structures, see: Yin et al. (2003 ); Wang et al. (2009 ).

Experimental

Crystal data

[Cd(C₈H₈O₅)(C₁₀H₈N₂)]·H₂O
M_r = 470.75
Triclinic, $[P \overline 1]$
a = 8.2599 (1) Å
b = 10.5950 (2) Å
c = 11.1097 (2) Å
α = 111.784 (1)°
β = 94.066 (1)°
γ = 102.749 (1)°
V = 867.94 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 296 K
0.33 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.803, T_max = 0.918
13190 measured reflections
3972 independent reflections
3699 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.059
S = 0.95
3972 reflections
250 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3ⁱ	0.92 (2)	2.19 (4)	2.980 (4)	144 (5)
O1W—H1WA⋯O1Wⁱⁱ	0.92 (2)	2.38 (6)	2.833 (8)	110 (5)
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2001 ); 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 datablock global. DOI: https://doi.org/10.1107/S1600536811036634/zb2016sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036634/zb2016Isup2.hkl

checkCIF report

Comment top

7-oxabicyclo(2,2,1)heptane-2,3-dicarboxylic anhydride (norcantharidin) is a variety of pharmacologically important compound such as protein kinase inhibitors and antitumor properties (Wang, 1989). Demethylcantharate is the acid radical of norcantharidin. A copper complex of 2,2'-bipyridine and demethylcantharate was reported (Yin et al., 2003); and a similar cadmium complex of demethylcantharate (Wang et al., 2009) has been reported.

Cadmium acetate can react with 2,2'-bipyridine and norcantharidin to form the title compound. X-ray crystallography measurement confirmed the molecular structure and the atom connectivity for the title compound (Fig. 1). The cadmium atom is seven-coordinated in a distorted pentagonal bipyramidal configuration, defined by five oxygen atoms (O1,O2,O1A,O3B,O4B) from carboxylate groups of three demethylcantharates and two nitrogen atoms (N1,N2) from 2,2'-bipyridine. O1 and O1A link two cadmium atoms(Cd1,Cd1A) to form a dinuclear center, and the The angle of the bridging O1(Cd1—O1—Cd1A)), is 110.19 (6)°.Each demethylcantharate acts as a four-coordinated bridging linker that connects two cadmium centers.

It showed that the polymeric molecules grow in [100] direction,and are linked by H-bonds(O1W—H1WA···O3; O1W—H1WA···O1W) to form a plane. Extensive pi-stacking is observed between 2,2-bypiridine ligands propagated along [010], linking the planes with the distance between planes of 3.4738 Å.

Related literature top

For background to the applications of norcantharidin [systematic name: 7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride], see: Wang et al. (1989). F or related structures, see: Yin et al. (2003); Wang et al. (2009).

Experimental top

A mixture of 0.5 mmol norcantharidin, 0.5 mmol 2,2'-bipyridine,0.5 mmol cadmium acetate and 10 mL distilled water was sealed in a 25 mL Teflon-lined stainless vessel and heated at 433 K for 3 d, then cooled slowly to room temperature. The solution was filtered and block shaped colorless transparent crystals were obtained.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. A view of the molecule of (I) showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability, hydrogen atoms and water molecules were omitted.

Poly[[(2,2'-bipyridine)(µ₃-7-oxabicyclo[2.2.1]heptane-2,3- dicarboxylato)cadmium] monohydrate] top

Crystal data top

[Cd(C₈H₈O₅)(C₁₀H₈N₂)]·H₂O	Z = 2
M_r = 470.75	F(000) = 472
Triclinic, P1	D_x = 1.801 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2599 (1) Å	Cell parameters from 7860 reflections
b = 10.5950 (2) Å	θ = 2.0–27.6°
c = 11.1097 (2) Å	µ = 1.30 mm⁻¹
α = 111.784 (1)°	T = 296 K
β = 94.066 (1)°	Block, colourless
γ = 102.749 (1)°	0.33 × 0.14 × 0.07 mm
V = 867.94 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.803, T_max = 0.918	k = −13→13
13190 measured reflections	l = −14→14

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0358P)² + 0.509P] where P = (F_o² + 2F_c²)/3
3972 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 0.34 e Å⁻³
3 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Cd(C₈H₈O₅)(C₁₀H₈N₂)]·H₂O	γ = 102.749 (1)°
M_r = 470.75	V = 867.94 (2) Å³
Triclinic, P1	Z = 2
a = 8.2599 (1) Å	Mo Kα radiation
b = 10.5950 (2) Å	µ = 1.30 mm⁻¹
c = 11.1097 (2) Å	T = 296 K
α = 111.784 (1)°	0.33 × 0.14 × 0.07 mm
β = 94.066 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3972 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3699 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.918	R_int = 0.021
13190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	3 restraints
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.34 e Å⁻³
3972 reflections	Δρ_min = −0.56 e Å⁻³
250 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	0.622884 (17)	0.135016 (14)	0.438680 (14)	0.02838 (6)
N1	0.7226 (2)	0.34613 (18)	0.41261 (17)	0.0312 (4)
N2	0.5919 (2)	0.32243 (19)	0.62096 (18)	0.0329 (4)
O1W	0.4578 (5)	0.1298 (4)	0.0551 (3)	0.1174 (12)
H1WA	0.411 (7)	0.057 (5)	−0.024 (3)	0.176*
H1WB	0.400 (8)	0.088 (6)	0.104 (5)	0.176*
O1	0.37311 (19)	−0.02140 (17)	0.40538 (16)	0.0371 (3)
O2	0.3303 (2)	0.11060 (18)	0.30183 (19)	0.0449 (4)
O3	−0.3040 (2)	−0.0038 (2)	0.22846 (18)	0.0500 (5)
O4	−0.1199 (2)	0.09023 (19)	0.40964 (15)	0.0432 (4)
O5	−0.0940 (2)	−0.27932 (18)	0.14335 (18)	0.0474 (4)
C1	0.2765 (2)	0.0124 (2)	0.33481 (19)	0.0274 (4)
C2	0.0974 (2)	−0.0774 (2)	0.29330 (19)	0.0267 (4)
H2A	0.0520	−0.0788	0.3721	0.032*
C3	0.0822 (3)	−0.2314 (2)	0.1986 (2)	0.0361 (5)
H3A	0.1177	−0.2882	0.2426	0.043*
C4	0.1675 (3)	−0.2356 (3)	0.0796 (2)	0.0452 (6)
H4A	0.1784	−0.3293	0.0290	0.054*
H4B	0.2776	−0.1685	0.1058	0.054*
C5	0.0417 (4)	−0.1935 (4)	0.0024 (3)	0.0565 (7)
H5A	0.0937	−0.1068	−0.0067	0.068*
H5B	−0.0049	−0.2675	−0.0841	0.068*
C6	−0.0928 (3)	−0.1738 (3)	0.0910 (2)	0.0439 (6)
H6A	−0.2029	−0.1827	0.0448	0.053*
C7	−0.0255 (3)	−0.0357 (2)	0.21353 (19)	0.0296 (4)
H7A	0.0382	0.0371	0.1878	0.036*
C8	−0.1600 (3)	0.0185 (2)	0.2884 (2)	0.0305 (4)
C9	0.7903 (3)	0.3532 (3)	0.3088 (2)	0.0402 (5)
H9A	0.7896	0.2695	0.2400	0.048*
C10	0.8609 (3)	0.4784 (3)	0.2992 (3)	0.0465 (6)
H10A	0.9063	0.4794	0.2252	0.056*
C11	0.8631 (4)	0.6025 (3)	0.4012 (3)	0.0477 (6)
H11A	0.9115	0.6889	0.3979	0.057*
C12	0.7923 (3)	0.5967 (2)	0.5088 (2)	0.0407 (5)
H12A	0.7914	0.6793	0.5784	0.049*
C13	0.7229 (3)	0.4670 (2)	0.5117 (2)	0.0295 (4)
C14	0.6425 (3)	0.4529 (2)	0.6236 (2)	0.0295 (4)
C15	0.6177 (3)	0.5688 (2)	0.7256 (2)	0.0393 (5)
H15A	0.6548	0.6591	0.7273	0.047*
C16	0.5372 (4)	0.5476 (3)	0.8235 (2)	0.0476 (6)
H16A	0.5199	0.6237	0.8924	0.057*
C17	0.4825 (3)	0.4128 (3)	0.8190 (2)	0.0463 (6)
H17A	0.4261	0.3964	0.8835	0.056*
C18	0.5134 (3)	0.3037 (3)	0.7171 (2)	0.0410 (5)
H18A	0.4784	0.2129	0.7145	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02580 (9)	0.02276 (9)	0.03633 (9)	0.00709 (6)	0.00848 (6)	0.01055 (6)
N1	0.0303 (9)	0.0274 (9)	0.0358 (9)	0.0080 (7)	0.0086 (7)	0.0118 (7)
N2	0.0360 (10)	0.0287 (9)	0.0367 (9)	0.0109 (7)	0.0097 (8)	0.0139 (7)
O1W	0.152 (3)	0.093 (2)	0.087 (2)	0.012 (2)	−0.004 (2)	0.0295 (18)
O1	0.0269 (8)	0.0421 (9)	0.0458 (9)	0.0071 (6)	0.0014 (6)	0.0233 (7)
O2	0.0348 (9)	0.0379 (9)	0.0687 (11)	0.0044 (7)	0.0074 (8)	0.0317 (8)
O3	0.0282 (8)	0.0570 (11)	0.0526 (10)	0.0190 (8)	0.0038 (7)	0.0047 (8)
O4	0.0451 (10)	0.0547 (10)	0.0328 (8)	0.0276 (8)	0.0114 (7)	0.0118 (7)
O5	0.0317 (9)	0.0380 (9)	0.0558 (10)	0.0016 (7)	0.0018 (7)	0.0058 (8)
C1	0.0246 (9)	0.0265 (10)	0.0305 (9)	0.0095 (7)	0.0078 (8)	0.0086 (8)
C2	0.0238 (9)	0.0296 (10)	0.0299 (9)	0.0072 (8)	0.0074 (7)	0.0147 (8)
C3	0.0306 (11)	0.0291 (11)	0.0454 (12)	0.0065 (8)	0.0051 (9)	0.0122 (9)
C4	0.0414 (13)	0.0494 (14)	0.0414 (12)	0.0219 (11)	0.0124 (10)	0.0078 (11)
C5	0.0595 (17)	0.078 (2)	0.0342 (12)	0.0364 (15)	0.0134 (12)	0.0131 (13)
C6	0.0334 (12)	0.0545 (15)	0.0339 (11)	0.0177 (11)	−0.0002 (9)	0.0042 (10)
C7	0.0254 (10)	0.0361 (11)	0.0298 (9)	0.0104 (8)	0.0068 (8)	0.0144 (8)
C8	0.0291 (10)	0.0288 (10)	0.0385 (11)	0.0101 (8)	0.0113 (8)	0.0163 (9)
C9	0.0457 (13)	0.0340 (12)	0.0401 (12)	0.0102 (10)	0.0141 (10)	0.0130 (10)
C10	0.0549 (15)	0.0436 (14)	0.0423 (13)	0.0054 (11)	0.0162 (11)	0.0212 (11)
C11	0.0589 (16)	0.0339 (13)	0.0485 (14)	−0.0002 (11)	0.0099 (12)	0.0214 (11)
C12	0.0507 (14)	0.0261 (11)	0.0401 (12)	0.0038 (10)	0.0052 (10)	0.0115 (9)
C13	0.0264 (10)	0.0273 (10)	0.0334 (10)	0.0066 (8)	0.0009 (8)	0.0117 (8)
C14	0.0283 (10)	0.0273 (10)	0.0324 (10)	0.0087 (8)	0.0017 (8)	0.0110 (8)
C15	0.0475 (13)	0.0276 (11)	0.0396 (12)	0.0107 (9)	0.0082 (10)	0.0091 (9)
C16	0.0561 (16)	0.0411 (14)	0.0384 (12)	0.0153 (11)	0.0118 (11)	0.0058 (10)
C17	0.0537 (15)	0.0497 (15)	0.0385 (12)	0.0149 (12)	0.0174 (11)	0.0186 (11)
C18	0.0489 (14)	0.0344 (12)	0.0436 (12)	0.0112 (10)	0.0156 (11)	0.0183 (10)

Geometric parameters (Å, º) top

Cd1—O1	2.2511 (15)	C3—H3A	0.9800
Cd1—O4ⁱ	2.2963 (16)	C4—C5	1.541 (4)
Cd1—N2	2.3285 (18)	C4—H4A	0.9700
Cd1—N1	2.3382 (17)	C4—H4B	0.9700
Cd1—O1ⁱⁱ	2.4513 (15)	C5—C6	1.534 (3)
Cd1—O3ⁱ	2.4546 (17)	C5—H5A	0.9700
Cd1—O2	2.6704 (17)	C5—H5B	0.9700
Cd1—C8ⁱ	2.720 (2)	C6—C7	1.535 (3)
Cd1—C1	2.826 (2)	C6—H6A	0.9800
N1—C9	1.336 (3)	C7—C8	1.521 (3)
N1—C13	1.343 (3)	C7—H7A	0.9800
N2—C18	1.341 (3)	C8—Cd1ⁱⁱⁱ	2.720 (2)
N2—C14	1.341 (3)	C9—C10	1.373 (3)
O1W—H1WA	0.915 (19)	C9—H9A	0.9300
O1W—H1WB	0.922 (19)	C10—C11	1.377 (4)
O1—C1	1.275 (2)	C10—H10A	0.9300
O1—Cd1ⁱⁱ	2.4513 (15)	C11—C12	1.383 (3)
O2—C1	1.232 (3)	C11—H11A	0.9300
O3—C8	1.249 (3)	C12—C13	1.381 (3)
O3—Cd1ⁱⁱⁱ	2.4546 (17)	C12—H12A	0.9300
O4—C8	1.252 (3)	C13—C14	1.490 (3)
O4—Cd1ⁱⁱⁱ	2.2963 (16)	C14—C15	1.395 (3)
O5—C3	1.438 (3)	C15—C16	1.376 (4)
O5—C6	1.438 (3)	C15—H15A	0.9300
C1—C2	1.504 (3)	C16—C17	1.380 (4)
C2—C7	1.540 (3)	C16—H16A	0.9300
C2—C3	1.550 (3)	C17—C18	1.373 (3)
C2—H2A	0.9800	C17—H17A	0.9300
C3—C4	1.533 (3)	C18—H18A	0.9300

O1—Cd1—O4ⁱ	127.85 (6)	C7—C2—H2A	108.5
O1—Cd1—N2	99.82 (6)	C3—C2—H2A	108.5
O4ⁱ—Cd1—N2	121.75 (6)	O5—C3—C4	102.84 (19)
O1—Cd1—N1	137.35 (6)	O5—C3—C2	101.22 (16)
O4ⁱ—Cd1—N1	88.94 (6)	C4—C3—C2	110.98 (19)
N2—Cd1—N1	70.49 (6)	O5—C3—H3A	113.6
O1—Cd1—O1ⁱⁱ	69.81 (6)	C4—C3—H3A	113.6
O4ⁱ—Cd1—O1ⁱⁱ	84.38 (6)	C2—C3—H3A	113.6
N2—Cd1—O1ⁱⁱ	83.14 (6)	C3—C4—C5	101.08 (19)
N1—Cd1—O1ⁱⁱ	143.93 (6)	C3—C4—H4A	111.6
O1—Cd1—O3ⁱ	93.72 (6)	C5—C4—H4A	111.6
O4ⁱ—Cd1—O3ⁱ	54.58 (6)	C3—C4—H4B	111.6
N2—Cd1—O3ⁱ	162.62 (7)	C5—C4—H4B	111.6
N1—Cd1—O3ⁱ	92.16 (7)	H4A—C4—H4B	109.4
O1ⁱⁱ—Cd1—O3ⁱ	111.97 (6)	C6—C5—C4	101.4 (2)
O1—Cd1—O2	51.77 (5)	C6—C5—H5A	111.5
O4ⁱ—Cd1—O2	141.20 (6)	C4—C5—H5A	111.5
N2—Cd1—O2	92.73 (6)	C6—C5—H5B	111.5
N1—Cd1—O2	86.47 (5)	C4—C5—H5B	111.5
O1ⁱⁱ—Cd1—O2	119.82 (5)	H5A—C5—H5B	109.3
O3ⁱ—Cd1—O2	87.10 (6)	O5—C6—C5	102.7 (2)
O1—Cd1—C8ⁱ	112.42 (6)	O5—C6—C7	102.64 (18)
O4ⁱ—Cd1—C8ⁱ	27.27 (6)	C5—C6—C7	109.6 (2)
N2—Cd1—C8ⁱ	146.41 (7)	O5—C6—H6A	113.6
N1—Cd1—C8ⁱ	90.67 (6)	C5—C6—H6A	113.6
O1ⁱⁱ—Cd1—C8ⁱ	98.88 (6)	C7—C6—H6A	113.6
O3ⁱ—Cd1—C8ⁱ	27.32 (6)	C8—C7—C6	114.70 (18)
O2—Cd1—C8ⁱ	114.24 (6)	C8—C7—C2	113.22 (16)
O1—Cd1—C1	26.07 (5)	C6—C7—C2	101.20 (17)
O4ⁱ—Cd1—C1	140.84 (6)	C8—C7—H7A	109.1
N2—Cd1—C1	96.88 (6)	C6—C7—H7A	109.1
N1—Cd1—C1	111.81 (6)	C2—C7—H7A	109.1
O1ⁱⁱ—Cd1—C1	95.02 (5)	O3—C8—O4	121.56 (19)
O3ⁱ—Cd1—C1	90.48 (6)	O3—C8—C7	120.25 (19)
O2—Cd1—C1	25.70 (5)	O4—C8—C7	118.12 (18)
C8ⁱ—Cd1—C1	116.18 (6)	O3—C8—Cd1ⁱⁱⁱ	64.41 (12)
O1—Cd1—Cd1ⁱⁱ	36.61 (4)	O4—C8—Cd1ⁱⁱⁱ	57.15 (11)
O4ⁱ—Cd1—Cd1ⁱⁱ	107.21 (5)	C7—C8—Cd1ⁱⁱⁱ	174.70 (15)
N2—Cd1—Cd1ⁱⁱ	91.35 (5)	N1—C9—C10	123.0 (2)
N1—Cd1—Cd1ⁱⁱ	160.51 (4)	N1—C9—H9A	118.5
O1ⁱⁱ—Cd1—Cd1ⁱⁱ	33.21 (4)	C10—C9—H9A	118.5
O3ⁱ—Cd1—Cd1ⁱⁱ	105.99 (5)	C9—C10—C11	118.7 (2)
O2—Cd1—Cd1ⁱⁱ	87.42 (3)	C9—C10—H10A	120.7
C8ⁱ—Cd1—Cd1ⁱⁱ	108.70 (4)	C11—C10—H10A	120.7
C1—Cd1—Cd1ⁱⁱ	62.06 (4)	C10—C11—C12	119.0 (2)
C9—N1—C13	118.48 (19)	C10—C11—H11A	120.5
C9—N1—Cd1	123.34 (14)	C12—C11—H11A	120.5
C13—N1—Cd1	117.99 (14)	C13—C12—C11	119.3 (2)
C18—N2—C14	119.07 (19)	C13—C12—H12A	120.4
C18—N2—Cd1	122.58 (15)	C11—C12—H12A	120.4
C14—N2—Cd1	118.11 (14)	N1—C13—C12	121.7 (2)
H1WA—O1W—H1WB	95 (2)	N1—C13—C14	116.21 (18)
C1—O1—Cd1	103.02 (13)	C12—C13—C14	122.13 (19)
C1—O1—Cd1ⁱⁱ	143.44 (13)	N2—C14—C15	121.1 (2)
Cd1—O1—Cd1ⁱⁱ	110.19 (6)	N2—C14—C13	116.89 (18)
C1—O2—Cd1	84.22 (12)	C15—C14—C13	121.98 (19)
C8—O3—Cd1ⁱⁱⁱ	88.27 (13)	C16—C15—C14	119.0 (2)
C8—O4—Cd1ⁱⁱⁱ	95.58 (13)	C16—C15—H15A	120.5
C3—O5—C6	96.14 (17)	C14—C15—H15A	120.5
O2—C1—O1	120.98 (19)	C15—C16—C17	119.7 (2)
O2—C1—C2	123.43 (18)	C15—C16—H16A	120.2
O1—C1—C2	115.57 (17)	C17—C16—H16A	120.2
O2—C1—Cd1	70.08 (12)	C18—C17—C16	118.4 (2)
O1—C1—Cd1	50.91 (10)	C18—C17—H17A	120.8
C2—C1—Cd1	166.44 (14)	C16—C17—H17A	120.8
C1—C2—C7	117.17 (16)	N2—C18—C17	122.8 (2)
C1—C2—C3	112.65 (16)	N2—C18—H18A	118.6
C7—C2—C3	101.19 (16)	C17—C18—H18A	118.6
C1—C2—H2A	108.5

O1—Cd1—N1—C9	−98.43 (19)	N1—Cd1—C1—O1	−170.00 (12)
O4ⁱ—Cd1—N1—C9	53.92 (18)	O1ⁱⁱ—Cd1—C1—O1	−14.62 (16)
N2—Cd1—N1—C9	178.32 (19)	O3ⁱ—Cd1—C1—O1	97.48 (13)
O1ⁱⁱ—Cd1—N1—C9	132.87 (17)	O2—Cd1—C1—O1	179.8 (2)
O3ⁱ—Cd1—N1—C9	−0.57 (18)	C8ⁱ—Cd1—C1—O1	87.84 (13)
O2—Cd1—N1—C9	−87.53 (18)	Cd1ⁱⁱ—Cd1—C1—O1	−10.42 (11)
C8ⁱ—Cd1—N1—C9	26.71 (18)	O1—Cd1—C1—C2	−4.7 (5)
C1—Cd1—N1—C9	−91.96 (18)	O4ⁱ—Cd1—C1—C2	68.0 (6)
Cd1ⁱⁱ—Cd1—N1—C9	−159.50 (14)	N2—Cd1—C1—C2	−103.0 (6)
O1—Cd1—N1—C13	86.62 (17)	N1—Cd1—C1—C2	−174.7 (5)
O4ⁱ—Cd1—N1—C13	−121.02 (15)	O1ⁱⁱ—Cd1—C1—C2	−19.3 (6)
N2—Cd1—N1—C13	3.37 (14)	O3ⁱ—Cd1—C1—C2	92.8 (6)
O1ⁱⁱ—Cd1—N1—C13	−42.07 (19)	O2—Cd1—C1—C2	175.1 (6)
O3ⁱ—Cd1—N1—C13	−175.52 (15)	C8ⁱ—Cd1—C1—C2	83.2 (6)
O2—Cd1—N1—C13	97.52 (15)	Cd1ⁱⁱ—Cd1—C1—C2	−15.1 (5)
C8ⁱ—Cd1—N1—C13	−148.23 (15)	O2—C1—C2—C7	−4.4 (3)
C1—Cd1—N1—C13	93.09 (15)	O1—C1—C2—C7	177.14 (17)
Cd1ⁱⁱ—Cd1—N1—C13	25.6 (2)	Cd1—C1—C2—C7	−178.8 (5)
O1—Cd1—N2—C18	37.44 (19)	O2—C1—C2—C3	112.4 (2)
O4ⁱ—Cd1—N2—C18	−109.65 (19)	O1—C1—C2—C3	−66.1 (2)
N1—Cd1—N2—C18	174.4 (2)	Cd1—C1—C2—C3	−62.1 (6)
O1ⁱⁱ—Cd1—N2—C18	−30.63 (18)	C6—O5—C3—C4	−56.7 (2)
O3ⁱ—Cd1—N2—C18	178.09 (18)	C6—O5—C3—C2	58.15 (19)
O2—Cd1—N2—C18	89.09 (18)	C1—C2—C3—O5	−162.72 (17)
C8ⁱ—Cd1—N2—C18	−126.37 (18)	C7—C2—C3—O5	−36.8 (2)
C1—Cd1—N2—C18	63.63 (19)	C1—C2—C3—C4	−54.1 (2)
Cd1ⁱⁱ—Cd1—N2—C18	1.61 (18)	C7—C2—C3—C4	71.8 (2)
O1—Cd1—N2—C14	−136.90 (15)	O5—C3—C4—C5	34.9 (2)
O4ⁱ—Cd1—N2—C14	76.02 (16)	C2—C3—C4—C5	−72.7 (2)
N1—Cd1—N2—C14	0.04 (14)	C3—C4—C5—C6	−0.3 (3)
O1ⁱⁱ—Cd1—N2—C14	155.04 (16)	C3—O5—C6—C5	56.3 (2)
O3ⁱ—Cd1—N2—C14	3.8 (3)	C3—O5—C6—C7	−57.48 (19)
O2—Cd1—N2—C14	−85.25 (15)	C4—C5—C6—O5	−34.4 (3)
C8ⁱ—Cd1—N2—C14	59.3 (2)	C4—C5—C6—C7	74.2 (3)
C1—Cd1—N2—C14	−110.71 (15)	O5—C6—C7—C8	−88.6 (2)
Cd1ⁱⁱ—Cd1—N2—C14	−172.72 (15)	C5—C6—C7—C8	162.76 (19)
O4ⁱ—Cd1—O1—C1	−130.25 (12)	O5—C6—C7—C2	33.6 (2)
N2—Cd1—O1—C1	85.57 (13)	C5—C6—C7—C2	−75.0 (2)
N1—Cd1—O1—C1	13.77 (17)	C1—C2—C7—C8	−111.9 (2)
O1ⁱⁱ—Cd1—O1—C1	164.46 (17)	C3—C2—C7—C8	125.18 (18)
O3ⁱ—Cd1—O1—C1	−83.48 (13)	C1—C2—C7—C6	124.80 (19)
O2—Cd1—O1—C1	−0.13 (11)	C3—C2—C7—C6	1.9 (2)
C8ⁱ—Cd1—O1—C1	−104.04 (13)	Cd1ⁱⁱⁱ—O3—C8—O4	−0.2 (2)
Cd1ⁱⁱ—Cd1—O1—C1	164.46 (17)	Cd1ⁱⁱⁱ—O3—C8—C7	−177.16 (17)
O4ⁱ—Cd1—O1—Cd1ⁱⁱ	65.30 (9)	Cd1ⁱⁱⁱ—O4—C8—O3	0.2 (2)
N2—Cd1—O1—Cd1ⁱⁱ	−78.88 (7)	Cd1ⁱⁱⁱ—O4—C8—C7	177.23 (16)
N1—Cd1—O1—Cd1ⁱⁱ	−150.68 (7)	C6—C7—C8—O3	−31.7 (3)
O1ⁱⁱ—Cd1—O1—Cd1ⁱⁱ	0.0	C2—C7—C8—O3	−147.1 (2)
O3ⁱ—Cd1—O1—Cd1ⁱⁱ	112.06 (7)	C6—C7—C8—O4	151.3 (2)
O2—Cd1—O1—Cd1ⁱⁱ	−164.59 (10)	C2—C7—C8—O4	35.8 (3)
C8ⁱ—Cd1—O1—Cd1ⁱⁱ	91.51 (8)	C13—N1—C9—C10	0.4 (4)
C1—Cd1—O1—Cd1ⁱⁱ	−164.46 (17)	Cd1—N1—C9—C10	−174.6 (2)
O1—Cd1—O2—C1	0.13 (12)	N1—C9—C10—C11	0.4 (4)
O4ⁱ—Cd1—O2—C1	105.62 (14)	C9—C10—C11—C12	−0.9 (4)
N2—Cd1—O2—C1	−100.23 (13)	C10—C11—C12—C13	0.7 (4)
N1—Cd1—O2—C1	−170.48 (13)	C9—N1—C13—C12	−0.6 (3)
O1ⁱⁱ—Cd1—O2—C1	−16.58 (15)	Cd1—N1—C13—C12	174.62 (17)
O3ⁱ—Cd1—O2—C1	97.17 (13)	C9—N1—C13—C14	178.72 (19)
C8ⁱ—Cd1—O2—C1	100.38 (13)	Cd1—N1—C13—C14	−6.1 (2)
Cd1ⁱⁱ—Cd1—O2—C1	−9.00 (12)	C11—C12—C13—N1	0.1 (4)
Cd1—O2—C1—O1	−0.22 (19)	C11—C12—C13—C14	−179.2 (2)
Cd1—O2—C1—C2	−178.62 (18)	C18—N2—C14—C15	1.2 (3)
Cd1—O1—C1—O2	0.3 (2)	Cd1—N2—C14—C15	175.77 (16)
Cd1ⁱⁱ—O1—C1—O2	155.28 (18)	C18—N2—C14—C13	−177.6 (2)
Cd1—O1—C1—C2	178.79 (13)	Cd1—N2—C14—C13	−3.1 (2)
Cd1ⁱⁱ—O1—C1—C2	−26.2 (3)	N1—C13—C14—N2	6.1 (3)
Cd1ⁱⁱ—O1—C1—Cd1	155.0 (3)	C12—C13—C14—N2	−174.6 (2)
O1—Cd1—C1—O2	−179.8 (2)	N1—C13—C14—C15	−172.8 (2)
O4ⁱ—Cd1—C1—O2	−107.13 (14)	C12—C13—C14—C15	6.5 (3)
N2—Cd1—C1—O2	81.94 (13)	N2—C14—C15—C16	−1.1 (3)
N1—Cd1—C1—O2	10.24 (14)	C13—C14—C15—C16	177.7 (2)
O1ⁱⁱ—Cd1—C1—O2	165.61 (13)	C14—C15—C16—C17	−0.2 (4)
O3ⁱ—Cd1—C1—O2	−82.28 (13)	C15—C16—C17—C18	1.2 (4)
C8ⁱ—Cd1—C1—O2	−91.92 (13)	C14—N2—C18—C17	−0.1 (4)
Cd1ⁱⁱ—Cd1—C1—O2	169.82 (14)	Cd1—N2—C18—C17	−174.43 (19)
O4ⁱ—Cd1—C1—O1	72.63 (16)	C16—C17—C18—N2	−1.1 (4)
N2—Cd1—C1—O1	−98.30 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3^iv	0.92 (2)	2.19 (4)	2.980 (4)	144 (5)
O1W—H1WA···O1W^v	0.92 (2)	2.38 (6)	2.833 (8)	110 (5)

Symmetry codes: (iv) −x, −y, −z; (v) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₈O₅)(C₁₀H₈N₂)]·H₂O
M_r	470.75
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2599 (1), 10.5950 (2), 11.1097 (2)
α, β, γ (°)	111.784 (1), 94.066 (1), 102.749 (1)
V (Å³)	867.94 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.33 × 0.14 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.803, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	13190, 3972, 3699
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.059, 0.95
No. of reflections	3972
No. of parameters	250
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.56

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2001), 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
O1W—H1WA···O3ⁱ	0.915 (19)	2.19 (4)	2.980 (4)	144 (5)
O1W—H1WA···O1Wⁱⁱ	0.915 (19)	2.38 (6)	2.833 (8)	110 (5)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z.

Acknowledgements

The authors are grateful for financial support from the undergraduate innovative project of Zhejiang Province, China.

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Wang, N., Wang, Y.-J. & Lin, Q.-Y. (2009). Acta Cryst. E65, m782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yin, F.-L., Shen, J., Zou, J.-J. & Li, R.-C. (2003). Acta Chim. Sin. 61, 556–561. CAS Google Scholar

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