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

Ling-Ling Zhang; Shi-Kun Li; Jie Feng; Qiu-Yue Lin

doi:10.1107/S1600536811036634

. 2011 Sep 14;67(Pt 10):m1390–m1391. doi: 10.1107/S1600536811036634

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

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

PMCID: PMC3201414 PMID: 22065044

Abstract

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,
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[F ² > 2σ(F ²)] = 0.022
wR(F ²) = 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

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.

Supplementary Material

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811036634/zb2016sup1.cif

e-67-m1390-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036634/zb2016Isup2.hkl

e-67-m1390-Isup2.hkl^{(194.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.