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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m637.
Published online 2010 May 12. doi:  10.1107/S1600536810016387
PMCID: PMC2979598

Bis(μ-biphenyl-2,2′-dicarboxyl­ato)bis­[aqua­(2,2′-bipyridine)cadmium(II)]

Abstract

In the centrosymmetric dinuclear mol­ecule of the title compound, [Cd2(C14H8O4)2(C10H8N2)2(H2O)2], the Cd2+ ion is coordinated by three O atoms from two different diphenyl­dicarboxyl­ate (dpa) ligands (one O,O′-bidentate and one monodentate), a chelating bipyridine ligand and a water mol­ecule, generating an extremely distorted trigonal-prismatic (or irregular) CdN2O4 coordination geometry for the metal ion. The bridging ligands generate an 18-membered ring, which is stabilized by two pairs of intra­molecular O—H(...)O hydrogen bonds.

Related literature

For background to coordination polymers, see: Hagrman et al. (1999 [triangle]); Ghosh & Bharadwaj (2004 [triangle]); Evans et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m637-scheme1.jpg

Experimental

Crystal data

  • [Cd2(C14H8O4)2(C10H8N2)2(H2O)2]
  • M r = 1053.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m637-efi1.jpg
  • a = 11.532 (2) Å
  • b = 10.961 (2) Å
  • c = 16.891 (3) Å
  • β = 98.37 (3)°
  • V = 2112.4 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.07 mm−1
  • T = 295 K
  • 0.12 × 0.10 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.882, T max = 0.919
  • 15936 measured reflections
  • 3697 independent reflections
  • 3223 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.063
  • S = 1.00
  • 3697 reflections
  • 295 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016387/hb5426sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016387/hb5426Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the program for talent introduction in Guangdong Higher Education Institutions (grant No. 201191) and the scientific research start-up funds of talent introduction in Maoming University (grant No. 208058).

supplementary crystallographic information

Comment

The design of inorganic-organic supramolecular complexes has received long-lasting research interest not only because of their appealing structural and topological novelty but also due to their unusual optical, electronic, magnetic and catalytic properties, and their further potential medical value derived from their antiviral and the inhibition of angiogenesis (Hagrman et al., 1999; Ghosh et al., 2004; Evans et al., 1999). In this paper, we report one new metal complexes constructed from 2,2-bipyridine, diphenate, and cadmium(II) ion.

Figure 1 gives the Cd atom is coordinated by three oxygen atoms from two different dpa ligands with Cd—O bond distance range from 2.1964 (19) to 2.586 (2) %A, and two nitrogen atoms from one bipyridine ligand (average Cd—N distance 2.343 %A). Two such asymmetric units connect to form an 18-numbered ring, which contains two Cd atoms, two dpa ligands, and two bipyridine ligands.

Experimental

A mixture of cadmium(II) acetate (1 mmol), diphenic acid (1 mmol), 2,2'-bipyridine (1 mmol), sodium hydroxide (2 mmol)and water (15 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colorless prisms of (I) were obtained from the reaction mixture.

Refinement

The water H atoms were located in a difference map and freely refined. All C-bound H atoms were placed in calculated positions with C—H = 0.93Å and refined as riding with Uiso(H) = 1.2Ueq(carrier).

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms. Unlablled atoms are generated by (1–x, 1–y, –z).

Crystal data

[Cd2(C14H8O4)2(C10H8N2)2(H2O)2]F(000) = 1056
Mr = 1053.61Dx = 1.656 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3697 reflections
a = 11.532 (2) Åθ = 3.1–25.0°
b = 10.961 (2) ŵ = 1.07 mm1
c = 16.891 (3) ÅT = 295 K
β = 98.37 (3)°Block, colorless
V = 2112.4 (7) Å30.12 × 0.10 × 0.08 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer3697 independent reflections
Radiation source: fine-focus sealed tube3223 reflections with I > 2σ(I)
graphiteRint = 0.030
phi and ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −13→13
Tmin = 0.882, Tmax = 0.919k = −12→13
15936 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0345P)2 + 0.8848P] where P = (Fo2 + 2Fc2)/3
3697 reflections(Δ/σ)max = 0.003
295 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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

xyzUiso*/Ueq
C10.7107 (2)0.6689 (2)−0.01343 (15)0.0395 (6)
C20.8213 (2)0.6527 (2)−0.04980 (14)0.0346 (5)
C30.9266 (2)0.6536 (2)0.00182 (15)0.0432 (6)
H30.92510.66070.05650.052*
C41.0330 (2)0.6445 (3)−0.02535 (17)0.0531 (7)
H41.10250.64640.01030.064*
C51.0349 (2)0.6323 (3)−0.10596 (18)0.0616 (8)
H51.10620.6257−0.12530.074*
C60.9320 (2)0.6300 (3)−0.15806 (16)0.0534 (7)
H60.93510.6218−0.21250.064*
C70.8229 (2)0.6394 (2)−0.13230 (14)0.0375 (5)
C80.6572 (3)0.8714 (3)0.17640 (18)0.0637 (8)
H80.70790.80550.17590.076*
C90.6904 (3)0.9662 (4)0.22807 (19)0.0726 (10)
H90.76030.96310.26330.087*
C100.6179 (3)1.0650 (3)0.2263 (2)0.0730 (9)
H100.63881.13110.25990.088*
C110.5144 (3)1.0669 (3)0.17499 (19)0.0603 (8)
H110.46541.13460.17240.072*
C120.4840 (2)0.9658 (2)0.12683 (15)0.0434 (6)
C130.3711 (2)0.9582 (2)0.07259 (16)0.0415 (6)
C140.2774 (3)1.0359 (2)0.0786 (2)0.0586 (8)
H140.28331.09470.11870.070*
C150.1764 (3)1.0254 (3)0.0250 (2)0.0705 (9)
H150.11331.07710.02840.085*
C160.1693 (3)0.9385 (3)−0.0332 (2)0.0696 (9)
H160.10220.9311−0.07080.084*
C170.2630 (3)0.8622 (3)−0.03524 (19)0.0573 (7)
H170.25750.8022−0.07450.069*
C180.3844 (2)0.5407 (2)0.13566 (14)0.0378 (5)
C190.3754 (2)0.4450 (2)0.19899 (14)0.0373 (5)
C200.4655 (2)0.4387 (3)0.26274 (15)0.0495 (7)
H200.52710.49400.26530.059*
C210.4666 (3)0.3531 (3)0.32235 (17)0.0628 (8)
H210.52820.35080.36450.075*
C220.3765 (3)0.2714 (3)0.31919 (18)0.0635 (9)
H220.37670.21270.35890.076*
C230.2850 (3)0.2767 (3)0.25660 (17)0.0519 (7)
H230.22360.22130.25520.062*
C240.2821 (2)0.3629 (2)0.19543 (14)0.0383 (5)
Cd10.495536 (15)0.710476 (16)0.035750 (10)0.03941 (8)
N10.5558 (2)0.8693 (2)0.12699 (13)0.0474 (5)
N20.36180 (19)0.87021 (19)0.01676 (13)0.0437 (5)
O10.62029 (16)0.71087 (16)−0.05533 (11)0.0462 (4)
O20.71202 (18)0.6405 (2)0.05848 (11)0.0609 (5)
O30.29828 (17)0.58894 (17)0.09796 (11)0.0519 (5)
O40.49025 (16)0.56627 (16)0.12540 (11)0.0494 (4)
O50.37320 (18)0.60995 (18)−0.07047 (13)0.0514 (5)
H1W0.417 (3)0.566 (3)−0.091 (2)0.080*
H2W0.330 (3)0.563 (3)−0.053 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0421 (15)0.0358 (12)0.0425 (15)−0.0027 (11)0.0129 (12)−0.0079 (11)
C20.0344 (13)0.0329 (12)0.0377 (13)−0.0020 (10)0.0088 (10)−0.0028 (10)
C30.0428 (15)0.0466 (14)0.0400 (14)−0.0024 (12)0.0056 (11)−0.0080 (12)
C40.0339 (15)0.0671 (19)0.0553 (17)−0.0017 (13)−0.0031 (12)−0.0098 (15)
C50.0313 (15)0.094 (2)0.0616 (18)−0.0063 (15)0.0133 (13)−0.0190 (18)
C60.0382 (15)0.082 (2)0.0422 (14)−0.0055 (14)0.0144 (12)−0.0101 (15)
C70.0350 (13)0.0397 (13)0.0385 (13)−0.0046 (11)0.0084 (10)−0.0027 (11)
C80.0521 (19)0.078 (2)0.0586 (18)0.0112 (16)−0.0011 (15)−0.0007 (17)
C90.056 (2)0.102 (3)0.0561 (19)−0.014 (2)−0.0035 (15)−0.0080 (19)
C100.076 (2)0.073 (2)0.070 (2)−0.016 (2)0.0110 (19)−0.0173 (18)
C110.063 (2)0.0493 (16)0.070 (2)−0.0067 (14)0.0148 (16)−0.0082 (15)
C120.0482 (16)0.0409 (14)0.0443 (14)−0.0029 (12)0.0174 (12)0.0052 (12)
C130.0433 (15)0.0298 (12)0.0543 (15)0.0016 (11)0.0168 (12)0.0089 (12)
C140.056 (2)0.0354 (14)0.087 (2)0.0062 (13)0.0204 (17)−0.0016 (14)
C150.0437 (19)0.0454 (17)0.122 (3)0.0111 (14)0.0120 (18)0.0057 (19)
C160.0488 (19)0.0480 (17)0.106 (3)0.0099 (14)−0.0086 (17)0.0095 (18)
C170.0501 (18)0.0490 (16)0.0695 (19)0.0062 (14)−0.0026 (15)0.0035 (15)
C180.0421 (15)0.0355 (12)0.0373 (13)−0.0017 (11)0.0103 (11)−0.0066 (11)
C190.0373 (14)0.0421 (13)0.0329 (12)−0.0012 (11)0.0066 (10)−0.0024 (11)
C200.0454 (16)0.0560 (16)0.0446 (15)−0.0121 (13)−0.0019 (12)0.0008 (13)
C210.064 (2)0.072 (2)0.0460 (16)−0.0134 (17)−0.0120 (14)0.0123 (16)
C220.075 (2)0.070 (2)0.0425 (16)−0.0123 (17)−0.0016 (15)0.0205 (15)
C230.0537 (18)0.0588 (17)0.0431 (15)−0.0147 (14)0.0068 (13)0.0064 (13)
C240.0354 (13)0.0469 (14)0.0339 (12)−0.0030 (11)0.0093 (10)−0.0009 (11)
Cd10.03751 (12)0.04095 (12)0.04107 (12)0.00950 (8)0.01014 (8)0.00319 (8)
N10.0439 (13)0.0520 (13)0.0469 (12)0.0065 (11)0.0083 (10)0.0021 (11)
N20.0412 (12)0.0378 (11)0.0520 (13)0.0066 (9)0.0073 (10)0.0055 (10)
O10.0362 (10)0.0566 (11)0.0475 (10)0.0040 (8)0.0119 (8)−0.0030 (9)
O20.0582 (13)0.0849 (15)0.0443 (11)0.0056 (11)0.0225 (9)0.0077 (11)
O30.0480 (12)0.0506 (11)0.0569 (11)0.0086 (9)0.0069 (9)0.0115 (9)
O40.0416 (11)0.0511 (10)0.0575 (11)−0.0050 (9)0.0132 (9)0.0107 (9)
O50.0435 (12)0.0496 (12)0.0609 (13)−0.0003 (9)0.0073 (9)0.0015 (10)

Geometric parameters (Å, °)

C1—O21.252 (3)C15—C161.363 (5)
C1—O11.259 (3)C15—H150.9300
C1—C21.505 (3)C16—C171.370 (4)
C2—C31.388 (3)C16—H160.9300
C2—C71.404 (3)C17—N21.337 (4)
C3—C41.375 (3)C17—H170.9300
C3—H30.9300C18—O31.219 (3)
C4—C51.371 (4)C18—O41.289 (3)
C4—H40.9300C18—C191.513 (3)
C5—C61.371 (4)C19—C201.385 (4)
C5—H50.9300C19—C241.397 (3)
C6—C71.394 (3)C20—C211.375 (4)
C6—H60.9300C20—H200.9300
C7—C24i1.493 (3)C21—C221.367 (4)
C8—N11.334 (4)C21—H210.9300
C8—C91.375 (5)C22—C231.382 (4)
C8—H80.9300C22—H220.9300
C9—C101.366 (5)C23—C241.397 (4)
C9—H90.9300C23—H230.9300
C10—C111.369 (5)C24—C7i1.493 (3)
C10—H100.9300Cd1—O42.1960 (18)
C11—C121.389 (4)Cd1—O12.2540 (18)
C11—H110.9300Cd1—N22.324 (2)
C12—N11.343 (3)Cd1—N12.362 (2)
C12—C131.481 (4)Cd1—O52.385 (2)
C13—N21.342 (3)Cd1—O22.586 (2)
C13—C141.391 (4)O5—H1W0.81 (4)
C14—C151.372 (5)O5—H2W0.80 (4)
C14—H140.9300
O2—C1—O1121.9 (2)C16—C17—H17118.5
O2—C1—C2118.4 (2)O3—C18—O4123.4 (2)
O1—C1—C2119.7 (2)O3—C18—C19122.4 (2)
C3—C2—C7119.2 (2)O4—C18—C19114.2 (2)
C3—C2—C1117.3 (2)C20—C19—C24119.2 (2)
C7—C2—C1123.5 (2)C20—C19—C18117.6 (2)
C4—C3—C2122.1 (2)C24—C19—C18123.2 (2)
C4—C3—H3119.0C21—C20—C19122.0 (3)
C2—C3—H3119.0C21—C20—H20119.0
C5—C4—C3118.8 (3)C19—C20—H20119.0
C5—C4—H4120.6C22—C21—C20119.5 (3)
C3—C4—H4120.6C22—C21—H21120.3
C6—C5—C4120.1 (2)C20—C21—H21120.3
C6—C5—H5119.9C21—C22—C23119.6 (3)
C4—C5—H5119.9C21—C22—H22120.2
C5—C6—C7122.3 (2)C23—C22—H22120.2
C5—C6—H6118.8C22—C23—C24121.8 (3)
C7—C6—H6118.8C22—C23—H23119.1
C6—C7—C2117.4 (2)C24—C23—H23119.1
C6—C7—C24i116.8 (2)C23—C24—C19117.9 (2)
C2—C7—C24i125.8 (2)C23—C24—C7i116.5 (2)
N1—C8—C9123.2 (3)C19—C24—C7i125.5 (2)
N1—C8—H8118.4O4—Cd1—O1123.82 (7)
C9—C8—H8118.4O4—Cd1—N2123.57 (7)
C10—C9—C8118.2 (3)O1—Cd1—N2112.39 (7)
C10—C9—H9120.9O4—Cd1—N196.65 (8)
C8—C9—H9120.9O1—Cd1—N1106.70 (7)
C9—C10—C11120.0 (3)N2—Cd1—N170.19 (8)
C9—C10—H10120.0O4—Cd1—O596.51 (7)
C11—C10—H10120.0O1—Cd1—O581.60 (7)
C10—C11—C12118.7 (3)N2—Cd1—O586.34 (8)
C10—C11—H11120.6N1—Cd1—O5156.53 (7)
C12—C11—H11120.6O4—Cd1—O278.88 (7)
N1—C12—C11121.6 (3)O1—Cd1—O253.40 (6)
N1—C12—C13116.3 (2)N2—Cd1—O2148.28 (7)
C11—C12—C13122.1 (3)N1—Cd1—O286.32 (8)
N2—C13—C14120.5 (3)O5—Cd1—O2115.29 (7)
N2—C13—C12116.7 (2)C8—N1—C12118.2 (3)
C14—C13—C12122.8 (3)C8—N1—Cd1124.6 (2)
C15—C14—C13119.7 (3)C12—N1—Cd1117.16 (18)
C15—C14—H14120.2C17—N2—C13118.8 (2)
C13—C14—H14120.2C17—N2—Cd1121.77 (18)
C16—C15—C14119.4 (3)C13—N2—Cd1117.42 (17)
C16—C15—H15120.3C1—O1—Cd1100.02 (15)
C14—C15—H15120.3C1—O2—Cd184.66 (16)
C15—C16—C17118.7 (3)C18—O4—Cd1111.79 (16)
C15—C16—H16120.7Cd1—O5—H1W105 (3)
C17—C16—H16120.7Cd1—O5—H2W110 (3)
N2—C17—C16122.9 (3)H1W—O5—H2W104 (4)
N2—C17—H17118.5

Symmetry codes: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H1W···O4i0.81 (4)1.94 (4)2.738 (3)168 (4)
O5—H2W···O2i0.80 (4)2.28 (4)2.932 (3)138 (3)

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5426).

References

  • Bruker (2001). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Evans, O. R., Xiong, R., Wang, Z., Wong, G. K. & Lin, W. (1999). Angew. Chem. Int. Ed.111, 557–559.
  • Ghosh, S. K. & Bharadwaj, P. K. (2004). Inorg. Chem.43, 2293–2298. [PubMed]
  • Hagrman, P. J., Hagrman, D. & Zubieta, J. (1999). Angew. Chem. Int. Ed.38, 2638–2684. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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