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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m34.
Published online 2007 December 6. doi:  10.1107/S1600536807053664
PMCID: PMC2914923

Bis(3,5-dicarboxy­benzoato-κ2 O,O′)(1,10-phenanthroline-κ2 N,N′)cadmium(II)

Abstract

The mol­ecule of the title compound, [Cd(C9H5O6)2(C12H8N2)], has crystallographic twofold rotation symmetry. The CdII atom, located on the twofold axis, assumes a CdO4N2 distorted octa­hedral coordination geometry. In the crystal structure, the mol­ecules link to each other by O—H(...)O and C—H(...)O hydrogen bonding to form a three-dimensional supra­molecular network.

Related literature

For general background, see: Shi et al. (2004 [triangle]); Han et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00m34-scheme1.jpg

Experimental

Crystal data

  • [Cd(C9H5O6)2(C12H8N2)]
  • M r = 710.86
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m34-efi1.jpg
  • a = 9.838 (2) Å
  • b = 16.541 (3) Å
  • c = 16.681 (3) Å
  • β = 96.32 (3)°
  • V = 2698.1 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.88 mm−1
  • T = 298 (2) K
  • 0.32 × 0.26 × 0.24 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.765, T max = 0.816
  • 5790 measured reflections
  • 3095 independent reflections
  • 2834 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.073
  • S = 1.05
  • 3095 reflections
  • 204 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807053664/xu2344sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807053664/xu2344Isup2.hkl

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

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (grant No. 20701006), the Foundation for Excellent Youth of Jilin, China (grant No. 20070103) and the Science Foundation for Young Teachers of Northeast Normal University, China (grant No. 20070303).

supplementary crystallographic information

Comment

As part of an ongoing investigation of metal complexes with the benzene-1,3,5-tricarboxylate ligand (Shi et al., 2004; Han et al., 2005), the structure of the title CdII complex is reported here. The asymmetric unit contains a half of CdII complex, with the CdII atom residing on a crystallographic twofold axis. The CdII ion has a distorted octahedral coordination geometry formed by four O atoms and two N atoms (Table 1). This arrangement appears to be the effect of the small bite angles produced by the chelating ligands. In the crystal the molecules are connected with O—H···O and C—H···O hydrogen bonding (Table 2), forming a three-dimensional supramolecular network.

Experimental

The compound was prepared by a hydrothermal method. A mixture of Cd(NO3)2.4H2O (0.5 mmol), benzene-1,3,5-tricarboxylic acid (0.6 mmol), 1,10-phenanthroline (0.6 mmol) and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 h under autogenous pressure. Single crystals were obtained after cooling to room temperature.

Refinement

H atoms were placed in calculated positions with C—H = 0.93 Å and O—H = 0.82 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

[Cd(C9H5O6)2(C12H8N2)]F000 = 1424
Mr = 710.86Dx = 1.750 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 5790 reflections
a = 9.838 (2) Åθ = 2.4–27.5º
b = 16.541 (3) ŵ = 0.88 mm1
c = 16.681 (3) ÅT = 298 (2) K
β = 96.32 (3)ºBlock, colourless
V = 2698.1 (9) Å30.32 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer3095 independent reflections
Radiation source: fine-focus sealed tube2834 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 298(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.765, Tmax = 0.816k = −21→21
5790 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.073  w = 1/[σ2(Fo2) + (0.0396P)2 + 1.679P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3095 reflectionsΔρmax = 0.46 e Å3
204 parametersΔρmin = −0.56 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cd10.00000.095232 (10)0.25000.03259 (8)
O1−0.04641 (13)0.16023 (9)0.36635 (9)0.0375 (3)
O20.15070 (14)0.18897 (9)0.32348 (10)0.0413 (3)
O3−0.22565 (16)0.33500 (11)0.56195 (12)0.0573 (5)
H3A−0.28370.34820.59110.086*
O4−0.10746 (19)0.43487 (13)0.62596 (12)0.0609 (5)
O50.42788 (16)0.41835 (12)0.44051 (11)0.0528 (5)
H5A0.49280.44960.44800.079*
O60.34627 (16)0.49693 (11)0.53307 (11)0.0512 (4)
N10.13969 (15)−0.01388 (10)0.26674 (9)0.0307 (3)
C10.07969 (18)0.27267 (11)0.42660 (11)0.0292 (3)
C2−0.02139 (18)0.29186 (12)0.47520 (12)0.0327 (4)
H2−0.09850.25930.47450.039*
C4−0.00817 (18)0.35978 (12)0.52518 (12)0.0328 (4)
C50.1072 (2)0.40796 (12)0.52686 (13)0.0340 (4)
H50.11620.45340.55990.041*
C60.20969 (19)0.38836 (12)0.47902 (12)0.0319 (4)
C70.19579 (18)0.32127 (12)0.42853 (12)0.0312 (4)
H70.26390.30880.39610.037*
C80.06177 (17)0.20275 (11)0.36910 (11)0.0296 (3)
C9−0.1171 (2)0.38168 (14)0.57696 (14)0.0395 (4)
C100.2741 (2)−0.01298 (14)0.28658 (13)0.0409 (4)
H100.31930.03650.29070.049*
C110.3497 (2)−0.08376 (17)0.30141 (16)0.0496 (6)
H110.4434−0.08120.31690.060*
C120.2851 (2)−0.15675 (15)0.29300 (15)0.0496 (6)
H120.3348−0.20430.30200.060*
C130.1425 (2)−0.15987 (12)0.27059 (13)0.0383 (4)
C140.07359 (18)−0.08582 (10)0.25986 (11)0.0278 (3)
C150.0681 (3)−0.23439 (13)0.26011 (16)0.0517 (6)
H150.1146−0.28330.26740.062*
C170.33550 (19)0.43895 (13)0.48512 (12)0.0346 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.04347 (13)0.02012 (10)0.03363 (12)0.0000.00178 (8)0.000
O10.0322 (7)0.0345 (7)0.0470 (8)−0.0104 (5)0.0101 (6)−0.0124 (6)
O20.0349 (7)0.0409 (8)0.0502 (9)−0.0100 (6)0.0148 (6)−0.0157 (7)
O30.0398 (8)0.0598 (10)0.0774 (12)−0.0229 (8)0.0290 (8)−0.0310 (9)
O40.0555 (10)0.0641 (12)0.0674 (12)−0.0212 (9)0.0270 (9)−0.0347 (10)
O50.0361 (8)0.0668 (11)0.0580 (11)−0.0252 (7)0.0176 (7)−0.0225 (8)
O60.0420 (8)0.0523 (10)0.0612 (10)−0.0246 (7)0.0142 (7)−0.0223 (8)
N10.0301 (7)0.0288 (7)0.0329 (8)−0.0011 (6)0.0025 (6)−0.0002 (6)
C10.0274 (8)0.0265 (8)0.0333 (9)−0.0045 (6)0.0011 (6)−0.0018 (7)
C20.0291 (8)0.0313 (9)0.0378 (10)−0.0098 (7)0.0045 (7)−0.0042 (7)
C40.0301 (8)0.0329 (9)0.0360 (10)−0.0082 (7)0.0067 (7)−0.0053 (7)
C50.0325 (9)0.0334 (10)0.0364 (10)−0.0110 (7)0.0047 (7)−0.0082 (7)
C60.0282 (9)0.0334 (9)0.0339 (9)−0.0100 (7)0.0024 (7)−0.0021 (7)
C70.0261 (8)0.0328 (9)0.0345 (9)−0.0053 (7)0.0030 (6)−0.0018 (7)
C80.0281 (8)0.0261 (8)0.0342 (9)−0.0020 (6)0.0016 (6)−0.0006 (7)
C90.0368 (10)0.0383 (10)0.0455 (12)−0.0117 (8)0.0133 (8)−0.0105 (9)
C100.0348 (10)0.0482 (12)0.0392 (11)−0.0078 (8)0.0025 (8)−0.0022 (9)
C110.0318 (10)0.0682 (16)0.0482 (13)0.0088 (10)0.0018 (9)−0.0036 (11)
C120.0462 (12)0.0504 (14)0.0509 (13)0.0225 (10)−0.0002 (9)−0.0056 (10)
C130.0440 (11)0.0317 (10)0.0390 (11)0.0110 (8)0.0037 (8)−0.0008 (8)
C140.0315 (9)0.0260 (9)0.0261 (9)0.0015 (6)0.0043 (6)−0.0003 (6)
C150.0697 (15)0.0252 (10)0.0590 (15)0.0095 (9)0.0020 (11)−0.0005 (9)
C170.0313 (9)0.0375 (10)0.0354 (10)−0.0127 (8)0.0055 (7)−0.0045 (8)

Geometric parameters (Å, °)

Cd1—N1i2.2671 (16)C2—C41.397 (3)
Cd1—N12.2671 (16)C2—H20.9300
Cd1—O12.3079 (14)C4—C51.385 (2)
Cd1—O1i2.3079 (14)C4—C91.493 (3)
Cd1—O22.3883 (15)C5—C61.391 (3)
Cd1—O2i2.3883 (15)C5—H50.9300
Cd1—C82.6858 (19)C6—C71.391 (3)
Cd1—C8i2.6858 (19)C6—C171.488 (2)
O1—C81.272 (2)C7—H70.9300
O2—C81.242 (2)C10—C111.395 (3)
O3—C91.319 (2)C10—H100.9300
O3—H3A0.8200C11—C121.364 (4)
O4—C91.198 (3)C11—H110.9300
O5—C171.283 (3)C12—C131.412 (3)
O5—H5A0.8200C12—H120.9300
O6—C171.246 (3)C13—C141.402 (3)
N1—C101.327 (2)C13—C151.434 (3)
N1—C141.355 (2)C14—C14i1.449 (4)
C1—C21.387 (3)C15—C15i1.345 (5)
C1—C71.394 (2)C15—H150.9300
C1—C81.500 (2)
N1i—Cd1—N174.48 (8)C5—C4—C9119.20 (18)
N1i—Cd1—O1107.52 (5)C2—C4—C9120.98 (16)
N1—Cd1—O1116.15 (6)C4—C5—C6119.90 (18)
N1i—Cd1—O1i116.15 (6)C4—C5—H5120.0
N1—Cd1—O1i107.52 (5)C6—C5—H5120.0
O1—Cd1—O1i124.47 (8)C7—C6—C5120.28 (16)
N1i—Cd1—O2156.02 (6)C7—C6—C17121.04 (18)
N1—Cd1—O296.89 (6)C5—C6—C17118.65 (17)
O1—Cd1—O255.61 (5)C6—C7—C1119.98 (17)
O1i—Cd1—O287.71 (6)C6—C7—H7120.0
N1i—Cd1—O2i96.89 (6)C1—C7—H7120.0
N1—Cd1—O2i156.02 (6)O2—C8—O1121.27 (17)
O1—Cd1—O2i87.71 (6)O2—C8—C1119.47 (16)
O1i—Cd1—O2i55.61 (5)O1—C8—C1119.22 (16)
O2—Cd1—O2i99.04 (8)O2—C8—Cd162.77 (10)
N1i—Cd1—C8134.67 (6)O1—C8—Cd159.14 (10)
N1—Cd1—C8110.57 (6)C1—C8—Cd1169.85 (13)
O1—Cd1—C828.25 (5)O4—C9—O3124.2 (2)
O1i—Cd1—C8105.31 (6)O4—C9—C4124.38 (18)
O2—Cd1—C827.55 (5)O3—C9—C4111.46 (18)
O2i—Cd1—C891.54 (6)N1—C10—C11122.1 (2)
N1i—Cd1—C8i110.57 (6)N1—C10—H10118.9
N1—Cd1—C8i134.67 (6)C11—C10—H10118.9
O1—Cd1—C8i105.31 (6)C12—C11—C10119.4 (2)
O1i—Cd1—C8i28.25 (5)C12—C11—H11120.3
O2—Cd1—C8i91.54 (6)C10—C11—H11120.3
O2i—Cd1—C8i27.55 (5)C11—C12—C13119.8 (2)
C8—Cd1—C8i97.07 (8)C11—C12—H12120.1
C8—O1—Cd192.62 (11)C13—C12—H12120.1
C8—O2—Cd189.68 (11)C14—C13—C12117.01 (19)
C9—O3—H3A109.5C14—C13—C15120.15 (19)
C17—O5—H5A109.5C12—C13—C15122.83 (19)
C10—N1—C14119.13 (17)N1—C14—C13122.39 (17)
C10—N1—Cd1126.54 (14)N1—C14—C14i118.52 (10)
C14—N1—Cd1114.20 (11)C13—C14—C14i119.08 (12)
C2—C1—C7119.52 (17)C15i—C15—C13120.75 (12)
C2—C1—C8120.57 (16)C15i—C15—H15119.6
C7—C1—C8119.83 (17)C13—C15—H15119.6
C1—C2—C4120.49 (16)O6—C17—O5124.15 (17)
C1—C2—H2119.8O6—C17—C6119.21 (18)
C4—C2—H2119.8O5—C17—C6116.62 (18)
C5—C4—C2119.82 (17)

Symmetry codes: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···O1ii0.821.892.656 (2)155
O5—H5A···O6iii0.821.812.623 (2)170
C2—H2···O3ii0.932.363.262 (3)164

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2344).

References

  • Bruker (1997). SMART Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Han, J.-Y., Wei, W.-Y., Dou, X. & Chang, H.-Y. (2005). Acta Cryst. E61, m2281–m2282.
  • Sheldrick, G. M. (1990). SHELXTL-Plus Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Shi, X., Zhu, G.-S., Fang, Q.-R., Wu, G., Tian, G., Wang, R.-W., Zhang, D.-L., Xue, M. & Qiu, S.-L. (2004). Eur. J. Inorg. Chem. pp. 185–191.

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