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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m655.
Published online 2008 April 10. doi:  10.1107/S1600536808009483
PMCID: PMC2961165

(2,2′-Bipyridine-κ2 N,N′)bis­(4-methyl­benzoato-κ2 O,O′)zinc(II)

Abstract

In the title compound, [Zn(C8H7O2)2(C10H8N2)], the ZnII atom is coordinated by four O atoms from two chelating 4-methyl­benzoate ligands and two N atoms from a 2,2′-bipyridine ligand, displaying a disordered octahedral geometry. C—H(...)O hydrogen bonds connect the complex mol­ecules into a three-dimensional supra­molecular structure.

Related literature

For related literature, see: Choi & Jeon (2003 [triangle]); Guilera & Steed (1999 [triangle]); Tao et al. (2000 [triangle]).

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Object name is e-64-0m655-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H7O2)2(C10H8N2)]
  • M r = 491.83
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m655-efi1.jpg
  • a = 7.6172 (3) Å
  • b = 9.8211 (4) Å
  • c = 15.7595 (6) Å
  • α = 79.130 (2)°
  • β = 83.977 (2)°
  • γ = 79.958 (2)°
  • V = 1136.90 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.12 mm−1
  • T = 296 (2) K
  • 0.26 × 0.23 × 0.21 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.760, T max = 0.799
  • 10295 measured reflections
  • 4047 independent reflections
  • 3281 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.087
  • S = 1.02
  • 4047 reflections
  • 300 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; 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 geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009483/hy2125sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009483/hy2125Isup2.hkl

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

Acknowledgments

The author acknowledges Mudanjiang Normal College for supporting this work.

supplementary crystallographic information

Comment

Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Tao et al., 2000; Choi & Jeon, 2003). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metal ions and the bridging building blocks, as well as on the influence of weaker non-covalent interactions, such as hydrogen bonds and π–π stacking interactions. As a building block, 4-methylbenzoate is an excellent candidate for the construction of supramolecular complexes. Recently, we obtained the title mononuclear complex by the reaction of cadmium chloride with 4-methylbenzoic acid and 2,2'-bipyridine in an aqueous solution and its crystal structure is reported here.

As depicted in Fig. 1, the ZnII atom is coordinated by four O atoms from two 4-methylbenzoate ligands and two N atoms from one 2,2'-bipyridine ligand. The 4-methylbenzoates act as bidentate chelating ligands. The Zn1—O1 distance of 2.509 (2) Å (Table 1) suggests a non-negligible interaction, or a chelating coordination mode (Guilera & Steed, 1999). The complex molecules are connected by C—H···O hydrogen bonds (Table 2), resulting in a three-dimensional supramolecular network.

Experimental

The title compound was prepared by the addition of a stoichiometric amount of cadmium chloride (0.228 g, 1 mmol) and 2,2'-bipyridine (0.156 g, 1 mmol) to a hot aqueous solution (25 ml) of 4-methylbenzoic acid (2.72 g, 20 mmol). The pH value was then adjusted to 7.0 to 8.0 with NaOH (1 mmol). The resulting solution was filtered, and colorless single crystals were obtained at room temperature over several days.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic groups and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[Zn(C8H7O2)2(C10H8N2)]Z = 2
Mr = 491.83F000 = 508
Triclinic, P1Dx = 1.437 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.6172 (3) ÅCell parameters from 3500 reflections
b = 9.8211 (4) Åθ = 1.3–28.0º
c = 15.7595 (6) ŵ = 1.12 mm1
α = 79.130 (2)ºT = 296 (2) K
β = 83.977 (2)ºBlock, colorless
γ = 79.958 (2)º0.26 × 0.23 × 0.21 mm
V = 1136.90 (8) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4047 independent reflections
Radiation source: fine-focus sealed tube3281 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 296(2) Kθmax = 25.2º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −9→9
Tmin = 0.760, Tmax = 0.800k = −11→11
10295 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.087  w = 1/[σ2(Fo2) + (0.0378P)2 + 0.345P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4047 reflectionsΔρmax = 0.22 e Å3
300 parametersΔρmin = −0.29 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
C1−0.0510 (3)0.7966 (3)0.21798 (15)0.0470 (6)
C2−0.2171 (3)0.8766 (2)0.25555 (15)0.0411 (6)
C3−0.3837 (3)0.8465 (3)0.24538 (16)0.0453 (6)
H3−0.39250.77840.21300.054*
C4−0.5367 (3)0.9160 (3)0.28257 (17)0.0487 (6)
H4−0.64760.89660.27310.058*
C5−0.5282 (4)1.0141 (3)0.33374 (17)0.0497 (6)
C6−0.3604 (4)1.0445 (3)0.34364 (17)0.0531 (7)
H6−0.35121.11050.37750.064*
C7−0.2073 (4)0.9783 (3)0.30400 (16)0.0486 (6)
H7−0.09701.00230.30990.058*
C8−0.6941 (4)1.0840 (3)0.3795 (2)0.0725 (9)
H8A−0.79711.05150.36500.109*
H8B−0.70591.18390.36140.109*
H8C−0.68481.06100.44090.109*
C90.3993 (3)0.4970 (3)0.29191 (16)0.0446 (6)
C100.5328 (3)0.4398 (2)0.35701 (15)0.0404 (6)
C110.4819 (4)0.3697 (3)0.43803 (16)0.0455 (6)
H110.36310.35840.45220.055*
C120.6075 (4)0.3164 (3)0.49798 (16)0.0517 (7)
H120.57150.26950.55220.062*
C130.7847 (4)0.3311 (3)0.47934 (17)0.0513 (7)
C140.8342 (4)0.4020 (3)0.39820 (18)0.0566 (7)
H140.95310.41320.38420.068*
C150.7102 (3)0.4562 (3)0.33780 (16)0.0505 (7)
H150.74610.50420.28380.061*
C160.9214 (5)0.2747 (4)0.5456 (2)0.0805 (10)
H16A0.86290.23480.59920.121*
H16B0.97850.34980.55500.121*
H16C1.00960.20380.52470.121*
C170.3103 (4)0.8005 (4)0.0171 (2)0.0748 (9)
H170.30610.86200.05580.090*
C180.3617 (5)0.8439 (5)−0.0679 (3)0.1067 (16)
H180.38890.9339−0.08700.128*
C190.3723 (5)0.7545 (6)−0.1234 (3)0.118 (2)
H190.41010.7814−0.18130.142*
C200.3270 (4)0.6220 (5)−0.0949 (2)0.0895 (13)
H200.33280.5596−0.13310.107*
C210.2722 (3)0.5840 (3)−0.00735 (16)0.0585 (8)
C220.2212 (3)0.4456 (3)0.03117 (18)0.0554 (7)
C230.2133 (5)0.3418 (5)−0.0157 (2)0.0829 (11)
H230.24050.3565−0.07530.099*
C240.1654 (5)0.2173 (5)0.0259 (3)0.0984 (15)
H240.15840.1474−0.00540.118*
C250.1274 (4)0.1953 (4)0.1141 (3)0.0843 (11)
H250.09720.11020.14350.101*
C260.1355 (4)0.3035 (3)0.1576 (2)0.0640 (8)
H260.10880.29010.21730.077*
N10.2659 (3)0.6739 (2)0.04704 (14)0.0531 (6)
N20.1801 (3)0.4265 (2)0.11749 (13)0.0491 (5)
O10.0937 (3)0.8418 (2)0.21029 (14)0.0713 (6)
O2−0.0627 (2)0.68095 (19)0.19582 (11)0.0527 (5)
O30.4440 (2)0.57256 (18)0.22078 (11)0.0525 (5)
O40.2425 (2)0.4705 (2)0.30517 (12)0.0621 (5)
Zn10.19260 (4)0.59907 (3)0.176739 (18)0.04603 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0471 (16)0.0555 (18)0.0358 (13)−0.0043 (13)−0.0065 (11)−0.0032 (12)
C20.0455 (15)0.0373 (14)0.0384 (13)−0.0039 (11)−0.0066 (11)−0.0020 (11)
C30.0517 (16)0.0425 (15)0.0434 (14)−0.0104 (12)−0.0069 (12)−0.0071 (12)
C40.0411 (15)0.0476 (16)0.0574 (16)−0.0115 (12)−0.0029 (12)−0.0055 (13)
C50.0540 (17)0.0377 (15)0.0523 (15)−0.0027 (12)0.0000 (13)−0.0018 (12)
C60.0627 (18)0.0482 (16)0.0517 (16)−0.0059 (14)−0.0093 (13)−0.0170 (13)
C70.0457 (15)0.0478 (16)0.0545 (16)−0.0062 (12)−0.0113 (12)−0.0117 (13)
C80.063 (2)0.064 (2)0.088 (2)−0.0048 (16)0.0114 (17)−0.0212 (18)
C90.0499 (16)0.0399 (15)0.0460 (15)−0.0036 (12)−0.0021 (12)−0.0166 (12)
C100.0483 (15)0.0362 (14)0.0381 (13)−0.0069 (11)−0.0014 (11)−0.0104 (11)
C110.0501 (15)0.0447 (15)0.0435 (14)−0.0115 (12)0.0036 (12)−0.0126 (12)
C120.0713 (19)0.0448 (16)0.0380 (14)−0.0110 (14)0.0028 (13)−0.0072 (12)
C130.0602 (18)0.0475 (16)0.0468 (15)−0.0029 (13)−0.0108 (13)−0.0108 (13)
C140.0454 (16)0.0673 (19)0.0563 (17)−0.0121 (14)−0.0045 (13)−0.0052 (15)
C150.0521 (17)0.0554 (17)0.0419 (14)−0.0128 (13)−0.0012 (12)−0.0005 (12)
C160.083 (2)0.091 (3)0.065 (2)−0.002 (2)−0.0273 (18)−0.0045 (18)
C170.0556 (19)0.076 (2)0.075 (2)−0.0037 (16)0.0001 (16)0.0213 (18)
C180.065 (2)0.118 (4)0.095 (3)0.006 (2)0.015 (2)0.054 (3)
C190.071 (3)0.170 (5)0.060 (2)0.035 (3)0.019 (2)0.051 (3)
C200.065 (2)0.137 (4)0.0404 (17)0.038 (2)0.0007 (15)−0.005 (2)
C210.0404 (15)0.085 (2)0.0358 (14)0.0209 (15)−0.0045 (11)−0.0023 (15)
C220.0424 (15)0.071 (2)0.0486 (16)0.0188 (14)−0.0149 (12)−0.0199 (15)
C230.076 (2)0.099 (3)0.077 (2)0.033 (2)−0.0329 (19)−0.052 (2)
C240.082 (3)0.091 (3)0.139 (4)0.026 (2)−0.050 (3)−0.076 (3)
C250.066 (2)0.060 (2)0.134 (4)−0.0004 (17)−0.028 (2)−0.033 (2)
C260.0607 (19)0.0565 (19)0.077 (2)−0.0072 (15)−0.0087 (15)−0.0156 (17)
N10.0446 (13)0.0597 (15)0.0449 (13)0.0013 (11)0.0001 (10)0.0051 (12)
N20.0439 (13)0.0557 (14)0.0469 (13)−0.0007 (10)−0.0046 (10)−0.0127 (11)
O10.0465 (12)0.0895 (16)0.0860 (15)−0.0154 (11)−0.0004 (10)−0.0336 (13)
O20.0564 (12)0.0468 (11)0.0540 (11)−0.0047 (9)0.0036 (9)−0.0144 (9)
O30.0564 (12)0.0522 (11)0.0483 (10)−0.0132 (9)−0.0096 (9)−0.0004 (9)
O40.0450 (11)0.0880 (15)0.0530 (11)−0.0139 (10)−0.0029 (9)−0.0089 (10)
Zn10.0458 (2)0.0512 (2)0.04008 (18)−0.00641 (14)−0.00186 (12)−0.00715 (13)

Geometric parameters (Å, °)

C1—O11.244 (3)C16—H16A0.9600
C1—O21.270 (3)C16—H16B0.9600
C1—C21.496 (4)C16—H16C0.9600
C2—C71.383 (3)C17—N11.332 (4)
C2—C31.384 (3)C17—C181.366 (5)
C3—C41.378 (4)C17—H170.9300
C3—H30.9300C18—C191.339 (6)
C4—C51.381 (4)C18—H180.9300
C4—H40.9300C19—C201.384 (6)
C5—C61.393 (4)C19—H190.9300
C5—C81.510 (4)C20—C211.398 (4)
C6—C71.382 (4)C20—H200.9300
C6—H60.9300C21—N11.334 (4)
C7—H70.9300C21—C221.480 (4)
C8—H8A0.9600C22—N21.349 (3)
C8—H8B0.9600C22—C231.380 (4)
C8—H8C0.9600C23—C241.364 (6)
C9—O41.254 (3)C23—H230.9300
C9—O31.272 (3)C24—C251.372 (6)
C9—C101.485 (3)C24—H240.9300
C10—C111.383 (3)C25—C261.383 (4)
C10—C151.384 (3)C25—H250.9300
C11—C121.382 (4)C26—N21.336 (4)
C11—H110.9300C26—H260.9300
C12—C131.377 (4)N1—Zn12.090 (2)
C12—H120.9300N2—Zn12.103 (2)
C13—C141.384 (4)O1—Zn12.509 (2)
C13—C161.514 (4)O2—Zn11.9852 (18)
C14—C151.380 (4)O3—Zn12.0626 (17)
C14—H140.9300O4—Zn12.2058 (19)
C15—H150.9300
O1—C1—O2121.5 (3)N1—C17—C18122.8 (4)
O1—C1—C2120.6 (2)N1—C17—H17118.6
O2—C1—C2117.8 (2)C18—C17—H17118.6
C7—C2—C3118.5 (2)C19—C18—C17118.8 (4)
C7—C2—C1120.8 (2)C19—C18—H18120.6
C3—C2—C1120.7 (2)C17—C18—H18120.6
C4—C3—C2121.0 (2)C18—C19—C20120.2 (4)
C4—C3—H3119.5C18—C19—H19119.9
C2—C3—H3119.5C20—C19—H19119.9
C3—C4—C5121.1 (2)C19—C20—C21118.6 (4)
C3—C4—H4119.5C19—C20—H20120.7
C5—C4—H4119.5C21—C20—H20120.7
C4—C5—C6117.8 (2)N1—C21—C20120.1 (3)
C4—C5—C8121.5 (3)N1—C21—C22116.0 (2)
C6—C5—C8120.7 (3)C20—C21—C22123.8 (3)
C7—C6—C5121.1 (2)N2—C22—C23121.0 (3)
C7—C6—H6119.4N2—C22—C21115.0 (2)
C5—C6—H6119.4C23—C22—C21124.0 (3)
C6—C7—C2120.4 (2)C24—C23—C22119.6 (4)
C6—C7—H7119.8C24—C23—H23120.2
C2—C7—H7119.8C22—C23—H23120.2
C5—C8—H8A109.5C23—C24—C25120.0 (3)
C5—C8—H8B109.5C23—C24—H24120.0
H8A—C8—H8B109.5C25—C24—H24120.0
C5—C8—H8C109.5C24—C25—C26117.9 (4)
H8A—C8—H8C109.5C24—C25—H25121.0
H8B—C8—H8C109.5C26—C25—H25121.0
O4—C9—O3118.9 (2)N2—C26—C25122.6 (3)
O4—C9—C10121.1 (2)N2—C26—H26118.7
O3—C9—C10119.9 (2)C25—C26—H26118.7
C11—C10—C15118.8 (2)C17—N1—C21119.5 (3)
C11—C10—C9120.6 (2)C17—N1—Zn1124.7 (2)
C15—C10—C9120.6 (2)C21—N1—Zn1115.76 (18)
C12—C11—C10120.1 (2)C26—N2—C22118.8 (3)
C12—C11—H11120.0C26—N2—Zn1125.87 (19)
C10—C11—H11120.0C22—N2—Zn1115.32 (19)
C13—C12—C11121.6 (2)C1—O2—Zn1101.97 (16)
C13—C12—H12119.2C9—O3—Zn192.93 (15)
C11—C12—H12119.2C9—O4—Zn186.93 (15)
C12—C13—C14117.9 (2)O1—Zn1—O257.03 (7)
C12—C13—C16121.5 (3)O1—Zn1—O395.86 (7)
C14—C13—C16120.6 (3)O1—Zn1—O4103.13 (7)
C15—C14—C13121.1 (3)O1—Zn1—N192.92 (7)
C15—C14—H14119.4O1—Zn1—N2155.41 (8)
C13—C14—H14119.4O2—Zn1—O3145.10 (8)
C14—C15—C10120.4 (2)O2—Zn1—N1105.58 (8)
C14—C15—H15119.8O3—Zn1—N196.58 (8)
C10—C15—H15119.8O2—Zn1—N2103.12 (8)
C13—C16—H16A109.5O3—Zn1—N2107.73 (8)
C13—C16—H16B109.5N1—Zn1—N277.88 (9)
H16A—C16—H16B109.5O2—Zn1—O4100.93 (7)
C13—C16—H16C109.5O3—Zn1—O461.19 (7)
H16A—C16—H16C109.5N1—Zn1—O4153.43 (8)
H16B—C16—H16C109.5N2—Zn1—O494.46 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O3i0.932.533.293 (3)139
C4—H4···O1i0.932.483.385 (3)165
C14—H14···O4ii0.932.513.417 (3)164
C15—H15···O2ii0.932.573.395 (3)148
C20—H20···O3iii0.932.433.189 (4)139
C23—H23···O2iv0.932.563.230 (4)129

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2125).

References

  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Choi, K. Y. & Jeon, Y. M. (2003). Inorg. Chem. Commun.6, 1294–1296.
  • Guilera, G. & Steed, J. W. (1999). Chem. Commun. pp. 1563–1564.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tao, J., Tong, M. L. & Chen, X. M. (2000). J. Chem. Soc. Dalton Trans. pp. 3669–3674.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography