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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1408.
Published online 2009 October 23. doi:  10.1107/S1600536809042093
PMCID: PMC2971133

Dibenzoato-κO2 O,O′-(6,6′-dimethyl-2,2′-bipyridine-κ2 N,N′)zinc(II)–benzoic acid (1/1)

Abstract

In the crystal structure of the title compound, [Zn(C6H5COO)2(C12H12N2)]·C6H5COOH, the Zn atom is penta­coordinated in distorted square-pyramidal geometry by two O atoms of a benzoate anion and two N atoms of a 6,6′-dimethyl-2,2′-bipyridine ligand occupying the basal plane and an O atom of another benzoate anion located at the apical site. In the crystal structure, inter­molecular O—H(...)O and C—H(...)O hydrogen bonds and C—H(...)π inter­actions are present.

Related literature

For related structures, see: Alizadeh et al. (2009 [triangle]); Cui et al. (2005 [triangle]); Hökelek et al. (2009a [triangle],b [triangle]); Klausmeyer et al. (2007 [triangle]); Phatchimkun et al. (2009 [triangle]); Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1408-scheme1.jpg

Experimental

Crystal data

  • [Zn(C7H5O2)2(C12H12N2)]·C7H6O2
  • M r = 613.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1408-efi1.jpg
  • a = 9.974 (6) Å
  • b = 12.546 (7) Å
  • c = 12.798 (8) Å
  • α = 96.631 (11)°
  • β = 97.016 (12)°
  • γ = 105.060 (12)°
  • V = 1516.7 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.86 mm−1
  • T = 296 K
  • 0.16 × 0.14 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.875, T max = 0.904
  • 8123 measured reflections
  • 5295 independent reflections
  • 2785 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.136
  • S = 1.04
  • 5295 reflections
  • 370 parameters
  • 14 restraints
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042093/rk2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042093/rk2173Isup2.hkl

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

supplementary crystallographic information

Comment

As a contribution to structural characterization of 6,6'-dimethyl-2,2'-bipyridine complexes [Alizadeh et al., (2009); Cui et al., (2005); Hökelek et al., (2009a,b); Klausmeyer et al., (2007); Phatchimkun et al. (2009); Zhang et al., (2009)], we present here the molecular structure of the title complex, ZnL(C6H5COO)2.C6H5COOH, where L is 6,6'-dimethyl-2,2'-bipyridine.

The title compound, contains two benzoate anions, one 6,6'-dimethyl-2,2'-bipyridine ligand and one benzoic acid molecules. One of the benzoate anions acts as a bidentate ligand, while the other is monodentate.

The molecular structure of the title complex is shown on Fig. 1. In the crystal structure, the face-to-face separation of 3.783 (4)Å suggests no π···π stacking between parallel bipyridine ring systems, intermolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into a one dimensional structure, in which they may be effective in the stabilization of the structure. One weak C—H···π interactions (Table 1) are also found. Cg1 is the centroid of the C9iii-C14iii ring. Symmetry code: (iii) 1-x, 1-y, -z.

Experimental

The title complound was synthesized hydrothermally in a teflon-lined autoclave (25 ml) by heating a mixture of 6,6'-dimethyl-2,2'-bipyridine (0.2 mmol), benzoic acid (0.4 mmol) and ZnSO4.H2O (0.2 mmol) in water (10 ml) at 393 K for 3 d. Crystals suitable for X-ray analysis were obtained.

Refinement

The carboxy H atom was located in a difference Fourier map and refined with a O—H distance of 0.82Å [Uiso(H) = 1.5Ueq(O)]. H atoms bonded to C atoms were positioned geometrically and refined using a riding model with C—H = 0.93Å and 0.96Å for aromatic and methyl H atoms, respectively, and Uiso(H) values were calculated at 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for aromatic.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.

Crystal data

[Zn(C7H5O2)2(C12H12N2)]·C7H6O2Z = 2
Mr = 613.96F(000) = 636
Triclinic, P1Dx = 1.344 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.974 (6) ÅCell parameters from 1683 reflections
b = 12.546 (7) Åθ = 2.5–27.8°
c = 12.798 (8) ŵ = 0.86 mm1
α = 96.631 (11)°T = 296 K
β = 97.016 (12)°Block, colourless
γ = 105.060 (12)°0.16 × 0.14 × 0.12 mm
V = 1516.7 (16) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer5295 independent reflections
Radiation source: fine-focus sealed tube2785 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi]– and ω–scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −10→11
Tmin = 0.875, Tmax = 0.904k = −14→13
8123 measured reflectionsl = −15→15

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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0455P)2] where P = (Fo2 + 2Fc2)/3
5295 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.64 e Å3
14 restraintsΔρmin = −0.64 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Zn10.41555 (6)0.22239 (5)0.15235 (4)0.0561 (2)
N10.2722 (4)0.0734 (3)0.0835 (3)0.0509 (10)
N20.4792 (4)0.2028 (3)0.0057 (3)0.0461 (10)
O10.6236 (4)0.2621 (4)0.2360 (3)0.1060 (12)
O20.4751 (4)0.1472 (3)0.2994 (3)0.0945 (13)
O30.3506 (4)0.3454 (3)0.2070 (3)0.0708 (10)
O40.2026 (4)0.3185 (3)0.0566 (2)0.0672 (10)
O50.1962 (4)0.1688 (3)0.8042 (3)0.0760 (11)
O60.2806 (4)0.3497 (3)0.8688 (3)0.0717 (10)
H60.25200.32870.92250.108*
C10.5999 (8)0.1987 (7)0.3044 (5)0.1025 (12)
C20.7122 (5)0.1859 (4)0.3773 (3)0.0997 (13)
C30.8523 (6)0.2392 (4)0.3750 (4)0.128 (3)
H30.87550.28820.32650.153*
C40.9579 (4)0.2192 (5)0.4450 (5)0.164 (4)
H41.05170.25490.44340.196*
C50.9232 (6)0.1460 (5)0.5174 (4)0.172 (5)
H50.99380.13260.56420.206*
C60.7831 (7)0.0926 (4)0.5197 (4)0.153 (4)
H6A0.75990.04360.56810.183*
C70.6775 (5)0.1126 (4)0.4497 (4)0.111 (3)
H70.58370.07690.45130.134*
C80.2506 (6)0.3676 (4)0.1480 (4)0.0535 (13)
C90.1893 (5)0.4536 (4)0.1966 (4)0.0537 (13)
C100.2524 (7)0.5206 (5)0.2920 (4)0.0894 (19)
H100.33460.51140.32770.107*
C110.1952 (9)0.6015 (6)0.3357 (5)0.116 (2)
H110.23830.64630.40030.139*
C120.0740 (9)0.6148 (6)0.2822 (7)0.125 (3)
H120.03240.66680.31200.150*
C130.0151 (7)0.5522 (6)0.1864 (7)0.117 (3)
H13−0.06540.56310.14960.140*
C140.0726 (6)0.4730 (4)0.1430 (5)0.0780 (17)
H140.03200.43180.07630.094*
C150.2525 (5)0.2627 (5)0.7920 (4)0.0529 (13)
C160.2973 (5)0.2925 (5)0.6902 (4)0.0538 (13)
C170.3171 (6)0.3999 (5)0.6671 (4)0.0758 (16)
H170.30700.45640.71670.091*
C180.3528 (7)0.4224 (6)0.5677 (5)0.097 (2)
H180.36600.49410.55080.116*
C190.3684 (7)0.3383 (7)0.4953 (5)0.098 (2)
H190.39100.35330.42910.118*
C200.3510 (6)0.2331 (6)0.5199 (5)0.0866 (19)
H200.36530.17710.47200.104*
C210.3122 (5)0.2107 (5)0.6159 (4)0.0689 (15)
H210.29550.13800.63080.083*
C220.1317 (6)0.0689 (5)0.2271 (4)0.0847 (18)
H22A0.20670.07470.28400.127*
H22B0.04520.02410.24310.127*
H22C0.12320.14210.21920.127*
C230.1631 (6)0.0156 (5)0.1256 (4)0.0633 (15)
C240.0820 (6)−0.0880 (5)0.0732 (6)0.0798 (18)
H240.0049−0.12670.10090.096*
C250.1145 (7)−0.1335 (5)−0.0189 (6)0.087 (2)
H250.0622−0.2045−0.05240.105*
C260.2243 (6)−0.0747 (4)−0.0621 (4)0.0719 (16)
H260.2461−0.1040−0.12590.086*
C270.3021 (5)0.0296 (4)−0.0087 (4)0.0482 (12)
C280.4195 (5)0.1021 (4)−0.0519 (4)0.0471 (12)
C290.4627 (6)0.0693 (5)−0.1451 (4)0.0648 (15)
H290.4218−0.0020−0.18320.078*
C300.5682 (7)0.1441 (6)−0.1813 (4)0.0785 (17)
H300.59970.1236−0.24400.094*
C310.6250 (6)0.2471 (5)−0.1248 (5)0.0753 (16)
H310.69510.2982−0.14920.090*
C320.5798 (6)0.2774 (4)−0.0311 (4)0.0601 (14)
C330.6386 (6)0.3902 (4)0.0338 (5)0.095 (2)
H33A0.56300.42000.05070.142*
H33B0.69620.4388−0.00600.142*
H33C0.69440.38460.09850.142*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0556 (4)0.0578 (4)0.0511 (4)0.0185 (3)−0.0002 (3)−0.0035 (3)
N10.040 (2)0.057 (3)0.053 (3)0.013 (2)−0.002 (2)0.013 (2)
N20.038 (2)0.046 (3)0.054 (2)0.016 (2)0.005 (2)0.002 (2)
O10.0884 (18)0.162 (3)0.069 (2)0.063 (2)−0.0244 (18)−0.003 (2)
O20.093 (3)0.124 (3)0.066 (2)0.061 (3)−0.034 (2)−0.0054 (18)
O30.081 (3)0.074 (2)0.056 (2)0.037 (2)−0.008 (2)−0.0079 (18)
O40.078 (3)0.075 (2)0.044 (2)0.0216 (19)0.0045 (19)−0.0047 (18)
O50.092 (3)0.073 (3)0.065 (2)0.021 (2)0.019 (2)0.014 (2)
O60.100 (3)0.068 (2)0.051 (2)0.030 (2)0.016 (2)0.0073 (19)
C10.086 (2)0.158 (3)0.066 (2)0.065 (2)−0.0219 (19)−0.006 (2)
C20.084 (2)0.155 (4)0.064 (2)0.066 (2)−0.021 (2)−0.007 (2)
C30.075 (5)0.201 (8)0.097 (5)0.050 (5)0.003 (4)−0.027 (5)
C40.096 (6)0.256 (12)0.121 (7)0.078 (7)−0.032 (6)−0.055 (7)
C50.135 (9)0.205 (11)0.155 (9)0.101 (8)−0.086 (7)−0.069 (8)
C60.211 (10)0.094 (6)0.134 (7)0.068 (6)−0.083 (7)−0.003 (5)
C70.117 (6)0.095 (5)0.100 (5)0.043 (4)−0.057 (5)−0.030 (4)
C80.068 (4)0.049 (3)0.042 (3)0.014 (3)0.014 (3)0.003 (3)
C90.059 (3)0.053 (3)0.047 (3)0.019 (3)0.006 (3)−0.002 (3)
C100.120 (5)0.095 (5)0.063 (4)0.058 (4)0.004 (4)−0.005 (3)
C110.160 (8)0.120 (6)0.075 (5)0.071 (6)0.012 (5)−0.024 (4)
C120.114 (7)0.120 (6)0.147 (7)0.064 (5)0.025 (6)−0.030 (6)
C130.071 (5)0.101 (6)0.166 (8)0.039 (4)−0.012 (5)−0.033 (5)
C140.060 (4)0.068 (4)0.096 (4)0.021 (3)−0.003 (4)−0.016 (3)
C150.048 (3)0.059 (4)0.055 (3)0.022 (3)0.005 (3)0.011 (3)
C160.049 (3)0.066 (4)0.045 (3)0.016 (3)0.002 (3)0.009 (3)
C170.075 (4)0.082 (5)0.065 (4)0.012 (3)0.011 (3)0.013 (3)
C180.103 (5)0.101 (5)0.074 (4)−0.001 (4)0.018 (4)0.028 (4)
C190.090 (5)0.141 (7)0.055 (4)0.014 (5)0.017 (4)0.018 (5)
C200.084 (5)0.117 (6)0.060 (4)0.031 (4)0.015 (3)0.002 (4)
C210.072 (4)0.082 (4)0.054 (3)0.026 (3)0.009 (3)0.006 (3)
C220.063 (4)0.116 (5)0.078 (4)0.021 (4)0.014 (3)0.026 (4)
C230.052 (4)0.069 (4)0.069 (4)0.018 (3)−0.006 (3)0.025 (3)
C240.058 (4)0.065 (5)0.110 (5)0.003 (3)0.001 (4)0.034 (4)
C250.075 (5)0.056 (4)0.114 (6)0.004 (4)−0.017 (4)0.008 (4)
C260.069 (4)0.054 (4)0.079 (4)0.011 (3)−0.012 (3)−0.004 (3)
C270.046 (3)0.043 (3)0.051 (3)0.015 (3)−0.012 (3)0.002 (3)
C280.047 (3)0.046 (3)0.051 (3)0.025 (3)−0.003 (3)0.000 (3)
C290.076 (4)0.061 (4)0.060 (4)0.032 (3)0.005 (3)−0.008 (3)
C300.096 (5)0.104 (5)0.055 (4)0.053 (4)0.030 (4)0.016 (4)
C310.073 (4)0.086 (5)0.074 (4)0.030 (4)0.019 (3)0.017 (4)
C320.060 (4)0.056 (4)0.064 (4)0.019 (3)0.005 (3)0.009 (3)
C330.099 (5)0.066 (4)0.099 (4)−0.012 (3)0.023 (4)0.005 (4)

Geometric parameters (Å, °)

Zn1—O31.917 (3)C13—H130.9300
Zn1—N12.059 (4)C14—H140.9300
Zn1—N22.062 (4)C15—C161.484 (7)
Zn1—O12.120 (4)C16—C211.368 (6)
Zn1—O22.283 (4)C16—C171.381 (7)
N1—C271.344 (6)C17—C181.402 (7)
N1—C231.350 (6)C17—H170.9300
N2—C281.335 (5)C18—C191.375 (8)
N2—C321.353 (6)C18—H180.9300
O1—C11.252 (8)C19—C201.365 (8)
O2—C11.235 (8)C19—H190.9300
O3—C81.285 (5)C20—C211.369 (7)
O4—C81.233 (5)C20—H200.9300
O5—C151.204 (5)C21—H210.9300
O6—C151.327 (5)C22—C231.496 (7)
O6—H60.8200C22—H22A0.9600
C1—C21.423 (7)C22—H22B0.9600
C2—C31.3900C22—H22C0.9600
C2—C71.3900C23—C241.384 (7)
C3—C41.3900C24—C251.362 (8)
C3—H30.9300C24—H240.9300
C4—C51.3900C25—C261.368 (8)
C4—H40.9300C25—H250.9300
C5—C61.3900C26—C271.384 (6)
C5—H50.9300C26—H260.9300
C6—C71.3900C27—C281.492 (6)
C6—H6A0.9300C28—C291.372 (6)
C7—H70.9300C29—C301.382 (7)
C8—C91.485 (7)C29—H290.9300
C9—C141.369 (6)C30—C311.349 (7)
C9—C101.377 (6)C30—H300.9300
C10—C111.384 (8)C31—C321.379 (7)
C10—H100.9300C31—H310.9300
C11—C121.374 (9)C32—C331.488 (7)
C11—H110.9300C33—H33A0.9600
C12—C131.352 (8)C33—H33B0.9600
C12—H120.9300C33—H33C0.9600
C13—C141.369 (8)
O3—Zn1—N1119.74 (16)O5—C15—C16123.5 (5)
O3—Zn1—N2124.65 (15)O6—C15—C16113.6 (5)
N1—Zn1—N280.07 (17)C21—C16—C17119.5 (5)
O3—Zn1—O1102.78 (16)C21—C16—C15119.1 (5)
N1—Zn1—O1132.61 (16)C17—C16—C15121.3 (5)
N2—Zn1—O193.04 (16)C16—C17—C18119.0 (6)
O3—Zn1—O2104.33 (15)C16—C17—H17120.5
N1—Zn1—O291.25 (15)C18—C17—H17120.5
N2—Zn1—O2127.89 (14)C19—C18—C17120.0 (6)
O1—Zn1—O256.64 (17)C19—C18—H18120.0
C27—N1—C23119.8 (4)C17—C18—H18120.0
C27—N1—Zn1113.4 (3)C20—C19—C18120.4 (6)
C23—N1—Zn1126.6 (4)C20—C19—H19119.8
C28—N2—C32119.6 (4)C18—C19—H19119.8
C28—N2—Zn1113.8 (3)C19—C20—C21119.4 (6)
C32—N2—Zn1126.4 (3)C19—C20—H20120.3
C1—O1—Zn198.0 (4)C21—C20—H20120.3
C1—O2—Zn190.6 (4)C20—C21—C16121.6 (6)
C8—O3—Zn1117.4 (3)C20—C21—H21119.2
C15—O6—H6109.5C16—C21—H21119.2
O2—C1—O1114.7 (6)C23—C22—H22A109.5
O2—C1—C2124.5 (7)C23—C22—H22B109.5
O1—C1—C2120.8 (7)H22A—C22—H22B109.5
C3—C2—C7120.0C23—C22—H22C109.5
C3—C2—C1122.6 (5)H22A—C22—H22C109.5
C7—C2—C1117.3 (5)H22B—C22—H22C109.5
C4—C3—C2120.0N1—C23—C24119.8 (5)
C4—C3—H3120.0N1—C23—C22117.9 (5)
C2—C3—H3120.0C24—C23—C22122.2 (6)
C3—C4—C5120.0C25—C24—C23120.2 (6)
C3—C4—H4120.0C25—C24—H24119.9
C5—C4—H4120.0C23—C24—H24119.9
C4—C5—C6120.0C24—C25—C26120.0 (6)
C4—C5—H5120.0C24—C25—H25120.0
C6—C5—H5120.0C26—C25—H25120.0
C7—C6—C5120.0C25—C26—C27118.4 (6)
C7—C6—H6A120.0C25—C26—H26120.8
C5—C6—H6A120.0C27—C26—H26120.8
C6—C7—C2120.0N1—C27—C26121.7 (5)
C6—C7—H7120.0N1—C27—C28115.9 (4)
C2—C7—H7120.0C26—C27—C28122.4 (5)
O4—C8—O3123.0 (5)N2—C28—C29121.7 (5)
O4—C8—C9120.3 (5)N2—C28—C27115.4 (4)
O3—C8—C9116.7 (4)C29—C28—C27122.9 (5)
C14—C9—C10118.3 (5)C28—C29—C30118.8 (5)
C14—C9—C8120.0 (5)C28—C29—H29120.6
C10—C9—C8121.6 (5)C30—C29—H29120.6
C9—C10—C11121.0 (6)C31—C30—C29119.3 (5)
C9—C10—H10119.5C31—C30—H30120.4
C11—C10—H10119.5C29—C30—H30120.4
C12—C11—C10119.1 (6)C30—C31—C32120.5 (6)
C12—C11—H11120.5C30—C31—H31119.7
C10—C11—H11120.5C32—C31—H31119.7
C13—C12—C11120.0 (7)N2—C32—C31120.0 (5)
C13—C12—H12120.0N2—C32—C33117.5 (5)
C11—C12—H12120.0C31—C32—C33122.5 (5)
C12—C13—C14120.8 (7)C32—C33—H33A109.5
C12—C13—H13119.6C32—C33—H33B109.5
C14—C13—H13119.6H33A—C33—H33B109.5
C9—C14—C13120.8 (6)C32—C33—H33C109.5
C9—C14—H14119.6H33A—C33—H33C109.5
C13—C14—H14119.6H33B—C33—H33C109.5
O5—C15—O6122.9 (5)
O3—Zn1—N1—C27134.4 (3)C8—C9—C10—C11179.1 (6)
N2—Zn1—N1—C2710.0 (3)C9—C10—C11—C12−0.2 (11)
O1—Zn1—N1—C27−74.9 (4)C10—C11—C12—C13−2.5 (13)
O2—Zn1—N1—C27−118.3 (3)C11—C12—C13—C141.9 (13)
O3—Zn1—N1—C23−50.8 (4)C10—C9—C14—C13−4.0 (9)
N2—Zn1—N1—C23−175.2 (4)C8—C9—C14—C13−179.8 (6)
O1—Zn1—N1—C2399.9 (4)C12—C13—C14—C91.4 (11)
O2—Zn1—N1—C2356.5 (4)O5—C15—C16—C21−18.5 (7)
O3—Zn1—N2—C28−130.2 (3)O6—C15—C16—C21161.4 (4)
N1—Zn1—N2—C28−10.8 (3)O5—C15—C16—C17158.1 (5)
O1—Zn1—N2—C28122.0 (3)O6—C15—C16—C17−22.0 (6)
O2—Zn1—N2—C2873.0 (3)C21—C16—C17—C18−0.3 (8)
O3—Zn1—N2—C3255.2 (4)C15—C16—C17—C18−176.9 (5)
N1—Zn1—N2—C32174.6 (4)C16—C17—C18—C19−0.4 (9)
O1—Zn1—N2—C32−52.6 (4)C17—C18—C19—C20−0.8 (10)
O2—Zn1—N2—C32−101.6 (4)C18—C19—C20—C212.6 (10)
O3—Zn1—O1—C1100.7 (4)C19—C20—C21—C16−3.4 (9)
N1—Zn1—O1—C1−53.5 (5)C17—C16—C21—C202.2 (8)
N2—Zn1—O1—C1−132.8 (4)C15—C16—C21—C20178.9 (5)
O2—Zn1—O1—C11.8 (4)C27—N1—C23—C24−0.5 (7)
O3—Zn1—O2—C1−97.8 (4)Zn1—N1—C23—C24−175.0 (4)
N1—Zn1—O2—C1141.0 (4)C27—N1—C23—C22−178.6 (4)
N2—Zn1—O2—C162.6 (4)Zn1—N1—C23—C226.9 (6)
O1—Zn1—O2—C1−1.8 (4)N1—C23—C24—C252.1 (8)
N1—Zn1—O3—C8−45.9 (4)C22—C23—C24—C25−179.9 (5)
N2—Zn1—O3—C852.9 (4)C23—C24—C25—C26−2.7 (9)
O1—Zn1—O3—C8155.8 (3)C24—C25—C26—C271.6 (8)
O2—Zn1—O3—C8−145.8 (3)C23—N1—C27—C26−0.6 (6)
Zn1—O2—C1—O12.8 (6)Zn1—N1—C27—C26174.6 (3)
Zn1—O2—C1—C2−174.3 (6)C23—N1—C27—C28176.8 (4)
Zn1—O1—C1—O2−3.0 (7)Zn1—N1—C27—C28−7.9 (5)
Zn1—O1—C1—C2174.2 (5)C25—C26—C27—N10.1 (7)
O2—C1—C2—C3175.0 (5)C25—C26—C27—C28−177.2 (5)
O1—C1—C2—C3−1.9 (8)C32—N2—C28—C293.7 (6)
O2—C1—C2—C7−2.0 (8)Zn1—N2—C28—C29−171.4 (3)
O1—C1—C2—C7−178.9 (5)C32—N2—C28—C27−175.3 (4)
C7—C2—C3—C40.0Zn1—N2—C28—C279.7 (4)
C1—C2—C3—C4−176.9 (5)N1—C27—C28—N2−1.2 (5)
C2—C3—C4—C50.0C26—C27—C28—N2176.3 (4)
C3—C4—C5—C60.0N1—C27—C28—C29179.9 (4)
C4—C5—C6—C70.0C26—C27—C28—C29−2.7 (7)
C5—C6—C7—C20.0N2—C28—C29—C30−1.8 (7)
C3—C2—C7—C60.0C27—C28—C29—C30177.1 (4)
C1—C2—C7—C6177.1 (4)C28—C29—C30—C31−0.5 (8)
Zn1—O3—C8—O4−5.0 (6)C29—C30—C31—C320.8 (8)
Zn1—O3—C8—C9172.6 (3)C28—N2—C32—C31−3.3 (7)
O4—C8—C9—C144.8 (7)Zn1—N2—C32—C31171.1 (3)
O3—C8—C9—C14−172.9 (5)C28—N2—C32—C33177.4 (4)
O4—C8—C9—C10−170.8 (5)Zn1—N2—C32—C33−8.2 (6)
O3—C8—C9—C1011.5 (7)C30—C31—C32—N21.0 (8)
C14—C9—C10—C113.4 (9)C30—C31—C32—C33−179.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C24—H24···O5i0.932.443.340 (8)162
C33—H33C···O10.962.523.199 (8)128
C22—H22A···O20.962.573.289 (7)132
O6—H6···O4ii0.821.852.655 (5)166
C31—H31···Cg1iii0.932.793.708 (7)170

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2173).

References

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