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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m525–m526.
Published online 2008 March 7. doi:  10.1107/S1600536808005862
PMCID: PMC2961034

[2-(2-Carboxy­phen­yl)benzoato]bis­(1,10-phenanthroline)zinc(II) 2-(2-carboxy­phen­yl)benzoate monohydrate

Abstract

In the title compound, [Zn(C14H9O4)(C12H8N2)2](C14H9O4)·H2O, the ZnII atom of the complex cation is six-coordinated in an octa­hedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxyl­ate group from a singly deprotonated diphenic acid. The phenanthroline and carboxylate ligands act as chelating ligands. The dihedral angles between the two benzene rings in the deprotonated diphenic acid groups are 81.05 (2) (ligand) and 89.10 (2)° (anion). O—H(...)O and C—H(...)O hydrogen bonds link the components into a three-dimensional network.

Related literature

For related structures containing the diphenic acid anion, see: Wan & Zhang (2003 [triangle]); Vodak et al. (2001 [triangle]); Chui et al. (2001 [triangle]); Fernandes et al. (2001 [triangle]); Trombe et al. (2002 [triangle]); Xu et al. (2003 [triangle]); Nie et al. (2001 [triangle]); Sun et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m525-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H9O4)(C12H8N2)2](C14H9O4)·H2O
  • M r = 926.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m525-efi1.jpg
  • a = 10.8208 (11) Å
  • b = 13.7475 (14) Å
  • c = 14.9231 (16) Å
  • α = 77.824 (2)°
  • β = 77.294 (2)°
  • γ = 85.052 (2)°
  • V = 2115.0 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.65 mm−1
  • T = 298 (2) K
  • 0.46 × 0.28 × 0.07 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.800, T max = 0.960
  • 13020 measured reflections
  • 9403 independent reflections
  • 4505 reflections with I > 2σ(I)
  • R int = 0.103

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.144
  • S = 0.82
  • 9403 reflections
  • 603 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.89 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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/S1600536808005862/ci2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005862/ci2560Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Science and Technology Foundation of Shanghai (grant No. 065212050) and the Foundation of Shanghai Higher Education (grant No. 07ZZ68).

supplementary crystallographic information

Comment

In all types of carboxylic acids, diphenic acid is widely used in the construction of coordination polymers due to their capability of acting as bridging and chelating ligand in various coordination modes (Wan & Zhang, 2003). Much interest has been paid to the preparation of metal aromatic carboxylates under hydrothermal conditions (Vodak et al., 2001; Chui et al., 2001; Nie et al., 2001; Sun et al., 2001; Fernandes et al., 2001; Trombe et al. 2002; Xu et al. 2003). Recently, we have prepared the title compound and report here its crystal structure.

The asymmetric unit of the title compound consists of a [Zn(C12H8N2)2(C14H9O4)]+ complex cation, one singly deprotonated diphenic acid anion (C14H9O4-) and one water molecule (Fig. 1). In the complex cation, the ZnII atom is six-coordinated in an octahedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxylate group from a diphenic acid, with Zn—N distances of 2.128 (3)–2.145 (4) Å and Zn—O distances of 2.078 (3) and 2.334 (3) Å. The N—Zn—N, N—Zn—O and O—Zn—O bond angles are in the ranges 77.99 (14)–167.99 (13)°, 86.71 (11)–155.23 (11)° and 59.17 (10)°, respectively (Table 1). The phenanthroline and diphenic acid act as chelating ligands (Table 1 and Fig.1). The dihedral angle between the two benzene rings in diphenic acid is ca 81.05 (2)° (cation) and 89.10 (2)° (anion).

Intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) link complex cations, anions and water molecules to form a three-dimensional network (Fig. 2).

Experimental

A mixture of diphenic acid (0.0484 g, 0.2 mmol), phenanthroline (0.04 g, 0.2 mmol), Zn(NO3)2.6H2O (0.1 mmol) and NaOH (0.012 g, 0.3 mmol) with a molar ratio of 2/2/1/3 in H2O—CH3CH2OH (v/v 4/1) (15 ml) was sealed in a Teflon-lined stainless steel Parr bomb. The bomb was heated to 433 K for 72 h and then cooled to room temperature at 5 K h-1. A large amount of yellow crystals formed, which were collected by filtration, washed with water, and dried in air.

Refinement

The water H atoms were located in a difference map and their positional parameters were refined with O—H distances restrained to 0.85 (3) Å. The remaining H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å, O—H = 0.82 Å and Uiso(H) = 1.2Ueq(C) and 1.2Ueq(O). The components of the displacement parameters in the direction of the C31—C32 bond were restrained to be equal.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
Fig. 2.
The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

[Zn(C14H9O4)(C12H8N2)2](C14H9O4)·H2OZ = 2
Mr = 926.24F000 = 956
Triclinic, P1Dx = 1.454 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.8208 (11) ÅCell parameters from 1630 reflections
b = 13.7475 (14) Åθ = 4.8–40.2º
c = 14.9231 (16) ŵ = 0.65 mm1
α = 77.824 (2)ºT = 298 (2) K
β = 77.294 (2)ºBlock, yellow
γ = 85.052 (2)º0.46 × 0.28 × 0.07 mm
V = 2115.0 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer9403 independent reflections
Radiation source: fine-focus sealed tube4505 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.103
T = 298(2) Kθmax = 28.3º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 1998)h = −11→14
Tmin = 0.800, Tmax = 0.960k = −17→17
13020 measured reflectionsl = −16→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0297P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.001
9403 reflectionsΔρmax = 0.89 e Å3
603 parametersΔρmin = −0.48 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
Zn10.64423 (5)0.88673 (4)0.74002 (3)0.03550 (16)
O10.7838 (3)1.0069 (2)0.64852 (19)0.0426 (8)
O20.8139 (3)0.9051 (2)0.77676 (18)0.0405 (7)
O30.7914 (4)1.2521 (3)0.7375 (3)0.0767 (12)
O40.7058 (4)1.3718 (3)0.6419 (3)0.0865 (13)
H4B0.66441.38400.69160.130*
N10.5364 (3)0.8073 (2)0.8672 (2)0.0368 (9)
N20.5425 (3)1.0045 (2)0.8031 (2)0.0355 (8)
N30.5155 (3)0.9006 (2)0.6470 (2)0.0366 (9)
N40.7090 (3)0.7673 (2)0.6686 (2)0.0369 (9)
C10.4516 (4)0.8671 (3)0.9161 (3)0.0350 (10)
C20.4569 (4)0.9721 (3)0.8828 (3)0.0339 (10)
C30.5528 (4)1.1024 (3)0.7720 (3)0.0469 (12)
H30.61331.12520.71850.056*
C40.4759 (4)1.1718 (3)0.8172 (3)0.0491 (12)
H4A0.48361.23960.79300.059*
C50.3890 (4)1.1393 (3)0.8973 (3)0.0483 (12)
H50.33761.18500.92810.058*
C60.3773 (4)1.0374 (3)0.9329 (3)0.0384 (11)
C70.2920 (4)0.9964 (4)1.0161 (3)0.0522 (13)
H70.23911.03901.04990.063*
C80.2853 (4)0.8969 (4)1.0478 (3)0.0514 (13)
H8A0.22760.87271.10250.062*
C90.3653 (4)0.8282 (3)0.9989 (3)0.0428 (11)
C100.3674 (5)0.7248 (4)1.0305 (3)0.0557 (14)
H100.31050.69641.08410.067*
C110.4531 (5)0.6656 (4)0.9822 (3)0.0609 (15)
H110.45680.59701.00350.073*
C120.5357 (5)0.7098 (3)0.9000 (3)0.0501 (13)
H120.59270.66880.86700.060*
C130.5415 (4)0.8322 (3)0.5895 (3)0.0365 (10)
C140.6448 (4)0.7631 (3)0.6003 (3)0.0374 (11)
C150.8014 (5)0.6997 (3)0.6810 (3)0.0495 (12)
H150.84430.70030.72850.059*
C160.8374 (5)0.6272 (3)0.6259 (4)0.0617 (15)
H160.90420.58170.63600.074*
C170.7750 (5)0.6236 (4)0.5582 (4)0.0600 (15)
H170.79840.57570.52130.072*
C180.6766 (5)0.6907 (3)0.5438 (3)0.0482 (13)
C190.6023 (5)0.6905 (4)0.4744 (3)0.0641 (16)
H190.62320.64500.43480.077*
C200.5024 (6)0.7560 (4)0.4665 (3)0.0661 (16)
H200.45510.75320.42210.079*
C210.4670 (5)0.8289 (4)0.5235 (3)0.0464 (12)
C220.3630 (5)0.8974 (4)0.5197 (3)0.0579 (14)
H220.31200.89710.47710.070*
C230.3367 (5)0.9635 (4)0.5774 (3)0.0518 (13)
H230.26731.00820.57570.062*
C240.4157 (4)0.9631 (3)0.6391 (3)0.0451 (12)
H240.39761.00970.67770.054*
C250.8448 (4)0.9804 (3)0.7112 (3)0.0355 (10)
C260.9559 (4)1.0368 (3)0.7160 (3)0.0335 (10)
C271.0267 (5)0.9982 (4)0.7824 (3)0.0525 (13)
H271.00550.93690.82100.063*
C281.1267 (5)1.0449 (4)0.7949 (4)0.0639 (15)
H281.17241.01550.84030.077*
C291.1583 (5)1.1361 (4)0.7392 (4)0.0597 (15)
H291.22541.16960.74640.072*
C301.0889 (5)1.1765 (4)0.6728 (3)0.0545 (14)
H301.11051.23830.63550.065*
C310.9879 (4)1.1300 (3)0.6582 (3)0.0382 (11)
C320.9304 (4)1.1779 (3)0.5740 (3)0.0467 (12)
C330.9827 (5)1.1414 (3)0.4889 (3)0.0505 (13)
H331.04071.08740.48960.061*
C340.9473 (5)1.1854 (4)0.4096 (4)0.0703 (17)
H340.97601.15920.35580.084*
C350.8636 (5)1.2748 (4)0.4069 (4)0.0711 (17)
H350.84311.30820.35070.085*
C360.8155 (5)1.3089 (4)0.4883 (3)0.0525 (13)
H360.76141.36530.48750.063*
C370.8477 (5)1.2592 (4)0.5721 (3)0.0515 (13)
C380.7835 (5)1.2933 (4)0.6589 (4)0.0517 (13)
O50.5364 (3)0.4416 (3)0.7713 (2)0.0637 (10)
O60.3732 (3)0.3897 (2)0.7279 (2)0.0534 (9)
O7−0.0451 (4)0.4415 (3)0.7539 (3)0.0927 (13)
O80.1589 (4)0.4398 (3)0.6921 (2)0.0643 (10)
H8B0.22550.42240.70970.096*
C390.4238 (5)0.4485 (3)0.7635 (3)0.0440 (12)
C400.3400 (4)0.5330 (3)0.7956 (3)0.0378 (11)
C410.3802 (4)0.6285 (3)0.7610 (3)0.0513 (13)
H410.46010.63810.72250.062*
C420.3053 (5)0.7102 (3)0.7819 (3)0.0567 (14)
H420.33230.77430.75530.068*
C430.1916 (5)0.6958 (3)0.8416 (3)0.0568 (14)
H430.14070.75010.85770.068*
C440.1511 (4)0.5996 (3)0.8790 (3)0.0496 (13)
H440.07370.59040.92110.059*
C450.2223 (4)0.5183 (3)0.8554 (3)0.0352 (10)
C460.1725 (4)0.4179 (3)0.8974 (3)0.0373 (11)
C470.1929 (4)0.3696 (3)0.9849 (3)0.0471 (12)
H470.24180.39941.01490.057*
C480.1422 (5)0.2782 (4)1.0288 (3)0.0571 (14)
H480.16030.24511.08590.069*
C490.0635 (5)0.2368 (4)0.9855 (4)0.0640 (16)
H490.02850.17571.01420.077*
C500.0370 (4)0.2852 (3)0.9012 (4)0.0541 (14)
H50−0.01880.25830.87460.065*
C510.0930 (4)0.3744 (3)0.8553 (3)0.0431 (11)
C520.0630 (6)0.4223 (4)0.7638 (4)0.0559 (13)
O90.7109 (4)0.5128 (3)0.8546 (3)0.0742 (11)
H9A0.652 (4)0.497 (5)0.830 (4)0.111*
H9B0.785 (3)0.495 (5)0.830 (4)0.111*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0397 (3)0.0354 (3)0.0325 (3)−0.0046 (2)−0.0036 (2)−0.0120 (2)
O10.043 (2)0.0487 (19)0.0378 (18)−0.0073 (15)−0.0123 (15)−0.0061 (15)
O20.0471 (19)0.0346 (17)0.0341 (17)−0.0083 (14)−0.0023 (14)0.0018 (14)
O30.098 (3)0.065 (2)0.056 (2)0.011 (2)0.004 (2)−0.014 (2)
O40.099 (3)0.088 (3)0.070 (3)0.031 (3)−0.016 (2)−0.026 (2)
N10.049 (2)0.030 (2)0.033 (2)−0.0050 (17)−0.0075 (17)−0.0103 (16)
N20.039 (2)0.033 (2)0.036 (2)−0.0035 (17)−0.0071 (17)−0.0091 (16)
N30.040 (2)0.035 (2)0.033 (2)−0.0099 (18)−0.0012 (17)−0.0070 (16)
N40.041 (2)0.034 (2)0.032 (2)−0.0026 (18)−0.0001 (17)−0.0033 (16)
C10.037 (3)0.038 (3)0.033 (2)−0.005 (2)−0.012 (2)−0.006 (2)
C20.034 (3)0.042 (3)0.030 (2)−0.004 (2)−0.0107 (19)−0.011 (2)
C30.057 (3)0.037 (3)0.044 (3)−0.005 (2)−0.007 (2)−0.007 (2)
C40.055 (3)0.031 (2)0.064 (3)0.004 (2)−0.014 (3)−0.015 (2)
C50.046 (3)0.048 (3)0.058 (3)0.010 (2)−0.013 (2)−0.027 (3)
C60.036 (3)0.046 (3)0.036 (3)0.000 (2)−0.008 (2)−0.016 (2)
C70.045 (3)0.068 (4)0.046 (3)0.004 (3)−0.002 (2)−0.027 (3)
C80.048 (3)0.072 (4)0.029 (2)0.003 (3)0.005 (2)−0.013 (2)
C90.043 (3)0.052 (3)0.033 (2)−0.011 (2)−0.002 (2)−0.009 (2)
C100.066 (4)0.053 (3)0.039 (3)−0.014 (3)0.004 (2)0.000 (2)
C110.082 (4)0.040 (3)0.050 (3)−0.011 (3)0.000 (3)0.002 (2)
C120.060 (3)0.042 (3)0.046 (3)−0.005 (3)−0.009 (2)−0.006 (2)
C130.043 (3)0.035 (2)0.029 (2)−0.013 (2)−0.002 (2)−0.0024 (19)
C140.042 (3)0.040 (3)0.028 (2)−0.013 (2)0.003 (2)−0.008 (2)
C150.057 (3)0.048 (3)0.037 (3)0.004 (3)−0.003 (2)−0.003 (2)
C160.065 (4)0.037 (3)0.065 (4)0.012 (3)0.010 (3)−0.003 (3)
C170.076 (4)0.045 (3)0.054 (3)−0.009 (3)0.014 (3)−0.024 (3)
C180.056 (3)0.046 (3)0.041 (3)−0.014 (3)0.008 (2)−0.019 (2)
C190.080 (4)0.077 (4)0.041 (3)−0.026 (3)0.003 (3)−0.031 (3)
C200.074 (4)0.095 (5)0.038 (3)−0.028 (4)−0.009 (3)−0.026 (3)
C210.053 (3)0.055 (3)0.031 (3)−0.024 (3)−0.009 (2)0.001 (2)
C220.060 (4)0.072 (4)0.043 (3)−0.030 (3)−0.022 (3)0.008 (3)
C230.049 (3)0.053 (3)0.052 (3)−0.010 (3)−0.016 (3)0.002 (3)
C240.041 (3)0.043 (3)0.051 (3)−0.007 (2)−0.008 (2)−0.007 (2)
C250.031 (3)0.039 (3)0.039 (3)0.006 (2)−0.004 (2)−0.020 (2)
C260.031 (3)0.037 (2)0.033 (2)0.004 (2)−0.0042 (19)−0.012 (2)
C270.054 (3)0.055 (3)0.047 (3)−0.005 (3)−0.012 (3)−0.006 (2)
C280.055 (4)0.080 (4)0.064 (4)−0.013 (3)−0.026 (3)−0.015 (3)
C290.038 (3)0.084 (4)0.067 (4)−0.015 (3)−0.006 (3)−0.035 (3)
C300.050 (3)0.058 (3)0.059 (3)−0.016 (3)−0.003 (3)−0.021 (3)
C310.032 (3)0.046 (3)0.038 (2)−0.004 (2)−0.002 (2)−0.017 (2)
C320.034 (3)0.035 (3)0.067 (3)−0.013 (2)0.003 (2)−0.012 (2)
C330.064 (4)0.049 (3)0.034 (3)−0.013 (3)0.005 (2)−0.008 (2)
C340.056 (4)0.098 (5)0.051 (4)−0.003 (3)0.008 (3)−0.022 (3)
C350.074 (4)0.090 (5)0.050 (3)−0.019 (4)−0.013 (3)−0.007 (3)
C360.057 (3)0.063 (3)0.037 (3)−0.014 (3)−0.009 (2)−0.003 (2)
C370.049 (3)0.053 (3)0.051 (3)−0.018 (3)0.007 (2)−0.019 (3)
C380.063 (4)0.052 (3)0.042 (3)−0.013 (3)0.000 (3)−0.019 (3)
O50.039 (2)0.078 (3)0.076 (2)0.0133 (19)−0.0019 (18)−0.038 (2)
O60.065 (2)0.0467 (19)0.050 (2)0.0005 (17)−0.0018 (17)−0.0241 (16)
O70.067 (3)0.101 (3)0.114 (4)0.006 (3)−0.042 (3)−0.009 (3)
O80.076 (3)0.073 (3)0.048 (2)−0.005 (2)−0.021 (2)−0.0099 (18)
C390.046 (3)0.044 (3)0.036 (3)0.002 (2)0.005 (2)−0.009 (2)
C400.042 (3)0.034 (2)0.035 (2)−0.003 (2)0.001 (2)−0.010 (2)
C410.047 (3)0.048 (3)0.052 (3)−0.009 (3)0.009 (2)−0.011 (2)
C420.064 (4)0.034 (3)0.062 (3)−0.010 (3)0.008 (3)−0.007 (2)
C430.058 (4)0.034 (3)0.072 (4)0.005 (2)0.006 (3)−0.018 (2)
C440.045 (3)0.039 (3)0.053 (3)0.001 (2)0.015 (2)−0.010 (2)
C450.033 (3)0.034 (2)0.038 (2)−0.001 (2)−0.002 (2)−0.0104 (19)
C460.036 (3)0.034 (2)0.037 (3)0.001 (2)0.004 (2)−0.008 (2)
C470.046 (3)0.048 (3)0.040 (3)0.004 (2)0.005 (2)−0.009 (2)
C480.058 (4)0.054 (3)0.044 (3)0.012 (3)0.012 (3)−0.004 (3)
C490.071 (4)0.035 (3)0.065 (4)−0.001 (3)0.025 (3)−0.002 (3)
C500.048 (3)0.039 (3)0.073 (4)−0.010 (2)0.002 (3)−0.018 (3)
C510.044 (3)0.032 (2)0.049 (3)−0.002 (2)0.000 (2)−0.009 (2)
C520.060 (4)0.045 (3)0.066 (4)0.002 (3)−0.023 (3)−0.010 (3)
O90.089 (3)0.065 (3)0.071 (3)−0.009 (3)−0.008 (2)−0.024 (2)

Geometric parameters (Å, °)

Zn1—O22.078 (3)C23—C241.387 (6)
Zn1—N12.128 (3)C23—H230.93
Zn1—N42.130 (3)C24—H240.93
Zn1—N32.145 (4)C25—C261.507 (5)
Zn1—N22.145 (3)C26—C271.375 (6)
Zn1—O12.334 (3)C26—C311.409 (6)
Zn1—C252.528 (4)C27—C281.371 (6)
O1—C251.237 (5)C27—H270.93
O2—C251.276 (5)C28—C291.374 (7)
O3—C381.207 (5)C28—H280.93
O4—C381.326 (6)C29—C301.370 (6)
O4—H4B0.82C29—H290.93
N1—C121.327 (5)C30—C311.391 (6)
N1—C11.370 (5)C30—H300.93
N2—C31.333 (5)C31—C321.525 (6)
N2—C21.355 (5)C32—C371.369 (6)
N3—C241.331 (5)C32—C331.446 (6)
N3—C131.373 (5)C33—C341.331 (6)
N4—C151.321 (5)C33—H330.93
N4—C141.366 (5)C34—C351.462 (7)
C1—C91.409 (5)C34—H340.93
C1—C21.426 (5)C35—C361.374 (6)
C2—C61.405 (5)C35—H350.93
C3—C41.394 (6)C36—C371.394 (6)
C3—H30.93C36—H360.93
C4—C51.366 (6)C37—C381.478 (6)
C4—H4A0.93O5—C391.243 (5)
C5—C61.394 (6)O6—C391.274 (5)
C5—H50.93O7—C521.211 (6)
C6—C71.415 (5)O8—C521.314 (6)
C7—C81.353 (6)O8—H8B0.82
C7—H70.93C39—C401.503 (6)
C8—C91.430 (6)C40—C411.376 (6)
C8—H8A0.93C40—C451.389 (5)
C9—C101.400 (6)C41—C421.377 (6)
C10—C111.365 (6)C41—H410.93
C10—H100.93C42—C431.353 (6)
C11—C121.403 (6)C42—H420.93
C11—H110.93C43—C441.390 (6)
C12—H120.93C43—H430.93
C13—C211.414 (6)C44—C451.365 (5)
C13—C141.418 (6)C44—H440.93
C14—C181.410 (6)C45—C461.484 (5)
C15—C161.401 (6)C46—C471.390 (6)
C15—H150.93C46—C511.407 (6)
C16—C171.343 (7)C47—C481.387 (6)
C16—H160.93C47—H470.93
C17—C181.370 (7)C48—C491.395 (7)
C17—H170.93C48—H480.93
C18—C191.444 (7)C49—C501.371 (7)
C19—C201.356 (7)C49—H490.93
C19—H190.93C50—C511.389 (6)
C20—C211.423 (6)C50—H500.93
C20—H200.93C51—C521.477 (6)
C21—C221.406 (7)O9—H9A0.87 (5)
C22—C231.351 (6)O9—H9B0.84 (2)
C22—H220.93
O2—Zn1—N1102.73 (12)C23—C22—C21120.6 (5)
O2—Zn1—N497.11 (12)C23—C22—H22119.7
N1—Zn1—N4100.12 (12)C21—C22—H22119.7
O2—Zn1—N3155.43 (11)C22—C23—C24118.4 (5)
N1—Zn1—N3101.83 (13)C22—C23—H23120.8
N4—Zn1—N377.99 (14)C24—C23—H23120.8
O2—Zn1—N294.88 (12)N3—C24—C23124.5 (4)
N1—Zn1—N277.67 (12)N3—C24—H24117.8
N4—Zn1—N2167.99 (13)C23—C24—H24117.8
N3—Zn1—N290.84 (13)O1—C25—O2121.2 (4)
O2—Zn1—O159.17 (10)O1—C25—C26122.0 (4)
N1—Zn1—O1155.22 (11)O2—C25—C26116.7 (4)
N4—Zn1—O198.98 (11)O1—C25—Zn166.7 (2)
N3—Zn1—O197.46 (11)O2—C25—Zn155.0 (2)
N2—Zn1—O186.71 (11)C26—C25—Zn1167.7 (3)
O2—Zn1—C2530.21 (12)C27—C26—C31117.9 (4)
N1—Zn1—C25129.98 (14)C27—C26—C25119.0 (4)
N4—Zn1—C25101.56 (13)C31—C26—C25123.1 (4)
N3—Zn1—C25126.52 (13)C28—C27—C26123.7 (5)
N2—Zn1—C2588.57 (12)C28—C27—H27118.1
O1—Zn1—C2529.12 (11)C26—C27—H27118.1
C25—O1—Zn184.2 (2)C27—C28—C29118.9 (5)
C25—O2—Zn194.8 (3)C27—C28—H28120.6
C38—O4—H4B109.5C29—C28—H28120.6
C12—N1—C1118.0 (4)C30—C29—C28118.6 (5)
C12—N1—Zn1128.5 (3)C30—C29—H29120.7
C1—N1—Zn1113.3 (3)C28—C29—H29120.7
C3—N2—C2118.5 (4)C29—C30—C31123.6 (5)
C3—N2—Zn1127.8 (3)C29—C30—H30118.2
C2—N2—Zn1113.7 (3)C31—C30—H30118.2
C24—N3—C13117.3 (4)C30—C31—C26117.4 (4)
C24—N3—Zn1129.6 (3)C30—C31—C32117.4 (4)
C13—N3—Zn1113.1 (3)C26—C31—C32124.8 (4)
C15—N4—C14117.6 (4)C37—C32—C33120.0 (5)
C15—N4—Zn1129.0 (3)C37—C32—C31124.1 (4)
C14—N4—Zn1113.5 (3)C33—C32—C31115.4 (4)
N1—C1—C9122.2 (4)C34—C33—C32119.6 (5)
N1—C1—C2117.6 (4)C34—C33—H33120.2
C9—C1—C2120.1 (4)C32—C33—H33120.2
N2—C2—C6122.6 (4)C33—C34—C35120.2 (5)
N2—C2—C1117.1 (4)C33—C34—H34119.9
C6—C2—C1120.3 (4)C35—C34—H34119.9
N2—C3—C4122.2 (4)C36—C35—C34119.2 (5)
N2—C3—H3118.9C36—C35—H35120.4
C4—C3—H3118.9C34—C35—H35120.4
C5—C4—C3119.4 (4)C35—C36—C37120.2 (5)
C5—C4—H4A120.3C35—C36—H36119.9
C3—C4—H4A120.3C37—C36—H36119.9
C4—C5—C6120.0 (4)C32—C37—C36120.7 (4)
C4—C5—H5120.0C32—C37—C38121.5 (5)
C6—C5—H5120.0C36—C37—C38117.7 (5)
C5—C6—C2117.3 (4)O3—C38—O4122.4 (5)
C5—C6—C7124.3 (4)O3—C38—C37125.5 (5)
C2—C6—C7118.4 (4)O4—C38—C37111.9 (5)
C8—C7—C6121.8 (4)C52—O8—H8B109.5
C8—C7—H7119.1O5—C39—O6124.5 (4)
C6—C7—H7119.1O5—C39—C40119.0 (4)
C7—C8—C9121.3 (4)O6—C39—C40116.4 (4)
C7—C8—H8A119.3C41—C40—C45119.1 (4)
C9—C8—H8A119.3C41—C40—C39118.3 (4)
C10—C9—C1117.8 (4)C45—C40—C39122.5 (4)
C10—C9—C8124.1 (4)C40—C41—C42121.8 (4)
C1—C9—C8118.0 (4)C40—C41—H41119.1
C11—C10—C9119.8 (4)C42—C41—H41119.1
C11—C10—H10120.1C43—C42—C41118.9 (4)
C9—C10—H10120.1C43—C42—H42120.5
C10—C11—C12119.1 (5)C41—C42—H42120.5
C10—C11—H11120.5C42—C43—C44119.9 (4)
C12—C11—H11120.5C42—C43—H43120.0
N1—C12—C11123.1 (4)C44—C43—H43120.0
N1—C12—H12118.5C45—C44—C43121.5 (4)
C11—C12—H12118.5C45—C44—H44119.2
N3—C13—C21121.7 (4)C43—C44—H44119.2
N3—C13—C14117.4 (4)C44—C45—C40118.6 (4)
C21—C13—C14120.9 (4)C44—C45—C46118.6 (4)
N4—C14—C18121.7 (4)C40—C45—C46122.8 (4)
N4—C14—C13117.9 (4)C47—C46—C51118.4 (4)
C18—C14—C13120.4 (4)C47—C46—C45119.9 (4)
N4—C15—C16122.8 (5)C51—C46—C45121.3 (4)
N4—C15—H15118.6C48—C47—C46121.7 (5)
C16—C15—H15118.6C48—C47—H47119.2
C17—C16—C15119.6 (5)C46—C47—H47119.2
C17—C16—H16120.2C47—C48—C49118.6 (5)
C15—C16—H16120.2C47—C48—H48120.7
C16—C17—C18119.9 (5)C49—C48—H48120.7
C16—C17—H17120.1C50—C49—C48120.8 (5)
C18—C17—H17120.1C50—C49—H49119.6
C17—C18—C14118.5 (5)C48—C49—H49119.6
C17—C18—C19123.5 (5)C49—C50—C51120.3 (5)
C14—C18—C19118.0 (5)C49—C50—H50119.8
C20—C19—C18120.6 (5)C51—C50—H50119.8
C20—C19—H19119.7C50—C51—C46120.0 (5)
C18—C19—H19119.7C50—C51—C52118.0 (5)
C19—C20—C21122.5 (5)C46—C51—C52121.9 (4)
C19—C20—H20118.7O7—C52—O8121.0 (5)
C21—C20—H20118.7O7—C52—C51121.9 (5)
C22—C21—C13117.5 (4)O8—C52—C51117.0 (5)
C22—C21—C20125.0 (5)H9A—O9—H9B115 (6)
C13—C21—C20117.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O9—H9B···O7i0.84 (4)2.10 (5)2.936 (6)171 (6)
O4—H4B···O5ii0.821.862.633 (5)158
O9—H9A···O50.87 (5)1.96 (6)2.817 (6)171 (7)
O8—H8B···O60.821.692.500 (5)171
C3—H3···O10.932.553.130 (5)121
C4—H4A···O6ii0.932.423.221 (5)144
C12—H12···O90.932.423.273 (6)152
C16—H16···O7i0.932.433.199 (7)139
C19—H19···O6iii0.932.563.377 (5)146
C22—H22···O1iv0.932.433.249 (6)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2560).

References

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