PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m729–m730.
Published online 2009 June 6. doi:  10.1107/S1600536809020716
PMCID: PMC2969424

(μ-Acetato){μ-1,3-bis[2-(2-oxidobenzylideneamino)ethyl]-2-(2-oxidophenyl)-1,3-imidazolidine}dizinc(II) ethanol disolvate dihydrate

Abstract

In the title binuclear compound, [Zn2(C27H27N4O3)(C2H3O2)]·2CH3CH2OH·2H2O, both Zn cations adopt distorted ZnO3N2 trigonal-bipyramidal geometries with one N atom in a axial site and one N atom in an equatorial site, arising from coordination by the N,N,N,N,O,O,O-hepta­dentate ligand and a bridging acetate ion. In the crystal, inter­molecular O—H(...)O hydrogen bonds link the component units into a three-dimensional network. Two short C—H(...)O contacts are also seen.

Related literature

For further synthetic details, see: Sarma & Bailar (1955 [triangle]); Lu et al. (2007 [triangle]). For background information on the ligand, see: Fondo et al. (2002 [triangle]); Fondo et al. (2004 [triangle]); Prasant Kumar et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m729-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2O
  • M r = 773.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m729-efi1.jpg
  • a = 10.140 (3) Å
  • b = 11.540 (4) Å
  • c = 16.066 (5) Å
  • α = 91.972 (6)°
  • β = 93.944 (5)°
  • γ = 110.833 (5)°
  • V = 1749.4 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.43 mm−1
  • T = 298 K
  • 0.22 × 0.20 × 0.03 mm

Data collection

  • SMART 1K CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.744, T max = 0.958
  • 8975 measured reflections
  • 5943 independent reflections
  • 4785 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.151
  • S = 1.09
  • 5943 reflections
  • 437 parameters
  • 14 restraints
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL/PC.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020716/hb2964sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020716/hb2964Isup2.hkl

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

Acknowledgments

The authors acknowledge the National and Shanxi Provincial Natural Science Foundation of China (grant Nos. 20471033 and 20051013) as well as the Overseas Returned Scholar Foundation of Shanxi Province of China in 2008 for financial support.

supplementary crystallographic information

Comment

In earlier studies of binuclear and tetranuclear complexes of a heptadentate Schiff base, 2-(2-hydroxyphenyl)-1,3-bis[4-(2-hydroxyphenyl)-3-azabut-3-enyl]- 1,3-imidazolidine (H3L), researchers reported attractive results, such as fixed atmospheric carbon dioxide (Fondo et al., 2002), magnetic properties (Fondo et al., 2004; Prasant Kumar et al., 2006). As part of our own work, the title complex, (I), has been syhtheszed in order to study its inhibiting activity on protein tyrosine phosphatase 1B (PTP1B), and its crystal structure is presented here.

The Zn—N and Zn—O distances and bond anges around two metal ions are in the normal range (Table 1). The molecular structure is illustrated in Fig. 1. Binuclear phenolic Schiff base complex (I) consists of Zn2L(OOCCH3) units with ethanol and water as solvates. Each zinc atom is coordinated by two N atoms and three O atoms from the heptadentate Schiff base ligand and an acetate. The intermetallic separation is 3.229 (2) Å shorter than that in Zn2L(OOCCH3).methanol.2H2O (Fondo et al., 2002). Two zinc ions are linked by dibridges with one phenol oxygen atom of the ligand and another bidentate acetate group.

Experimental

The heptadentate Schiff base has been prepared following a modified literature procedure (Sarma & Bailar, 1955; Lu, et al. 2007). The ligand was collected by filtration and recrystallized from warm ethanol. Compared IR spectroscopic data with the literature values has checked identity and purity of the ligand. The title compound (I) was synthesized as following. 0.0885 g Zn(CH3CH2O)2.2H2O was added to 0.0548 g H3L in 25 ml of ethanol solution with stirring, in a 1:1 molar ratio. Refluxed for 2 h, adjusted pH 8 with 1 M NaOH after the solution cooled to room temperature, filtered. Colourless blocks of (I) were grown from the filtrate by slow evaporation.

Refinement

H atoms attached to C atoms and O(ethanol) of (I) were placed in geometrically idealized positions, with Csp2—H = 0.93, Csp3H(methylene) = 0.97, Csp3H(methyl) = 0.96, Csp3—H = 0.98, O—H = 0.82 Å and refined with Uiso(H)=1.2Ueq or 1.5Ueq(methyl, ethanol). The water H atoms were located in a difference map and refined as riding in their as-found relative positions.

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids drawn at the 30% probability level for Non-H atoms.

Crystal data

[Zn2(C27H27N4O3)(C2H3O2)]·2CH6O·2H2OZ = 2
Mr = 773.48F(000) = 808
Triclinic, P1Dx = 1.468 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.140 (3) ÅCell parameters from 4728 reflections
b = 11.540 (4) Åθ = 2.2–26.5°
c = 16.066 (5) ŵ = 1.43 mm1
α = 91.972 (6)°T = 298 K
β = 93.944 (5)°Block, colourless
γ = 110.833 (5)°0.22 × 0.20 × 0.03 mm
V = 1749.4 (10) Å3

Data collection

SMART 1K CCD diffractometer5943 independent reflections
Radiation source: fine-focus sealed tube4785 reflections with I > 2σ(I)
graphiteRint = 0.018
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS;Bruker, 2000)h = −12→11
Tmin = 0.744, Tmax = 0.958k = −13→10
8975 measured reflectionsl = −19→17

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0929P)2 + 0.4983P] where P = (Fo2 + 2Fc2)/3
5943 reflections(Δ/σ)max = 0.009
437 parametersΔρmax = 0.82 e Å3
14 restraintsΔρmin = −0.60 e Å3

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
Zn10.08495 (4)0.22680 (4)0.14633 (3)0.05247 (17)
Zn20.20169 (5)0.50951 (4)0.22548 (3)0.05443 (17)
N10.0865 (3)0.0549 (3)0.1233 (2)0.0569 (8)
N20.3245 (3)0.2542 (3)0.1953 (2)0.0536 (7)
N30.4056 (3)0.4539 (3)0.2503 (2)0.0566 (8)
N40.3384 (3)0.6668 (3)0.2863 (2)0.0618 (8)
C1−0.2122 (4)0.0545 (4)0.1133 (2)0.0597 (10)
C2−0.3590 (4)0.0315 (4)0.1036 (3)0.0719 (12)
H2−0.38980.09830.10700.086*
C3−0.4571 (5)−0.0861 (5)0.0895 (3)0.0774 (13)
H3−0.5528−0.09750.08380.093*
C4−0.4167 (5)−0.1883 (5)0.0836 (3)0.0751 (12)
H4−0.4839−0.26820.07520.090*
C5−0.2739 (5)−0.1683 (4)0.0907 (3)0.0692 (11)
H5−0.2455−0.23640.08610.083*
C6−0.1709 (4)−0.0504 (3)0.1043 (2)0.0544 (9)
C7−0.0231 (4)−0.0419 (4)0.1092 (2)0.0566 (9)
H7−0.0080−0.11630.10110.068*
C80.2267 (4)0.0441 (4)0.1272 (3)0.0612 (10)
H8A0.27100.07090.07610.073*
H8B0.2175−0.04180.13320.073*
C90.3153 (4)0.1239 (4)0.2005 (3)0.0628 (10)
H9A0.27440.09210.25160.075*
H9B0.40980.12060.20240.075*
C100.4315 (4)0.3269 (4)0.1393 (3)0.0664 (11)
H10A0.50820.29540.13760.080*
H10B0.38820.32230.08290.080*
C110.4848 (4)0.4573 (4)0.1762 (3)0.0694 (11)
H11A0.58580.48530.19210.083*
H11B0.46700.51270.13660.083*
C120.3722 (4)0.3261 (4)0.2764 (2)0.0546 (9)
H120.45960.31640.29920.065*
C130.2647 (4)0.2889 (3)0.3391 (2)0.0520 (8)
C140.2967 (5)0.2487 (4)0.4157 (3)0.0667 (11)
H140.38540.24350.42760.080*
C150.1989 (5)0.2163 (5)0.4743 (3)0.0780 (13)
H150.22200.19060.52570.094*
C160.0674 (5)0.2222 (5)0.4565 (3)0.0785 (13)
H160.00100.19940.49580.094*
C170.0326 (4)0.2613 (4)0.3813 (3)0.0613 (10)
H17−0.05700.26520.37050.074*
C180.1289 (4)0.2953 (3)0.3212 (2)0.0477 (8)
C190.4876 (4)0.5472 (4)0.3184 (3)0.0697 (11)
H19A0.58460.54990.32420.084*
H19B0.44670.52350.37090.084*
C200.4862 (4)0.6744 (4)0.2993 (3)0.0731 (12)
H20A0.53510.73400.34540.088*
H20B0.53440.70170.24940.088*
C210.3042 (4)0.7583 (4)0.3131 (3)0.0612 (10)
H210.37720.82670.33920.073*
C220.1655 (4)0.7655 (4)0.3069 (2)0.0566 (9)
C230.1567 (5)0.8780 (4)0.3388 (3)0.0633 (10)
H230.23820.93910.36410.076*
C240.0333 (5)0.9001 (4)0.3339 (3)0.0696 (11)
H240.03070.97550.35450.084*
C25−0.0882 (5)0.8085 (4)0.2975 (3)0.0702 (11)
H25−0.17310.82250.29300.084*
C26−0.0841 (4)0.6961 (4)0.2678 (3)0.0630 (10)
H26−0.16770.63470.24520.076*
C270.0417 (4)0.6716 (4)0.2707 (2)0.0537 (9)
C280.1736 (4)0.4442 (5)0.0426 (3)0.0613 (10)
C290.1851 (7)0.4939 (6)−0.0427 (3)0.0991 (18)
H29A0.24440.4622−0.07330.149*
H29B0.22590.5830−0.03740.149*
H29C0.09260.4684−0.07190.149*
O1−0.1248 (3)0.1685 (3)0.1286 (2)0.0772 (9)
O20.0941 (2)0.3340 (2)0.24742 (14)0.0472 (5)
O30.1323 (4)0.3318 (3)0.04947 (18)0.0733 (8)
O40.2108 (4)0.5244 (3)0.1030 (2)0.0794 (9)
O50.0387 (3)0.5631 (3)0.2420 (2)0.0691 (8)
O60.2092 (3)0.6480 (3)0.7851 (2)0.0703 (8)
H6A0.20340.71530.80900.105*
H6B0.14180.58530.79900.105*
O70.1725 (9)0.7596 (7)0.0605 (5)0.213 (4)
H7A0.20310.70190.07180.320*
H7B0.20010.78600.01280.320*
C300.2098 (9)0.5605 (8)0.5762 (4)0.127 (3)
H30A0.22340.48440.59050.153*
H30B0.11170.55020.58170.153*
C310.2435 (14)0.5870 (10)0.4942 (5)0.199 (6)
H31A0.18940.63340.47100.299*
H31B0.22150.51070.46090.299*
H31C0.34270.63500.49440.299*
O80.3030 (4)0.6641 (5)0.6310 (3)0.1170 (15)
H80.28530.65090.67960.175*
C320.6498 (10)0.0359 (9)0.4137 (6)0.139 (3)
H32A0.6157−0.04670.43420.167*
H32B0.73380.08790.44820.167*
C330.6737 (12)0.0333 (9)0.3300 (7)0.185 (5)
H33A0.6241−0.04890.30490.278*
H33B0.77330.05570.32490.278*
H33C0.64020.09110.30220.278*
O90.5470 (10)0.0873 (7)0.4090 (7)0.232 (4)
H90.58420.16320.41120.349*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0555 (3)0.0558 (3)0.0513 (3)0.0263 (2)0.00372 (19)0.00521 (19)
Zn20.0532 (3)0.0547 (3)0.0556 (3)0.0197 (2)0.00390 (19)0.00497 (19)
N10.0601 (19)0.065 (2)0.0561 (18)0.0347 (17)0.0064 (15)0.0058 (15)
N20.0495 (17)0.0658 (19)0.0560 (18)0.0310 (15)0.0136 (14)0.0149 (15)
N30.0444 (16)0.064 (2)0.065 (2)0.0221 (15)0.0084 (14)0.0114 (15)
N40.0450 (17)0.067 (2)0.070 (2)0.0161 (15)0.0042 (15)0.0061 (17)
C10.055 (2)0.068 (3)0.058 (2)0.027 (2)0.0006 (18)−0.0042 (19)
C20.054 (2)0.071 (3)0.090 (3)0.025 (2)−0.003 (2)−0.010 (2)
C30.058 (3)0.094 (4)0.081 (3)0.028 (2)0.006 (2)−0.001 (3)
C40.068 (3)0.072 (3)0.071 (3)0.007 (2)0.002 (2)0.003 (2)
C50.081 (3)0.058 (2)0.070 (3)0.026 (2)0.002 (2)0.006 (2)
C60.061 (2)0.055 (2)0.049 (2)0.0223 (18)0.0014 (17)0.0055 (16)
C70.064 (2)0.052 (2)0.062 (2)0.0295 (19)0.0052 (18)0.0042 (17)
C80.059 (2)0.066 (2)0.070 (3)0.036 (2)0.0111 (19)0.004 (2)
C90.057 (2)0.079 (3)0.069 (2)0.043 (2)0.0110 (19)0.018 (2)
C100.053 (2)0.086 (3)0.069 (3)0.032 (2)0.0218 (19)0.017 (2)
C110.050 (2)0.079 (3)0.083 (3)0.023 (2)0.022 (2)0.020 (2)
C120.0420 (18)0.074 (2)0.052 (2)0.0271 (17)0.0007 (15)0.0081 (18)
C130.051 (2)0.060 (2)0.051 (2)0.0270 (17)0.0050 (16)0.0091 (16)
C140.060 (2)0.090 (3)0.059 (2)0.039 (2)0.0000 (19)0.013 (2)
C150.090 (3)0.101 (4)0.052 (2)0.044 (3)0.007 (2)0.023 (2)
C160.081 (3)0.105 (4)0.059 (3)0.040 (3)0.026 (2)0.024 (2)
C170.050 (2)0.077 (3)0.061 (2)0.0260 (19)0.0149 (18)0.010 (2)
C180.0456 (18)0.055 (2)0.0439 (18)0.0192 (16)0.0037 (14)0.0028 (15)
C190.041 (2)0.079 (3)0.083 (3)0.0179 (19)−0.0087 (19)−0.003 (2)
C200.048 (2)0.068 (3)0.095 (3)0.0106 (19)0.006 (2)0.003 (2)
C210.053 (2)0.055 (2)0.070 (3)0.0144 (18)0.0028 (19)0.0009 (19)
C220.059 (2)0.051 (2)0.059 (2)0.0181 (17)0.0044 (17)0.0121 (17)
C230.066 (2)0.055 (2)0.065 (2)0.0166 (19)0.0029 (19)0.0028 (18)
C240.086 (3)0.055 (2)0.074 (3)0.031 (2)0.020 (2)0.010 (2)
C250.068 (3)0.076 (3)0.074 (3)0.034 (2)0.014 (2)0.010 (2)
C260.054 (2)0.062 (2)0.070 (3)0.0180 (18)0.0047 (19)0.0014 (19)
C270.054 (2)0.053 (2)0.055 (2)0.0200 (17)0.0063 (16)0.0032 (17)
C280.061 (2)0.085 (3)0.053 (2)0.042 (2)0.0157 (18)0.017 (2)
C290.140 (5)0.107 (4)0.064 (3)0.057 (4)0.021 (3)0.029 (3)
O10.0533 (16)0.0614 (18)0.116 (3)0.0245 (14)−0.0111 (16)−0.0170 (17)
O20.0396 (12)0.0561 (14)0.0486 (13)0.0202 (10)0.0035 (10)0.0065 (10)
O30.097 (2)0.075 (2)0.0534 (16)0.0353 (17)0.0087 (15)0.0175 (14)
O40.110 (3)0.076 (2)0.0631 (19)0.0431 (19)0.0184 (17)0.0240 (16)
O50.0545 (15)0.0592 (17)0.090 (2)0.0205 (13)−0.0054 (14)−0.0136 (15)
O60.0563 (16)0.0773 (19)0.080 (2)0.0279 (14)0.0070 (14)0.0029 (15)
O70.290 (10)0.149 (6)0.199 (8)0.087 (6)−0.036 (7)0.008 (5)
C300.158 (7)0.158 (7)0.089 (4)0.090 (6)−0.008 (4)−0.005 (4)
C310.296 (15)0.171 (9)0.074 (5)0.011 (9)0.045 (6)−0.008 (5)
O80.094 (3)0.174 (4)0.076 (2)0.044 (3)−0.002 (2)−0.012 (3)
C320.139 (3)0.139 (3)0.139 (3)0.0500 (13)0.0112 (10)0.0098 (10)
C330.205 (11)0.136 (7)0.158 (9)−0.014 (7)0.053 (8)−0.001 (6)
O90.232 (4)0.232 (4)0.233 (4)0.0837 (17)0.0205 (11)0.0152 (11)

Geometric parameters (Å, °)

Zn1—O21.984 (2)C15—H150.9300
Zn1—O31.984 (3)C16—C171.370 (6)
Zn1—O11.986 (3)C16—H160.9300
Zn1—N12.011 (3)C17—C181.387 (5)
Zn1—N22.407 (3)C17—H170.9300
Zn2—O21.987 (2)C18—O21.350 (4)
Zn2—O41.987 (3)C19—C201.515 (7)
Zn2—O51.991 (3)C19—H19A0.9700
Zn2—N42.019 (3)C19—H19B0.9700
Zn2—N32.386 (3)C20—H20A0.9700
N1—C71.265 (5)C20—H20B0.9700
N1—C81.468 (5)C21—C221.435 (6)
N2—C121.474 (5)C21—H210.9300
N2—C91.479 (5)C22—C271.406 (5)
N2—C101.493 (5)C22—C231.414 (6)
N3—C121.474 (5)C23—C241.361 (6)
N3—C111.476 (5)C23—H230.9300
N3—C191.485 (5)C24—C251.381 (7)
N4—C211.292 (5)C24—H240.9300
N4—C201.469 (5)C25—C261.382 (6)
C1—O11.302 (5)C25—H250.9300
C1—C21.412 (6)C26—C271.400 (6)
C1—C61.421 (5)C26—H260.9300
C2—C31.368 (7)C27—O51.308 (5)
C2—H20.9300C28—O31.225 (5)
C3—C41.381 (7)C28—O41.256 (5)
C3—H30.9300C28—C291.500 (6)
C4—C51.378 (7)C29—H29A0.9600
C4—H40.9300C29—H29B0.9600
C5—C61.389 (6)C29—H29C0.9600
C5—H50.9300O6—H6A0.8774
C6—C71.463 (5)O6—H6B0.8491
C7—H70.9300O7—H7A0.8487
C8—C91.495 (6)O7—H7B0.8620
C8—H8A0.9700C30—C311.400 (10)
C8—H8B0.9700C30—O81.452 (9)
C9—H9A0.9700C30—H30A0.9700
C9—H9B0.9700C30—H30B0.9700
C10—C111.491 (7)C31—H31A0.9600
C10—H10A0.9700C31—H31B0.9600
C10—H10B0.9700C31—H31C0.9600
C11—H11A0.9700O8—H80.8200
C11—H11B0.9700C32—O91.370 (11)
C12—C131.496 (5)C32—C331.383 (12)
C12—H120.9800C32—H32A0.9700
C13—C141.387 (5)C32—H32B0.9700
C13—C181.415 (5)C33—H33A0.9600
C14—C151.378 (6)C33—H33B0.9600
C14—H140.9300C33—H33C0.9600
C15—C161.370 (7)O9—H90.8200
O2—Zn1—O3108.98 (12)C15—C14—C13120.9 (4)
O2—Zn1—O193.56 (11)C15—C14—H14119.5
O3—Zn1—O198.80 (15)C13—C14—H14119.5
O2—Zn1—N1135.96 (11)C16—C15—C14119.7 (4)
O3—Zn1—N1113.08 (13)C16—C15—H15120.1
O1—Zn1—N192.47 (13)C14—C15—H15120.1
O2—Zn1—N284.15 (10)C17—C16—C15120.7 (4)
O3—Zn1—N296.71 (12)C17—C16—H16119.6
O1—Zn1—N2164.21 (13)C15—C16—H16119.6
N1—Zn1—N278.67 (12)C16—C17—C18121.0 (4)
O2—Zn2—O4109.20 (12)C16—C17—H17119.5
O2—Zn2—O593.41 (11)C18—C17—H17119.5
O4—Zn2—O599.82 (14)O2—C18—C17120.8 (3)
O2—Zn2—N4139.65 (12)O2—C18—C13120.7 (3)
O4—Zn2—N4109.35 (14)C17—C18—C13118.6 (3)
O5—Zn2—N491.40 (13)N3—C19—C20110.2 (4)
O2—Zn2—N384.67 (10)N3—C19—H19A109.6
O4—Zn2—N397.01 (13)C20—C19—H19A109.6
O5—Zn2—N3162.73 (13)N3—C19—H19B109.6
N4—Zn2—N379.32 (13)C20—C19—H19B109.6
C7—N1—C8119.3 (3)H19A—C19—H19B108.1
C7—N1—Zn1124.7 (3)N4—C20—C19108.8 (3)
C8—N1—Zn1115.9 (3)N4—C20—H20A109.9
C12—N2—C9112.3 (3)C19—C20—H20A109.9
C12—N2—C10103.0 (3)N4—C20—H20B109.9
C9—N2—C10113.8 (3)C19—C20—H20B109.9
C12—N2—Zn1113.4 (2)H20A—C20—H20B108.3
C9—N2—Zn1101.4 (2)N4—C21—C22126.8 (4)
C10—N2—Zn1113.3 (2)N4—C21—H21116.6
C12—N3—C11103.6 (3)C22—C21—H21116.6
C12—N3—C19111.6 (3)C27—C22—C23118.9 (4)
C11—N3—C19113.1 (3)C27—C22—C21125.2 (4)
C12—N3—Zn2113.5 (2)C23—C22—C21115.9 (4)
C11—N3—Zn2114.1 (2)C24—C23—C22122.4 (4)
C19—N3—Zn2101.3 (2)C24—C23—H23118.8
C21—N4—C20119.6 (4)C22—C23—H23118.8
C21—N4—Zn2124.6 (3)C23—C24—C25118.7 (4)
C20—N4—Zn2115.8 (3)C23—C24—H24120.6
O1—C1—C2118.7 (4)C25—C24—H24120.6
O1—C1—C6124.7 (4)C24—C25—C26120.4 (4)
C2—C1—C6116.6 (4)C24—C25—H25119.8
C3—C2—C1121.9 (4)C26—C25—H25119.8
C3—C2—H2119.1C25—C26—C27122.1 (4)
C1—C2—H2119.1C25—C26—H26118.9
C2—C3—C4121.3 (4)C27—C26—H26118.9
C2—C3—H3119.4O5—C27—C26119.3 (4)
C4—C3—H3119.4O5—C27—C22123.3 (3)
C5—C4—C3118.1 (4)C26—C27—C22117.4 (4)
C5—C4—H4121.0O3—C28—O4124.7 (4)
C3—C4—H4121.0O3—C28—C29119.7 (4)
C4—C5—C6122.4 (4)O4—C28—C29115.7 (4)
C4—C5—H5118.8C28—C29—H29A109.5
C6—C5—H5118.8C28—C29—H29B109.5
C5—C6—C1119.6 (4)H29A—C29—H29B109.5
C5—C6—C7116.9 (4)C28—C29—H29C109.5
C1—C6—C7123.4 (3)H29A—C29—H29C109.5
N1—C7—C6127.4 (3)H29B—C29—H29C109.5
N1—C7—H7116.3C1—O1—Zn1127.1 (3)
C6—C7—H7116.3C18—O2—Zn1116.5 (2)
N1—C8—C9108.4 (3)C18—O2—Zn2116.3 (2)
N1—C8—H8A110.0Zn1—O2—Zn2108.80 (11)
C9—C8—H8A110.0C28—O3—Zn1133.2 (3)
N1—C8—H8B110.0C28—O4—Zn2131.8 (3)
C9—C8—H8B110.0C27—O5—Zn2128.0 (2)
H8A—C8—H8B108.4H6A—O6—H6B108.8
N2—C9—C8111.1 (3)H7A—O7—H7B108.3
N2—C9—H9A109.4C31—C30—O8107.5 (8)
C8—C9—H9A109.4C31—C30—H30A110.2
N2—C9—H9B109.4O8—C30—H30A110.2
C8—C9—H9B109.4C31—C30—H30B110.2
H9A—C9—H9B108.0O8—C30—H30B110.2
C11—C10—N2105.4 (3)H30A—C30—H30B108.5
C11—C10—H10A110.7C30—C31—H31A109.5
N2—C10—H10A110.7C30—C31—H31B109.5
C11—C10—H10B110.7H31A—C31—H31B109.5
N2—C10—H10B110.7C30—C31—H31C109.5
H10A—C10—H10B108.8H31A—C31—H31C109.5
N3—C11—C10105.2 (3)H31B—C31—H31C109.5
N3—C11—H11A110.7C30—O8—H8109.5
C10—C11—H11A110.7O9—C32—C3399.1 (10)
N3—C11—H11B110.7O9—C32—H32A111.9
C10—C11—H11B110.7C33—C32—H32A111.9
H11A—C11—H11B108.8O9—C32—H32B111.9
N3—C12—N2101.1 (3)C33—C32—H32B112.0
N3—C12—C13114.4 (3)H32A—C32—H32B109.6
N2—C12—C13113.5 (3)C32—C33—H33A109.5
N3—C12—H12109.2C32—C33—H33B109.5
N2—C12—H12109.2H33A—C33—H33B109.5
C13—C12—H12109.2C32—C33—H33C109.5
C14—C13—C18119.1 (3)H33A—C33—H33C109.5
C14—C13—C12120.7 (3)H33B—C33—H33C109.5
C18—C13—C12120.2 (3)C32—O9—H9109.5
O2—Zn1—N1—C794.1 (3)N3—C12—C13—C14−122.5 (4)
O3—Zn1—N1—C7−104.3 (3)N2—C12—C13—C14122.1 (4)
O1—Zn1—N1—C7−3.6 (3)N3—C12—C13—C1857.0 (5)
N2—Zn1—N1—C7163.2 (3)N2—C12—C13—C18−58.4 (5)
O2—Zn1—N1—C8−83.2 (3)C18—C13—C14—C15−0.7 (7)
O3—Zn1—N1—C878.5 (3)C12—C13—C14—C15178.9 (4)
O1—Zn1—N1—C8179.1 (3)C13—C14—C15—C160.9 (8)
N2—Zn1—N1—C8−14.1 (3)C14—C15—C16—C17−0.8 (8)
O2—Zn1—N2—C123.6 (2)C15—C16—C17—C180.4 (8)
O3—Zn1—N2—C12112.1 (3)C16—C17—C18—O2−179.9 (4)
O1—Zn1—N2—C12−78.7 (5)C16—C17—C18—C13−0.1 (6)
N1—Zn1—N2—C12−135.6 (3)C14—C13—C18—O2180.0 (4)
O2—Zn1—N2—C9124.3 (2)C12—C13—C18—O20.4 (5)
O3—Zn1—N2—C9−127.2 (2)C14—C13—C18—C170.3 (6)
O1—Zn1—N2—C941.9 (5)C12—C13—C18—C17−179.3 (4)
N1—Zn1—N2—C9−15.0 (2)C12—N3—C19—C20−164.7 (3)
O2—Zn1—N2—C10−113.3 (3)C11—N3—C19—C2078.9 (4)
O3—Zn1—N2—C10−4.8 (3)Zn2—N3—C19—C20−43.7 (4)
O1—Zn1—N2—C10164.3 (4)C21—N4—C20—C19142.6 (4)
N1—Zn1—N2—C10107.5 (3)Zn2—N4—C20—C19−37.8 (5)
O2—Zn2—N3—C12−4.4 (2)N3—C19—C20—N456.2 (5)
O4—Zn2—N3—C12−113.1 (3)C20—N4—C21—C22−179.0 (4)
O5—Zn2—N3—C1279.9 (5)Zn2—N4—C21—C221.4 (6)
N4—Zn2—N3—C12138.4 (3)N4—C21—C22—C270.7 (7)
O2—Zn2—N3—C11114.0 (3)N4—C21—C22—C23−177.9 (4)
O4—Zn2—N3—C115.3 (3)C27—C22—C23—C24−1.7 (6)
O5—Zn2—N3—C11−161.7 (4)C21—C22—C23—C24177.0 (4)
N4—Zn2—N3—C11−103.2 (3)C22—C23—C24—C251.1 (7)
O2—Zn2—N3—C19−124.1 (3)C23—C24—C25—C260.8 (7)
O4—Zn2—N3—C19127.2 (3)C24—C25—C26—C27−2.0 (7)
O5—Zn2—N3—C19−39.8 (5)C25—C26—C27—O5179.6 (4)
N4—Zn2—N3—C1918.7 (3)C25—C26—C27—C221.3 (6)
O2—Zn2—N4—C21−101.8 (4)C23—C22—C27—O5−177.7 (4)
O4—Zn2—N4—C2196.1 (4)C21—C22—C27—O53.6 (6)
O5—Zn2—N4—C21−4.9 (4)C23—C22—C27—C260.5 (6)
N3—Zn2—N4—C21−170.2 (4)C21—C22—C27—C26−178.1 (4)
O2—Zn2—N4—C2078.5 (3)C2—C1—O1—Zn1179.1 (3)
O4—Zn2—N4—C20−83.6 (3)C6—C1—O1—Zn1−1.6 (6)
O5—Zn2—N4—C20175.5 (3)O2—Zn1—O1—C1−132.8 (4)
N3—Zn2—N4—C2010.2 (3)O3—Zn1—O1—C1117.4 (4)
O1—C1—C2—C3−178.3 (5)N1—Zn1—O1—C13.6 (4)
C6—C1—C2—C32.4 (7)N2—Zn1—O1—C1−51.7 (7)
C1—C2—C3—C4−0.3 (8)C17—C18—O2—Zn1−114.9 (3)
C2—C3—C4—C5−1.3 (7)C13—C18—O2—Zn165.3 (4)
C3—C4—C5—C60.8 (7)C17—C18—O2—Zn2114.7 (3)
C4—C5—C6—C11.3 (6)C13—C18—O2—Zn2−65.0 (4)
C4—C5—C6—C7−179.0 (4)O3—Zn1—O2—C18−150.8 (2)
O1—C1—C6—C5177.9 (4)O1—Zn1—O2—C18108.6 (2)
C2—C1—C6—C5−2.8 (6)N1—Zn1—O2—C1811.3 (3)
O1—C1—C6—C7−1.7 (6)N2—Zn1—O2—C18−55.7 (2)
C2—C1—C6—C7177.6 (4)O3—Zn1—O2—Zn2−17.05 (15)
C8—N1—C7—C6179.0 (4)O1—Zn1—O2—Zn2−117.62 (13)
Zn1—N1—C7—C61.8 (6)N1—Zn1—O2—Zn2145.11 (15)
C5—C6—C7—N1−178.0 (4)N2—Zn1—O2—Zn278.06 (11)
C1—C6—C7—N11.6 (6)O4—Zn2—O2—C18151.3 (2)
C7—N1—C8—C9−135.9 (4)O5—Zn2—O2—C18−107.1 (2)
Zn1—N1—C8—C941.5 (4)N4—Zn2—O2—C18−10.9 (3)
C12—N2—C9—C8162.5 (3)N3—Zn2—O2—C1855.7 (2)
C10—N2—C9—C8−81.0 (4)O4—Zn2—O2—Zn117.41 (15)
Zn1—N2—C9—C841.1 (3)O5—Zn2—O2—Zn1119.05 (13)
N1—C8—C9—N2−56.5 (4)N4—Zn2—O2—Zn1−144.75 (16)
C12—N2—C10—C11−26.8 (4)N3—Zn2—O2—Zn1−78.17 (12)
C9—N2—C10—C11−148.6 (3)O4—C28—O3—Zn17.9 (7)
Zn1—N2—C10—C1196.2 (3)C29—C28—O3—Zn1−173.5 (4)
C12—N3—C11—C1028.0 (4)O2—Zn1—O3—C286.1 (4)
C19—N3—C11—C10149.0 (3)O1—Zn1—O3—C28103.0 (4)
Zn2—N3—C11—C10−95.8 (3)N1—Zn1—O3—C28−160.5 (4)
N2—C10—C11—N3−0.7 (4)N2—Zn1—O3—C28−80.0 (4)
C11—N3—C12—N2−44.8 (3)O3—C28—O4—Zn2−7.1 (7)
C19—N3—C12—N2−166.8 (3)C29—C28—O4—Zn2174.2 (4)
Zn2—N3—C12—N279.5 (3)O2—Zn2—O4—C28−7.3 (4)
C11—N3—C12—C13−167.2 (3)O5—Zn2—O4—C28−104.4 (4)
C19—N3—C12—C1370.8 (4)N4—Zn2—O4—C28160.6 (4)
Zn2—N3—C12—C13−42.9 (4)N3—Zn2—O4—C2879.5 (4)
C9—N2—C12—N3166.8 (3)C26—C27—O5—Zn2172.0 (3)
C10—N2—C12—N343.9 (3)C22—C27—O5—Zn2−9.8 (6)
Zn1—N2—C12—N3−79.0 (3)O2—Zn2—O5—C27149.1 (3)
C9—N2—C12—C13−70.2 (4)O4—Zn2—O5—C27−100.7 (3)
C10—N2—C12—C13166.9 (3)N4—Zn2—O5—C279.2 (3)
Zn1—N2—C12—C1344.1 (4)N3—Zn2—O5—C2766.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8B···O7i0.972.413.259 (8)145
C12—H12···O8ii0.982.523.482 (5)169
O6—H6B···O5iii0.852.062.804 (4)146
O6—H6A···O1iii0.882.052.896 (4)161
O7—H7A···O40.852.152.971 (8)162
O7—H7B···O1iv0.862.483.225 (9)145
O8—H8···O60.821.912.701 (5)163
O9—H9···O8ii0.822.082.849 (9)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2964).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fondo, M., García-Deibe, A. M., Bermejo, M. R., Sanmartín, J. & Llamas-Saiz, A. L. (2002). J. Chem. Soc. Dalton Trans pp. 4746–4750.
  • Fondo, M., García-Deibe, A. M., Corbella, M., Ribas, J., Llamas-Saiz, A., Bermejo, M. R. & Sanmartín, J. (2004). Dalton Trans pp. 3503–3507. [PubMed]
  • Lu, L.-P., Lu, X.-P. & Zhu, M.-L. (2007). Acta Cryst. C63, m374–m376. [PubMed]
  • Prasant Kumar, N., Guillem, A. & Debashis, R. (2006). Chem. Commun. pp. 3181–3183. [PubMed]
  • Sarma, B. D. & Bailar, J. C. (1955). J. Am. Chem. Soc.77, 5476–5480.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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