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Acta Cryst. (2009). E65, m576    [ doi:10.1107/S1600536809014755 ]

Tris(2-ethyl-1H-imidazole-[kappa]N3)(terephthalato-[kappa]O)zinc(II)

Q.-A. Xie, G.-Y. Dong, Y.-M. Yu and Y.-G. Wang

Abstract top

The title compound, [Zn(C8H4O4)(C5H8N2)3], has a neutral monomeric structure in which one terephthalate dianion and three 2-ethyl-1H-imidazole ligands coordinate to the ZnII ion in a distorted tetrahedral geometry. The methyl group of one of the ethyl groups is disordered over two positions with occupancies of 0.66 (2) and 0.34 (2). In the crystal structure, molecules are linked into a three-dimensional hydrogen-bonded network by intermolecular N-H...O interactions involving the uncoordinated carboxylate O atoms.

Comment top

Metal complexes with imidazole can serve as biomimetic ligands for histidine residues which frequently participate in the co-ordination spheres of metalloenzyme active sites. In particular, carboxylate-histidine-zinc triad systems are regularly observed, and play important roles in the catalytic processes of more than thirty zinc enzymes (Chen et al., 1994). However, crystal structure reports of such model zinc complexes containing neutral imidazole ligands are rather rare, and so far only a few examples have been presented (Kimura et al., 1991; Chen et al., 1994). Here, we report the synthesis and crystal structure of the title complex.

The title compound is a monomeric zinc(II) complex (Fig. 1). The ZnII center is four coordinated by three monodentate 2-ethyl-1H-imidazole ligands and by a monodentate terephthalate group, forming a distorted tetrahedral N3,O geometry. The Zn—N bond lengths are in the range 2.014 (6)–2.047 (7) Å and the Zn—O distance is 1.943 (6) Å (Table 1). The most distorted bond angle is O1—Zn1—N1 at 100.5 (3)°.

The N—H···O hydrogen bonds (Table 2) formed between three uncoordinated 2-ethyl-H-imidazole N atoms and two uncoordinated carboxylate O atoms, resulted in a three-dimensional hydrogen-bonded network.

Related literature top

For the crystal structures of related ZnII complexes, see: Chen et al. (1994); Kimura et al. (1991); Yang et al. (2002).

Experimental top

The title compound was synthesized by a solvothermal method from Zn(NO3)2.6H2O (29.8 mg, 0.1 mmol), terephthalic acid (77.6 mg,0.4 mmol), 2-ethylimidazole (38.4 mg, 0.4 mmol) and water-ethanol mixed slovent (3 ml). The starting mixture was homogenized and transferred to a sealed Teflon-lined solvothermal bomb (bomb volume: 25 ml) and heated at 433 K for 3 d under autogenous pressure. After cooling in a water bath, colourless crystals were obtained, which were washed and rinsed with distilled water and absolute ethyl alcohol (yield: 51.8% on the basis of Zn(NO3)2.6H2O). Analysis calculated (%) for C23H28N6O4Zn: C 53.34, H 5.45, N 16.23%; found: C 53.18, H 5.43, N 16.13.

Refinement top

The methyl C atom, C18, in one of the ethyl groups is disordered over two positions (C18A and C18B) with refined occupancies of 0.66 (2) and 0.34 (2). The C17—C18A and C17—C18B distances were restrained to 1.53 (1) Å. The displacement parameters of the disordered C atoms were also restrained to be approximately isotropic. The aromatic [C-H = 0.93 Å and Uiso(H) = 1.2Ueq(C)] and methylene H atoms [C-H = 0.96 Å and Uiso(H) = 1.5Ueq(C)] were included in the refinement in the riding-model approximation.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids. For clarity, H atoms have been omitted. Only the major disorder component is shown.
Tris(2-ethyl-1H-imidazole-κN3)(terephthalato-\ κO)zinc(II) top
Crystal data top
[Zn(C8H4O4)(C5H8N2)3]F(000) = 1080
Mr = 517.90Dx = 1.354 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1240 reflections
a = 11.548 (2) Åθ = 4.5–25.0°
b = 11.759 (2) ŵ = 1.01 mm−1
c = 18.719 (4) ÅT = 293 K
β = 91.79 (3)°Block, white
V = 2540.7 (8) Å30.30 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		5719 independent reflections
Radiation source: fine-focus sealed tube3534 reflections with I > 2σ(I)
graphiteRint = 0.086
φ and ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.742, Tmax = 0.812k = −15→15
13021 measured reflectionsl = −24→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0189P)2 + 0.8316P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
5719 reflectionsΔρmax = 0.51 e Å−3
317 parametersΔρmin = −0.28 e Å−3
16 restraintsAbsolute structure: Flack (1983), 2826 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.049 (15)
Crystal data top
[Zn(C8H4O4)(C5H8N2)3]V = 2540.7 (8) Å3
Mr = 517.90Z = 4
Monoclinic, CcMo Kα radiation
a = 11.548 (2) ŵ = 1.01 mm−1
b = 11.759 (2) ÅT = 293 K
c = 18.719 (4) Å0.30 × 0.25 × 0.22 mm
β = 91.79 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		5719 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3534 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 0.812Rint = 0.086
13021 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.073H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.51 e Å−3
S = 1.12Δρmin = −0.28 e Å−3
5719 reflectionsAbsolute structure: Flack (1983), 2826 Friedel pairs
317 parametersFlack parameter: 0.049 (15)
16 restraints
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Zn10.31207 (5)0.87464 (5)1.00368 (4)0.04221 (18)
O10.3327 (4)1.0107 (4)0.9463 (2)0.0616 (12)
O20.1668 (4)0.9779 (4)0.8862 (3)0.0651 (13)
O30.4207 (4)1.5052 (4)0.7476 (2)0.0570 (12)
O40.3054 (4)1.4345 (4)0.6625 (2)0.0628 (12)
N10.4459 (4)0.8920 (4)1.0769 (2)0.0459 (13)
N20.6080 (5)0.9487 (4)1.1293 (3)0.0647 (15)
H20.67680.97591.13550.078*
N30.1653 (4)0.8651 (4)1.0592 (2)0.0421 (11)
N40.0232 (5)0.8949 (5)1.1303 (3)0.0639 (15)
H4−0.01840.92591.16220.077*
N50.3423 (4)0.7220 (4)0.9580 (2)0.0436 (12)
N60.4022 (5)0.5903 (4)0.8863 (3)0.0529 (14)
H60.41810.55480.84770.063*
C10.2545 (6)1.0340 (5)0.8977 (3)0.0476 (15)
C20.2797 (5)1.1396 (5)0.8544 (3)0.0392 (14)
C30.3797 (5)1.2032 (5)0.8667 (3)0.0443 (15)
H30.43191.18160.90300.053*
C40.4029 (5)1.2980 (5)0.8259 (3)0.0420 (14)
H4A0.47021.33960.83510.050*
C50.3255 (5)1.3317 (4)0.7707 (3)0.0341 (13)
C60.2258 (5)1.2678 (5)0.7579 (3)0.0407 (15)
H6A0.17381.28850.72130.049*
C70.2034 (5)1.1723 (5)0.8001 (3)0.0447 (15)
H70.13621.13040.79130.054*
C80.3515 (5)1.4310 (5)0.7235 (3)0.0427 (15)
C90.5509 (6)0.9366 (5)1.0669 (3)0.0470 (15)
C100.5378 (8)0.9101 (7)1.1818 (4)0.088 (3)
H100.55530.90841.23060.106*
C110.4387 (6)0.8751 (6)1.1490 (4)0.074 (2)
H110.37540.84441.17170.088*
C120.6028 (5)0.9657 (5)0.9961 (3)0.0558 (18)
H12A0.66361.02181.00380.067*
H12B0.54360.99930.96490.067*
C130.6528 (8)0.8621 (7)0.9599 (4)0.101 (3)
H13A0.68460.88420.91520.152*
H13B0.59270.80700.95150.152*
H13C0.71280.82970.99020.152*
C140.1249 (5)0.9330 (5)1.1079 (3)0.0498 (16)
C15−0.0025 (6)0.7984 (6)1.0934 (4)0.066 (2)
H15−0.06830.75351.09740.080*
C160.0867 (5)0.7808 (5)1.0497 (4)0.0542 (17)
H160.09300.72031.01810.065*
C170.1830 (8)1.0329 (7)1.1407 (5)0.110 (3)
H17A0.14551.05151.18480.132*0.661 (18)
H17B0.26291.01341.15260.132*0.661 (18)
H17C0.25191.04601.11440.132*0.339 (18)
H17D0.20801.01001.18790.132*0.339 (18)
C18A0.1810 (13)1.1331 (11)1.0944 (8)0.115 (6)0.661 (18)
H18A0.22031.19481.11840.172*0.661 (18)
H18B0.10221.15441.08350.172*0.661 (18)
H18C0.21921.11581.05090.172*0.661 (18)
C18B0.1283 (18)1.1454 (12)1.1528 (14)0.079 (9)0.339 (18)
H18D0.18371.19551.17560.119*0.339 (18)
H18E0.06311.13621.18280.119*0.339 (18)
H18F0.10291.17721.10770.119*0.339 (18)
C190.3515 (5)0.6916 (5)0.8896 (3)0.0445 (15)
C200.4250 (6)0.5515 (5)0.9545 (3)0.0547 (17)
H200.46010.48320.96780.066*
C210.3857 (5)0.6335 (5)0.9983 (3)0.0482 (15)
H210.38790.63041.04800.058*
C220.3089 (7)0.7583 (6)0.8248 (4)0.070 (2)
H22A0.28040.70600.78830.085*
H22B0.24500.80670.83810.085*
C230.4025 (8)0.8302 (8)0.7949 (5)0.124 (4)
H23A0.37230.87130.75410.187*
H23B0.46530.78250.78080.187*
H23C0.43010.88310.83060.187*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0425 (3)0.0409 (3)0.0436 (4)0.0011 (5)0.0069 (2)0.0037 (4)
O10.059 (3)0.059 (3)0.067 (3)0.006 (2)0.004 (2)0.027 (2)
O20.052 (3)0.052 (3)0.092 (4)−0.005 (2)0.005 (3)0.017 (3)
O30.081 (3)0.052 (3)0.039 (3)−0.003 (3)0.015 (2)0.010 (2)
O40.066 (3)0.078 (3)0.044 (3)0.007 (3)−0.005 (2)0.020 (3)
N10.051 (3)0.050 (3)0.037 (3)−0.008 (3)0.003 (2)0.003 (2)
N20.060 (4)0.071 (4)0.062 (4)−0.004 (3)−0.012 (3)−0.011 (3)
N30.045 (3)0.042 (3)0.040 (3)0.000 (3)0.009 (2)−0.005 (3)
N40.063 (4)0.065 (4)0.064 (4)0.009 (3)0.021 (3)−0.012 (3)
N50.047 (3)0.050 (3)0.035 (3)0.003 (2)0.005 (2)0.001 (2)
N60.071 (4)0.043 (3)0.045 (3)0.007 (3)0.015 (3)0.000 (3)
C10.050 (4)0.042 (4)0.052 (4)0.013 (3)0.011 (3)0.002 (3)
C20.044 (3)0.035 (3)0.038 (3)0.005 (3)0.004 (3)0.002 (3)
C30.053 (4)0.040 (4)0.039 (4)0.007 (3)−0.007 (3)0.007 (3)
C40.041 (4)0.041 (4)0.043 (4)0.001 (3)−0.002 (3)0.001 (3)
C50.038 (3)0.039 (3)0.026 (3)0.010 (3)0.008 (2)0.002 (3)
C60.037 (4)0.051 (4)0.033 (3)0.009 (3)−0.006 (3)−0.002 (3)
C70.041 (4)0.050 (4)0.043 (4)0.003 (3)0.002 (3)−0.003 (3)
C80.041 (4)0.046 (4)0.042 (4)0.013 (3)0.013 (3)0.007 (3)
C90.058 (4)0.029 (3)0.053 (4)0.003 (3)0.000 (3)−0.006 (3)
C100.095 (7)0.127 (8)0.042 (5)0.006 (6)−0.003 (5)−0.008 (5)
C110.071 (5)0.096 (6)0.053 (5)−0.004 (5)0.002 (4)0.013 (4)
C120.042 (4)0.062 (5)0.064 (5)−0.010 (3)0.005 (3)0.004 (4)
C130.110 (7)0.102 (7)0.095 (7)−0.010 (6)0.047 (5)−0.036 (6)
C140.049 (4)0.049 (4)0.052 (4)−0.005 (3)0.004 (3)−0.010 (3)
C150.049 (4)0.060 (5)0.091 (6)−0.016 (4)0.011 (4)−0.008 (4)
C160.044 (4)0.046 (4)0.073 (5)−0.007 (3)0.008 (3)−0.019 (3)
C170.105 (8)0.092 (7)0.134 (8)−0.003 (6)0.015 (6)−0.032 (6)
C18A0.116 (9)0.103 (9)0.125 (10)−0.004 (7)0.002 (7)0.009 (7)
C18B0.077 (11)0.069 (12)0.092 (12)−0.004 (8)0.006 (8)−0.009 (8)
C190.051 (4)0.042 (4)0.041 (4)0.000 (3)0.009 (3)0.002 (3)
C200.066 (4)0.045 (4)0.053 (4)0.009 (3)0.007 (3)0.005 (3)
C210.052 (4)0.055 (4)0.038 (3)−0.001 (3)−0.001 (3)0.002 (3)
C220.101 (6)0.056 (5)0.054 (5)0.020 (4)0.012 (4)0.006 (4)
C230.119 (8)0.167 (10)0.089 (7)0.057 (7)0.028 (6)0.054 (7)
Geometric parameters (Å, °) top
Zn1—O11.947 (4)C10—C111.346 (10)
Zn1—N32.018 (4)C10—H100.93
Zn1—N52.023 (5)C11—H110.93
Zn1—N12.044 (5)C12—C131.516 (9)
O1—C11.291 (7)C12—H12A0.97
O2—C11.223 (7)C12—H12B0.97
O3—C81.257 (7)C13—H13A0.96
O4—C81.245 (7)C13—H13B0.96
N1—C91.339 (7)C13—H13C0.96
N1—C111.370 (8)C14—C171.477 (9)
N2—C91.331 (8)C15—C161.351 (8)
N2—C101.371 (9)C15—H150.93
N2—H20.86C16—H160.93
N3—C141.309 (7)C17—C18A1.462 (8)
N3—C161.352 (7)C17—C18B1.486 (9)
N4—C141.336 (7)C17—H17A0.97
N4—C151.356 (8)C17—H17B0.97
N4—H40.86C17—H17C0.96
N5—C191.337 (7)C17—H17D0.96
N5—C211.371 (7)C18A—H18A0.96
N6—C191.330 (7)C18A—H18B0.96
N6—C201.373 (7)C18A—H18C0.96
N6—H60.86C18B—H18D0.96
C1—C21.516 (8)C18B—H18E0.96
C2—C71.379 (7)C18B—H18F0.96
C2—C31.389 (8)C19—C221.513 (9)
C3—C41.382 (7)C20—C211.354 (7)
C3—H30.93C20—H200.93
C4—C51.402 (7)C21—H210.93
C4—H4A0.93C22—C231.495 (11)
C5—C61.389 (7)C22—H22A0.97
C5—C81.501 (7)C22—H22B0.97
C6—C71.401 (8)C23—H23A0.96
C6—H6A0.93C23—H23B0.96
C7—H70.93C23—H23C0.96
C9—C121.512 (8)
O1—Zn1—N3116.67 (18)C13—C12—H12B109.2
O1—Zn1—N5118.06 (18)H12A—C12—H12B107.9
N3—Zn1—N5109.09 (19)C12—C13—H13A109.5
O1—Zn1—N1100.7 (2)C12—C13—H13B109.5
N3—Zn1—N1106.87 (18)H13A—C13—H13B109.5
N5—Zn1—N1103.6 (2)C12—C13—H13C109.5
C1—O1—Zn1117.9 (4)H13A—C13—H13C109.5
C9—N1—C11106.1 (5)H13B—C13—H13C109.5
C9—N1—Zn1127.9 (4)N3—C14—N4110.5 (5)
C11—N1—Zn1125.3 (4)N3—C14—C17127.4 (6)
C9—N2—C10107.8 (6)N4—C14—C17121.9 (6)
C9—N2—H2126.1C16—C15—N4106.1 (6)
C10—N2—H2126.1C16—C15—H15127.0
C14—N3—C16106.6 (5)N4—C15—H15127.0
C14—N3—Zn1130.4 (4)C15—C16—N3109.3 (6)
C16—N3—Zn1123.0 (4)C15—C16—H16125.4
C14—N4—C15107.6 (5)N3—C16—H16125.4
C14—N4—H4126.2C18A—C17—C14113.4 (9)
C15—N4—H4126.2C14—C17—C18B125.6 (11)
C19—N5—C21106.6 (5)C18A—C17—H17A108.9
C19—N5—Zn1131.5 (4)C14—C17—H17A108.9
C21—N5—Zn1120.4 (4)C18A—C17—H17B108.9
C19—N6—C20109.1 (5)C14—C17—H17B108.9
C19—N6—H6125.4H17A—C17—H17B107.7
C20—N6—H6125.4C14—C17—H17C106.7
O2—C1—O1124.6 (6)C18B—C17—H17C107.3
O2—C1—C2121.3 (6)C14—C17—H17D106.2
O1—C1—C2114.1 (6)C18B—C17—H17D103.1
C7—C2—C3118.7 (5)H17C—C17—H17D106.7
C7—C2—C1119.6 (5)C17—C18A—H18A109.5
C3—C2—C1121.7 (5)C17—C18A—H18B109.5
C4—C3—C2121.2 (5)H18A—C18A—H18B109.5
C4—C3—H3119.4C17—C18A—H18C109.5
C2—C3—H3119.4H18A—C18A—H18C109.5
C3—C4—C5120.3 (5)H18B—C18A—H18C109.5
C3—C4—H4A119.8C17—C18B—H18D109.5
C5—C4—H4A119.8C17—C18B—H18E109.5
C6—C5—C4118.7 (5)H18D—C18B—H18E109.5
C6—C5—C8120.0 (5)C17—C18B—H18F109.5
C4—C5—C8121.3 (5)H18D—C18B—H18F109.5
C5—C6—C7120.2 (5)H18E—C18B—H18F109.5
C5—C6—H6A119.9N6—C19—N5109.4 (5)
C7—C6—H6A119.9N6—C19—C22124.1 (6)
C2—C7—C6120.9 (6)N5—C19—C22126.5 (6)
C2—C7—H7119.5C21—C20—N6105.6 (5)
C6—C7—H7119.5C21—C20—H20127.2
O4—C8—O3123.7 (6)N6—C20—H20127.2
O4—C8—C5118.5 (6)C20—C21—N5109.3 (5)
O3—C8—C5117.7 (5)C20—C21—H21125.3
N2—C9—N1110.3 (6)N5—C21—H21125.3
N2—C9—C12123.0 (6)C23—C22—C19111.9 (7)
N1—C9—C12126.7 (6)C23—C22—H22A109.2
C11—C10—N2106.8 (7)C19—C22—H22A109.2
C11—C10—H10126.6C23—C22—H22B109.2
N2—C10—H10126.6C19—C22—H22B109.2
C10—C11—N1109.1 (7)H22A—C22—H22B107.9
C10—C11—H11125.5C22—C23—H23A109.5
N1—C11—H11125.5C22—C23—H23B109.5
C9—C12—C13112.1 (5)H23A—C23—H23B109.5
C9—C12—H12A109.2C22—C23—H23C109.5
C13—C12—H12A109.2H23A—C23—H23C109.5
C9—C12—H12B109.2H23B—C23—H23C109.5
N3—Zn1—O1—C1−58.2 (5)C4—C5—C8—O3−23.6 (8)
N5—Zn1—O1—C174.8 (4)C10—N2—C9—N10.3 (7)
N1—Zn1—O1—C1−173.4 (4)C10—N2—C9—C12−177.4 (6)
O1—Zn1—N1—C9−34.4 (5)C11—N1—C9—N2−0.5 (7)
N3—Zn1—N1—C9−156.7 (5)Zn1—N1—C9—N2170.7 (4)
N5—Zn1—N1—C988.1 (5)C11—N1—C9—C12177.1 (6)
O1—Zn1—N1—C11135.2 (5)Zn1—N1—C9—C12−11.7 (9)
N3—Zn1—N1—C1112.9 (6)C9—N2—C10—C110.1 (8)
N5—Zn1—N1—C11−102.3 (6)N2—C10—C11—N1−0.3 (9)
O1—Zn1—N3—C14−58.6 (6)C9—N1—C11—C100.5 (8)
N5—Zn1—N3—C14164.5 (5)Zn1—N1—C11—C10−171.0 (5)
N1—Zn1—N3—C1453.0 (6)N2—C9—C12—C1396.4 (7)
O1—Zn1—N3—C16120.4 (5)N1—C9—C12—C13−80.8 (8)
N5—Zn1—N3—C16−16.6 (5)C16—N3—C14—N40.2 (7)
N1—Zn1—N3—C16−128.0 (5)Zn1—N3—C14—N4179.3 (4)
O1—Zn1—N5—C19−16.2 (6)C16—N3—C14—C17175.1 (7)
N3—Zn1—N5—C19120.0 (5)Zn1—N3—C14—C17−5.7 (10)
N1—Zn1—N5—C19−126.4 (5)C15—N4—C14—N3−0.4 (7)
O1—Zn1—N5—C21147.3 (4)C15—N4—C14—C17−175.7 (7)
N3—Zn1—N5—C21−76.4 (4)C14—N4—C15—C160.5 (8)
N1—Zn1—N5—C2137.2 (5)N4—C15—C16—N3−0.4 (8)
Zn1—O1—C1—O21.8 (8)C14—N3—C16—C150.1 (8)
Zn1—O1—C1—C2−178.4 (3)Zn1—N3—C16—C15−179.1 (5)
O2—C1—C2—C7−1.2 (8)N3—C14—C17—C18A77.0 (12)
O1—C1—C2—C7179.0 (5)N4—C14—C17—C18A−108.6 (11)
O2—C1—C2—C3−179.4 (5)N3—C14—C17—C18B135.1 (15)
O1—C1—C2—C30.8 (8)N4—C14—C17—C18B−50.5 (17)
C7—C2—C3—C40.4 (8)C20—N6—C19—N51.3 (7)
C1—C2—C3—C4178.6 (5)C20—N6—C19—C22−177.2 (6)
C2—C3—C4—C5−0.3 (8)C21—N5—C19—N6−2.1 (6)
C3—C4—C5—C6−0.2 (8)Zn1—N5—C19—N6163.1 (4)
C3—C4—C5—C8−177.1 (5)C21—N5—C19—C22176.4 (6)
C4—C5—C6—C70.5 (8)Zn1—N5—C19—C22−18.4 (9)
C8—C5—C6—C7177.5 (5)C19—N6—C20—C210.1 (7)
C3—C2—C7—C60.0 (8)N6—C20—C21—N5−1.4 (7)
C1—C2—C7—C6−178.3 (5)C19—N5—C21—C202.2 (7)
C5—C6—C7—C2−0.4 (8)Zn1—N5—C21—C20−165.0 (4)
C6—C5—C8—O4−21.7 (8)N6—C19—C22—C23−86.7 (9)
C4—C5—C8—O4155.2 (5)N5—C19—C22—C2395.0 (8)
C6—C5—C8—O3159.5 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.861.882.717 (7)165
N4—H4···O3ii0.861.942.787 (7)167
N6—H6···O3iii0.861.962.797 (7)163
Symmetry codes: (i) x+1/2, −y+5/2, z+1/2; (ii) x−1/2, −y+5/2, z+1/2; (iii) x, y−1, z.
Table 1
Selected geometric parameters (Å) top
Zn1—O11.947 (4)Zn1—N52.023 (5)
Zn1—N32.018 (4)Zn1—N12.044 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.861.882.717 (7)165
N4—H4···O3ii0.861.942.787 (7)167
N6—H6···O3iii0.861.962.797 (7)163
Symmetry codes: (i) x+1/2, −y+5/2, z+1/2; (ii) x−1/2, −y+5/2, z+1/2; (iii) x, y−1, z.
Acknowledgements top

The authors thank the China University of Mining and Technology (Beijing) and Hebei Polytechnic University for supporting this work.

references
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