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Acta Cryst. (2008). E64, m656    [ doi:10.1107/S1600536808009707 ]

Bis[2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazonato]zinc(II) monohydrate

X.-S. Tai, Y.-M. Feng and H.-X. Zhang

Abstract top

In the title compound, [Zn(C14H13N4O2)2]·H2O, the ZnII centre is six-coordinated by four N and two O donors of two 2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazonate ligands, and forms a distorted octahedral structure.

Comment top

Schiff-base ligands are able to coordinate metals through imine nitrogen and another group, usually linked to the aldehyde. Modern chemists still prepare Schiff-bases, and nowadays active and well designed Schiff-base ligands are considered to be "privileged ligands" (Tai & Feng, 2008; Tai, Feng, Kong, Wang & Tan, 2007; Tai et al., 2008; Tai, Yin & Feng, 2007; Tai, Yin, Feng & Kong, 2007; Tai, Yin & Hao, 2007; Tai et al., 2003; Wang et al., 2007). In fact, Schiff bases are able to stabilize many different metals in various oxidation states. Schiff bases and their metal complexes play a key role in understanding the coordination chemistry of transition metal ions (Tai et al., 2003). In particular, the bidentate ligands containing imine groups have been used as modulators of structural, electronic, antitumor activity and fluorescence properties of transition metal centres (Herzfeld & Nagy, 1999). In order to investigate further the coordination and the properties of zinc complexes with Schiff bases ligands, as parts of our studies on the synthesis, characterization and properties of Schiff bases ligands and their metal complexes, we herein report the synthesis and structural characterization of a new zinc complex, Zn(2-acetyl-3-methylpyrazine salicyloyl hydrazone), (I).

The title compound consists of neutral complex, Zn[2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazone]. The ZnII center is six-coordinate with four N and two O donors of 2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazonate, and forms a distorted octahedron structure. The Zn—O and Zn—N bond lengths are in the ranges 2.055 (3)–2.079 (3) and 2.239 (4)–2.283 (3) Å, respectively. The Zn—O bond lengths are much shorter than Zn—N, which shows that the Zn—O bonds are stronger than the Zn—N bonds.

Related literature top

For related literature, see: Herzfeld & Nagy (1999); Xi-Shi & Yi-Min (2008); Tai et al. (2003); Tai et al. (2008); Tai, Feng, Kong, Wang & Tan (2007); Tai, Yin & Feng (2007); Tai, Yin & Hao (2007); Tai, Yin, Feng & Kong (2007); Wang et al. (2007).

Experimental top

The title compound was prepared as following: 1 mmol of ZnII acetate was added to the solution of 2-acetyl-3-methylpyrazine salicyloyl hydrazone (1 mmol) in a 10 ml of CH3CH2OH. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then the product was collected by filtration, yield 68%. The single-crystal suitable for X-ray determination was obtained by evaporation from ethanol solution after two weeks. A ethanol solution of the title compound was slowly evaporated and pale crystals were obtained after a weeks.

Refinement top

The positions of all H atoms were fixed geometrically [C—H = 0.93 for aromatic H and 0.96 Å for methyl H , O—H = 0.82 for hydroxy group and O—H = 0.85 Å for water molecules] and refined as riding with Uiso(H) = 1.2 or 1.5 Ueq(carrier).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 molecule of the title compound, with 30% probabiility ellipsoids.
Bis[2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazonato]zinc(II) monohydrate top
Crystal data top
[Zn(C14H13N4O2)2]·H2OF000 = 1288
Mr = 621.95Dx = 1.444 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2538 reflections
a = 9.3794 (10) Åθ = 2.4–22.4º
b = 22.814 (2) ŵ = 0.91 mm−1
c = 13.9407 (14) ÅT = 298 (2) K
β = 106.402 (2)ºTabular, colourless
V = 2861.6 (5) Å30.32 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		5043 independent reflections
Radiation source: fine-focus sealed tube2831 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −9→11
Tmin = 0.759, Tmax = 0.868k = −27→23
14227 measured reflectionsl = −16→16
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.128  w = 1/[σ2(Fo2) + (0.0366P)2 + 2.1233P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5043 reflectionsΔρmax = 0.38 e Å−3
379 parametersΔρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C14H13N4O2)2]·H2OV = 2861.6 (5) Å3
Mr = 621.95Z = 4
Monoclinic, P21/nMo Kα
a = 9.3794 (10) ŵ = 0.91 mm−1
b = 22.814 (2) ÅT = 298 (2) K
c = 13.9407 (14) Å0.32 × 0.20 × 0.16 mm
β = 106.402 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5043 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2831 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.868Rint = 0.077
14227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047379 parameters
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.38 e Å−3
5043 reflectionsΔρmin = −0.35 e Å−3
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*/Ueq
Zn10.09167 (6)0.14093 (2)0.53708 (4)0.04641 (19)
N1−0.0550 (4)0.24903 (15)0.5747 (2)0.0414 (9)
N20.0653 (4)0.23093 (15)0.5435 (2)0.0402 (9)
N30.2582 (4)0.18422 (16)0.4675 (3)0.0443 (9)
N40.4647 (4)0.2484 (2)0.4049 (3)0.0592 (11)
N50.2455 (4)0.02711 (15)0.5545 (3)0.0461 (9)
N60.1370 (4)0.05900 (16)0.4881 (3)0.0441 (9)
N7−0.0643 (4)0.12679 (16)0.3845 (3)0.0453 (9)
N8−0.2259 (5)0.1065 (2)0.1898 (3)0.0636 (12)
O1−0.0809 (3)0.14991 (13)0.5998 (2)0.0559 (9)
O2−0.2266 (4)0.32101 (14)0.6299 (3)0.0695 (10)
H2−0.15140.31100.61510.104*
O30.2353 (3)0.10277 (13)0.6631 (2)0.0512 (8)
O40.4380 (4)−0.05320 (16)0.6118 (3)0.0852 (12)
H40.3692−0.03530.57370.128*
O50.7000 (4)0.3022 (2)0.3185 (3)0.1108 (16)
H5A0.61910.29400.33160.133*
H5B0.68380.32910.27460.133*
C1−0.1183 (5)0.2031 (2)0.6046 (3)0.0416 (11)
C2−0.2467 (4)0.21621 (19)0.6431 (3)0.0375 (10)
C3−0.2931 (5)0.2732 (2)0.6550 (3)0.0465 (11)
C4−0.4143 (5)0.2828 (2)0.6926 (3)0.0581 (13)
H4A−0.44390.32080.70180.070*
C5−0.4885 (5)0.2362 (3)0.7158 (3)0.0608 (14)
H5−0.56960.24290.74030.073*
C6−0.4470 (5)0.1797 (2)0.7039 (4)0.0610 (14)
H6−0.49950.14830.71940.073*
C7−0.3265 (5)0.1706 (2)0.6685 (3)0.0511 (12)
H7−0.29720.13230.66120.061*
C80.0648 (5)0.32827 (19)0.4706 (3)0.0518 (12)
H8A−0.04180.32680.45080.078*
H8B0.09850.34320.41640.078*
H8C0.09870.35350.52760.078*
C90.1257 (4)0.26797 (19)0.4972 (3)0.0390 (10)
C100.2528 (4)0.24350 (19)0.4667 (3)0.0401 (10)
C110.3614 (5)0.2760 (2)0.4387 (3)0.0472 (11)
C120.3827 (5)0.3412 (2)0.4497 (4)0.0720 (16)
H12A0.48530.35060.45830.108*
H12B0.35390.35430.50700.108*
H12C0.32240.36030.39080.108*
C130.4634 (5)0.1902 (3)0.4027 (4)0.0618 (14)
H130.53170.17060.37730.074*
C140.3641 (5)0.1584 (2)0.4370 (3)0.0526 (12)
H140.37110.11770.43890.063*
C150.2860 (5)0.0543 (2)0.6433 (3)0.0446 (11)
C160.4033 (5)0.02364 (19)0.7213 (3)0.0447 (11)
C170.4738 (5)−0.0274 (2)0.7028 (4)0.0594 (13)
C180.5834 (6)−0.0531 (2)0.7792 (4)0.0769 (17)
H180.6309−0.08670.76640.092*
C190.6226 (6)−0.0297 (3)0.8728 (5)0.0829 (18)
H190.6953−0.04790.92350.099*
C200.5561 (6)0.0201 (3)0.8929 (4)0.0797 (17)
H200.58470.03640.95660.096*
C210.4463 (5)0.0461 (2)0.8181 (4)0.0611 (14)
H210.39960.07950.83250.073*
C220.1358 (6)−0.0146 (2)0.3624 (4)0.0896 (19)
H22A0.2133−0.03160.41540.134*
H22B0.1733−0.00610.30660.134*
H22C0.0545−0.04170.34210.134*
C230.0833 (5)0.04049 (19)0.3982 (3)0.0436 (11)
C24−0.0357 (5)0.0788 (2)0.3363 (3)0.0440 (11)
C25−0.1161 (5)0.0696 (2)0.2352 (4)0.0555 (13)
C26−0.0901 (6)0.0220 (3)0.1688 (4)0.094 (2)
H26A−0.16010.02570.10390.141*
H26B−0.1026−0.01540.19690.141*
H26C0.00910.02510.16280.141*
C27−0.2551 (5)0.1511 (2)0.2407 (4)0.0602 (14)
H27−0.33340.17600.21030.072*
C28−0.1727 (5)0.1623 (2)0.3385 (4)0.0517 (12)
H28−0.19400.19510.37160.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0521 (3)0.0324 (3)0.0577 (3)0.0072 (3)0.0202 (3)0.0011 (3)
N10.040 (2)0.031 (2)0.057 (2)0.0013 (17)0.0200 (18)0.0008 (18)
N20.039 (2)0.034 (2)0.049 (2)0.0006 (17)0.0148 (17)0.0014 (17)
N30.042 (2)0.043 (3)0.050 (2)0.0068 (18)0.0173 (18)0.0016 (18)
N40.046 (2)0.066 (3)0.068 (3)−0.007 (2)0.020 (2)0.000 (2)
N50.050 (2)0.031 (2)0.053 (2)0.0095 (18)0.0082 (19)0.0026 (19)
N60.044 (2)0.039 (2)0.049 (2)0.0045 (18)0.0115 (18)0.0056 (19)
N70.044 (2)0.036 (2)0.057 (2)0.0001 (18)0.0151 (19)0.0035 (19)
N80.062 (3)0.064 (3)0.059 (3)0.005 (2)0.007 (2)0.007 (2)
O10.070 (2)0.0278 (19)0.083 (2)0.0063 (16)0.0433 (18)0.0034 (16)
O20.073 (2)0.040 (2)0.108 (3)0.0033 (18)0.047 (2)−0.010 (2)
O30.060 (2)0.038 (2)0.055 (2)0.0091 (16)0.0152 (16)−0.0037 (16)
O40.105 (3)0.067 (3)0.070 (2)0.047 (2)0.004 (2)−0.004 (2)
O50.083 (3)0.131 (4)0.118 (3)0.007 (3)0.028 (3)0.042 (3)
C10.047 (3)0.033 (3)0.046 (3)0.002 (2)0.015 (2)0.000 (2)
C20.038 (2)0.038 (3)0.037 (2)−0.001 (2)0.0099 (19)−0.002 (2)
C30.048 (3)0.040 (3)0.054 (3)0.003 (2)0.017 (2)−0.006 (2)
C40.056 (3)0.051 (3)0.072 (3)0.018 (3)0.025 (3)−0.005 (3)
C50.053 (3)0.076 (4)0.060 (3)0.005 (3)0.028 (3)−0.008 (3)
C60.061 (3)0.059 (4)0.073 (4)−0.010 (3)0.036 (3)−0.008 (3)
C70.062 (3)0.039 (3)0.057 (3)0.001 (2)0.025 (3)−0.005 (2)
C80.062 (3)0.036 (3)0.058 (3)0.006 (2)0.019 (2)0.013 (2)
C90.040 (3)0.036 (3)0.040 (2)−0.003 (2)0.009 (2)0.002 (2)
C100.042 (3)0.036 (3)0.040 (3)0.000 (2)0.008 (2)0.004 (2)
C110.046 (3)0.048 (3)0.047 (3)−0.004 (2)0.011 (2)0.000 (2)
C120.069 (4)0.059 (4)0.091 (4)−0.020 (3)0.028 (3)−0.006 (3)
C130.048 (3)0.069 (4)0.075 (4)0.005 (3)0.027 (3)−0.008 (3)
C140.051 (3)0.048 (3)0.062 (3)0.008 (2)0.021 (2)−0.002 (2)
C150.043 (3)0.035 (3)0.057 (3)−0.002 (2)0.016 (2)0.005 (2)
C160.051 (3)0.031 (3)0.050 (3)0.000 (2)0.010 (2)0.007 (2)
C170.066 (3)0.043 (3)0.067 (3)0.010 (3)0.017 (3)0.010 (3)
C180.080 (4)0.055 (4)0.085 (4)0.028 (3)0.007 (3)0.018 (3)
C190.091 (4)0.062 (4)0.075 (4)0.007 (3)−0.012 (3)0.022 (3)
C200.106 (5)0.052 (4)0.065 (4)0.007 (3)−0.001 (3)0.011 (3)
C210.074 (4)0.039 (3)0.063 (3)0.001 (3)0.009 (3)0.002 (3)
C220.122 (5)0.052 (4)0.075 (4)0.032 (3)−0.006 (3)−0.015 (3)
C230.050 (3)0.032 (3)0.051 (3)−0.003 (2)0.016 (2)0.001 (2)
C240.043 (3)0.041 (3)0.050 (3)−0.003 (2)0.016 (2)0.005 (2)
C250.064 (3)0.047 (3)0.053 (3)−0.008 (3)0.013 (3)0.002 (3)
C260.113 (5)0.091 (5)0.056 (3)0.023 (4)−0.010 (3)−0.020 (3)
C270.042 (3)0.065 (4)0.071 (4)0.003 (3)0.012 (3)0.020 (3)
C280.047 (3)0.046 (3)0.062 (3)0.009 (2)0.016 (3)0.005 (2)
Geometric parameters (Å, °) top
Zn1—O12.055 (3)C7—H70.9300
Zn1—N22.073 (3)C8—C91.496 (6)
Zn1—N62.075 (4)C8—H8A0.9600
Zn1—O32.079 (3)C8—H8B0.9600
Zn1—N72.239 (4)C8—H8C0.9600
Zn1—N32.283 (3)C9—C101.483 (6)
N1—C11.329 (5)C10—C111.401 (6)
N1—N21.381 (4)C11—C121.503 (6)
N2—C91.288 (5)C12—H12A0.9600
N3—C141.324 (5)C12—H12B0.9600
N3—C101.353 (5)C12—H12C0.9600
N4—C131.329 (6)C13—C141.370 (6)
N4—C111.346 (5)C13—H130.9300
N5—C151.341 (5)C14—H140.9300
N5—N61.374 (4)C15—C161.486 (6)
N6—C231.283 (5)C16—C211.391 (6)
N7—C281.317 (5)C16—C171.398 (6)
N7—C241.350 (5)C17—C181.385 (6)
N8—C271.314 (6)C18—C191.360 (7)
N8—C251.341 (6)C18—H180.9300
O1—C11.270 (5)C19—C201.363 (8)
O2—C31.351 (5)C19—H190.9300
O2—H20.8200C20—C211.376 (6)
O3—C151.264 (5)C20—H200.9300
O4—C171.351 (6)C21—H210.9300
O4—H40.8200C22—C231.487 (6)
O5—H5A0.8500C22—H22A0.9600
O5—H5B0.8500C22—H22B0.9600
C1—C21.482 (6)C22—H22C0.9600
C2—C71.384 (6)C23—C241.487 (6)
C2—C31.395 (6)C24—C251.413 (6)
C3—C41.398 (6)C25—C261.492 (7)
C4—C51.358 (7)C26—H26A0.9600
C4—H4A0.9300C26—H26B0.9600
C5—C61.370 (7)C26—H26C0.9600
C5—H50.9300C27—C281.388 (6)
C6—C71.372 (6)C27—H270.9300
C6—H60.9300C28—H280.9300
O1—Zn1—N276.41 (12)N3—C10—C11120.2 (4)
O1—Zn1—N6119.26 (13)N3—C10—C9113.9 (4)
N2—Zn1—N6160.85 (13)C11—C10—C9125.9 (4)
O1—Zn1—O394.73 (12)N4—C11—C10120.1 (4)
N2—Zn1—O3115.77 (12)N4—C11—C12114.2 (4)
N6—Zn1—O375.91 (13)C10—C11—C12125.6 (4)
O1—Zn1—N792.09 (13)C11—C12—H12A109.5
N2—Zn1—N797.47 (13)C11—C12—H12B109.5
N6—Zn1—N772.39 (14)H12A—C12—H12B109.5
O3—Zn1—N7146.75 (13)C11—C12—H12C109.5
O1—Zn1—N3148.55 (13)H12A—C12—H12C109.5
N2—Zn1—N372.21 (13)H12B—C12—H12C109.5
N6—Zn1—N391.23 (13)N4—C13—C14121.6 (5)
O3—Zn1—N3100.51 (12)N4—C13—H13119.2
N7—Zn1—N390.03 (12)C14—C13—H13119.2
C1—N1—N2109.9 (3)N3—C14—C13121.4 (5)
C9—N2—N1118.4 (3)N3—C14—H14119.3
C9—N2—Zn1123.6 (3)C13—C14—H14119.3
N1—N2—Zn1115.3 (2)O3—C15—N5125.5 (4)
C14—N3—C10118.2 (4)O3—C15—C16119.9 (4)
C14—N3—Zn1127.5 (3)N5—C15—C16114.6 (4)
C10—N3—Zn1114.0 (3)C21—C16—C17117.6 (4)
C13—N4—C11118.2 (4)C21—C16—C15119.2 (4)
C15—N5—N6109.9 (4)C17—C16—C15123.2 (4)
C23—N6—N5119.7 (4)O4—C17—C18118.1 (5)
C23—N6—Zn1123.9 (3)O4—C17—C16122.1 (4)
N5—N6—Zn1115.9 (3)C18—C17—C16119.8 (5)
C28—N7—C24119.5 (4)C19—C18—C17120.8 (5)
C28—N7—Zn1125.5 (3)C19—C18—H18119.6
C24—N7—Zn1114.9 (3)C17—C18—H18119.6
C27—N8—C25118.7 (4)C18—C19—C20120.6 (5)
C1—O1—Zn1112.3 (3)C18—C19—H19119.7
C3—O2—H2109.5C20—C19—H19119.7
C15—O3—Zn1112.1 (3)C19—C20—C21119.4 (5)
C17—O4—H4109.5C19—C20—H20120.3
H5A—O5—H5B108.9C21—C20—H20120.3
O1—C1—N1125.7 (4)C20—C21—C16121.8 (5)
O1—C1—C2118.5 (4)C20—C21—H21119.1
N1—C1—C2115.8 (4)C16—C21—H21119.1
C7—C2—C3117.5 (4)C23—C22—H22A109.5
C7—C2—C1119.6 (4)C23—C22—H22B109.5
C3—C2—C1122.9 (4)H22A—C22—H22B109.5
O2—C3—C2122.6 (4)C23—C22—H22C109.5
O2—C3—C4117.0 (4)H22A—C22—H22C109.5
C2—C3—C4120.3 (4)H22B—C22—H22C109.5
C5—C4—C3119.4 (5)N6—C23—C22122.0 (4)
C5—C4—H4A120.3N6—C23—C24113.4 (4)
C3—C4—H4A120.3C22—C23—C24124.6 (4)
C4—C5—C6121.7 (4)N7—C24—C25119.4 (4)
C4—C5—H5119.1N7—C24—C23114.2 (4)
C6—C5—H5119.1C25—C24—C23126.4 (4)
C5—C6—C7118.6 (5)N8—C25—C24120.0 (5)
C5—C6—H6120.7N8—C25—C26113.7 (4)
C7—C6—H6120.7C24—C25—C26126.3 (5)
C6—C7—C2122.5 (5)C25—C26—H26A109.5
C6—C7—H7118.8C25—C26—H26B109.5
C2—C7—H7118.8H26A—C26—H26B109.5
C9—C8—H8A109.5C25—C26—H26C109.5
C9—C8—H8B109.5H26A—C26—H26C109.5
H8A—C8—H8B109.5H26B—C26—H26C109.5
C9—C8—H8C109.5N8—C27—C28122.0 (5)
H8A—C8—H8C109.5N8—C27—H27119.0
H8B—C8—H8C109.5C28—C27—H27119.0
N2—C9—C10113.6 (4)N7—C28—C27120.3 (5)
N2—C9—C8122.5 (4)N7—C28—H28119.9
C10—C9—C8123.8 (4)C27—C28—H28119.9
C1—N1—N2—C9169.0 (4)C3—C4—C5—C60.5 (7)
C1—N1—N2—Zn17.0 (4)C4—C5—C6—C70.6 (8)
O1—Zn1—N2—C9−166.9 (3)C5—C6—C7—C2−0.9 (7)
N6—Zn1—N2—C9−20.1 (6)C3—C2—C7—C60.2 (6)
O3—Zn1—N2—C9104.4 (3)C1—C2—C7—C6−179.5 (4)
N7—Zn1—N2—C9−76.6 (3)N1—N2—C9—C10−179.5 (3)
N3—Zn1—N2—C911.0 (3)Zn1—N2—C9—C10−19.0 (5)
O1—Zn1—N2—N1−5.9 (2)N1—N2—C9—C8−3.9 (6)
N6—Zn1—N2—N1140.9 (4)Zn1—N2—C9—C8156.6 (3)
O3—Zn1—N2—N1−94.6 (3)C14—N3—C10—C11−2.9 (6)
N7—Zn1—N2—N184.5 (3)Zn1—N3—C10—C11171.5 (3)
N3—Zn1—N2—N1172.1 (3)C14—N3—C10—C9177.0 (3)
O1—Zn1—N3—C14177.5 (3)Zn1—N3—C10—C9−8.6 (4)
N2—Zn1—N3—C14173.7 (4)N2—C9—C10—N317.1 (5)
N6—Zn1—N3—C14−16.1 (4)C8—C9—C10—N3−158.5 (4)
O3—Zn1—N3—C1459.8 (4)N2—C9—C10—C11−162.9 (4)
N7—Zn1—N3—C14−88.5 (4)C8—C9—C10—C1121.5 (6)
O1—Zn1—N3—C103.7 (4)C13—N4—C11—C10−2.5 (6)
N2—Zn1—N3—C10−0.1 (3)C13—N4—C11—C12173.2 (4)
N6—Zn1—N3—C10170.2 (3)N3—C10—C11—N45.2 (6)
O3—Zn1—N3—C10−114.0 (3)C9—C10—C11—N4−174.7 (4)
N7—Zn1—N3—C1097.8 (3)N3—C10—C11—C12−169.9 (4)
C15—N5—N6—C23179.7 (4)C9—C10—C11—C1210.1 (7)
C15—N5—N6—Zn17.7 (4)C11—N4—C13—C14−2.4 (7)
O1—Zn1—N6—C2392.9 (3)C10—N3—C14—C13−1.9 (6)
N2—Zn1—N6—C23−49.5 (6)Zn1—N3—C14—C13−175.4 (3)
O3—Zn1—N6—C23−179.6 (4)N4—C13—C14—N34.7 (7)
N7—Zn1—N6—C2310.6 (3)Zn1—O3—C15—N5−5.1 (5)
N3—Zn1—N6—C23−79.1 (3)Zn1—O3—C15—C16173.2 (3)
O1—Zn1—N6—N5−95.5 (3)N6—N5—C15—O3−1.6 (6)
N2—Zn1—N6—N5122.1 (4)N6—N5—C15—C16−180.0 (3)
O3—Zn1—N6—N5−8.0 (3)O3—C15—C16—C215.8 (6)
N7—Zn1—N6—N5−177.8 (3)N5—C15—C16—C21−175.7 (4)
N3—Zn1—N6—N592.6 (3)O3—C15—C16—C17−174.3 (4)
O1—Zn1—N7—C2854.9 (4)N5—C15—C16—C174.1 (6)
N2—Zn1—N7—C28−21.7 (4)C21—C16—C17—O4178.7 (4)
N6—Zn1—N7—C28175.0 (4)C15—C16—C17—O4−1.1 (7)
O3—Zn1—N7—C28156.8 (3)C21—C16—C17—C18−0.9 (7)
N3—Zn1—N7—C28−93.7 (4)C15—C16—C17—C18179.3 (5)
O1—Zn1—N7—C24−128.8 (3)O4—C17—C18—C19−178.9 (5)
N2—Zn1—N7—C24154.6 (3)C16—C17—C18—C190.7 (8)
N6—Zn1—N7—C24−8.7 (3)C17—C18—C19—C20−1.0 (9)
O3—Zn1—N7—C24−26.9 (4)C18—C19—C20—C211.4 (9)
N3—Zn1—N7—C2482.6 (3)C19—C20—C21—C16−1.6 (8)
N2—Zn1—O1—C13.6 (3)C17—C16—C21—C201.3 (7)
N6—Zn1—O1—C1−164.5 (3)C15—C16—C21—C20−178.9 (5)
O3—Zn1—O1—C1119.0 (3)N5—N6—C23—C22−0.6 (6)
N7—Zn1—O1—C1−93.6 (3)Zn1—N6—C23—C22170.7 (4)
N3—Zn1—O1—C1−0.1 (4)N5—N6—C23—C24178.5 (3)
O1—Zn1—O3—C15125.7 (3)Zn1—N6—C23—C24−10.2 (5)
N2—Zn1—O3—C15−157.1 (3)C28—N7—C24—C254.0 (6)
N6—Zn1—O3—C156.7 (3)Zn1—N7—C24—C25−172.5 (3)
N7—Zn1—O3—C1524.6 (4)C28—N7—C24—C23−176.6 (4)
N3—Zn1—O3—C15−81.9 (3)Zn1—N7—C24—C236.8 (4)
Zn1—O1—C1—N1−0.9 (5)N6—C23—C24—N71.2 (5)
Zn1—O1—C1—C2176.8 (3)C22—C23—C24—N7−179.7 (4)
N2—N1—C1—O1−4.1 (6)N6—C23—C24—C25−179.4 (4)
N2—N1—C1—C2178.2 (3)C22—C23—C24—C25−0.4 (7)
O1—C1—C2—C7−2.9 (6)C27—N8—C25—C240.8 (7)
N1—C1—C2—C7175.0 (4)C27—N8—C25—C26−177.9 (5)
O1—C1—C2—C3177.4 (4)N7—C24—C25—N8−3.9 (7)
N1—C1—C2—C3−4.7 (6)C23—C24—C25—N8176.8 (4)
C7—C2—C3—O2−178.0 (4)N7—C24—C25—C26174.6 (5)
C1—C2—C3—O21.7 (7)C23—C24—C25—C26−4.7 (8)
C7—C2—C3—C40.9 (6)C25—N8—C27—C282.3 (7)
C1—C2—C3—C4−179.4 (4)C24—N7—C28—C27−1.1 (6)
O2—C3—C4—C5177.7 (4)Zn1—N7—C28—C27175.1 (3)
C2—C3—C4—C5−1.3 (7)N8—C27—C28—N7−2.2 (7)
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20671073), the National Natural Science Foundation of Shandong (grant No. Y2007B60) and Weifang University for research grants.

references
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