metal-organic compounds
Bis[2-acetyl-3-methylpyrazine (2-hydroxybenzoyl)hydrazonato]zinc(II) monohydrate
aDepartment of Chemistry, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: taixishi@lzu.edu.cn
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.
Related literature
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
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808009707/at2559sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009707/at2559Isup2.hkl
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.
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).
Data collection: SMART (Bruker, 2000); cell
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).[Zn(C14H13N4O2)2]·H2O | F(000) = 1288 |
Mr = 621.95 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2538 reflections |
a = 9.3794 (10) Å | θ = 2.4–22.4° |
b = 22.814 (2) Å | µ = 0.91 mm−1 |
c = 13.9407 (14) Å | T = 298 K |
β = 106.402 (2)° | Tabular, colourless |
V = 2861.6 (5) Å3 | 0.32 × 0.20 × 0.16 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5043 independent reflections |
Radiation source: fine-focus sealed tube | 2831 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→11 |
Tmin = 0.759, Tmax = 0.868 | k = −27→23 |
14227 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0366P)2 + 2.1233P] where P = (Fo2 + 2Fc2)/3 |
5043 reflections | (Δ/σ)max < 0.001 |
379 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
[Zn(C14H13N4O2)2]·H2O | V = 2861.6 (5) Å3 |
Mr = 621.95 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.3794 (10) Å | µ = 0.91 mm−1 |
b = 22.814 (2) Å | T = 298 K |
c = 13.9407 (14) Å | 0.32 × 0.20 × 0.16 mm |
β = 106.402 (2)° |
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 = 0.868 | Rint = 0.077 |
14227 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.38 e Å−3 |
5043 reflections | Δρmin = −0.35 e Å−3 |
379 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.09167 (6) | 0.14093 (2) | 0.53708 (4) | 0.04641 (19) | |
N1 | −0.0550 (4) | 0.24903 (15) | 0.5747 (2) | 0.0414 (9) | |
N2 | 0.0653 (4) | 0.23093 (15) | 0.5435 (2) | 0.0402 (9) | |
N3 | 0.2582 (4) | 0.18422 (16) | 0.4675 (3) | 0.0443 (9) | |
N4 | 0.4647 (4) | 0.2484 (2) | 0.4049 (3) | 0.0592 (11) | |
N5 | 0.2455 (4) | 0.02711 (15) | 0.5545 (3) | 0.0461 (9) | |
N6 | 0.1370 (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 | −0.1514 | 0.3110 | 0.6151 | 0.104* | |
O3 | 0.2353 (3) | 0.10277 (13) | 0.6631 (2) | 0.0512 (8) | |
O4 | 0.4380 (4) | −0.05320 (16) | 0.6118 (3) | 0.0852 (12) | |
H4 | 0.3692 | −0.0353 | 0.5737 | 0.128* | |
O5 | 0.7000 (4) | 0.3022 (2) | 0.3185 (3) | 0.1108 (16) | |
H5A | 0.6191 | 0.2940 | 0.3316 | 0.133* | |
H5B | 0.6838 | 0.3291 | 0.2746 | 0.133* | |
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 | −0.4439 | 0.3208 | 0.7018 | 0.070* | |
C5 | −0.4885 (5) | 0.2362 (3) | 0.7158 (3) | 0.0608 (14) | |
H5 | −0.5696 | 0.2429 | 0.7403 | 0.073* | |
C6 | −0.4470 (5) | 0.1797 (2) | 0.7039 (4) | 0.0610 (14) | |
H6 | −0.4995 | 0.1483 | 0.7194 | 0.073* | |
C7 | −0.3265 (5) | 0.1706 (2) | 0.6685 (3) | 0.0511 (12) | |
H7 | −0.2972 | 0.1323 | 0.6612 | 0.061* | |
C8 | 0.0648 (5) | 0.32827 (19) | 0.4706 (3) | 0.0518 (12) | |
H8A | −0.0418 | 0.3268 | 0.4508 | 0.078* | |
H8B | 0.0985 | 0.3432 | 0.4164 | 0.078* | |
H8C | 0.0987 | 0.3535 | 0.5276 | 0.078* | |
C9 | 0.1257 (4) | 0.26797 (19) | 0.4972 (3) | 0.0390 (10) | |
C10 | 0.2528 (4) | 0.24350 (19) | 0.4667 (3) | 0.0401 (10) | |
C11 | 0.3614 (5) | 0.2760 (2) | 0.4387 (3) | 0.0472 (11) | |
C12 | 0.3827 (5) | 0.3412 (2) | 0.4497 (4) | 0.0720 (16) | |
H12A | 0.4853 | 0.3506 | 0.4583 | 0.108* | |
H12B | 0.3539 | 0.3543 | 0.5070 | 0.108* | |
H12C | 0.3224 | 0.3603 | 0.3908 | 0.108* | |
C13 | 0.4634 (5) | 0.1902 (3) | 0.4027 (4) | 0.0618 (14) | |
H13 | 0.5317 | 0.1706 | 0.3773 | 0.074* | |
C14 | 0.3641 (5) | 0.1584 (2) | 0.4370 (3) | 0.0526 (12) | |
H14 | 0.3711 | 0.1177 | 0.4389 | 0.063* | |
C15 | 0.2860 (5) | 0.0543 (2) | 0.6433 (3) | 0.0446 (11) | |
C16 | 0.4033 (5) | 0.02364 (19) | 0.7213 (3) | 0.0447 (11) | |
C17 | 0.4738 (5) | −0.0274 (2) | 0.7028 (4) | 0.0594 (13) | |
C18 | 0.5834 (6) | −0.0531 (2) | 0.7792 (4) | 0.0769 (17) | |
H18 | 0.6309 | −0.0867 | 0.7664 | 0.092* | |
C19 | 0.6226 (6) | −0.0297 (3) | 0.8728 (5) | 0.0829 (18) | |
H19 | 0.6953 | −0.0479 | 0.9235 | 0.099* | |
C20 | 0.5561 (6) | 0.0201 (3) | 0.8929 (4) | 0.0797 (17) | |
H20 | 0.5847 | 0.0364 | 0.9566 | 0.096* | |
C21 | 0.4463 (5) | 0.0461 (2) | 0.8181 (4) | 0.0611 (14) | |
H21 | 0.3996 | 0.0795 | 0.8325 | 0.073* | |
C22 | 0.1358 (6) | −0.0146 (2) | 0.3624 (4) | 0.0896 (19) | |
H22A | 0.2133 | −0.0316 | 0.4154 | 0.134* | |
H22B | 0.1733 | −0.0061 | 0.3066 | 0.134* | |
H22C | 0.0545 | −0.0417 | 0.3421 | 0.134* | |
C23 | 0.0833 (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 | −0.1601 | 0.0257 | 0.1039 | 0.141* | |
H26B | −0.1026 | −0.0154 | 0.1969 | 0.141* | |
H26C | 0.0091 | 0.0251 | 0.1628 | 0.141* | |
C27 | −0.2551 (5) | 0.1511 (2) | 0.2407 (4) | 0.0602 (14) | |
H27 | −0.3334 | 0.1760 | 0.2103 | 0.072* | |
C28 | −0.1727 (5) | 0.1623 (2) | 0.3385 (4) | 0.0517 (12) | |
H28 | −0.1940 | 0.1951 | 0.3716 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0521 (3) | 0.0324 (3) | 0.0577 (3) | 0.0072 (3) | 0.0202 (3) | 0.0011 (3) |
N1 | 0.040 (2) | 0.031 (2) | 0.057 (2) | 0.0013 (17) | 0.0200 (18) | 0.0008 (18) |
N2 | 0.039 (2) | 0.034 (2) | 0.049 (2) | 0.0006 (17) | 0.0148 (17) | 0.0014 (17) |
N3 | 0.042 (2) | 0.043 (3) | 0.050 (2) | 0.0068 (18) | 0.0173 (18) | 0.0016 (18) |
N4 | 0.046 (2) | 0.066 (3) | 0.068 (3) | −0.007 (2) | 0.020 (2) | 0.000 (2) |
N5 | 0.050 (2) | 0.031 (2) | 0.053 (2) | 0.0095 (18) | 0.0082 (19) | 0.0026 (19) |
N6 | 0.044 (2) | 0.039 (2) | 0.049 (2) | 0.0045 (18) | 0.0115 (18) | 0.0056 (19) |
N7 | 0.044 (2) | 0.036 (2) | 0.057 (2) | 0.0001 (18) | 0.0151 (19) | 0.0035 (19) |
N8 | 0.062 (3) | 0.064 (3) | 0.059 (3) | 0.005 (2) | 0.007 (2) | 0.007 (2) |
O1 | 0.070 (2) | 0.0278 (19) | 0.083 (2) | 0.0063 (16) | 0.0433 (18) | 0.0034 (16) |
O2 | 0.073 (2) | 0.040 (2) | 0.108 (3) | 0.0033 (18) | 0.047 (2) | −0.010 (2) |
O3 | 0.060 (2) | 0.038 (2) | 0.055 (2) | 0.0091 (16) | 0.0152 (16) | −0.0037 (16) |
O4 | 0.105 (3) | 0.067 (3) | 0.070 (2) | 0.047 (2) | 0.004 (2) | −0.004 (2) |
O5 | 0.083 (3) | 0.131 (4) | 0.118 (3) | 0.007 (3) | 0.028 (3) | 0.042 (3) |
C1 | 0.047 (3) | 0.033 (3) | 0.046 (3) | 0.002 (2) | 0.015 (2) | 0.000 (2) |
C2 | 0.038 (2) | 0.038 (3) | 0.037 (2) | −0.001 (2) | 0.0099 (19) | −0.002 (2) |
C3 | 0.048 (3) | 0.040 (3) | 0.054 (3) | 0.003 (2) | 0.017 (2) | −0.006 (2) |
C4 | 0.056 (3) | 0.051 (3) | 0.072 (3) | 0.018 (3) | 0.025 (3) | −0.005 (3) |
C5 | 0.053 (3) | 0.076 (4) | 0.060 (3) | 0.005 (3) | 0.028 (3) | −0.008 (3) |
C6 | 0.061 (3) | 0.059 (4) | 0.073 (4) | −0.010 (3) | 0.036 (3) | −0.008 (3) |
C7 | 0.062 (3) | 0.039 (3) | 0.057 (3) | 0.001 (2) | 0.025 (3) | −0.005 (2) |
C8 | 0.062 (3) | 0.036 (3) | 0.058 (3) | 0.006 (2) | 0.019 (2) | 0.013 (2) |
C9 | 0.040 (3) | 0.036 (3) | 0.040 (2) | −0.003 (2) | 0.009 (2) | 0.002 (2) |
C10 | 0.042 (3) | 0.036 (3) | 0.040 (3) | 0.000 (2) | 0.008 (2) | 0.004 (2) |
C11 | 0.046 (3) | 0.048 (3) | 0.047 (3) | −0.004 (2) | 0.011 (2) | 0.000 (2) |
C12 | 0.069 (4) | 0.059 (4) | 0.091 (4) | −0.020 (3) | 0.028 (3) | −0.006 (3) |
C13 | 0.048 (3) | 0.069 (4) | 0.075 (4) | 0.005 (3) | 0.027 (3) | −0.008 (3) |
C14 | 0.051 (3) | 0.048 (3) | 0.062 (3) | 0.008 (2) | 0.021 (2) | −0.002 (2) |
C15 | 0.043 (3) | 0.035 (3) | 0.057 (3) | −0.002 (2) | 0.016 (2) | 0.005 (2) |
C16 | 0.051 (3) | 0.031 (3) | 0.050 (3) | 0.000 (2) | 0.010 (2) | 0.007 (2) |
C17 | 0.066 (3) | 0.043 (3) | 0.067 (3) | 0.010 (3) | 0.017 (3) | 0.010 (3) |
C18 | 0.080 (4) | 0.055 (4) | 0.085 (4) | 0.028 (3) | 0.007 (3) | 0.018 (3) |
C19 | 0.091 (4) | 0.062 (4) | 0.075 (4) | 0.007 (3) | −0.012 (3) | 0.022 (3) |
C20 | 0.106 (5) | 0.052 (4) | 0.065 (4) | 0.007 (3) | −0.001 (3) | 0.011 (3) |
C21 | 0.074 (4) | 0.039 (3) | 0.063 (3) | 0.001 (3) | 0.009 (3) | 0.002 (3) |
C22 | 0.122 (5) | 0.052 (4) | 0.075 (4) | 0.032 (3) | −0.006 (3) | −0.015 (3) |
C23 | 0.050 (3) | 0.032 (3) | 0.051 (3) | −0.003 (2) | 0.016 (2) | 0.001 (2) |
C24 | 0.043 (3) | 0.041 (3) | 0.050 (3) | −0.003 (2) | 0.016 (2) | 0.005 (2) |
C25 | 0.064 (3) | 0.047 (3) | 0.053 (3) | −0.008 (3) | 0.013 (3) | 0.002 (3) |
C26 | 0.113 (5) | 0.091 (5) | 0.056 (3) | 0.023 (4) | −0.010 (3) | −0.020 (3) |
C27 | 0.042 (3) | 0.065 (4) | 0.071 (4) | 0.003 (3) | 0.012 (3) | 0.020 (3) |
C28 | 0.047 (3) | 0.046 (3) | 0.062 (3) | 0.009 (2) | 0.016 (3) | 0.005 (2) |
Zn1—O1 | 2.055 (3) | C7—H7 | 0.9300 |
Zn1—N2 | 2.073 (3) | C8—C9 | 1.496 (6) |
Zn1—N6 | 2.075 (4) | C8—H8A | 0.9600 |
Zn1—O3 | 2.079 (3) | C8—H8B | 0.9600 |
Zn1—N7 | 2.239 (4) | C8—H8C | 0.9600 |
Zn1—N3 | 2.283 (3) | C9—C10 | 1.483 (6) |
N1—C1 | 1.329 (5) | C10—C11 | 1.401 (6) |
N1—N2 | 1.381 (4) | C11—C12 | 1.503 (6) |
N2—C9 | 1.288 (5) | C12—H12A | 0.9600 |
N3—C14 | 1.324 (5) | C12—H12B | 0.9600 |
N3—C10 | 1.353 (5) | C12—H12C | 0.9600 |
N4—C13 | 1.329 (6) | C13—C14 | 1.370 (6) |
N4—C11 | 1.346 (5) | C13—H13 | 0.9300 |
N5—C15 | 1.341 (5) | C14—H14 | 0.9300 |
N5—N6 | 1.374 (4) | C15—C16 | 1.486 (6) |
N6—C23 | 1.283 (5) | C16—C21 | 1.391 (6) |
N7—C28 | 1.317 (5) | C16—C17 | 1.398 (6) |
N7—C24 | 1.350 (5) | C17—C18 | 1.385 (6) |
N8—C27 | 1.314 (6) | C18—C19 | 1.360 (7) |
N8—C25 | 1.341 (6) | C18—H18 | 0.9300 |
O1—C1 | 1.270 (5) | C19—C20 | 1.363 (8) |
O2—C3 | 1.351 (5) | C19—H19 | 0.9300 |
O2—H2 | 0.8200 | C20—C21 | 1.376 (6) |
O3—C15 | 1.264 (5) | C20—H20 | 0.9300 |
O4—C17 | 1.351 (6) | C21—H21 | 0.9300 |
O4—H4 | 0.8200 | C22—C23 | 1.487 (6) |
O5—H5A | 0.8500 | C22—H22A | 0.9600 |
O5—H5B | 0.8500 | C22—H22B | 0.9600 |
C1—C2 | 1.482 (6) | C22—H22C | 0.9600 |
C2—C7 | 1.384 (6) | C23—C24 | 1.487 (6) |
C2—C3 | 1.395 (6) | C24—C25 | 1.413 (6) |
C3—C4 | 1.398 (6) | C25—C26 | 1.492 (7) |
C4—C5 | 1.358 (7) | C26—H26A | 0.9600 |
C4—H4A | 0.9300 | C26—H26B | 0.9600 |
C5—C6 | 1.370 (7) | C26—H26C | 0.9600 |
C5—H5 | 0.9300 | C27—C28 | 1.388 (6) |
C6—C7 | 1.372 (6) | C27—H27 | 0.9300 |
C6—H6 | 0.9300 | C28—H28 | 0.9300 |
O1—Zn1—N2 | 76.41 (12) | N3—C10—C11 | 120.2 (4) |
O1—Zn1—N6 | 119.26 (13) | N3—C10—C9 | 113.9 (4) |
N2—Zn1—N6 | 160.85 (13) | C11—C10—C9 | 125.9 (4) |
O1—Zn1—O3 | 94.73 (12) | N4—C11—C10 | 120.1 (4) |
N2—Zn1—O3 | 115.77 (12) | N4—C11—C12 | 114.2 (4) |
N6—Zn1—O3 | 75.91 (13) | C10—C11—C12 | 125.6 (4) |
O1—Zn1—N7 | 92.09 (13) | C11—C12—H12A | 109.5 |
N2—Zn1—N7 | 97.47 (13) | C11—C12—H12B | 109.5 |
N6—Zn1—N7 | 72.39 (14) | H12A—C12—H12B | 109.5 |
O3—Zn1—N7 | 146.75 (13) | C11—C12—H12C | 109.5 |
O1—Zn1—N3 | 148.55 (13) | H12A—C12—H12C | 109.5 |
N2—Zn1—N3 | 72.21 (13) | H12B—C12—H12C | 109.5 |
N6—Zn1—N3 | 91.23 (13) | N4—C13—C14 | 121.6 (5) |
O3—Zn1—N3 | 100.51 (12) | N4—C13—H13 | 119.2 |
N7—Zn1—N3 | 90.03 (12) | C14—C13—H13 | 119.2 |
C1—N1—N2 | 109.9 (3) | N3—C14—C13 | 121.4 (5) |
C9—N2—N1 | 118.4 (3) | N3—C14—H14 | 119.3 |
C9—N2—Zn1 | 123.6 (3) | C13—C14—H14 | 119.3 |
N1—N2—Zn1 | 115.3 (2) | O3—C15—N5 | 125.5 (4) |
C14—N3—C10 | 118.2 (4) | O3—C15—C16 | 119.9 (4) |
C14—N3—Zn1 | 127.5 (3) | N5—C15—C16 | 114.6 (4) |
C10—N3—Zn1 | 114.0 (3) | C21—C16—C17 | 117.6 (4) |
C13—N4—C11 | 118.2 (4) | C21—C16—C15 | 119.2 (4) |
C15—N5—N6 | 109.9 (4) | C17—C16—C15 | 123.2 (4) |
C23—N6—N5 | 119.7 (4) | O4—C17—C18 | 118.1 (5) |
C23—N6—Zn1 | 123.9 (3) | O4—C17—C16 | 122.1 (4) |
N5—N6—Zn1 | 115.9 (3) | C18—C17—C16 | 119.8 (5) |
C28—N7—C24 | 119.5 (4) | C19—C18—C17 | 120.8 (5) |
C28—N7—Zn1 | 125.5 (3) | C19—C18—H18 | 119.6 |
C24—N7—Zn1 | 114.9 (3) | C17—C18—H18 | 119.6 |
C27—N8—C25 | 118.7 (4) | C18—C19—C20 | 120.6 (5) |
C1—O1—Zn1 | 112.3 (3) | C18—C19—H19 | 119.7 |
C3—O2—H2 | 109.5 | C20—C19—H19 | 119.7 |
C15—O3—Zn1 | 112.1 (3) | C19—C20—C21 | 119.4 (5) |
C17—O4—H4 | 109.5 | C19—C20—H20 | 120.3 |
H5A—O5—H5B | 108.9 | C21—C20—H20 | 120.3 |
O1—C1—N1 | 125.7 (4) | C20—C21—C16 | 121.8 (5) |
O1—C1—C2 | 118.5 (4) | C20—C21—H21 | 119.1 |
N1—C1—C2 | 115.8 (4) | C16—C21—H21 | 119.1 |
C7—C2—C3 | 117.5 (4) | C23—C22—H22A | 109.5 |
C7—C2—C1 | 119.6 (4) | C23—C22—H22B | 109.5 |
C3—C2—C1 | 122.9 (4) | H22A—C22—H22B | 109.5 |
O2—C3—C2 | 122.6 (4) | C23—C22—H22C | 109.5 |
O2—C3—C4 | 117.0 (4) | H22A—C22—H22C | 109.5 |
C2—C3—C4 | 120.3 (4) | H22B—C22—H22C | 109.5 |
C5—C4—C3 | 119.4 (5) | N6—C23—C22 | 122.0 (4) |
C5—C4—H4A | 120.3 | N6—C23—C24 | 113.4 (4) |
C3—C4—H4A | 120.3 | C22—C23—C24 | 124.6 (4) |
C4—C5—C6 | 121.7 (4) | N7—C24—C25 | 119.4 (4) |
C4—C5—H5 | 119.1 | N7—C24—C23 | 114.2 (4) |
C6—C5—H5 | 119.1 | C25—C24—C23 | 126.4 (4) |
C5—C6—C7 | 118.6 (5) | N8—C25—C24 | 120.0 (5) |
C5—C6—H6 | 120.7 | N8—C25—C26 | 113.7 (4) |
C7—C6—H6 | 120.7 | C24—C25—C26 | 126.3 (5) |
C6—C7—C2 | 122.5 (5) | C25—C26—H26A | 109.5 |
C6—C7—H7 | 118.8 | C25—C26—H26B | 109.5 |
C2—C7—H7 | 118.8 | H26A—C26—H26B | 109.5 |
C9—C8—H8A | 109.5 | C25—C26—H26C | 109.5 |
C9—C8—H8B | 109.5 | H26A—C26—H26C | 109.5 |
H8A—C8—H8B | 109.5 | H26B—C26—H26C | 109.5 |
C9—C8—H8C | 109.5 | N8—C27—C28 | 122.0 (5) |
H8A—C8—H8C | 109.5 | N8—C27—H27 | 119.0 |
H8B—C8—H8C | 109.5 | C28—C27—H27 | 119.0 |
N2—C9—C10 | 113.6 (4) | N7—C28—C27 | 120.3 (5) |
N2—C9—C8 | 122.5 (4) | N7—C28—H28 | 119.9 |
C10—C9—C8 | 123.8 (4) | C27—C28—H28 | 119.9 |
C1—N1—N2—C9 | 169.0 (4) | C3—C4—C5—C6 | 0.5 (7) |
C1—N1—N2—Zn1 | 7.0 (4) | C4—C5—C6—C7 | 0.6 (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—C6 | 0.2 (6) |
O3—Zn1—N2—C9 | 104.4 (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—C9 | 11.0 (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—N1 | 140.9 (4) | Zn1—N2—C9—C8 | 156.6 (3) |
O3—Zn1—N2—N1 | −94.6 (3) | C14—N3—C10—C11 | −2.9 (6) |
N7—Zn1—N2—N1 | 84.5 (3) | Zn1—N3—C10—C11 | 171.5 (3) |
N3—Zn1—N2—N1 | 172.1 (3) | C14—N3—C10—C9 | 177.0 (3) |
O1—Zn1—N3—C14 | 177.5 (3) | Zn1—N3—C10—C9 | −8.6 (4) |
N2—Zn1—N3—C14 | 173.7 (4) | N2—C9—C10—N3 | 17.1 (5) |
N6—Zn1—N3—C14 | −16.1 (4) | C8—C9—C10—N3 | −158.5 (4) |
O3—Zn1—N3—C14 | 59.8 (4) | N2—C9—C10—C11 | −162.9 (4) |
N7—Zn1—N3—C14 | −88.5 (4) | C8—C9—C10—C11 | 21.5 (6) |
O1—Zn1—N3—C10 | 3.7 (4) | C13—N4—C11—C10 | −2.5 (6) |
N2—Zn1—N3—C10 | −0.1 (3) | C13—N4—C11—C12 | 173.2 (4) |
N6—Zn1—N3—C10 | 170.2 (3) | N3—C10—C11—N4 | 5.2 (6) |
O3—Zn1—N3—C10 | −114.0 (3) | C9—C10—C11—N4 | −174.7 (4) |
N7—Zn1—N3—C10 | 97.8 (3) | N3—C10—C11—C12 | −169.9 (4) |
C15—N5—N6—C23 | 179.7 (4) | C9—C10—C11—C12 | 10.1 (7) |
C15—N5—N6—Zn1 | 7.7 (4) | C11—N4—C13—C14 | −2.4 (7) |
O1—Zn1—N6—C23 | 92.9 (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—N3 | 4.7 (7) |
N7—Zn1—N6—C23 | 10.6 (3) | Zn1—O3—C15—N5 | −5.1 (5) |
N3—Zn1—N6—C23 | −79.1 (3) | Zn1—O3—C15—C16 | 173.2 (3) |
O1—Zn1—N6—N5 | −95.5 (3) | N6—N5—C15—O3 | −1.6 (6) |
N2—Zn1—N6—N5 | 122.1 (4) | N6—N5—C15—C16 | −180.0 (3) |
O3—Zn1—N6—N5 | −8.0 (3) | O3—C15—C16—C21 | 5.8 (6) |
N7—Zn1—N6—N5 | −177.8 (3) | N5—C15—C16—C21 | −175.7 (4) |
N3—Zn1—N6—N5 | 92.6 (3) | O3—C15—C16—C17 | −174.3 (4) |
O1—Zn1—N7—C28 | 54.9 (4) | N5—C15—C16—C17 | 4.1 (6) |
N2—Zn1—N7—C28 | −21.7 (4) | C21—C16—C17—O4 | 178.7 (4) |
N6—Zn1—N7—C28 | 175.0 (4) | C15—C16—C17—O4 | −1.1 (7) |
O3—Zn1—N7—C28 | 156.8 (3) | C21—C16—C17—C18 | −0.9 (7) |
N3—Zn1—N7—C28 | −93.7 (4) | C15—C16—C17—C18 | 179.3 (5) |
O1—Zn1—N7—C24 | −128.8 (3) | O4—C17—C18—C19 | −178.9 (5) |
N2—Zn1—N7—C24 | 154.6 (3) | C16—C17—C18—C19 | 0.7 (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—C21 | 1.4 (9) |
N3—Zn1—N7—C24 | 82.6 (3) | C19—C20—C21—C16 | −1.6 (8) |
N2—Zn1—O1—C1 | 3.6 (3) | C17—C16—C21—C20 | 1.3 (7) |
N6—Zn1—O1—C1 | −164.5 (3) | C15—C16—C21—C20 | −178.9 (5) |
O3—Zn1—O1—C1 | 119.0 (3) | N5—N6—C23—C22 | −0.6 (6) |
N7—Zn1—O1—C1 | −93.6 (3) | Zn1—N6—C23—C22 | 170.7 (4) |
N3—Zn1—O1—C1 | −0.1 (4) | N5—N6—C23—C24 | 178.5 (3) |
O1—Zn1—O3—C15 | 125.7 (3) | Zn1—N6—C23—C24 | −10.2 (5) |
N2—Zn1—O3—C15 | −157.1 (3) | C28—N7—C24—C25 | 4.0 (6) |
N6—Zn1—O3—C15 | 6.7 (3) | Zn1—N7—C24—C25 | −172.5 (3) |
N7—Zn1—O3—C15 | 24.6 (4) | C28—N7—C24—C23 | −176.6 (4) |
N3—Zn1—O3—C15 | −81.9 (3) | Zn1—N7—C24—C23 | 6.8 (4) |
Zn1—O1—C1—N1 | −0.9 (5) | N6—C23—C24—N7 | 1.2 (5) |
Zn1—O1—C1—C2 | 176.8 (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—C2 | 178.2 (3) | C22—C23—C24—C25 | −0.4 (7) |
O1—C1—C2—C7 | −2.9 (6) | C27—N8—C25—C24 | 0.8 (7) |
N1—C1—C2—C7 | 175.0 (4) | C27—N8—C25—C26 | −177.9 (5) |
O1—C1—C2—C3 | 177.4 (4) | N7—C24—C25—N8 | −3.9 (7) |
N1—C1—C2—C3 | −4.7 (6) | C23—C24—C25—N8 | 176.8 (4) |
C7—C2—C3—O2 | −178.0 (4) | N7—C24—C25—C26 | 174.6 (5) |
C1—C2—C3—O2 | 1.7 (7) | C23—C24—C25—C26 | −4.7 (8) |
C7—C2—C3—C4 | 0.9 (6) | C25—N8—C27—C28 | 2.3 (7) |
C1—C2—C3—C4 | −179.4 (4) | C24—N7—C28—C27 | −1.1 (6) |
O2—C3—C4—C5 | 177.7 (4) | Zn1—N7—C28—C27 | 175.1 (3) |
C2—C3—C4—C5 | −1.3 (7) | N8—C27—C28—N7 | −2.2 (7) |
Experimental details
Crystal data | |
Chemical formula | [Zn(C14H13N4O2)2]·H2O |
Mr | 621.95 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.3794 (10), 22.814 (2), 13.9407 (14) |
β (°) | 106.402 (2) |
V (Å3) | 2861.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.32 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.759, 0.868 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14227, 5043, 2831 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.128, 1.02 |
No. of reflections | 5043 |
No. of parameters | 379 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.35 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
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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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.