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Acta Cryst. (2008). E64, m502    [ doi:10.1107/S1600536808005060 ]

{2,2'-[4-Methyl-4-azaheptane-1,7-diylbis(nitrilomethylidyne)]diphenolato}zinc(II)

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

Abstract top

In the title compound, [Zn(C21H25N3O2)], the ZnII atom is five-coordinate from three N donor atoms and two O donor atoms of the dianion ligand in a distorted trigonal-bipyramidal arrangement. Three methylene groups of the ligand are disordered over two orientations in a 0.555 (6):0.445 (6) ratio.

Comment top

Schiff-base ligands are able to coordinate to metal ions through their imine nitrogen atoms and another group, usually linked to the aldehyde moiety. They have long played a key role in coordination chemistry (e.g. Niu et al., 2005; Herzfeld & Nagy, 1999). We now report the synthesis and structure of the title compound, (I).

The ZnII center in (I) is five-coordinate with three N donor atoms and two O donor atoms of salicylaldehyde-N,N-bis-(3-aminopropyl)methylamine, and forms a distorted trigonal bipyramidal arrangement (Table 1, Fig. 1) with the O atoms in the equatorial sites. The dihedral angle between the aromatic rings is 72.23 (19)°.

Related literature top

For related literature, see: Herzfeld & Nagy (1999); Niu et al. (2005).

Experimental top

1 mmol of ZnII acetate was added to a solution of salicylaldehyde-N,N-bis(3-aminopropyl)methylamine (1 mmol) in 10 ml of ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then the product was collected by filtration, yield 68%. IR (KBr disk): 1614 (m) (C=N). Colourless blocks of (I) were grown by slow evaporation of an ethanol solution.

Refinement top

Three methylene groups (C1, C4, C7) of the ligand are disordered over two positions in a 0.555 (6):0.445 (6) ratio (sum of occupancies constrained to unity). The positions of all H atoms were fixed geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

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 molecular structure of (I) with 30% probabiility ellipsoids (H atoms and the minor disorder component omitted for clarity).
{2,2'-[4-Methyl-4-azaheptane-1,7- diylbis(nitrilomethylidyne)]diphenolato}zinc(II) top
Crystal data top
[Zn(C21H25N3O2)]F000 = 872
Mr = 416.81Dx = 1.407 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3004 reflections
a = 6.7813 (6) Åθ = 2.5–24.4º
b = 13.9833 (12) ŵ = 1.27 mm−1
c = 20.766 (2) ÅT = 298 (2) K
β = 92.1460 (10)ºBlock, colourless
V = 1967.7 (3) Å30.42 × 0.30 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3465 independent reflections
Radiation source: fine-focus sealed tube2434 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −4→8
Tmin = 0.618, Tmax = 0.823k = −16→16
9657 measured reflectionsl = −24→23
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.094  w = 1/[σ2(Fo2) + (0.036P)2 + 1.2726P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3465 reflectionsΔρmax = 0.31 e Å−3
274 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C21H25N3O2)]V = 1967.7 (3) Å3
Mr = 416.81Z = 4
Monoclinic, P21/cMo Kα
a = 6.7813 (6) ŵ = 1.27 mm−1
b = 13.9833 (12) ÅT = 298 (2) K
c = 20.766 (2) Å0.42 × 0.30 × 0.16 mm
β = 92.1460 (10)º
Data collection top
Bruker SMART CCD
diffractometer		3465 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2434 reflections with I > 2σ(I)
Tmin = 0.618, Tmax = 0.823Rint = 0.031
9657 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039274 parameters
wR(F2) = 0.094H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å−3
3465 reflectionsΔρmin = −0.23 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*/UeqOcc. (<1)
Zn10.05456 (5)−0.00305 (3)0.296700 (17)0.04162 (13)
N10.0566 (4)0.1448 (2)0.32765 (15)0.0532 (7)
N20.2021 (4)−0.0409 (2)0.38237 (13)0.0497 (7)
N3−0.0914 (4)0.0382 (2)0.21187 (14)0.0478 (7)
O1−0.1738 (3)−0.07700 (18)0.32321 (12)0.0630 (7)
O20.2801 (3)−0.04353 (18)0.24716 (10)0.0547 (6)
C10.2519 (12)0.1720 (5)0.3548 (4)0.072 (3)0.555 (6)
H1A0.24790.23930.36600.087*0.555 (6)
H1B0.34680.16480.32140.087*0.555 (6)
C1'0.1189 (14)0.1529 (6)0.3952 (5)0.068 (3)0.445 (6)
H1'10.02530.11800.42050.081*0.445 (6)
H1'20.11050.21970.40740.081*0.445 (6)
C20.3289 (6)0.1166 (3)0.4143 (2)0.0795 (13)
H2A0.44530.14850.43250.095*0.555 (6)
H2B0.22910.11690.44660.095*0.555 (6)
H2'A0.42180.15770.39310.095*0.445 (6)
H2'B0.35090.12570.46030.095*0.445 (6)
C30.3807 (5)0.0136 (3)0.39799 (18)0.0650 (11)
H3A0.46620.01260.36160.078*
H3B0.4512−0.01560.43440.078*
C40.0020 (11)0.2101 (5)0.2725 (4)0.069 (2)0.555 (6)
H4A0.09410.20010.23850.083*0.555 (6)
H4B0.01630.27580.28700.083*0.555 (6)
C4'−0.1349 (14)0.1873 (6)0.3190 (5)0.068 (3)0.445 (6)
H4'1−0.13180.25070.33790.081*0.445 (6)
H4'2−0.22920.14940.34200.081*0.445 (6)
C5−0.2105 (6)0.1959 (3)0.2442 (2)0.0773 (13)
H5A−0.30160.21430.27690.093*0.555 (6)
H5B−0.23010.23980.20840.093*0.555 (6)
H5'A−0.32300.23850.24000.093*0.445 (6)
H5'B−0.10580.22140.21860.093*0.445 (6)
C6−0.2670 (5)0.0966 (3)0.22078 (19)0.0621 (10)
H6A−0.34970.06620.25190.075*
H6B−0.34220.10140.18030.075*
C7−0.0990 (11)0.1576 (5)0.3790 (4)0.069 (3)0.555 (6)
H7A−0.09950.22300.39310.104*0.555 (6)
H7B−0.06780.11660.41500.104*0.555 (6)
H7C−0.22690.14130.36080.104*0.555 (6)
C7'0.2059 (14)0.1965 (6)0.2876 (5)0.073 (3)0.445 (6)
H7'10.17200.18800.24270.109*0.445 (6)
H7'20.33510.17090.29690.109*0.445 (6)
H7'30.20490.26350.29790.109*0.445 (6)
C80.1539 (5)−0.1118 (3)0.41727 (16)0.0543 (9)
H80.2420−0.12870.45070.065*
C9−0.0230 (6)−0.1678 (2)0.40993 (16)0.0523 (9)
C10−0.1786 (5)−0.1465 (3)0.36458 (16)0.0496 (9)
C11−0.3492 (6)−0.2041 (3)0.36588 (19)0.0689 (11)
H11−0.4561−0.19050.33800.083*
C12−0.3599 (9)−0.2800 (3)0.4076 (2)0.0901 (17)
H12−0.4735−0.31730.40700.108*
C13−0.2084 (10)−0.3019 (3)0.4499 (2)0.0916 (17)
H13−0.2180−0.35400.47750.110*
C14−0.0421 (7)−0.2467 (3)0.45150 (17)0.0714 (12)
H140.0609−0.26140.48070.086*
C15−0.0409 (5)0.0154 (2)0.15601 (17)0.0539 (9)
H15−0.12700.03220.12200.065*
C160.1365 (5)−0.0338 (2)0.13989 (16)0.0466 (8)
C170.2905 (5)−0.0573 (2)0.18560 (15)0.0428 (8)
C180.4635 (6)−0.0977 (3)0.16172 (18)0.0579 (10)
H180.5671−0.11340.19040.070*
C190.4829 (7)−0.1144 (3)0.0972 (2)0.0728 (12)
H190.6002−0.13990.08300.087*
C200.3324 (8)−0.0942 (3)0.0531 (2)0.0824 (14)
H200.3459−0.10700.00950.099*
C210.1631 (7)−0.0552 (3)0.07466 (18)0.0714 (12)
H210.0606−0.04210.04490.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0380 (2)0.0434 (2)0.0434 (2)−0.00014 (19)0.00068 (15)0.00249 (18)
N10.0469 (18)0.0445 (17)0.069 (2)−0.0050 (14)0.0094 (15)−0.0073 (15)
N20.0418 (16)0.0634 (18)0.0437 (16)0.0007 (14)−0.0021 (13)−0.0026 (15)
N30.0404 (16)0.0486 (16)0.0541 (18)0.0054 (13)−0.0037 (14)0.0089 (13)
O10.0432 (14)0.0714 (18)0.0737 (16)−0.0154 (13)−0.0062 (12)0.0271 (14)
O20.0399 (13)0.0782 (17)0.0459 (14)0.0156 (12)−0.0010 (11)−0.0063 (12)
C10.068 (5)0.053 (5)0.096 (7)−0.012 (4)0.009 (5)−0.013 (4)
C1'0.069 (7)0.054 (6)0.081 (7)0.002 (5)0.008 (6)−0.013 (5)
C20.063 (3)0.089 (3)0.086 (3)−0.006 (2)−0.008 (2)−0.029 (3)
C30.046 (2)0.093 (3)0.055 (2)−0.005 (2)−0.0089 (17)−0.006 (2)
C40.070 (6)0.047 (4)0.091 (6)−0.006 (4)0.013 (5)−0.001 (4)
C4'0.064 (6)0.050 (5)0.090 (8)0.004 (5)0.010 (6)−0.009 (5)
C50.065 (3)0.061 (3)0.106 (4)0.022 (2)−0.001 (3)0.010 (2)
C60.044 (2)0.068 (3)0.074 (3)0.0147 (19)−0.0040 (19)0.015 (2)
C70.060 (5)0.071 (5)0.078 (6)0.003 (4)0.021 (4)−0.025 (4)
C7'0.070 (7)0.051 (5)0.098 (8)−0.019 (5)0.019 (6)0.005 (5)
C80.055 (2)0.071 (3)0.0370 (19)0.015 (2)−0.0002 (17)0.0036 (18)
C90.070 (3)0.046 (2)0.0424 (19)0.0061 (19)0.0162 (19)0.0017 (16)
C100.053 (2)0.050 (2)0.047 (2)−0.0071 (18)0.0126 (18)−0.0048 (17)
C110.073 (3)0.071 (3)0.063 (2)−0.026 (2)0.013 (2)−0.008 (2)
C120.134 (5)0.071 (3)0.068 (3)−0.051 (3)0.038 (3)−0.014 (2)
C130.166 (6)0.054 (3)0.057 (3)−0.021 (3)0.040 (3)0.001 (2)
C140.108 (4)0.059 (3)0.048 (2)0.011 (3)0.020 (2)0.0062 (19)
C150.055 (2)0.056 (2)0.049 (2)0.0014 (18)−0.0116 (17)0.0142 (17)
C160.055 (2)0.0400 (18)0.0454 (19)−0.0023 (16)0.0033 (17)0.0027 (15)
C170.046 (2)0.0357 (18)0.047 (2)0.0007 (15)0.0044 (16)0.0007 (15)
C180.058 (2)0.052 (2)0.064 (2)0.0077 (19)0.0106 (19)−0.0007 (18)
C190.084 (3)0.062 (3)0.075 (3)0.012 (2)0.032 (3)−0.003 (2)
C200.118 (4)0.076 (3)0.055 (3)0.005 (3)0.026 (3)−0.005 (2)
C210.098 (3)0.070 (3)0.046 (2)0.003 (3)−0.002 (2)0.009 (2)
Geometric parameters (Å, °) top
Zn1—O11.958 (2)C5—H5A0.9700
Zn1—O21.959 (2)C5—H5B0.9700
Zn1—N32.070 (3)C5—H5'A0.9700
Zn1—N22.077 (3)C5—H5'B0.9700
Zn1—N12.164 (3)C6—H6A0.9700
N1—C4'1.434 (9)C6—H6B0.9700
N1—C1'1.454 (9)C7—H7A0.9600
N1—C11.470 (8)C7—H7B0.9600
N1—C41.501 (8)C7—H7C0.9600
N1—C7'1.518 (9)C7'—H7'10.9600
N1—C71.539 (7)C7'—H7'20.9600
N2—C81.278 (4)C7'—H7'30.9600
N2—C31.457 (4)C8—C91.436 (5)
N3—C151.262 (4)C8—H80.9300
N3—C61.461 (4)C9—C141.409 (5)
O1—C101.298 (4)C9—C101.419 (5)
O2—C171.297 (4)C10—C111.411 (5)
C1—C21.532 (9)C11—C121.374 (6)
C1—H1A0.9700C11—H110.9300
C1—H1B0.9700C12—C131.361 (7)
C1'—C21.550 (10)C12—H120.9300
C1'—H1'10.9700C13—C141.367 (6)
C1'—H1'20.9700C13—H130.9300
C2—C31.525 (6)C14—H140.9300
C2—H2A0.9700C15—C161.436 (5)
C2—H2B0.9700C15—H150.9300
C2—H2'B0.9700C16—C211.405 (5)
C3—H3A0.9700C16—C171.423 (4)
C3—H3B0.9700C17—C181.409 (4)
C4—C51.549 (8)C18—C191.370 (5)
C4—H4A0.9700C18—H180.9300
C4—H4B0.9700C19—C201.375 (6)
C4'—C51.621 (11)C19—H190.9300
C4'—H4'10.9700C20—C211.362 (6)
C4'—H4'20.9700C20—H200.9300
C5—C61.515 (5)C21—H210.9300
O1—Zn1—O2129.52 (11)N1—C4—H5'B146.2
O1—Zn1—N391.62 (10)C5—C4—H5'B38.5
O2—Zn1—N389.51 (10)H4A—C4—H5'B75.7
O1—Zn1—N289.15 (11)H4B—C4—H5'B101.3
O2—Zn1—N290.90 (10)N1—C4'—C5113.8 (6)
N3—Zn1—N2178.59 (12)N1—C4'—H4'1108.8
O1—Zn1—N1114.66 (11)C5—C4'—H4'1108.8
O2—Zn1—N1115.81 (11)N1—C4'—H4'2108.8
N3—Zn1—N189.10 (12)C5—C4'—H4'2108.8
N2—Zn1—N189.51 (12)H4'1—C4'—H4'2107.7
C4'—N1—C1'108.5 (6)C6—C5—C4117.4 (4)
C4'—N1—C1137.7 (5)C6—C5—C4'107.9 (4)
C1'—N1—C152.0 (5)C4—C5—C4'52.4 (4)
C4'—N1—C457.0 (5)C6—C5—H5A108.0
C1'—N1—C4138.0 (5)C4—C5—H5A108.0
C1—N1—C4109.2 (5)C4'—C5—H5A62.3
C4'—N1—C7'110.7 (6)C6—C5—H5B108.0
C1'—N1—C7'108.4 (6)C4—C5—H5B108.0
C1—N1—C7'58.5 (5)C4'—C5—H5B144.1
C4—N1—C7'56.1 (5)H5A—C5—H5B107.2
C4'—N1—C752.9 (5)C6—C5—H5'A110.2
C1'—N1—C760.3 (5)C4—C5—H5'A132.3
C1—N1—C7109.6 (5)C4'—C5—H5'A110.6
C4—N1—C7107.5 (5)H5A—C5—H5'A51.7
C7'—N1—C7144.4 (5)H5B—C5—H5'A57.0
C4'—N1—Zn1111.3 (4)C6—C5—H5'B110.0
C1'—N1—Zn1111.1 (4)C4—C5—H5'B58.0
C1—N1—Zn1110.9 (3)C4'—C5—H5'B109.9
C4—N1—Zn1110.9 (3)H5A—C5—H5'B141.6
C7'—N1—Zn1106.9 (4)H5B—C5—H5'B55.2
C7—N1—Zn1108.7 (3)H5'A—C5—H5'B108.3
C8—N2—C3120.5 (3)N3—C6—C5110.8 (3)
C8—N2—Zn1124.0 (2)N3—C6—H6A109.5
C3—N2—Zn1115.3 (2)C5—C6—H6A109.5
C15—N3—C6120.5 (3)N3—C6—H6B109.5
C15—N3—Zn1125.0 (2)C5—C6—H6B109.5
C6—N3—Zn1114.4 (2)H6A—C6—H6B108.1
C10—O1—Zn1128.4 (2)N1—C7—H7A109.5
C17—O2—Zn1129.2 (2)N1—C7—H7B109.5
N1—C1—C2117.0 (6)N1—C7—H7C109.5
N1—C1—H1A108.1N1—C7'—H7'1109.5
C2—C1—H1A108.1N1—C7'—H7'2109.5
N1—C1—H1B108.1H7'1—C7'—H7'2109.5
C2—C1—H1B108.1N1—C7'—H7'3109.5
H1A—C1—H1B107.3H7'1—C7'—H7'3109.5
N1—C1—H2'A153.9H7'2—C7'—H7'3109.5
C2—C1—H2'A38.4N2—C8—C9126.4 (3)
H1A—C1—H2'A91.9N2—C8—H8116.8
H1B—C1—H2'A80.6C9—C8—H8116.8
N1—C1'—C2116.9 (7)C14—C9—C10119.2 (4)
N1—C1'—H1'1108.1C14—C9—C8117.2 (4)
C2—C1'—H1'1108.1C10—C9—C8123.6 (3)
N1—C1'—H1'2108.1O1—C10—C11118.8 (3)
C2—C1'—H1'2108.1O1—C10—C9124.0 (3)
H1'1—C1'—H1'2107.3C11—C10—C9117.2 (3)
C3—C2—C1111.9 (4)C12—C11—C10121.1 (4)
C3—C2—C1'118.0 (4)C12—C11—H11119.5
C1—C2—C1'49.2 (4)C10—C11—H11119.5
C3—C2—H2A109.2C13—C12—C11121.6 (4)
C1—C2—H2A109.2C13—C12—H12119.2
C1'—C2—H2A132.5C11—C12—H12119.2
C3—C2—H2B109.2C12—C13—C14119.4 (4)
C1—C2—H2B109.2C12—C13—H13120.3
C1'—C2—H2B61.1C14—C13—H13120.3
H2A—C2—H2B107.9C13—C14—C9121.5 (4)
C3—C2—H2'A107.5C13—C14—H14119.3
C1—C2—H2'A62.8C9—C14—H14119.3
C1'—C2—H2'A107.2N3—C15—C16126.4 (3)
H2A—C2—H2'A51.1N3—C15—H15116.8
H2B—C2—H2'A142.4C16—C15—H15116.8
C3—C2—H2'B108.3C21—C16—C17118.5 (3)
C1—C2—H2'B139.8C21—C16—C15117.7 (3)
C1'—C2—H2'B108.4C17—C16—C15123.7 (3)
H2A—C2—H2'B57.6O2—C17—C18118.9 (3)
H2B—C2—H2'B53.4O2—C17—C16123.9 (3)
H2'A—C2—H2'B107.0C18—C17—C16117.2 (3)
N2—C3—C2110.3 (3)C19—C18—C17121.6 (4)
N2—C3—H3A109.6C19—C18—H18119.2
C2—C3—H3A109.6C17—C18—H18119.2
N2—C3—H3B109.6C18—C19—C20121.4 (4)
C2—C3—H3B109.6C18—C19—H19119.3
H3A—C3—H3B108.1C20—C19—H19119.3
N1—C4—C5114.2 (5)C21—C20—C19118.5 (4)
N1—C4—H4A108.7C21—C20—H20120.8
C5—C4—H4A108.7C19—C20—H20120.8
N1—C4—H4B108.7C20—C21—C16122.8 (4)
C5—C4—H4B108.7C20—C21—H21118.6
H4A—C4—H4B107.6C16—C21—H21118.6
O1—Zn1—N1—C4'−43.0 (5)N1—C1—C2—C1'−39.1 (6)
O2—Zn1—N1—C4'137.4 (5)N1—C1'—C2—C3−56.1 (9)
N3—Zn1—N1—C4'48.4 (5)N1—C1'—C2—C139.6 (6)
N2—Zn1—N1—C4'−131.8 (5)C8—N2—C3—C2−116.9 (4)
O1—Zn1—N1—C1'78.0 (5)Zn1—N2—C3—C268.8 (4)
O2—Zn1—N1—C1'−101.6 (5)C1—C2—C3—N2−69.8 (5)
N3—Zn1—N1—C1'169.4 (5)C1'—C2—C3—N2−15.6 (7)
N2—Zn1—N1—C1'−10.8 (5)C4'—N1—C4—C5−38.7 (6)
O1—Zn1—N1—C1134.0 (4)C1'—N1—C4—C5−119.8 (8)
O2—Zn1—N1—C1−45.6 (4)C1—N1—C4—C5−173.8 (5)
N3—Zn1—N1—C1−134.6 (4)C7'—N1—C4—C5160.4 (8)
N2—Zn1—N1—C145.2 (4)C7—N1—C4—C5−55.0 (6)
O1—Zn1—N1—C4−104.5 (4)Zn1—N1—C4—C563.7 (6)
O2—Zn1—N1—C475.9 (4)C1'—N1—C4'—C5172.3 (6)
N3—Zn1—N1—C4−13.1 (4)C1—N1—C4'—C5119.0 (8)
N2—Zn1—N1—C4166.7 (4)C4—N1—C4'—C536.6 (5)
O1—Zn1—N1—C7'−163.9 (5)C7'—N1—C4'—C553.5 (8)
O2—Zn1—N1—C7'16.5 (5)C7—N1—C4'—C5−163.0 (9)
N3—Zn1—N1—C7'−72.5 (5)Zn1—N1—C4'—C5−65.2 (7)
N2—Zn1—N1—C7'107.3 (5)N1—C4—C5—C6−56.3 (7)
O1—Zn1—N1—C713.5 (4)N1—C4—C5—C4'35.9 (5)
O2—Zn1—N1—C7−166.1 (4)N1—C4'—C5—C673.6 (7)
N3—Zn1—N1—C7104.9 (4)N1—C4'—C5—C4−37.6 (5)
N2—Zn1—N1—C7−75.3 (4)C15—N3—C6—C5−109.7 (4)
O1—Zn1—N2—C819.3 (3)Zn1—N3—C6—C571.3 (3)
O2—Zn1—N2—C8−110.2 (3)C4—C5—C6—N3−16.8 (6)
N3—Zn1—N2—C8143 (4)C4'—C5—C6—N3−73.1 (5)
N1—Zn1—N2—C8134.0 (3)C3—N2—C8—C9175.9 (3)
O1—Zn1—N2—C3−166.6 (2)Zn1—N2—C8—C9−10.3 (5)
O2—Zn1—N2—C363.9 (2)N2—C8—C9—C14176.4 (3)
N3—Zn1—N2—C3−43 (4)N2—C8—C9—C10−5.1 (6)
N1—Zn1—N2—C3−51.9 (2)Zn1—O1—C10—C11−165.7 (3)
O1—Zn1—N3—C15−115.6 (3)Zn1—O1—C10—C915.4 (5)
O2—Zn1—N3—C1513.9 (3)C14—C9—C10—O1−178.3 (3)
N2—Zn1—N3—C15121 (4)C8—C9—C10—O13.2 (5)
N1—Zn1—N3—C15129.7 (3)C14—C9—C10—C112.7 (5)
O1—Zn1—N3—C663.3 (2)C8—C9—C10—C11−175.8 (3)
O2—Zn1—N3—C6−167.2 (2)O1—C10—C11—C12178.4 (4)
N2—Zn1—N3—C6−60 (4)C9—C10—C11—C12−2.6 (5)
N1—Zn1—N3—C6−51.3 (2)C10—C11—C12—C130.9 (7)
O2—Zn1—O1—C1068.2 (3)C11—C12—C13—C140.7 (7)
N3—Zn1—O1—C10158.9 (3)C12—C13—C14—C9−0.5 (6)
N2—Zn1—O1—C10−22.3 (3)C10—C9—C14—C13−1.2 (5)
N1—Zn1—O1—C10−111.3 (3)C8—C9—C14—C13177.3 (4)
O1—Zn1—O2—C1777.3 (3)C6—N3—C15—C16173.9 (3)
N3—Zn1—O2—C17−14.4 (3)Zn1—N3—C15—C16−7.2 (5)
N2—Zn1—O2—C17166.9 (3)N3—C15—C16—C21178.1 (4)
N1—Zn1—O2—C17−103.2 (3)N3—C15—C16—C17−5.4 (6)
C4'—N1—C1—C2115.1 (9)Zn1—O2—C17—C18−172.4 (2)
C1'—N1—C1—C240.2 (6)Zn1—O2—C17—C167.7 (5)
C4—N1—C1—C2176.8 (5)C21—C16—C17—O2−177.9 (3)
C7'—N1—C1—C2−158.2 (8)C15—C16—C17—O25.6 (5)
C7—N1—C1—C259.2 (7)C21—C16—C17—C182.2 (5)
Zn1—N1—C1—C2−60.8 (6)C15—C16—C17—C18−174.2 (3)
C4'—N1—C1'—C2−176.4 (6)O2—C17—C18—C19179.7 (3)
C1—N1—C1'—C2−39.6 (6)C16—C17—C18—C19−0.5 (5)
C4—N1—C1'—C2−115.5 (8)C17—C18—C19—C20−1.4 (6)
C7'—N1—C1'—C2−56.1 (8)C18—C19—C20—C211.3 (7)
C7—N1—C1'—C2161.1 (9)C19—C20—C21—C160.6 (7)
Zn1—N1—C1'—C261.0 (7)C17—C16—C21—C20−2.4 (6)
N1—C1—C2—C369.7 (7)C15—C16—C21—C20174.3 (4)
Table 1
Selected geometric parameters (Å, °) top
Zn1—O11.958 (2)Zn1—N22.077 (3)
Zn1—O21.959 (2)Zn1—N12.164 (3)
Zn1—N32.070 (3)
N3—Zn1—N2178.59 (12)
Acknowledgements top

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

references
References top

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Herzfeld, R. & Nagy, P. (1999). Spectrosc. Lett. 31, 57–65.

Niu, S. Y., Jie, G. F., Zhang, S. S., Li, Y. & Yang, F. (2005). Chem. Res. Chin. Univ. 21, 149–153.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.