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Acta Cryst. (2007). E63, m1927-m1928    [ doi:10.1107/S1600536807028917 ]

Bis(4-methoxybenzaldehyde 2-hydroxybenzoylhydrazonato)pyridinezinc(II) pyridine solvate

X.-S. Tai, J. Yin and M.-Y. Hao

Abstract top

In the title compound, [Zn(C15H13N2O3)2(C5H5N)]·C5H5N, a distorted ZnN3O2 trigonal-bipyramidal coordination geometry results from the coordination of the two bidentate ligands and one pyridine molecule. A crystallographic twofold rotation axis passes through Zn and the pyridine ligand. The pyridine solvent molecule is disordered over an inversion centre. Intermolecular C-H...O and intramolecular C-H...O and O-H...N hydrogen-bonding interactions help to establish the crystal packing.

Comment top

As part of our onging studies of metal coordination complexes with multidentate ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported.

Two N,O-bidentate ligands and one pyridine molecule are attached to the zinc atom, resulting in a distorted ZnN3O2 trigonal bipyramidal co-ordination geometry (Fig. 1). The C1═O1 [1.287 (4) Å] and C8═N2 [1.290 (5) Å] bond lengths implies double bond character. The dihedral angle between the (C2—C7) and (C9—C14) planes is 29.0 (2)°. The geometrical parameters for (I) are normal.

Two molecules of pyridine complete the structure of (I) and the intermolecular C—H···O, and intramolecular C—H···O and O—H···N hydrogen bonding interactions help to establish the crystal packing..

Related literature top

For related literature, see: Tai et al. (2005).

Experimental top

1 mmol of Zinc acetate was added to a solution of nisoldehyde-salicyloyl hydrazone (2 mmol) in 10 ml of CH3OH/pyridine (v/v 10:1). The mixture was continuously stirred for 6 h at refluxing temperature, evaporating some solvent, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 58%). Clear blocks of (I) were obtained by evaporation from a methanol solution after two week.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(Cmethyl,Ohydroxy).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The complex molecule in (I), with 50% probabiility ellipsoids.
Bis(4-methoxybenzaldehyde 2-hydroxybenzoylhydrazonato)pyridinezinc(II) pyridine solvate top
Crystal data top
[Zn(C15H13N2O3)2(C5H5N)]·C5H5NF000 = 1584
Mr = 762.14Dx = 1.387 Mg m−3
Orthorhombic, PbcnMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 1992 reflections
a = 15.447 (2) Åθ = 2.4–23.0º
b = 10.0122 (17) ŵ = 0.73 mm−1
c = 23.598 (3) ÅT = 298 K
V = 3649.6 (9) Å3Laminar, colourless
Z = 40.43 × 0.32 × 0.19 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3183 independent reflections
Radiation source: fine-focus sealed tube1794 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.068
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −18→16
Tmin = 0.744, Tmax = 0.874k = −10→11
14274 measured reflectionsl = −27→27
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0568P)2 + 2.7233P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3183 reflectionsΔρmax = 0.30 e Å−3
241 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C15H13N2O3)2(C5H5N)]·C5H5NV = 3649.6 (9) Å3
Mr = 762.14Z = 4
Orthorhombic, PbcnMo Kα
a = 15.447 (2) ŵ = 0.73 mm−1
b = 10.0122 (17) ÅT = 298 K
c = 23.598 (3) Å0.43 × 0.32 × 0.19 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3183 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1794 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.874Rint = 0.068
14274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044241 parameters
wR(F2) = 0.144H-atom parameters constrained
S = 1.06Δρmax = 0.30 e Å−3
3183 reflectionsΔρmin = −0.41 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating –R-factor-obs 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)
Zn10.000000.36156 (7)0.250000.0450 (3)
O10.01587 (16)0.2491 (3)0.18135 (13)0.0527 (10)
O20.26418 (18)0.0842 (3)0.15935 (14)0.0655 (11)
O30.2533 (2)0.7767 (3)0.43932 (15)0.0750 (14)
N10.1609 (2)0.2463 (3)0.20545 (15)0.0461 (13)
N20.14146 (19)0.3425 (3)0.24685 (15)0.0411 (11)
N30.000000.5678 (5)0.250000.0460 (16)
C10.0935 (2)0.2040 (4)0.17617 (18)0.0393 (14)
C20.1130 (2)0.0966 (4)0.13529 (18)0.0403 (14)
C30.1957 (3)0.0397 (4)0.13005 (19)0.0443 (16)
C40.2087 (3)−0.0664 (5)0.0931 (2)0.0567 (17)
C50.1428 (3)−0.1155 (5)0.0603 (2)0.069 (2)
C60.0614 (3)−0.0602 (5)0.0644 (2)0.072 (2)
C70.0471 (3)0.0440 (5)0.1016 (2)0.0597 (18)
C80.2098 (3)0.3930 (4)0.26981 (19)0.0500 (16)
C90.2142 (3)0.4902 (4)0.31474 (19)0.0463 (16)
C100.2943 (3)0.5537 (4)0.3236 (2)0.0540 (17)
C110.3043 (3)0.6484 (5)0.3644 (2)0.0600 (19)
C120.2361 (3)0.6831 (4)0.3983 (2)0.0530 (17)
C130.1564 (3)0.6219 (5)0.3912 (2)0.0570 (17)
C140.1464 (3)0.5250 (5)0.34936 (19)0.0543 (16)
C150.1843 (4)0.8321 (6)0.4695 (3)0.097 (3)
C160.0500 (3)0.6355 (5)0.2142 (2)0.0570 (18)
C170.0512 (3)0.7726 (5)0.2125 (2)0.071 (2)
C180.000000.8425 (7)0.250000.082 (3)
N40.0692 (4)0.5482 (7)0.0272 (3)0.107 (3)0.500
C190.0303 (4)0.4354 (6)0.0459 (3)0.084 (3)
C20−0.0386 (4)0.3879 (6)0.0180 (3)0.089 (3)
C210.0692 (4)0.5482 (7)0.0272 (3)0.107 (3)0.500
H20.249200.146300.179800.0980*
H40.26330−0.104900.090500.0680*
H50.15300−0.185800.035400.0830*
H60.01630−0.092800.042200.0870*
H7−0.008200.080300.104200.0720*
H80.262600.363000.255700.0600*
H100.341400.530400.301200.0650*
H110.357700.689800.369200.0720*
H130.109900.645300.414200.0690*
H140.093000.483300.344800.0650*
H15A0.143400.870100.443500.1460*
H15B0.205600.900600.494400.1460*
H15C0.156500.763800.491500.1460*
H160.085400.588300.189500.0680*
H170.086000.817400.186600.0850*
H180.000000.935300.250000.0980*
H190.051300.391300.077700.1000*
H20−0.065300.309800.030300.1070*
H210.117500.581300.046100.1290*0.500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0366 (4)0.0443 (4)0.0541 (5)0.00000.0067 (4)0.0000
O10.0335 (15)0.0647 (19)0.060 (2)0.0082 (14)−0.0031 (14)−0.0111 (16)
O20.0406 (17)0.074 (2)0.082 (2)0.0109 (15)−0.0115 (16)−0.0238 (19)
O30.068 (2)0.078 (2)0.079 (3)−0.0053 (19)−0.0110 (19)−0.025 (2)
N10.0343 (18)0.048 (2)0.056 (3)0.0005 (16)0.0005 (17)−0.0103 (19)
N20.0333 (17)0.0440 (19)0.046 (2)−0.0009 (14)0.0023 (17)−0.003 (2)
N30.030 (2)0.048 (3)0.060 (3)0.00000.009 (3)0.0000
C10.032 (2)0.044 (2)0.042 (3)0.0010 (18)−0.0018 (19)0.006 (2)
C20.036 (2)0.041 (2)0.044 (3)0.0001 (18)−0.0008 (19)0.000 (2)
C30.040 (2)0.045 (3)0.048 (3)0.0008 (19)−0.001 (2)0.000 (2)
C40.051 (3)0.055 (3)0.064 (3)0.009 (2)0.005 (2)−0.009 (3)
C50.071 (3)0.063 (4)0.073 (4)−0.001 (3)0.006 (3)−0.025 (3)
C60.056 (3)0.077 (4)0.083 (4)−0.005 (3)−0.014 (3)−0.028 (3)
C70.042 (2)0.068 (3)0.069 (4)0.004 (2)−0.005 (2)−0.013 (3)
C80.040 (2)0.052 (3)0.058 (3)0.001 (2)0.002 (2)−0.005 (2)
C90.041 (2)0.049 (3)0.049 (3)−0.002 (2)−0.002 (2)−0.001 (2)
C100.043 (3)0.058 (3)0.061 (3)−0.003 (2)0.005 (2)−0.004 (3)
C110.043 (3)0.064 (3)0.073 (4)−0.011 (2)−0.001 (2)−0.011 (3)
C120.056 (3)0.046 (3)0.057 (3)−0.003 (2)−0.016 (2)−0.004 (2)
C130.048 (3)0.063 (3)0.060 (3)0.002 (2)0.004 (2)−0.006 (3)
C140.042 (2)0.067 (3)0.054 (3)−0.007 (2)−0.001 (2)−0.008 (3)
C150.094 (4)0.105 (5)0.093 (5)0.018 (4)0.000 (4)−0.042 (4)
C160.041 (2)0.057 (3)0.073 (4)−0.001 (2)0.013 (2)0.004 (3)
C170.055 (3)0.064 (4)0.094 (5)−0.013 (3)0.000 (3)0.026 (3)
C180.070 (5)0.042 (4)0.134 (8)0.0000−0.011 (6)0.0000
N40.087 (4)0.104 (5)0.131 (6)−0.011 (4)−0.016 (4)−0.002 (5)
C190.091 (4)0.070 (4)0.090 (5)0.005 (3)0.004 (4)0.014 (4)
C200.084 (4)0.068 (4)0.115 (6)−0.022 (3)0.009 (4)0.016 (4)
C210.087 (4)0.104 (5)0.131 (6)−0.011 (4)−0.016 (4)−0.002 (5)
Geometric parameters (Å, °) top
Zn1—O11.988 (3)C9—C101.407 (6)
Zn1—N22.195 (3)C10—C111.360 (7)
Zn1—N32.065 (5)C11—C121.368 (7)
Zn1—O1i1.988 (3)C12—C131.385 (7)
Zn1—N2i2.195 (3)C13—C141.393 (7)
O1—C11.287 (4)C16—C171.373 (7)
O2—C31.340 (5)C17—C181.378 (6)
O3—C121.373 (5)C4—H40.9300
O3—C151.397 (7)C5—H50.9300
O2—H20.8200C6—H60.9300
N1—C11.319 (5)C7—H70.9300
N1—N21.404 (5)C8—H80.9300
N2—C81.290 (5)C10—H100.9300
N3—C16i1.330 (5)C11—H110.9300
N3—C161.330 (5)C13—H130.9300
N4—C191.353 (9)C14—H140.9300
N4—C20ii1.331 (10)C15—H15B0.9600
N4—H210.9300C15—H15C0.9600
C1—C21.476 (6)C15—H15A0.9600
C2—C31.404 (6)C16—H160.9300
C2—C71.395 (6)C17—H170.9300
C3—C41.389 (6)C18—H180.9300
C4—C51.370 (7)C19—C201.339 (9)
C5—C61.377 (7)C19—C211.353 (9)
C6—C71.381 (7)C19—H190.9300
C8—C91.441 (6)C20—H200.9300
C9—C141.373 (6)C21—H210.9300
Zn1···C143.646 (5)C13···H15C2.7600
Zn1···C14i3.646 (5)C13···H15A2.7800
Zn1···H142.9200C15···H132.5500
Zn1···H14i2.9200C16···H14i3.0200
O1···N12.312 (4)C19···H15Cix3.0700
O1···N22.651 (4)C20···H5x2.9700
O1···N2i3.107 (4)C21···H5xi2.9700
O2···C16iii3.190 (6)H2···N11.8000
O2···N12.522 (4)H2···C12.4700
O2···C8iii3.259 (5)H5···C21viii2.9700
O1···H72.5100H5···H21viii2.4100
O1···H192.8800H5···H20x2.4000
O1···H11iv2.7800H5···C20x2.9700
O2···H16iii2.4300H5···O3xii2.8400
O3···H5v2.8400H6···H15Axiii2.5200
O3···H20vi2.9100H7···C11iv3.0700
N1···O12.312 (4)H7···O12.5100
N1···O22.522 (4)H7···H11iv2.4300
N2···O1i3.107 (4)H8···H102.3300
N2···O12.651 (4)H10···H82.3300
N2···N33.142 (5)H11···O1vi2.7800
N2···C12.292 (5)H11···H7vi2.4300
N2···C163.346 (6)H13···H15A2.4100
N3···C14i3.286 (5)H13···C152.5500
N3···C143.286 (5)H13···H15C2.2900
N3···N23.142 (5)H14···Zn12.9200
N3···N2i3.142 (5)H14···N22.8100
N1···H21.8000H14···C16i3.0200
N2···H162.9400H14···N32.7900
N2···H142.8100H15A···H6xiv2.5200
N3···H142.7900H15A···H132.4100
N3···H14i2.7900H15A···C132.7800
C8···O2vii3.259 (5)H15B···C4xv2.8600
C8···C11iii3.321 (6)H15B···C5xv2.8300
C11···C8vii3.321 (6)H15C···C132.7600
C14···N33.286 (5)H15C···H132.2900
C14···C16i3.561 (7)H15C···C19xv3.0700
C14···Zn13.646 (5)H16···O2vii2.4300
C16···C14i3.561 (7)H16···N22.9400
C16···O2vii3.190 (6)H17···C2xi3.0700
C1···H193.0600H17···C3xi3.1000
C1···H22.4700H17···C7xi3.0900
C2···H17viii3.0700H19···O12.8800
C3···H17viii3.1000H19···C13.0600
C4···H15Bix2.8600H20···H5x2.4000
C5···H21viii3.0800H20···O3iv2.9100
C5···H15Bix2.8300H21···C5xi3.0800
C7···H17viii3.0900H21···H5xi2.4100
C11···H7vi3.0700
O1—Zn1—N278.49 (11)C9—C14—C13120.9 (4)
O1—Zn1—N3124.50 (9)N3—C16—C17122.4 (4)
O1—Zn1—O1i111.01 (13)C16—C17—C18118.8 (5)
O1—Zn1—N2i95.80 (11)C17—C18—C17i119.0 (6)
N2—Zn1—N394.99 (8)C5—C4—H4119.00
O1i—Zn1—N295.80 (11)C3—C4—H4119.00
N2—Zn1—N2i170.02 (12)C6—C5—H5120.00
O1i—Zn1—N3124.50 (9)C4—C5—H5120.00
N2i—Zn1—N394.99 (8)C7—C6—H6120.00
O1i—Zn1—N2i78.49 (11)C5—C6—H6120.00
Zn1—O1—C1113.0 (3)C6—C7—H7119.00
C12—O3—C15118.9 (4)C2—C7—H7119.00
C3—O2—H2109.00C9—C8—H8116.00
N2—N1—C1114.6 (3)N2—C8—H8116.00
Zn1—N2—N1107.2 (2)C9—C10—H10119.00
Zn1—N2—C8140.1 (3)C11—C10—H10119.00
N1—N2—C8112.7 (3)C10—C11—H11120.00
Zn1—N3—C16i120.6 (3)C12—C11—H11120.00
C16—N3—C16i118.7 (5)C14—C13—H13120.00
Zn1—N3—C16120.6 (3)C12—C13—H13120.00
C19—N4—C20ii120.3 (6)C13—C14—H14120.00
C20ii—N4—H21120.00C9—C14—H14120.00
C19—N4—H21120.00O3—C15—H15B110.00
O1—C1—N1125.0 (4)O3—C15—H15A110.00
N1—C1—C2114.5 (3)H15A—C15—H15C109.00
O1—C1—C2120.5 (3)H15B—C15—H15C109.00
C1—C2—C7119.9 (3)O3—C15—H15C110.00
C1—C2—C3122.6 (3)H15A—C15—H15B109.00
C3—C2—C7117.4 (4)N3—C16—H16119.00
O2—C3—C4117.7 (4)C17—C16—H16119.00
C2—C3—C4119.8 (4)C16—C17—H17121.00
O2—C3—C2122.5 (4)C18—C17—H17121.00
C3—C4—C5121.5 (4)C17—C18—H18121.00
C4—C5—C6119.6 (5)C17i—C18—H18121.00
C5—C6—C7119.6 (4)N4—C19—C20119.3 (6)
C2—C7—C6122.1 (4)C20—C19—C21119.3 (6)
N2—C8—C9127.8 (4)N4ii—C20—C19120.4 (6)
C10—C9—C14117.9 (4)C19—C21—C20ii120.3 (6)
C8—C9—C14125.0 (4)N4—C19—H19120.00
C8—C9—C10117.1 (4)C20—C19—H19120.00
C9—C10—C11121.3 (4)C21—C19—H19120.00
C10—C11—C12120.2 (4)C19—C20—H20120.00
O3—C12—C11115.9 (4)N4ii—C20—H20120.00
O3—C12—C13124.0 (4)C19—C21—H21120.00
C11—C12—C13120.1 (4)C20ii—C21—H21120.00
C12—C13—C14119.5 (4)
N2—Zn1—O1—C111.7 (3)O1—C1—C2—C70.5 (6)
N3—Zn1—O1—C199.8 (3)N1—C1—C2—C33.0 (6)
O1i—Zn1—O1—C1−80.2 (3)O1—C1—C2—C3−176.8 (4)
N2i—Zn1—O1—C1−160.1 (3)C1—C2—C3—C4176.3 (4)
O1—Zn1—N2—N1−9.7 (2)C7—C2—C3—O2178.5 (4)
O1—Zn1—N2—C8168.4 (5)C1—C2—C3—O2−4.1 (6)
N3—Zn1—N2—N1−133.9 (2)C1—C2—C7—C6−177.3 (4)
N3—Zn1—N2—C844.2 (4)C3—C2—C7—C60.2 (7)
O1i—Zn1—N2—N1100.6 (2)C7—C2—C3—C4−1.2 (6)
O1i—Zn1—N2—C8−81.3 (5)C2—C3—C4—C51.6 (7)
O1—Zn1—N3—C16−33.8 (2)O2—C3—C4—C5−178.1 (4)
O1—Zn1—N3—C16i146.2 (2)C3—C4—C5—C6−0.9 (7)
N2—Zn1—N3—C1645.6 (3)C4—C5—C6—C7−0.1 (7)
N2—Zn1—N3—C16i−134.4 (3)C5—C6—C7—C20.5 (7)
O1i—Zn1—N3—C16146.2 (2)N2—C8—C9—C1414.9 (7)
N2i—Zn1—N3—C16−134.4 (3)N2—C8—C9—C10−165.2 (4)
Zn1—O1—C1—N1−13.0 (5)C10—C9—C14—C131.2 (7)
Zn1—O1—C1—C2166.8 (3)C8—C9—C14—C13−178.9 (4)
C15—O3—C12—C11170.1 (5)C8—C9—C10—C11178.9 (4)
C15—O3—C12—C13−11.8 (7)C14—C9—C10—C11−1.2 (7)
C1—N1—N2—Zn16.5 (4)C9—C10—C11—C120.6 (7)
N2—N1—C1—C2−176.2 (3)C10—C11—C12—C130.0 (7)
N2—N1—C1—O13.6 (6)C10—C11—C12—O3178.1 (4)
C1—N1—N2—C8−172.2 (4)C11—C12—C13—C140.0 (7)
Zn1—N2—C8—C94.2 (8)O3—C12—C13—C14−178.0 (4)
N1—N2—C8—C9−177.7 (4)C12—C13—C14—C9−0.6 (7)
C16i—N3—C16—C17−0.7 (6)N3—C16—C17—C181.3 (7)
Zn1—N3—C16—C17179.3 (3)C16—C17—C18—C17i−0.6 (5)
C19—N4—C20ii—C19ii−0.9 (10)N4—C19—C20—N4ii−0.9 (10)
C20ii—N4—C19—C200.9 (10)C21—C19—C20—N4ii−0.9 (10)
N1—C1—C2—C7−179.7 (4)C20—C19—C21—C20ii0.9 (10)
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+1, −z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, y−1/2, −z+1/2; (v) −x+1/2, −y+1/2, z+1/2; (vi) x+1/2, y+1/2, −z+1/2; (vii) −x+1/2, y+1/2, z; (viii) x, y−1, z; (ix) x, −y+1, z−1/2; (x) −x, −y, −z; (xi) x, y+1, z; (xii) −x+1/2, −y+1/2, z−1/2; (xiii) −x, y−1, −z+1/2; (xiv) −x, y+1, −z+1/2; (xv) x, −y+1, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.802.522 (4)147
C7—H7···O10.932.512.827 (6)100
C16—H16···O2vii0.932.433.190 (6)139
Symmetry codes: (vii) −x+1/2, y+1/2, z.
Selected geometric parameters (Å, °) top
Zn1—O11.988 (3)O3—C151.397 (7)
Zn1—N22.195 (3)N1—C11.319 (5)
Zn1—N32.065 (5)N1—N21.404 (5)
Zn1—O1i1.988 (3)N2—C81.290 (5)
Zn1—N2i2.195 (3)N3—C16i1.330 (5)
O1—C11.287 (4)N3—C161.330 (5)
O2—C31.340 (5)N4—C191.353 (9)
O3—C121.373 (5)N4—C20ii1.331 (10)
O1—Zn1—N278.49 (11)Zn1—N3—C16i120.6 (3)
O1—Zn1—N3124.50 (9)C16—N3—C16i118.7 (5)
O1—Zn1—O1i111.01 (13)Zn1—N3—C16120.6 (3)
O1—Zn1—N2i95.80 (11)C19—N4—C20ii120.3 (6)
N2—Zn1—N394.99 (8)O1—C1—N1125.0 (4)
O1i—Zn1—N295.80 (11)N1—C1—C2114.5 (3)
N2—Zn1—N2i170.02 (12)O1—C1—C2120.5 (3)
O1i—Zn1—N3124.50 (9)O2—C3—C4117.7 (4)
N2i—Zn1—N394.99 (8)O2—C3—C2122.5 (4)
O1i—Zn1—N2i78.49 (11)N2—C8—C9127.8 (4)
Zn1—O1—C1113.0 (3)O3—C12—C11115.9 (4)
C12—O3—C15118.9 (4)O3—C12—C13124.0 (4)
N2—N1—C1114.6 (3)N3—C16—C17122.4 (4)
Zn1—N2—N1107.2 (2)N4—C19—C20119.3 (6)
Zn1—N2—C8140.1 (3)N4ii—C20—C19120.4 (6)
N1—N2—C8112.7 (3)
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.802.522 (4)147
C7—H7···O10.932.512.827 (6)100
C16—H16···O2iii0.932.433.190 (6)139
Symmetry codes: (iii) −x+1/2, y+1/2, z.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20671073), NingXia Natural Gas Transfering Key Laboratory (grant No. 2004007), the Science and Technology Foundation of Weifang and Weifang University for research grants.

references
References top

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

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Tai, X.-S., Liu, W.-Y., Liu, Y.-Z. & Li, Y.-Z. (2005). Acta Cryst. E61, o389–o390.