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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): m502.
Published online 2008 February 29. doi:  10.1107/S1600536808005060
PMCID: PMC2960793

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

Abstract

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.

Related literature

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

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Object name is e-64-0m502-scheme1.jpg

Experimental

Crystal data

  • [Zn(C21H25N3O2)]
  • M r = 416.81
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m502-efi1.jpg
  • a = 6.7813 (6) Å
  • b = 13.9833 (12) Å
  • c = 20.766 (2) Å
  • β = 92.146 (1)°
  • V = 1967.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.27 mm−1
  • T = 298 (2) K
  • 0.42 × 0.30 × 0.16 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.618, T max = 0.823
  • 9657 measured reflections
  • 3465 independent reflections
  • 2434 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.094
  • S = 1.04
  • 3465 reflections
  • 274 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005060/hb2702sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005060/hb2702Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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)°.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) with 30% probabiility ellipsoids (H atoms and the minor disorder component omitted for clarity).

Crystal data

[Zn(C21H25N3O2)]F000 = 872
Mr = 416.81Dx = 1.407 Mg m3
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 mm1
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

Bruker SMART CCD diffractometer3465 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

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 Å3
274 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2702).

References

  • 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. [PubMed]

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