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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1134.
Published online 2009 August 26. doi:  10.1107/S1600536809033170
PMCID: PMC2969951

[N′-(3-Meth­oxy-2-oxidobenzyl­idene)nicotinohydrazidato]diphenyl­tin(IV)

Abstract

The asymmetric unit of the title compound, [Sn(C6H5)2(C14H11N3O3)], contains two crystallographically independent mol­ecules that differ predominantly in the torsion of the phenyl rings. In both mol­ecules, the SnIV ion is in a distored trigonal-bipyramidal geometry. The Sn—O distances are in the range 2.055 (2)–2.143 (2) Å.

Related literature

For covalent radii see: Sanderson (1967 [triangle]). For a related structure see: Yearwood et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1134-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H5)2(C14H11N3O3)]
  • M r = 542.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1134-efi1.jpg
  • a = 8.9653 (14) Å
  • b = 20.771 (3) Å
  • c = 12.903 (2) Å
  • β = 106.015 (2)°
  • V = 2309.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.14 mm−1
  • T = 298 K
  • 0.49 × 0.45 × 0.34 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.605, T max = 0.698
  • 9743 measured reflections
  • 7970 independent reflections
  • 7720 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.057
  • S = 1.02
  • 7970 reflections
  • 597 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.49 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3753 Friedel pairs
  • Flack parameter: 0.0342

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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 I, global. DOI: 10.1107/S1600536809033170/nc2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033170/nc2154Isup2.hkl

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

Acknowledgments

We acknowledge financial support by the Jining University Science Foundation and the State Key Laboratory of Crystal Materials, Shandong University.

supplementary crystallographic information

Comment

The structure determination was undertaken as a part of a project on the synthesis and structural characterization of Schiff base complexes. In the crystal structure of the title compound two crystallographically independent molecules are found. Differences are found predominantly in the torsion of the phenyl rings. The Sn1 atoms are five-coordinated by two O atoms, two C atoms and one N atom in a disorted trigonal-bipyramidal coodination (Table 1). The Schiff base is coordinated to the Sn1 atom as a tridentate ligand via the azomethine N atom, the hydroxyl O atom and the carbonyl O atom. The Sn1—N1 distances are close to the sum of the covalent radii of 2.15 Å (Sanderson, 1967), indicating a strong Sn—N interaction. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002).

Experimental

A mixture of diphenyltin oxide (0.5778 g, 2.0 mmol) and 3-Methoxy-2-oxideobenzaldehyde(3-pyridyl)methyl-hydrazone (0.5420 g, 2.0 mmol) in methanol (60 ml) was heated under reflux for 6 h. The obtained clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol (1:1) to yield blocks of (I). Yield 0.8347 g, 77%, m.p. 476 K, analysis, calculated for C26H21N3O3Sn: C 57.60, H, 3.90; N 7.75%; found: C 57.66, H 3.93, N, 7.71%.

Refinement

H atoms were positioned with idelaized geometry with C-H = 0.93 Å for aromatic H atoms and 0.96 Å for methyl H atoms and were constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(for methyl groups). The absolute structure was determined on the basis of 3753 Friedel pairs.

Figures

Fig. 1.
The molecular structure of the title complex with labeling and 30% displacement ellipsoids (H atoms omitted for clarity).

Crystal data

[Sn(C6H5)2(C14H11N3O3)]F(000) = 1088
Mr = 542.15Dx = 1.559 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9021 reflections
a = 8.9653 (14) Åθ = 2.4–28.1°
b = 20.771 (3) ŵ = 1.14 mm1
c = 12.903 (2) ÅT = 298 K
β = 106.015 (2)°Block, yellow
V = 2309.5 (6) Å30.49 × 0.45 × 0.34 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer7970 independent reflections
Radiation source: fine-focus sealed tube7720 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.605, Tmax = 0.698k = −24→23
9743 measured reflectionsl = −15→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.057w = 1/[σ2(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7970 reflectionsΔρmax = 0.26 e Å3
597 parametersΔρmin = −0.49 e Å3
1 restraintAbsolute structure: Flack (1983), 3753 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.0342

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*/Ueq
C10.8744 (5)0.6897 (3)−0.3633 (3)0.0776 (13)
H10.91240.6724−0.41740.093*
C20.8341 (5)0.6481 (2)−0.2940 (3)0.0701 (11)
H20.84510.6038−0.30000.084*
C30.7773 (5)0.67369 (19)−0.2162 (3)0.0616 (10)
H30.74830.6464−0.16800.074*
C40.7615 (4)0.73871 (18)−0.2066 (3)0.0464 (8)
C50.8047 (5)0.7776 (2)−0.2807 (3)0.0636 (9)
H50.79280.8219−0.27650.076*
C60.7003 (3)0.76720 (19)−0.1211 (2)0.0439 (7)
C70.6190 (4)0.9109 (2)−0.0230 (3)0.0493 (8)
H70.64550.9369−0.07390.059*
C80.5591 (4)0.94252 (17)0.0557 (3)0.0450 (7)
C90.5271 (5)1.00873 (19)0.0427 (3)0.0617 (10)
H90.55051.0306−0.01370.074*
C100.4628 (5)1.04139 (19)0.1105 (3)0.0663 (11)
H100.44331.08530.10080.080*
C110.4258 (4)1.00908 (19)0.1950 (3)0.0562 (9)
H110.37981.03150.24050.067*
C120.4566 (4)0.94435 (17)0.2120 (3)0.0451 (8)
C130.5281 (3)0.9105 (2)0.1433 (2)0.0423 (7)
C140.3611 (6)0.9384 (2)0.3658 (3)0.0778 (14)
H14A0.42950.97130.40400.117*
H14B0.34450.90700.41610.117*
H14C0.26360.95720.32780.117*
C150.7839 (4)0.73385 (18)0.1970 (3)0.0467 (8)
C160.8784 (4)0.7704 (3)0.2785 (3)0.0642 (10)
H160.86720.81500.27830.077*
C170.9909 (5)0.7405 (3)0.3613 (3)0.0903 (17)
H171.05560.76500.41580.108*
C181.0053 (6)0.6746 (4)0.3617 (4)0.0964 (19)
H181.07990.65470.41700.116*
C190.9121 (5)0.6382 (3)0.2823 (4)0.0799 (13)
H190.92180.59360.28380.096*
C200.8033 (4)0.6679 (2)0.1997 (3)0.0619 (10)
H200.74150.64290.14460.074*
C210.3786 (4)0.73152 (16)0.0491 (2)0.0431 (7)
C220.2814 (4)0.75321 (18)0.1083 (3)0.0557 (9)
H220.31080.78790.15500.067*
C230.1402 (5)0.7230 (2)0.0975 (4)0.0725 (12)
H230.07530.73720.13800.087*
C240.0961 (5)0.6727 (2)0.0281 (4)0.0723 (12)
H240.00050.65300.02050.087*
C250.1911 (5)0.6512 (2)−0.0301 (3)0.0703 (11)
H250.16050.6169−0.07750.084*
C260.3332 (4)0.68023 (18)−0.0189 (3)0.0525 (8)
H260.39880.6648−0.05790.063*
C270.0013 (5)0.9828 (3)1.1151 (4)0.0785 (14)
H27−0.03410.99801.17190.094*
C280.0037 (5)0.9185 (3)1.1010 (3)0.0764 (11)
H28−0.02800.89071.14740.092*
C290.0535 (5)0.8947 (2)1.0178 (3)0.0643 (11)
H290.05530.85061.00610.077*
C300.1012 (4)0.93724 (18)0.9516 (3)0.0499 (8)
C310.0949 (5)1.0015 (2)0.9724 (3)0.0693 (11)
H310.12681.03020.92740.083*
C320.1608 (4)0.9145 (2)0.8613 (2)0.0474 (7)
C330.2466 (4)0.7762 (2)0.7514 (2)0.0496 (8)
H330.21180.74880.79680.060*
C340.3089 (4)0.74560 (17)0.6728 (3)0.0457 (8)
C350.3156 (5)0.67813 (19)0.6717 (3)0.0589 (9)
H350.27720.65470.72020.071*
C360.3774 (5)0.64637 (19)0.6007 (3)0.0630 (10)
H360.38090.60160.60080.076*
C370.4350 (5)0.68106 (19)0.5283 (3)0.0565 (9)
H370.47770.65940.48020.068*
C380.4295 (4)0.74709 (17)0.5272 (3)0.0478 (8)
C390.3666 (4)0.78110 (17)0.6002 (2)0.0443 (7)
C400.5481 (6)0.7553 (2)0.3835 (3)0.0762 (13)
H40A0.63480.72930.42070.114*
H40B0.58230.78750.34180.114*
H40C0.47110.72860.33640.114*
C410.4735 (4)0.97590 (17)0.6996 (3)0.0476 (8)
C420.4710 (5)1.03547 (19)0.7470 (3)0.0603 (10)
H420.38371.04770.76780.072*
C430.5954 (6)1.0772 (2)0.7640 (4)0.0797 (13)
H430.59161.11720.79550.096*
C440.7229 (6)1.0592 (3)0.7345 (5)0.0973 (17)
H440.80711.08700.74620.117*
C450.7294 (6)1.0005 (3)0.6876 (5)0.0980 (17)
H450.81820.98860.66840.118*
C460.6038 (5)0.9588 (2)0.6685 (3)0.0699 (11)
H460.60730.91940.63500.084*
C470.0803 (4)0.94225 (17)0.5471 (3)0.0460 (7)
C480.0773 (5)1.0006 (2)0.4981 (3)0.0672 (11)
H480.16311.02760.51970.081*
C49−0.0503 (6)1.0207 (3)0.4169 (4)0.0865 (15)
H49−0.05151.06120.38590.104*
C50−0.1721 (5)0.9809 (3)0.3834 (4)0.0833 (14)
H50−0.25680.99370.32750.100*
C51−0.1740 (5)0.9226 (3)0.4294 (4)0.0919 (15)
H51−0.25970.89580.40580.110*
C52−0.0482 (5)0.9032 (2)0.5116 (4)0.0753 (13)
H52−0.04990.86320.54360.090*
N10.6398 (3)0.84948 (14)−0.0300 (2)0.0438 (6)
N20.6926 (4)0.82985 (15)−0.1167 (2)0.0502 (7)
N30.1728 (4)0.85239 (16)0.8523 (2)0.0571 (8)
N40.2328 (3)0.83689 (15)0.7669 (2)0.0473 (7)
N50.8630 (5)0.7541 (2)−0.3585 (3)0.0853 (13)
N60.0461 (5)1.0262 (2)1.0533 (3)0.0824 (11)
O10.5663 (3)0.84980 (12)0.16702 (17)0.0551 (6)
O20.4289 (3)0.90798 (15)0.29086 (18)0.0591 (7)
O30.6595 (3)0.72733 (11)−0.05616 (18)0.0519 (6)
O40.1992 (3)0.95651 (12)0.8002 (2)0.0596 (7)
O50.3664 (3)0.84455 (12)0.5949 (2)0.0608 (7)
O60.4834 (3)0.78554 (13)0.4596 (2)0.0646 (7)
Sn10.60021 (2)0.773826 (10)0.074059 (15)0.03996 (6)
Sn20.27721 (3)0.915473 (10)0.672005 (17)0.04469 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.085 (3)0.100 (4)0.061 (2)0.023 (3)0.042 (2)−0.005 (2)
C20.094 (3)0.064 (3)0.064 (2)0.010 (2)0.043 (2)−0.008 (2)
C30.082 (3)0.056 (2)0.057 (2)−0.008 (2)0.039 (2)−0.0040 (17)
C40.0432 (17)0.060 (2)0.0395 (17)−0.0020 (16)0.0167 (14)−0.0014 (15)
C50.082 (2)0.061 (2)0.059 (2)0.009 (2)0.0384 (18)0.009 (2)
C60.0449 (16)0.055 (2)0.0354 (15)−0.0008 (17)0.0168 (12)−0.0034 (16)
C70.061 (2)0.047 (2)0.0442 (17)−0.0035 (19)0.0220 (14)0.0087 (17)
C80.0499 (18)0.0440 (19)0.0437 (17)0.0006 (15)0.0172 (14)0.0031 (14)
C90.079 (3)0.051 (2)0.066 (2)0.008 (2)0.038 (2)0.0156 (17)
C100.088 (3)0.042 (2)0.080 (3)0.010 (2)0.041 (2)0.0101 (18)
C110.062 (2)0.053 (2)0.059 (2)0.0109 (18)0.0256 (18)−0.0009 (17)
C120.0495 (19)0.0454 (19)0.0402 (17)−0.0005 (15)0.0120 (14)−0.0025 (14)
C130.0419 (16)0.0421 (19)0.0403 (16)0.0008 (16)0.0071 (12)0.0020 (17)
C140.115 (4)0.075 (3)0.059 (2)0.025 (3)0.050 (2)0.006 (2)
C150.0395 (17)0.062 (2)0.0421 (17)0.0066 (15)0.0179 (13)0.0091 (16)
C160.056 (2)0.084 (3)0.053 (2)0.003 (2)0.0153 (16)−0.009 (2)
C170.058 (3)0.159 (6)0.049 (2)0.005 (3)0.007 (2)−0.018 (3)
C180.068 (3)0.152 (6)0.072 (3)0.044 (4)0.022 (3)0.035 (4)
C190.067 (3)0.091 (3)0.086 (3)0.027 (3)0.027 (2)0.032 (3)
C200.050 (2)0.069 (3)0.072 (2)0.0092 (18)0.0244 (18)0.019 (2)
C210.0407 (16)0.0498 (19)0.0387 (16)0.0030 (14)0.0107 (13)0.0099 (14)
C220.0511 (19)0.060 (2)0.062 (2)0.0048 (16)0.0253 (17)−0.0002 (16)
C230.056 (2)0.084 (3)0.087 (3)0.008 (2)0.036 (2)0.008 (3)
C240.050 (2)0.087 (3)0.082 (3)−0.013 (2)0.022 (2)0.012 (3)
C250.073 (3)0.074 (3)0.062 (2)−0.025 (2)0.015 (2)−0.004 (2)
C260.060 (2)0.057 (2)0.0459 (18)−0.0020 (17)0.0219 (16)−0.0008 (16)
C270.070 (3)0.110 (4)0.062 (3)0.025 (3)0.030 (2)−0.009 (3)
C280.079 (3)0.099 (4)0.062 (2)0.003 (3)0.037 (2)0.003 (3)
C290.073 (3)0.067 (3)0.062 (2)0.004 (2)0.034 (2)0.0059 (19)
C300.0490 (19)0.060 (2)0.0419 (18)0.0080 (16)0.0142 (15)0.0009 (15)
C310.085 (3)0.065 (3)0.067 (3)0.012 (2)0.038 (2)0.005 (2)
C320.0539 (18)0.0483 (19)0.0430 (16)0.0005 (19)0.0186 (14)0.0032 (18)
C330.064 (2)0.0441 (19)0.0452 (17)−0.005 (2)0.0219 (14)0.0073 (18)
C340.0499 (18)0.0388 (18)0.0484 (19)0.0013 (15)0.0135 (15)0.0012 (13)
C350.076 (3)0.047 (2)0.060 (2)−0.0009 (18)0.0286 (19)0.0061 (17)
C360.080 (3)0.039 (2)0.075 (3)0.0052 (19)0.029 (2)0.0006 (18)
C370.067 (2)0.050 (2)0.054 (2)0.0110 (18)0.0191 (18)−0.0052 (17)
C380.051 (2)0.0458 (19)0.0454 (19)0.0032 (15)0.0121 (15)0.0017 (14)
C390.0524 (18)0.0377 (18)0.0407 (16)0.0022 (16)0.0093 (13)0.0019 (15)
C400.108 (4)0.076 (3)0.057 (2)0.017 (3)0.043 (2)0.001 (2)
C410.055 (2)0.0483 (19)0.0407 (17)−0.0021 (15)0.0143 (14)0.0044 (14)
C420.067 (2)0.053 (2)0.068 (2)−0.0056 (19)0.030 (2)−0.0070 (18)
C430.097 (3)0.071 (3)0.075 (3)−0.028 (3)0.031 (3)−0.013 (2)
C440.088 (4)0.104 (4)0.110 (4)−0.045 (3)0.045 (3)−0.031 (3)
C450.068 (3)0.121 (5)0.119 (4)−0.021 (3)0.049 (3)−0.032 (4)
C460.067 (3)0.072 (3)0.076 (3)−0.001 (2)0.029 (2)−0.012 (2)
C470.0522 (19)0.0438 (18)0.0445 (17)0.0013 (15)0.0177 (14)−0.0047 (14)
C480.062 (2)0.061 (2)0.070 (3)−0.007 (2)0.0053 (19)0.017 (2)
C490.079 (3)0.078 (3)0.088 (3)0.004 (3)−0.002 (3)0.027 (3)
C500.067 (3)0.083 (4)0.085 (3)0.012 (3)−0.005 (2)−0.018 (3)
C510.068 (3)0.077 (3)0.115 (4)−0.017 (3)−0.001 (3)−0.039 (3)
C520.066 (3)0.055 (3)0.100 (3)−0.014 (2)0.016 (2)−0.014 (2)
N10.0552 (17)0.0433 (17)0.0377 (14)−0.0021 (13)0.0209 (12)0.0029 (12)
N20.0674 (19)0.0473 (19)0.0445 (16)0.0007 (15)0.0301 (14)0.0017 (13)
N30.074 (2)0.054 (2)0.0528 (18)0.0053 (16)0.0345 (16)0.0043 (15)
N40.0607 (18)0.0429 (18)0.0456 (17)0.0028 (14)0.0268 (13)0.0037 (13)
N50.104 (3)0.100 (3)0.075 (2)0.021 (2)0.063 (2)0.013 (2)
N60.104 (3)0.077 (3)0.078 (2)0.022 (2)0.045 (2)−0.008 (2)
O10.0940 (19)0.0379 (13)0.0410 (12)0.0060 (13)0.0315 (12)−0.0007 (11)
O20.0863 (17)0.0531 (16)0.0475 (12)0.0106 (15)0.0347 (12)0.0042 (12)
O30.0746 (16)0.0436 (13)0.0481 (14)−0.0028 (12)0.0350 (12)−0.0007 (11)
O40.0888 (19)0.0440 (14)0.0577 (15)0.0000 (13)0.0397 (14)0.0001 (12)
O50.099 (2)0.0379 (14)0.0622 (16)0.0050 (13)0.0495 (14)0.0031 (12)
O60.0962 (19)0.0523 (17)0.0597 (15)0.0075 (14)0.0455 (14)0.0014 (12)
Sn10.04690 (12)0.04038 (12)0.03702 (11)0.00066 (11)0.01897 (8)0.00278 (10)
Sn20.05794 (14)0.03805 (12)0.04156 (12)0.00031 (11)0.01956 (10)0.00249 (10)

Geometric parameters (Å, °)

C1—N51.345 (6)C28—H280.9300
C1—C21.361 (6)C29—C301.377 (5)
C1—H10.9300C29—H290.9300
C2—C31.354 (5)C30—C311.367 (5)
C2—H20.9300C30—C321.487 (5)
C3—C41.367 (5)C31—N61.340 (5)
C3—H30.9300C31—H310.9300
C4—C51.386 (5)C32—O41.285 (4)
C4—C61.485 (4)C32—N31.302 (5)
C5—N51.345 (5)C33—N41.288 (6)
C5—H50.9300C33—C341.434 (5)
C6—O31.300 (4)C33—H330.9300
C6—N21.305 (5)C34—C391.399 (5)
C7—N11.296 (5)C34—C351.403 (5)
C7—C81.432 (5)C35—C361.365 (5)
C7—H70.9300C35—H350.9300
C8—C131.404 (5)C36—C371.387 (5)
C8—C91.405 (5)C36—H360.9300
C9—C101.355 (5)C37—C381.372 (5)
C9—H90.9300C37—H370.9300
C10—C111.396 (5)C38—O61.366 (4)
C10—H100.9300C38—C391.413 (5)
C11—C121.378 (5)C39—O51.320 (4)
C11—H110.9300C40—O61.417 (4)
C12—O21.344 (4)C40—H40A0.9600
C12—C131.416 (5)C40—H40B0.9600
C13—O11.321 (5)C40—H40C0.9600
C14—O21.424 (4)C41—C461.382 (5)
C14—H14A0.9600C41—C421.383 (5)
C14—H14B0.9600C41—Sn22.111 (3)
C14—H14C0.9600C42—C431.381 (6)
C15—C201.381 (6)C42—H420.9300
C15—C161.383 (5)C43—C441.354 (7)
C15—Sn12.115 (3)C43—H430.9300
C16—C171.396 (7)C44—C451.370 (8)
C16—H160.9300C44—H440.9300
C17—C181.374 (8)C45—C461.388 (7)
C17—H170.9300C45—H450.9300
C18—C191.359 (8)C46—H460.9300
C18—H180.9300C47—C481.364 (5)
C19—C201.375 (6)C47—C521.380 (5)
C19—H190.9300C47—Sn22.110 (3)
C20—H200.9300C48—C491.386 (6)
C21—C261.369 (5)C48—H480.9300
C21—C221.382 (5)C49—C501.342 (7)
C21—Sn12.115 (3)C49—H490.9300
C22—C231.385 (6)C50—C511.351 (8)
C22—H220.9300C50—H500.9300
C23—C241.363 (7)C51—C521.379 (7)
C23—H230.9300C51—H510.9300
C24—C251.357 (6)C52—H520.9300
C24—H240.9300N1—N21.390 (4)
C25—C261.381 (5)N1—Sn12.159 (3)
C25—H250.9300N3—N41.390 (4)
C26—H260.9300N4—Sn22.143 (3)
C27—N61.337 (6)O1—Sn12.055 (2)
C27—C281.350 (8)O3—Sn12.129 (2)
C27—H270.9300O4—Sn22.143 (2)
C28—C291.364 (6)O5—Sn22.059 (2)
N5—C1—C2124.3 (4)N4—C33—C34128.1 (3)
N5—C1—H1117.8N4—C33—H33116.0
C2—C1—H1117.8C34—C33—H33116.0
C3—C2—C1117.4 (4)C39—C34—C35119.7 (3)
C3—C2—H2121.3C39—C34—C33121.9 (3)
C1—C2—H2121.3C35—C34—C33118.4 (3)
C2—C3—C4121.6 (4)C36—C35—C34121.0 (4)
C2—C3—H3119.2C36—C35—H35119.5
C4—C3—H3119.2C34—C35—H35119.5
C3—C4—C5117.3 (3)C35—C36—C37119.8 (4)
C3—C4—C6122.0 (3)C35—C36—H36120.1
C5—C4—C6120.7 (4)C37—C36—H36120.1
N5—C5—C4122.9 (5)C38—C37—C36120.5 (4)
N5—C5—H5118.6C38—C37—H37119.8
C4—C5—H5118.6C36—C37—H37119.8
O3—C6—N2125.4 (3)O6—C38—C37125.0 (3)
O3—C6—C4116.9 (3)O6—C38—C39114.2 (3)
N2—C6—C4117.7 (3)C37—C38—C39120.8 (3)
N1—C7—C8126.1 (3)O5—C39—C34124.4 (3)
N1—C7—H7116.9O5—C39—C38117.4 (3)
C8—C7—H7116.9C34—C39—C38118.2 (3)
C13—C8—C9118.7 (3)O6—C40—H40A109.5
C13—C8—C7123.4 (4)O6—C40—H40B109.5
C9—C8—C7117.9 (3)H40A—C40—H40B109.5
C10—C9—C8121.5 (3)O6—C40—H40C109.5
C10—C9—H9119.3H40A—C40—H40C109.5
C8—C9—H9119.3H40B—C40—H40C109.5
C9—C10—C11119.9 (4)C46—C41—C42118.5 (4)
C9—C10—H10120.0C46—C41—Sn2122.0 (3)
C11—C10—H10120.0C42—C41—Sn2119.5 (3)
C12—C11—C10120.9 (3)C43—C42—C41121.4 (4)
C12—C11—H11119.6C43—C42—H42119.3
C10—C11—H11119.6C41—C42—H42119.3
O2—C12—C11126.7 (3)C44—C43—C42119.3 (5)
O2—C12—C13113.9 (3)C44—C43—H43120.3
C11—C12—C13119.3 (3)C42—C43—H43120.3
O1—C13—C8122.8 (3)C43—C44—C45120.8 (5)
O1—C13—C12117.5 (3)C43—C44—H44119.6
C8—C13—C12119.6 (4)C45—C44—H44119.6
O2—C14—H14A109.5C44—C45—C46120.2 (5)
O2—C14—H14B109.5C44—C45—H45119.9
H14A—C14—H14B109.5C46—C45—H45119.9
O2—C14—H14C109.5C41—C46—C45119.8 (4)
H14A—C14—H14C109.5C41—C46—H46120.1
H14B—C14—H14C109.5C45—C46—H46120.1
C20—C15—C16118.7 (4)C48—C47—C52117.5 (4)
C20—C15—Sn1118.4 (3)C48—C47—Sn2119.6 (3)
C16—C15—Sn1122.8 (3)C52—C47—Sn2123.0 (3)
C15—C16—C17119.9 (5)C47—C48—C49121.7 (4)
C15—C16—H16120.0C47—C48—H48119.2
C17—C16—H16120.0C49—C48—H48119.2
C18—C17—C16119.6 (5)C50—C49—C48119.1 (5)
C18—C17—H17120.2C50—C49—H49120.4
C16—C17—H17120.2C48—C49—H49120.4
C19—C18—C17120.9 (5)C49—C50—C51121.2 (4)
C19—C18—H18119.6C49—C50—H50119.4
C17—C18—H18119.6C51—C50—H50119.4
C18—C19—C20119.5 (5)C50—C51—C52119.6 (4)
C18—C19—H19120.3C50—C51—H51120.2
C20—C19—H19120.3C52—C51—H51120.2
C19—C20—C15121.5 (5)C51—C52—C47120.9 (5)
C19—C20—H20119.3C51—C52—H52119.5
C15—C20—H20119.3C47—C52—H52119.5
C26—C21—C22119.1 (3)C7—N1—N2115.6 (3)
C26—C21—Sn1121.4 (2)C7—N1—Sn1128.4 (2)
C22—C21—Sn1119.3 (3)N2—N1—Sn1115.9 (2)
C21—C22—C23119.7 (4)C6—N2—N1111.2 (3)
C21—C22—H22120.2C32—N3—N4111.1 (3)
C23—C22—H22120.2C33—N4—N3115.1 (3)
C24—C23—C22120.3 (4)C33—N4—Sn2128.0 (2)
C24—C23—H23119.8N3—N4—Sn2116.7 (2)
C22—C23—H23119.8C1—N5—C5116.5 (4)
C25—C24—C23120.2 (4)C27—N6—C31115.0 (4)
C25—C24—H24119.9C13—O1—Sn1131.97 (19)
C23—C24—H24119.9C12—O2—C14117.9 (3)
C24—C25—C26120.0 (4)C6—O3—Sn1113.3 (2)
C24—C25—H25120.0C32—O4—Sn2113.7 (2)
C26—C25—H25120.0C39—O5—Sn2133.2 (2)
C21—C26—C25120.6 (4)C38—O6—C40117.9 (3)
C21—C26—H26119.7O1—Sn1—C2197.12 (12)
C25—C26—H26119.7O1—Sn1—C1594.22 (12)
N6—C27—C28124.7 (4)C21—Sn1—C15117.09 (12)
N6—C27—H27117.7O1—Sn1—O3156.71 (9)
C28—C27—H27117.7C21—Sn1—O396.90 (11)
C27—C28—C29119.0 (5)C15—Sn1—O395.83 (12)
C27—C28—H28120.5O1—Sn1—N183.12 (11)
C29—C28—H28120.5C21—Sn1—N1121.10 (11)
C28—C29—C30118.8 (4)C15—Sn1—N1121.65 (12)
C28—C29—H29120.6O3—Sn1—N173.72 (11)
C30—C29—H29120.6O5—Sn2—C47100.04 (12)
C31—C30—C29117.9 (4)O5—Sn2—C4195.16 (12)
C31—C30—C32120.6 (4)C47—Sn2—C41117.07 (13)
C29—C30—C32121.5 (4)O5—Sn2—O4155.61 (9)
N6—C31—C30124.5 (4)C47—Sn2—O495.87 (11)
N6—C31—H31117.7C41—Sn2—O493.89 (12)
C30—C31—H31117.7O5—Sn2—N483.65 (11)
O4—C32—N3125.2 (3)C47—Sn2—N4112.89 (12)
O4—C32—C30118.6 (4)C41—Sn2—N4129.37 (12)
N3—C32—C30116.2 (3)O4—Sn2—N473.13 (11)
N5—C1—C2—C30.7 (8)C7—N1—N2—C6−175.9 (3)
C1—C2—C3—C4−0.3 (7)Sn1—N1—N2—C63.4 (4)
C2—C3—C4—C50.6 (6)O4—C32—N3—N4−0.2 (5)
C2—C3—C4—C6−179.6 (4)C30—C32—N3—N4−178.6 (3)
C3—C4—C5—N5−1.3 (6)C34—C33—N4—N3−177.8 (3)
C6—C4—C5—N5178.9 (4)C34—C33—N4—Sn26.4 (5)
C3—C4—C6—O3−1.1 (5)C32—N3—N4—C33−179.1 (3)
C5—C4—C6—O3178.6 (3)C32—N3—N4—Sn2−2.8 (4)
C3—C4—C6—N2178.5 (4)C2—C1—N5—C5−1.4 (8)
C5—C4—C6—N2−1.8 (5)C4—C5—N5—C11.7 (7)
N1—C7—C8—C136.3 (6)C28—C27—N6—C310.4 (7)
N1—C7—C8—C9−172.4 (4)C30—C31—N6—C27−0.2 (7)
C13—C8—C9—C10−2.1 (6)C8—C13—O1—Sn1−25.6 (5)
C7—C8—C9—C10176.6 (4)C12—C13—O1—Sn1156.2 (2)
C8—C9—C10—C11−0.5 (7)C11—C12—O2—C14−0.1 (6)
C9—C10—C11—C121.3 (6)C13—C12—O2—C14178.3 (3)
C10—C11—C12—O2179.0 (4)N2—C6—O3—Sn1−6.7 (4)
C10—C11—C12—C130.6 (6)C4—C6—O3—Sn1172.9 (2)
C9—C8—C13—O1−174.2 (3)N3—C32—O4—Sn23.0 (4)
C7—C8—C13—O17.2 (5)C30—C32—O4—Sn2−178.6 (2)
C9—C8—C13—C124.0 (5)C34—C39—O5—Sn2−5.2 (5)
C7—C8—C13—C12−174.6 (3)C38—C39—O5—Sn2174.8 (2)
O2—C12—C13—O1−3.6 (4)C37—C38—O6—C401.0 (6)
C11—C12—C13—O1175.0 (3)C39—C38—O6—C40−179.9 (3)
O2—C12—C13—C8178.1 (3)C13—O1—Sn1—C21−98.2 (3)
C11—C12—C13—C8−3.3 (5)C13—O1—Sn1—C15143.8 (3)
C20—C15—C16—C170.1 (5)C13—O1—Sn1—O328.4 (5)
Sn1—C15—C16—C17175.7 (3)C13—O1—Sn1—N122.4 (3)
C15—C16—C17—C18−0.8 (7)C26—C21—Sn1—O1173.8 (3)
C16—C17—C18—C190.3 (8)C22—C21—Sn1—O1−10.7 (3)
C17—C18—C19—C200.9 (8)C26—C21—Sn1—C15−87.7 (3)
C18—C19—C20—C15−1.6 (7)C22—C21—Sn1—C1587.8 (3)
C16—C15—C20—C191.1 (6)C26—C21—Sn1—O312.5 (3)
Sn1—C15—C20—C19−174.7 (3)C22—C21—Sn1—O3−172.0 (3)
C26—C21—C22—C23−0.2 (5)C26—C21—Sn1—N187.6 (3)
Sn1—C21—C22—C23−175.8 (3)C22—C21—Sn1—N1−96.9 (3)
C21—C22—C23—C24−0.9 (6)C20—C15—Sn1—O1148.8 (3)
C22—C23—C24—C250.9 (7)C16—C15—Sn1—O1−26.8 (3)
C23—C24—C25—C260.1 (7)C20—C15—Sn1—C2148.6 (3)
C22—C21—C26—C251.3 (5)C16—C15—Sn1—C21−127.0 (3)
Sn1—C21—C26—C25176.8 (3)C20—C15—Sn1—O3−52.3 (3)
C24—C25—C26—C21−1.2 (6)C16—C15—Sn1—O3132.1 (3)
N6—C27—C28—C29−0.7 (8)C20—C15—Sn1—N1−126.7 (3)
C27—C28—C29—C300.7 (7)C16—C15—Sn1—N157.7 (3)
C28—C29—C30—C31−0.5 (6)C6—O3—Sn1—O1−0.4 (4)
C28—C29—C30—C32178.3 (4)C6—O3—Sn1—C21126.2 (2)
C29—C30—C31—N60.2 (7)C6—O3—Sn1—C15−115.5 (2)
C32—C30—C31—N6−178.5 (4)C6—O3—Sn1—N15.8 (2)
C31—C30—C32—O4−3.3 (5)C7—N1—Sn1—O1−8.3 (3)
C29—C30—C32—O4178.0 (3)N2—N1—Sn1—O1172.5 (2)
C31—C30—C32—N3175.3 (4)C7—N1—Sn1—C2185.9 (3)
C29—C30—C32—N3−3.5 (5)N2—N1—Sn1—C21−93.3 (3)
N4—C33—C34—C390.6 (6)C7—N1—Sn1—C15−99.0 (3)
N4—C33—C34—C35178.7 (4)N2—N1—Sn1—C1581.8 (3)
C39—C34—C35—C36−0.1 (6)C7—N1—Sn1—O3174.1 (3)
C33—C34—C35—C36−178.3 (4)N2—N1—Sn1—O3−5.0 (2)
C34—C35—C36—C370.1 (6)C39—O5—Sn2—C47−103.9 (3)
C35—C36—C37—C38−0.4 (6)C39—O5—Sn2—C41137.4 (3)
C36—C37—C38—O6179.8 (3)C39—O5—Sn2—O426.1 (5)
C36—C37—C38—C390.6 (6)C39—O5—Sn2—N48.3 (3)
C35—C34—C39—O5−179.7 (3)C48—C47—Sn2—O5−109.5 (3)
C33—C34—C39—O5−1.6 (5)C52—C47—Sn2—O570.5 (3)
C35—C34—C39—C380.3 (5)C48—C47—Sn2—C41−8.4 (4)
C33—C34—C39—C38178.4 (3)C52—C47—Sn2—C41171.6 (3)
O6—C38—C39—O50.2 (4)C48—C47—Sn2—O489.0 (3)
C37—C38—C39—O5179.4 (3)C52—C47—Sn2—O4−91.0 (3)
O6—C38—C39—C34−179.8 (3)C48—C47—Sn2—N4163.2 (3)
C37—C38—C39—C34−0.6 (5)C52—C47—Sn2—N4−16.8 (3)
C46—C41—C42—C43−0.5 (6)C46—C41—Sn2—O5−1.4 (3)
Sn2—C41—C42—C43−178.4 (3)C42—C41—Sn2—O5176.4 (3)
C41—C42—C43—C44−0.5 (7)C46—C41—Sn2—C47−105.4 (3)
C42—C43—C44—C450.3 (9)C42—C41—Sn2—C4772.4 (3)
C43—C44—C45—C460.7 (10)C46—C41—Sn2—O4155.9 (3)
C42—C41—C46—C451.5 (6)C42—C41—Sn2—O4−26.2 (3)
Sn2—C41—C46—C45179.4 (4)C46—C41—Sn2—N484.6 (3)
C44—C45—C46—C41−1.7 (9)C42—C41—Sn2—N4−97.5 (3)
C52—C47—C48—C491.0 (7)C32—O4—Sn2—O5−21.6 (4)
Sn2—C47—C48—C49−179.0 (4)C32—O4—Sn2—C47109.0 (3)
C47—C48—C49—C50−2.0 (8)C32—O4—Sn2—C41−133.2 (2)
C48—C49—C50—C511.8 (9)C32—O4—Sn2—N4−3.2 (2)
C49—C50—C51—C52−0.6 (8)C33—N4—Sn2—O5−8.6 (3)
C50—C51—C52—C47−0.5 (8)N3—N4—Sn2—O5175.7 (3)
C48—C47—C52—C510.3 (7)C33—N4—Sn2—C4789.7 (3)
Sn2—C47—C52—C51−179.7 (3)N3—N4—Sn2—C47−86.1 (3)
C8—C7—N1—N2177.0 (3)C33—N4—Sn2—C41−100.1 (3)
C8—C7—N1—Sn1−2.1 (5)N3—N4—Sn2—C4184.2 (3)
O3—C6—N2—N12.2 (5)C33—N4—Sn2—O4179.0 (3)
C4—C6—N2—N1−177.4 (3)N3—N4—Sn2—O43.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2154).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sanderson, R. T. (1967). Inorganic Chemistry, p. 74. New York: Reinhold.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yearwood, B., Parkin, C. H. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124–131.

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