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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m803.
Published online 2010 June 16. doi:  10.1107/S1600536810021896
PMCID: PMC3006936

Dibut­yl{N′-[1-(5-chloro-2-oxidophenyl-κO)ethyl­idene]-3-hy­droxy-2-naphtho­hydrazidato-κ2 N′,O 2}tin(IV)

Abstract

The five-coordinate SnIV atoms in the two crystallographically independent mol­ecules of the title compound, [Sn(C4H9)2(C19H13ClN2O3)], are in distorted cis-C2NO2Sn trigonal-bipyramidal coordination environments. The tridentate dianion of the Schiff base, N′-[1-(5-chloro-2-oxidophen­yl)ethyl­idene]-3-hy­droxy-2-naphtho­hydrazide, displays inter­molecular O—H(...)N hydrogen bonding, which stabilizes the overall compound.

Related literature

For a related structure, see: Lee et al. (2009 [triangle]). For the specific biological activity of metal complexes with hydrazone ligands, see: Bernhardt et al. (2006 [triangle]); Ainscough et al. (1999 [triangle]); Mohd Ali et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m803-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C19H13ClN2O3)]
  • M r = 585.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m803-efi1.jpg
  • a = 24.8256 (13) Å
  • b = 7.1994 (4) Å
  • c = 28.3649 (15) Å
  • β = 96.376 (1)°
  • V = 5038.3 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.15 mm−1
  • T = 100 K
  • 0.25 × 0.25 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.762, T max = 0.846
  • 37459 measured reflections
  • 8881 independent reflections
  • 8369 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.101
  • S = 1.32
  • 8881 reflections
  • 621 parameters
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −1.50 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021896/hg2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021896/hg2693Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant Nos. PS348/2009 C and RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Schiff bases derived from substituted salicylaldehydes have been widely used as polydentate ligands in the preparation of metal complexes. The metal complexes of these hydrazones with substituted salicylaldehydes are known to possess potential biological activities such as antifungal, anticancer and many others [Bernhardt et al. (2006), Ainscough et al. (1999), Mohd Ali et al. (2004)]. We have earlier reported the synthesis and molecular structure of a diphenyltin complex of the Schiff base derived from the reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chlorobenzaldehyde [Lee et al. (2009)]. The crystal structure of this complex consists of discrete molecules in which the tin atom is O,N, O'-chelated by the deprotonated Schiff base ligand. As an extension of our work in structural characterization of organotin with hydrazones, we report here the molecular structure of a dibutyltin complex of a Schiff base derived from the reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chloro-2-hydroxyacetophenone. The unit cell of the title complex consists of two crystallographically independent molecules. In both molecules, the Schiff base ligand, N'-[1-(5-chloro-2-oxidophenyl)ethylidene-3-hydroxy-2-naphthohydrazone] forms a tridentate dianion which coordinated to the dibutyltin fragment in a distorted cis-C2NO2Sn trigonal bipyramidal configuration; the axial O—Sn—O angle are 153.03 (13)o and 152.41 (13)o.

Experimental

The Schiff base ligand was prepared by the condensation reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chloro-2-hydroxyacetophenone. The prepared Schiff base (0.74 g, 2.0 mmol), dibutyltin dichloride (0.61 g, 2 mmol) and triethylamine (0.6 ml) were refluxed in 50 ml of ethanol for 5 h. The solution was left for crystallizaton at room temperature during which yellow crystals were obtained.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95 to 0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The hydroxy-H was refined with a restraint of 0.84 ± 0.01 Å.

Figures

Fig. 1.
The molecular structure of {N'-[1-(5-chloro-2-oxidophenyl-κO)ethylidene]-3-hydroxy-2- naphthohydrazidato-κ2N',O}dibutyltin(IV) showing 50% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres ...

Crystal data

[Sn(C4H9)2(C19H13ClN2O3)]F(000) = 2384
Mr = 585.67Dx = 1.544 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9440 reflections
a = 24.8256 (13) Åθ = 3.0–28.3°
b = 7.1994 (4) ŵ = 1.15 mm1
c = 28.3649 (15) ÅT = 100 K
β = 96.376 (1)°Prism, yellow
V = 5038.3 (5) Å30.25 × 0.25 × 0.15 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer8881 independent reflections
Radiation source: fine-focus sealed tube8369 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −29→29
Tmin = 0.762, Tmax = 0.846k = −8→8
37459 measured reflectionsl = −33→33

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.32w = 1/[σ2(Fo2) + (0.0158P)2 + 27.1939P] where P = (Fo2 + 2Fc2)/3
8881 reflections(Δ/σ)max = 0.002
621 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = −1.50 e Å3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
Sn10.339899 (13)0.57545 (4)0.642199 (11)0.01339 (9)
Sn20.663321 (13)0.45272 (4)0.866500 (11)0.01362 (9)
Cl10.09889 (5)0.79045 (19)0.48251 (5)0.0265 (3)
Cl20.90500 (5)0.15766 (18)1.01382 (4)0.0222 (3)
N10.26021 (16)0.6163 (5)0.66655 (13)0.0155 (9)
N20.26107 (16)0.6250 (5)0.71576 (13)0.0156 (9)
N30.73912 (16)0.3783 (5)0.83779 (13)0.0143 (8)
N40.73331 (17)0.3608 (5)0.78836 (13)0.0154 (9)
O10.29315 (13)0.4587 (5)0.58494 (11)0.0181 (7)
O20.35201 (13)0.6827 (5)0.71334 (11)0.0169 (7)
O30.22477 (14)0.5987 (6)0.79810 (12)0.0249 (8)
H3A0.22360.59800.76840.037*
O40.71848 (14)0.5613 (5)0.91961 (11)0.0190 (7)
O50.64255 (13)0.3284 (5)0.79779 (11)0.0172 (7)
O60.76138 (14)0.3611 (6)0.70211 (12)0.0240 (8)
H6A0.76620.36110.73190.036*
C10.2097 (2)0.6282 (6)0.58896 (17)0.0161 (10)
C20.24893 (19)0.5410 (6)0.56375 (17)0.0158 (10)
C30.2405 (2)0.5362 (7)0.51393 (17)0.0180 (10)
H30.26680.47810.49700.022*
C40.1953 (2)0.6129 (7)0.48898 (17)0.0175 (10)
H40.19050.60960.45530.021*
C50.1570 (2)0.6953 (7)0.51414 (18)0.0191 (11)
C60.1634 (2)0.7064 (7)0.56248 (17)0.0185 (11)
H60.13670.76700.57850.022*
C70.2130 (2)0.6357 (6)0.64094 (17)0.0157 (10)
C80.3104 (2)0.6565 (6)0.73630 (16)0.0144 (10)
C90.3190 (2)0.6643 (6)0.78861 (17)0.0157 (10)
C100.27594 (19)0.6359 (7)0.81743 (17)0.0167 (10)
C110.2865 (2)0.6438 (7)0.86580 (17)0.0188 (11)
H110.25800.62140.88470.023*
C120.3386 (2)0.6845 (7)0.88818 (17)0.0174 (10)
C130.3501 (2)0.7017 (7)0.93840 (18)0.0221 (11)
H130.32210.68130.95810.027*
C140.4011 (2)0.7474 (7)0.95847 (18)0.0253 (12)
H140.40790.76040.99190.030*
C150.4434 (2)0.7753 (8)0.93039 (18)0.0258 (12)
H150.47860.80630.94500.031*
C160.4345 (2)0.7584 (7)0.88228 (18)0.0231 (11)
H160.46360.77670.86360.028*
C170.3820 (2)0.7133 (6)0.85986 (17)0.0164 (10)
C180.3703 (2)0.7002 (6)0.81034 (17)0.0164 (10)
H180.39890.71690.79110.020*
C190.1629 (2)0.6682 (7)0.66458 (18)0.0198 (11)
H19A0.16570.60110.69480.030*
H19B0.13130.62340.64400.030*
H19C0.15890.80140.67040.030*
C200.3635 (2)0.8241 (7)0.60966 (17)0.0181 (10)
H20A0.33160.87510.58980.022*
H20B0.37450.91620.63480.022*
C210.4097 (2)0.8011 (7)0.57894 (17)0.0196 (11)
H21A0.39850.71280.55290.024*
H21B0.41720.92220.56450.024*
C220.4611 (2)0.7306 (8)0.60696 (19)0.0261 (12)
H22A0.45330.61150.62220.031*
H22B0.47290.82080.63240.031*
C230.5069 (2)0.7017 (8)0.5766 (2)0.0341 (14)
H23A0.53910.65690.59650.051*
H23B0.51530.81960.56180.051*
H23C0.49600.60980.55190.051*
C240.3781 (2)0.3161 (6)0.66053 (16)0.0158 (10)
H24A0.34970.21970.66060.019*
H24B0.40130.28270.63560.019*
C250.4127 (2)0.3118 (7)0.70831 (18)0.0218 (11)
H25A0.39160.36490.73270.026*
H25B0.44490.39160.70660.026*
C260.4315 (2)0.1172 (7)0.72372 (18)0.0233 (12)
H26A0.45260.06280.69950.028*
H26B0.39960.03710.72630.028*
C270.4666 (2)0.1227 (9)0.7715 (2)0.0330 (14)
H27A0.4744−0.00440.78260.050*
H27B0.44720.18880.79470.050*
H27C0.50070.18730.76790.050*
C280.79522 (19)0.3650 (6)0.91222 (16)0.0143 (10)
C290.76097 (18)0.4648 (6)0.93933 (16)0.0133 (9)
C300.7725 (2)0.4687 (7)0.98883 (17)0.0168 (10)
H300.74960.53761.00710.020*
C310.8163 (2)0.3747 (7)1.01155 (17)0.0167 (10)
H310.82340.37751.04510.020*
C320.84958 (19)0.2763 (6)0.98459 (17)0.0150 (10)
C330.84028 (19)0.2696 (6)0.93631 (17)0.0138 (10)
H330.86400.20100.91880.017*
C340.7875 (2)0.3568 (6)0.86017 (17)0.0156 (10)
C350.68199 (19)0.3368 (6)0.77180 (17)0.0153 (10)
C360.66883 (19)0.3165 (6)0.71995 (16)0.0148 (10)
C370.70804 (19)0.3304 (7)0.68733 (17)0.0165 (10)
C380.69298 (19)0.3140 (7)0.63940 (17)0.0172 (10)
H380.71960.32570.61800.021*
C390.6383 (2)0.2799 (6)0.62151 (17)0.0159 (10)
C400.6216 (2)0.2574 (7)0.57239 (18)0.0221 (11)
H400.64750.26850.55030.027*
C410.5690 (2)0.2201 (7)0.55652 (18)0.0236 (12)
H410.55870.20240.52360.028*
C420.5290 (2)0.2073 (7)0.58903 (18)0.0237 (12)
H420.49230.18280.57760.028*
C430.5438 (2)0.2303 (7)0.63622 (18)0.0223 (11)
H430.51720.22220.65770.027*
C440.5990 (2)0.2664 (6)0.65380 (17)0.0164 (10)
C450.6156 (2)0.2860 (7)0.70265 (17)0.0169 (10)
H450.58920.27770.72440.020*
C460.8346 (2)0.3182 (7)0.83287 (17)0.0183 (11)
H46A0.83280.40060.80520.028*
H46B0.83320.18860.82220.028*
H46C0.86850.34010.85330.028*
C470.6361 (2)0.2234 (7)0.90457 (18)0.0217 (11)
H47A0.65780.11340.89750.026*
H47B0.64430.24980.93890.026*
C480.5764 (2)0.1718 (7)0.89511 (19)0.0246 (12)
H48A0.56900.06510.91540.029*
H48B0.56840.13240.86160.029*
C490.5389 (2)0.3319 (7)0.90469 (19)0.0229 (11)
H49A0.55180.38910.93560.028*
H49B0.54040.42770.87980.028*
C500.4805 (2)0.2693 (8)0.9054 (2)0.0328 (14)
H50A0.45760.37750.90970.049*
H50B0.47830.18220.93160.049*
H50C0.46800.20790.87530.049*
C510.6336 (2)0.7244 (7)0.84806 (17)0.0185 (11)
H51A0.60490.75460.86840.022*
H51B0.66360.81380.85600.022*
C520.61069 (19)0.7563 (7)0.79624 (17)0.0182 (11)
H52A0.60910.89180.79020.022*
H52B0.63610.70210.77550.022*
C530.5552 (2)0.6757 (7)0.78225 (18)0.0220 (11)
H53A0.52940.72980.80270.026*
H53B0.55640.53990.78780.026*
C540.5348 (2)0.7132 (8)0.73038 (19)0.0292 (13)
H54A0.49670.67580.72420.044*
H54B0.55650.64180.70990.044*
H54C0.53810.84600.72370.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01504 (18)0.01007 (16)0.01526 (16)0.00157 (13)0.00262 (12)0.00071 (12)
Sn20.01455 (18)0.01240 (16)0.01387 (16)0.00251 (13)0.00139 (12)−0.00070 (13)
Cl10.0267 (7)0.0260 (7)0.0248 (7)0.0067 (6)−0.0070 (5)0.0001 (5)
Cl20.0198 (6)0.0236 (6)0.0222 (6)0.0062 (5)−0.0030 (5)0.0017 (5)
N10.020 (2)0.012 (2)0.015 (2)0.0007 (17)0.0031 (17)−0.0005 (16)
N20.018 (2)0.014 (2)0.014 (2)0.0022 (17)0.0020 (16)0.0017 (16)
N30.018 (2)0.0119 (19)0.0124 (19)0.0017 (16)0.0003 (16)−0.0001 (15)
N40.021 (2)0.012 (2)0.013 (2)0.0044 (17)0.0009 (16)−0.0008 (16)
O10.0158 (18)0.0165 (17)0.0218 (17)0.0034 (14)0.0014 (14)−0.0027 (14)
O20.0186 (18)0.0145 (17)0.0179 (17)0.0014 (14)0.0039 (14)−0.0009 (14)
O30.0180 (19)0.037 (2)0.0202 (18)−0.0022 (17)0.0053 (15)−0.0045 (17)
O40.0200 (18)0.0168 (17)0.0195 (17)0.0036 (15)−0.0007 (14)−0.0050 (14)
O50.0149 (18)0.0212 (18)0.0158 (16)−0.0008 (14)0.0034 (14)−0.0036 (14)
O60.0142 (19)0.038 (2)0.0196 (18)0.0012 (16)0.0028 (14)−0.0021 (17)
C10.018 (3)0.008 (2)0.022 (2)−0.0023 (19)0.001 (2)0.0013 (19)
C20.015 (2)0.009 (2)0.023 (2)0.0003 (19)0.0003 (19)0.001 (2)
C30.023 (3)0.010 (2)0.021 (2)0.000 (2)0.004 (2)−0.001 (2)
C40.022 (3)0.014 (2)0.016 (2)−0.002 (2)0.000 (2)−0.0022 (19)
C50.021 (3)0.012 (2)0.023 (3)0.000 (2)−0.003 (2)0.001 (2)
C60.021 (3)0.011 (2)0.023 (3)0.001 (2)0.002 (2)−0.002 (2)
C70.021 (3)0.004 (2)0.022 (3)−0.0004 (19)0.003 (2)−0.0012 (18)
C80.020 (3)0.008 (2)0.016 (2)0.0071 (19)0.005 (2)−0.0004 (18)
C90.018 (3)0.009 (2)0.021 (2)0.0017 (19)0.003 (2)0.0001 (19)
C100.011 (2)0.015 (2)0.025 (3)0.0046 (19)0.007 (2)−0.001 (2)
C110.017 (3)0.017 (3)0.024 (3)0.004 (2)0.010 (2)0.002 (2)
C120.022 (3)0.011 (2)0.021 (2)0.005 (2)0.005 (2)0.0002 (19)
C130.031 (3)0.014 (2)0.022 (3)0.003 (2)0.006 (2)0.002 (2)
C140.042 (3)0.018 (3)0.015 (2)0.007 (2)0.000 (2)0.000 (2)
C150.029 (3)0.023 (3)0.023 (3)0.000 (2)−0.006 (2)0.001 (2)
C160.025 (3)0.022 (3)0.022 (3)0.000 (2)0.002 (2)0.002 (2)
C170.020 (3)0.010 (2)0.020 (2)0.004 (2)0.003 (2)0.0007 (19)
C180.019 (3)0.011 (2)0.020 (2)0.003 (2)0.007 (2)−0.0010 (19)
C190.020 (3)0.016 (2)0.023 (3)0.000 (2)0.002 (2)0.000 (2)
C200.019 (3)0.013 (2)0.023 (3)0.004 (2)0.006 (2)0.002 (2)
C210.023 (3)0.017 (2)0.019 (2)−0.002 (2)0.003 (2)0.002 (2)
C220.027 (3)0.022 (3)0.029 (3)−0.002 (2)0.004 (2)0.007 (2)
C230.029 (3)0.017 (3)0.058 (4)−0.002 (2)0.011 (3)0.004 (3)
C240.020 (3)0.009 (2)0.019 (2)0.006 (2)0.004 (2)0.0058 (19)
C250.018 (3)0.023 (3)0.024 (3)0.006 (2)0.001 (2)0.004 (2)
C260.022 (3)0.025 (3)0.022 (3)0.008 (2)0.004 (2)0.007 (2)
C270.036 (3)0.034 (3)0.029 (3)0.014 (3)0.003 (3)0.009 (3)
C280.015 (2)0.011 (2)0.017 (2)−0.0028 (19)0.0004 (19)−0.0012 (18)
C290.009 (2)0.012 (2)0.019 (2)−0.0032 (19)0.0009 (18)−0.0004 (19)
C300.017 (3)0.013 (2)0.021 (2)−0.004 (2)0.006 (2)−0.004 (2)
C310.018 (3)0.013 (2)0.019 (2)−0.003 (2)0.001 (2)−0.0006 (19)
C320.010 (2)0.012 (2)0.022 (3)0.0022 (19)−0.0038 (19)−0.0013 (19)
C330.011 (2)0.009 (2)0.022 (2)−0.0018 (18)0.0026 (19)−0.0027 (19)
C340.019 (3)0.009 (2)0.019 (2)−0.0020 (19)0.002 (2)−0.0008 (19)
C350.014 (3)0.010 (2)0.022 (2)0.0049 (19)0.002 (2)−0.0015 (19)
C360.017 (3)0.010 (2)0.017 (2)0.0046 (19)0.0026 (19)0.0000 (19)
C370.010 (2)0.014 (2)0.025 (3)0.0009 (19)0.004 (2)−0.003 (2)
C380.013 (2)0.021 (3)0.019 (2)0.004 (2)0.0044 (19)0.000 (2)
C390.017 (3)0.012 (2)0.018 (2)0.007 (2)0.0003 (19)0.0004 (19)
C400.029 (3)0.017 (3)0.020 (3)0.005 (2)0.000 (2)0.000 (2)
C410.030 (3)0.020 (3)0.019 (3)0.003 (2)−0.004 (2)−0.003 (2)
C420.025 (3)0.018 (3)0.026 (3)−0.003 (2)−0.006 (2)0.002 (2)
C430.023 (3)0.020 (3)0.024 (3)−0.002 (2)0.002 (2)0.000 (2)
C440.017 (3)0.012 (2)0.020 (2)0.003 (2)−0.001 (2)0.0004 (19)
C450.016 (3)0.014 (2)0.021 (2)0.005 (2)0.003 (2)−0.001 (2)
C460.023 (3)0.015 (2)0.017 (2)0.001 (2)0.001 (2)−0.001 (2)
C470.027 (3)0.015 (2)0.024 (3)0.002 (2)0.006 (2)0.004 (2)
C480.034 (3)0.017 (3)0.024 (3)−0.007 (2)0.008 (2)0.000 (2)
C490.023 (3)0.017 (3)0.029 (3)0.002 (2)−0.001 (2)0.004 (2)
C500.023 (3)0.025 (3)0.052 (4)−0.006 (2)0.011 (3)−0.007 (3)
C510.019 (3)0.019 (3)0.018 (2)0.003 (2)0.005 (2)0.001 (2)
C520.011 (2)0.020 (3)0.024 (3)0.004 (2)0.003 (2)0.004 (2)
C530.013 (3)0.021 (3)0.032 (3)0.003 (2)0.002 (2)0.005 (2)
C540.030 (3)0.027 (3)0.029 (3)0.001 (3)−0.007 (2)0.000 (2)

Geometric parameters (Å, °)

Sn1—O12.067 (3)C23—H23C0.9800
Sn1—C202.126 (5)C24—C251.522 (7)
Sn1—C242.132 (4)C24—H24A0.9900
Sn1—O22.150 (3)C24—H24B0.9900
Sn1—N12.186 (4)C25—C261.526 (7)
Sn2—O42.073 (3)C25—H25A0.9900
Sn2—C472.123 (5)C25—H25B0.9900
Sn2—C512.135 (5)C26—C271.528 (7)
Sn2—O52.155 (3)C26—H26A0.9900
Sn2—N32.198 (4)C26—H26B0.9900
Cl1—C51.751 (5)C27—H27A0.9800
Cl2—C321.748 (5)C27—H27B0.9800
N1—C71.316 (6)C27—H27C0.9800
N1—N21.395 (5)C28—C291.406 (7)
N2—C81.316 (6)C28—C331.421 (7)
N3—C341.304 (6)C28—C341.469 (6)
N3—N41.399 (5)C29—C301.402 (6)
N4—C351.319 (6)C30—C311.378 (7)
O1—C21.331 (6)C30—H300.9500
O2—C81.294 (6)C31—C321.383 (7)
O3—C101.353 (6)C31—H310.9500
O3—H3A0.8400C32—C331.364 (7)
O4—C291.333 (6)C33—H330.9500
O5—C351.291 (6)C34—C461.498 (7)
O6—C371.362 (6)C35—C361.478 (6)
O6—H6A0.8400C36—C451.375 (7)
C1—C21.417 (7)C36—C371.419 (7)
C1—C61.418 (7)C37—C381.375 (7)
C1—C71.469 (7)C38—C391.418 (7)
C2—C31.406 (7)C38—H380.9500
C3—C41.374 (7)C39—C441.414 (7)
C3—H30.9500C39—C401.418 (7)
C4—C51.385 (7)C40—C411.359 (8)
C4—H40.9500C40—H400.9500
C5—C61.365 (7)C41—C421.431 (8)
C6—H60.9500C41—H410.9500
C7—C191.496 (7)C42—C431.358 (7)
C8—C91.476 (6)C42—H420.9500
C9—C181.377 (7)C43—C441.427 (7)
C9—C101.431 (7)C43—H430.9500
C10—C111.369 (7)C44—C451.408 (7)
C11—C121.407 (7)C45—H450.9500
C11—H110.9500C46—H46A0.9800
C12—C131.427 (7)C46—H46B0.9800
C12—C171.427 (7)C46—H46C0.9800
C13—C141.370 (8)C47—C481.524 (7)
C13—H130.9500C47—H47A0.9900
C14—C151.402 (8)C47—H47B0.9900
C14—H140.9500C48—C491.525 (7)
C15—C161.363 (7)C48—H48A0.9900
C15—H150.9500C48—H48B0.9900
C16—C171.424 (7)C49—C501.519 (7)
C16—H160.9500C49—H49A0.9900
C17—C181.405 (7)C49—H49B0.9900
C18—H180.9500C50—H50A0.9800
C19—H19A0.9800C50—H50B0.9800
C19—H19B0.9800C50—H50C0.9800
C19—H19C0.9800C51—C521.533 (7)
C20—C211.525 (7)C51—H51A0.9900
C20—H20A0.9900C51—H51B0.9900
C20—H20B0.9900C52—C531.507 (7)
C21—C221.514 (7)C52—H52A0.9900
C21—H21A0.9900C52—H52B0.9900
C21—H21B0.9900C53—C541.526 (7)
C22—C231.514 (8)C53—H53A0.9900
C22—H22A0.9900C53—H53B0.9900
C22—H22B0.9900C54—H54A0.9800
C23—H23A0.9800C54—H54B0.9800
C23—H23B0.9800C54—H54C0.9800
O1—Sn1—C2099.15 (17)C24—C25—H25A108.9
O1—Sn1—C2491.79 (16)C26—C25—H25A108.9
C20—Sn1—C24134.95 (19)C24—C25—H25B108.9
O1—Sn1—O2153.02 (13)C26—C25—H25B108.9
C20—Sn1—O295.08 (16)H25A—C25—H25B107.7
C24—Sn1—O294.22 (15)C25—C26—C27110.9 (5)
O1—Sn1—N181.61 (14)C25—C26—H26A109.5
C20—Sn1—N1109.07 (16)C27—C26—H26A109.5
C24—Sn1—N1115.74 (17)C25—C26—H26B109.5
O2—Sn1—N172.08 (13)C27—C26—H26B109.5
O4—Sn2—C4798.34 (17)H26A—C26—H26B108.1
O4—Sn2—C5190.85 (17)C26—C27—H27A109.5
C47—Sn2—C51135.8 (2)C26—C27—H27B109.5
O4—Sn2—O5152.42 (13)H27A—C27—H27B109.5
C47—Sn2—O594.55 (17)C26—C27—H27C109.5
C51—Sn2—O596.75 (16)H27A—C27—H27C109.5
O4—Sn2—N380.65 (14)H27B—C27—H27C109.5
C47—Sn2—N3109.41 (17)C29—C28—C33118.4 (4)
C51—Sn2—N3114.78 (17)C29—C28—C34123.4 (4)
O5—Sn2—N372.08 (13)C33—C28—C34118.2 (4)
C7—N1—N2117.5 (4)O4—C29—C30118.3 (4)
C7—N1—Sn1128.4 (3)O4—C29—C28122.4 (4)
N2—N1—Sn1114.1 (3)C30—C29—C28119.3 (4)
C8—N2—N1111.1 (4)C31—C30—C29121.4 (4)
C34—N3—N4117.7 (4)C31—C30—H30119.3
C34—N3—Sn2129.0 (3)C29—C30—H30119.3
N4—N3—Sn2113.3 (3)C30—C31—C32118.8 (4)
C35—N4—N3110.9 (4)C30—C31—H31120.6
C2—O1—Sn1122.5 (3)C32—C31—H31120.6
C8—O2—Sn1112.6 (3)C33—C32—C31121.9 (4)
C10—O3—H3A109.5C33—C32—Cl2119.7 (4)
C29—O4—Sn2122.5 (3)C31—C32—Cl2118.4 (4)
C35—O5—Sn2112.1 (3)C32—C33—C28120.1 (4)
C37—O6—H6A109.5C32—C33—H33119.9
C2—C1—C6118.1 (4)C28—C33—H33119.9
C2—C1—C7123.9 (4)N3—C34—C28119.7 (4)
C6—C1—C7118.0 (4)N3—C34—C46120.0 (4)
O1—C2—C3117.8 (4)C28—C34—C46120.3 (4)
O1—C2—C1123.2 (4)O5—C35—N4124.5 (4)
C3—C2—C1118.9 (4)O5—C35—C36117.8 (4)
C4—C3—C2122.0 (5)N4—C35—C36117.7 (4)
C4—C3—H3119.0C45—C36—C37118.7 (4)
C2—C3—H3119.0C45—C36—C35117.9 (4)
C3—C4—C5118.4 (5)C37—C36—C35123.4 (4)
C3—C4—H4120.8O6—C37—C38117.8 (4)
C5—C4—H4120.8O6—C37—C36121.6 (4)
C6—C5—C4122.1 (5)C38—C37—C36120.5 (4)
C6—C5—Cl1119.3 (4)C37—C38—C39120.9 (4)
C4—C5—Cl1118.5 (4)C37—C38—H38119.6
C5—C6—C1120.5 (5)C39—C38—H38119.6
C5—C6—H6119.8C44—C39—C38118.9 (4)
C1—C6—H6119.8C44—C39—C40118.8 (5)
N1—C7—C1119.9 (4)C38—C39—C40122.4 (5)
N1—C7—C19120.2 (4)C41—C40—C39120.9 (5)
C1—C7—C19119.9 (4)C41—C40—H40119.6
O2—C8—N2123.9 (4)C39—C40—H40119.6
O2—C8—C9117.8 (4)C40—C41—C42120.6 (5)
N2—C8—C9118.3 (4)C40—C41—H41119.7
C18—C9—C10118.9 (4)C42—C41—H41119.7
C18—C9—C8118.7 (4)C43—C42—C41119.8 (5)
C10—C9—C8122.4 (4)C43—C42—H42120.1
O3—C10—C11118.8 (4)C41—C42—H42120.1
O3—C10—C9121.6 (4)C42—C43—C44120.7 (5)
C11—C10—C9119.6 (5)C42—C43—H43119.7
C10—C11—C12121.7 (5)C44—C43—H43119.7
C10—C11—H11119.2C45—C44—C39118.8 (4)
C12—C11—H11119.2C45—C44—C43121.8 (5)
C11—C12—C13122.6 (5)C39—C44—C43119.3 (4)
C11—C12—C17119.3 (4)C36—C45—C44122.2 (5)
C13—C12—C17118.1 (5)C36—C45—H45118.9
C14—C13—C12120.5 (5)C44—C45—H45118.9
C14—C13—H13119.7C34—C46—H46A109.5
C12—C13—H13119.7C34—C46—H46B109.5
C13—C14—C15121.0 (5)H46A—C46—H46B109.5
C13—C14—H14119.5C34—C46—H46C109.5
C15—C14—H14119.5H46A—C46—H46C109.5
C16—C15—C14120.5 (5)H46B—C46—H46C109.5
C16—C15—H15119.7C48—C47—Sn2117.3 (3)
C14—C15—H15119.7C48—C47—H47A108.0
C15—C16—C17120.4 (5)Sn2—C47—H47A108.0
C15—C16—H16119.8C48—C47—H47B108.0
C17—C16—H16119.8Sn2—C47—H47B108.0
C18—C17—C16122.6 (5)H47A—C47—H47B107.2
C18—C17—C12117.9 (5)C47—C48—C49112.7 (4)
C16—C17—C12119.5 (5)C47—C48—H48A109.0
C9—C18—C17122.5 (5)C49—C48—H48A109.0
C9—C18—H18118.7C47—C48—H48B109.0
C17—C18—H18118.7C49—C48—H48B109.0
C7—C19—H19A109.5H48A—C48—H48B107.8
C7—C19—H19B109.5C50—C49—C48112.4 (4)
H19A—C19—H19B109.5C50—C49—H49A109.1
C7—C19—H19C109.5C48—C49—H49A109.1
H19A—C19—H19C109.5C50—C49—H49B109.1
H19B—C19—H19C109.5C48—C49—H49B109.1
C21—C20—Sn1114.7 (3)H49A—C49—H49B107.9
C21—C20—H20A108.6C49—C50—H50A109.5
Sn1—C20—H20A108.6C49—C50—H50B109.5
C21—C20—H20B108.6H50A—C50—H50B109.5
Sn1—C20—H20B108.6C49—C50—H50C109.5
H20A—C20—H20B107.6H50A—C50—H50C109.5
C22—C21—C20112.4 (4)H50B—C50—H50C109.5
C22—C21—H21A109.1C52—C51—Sn2117.0 (3)
C20—C21—H21A109.1C52—C51—H51A108.1
C22—C21—H21B109.1Sn2—C51—H51A108.1
C20—C21—H21B109.1C52—C51—H51B108.1
H21A—C21—H21B107.9Sn2—C51—H51B108.1
C21—C22—C23112.9 (5)H51A—C51—H51B107.3
C21—C22—H22A109.0C53—C52—C51115.2 (4)
C23—C22—H22A109.0C53—C52—H52A108.5
C21—C22—H22B109.0C51—C52—H52A108.5
C23—C22—H22B109.0C53—C52—H52B108.5
H22A—C22—H22B107.8C51—C52—H52B108.5
C22—C23—H23A109.5H52A—C52—H52B107.5
C22—C23—H23B109.5C52—C53—C54112.4 (4)
H23A—C23—H23B109.5C52—C53—H53A109.1
C22—C23—H23C109.5C54—C53—H53A109.1
H23A—C23—H23C109.5C52—C53—H53B109.1
H23B—C23—H23C109.5C54—C53—H53B109.1
C25—C24—Sn1115.3 (3)H53A—C53—H53B107.8
C25—C24—H24A108.5C53—C54—H54A109.5
Sn1—C24—H24A108.5C53—C54—H54B109.5
C25—C24—H24B108.5H54A—C54—H54B109.5
Sn1—C24—H24B108.5C53—C54—H54C109.5
H24A—C24—H24B107.5H54A—C54—H54C109.5
C24—C25—C26113.5 (4)H54B—C54—H54C109.5
O1—Sn1—N1—C7−27.5 (4)C11—C12—C17—C16178.7 (5)
C20—Sn1—N1—C769.4 (4)C13—C12—C17—C16−0.2 (7)
C24—Sn1—N1—C7−115.4 (4)C10—C9—C18—C17−1.1 (7)
O2—Sn1—N1—C7158.6 (4)C8—C9—C18—C17178.9 (4)
O1—Sn1—N1—N2153.6 (3)C16—C17—C18—C9−177.2 (5)
C20—Sn1—N1—N2−109.6 (3)C12—C17—C18—C91.2 (7)
C24—Sn1—N1—N265.7 (3)O1—Sn1—C20—C21−79.3 (4)
O2—Sn1—N1—N2−20.3 (3)C24—Sn1—C20—C2122.6 (5)
C7—N1—N2—C8−162.1 (4)O2—Sn1—C20—C21123.7 (4)
Sn1—N1—N2—C817.0 (5)N1—Sn1—C20—C21−163.5 (3)
O4—Sn2—N3—C3423.2 (4)Sn1—C20—C21—C22−60.6 (5)
C47—Sn2—N3—C34−72.5 (4)C20—C21—C22—C23178.3 (4)
C51—Sn2—N3—C34109.8 (4)O1—Sn1—C24—C25−169.9 (4)
O5—Sn2—N3—C34−161.0 (4)C20—Sn1—C24—C2585.2 (4)
O4—Sn2—N3—N4−153.8 (3)O2—Sn1—C24—C25−16.3 (4)
C47—Sn2—N3—N4110.6 (3)N1—Sn1—C24—C25−88.4 (4)
C51—Sn2—N3—N4−67.2 (3)Sn1—C24—C25—C26170.4 (3)
O5—Sn2—N3—N422.1 (3)C24—C25—C26—C27179.2 (4)
C34—N3—N4—C35163.4 (4)Sn2—O4—C29—C30−135.1 (4)
Sn2—N3—N4—C35−19.3 (4)Sn2—O4—C29—C2846.9 (6)
C20—Sn1—O1—C2−61.1 (4)C33—C28—C29—O4178.6 (4)
C24—Sn1—O1—C2162.8 (4)C34—C28—C29—O4−0.2 (7)
O2—Sn1—O1—C259.9 (5)C33—C28—C29—C300.6 (7)
N1—Sn1—O1—C247.0 (4)C34—C28—C29—C30−178.2 (4)
O1—Sn1—O2—C87.4 (5)O4—C29—C30—C31−178.9 (4)
C20—Sn1—O2—C8129.2 (3)C28—C29—C30—C31−0.9 (7)
C24—Sn1—O2—C8−95.0 (3)C29—C30—C31—C320.6 (7)
N1—Sn1—O2—C820.7 (3)C30—C31—C32—C33−0.1 (7)
C47—Sn2—O4—C2960.2 (4)C30—C31—C32—Cl2180.0 (4)
C51—Sn2—O4—C29−163.2 (4)C31—C32—C33—C28−0.2 (7)
O5—Sn2—O4—C29−56.8 (5)Cl2—C32—C33—C28179.8 (4)
N3—Sn2—O4—C29−48.2 (3)C29—C28—C33—C32−0.1 (7)
O4—Sn2—O5—C35−12.8 (5)C34—C28—C33—C32178.8 (4)
C47—Sn2—O5—C35−130.6 (3)N4—N3—C34—C28−177.1 (4)
C51—Sn2—O5—C3592.2 (3)Sn2—N3—C34—C286.1 (6)
N3—Sn2—O5—C35−21.7 (3)N4—N3—C34—C461.0 (6)
Sn1—O1—C2—C3138.3 (4)Sn2—N3—C34—C46−175.8 (3)
Sn1—O1—C2—C1−43.3 (6)C29—C28—C34—N3−26.8 (7)
C6—C1—C2—O1−178.1 (4)C33—C28—C34—N3154.4 (4)
C7—C1—C2—O1−0.7 (7)C29—C28—C34—C46155.1 (5)
C6—C1—C2—C30.2 (7)C33—C28—C34—C46−23.7 (6)
C7—C1—C2—C3177.6 (4)Sn2—O5—C35—N420.6 (6)
O1—C2—C3—C4178.2 (4)Sn2—O5—C35—C36−159.9 (3)
C1—C2—C3—C4−0.2 (7)N3—N4—C35—O5−0.7 (6)
C2—C3—C4—C5−0.7 (7)N3—N4—C35—C36179.8 (4)
C3—C4—C5—C61.7 (8)O5—C35—C36—C45−1.4 (7)
C3—C4—C5—Cl1−179.2 (4)N4—C35—C36—C45178.1 (4)
C4—C5—C6—C1−1.8 (8)O5—C35—C36—C37177.4 (4)
Cl1—C5—C6—C1179.1 (4)N4—C35—C36—C37−3.1 (7)
C2—C1—C6—C50.8 (7)C45—C36—C37—O6179.8 (4)
C7—C1—C6—C5−176.8 (4)C35—C36—C37—O61.0 (7)
N2—N1—C7—C1179.9 (4)C45—C36—C37—C380.2 (7)
Sn1—N1—C7—C10.9 (6)C35—C36—C37—C38−178.6 (4)
N2—N1—C7—C190.8 (6)O6—C37—C38—C39179.3 (4)
Sn1—N1—C7—C19−178.2 (3)C36—C37—C38—C39−1.1 (7)
C2—C1—C7—N122.4 (7)C37—C38—C39—C441.2 (7)
C6—C1—C7—N1−160.2 (4)C37—C38—C39—C40−178.3 (5)
C2—C1—C7—C19−158.6 (5)C44—C39—C40—C41−1.2 (7)
C6—C1—C7—C1918.8 (6)C38—C39—C40—C41178.3 (5)
Sn1—O2—C8—N2−20.6 (6)C39—C40—C41—C421.6 (8)
Sn1—O2—C8—C9159.9 (3)C40—C41—C42—C43−0.8 (8)
N1—N2—C8—O22.4 (6)C41—C42—C43—C44−0.2 (8)
N1—N2—C8—C9−178.2 (4)C38—C39—C44—C45−0.5 (7)
O2—C8—C9—C180.5 (6)C40—C39—C44—C45179.0 (4)
N2—C8—C9—C18−179.0 (4)C38—C39—C44—C43−179.4 (5)
O2—C8—C9—C10−179.5 (4)C40—C39—C44—C430.2 (7)
N2—C8—C9—C101.1 (7)C42—C43—C44—C45−178.3 (5)
C18—C9—C10—O3−179.5 (4)C42—C43—C44—C390.6 (7)
C8—C9—C10—O30.5 (7)C37—C36—C45—C440.6 (7)
C18—C9—C10—C11−0.3 (7)C35—C36—C45—C44179.4 (4)
C8—C9—C10—C11179.6 (4)C39—C44—C45—C36−0.4 (7)
O3—C10—C11—C12−179.1 (4)C43—C44—C45—C36178.5 (5)
C9—C10—C11—C121.7 (7)O4—Sn2—C47—C48143.3 (4)
C10—C11—C12—C13177.1 (5)C51—Sn2—C47—C4843.4 (5)
C10—C11—C12—C17−1.7 (7)O5—Sn2—C47—C48−61.2 (4)
C11—C12—C13—C14−177.9 (5)N3—Sn2—C47—C48−133.7 (4)
C17—C12—C13—C141.0 (7)Sn2—C47—C48—C49−57.6 (5)
C12—C13—C14—C15−1.0 (8)C47—C48—C49—C50−167.9 (5)
C13—C14—C15—C160.3 (8)O4—Sn2—C51—C52150.9 (4)
C14—C15—C16—C170.4 (8)C47—Sn2—C51—C52−106.2 (4)
C15—C16—C17—C18177.9 (5)O5—Sn2—C51—C52−2.6 (4)
C15—C16—C17—C12−0.5 (7)N3—Sn2—C51—C5270.8 (4)
C11—C12—C17—C180.2 (7)Sn2—C51—C52—C5375.6 (5)
C13—C12—C17—C18−178.6 (4)C51—C52—C53—C54179.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···N20.841.852.602 (5)147
O6—H6A···N40.841.882.617 (5)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2693).

References

  • Ainscough, E. W., Brodie, A. M., Denny, W. A., Finlay, G. J., Gothe, S. A. & Ranford, J. D. (1999). J. Inorg. Biochem.77, 125–133 [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bernhardt, P. V., Mattsson, J. & Richardson, D. R. (2006). Inorg. Chem.45, 752–760. [PubMed]
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, m1689. [PMC free article] [PubMed]
  • Mohd Ali, H. M., Zain, S., Basirun, W. J., Rahuma, S. M., Sharifah Rohaiza, S. O., Abdullah, N. & Teoh, H. L. (2004). Malays. J. Sci.23, 119–127.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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