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Acta Cryst. (2007). E63, m1843    [ doi:10.1107/S1600536807027298 ]

{(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]benzoato}triphenyltin(IV)

X.-N. Fang, Y. Sui, R.-H. Hu, Q.-Y. Luo and H.-Q. Qin

Abstract top

The title compound, [Sn(C6H5)3(C19H16N3O3)], is a four-coordinate SnIV complex, with a distorted tetrahedral geometry and one disordered (0.54:0.46) phenyl ring. The Schiff base carboxylate group acts as a monodentate ligand coordinating through the deprotonated hydroxyl O atom. In the crystal structure, a weak offset face-to-face aromatic [pi]-[pi] stacking interaction can be found between the pyrazole ring and the benzene ring of 4-formylbenzoic acid. The centroid-to-centroid distance is 3.858 (2) Å and the interplanar distance is 3.375 (4) Å.

Comment top

4-aminoantipyrine and its derivatives are important compounds in pharmacology and biochemistry. They are especially used as anti-inflammatory drugs (Hökelek et al., 2002). The structural chemistry of organotin carboxylate complexs has attracted considerable attention, owing to their good antitumor activities (Barbieri et al., 2001; Zhou et al., 2005), their versatile molecular structures and the supramolecular architectures exhibited by these complexes (Ma et al., 2005). In the context of our continued interest in the structural and biological properties of organotin complexes (Fang et al., 2001; Fang, et al., 2006), we have been interested in studying the biologigal properties of the title compound.

The title compound (E)-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl] benzoato-triphenyltin (IV), is a four-coordinate SnIV complex, with a distorted tetrahedron geometry (Fig. 1). The (E)-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl) benzoate ligand, coordinates in monodentate mode bonding with the triphenyltin group. The Sn1—O1 bond length is 2.044 (2) Å, which is slightly shorter than the value of 2.121 (3)Å reported by Fang, Sui et al. (2006a). The double bond C═ N length is 1.271 (3) Å, and this is comparable to the analogue of 1.280 (3)Å found by Hu et al. (2006).

The ring of pyrazole is well coplanar, with a mean deviation from the plane of 0.027 (3) Å, and makes an angle of 49.9 (2)° with the substituent phenyl (C1 to C6) and 20.7 (2)° with the benzene ring of 4-formylbenzoic acid (C13 to C18).

In the crystal lattice (Fig. 2), a weak aromatic π-π stacking interaction can be found between the pyrazole ring (Cg1) and benzene ring (Cg2) of 4-formylbenzoic acid [the distance of Cg1···Cg2i is 3.858 (2) Å; and the C10···C18i distance in the offset face-to-face interaction is 3.375 (4) Å; symmetry code: (i) 1 − x, 1 − y, −z)].

Related literature top

For related literature, see: Barbieri et al. (2001); Fang et al. (2001); Fang, Sui, Ying, Xu & Guo (2006); Fang, Xu, Guo & Zeng (2006); Hökelek et al. (2002); Ma et al. (2005); Zhou et al. (2005).

Experimental top

The title compound (I) was prepared by the following procedure: A solution of Schiff base ligand, (E)-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl)\ benzoic acid, (0.335 g, 1 m mol) and triphenyltin hydroxide (0.367 g, 1 mmol) in 20 ml mixed solvent (benzene:toluene = 1:1) was heated for 6 h under reflux. The solvent was removed by vacuum distillation in a rotary evaporator and a yellow solid product was obtained (yield 83%, m.p. 497–498 K). When the solid was recrystallized from toluene, single crystals suitable for X-ray diffraction analysis precipitated after several days.

Refinement top

One phenyl ring of the triphenyltin is disordered in the crystal structure. Each of the six atoms can be splitted into two parts to form two six-membered rings, and the positional occupancy factors is 0.54. A l l the H atoms were positioned in idealized locations and refined as riding on their carrier atoms, with C—H distances of 0.93 (aryl) and 0.96Å (methyl) with Uiso(H) = 1.5Ueq(C) for methyl and Uiso(H) = 1.2Ueq(C) for aryl.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing 30% probability displacement ellipsoids. All the H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing diagram of (I), viewed down the a axis. All the H atoms and part of the disordered phenyl have been omitted for clarity.
{(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]\ benzoato}triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C19H16N3O3)]Z = 2
Mr = 684.34F(000) = 696
Triclinic, P1Dx = 1.408 Mg m−3
Hall symbol: -P 1Melting point = 497–498 K
a = 9.2009 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6299 (19) ÅCell parameters from 5058 reflections
c = 15.598 (2) Åθ = 2.4–29.2°
α = 74.435 (2)°µ = 0.83 mm−1
β = 77.913 (2)°T = 296 K
γ = 68.677 (2)°Block, yellow
V = 1613.9 (4) Å30.41 × 0.39 × 0.31 mm
Data collection top
Bruker APEX II area-detector
diffractometer		5246 independent reflections
Radiation source: fine-focus sealed tube5039 reflections with I > 2σ(I)
graphiteRint = 0.011
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −10→10
Tmin = 0.727, Tmax = 0.783k = −15→14
9137 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0309P)2 + 0.6678P]
where P = (Fo2 + 2Fc2)/3
5246 reflections(Δ/σ)max = 0.002
388 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
[Sn(C6H5)3(C19H16N3O3)]γ = 68.677 (2)°
Mr = 684.34V = 1613.9 (4) Å3
Triclinic, P1Z = 2
a = 9.2009 (14) ÅMo Kα radiation
b = 12.6299 (19) ŵ = 0.83 mm−1
c = 15.598 (2) ÅT = 296 K
α = 74.435 (2)°0.41 × 0.39 × 0.31 mm
β = 77.913 (2)°
Data collection top
Bruker APEX II area-detector
diffractometer		5246 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		5039 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.783Rint = 0.011
9137 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.060Δρmax = 0.37 e Å−3
S = 1.04Δρmin = −0.27 e Å−3
5246 reflectionsAbsolute structure: ?
388 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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)
C320.5054 (2)0.77153 (16)0.45208 (11)0.0465 (6)0.536 (3)
C330.5808 (2)0.75898 (14)0.52445 (12)0.0605 (9)0.536 (3)
H330.62720.81320.52460.073*0.536 (3)
C340.5868 (3)0.66540 (18)0.59664 (11)0.0714 (13)0.536 (3)
H340.63720.65700.64510.086*0.536 (3)
C350.5174 (3)0.58438 (18)0.59645 (17)0.0784 (16)0.536 (3)
H350.52140.52180.64480.094*0.536 (3)
C360.4420 (4)0.5969 (2)0.5241 (2)0.0808 (13)0.536 (3)
H360.39560.54270.52400.097*0.536 (3)
C370.4360 (3)0.6905 (2)0.45190 (17)0.0650 (10)0.536 (3)
H370.38560.69890.40350.078*0.536 (3)
C32A0.5064 (2)0.78462 (14)0.46971 (11)0.0465 (6)0.464 (3)
C33A0.6317 (3)0.75826 (18)0.51712 (14)0.0605 (9)0.464 (3)
H33A0.70720.79520.49660.073*0.464 (3)
C34A0.6397 (3)0.6752 (2)0.59586 (13)0.0714 (13)0.464 (3)
H34A0.72500.65170.62760.086*0.464 (3)
C35A0.5229 (3)0.6275 (2)0.62702 (12)0.0784 (16)0.464 (3)
H35A0.52950.57110.67980.094*0.464 (3)
C36A0.3992 (3)0.6606 (2)0.58286 (17)0.0808 (13)0.464 (3)
H36A0.31790.62990.60640.097*0.464 (3)
C37A0.39118 (18)0.7403 (2)0.50232 (16)0.0650 (10)0.464 (3)
H37A0.30530.76270.47120.078*0.464 (3)
C10.1119 (2)0.41572 (17)−0.22321 (13)0.0423 (4)
C20.2001 (3)0.4252 (2)−0.30692 (14)0.0501 (5)
H20.30110.4287−0.31300.060*
C30.1371 (3)0.4295 (2)−0.38092 (15)0.0584 (6)
H30.19510.4378−0.43740.070*
C4−0.0104 (3)0.4217 (2)−0.37211 (16)0.0655 (7)
H4−0.05170.4234−0.42220.079*
C5−0.0974 (3)0.4114 (2)−0.28821 (17)0.0633 (6)
H5−0.19710.4055−0.28200.076*
C6−0.0374 (3)0.4097 (2)−0.21355 (15)0.0512 (5)
H6−0.09700.4047−0.15750.061*
C70.1644 (3)0.2264 (2)−0.05646 (17)0.0622 (6)
H7A0.26910.1866−0.08080.093*
H7B0.08990.2224−0.08940.093*
H7C0.14550.19030.00550.093*
C80.1921 (4)0.3250 (2)0.09253 (16)0.0676 (7)
H8A0.09270.31310.11560.101*
H8B0.21050.37090.12670.101*
H8C0.27430.25110.09710.101*
C90.1902 (3)0.38690 (19)−0.00328 (14)0.0471 (5)
C100.2312 (2)0.48386 (19)−0.04414 (13)0.0444 (5)
C110.2225 (3)0.50515 (19)−0.13904 (14)0.0467 (5)
C120.3037 (3)0.6390 (2)−0.03608 (15)0.0546 (5)
H120.30230.6662−0.09760.066*
C130.3429 (3)0.7033 (2)0.01676 (15)0.0511 (5)
C140.3378 (4)0.8184 (2)−0.01735 (17)0.0685 (7)
H140.31690.8535−0.07600.082*
C150.3635 (3)0.8807 (2)0.03530 (17)0.0665 (7)
H150.35820.95780.01200.080*
C160.3970 (3)0.8293 (2)0.12243 (14)0.0487 (5)
C170.4097 (3)0.7134 (2)0.15472 (15)0.0503 (5)
H170.43630.67720.21230.060*
C180.3834 (3)0.6508 (2)0.10266 (15)0.0503 (5)
H180.39290.57290.12540.060*
C190.4175 (3)0.8982 (2)0.18055 (15)0.0540 (6)
C200.6833 (3)0.97250 (19)0.29455 (14)0.0477 (5)
C210.6816 (3)1.0830 (2)0.29179 (17)0.0617 (6)
H210.58931.13710.31160.074*
C220.8154 (4)1.1144 (3)0.2600 (2)0.0774 (8)
H220.81321.18890.25900.093*
C230.9509 (4)1.0356 (3)0.2300 (2)0.0861 (9)
H231.04091.05650.20850.103*
C240.9544 (4)0.9259 (3)0.2316 (3)0.0909 (10)
H241.04650.87260.21070.109*
C250.8211 (3)0.8941 (2)0.2643 (2)0.0686 (7)
H250.82440.81920.26590.082*
C260.2702 (3)1.0560 (2)0.37759 (14)0.0498 (5)
C270.1939 (3)1.0432 (2)0.46467 (17)0.0641 (6)
H270.23240.97520.50660.077*
C280.0620 (4)1.1302 (3)0.4896 (2)0.0955 (11)
H280.01061.12090.54780.115*
C290.0069 (5)1.2307 (3)0.4277 (3)0.1140 (14)
H29−0.08141.29000.44470.137*
C300.0794 (5)1.2453 (3)0.3415 (3)0.1008 (11)
H300.04011.31360.30010.121*
C310.2119 (3)1.1576 (2)0.31647 (18)0.0697 (7)
H310.26191.16730.25800.084*
N10.2718 (2)0.54639 (17)0.00252 (12)0.0485 (4)
N20.1793 (2)0.41422 (16)−0.14869 (11)0.0467 (4)
N30.1472 (2)0.34757 (15)−0.06359 (11)0.0466 (4)
O10.4520 (2)0.83730 (15)0.26047 (11)0.0618 (4)
O20.4028 (3)1.00110 (17)0.15681 (13)0.0770 (5)
O30.2441 (2)0.58297 (16)−0.20178 (11)0.0671 (5)
Sn10.480454 (17)0.922187 (12)0.347192 (9)0.04610 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C320.0509 (13)0.0475 (15)0.0381 (14)−0.0128 (11)−0.0024 (10)−0.0110 (11)
C330.078 (3)0.0494 (16)0.0603 (16)−0.0201 (16)−0.0200 (17)−0.0135 (13)
C340.086 (3)0.064 (2)0.0606 (18)−0.010 (2)−0.0268 (19)−0.0137 (15)
C350.084 (3)0.063 (3)0.073 (3)−0.024 (2)−0.013 (2)0.013 (2)
C360.080 (3)0.069 (3)0.094 (3)−0.046 (2)−0.015 (2)0.014 (2)
C370.062 (2)0.069 (3)0.066 (3)−0.034 (2)−0.0151 (19)0.0047 (17)
C32A0.0509 (13)0.0475 (15)0.0381 (14)−0.0128 (11)−0.0024 (10)−0.0110 (11)
C33A0.078 (3)0.0494 (16)0.0603 (16)−0.0201 (16)−0.0200 (17)−0.0135 (13)
C34A0.086 (3)0.064 (2)0.0606 (18)−0.010 (2)−0.0268 (19)−0.0137 (15)
C35A0.084 (3)0.063 (3)0.073 (3)−0.024 (2)−0.013 (2)0.013 (2)
C36A0.080 (3)0.069 (3)0.094 (3)−0.046 (2)−0.015 (2)0.014 (2)
C37A0.062 (2)0.069 (3)0.066 (3)−0.034 (2)−0.0151 (19)0.0047 (17)
C10.0539 (12)0.0341 (11)0.0399 (10)−0.0141 (9)−0.0064 (8)−0.0091 (8)
C20.0547 (12)0.0479 (13)0.0464 (12)−0.0179 (10)−0.0017 (9)−0.0096 (10)
C30.0740 (16)0.0575 (15)0.0398 (11)−0.0196 (12)−0.0017 (10)−0.0108 (10)
C40.0819 (18)0.0727 (18)0.0473 (13)−0.0246 (14)−0.0194 (12)−0.0137 (12)
C50.0586 (14)0.0754 (18)0.0614 (15)−0.0252 (13)−0.0145 (11)−0.0133 (13)
C60.0535 (12)0.0548 (14)0.0445 (11)−0.0184 (10)0.0000 (9)−0.0128 (10)
C70.0867 (18)0.0441 (14)0.0575 (14)−0.0269 (12)−0.0085 (12)−0.0063 (11)
C80.097 (2)0.0619 (17)0.0429 (12)−0.0285 (14)−0.0115 (12)−0.0043 (11)
C90.0529 (12)0.0458 (13)0.0389 (10)−0.0128 (10)−0.0045 (9)−0.0086 (9)
C100.0465 (11)0.0453 (12)0.0418 (11)−0.0138 (9)−0.0041 (8)−0.0123 (9)
C110.0553 (12)0.0453 (13)0.0443 (11)−0.0217 (10)−0.0055 (9)−0.0104 (10)
C120.0660 (14)0.0589 (15)0.0458 (12)−0.0255 (12)−0.0063 (10)−0.0155 (11)
C130.0546 (12)0.0557 (14)0.0498 (12)−0.0232 (11)−0.0011 (9)−0.0188 (10)
C140.105 (2)0.0661 (17)0.0467 (13)−0.0423 (15)−0.0147 (13)−0.0075 (12)
C150.098 (2)0.0545 (15)0.0580 (14)−0.0390 (14)−0.0117 (13)−0.0087 (12)
C160.0505 (12)0.0531 (14)0.0484 (12)−0.0216 (10)−0.0002 (9)−0.0181 (10)
C170.0507 (12)0.0549 (14)0.0496 (12)−0.0182 (10)−0.0080 (9)−0.0152 (10)
C180.0507 (12)0.0480 (13)0.0562 (13)−0.0178 (10)−0.0076 (10)−0.0146 (10)
C190.0579 (13)0.0596 (16)0.0527 (13)−0.0262 (11)0.0015 (10)−0.0215 (11)
C200.0576 (13)0.0477 (13)0.0417 (11)−0.0233 (10)−0.0057 (9)−0.0077 (9)
C210.0731 (16)0.0491 (14)0.0647 (15)−0.0231 (12)−0.0063 (12)−0.0123 (11)
C220.100 (2)0.0607 (18)0.086 (2)−0.0478 (17)−0.0129 (16)−0.0063 (15)
C230.0746 (19)0.095 (2)0.098 (2)−0.0501 (19)0.0008 (16)−0.0129 (19)
C240.0642 (18)0.083 (2)0.122 (3)−0.0289 (16)0.0144 (17)−0.031 (2)
C250.0681 (16)0.0535 (16)0.0856 (18)−0.0238 (13)0.0043 (13)−0.0218 (13)
C260.0600 (13)0.0457 (13)0.0468 (12)−0.0193 (10)−0.0061 (10)−0.0125 (10)
C270.0788 (17)0.0548 (15)0.0576 (14)−0.0278 (13)0.0038 (12)−0.0113 (12)
C280.105 (2)0.076 (2)0.088 (2)−0.0301 (19)0.0373 (19)−0.0272 (18)
C290.100 (3)0.070 (2)0.131 (3)0.0009 (19)0.029 (2)−0.027 (2)
C300.110 (3)0.058 (2)0.098 (3)0.0032 (18)−0.008 (2)−0.0051 (17)
C310.0848 (18)0.0567 (16)0.0538 (14)−0.0108 (14)−0.0067 (12)−0.0081 (12)
N10.0516 (10)0.0518 (11)0.0460 (10)−0.0171 (9)−0.0046 (8)−0.0176 (8)
N20.0629 (11)0.0457 (11)0.0360 (9)−0.0258 (9)−0.0069 (7)−0.0041 (7)
N30.0629 (11)0.0388 (10)0.0386 (9)−0.0204 (8)−0.0059 (8)−0.0041 (7)
O10.0841 (12)0.0599 (11)0.0540 (9)−0.0310 (9)−0.0121 (8)−0.0193 (8)
O20.1188 (16)0.0598 (12)0.0684 (11)−0.0432 (11)−0.0131 (11)−0.0185 (9)
O30.1088 (14)0.0638 (11)0.0454 (9)−0.0542 (10)−0.0106 (9)−0.0012 (8)
Sn10.05547 (10)0.04475 (10)0.04128 (9)−0.02024 (7)−0.00573 (6)−0.00908 (6)
Geometric parameters (Å, °) top
C32—C331.3900C10—N11.389 (3)
C32—C371.3900C10—C111.446 (3)
C32—Sn12.126 (2)C11—O31.228 (3)
C33—C341.3900C11—N21.396 (3)
C33—H330.93C12—N11.271 (3)
C34—C351.3900C12—C131.471 (3)
C34—H340.93C12—H120.93
C35—C361.3900C13—C181.388 (3)
C35—H350.93C13—C141.394 (4)
C36—C371.3900C14—C151.384 (4)
C36—H360.93C14—H140.93
C37—H370.93C15—C161.386 (3)
C32A—C37A1.3224C15—H150.93
C32A—C33A1.3900C16—C171.384 (3)
C32A—Sn12.199 (2)C16—C191.493 (3)
C33A—C34A1.3802C17—C181.382 (3)
C33A—H33A0.93C17—H170.93
C34A—C35A1.3592C18—H180.93
C34A—H34A0.93C19—O21.216 (3)
C35A—C36A1.3313C19—O11.311 (3)
C35A—H35A0.93C20—C251.377 (3)
C36A—C37A1.3792C20—C211.379 (3)
C36A—H36A0.93C20—Sn12.122 (2)
C37A—H37A0.93C21—C221.382 (4)
C1—C61.377 (3)C21—H210.9300
C1—C21.386 (3)C22—C231.366 (5)
C1—N21.421 (3)C22—H220.93
C2—C31.376 (3)C23—C241.367 (5)
C2—H20.93C23—H230.93
C3—C41.372 (4)C24—C251.382 (4)
C3—H30.93C24—H240.93
C4—C51.384 (4)C25—H250.93
C4—H40.93C26—C311.379 (3)
C5—C61.382 (3)C26—C271.389 (3)
C5—H50.93C26—Sn12.119 (2)
C6—H60.93C27—C281.376 (4)
C7—N31.456 (3)C27—H270.93
C7—H7A0.96C28—C291.370 (5)
C7—H7B0.96C28—H280.93
C7—H7C0.96C29—C301.367 (5)
C8—C91.490 (3)C29—H290.93
C8—H8A0.96C30—C311.384 (4)
C8—H8B0.96C30—H300.93
C8—H8C0.96C31—H310.93
C9—N31.356 (3)N2—N31.405 (2)
C9—C101.366 (3)O1—Sn12.044 (2)
C33—C32—C37120.0C13—C12—H12120.0
C33—C32—Sn1119.62 (10)C18—C13—C14118.5 (2)
C37—C32—Sn1120.19 (10)C18—C13—C12120.4 (2)
C32—C33—C34120.0C14—C13—C12121.1 (2)
C32—C33—H33120.0C15—C14—C13120.6 (2)
C34—C33—H33120.0C15—C14—H14119.7
C33—C34—C35120.0C13—C14—H14119.7
C33—C34—H34120.0C14—C15—C16120.6 (2)
C35—C34—H34120.0C14—C15—H15119.7
C34—C35—C36120.0C16—C15—H15119.7
C34—C35—H35120.0C17—C16—C15118.8 (2)
C36—C35—H35120.0C17—C16—C19120.7 (2)
C37—C36—C35120.0C15—C16—C19120.5 (2)
C37—C36—H36120.0C18—C17—C16120.9 (2)
C35—C36—H36120.0C18—C17—H17119.5
C36—C37—C32120.0C16—C17—H17119.5
C36—C37—H37120.0C17—C18—C13120.5 (2)
C32—C37—H37120.0C17—C18—H18119.7
C37A—C32A—C33A121.6C13—C18—H18119.7
C37A—C32A—Sn1118.54 (10)O2—C19—O1122.9 (2)
C33A—C32A—Sn1119.23 (10)O2—C19—C16123.6 (2)
C34A—C33A—C32A117.4O1—C19—C16113.5 (2)
C34A—C33A—H33A121.3C25—C20—C21118.5 (2)
C32A—C33A—H33A121.3C25—C20—Sn1120.44 (18)
C35A—C34A—C33A120.1C21—C20—Sn1121.00 (18)
C35A—C34A—H34A120.0C20—C21—C22120.8 (3)
C33A—C34A—H34A120.0C20—C21—H21119.6
C36A—C35A—C34A120.8C22—C21—H21119.6
C36A—C35A—H35A119.6C23—C22—C21119.8 (3)
C34A—C35A—H35A119.6C23—C22—H22120.1
C35A—C36A—C37A120.3C21—C22—H22120.1
C35A—C36A—H36A119.9C22—C23—C24120.2 (3)
C37A—C36A—H36A119.9C22—C23—H23119.9
C32A—C37A—C36A119.6C24—C23—H23119.9
C32A—C37A—H37A120.2C23—C24—C25120.0 (3)
C36A—C37A—H37A120.2C23—C24—H24120.0
C6—C1—C2120.57 (19)C25—C24—H24120.0
C6—C1—N2121.49 (18)C20—C25—C24120.6 (3)
C2—C1—N2117.93 (19)C20—C25—H25119.7
C3—C2—C1119.5 (2)C24—C25—H25119.7
C3—C2—H2120.2C31—C26—C27118.9 (2)
C1—C2—H2120.2C31—C26—Sn1122.89 (18)
C4—C3—C2120.6 (2)C27—C26—Sn1118.11 (18)
C4—C3—H3119.7C28—C27—C26120.7 (3)
C2—C3—H3119.7C28—C27—H27119.7
C3—C4—C5119.6 (2)C26—C27—H27119.7
C3—C4—H4120.2C29—C28—C27119.3 (3)
C5—C4—H4120.2C29—C28—H28120.3
C6—C5—C4120.5 (2)C27—C28—H28120.3
C6—C5—H5119.7C30—C29—C28121.2 (3)
C4—C5—H5119.7C30—C29—H29119.4
C1—C6—C5119.2 (2)C28—C29—H29119.4
C1—C6—H6120.4C29—C30—C31119.4 (3)
C5—C6—H6120.4C29—C30—H30120.3
N3—C7—H7A109.5C31—C30—H30120.3
N3—C7—H7B109.5C26—C31—C30120.5 (3)
H7A—C7—H7B109.5C26—C31—H31119.7
N3—C7—H7C109.5C30—C31—H31119.7
H7A—C7—H7C109.5C12—N1—C10122.07 (19)
H7B—C7—H7C109.5C11—N2—N3109.44 (16)
C9—C8—H8A109.5C11—N2—C1124.73 (17)
C9—C8—H8B109.5N3—N2—C1120.68 (16)
H8A—C8—H8B109.5C9—N3—N2106.94 (16)
C9—C8—H8C109.5C9—N3—C7124.42 (18)
H8A—C8—H8C109.5N2—N3—C7118.36 (17)
H8B—C8—H8C109.5C19—O1—Sn1117.4 (2)
N3—C9—C10110.51 (18)O1—Sn1—C26111.39 (8)
N3—C9—C8121.1 (2)O1—Sn1—C20107.81 (8)
C10—C9—C8128.3 (2)C26—Sn1—C20116.41 (9)
C9—C10—N1122.92 (19)O1—Sn1—C3291.00 (8)
C9—C10—C11107.82 (18)C26—Sn1—C32110.05 (8)
N1—C10—C11129.26 (19)C20—Sn1—C32117.23 (8)
O3—C11—N2123.60 (19)O1—Sn1—C32A100.30 (7)
O3—C11—C10131.7 (2)C26—Sn1—C32A105.28 (8)
N2—C11—C10104.70 (17)C20—Sn1—C32A114.52 (8)
N1—C12—C13119.9 (2)C32—Sn1—C32A9.4
N1—C12—H12120.0
Table 1
Selected geometric parameters (Å, °) top
C32—Sn12.126 (2)C19—O11.311 (3)
C32A—Sn12.199 (2)C20—Sn12.122 (2)
C11—O31.228 (3)C26—Sn12.119 (2)
C12—N11.271 (3)O1—Sn12.044 (2)
C19—O21.216 (3)
O2—C19—O1122.9 (2)C26—Sn1—C20116.41 (9)
C19—O1—Sn1117.4 (2)O1—Sn1—C3291.00 (8)
O1—Sn1—C26111.39 (8)C26—Sn1—C32110.05 (8)
O1—Sn1—C20107.81 (8)C20—Sn1—C32117.23 (8)
Acknowledgements top

The authors acknowledge the financial support granted by the Natural Science Foundation of JiangXi Province (grant No. 0620029) and the Education Department of Jiangxi Province (grant No. 05YB195).

references
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