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Acta Cryst. (2007). E63, m1525-m1526    [ doi:10.1107/S1600536807020090 ]

The first example of a dinuclear organotin complex with a C2N2S2Sn2 planar dicyclo fragment

X.-N. Fang, J.-H. Wu, Y. Sui, P. Hu and R.-H. Hu

Abstract top

The asymmetric unit of the unexpected title compound, 2,2,6,6-tetra-n-butyl-2,6-dichloro-4,8-bis{[(1E)-4-methoxybenzylidene]hydrazino}-1,5-diaza-2,6-distanna-3,7-dithiabicyclo[3.3.0]octa-3,7-diene bis{1,5[(1E)-4-methoxybenzylidene]thiocarbonohydrazide} ethanol disolvate, [Sn2(C4H9)4Cl2(C18H18N6O2S2)]·2C17H18N4O2S·2C2H5OH, comprises one half-molecule of the organotin complex, one thiocarbonohydrazide molecule and one ethanol solvent molecule, and is the first example of a substituted C2N2S2Sn2 planar dicyclo-organotin complex. Each SnIV atom is pentacoordinated with a distorted trigonal-bipyramidal geometry and the complex is disposed across a crystallographic centre of inversion. Weak intermolecular N-H...Cl and C-H...Cl hydrogen bonds and weak S...S interactions link the molecules of the organotin complex into one-dimensional infinite chains.

Comment top

Organotin complexes have attracted attention in supermolecular chemistry in recent years (Ma et al., 2005; Barbieri et al., 2001), whereas thiosemicarbazones and their complexes have a wide range of applications in biology (Casas et al., 2000). In the context of our continuous interest for the structural and biological properties of organotin compounds (Fang et al., 2001; 2006a), we report here the crystal structure of the title complex, (I). To the best of our knowledge, this is the first example of organotin complex containing C2N2S2Sn2 planar dicyclo fragment.

The structure of (I) is an unexpected product in our work. It crystallizes in space group P-1, with one half-molecule of an organotin complex [2,2,6,6-Tetra-n-butyl-2,6-dichloro-4,8-di[(1E)-4-methoxybenzylidene]\ hydrazino-1,5-diaza-2,6-distanna-3,7-dithiabicyclo[3.3.0]octane], one substituted thiocarbonohydrazide ligand [1,5-Bis[(1E)-4-methoxybenzylidene]thiocarbonohydrazide] and one ethanol molecule in the asymmetric unit (Fig. 1). Part of the thiocarbonohydrazide ligand molecules were cracked to form a novel substituted C2N2S2Sn2 planar dicyclo organotin complex. The five-membered ring Sn1—S1—C1—N1A—N1 is coplanar with a mean deviation of 0.024 (3) Å. The inversion center is situated at the midpoint of N1—N1A bond, and it is by this bond that the two five-membered rings are fused together. Both of the SnIV atoms are penta-coordinated with distorted trigonal-bipyramidal geometry. C10, C14 (from butyl groups) and S1 atom occupy the equatorial plane, these equatorial atoms and relative Sn atom are nearly coplanar, the mean deviation from the plane is 0.031 (4) Å. Cl1 and N1 atoms occupy the axial positions with the N1—Sn1—Cl1 bond angle 160.11 (6)°. All the C═ N bonds exist in E-configuration, and all the bond lengths in (I) are within the expected range and agree well with literature values (Altmann et al., 1998; Fang et al., 2006).

In the crystal lattice, every two molecules of the ligand are linked by the weak hydrogen bonds N6—H6···S2i to form dimers, with the attached two ethanol molecules by the strong N5—H5···O4ii and weak C25—H25···O4ii hydrogen bonds. The molecules of organotin are linked by S···S interactions (Wang et al., 2004). and N—H···Cliii, C—H···Cliii weak hydrogen bonds involving all potential S and Cl atom donors, generating one-dimensional infinite chains parallel to the a axis, as shown in Fig. 2. The 4-methoxyphenyl rings protrude on both sides of these chains and have no special intercalations [symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 1, -y + 2, -z + 1; (iii) -x + 1, -y + 2, -z].

Related literature top

For related literature, see: Altmann et al. (1998); Barbieri et al. (2001); Casas et al. (2000); Fang et al. (2001, 2006a); Ma et al. (2005); Wang et al. (2004).

For related literature, see: Fang et al. (2006b). Comment section contains one ambiguous reference to Fang et al. (2006); should this be 2006b?

Experimental top

The title compound (I) was prepared as an unexpected product in our work by the following procedure: A solution of Schiff base ligand, 1,5-Bis[(1E)-4-methoxybenzylidene]thiocarbonohydrazide, (0.342 g, 1 m mol) and dibutyltin dichloride (0.304 g, 1 m mol) in acetonitrile (20 ml) was heated for 8 h under reflux. The reaction mixture was then cooled and the pale yellow precipitate that had formed was filtered off. Recrystallization of the crude product from ethanol-DMF solution resulted in single crystals of (I) suitable for X-ray diffraction analysis after several days.

Refinement top

Slightly disorder in the ethanol was identified from the difference map. Disordered atoms were refined by applying restraints to the bond lengths [1.540 (2)Å for C35—C36 and 1.340 (2)Å for C35—O4]. All the H atoms were positioned in idealized locations and refined as riding on their carrier atoms, with O—H distances of 0.82 (hydroxyl), C—H distances of 0.93 (aryl), 0.97 (methylene) and 0.96Å (methyl) with Uiso(H) = 1.5Ueq(C) for hydroxyl and methyl, Uiso(H) = 1.2Ueq(C) for the other atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; 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 25% probability displacement ellipsoids. H atoms not involved in hydrogen bonding have been omitted. The symmetry code for A is 2 - x, 2 - y, -z.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis, hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
2,2,6,6-Tetra-n-butyl-2,6-dichloro-4,8- bis{[(1E)-4-methoxybenzylidene]hydrazino}- 1,5-diaza-2,6-distanna-3,7-dithiabicyclo[3.3.0]octa-3,7-diene 1,5-bis[(1E)-4-methoxybenzylidene]thiocarbonohydrazide ethanol solvate top
Crystal data top
[Sn2(C4H9)4Cl2(C18H18N6O2S2)]·2C17H18N4O2S·2C2H6OZ = 1
Mr = 1728.20F(000) = 894
Triclinic, P1Dx = 1.382 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9295 (6) ÅCell parameters from 9573 reflections
b = 10.3932 (7) Åθ = 2.2–28.2°
c = 24.015 (2) ŵ = 0.83 mm−1
α = 81.439 (1)°T = 296 K
β = 85.350 (1)°Block, pale yellow
γ = 70.521 (1)°0.40 × 0.31 × 0.31 mm
V = 2076.6 (3) Å3
Data collection top
Bruker APEX II area-detector
diffractometer		7145 independent reflections
Radiation source: fine-focus sealed tube6432 reflections with I > 2σ(I)
graphiteRint = 0.014
φ and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −10→10
Tmin = 0.74, Tmax = 0.77k = −12→12
13116 measured reflectionsl = −28→28
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.6928P]
where P = (Fo2 + 2Fc2)/3
7145 reflections(Δ/σ)max = 0.001
467 parametersΔρmax = 0.58 e Å−3
2 restraintsΔρmin = −0.39 e Å−3
Crystal data top
[Sn2(C4H9)4Cl2(C18H18N6O2S2)]·2C17H18N4O2S·2C2H6Oγ = 70.521 (1)°
Mr = 1728.20V = 2076.6 (3) Å3
Triclinic, P1Z = 1
a = 8.9295 (6) ÅMo Kα radiation
b = 10.3932 (7) ŵ = 0.83 mm−1
c = 24.015 (2) ÅT = 296 K
α = 81.439 (1)°0.40 × 0.31 × 0.31 mm
β = 85.350 (1)°
Data collection top
Bruker APEX II area-detector
diffractometer		7145 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		6432 reflections with I > 2σ(I)
Tmin = 0.74, Tmax = 0.77Rint = 0.014
13116 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.58 e Å−3
S = 1.04Δρmin = −0.39 e Å−3
7145 reflectionsAbsolute structure: ?
467 parametersFlack parameter: ?
2 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*/Ueq
Sn10.812698 (18)1.104088 (18)−0.091670 (7)0.04294 (8)
S10.70369 (8)0.97683 (9)−0.01266 (3)0.05509 (19)
S20.60672 (15)0.63859 (11)0.44775 (4)0.0835 (3)
O11.1578 (3)0.6447 (3)0.38324 (10)0.0870 (8)
O21.0079 (4)1.2706 (4)0.32703 (14)0.1100 (10)
O30.4216 (4)0.6818 (3)0.87416 (10)0.0846 (7)
O40.4485 (5)0.9813 (4)0.38112 (15)0.1195 (12)
H4A0.53880.95190.36760.179*
N11.0120 (2)1.0342 (2)−0.02674 (9)0.0428 (5)
N20.8235 (2)0.8662 (3)0.08325 (9)0.0499 (5)
H20.73850.84370.08650.060*
N30.9227 (2)0.8296 (2)0.12835 (9)0.0474 (5)
N40.6883 (3)0.8739 (3)0.47857 (11)0.0608 (6)
N50.6294 (3)0.7983 (3)0.52189 (11)0.0623 (6)
H50.61810.82060.55540.075*
N60.5359 (3)0.6237 (3)0.55591 (10)0.0635 (7)
H60.50710.55480.55140.076*
N70.5255 (3)0.6639 (3)0.60890 (10)0.0609 (6)
Cl10.53743 (9)1.14405 (9)−0.13637 (3)0.0652 (2)
C10.8556 (3)0.9364 (3)0.03407 (10)0.0408 (5)
C20.8603 (3)0.7939 (3)0.17573 (12)0.0564 (7)
H2A0.75610.79390.17600.068*
C30.9413 (3)0.7534 (3)0.22894 (12)0.0556 (7)
C41.1033 (3)0.7185 (3)0.23344 (13)0.0615 (8)
H41.16770.71840.20100.074*
C51.1705 (4)0.6837 (4)0.28516 (15)0.0696 (9)
H5A1.28010.65990.28740.084*
C61.0777 (4)0.6836 (3)0.33429 (14)0.0654 (8)
C70.9148 (4)0.7165 (4)0.33124 (15)0.0749 (10)
H70.85060.71570.36370.090*
C80.8499 (4)0.7509 (4)0.27789 (14)0.0722 (9)
H80.74060.77300.27530.087*
C91.0686 (6)0.6324 (5)0.43472 (16)0.1052 (15)
H9A0.99380.72080.44040.158*
H9B1.13960.59920.46550.158*
H9C1.01260.56880.43290.158*
C100.7273 (4)1.3153 (3)−0.07763 (14)0.0602 (7)
H10A0.74751.3702−0.11190.072*
H10B0.61291.3418−0.07150.072*
C110.7951 (4)1.3536 (3)−0.02949 (14)0.0634 (8)
H11A0.90841.3343−0.03660.076*
H11B0.78061.29590.00480.076*
C120.7209 (5)1.5024 (4)−0.02030 (19)0.0827 (11)
H12A0.74441.5594−0.05340.099*
H12B0.60641.5237−0.01720.099*
C130.7737 (7)1.5411 (6)0.0304 (2)0.1180 (18)
H13A0.73331.49890.06380.177*
H13B0.73401.63930.02950.177*
H13C0.88771.50990.03040.177*
C140.9298 (4)0.9572 (3)−0.14765 (14)0.0628 (8)
H14A0.90711.0019−0.18590.075*
H14B1.04350.9324−0.14350.075*
C150.8890 (5)0.8280 (4)−0.14076 (19)0.0847 (11)
H15A0.91000.7834−0.10240.102*
H15B0.77590.8519−0.14600.102*
C160.9757 (6)0.7283 (5)−0.1798 (2)0.0995 (14)
H16A0.95390.7737−0.21800.119*
H16B1.08860.7064−0.17480.119*
C170.9413 (8)0.5976 (5)−0.1746 (3)0.130 (2)
H17A0.94350.5587−0.13570.194*
H17B1.02000.5345−0.19600.194*
H17C0.83810.6146−0.18880.194*
C181.0726 (9)1.3605 (7)0.3415 (3)0.151 (3)
H18A0.99781.42140.36480.226*
H18B1.09901.41310.30810.226*
H18C1.16721.31100.36200.226*
C190.9364 (5)1.2028 (4)0.37029 (17)0.0806 (10)
C200.9198 (5)1.2282 (4)0.4242 (2)0.0896 (12)
H200.95491.29570.43460.108*
C210.8485 (5)1.1514 (4)0.46519 (18)0.0841 (11)
H210.83651.16850.50250.101*
C220.7980 (4)1.0529 (3)0.44951 (14)0.0633 (8)
C230.8144 (4)1.0330 (4)0.39310 (15)0.0739 (9)
H230.77730.96770.38170.089*
C240.8832 (5)1.1063 (5)0.35441 (18)0.0852 (11)
H240.89391.09050.31700.102*
C250.7306 (4)0.9690 (3)0.49192 (14)0.0636 (8)
H250.71880.98630.52920.076*
C260.5903 (4)0.6915 (3)0.51171 (13)0.0595 (7)
C270.4748 (4)0.5921 (3)0.64858 (13)0.0612 (7)
H270.44800.51820.64020.073*
C280.4574 (4)0.6212 (3)0.70636 (13)0.0581 (7)
C290.4751 (5)0.7397 (4)0.72069 (14)0.0690 (9)
H290.49510.80430.69250.083*
C300.4635 (5)0.7629 (4)0.77620 (14)0.0720 (9)
H300.47480.84320.78520.086*
C310.4354 (4)0.6676 (4)0.81836 (13)0.0630 (8)
C320.4171 (4)0.5487 (4)0.80527 (14)0.0681 (9)
H320.39840.48400.83370.082*
C330.4268 (4)0.5273 (4)0.74950 (14)0.0665 (8)
H330.41250.44820.74060.080*
C340.4351 (6)0.8029 (4)0.89018 (17)0.0885 (12)
H34A0.53730.81020.87780.133*
H34B0.42420.79900.93040.133*
H34C0.35310.88150.87320.133*
C350.3503 (8)0.9364 (8)0.3557 (2)0.154 (3)
H35A0.24180.98810.36580.185*
H35B0.36770.84080.37060.185*
C360.3665 (12)0.9471 (10)0.2915 (2)0.201 (4)
H36A0.40871.01970.27720.302*
H36B0.26400.96670.27620.302*
H36C0.43700.86160.28070.302*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03414 (10)0.04993 (13)0.04704 (12)−0.01539 (8)−0.00385 (7)−0.00810 (8)
S10.0380 (3)0.0843 (5)0.0499 (4)−0.0309 (3)−0.0072 (3)−0.0015 (3)
S20.1316 (9)0.0845 (7)0.0550 (5)−0.0642 (6)0.0080 (5)−0.0114 (4)
O10.0871 (18)0.103 (2)0.0635 (15)−0.0213 (15)−0.0233 (13)−0.0003 (14)
O20.128 (3)0.113 (3)0.107 (2)−0.072 (2)0.0075 (19)−0.0039 (19)
O30.117 (2)0.0871 (18)0.0569 (13)−0.0421 (16)0.0087 (13)−0.0187 (12)
O40.123 (3)0.144 (3)0.108 (2)−0.072 (3)−0.032 (2)0.016 (2)
N10.0316 (10)0.0512 (13)0.0465 (11)−0.0142 (9)−0.0047 (8)−0.0061 (9)
N20.0348 (11)0.0678 (15)0.0511 (13)−0.0232 (10)−0.0059 (9)−0.0025 (11)
N30.0385 (11)0.0530 (13)0.0531 (13)−0.0184 (10)−0.0079 (9)−0.0023 (10)
N40.0718 (17)0.0540 (15)0.0574 (15)−0.0246 (13)0.0011 (12)−0.0018 (12)
N50.0788 (18)0.0582 (16)0.0540 (14)−0.0292 (14)0.0021 (12)−0.0066 (12)
N60.0831 (18)0.0598 (16)0.0535 (14)−0.0322 (14)0.0005 (12)−0.0065 (12)
N70.0720 (17)0.0575 (15)0.0530 (14)−0.0217 (13)0.0003 (12)−0.0060 (12)
Cl10.0440 (4)0.0873 (6)0.0691 (5)−0.0273 (4)−0.0169 (3)−0.0028 (4)
C10.0319 (11)0.0455 (14)0.0467 (14)−0.0142 (10)−0.0009 (9)−0.0072 (11)
C20.0452 (15)0.069 (2)0.0595 (17)−0.0265 (14)−0.0058 (12)−0.0001 (14)
C30.0534 (16)0.0594 (18)0.0563 (17)−0.0239 (14)−0.0066 (12)0.0010 (13)
C40.0484 (16)0.072 (2)0.0597 (18)−0.0174 (15)−0.0036 (13)0.0017 (15)
C50.0524 (17)0.080 (2)0.072 (2)−0.0189 (16)−0.0111 (15)0.0019 (17)
C60.070 (2)0.061 (2)0.0615 (19)−0.0157 (16)−0.0144 (15)−0.0029 (15)
C70.067 (2)0.088 (3)0.060 (2)−0.0150 (18)−0.0011 (15)−0.0042 (17)
C80.0495 (17)0.094 (3)0.068 (2)−0.0219 (17)−0.0037 (14)0.0032 (18)
C90.124 (4)0.117 (4)0.054 (2)−0.009 (3)−0.013 (2)−0.014 (2)
C100.0494 (16)0.0533 (17)0.075 (2)−0.0076 (13)−0.0078 (14)−0.0172 (15)
C110.0637 (19)0.0587 (19)0.071 (2)−0.0210 (15)0.0015 (15)−0.0193 (15)
C120.080 (2)0.068 (2)0.105 (3)−0.0251 (19)0.010 (2)−0.032 (2)
C130.136 (4)0.119 (4)0.126 (4)−0.061 (3)0.028 (3)−0.074 (3)
C140.0591 (18)0.067 (2)0.0679 (19)−0.0245 (15)0.0097 (14)−0.0247 (16)
C150.091 (3)0.074 (2)0.099 (3)−0.039 (2)0.022 (2)−0.031 (2)
C160.117 (4)0.081 (3)0.109 (3)−0.036 (3)0.020 (3)−0.043 (3)
C170.165 (5)0.089 (3)0.153 (5)−0.058 (4)0.020 (4)−0.050 (3)
C180.210 (7)0.126 (5)0.157 (5)−0.114 (5)−0.002 (5)−0.002 (4)
C190.085 (3)0.079 (3)0.077 (2)−0.031 (2)−0.0040 (19)0.006 (2)
C200.101 (3)0.071 (2)0.112 (3)−0.049 (2)−0.006 (2)−0.012 (2)
C210.105 (3)0.074 (2)0.085 (3)−0.046 (2)−0.007 (2)−0.007 (2)
C220.0634 (18)0.0535 (18)0.074 (2)−0.0211 (15)−0.0047 (15)−0.0033 (15)
C230.080 (2)0.075 (2)0.071 (2)−0.0339 (19)0.0033 (17)−0.0082 (18)
C240.091 (3)0.094 (3)0.077 (2)−0.044 (2)0.006 (2)−0.006 (2)
C250.073 (2)0.0599 (19)0.0606 (18)−0.0247 (16)−0.0019 (15)−0.0083 (15)
C260.0691 (19)0.0536 (18)0.0560 (17)−0.0225 (15)−0.0039 (14)−0.0010 (14)
C270.072 (2)0.0545 (18)0.0591 (18)−0.0241 (15)0.0011 (14)−0.0068 (14)
C280.0642 (18)0.0535 (18)0.0554 (17)−0.0201 (14)−0.0005 (13)−0.0025 (13)
C290.093 (2)0.059 (2)0.0590 (19)−0.0350 (18)−0.0019 (16)0.0014 (15)
C300.093 (3)0.062 (2)0.069 (2)−0.0341 (19)0.0013 (18)−0.0119 (17)
C310.0655 (19)0.066 (2)0.0561 (18)−0.0204 (16)0.0046 (14)−0.0095 (15)
C320.084 (2)0.063 (2)0.0586 (19)−0.0298 (18)0.0106 (16)−0.0053 (15)
C330.077 (2)0.059 (2)0.067 (2)−0.0284 (17)0.0112 (16)−0.0123 (16)
C340.109 (3)0.088 (3)0.074 (2)−0.034 (2)0.006 (2)−0.029 (2)
C350.147 (6)0.199 (8)0.132 (5)−0.087 (5)−0.043 (4)0.020 (5)
C360.276 (11)0.247 (10)0.162 (7)−0.181 (9)0.009 (7)−0.060 (7)
Geometric parameters (Å, °) top
Sn1—C142.133 (3)C12—H12B0.9700
Sn1—C102.140 (3)C13—H13A0.9600
Sn1—N12.319 (2)C13—H13B0.9600
Sn1—S12.4717 (7)C13—H13C0.9600
Sn1—Cl12.6421 (7)C14—C151.488 (5)
S1—C11.732 (2)C14—H14A0.9700
S2—C261.687 (3)C14—H14B0.9700
O1—C61.364 (4)C15—C161.479 (5)
O1—C91.428 (5)C15—H15A0.9700
O2—C181.349 (6)C15—H15B0.9700
O2—C191.399 (5)C16—C171.475 (6)
O3—C311.361 (4)C16—H16A0.9700
O3—C341.413 (5)C16—H16B0.9700
O4—C351.343 (8)C17—H17A0.9600
O4—H4A0.8200C17—H17B0.9600
N1—C1i1.309 (3)C17—H17C0.9600
N1—N1i1.409 (4)C18—H18A0.9600
N2—C11.355 (3)C18—H18B0.9600
N2—N31.382 (3)C18—H18C0.9600
N2—H20.8600C19—C201.346 (6)
N3—C21.286 (4)C19—C241.356 (6)
N4—C251.260 (4)C20—C211.419 (6)
N4—N51.385 (4)C20—H200.9300
N5—C261.329 (4)C21—C221.358 (5)
N5—H50.8600C21—H210.9300
N6—C261.335 (4)C22—C231.389 (5)
N6—N71.384 (3)C22—C251.465 (5)
N6—H60.8600C23—C241.352 (5)
N7—C271.270 (4)C23—H230.9300
C1—N1i1.309 (3)C24—H240.9300
C2—C31.456 (4)C25—H250.9300
C2—H2A0.9300C27—C281.449 (4)
C3—C81.378 (4)C27—H270.9300
C3—C41.379 (4)C28—C291.388 (5)
C4—C51.370 (4)C28—C331.389 (5)
C4—H40.9300C29—C301.379 (5)
C5—C61.386 (5)C29—H290.9300
C5—H5A0.9300C30—C311.377 (5)
C6—C71.384 (5)C30—H300.9300
C7—C81.397 (5)C31—C321.382 (5)
C7—H70.9300C32—C331.381 (5)
C8—H80.9300C32—H320.9300
C9—H9A0.9600C33—H330.9300
C9—H9B0.9600C34—H34A0.9600
C9—H9C0.9600C34—H34B0.9600
C10—C111.507 (4)C34—H34C0.9600
C10—H10A0.9700C35—C361.528 (7)
C10—H10B0.9700C35—H35A0.9700
C11—C121.509 (5)C35—H35B0.9700
C11—H11A0.9700C36—H36A0.9600
C11—H11B0.9700C36—H36B0.9600
C12—C131.493 (6)C36—H36C0.9600
C12—H12A0.9700
C14—Sn1—C10147.6 (2)H14A—C14—H14B107.3
C14—Sn1—N196.5 (2)C16—C15—C14115.1 (3)
C10—Sn1—N195.9 (2)C16—C15—H15A108.5
C14—Sn1—S1105.58 (9)C14—C15—H15A108.5
C10—Sn1—S1106.3 (2)C16—C15—H15B108.5
N1—Sn1—S177.13 (6)C14—C15—H15B108.5
C14—Sn1—Cl190.29 (9)H15A—C15—H15B107.5
C10—Sn1—Cl188.08 (8)C17—C16—C15117.6 (4)
N1—Sn1—Cl1160.11 (6)C17—C16—H16A107.9
S1—Sn1—Cl183.04 (2)C15—C16—H16A107.9
C1—S1—Sn199.19 (9)C17—C16—H16B107.9
C6—O1—C9117.9 (3)C15—C16—H16B107.9
C18—O2—C19117.2 (4)H16A—C16—H16B107.2
C31—O3—C34118.2 (3)C16—C17—H17A109.5
C35—O4—H4A109.5C16—C17—H17B109.5
C1i—N1—N1i115.5 (2)H17A—C17—H17B109.5
C1i—N1—Sn1124.44 (18)C16—C17—H17C109.5
N1i—N1—Sn1119.78 (19)H17A—C17—H17C109.5
C1—N2—N3122.2 (2)H17B—C17—H17C109.5
C1—N2—H2118.9O2—C18—H18A109.5
N3—N2—H2118.9O2—C18—H18B109.5
C2—N3—N2115.0 (2)H18A—C18—H18B109.5
C25—N4—N5116.5 (3)O2—C18—H18C109.5
C26—N5—N4120.1 (3)H18A—C18—H18C109.5
C26—N5—H5119.9H18B—C18—H18C109.5
N4—N5—H5119.9C20—C19—C24120.7 (4)
C26—N6—N7120.2 (3)C20—C19—O2124.2 (4)
C26—N6—H6119.9C24—C19—O2115.1 (4)
N7—N6—H6119.9C19—C20—C21119.8 (4)
C27—N7—N6115.9 (3)C19—C20—H20120.1
N1i—C1—N2120.3 (2)C21—C20—H20120.1
N1i—C1—S1128.1 (2)C22—C21—C20119.5 (4)
N2—C1—S1111.53 (17)C22—C21—H21120.3
N3—C2—C3124.6 (3)C20—C21—H21120.3
N3—C2—H2A117.7C21—C22—C23118.5 (3)
C3—C2—H2A117.7C21—C22—C25119.9 (3)
C8—C3—C4118.0 (3)C23—C22—C25121.6 (3)
C8—C3—C2117.8 (3)C24—C23—C22121.5 (4)
C4—C3—C2124.1 (3)C24—C23—H23119.2
C5—C4—C3120.7 (3)C22—C23—H23119.2
C5—C4—H4119.6C23—C24—C19120.0 (4)
C3—C4—H4119.6C23—C24—H24120.0
C4—C5—C6121.0 (3)C19—C24—H24120.0
C4—C5—H5A119.5N4—C25—C22120.9 (3)
C6—C5—H5A119.5N4—C25—H25119.6
O1—C6—C7124.4 (3)C22—C25—H25119.6
O1—C6—C5115.8 (3)N5—C26—N6116.2 (3)
C7—C6—C5119.7 (3)N5—C26—S2124.2 (2)
C6—C7—C8117.9 (3)N6—C26—S2119.6 (2)
C6—C7—H7121.0N7—C27—C28122.4 (3)
C8—C7—H7121.0N7—C27—H27118.8
C3—C8—C7122.6 (3)C28—C27—H27118.8
C3—C8—H8118.7C29—C28—C33118.0 (3)
C7—C8—H8118.7C29—C28—C27121.8 (3)
O1—C9—H9A109.5C33—C28—C27120.1 (3)
O1—C9—H9B109.5C30—C29—C28120.8 (3)
H9A—C9—H9B109.5C30—C29—H29119.6
O1—C9—H9C109.5C28—C29—H29119.6
H9A—C9—H9C109.5C31—C30—C29120.2 (3)
H9B—C9—H9C109.5C31—C30—H30119.9
C11—C10—Sn1117.4 (2)C29—C30—H30119.9
C11—C10—H10A107.9O3—C31—C30124.3 (3)
Sn1—C10—H10A107.9O3—C31—C32115.5 (3)
C11—C10—H10B107.9C30—C31—C32120.2 (3)
Sn1—C10—H10B107.9C33—C32—C31119.2 (3)
H10A—C10—H10B107.2C33—C32—H32120.4
C10—C11—C12113.9 (3)C31—C32—H32120.4
C10—C11—H11A108.8C32—C33—C28121.6 (3)
C12—C11—H11A108.8C32—C33—H33119.2
C10—C11—H11B108.8C28—C33—H33119.2
C12—C11—H11B108.8O3—C34—H34A109.5
H11A—C11—H11B107.7O3—C34—H34B109.5
C13—C12—C11115.5 (4)H34A—C34—H34B109.5
C13—C12—H12A108.4O3—C34—H34C109.5
C11—C12—H12A108.4H34A—C34—H34C109.5
C13—C12—H12B108.4H34B—C34—H34C109.5
C11—C12—H12B108.4O4—C35—C36116.3 (5)
H12A—C12—H12B107.5O4—C35—H35A108.2
C12—C13—H13A109.5C36—C35—H35A108.2
C12—C13—H13B109.5O4—C35—H35B108.2
H13A—C13—H13B109.5C36—C35—H35B108.2
C12—C13—H13C109.5H35A—C35—H35B107.4
H13A—C13—H13C109.5C35—C36—H36A109.5
H13B—C13—H13C109.5C35—C36—H36B109.5
C15—C14—Sn1117.1 (2)H36A—C36—H36B109.5
C15—C14—H14A108.0C35—C36—H36C109.5
Sn1—C14—H14A108.0H36A—C36—H36C109.5
C15—C14—H14B108.0H36B—C36—H36C109.5
Sn1—C14—H14B108.0
Symmetry codes: (i) −x+2, −y+2, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N70.862.262.619 (4)105
C2—H2A···Cl1ii0.932.703.572 (3)157
C25—H25···O4iii0.932.523.354 (5)150
N2—H2···Cl1ii0.862.623.398 (2)151
N6—H6···S2iv0.862.533.386 (3)171
N5—H5···O4iii0.862.623.379 (5)147
Symmetry codes: (ii) −x+1, −y+2, −z; (iii) −x+1, −y+2, −z+1; (iv) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Sn1—C142.133 (3)Sn1—S12.4717 (7)
Sn1—C102.140 (3)Sn1—Cl12.6421 (7)
Sn1—N12.319 (2)S1—C11.732 (2)
C14—Sn1—C10147.6 (2)N1—Sn1—S177.13 (6)
C14—Sn1—N196.5 (2)C14—Sn1—Cl190.29 (9)
C10—Sn1—N195.9 (2)C10—Sn1—Cl188.08 (8)
C14—Sn1—S1105.58 (9)N1—Sn1—Cl1160.11 (6)
C10—Sn1—S1106.3 (2)S1—Sn1—Cl183.04 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N70.862.262.619 (4)105
C2—H2A···Cl1i0.932.703.572 (3)157
C25—H25···O4ii0.932.523.354 (5)150
N2—H2···Cl1i0.862.623.398 (2)151
N6—H6···S2iii0.862.533.386 (3)171
N5—H5···O4ii0.862.623.379 (5)147
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

We gratefully acknowledge financial support from the Natural Science Foundation of JiangXi Province (No. 0620029).

references
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