Tris(2,4-dimethyl­benzene­thiol­ato)phenyl­tin(IV)

Flores-Figueroa, A.; Hernández-Ortega, S.; Castillo, I.

doi:10.1107/S1600536810039851

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1389-m1390

https://doi.org/10.1107/S1600536810039851

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Tris(2,4-dimethylbenzenethiolato)phenyltin(IV)

Aarón Flores-Figueroa,^a Simón Hernández-Ortega ^a ^* and Ivan Castillo ^a ^*

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
^*Correspondence e-mail: simonho@unam.mx, joseivan@unam.mx

(Received 20 September 2010; accepted 5 October 2010; online 13 October 2010)

In the title compound, [Sn(C₆H₅)(C₈H₉S)₃], the Sn atom has an approximately tetrahedral SNCS₃ geometry, with angles at this atom ranging from 105.13 (3) to 113.54 (9)°. The crystal packing does not involve any significant intermolecular interactions, although the benzene rings are involved in a number of weak intra- and intermolecular C—H⋯π interactions.

Related literature

For background to the development of synthetic methods for highly substituted thiophenols with varying degrees of steric hindrance, see: Lloyd-Jones et al. (2008 ); Fleischer (2005 ); Huber et al. (1997 ); Estudiante-Negrete et al. (2007 ). For the synthesis of phenol derivatives, see: Flores-Figueroa et al. (2005 ); Mondragón et al. (2010 ). For similar structures, see: Huber et al. (1997); Li et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Sn(C₆H₅)(C₈H₉S)₃]
M_r = 607.43
Triclinic, $[P \overline 1]$
a = 9.2717 (7) Å
b = 10.6370 (8) Å
c = 15.6486 (11) Å
α = 93.420 (2)°
β = 93.520 (1)°
γ = 105.800 (1)°
V = 1477.51 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 298 K
0.32 × 0.26 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.705, T_max = 0.958
12493 measured reflections
5416 independent reflections
4057 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.061
S = 0.86
5416 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1	0.93	2.72	3.557 (3)	149
C13—H13C⋯Cg2ⁱ	0.96	2.75	3.579 (3)	144
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810039851/fj2342sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039851/fj2342Isup2.hkl

checkCIF report

Comment top

The development of synthetic methods for highly substituted thiophenols with varying degrees of steric hindrance has been an active field of research (Lloyd-Jones et al., 2008), due in part to the potential of sterically encumbered thiophenols to emulate the active site of sulfur-rich metalloenzymes (Fleischer, 2005). In this context, we developed a series of 2,4-disubstituted thiophenols (Flores-Figueroa et al., 2005, Mondragón et al.,2010), among which 2,4-dimethylthiophenol represents a commercially available ligand. In order to assess the steric properties of this thiophenol, we soughtout to prepare a metal-thiolate derivative amenable to structural characterization. Since phenyl- and diphenyltin (IV) derivatives tend to be crystalline materials (Huber et al., 1997 & Estudiante-Negrete et al., 2007), we decided to employ PhSnCl₃ to introduce the 2,4-dimethylthiophenolate moiety. Thus, the reaction of 3 equivalents of 2,4-Me₂C₆H₃SH with PhSnCl₃ in the presence of 3 equivalents of triethylamine afforded the title compound phenyl tris(2,4-dimethylphenylthiolate)tin (IV) (I) in good yield.

The structure of the title compound (PhSn(S-2,4-Me₂C₆H₃)₃,) is shown with numbering scheme in Figure 1. According to the bond angles, (I) exhibits a slightly distorted tetrahedral geometry. The phenyl ring (C1—C6) is in a close to coplanar disposition with respect to one of the 2,4-dimethylphenyl groups (C23–C30), forming a dihedral angle of 25.3 (2)°. The Sn—C distance (2.114 (3) Å) is slightly shorter than those described for the related compounds (Allen et al., 1987) phenyl tris(pyridinthiolate)tin [2.139 (5) Å, PhSn(SPy)₃ (Huber et al., 1997)] and phenyl tris(pyrimidinethiolato)tin [2.139 (3) Å, PhSn(SPym)₃ (Li et al., 2006)]. The Sn—S distances are shorter than those in PhSn(SPy)₃ [2.491–2.576 Å], and PhSn(SPym)₃[2.455–2.552 Å]. Due to the geometry adopted, in the crystal structure, there are C—H-π, intra and intermolecular interactions.

Related literature top

For background to the development of synthetic methods for highly substituted thiophenols with varying degrees of steric hindrance, see: Lloyd-Jones et al. (2008); Fleischer (2005);dn Huber et al. (1997); Estudiante-Negrete et al. (2007). For the synthesis of phenol derivatives, see: Flores-Figueroa et al. (2005); Mondragón et al. (2010). For similar structures, see; Huber et al. (1997); Li et al. (2006) et al.987 . For bond-length data, see: Allen et al. (1987).

Experimental top

To a tetrahydrofuran solution of 2,4-dimethylthiophenol (0.50 g, 3.70 mmol) was added triethylamine (0.65 ml, 4.07 mmol) under an atmosphere of N₂. After stirring for 1 h, PhSnCl₃ (0.20 mL, 1.23 mmol) was added via syringe, and the mixture was stirred overnight. The volatile materials were evaporated under reduced pressure, and the solid was extracted with hexane (2 x 15 ml), and X-ray quality crystals were obtained by slow evaporation of the solution. Yield: 0.48 g (64%); m.p. 320–323 K; IR (KBr, cm^-1) 3056, 3012, 2916, 2859, 2728, 1898, 1753, 1598, 1471, 1434, 1373, 1266,1229, 1162, 1138, 1069, 1042, 876, 811, 728, 695, 620, 543, 443, 372, 299; ¹H NMR (300 MHz, CDCl₃, TMS internal reference δ p.p.m.)7.20 (2H, m, Ph) 7.11 (3H, d,ArH), 7.08 (1H, s, Ph), 6.95 (2H, d, Ph), 6.85 (3H, s, ArH), 6.69 (3H, d,ArH), 2.18 (18H, s, ArMe); ¹³C NMR (75 MHz, CDCl₃, TMS internal reference, δ p.p.m.)142.29, 139.48, 137.62, 136. 60, 135.17, 131.58, 130.44, 128.69, 127.32,123.88, 22.19, 21.03.

Structure description top

For background to the development of synthetic methods for highly substituted thiophenols with varying degrees of steric hindrance, see: Lloyd-Jones et al. (2008); Fleischer (2005);dn Huber et al. (1997); Estudiante-Negrete et al. (2007). For the synthesis of phenol derivatives, see: Flores-Figueroa et al. (2005); Mondragón et al. (2010). For similar structures, see; Huber et al. (1997); Li et al. (2006) et al.987 . For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. The molecular structure of PhSn(SMe₂Ph)₃ with numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Only the H atoms involved in C—H-π and S-π interactions are shown.

Tris(2,4-dimethylbenzenethiolato)phenyltin(IV) top

Crystal data top

[Sn(C₆H₅)(C₈H₉S)₃]	Z = 2
M_r = 607.43	F(000) = 620
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2717 (7) Å	Cell parameters from 6072 reflections
b = 10.6370 (8) Å	θ = 2.3–25.4°
c = 15.6486 (11) Å	µ = 1.09 mm⁻¹
α = 93.420 (2)°	T = 298 K
β = 93.520 (1)°	Prism-lamina, colourless
γ = 105.800 (1)°	0.32 × 0.26 × 0.04 mm
V = 1477.51 (19) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5416 independent reflections
Radiation source: fine-focus sealed tube	4057 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 0.83 pixels mm^-1	θ_max = 25.4°, θ_min = 1.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	k = −12→12
T_min = 0.705, T_max = 0.958	l = −18→18
12493 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.021P)²] where P = (F_o² + 2F_c²)/3
5416 reflections	(Δ/σ)_max = 0.002
313 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Sn(C₆H₅)(C₈H₉S)₃]	γ = 105.800 (1)°
M_r = 607.43	V = 1477.51 (19) Å³
Triclinic, P1	Z = 2
a = 9.2717 (7) Å	Mo Kα radiation
b = 10.6370 (8) Å	µ = 1.09 mm⁻¹
c = 15.6486 (11) Å	T = 298 K
α = 93.420 (2)°	0.32 × 0.26 × 0.04 mm
β = 93.520 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5416 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	4057 reflections with I > 2σ(I)
T_min = 0.705, T_max = 0.958	R_int = 0.036
12493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 0.86	Δρ_max = 0.64 e Å⁻³
5416 reflections	Δρ_min = −0.37 e Å⁻³
313 parameters

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

	x	y	z	U_iso*/U_eq
Sn	0.76585 (2)	0.68776 (2)	0.732737 (14)	0.04856 (8)
S1	0.79793 (10)	0.74342 (8)	0.88495 (5)	0.0604 (2)
S2	0.76443 (10)	0.46303 (9)	0.70323 (6)	0.0713 (3)
S3	0.97179 (9)	0.83866 (9)	0.67586 (6)	0.0649 (3)
C1	0.5620 (3)	0.7073 (3)	0.6745 (2)	0.0493 (8)
C2	0.4930 (4)	0.7944 (3)	0.7097 (2)	0.0613 (9)
H2	0.5331	0.8414	0.7617	0.074*
C3	0.3652 (4)	0.8137 (4)	0.6695 (3)	0.0784 (11)
H3	0.3188	0.8721	0.6949	0.094*
C4	0.3072 (4)	0.7475 (4)	0.5931 (3)	0.0784 (12)
H4	0.2211	0.7607	0.5659	0.094*
C5	0.3745 (4)	0.6615 (4)	0.5557 (2)	0.0799 (12)
H5	0.3355	0.6172	0.5027	0.096*
C6	0.5015 (4)	0.6405 (4)	0.5974 (2)	0.0698 (10)
H6	0.5460	0.5803	0.5726	0.084*
C7	0.9858 (3)	0.8485 (3)	0.88924 (18)	0.0480 (8)
C8	1.0125 (4)	0.9837 (3)	0.88760 (18)	0.0503 (8)
C9	1.1612 (4)	1.0570 (3)	0.89292 (19)	0.0615 (9)
H9	1.1811	1.1475	0.8925	0.074*
C10	1.2818 (4)	1.0050 (4)	0.8988 (2)	0.0627 (9)
C11	1.2497 (4)	0.8703 (4)	0.8994 (2)	0.0652 (10)
H11	1.3281	0.8313	0.9029	0.078*
C12	1.1045 (4)	0.7937 (3)	0.89512 (19)	0.0558 (9)
H12	1.0855	0.7034	0.8961	0.067*
C13	0.8877 (4)	1.0482 (3)	0.8784 (2)	0.0729 (10)
H13A	0.8203	1.0071	0.8294	0.109*
H13B	0.9292	1.1395	0.8707	0.109*
H13C	0.8338	1.0392	0.9292	0.109*
C14	1.4406 (4)	1.0917 (4)	0.9042 (3)	0.1016 (14)
H14A	1.4584	1.1336	0.8517	0.152*
H14B	1.5094	1.0398	0.9131	0.152*
H14C	1.4553	1.1572	0.9513	0.152*
C15	0.9354 (3)	0.4663 (3)	0.7653 (2)	0.0525 (8)
C16	0.9311 (3)	0.4193 (3)	0.8463 (2)	0.0519 (8)
C17	1.0672 (4)	0.4228 (3)	0.8900 (2)	0.0564 (9)
H17	1.0661	0.3920	0.9444	0.068*
C18	1.2041 (4)	0.4697 (3)	0.8564 (2)	0.0584 (9)
C19	1.2029 (4)	0.5147 (3)	0.7760 (2)	0.0673 (10)
H19	1.2935	0.5469	0.7517	0.081*
C20	1.0702 (4)	0.5132 (3)	0.7307 (2)	0.0645 (9)
H20	1.0720	0.5441	0.6763	0.077*
C21	0.7866 (4)	0.3664 (3)	0.8865 (2)	0.0773 (11)
H21A	0.7355	0.4334	0.8922	0.116*
H21B	0.8074	0.3391	0.9422	0.116*
H21C	0.7240	0.2928	0.8508	0.116*
C22	1.3519 (4)	0.4742 (4)	0.9061 (2)	0.0858 (12)
H22A	1.4186	0.4506	0.8676	0.129*
H22B	1.3332	0.4137	0.9500	0.129*
H22C	1.3970	0.5613	0.9322	0.129*
C23	0.8789 (3)	0.8297 (3)	0.5717 (2)	0.0579 (9)
C24	0.8116 (4)	0.9252 (3)	0.5474 (2)	0.0661 (10)
C25	0.7413 (5)	0.9110 (4)	0.4651 (3)	0.0882 (13)
H25	0.6951	0.9741	0.4485	0.106*
C26	0.7372 (5)	0.8077 (5)	0.4068 (3)	0.0920 (14)
C27	0.8052 (5)	0.7156 (4)	0.4322 (3)	0.0902 (13)
H27	0.8037	0.6447	0.3941	0.108*
C28	0.8759 (4)	0.7266 (4)	0.5136 (2)	0.0759 (11)
H28	0.9223	0.6632	0.5294	0.091*
C29	0.8112 (5)	1.0413 (4)	0.6079 (3)	0.0950 (13)
H29A	0.7519	1.0114	0.6547	0.143*
H29B	0.7690	1.1005	0.5776	0.143*
H29C	0.9124	1.0857	0.6299	0.143*
C30	0.6584 (6)	0.7974 (5)	0.3179 (3)	0.146 (2)
H30A	0.5860	0.8471	0.3188	0.219*
H30B	0.6081	0.7072	0.3006	0.219*
H30C	0.7310	0.8315	0.2780	0.219*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.04127 (13)	0.05660 (15)	0.04794 (14)	0.01525 (11)	−0.00392 (9)	0.00492 (10)
S1	0.0608 (6)	0.0633 (6)	0.0494 (5)	0.0041 (5)	0.0036 (4)	0.0058 (4)
S2	0.0706 (6)	0.0607 (6)	0.0782 (7)	0.0212 (5)	−0.0255 (5)	−0.0114 (5)
S3	0.0442 (5)	0.0874 (7)	0.0578 (6)	0.0085 (5)	0.0002 (4)	0.0123 (5)
C1	0.0378 (18)	0.057 (2)	0.053 (2)	0.0136 (16)	0.0015 (15)	0.0104 (17)
C2	0.050 (2)	0.066 (2)	0.069 (2)	0.0185 (19)	−0.0010 (18)	0.0057 (19)
C3	0.060 (3)	0.080 (3)	0.104 (3)	0.036 (2)	0.005 (2)	0.009 (2)
C4	0.048 (2)	0.098 (3)	0.094 (3)	0.026 (2)	−0.006 (2)	0.034 (3)
C5	0.058 (2)	0.112 (3)	0.063 (3)	0.021 (2)	−0.0156 (19)	−0.003 (2)
C6	0.050 (2)	0.089 (3)	0.074 (3)	0.029 (2)	−0.0029 (19)	−0.008 (2)
C7	0.057 (2)	0.047 (2)	0.0360 (18)	0.0095 (17)	−0.0030 (15)	−0.0001 (14)
C8	0.062 (2)	0.049 (2)	0.0385 (18)	0.0144 (18)	−0.0052 (15)	0.0018 (15)
C9	0.081 (3)	0.046 (2)	0.048 (2)	0.005 (2)	−0.0101 (18)	0.0026 (16)
C10	0.057 (2)	0.073 (3)	0.050 (2)	0.005 (2)	−0.0043 (17)	0.0099 (19)
C11	0.062 (2)	0.083 (3)	0.054 (2)	0.028 (2)	−0.0076 (17)	0.0047 (19)
C12	0.066 (2)	0.052 (2)	0.049 (2)	0.017 (2)	−0.0063 (17)	0.0040 (16)
C13	0.087 (3)	0.061 (2)	0.074 (3)	0.031 (2)	−0.008 (2)	0.0000 (19)
C14	0.069 (3)	0.115 (3)	0.098 (3)	−0.014 (3)	−0.015 (2)	0.027 (3)
C15	0.054 (2)	0.0442 (19)	0.060 (2)	0.0171 (17)	−0.0060 (17)	−0.0017 (16)
C16	0.051 (2)	0.0379 (18)	0.067 (2)	0.0131 (16)	0.0047 (17)	0.0106 (16)
C17	0.059 (2)	0.047 (2)	0.065 (2)	0.0169 (18)	0.0013 (18)	0.0151 (17)
C18	0.053 (2)	0.047 (2)	0.077 (3)	0.0186 (18)	−0.0001 (19)	0.0082 (18)
C19	0.052 (2)	0.066 (2)	0.090 (3)	0.0209 (19)	0.020 (2)	0.018 (2)
C20	0.074 (3)	0.069 (2)	0.060 (2)	0.030 (2)	0.014 (2)	0.0170 (18)
C21	0.061 (2)	0.068 (2)	0.103 (3)	0.013 (2)	0.011 (2)	0.029 (2)
C22	0.059 (2)	0.087 (3)	0.113 (3)	0.027 (2)	−0.013 (2)	0.010 (2)
C23	0.052 (2)	0.068 (2)	0.050 (2)	0.0091 (19)	0.0078 (16)	0.0087 (19)
C24	0.075 (3)	0.062 (2)	0.054 (2)	0.005 (2)	0.0029 (19)	0.0147 (19)
C25	0.106 (3)	0.079 (3)	0.075 (3)	0.018 (3)	−0.007 (3)	0.027 (2)
C26	0.113 (4)	0.091 (3)	0.055 (3)	0.002 (3)	−0.007 (2)	0.015 (3)
C27	0.116 (4)	0.089 (3)	0.058 (3)	0.020 (3)	0.007 (2)	−0.008 (2)
C28	0.074 (3)	0.090 (3)	0.066 (3)	0.025 (2)	0.009 (2)	0.006 (2)
C29	0.125 (4)	0.072 (3)	0.092 (3)	0.031 (3)	0.005 (3)	0.015 (2)
C30	0.197 (6)	0.145 (5)	0.072 (3)	0.017 (4)	−0.044 (3)	0.016 (3)

Geometric parameters (Å, º) top

Sn—C1	2.114 (3)	C15—C20	1.371 (4)
Sn—S3	2.3927 (9)	C15—C16	1.390 (4)
Sn—S1	2.4002 (9)	C16—C17	1.388 (4)
Sn—S2	2.4037 (9)	C16—C21	1.498 (4)
S1—C7	1.790 (3)	C17—C18	1.380 (4)
S2—C15	1.798 (3)	C17—H17	0.9300
S3—C23	1.782 (3)	C18—C19	1.373 (4)
C1—C6	1.368 (4)	C18—C22	1.521 (4)
C1—C2	1.370 (4)	C19—C20	1.378 (4)
C2—C3	1.378 (4)	C19—H19	0.9300
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.353 (5)	C21—H21A	0.9600
C3—H3	0.9300	C21—H21B	0.9600
C4—C5	1.363 (5)	C21—H21C	0.9600
C4—H4	0.9300	C22—H22A	0.9600
C5—C6	1.389 (4)	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—H6	0.9300	C23—C28	1.375 (4)
C7—C12	1.379 (4)	C23—C24	1.388 (4)
C7—C8	1.394 (4)	C24—C25	1.388 (5)
C8—C9	1.381 (4)	C24—C29	1.512 (5)
C8—C13	1.501 (4)	C25—C26	1.376 (5)
C9—C10	1.377 (4)	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.365 (5)
C10—C11	1.382 (4)	C26—C30	1.516 (5)
C10—C14	1.504 (4)	C27—C28	1.380 (5)
C11—C12	1.365 (4)	C27—H27	0.9300
C11—H11	0.9300	C28—H28	0.9300
C12—H12	0.9300	C29—H29A	0.9600
C13—H13A	0.9600	C29—H29B	0.9600
C13—H13B	0.9600	C29—H29C	0.9600
C13—H13C	0.9600	C30—H30A	0.9600
C14—H14A	0.9600	C30—H30B	0.9600
C14—H14B	0.9600	C30—H30C	0.9600
C14—H14C	0.9600

C1—Sn—S3	108.97 (8)	C16—C15—S2	120.6 (3)
C1—Sn—S1	113.54 (9)	C17—C16—C15	117.5 (3)
S3—Sn—S1	105.13 (3)	C17—C16—C21	120.3 (3)
C1—Sn—S2	106.68 (9)	C15—C16—C21	122.2 (3)
S3—Sn—S2	112.83 (4)	C18—C17—C16	123.1 (3)
S1—Sn—S2	109.83 (3)	C18—C17—H17	118.5
C7—S1—Sn	97.37 (10)	C16—C17—H17	118.5
C15—S2—Sn	98.83 (10)	C19—C18—C17	117.4 (3)
C23—S3—Sn	95.05 (11)	C19—C18—C22	120.6 (3)
C6—C1—C2	118.1 (3)	C17—C18—C22	122.0 (3)
C6—C1—Sn	120.8 (2)	C18—C19—C20	121.3 (3)
C2—C1—Sn	120.9 (2)	C18—C19—H19	119.4
C1—C2—C3	121.3 (3)	C20—C19—H19	119.4
C1—C2—H2	119.3	C15—C20—C19	120.4 (3)
C3—C2—H2	119.3	C15—C20—H20	119.8
C4—C3—C2	119.8 (4)	C19—C20—H20	119.8
C4—C3—H3	120.1	C16—C21—H21A	109.5
C2—C3—H3	120.1	C16—C21—H21B	109.5
C3—C4—C5	120.3 (3)	H21A—C21—H21B	109.5
C3—C4—H4	119.8	C16—C21—H21C	109.5
C5—C4—H4	119.8	H21A—C21—H21C	109.5
C4—C5—C6	119.6 (4)	H21B—C21—H21C	109.5
C4—C5—H5	120.2	C18—C22—H22A	109.5
C6—C5—H5	120.2	C18—C22—H22B	109.5
C1—C6—C5	120.8 (3)	H22A—C22—H22B	109.5
C1—C6—H6	119.6	C18—C22—H22C	109.5
C5—C6—H6	119.6	H22A—C22—H22C	109.5
C12—C7—C8	120.2 (3)	H22B—C22—H22C	109.5
C12—C7—S1	119.0 (2)	C28—C23—C24	119.4 (3)
C8—C7—S1	120.8 (3)	C28—C23—S3	119.0 (3)
C9—C8—C7	116.6 (3)	C24—C23—S3	121.6 (3)
C9—C8—C13	120.8 (3)	C23—C24—C25	118.1 (4)
C7—C8—C13	122.5 (3)	C23—C24—C29	122.1 (3)
C10—C9—C8	124.3 (3)	C25—C24—C29	119.8 (4)
C10—C9—H9	117.8	C26—C25—C24	122.8 (4)
C8—C9—H9	117.8	C26—C25—H25	118.6
C9—C10—C11	116.9 (3)	C24—C25—H25	118.6
C9—C10—C14	121.0 (4)	C27—C26—C25	117.9 (4)
C11—C10—C14	122.0 (4)	C27—C26—C30	121.8 (5)
C12—C11—C10	120.9 (3)	C25—C26—C30	120.4 (5)
C12—C11—H11	119.5	C26—C27—C28	120.9 (4)
C10—C11—H11	119.5	C26—C27—H27	119.6
C11—C12—C7	121.0 (3)	C28—C27—H27	119.6
C11—C12—H12	119.5	C23—C28—C27	121.0 (4)
C7—C12—H12	119.5	C23—C28—H28	119.5
C8—C13—H13A	109.5	C27—C28—H28	119.5
C8—C13—H13B	109.5	C24—C29—H29A	109.5
H13A—C13—H13B	109.5	C24—C29—H29B	109.5
C8—C13—H13C	109.5	H29A—C29—H29B	109.5
H13A—C13—H13C	109.5	C24—C29—H29C	109.5
H13B—C13—H13C	109.5	H29A—C29—H29C	109.5
C10—C14—H14A	109.5	H29B—C29—H29C	109.5
C10—C14—H14B	109.5	C26—C30—H30A	109.5
H14A—C14—H14B	109.5	C26—C30—H30B	109.5
C10—C14—H14C	109.5	H30A—C30—H30B	109.5
H14A—C14—H14C	109.5	C26—C30—H30C	109.5
H14B—C14—H14C	109.5	H30A—C30—H30C	109.5
C20—C15—C16	120.3 (3)	H30B—C30—H30C	109.5
C20—C15—S2	119.0 (3)

C1—Sn—S1—C7	−131.63 (14)	C14—C10—C11—C12	179.5 (3)
S3—Sn—S1—C7	−12.61 (11)	C10—C11—C12—C7	0.6 (5)
S2—Sn—S1—C7	109.04 (11)	C8—C7—C12—C11	0.0 (5)
C1—Sn—S2—C15	−175.21 (14)	S1—C7—C12—C11	−179.3 (2)
S3—Sn—S2—C15	65.16 (12)	Sn—S2—C15—C20	−81.6 (3)
S1—Sn—S2—C15	−51.77 (12)	Sn—S2—C15—C16	99.9 (2)
C1—Sn—S3—C23	−32.90 (16)	C20—C15—C16—C17	0.4 (5)
S1—Sn—S3—C23	−154.93 (13)	S2—C15—C16—C17	178.9 (2)
S2—Sn—S3—C23	85.39 (13)	C20—C15—C16—C21	−179.6 (3)
S3—Sn—C1—C6	85.5 (3)	S2—C15—C16—C21	−1.1 (4)
S1—Sn—C1—C6	−157.8 (2)	C15—C16—C17—C18	−0.3 (5)
S2—Sn—C1—C6	−36.6 (3)	C21—C16—C17—C18	179.7 (3)
S3—Sn—C1—C2	−89.7 (3)	C16—C17—C18—C19	0.1 (5)
S1—Sn—C1—C2	27.1 (3)	C16—C17—C18—C22	179.1 (3)
S2—Sn—C1—C2	148.2 (2)	C17—C18—C19—C20	0.0 (5)
C6—C1—C2—C3	0.7 (5)	C22—C18—C19—C20	−179.0 (3)
Sn—C1—C2—C3	176.0 (3)	C16—C15—C20—C19	−0.3 (5)
C1—C2—C3—C4	−1.1 (6)	S2—C15—C20—C19	−178.8 (3)
C2—C3—C4—C5	0.2 (6)	C18—C19—C20—C15	0.1 (5)
C3—C4—C5—C6	1.1 (6)	Sn—S3—C23—C28	−81.4 (3)
C2—C1—C6—C5	0.6 (5)	Sn—S3—C23—C24	99.6 (3)
Sn—C1—C6—C5	−174.6 (3)	C28—C23—C24—C25	1.0 (5)
C4—C5—C6—C1	−1.6 (6)	S3—C23—C24—C25	−179.9 (3)
Sn—S1—C7—C12	−85.7 (2)	C28—C23—C24—C29	−179.8 (3)
Sn—S1—C7—C8	95.0 (2)	S3—C23—C24—C29	−0.8 (5)
C12—C7—C8—C9	−0.6 (4)	C23—C24—C25—C26	−0.7 (6)
S1—C7—C8—C9	178.7 (2)	C29—C24—C25—C26	−179.8 (4)
C12—C7—C8—C13	178.0 (3)	C24—C25—C26—C27	0.3 (7)
S1—C7—C8—C13	−2.7 (4)	C24—C25—C26—C30	179.9 (4)
C7—C8—C9—C10	0.6 (5)	C25—C26—C27—C28	−0.2 (7)
C13—C8—C9—C10	−178.0 (3)	C30—C26—C27—C28	−179.8 (4)
C8—C9—C10—C11	−0.1 (5)	C24—C23—C28—C27	−1.0 (5)
C8—C9—C10—C14	179.9 (3)	S3—C23—C28—C27	179.9 (3)
C9—C10—C11—C12	−0.6 (5)	C26—C27—C28—C23	0.6 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C15–C20 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1	0.93	2.72	3.557 (3)	149
C13—H13C···Cg2ⁱ	0.96	2.75	3.579 (3)	144

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)(C₈H₉S)₃]
M_r	607.43
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.2717 (7), 10.6370 (8), 15.6486 (11)
α, β, γ (°)	93.420 (2), 93.520 (1), 105.800 (1)
V (Å³)	1477.51 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.32 × 0.26 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.705, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	12493, 5416, 4057
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.061, 0.86
No. of reflections	5416
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.37

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C15–C20 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1	0.93	2.72	3.557 (3)	149
C13—H13C···Cg2ⁱ	0.96	2.75	3.579 (3)	144

Symmetry code: (i) −x+2, −y+2, −z+2.

Acknowledgements

The authors thank the Instituto Rcxaslan-CSIC, Spain for a license to use the Cambridge Structural Database (Allen, 2002 ).

References

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Volume 66| Part 11| November 2010| Pages m1389-m1390

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