Bis(tetra­phenyl­phospho­nium) tris­[N-(methyl­sulfon­yl)dithio­carbimato(2−)-κ2S,S′]stannate(IV)

Barolli, J.P.; Oliveira, M.R.L.; Corrêa, R.S.; Ellena, J.

doi:10.1107/S1600536809034114

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1154-m1155

doi:10.1107/S1600536809034114

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Bis(tetraphenylphosphonium) tris[N-(methylsulfonyl)dithiocarbimato(2−)-κ²S,S′]stannate(IV)

João P. Barolli,^a Marcelo R. L. Oliveira,^a Rodrigo S. Corrêa ^b ^* and Javier Ellena ^b

^aDepartamento de Química, UFV, 36570-000 Viçosa, MG, Brazil, and ^bInstituto de Física de São Carlos, Universidade de São Paulo, 13560-970, São Carlos, SP, Brazil
^*Correspondence e-mail: rodrigocorrea@ursa.ifsc.usp.br

(Received 1 July 2009; accepted 25 August 2009; online 5 September 2009)

In the title complex, (C₂₄H₂₀P)₂[Sn(C₂H₃NO₂S₃)₃], the Sn^IV atom is coordinated by three N-(methylsulfonyl)dithiocarbimate bidentate ligands through the anionic S atoms in a slightly distorted octahedral coordination geometry. There is one half-molecule in the asymmetric unit; the complex is located on a crystallographic twofold rotation axis passing through the cation and bisecting one of the (non-symmetric) ligands, which appears thus disordered over two sites of equal occupancy. In the crystal structure, weak intermolecular C—H⋯O and C—H⋯S interactions contribute to the packing stabilization.

Related literature

For general background to tin(IV) dithiocarbamates, see: Barone et al. (2002 ); Coucouvanis (1979 ); Heard (2005 ); Menezes et al. (2005 ); Seth et al. (1992 ). For related structures of transition metal (Ni, Pt and Zn) complexes with dithiocarbimates derived from sulfonamides, see: Alves et al. (2009 ); Amim et al. (2008 ); Franca et al. (2006 ); Menezes et al. (2005). For the ligand synthesis, see: Hartke (1966 ).

Experimental

Crystal data

(C₂₄H₂₀P)₂[Sn(C₂H₃NO₂S₃)₃]
M_r = 1305.13
Monoclinic, C 2/c
a = 18.5563 (3) Å
b = 13.6096 (2) Å
c = 23.3203 (3) Å
β = 91.355 (1)°
V = 5887.75 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 298 K
0.40 × 0.11 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: gaussian (Coppens et al., 1965 ) T_min = 0.726, T_max = 0.943
17695 measured reflections
5178 independent reflections
4871 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.138
S = 1.25
5178 reflections
372 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O4ⁱ	0.96	2.35	3.284 (13)	166
C16—H16⋯O3ⁱⁱ	0.93	2.60	3.2203 (10)	125
C19—H19⋯O1ⁱⁱⁱ	0.93	2.47	3.296 (7)	148
C28—H28⋯S4ⁱⁱ	0.93	2.69	3.345 (5)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034114/bg2277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034114/bg2277Isup2.hkl

checkCIF report

Comment top

We became interested in the syntheses and characterization of tin(IV) dithiocarbimate complexes due to their similarity with the dithiocarbamate analogues, which have shown antifungal activity (Menezes et al., 2005). Tin dithiocarbamates have also been used as molecular tin sulfide precursors for semiconductor films (Barone et al., 2002). To the best of our knowledge, the title compound is the first member of a class of Sn complexes with general formula [Sn(RSO₂N=CS₂)₃]^2-. This class is related to tin(IV) dithiocarbamates (Coucouvanis, 1979; Heard, 2005 and Seth et al., 1992). However, differently from the dithiocarbamates, these are anionic species. Some crystallographic structures of transition metal (Ni, Pt and Zn) complexes with dithiocarbimates derivated from sulfonamides are described in the literature (Alves et al.,2009; Amim et al., 2008 and Franca et al.; 2006).

The title compound, which is quite stable under ambient conditions, comprises a complex dianion and two tetraphenylphosphonium cations, with the formula (Ph₄P)₂[Sn(CH₃SO₂N=CS₂)₂] (scheme). To the best of our knowledge the tris(methyldithiocarbimato)estannate(IV) anion is the first example of tin complexes with dithiocarbimate ligands derived from sulfonamides. So, in this paper we report the crystal structure of the title compound. The complex presents an octahedral environment around the Sn^IV atom with the ligands coordinating in a relatively distorted manner (Figure 1). The Sn—S bond lengths lie within the range 2.443 (3)–2.646 (2) Å. In the chelate rings the C—S fragments present bond lengths which are characteristic of a single bond [1.75 (1)–1.77 (1) Å]. These values are in agreement with related structures (Menezes et al., 2005). One of the ligands appears disordered into two sites (arounf the twofold symmetry axis) with occupancy factor 0.5. Weak intermolecular C—H···O and C—H···S interactions contribute to packing stabilization (Table 1). Figure 2 shows a crystal packing view of the complex projected onto the bc plane, where two independent sheets are clearly visible: one of them formed by the complex (green in Figure 2) and another defined by phosphonium units (blue in Figure 2). Both sheets are linked by weak hydrogen bonds (Table 1).

Related literature top

For general background to tin(IV) dithiocarbamates, see: Barone et al. (2002); Coucouvanis (1979); Heard (2005); Menezes et al. (2005); Seth et al. (1992). For related structures of transition metal (Ni, Pt and Zn) complexes with dithiocarbimates derived from sulfonamides, see: Alves et al.(2009); Amim et al. (2008); Franca et al. (2006); Menezes et al. (2005). For the ligand synthesis, see: Hartke (1966).

Experimental top

The potassium methylsulfonyldithiocarbimate dihydrate was prepared from methanesulfonamide as described in the literature (Hartke,1966). The compound (1) was prepared in DMF (10 ml). Tin(IV) iodide (0.7 mmol) was added to a suspension of the potassium methylsulfonyldithiocarbimate dihydrate (2.1 mmol). The mixture was stirred for 1.5 h at room temperature and filtered. Water (15 ml) and tetraphenylphosphonium bromide (1.4 mmol) were added to the solution obtained. The mixture was stirred for 15 min and the solid product obtained was filtered, washed with distilled water and dried under reduced pressure for 1 day, yielding (Ph₄P)₂[Sn(CH₃SO₂N=CS₂)₃] (ca 70%). Suitable crystals of (1) were obtained by slow evaporation of the solution of the compound in methanol/water (1:1 v/v); m. pt 420.6–422.0 K. Analysis found: C49.69, H 3.91, N 3.04%; C₅₄H₄₉N₃O₆P₂S₉Sn requires: C 49.69, H 3.78, N 3.22%. IR (most important bands, cm^-1): 1437 v(C=N); 1291 v_ass(SO₂); 1127 v_sim(SO₂); 938 v_ass(CS₂) and 317 v(SnS).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: Please supply; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Structure of the complex showing atom labels, with ellipsoids drawn at the 30% probability level. One of the two moieties in the disordered ligand is presented in open bonds. For clarity, H atoms have been omitted. [Symmetry code: i= -x, y, 1/2-z].
	Fig. 2. Crystal packing of the title compound forming two independents sheets. The complex are displayed in green and the phosphonium in blue.

Bis(tetraphenylphosphonium) tris[N-(methylsulfonyl)dithiocarbimato(2-)- κ²S,S']stannate(IV) top

Crystal data top

(C₂₄H₂₀P)₂[Sn(C₂H₃NO₂S₃)₃]	F(000) = 2664
M_r = 1305.13	D_x = 1.472 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 37024 reflections
a = 18.5563 (3) Å	θ = 2.9–26.4°
b = 13.6096 (2) Å	µ = 0.86 mm⁻¹
c = 23.3203 (3) Å	T = 298 K
β = 91.355 (1)°	Prism, colourless
V = 5887.75 (15) Å³	0.40 × 0.11 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4871 reflections with I > 2σ(I)
CCD rotation images, thick slices scans	R_int = 0.049
Absorption correction: gaussian (Coppens et al., 1965)	θ_max = 25.0°, θ_min = 3.2°
T_min = 0.726, T_max = 0.943	h = −22→22
17695 measured reflections	k = −16→15
5178 independent reflections	l = −27→27

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.068	w = 1/[σ²(F_o²) + (0.0524P)² + 7.2513P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.138	(Δ/σ)_max < 0.001
S = 1.25	Δρ_max = 0.62 e Å⁻³
5178 reflections	Δρ_min = −0.80 e Å⁻³
372 parameters

Crystal data top

(C₂₄H₂₀P)₂[Sn(C₂H₃NO₂S₃)₃]	V = 5887.75 (15) Å³
M_r = 1305.13	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.5563 (3) Å	µ = 0.86 mm⁻¹
b = 13.6096 (2) Å	T = 298 K
c = 23.3203 (3) Å	0.40 × 0.11 × 0.07 mm
β = 91.355 (1)°

Data collection top

Nonius KappaCCD diffractometer	5178 independent reflections
Absorption correction: gaussian (Coppens et al., 1965)	4871 reflections with I > 2σ(I)
T_min = 0.726, T_max = 0.943	R_int = 0.049
17695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1 restraint
wR(F²) = 0.138	H-atom parameters constrained
S = 1.25	Δρ_max = 0.62 e Å⁻³
5178 reflections	Δρ_min = −0.80 e Å⁻³
372 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.1377 (2)	0.3823 (4)	0.23827 (19)	0.0512 (11)
C2	0.3047 (4)	0.2250 (6)	0.2112 (3)	0.097 (2)
H2A	0.2987	0.1898	0.2464	0.146*
H2B	0.3355	0.2807	0.218	0.146*
H2C	0.3261	0.1825	0.1835	0.146*
C3	0.0123 (6)	0.7091 (10)	0.2265 (5)	0.054 (3)	0.5
C4	0.0208 (8)	0.9908 (8)	0.2192 (6)	0.084 (4)	0.5
H4A	0	1.0435	0.25	0.126*
H4B	0.0692	0.9963	0.2088	0.126*	0.5
H4C	−0.01	0.9968	0.1853	0.126*	0.5
C5	0.1135 (3)	0.1693 (4)	0.42704 (19)	0.0513 (11)
C6	0.1645 (3)	0.0950 (4)	0.4278 (2)	0.0630 (13)
H6	0.1825	0.071	0.4626	0.076*
C7	0.1888 (4)	0.0563 (4)	0.3767 (3)	0.0807 (17)
H7	0.2227	0.006	0.3773	0.097*
C8	0.1626 (4)	0.0925 (5)	0.3254 (3)	0.0826 (19)
H8	0.1788	0.0661	0.2912	0.099*
C9	0.1128 (3)	0.1669 (5)	0.3238 (2)	0.0737 (16)
H9	0.0957	0.1912	0.2888	0.088*
C10	0.0883 (3)	0.2056 (4)	0.3743 (2)	0.0602 (13)
H10	0.0546	0.2563	0.3733	0.072*
C11	−0.0120 (2)	0.1986 (3)	0.50305 (17)	0.0482 (11)
C12	−0.0622 (3)	0.1985 (4)	0.45823 (19)	0.0546 (12)
H12	−0.0472	0.207	0.4208	0.065*
C13	−0.1347 (3)	0.1858 (4)	0.4689 (2)	0.0617 (13)
H13	−0.1682	0.1852	0.4386	0.074*
C14	−0.1570 (3)	0.1742 (4)	0.5237 (2)	0.0656 (14)
H14	−0.2057	0.1654	0.5307	0.079*
C15	−0.1080 (3)	0.1753 (4)	0.5685 (2)	0.0715 (15)
H15	−0.1237	0.1677	0.6058	0.086*
C16	−0.0362 (3)	0.1877 (4)	0.5588 (2)	0.0654 (14)
H16	−0.0034	0.1887	0.5896	0.079*
C17	0.1296 (2)	0.1673 (4)	0.55250 (18)	0.0492 (11)
C18	0.1161 (3)	0.0707 (4)	0.5669 (2)	0.0622 (13)
H18	0.0847	0.0335	0.5441	0.075*
C19	0.1486 (3)	0.0285 (4)	0.6148 (2)	0.0689 (14)
H19	0.1392	−0.0366	0.6243	0.083*
C20	0.1953 (3)	0.0845 (5)	0.6485 (2)	0.0722 (16)
H20	0.2174	0.0568	0.6809	0.087*
C21	0.2091 (3)	0.1798 (5)	0.6346 (2)	0.0731 (17)
H21	0.2405	0.2167	0.6577	0.088*
C22	0.1768 (3)	0.2223 (4)	0.5866 (2)	0.0622 (13)
H22	0.1868	0.2873	0.5772	0.075*
C23	0.0993 (3)	0.3510 (4)	0.4934 (2)	0.0541 (12)
C24	0.1468 (3)	0.3929 (4)	0.4560 (3)	0.0711 (15)
H24	0.1673	0.355	0.4275	0.085*
C25	0.1640 (4)	0.4919 (4)	0.4611 (3)	0.092 (2)
H25	0.1957	0.5206	0.4356	0.11*
C26	0.1348 (4)	0.5465 (5)	0.5030 (4)	0.102 (2)
H26	0.1471	0.6125	0.5067	0.122*
C27	0.0883 (5)	0.5062 (5)	0.5395 (4)	0.114 (3)
H27	0.0688	0.5445	0.5683	0.137*
C28	0.0690 (4)	0.4077 (5)	0.5346 (3)	0.093 (2)
H28	0.0356	0.3808	0.5592	0.111*
N1	0.1997 (2)	0.3395 (3)	0.23680 (16)	0.0549 (10)
N3	0.0164 (4)	0.8014 (7)	0.2123 (3)	0.059 (2)	0.5
O1	0.1729 (2)	0.1825 (3)	0.18192 (17)	0.0874 (13)
O2	0.2311 (2)	0.3177 (3)	0.13255 (15)	0.0814 (12)
O3	−0.0270 (8)	0.8837 (7)	0.1904 (4)	0.134 (5)	0.5
O4	−0.0792 (5)	0.8933 (8)	0.2542 (6)	0.132 (4)	0.5
P1	0.08248 (6)	0.22110 (9)	0.49273 (5)	0.0472 (3)
S1	0.12124 (7)	0.45967 (11)	0.29633 (6)	0.0639 (4)
S2	0.06587 (7)	0.37025 (12)	0.18873 (5)	0.0676 (4)
S3	0.22079 (7)	0.26505 (11)	0.18510 (5)	0.0629 (4)
S5	0.01886 (19)	0.6562 (3)	0.21037 (15)	0.0599 (8)	0.5
S4	0.04165 (16)	0.6248 (2)	0.17458 (13)	0.0629 (7)	0.5
S6	0	0.88818 (17)	0.25	0.0880 (7)
Sn1	0	0.49240 (4)	0.25	0.0642 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.053 (3)	0.047 (2)	−0.009 (2)	−0.010 (2)	0.005 (2)
C2	0.091 (4)	0.108 (5)	0.092 (5)	0.040 (4)	−0.011 (4)	−0.022 (4)
C3	0.041 (6)	0.061 (9)	0.060 (7)	−0.007 (6)	0.001 (5)	0.002 (6)
C4	0.109 (10)	0.043 (7)	0.099 (9)	0.013 (6)	0.004 (7)	0.007 (6)
C5	0.059 (3)	0.047 (3)	0.047 (3)	−0.009 (2)	0.002 (2)	−0.002 (2)
C6	0.075 (3)	0.056 (3)	0.059 (3)	0.008 (3)	0.009 (2)	−0.001 (2)
C7	0.103 (5)	0.056 (4)	0.085 (4)	0.004 (3)	0.028 (4)	−0.012 (3)
C8	0.115 (5)	0.071 (4)	0.062 (4)	−0.029 (4)	0.026 (3)	−0.023 (3)
C9	0.095 (4)	0.076 (4)	0.050 (3)	−0.026 (4)	0.002 (3)	−0.003 (3)
C10	0.071 (3)	0.061 (3)	0.048 (3)	−0.009 (3)	0.002 (2)	−0.001 (2)
C11	0.056 (3)	0.047 (3)	0.041 (2)	−0.003 (2)	−0.003 (2)	−0.0003 (19)
C12	0.064 (3)	0.057 (3)	0.042 (2)	0.001 (2)	−0.008 (2)	0.000 (2)
C13	0.057 (3)	0.063 (3)	0.064 (3)	0.001 (2)	−0.017 (2)	−0.001 (3)
C14	0.051 (3)	0.066 (4)	0.080 (4)	−0.004 (3)	0.001 (3)	0.007 (3)
C15	0.064 (3)	0.090 (4)	0.061 (3)	−0.003 (3)	0.006 (3)	0.012 (3)
C16	0.057 (3)	0.089 (4)	0.049 (3)	−0.005 (3)	−0.008 (2)	0.006 (3)
C17	0.047 (2)	0.059 (3)	0.041 (2)	0.000 (2)	−0.0049 (19)	−0.004 (2)
C18	0.070 (3)	0.060 (4)	0.055 (3)	0.002 (3)	−0.015 (2)	−0.003 (2)
C19	0.075 (4)	0.070 (4)	0.061 (3)	0.013 (3)	−0.009 (3)	0.009 (3)
C20	0.058 (3)	0.106 (5)	0.051 (3)	0.019 (3)	−0.010 (2)	0.005 (3)
C21	0.055 (3)	0.115 (6)	0.049 (3)	−0.008 (3)	−0.011 (2)	−0.007 (3)
C22	0.058 (3)	0.077 (4)	0.051 (3)	−0.008 (3)	−0.003 (2)	−0.002 (3)
C23	0.060 (3)	0.045 (3)	0.057 (3)	−0.002 (2)	0.002 (2)	−0.009 (2)
C24	0.075 (4)	0.051 (3)	0.087 (4)	−0.004 (3)	0.014 (3)	−0.009 (3)
C25	0.096 (5)	0.056 (4)	0.125 (6)	−0.016 (3)	0.028 (4)	−0.008 (4)
C26	0.108 (5)	0.054 (4)	0.143 (7)	−0.012 (4)	0.016 (5)	−0.017 (4)
C27	0.154 (7)	0.066 (5)	0.126 (6)	−0.003 (5)	0.041 (6)	−0.044 (4)
C28	0.119 (5)	0.067 (4)	0.094 (4)	−0.008 (4)	0.042 (4)	−0.026 (4)
N1	0.052 (2)	0.060 (3)	0.052 (2)	0.001 (2)	−0.0102 (17)	−0.0085 (19)
N3	0.066 (5)	0.058 (6)	0.054 (5)	0.002 (4)	0.007 (4)	−0.012 (4)
O1	0.110 (3)	0.079 (3)	0.074 (3)	−0.031 (2)	0.014 (2)	−0.023 (2)
O2	0.080 (3)	0.110 (3)	0.055 (2)	−0.010 (2)	0.0100 (18)	0.006 (2)
O3	0.270 (15)	0.073 (6)	0.058 (5)	−0.038 (8)	−0.046 (7)	0.013 (4)
O4	0.095 (7)	0.110 (8)	0.193 (12)	−0.006 (6)	0.054 (7)	−0.038 (8)
P1	0.0522 (7)	0.0475 (7)	0.0416 (6)	−0.0017 (5)	−0.0034 (5)	−0.0020 (5)
S1	0.0551 (7)	0.0641 (9)	0.0713 (8)	0.0058 (6)	−0.0250 (6)	−0.0177 (7)
S2	0.0568 (7)	0.0928 (11)	0.0523 (7)	−0.0070 (7)	−0.0166 (6)	−0.0055 (7)
S3	0.0668 (8)	0.0698 (9)	0.0521 (7)	−0.0048 (7)	−0.0010 (6)	−0.0083 (6)
S5	0.0665 (19)	0.060 (2)	0.053 (2)	−0.0027 (18)	0.0020 (15)	0.0058 (16)
S4	0.0832 (19)	0.0563 (17)	0.0500 (15)	−0.0006 (14)	0.0157 (14)	−0.0023 (13)
S6	0.112 (2)	0.0629 (14)	0.0878 (16)	0	−0.0187 (13)	0
Sn1	0.0555 (3)	0.0525 (4)	0.0834 (4)	0	−0.0268 (3)	0

Geometric parameters (Å, º) top

C1—N1	1.290 (6)	C17—P1	1.785 (4)
C1—S1	1.748 (5)	C18—C19	1.381 (7)
C1—S2	1.751 (4)	C18—H18	0.93
C2—S3	1.746 (6)	C19—C20	1.385 (8)
C2—H2A	0.96	C19—H19	0.93
C2—H2B	0.96	C20—C21	1.363 (8)
C2—H2C	0.96	C20—H20	0.93
C3—S5	0.822 (12)	C21—C22	1.385 (7)
C3—N3	1.302 (15)	C21—H21	0.93
C3—S5ⁱ	1.750 (12)	C22—H22	0.93
C3—S4	1.763 (14)	C23—C28	1.364 (7)
C4—S6	1.621 (11)	C23—C24	1.378 (7)
C4—O4ⁱ	1.813 (16)	C23—P1	1.795 (5)
C4—O3	1.826 (16)	C24—C25	1.389 (8)
C4—H4A	1.0919	C24—H24	0.93
C4—H4B	0.9393	C25—C26	1.352 (9)
C4—H4C	0.9675	C25—H25	0.93
C5—C6	1.383 (7)	C26—C27	1.343 (10)
C5—C10	1.396 (7)	C26—H26	0.93
C5—P1	1.794 (5)	C27—C28	1.391 (9)
C6—C7	1.387 (7)	C27—H27	0.93
C6—H6	0.93	C28—H28	0.93
C7—C8	1.373 (9)	N1—S3	1.630 (4)
C7—H7	0.93	N3—S6	1.508 (8)
C8—C9	1.370 (9)	N3—S5	1.977 (9)
C8—H8	0.93	O1—S3	1.433 (4)
C9—C10	1.378 (7)	O2—S3	1.436 (4)
C9—H9	0.93	O3—S6	1.469 (8)
C10—H10	0.93	O4—S6	1.477 (9)
C11—C12	1.383 (6)	S1—Sn1	2.5125 (12)
C11—C16	1.394 (6)	S2—Sn1	2.5262 (15)
C11—P1	1.802 (5)	S5—C3ⁱ	1.750 (12)
C12—C13	1.384 (7)	S5—Sn1	2.441 (4)
C12—H12	0.93	S4—Sn1	2.646 (3)
C13—C14	1.361 (7)	S6—O3ⁱ	1.469 (8)
C13—H13	0.93	S6—O4ⁱ	1.477 (9)
C14—C15	1.369 (7)	S6—N3ⁱ	1.508 (8)
C14—H14	0.93	S6—C4ⁱ	1.621 (11)
C15—C16	1.367 (7)	Sn1—S5ⁱ	2.441 (4)
C15—H15	0.93	Sn1—S1ⁱ	2.5125 (12)
C16—H16	0.93	Sn1—S2ⁱ	2.5262 (15)
C17—C18	1.382 (7)	Sn1—S4ⁱ	2.646 (3)
C17—C22	1.388 (7)

N1—C1—S1	117.7 (3)	C26—C25—C24	120.0 (6)
N1—C1—S2	127.2 (4)	C26—C25—H25	120
S1—C1—S2	115.1 (3)	C24—C25—H25	120
S3—C2—H2A	109.5	C27—C26—C25	120.5 (6)
S3—C2—H2B	109.5	C27—C26—H26	119.7
H2A—C2—H2B	109.5	C25—C26—H26	119.7
S3—C2—H2C	109.5	C26—C27—C28	120.7 (6)
H2A—C2—H2C	109.5	C26—C27—H27	119.7
H2B—C2—H2C	109.5	C28—C27—H27	119.7
S5—C3—N3	136.0 (15)	C23—C28—C27	119.5 (6)
S5—C3—S5ⁱ	94.5 (11)	C23—C28—H28	120.2
N3—C3—S5ⁱ	129.3 (10)	C27—C28—H28	120.2
N3—C3—S4	115.7 (9)	C1—N1—S3	122.0 (3)
S5ⁱ—C3—S4	115.0 (7)	C3—N3—O3	142.3 (10)
S6—C4—H4A	100.5	C3—N3—S6	126.4 (9)
O4ⁱ—C4—H4A	118.3	O3—N3—S5	140.2 (7)
O3—C4—H4A	126.2	S6—N3—S5	143.2 (6)
S6—C4—H4B	115	N3—O3—O4	94.0 (7)
C4ⁱ—C4—H4B	134.1	N3—O3—C4	102.9 (8)
O3—C4—H4B	115.4	C17—P1—C5	110.1 (2)
H4A—C4—H4B	118.2	C17—P1—C23	108.4 (2)
S6—C4—H4C	107	C5—P1—C23	109.6 (2)
C4ⁱ—C4—H4C	115.6	C17—P1—C11	106.7 (2)
O4ⁱ—C4—H4C	132.7	C5—P1—C11	112.4 (2)
H4A—C4—H4C	105.7	C23—P1—C11	109.6 (2)
H4B—C4—H4C	109.4	C1—S1—Sn1	86.82 (15)
C6—C5—C10	119.0 (4)	C1—S2—Sn1	86.33 (17)
C6—C5—P1	120.7 (4)	O1—S3—O2	116.2 (2)
C10—C5—P1	120.3 (4)	O1—S3—N1	111.5 (2)
C5—C6—C7	120.2 (5)	O2—S3—N1	111.1 (2)
C5—C6—H6	119.9	O1—S3—C2	108.7 (3)
C7—C6—H6	119.9	O2—S3—C2	108.5 (3)
C8—C7—C6	119.8 (6)	N1—S3—C2	99.5 (3)
C8—C7—H7	120.1	C3—S5—S4	142.7 (11)
C6—C7—H7	120.1	S4—S5—C3ⁱ	175.2 (4)
C9—C8—C7	120.8 (5)	S4—S5—N3	116.1 (3)
C9—C8—H8	119.6	C3ⁱ—S5—N3	64.0 (4)
C7—C8—H8	119.6	C3—S5—Sn1	127.1 (10)
C8—C9—C10	119.8 (5)	S4—S5—Sn1	89.6 (3)
C8—C9—H9	120.1	C3ⁱ—S5—Sn1	90.2 (5)
C10—C9—H9	120.1	N3—S5—Sn1	154.2 (3)
C9—C10—C5	120.4 (5)	S5—S4—Sn1	67.3 (3)
C9—C10—H10	119.8	C3—S4—Sn1	83.5 (4)
C5—C10—H10	119.8	O3ⁱ—S6—O3	175.2 (8)
C12—C11—C16	118.7 (4)	O3ⁱ—S6—O4	104.9 (7)
C12—C11—P1	122.6 (3)	O3—S6—O4	75.4 (7)
C16—C11—P1	118.6 (3)	O4ⁱ—S6—O4	174.6 (9)
C11—C12—C13	120.2 (4)	O3—S6—N3ⁱ	116.8 (5)
C11—C12—H12	119.9	O4ⁱ—S6—N3ⁱ	106.9 (5)
C13—C12—H12	119.9	O4—S6—N3ⁱ	77.4 (6)
C14—C13—C12	120.1 (5)	O3ⁱ—S6—N3	116.8 (5)
C14—C13—H13	119.9	O3—S6—N3	59.0 (5)
C12—C13—H13	119.9	O4ⁱ—S6—N3	77.4 (6)
C13—C14—C15	120.3 (5)	O4—S6—N3	106.9 (5)
C13—C14—H14	119.9	N3ⁱ—S6—N3	76.9 (7)
C15—C14—H14	119.9	O3ⁱ—S6—C4ⁱ	72.3 (6)
C16—C15—C14	120.5 (5)	O3—S6—C4ⁱ	112.1 (7)
C16—C15—H15	119.7	O4ⁱ—S6—C4ⁱ	103.7 (7)
C14—C15—H15	119.7	O4—S6—C4ⁱ	71.5 (6)
C15—C16—C11	120.2 (5)	N3ⁱ—S6—C4ⁱ	111.3 (6)
C15—C16—H16	119.9	N3—S6—C4ⁱ	170.6 (6)
C11—C16—H16	119.9	O3ⁱ—S6—C4	112.1 (7)
C18—C17—C22	119.3 (4)	O3—S6—C4	72.3 (6)
C18—C17—P1	119.5 (3)	O4ⁱ—S6—C4	71.5 (6)
C22—C17—P1	121.1 (4)	O4—S6—C4	103.7 (7)
C19—C18—C17	120.9 (5)	N3—S6—C4	111.3 (6)
C19—C18—H18	119.5	S5ⁱ—Sn1—S5	48.15 (19)
C17—C18—H18	119.5	S5ⁱ—Sn1—S1	97.70 (9)
C18—C19—C20	119.0 (6)	S5—Sn1—S1	100.94 (9)
C18—C19—H19	120.5	S5—Sn1—S1ⁱ	97.70 (9)
C20—C19—H19	120.5	S5ⁱ—Sn1—S2ⁱ	108.13 (10)
C21—C20—C19	120.5 (5)	S5—Sn1—S2ⁱ	152.94 (10)
C21—C20—H20	119.7	S1—Sn1—S2ⁱ	94.61 (5)
C19—C20—H20	119.7	S1ⁱ—Sn1—S2ⁱ	71.71 (4)
C20—C21—C22	120.7 (5)	S5ⁱ—Sn1—S2	152.94 (10)
C20—C21—H21	119.7	S5—Sn1—S2	108.13 (10)
C22—C21—H21	119.7	S1—Sn1—S2	71.71 (4)
C21—C22—C17	119.5 (5)	S1ⁱ—Sn1—S2	94.61 (5)
C21—C22—H22	120.2	S5—Sn1—S4ⁱ	71.14 (14)
C17—C22—H22	120.2	S1—Sn1—S4ⁱ	96.17 (7)
C28—C23—C24	119.5 (5)	S2ⁱ—Sn1—S4ⁱ	85.36 (8)
C28—C23—P1	119.3 (4)	S2—Sn1—S4ⁱ	167.66 (7)
C24—C23—P1	121.0 (4)	S1—Sn1—S4	97.69 (8)
C23—C24—C25	119.8 (5)	S1ⁱ—Sn1—S4	96.17 (7)
C23—C24—H24	120.1	S2ⁱ—Sn1—S4	167.66 (7)
C25—C24—H24	120.1	S2—Sn1—S4	85.36 (8)

C10—C5—C6—C7	−1.3 (8)	C3ⁱ—C3—N3—S6	5.2 (18)
P1—C5—C6—C7	−179.2 (4)	S5ⁱ—C3—N3—S6	5.2 (15)
C5—C6—C7—C8	0.6 (9)	S4—C3—N3—S6	−175.4 (6)
C6—C7—C8—C9	0.3 (9)	S4—C3—N3—N3ⁱ	−177.0 (8)
C7—C8—C9—C10	−0.5 (9)	C3ⁱ—C3—N3—S5	−173 (3)
C8—C9—C10—C5	−0.2 (8)	S5ⁱ—C3—N3—S5	−173 (3)
C6—C5—C10—C9	1.1 (7)	S4—C3—N3—S5	6.0 (12)
P1—C5—C10—C9	179.1 (4)	C18—C17—P1—C5	−70.6 (4)
C16—C11—C12—C13	−1.2 (7)	C22—C17—P1—C5	112.8 (4)
P1—C11—C12—C13	−176.7 (4)	C18—C17—P1—C23	169.5 (4)
C11—C12—C13—C14	0.5 (8)	C22—C17—P1—C23	−7.1 (4)
C12—C13—C14—C15	0.2 (8)	C18—C17—P1—C11	51.6 (4)
C13—C14—C15—C16	−0.3 (9)	C22—C17—P1—C11	−125.0 (4)
C14—C15—C16—C11	−0.4 (9)	C6—C5—P1—C17	2.9 (5)
C12—C11—C16—C15	1.1 (8)	C10—C5—P1—C17	−175.1 (4)
P1—C11—C16—C15	176.8 (4)	C6—C5—P1—C23	122.0 (4)
C22—C17—C18—C19	0.3 (7)	C10—C5—P1—C23	−55.9 (4)
P1—C17—C18—C19	−176.3 (4)	C6—C5—P1—C11	−115.9 (4)
C17—C18—C19—C20	0.0 (8)	C10—C5—P1—C11	66.2 (4)
C18—C19—C20—C21	−0.1 (8)	C28—C23—P1—C17	−71.1 (5)
C19—C20—C21—C22	−0.2 (8)	C24—C23—P1—C17	103.7 (5)
C20—C21—C22—C17	0.5 (8)	C28—C23—P1—C5	168.7 (5)
C18—C17—C22—C21	−0.5 (7)	C24—C23—P1—C5	−16.5 (5)
P1—C17—C22—C21	176.1 (4)	C28—C23—P1—C11	45.0 (5)
C28—C23—C24—C25	0.9 (9)	C24—C23—P1—C11	−140.3 (4)
P1—C23—C24—C25	−173.9 (5)	C12—C11—P1—C17	−157.2 (4)
C23—C24—C25—C26	0.7 (11)	C16—C11—P1—C17	27.3 (5)
C24—C25—C26—C27	−1.0 (13)	C12—C11—P1—C5	−36.4 (5)
C25—C26—C27—C28	−0.3 (14)	C16—C11—P1—C5	148.1 (4)
C24—C23—C28—C27	−2.2 (10)	C12—C11—P1—C23	85.7 (5)
P1—C23—C28—C27	172.7 (6)	C16—C11—P1—C23	−89.8 (4)
C26—C27—C28—C23	2.0 (13)	N1—C1—S1—Sn1	178.7 (4)
S1—C1—N1—S3	179.5 (2)	S2—C1—S1—Sn1	−2.4 (2)
S2—C1—N1—S3	0.7 (6)	N1—C1—S2—Sn1	−178.8 (4)
S5—C3—N3—O3	94 (2)	S1—C1—S2—Sn1	2.4 (2)
C3ⁱ—C3—N3—O3	−80 (2)	C1—N1—S3—O1	−60.3 (5)
S4—C3—N3—O3	99.6 (15)	C1—N1—S3—O2	71.0 (5)
S5—C3—N3—S6	178.6 (15)	C1—N1—S3—C2	−174.8 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4ⁱⁱ	0.96	2.35	3.284 (13)	166
C16—H16···O3ⁱⁱⁱ	0.93	2.60	3.2203 (10)	125
C19—H19···O1^iv	0.93	2.47	3.296 (7)	148
C28—H28···S4ⁱⁱⁱ	0.93	2.69	3.345 (5)	128

Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) x, −y+1, z+1/2; (iv) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	(C₂₄H₂₀P)₂[Sn(C₂H₃NO₂S₃)₃]
M_r	1305.13
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	18.5563 (3), 13.6096 (2), 23.3203 (3)
β (°)	91.355 (1)
V (Å³)	5887.75 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.40 × 0.11 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Gaussian (Coppens et al., 1965)
T_min, T_max	0.726, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	17695, 5178, 4871
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.138, 1.25
No. of reflections	5178
No. of parameters	372
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.80

Computer programs: COLLECT (Nonius, 2000), Please supply, DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4ⁱ	0.96	2.35	3.284 (13)	166
C16—H16···O3ⁱⁱ	0.93	2.60	3.2203 (10)	125
C19—H19···O1ⁱⁱⁱ	0.93	2.47	3.296 (7)	148
C28—H28···S4ⁱⁱ	0.93	2.69	3.345 (5)	128

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z+1/2; (iii) x, −y, z+1/2.

Acknowledgements

The authors are grateful to FAPEMIG and CNPq for financial support.

References

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