μ2-Oxalato-bis­[triphen­yl(thio­urea-κS)tin(IV)]

Sow, Y.; Diop, L.; Molloy, K.C.; Kociok-Kohn, G.

doi:10.1107/S1600536812040706

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1337

doi:10.1107/S1600536812040706

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μ₂-Oxalato-bis[triphenyl(thiourea-κS)tin(IV)]

Yaya Sow,^a ^* Libasse Diop,^a Kieran C. Molloy ^b and Gabrielle Kociok-Kohn ^b

^aLaboratoire de Chimie Minerale et Analytique (LACHIMIA), Departement de Chimie, Faculte des Sciences et Techniques, Universite Cheikh, Anta Diop Dakar Senegal, and ^bDepartment of Chemistry, University of Bath, Bath BA2 7AY, England
^*Correspondence e-mail: yayasow81@yahoo.fr

(Received 15 July 2012; accepted 26 September 2012; online 6 October 2012)

The asymmetric unit of the binuclear title compound, [Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂], consists of one half of the organotin(IV) molecule. The remainder is generated by a twofold rotation axis passing through the mid-point of the oxalate C—C bond. The Sn^IV atom exhibits a distorted trigonal–bipyramidal coordination environment with the phenyl groups in equatorial positions and the thiourea and the monodentately bridging oxalate anion in axial positions. The molecules are linked through N—H⋯O hydrogen bonds involving the amino group of the thiourea ligand and the uncoordinating oxalate O atoms, forming layers parallel to (001). Weak C—H⋯O interactions are also present.

Related literature

For background to organotin(IV) chemistry, see: Evans & Karpel (1985 ); Gielen et al. (1995 ). For triphenyltin(IV)-containing compounds and their biological activity, see: Kamruddin et al. (1996 ). For related compounds, see: Diallo et al. (2009 ); Diasse-Sarr et al. (1997 ); Diop et al. (1997 , 1999 , 2003 ); Tiekink (1992 ).

Experimental

Crystal data

[Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂]
M_r = 940.24
Monoclinic, C 2/c
a = 12.9161 (2) Å
b = 13.9870 (2) Å
c = 21.8215 (3) Å
β = 99.238 (1)°
V = 3891.09 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 150 K
0.30 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.659, T_max = 0.747
31403 measured reflections
4472 independent reflections
3665 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.066
S = 1.09
4472 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.34 e Å⁻³
Δρ_min = −1.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.81 (4)	2.06 (4)	2.824 (3)	157 (4)
N2—H2A⋯O2ⁱⁱ	0.86 (4)	2.14 (4)	2.970 (3)	164 (3)
C6—H6⋯O1	0.95	2.44	2.957 (3)	114
C18—H18⋯O2	0.95	2.39	3.234 (3)	147
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia,1999 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812040706/wm2662sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040706/wm2662Isup2.hkl

checkCIF report

Comment top

Interest in organotin (IV) chemistry remains high because of several applications found in molecules belonging to this family (Evans & Karpel, 1985; Gielen et al., 1995), specifically triphenyltin(IV)-residue containing compounds for which biological activity has been reported (Kamruddin et al., 1996). Our specific interest lies also in the coordinating behavior of oxy-anions to these organometallic centers; we have previously published several crystal structures dealing with such systems (Diallo et al., 2009; Diasse-Sarr et al., 1997; Diop et al., 1997). Moreover, we have reported spectroscopic data (Diop et al., 1999) and the crystal structure of [Sn₂(C₂O₄)(C₆H₅)₆] which exhibits tetrahedrally coordinate tin atoms (Diop et al., 2003). Here we report a study of the interactions between this species and thiourea, which has yielded the title compound, [Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂].

The molecule of the title compound has site symmetry 2 with the twofold rotation axcis passing through the mid-point of the central oxalate C—C bond. The Sn(IV) atom is five-coordinate by one oxygen atom of the oxalate anion, a sulfur atom of the thiourea ligand [Sn—O 2.2471 (17), Sn—S 2.6945 (7) Å] which are in apical positions and to three phenyl groups [Sn—C 2.146 (2), 2.139 (2), 2.139 (2) Å] occupying the equatorial positions of the trigonal bipyramid (Fig. 1). The Sn—S bond length is longer than the Sn—S bond length [2.573 (1) Å] found, for example, in {^t(C₄H₉)₂Sn[S₂CN(CH₃)₂]₂} which contains a trigonal bipyramidally coordinate tin(IV) atom (Tiekink, 1992). The angle S—Sn—O [175.97 (5)°] deviates slightly from linearity. The sum of the C—Sn—C angles (359.96°) indicates a nearly perfectly planar Sn(C₆H₅)₃ residue consistent with the near linearity of the axial substituents. The Sn—O bond length is remarkably long when compared with the Sn—O distance [2.111 (1) Å] in the tetrahedrally coordinate tin(IV) atom in [Sn₂(C₂O₄)(C₆H₅)₆] (Diop et al., 2003). The addition of SC(NH₂)₂ apparently has caused a change in the coordination from tetrahedral to trigonal-bipyramidal along with a Sn—O bond length increase. The two C—O bond length of the oxalate anion are slightly different because the O atom of the C19—O1 bond [1.269 (3) Å] is also involved in bonding to the Sn(IV) atom, whereas the O atom of the C19—O2 bond [1.243 (3) Å] is involved in hydrogen bonding with the amino group. These interactions lead to the formation of layers parallel to (001) (Figs. 2,3). Weak C—H···O hydrogen bonding is also observed.

Related literature top

For background to organotin(IV) chemistry, see: Evans & Karpel (1985); Gielen et al. (1995). For triphenyltin(IV)-containing compounds and their biological activity, see: Kamruddin et al. (1996). For related compounds, see: Diallo et al. (2009); Diasse-Sarr et al. (1997); Diop et al. (1997, 1999, 2003); Tiekink (1992).

Experimental top

All chemicals were purchased from Aldrich or Merck and used without any further purification. [Sn₂(C₂O₄)(C₆H₅)₆] has been obtained on allowing Sn(C₆H₅)₃OH to react with oxalic acid in a 2:1 ratio in ethanol. A white powder is collected after slow evaporation. When [Sn₂(C₂O₄)(C₆H₅)₆] is mixed with SC(NH₂)₂ in a 1:2 ratio, both as ethanolic solutions, a colorless solution is obtained which gives crystals of [Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂] suitable for X-ray work, after a slow solvent evaporation.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia,1999).

Figures top

	Fig. 1. The molecule of the title complex showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code a) -x, y, -z + 1/2.]
	Fig. 2. View of the N—H···O hydrogen bonding system (dashed lines) assured by pairs of oxygen atoms of the oxalate and H atoms of thiourea.
	Fig. 3. The packing of the structure showing N—H···O hydrogen bonding interactions as dashed lines

µ₂-Oxalato-bis[triphenyl(thiourea-κS)tin(IV)] top

Crystal data top

[Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂]	F(000) = 1880
M_r = 940.24	D_x = 1.605 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 26977 reflections
a = 12.9161 (2) Å	θ = 2.9–27.5°
b = 13.9870 (2) Å	µ = 1.44 mm⁻¹
c = 21.8215 (3) Å	T = 150 K
β = 99.238 (1)°	Block, colourless
V = 3891.09 (10) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4472 independent reflections
Radiation source: fine-focus sealed tube	3665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
400 1.5 degree images with ϕ and ω scans	θ_max = 27.5°, θ_min = 3.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −16→16
T_min = 0.659, T_max = 0.747	k = −18→18
31403 measured reflections	l = −28→28

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0248P)² + 7.4801P] where P = (F_o² + 2F_c²)/3
4472 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −1.11 e Å⁻³

Crystal data top

[Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂]	V = 3891.09 (10) Å³
M_r = 940.24	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.9161 (2) Å	µ = 1.44 mm⁻¹
b = 13.9870 (2) Å	T = 150 K
c = 21.8215 (3) Å	0.30 × 0.30 × 0.20 mm
β = 99.238 (1)°

Data collection top

Nonius KappaCCD diffractometer	4472 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3665 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.747	R_int = 0.057
31403 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.34 e Å⁻³
4472 reflections	Δρ_min = −1.11 e Å⁻³
251 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	0.165377 (13)	0.128741 (12)	0.141781 (7)	0.01783 (7)
S	0.33347 (5)	0.18709 (5)	0.09290 (3)	0.02648 (16)
O1	0.03210 (13)	0.08111 (13)	0.18919 (8)	0.0223 (4)
O2	0.09855 (14)	−0.05868 (13)	0.22806 (8)	0.0247 (4)
N1	0.3214 (2)	0.34372 (19)	0.16116 (13)	0.0319 (6)
H1A	0.340 (3)	0.385 (3)	0.1866 (18)	0.050 (12)*
H1B	0.256 (3)	0.351 (2)	0.1449 (16)	0.040 (10)*
N2	0.4815 (2)	0.2725 (2)	0.17068 (13)	0.0342 (6)
H2A	0.509 (3)	0.319 (3)	0.1931 (16)	0.044 (10)*
H2B	0.519 (3)	0.228 (3)	0.1620 (17)	0.050 (12)*
C1	0.07308 (19)	0.25438 (17)	0.11628 (11)	0.0190 (5)
C2	0.0815 (2)	0.30357 (19)	0.06162 (12)	0.0245 (6)
H2	0.1363	0.2876	0.0392	0.029*
C3	0.0110 (2)	0.3755 (2)	0.03950 (14)	0.0308 (6)
H3	0.0181	0.4082	0.0023	0.037*
C4	−0.0697 (2)	0.3998 (2)	0.07159 (14)	0.0317 (7)
H4	−0.1187	0.4480	0.0560	0.038*
C5	−0.0780 (2)	0.35315 (19)	0.12646 (13)	0.0266 (6)
H5	−0.1323	0.3702	0.1491	0.032*
C6	−0.0075 (2)	0.28136 (19)	0.14865 (12)	0.0229 (6)
H6	−0.0140	0.2500	0.1865	0.027*
C7	0.2578 (2)	0.11799 (18)	0.23207 (12)	0.0215 (5)
C8	0.2292 (2)	0.1691 (3)	0.28081 (13)	0.0410 (8)
H8	0.1752	0.2157	0.2724	0.049*
C9	0.2764 (3)	0.1547 (4)	0.34114 (15)	0.0574 (11)
H9	0.2549	0.1913	0.3735	0.069*
C10	0.3516 (3)	0.0900 (3)	0.35449 (15)	0.0576 (12)
H10	0.3830	0.0797	0.3964	0.069*
C11	0.3848 (4)	0.0368 (3)	0.3069 (2)	0.0700 (14)
H11	0.4388	−0.0095	0.3162	0.084*
C12	0.3373 (3)	0.0529 (2)	0.24521 (16)	0.0515 (10)
H12	0.3605	0.0184	0.2125	0.062*
C13	0.15172 (19)	0.01853 (18)	0.07300 (11)	0.0202 (5)
C14	0.1501 (2)	0.0447 (2)	0.01093 (12)	0.0298 (6)
H14	0.1558	0.1102	0.0004	0.036*
C15	0.1403 (2)	−0.0245 (2)	−0.03532 (13)	0.0360 (7)
H15	0.1396	−0.0062	−0.0773	0.043*
C16	0.1317 (2)	−0.1194 (2)	−0.02054 (14)	0.0333 (7)
H16	0.1249	−0.1665	−0.0523	0.040*
C17	0.1328 (2)	−0.1461 (2)	0.04042 (14)	0.0343 (7)
H17	0.1266	−0.2117	0.0506	0.041*
C18	0.1429 (2)	−0.0774 (2)	0.08685 (12)	0.0270 (6)
H18	0.1438	−0.0964	0.1287	0.032*
C19	0.03827 (19)	0.01088 (18)	0.22640 (11)	0.0190 (5)
C20	0.3813 (2)	0.2744 (2)	0.14526 (12)	0.0260 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02036 (10)	0.01769 (10)	0.01559 (9)	0.00087 (7)	0.00337 (6)	−0.00049 (7)
S	0.0272 (3)	0.0299 (4)	0.0242 (3)	−0.0054 (3)	0.0098 (3)	−0.0070 (3)
O1	0.0227 (9)	0.0238 (10)	0.0211 (9)	0.0002 (8)	0.0056 (7)	0.0060 (8)
O2	0.0294 (10)	0.0208 (10)	0.0254 (10)	0.0042 (8)	0.0093 (8)	0.0000 (8)
N1	0.0311 (15)	0.0292 (14)	0.0346 (14)	−0.0033 (12)	0.0029 (11)	−0.0081 (12)
N2	0.0297 (14)	0.0301 (15)	0.0427 (16)	−0.0074 (13)	0.0057 (12)	−0.0087 (13)
C1	0.0217 (13)	0.0153 (12)	0.0193 (12)	−0.0001 (10)	0.0011 (10)	0.0000 (10)
C2	0.0277 (14)	0.0250 (14)	0.0208 (13)	0.0001 (11)	0.0039 (11)	0.0013 (11)
C3	0.0364 (16)	0.0237 (15)	0.0309 (15)	0.0021 (13)	0.0015 (12)	0.0069 (12)
C4	0.0295 (15)	0.0247 (15)	0.0389 (17)	0.0063 (12)	−0.0006 (12)	0.0012 (13)
C5	0.0222 (14)	0.0216 (14)	0.0358 (15)	0.0014 (11)	0.0046 (11)	−0.0065 (12)
C6	0.0255 (14)	0.0197 (13)	0.0240 (13)	−0.0012 (11)	0.0054 (10)	−0.0013 (11)
C7	0.0205 (12)	0.0232 (14)	0.0201 (12)	−0.0027 (11)	0.0015 (10)	0.0026 (11)
C8	0.0254 (15)	0.072 (2)	0.0251 (15)	0.0055 (16)	0.0021 (12)	−0.0117 (15)
C9	0.0331 (18)	0.117 (4)	0.0207 (16)	−0.010 (2)	0.0009 (13)	−0.0065 (19)
C10	0.069 (3)	0.075 (3)	0.0207 (16)	−0.046 (2)	−0.0189 (16)	0.0201 (17)
C11	0.077 (3)	0.037 (2)	0.077 (3)	0.012 (2)	−0.045 (2)	0.006 (2)
C12	0.062 (2)	0.039 (2)	0.044 (2)	0.0230 (18)	−0.0196 (17)	−0.0121 (16)
C13	0.0170 (12)	0.0228 (14)	0.0202 (12)	0.0005 (10)	0.0017 (10)	−0.0059 (10)
C14	0.0387 (17)	0.0275 (15)	0.0224 (14)	0.0005 (13)	0.0024 (12)	−0.0017 (11)
C15	0.0424 (18)	0.046 (2)	0.0187 (14)	−0.0021 (15)	0.0026 (12)	−0.0073 (13)
C16	0.0330 (16)	0.0374 (18)	0.0292 (15)	−0.0032 (14)	0.0036 (12)	−0.0176 (13)
C17	0.0414 (17)	0.0265 (16)	0.0350 (16)	−0.0030 (13)	0.0064 (13)	−0.0084 (13)
C18	0.0292 (14)	0.0288 (15)	0.0234 (14)	−0.0015 (12)	0.0051 (11)	−0.0032 (12)
C19	0.0217 (13)	0.0192 (13)	0.0164 (12)	−0.0032 (11)	0.0042 (10)	−0.0016 (10)
C20	0.0303 (15)	0.0252 (14)	0.0241 (14)	−0.0062 (12)	0.0095 (11)	0.0012 (11)

Geometric parameters (Å, º) top

Sn—C7	2.139 (2)	C6—H6	0.9500
Sn—C13	2.139 (2)	C7—C12	1.368 (4)
Sn—C1	2.146 (2)	C7—C8	1.381 (4)
Sn—O1	2.2471 (17)	C8—C9	1.374 (4)
Sn—S	2.6945 (7)	C8—H8	0.9500
S—C20	1.718 (3)	C9—C10	1.325 (6)
O1—C19	1.269 (3)	C9—H9	0.9500
O2—C19	1.243 (3)	C10—C11	1.398 (6)
N1—C20	1.321 (4)	C10—H10	0.9500
N1—H1A	0.81 (4)	C11—C12	1.406 (5)
N1—H1B	0.86 (4)	C11—H11	0.9500
N2—C20	1.324 (4)	C12—H12	0.9500
N2—H2A	0.85 (4)	C13—C18	1.384 (4)
N2—H2B	0.82 (4)	C13—C14	1.400 (4)
C1—C2	1.396 (3)	C14—C15	1.389 (4)
C1—C6	1.400 (4)	C14—H14	0.9500
C2—C3	1.391 (4)	C15—C16	1.375 (4)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.388 (4)	C16—C17	1.380 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.383 (4)	C17—C18	1.388 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.390 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C19ⁱ	1.538 (5)

C7—Sn—C13	124.52 (10)	C9—C8—C7	122.0 (3)
C7—Sn—C1	120.08 (9)	C9—C8—H8	119.0
C13—Sn—C1	115.36 (9)	C7—C8—H8	119.0
C7—Sn—O1	84.87 (8)	C10—C9—C8	120.5 (4)
C13—Sn—O1	97.26 (8)	C10—C9—H9	119.7
C1—Sn—O1	85.84 (8)	C8—C9—H9	119.7
C7—Sn—S	91.14 (7)	C9—C10—C11	120.1 (3)
C13—Sn—S	85.49 (7)	C9—C10—H10	120.0
C1—Sn—S	95.66 (7)	C11—C10—H10	120.0
O1—Sn—S	175.97 (5)	C10—C11—C12	119.2 (3)
C20—S—Sn	100.29 (9)	C10—C11—H11	120.4
C19—O1—Sn	123.37 (16)	C12—C11—H11	120.4
C20—N1—H1A	126 (3)	C7—C12—C11	120.3 (3)
C20—N1—H1B	123 (2)	C7—C12—H12	119.8
H1A—N1—H1B	111 (3)	C11—C12—H12	119.8
C20—N2—H2A	121 (2)	C18—C13—C14	118.4 (2)
C20—N2—H2B	119 (3)	C18—C13—Sn	123.08 (19)
H2A—N2—H2B	120 (3)	C14—C13—Sn	118.5 (2)
C2—C1—C6	117.7 (2)	C15—C14—C13	120.4 (3)
C2—C1—Sn	120.59 (19)	C15—C14—H14	119.8
C6—C1—Sn	121.12 (18)	C13—C14—H14	119.8
C3—C2—C1	121.1 (3)	C16—C15—C14	120.2 (3)
C3—C2—H2	119.4	C16—C15—H15	119.9
C1—C2—H2	119.4	C14—C15—H15	119.9
C4—C3—C2	120.3 (3)	C15—C16—C17	120.0 (3)
C4—C3—H3	119.8	C15—C16—H16	120.0
C2—C3—H3	119.8	C17—C16—H16	120.0
C5—C4—C3	119.4 (3)	C16—C17—C18	120.1 (3)
C5—C4—H4	120.3	C16—C17—H17	120.0
C3—C4—H4	120.3	C18—C17—H17	120.0
C4—C5—C6	120.3 (3)	C13—C18—C17	120.9 (3)
C4—C5—H5	119.9	C13—C18—H18	119.5
C6—C5—H5	119.9	C17—C18—H18	119.5
C5—C6—C1	121.2 (3)	O2—C19—O1	126.8 (2)
C5—C6—H6	119.4	O2—C19—C19ⁱ	116.57 (17)
C1—C6—H6	119.4	O1—C19—C19ⁱ	116.58 (18)
C12—C7—C8	117.9 (3)	N1—C20—N2	118.6 (3)
C12—C7—Sn	121.9 (2)	N1—C20—S	122.2 (2)
C8—C7—Sn	119.6 (2)	N2—C20—S	119.2 (2)

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
N1—H1A···O2ⁱⁱ	0.81 (4)	2.06 (4)	2.824 (3)	157 (4)
N2—H2A···O2ⁱⁱⁱ	0.86 (4)	2.14 (4)	2.970 (3)	164 (3)
C6—H6···O1	0.95	2.44	2.957 (3)	114
C18—H18···O2	0.95	2.39	3.234 (3)	147

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

Experimental details

Crystal data
Chemical formula	[Sn₂(C₂O₄)(C₆H₅)₆(CH₄N₂S)₂]
M_r	940.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	12.9161 (2), 13.9870 (2), 21.8215 (3)
β (°)	99.238 (1)
V (Å³)	3891.09 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.659, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	31403, 4472, 3665
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.066, 1.09
No. of reflections	4472
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.34, −1.11

Computer programs: COLLECT (Nonius, 1999), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia,1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.81 (4)	2.06 (4)	2.824 (3)	157 (4)
N2—H2A···O2ⁱⁱ	0.86 (4)	2.14 (4)	2.970 (3)	164 (3)
C6—H6···O1	0.95	2.44	2.957 (3)	114
C18—H18···O2	0.95	2.39	3.234 (3)	147

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

References

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Volume 68| Part 11| November 2012| Page m1337

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