μ(2)-Oxalato-bis-[triphen-yl(thio-urea-κS)tin(IV)].

The asymmetric unit of the binuclear title compound, [Sn(2)(C(2)O(4))(C(6)H(5))(6)(CH(4)N(2)S)(2)], consists of one half of the organotin(IV) mol-ecule. 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 thio-urea and the monodentately bridging oxalate anion in axial positions. The mol-ecules are linked through N-H⋯O hydrogen bonds involving the amino group of the thio-urea ligand and the uncoordinating oxalate O atoms, forming layers parallel to (001). Weak C-H⋯O inter-actions 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 = 940.24

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.066

S = 1.09

4472 reflections

251 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.34 e Å−3

Δρmin = −1.11 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812040706/wm2662sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn2(C2O4)(C6H5)6(CH4N2S)2]	F(000) = 1880
Mr = 940.24	Dx = 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

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

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(Fo2) + (0.0248P)2 + 7.4801P] where P = (Fo2 + 2Fc2)/3
4472 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 1.34 e Å−3
0 restraints	Δρmin = −1.11 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .