Bis(2-ethoxy-carbonyl-ethyl-κC,O)(2-thioxo-1,3-dithiole-4,5-dithiol-ato-κS,S)tin(IV).

In the title compound, [Sn(C(5)H(9)O(2))(2)(C(3)S(5))], the immediate environment around the Sn centre is defined by two S and two C atoms that define an approximately tetra-hedral geometry. The close approach of the pendant carbonyl O atoms [Sn-O = 2.577 (3) and 2.573 (3) Å] increases the coordination number to six. Supra-molecular chains are formed along the a axis in the crystal structure owing to the presence of C-H⋯O contacts.

Related literature

For original industrial inter­est in functionally substituted-alkyl-tin compounds, see: Lanigen & Weinberg (1976 ▶). For studies concerning the coordination chemistry of functionally substituted-alkyl-tin compounds, see: Harrison et al. (1979 ▶); Balasubramanian et al. (1997 ▶); Milne et al. (2005 ▶); Tian et al. (2005 ▶); de Lima et al. (2009 ▶). For related structures of functionally substituted-alkyl-tin compounds, see: Buchanan et al. (1996 ▶); Howie & Wardell, (2001 ▶). For the synthesis, see: Hutton & Oakes (1976 ▶); Valade et al. (1985 ▶).

Experimental

Crystal data

[Sn(C5H9O2)2(C3S5)]

M = 517.26

Orthorhombic,

a = 12.1224 (2) Å

b = 13.3825 (2) Å

c = 11.9228 (2) Å

V = 1934.21 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.87 mm−1

T = 120 K

0.25 × 0.10 × 0.08 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.025, T max = 0.052

14014 measured reflections

3895 independent reflections

3457 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.064

S = 1.04

3895 reflections

211 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048971/im2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048971/im2162Isup2.hkl

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

[Sn(C5H9O2)2(C3S5)]	F(000) = 1032
Mr = 517.26	Dx = 1.776 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2n	Cell parameters from 16139 reflections
a = 12.1224 (2) Å	θ = 2.9–27.5°
b = 13.3825 (2) Å	µ = 1.87 mm−1
c = 11.9228 (2) Å	T = 120 K
V = 1934.21 (5) Å3	Block, orange
Z = 4	0.25 × 0.10 × 0.08 mm

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	3895 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3457 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −17→17
Tmin = 0.025, Tmax = 0.052	l = −13→15
14014 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0188P)2 + 0.7375P] where P = (Fo2 + 2Fc2)/3
3895 reflections	(Δ/σ)max = 0.002
211 parameters	Δρmax = 0.64 e Å−3
15 restraints	Δρmin = −0.48 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.529829 (17)	0.337064 (17)	0.45100 (3)	0.02754 (8)
S1	0.53453 (8)	0.51943 (8)	0.41409 (10)	0.0335 (3)
S2	0.73501 (8)	0.33979 (7)	0.46792 (12)	0.0345 (3)
S3	0.88592 (8)	0.51390 (8)	0.48204 (9)	0.0346 (3)
S4	0.72095 (7)	0.66289 (7)	0.43844 (12)	0.0321 (2)
S5	0.94961 (10)	0.72872 (9)	0.49178 (10)	0.0453 (3)
O1	0.5826 (3)	0.1584 (2)	0.5112 (3)	0.0379 (7)
O2	0.6277 (3)	0.0814 (3)	0.6703 (3)	0.0573 (10)
O3	0.3343 (2)	0.3912 (2)	0.3931 (2)	0.0309 (6)
O4	0.2446 (2)	0.4120 (2)	0.2305 (2)	0.0360 (7)
C1	0.6756 (3)	0.5390 (3)	0.4401 (4)	0.0295 (9)
C2	0.7527 (3)	0.4689 (3)	0.4608 (5)	0.0307 (8)
C3	0.8572 (3)	0.6406 (3)	0.4716 (4)	0.0313 (10)
C4	0.4687 (4)	0.3126 (4)	0.6175 (4)	0.0356 (11)
H4A	0.4635	0.3773	0.6572	0.043*
H4B	0.3938	0.2834	0.6134	0.043*
C5	0.5442 (4)	0.2423 (4)	0.6830 (4)	0.0417 (11)
H5A	0.6080	0.2807	0.7119	0.050*
H5B	0.5033	0.2154	0.7483	0.050*
C6	0.5855 (4)	0.1571 (3)	0.6132 (4)	0.0412 (11)
C7	0.6762 (6)	0.0013 (4)	0.6013 (5)	0.0691 (19)
H7A	0.7202	0.0313	0.5399	0.083*
H7B	0.6164	−0.0389	0.5671	0.083*
C8	0.7474 (5)	−0.0643 (6)	0.6694 (5)	0.086 (2)
H8A	0.8081	−0.0250	0.7012	0.129*
H8B	0.7776	−0.1175	0.6220	0.129*
H8C	0.7040	−0.0939	0.7302	0.129*
C9	0.4905 (3)	0.2620 (3)	0.2973 (3)	0.0314 (10)
H9A	0.5593	0.2486	0.2552	0.038*
H9B	0.4553	0.1970	0.3145	0.038*
C10	0.4131 (4)	0.3238 (3)	0.2247 (4)	0.0367 (10)
H10A	0.4569	0.3730	0.1817	0.044*
H10B	0.3758	0.2792	0.1704	0.044*
C11	0.3272 (3)	0.3782 (3)	0.2923 (4)	0.0301 (9)
C12	0.1619 (4)	0.4726 (4)	0.2870 (4)	0.0392 (11)
H12A	0.1468	0.4441	0.3621	0.047*
H12B	0.0924	0.4710	0.2434	0.047*
C13	0.1992 (4)	0.5781 (3)	0.2994 (4)	0.0445 (11)
H13A	0.2706	0.5796	0.3379	0.067*
H13B	0.1448	0.6156	0.3433	0.067*
H13C	0.2068	0.6086	0.2250	0.067*

	U11	U22	U33	U12	U13	U23
Sn	0.02877 (12)	0.02691 (13)	0.02694 (13)	−0.00144 (10)	0.00049 (14)	−0.00137 (15)
S1	0.0284 (5)	0.0272 (5)	0.0451 (7)	0.0013 (4)	−0.0039 (4)	0.0017 (4)
S2	0.0292 (4)	0.0272 (5)	0.0472 (9)	0.0016 (4)	−0.0027 (5)	0.0020 (6)
S3	0.0289 (4)	0.0381 (5)	0.0368 (7)	−0.0026 (4)	−0.0014 (4)	−0.0022 (5)
S4	0.0363 (4)	0.0271 (4)	0.0330 (7)	−0.0037 (4)	0.0001 (5)	−0.0019 (5)
S5	0.0491 (6)	0.0502 (7)	0.0367 (6)	−0.0208 (6)	0.0015 (5)	−0.0058 (6)
O1	0.0438 (18)	0.0333 (16)	0.0365 (19)	0.0018 (13)	−0.0047 (14)	−0.0023 (13)
O2	0.075 (3)	0.049 (2)	0.048 (2)	0.0012 (18)	−0.0188 (18)	0.0071 (18)
O3	0.0315 (13)	0.0359 (16)	0.0254 (16)	0.0003 (13)	−0.0035 (12)	−0.0002 (13)
O4	0.0329 (15)	0.0445 (19)	0.0306 (18)	0.0062 (14)	−0.0022 (13)	−0.0018 (15)
C1	0.0323 (17)	0.0266 (17)	0.030 (2)	−0.0050 (15)	−0.003 (2)	0.001 (2)
C2	0.0297 (16)	0.0280 (18)	0.034 (2)	−0.0046 (14)	−0.002 (2)	−0.009 (2)
C3	0.0352 (18)	0.038 (2)	0.021 (3)	−0.0066 (16)	0.0031 (17)	0.0026 (19)
C4	0.039 (3)	0.035 (3)	0.032 (3)	−0.0048 (19)	0.0015 (18)	−0.004 (2)
C5	0.051 (3)	0.047 (3)	0.027 (2)	−0.010 (2)	−0.001 (2)	0.004 (2)
C6	0.042 (3)	0.039 (3)	0.043 (3)	−0.014 (2)	−0.005 (2)	0.008 (2)
C7	0.092 (5)	0.051 (4)	0.065 (4)	0.018 (3)	−0.031 (4)	−0.016 (3)
C8	0.069 (4)	0.121 (7)	0.069 (5)	0.021 (4)	−0.012 (3)	−0.022 (4)
C9	0.034 (2)	0.031 (2)	0.029 (2)	0.0001 (19)	0.0013 (18)	−0.002 (2)
C10	0.036 (2)	0.046 (3)	0.028 (2)	0.006 (2)	−0.003 (2)	−0.003 (2)
C11	0.031 (2)	0.027 (2)	0.032 (3)	0.0007 (18)	−0.0012 (18)	0.0004 (18)
C12	0.032 (2)	0.048 (3)	0.038 (3)	0.007 (2)	0.0047 (19)	−0.002 (2)
C13	0.044 (3)	0.038 (3)	0.051 (3)	0.005 (2)	0.001 (2)	0.006 (2)

Sn—C4	2.144 (5)	C4—H4B	0.9900
Sn—C9	2.144 (4)	C5—C6	1.498 (7)
Sn—S1	2.4805 (11)	C5—H5A	0.9900
Sn—S2	2.4958 (9)	C5—H5B	0.9900
Sn—O3	2.573 (3)	C7—C8	1.475 (4)
Sn—O1	2.577 (3)	C7—H7A	0.9900
S1—C1	1.758 (4)	C7—H7B	0.9900
S2—C2	1.743 (4)	C8—H8A	0.9800
S3—C3	1.735 (4)	C8—H8B	0.9800
S3—C2	1.742 (3)	C8—H8C	0.9800
S4—C3	1.724 (4)	C9—C10	1.520 (6)
S4—C1	1.746 (4)	C9—H9A	0.9900
S5—C3	1.644 (4)	C9—H9B	0.9900
O1—C6	1.217 (5)	C10—C11	1.505 (6)
O2—C6	1.324 (6)	C10—H10A	0.9900
O2—C7	1.474 (4)	C10—H10B	0.9900
O3—C11	1.217 (5)	C12—C13	1.490 (6)
O4—C11	1.323 (5)	C12—H12A	0.9900
O4—C12	1.454 (5)	C12—H12B	0.9900
C1—C2	1.348 (5)	C13—H13A	0.9800
C4—C5	1.527 (6)	C13—H13B	0.9800
C4—H4A	0.9900	C13—H13C	0.9800
C4—Sn—C9	130.01 (17)	H5A—C5—H5B	107.8
C4—Sn—S1	108.82 (14)	O1—C6—O2	122.4 (5)
C9—Sn—S1	108.33 (12)	O1—C6—C5	122.3 (4)
C4—Sn—S2	105.78 (12)	O2—C6—C5	115.2 (4)
C9—Sn—S2	107.32 (11)	O2—C7—C8	111.0 (5)
S1—Sn—S2	88.68 (3)	O2—C7—H7A	109.4
C4—Sn—O3	88.46 (13)	C8—C7—H7A	109.4
C9—Sn—O3	72.38 (13)	O2—C7—H7B	109.4
S1—Sn—O3	72.34 (7)	C8—C7—H7B	109.4
S2—Sn—O3	159.35 (7)	H7A—C7—H7B	108.0
C4—Sn—O1	71.72 (15)	C7—C8—H8A	109.5
C9—Sn—O1	81.87 (14)	C7—C8—H8B	109.5
S1—Sn—O1	163.04 (7)	H8A—C8—H8B	109.5
S2—Sn—O1	75.14 (7)	C7—C8—H8C	109.5
O3—Sn—O1	124.38 (9)	H8A—C8—H8C	109.5
C1—S1—Sn	97.92 (13)	H8B—C8—H8C	109.5
C2—S2—Sn	97.66 (11)	C10—C9—Sn	111.7 (3)
C3—S3—C2	98.14 (18)	C10—C9—H9A	109.3
C3—S4—C1	97.73 (18)	Sn—C9—H9A	109.3
C6—O1—Sn	107.4 (3)	C10—C9—H9B	109.3
C6—O2—C7	115.0 (4)	Sn—C9—H9B	109.3
C11—O3—Sn	106.9 (2)	H9A—C9—H9B	108.0
C11—O4—C12	117.1 (3)	C11—C10—C9	112.7 (4)
C2—C1—S4	116.4 (3)	C11—C10—H10A	109.1
C2—C1—S1	127.1 (3)	C9—C10—H10A	109.1
S4—C1—S1	116.5 (2)	C11—C10—H10B	109.1
C1—C2—S3	115.4 (3)	C9—C10—H10B	109.1
C1—C2—S2	127.9 (3)	H10A—C10—H10B	107.8
S3—C2—S2	116.7 (2)	O3—C11—O4	123.7 (4)
S5—C3—S4	124.2 (2)	O3—C11—C10	123.2 (4)
S5—C3—S3	123.6 (2)	O4—C11—C10	113.1 (4)
S4—C3—S3	112.2 (2)	O4—C12—C13	111.4 (4)
C5—C4—Sn	111.2 (3)	O4—C12—H12A	109.3
C5—C4—H4A	109.4	C13—C12—H12A	109.3
Sn—C4—H4A	109.4	O4—C12—H12B	109.3
C5—C4—H4B	109.4	C13—C12—H12B	109.3
Sn—C4—H4B	109.4	H12A—C12—H12B	108.0
H4A—C4—H4B	108.0	C12—C13—H13A	109.5
C6—C5—C4	112.6 (4)	C12—C13—H13B	109.5
C6—C5—H5A	109.1	H13A—C13—H13B	109.5
C4—C5—H5A	109.1	C12—C13—H13C	109.5
C6—C5—H5B	109.1	H13A—C13—H13C	109.5
C4—C5—H5B	109.1	H13B—C13—H13C	109.5
C4—Sn—S1—C1	99.3 (2)	Sn—S2—C2—S3	174.2 (3)
C9—Sn—S1—C1	−114.8 (2)	C1—S4—C3—S5	−176.2 (3)
S2—Sn—S1—C1	−6.96 (17)	C1—S4—C3—S3	3.4 (3)
O3—Sn—S1—C1	−178.67 (18)	C2—S3—C3—S5	176.1 (3)
O1—Sn—S1—C1	10.3 (3)	C2—S3—C3—S4	−3.5 (3)
C4—Sn—S2—C2	−102.3 (2)	C9—Sn—C4—C5	94.0 (3)
C9—Sn—S2—C2	115.7 (2)	S1—Sn—C4—C5	−129.9 (3)
S1—Sn—S2—C2	6.90 (19)	S2—Sn—C4—C5	−35.8 (3)
O3—Sn—S2—C2	29.8 (3)	O3—Sn—C4—C5	159.3 (3)
O1—Sn—S2—C2	−168.0 (2)	O1—Sn—C4—C5	32.2 (3)
C4—Sn—O1—C6	−24.6 (3)	Sn—C4—C5—C6	−40.7 (5)
C9—Sn—O1—C6	−161.6 (3)	Sn—O1—C6—O2	−168.4 (4)
S1—Sn—O1—C6	70.1 (4)	Sn—O1—C6—C5	9.8 (5)
S2—Sn—O1—C6	88.0 (3)	C7—O2—C6—O1	3.0 (7)
O3—Sn—O1—C6	−99.5 (3)	C7—O2—C6—C5	−175.4 (5)
C4—Sn—O3—C11	−156.3 (3)	C4—C5—C6—O1	17.7 (6)
C9—Sn—O3—C11	−23.1 (3)	C4—C5—C6—O2	−163.9 (4)
S1—Sn—O3—C11	93.4 (3)	C6—O2—C7—C8	164.1 (5)
S2—Sn—O3—C11	69.3 (4)	C4—Sn—C9—C10	102.9 (4)
O1—Sn—O3—C11	−89.7 (3)	S1—Sn—C9—C10	−33.2 (3)
C3—S4—C1—C2	−2.0 (4)	S2—Sn—C9—C10	−127.7 (3)
C3—S4—C1—S1	178.3 (3)	O3—Sn—C9—C10	30.6 (3)
Sn—S1—C1—C2	6.4 (5)	O1—Sn—C9—C10	160.7 (3)
Sn—S1—C1—S4	−173.9 (2)	Sn—C9—C10—C11	−38.3 (4)
S4—C1—C2—S3	−0.2 (5)	Sn—O3—C11—O4	−169.2 (3)
S1—C1—C2—S3	179.5 (3)	Sn—O3—C11—C10	9.5 (5)
S4—C1—C2—S2	−179.9 (3)	C12—O4—C11—O3	3.7 (6)
S1—C1—C2—S2	−0.2 (7)	C12—O4—C11—C10	−175.2 (4)
C3—S3—C2—C1	2.3 (4)	C9—C10—C11—O3	16.6 (6)
C3—S3—C2—S2	−178.0 (3)	C9—C10—C11—O4	−164.6 (4)
Sn—S2—C2—C1	−6.1 (5)	C11—O4—C12—C13	81.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12a···O1i	0.99	2.38	3.338 (6)	164
C7—H7a···O3ii	0.99	2.46	3.450 (7)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12a⋯O1i	0.99	2.38	3.338 (6)	164
C7—H7a⋯O3ii	0.99	2.46	3.450 (7)	178

Symmetry codes: (i) ; (ii) .