Tetra­chloridobis(dibenzyl sulfoxide-κO)tin(IV)

Keng, T.C.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811015704

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m660

doi:10.1107/S1600536811015704

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Tetrachloridobis(dibenzyl sulfoxide-κO)tin(IV)

Thy Chun Keng,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 April 2011; accepted 26 April 2011; online 7 May 2011)

The six-coordinate Sn^IV atom in the title compound, [SnCl₄(C₁₄H₁₄OS)₂], exists in a cis-SnCl₄O₂ octahedral geometry. Of the four Cl atoms, two are close to adjacent S atoms [Cl⋯S = 3.320 (1) and 3.376 (1) Å]; the Sn—Cl bonds involving these two Cl atoms are longer than the other two Sn—Cl bonds.

Related literature

For the SnCl₄(DMSO)₂ adduct (DMSO is dimethyl sulfoxide), see: Kisenyi et al. (1985 ). For the tetrahydrothiophene-1-oxide adduct, see: Howie et al. (2010 ).

Experimental

Crystal data

[SnCl₄(C₁₄H₁₄OS)₂]
M_r = 721.11
Triclinic, $[P \overline 1]$
a = 10.7982 (1) Å
b = 11.1469 (1) Å
c = 14.9456 (2) Å
α = 80.8623 (6)°
β = 87.8310 (5)°
γ = 61.4279 (6)°
V = 1558.31 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.693, T_max = 0.693
14537 measured reflections
7139 independent reflections
6609 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.05
7139 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −1.02 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015704/bt5525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015704/bt5525Isup2.hkl

checkCIF report

Comment top

The attempted synthesis of the dibenzyl sulfoxide adduct of dibenzyltin chloride resulted in the cleavage both tin-carbon bonds to yield the 1:2 stannic chloride–dibenzyl sulfoxide adduct (Scheme I, Fig. 1). The six-coordinate Sn^IV atom exists in cis-SnCl₄O₂ octahedral geometry (Fig. 1). The adduct exists as a discrete molecule and there are no chlorine···chlorine contacts. The corresponding DMSO adduct shows a similar geometry (Kisenyi et al., 1985) as does the tetrahydrothiophenene-1-oxide adduct (Howie et al., 2010).

Related literature top

For the SnCl₄(DMSO)₂ adduct, see: Kisenyi et al. (1985). For the tetrahydrothiophene-1-oxide adduct, see: Howie et al. (2010).

Experimental top

Dibenzyltin dichloride (0.37 g, 1 mmol) and dibenzylsulfoxide (0.46 g, 2 mmol) were heated in ethanol (100 ml) for an hour. The solution was filtered and then set aside for the growth of colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl₄(C₁₄H₁₄OS)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Tetrachloridobis(dibenzyl sulfoxide-κO)tin(IV) top

Crystal data top

[SnCl₄(C₁₄H₁₄OS)₂]	Z = 2
M_r = 721.11	F(000) = 724
Triclinic, P1	D_x = 1.537 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7982 (1) Å	Cell parameters from 9933 reflections
b = 11.1469 (1) Å	θ = 2.3–28.3°
c = 14.9456 (2) Å	µ = 1.32 mm⁻¹
α = 80.8623 (6)°	T = 100 K
β = 87.8310 (5)°	Cuboic, colorless
γ = 61.4279 (6)°	0.30 × 0.30 × 0.30 mm
V = 1558.31 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	7139 independent reflections
Radiation source: fine-focus sealed tube	6609 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.693, T_max = 0.693	k = −14→14
14537 measured reflections	l = −19→19

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0353P)² + 1.7363P] where P = (F_o² + 2F_c²)/3
7139 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[SnCl₄(C₁₄H₁₄OS)₂]	γ = 61.4279 (6)°
M_r = 721.11	V = 1558.31 (3) Å³
Triclinic, P1	Z = 2
a = 10.7982 (1) Å	Mo Kα radiation
b = 11.1469 (1) Å	µ = 1.32 mm⁻¹
c = 14.9456 (2) Å	T = 100 K
α = 80.8623 (6)°	0.30 × 0.30 × 0.30 mm
β = 87.8310 (5)°

Data collection top

Bruker SMART APEX diffractometer	7139 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6609 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.693	R_int = 0.019
14537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.05	Δρ_max = 0.83 e Å⁻³
7139 reflections	Δρ_min = −1.02 e Å⁻³
334 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.596648 (15)	0.444875 (15)	0.252840 (10)	0.01653 (5)
Cl1	0.38718 (6)	0.50368 (6)	0.34078 (4)	0.02255 (12)
Cl2	0.73128 (6)	0.23980 (6)	0.35805 (4)	0.02240 (12)
Cl3	0.79172 (6)	0.41742 (6)	0.16256 (4)	0.02173 (11)
Cl4	0.51422 (7)	0.34402 (7)	0.15481 (4)	0.02784 (13)
S1	0.46614 (6)	0.65868 (6)	0.06715 (4)	0.01692 (11)
S2	0.63003 (5)	0.55337 (5)	0.43151 (4)	0.01626 (11)
O1	0.47446 (16)	0.64050 (16)	0.17213 (10)	0.0186 (3)
O2	0.63931 (16)	0.56674 (16)	0.32657 (10)	0.0180 (3)
C1	0.4837 (2)	0.8131 (2)	0.03527 (16)	0.0220 (5)
H1A	0.4505	0.8534	−0.0287	0.026*
H1B	0.4254	0.8828	0.0739	0.026*
C2	0.6361 (2)	0.7760 (2)	0.04695 (17)	0.0230 (5)
C3	0.7306 (3)	0.7160 (3)	−0.01962 (17)	0.0261 (5)
H3	0.6970	0.7040	−0.0736	0.031*
C4	0.8721 (3)	0.6743 (3)	−0.0072 (2)	0.0336 (6)
H4	0.9359	0.6332	−0.0524	0.040*
C5	0.9213 (3)	0.6923 (3)	0.0710 (2)	0.0390 (7)
H5	1.0188	0.6634	0.0795	0.047*
C6	0.8287 (3)	0.7522 (3)	0.1369 (2)	0.0375 (6)
H6	0.8627	0.7655	0.1903	0.045*
C7	0.6863 (3)	0.7931 (3)	0.12542 (19)	0.0294 (5)
H7	0.6232	0.8328	0.1713	0.035*
C8	0.2791 (2)	0.7253 (3)	0.04071 (16)	0.0219 (5)
H8A	0.2587	0.7669	−0.0242	0.026*
H8B	0.2580	0.6471	0.0502	0.026*
C9	0.1836 (2)	0.8315 (2)	0.09659 (16)	0.0211 (5)
C10	0.1443 (2)	0.7906 (3)	0.18065 (17)	0.0250 (5)
H10	0.1788	0.6949	0.2027	0.030*
C11	0.0553 (3)	0.8881 (3)	0.23263 (18)	0.0307 (6)
H11	0.0295	0.8589	0.2902	0.037*
C12	0.0036 (3)	1.0280 (3)	0.2011 (2)	0.0334 (6)
H12	−0.0575	1.0948	0.2367	0.040*
C13	0.0418 (3)	1.0697 (3)	0.1173 (2)	0.0305 (6)
H13	0.0064	1.1655	0.0954	0.037*
C14	0.1313 (3)	0.9726 (3)	0.06500 (18)	0.0258 (5)
H14	0.1572	1.0022	0.0076	0.031*
C15	0.7840 (2)	0.5654 (2)	0.46182 (16)	0.0207 (4)
H15A	0.7877	0.6433	0.4219	0.025*
H15B	0.7804	0.5812	0.5254	0.025*
C16	0.9120 (2)	0.4305 (3)	0.45052 (17)	0.0224 (5)
C17	0.9583 (3)	0.3185 (3)	0.52021 (19)	0.0289 (5)
H17	0.9121	0.3281	0.5760	0.035*
C18	1.0721 (3)	0.1923 (3)	0.5085 (2)	0.0358 (6)
H18	1.1032	0.1156	0.5562	0.043*
C19	1.1403 (3)	0.1780 (3)	0.4276 (2)	0.0377 (7)
H19	1.2188	0.0918	0.4200	0.045*
C20	1.0945 (3)	0.2887 (3)	0.3583 (2)	0.0397 (7)
H20	1.1411	0.2786	0.3026	0.048*
C21	0.9800 (3)	0.4155 (3)	0.36924 (18)	0.0302 (6)
H21	0.9485	0.4916	0.3211	0.036*
C22	0.4876 (2)	0.7197 (2)	0.45106 (16)	0.0209 (4)
H22A	0.3974	0.7174	0.4483	0.025*
H22B	0.5011	0.7332	0.5132	0.025*
C23	0.4757 (2)	0.8415 (2)	0.38565 (16)	0.0190 (4)
C24	0.3880 (2)	0.8883 (2)	0.30771 (16)	0.0227 (5)
H24	0.3403	0.8397	0.2948	0.027*
C25	0.3701 (3)	1.0057 (3)	0.24878 (18)	0.0310 (6)
H25	0.3087	1.0385	0.1964	0.037*
C26	0.4414 (3)	1.0743 (3)	0.2664 (2)	0.0361 (6)
H26	0.4290	1.1543	0.2258	0.043*
C27	0.5305 (3)	1.0283 (3)	0.3421 (2)	0.0373 (7)
H27	0.5805	1.0756	0.3531	0.045*
C28	0.5472 (3)	0.9122 (3)	0.40263 (19)	0.0281 (5)
H28	0.6073	0.8812	0.4555	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01704 (8)	0.01775 (8)	0.01609 (8)	−0.00884 (6)	0.00230 (5)	−0.00479 (6)
Cl1	0.0173 (2)	0.0304 (3)	0.0187 (2)	−0.0110 (2)	0.00222 (19)	−0.0022 (2)
Cl2	0.0230 (3)	0.0175 (2)	0.0230 (3)	−0.0069 (2)	0.0030 (2)	−0.0033 (2)
Cl3	0.0194 (3)	0.0212 (3)	0.0227 (3)	−0.0080 (2)	0.0060 (2)	−0.0054 (2)
Cl4	0.0408 (3)	0.0343 (3)	0.0217 (3)	−0.0275 (3)	0.0037 (2)	−0.0089 (2)
S1	0.0149 (2)	0.0185 (3)	0.0168 (2)	−0.0072 (2)	0.00010 (18)	−0.00387 (19)
S2	0.0157 (2)	0.0143 (2)	0.0170 (2)	−0.0053 (2)	0.00029 (18)	−0.00397 (19)
O1	0.0186 (8)	0.0201 (8)	0.0166 (7)	−0.0080 (6)	0.0013 (6)	−0.0057 (6)
O2	0.0187 (8)	0.0192 (8)	0.0167 (7)	−0.0091 (6)	0.0022 (6)	−0.0050 (6)
C1	0.0229 (11)	0.0199 (11)	0.0238 (11)	−0.0110 (9)	0.0006 (9)	−0.0024 (9)
C2	0.0210 (11)	0.0222 (11)	0.0277 (12)	−0.0127 (10)	0.0005 (9)	−0.0015 (9)
C3	0.0250 (12)	0.0276 (12)	0.0287 (12)	−0.0150 (10)	0.0045 (10)	−0.0053 (10)
C4	0.0252 (13)	0.0325 (14)	0.0443 (16)	−0.0150 (11)	0.0114 (11)	−0.0076 (12)
C5	0.0230 (13)	0.0426 (17)	0.0575 (19)	−0.0210 (13)	0.0022 (12)	−0.0066 (14)
C6	0.0311 (14)	0.0475 (17)	0.0430 (16)	−0.0254 (13)	−0.0047 (12)	−0.0085 (13)
C7	0.0284 (13)	0.0331 (14)	0.0331 (13)	−0.0188 (11)	0.0038 (10)	−0.0094 (11)
C8	0.0152 (10)	0.0269 (12)	0.0244 (11)	−0.0095 (9)	−0.0021 (8)	−0.0075 (9)
C9	0.0120 (10)	0.0251 (12)	0.0250 (11)	−0.0072 (9)	−0.0019 (8)	−0.0059 (9)
C10	0.0175 (11)	0.0263 (12)	0.0287 (12)	−0.0086 (10)	0.0006 (9)	−0.0039 (10)
C11	0.0231 (12)	0.0369 (15)	0.0272 (13)	−0.0104 (11)	0.0055 (10)	−0.0059 (11)
C12	0.0240 (13)	0.0346 (15)	0.0388 (15)	−0.0092 (11)	0.0083 (11)	−0.0165 (12)
C13	0.0202 (12)	0.0240 (12)	0.0442 (15)	−0.0075 (10)	0.0032 (10)	−0.0082 (11)
C14	0.0186 (11)	0.0268 (12)	0.0288 (12)	−0.0088 (10)	−0.0003 (9)	−0.0024 (10)
C15	0.0179 (10)	0.0185 (11)	0.0246 (11)	−0.0067 (9)	−0.0013 (8)	−0.0066 (9)
C16	0.0156 (10)	0.0241 (12)	0.0268 (12)	−0.0072 (9)	−0.0015 (9)	−0.0094 (9)
C17	0.0222 (12)	0.0270 (13)	0.0326 (13)	−0.0072 (10)	0.0005 (10)	−0.0070 (10)
C18	0.0272 (14)	0.0254 (13)	0.0441 (16)	−0.0041 (11)	−0.0076 (12)	−0.0028 (12)
C19	0.0205 (13)	0.0331 (15)	0.0479 (17)	0.0003 (11)	−0.0049 (11)	−0.0187 (13)
C20	0.0239 (13)	0.0480 (18)	0.0355 (15)	−0.0049 (13)	0.0027 (11)	−0.0174 (13)
C21	0.0240 (12)	0.0341 (14)	0.0273 (13)	−0.0087 (11)	−0.0005 (10)	−0.0082 (11)
C22	0.0191 (11)	0.0151 (10)	0.0226 (11)	−0.0032 (9)	0.0040 (8)	−0.0051 (9)
C23	0.0173 (10)	0.0158 (10)	0.0231 (11)	−0.0062 (8)	0.0042 (8)	−0.0081 (8)
C24	0.0207 (11)	0.0186 (11)	0.0263 (12)	−0.0062 (9)	0.0010 (9)	−0.0078 (9)
C25	0.0342 (14)	0.0223 (12)	0.0239 (12)	−0.0040 (11)	0.0007 (10)	−0.0022 (10)
C26	0.0357 (15)	0.0210 (12)	0.0437 (16)	−0.0098 (11)	0.0121 (12)	0.0007 (11)
C27	0.0305 (14)	0.0231 (13)	0.065 (2)	−0.0169 (11)	0.0101 (13)	−0.0136 (13)
C28	0.0211 (12)	0.0222 (12)	0.0411 (15)	−0.0083 (10)	−0.0038 (10)	−0.0111 (11)

Geometric parameters (Å, º) top

Sn1—O2	2.0938 (16)	C11—H11	0.9500
Sn1—O1	2.1176 (16)	C12—C13	1.383 (4)
Sn1—Cl3	2.3772 (5)	C12—H12	0.9500
Sn1—Cl2	2.3800 (6)	C13—C14	1.389 (4)
Sn1—Cl4	2.4045 (6)	C13—H13	0.9500
Sn1—Cl1	2.4297 (5)	C14—H14	0.9500
S1—O1	1.5502 (16)	C15—C16	1.508 (3)
S1—C1	1.809 (2)	C15—H15A	0.9900
S1—C8	1.822 (2)	C15—H15B	0.9900
S2—O2	1.5558 (16)	C16—C21	1.386 (4)
S2—C15	1.810 (2)	C16—C17	1.387 (4)
S2—C22	1.816 (2)	C17—C18	1.388 (4)
C1—C2	1.503 (3)	C17—H17	0.9500
C1—H1A	0.9900	C18—C19	1.382 (4)
C1—H1B	0.9900	C18—H18	0.9500
C2—C7	1.387 (4)	C19—C20	1.375 (5)
C2—C3	1.400 (3)	C19—H19	0.9500
C3—C4	1.379 (4)	C20—C21	1.393 (4)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.383 (4)	C21—H21	0.9500
C4—H4	0.9500	C22—C23	1.495 (3)
C5—C6	1.383 (4)	C22—H22A	0.9900
C5—H5	0.9500	C22—H22B	0.9900
C6—C7	1.388 (4)	C23—C28	1.393 (3)
C6—H6	0.9500	C23—C24	1.394 (3)
C7—H7	0.9500	C24—C25	1.390 (4)
C8—C9	1.498 (3)	C24—H24	0.9500
C8—H8A	0.9900	C25—C26	1.374 (4)
C8—H8B	0.9900	C25—H25	0.9500
C9—C10	1.389 (3)	C26—C27	1.377 (5)
C9—C14	1.397 (3)	C26—H26	0.9500
C10—C11	1.386 (4)	C27—C28	1.394 (4)
C10—H10	0.9500	C27—H27	0.9500
C11—C12	1.386 (4)	C28—H28	0.9500

O2—Sn1—O1	81.00 (6)	C10—C11—H11	119.8
O2—Sn1—Cl3	88.98 (4)	C12—C11—H11	119.8
O1—Sn1—Cl3	88.48 (4)	C13—C12—C11	119.5 (3)
O2—Sn1—Cl2	92.70 (4)	C13—C12—H12	120.3
O1—Sn1—Cl2	173.13 (4)	C11—C12—H12	120.3
Cl3—Sn1—Cl2	94.17 (2)	C12—C13—C14	120.5 (3)
O2—Sn1—Cl4	169.67 (5)	C12—C13—H13	119.7
O1—Sn1—Cl4	88.95 (4)	C14—C13—H13	119.7
Cl3—Sn1—Cl4	93.16 (2)	C13—C14—C9	120.2 (2)
Cl2—Sn1—Cl4	97.22 (2)	C13—C14—H14	119.9
O2—Sn1—Cl1	86.64 (4)	C9—C14—H14	119.9
O1—Sn1—Cl1	85.29 (4)	C16—C15—S2	107.39 (16)
Cl3—Sn1—Cl1	172.87 (2)	C16—C15—H15A	110.2
Cl2—Sn1—Cl1	91.656 (19)	S2—C15—H15A	110.2
Cl4—Sn1—Cl1	90.18 (2)	C16—C15—H15B	110.2
O1—S1—C1	101.73 (10)	S2—C15—H15B	110.2
O1—S1—C8	103.26 (10)	H15A—C15—H15B	108.5
C1—S1—C8	101.23 (11)	C21—C16—C17	119.5 (2)
O2—S2—C15	100.62 (10)	C21—C16—C15	120.5 (2)
O2—S2—C22	104.75 (10)	C17—C16—C15	119.9 (2)
C15—S2—C22	101.73 (11)	C16—C17—C18	120.1 (3)
S1—O1—Sn1	121.84 (9)	C16—C17—H17	119.9
S2—O2—Sn1	121.81 (9)	C18—C17—H17	119.9
C2—C1—S1	108.98 (16)	C19—C18—C17	120.2 (3)
C2—C1—H1A	109.9	C19—C18—H18	119.9
S1—C1—H1A	109.9	C17—C18—H18	119.9
C2—C1—H1B	109.9	C20—C19—C18	119.9 (3)
S1—C1—H1B	109.9	C20—C19—H19	120.1
H1A—C1—H1B	108.3	C18—C19—H19	120.1
C7—C2—C3	119.4 (2)	C19—C20—C21	120.3 (3)
C7—C2—C1	120.7 (2)	C19—C20—H20	119.8
C3—C2—C1	119.8 (2)	C21—C20—H20	119.8
C4—C3—C2	120.3 (2)	C16—C21—C20	119.9 (3)
C4—C3—H3	119.9	C16—C21—H21	120.0
C2—C3—H3	119.9	C20—C21—H21	120.0
C3—C4—C5	120.0 (3)	C23—C22—S2	114.98 (16)
C3—C4—H4	120.0	C23—C22—H22A	108.5
C5—C4—H4	120.0	S2—C22—H22A	108.5
C4—C5—C6	120.2 (3)	C23—C22—H22B	108.5
C4—C5—H5	119.9	S2—C22—H22B	108.5
C6—C5—H5	119.9	H22A—C22—H22B	107.5
C5—C6—C7	120.2 (3)	C28—C23—C24	119.2 (2)
C5—C6—H6	119.9	C28—C23—C22	121.2 (2)
C7—C6—H6	119.9	C24—C23—C22	119.6 (2)
C6—C7—C2	120.0 (3)	C25—C24—C23	120.2 (2)
C6—C7—H7	120.0	C25—C24—H24	119.9
C2—C7—H7	120.0	C23—C24—H24	119.9
C9—C8—S1	113.76 (16)	C26—C25—C24	119.9 (3)
C9—C8—H8A	108.8	C26—C25—H25	120.1
S1—C8—H8A	108.8	C24—C25—H25	120.1
C9—C8—H8B	108.8	C25—C26—C27	120.8 (3)
S1—C8—H8B	108.8	C25—C26—H26	119.6
H8A—C8—H8B	107.7	C27—C26—H26	119.6
C10—C9—C14	118.9 (2)	C26—C27—C28	119.8 (3)
C10—C9—C8	120.2 (2)	C26—C27—H27	120.1
C14—C9—C8	120.9 (2)	C28—C27—H27	120.1
C11—C10—C9	120.6 (2)	C23—C28—C27	120.0 (2)
C11—C10—H10	119.7	C23—C28—H28	120.0
C9—C10—H10	119.7	C27—C28—H28	120.0
C10—C11—C12	120.3 (2)

C1—S1—O1—Sn1	−136.20 (11)	C9—C10—C11—C12	0.3 (4)
C8—S1—O1—Sn1	119.12 (11)	C10—C11—C12—C13	−0.1 (4)
O2—Sn1—O1—S1	140.81 (11)	C11—C12—C13—C14	−0.2 (4)
Cl3—Sn1—O1—S1	51.60 (10)	C12—C13—C14—C9	0.2 (4)
Cl4—Sn1—O1—S1	−41.59 (10)	C10—C9—C14—C13	0.1 (4)
Cl1—Sn1—O1—S1	−131.86 (10)	C8—C9—C14—C13	179.4 (2)
C15—S2—O2—Sn1	138.94 (11)	O2—S2—C15—C16	−73.55 (17)
C22—S2—O2—Sn1	−115.80 (11)	C22—S2—C15—C16	178.78 (16)
O1—Sn1—O2—S2	132.52 (11)	S2—C15—C16—C21	92.2 (2)
Cl3—Sn1—O2—S2	−138.85 (10)	S2—C15—C16—C17	−84.7 (2)
Cl2—Sn1—O2—S2	−44.73 (10)	C21—C16—C17—C18	0.1 (4)
Cl4—Sn1—O2—S2	119.0 (2)	C15—C16—C17—C18	177.0 (2)
Cl1—Sn1—O2—S2	46.77 (10)	C16—C17—C18—C19	0.4 (4)
O1—S1—C1—C2	77.36 (18)	C17—C18—C19—C20	−0.6 (4)
C8—S1—C1—C2	−176.37 (17)	C18—C19—C20—C21	0.3 (5)
S1—C1—C2—C7	−96.3 (2)	C17—C16—C21—C20	−0.4 (4)
S1—C1—C2—C3	80.0 (2)	C15—C16—C21—C20	−177.3 (2)
C7—C2—C3—C4	0.1 (4)	C19—C20—C21—C16	0.2 (4)
C1—C2—C3—C4	−176.3 (2)	O2—S2—C22—C23	−35.0 (2)
C2—C3—C4—C5	−0.3 (4)	C15—S2—C22—C23	69.5 (2)
C3—C4—C5—C6	−0.1 (4)	S2—C22—C23—C28	−90.2 (2)
C4—C5—C6—C7	0.8 (5)	S2—C22—C23—C24	92.0 (2)
C5—C6—C7—C2	−1.1 (4)	C28—C23—C24—C25	−1.3 (4)
C3—C2—C7—C6	0.6 (4)	C22—C23—C24—C25	176.6 (2)
C1—C2—C7—C6	177.0 (2)	C23—C24—C25—C26	1.4 (4)
O1—S1—C8—C9	41.3 (2)	C24—C25—C26—C27	−0.2 (4)
C1—S1—C8—C9	−63.7 (2)	C25—C26—C27—C28	−1.1 (4)
S1—C8—C9—C10	−86.7 (2)	C24—C23—C28—C27	0.1 (4)
S1—C8—C9—C14	94.0 (2)	C22—C23—C28—C27	−177.8 (2)
C14—C9—C10—C11	−0.3 (4)	C26—C27—C28—C23	1.1 (4)
C8—C9—C10—C11	−179.6 (2)

Experimental details

Crystal data
Chemical formula	[SnCl₄(C₁₄H₁₄OS)₂]
M_r	721.11
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.7982 (1), 11.1469 (1), 14.9456 (2)
α, β, γ (°)	80.8623 (6), 87.8310 (5), 61.4279 (6)
V (Å³)	1558.31 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.693, 0.693
No. of measured, independent and observed [I > 2σ(I)] reflections	14537, 7139, 6609
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.05
No. of reflections	7139
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −1.02

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya (Ggrant No. RG020/09AFR) for supporting this study.

References

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