(Benzyl phenyl sulfoxide-κO)-chlorido-triphenyl-tin(IV).

The Sn(IV) atom in the title compound, [Sn(C(6)H(5))(3)Cl(C(13)H(12)OS)], is situated within a distorted C(3)ClO trigonal-bipyramidal coordination geometry with a mean Sn-C distance of 2.136 (6) Å and with an Sn-O distance of 2.393 (4) Å. The Sn(IV) atom lies 0.171 (3) Å out of the equatorial C(3) plane in the direction of the axially bound Cl atom.

Related literature

For background to the structures, biological activities and industrial applications of triorganotin(IV) complexes, see: Davies et al. (2008 ▶); Tian et al. (2005 ▶). For related organotin sulfoxide structures, see: Fuller et al. (2009 ▶); Kumar et al. (2009 ▶); Filgueiras et al. (1982 ▶); Dokorou et al. (2011 ▶).

Experimental

Crystal data

[Sn(C6H5)3Cl(C13H12OS)]

M = 601.73

Orthorhombic,

a = 9.744 (5) Å

b = 10.016 (3) Å

c = 28.840 (5) Å

V = 2814.7 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.10 mm−1

T = 295 K

0.32 × 0.28 × 0.21 mm

Data collection

Bruker P4 diffractometer

Absorption correction: ψ scan (XSCANS; Bruker, 1996 ▶) T min = 0.720, T max = 0.802

3690 measured reflections

3463 independent reflections

2794 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 97 reflections intensity decay: 2.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.067

S = 1.02

3463 reflections

306 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 626 Friedel pairs

Flack parameter: 0.02 (3)

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005910/tk5048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005910/tk5048Isup2.hkl

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

[Sn(C6H5)3Cl(C13H12OS)]	F(000) = 1216
Mr = 601.73	Dx = 1.420 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 35 reflections
a = 9.744 (5) Å	θ = 5.1–12.5°
b = 10.016 (3) Å	µ = 1.10 mm−1
c = 28.840 (5) Å	T = 295 K
V = 2814.7 (17) Å3	Block, colourless
Z = 4	0.32 × 0.28 × 0.21 mm

Bruker P4 diffractometer	2794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω scans	h = −1→11
Absorption correction: ψ scan (XSCANS; Bruker, 1996)	k = −1→11
Tmin = 0.720, Tmax = 0.802	l = −1→34
3690 measured reflections	3 standard reflections every 97 reflections
3463 independent reflections	intensity decay: 2.3%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.024P)2 + 0.0502P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.067	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.37 e Å−3
3463 reflections	Δρmin = −0.40 e Å−3
306 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.00117 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 626 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (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
Sn1	0.09780 (5)	0.65032 (4)	0.122403 (15)	0.04029 (13)
O1	−0.1431 (4)	0.6938 (4)	0.12855 (16)	0.0497 (12)
Cl1	0.34939 (15)	0.60290 (16)	0.12177 (6)	0.0534 (4)
S1	−0.19603 (16)	0.83689 (17)	0.13031 (6)	0.0502 (4)
C1	0.0329 (7)	0.4480 (6)	0.1119 (2)	0.0423 (17)
C2	−0.0971 (9)	0.4170 (7)	0.0986 (2)	0.064 (2)
H2	−0.1620	0.4846	0.0959	0.077*
C3	−0.1346 (9)	0.2866 (8)	0.0890 (3)	0.086 (3)
H3	−0.2243	0.2680	0.0800	0.103*
C4	−0.0424 (9)	0.1856 (7)	0.0925 (3)	0.076 (3)
H4	−0.0676	0.0985	0.0854	0.091*
C5	0.0869 (9)	0.2137 (7)	0.1067 (3)	0.079 (3)
H5	0.1504	0.1452	0.1101	0.095*
C6	0.1254 (7)	0.3454 (7)	0.1162 (2)	0.066 (2)
H6	0.2147	0.3636	0.1256	0.079*
C7	0.1114 (6)	0.7524 (5)	0.18703 (12)	0.0494 (18)
C8	0.2066 (6)	0.8553 (5)	0.19079 (17)	0.089 (3)
H8	0.2597	0.8792	0.1653	0.107*
C9	0.2224 (6)	0.9224 (5)	0.2326 (2)	0.122 (4)
H9	0.2861	0.9912	0.2351	0.146*
C10	0.1431 (7)	0.8867 (6)	0.27072 (15)	0.111 (4)
H10	0.1536	0.9316	0.2987	0.133*
C11	0.0479 (6)	0.7838 (6)	0.26696 (13)	0.098 (4)
H11	−0.0052	0.7599	0.2924	0.117*
C12	0.0321 (5)	0.7167 (5)	0.22511 (18)	0.070 (2)
H12	−0.0316	0.6479	0.2226	0.084*
C13	−0.2771 (7)	0.8539 (7)	0.1851 (2)	0.0495 (16)
C14	−0.3607 (8)	0.7581 (7)	0.2023 (3)	0.066 (2)
H14	−0.3769	0.6807	0.1853	0.079*
C15	−0.4224 (9)	0.7757 (8)	0.2452 (3)	0.078 (2)
H15	−0.4808	0.7106	0.2570	0.093*
C16	−0.3965 (10)	0.8893 (9)	0.2701 (3)	0.087 (3)
H16	−0.4384	0.9019	0.2988	0.105*
C17	−0.3094 (9)	0.9846 (9)	0.2530 (3)	0.088 (3)
H17	−0.2907	1.0608	0.2703	0.106*
C18	−0.2498 (8)	0.9676 (7)	0.2103 (3)	0.066 (2)
H18	−0.1912	1.0325	0.1985	0.079*
C19	−0.3445 (6)	0.8314 (7)	0.0924 (2)	0.0564 (19)
H19A	−0.3179	0.7908	0.0632	0.068*
H19B	−0.4140	0.7750	0.1064	0.068*
C20	−0.4055 (8)	0.9656 (7)	0.0828 (2)	0.0556 (17)
C21	−0.4840 (8)	1.0320 (8)	0.1156 (3)	0.074 (2)
H21A	−0.4991	0.9929	0.1444	0.088*
C22	−0.5403 (9)	1.1564 (10)	0.1058 (4)	0.103 (3)
H22A	−0.5896	1.2019	0.1285	0.124*
C23	−0.5235 (11)	1.2117 (10)	0.0632 (5)	0.109 (4)
H23A	−0.5649	1.2932	0.0566	0.131*
C24	−0.4459 (10)	1.1491 (10)	0.0294 (4)	0.104 (4)
H24A	−0.4332	1.1880	0.0004	0.125*
C25	−0.3872 (9)	1.0254 (8)	0.0401 (3)	0.076 (2)
H25A	−0.3344	0.9821	0.0178	0.091*
C26	0.0997 (7)	0.7770 (6)	0.06277 (19)	0.0376 (14)
C27	0.2015 (7)	0.8674 (7)	0.0545 (2)	0.0555 (19)
H27	0.2750	0.8713	0.0750	0.067*
C28	0.2003 (9)	0.9535 (7)	0.0170 (3)	0.067 (2)
H28	0.2710	1.0146	0.0127	0.080*
C29	0.0934 (11)	0.9471 (7)	−0.0136 (2)	0.069 (2)
H29	0.0913	1.0040	−0.0391	0.082*
C30	−0.0101 (8)	0.8575 (9)	−0.0068 (2)	0.068 (2)
H30	−0.0821	0.8530	−0.0279	0.082*
C31	−0.0087 (7)	0.7734 (7)	0.0310 (2)	0.0533 (19)
H31	−0.0806	0.7137	0.0355	0.064*

	U11	U22	U33	U12	U13	U23
Sn1	0.0418 (2)	0.0370 (2)	0.0421 (2)	−0.0018 (3)	0.0005 (3)	0.0007 (2)
O1	0.038 (2)	0.037 (2)	0.074 (3)	0.0086 (19)	0.003 (2)	−0.006 (2)
Cl1	0.0402 (9)	0.0677 (10)	0.0523 (8)	0.0007 (8)	0.0055 (10)	0.0088 (10)
S1	0.0432 (9)	0.0374 (8)	0.0701 (11)	−0.0007 (9)	−0.0056 (9)	−0.0031 (11)
C1	0.044 (4)	0.034 (3)	0.049 (4)	0.002 (3)	0.004 (3)	−0.004 (3)
C2	0.051 (5)	0.046 (4)	0.094 (5)	0.007 (5)	−0.017 (5)	−0.009 (4)
C3	0.063 (6)	0.069 (5)	0.125 (7)	−0.018 (5)	−0.013 (5)	−0.014 (6)
C4	0.081 (6)	0.040 (5)	0.107 (6)	−0.012 (5)	0.012 (5)	−0.007 (4)
C5	0.067 (5)	0.044 (4)	0.126 (8)	0.008 (5)	−0.004 (6)	−0.012 (4)
C6	0.051 (4)	0.046 (3)	0.100 (5)	0.009 (4)	0.000 (5)	−0.011 (6)
C7	0.054 (5)	0.047 (4)	0.047 (4)	0.011 (5)	−0.001 (4)	−0.004 (3)
C8	0.105 (7)	0.083 (6)	0.080 (5)	−0.021 (7)	0.011 (5)	−0.042 (6)
C9	0.131 (9)	0.124 (9)	0.111 (8)	−0.033 (8)	0.008 (8)	−0.075 (7)
C10	0.120 (10)	0.144 (10)	0.068 (6)	0.055 (8)	−0.017 (6)	−0.043 (7)
C11	0.134 (10)	0.112 (7)	0.047 (5)	0.058 (7)	0.006 (5)	−0.005 (5)
C12	0.085 (6)	0.077 (5)	0.048 (4)	0.013 (5)	0.010 (4)	0.009 (4)
C13	0.047 (4)	0.041 (4)	0.060 (4)	0.006 (4)	−0.004 (4)	−0.009 (4)
C14	0.079 (6)	0.046 (4)	0.073 (5)	−0.002 (5)	0.010 (5)	−0.009 (4)
C15	0.078 (7)	0.090 (6)	0.066 (5)	−0.011 (6)	0.008 (5)	0.008 (5)
C16	0.082 (6)	0.115 (8)	0.065 (5)	0.022 (7)	−0.009 (6)	−0.029 (6)
C17	0.089 (8)	0.077 (6)	0.099 (7)	0.006 (6)	−0.017 (6)	−0.044 (6)
C18	0.060 (6)	0.061 (5)	0.077 (5)	−0.004 (5)	−0.009 (5)	−0.024 (5)
C19	0.050 (4)	0.054 (5)	0.065 (4)	0.003 (4)	−0.008 (4)	−0.009 (4)
C20	0.043 (4)	0.053 (4)	0.071 (4)	−0.003 (5)	−0.016 (5)	−0.001 (4)
C21	0.054 (5)	0.071 (5)	0.096 (6)	0.010 (5)	−0.019 (5)	−0.007 (6)
C22	0.072 (6)	0.075 (6)	0.163 (10)	0.024 (6)	−0.038 (7)	−0.020 (7)
C23	0.081 (8)	0.061 (6)	0.185 (13)	0.000 (6)	−0.077 (9)	0.020 (7)
C24	0.098 (9)	0.090 (7)	0.125 (8)	−0.016 (8)	−0.038 (7)	0.047 (7)
C25	0.068 (6)	0.080 (6)	0.080 (5)	−0.012 (6)	−0.017 (5)	0.011 (5)
C26	0.034 (3)	0.037 (3)	0.042 (3)	0.001 (4)	−0.001 (4)	0.001 (3)
C27	0.055 (5)	0.056 (5)	0.055 (4)	−0.008 (5)	−0.006 (4)	0.001 (4)
C28	0.086 (6)	0.044 (4)	0.070 (5)	−0.004 (5)	0.014 (5)	0.011 (4)
C29	0.098 (6)	0.056 (4)	0.051 (4)	0.004 (6)	0.013 (6)	0.011 (4)
C30	0.076 (5)	0.087 (6)	0.042 (4)	0.026 (6)	−0.013 (4)	−0.002 (5)
C31	0.053 (4)	0.061 (5)	0.046 (4)	−0.008 (4)	0.000 (4)	−0.003 (4)

Sn1—C7	2.130 (3)	C14—H14	0.9300
Sn1—C26	2.138 (5)	C15—C16	1.369 (10)
Sn1—C1	2.145 (6)	C15—H15	0.9300
Sn1—O1	2.394 (4)	C16—C17	1.369 (11)
Sn1—Cl1	2.4972 (19)	C16—H16	0.9300
O1—S1	1.524 (4)	C17—C18	1.371 (10)
S1—C13	1.774 (6)	C17—H17	0.9300
S1—C19	1.815 (6)	C18—H18	0.9300
C1—C2	1.359 (9)	C19—C20	1.496 (9)
C1—C6	1.373 (8)	C19—H19A	0.9700
C2—C3	1.384 (9)	C19—H19B	0.9700
C2—H2	0.9300	C20—C25	1.380 (9)
C3—C4	1.357 (10)	C20—C21	1.386 (9)
C3—H3	0.9300	C21—C22	1.391 (10)
C4—C5	1.354 (10)	C21—H21A	0.9300
C4—H4	0.9300	C22—C23	1.358 (12)
C5—C6	1.398 (9)	C22—H22A	0.9300
C5—H5	0.9300	C23—C24	1.384 (13)
C6—H6	0.9300	C23—H23A	0.9300
C7—C8	1.3900	C24—C25	1.399 (11)
C7—C12	1.3900	C24—H24A	0.9300
C8—C9	1.3900	C25—H25A	0.9300
C8—H8	0.9300	C26—C27	1.364 (8)
C9—C10	1.3900	C26—C31	1.398 (8)
C9—H9	0.9300	C27—C28	1.382 (9)
C10—C11	1.3900	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.367 (11)
C11—C12	1.3900	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.364 (10)
C12—H12	0.9300	C29—H29	0.9300
C13—C14	1.353 (9)	C30—C31	1.379 (9)
C13—C18	1.378 (9)	C30—H30	0.9300
C14—C15	1.388 (9)	C31—H31	0.9300
C7—Sn1—C26	114.73 (19)	C15—C14—H14	120.1
C7—Sn1—C1	126.6 (2)	C16—C15—C14	119.6 (8)
C26—Sn1—C1	116.7 (2)	C16—C15—H15	120.2
C7—Sn1—O1	84.78 (19)	C14—C15—H15	120.2
C26—Sn1—O1	87.7 (2)	C17—C16—C15	120.3 (9)
C1—Sn1—O1	83.87 (19)	C17—C16—H16	119.8
C7—Sn1—Cl1	92.09 (16)	C15—C16—H16	119.8
C26—Sn1—Cl1	95.67 (19)	C16—C17—C18	120.0 (8)
C1—Sn1—Cl1	96.24 (18)	C16—C17—H17	120.0
O1—Sn1—Cl1	176.15 (12)	C18—C17—H17	120.0
S1—O1—Sn1	120.4 (2)	C17—C18—C13	119.7 (8)
O1—S1—C13	105.7 (3)	C17—C18—H18	120.2
O1—S1—C19	102.8 (3)	C13—C18—H18	120.2
C13—S1—C19	100.7 (3)	C20—C19—S1	113.6 (5)
C2—C1—C6	117.8 (6)	C20—C19—H19A	108.8
C2—C1—Sn1	122.0 (5)	S1—C19—H19A	108.8
C6—C1—Sn1	120.1 (5)	C20—C19—H19B	108.8
C1—C2—C3	121.2 (7)	S1—C19—H19B	108.8
C1—C2—H2	119.4	H19A—C19—H19B	107.7
C3—C2—H2	119.4	C25—C20—C21	118.2 (7)
C4—C3—C2	120.9 (8)	C25—C20—C19	120.2 (8)
C4—C3—H3	119.5	C21—C20—C19	121.6 (7)
C2—C3—H3	119.5	C20—C21—C22	120.6 (9)
C5—C4—C3	118.9 (7)	C20—C21—H21A	119.7
C5—C4—H4	120.5	C22—C21—H21A	119.7
C3—C4—H4	120.5	C23—C22—C21	120.1 (10)
C4—C5—C6	120.3 (7)	C23—C22—H22A	120.0
C4—C5—H5	119.8	C21—C22—H22A	120.0
C6—C5—H5	119.8	C22—C23—C24	121.3 (10)
C1—C6—C5	120.8 (7)	C22—C23—H23A	119.4
C1—C6—H6	119.6	C24—C23—H23A	119.4
C5—C6—H6	119.6	C23—C24—C25	117.9 (10)
C8—C7—C12	120.0	C23—C24—H24A	121.0
C8—C7—Sn1	117.8 (3)	C25—C24—H24A	121.0
C12—C7—Sn1	122.2 (3)	C20—C25—C24	121.9 (9)
C7—C8—C9	120.0	C20—C25—H25A	119.0
C7—C8—H8	120.0	C24—C25—H25A	119.0
C9—C8—H8	120.0	C27—C26—C31	116.9 (6)
C10—C9—C8	120.0	C27—C26—Sn1	122.8 (5)
C10—C9—H9	120.0	C31—C26—Sn1	120.3 (5)
C8—C9—H9	120.0	C26—C27—C28	123.0 (7)
C9—C10—C11	120.0	C26—C27—H27	118.5
C9—C10—H10	120.0	C28—C27—H27	118.5
C11—C10—H10	120.0	C29—C28—C27	118.8 (8)
C10—C11—C12	120.0	C29—C28—H28	120.6
C10—C11—H11	120.0	C27—C28—H28	120.6
C12—C11—H11	120.0	C30—C29—C28	120.1 (7)
C11—C12—C7	120.0	C30—C29—H29	119.9
C11—C12—H12	120.0	C28—C29—H29	119.9
C7—C12—H12	120.0	C29—C30—C31	120.5 (7)
C14—C13—C18	120.6 (6)	C29—C30—H30	119.8
C14—C13—S1	121.7 (5)	C31—C30—H30	119.8
C18—C13—S1	117.7 (6)	C30—C31—C26	120.7 (7)
C13—C14—C15	119.8 (7)	C30—C31—H31	119.7
C13—C14—H14	120.1	C26—C31—H31	119.7