(Benzyl phenyl sulfoxide-κO)dichloridodiphenyl-tin(IV).

The Sn(IV) atom in the title compound, [Sn(C(6)H(5))(2)Cl(2)(C(13)H(12)OS)], displays a distorted C(2)Cl(2)O trigonal-bipyramidal coordination environment, with a mean Sn-C distance of 2.121 (9) Å and with Sn-O = 2.331 (2) Å. The Sn(IV) atom is displaced by 0.169 (2) Å from the equatorial C(2)Cl plane towards the direction of the second axially bonded Cl atom.

Related literature

For background to organotin compounds, see: Davies et al. (2008 ▶); Tian et al. (2005 ▶). For related structures, see: Sadiq-ur-Rehman et al. (2007 ▶); Ng & Rheingold (1989 ▶); Bao et al. (1995 ▶); Dang (2009 ▶); Sousa et al. (2009 ▶); Yu et al. (1992 ▶).

Experimental

Crystal data

[Sn(C6H5)2Cl2(C13H12OS)]

M = 560.08

Triclinic,

a = 9.979 (5) Å

b = 10.577 (6) Å

c = 12.104 (4) Å

α = 87.728 (5)°

β = 81.196 (3)°

γ = 69.995 (5)°

V = 1186.2 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.41 mm−1

T = 295 K

0.31 × 0.24 × 0.20 mm

Data collection

Bruker P4 diffractometer

Absorption correction: ψ scan (XSCANS; Bruker, 1996 ▶) T min = 0.670, T max = 0.766

4959 measured reflections

4170 independent reflections

3546 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 97 reflections intensity decay: 1.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.056

S = 1.01

4170 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.34 e Å−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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014474/wm2481sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014474/wm2481Isup2.hkl

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

[Sn(C6H5)2Cl2(C13H12OS)]	Z = 2
Mr = 560.08	F(000) = 560
Triclinic, P1	Dx = 1.568 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.979 (5) Å	Cell parameters from 28 reflections
b = 10.577 (6) Å	θ = 5.4–12.5°
c = 12.104 (4) Å	µ = 1.41 mm−1
α = 87.728 (5)°	T = 295 K
β = 81.196 (3)°	Block, colourless
γ = 69.995 (5)°	0.31 × 0.24 × 0.20 mm
V = 1186.2 (10) Å3

Bruker P4 diffractometer	3546 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.0°, θmin = 2.1°
ω scans	h = −11→1
Absorption correction: ψ scan (XSCANS; Bruker, 1996)	k = −12→12
Tmin = 0.670, Tmax = 0.766	l = −14→14
4959 measured reflections	3 standard reflections every 97 reflections
4170 independent reflections	intensity decay: 1.9%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.056	w = 1/[σ2(Fo2) + (0.0246P)2 + 0.1469P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4170 reflections	Δρmax = 0.26 e Å−3
272 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0111 (5)

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
C1	0.7386 (3)	0.1721 (3)	1.0500 (2)	0.0430 (7)
H1A	0.8239	0.1008	1.0298	0.052*
C2	0.7161 (3)	0.2382 (3)	1.1502 (3)	0.0522 (8)
H2A	0.7858	0.2109	1.1974	0.063*
C3	0.5907 (3)	0.3446 (3)	1.1814 (3)	0.0495 (8)
H3A	0.5759	0.3890	1.2493	0.059*
C4	0.4878 (3)	0.3847 (3)	1.1118 (3)	0.0503 (8)
H4A	0.4032	0.4567	1.1325	0.060*
C5	0.5097 (3)	0.3183 (3)	1.0111 (2)	0.0442 (7)
H5A	0.4394	0.3459	0.9644	0.053*
C6	0.6355 (3)	0.2108 (3)	0.9784 (2)	0.0358 (6)
C7	0.7105 (3)	0.1817 (3)	0.6623 (2)	0.0398 (6)
C8	0.7903 (3)	0.0972 (3)	0.5733 (3)	0.0545 (8)
H8A	0.8277	0.0049	0.5841	0.065*
C9	0.8148 (4)	0.1490 (5)	0.4686 (3)	0.0718 (11)
H9A	0.8674	0.0916	0.4091	0.086*
C10	0.7618 (4)	0.2846 (5)	0.4527 (3)	0.0731 (11)
H10A	0.7797	0.3194	0.3824	0.088*
C11	0.6830 (5)	0.3691 (4)	0.5390 (3)	0.0814 (12)
H11A	0.6472	0.4614	0.5277	0.098*
C12	0.6561 (4)	0.3176 (3)	0.6440 (3)	0.0619 (9)
H12A	0.6007	0.3755	0.7025	0.074*
C13	0.2765 (3)	0.0805 (3)	0.7273 (3)	0.0526 (8)
H13A	0.3563	−0.0034	0.7113	0.063*
H13B	0.1895	0.0584	0.7488	0.063*
C14	0.2623 (3)	0.1608 (3)	0.6234 (3)	0.0473 (7)
C15	0.3841 (4)	0.1643 (4)	0.5531 (3)	0.0602 (9)
H15A	0.4750	0.1160	0.5710	0.072*
C16	0.3713 (5)	0.2394 (4)	0.4561 (3)	0.0794 (12)
H16A	0.4535	0.2421	0.4095	0.095*
C17	0.2376 (6)	0.3093 (4)	0.4293 (4)	0.0875 (13)
H17A	0.2291	0.3590	0.3640	0.105*
C18	0.1176 (5)	0.3065 (4)	0.4974 (4)	0.0804 (12)
H18A	0.0272	0.3550	0.4788	0.096*
C19	0.1282 (4)	0.2322 (3)	0.5946 (3)	0.0607 (9)
H19A	0.0451	0.2303	0.6404	0.073*
C20	0.1536 (3)	0.3141 (3)	0.8516 (2)	0.0427 (7)
C21	0.1612 (3)	0.4285 (3)	0.7968 (3)	0.0536 (8)
H21A	0.2477	0.4298	0.7561	0.064*
C22	0.0383 (4)	0.5415 (3)	0.8031 (3)	0.0615 (9)
H22A	0.0424	0.6201	0.7677	0.074*
C23	−0.0899 (4)	0.5380 (3)	0.8615 (3)	0.0599 (9)
H23A	−0.1727	0.6136	0.8648	0.072*
C24	−0.0951 (3)	0.4224 (4)	0.9152 (3)	0.0598 (9)
H24A	−0.1821	0.4206	0.9545	0.072*
C25	0.0255 (3)	0.3099 (3)	0.9117 (3)	0.0537 (8)
H25A	0.0215	0.2323	0.9489	0.064*
Cl1	0.61881 (10)	−0.09242 (8)	0.83415 (8)	0.0626 (2)
Cl2	0.93145 (8)	−0.02330 (10)	0.82750 (7)	0.0661 (3)
O1	0.43433 (19)	0.20989 (19)	0.80186 (16)	0.0443 (5)
S1	0.30677 (8)	0.16446 (8)	0.84580 (6)	0.04423 (19)
Sn1	0.67532 (2)	0.10548 (2)	0.824114 (16)	0.03808 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0342 (16)	0.0413 (16)	0.0478 (17)	−0.0049 (13)	−0.0073 (13)	0.0003 (13)
C2	0.0475 (19)	0.0552 (19)	0.0500 (18)	−0.0069 (16)	−0.0201 (15)	−0.0006 (15)
C3	0.054 (2)	0.0461 (18)	0.0476 (18)	−0.0138 (16)	−0.0096 (15)	−0.0060 (14)
C4	0.0411 (18)	0.0449 (18)	0.0565 (19)	−0.0040 (14)	−0.0056 (15)	−0.0063 (14)
C5	0.0358 (16)	0.0427 (17)	0.0503 (17)	−0.0068 (13)	−0.0109 (14)	0.0014 (13)
C6	0.0322 (15)	0.0379 (15)	0.0371 (14)	−0.0128 (12)	−0.0038 (12)	0.0041 (12)
C7	0.0388 (16)	0.0450 (16)	0.0362 (15)	−0.0150 (13)	−0.0053 (12)	−0.0022 (12)
C8	0.0489 (19)	0.057 (2)	0.0492 (19)	−0.0089 (16)	−0.0008 (15)	−0.0081 (15)
C9	0.069 (3)	0.104 (3)	0.0415 (19)	−0.030 (2)	0.0020 (18)	−0.014 (2)
C10	0.082 (3)	0.110 (3)	0.045 (2)	−0.056 (3)	−0.0114 (19)	0.017 (2)
C11	0.115 (4)	0.062 (2)	0.075 (3)	−0.038 (2)	−0.024 (3)	0.025 (2)
C12	0.075 (2)	0.050 (2)	0.053 (2)	−0.0143 (18)	−0.0022 (18)	−0.0014 (16)
C13	0.0453 (18)	0.0452 (18)	0.070 (2)	−0.0173 (15)	−0.0125 (16)	−0.0030 (15)
C14	0.0482 (19)	0.0409 (17)	0.0559 (19)	−0.0146 (15)	−0.0163 (15)	−0.0074 (14)
C15	0.053 (2)	0.066 (2)	0.061 (2)	−0.0161 (18)	−0.0111 (17)	−0.0123 (18)
C16	0.093 (3)	0.097 (3)	0.058 (2)	−0.046 (3)	−0.010 (2)	−0.001 (2)
C17	0.123 (4)	0.090 (3)	0.064 (3)	−0.048 (3)	−0.035 (3)	0.013 (2)
C18	0.086 (3)	0.072 (3)	0.086 (3)	−0.014 (2)	−0.048 (3)	0.000 (2)
C19	0.051 (2)	0.064 (2)	0.070 (2)	−0.0184 (18)	−0.0192 (18)	−0.0073 (18)
C20	0.0330 (16)	0.0493 (17)	0.0436 (16)	−0.0112 (14)	−0.0061 (13)	0.0009 (13)
C21	0.0438 (18)	0.054 (2)	0.061 (2)	−0.0180 (16)	0.0014 (15)	0.0038 (16)
C22	0.055 (2)	0.049 (2)	0.073 (2)	−0.0116 (17)	−0.0039 (18)	0.0097 (17)
C23	0.0437 (19)	0.053 (2)	0.070 (2)	−0.0004 (16)	−0.0088 (17)	−0.0004 (17)
C24	0.0327 (17)	0.073 (2)	0.068 (2)	−0.0128 (17)	−0.0013 (15)	0.0051 (18)
C25	0.0412 (18)	0.061 (2)	0.0567 (19)	−0.0175 (16)	−0.0034 (15)	0.0114 (16)
Cl1	0.0650 (6)	0.0415 (4)	0.0815 (6)	−0.0173 (4)	−0.0152 (5)	0.0066 (4)
Cl2	0.0340 (4)	0.0797 (6)	0.0649 (5)	0.0063 (4)	−0.0071 (4)	−0.0047 (4)
O1	0.0304 (10)	0.0503 (12)	0.0515 (12)	−0.0122 (9)	−0.0082 (9)	0.0028 (9)
S1	0.0355 (4)	0.0484 (4)	0.0464 (4)	−0.0117 (3)	−0.0062 (3)	0.0047 (3)
Sn1	0.03092 (12)	0.04049 (12)	0.03830 (12)	−0.00709 (8)	−0.00347 (8)	0.00064 (8)

C1—C2	1.373 (4)	C14—C19	1.383 (4)
C1—C6	1.391 (4)	C14—C15	1.383 (4)
C1—H1A	0.9300	C15—C16	1.389 (5)
C2—C3	1.378 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.368 (6)
C3—C4	1.372 (4)	C16—H16A	0.9300
C3—H3A	0.9300	C17—C18	1.355 (6)
C4—C5	1.382 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.386 (5)
C5—C6	1.390 (4)	C18—H18A	0.9300
C5—H5A	0.9300	C19—H19A	0.9300
C6—Sn1	2.127 (3)	C20—C21	1.376 (4)
C7—C12	1.373 (4)	C20—C25	1.385 (4)
C7—C8	1.386 (4)	C20—S1	1.780 (3)
C7—Sn1	2.114 (3)	C21—C22	1.384 (4)
C8—C9	1.380 (5)	C21—H21A	0.9300
C8—H8A	0.9300	C22—C23	1.376 (4)
C9—C10	1.365 (5)	C22—H22A	0.9300
C9—H9A	0.9300	C23—C24	1.375 (5)
C10—C11	1.360 (5)	C23—H23A	0.9300
C10—H10A	0.9300	C24—C25	1.370 (4)
C11—C12	1.387 (5)	C24—H24A	0.9300
C11—H11A	0.9300	C25—H25A	0.9300
C12—H12A	0.9300	Cl1—Sn1	2.3410 (13)
C13—C14	1.487 (4)	Cl2—Sn1	2.4567 (14)
C13—S1	1.831 (3)	O1—S1	1.525 (2)
C13—H13A	0.9700	O1—Sn1	2.331 (2)
C13—H13B	0.9700
C2—C1—C6	120.8 (3)	C14—C15—H15A	119.8
C2—C1—H1A	119.6	C16—C15—H15A	119.8
C6—C1—H1A	119.6	C17—C16—C15	119.8 (4)
C1—C2—C3	120.4 (3)	C17—C16—H16A	120.1
C1—C2—H2A	119.8	C15—C16—H16A	120.1
C3—C2—H2A	119.8	C18—C17—C16	120.3 (4)
C4—C3—C2	119.8 (3)	C18—C17—H17A	119.9
C4—C3—H3A	120.1	C16—C17—H17A	119.9
C2—C3—H3A	120.1	C17—C18—C19	120.7 (4)
C3—C4—C5	120.0 (3)	C17—C18—H18A	119.6
C3—C4—H4A	120.0	C19—C18—H18A	119.6
C5—C4—H4A	120.0	C14—C19—C18	120.0 (4)
C4—C5—C6	120.9 (3)	C14—C19—H19A	120.0
C4—C5—H5A	119.5	C18—C19—H19A	120.0
C6—C5—H5A	119.5	C21—C20—C25	121.3 (3)
C5—C6—C1	118.1 (3)	C21—C20—S1	121.5 (2)
C5—C6—Sn1	122.5 (2)	C25—C20—S1	117.2 (2)
C1—C6—Sn1	119.4 (2)	C20—C21—C22	119.0 (3)
C12—C7—C8	118.6 (3)	C20—C21—H21A	120.5
C12—C7—Sn1	120.1 (2)	C22—C21—H21A	120.5
C8—C7—Sn1	121.3 (2)	C23—C22—C21	120.2 (3)
C9—C8—C7	120.5 (3)	C23—C22—H22A	119.9
C9—C8—H8A	119.8	C21—C22—H22A	119.9
C7—C8—H8A	119.8	C24—C23—C22	119.8 (3)
C10—C9—C8	119.9 (3)	C24—C23—H23A	120.1
C10—C9—H9A	120.0	C22—C23—H23A	120.1
C8—C9—H9A	120.0	C25—C24—C23	121.2 (3)
C11—C10—C9	120.4 (3)	C25—C24—H24A	119.4
C11—C10—H10A	119.8	C23—C24—H24A	119.4
C9—C10—H10A	119.8	C24—C25—C20	118.5 (3)
C10—C11—C12	120.0 (4)	C24—C25—H25A	120.7
C10—C11—H11A	120.0	C20—C25—H25A	120.7
C12—C11—H11A	120.0	S1—O1—Sn1	127.97 (11)
C7—C12—C11	120.5 (3)	O1—S1—C20	104.46 (13)
C7—C12—H12A	119.7	O1—S1—C13	105.54 (13)
C11—C12—H12A	119.7	C20—S1—C13	98.91 (14)
C14—C13—S1	114.6 (2)	C7—Sn1—C6	126.64 (11)
C14—C13—H13A	108.6	C7—Sn1—O1	82.35 (9)
S1—C13—H13A	108.6	C6—Sn1—O1	89.84 (9)
C14—C13—H13B	108.6	C7—Sn1—Cl1	116.24 (8)
S1—C13—H13B	108.6	C6—Sn1—Cl1	115.33 (8)
H13A—C13—H13B	107.6	O1—Sn1—Cl1	84.46 (6)
C19—C14—C15	118.8 (3)	C7—Sn1—Cl2	94.39 (8)
C19—C14—C13	121.0 (3)	C6—Sn1—Cl2	97.34 (8)
C15—C14—C13	120.2 (3)	O1—Sn1—Cl2	172.69 (5)
C14—C15—C16	120.4 (3)	Cl1—Sn1—Cl2	91.18 (4)