Bis(benzyl phenyl sulfoxide-κO)dichloridodiphenyl-tin(IV).

The mol-ecule of the title compound, [Sn(C(6)H(5))(2)Cl(2)(C(13)H(12)OS)(2)], has crystallographic twofold symmetry. The Sn(IV) atom is six-coordinate within a distored octa-hedral geometry defined by a C(2)Cl(2)O(2) donor set.

Related literature

For general background to organotin compounds and their applications, see: Davies (2004 ▶); Tian et al. (2005 ▶); Hadjikakou & Hadjiliadis (2009 ▶). For related structures, see: Ng & Rheingold (1989 ▶); Boa et al. (1995 ▶); Tian et al. (1998 ▶); Sadiq-ur-Rehman et al. (2007 ▶).

Experimental

Crystal data

[Sn(C6H5)2Cl2(C13H12OS)2]

M = 776.40

Monoclinic,

a = 22.7485 (19) Å

b = 11.5478 (14) Å

c = 16.984 (2) Å

β = 126.633 (6)°

V = 3580.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 295 K

0.25 × 0.22 × 0.11 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.786, T max = 0.897

9821 measured reflections

3512 independent reflections

3003 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 1.03

3512 reflections

204 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536809039269/tk2538sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039269/tk2538Isup2.hkl

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

[Sn(C6H5)2Cl2(C13H12OS)2]	F(000) = 1576
Mr = 776.40	Dx = 1.440 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3086 reflections
a = 22.7485 (19) Å	θ = 2.7–24.9°
b = 11.5478 (14) Å	µ = 1.01 mm−1
c = 16.984 (2) Å	T = 295 K
β = 126.633 (6)°	Block, colourless
V = 3580.3 (7) Å3	0.25 × 0.22 × 0.11 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	3003 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −24→28
Tmin = 0.786, Tmax = 0.897	k = −14→12
9821 measured reflections	l = −20→20

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0324P)2 + 1.727P] where P = (Fo2 + 2Fc2)/3
3512 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.37 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
Sn1	1.0000	0.87434 (2)	0.2500	0.03980 (10)
Cl1	0.90700 (5)	1.01568 (7)	0.21844 (6)	0.0683 (2)
S1	0.84234 (4)	0.71126 (7)	0.15603 (5)	0.0544 (2)
O1	0.92338 (10)	0.72512 (16)	0.23458 (13)	0.0499 (5)
C1	1.04788 (14)	0.8471 (2)	0.40104 (18)	0.0396 (6)
C2	1.06132 (16)	0.9415 (2)	0.45947 (19)	0.0489 (7)
H2	1.0526	1.0158	0.4334	0.059*
C3	1.08741 (18)	0.9272 (3)	0.5554 (2)	0.0600 (8)
H3	1.0954	0.9916	0.5936	0.072*
C4	1.10169 (17)	0.8184 (3)	0.5954 (2)	0.0589 (8)
H4	1.1197	0.8089	0.6605	0.071*
C5	1.08941 (18)	0.7241 (3)	0.5389 (2)	0.0585 (8)
H5	1.0989	0.6502	0.5658	0.070*
C6	1.06288 (16)	0.7378 (2)	0.4418 (2)	0.0493 (7)
H6	1.0552	0.6732	0.4040	0.059*
C7	0.82742 (17)	0.5595 (3)	0.1480 (2)	0.0558 (8)
C8	0.7599 (2)	0.5161 (4)	0.0741 (3)	0.0748 (10)
H8	0.7222	0.5655	0.0287	0.090*
C9	0.7489 (3)	0.3981 (4)	0.0682 (4)	0.0967 (15)
H9	0.7028	0.3680	0.0198	0.116*
C10	0.8041 (3)	0.3252 (4)	0.1318 (4)	0.0978 (15)
H10	0.7960	0.2457	0.1265	0.117*
C11	0.8722 (3)	0.3686 (3)	0.2041 (3)	0.0867 (13)
H11	0.9103	0.3184	0.2472	0.104*
C12	0.8842 (2)	0.4863 (3)	0.2131 (2)	0.0645 (9)
H12	0.9301	0.5161	0.2624	0.077*
C13	0.79848 (19)	0.7551 (3)	0.2128 (3)	0.0685 (9)
H13A	0.8046	0.8381	0.2236	0.082*
H13B	0.7464	0.7400	0.1666	0.082*
C14	0.82573 (17)	0.6978 (2)	0.3077 (2)	0.0537 (7)
C15	0.8879 (2)	0.7370 (3)	0.3947 (3)	0.0699 (10)
H15	0.9147	0.7972	0.3940	0.084*
C16	0.9109 (2)	0.6882 (4)	0.4823 (3)	0.0849 (12)
H16	0.9526	0.7160	0.5407	0.102*
C17	0.8720 (2)	0.5978 (3)	0.4837 (3)	0.0789 (11)
H17	0.8873	0.5646	0.5431	0.095*
C18	0.8116 (2)	0.5575 (3)	0.3988 (3)	0.0715 (10)
H18	0.7855	0.4963	0.4000	0.086*
C19	0.7882 (2)	0.6056 (3)	0.3109 (3)	0.0637 (9)
H19	0.7469	0.5762	0.2529	0.076*

	U11	U22	U33	U12	U13	U23
Sn1	0.04550 (17)	0.04045 (16)	0.03513 (15)	0.000	0.02496 (13)	0.000
Cl1	0.0833 (6)	0.0662 (5)	0.0587 (5)	0.0318 (4)	0.0441 (5)	0.0117 (4)
S1	0.0453 (4)	0.0608 (5)	0.0503 (4)	−0.0038 (3)	0.0249 (4)	0.0146 (3)
O1	0.0448 (11)	0.0542 (12)	0.0485 (11)	−0.0061 (9)	0.0266 (10)	0.0059 (9)
C1	0.0386 (15)	0.0442 (15)	0.0390 (14)	0.0034 (11)	0.0248 (13)	0.0039 (11)
C2	0.0582 (19)	0.0468 (16)	0.0419 (15)	0.0056 (14)	0.0301 (15)	0.0013 (12)
C3	0.062 (2)	0.070 (2)	0.0458 (17)	0.0032 (17)	0.0311 (16)	−0.0098 (16)
C4	0.0514 (19)	0.086 (2)	0.0390 (16)	0.0066 (17)	0.0267 (15)	0.0091 (16)
C5	0.061 (2)	0.0587 (19)	0.0521 (18)	0.0103 (15)	0.0313 (17)	0.0199 (15)
C6	0.0501 (17)	0.0461 (16)	0.0485 (16)	0.0052 (13)	0.0277 (15)	−0.0004 (13)
C7	0.059 (2)	0.065 (2)	0.0481 (17)	−0.0162 (16)	0.0346 (16)	−0.0010 (15)
C8	0.058 (2)	0.100 (3)	0.065 (2)	−0.026 (2)	0.0362 (19)	−0.015 (2)
C9	0.105 (4)	0.110 (4)	0.095 (3)	−0.063 (3)	0.070 (3)	−0.043 (3)
C10	0.156 (5)	0.071 (3)	0.108 (4)	−0.045 (3)	0.101 (4)	−0.023 (3)
C11	0.123 (4)	0.064 (2)	0.074 (3)	−0.012 (2)	0.060 (3)	0.0100 (19)
C12	0.074 (2)	0.058 (2)	0.0545 (19)	−0.0076 (17)	0.0350 (19)	0.0064 (16)
C13	0.058 (2)	0.059 (2)	0.095 (3)	0.0126 (16)	0.049 (2)	0.0185 (18)
C14	0.0533 (19)	0.0466 (17)	0.075 (2)	0.0061 (14)	0.0458 (18)	0.0034 (15)
C15	0.076 (2)	0.065 (2)	0.094 (3)	−0.0187 (18)	0.064 (2)	−0.019 (2)
C16	0.078 (3)	0.121 (3)	0.066 (2)	−0.013 (2)	0.049 (2)	−0.020 (2)
C17	0.097 (3)	0.086 (3)	0.080 (3)	0.005 (2)	0.067 (3)	0.005 (2)
C18	0.088 (3)	0.060 (2)	0.086 (3)	−0.0102 (19)	0.063 (2)	−0.0022 (19)
C19	0.063 (2)	0.058 (2)	0.077 (2)	−0.0051 (16)	0.046 (2)	−0.0049 (16)

Sn1—C1	2.129 (2)	C8—H8	0.9300
Sn1—C1i	2.129 (2)	C9—C10	1.355 (7)
Sn1—O1	2.3519 (18)	C9—H9	0.9300
Sn1—O1i	2.3519 (18)	C10—C11	1.375 (6)
Sn1—Cl1i	2.4645 (8)	C10—H10	0.9300
Sn1—Cl1	2.4645 (8)	C11—C12	1.376 (4)
S1—O1	1.506 (2)	C11—H11	0.9300
S1—C7	1.775 (3)	C12—H12	0.9300
S1—C13	1.824 (3)	C13—C14	1.492 (4)
C1—C6	1.380 (4)	C13—H13A	0.9700
C1—C2	1.381 (4)	C13—H13B	0.9700
C2—C3	1.372 (4)	C14—C15	1.377 (5)
C2—H2	0.9300	C14—C19	1.386 (4)
C3—C4	1.372 (4)	C15—C16	1.370 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.364 (4)	C16—C17	1.379 (5)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.387 (4)	C17—C18	1.349 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.369 (5)
C7—C8	1.374 (4)	C18—H18	0.9300
C7—C12	1.379 (4)	C19—H19	0.9300
C8—C9	1.379 (5)
C1—Sn1—C1i	162.98 (14)	C7—C8—C9	118.8 (4)
C1—Sn1—O1	80.68 (8)	C7—C8—H8	120.6
C1i—Sn1—O1	86.85 (8)	C9—C8—H8	120.6
C1—Sn1—O1i	86.85 (8)	C10—C9—C8	121.0 (4)
C1i—Sn1—O1i	80.68 (8)	C10—C9—H9	119.5
O1—Sn1—O1i	85.78 (10)	C8—C9—H9	119.5
C1—Sn1—Cl1i	94.61 (7)	C9—C10—C11	120.0 (4)
C1i—Sn1—Cl1i	96.64 (7)	C9—C10—H10	120.0
O1—Sn1—Cl1i	172.95 (5)	C11—C10—H10	120.0
O1i—Sn1—Cl1i	88.74 (6)	C10—C11—C12	120.2 (4)
C1—Sn1—Cl1	96.64 (7)	C10—C11—H11	119.9
C1i—Sn1—Cl1	94.61 (7)	C12—C11—H11	119.9
O1—Sn1—Cl1	88.74 (6)	C11—C12—C7	119.2 (4)
O1i—Sn1—Cl1	172.95 (5)	C11—C12—H12	120.4
Cl1i—Sn1—Cl1	97.05 (5)	C7—C12—H12	120.4
O1—S1—C7	104.46 (13)	C14—C13—S1	116.2 (2)
O1—S1—C13	105.59 (14)	C14—C13—H13A	108.2
C7—S1—C13	100.05 (14)	S1—C13—H13A	108.2
S1—O1—Sn1	127.62 (10)	C14—C13—H13B	108.2
C6—C1—C2	118.6 (2)	S1—C13—H13B	108.2
C6—C1—Sn1	122.35 (19)	H13A—C13—H13B	107.4
C2—C1—Sn1	118.93 (18)	C15—C14—C19	118.2 (3)
C3—C2—C1	120.8 (3)	C15—C14—C13	120.8 (3)
C3—C2—H2	119.6	C19—C14—C13	121.0 (3)
C1—C2—H2	119.6	C16—C15—C14	120.8 (3)
C4—C3—C2	120.3 (3)	C16—C15—H15	119.6
C4—C3—H3	119.9	C14—C15—H15	119.6
C2—C3—H3	119.9	C15—C16—C17	119.9 (4)
C5—C4—C3	119.7 (3)	C15—C16—H16	120.1
C5—C4—H4	120.2	C17—C16—H16	120.1
C3—C4—H4	120.2	C18—C17—C16	119.8 (3)
C4—C5—C6	120.4 (3)	C18—C17—H17	120.1
C4—C5—H5	119.8	C16—C17—H17	120.1
C6—C5—H5	119.8	C17—C18—C19	120.7 (3)
C1—C6—C5	120.2 (3)	C17—C18—H18	119.6
C1—C6—H6	119.9	C19—C18—H18	119.6
C5—C6—H6	119.9	C18—C19—C14	120.5 (3)
C8—C7—C12	120.8 (3)	C18—C19—H19	119.7
C8—C7—S1	119.2 (3)	C14—C19—H19	119.7
C12—C7—S1	119.9 (2)
C7—S1—O1—Sn1	151.62 (14)	C13—S1—C7—C8	78.8 (3)
C13—S1—O1—Sn1	−103.37 (15)	O1—S1—C7—C12	5.1 (3)
C1—Sn1—O1—S1	143.25 (16)	C13—S1—C7—C12	−104.0 (3)
C1i—Sn1—O1—S1	−48.38 (15)	C12—C7—C8—C9	2.5 (5)
O1i—Sn1—O1—S1	−129.25 (17)	S1—C7—C8—C9	179.7 (3)
Cl1—Sn1—O1—S1	46.31 (14)	C7—C8—C9—C10	−2.3 (6)
O1—Sn1—C1—C6	45.7 (2)	C8—C9—C10—C11	0.6 (7)
O1i—Sn1—C1—C6	−40.5 (2)	C9—C10—C11—C12	0.9 (6)
Cl1i—Sn1—C1—C6	−129.0 (2)	C10—C11—C12—C7	−0.7 (6)
Cl1—Sn1—C1—C6	133.3 (2)	C8—C7—C12—C11	−1.0 (5)
C1i—Sn1—C1—C2	−174.6 (2)	S1—C7—C12—C11	−178.2 (3)
O1—Sn1—C1—C2	−131.2 (2)	O1—S1—C13—C14	−52.3 (3)
O1i—Sn1—C1—C2	142.6 (2)	C7—S1—C13—C14	55.9 (3)
Cl1i—Sn1—C1—C2	54.1 (2)	S1—C13—C14—C15	82.2 (4)
Cl1—Sn1—C1—C2	−43.6 (2)	S1—C13—C14—C19	−99.3 (3)
C6—C1—C2—C3	−1.5 (4)	C19—C14—C15—C16	−1.9 (5)
Sn1—C1—C2—C3	175.5 (2)	C13—C14—C15—C16	176.6 (3)
C1—C2—C3—C4	1.1 (5)	C14—C15—C16—C17	0.9 (6)
C2—C3—C4—C5	−0.4 (5)	C15—C16—C17—C18	0.2 (6)
C3—C4—C5—C6	0.2 (5)	C16—C17—C18—C19	−0.2 (6)
C2—C1—C6—C5	1.4 (4)	C17—C18—C19—C14	−0.9 (5)
Sn1—C1—C6—C5	−175.6 (2)	C15—C14—C19—C18	1.9 (5)
C4—C5—C6—C1	−0.7 (5)	C13—C14—C19—C18	−176.6 (3)
O1—S1—C7—C8	−172.1 (2)