Chlorido(dimethyl sulfoxide-κO)triphenyl-tin(IV).

In the title compound, [Sn(C(6)H(5))(3)Cl(C(2)H(6)OS)], the Sn(IV) atom is coordinated by three phenyl groups, a chloride ion and a dimethyl sulfoxide mol-ecule in a distorted trigonal-bipyramidal geometry. In the crystal, adjacent mol-ecules are linked through inter-molecular C-H⋯Cl hydrogen bonds, weak C-H⋯π inter-actions and π-π inter-actions [centroid-centroid distance = 3.934 (3) Å. An intra-molecular C-H⋯π inter-action is also observed.

Related literature

For general background to the biological activity and industrial applications of triorganotin(IV) complexes, see: Willem et al. (1997 ▶); Gielen et al. (2000 ▶); Tian et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For some unusual examples of [Sn(C6H5)3(C16H10NO3)(C2H6O)] adducts with oxygen-donor ligands, see: Lo & Ng (2009 ▶); Ng & Kumar Das (1997 ▶).

Experimental

Crystal data

[Sn(C6H5)3Cl(C2H6OS)]

M = 463.57

Orthorhombic,

a = 10.417 (5) Å

b = 13.235 (5) Å

c = 14.302 (5) Å

V = 1971.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.54 mm−1

T = 293 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 2004 ▶) T min = 0.677, T max = 0.712

11203 measured reflections

4052 independent reflections

3877 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.15

4052 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.18 e Å−3

Δρmin = −0.86 e Å−3

Absolute structure: Flack (1983 ▶), 1732 Friedel pairs

Flack parameter: −0.07 (3)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048090/is2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048090/is2466Isup2.hkl

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

[Sn(C6H5)3Cl(C2H6OS)]	F(000) = 928
Mr = 463.57	Dx = 1.562 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6343 reflections
a = 10.417 (5) Å	θ = 2.4–28.3°
b = 13.235 (5) Å	µ = 1.54 mm−1
c = 14.302 (5) Å	T = 293 K
V = 1971.8 (14) Å3	Prism, colorless
Z = 4	0.26 × 0.24 × 0.22 mm

Bruker SMART CCD diffractometer	4052 independent reflections
Radiation source: fine-focus sealed tube	3877 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→12
Tmin = 0.677, Tmax = 0.712	k = −16→15
11203 measured reflections	l = −15→17

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0344P)2 + 2.3774P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
4052 reflections	Δρmax = 1.18 e Å−3
217 parameters	Δρmin = −0.86 e Å−3
0 restraints	Absolute structure: Flack (1983), 1732 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.07 (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	0.65650 (3)	0.90124 (2)	0.76810 (2)	0.01581 (9)
Cl1	0.70946 (11)	1.06792 (8)	0.69548 (9)	0.0215 (2)
S1	0.60492 (11)	0.71709 (9)	0.93706 (8)	0.0203 (2)
O1	0.6043 (3)	0.7472 (2)	0.8339 (2)	0.0212 (7)
C17	0.5280 (5)	1.0132 (4)	1.0442 (4)	0.0253 (11)
H17	0.5586	1.0112	1.1053	0.030*
C14	0.4365 (4)	1.0183 (4)	0.8606 (4)	0.0227 (10)
H14	0.4060	1.0203	0.7995	0.027*
C3	1.0216 (5)	0.7334 (4)	0.7804 (3)	0.0295 (12)
H3	1.0461	0.6662	0.7735	0.035*
C2	0.8928 (5)	0.7602 (4)	0.7732 (4)	0.0246 (10)
H2	0.8319	0.7104	0.7614	0.030*
C9	0.3759 (5)	0.7531 (4)	0.5849 (4)	0.0287 (12)
H9	0.3023	0.7144	0.5939	0.034*
C18	0.5971 (5)	0.9694 (3)	0.9717 (3)	0.0211 (10)
H18	0.6751	0.9384	0.9851	0.025*
C13	0.5538 (4)	0.9702 (3)	0.8800 (3)	0.0179 (9)
C12	0.5932 (5)	0.8685 (4)	0.5590 (3)	0.0198 (10)
H12	0.6661	0.9078	0.5497	0.024*
C8	0.4438 (4)	0.7872 (4)	0.6612 (4)	0.0227 (10)
H8	0.4163	0.7705	0.7211	0.027*
C7	0.5534 (4)	0.8467 (3)	0.6496 (3)	0.0185 (10)
C19	0.6133 (5)	0.5836 (4)	0.9315 (4)	0.0279 (11)
H19A	0.6975	0.5636	0.9114	0.042*
H19B	0.5506	0.5590	0.8878	0.042*
H19C	0.5963	0.5557	0.9922	0.042*
C10	0.4154 (5)	0.7756 (4)	0.4954 (4)	0.0256 (11)
H10	0.3687	0.7527	0.4443	0.031*
C20	0.4428 (5)	0.7303 (4)	0.9743 (4)	0.0265 (11)
H20A	0.4226	0.8007	0.9809	0.040*
H20B	0.4316	0.6969	1.0333	0.040*
H20C	0.3868	0.7004	0.9287	0.040*
C11	0.5260 (5)	0.8328 (4)	0.4823 (4)	0.0249 (11)
H11	0.5547	0.8470	0.4221	0.030*
C4	1.1127 (5)	0.8061 (4)	0.7976 (4)	0.0310 (12)
H4	1.1988	0.7883	0.8023	0.037*
C6	0.9465 (4)	0.9331 (4)	0.8018 (4)	0.0233 (10)
H6	0.9223	1.0002	0.8101	0.028*
C1	0.8536 (4)	0.8603 (3)	0.7833 (3)	0.0187 (9)
C16	0.4115 (5)	1.0605 (4)	1.0232 (4)	0.0262 (11)
H16	0.3640	1.0906	1.0706	0.031*
C5	1.0761 (5)	0.9062 (5)	0.8081 (4)	0.0313 (12)
H5	1.1378	0.9556	0.8192	0.038*
C15	0.3661 (5)	1.0628 (4)	0.9314 (4)	0.0293 (12)
H15	0.2884	1.0942	0.9179	0.035*

	U11	U22	U33	U12	U13	U23
Sn1	0.01343 (14)	0.01702 (14)	0.01697 (15)	0.00044 (12)	0.00008 (12)	0.00061 (12)
Cl1	0.0183 (5)	0.0193 (5)	0.0268 (6)	−0.0005 (4)	−0.0006 (5)	0.0046 (4)
S1	0.0192 (5)	0.0212 (6)	0.0205 (6)	−0.0035 (5)	−0.0025 (5)	0.0022 (5)
O1	0.0262 (16)	0.0221 (17)	0.0152 (16)	0.0020 (14)	0.0026 (14)	0.0018 (13)
C17	0.033 (3)	0.023 (2)	0.020 (3)	−0.004 (2)	0.003 (2)	−0.001 (2)
C14	0.018 (2)	0.025 (2)	0.025 (3)	0.002 (2)	0.000 (2)	−0.001 (2)
C3	0.030 (3)	0.039 (3)	0.020 (3)	0.020 (2)	0.000 (2)	−0.007 (2)
C2	0.022 (2)	0.028 (2)	0.025 (2)	0.0069 (19)	−0.004 (2)	−0.002 (2)
C9	0.020 (3)	0.026 (3)	0.040 (3)	−0.002 (2)	−0.006 (2)	−0.006 (2)
C18	0.021 (2)	0.014 (2)	0.029 (3)	−0.0012 (19)	0.000 (2)	−0.001 (2)
C13	0.018 (2)	0.019 (2)	0.017 (2)	−0.0021 (19)	0.0027 (19)	−0.0019 (18)
C12	0.021 (2)	0.023 (2)	0.015 (2)	−0.0004 (19)	0.0012 (19)	−0.0036 (18)
C8	0.017 (2)	0.025 (2)	0.026 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C7	0.016 (2)	0.018 (2)	0.022 (2)	0.0074 (18)	−0.0002 (19)	0.0010 (19)
C19	0.035 (3)	0.020 (3)	0.028 (3)	0.004 (2)	−0.004 (2)	0.006 (2)
C10	0.029 (3)	0.025 (3)	0.024 (3)	0.005 (2)	−0.009 (2)	−0.008 (2)
C20	0.027 (3)	0.036 (3)	0.017 (2)	−0.007 (2)	0.002 (2)	0.002 (2)
C11	0.033 (3)	0.022 (2)	0.020 (2)	0.006 (2)	0.003 (2)	0.0051 (19)
C4	0.021 (2)	0.052 (3)	0.020 (2)	0.012 (2)	0.001 (2)	0.004 (2)
C6	0.017 (2)	0.029 (3)	0.024 (2)	0.0002 (19)	−0.001 (2)	0.003 (2)
C1	0.015 (2)	0.025 (2)	0.016 (2)	0.0042 (18)	−0.001 (2)	0.0016 (17)
C16	0.024 (3)	0.029 (3)	0.025 (3)	−0.005 (2)	0.005 (2)	−0.011 (2)
C5	0.018 (2)	0.046 (3)	0.029 (3)	−0.001 (2)	0.003 (2)	0.010 (3)
C15	0.017 (3)	0.033 (3)	0.038 (3)	0.002 (2)	0.003 (2)	−0.005 (2)

Sn1—Cl1	2.4999 (14)	C12—C11	1.384 (7)
Sn1—O1	2.311 (3)	C12—C7	1.391 (7)
Sn1—C1	2.134 (5)	C12—H12	0.9300
Sn1—C7	2.132 (5)	C8—C7	1.397 (7)
Sn1—C13	2.131 (5)	C8—H8	0.9300
S1—O1	1.529 (3)	C19—H19A	0.9600
S1—C19	1.771 (5)	C19—H19B	0.9600
S1—C20	1.779 (5)	C19—H19C	0.9600
C17—C18	1.389 (7)	C10—C11	1.391 (7)
C17—C16	1.399 (8)	C10—H10	0.9300
C17—H17	0.9300	C20—H20A	0.9600
C14—C15	1.382 (7)	C20—H20B	0.9600
C14—C13	1.405 (7)	C20—H20C	0.9600
C14—H14	0.9300	C11—H11	0.9300
C3—C4	1.374 (8)	C4—C5	1.387 (8)
C3—C2	1.391 (7)	C4—H4	0.9300
C3—H3	0.9300	C6—C1	1.392 (7)
C2—C1	1.394 (6)	C6—C5	1.398 (7)
C2—H2	0.9300	C6—H6	0.9300
C9—C10	1.377 (8)	C16—C15	1.395 (8)
C9—C8	1.376 (7)	C16—H16	0.9300
C9—H9	0.9300	C5—H5	0.9300
C18—C13	1.387 (7)	C15—H15	0.9300
C18—H18	0.9300
C13—Sn1—C7	119.29 (18)	C7—C8—H8	119.6
C13—Sn1—C1	121.03 (17)	C12—C7—C8	118.1 (4)
C7—Sn1—C1	118.63 (17)	C12—C7—Sn1	121.4 (3)
C13—Sn1—O1	87.39 (15)	C8—C7—Sn1	120.6 (4)
C7—Sn1—O1	84.62 (15)	S1—C19—H19A	109.5
C1—Sn1—O1	87.74 (15)	S1—C19—H19B	109.5
C13—Sn1—Cl1	92.56 (13)	H19A—C19—H19B	109.5
C7—Sn1—Cl1	94.58 (13)	S1—C19—H19C	109.5
C1—Sn1—Cl1	93.10 (12)	H19A—C19—H19C	109.5
O1—Sn1—Cl1	179.04 (9)	H19B—C19—H19C	109.5
O1—S1—C19	102.5 (2)	C9—C10—C11	119.4 (5)
O1—S1—C20	105.1 (2)	C9—C10—H10	120.3
C19—S1—C20	99.1 (3)	C11—C10—H10	120.3
S1—O1—Sn1	128.46 (19)	S1—C20—H20A	109.5
C18—C17—C16	118.4 (5)	S1—C20—H20B	109.5
C18—C17—H17	120.8	H20A—C20—H20B	109.5
C16—C17—H17	120.8	S1—C20—H20C	109.5
C15—C14—C13	120.7 (5)	H20A—C20—H20C	109.5
C15—C14—H14	119.7	H20B—C20—H20C	109.5
C13—C14—H14	119.7	C12—C11—C10	119.8 (5)
C4—C3—C2	120.1 (5)	C12—C11—H11	120.1
C4—C3—H3	120.0	C10—C11—H11	120.1
C2—C3—H3	120.0	C3—C4—C5	119.9 (5)
C3—C2—C1	121.2 (5)	C3—C4—H4	120.1
C3—C2—H2	119.4	C5—C4—H4	120.1
C1—C2—H2	119.4	C1—C6—C5	120.5 (5)
C10—C9—C8	120.8 (5)	C1—C6—H6	119.8
C10—C9—H9	119.6	C5—C6—H6	119.8
C8—C9—H9	119.6	C6—C1—C2	118.3 (4)
C13—C18—C17	122.3 (5)	C6—C1—Sn1	120.8 (3)
C13—C18—H18	118.8	C2—C1—Sn1	120.9 (3)
C17—C18—H18	118.8	C15—C16—C17	120.4 (5)
C18—C13—C14	118.2 (4)	C15—C16—H16	119.8
C18—C13—Sn1	122.9 (3)	C17—C16—H16	119.8
C14—C13—Sn1	118.9 (3)	C4—C5—C6	120.1 (5)
C11—C12—C7	121.1 (5)	C4—C5—H5	119.9
C11—C12—H12	119.4	C6—C5—H5	119.9
C7—C12—H12	119.4	C14—C15—C16	120.0 (5)
C9—C8—C7	120.7 (5)	C14—C15—H15	120.0
C9—C8—H8	119.6	C16—C15—H15	120.0
C19—S1—O1—Sn1	−159.5 (3)	Cl1—Sn1—C7—C12	37.2 (4)
C20—S1—O1—Sn1	97.4 (3)	C13—Sn1—C7—C8	−47.5 (4)
C13—Sn1—O1—S1	−41.8 (3)	C1—Sn1—C7—C8	120.9 (4)
C7—Sn1—O1—S1	−161.5 (3)	O1—Sn1—C7—C8	36.4 (4)
C1—Sn1—O1—S1	79.4 (3)	Cl1—Sn1—C7—C8	−143.1 (4)
C4—C3—C2—C1	−0.1 (8)	C8—C9—C10—C11	0.5 (8)
C16—C17—C18—C13	−0.6 (7)	C7—C12—C11—C10	1.2 (7)
C17—C18—C13—C14	0.7 (7)	C9—C10—C11—C12	−1.5 (7)
C17—C18—C13—Sn1	−178.9 (4)	C2—C3—C4—C5	0.2 (8)
C15—C14—C13—C18	−0.5 (7)	C5—C6—C1—C2	1.4 (7)
C15—C14—C13—Sn1	179.1 (4)	C5—C6—C1—Sn1	−177.5 (4)
C7—Sn1—C13—C18	152.0 (4)	C3—C2—C1—C6	−0.7 (8)
C1—Sn1—C13—C18	−16.1 (5)	C3—C2—C1—Sn1	178.2 (4)
O1—Sn1—C13—C18	69.7 (4)	C13—Sn1—C1—C6	−61.1 (4)
Cl1—Sn1—C13—C18	−111.3 (4)	C7—Sn1—C1—C6	130.6 (4)
C7—Sn1—C13—C14	−27.5 (4)	O1—Sn1—C1—C6	−146.7 (4)
C1—Sn1—C13—C14	164.3 (3)	Cl1—Sn1—C1—C6	33.7 (4)
O1—Sn1—C13—C14	−109.9 (4)	C13—Sn1—C1—C2	120.0 (4)
Cl1—Sn1—C13—C14	69.2 (4)	C7—Sn1—C1—C2	−48.2 (4)
C10—C9—C8—C7	0.9 (8)	O1—Sn1—C1—C2	34.4 (4)
C11—C12—C7—C8	0.2 (7)	Cl1—Sn1—C1—C2	−145.1 (4)
C11—C12—C7—Sn1	179.9 (4)	C18—C17—C16—C15	0.3 (8)
C9—C8—C7—C12	−1.3 (7)	C3—C4—C5—C6	0.5 (8)
C9—C8—C7—Sn1	179.0 (4)	C1—C6—C5—C4	−1.3 (8)
C13—Sn1—C7—C12	132.8 (4)	C13—C14—C15—C16	0.2 (8)
C1—Sn1—C7—C12	−58.8 (4)	C17—C16—C15—C14	−0.2 (8)
O1—Sn1—C7—C12	−143.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···Cl1i	0.96	2.69	3.610 (6)	161
C20—H20A···Cg3	0.96	2.94	3.813 (6)	151
C20—H20B···Cg1ii	0.96	2.61	3.490 (6)	153

Table 1

Selected bond lengths (Å)

Sn1—Cl1	2.4999 (14)
Sn1—O1	2.311 (3)
Sn1—C1	2.134 (5)
Sn1—C7	2.132 (5)
Sn1—C13	2.131 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20C⋯Cl1i	0.96	2.69	3.610 (6)	161
C20—H20A⋯Cg3	0.96	2.94	3.813 (6)	151
C20—H20B⋯Cg1ii	0.96	2.61	3.490 (6)	153

Symmetry codes: (i) ; (ii) . Cg1 and Cg3 are the centroids of the C1–C6 and C13–C18 rings, respectively.