Chlorido(dimethyl sulfoxide-κO)triphenyl­tin(IV)

Kumar, S.; Shadab, S.M.; Idrees, M.

doi:10.1107/S1600536809048090

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1602-m1603

doi:10.1107/S1600536809048090

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Chlorido(dimethyl sulfoxide-κO)triphenyltin(IV)

Sarvendra Kumar,^a Shah Mohammad Shadab ^b and Mohammad Idrees ^b ^*

^aIndian Institute of Technology, Kanpur, India, and ^bDepartment of Chemical Engineering, Aligarh Muslim University, Aligarh, India
^*Correspondence e-mail: skumarchem01@gmail.com

(Received 25 September 2009; accepted 12 November 2009; online 18 November 2009)

In the title compound, [Sn(C₆H₅)₃Cl(C₂H₆OS)], the Sn^IV atom is coordinated by three phenyl groups, a chloride ion and a dimethyl sulfoxide molecule in a distorted trigonal-bipyramidal geometry. In the crystal, adjacent molecules are linked through intermolecular C—H⋯Cl hydrogen bonds, weak C—H⋯π interactions and π–π interactions [centroid–centroid distance = 3.934 (3) Å. An intramolecular C—H⋯π interaction 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_r = 463.57
Orthorhombic, P 2₁ 2₁ 2₁
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 (SADABS; 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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.15
4052 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.86 e Å⁻³
Absolute structure: Flack (1983 ), 1732 Friedel pairs
Flack parameter: −0.07 (3)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ . Cg1 and Cg3 are the centroids of the C1–C6 and C13–C18 rings, respectively.

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.

Supporting information

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

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

checkCIF report

Comment top

Triorganotin(IV) complexes are well known for their biological activities as well as industrial applications (Willem et al., 1997; Gielen et al., 2000; Tian et al., 2005). Owing to wide spread applications of organotin compounds, their synthesis and characterization with O–containing ligands have been a continuing subject in recent years (Lo & Ng, 2009, Ng & Kumar Das, 1997). There are very rare examples of the triorganotin(IV) complexes with solvent molecules (Lo & Ng, 2009), in which solvent molecule acts as a chelator ligand.

The bond lengths and bond angles in the molecules are within normal ranges (Allen et al. 1987). The Sn^IV atom is coordinated by three phenyl groups, one chloride ion and one solvent molecule (DMSO) in a distorted trigonal biyramidal geometry (Fig. 1). The three phenyl groups are attached in a plane to the Sn atom and seemed like as three pedal of ceiling fan. The one chloride and one solvent molecule are located at axial positions and three phenyl groups are located at equatorial positions. Each phenyl group of the one compound is interacted with another phenyl group of another molecule by a π–π interaction and further interacted by a C—H···π interaction. The neighboring molecules are bound by C—H···Cl, C—H···π (Table 2) and a π–π interaction with a centroid-centroid distance of 3.934 (3) Å (Fig. 2).

Related literature top

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 adducts with orxygen-donor ligands, see: Lo & Ng (2009); Ng & Kumar Das (1997). Cg1 and Cg3 are the centroids of the C1–C6 and C13–C18 rings, respectively.

Experimental top

Triphenyltinchloride (0.385 g, 1 mmol) was dissolved in DMSO (4 ml) and heated until the reactant dissolved completely. The solution was filtered and solvent allowed evaporating slowly. Fine colorless crystal produced after 3 days. Crystals are stable at room temperature. Analysis calc. for C₂₀H₂₁SOClSn: C 51.81, H 4.57, S 6.92. Found: C 51.68, H 4.56, S 6.95.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP diagram of the title compound, with displacement ellipsoids drawn at the 50% probability level for non-hydrogen atoms.
	Fig. 2. In the packing diagram, molecules are bounded by weak intermolecular weak hydrogen bonds.

Chlorido(dimethyl sulfoxide-κO)triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃Cl(C₂H₆OS)]	F(000) = 928
M_r = 463.57	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0344P)² + 2.3774P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
4052 reflections	Δρ_max = 1.18 e Å⁻³
217 parameters	Δρ_min = −0.86 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1732 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (3)

Crystal data top

[Sn(C₆H₅)₃Cl(C₂H₆OS)]	V = 1971.8 (14) Å³
M_r = 463.57	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.417 (5) Å	µ = 1.54 mm⁻¹
b = 13.235 (5) Å	T = 293 K
c = 14.302 (5) Å	0.26 × 0.24 × 0.22 mm

Data collection top

Bruker SMART CCD diffractometer	4052 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3877 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.712	R_int = 0.048
11203 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.085	Δρ_max = 1.18 e Å⁻³
S = 1.15	Δρ_min = −0.86 e Å⁻³
4052 reflections	Absolute structure: Flack (1983), 1732 Friedel pairs
217 parameters	Absolute structure parameter: −0.07 (3)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃Cl(C₂H₆OS)]
M_r	463.57
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	10.417 (5), 13.235 (5), 14.302 (5)
V (Å³)	1971.8 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.54
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.677, 0.712
No. of measured, independent and observed [I > 2σ(I)] reflections	11203, 4052, 3877
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.15
No. of reflections	4052
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.86
Absolute structure	Flack (1983), 1732 Friedel pairs
Absolute structure parameter	−0.07 (3)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+2.

Acknowledgements

SMS is grateful to the Council of Science and Technology, UP (CST, UP), India, for providing grants under the Young Scientists Scheme [ref No. CST/SERPD/D-3505.2008].

References

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