Triphen­yl(pyrrolidine-1-carbodi­thio­ato-κS)tin(IV)

Sirajuddin, M.; Uddin, N.; Ali, S.

doi:10.1107/S1600536813022472

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page m497

doi:10.1107/S1600536813022472

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Triphenyl(pyrrolidine-1-carbodithioato-κS)tin(IV)

Muhammad Sirajuddin,^a ^* Noor Uddin ^a and Saqib Ali ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
^*Correspondence e-mail: m.siraj09@yahoo.com

(Received 7 August 2013; accepted 9 August 2013; online 17 August 2013)

In the title compound, [Sn(C₆H₅)₃(C₅H₈NS₂)], the Sn^IV atom adopts a distorted SnC₃S tetrahedral coordination geometry [spread of bond angles = 94.43 (7)–120.74 (7)°]. A short intramolecular Sn⋯S contact [3.0270 (9) Å] occurs and two intramolecular C—H⋯S interactions help to establish the conformation. Three of the methylene groups of the pyrrolidine-1-carbodithioate ligand are disordered over two sets of sites of equal occupancy. In the crystal, very weak C—H⋯S interactions link the molecules into a three-dimensional network, with both S atoms acting as acceptors.

Related literature

For background to the structures and applications of organotin compounds, see: Abbas et al. (2013 ); Pellerito & Nagy (2002 ); Ronconi et al. (2005 ); Shahzadi et al. (2006 , 2008 ); Sirajuddin et al. (2012 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₅H₈NS₂)]
M_r = 496.23
Monoclinic, P 2₁ /c
a = 12.3467 (4) Å
b = 10.3227 (3) Å
c = 17.0611 (6) Å
β = 90.864 (2)°
V = 2174.21 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.667, T_max = 0.734
16466 measured reflections
4265 independent reflections
3567 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.062
S = 1.01
4265 reflections
253 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C6	2.160 (2)
Sn1—C12	2.134 (2)
Sn1—C18	2.149 (2)
Sn1—S1	2.4710 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯S1	0.93	2.75	3.384 (3)	127
C23—H23⋯S2	0.93	2.77	3.424 (3)	129
C2—H2B⋯S2ⁱ	0.97	2.96	3.759 (3)	141
C5—H5B⋯S1ⁱⁱ	0.97	2.98	3.750 (3)	137
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813022472/hb7122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813022472/hb7122Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813022472/hb7122Isup3.cml

checkCIF report

Related literature top

For background to the structures and applications of organotin compounds, see: Abbas et al. (2013); Pellerito & Nagy (2002); Ronconi et al. (2005); Shahzadi et al. (2006, 2008); Sirajuddin et al. (2012).

Experimental top

Stoichiometric amount of sodium salt of pyrrolidine-1-carbodithioate was suspended in dry toluene and to it calculated amount of triphenyltin(IV) chloride, Ph₃SnCl, (5 mmol of each, 1:1 ratio) was added. The mixture was stirred and refluxed for 3–4 h, and then it was cooled and filtered to remove NaCl. The filterate was rotary evaporated to get the product which was recystallized from chloroform solution to yield colourless prisms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules form dimers due to C—H···S bonds.

Triphenyl(pyrrolidine-1-carbodithioato-κS)tin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₅H₈NS₂)]	Z = 4
M_r = 496.23	F(000) = 1000
Monoclinic, P2₁/c	D_x = 1.516 Mg m⁻³
a = 12.3467 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3227 (3) Å	µ = 1.38 mm⁻¹
c = 17.0611 (6) Å	T = 296 K
β = 90.864 (2)°	Prism, colourless
V = 2174.21 (12) Å³	0.32 × 0.26 × 0.24 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→12
T_min = 0.667, T_max = 0.734	k = −12→12
16466 measured reflections	l = −20→21
4265 independent reflections

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.0255P)² + 1.8846P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4265 reflections	Δρ_max = 0.39 e Å⁻³
253 parameters	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₅H₈NS₂)]	V = 2174.21 (12) Å³
M_r = 496.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3467 (4) Å	µ = 1.38 mm⁻¹
b = 10.3227 (3) Å	T = 296 K
c = 17.0611 (6) Å	0.32 × 0.26 × 0.24 mm
β = 90.864 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4265 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3567 reflections with I > 2σ(I)
T_min = 0.667, T_max = 0.734	R_int = 0.020
16466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	3 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
4265 reflections	Δρ_min = −0.47 e Å⁻³
253 parameters

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.43914 (19)	0.5449 (2)	0.19935 (15)	0.0395 (5)
C2	0.6278 (2)	0.4746 (3)	0.22777 (17)	0.0523 (7)
H2A	0.6637	0.5121	0.1830	0.063*
H2B	0.6145	0.3835	0.2178	0.063*
C3	0.6941 (3)	0.4935 (4)	0.3019 (2)	0.0806 (11)	0.5
H3A	0.6860	0.4194	0.3363	0.097*	0.5
H3B	0.7701	0.5026	0.2896	0.097*	0.5
C4	0.6549 (5)	0.6099 (7)	0.3397 (4)	0.0552 (17)	0.5
H4A	0.6913	0.6861	0.3198	0.066*	0.5
H4B	0.6665	0.6055	0.3960	0.066*	0.5
C5	0.5338 (2)	0.6133 (3)	0.31911 (18)	0.0670 (9)	0.5
H5A	0.4918	0.5703	0.3591	0.080*	0.5
H5B	0.5083	0.7017	0.3134	0.080*	0.5
C3'	0.6941 (3)	0.4935 (4)	0.3019 (2)	0.0806 (11)	0.5
H3'1	0.7241	0.4113	0.3192	0.097*	0.5
H3'2	0.7536	0.5525	0.2923	0.097*	0.5
C4'	0.6248 (7)	0.5461 (10)	0.3617 (4)	0.083 (3)	0.5
H4'1	0.6646	0.6069	0.3945	0.100*	0.5
H4'2	0.5970	0.4773	0.3945	0.100*	0.5
C5'	0.5338 (2)	0.6133 (3)	0.31911 (18)	0.0670 (9)	0.5
H5'1	0.4668	0.6064	0.3478	0.080*	0.5
H5'2	0.5503	0.7041	0.3109	0.080*	0.5
C6	0.2627 (2)	0.3725 (2)	−0.03124 (14)	0.0419 (5)
C7	0.3521 (2)	0.2959 (3)	−0.04850 (16)	0.0520 (6)
H7	0.4133	0.2995	−0.0162	0.062*
C8	0.3512 (3)	0.2147 (3)	−0.11275 (18)	0.0650 (8)
H8	0.4119	0.1648	−0.1234	0.078*
C9	0.2618 (3)	0.2069 (3)	−0.16087 (18)	0.0692 (9)
H9	0.2611	0.1504	−0.2033	0.083*
C10	0.1735 (3)	0.2826 (3)	−0.14625 (18)	0.0677 (9)
H10	0.1131	0.2787	−0.1794	0.081*
C11	0.1740 (2)	0.3653 (3)	−0.08204 (16)	0.0545 (7)
H11	0.1137	0.4169	−0.0729	0.065*
C12	0.22278 (19)	0.6899 (2)	0.03333 (14)	0.0402 (5)
C13	0.1372 (2)	0.7587 (3)	0.06383 (16)	0.0508 (6)
H13	0.0922	0.7191	0.0999	0.061*
C14	0.1174 (2)	0.8859 (3)	0.04166 (17)	0.0583 (7)
H14	0.0593	0.9305	0.0627	0.070*
C15	0.1829 (3)	0.9458 (3)	−0.01099 (19)	0.0636 (8)
H15	0.1707	1.0316	−0.0250	0.076*
C16	0.2661 (3)	0.8784 (3)	−0.0427 (2)	0.0751 (10)
H16	0.3101	0.9182	−0.0793	0.090*
C17	0.2860 (2)	0.7515 (3)	−0.02123 (19)	0.0641 (8)
H17	0.3430	0.7069	−0.0439	0.077*
C18	0.12332 (19)	0.4161 (2)	0.13624 (14)	0.0404 (5)
C19	0.0755 (2)	0.3023 (3)	0.11048 (17)	0.0552 (7)
H19	0.1057	0.2566	0.0692	0.066*
C20	−0.0173 (3)	0.2559 (3)	0.1459 (2)	0.0666 (8)
H20	−0.0485	0.1791	0.1282	0.080*
C21	−0.0632 (2)	0.3217 (3)	0.20636 (18)	0.0618 (8)
H21	−0.1261	0.2908	0.2291	0.074*
C22	−0.0157 (2)	0.4337 (3)	0.23320 (18)	0.0579 (7)
H22	−0.0459	0.4783	0.2749	0.069*
C23	0.0769 (2)	0.4804 (3)	0.19850 (17)	0.0490 (6)
H23	0.1085	0.5562	0.2173	0.059*
N1	0.52626 (16)	0.5437 (2)	0.24462 (13)	0.0433 (5)
S1	0.44472 (5)	0.45725 (7)	0.11166 (4)	0.04934 (16)
S2	0.32513 (6)	0.62405 (8)	0.22271 (5)	0.0592 (2)
Sn1	0.25469 (2)	0.49609 (2)	0.07066 (2)	0.03669 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0373 (12)	0.0355 (12)	0.0456 (14)	−0.0018 (10)	−0.0042 (10)	0.0014 (10)
C2	0.0416 (14)	0.0586 (16)	0.0563 (17)	0.0107 (12)	−0.0099 (12)	−0.0057 (13)
C3	0.059 (2)	0.105 (3)	0.077 (2)	0.0268 (19)	−0.0302 (18)	−0.022 (2)
C4	0.045 (4)	0.067 (4)	0.053 (4)	0.002 (3)	−0.018 (3)	−0.010 (3)
C5	0.0516 (17)	0.086 (2)	0.0628 (19)	0.0106 (16)	−0.0160 (14)	−0.0287 (17)
C3'	0.059 (2)	0.105 (3)	0.077 (2)	0.0268 (19)	−0.0302 (18)	−0.022 (2)
C4'	0.065 (5)	0.130 (8)	0.053 (5)	0.010 (5)	−0.023 (4)	−0.007 (5)
C5'	0.0516 (17)	0.086 (2)	0.0628 (19)	0.0106 (16)	−0.0160 (14)	−0.0287 (17)
C6	0.0453 (13)	0.0420 (13)	0.0383 (13)	−0.0054 (11)	−0.0002 (10)	0.0002 (10)
C7	0.0550 (16)	0.0483 (15)	0.0527 (16)	0.0029 (13)	−0.0052 (13)	−0.0009 (13)
C8	0.083 (2)	0.0484 (16)	0.0636 (19)	0.0115 (15)	0.0071 (17)	−0.0067 (14)
C9	0.107 (3)	0.0500 (17)	0.0508 (17)	−0.0113 (18)	−0.0021 (18)	−0.0096 (14)
C10	0.075 (2)	0.074 (2)	0.0537 (18)	−0.0202 (18)	−0.0182 (16)	−0.0070 (16)
C11	0.0488 (15)	0.0648 (18)	0.0496 (16)	−0.0037 (13)	−0.0036 (12)	−0.0038 (13)
C12	0.0369 (12)	0.0403 (13)	0.0433 (13)	0.0008 (10)	−0.0051 (10)	0.0001 (10)
C13	0.0476 (14)	0.0576 (16)	0.0471 (15)	0.0093 (12)	0.0033 (12)	0.0084 (12)
C14	0.0624 (18)	0.0587 (17)	0.0534 (17)	0.0233 (14)	−0.0073 (14)	−0.0023 (14)
C15	0.077 (2)	0.0455 (15)	0.068 (2)	0.0063 (15)	−0.0095 (17)	0.0103 (15)
C16	0.071 (2)	0.061 (2)	0.094 (3)	−0.0021 (17)	0.0201 (19)	0.0274 (18)
C17	0.0563 (17)	0.0556 (17)	0.081 (2)	0.0090 (14)	0.0231 (16)	0.0119 (15)
C18	0.0362 (12)	0.0435 (13)	0.0413 (13)	−0.0033 (10)	−0.0030 (10)	0.0049 (11)
C19	0.0589 (17)	0.0559 (16)	0.0507 (16)	−0.0126 (14)	0.0020 (13)	−0.0050 (13)
C20	0.0636 (19)	0.0608 (18)	0.075 (2)	−0.0271 (16)	−0.0033 (16)	0.0026 (16)
C21	0.0462 (15)	0.073 (2)	0.0663 (19)	−0.0117 (15)	0.0057 (14)	0.0158 (16)
C22	0.0481 (16)	0.0658 (19)	0.0601 (18)	0.0026 (14)	0.0113 (13)	0.0057 (15)
C23	0.0455 (14)	0.0476 (15)	0.0540 (16)	−0.0032 (11)	0.0033 (12)	0.0001 (12)
N1	0.0353 (11)	0.0441 (11)	0.0502 (12)	0.0024 (9)	−0.0086 (9)	−0.0053 (10)
S1	0.0406 (3)	0.0563 (4)	0.0507 (4)	0.0078 (3)	−0.0098 (3)	−0.0116 (3)
S2	0.0398 (3)	0.0698 (5)	0.0678 (5)	0.0120 (3)	−0.0098 (3)	−0.0196 (4)
Sn1	0.03201 (10)	0.03739 (10)	0.04059 (10)	−0.00054 (6)	−0.00174 (7)	−0.00022 (7)

Geometric parameters (Å, º) top

C1—N1	1.315 (3)	C11—H11	0.9300
C1—S2	1.681 (2)	C12—C17	1.379 (4)
C1—S1	1.750 (3)	C12—C13	1.381 (3)
C2—N1	1.474 (3)	C13—C14	1.387 (4)
C2—C3	1.509 (4)	C13—H13	0.9300
C2—H2A	0.9700	C14—C15	1.365 (4)
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.451 (7)	C15—C16	1.360 (5)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.381 (4)
C4—C5	1.532 (7)	C16—H16	0.9300
C4—H4A	0.9700	C17—H17	0.9300
C4—H4B	0.9700	C18—C23	1.384 (4)
C5—N1	1.462 (3)	C18—C19	1.384 (4)
C5—H5A	0.9700	C19—C20	1.388 (4)
C5—H5B	0.9700	C19—H19	0.9300
C4'—H4'1	0.9700	C20—C21	1.366 (4)
C4'—H4'2	0.9700	C20—H20	0.9300
C6—C11	1.389 (4)	C21—C22	1.372 (4)
C6—C7	1.393 (4)	C21—H21	0.9300
C7—C8	1.380 (4)	C22—C23	1.382 (4)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.368 (5)	C23—H23	0.9300
C8—H8	0.9300	Sn1—C6	2.160 (2)
C9—C10	1.367 (5)	Sn1—C12	2.134 (2)
C9—H9	0.9300	Sn1—C18	2.149 (2)
C10—C11	1.389 (4)	Sn1—S1	2.4710 (7)
C10—H10	0.9300

N1—C1—S2	123.1 (2)	C17—C12—C13	117.5 (2)
N1—C1—S1	117.06 (18)	C17—C12—Sn1	121.97 (19)
S2—C1—S1	119.85 (14)	C13—C12—Sn1	120.56 (19)
N1—C2—C3	103.1 (2)	C12—C13—C14	121.1 (3)
N1—C2—H2A	111.1	C12—C13—H13	119.4
C3—C2—H2A	111.1	C14—C13—H13	119.4
N1—C2—H2B	111.1	C15—C14—C13	120.3 (3)
C3—C2—H2B	111.1	C15—C14—H14	119.9
H2A—C2—H2B	109.1	C13—C14—H14	119.9
C4—C3—C2	107.4 (4)	C16—C15—C14	119.3 (3)
C4—C3—H3A	110.2	C16—C15—H15	120.4
C2—C3—H3A	110.2	C14—C15—H15	120.4
C4—C3—H3B	110.2	C15—C16—C17	120.8 (3)
C2—C3—H3B	110.2	C15—C16—H16	119.6
H3A—C3—H3B	108.5	C17—C16—H16	119.6
C3—C4—C5	104.3 (4)	C12—C17—C16	121.0 (3)
C3—C4—H4A	110.9	C12—C17—H17	119.5
C5—C4—H4A	110.9	C16—C17—H17	119.5
C3—C4—H4B	110.9	C23—C18—C19	118.1 (2)
C5—C4—H4B	110.9	C23—C18—Sn1	122.71 (18)
H4A—C4—H4B	108.9	C19—C18—Sn1	118.86 (19)
N1—C5—C4	103.7 (3)	C18—C19—C20	120.4 (3)
N1—C5—H5A	111.0	C18—C19—H19	119.8
C4—C5—H5A	111.0	C20—C19—H19	119.8
N1—C5—H5B	111.0	C21—C20—C19	120.8 (3)
C4—C5—H5B	111.0	C21—C20—H20	119.6
H5A—C5—H5B	109.0	C19—C20—H20	119.6
H4'1—C4'—H4'2	108.7	C20—C21—C22	119.4 (3)
C11—C6—C7	117.2 (2)	C20—C21—H21	120.3
C11—C6—Sn1	119.27 (19)	C22—C21—H21	120.3
C7—C6—Sn1	123.48 (19)	C21—C22—C23	120.2 (3)
C8—C7—C6	121.1 (3)	C21—C22—H22	119.9
C8—C7—H7	119.5	C23—C22—H22	119.9
C6—C7—H7	119.5	C18—C23—C22	121.1 (3)
C9—C8—C7	120.6 (3)	C18—C23—H23	119.4
C9—C8—H8	119.7	C22—C23—H23	119.4
C7—C8—H8	119.7	C1—N1—C5	123.2 (2)
C10—C9—C8	119.7 (3)	C1—N1—C2	125.5 (2)
C10—C9—H9	120.2	C5—N1—C2	111.4 (2)
C8—C9—H9	120.2	C1—S1—Sn1	96.24 (8)
C9—C10—C11	120.1 (3)	C12—Sn1—C18	112.21 (9)
C9—C10—H10	120.0	C12—Sn1—C6	108.90 (9)
C11—C10—H10	120.0	C18—Sn1—C6	103.66 (9)
C6—C11—C10	121.3 (3)	C12—Sn1—S1	114.00 (6)
C6—C11—H11	119.4	C18—Sn1—S1	120.74 (7)
C10—C11—H11	119.4	C6—Sn1—S1	94.43 (7)

N1—C2—C3—C4	−24.6 (5)	C23—C18—C19—C20	0.9 (4)
C2—C3—C4—C5	32.6 (6)	Sn1—C18—C19—C20	−172.5 (2)
C3—C4—C5—N1	−27.4 (6)	C18—C19—C20—C21	0.2 (5)
C11—C6—C7—C8	−1.1 (4)	C19—C20—C21—C22	−1.2 (5)
Sn1—C6—C7—C8	177.4 (2)	C20—C21—C22—C23	1.0 (5)
C6—C7—C8—C9	−0.5 (5)	C19—C18—C23—C22	−1.1 (4)
C7—C8—C9—C10	1.6 (5)	Sn1—C18—C23—C22	172.0 (2)
C8—C9—C10—C11	−1.1 (5)	C21—C22—C23—C18	0.2 (4)
C7—C6—C11—C10	1.6 (4)	S2—C1—N1—C5	−1.3 (4)
Sn1—C6—C11—C10	−176.9 (2)	S1—C1—N1—C5	179.4 (2)
C9—C10—C11—C6	−0.5 (5)	S2—C1—N1—C2	179.1 (2)
C17—C12—C13—C14	−1.4 (4)	S1—C1—N1—C2	−0.2 (4)
Sn1—C12—C13—C14	178.2 (2)	C4—C5—N1—C1	−167.1 (4)
C12—C13—C14—C15	−0.2 (4)	C4—C5—N1—C2	12.6 (4)
C13—C14—C15—C16	1.5 (5)	C3—C2—N1—C1	−173.9 (3)
C14—C15—C16—C17	−1.2 (6)	C3—C2—N1—C5	6.5 (3)
C13—C12—C17—C16	1.8 (5)	N1—C1—S1—Sn1	176.18 (19)
Sn1—C12—C17—C16	−177.9 (3)	S2—C1—S1—Sn1	−3.10 (16)
C15—C16—C17—C12	−0.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1	0.93	2.75	3.384 (3)	127
C23—H23···S2	0.93	2.77	3.424 (3)	129
C2—H2B···S2ⁱ	0.97	2.96	3.759 (3)	141
C5—H5B···S1ⁱⁱ	0.97	2.98	3.750 (3)	137

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Selected bond lengths (Å) top

Sn1—C6	2.160 (2)	Sn1—C18	2.149 (2)
Sn1—C12	2.134 (2)	Sn1—S1	2.4710 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1	0.93	2.75	3.384 (3)	127
C23—H23···S2	0.93	2.77	3.424 (3)	129
C2—H2B···S2ⁱ	0.97	2.96	3.759 (3)	141
C5—H5B···S1ⁱⁱ	0.97	2.98	3.750 (3)	137

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Quaid-i-Azam University Islamabad Pakistan for providing the research facilites as well as University Research Fund (URF) for financial support.

References

Abbas, S. M., Sirajuddin, M., Ali, S., Hussain, S. T., Shah, F. A. & Meetsma, A. (2013). J. Chem. Soc. Pak. 35, 859–867. Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pellerito, L. & Nagy, L. (2002). Coord. Chem. Rev. 224, 111–150. Web of Science CrossRef CAS Google Scholar
Ronconi, L., Maccato, C., Barreca, D., Saini, R., Zancato, M. & Fregona, D. (2005). Polyhedron, 24, 521–531. Web of Science CrossRef CAS Google Scholar
Shahzadi, S., Ali, S., Bhatti, M. H., Fettouhi, M. & Athar, M. (2006). J. Organomet. Chem. 691, 1797–1802. Web of Science CSD CrossRef CAS Google Scholar
Shahzadi, S., Ali, S. & Fettouhi, M. (2008). J. Chem. Crystallogr. 38, 273–278. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany. Google Scholar
Sirajuddin, M., Ali, S., Haider, A., Shah, N. A., Shah, A. & Khan, M. R. (2012). Polyhedron, 40, 19–31. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar