Dichlorido{4-cyclo­hexyl-1-[1-(2-pyridyl-κN)ethyl­idene]thio­semicarbazidato-κ2N1,S}phenyl­tin(IV)

Salam, M.A.; Affan, M.A.; Ahmad, F.B.; Tahir, M.I.M.; Tiekink, E.R.T.

doi:10.1107/S1600536810044247

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1503-m1504

https://doi.org/10.1107/S1600536810044247

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Dichlorido{4-cyclohexyl-1-[1-(2-pyridyl-κN)ethylidene]thiosemicarbazidato-κ²N¹,S}phenyltin(IV)

Md. Abdus Salam,^a Md. Abu Affan,^a ‡ Fasihuddin B. Ahmad,^a M. Ibrahim Mohamed Tahir ^b and Edward R. T. Tiekink ^c ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, ^bFaculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 October 2010; accepted 28 October 2010; online 6 November 2010)

The Sn^IV atom in the title compound, [Sn(C₆H₅)(C₁₄H₁₉N₄S)Cl₂], exists within a distorted octahedral geometry defined by the N,N′,S-tridentate monodeprotonated Schiff base ligand, two mutually trans Cl atoms, and the ipso-C atom of the Sn-bound phenyl group; the latter is trans to the azo-N atom. The greatest distortion from the ideal geometry is found in the nominally trans angle formed by the S and pyridyl-N atoms at Sn [151.03 (4)°]. With the exception of the cyclohexyl group (chair form), the Schiff base ligand is almost planar (r.m.s. deviation of non-H and Sn atoms = 0.053 Å). The nearly orthogonal orientation of the Sn-bound phenyl group [N—Sn—C—C torsion angle = 70.8 (5)°] to the planar portion of the Schiff base allows for the formation of significant intramolecular C—H⋯Cl interactions which preclude the Cl atoms from participating in N—H⋯Cl hydrogen bonds. Instead, C—H⋯π contacts, involving methylene H and the Sn-bound phenyl group, lead to the formation of supramolecular chains that pack in the bc plane. Connections between these layers are of the type C—H⋯Cl.

Related literature

For the structure of the methyltin derivative, see: Salam et al. (2010 ).

Experimental

Crystal data

[Sn(C₆H₅)(C₁₄H₁₉N₄S)Cl₂]
M_r = 542.08
Monoclinic, P 2₁ /n
a = 11.5213 (2) Å
b = 13.3795 (2) Å
c = 15.2648 (2) Å
β = 109.630 (2)°
V = 2216.30 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.50 mm⁻¹
T = 150 K
0.37 × 0.21 × 0.15 mm

Data collection

Area diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.730, T_max = 0.798
23984 measured reflections
3900 independent reflections
3642 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.047
S = 1.02
3900 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—Cl1	2.4587 (5)
Sn—Cl2	2.5083 (5)
Sn—S1	2.4768 (5)
Sn—N1	2.2552 (15)
Sn—N2	2.2309 (15)
Sn—C15	2.1552 (17)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1ⁱ	0.99	2.60	3.522 (2)	155
C13—H13B⋯Cl1ⁱⁱ	0.99	2.80	3.632 (2)	142
C16—H16⋯Cl2	0.95	2.66	3.350 (2)	130
C20—H20⋯Cl1	0.95	2.70	3.363 (2)	127
Symmetry codes: (i) x, y-1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 $[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044247/hb5715sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044247/hb5715Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is the phenyltin derivative of the recently described structure of dichlorido{4-cyclohexyl-1-[1-(2-pyridyl-κN)ethylidene]thiosemicarbazidato-κ²N¹,S}methyltin(IV) (Salam et al., 2010).

The Sn atom in (I), Fig. 1, exists within a six atom CCl₂N₂S donor set defined by the tridentate monodeprotonated Schiff base ligand, two mutually trans chlorido atoms, and the ispo-C atom of the Sn-bound phenyl group which is trans to the azo-N atom, Table 1. Distortions from the ideal octahedral geometry are ascribed primarily to the restricted bite distances formed by the Schiff base which results in an angle of 151.03 (4) ° for the nominally trans S1—Sn—N1 angle. The disposition of donor atoms resembles that found in the structure of the methyltin derivative (Salam et al., 2010). With the exception of the cyclohexyl group, which adopts a chair conformation, the Schiff base ligand is planar. Thus, the r.m.s. deviation from the least-squares plane through the 15 non-H atoms in the conjugated part of the ligand including the Sn and methine-C15 atoms, i.e. Sn,S1,N1–N4,C1–C9, is 0.053 Å. The Sn-bound phenyl group occupies a position almost orthogonal to the chelate rings as seen in the N2—Sn—C15—C16 torsion angle of 70.8 (5) Å.

In the crystal, supramolecular chains along the b axis are mediated by C—H···π interactions involving a methylene-H interacting with the Sn-bound phenyl group, Table 1. The chains pack in the bc plane and connections between the layers stacked along the a axis are of the type C—H···Cl, Fig. 2 and Table 1. The non-participation of the N—H atom in forming a significant intermolecular interaction contrasts the formation of N—H···Cl interactions in the methyltin derivative (Salam et al., 2010). It is noted that the orthogonal orientation of the Sn-bound phenyl group allows for the formation of close intramolecular C—H···Cl contacts, Table 1, which probably deactivate the chlorido atoms from forming significant hydrogen bonds. Further, it is noted that the C—H···π interactions present in (I) involves the Sn-bound phenyl group as as the acceptor, and that these are not possible in the methyltin derivative. Together, these factors explain the absence of significant hydrogen bonding interactions involving the N—H atom.

Related literature top

For the structure of the methyltin derivative, see: Salam et al. (2010).

Experimental top

2-Acetylpyridine-N-cyclohexyl thiosemicarbazone (0.28 g, 1.0 mmol) was dissolved in absolute methanol (10 ml) in a Schlenk round bottom flask under a nitrogen atmosphere and stirred for 30 min. Then, a 10 ml me thanolic solution of phenyltin(IV) trichloride (0.302 g, 1.0 mmol) was added drop wise while stirring which resulted in the formation of a yellow solution. The reaction mixture was refluxed for 4 h. and then cooled to room temperature. Yellow micro crystals of (I) were obtained from the slow evaporation of the solution at room temperature. The micro crystals were filtered off, washed with a small amount of cool methanol and dried in vacuo over silica gel. Light-yellow crystals were obtained from the slow evaporation of a chloroform/methanol (1/1) solution of (I) held at room temperature. Yield: 0.45 g, 77%: M.pt.: 523–525 K. Anal. Calc. for C₂₀H₂₄Cl₂N₄SSn: C, 44.30; H, 4.46; N, 10.33%. Found: C, 44.12; H, 4.27; N, 10.18%.

Structure description top

For the structure of the methyltin derivative, see: Salam et al. (2010).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Unit-cell contents shown in projection down the c axis in (I). The C–H···Cl and C–H···π contacts are shown as orange and purple dashed lines, respectively.

Dichlorido{4-cyclohexyl-1-[1-(2-pyridyl- κN)ethylidene]thiosemicarbazidato- κ²N¹,S}phenyltin(IV) top

Crystal data top

[Sn(C₆H₅)(C₁₄H₁₉N₄S)Cl₂]	F(000) = 1088
M_r = 542.08	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17836 reflections
a = 11.5213 (2) Å	θ = 2.4–28.9°
b = 13.3795 (2) Å	µ = 1.50 mm⁻¹
c = 15.2648 (2) Å	T = 150 K
β = 109.630 (2)°	Prism, orange
V = 2216.30 (6) Å³	0.37 × 0.21 × 0.15 mm
Z = 4

Data collection top

Area diffractometer	3642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω/2θ scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)	h = −13→13
T_min = 0.730, T_max = 0.798	k = −15→15
23984 measured reflections	l = −18→18
3900 independent reflections

Refinement top

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0232P)² + 1.3698P] where P = (F_o² + 2F_c²)/3
3900 reflections	(Δ/σ)_max = 0.003
257 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Sn(C₆H₅)(C₁₄H₁₉N₄S)Cl₂]	V = 2216.30 (6) Å³
M_r = 542.08	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5213 (2) Å	µ = 1.50 mm⁻¹
b = 13.3795 (2) Å	T = 150 K
c = 15.2648 (2) Å	0.37 × 0.21 × 0.15 mm
β = 109.630 (2)°

Data collection top

Area diffractometer	3900 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)	3642 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.798	R_int = 0.034
23984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	1 restraint
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3900 reflections	Δρ_min = −0.45 e Å⁻³
257 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Sn	0.473542 (11)	0.564452 (9)	0.716818 (8)	0.01429 (6)
Cl1	0.25305 (5)	0.55811 (4)	0.62427 (4)	0.02697 (12)
Cl2	0.67571 (4)	0.56343 (3)	0.84773 (3)	0.02149 (11)
S1	0.52690 (6)	0.41751 (4)	0.63924 (4)	0.02665 (13)
N1	0.39962 (14)	0.63184 (11)	0.82288 (10)	0.0162 (3)
N2	0.43068 (15)	0.43990 (10)	0.79821 (11)	0.0163 (3)
N3	0.45002 (15)	0.34299 (11)	0.78079 (11)	0.0186 (3)
N4	0.51413 (16)	0.23328 (12)	0.69436 (11)	0.0214 (4)
H4N	0.5435 (19)	0.2243 (16)	0.6499 (11)	0.026*
C1	0.36701 (17)	0.56662 (13)	0.87825 (13)	0.0160 (4)
C2	0.31498 (17)	0.60120 (15)	0.94234 (13)	0.0198 (4)
H2	0.2945	0.5557	0.9827	0.024*
C3	0.29312 (18)	0.70261 (15)	0.94712 (13)	0.0230 (4)
H3	0.2559	0.7269	0.9898	0.028*
C4	0.32570 (19)	0.76806 (15)	0.88952 (14)	0.0242 (4)
H4	0.3110	0.8377	0.8916	0.029*
C5	0.38022 (18)	0.72975 (14)	0.82871 (13)	0.0203 (4)
H5	0.4047	0.7744	0.7898	0.024*
C6	0.38569 (17)	0.46014 (14)	0.86329 (13)	0.0166 (4)
C7	0.3507 (2)	0.38016 (14)	0.91856 (14)	0.0240 (4)
H7A	0.2608	0.3740	0.8978	0.036*
H7B	0.3817	0.3978	0.9847	0.036*
H7C	0.3867	0.3164	0.9093	0.036*
C8	0.49310 (18)	0.32842 (14)	0.71163 (12)	0.0193 (4)
C9	0.49837 (18)	0.14827 (13)	0.75032 (13)	0.0186 (4)
H9	0.4180	0.1560	0.7613	0.022*
C10	0.49480 (18)	0.05184 (13)	0.69666 (14)	0.0179 (4)
H10A	0.5731	0.0436	0.6841	0.022*
H10B	0.4268	0.0548	0.6363	0.022*
C11	0.47560 (19)	−0.03703 (14)	0.75323 (14)	0.0213 (4)
H11A	0.3950	−0.0304	0.7626	0.026*
H11B	0.4745	−0.0996	0.7184	0.026*
C12	0.5780 (2)	−0.04246 (15)	0.84755 (15)	0.0301 (5)
H12A	0.6577	−0.0555	0.8383	0.036*
H12B	0.5615	−0.0985	0.8841	0.036*
C13	0.5861 (2)	0.05525 (15)	0.90122 (15)	0.0305 (5)
H13A	0.5103	0.0639	0.9173	0.037*
H13B	0.6571	0.0522	0.9599	0.037*
C14	0.6013 (2)	0.14412 (15)	0.84392 (14)	0.0272 (5)
H14A	0.6011	0.2066	0.8786	0.033*
H14B	0.6816	0.1392	0.8339	0.033*
C15	0.51354 (17)	0.69707 (13)	0.65203 (12)	0.0151 (4)
C16	0.62574 (18)	0.74626 (14)	0.68942 (14)	0.0204 (4)
H16	0.6849	0.7224	0.7453	0.024*
C17	0.65198 (19)	0.83006 (14)	0.64572 (15)	0.0242 (4)
H17	0.7292	0.8628	0.6714	0.029*
C18	0.5663 (2)	0.86581 (14)	0.56524 (14)	0.0245 (5)
H18	0.5845	0.9231	0.5355	0.029*
C19	0.45379 (19)	0.81846 (15)	0.52775 (13)	0.0242 (4)
H19	0.3943	0.8439	0.4728	0.029*
C20	0.42738 (18)	0.73337 (14)	0.57055 (13)	0.0199 (4)
H20	0.3506	0.7002	0.5441	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01933 (9)	0.01020 (8)	0.01541 (8)	−0.00154 (5)	0.00855 (6)	−0.00036 (4)
Cl1	0.0224 (3)	0.0325 (3)	0.0231 (3)	−0.0101 (2)	0.0038 (2)	−0.0018 (2)
Cl2	0.0195 (2)	0.0233 (3)	0.0212 (2)	0.00270 (18)	0.00619 (19)	0.00428 (18)
S1	0.0507 (4)	0.0124 (2)	0.0274 (3)	−0.0002 (2)	0.0270 (3)	−0.0005 (2)
N1	0.0174 (8)	0.0144 (8)	0.0174 (8)	−0.0014 (6)	0.0068 (6)	−0.0016 (6)
N2	0.0219 (9)	0.0122 (8)	0.0161 (8)	−0.0020 (6)	0.0081 (7)	−0.0011 (6)
N3	0.0283 (9)	0.0094 (7)	0.0211 (8)	−0.0005 (7)	0.0122 (7)	−0.0015 (6)
N4	0.0340 (10)	0.0133 (8)	0.0220 (9)	0.0000 (7)	0.0163 (8)	−0.0012 (7)
C1	0.0135 (9)	0.0182 (10)	0.0153 (9)	−0.0033 (7)	0.0037 (7)	−0.0016 (7)
C2	0.0200 (10)	0.0242 (10)	0.0162 (9)	−0.0029 (8)	0.0074 (8)	−0.0020 (8)
C3	0.0213 (10)	0.0274 (11)	0.0226 (10)	−0.0012 (9)	0.0102 (8)	−0.0098 (8)
C4	0.0271 (11)	0.0163 (10)	0.0290 (11)	0.0008 (8)	0.0094 (9)	−0.0064 (8)
C5	0.0240 (10)	0.0144 (9)	0.0228 (10)	−0.0025 (8)	0.0081 (8)	−0.0021 (8)
C6	0.0173 (9)	0.0166 (9)	0.0154 (9)	−0.0020 (8)	0.0048 (8)	0.0004 (7)
C7	0.0318 (11)	0.0207 (10)	0.0248 (10)	−0.0027 (9)	0.0166 (9)	0.0026 (8)
C8	0.0255 (10)	0.0139 (9)	0.0184 (9)	0.0000 (8)	0.0072 (8)	−0.0010 (7)
C9	0.0241 (10)	0.0132 (9)	0.0199 (9)	−0.0015 (8)	0.0094 (8)	0.0003 (8)
C10	0.0208 (10)	0.0145 (9)	0.0198 (10)	0.0009 (8)	0.0085 (8)	−0.0012 (7)
C11	0.0271 (11)	0.0128 (9)	0.0270 (11)	−0.0035 (8)	0.0129 (9)	−0.0024 (8)
C12	0.0369 (13)	0.0184 (10)	0.0322 (12)	−0.0001 (9)	0.0080 (10)	0.0088 (9)
C13	0.0373 (13)	0.0275 (12)	0.0212 (11)	−0.0025 (9)	0.0024 (10)	0.0039 (9)
C14	0.0309 (11)	0.0200 (10)	0.0261 (11)	−0.0066 (9)	0.0035 (9)	−0.0006 (8)
C15	0.0206 (9)	0.0108 (8)	0.0183 (9)	0.0021 (7)	0.0121 (8)	−0.0005 (7)
C16	0.0197 (10)	0.0174 (9)	0.0256 (10)	0.0028 (8)	0.0096 (8)	0.0025 (8)
C17	0.0246 (10)	0.0153 (9)	0.0380 (12)	−0.0016 (8)	0.0173 (9)	0.0002 (9)
C18	0.0379 (12)	0.0142 (9)	0.0322 (11)	0.0037 (9)	0.0261 (10)	0.0057 (8)
C19	0.0347 (12)	0.0226 (10)	0.0197 (10)	0.0100 (9)	0.0150 (9)	0.0064 (8)
C20	0.0227 (10)	0.0194 (10)	0.0196 (9)	0.0017 (8)	0.0096 (8)	−0.0005 (8)

Geometric parameters (Å, º) top

Sn—Cl1	2.4587 (5)	C9—C10	1.521 (2)
Sn—Cl2	2.5083 (5)	C9—C14	1.520 (3)
Sn—S1	2.4768 (5)	C9—H9	1.0000
Sn—N1	2.2552 (15)	C10—C11	1.529 (3)
Sn—N2	2.2309 (15)	C10—H10A	0.9900
Sn—C15	2.1552 (17)	C10—H10B	0.9900
S1—C8	1.7558 (19)	C11—C12	1.526 (3)
N1—C5	1.337 (2)	C11—H11A	0.9900
N1—C1	1.353 (2)	C11—H11B	0.9900
N2—C6	1.294 (2)	C12—C13	1.529 (3)
N2—N3	1.357 (2)	C12—H12A	0.9900
N3—C8	1.323 (2)	C12—H12B	0.9900
N4—C8	1.338 (2)	C13—C14	1.520 (3)
N4—C9	1.470 (2)	C13—H13A	0.9900
N4—H4N	0.863 (19)	C13—H13B	0.9900
C1—C2	1.387 (3)	C14—H14A	0.9900
C1—C6	1.470 (3)	C14—H14B	0.9900
C2—C3	1.386 (3)	C15—C16	1.391 (3)
C2—H2	0.9500	C15—C20	1.392 (3)
C3—C4	1.379 (3)	C16—C17	1.389 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.382 (3)	C17—C18	1.378 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.382 (3)
C6—C7	1.499 (3)	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.396 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—H20	0.9500

C15—Sn—N2	172.75 (6)	N4—C9—C14	111.40 (16)
C15—Sn—N1	101.00 (6)	C10—C9—C14	110.28 (16)
N2—Sn—N1	72.01 (5)	N4—C9—H9	108.6
C15—Sn—Cl1	95.95 (5)	C10—C9—H9	108.6
N2—Sn—Cl1	85.12 (4)	C14—C9—H9	108.6
N1—Sn—Cl1	81.94 (4)	C9—C10—C11	109.78 (16)
C15—Sn—S1	107.97 (5)	C9—C10—H10A	109.7
N2—Sn—S1	79.07 (4)	C11—C10—H10A	109.7
N1—Sn—S1	151.03 (4)	C9—C10—H10B	109.7
Cl1—Sn—S1	94.152 (19)	C11—C10—H10B	109.7
C15—Sn—Cl2	94.91 (5)	H10A—C10—H10B	108.2
N2—Sn—Cl2	82.66 (4)	C12—C11—C10	110.94 (16)
N1—Sn—Cl2	84.48 (4)	C12—C11—H11A	109.5
Cl1—Sn—Cl2	164.001 (18)	C10—C11—H11A	109.5
S1—Sn—Cl2	93.632 (18)	C12—C11—H11B	109.5
C8—S1—Sn	95.44 (6)	C10—C11—H11B	109.5
C5—N1—C1	120.18 (16)	H11A—C11—H11B	108.0
C5—N1—Sn	123.46 (13)	C11—C12—C13	110.71 (17)
C1—N1—Sn	116.22 (11)	C11—C12—H12A	109.5
C6—N2—N3	119.00 (15)	C13—C12—H12A	109.5
C6—N2—Sn	119.47 (12)	C11—C12—H12B	109.5
N3—N2—Sn	121.53 (11)	C13—C12—H12B	109.5
C8—N3—N2	115.31 (15)	H12A—C12—H12B	108.1
C8—N4—C9	123.75 (16)	C14—C13—C12	111.01 (18)
C8—N4—H4N	115.6 (15)	C14—C13—H13A	109.4
C9—N4—H4N	120.5 (14)	C12—C13—H13A	109.4
N1—C1—C2	120.13 (16)	C14—C13—H13B	109.4
N1—C1—C6	116.24 (16)	C12—C13—H13B	109.4
C2—C1—C6	123.59 (17)	H13A—C13—H13B	108.0
C1—C2—C3	119.52 (18)	C9—C14—C13	111.42 (16)
C1—C2—H2	120.2	C9—C14—H14A	109.3
C3—C2—H2	120.2	C13—C14—H14A	109.3
C4—C3—C2	119.64 (18)	C9—C14—H14B	109.3
C4—C3—H3	120.2	C13—C14—H14B	109.3
C2—C3—H3	120.2	H14A—C14—H14B	108.0
C3—C4—C5	118.37 (18)	C16—C15—C20	119.14 (17)
C3—C4—H4	120.8	C16—C15—Sn	120.92 (13)
C5—C4—H4	120.8	C20—C15—Sn	119.93 (13)
N1—C5—C4	122.13 (18)	C15—C16—C17	120.47 (18)
N1—C5—H5	118.9	C15—C16—H16	119.8
C4—C5—H5	118.9	C17—C16—H16	119.8
N2—C6—C1	116.06 (16)	C18—C17—C16	120.14 (19)
N2—C6—C7	122.37 (17)	C18—C17—H17	119.9
C1—C6—C7	121.55 (17)	C16—C17—H17	119.9
C6—C7—H7A	109.5	C17—C18—C19	120.10 (18)
C6—C7—H7B	109.5	C17—C18—H18	119.9
H7A—C7—H7B	109.5	C19—C18—H18	119.9
C6—C7—H7C	109.5	C18—C19—C20	120.10 (18)
H7A—C7—H7C	109.5	C18—C19—H19	120.0
H7B—C7—H7C	109.5	C20—C19—H19	120.0
N3—C8—N4	116.01 (17)	C15—C20—C19	120.03 (18)
N3—C8—S1	128.61 (14)	C15—C20—H20	120.0
N4—C8—S1	115.38 (14)	C19—C20—H20	120.0
N4—C9—C10	109.25 (15)

C15—Sn—S1—C8	176.61 (8)	N3—N2—C6—C7	−1.8 (3)
N2—Sn—S1—C8	−1.55 (8)	Sn—N2—C6—C7	177.87 (14)
N1—Sn—S1—C8	−4.91 (11)	N1—C1—C6—N2	−0.4 (3)
Cl1—Sn—S1—C8	−85.76 (7)	C2—C1—C6—N2	177.22 (17)
Cl2—Sn—S1—C8	80.26 (7)	N1—C1—C6—C7	−178.61 (17)
C15—Sn—N1—C5	5.52 (16)	C2—C1—C6—C7	−1.0 (3)
N2—Sn—N1—C5	−176.48 (16)	N2—N3—C8—N4	179.18 (16)
Cl1—Sn—N1—C5	−89.02 (15)	N2—N3—C8—S1	−0.7 (3)
S1—Sn—N1—C5	−173.00 (11)	C9—N4—C8—N3	−3.4 (3)
Cl2—Sn—N1—C5	99.47 (15)	C9—N4—C8—S1	176.47 (14)
C15—Sn—N1—C1	−178.78 (13)	Sn—S1—C8—N3	1.86 (19)
N2—Sn—N1—C1	−0.78 (12)	Sn—S1—C8—N4	−177.98 (14)
Cl1—Sn—N1—C1	86.68 (12)	C8—N4—C9—C10	164.24 (18)
S1—Sn—N1—C1	2.70 (18)	C8—N4—C9—C14	−73.7 (2)
Cl2—Sn—N1—C1	−84.83 (12)	N4—C9—C10—C11	−178.77 (16)
C15—Sn—N2—C6	16.3 (6)	C14—C9—C10—C11	58.5 (2)
N1—Sn—N2—C6	0.57 (14)	C9—C10—C11—C12	−58.4 (2)
Cl1—Sn—N2—C6	−82.53 (14)	C10—C11—C12—C13	56.4 (2)
S1—Sn—N2—C6	−177.72 (15)	C11—C12—C13—C14	−54.7 (3)
Cl2—Sn—N2—C6	87.12 (14)	N4—C9—C14—C13	−179.10 (17)
C15—Sn—N2—N3	−164.1 (4)	C10—C9—C14—C13	−57.6 (2)
N1—Sn—N2—N3	−179.81 (15)	C12—C13—C14—C9	55.6 (3)
Cl1—Sn—N2—N3	97.10 (13)	N2—Sn—C15—C16	70.8 (5)
S1—Sn—N2—N3	1.90 (13)	N1—Sn—C15—C16	86.01 (15)
Cl2—Sn—N2—N3	−93.26 (13)	Cl1—Sn—C15—C16	168.92 (14)
C6—N2—N3—C8	178.28 (17)	S1—Sn—C15—C16	−94.74 (14)
Sn—N2—N3—C8	−1.3 (2)	Cl2—Sn—C15—C16	0.69 (14)
C5—N1—C1—C2	−1.0 (3)	N2—Sn—C15—C20	−110.5 (5)
Sn—N1—C1—C2	−176.82 (14)	N1—Sn—C15—C20	−95.31 (14)
C5—N1—C1—C6	176.77 (17)	Cl1—Sn—C15—C20	−12.40 (14)
Sn—N1—C1—C6	0.9 (2)	S1—Sn—C15—C20	83.93 (14)
N1—C1—C2—C3	2.0 (3)	Cl2—Sn—C15—C20	179.37 (13)
C6—C1—C2—C3	−175.53 (18)	C20—C15—C16—C17	−0.5 (3)
C1—C2—C3—C4	−1.4 (3)	Sn—C15—C16—C17	178.20 (14)
C2—C3—C4—C5	−0.3 (3)	C15—C16—C17—C18	0.6 (3)
C1—N1—C5—C4	−0.8 (3)	C16—C17—C18—C19	0.1 (3)
Sn—N1—C5—C4	174.74 (14)	C17—C18—C19—C20	−1.0 (3)
C3—C4—C5—N1	1.4 (3)	C16—C15—C20—C19	−0.4 (3)
N3—N2—C6—C1	−179.92 (15)	Sn—C15—C20—C19	−179.10 (13)
Sn—N2—C6—C1	−0.3 (2)	C18—C19—C20—C15	1.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of benzene ring C15–C20.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.99	2.60	3.522 (2)	155
C13—H13B···Cl1ⁱⁱ	0.99	2.80	3.632 (2)	142
C16—H16···Cl2	0.95	2.66	3.350 (2)	130
C20—H20···Cl1	0.95	2.70	3.363 (2)	127

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)(C₁₄H₁₉N₄S)Cl₂]
M_r	542.08
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	11.5213 (2), 13.3795 (2), 15.2648 (2)
β (°)	109.630 (2)
V (Å³)	2216.30 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.37 × 0.21 × 0.15

Data collection
Diffractometer	Area
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2002)
T_min, T_max	0.730, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	23984, 3900, 3642
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.047, 1.02
No. of reflections	3900
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.45

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn—Cl1	2.4587 (5)	Sn—N1	2.2552 (15)
Sn—Cl2	2.5083 (5)	Sn—N2	2.2309 (15)
Sn—S1	2.4768 (5)	Sn—C15	2.1552 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of benzene ring C15–C20.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.99	2.60	3.522 (2)	155
C13—H13B···Cl1ⁱⁱ	0.99	2.80	3.632 (2)	142
C16—H16···Cl2	0.95	2.66	3.350 (2)	130
C20—H20···Cl1	0.95	2.70	3.363 (2)	127

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

Footnotes

‡Additional correspondence author, e-mail: maaffan@yahoo.com.

Acknowledgements

The authors thank MOSTI (grant No. 06-01-09-SF0046) and the Universiti Malaysia Sarawak for supporting this study.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Salam, M. A., Affan, M. A., Shamsuddin, M. & Ng, S. W. (2010). Acta Cryst. E66, m570. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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