Chlorido{4-cyclo­hexyl-1-[1-(pyridin-2-yl-κN)ethyl­idene]thio­semicarbazidato-κ2N1,S}diphenyl­tin(IV)

Affan, M.A.; Salam, M.A.; Jusoh, I.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812010902

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m435-m436

doi:10.1107/S1600536812010902

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Chlorido{4-cyclohexyl-1-[1-(pyridin-2-yl-κN)ethylidene]thiosemicarbazidato-κ²N¹,S}diphenyltin(IV)

Md. Abu Affan,^a Md. Abdus Salam,^a Ismail Jusoh,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samaharan, Sawarak, Malaysia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 8 March 2012; accepted 13 March 2012; online 17 March 2012)

The distorted octahedral geometry about the Sn^IV atom in the title compound, [Sn(C₆H₅)₂(C₁₄H₁₉N₄S)Cl], is defined by the N,N,S-tridentate Schiff base ligand, two mutually trans ipso-C atoms of the Sn-bound phenyl groups, and the Cl atom which is trans to the azo N atom. The two five-membered chelate rings and pyridyl ring are almost coplanar with the dihedral angle between the outer five-membered chelate and pyridine rings being 5.39 (8)°. Centrosymmetric dimers feature in the crystal packing mediated by N—H⋯S hydrogen bonds, leading to eight-membered {⋯HNCS}₂ synthons. The dimeric aggregates are connected into a three-dimensional architecture by C—H⋯Cl and C—H⋯π interactions, as well as π–π interactions occurring between centrosymmetrically related pyridine rings [centroid–centroid distance = 3.6322 (13) Å].

Related literature

For the crystal structure of the dichloridophenyl analogue, see: Salam et al. (2010 ). For a related structure, see: de Sousa et al. (2007 ).

Experimental

Crystal data

[Sn(C₆H₅)₂(C₁₄H₁₉N₄S)Cl]
M_r = 583.73
Triclinic, $[P \overline 1]$
a = 9.7368 (4) Å
b = 9.9771 (4) Å
c = 13.4045 (5) Å
α = 90.103 (3)°
β = 97.013 (3)°
γ = 100.931 (4)°
V = 1268.57 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.642, T_max = 0.793
8973 measured reflections
5781 independent reflections
5122 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.061
S = 1.00
5781 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—C1	2.152 (2)
Sn—C7	2.159 (2)
Sn—N2	2.3100 (19)
Sn—N1	2.3869 (19)
Sn—S1	2.5209 (6)
Sn—Cl1	2.5449 (6)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1⋯S1ⁱ	0.88	2.62	3.489 (2)	171
C13—H13⋯Cl1ⁱⁱ	0.95	2.73	3.415 (3)	129
C19—H19C⋯Cl1ⁱⁱⁱ	0.98	2.85	3.809 (2)	166
C15—H15⋯Cg1^iv	0.95	2.47	3.384 (3)	162
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+2; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010902/zl2462sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010902/zl2462Isup2.hkl

checkCIF report

Comment top

The synthesis and crystal structure of the title compound was determined in connection with recent structural studies of organotin chlorido derivatives of thiosemicarbazones (Salam et al., 2010).

The Sn atom in the title compound, Fig. 1, exists within a six atom C₂ClN₂S donor set defined by the tridentate monodeprotonated Schiff base ligand, two mutually trans ipso-C atoms of the Sn-bound phenyl groups, and the Cl atom which is trans to the azo-N atom, Table 1. There are distortions from the ideal octahedral geometry which are ascribed to the restricted bite angles formed by the Schiff base ligand which result in an angle of 145.90 (5)° for the nominally trans S1—–Sn—–N1 angle. The disposition of donor atoms resembles that found in the structure of the N-4-morpholinyl derivative (de Sousa et al., 2007). Both five-membered rings are essentially planar with the r.m.s. deviations being 0.111 and 0.020 Å for the SnSN₂C and SnN₂C₂ rings, respectively; the former ring has a small twist about the Sn—S1 bond with Sn and S1 atoms lying 0.068 (1) and -0.081 (1) Å out of the least-squares plane, respectively. The dihedral angle between the chelate rings is 3.42 (7)° and those between each of these and the pyridyl ring are 5.39 (8) and 2.29 (9)°, respectively, indicating an essentially planar arrangement of fused rings. Finally, the Sn-bound benzene rings are almost parallel with the dihedral angle being 8.72 (12)°.

The most significant feature in the crystal packing of the title compound is the formation of centrosymmetric dimers via N—H···S hydrogen bonds that lead to flat, eight-membered {···HNCS}₂ synthons, Table 1. The dimeric aggregates are connected into a three dimensional architecture by C—H···Cl and C—H···π interactions, Table 1, as well as π—π interactions occurring between centrosymmetrically related pyridyl rings [centroid···centroid distance = 3.6322 (13) Å for symmetry operation: 1 - x, 1 - y, 2 - z], Fig. 2.

Related literature top

For the crystal structure of the dichloridophenyl analogue, see: Salam et al. (2010). For a related structure, see: de Sousa et al. (2007).

Experimental top

2-Acetylpyridine-N-cyclohexylthiosemicarbazone (0.28 g, 1 mmol) was dissolved in methanol (10 ml) in a Schlenk flask under a nitrogen atmosphere. Diphenyltin(IV) dichloride (0.34 g, 1 mmol) dissolved in methanol (10 ml) was added. The yellow solution was refluxed for 4 h. Slow evaporation of the solvent gave a yellow compound (0.423 g). Recrystallization from a chloroform/methanol (1/1) mixture gave small dark-yellow prisms embedded in large light-yellow blocks. A small light-yellow specimen was cut from a light-yellow block for the diffraction measurements. The dark-yellow specimen proved to be (C₆H₅)Sn(C₁₄H₁₉N₄S)Cl₂ from unit cell determination (Salam et al., 2010).

Structure description top

The synthesis and crystal structure of the title compound was determined in connection with recent structural studies of organotin chlorido derivatives of thiosemicarbazones (Salam et al., 2010).

For the crystal structure of the dichloridophenyl analogue, see: Salam et al. (2010). For a related structure, see: de Sousa et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents of the title compound. The N—H···S, C—H···Cl, C—H···π and π—π interactions are shown as orange, blue, brown and purple dashed lines, respectively.

Chlorido{4-cyclohexyl-1-[1-(pyridin-2-yl- κN)ethylidene]thiosemicarbazidato- κ²N¹,S}diphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₂(C₁₄H₁₉N₄S)Cl]	Z = 2
M_r = 583.73	F(000) = 592
Triclinic, P1	D_x = 1.528 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7368 (4) Å	Cell parameters from 5479 reflections
b = 9.9771 (4) Å	θ = 2.5–27.5°
c = 13.4045 (5) Å	µ = 1.22 mm⁻¹
α = 90.103 (3)°	T = 100 K
β = 97.013 (3)°	Irregular, light-yellow
γ = 100.931 (4)°	0.40 × 0.30 × 0.20 mm
V = 1268.57 (9) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5781 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5122 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→12
T_min = 0.642, T_max = 0.793	l = −17→17
8973 measured 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0216P)²] where P = (F_o² + 2F_c²)/3
5781 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Sn(C₆H₅)₂(C₁₄H₁₉N₄S)Cl]	γ = 100.931 (4)°
M_r = 583.73	V = 1268.57 (9) Å³
Triclinic, P1	Z = 2
a = 9.7368 (4) Å	Mo Kα radiation
b = 9.9771 (4) Å	µ = 1.22 mm⁻¹
c = 13.4045 (5) Å	T = 100 K
α = 90.103 (3)°	0.40 × 0.30 × 0.20 mm
β = 97.013 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5781 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	5122 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.793	R_int = 0.029
8973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.00	Δρ_max = 0.51 e Å⁻³
5781 reflections	Δρ_min = −0.58 e Å⁻³
299 parameters

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

	x	y	z	U_iso*/U_eq
Sn	0.336547 (16)	0.124100 (16)	0.775567 (11)	0.01076 (5)
Cl1	0.34918 (7)	−0.11363 (6)	0.83991 (5)	0.02221 (14)
S1	0.13930 (6)	0.06101 (6)	0.63351 (4)	0.01420 (13)
N1	0.49818 (19)	0.3058 (2)	0.86673 (14)	0.0128 (4)
N2	0.31702 (19)	0.33125 (19)	0.70413 (14)	0.0111 (4)
N3	0.23447 (19)	0.3390 (2)	0.61378 (14)	0.0130 (4)
N4	0.08466 (19)	0.2234 (2)	0.48652 (14)	0.0144 (4)
H1	0.0336	0.1458	0.4612	0.017*
C1	0.5121 (2)	0.1152 (2)	0.69424 (17)	0.0139 (5)
C2	0.6324 (3)	0.0724 (3)	0.74073 (19)	0.0227 (6)
H2	0.6366	0.0452	0.8087	0.027*
C3	0.7461 (3)	0.0697 (3)	0.6874 (2)	0.0272 (6)
H3	0.8280	0.0414	0.7195	0.033*
C4	0.7409 (3)	0.1074 (3)	0.58891 (19)	0.0226 (6)
H4	0.8189	0.1052	0.5531	0.027*
C5	0.6220 (3)	0.1485 (3)	0.54170 (19)	0.0222 (6)
H5	0.6178	0.1733	0.4732	0.027*
C6	0.5085 (3)	0.1535 (3)	0.59448 (18)	0.0190 (5)
H6	0.4278	0.1835	0.5620	0.023*
C7	0.2074 (2)	0.1485 (2)	0.89180 (17)	0.0118 (5)
C8	0.2437 (3)	0.1153 (2)	0.99069 (17)	0.0173 (5)
H8	0.3282	0.0817	1.0086	0.021*
C9	0.1577 (3)	0.1305 (2)	1.06400 (18)	0.0187 (5)
H9	0.1843	0.1085	1.1316	0.022*
C10	0.0328 (3)	0.1780 (2)	1.03850 (19)	0.0189 (5)
H10	−0.0268	0.1868	1.0882	0.023*
C11	−0.0035 (2)	0.2120 (2)	0.94064 (18)	0.0184 (5)
H11	−0.0885	0.2447	0.9230	0.022*
C12	0.0832 (2)	0.1989 (2)	0.86723 (18)	0.0152 (5)
H12	0.0579	0.2243	0.8002	0.018*
C13	0.5906 (2)	0.2890 (3)	0.94570 (17)	0.0162 (5)
H13	0.5921	0.1992	0.9687	0.019*
C14	0.6845 (2)	0.3973 (3)	0.99555 (18)	0.0171 (5)
H14	0.7496	0.3821	1.0512	0.021*
C15	0.6809 (2)	0.5272 (3)	0.96253 (18)	0.0176 (5)
H15	0.7435	0.6035	0.9955	0.021*
C16	0.5851 (2)	0.5460 (2)	0.88041 (17)	0.0150 (5)
H16	0.5808	0.6352	0.8572	0.018*
C17	0.4954 (2)	0.4324 (2)	0.83251 (17)	0.0128 (5)
C18	0.3979 (2)	0.4439 (2)	0.74072 (17)	0.0128 (5)
C19	0.4031 (2)	0.5785 (2)	0.69161 (18)	0.0173 (5)
H19A	0.3328	0.5687	0.6319	0.026*
H19B	0.4973	0.6103	0.6718	0.026*
H19C	0.3828	0.6450	0.7389	0.026*
C20	0.1583 (2)	0.2215 (2)	0.57772 (17)	0.0125 (5)
C21	0.0833 (2)	0.3452 (2)	0.42632 (17)	0.0139 (5)
H21	0.0663	0.4201	0.4702	0.017*
C22	−0.0388 (2)	0.3141 (3)	0.34146 (18)	0.0179 (5)
H22A	−0.0269	0.2359	0.3000	0.022*
H22B	−0.1285	0.2879	0.3705	0.022*
C23	−0.0460 (3)	0.4371 (3)	0.27500 (19)	0.0235 (6)
H23A	−0.1208	0.4111	0.2176	0.028*
H23B	−0.0713	0.5110	0.3142	0.028*
C24	0.0936 (3)	0.4897 (3)	0.23527 (18)	0.0224 (6)
H24A	0.0875	0.5736	0.1971	0.027*
H24B	0.1133	0.4203	0.1890	0.027*
C25	0.2134 (3)	0.5208 (3)	0.32162 (19)	0.0222 (6)
H25A	0.3037	0.5521	0.2943	0.027*
H25B	0.1972	0.5950	0.3652	0.027*
C26	0.2223 (2)	0.3940 (3)	0.38360 (18)	0.0175 (5)
H26A	0.3003	0.4156	0.4393	0.021*
H26B	0.2419	0.3207	0.3407	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01145 (9)	0.01048 (9)	0.01016 (9)	0.00200 (6)	0.00073 (6)	−0.00036 (6)
Cl1	0.0329 (4)	0.0148 (3)	0.0222 (3)	0.0097 (3)	0.0083 (3)	0.0050 (2)
S1	0.0159 (3)	0.0116 (3)	0.0131 (3)	0.0000 (2)	−0.0020 (2)	0.0002 (2)
N1	0.0120 (10)	0.0146 (10)	0.0119 (10)	0.0019 (8)	0.0025 (8)	−0.0009 (8)
N2	0.0097 (9)	0.0130 (10)	0.0109 (9)	0.0024 (8)	0.0019 (8)	0.0010 (8)
N3	0.0124 (10)	0.0128 (10)	0.0126 (10)	0.0018 (8)	−0.0021 (8)	0.0013 (8)
N4	0.0152 (10)	0.0128 (10)	0.0127 (10)	−0.0013 (8)	−0.0017 (8)	0.0013 (8)
C1	0.0124 (12)	0.0134 (12)	0.0148 (12)	−0.0001 (10)	0.0016 (9)	−0.0014 (10)
C2	0.0195 (13)	0.0308 (16)	0.0201 (14)	0.0093 (12)	0.0041 (11)	0.0063 (12)
C3	0.0187 (14)	0.0354 (17)	0.0311 (16)	0.0123 (13)	0.0054 (12)	0.0020 (13)
C4	0.0183 (13)	0.0228 (14)	0.0276 (15)	0.0014 (11)	0.0108 (11)	−0.0054 (11)
C5	0.0243 (14)	0.0253 (15)	0.0168 (13)	0.0014 (12)	0.0074 (11)	0.0002 (11)
C6	0.0166 (13)	0.0228 (14)	0.0188 (13)	0.0072 (11)	0.0017 (10)	0.0000 (11)
C7	0.0122 (11)	0.0097 (11)	0.0124 (11)	−0.0019 (9)	0.0030 (9)	−0.0020 (9)
C8	0.0194 (13)	0.0150 (13)	0.0175 (13)	0.0035 (10)	0.0022 (10)	0.0001 (10)
C9	0.0258 (14)	0.0164 (13)	0.0119 (12)	−0.0011 (11)	0.0030 (10)	0.0015 (10)
C10	0.0197 (13)	0.0147 (13)	0.0229 (13)	−0.0004 (11)	0.0111 (11)	−0.0037 (10)
C11	0.0139 (12)	0.0172 (13)	0.0247 (14)	0.0034 (10)	0.0037 (10)	−0.0019 (11)
C12	0.0158 (12)	0.0129 (12)	0.0161 (12)	0.0014 (10)	0.0004 (10)	0.0010 (10)
C13	0.0173 (12)	0.0201 (13)	0.0117 (12)	0.0050 (11)	0.0014 (10)	−0.0015 (10)
C14	0.0133 (12)	0.0250 (14)	0.0119 (12)	0.0019 (11)	−0.0007 (9)	−0.0028 (10)
C15	0.0141 (12)	0.0201 (13)	0.0163 (12)	−0.0030 (10)	0.0030 (10)	−0.0042 (10)
C16	0.0144 (12)	0.0138 (12)	0.0164 (12)	0.0001 (10)	0.0042 (10)	−0.0007 (10)
C17	0.0119 (11)	0.0145 (12)	0.0128 (11)	0.0018 (10)	0.0060 (9)	0.0004 (9)
C18	0.0088 (11)	0.0153 (12)	0.0149 (12)	0.0025 (10)	0.0034 (9)	−0.0014 (10)
C19	0.0155 (12)	0.0123 (12)	0.0236 (13)	0.0009 (10)	0.0033 (10)	0.0004 (10)
C20	0.0095 (11)	0.0153 (12)	0.0140 (12)	0.0040 (10)	0.0034 (9)	−0.0001 (9)
C21	0.0139 (12)	0.0124 (12)	0.0151 (12)	0.0013 (10)	0.0026 (9)	0.0043 (9)
C22	0.0151 (12)	0.0233 (14)	0.0147 (12)	0.0039 (11)	−0.0015 (10)	0.0046 (10)
C23	0.0264 (14)	0.0284 (15)	0.0183 (13)	0.0127 (12)	0.0018 (11)	0.0063 (11)
C24	0.0300 (15)	0.0214 (14)	0.0190 (13)	0.0096 (12)	0.0083 (11)	0.0070 (11)
C25	0.0263 (14)	0.0204 (14)	0.0212 (14)	0.0027 (12)	0.0101 (11)	0.0016 (11)
C26	0.0142 (12)	0.0208 (13)	0.0172 (12)	0.0019 (10)	0.0035 (10)	0.0011 (10)

Geometric parameters (Å, º) top

Sn—C1	2.152 (2)	C11—C12	1.394 (3)
Sn—C7	2.159 (2)	C11—H11	0.9500
Sn—N2	2.3100 (19)	C12—H12	0.9500
Sn—N1	2.3869 (19)	C13—C14	1.387 (3)
Sn—S1	2.5209 (6)	C13—H13	0.9500
Sn—Cl1	2.5449 (6)	C14—C15	1.376 (3)
S1—C20	1.756 (2)	C14—H14	0.9500
N1—C13	1.335 (3)	C15—C16	1.391 (3)
N1—C17	1.349 (3)	C15—H15	0.9500
N2—C18	1.300 (3)	C16—C17	1.394 (3)
N2—N3	1.380 (3)	C16—H16	0.9500
N3—C20	1.319 (3)	C17—C18	1.478 (3)
N4—C20	1.342 (3)	C18—C19	1.492 (3)
N4—C21	1.461 (3)	C19—H19A	0.9800
N4—H1	0.8800	C19—H19B	0.9800
C1—C6	1.390 (3)	C19—H19C	0.9800
C1—C2	1.398 (3)	C21—C22	1.527 (3)
C2—C3	1.394 (3)	C21—C26	1.529 (3)
C2—H2	0.9500	C21—H21	1.0000
C3—C4	1.370 (4)	C22—C23	1.525 (3)
C3—H3	0.9500	C22—H22A	0.9900
C4—C5	1.382 (3)	C22—H22B	0.9900
C4—H4	0.9500	C23—C24	1.521 (3)
C5—C6	1.391 (3)	C23—H23A	0.9900
C5—H5	0.9500	C23—H23B	0.9900
C6—H6	0.9500	C24—C25	1.526 (4)
C7—C8	1.387 (3)	C24—H24A	0.9900
C7—C12	1.399 (3)	C24—H24B	0.9900
C8—C9	1.393 (3)	C25—C26	1.525 (3)
C8—H8	0.9500	C25—H25A	0.9900
C9—C10	1.391 (3)	C25—H25B	0.9900
C9—H9	0.9500	C26—H26A	0.9900
C10—C11	1.377 (3)	C26—H26B	0.9900
C10—H10	0.9500

C1—Sn—C7	163.82 (9)	N1—C13—H13	118.7
C1—Sn—N2	89.52 (8)	C14—C13—H13	118.7
C7—Sn—N2	94.19 (7)	C15—C14—C13	118.4 (2)
C1—Sn—N1	83.36 (7)	C15—C14—H14	120.8
C7—Sn—N1	83.23 (7)	C13—C14—H14	120.8
N2—Sn—N1	69.43 (6)	C14—C15—C16	119.4 (2)
C1—Sn—S1	98.90 (6)	C14—C15—H15	120.3
C7—Sn—S1	97.28 (6)	C16—C15—H15	120.3
N2—Sn—S1	76.55 (5)	C15—C16—C17	119.3 (2)
N1—Sn—S1	145.90 (5)	C15—C16—H16	120.4
C1—Sn—Cl1	89.13 (6)	C17—C16—H16	120.4
C7—Sn—Cl1	88.37 (6)	N1—C17—C16	120.7 (2)
N2—Sn—Cl1	175.15 (5)	N1—C17—C18	117.1 (2)
N1—Sn—Cl1	115.02 (5)	C16—C17—C18	122.1 (2)
S1—Sn—Cl1	99.07 (2)	N2—C18—C17	116.6 (2)
C20—S1—Sn	96.99 (8)	N2—C18—C19	123.7 (2)
C13—N1—C17	119.5 (2)	C17—C18—C19	119.6 (2)
C13—N1—Sn	124.50 (16)	C18—C19—H19A	109.5
C17—N1—Sn	115.98 (15)	C18—C19—H19B	109.5
C18—N2—N3	116.92 (19)	H19A—C19—H19B	109.5
C18—N2—Sn	120.81 (15)	C18—C19—H19C	109.5
N3—N2—Sn	121.65 (14)	H19A—C19—H19C	109.5
C20—N3—N2	114.79 (19)	H19B—C19—H19C	109.5
C20—N4—C21	124.7 (2)	N3—C20—N4	116.4 (2)
C20—N4—H1	117.7	N3—C20—S1	128.57 (18)
C21—N4—H1	117.7	N4—C20—S1	114.99 (17)
C6—C1—C2	118.7 (2)	N4—C21—C22	108.65 (19)
C6—C1—Sn	120.44 (17)	N4—C21—C26	112.62 (19)
C2—C1—Sn	120.87 (17)	C22—C21—C26	110.39 (19)
C3—C2—C1	120.1 (2)	N4—C21—H21	108.4
C3—C2—H2	120.0	C22—C21—H21	108.4
C1—C2—H2	120.0	C26—C21—H21	108.4
C4—C3—C2	120.6 (2)	C23—C22—C21	111.4 (2)
C4—C3—H3	119.7	C23—C22—H22A	109.3
C2—C3—H3	119.7	C21—C22—H22A	109.3
C3—C4—C5	120.0 (2)	C23—C22—H22B	109.3
C3—C4—H4	120.0	C21—C22—H22B	109.3
C5—C4—H4	120.0	H22A—C22—H22B	108.0
C4—C5—C6	120.0 (2)	C24—C23—C22	111.7 (2)
C4—C5—H5	120.0	C24—C23—H23A	109.3
C6—C5—H5	120.0	C22—C23—H23A	109.3
C5—C6—C1	120.7 (2)	C24—C23—H23B	109.3
C5—C6—H6	119.7	C22—C23—H23B	109.3
C1—C6—H6	119.7	H23A—C23—H23B	107.9
C8—C7—C12	118.7 (2)	C23—C24—C25	110.7 (2)
C8—C7—Sn	121.86 (17)	C23—C24—H24A	109.5
C12—C7—Sn	119.42 (17)	C25—C24—H24A	109.5
C7—C8—C9	120.7 (2)	C23—C24—H24B	109.5
C7—C8—H8	119.6	C25—C24—H24B	109.5
C9—C8—H8	119.6	H24A—C24—H24B	108.1
C10—C9—C8	120.2 (2)	C26—C25—C24	110.5 (2)
C10—C9—H9	119.9	C26—C25—H25A	109.5
C8—C9—H9	119.9	C24—C25—H25A	109.5
C11—C10—C9	119.4 (2)	C26—C25—H25B	109.5
C11—C10—H10	120.3	C24—C25—H25B	109.5
C9—C10—H10	120.3	H25A—C25—H25B	108.1
C10—C11—C12	120.6 (2)	C25—C26—C21	109.84 (19)
C10—C11—H11	119.7	C25—C26—H26A	109.7
C12—C11—H11	119.7	C21—C26—H26A	109.7
C11—C12—C7	120.3 (2)	C25—C26—H26B	109.7
C11—C12—H12	119.9	C21—C26—H26B	109.7
C7—C12—H12	119.9	H26A—C26—H26B	108.2
N1—C13—C14	122.7 (2)

C1—Sn—S1—C20	−78.66 (10)	C1—Sn—C7—C12	146.1 (3)
C7—Sn—S1—C20	101.29 (9)	N2—Sn—C7—C12	43.22 (19)
N2—Sn—S1—C20	8.70 (8)	N1—Sn—C7—C12	111.91 (18)
N1—Sn—S1—C20	12.62 (11)	S1—Sn—C7—C12	−33.73 (18)
Cl1—Sn—S1—C20	−169.21 (7)	Cl1—Sn—C7—C12	−132.66 (18)
C1—Sn—N1—C13	−85.65 (17)	C12—C7—C8—C9	0.6 (4)
C7—Sn—N1—C13	85.28 (17)	Sn—C7—C8—C9	−179.28 (17)
N2—Sn—N1—C13	−177.64 (18)	C7—C8—C9—C10	0.8 (4)
S1—Sn—N1—C13	178.28 (13)	C8—C9—C10—C11	−1.2 (4)
Cl1—Sn—N1—C13	0.27 (18)	C9—C10—C11—C12	0.2 (4)
C1—Sn—N1—C17	92.66 (16)	C10—C11—C12—C7	1.2 (4)
C7—Sn—N1—C17	−96.41 (16)	C8—C7—C12—C11	−1.5 (3)
N2—Sn—N1—C17	0.67 (14)	Sn—C7—C12—C11	178.33 (17)
S1—Sn—N1—C17	−3.4 (2)	C17—N1—C13—C14	0.6 (3)
Cl1—Sn—N1—C17	178.58 (13)	Sn—N1—C13—C14	178.85 (16)
C1—Sn—N2—C18	−81.56 (17)	N1—C13—C14—C15	0.6 (3)
C7—Sn—N2—C18	82.68 (17)	C13—C14—C15—C16	−0.5 (3)
N1—Sn—N2—C18	1.53 (15)	C14—C15—C16—C17	−0.7 (3)
S1—Sn—N2—C18	179.18 (17)	C13—N1—C17—C16	−1.8 (3)
C1—Sn—N2—N3	89.24 (15)	Sn—N1—C17—C16	179.77 (15)
C7—Sn—N2—N3	−106.53 (15)	C13—N1—C17—C18	175.89 (18)
N1—Sn—N2—N3	172.32 (16)	Sn—N1—C17—C18	−2.5 (2)
S1—Sn—N2—N3	−10.03 (13)	C15—C16—C17—N1	1.9 (3)
C18—N2—N3—C20	177.56 (19)	C15—C16—C17—C18	−175.72 (19)
Sn—N2—N3—C20	6.4 (2)	N3—N2—C18—C17	−174.55 (17)
C7—Sn—C1—C6	−145.4 (3)	Sn—N2—C18—C17	−3.3 (3)
N2—Sn—C1—C6	−41.8 (2)	N3—N2—C18—C19	1.3 (3)
N1—Sn—C1—C6	−111.2 (2)	Sn—N2—C18—C19	172.46 (16)
S1—Sn—C1—C6	34.5 (2)	N1—C17—C18—N2	3.9 (3)
Cl1—Sn—C1—C6	133.5 (2)	C16—C17—C18—N2	−178.5 (2)
C7—Sn—C1—C2	33.9 (4)	N1—C17—C18—C19	−172.12 (19)
N2—Sn—C1—C2	137.4 (2)	C16—C17—C18—C19	5.6 (3)
N1—Sn—C1—C2	68.1 (2)	N2—N3—C20—N4	−175.27 (17)
S1—Sn—C1—C2	−146.28 (19)	N2—N3—C20—S1	4.9 (3)
Cl1—Sn—C1—C2	−47.2 (2)	C21—N4—C20—N3	−0.3 (3)
C6—C1—C2—C3	0.4 (4)	C21—N4—C20—S1	179.50 (16)
Sn—C1—C2—C3	−178.8 (2)	Sn—S1—C20—N3	−11.4 (2)
C1—C2—C3—C4	−0.6 (4)	Sn—S1—C20—N4	168.86 (15)
C2—C3—C4—C5	0.0 (4)	C20—N4—C21—C22	−165.9 (2)
C3—C4—C5—C6	0.9 (4)	C20—N4—C21—C26	71.5 (3)
C4—C5—C6—C1	−1.2 (4)	N4—C21—C22—C23	−179.67 (18)
C2—C1—C6—C5	0.5 (4)	C26—C21—C22—C23	−55.7 (3)
Sn—C1—C6—C5	179.74 (18)	C21—C22—C23—C24	54.1 (3)
C1—Sn—C7—C8	−34.0 (4)	C22—C23—C24—C25	−54.7 (3)
N2—Sn—C7—C8	−136.91 (19)	C23—C24—C25—C26	57.5 (3)
N1—Sn—C7—C8	−68.22 (19)	C24—C25—C26—C21	−59.4 (3)
S1—Sn—C7—C8	146.14 (19)	N4—C21—C26—C25	179.88 (19)
Cl1—Sn—C7—C8	47.21 (19)	C22—C21—C26—C25	58.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1···S1ⁱ	0.88	2.62	3.489 (2)	171
C13—H13···Cl1ⁱⁱ	0.95	2.73	3.415 (3)	129
C19—H19C···Cl1ⁱⁱⁱ	0.98	2.85	3.809 (2)	166
C15—H15···Cg1^iv	0.95	2.47	3.384 (3)	162

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₁₄H₁₉N₄S)Cl]
M_r	583.73
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.7368 (4), 9.9771 (4), 13.4045 (5)
α, β, γ (°)	90.103 (3), 97.013 (3), 100.931 (4)
V (Å³)	1268.57 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.642, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	8973, 5781, 5122
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.061, 1.00
No. of reflections	5781
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.58

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn—C1	2.152 (2)	Sn—N1	2.3869 (19)
Sn—C7	2.159 (2)	Sn—S1	2.5209 (6)
Sn—N2	2.3100 (19)	Sn—Cl1	2.5449 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1···S1ⁱ	0.88	2.62	3.489 (2)	171
C13—H13···Cl1ⁱⁱ	0.95	2.73	3.415 (3)	129
C19—H19C···Cl1ⁱⁱⁱ	0.98	2.85	3.809 (2)	166
C15—H15···Cg1^iv	0.95	2.47	3.384 (3)	162

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

Acknowledgements

We thank MOSTI (grant No. 06–01-09-SF0046) and the Universiti Malaysia Sarawak for supporting this study. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Salam, M. A., Affan, M. A., Ahmad, F. B., Tahir, M. I. M. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1503–m1504. 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
Sousa, G. F. de, Manso, L. C. C., Lang, E. S., Gatto, C. C. & Mahieu, B. (2007). J. Mol. Struct. 826, 185–191. 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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Volume 68| Part 4| April 2012| Pages m435-m436

doi:10.1107/S1600536812010902

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