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

Salam, M.A.; Affan, M.A.; Shamsuddin, M.; Ng, S.W.

doi:10.1107/S1600536810014443

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m570

https://doi.org/10.1107/S1600536810014443

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ADDENDA AND ERRATA

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

Md. Abdus Salam,^a Md. Abu Affan,^a Mustaffa Shamsuddin ^a and Seik Weng Ng ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 April 2010; accepted 20 April 2010; online 24 April 2010)

The monodeprotonated Schiff base ligand in the title compound, [Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂], N,N′,S-chelates to the Sn atom, which is six-coordinated in an octahedral environment. The three coordinating atoms along with the methyl C atom comprise a square plane, above and below which are positioned the Cl atoms. The amino group is a hydrogen-bond donor to a Cl atom of an adjacent molecule, the hydrogen bond giving rise to a helical chain extending parallel to [100].

Related literature

For the crystal structures of other metal derivatives of the Schiff base, see: Joseph et al. (2004 ); Kovala-Demertzi et al. (2007 ).

Experimental

Crystal data

[Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂]
M_r = 480.02
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.2016 (5) Å
b = 12.2434 (7) Å
c = 17.4544 (10) Å
V = 1966.39 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.633, T_max = 0.730
18838 measured reflections
4498 independent reflections
4223 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.054
S = 1.02
4498 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 1493 Friedel pairs
Flack parameter: −0.020 (17)

Table 1
Selected bond lengths (Å)

Sn1—C1	2.136 (3)
Sn1—N1	2.269 (2)
Sn1—N2	2.224 (2)
Sn1—S1	2.4814 (7)
Sn1—Cl1	2.4960 (7)
Sn1—Cl2	2.4701 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl1ⁱ	0.86 (1)	2.36 (1)	3.219 (3)	177 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810014443/bt5250sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014443/bt5250Isup2.hkl

checkCIF report

Comment top

The mono-deprotonated anion of 2-acetylpyridine 4-cyclohexyl thiosemicarbazone is a ligand that N,N',S-binds to metal atoms (Joseph et al., 2004). Whereas similar ligands have been complexed with diorganotin and triorganotin systems, the monoorganotin analogues have not been so extensively studied. The mono-deprotonated Schiff-base ligand in SnCl₂(CH₃)(C₁₄H₁₉N₄S) N,N',S-chelates to the tin atom, which is six-coordinate in an octahedral environment (Scheme I, Fig. 1). The three coordinating atoms along with the methyl carbon comprise a square plane, above and below which are positioned the chlorine atoms.

Related literature top

For the crystal structures of other metal derivatives of the Schiff base, see: Joseph et al. (2004); Kovala-Demertzi et al. (2007).

Experimental top

2-Acetylpyridine 4-cyclohexyl thiosemicarbazone was synthesized by using a literature method (Joseph et al., 2004). The compound (0.28 g, 1 mmol) was dissolved in dry methanol (10 ml) in a Schlenk apparatus under a nitrogen atmosphere. Methyltin trichoride (0.24 g, 1 mmol) dissolved in methanol (10 ml) was added. The mixture was heated for an hour. The solvent was removed and the yellow compound recrystallized from chloroform/methanol (1:1) in 70% yield, m.p. 551-553 K.

Structure description top

For the crystal structures of other metal derivatives of the Schiff base, see: Joseph et al. (2004); Kovala-Demertzi et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl₂(CH₃)(C₁₄H₁₉N₄S) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

[Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂]	F(000) = 960
M_r = 480.02	D_x = 1.621 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8827 reflections
a = 9.2016 (5) Å	θ = 2.3–27.7°
b = 12.2434 (7) Å	µ = 1.68 mm⁻¹
c = 17.4544 (10) Å	T = 293 K
V = 1966.39 (19) Å³	Prism, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	4498 independent reflections
Radiation source: fine-focus sealed tube	4223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.633, T_max = 0.730	k = −15→15
18838 measured reflections	l = −22→22

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)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.032P)² + 0.1524P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4498 reflections	Δρ_max = 0.29 e Å⁻³
214 parameters	Δρ_min = −0.41 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1493 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.020 (17)

Crystal data top

[Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂]	V = 1966.39 (19) Å³
M_r = 480.02	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.2016 (5) Å	µ = 1.68 mm⁻¹
b = 12.2434 (7) Å	T = 293 K
c = 17.4544 (10) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	4498 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4223 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.730	R_int = 0.025
18838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.054	Δρ_max = 0.29 e Å⁻³
S = 1.02	Δρ_min = −0.41 e Å⁻³
4498 reflections	Absolute structure: Flack (1983), 1493 Friedel pairs
214 parameters	Absolute structure parameter: −0.020 (17)
1 restraint

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

	x	y	z	U_iso*/U_eq
Sn1	1.061930 (18)	0.634199 (13)	0.160119 (10)	0.03748 (6)
Cl1	0.97585 (8)	0.54078 (6)	0.04139 (4)	0.04922 (17)
Cl2	1.10680 (12)	0.73379 (8)	0.28090 (5)	0.0724 (3)
S1	1.22890 (7)	0.75142 (6)	0.08461 (5)	0.04529 (16)
N1	0.8388 (3)	0.59846 (18)	0.20943 (13)	0.0411 (5)
N2	0.9157 (2)	0.77150 (16)	0.12825 (11)	0.0351 (5)
N3	0.9636 (2)	0.85860 (18)	0.08811 (12)	0.0398 (5)
N4	1.1533 (3)	0.9409 (2)	0.02881 (19)	0.0602 (7)
H4	1.2404 (17)	0.944 (3)	0.0111 (18)	0.063 (11)*
C1	1.1749 (4)	0.4916 (3)	0.1978 (2)	0.0687 (10)
H1A	1.1755	0.4893	0.2527	0.103*
H1B	1.2731	0.4936	0.1792	0.103*
H1C	1.1270	0.4277	0.1783	0.103*
C2	0.8073 (4)	0.5114 (2)	0.25205 (17)	0.0524 (7)
H2	0.8783	0.4586	0.2602	0.063*
C3	0.6713 (4)	0.4978 (3)	0.28448 (19)	0.0599 (9)
H3	0.6513	0.4370	0.3146	0.072*
C4	0.5676 (4)	0.5746 (3)	0.27171 (17)	0.0589 (8)
H4A	0.4761	0.5675	0.2938	0.071*
C5	0.5985 (3)	0.6628 (2)	0.22600 (16)	0.0490 (7)
H5	0.5271	0.7146	0.2157	0.059*
C6	0.7362 (3)	0.6743 (2)	0.19527 (14)	0.0372 (6)
C7	0.7802 (3)	0.7679 (2)	0.14765 (14)	0.0363 (5)
C8	0.6739 (3)	0.8530 (3)	0.12494 (18)	0.0517 (7)
H8A	0.7240	0.9121	0.1002	0.077*
H8B	0.6249	0.8799	0.1697	0.077*
H8C	0.6042	0.8222	0.0902	0.077*
C9	1.1021 (3)	0.8555 (2)	0.06741 (14)	0.0400 (6)
C10	1.0719 (4)	1.0403 (2)	0.0096 (2)	0.0595 (8)
H10	0.9725	1.0328	0.0290	0.071*
C11	1.1403 (6)	1.1369 (3)	0.0467 (2)	0.0941 (16)
H11A	1.2421	1.1404	0.0324	0.113*
H11B	1.1351	1.1288	0.1019	0.113*
C12	1.0651 (7)	1.2431 (3)	0.0232 (2)	0.0936 (15)
H12A	0.9671	1.2436	0.0437	0.112*
H12B	1.1171	1.3044	0.0452	0.112*
C13	1.0586 (6)	1.2563 (3)	−0.0593 (2)	0.0750 (11)
H13A	1.1561	1.2688	−0.0786	0.090*
H13B	1.0007	1.3203	−0.0712	0.090*
C14	0.9968 (8)	1.1623 (3)	−0.0982 (3)	0.123 (2)
H14A	1.0086	1.1717	−0.1531	0.147*
H14B	0.8935	1.1592	−0.0875	0.147*
C15	1.0660 (8)	1.0544 (3)	−0.0745 (2)	0.115 (2)
H15A	1.0109	0.9947	−0.0967	0.138*
H15B	1.1639	1.0509	−0.0950	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03555 (9)	0.03065 (8)	0.04623 (9)	0.00216 (7)	−0.00566 (7)	0.00345 (7)
Cl1	0.0458 (4)	0.0469 (4)	0.0550 (4)	0.0002 (3)	−0.0045 (3)	−0.0088 (3)
Cl2	0.0986 (7)	0.0686 (5)	0.0500 (4)	−0.0184 (5)	−0.0149 (4)	−0.0065 (4)
S1	0.0341 (3)	0.0362 (3)	0.0656 (4)	0.0016 (3)	0.0043 (3)	0.0044 (3)
N1	0.0436 (13)	0.0366 (11)	0.0431 (11)	−0.0039 (10)	−0.0010 (9)	0.0059 (9)
N2	0.0395 (12)	0.0274 (10)	0.0383 (10)	0.0034 (9)	0.0030 (9)	0.0019 (8)
N3	0.0371 (11)	0.0332 (10)	0.0491 (11)	0.0028 (10)	0.0050 (9)	0.0071 (10)
N4	0.0442 (15)	0.0431 (14)	0.093 (2)	0.0067 (11)	0.0179 (14)	0.0239 (14)
C1	0.060 (2)	0.0515 (19)	0.095 (3)	0.0150 (17)	−0.021 (2)	0.0203 (18)
C2	0.061 (2)	0.0445 (16)	0.0518 (16)	−0.0074 (15)	−0.0060 (15)	0.0125 (13)
C3	0.067 (2)	0.058 (2)	0.0554 (17)	−0.0250 (18)	−0.0023 (16)	0.0152 (15)
C4	0.0554 (18)	0.067 (2)	0.0543 (16)	−0.0200 (19)	0.0087 (16)	0.0020 (14)
C5	0.0451 (17)	0.0505 (17)	0.0513 (15)	−0.0044 (12)	0.0106 (13)	−0.0029 (12)
C6	0.0389 (14)	0.0353 (13)	0.0375 (12)	−0.0017 (11)	0.0023 (11)	−0.0067 (10)
C7	0.0371 (13)	0.0348 (12)	0.0371 (13)	0.0036 (10)	0.0032 (10)	−0.0028 (10)
C8	0.0415 (15)	0.0502 (17)	0.0632 (16)	0.0141 (14)	0.0045 (13)	0.0060 (14)
C9	0.0426 (14)	0.0317 (13)	0.0458 (13)	−0.0002 (12)	0.0011 (10)	0.0017 (11)
C10	0.0435 (15)	0.0419 (15)	0.093 (2)	0.0065 (15)	0.0162 (18)	0.0256 (15)
C11	0.159 (5)	0.059 (2)	0.064 (2)	0.046 (3)	−0.036 (3)	−0.0167 (19)
C12	0.154 (4)	0.052 (2)	0.075 (2)	0.032 (3)	−0.021 (3)	−0.0103 (19)
C13	0.092 (3)	0.0485 (18)	0.085 (2)	0.013 (2)	0.013 (2)	0.0252 (17)
C14	0.214 (7)	0.071 (3)	0.083 (3)	0.057 (3)	−0.064 (4)	−0.008 (2)
C15	0.197 (6)	0.058 (2)	0.090 (3)	0.049 (3)	−0.067 (4)	−0.022 (2)

Geometric parameters (Å, º) top

Sn1—C1	2.136 (3)	C5—C6	1.383 (4)
Sn1—N1	2.269 (2)	C5—H5	0.9300
Sn1—N2	2.224 (2)	C6—C7	1.473 (4)
Sn1—S1	2.4814 (7)	C7—C8	1.483 (4)
Sn1—Cl1	2.4960 (7)	C8—H8A	0.9600
Sn1—Cl2	2.4701 (8)	C8—H8B	0.9600
S1—C9	1.753 (3)	C8—H8C	0.9600
N1—C2	1.332 (4)	C10—C15	1.479 (5)
N1—C6	1.348 (3)	C10—C11	1.488 (6)
N2—C7	1.292 (3)	C10—H10	0.9800
N2—N3	1.350 (3)	C11—C12	1.529 (5)
N3—C9	1.326 (3)	C11—H11A	0.9700
N4—C9	1.330 (4)	C11—H11B	0.9700
N4—C10	1.468 (4)	C12—C13	1.450 (5)
N4—H4	0.861 (10)	C12—H12A	0.9700
C1—H1A	0.9600	C12—H12B	0.9700
C1—H1B	0.9600	C13—C14	1.453 (6)
C1—H1C	0.9600	C13—H13A	0.9700
C2—C3	1.383 (5)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.523 (5)
C3—C4	1.359 (5)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.372 (4)	C15—H15A	0.9700
C4—H4A	0.9300	C15—H15B	0.9700

C1—Sn1—N2	171.66 (12)	N2—C7—C8	122.8 (2)
C1—Sn1—N1	99.56 (12)	C6—C7—C8	121.1 (2)
N2—Sn1—N1	72.12 (8)	C7—C8—H8A	109.5
C1—Sn1—Cl2	93.43 (11)	C7—C8—H8B	109.5
N2—Sn1—Cl2	86.65 (6)	H8A—C8—H8B	109.5
N1—Sn1—Cl2	85.57 (6)	C7—C8—H8C	109.5
C1—Sn1—S1	109.56 (11)	H8A—C8—H8C	109.5
N2—Sn1—S1	78.74 (6)	H8B—C8—H8C	109.5
N1—Sn1—S1	150.85 (6)	N3—C9—N4	117.1 (3)
Cl2—Sn1—S1	93.69 (3)	N3—C9—S1	127.9 (2)
C1—Sn1—Cl1	92.01 (11)	N4—C9—S1	115.0 (2)
N2—Sn1—Cl1	86.94 (6)	N4—C10—C15	110.0 (3)
N1—Sn1—Cl1	86.53 (6)	N4—C10—C11	110.1 (3)
Cl2—Sn1—Cl1	171.05 (3)	C15—C10—C11	110.8 (3)
S1—Sn1—Cl1	91.18 (3)	N4—C10—H10	108.6
C9—S1—Sn1	95.70 (9)	C15—C10—H10	108.6
C2—N1—C6	120.1 (3)	C11—C10—H10	108.6
C2—N1—Sn1	124.3 (2)	C10—C11—C12	111.5 (3)
C6—N1—Sn1	115.58 (17)	C10—C11—H11A	109.3
C7—N2—N3	118.5 (2)	C12—C11—H11A	109.3
C7—N2—Sn1	119.51 (17)	C10—C11—H11B	109.3
N3—N2—Sn1	121.94 (16)	C12—C11—H11B	109.3
C9—N3—N2	115.7 (2)	H11A—C11—H11B	108.0
C9—N4—C10	126.0 (3)	C13—C12—C11	112.3 (3)
C9—N4—H4	123 (2)	C13—C12—H12A	109.1
C10—N4—H4	111 (2)	C11—C12—H12A	109.1
Sn1—C1—H1A	109.5	C13—C12—H12B	109.1
Sn1—C1—H1B	109.5	C11—C12—H12B	109.1
H1A—C1—H1B	109.5	H12A—C12—H12B	107.9
Sn1—C1—H1C	109.5	C12—C13—C14	113.1 (4)
H1A—C1—H1C	109.5	C12—C13—H13A	109.0
H1B—C1—H1C	109.5	C14—C13—H13A	109.0
N1—C2—C3	121.5 (3)	C12—C13—H13B	109.0
N1—C2—H2	119.3	C14—C13—H13B	109.0
C3—C2—H2	119.3	H13A—C13—H13B	107.8
C4—C3—C2	119.0 (3)	C13—C14—C15	113.3 (4)
C4—C3—H3	120.5	C13—C14—H14A	108.9
C2—C3—H3	120.5	C15—C14—H14A	108.9
C3—C4—C5	119.6 (3)	C13—C14—H14B	108.9
C3—C4—H4A	120.2	C15—C14—H14B	108.9
C5—C4—H4A	120.2	H14A—C14—H14B	107.7
C4—C5—C6	119.7 (3)	C10—C15—C14	112.7 (4)
C4—C5—H5	120.1	C10—C15—H15A	109.0
C6—C5—H5	120.1	C14—C15—H15A	109.0
N1—C6—C5	120.1 (2)	C10—C15—H15B	109.0
N1—C6—C7	116.6 (2)	C14—C15—H15B	109.0
C5—C6—C7	123.4 (2)	H15A—C15—H15B	107.8
N2—C7—C6	116.1 (2)

C1—Sn1—S1—C9	−178.73 (15)	C3—C4—C5—C6	−1.9 (5)
N2—Sn1—S1—C9	2.07 (10)	C2—N1—C6—C5	1.0 (4)
N1—Sn1—S1—C9	3.74 (16)	Sn1—N1—C6—C5	−176.8 (2)
Cl2—Sn1—S1—C9	−83.77 (9)	C2—N1—C6—C7	180.0 (2)
Cl1—Sn1—S1—C9	88.72 (9)	Sn1—N1—C6—C7	2.1 (3)
C1—Sn1—N1—C2	2.9 (3)	C4—C5—C6—N1	0.8 (4)
N2—Sn1—N1—C2	−177.8 (2)	C4—C5—C6—C7	−178.0 (3)
Cl2—Sn1—N1—C2	−89.9 (2)	N3—N2—C7—C6	−176.5 (2)
S1—Sn1—N1—C2	−179.50 (18)	Sn1—N2—C7—C6	4.4 (3)
Cl1—Sn1—N1—C2	94.3 (2)	N3—N2—C7—C8	2.6 (4)
C1—Sn1—N1—C6	−179.4 (2)	Sn1—N2—C7—C8	−176.5 (2)
N2—Sn1—N1—C6	−0.01 (17)	N1—C6—C7—N2	−4.3 (3)
Cl2—Sn1—N1—C6	87.89 (18)	C5—C6—C7—N2	174.6 (2)
S1—Sn1—N1—C6	−1.7 (3)	N1—C6—C7—C8	176.6 (2)
Cl1—Sn1—N1—C6	−87.92 (18)	C5—C6—C7—C8	−4.5 (4)
C1—Sn1—N2—C7	1.9 (9)	N2—N3—C9—N4	−179.0 (3)
N1—Sn1—N2—C7	−2.46 (18)	N2—N3—C9—S1	1.1 (3)
Cl2—Sn1—N2—C7	−88.88 (19)	C10—N4—C9—N3	2.6 (5)
S1—Sn1—N2—C7	176.68 (19)	C10—N4—C9—S1	−177.5 (3)
Cl1—Sn1—N2—C7	84.87 (19)	Sn1—S1—C9—N3	−2.6 (3)
C1—Sn1—N2—N3	−177.3 (8)	Sn1—S1—C9—N4	177.5 (2)
N1—Sn1—N2—N3	178.4 (2)	C9—N4—C10—C15	−120.0 (5)
Cl2—Sn1—N2—N3	91.99 (17)	C9—N4—C10—C11	117.6 (4)
S1—Sn1—N2—N3	−2.45 (17)	N4—C10—C11—C12	175.8 (4)
Cl1—Sn1—N2—N3	−94.26 (17)	C15—C10—C11—C12	53.9 (6)
C7—N2—N3—C9	−177.5 (2)	C10—C11—C12—C13	−54.4 (7)
Sn1—N2—N3—C9	1.6 (3)	C11—C12—C13—C14	52.4 (7)
C6—N1—C2—C3	−1.8 (4)	C12—C13—C14—C15	−50.4 (8)
Sn1—N1—C2—C3	175.8 (2)	N4—C10—C15—C14	−174.0 (5)
N1—C2—C3—C4	0.7 (5)	C11—C10—C15—C14	−52.0 (7)
C2—C3—C4—C5	1.2 (5)	C13—C14—C15—C10	50.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl1ⁱ	0.86 (1)	2.36 (1)	3.219 (3)	177 (3)

Symmetry code: (i) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)(C₁₄H₁₉N₄S)Cl₂]
M_r	480.02
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.2016 (5), 12.2434 (7), 17.4544 (10)
V (Å³)	1966.39 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.68
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.633, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	18838, 4498, 4223
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.054, 1.02
No. of reflections	4498
No. of parameters	214
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)	0.29, −0.41
Absolute structure	Flack (1983), 1493 Friedel pairs
Absolute structure parameter	−0.020 (17)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—C1	2.136 (3)	Sn1—S1	2.4814 (7)
Sn1—N1	2.269 (2)	Sn1—Cl1	2.4960 (7)
Sn1—N2	2.224 (2)	Sn1—Cl2	2.4701 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl1ⁱ	0.86 (1)	2.36 (1)	3.219 (3)	177 (3)

Symmetry code: (i) x+1/2, −y+3/2, −z.

Acknowledgements

We thank MOSTI (grant No. 06-01-09-SF0046), Universiti Malaysia Sarawak and the University of Malaya for supporting this study.

References

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