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

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

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

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].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810014443/bt5250sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810014443/bt5250Isup2.hkl Contains datablock I

CCDC reference: 777886

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.021
wR factor = 0.054
Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C13

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.49
           From the CIF: _reflns_number_total               4498
           Count of symmetry unique reflns         2554
           Completeness (_total/calc)            176.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1944
           Fraction of Friedel pairs measured     0.761
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            C1  -SN1 -N2  -C7      1.90  0.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            C1  -SN1 -N2  -N3   -177.30  0.80   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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)