Bis(cyclo­hexyl­ammonium) tetra­chlorido­(oxalato)stannate(IV)

Sarr, M.; Diasse-Sarr, A.; Diallo, W.; Plasseraud, L.; Cattey, H.

doi:10.1107/S1600536813019284

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages m473-m474

doi:10.1107/S1600536813019284

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Bis(cyclohexylammonium) tetrachlorido(oxalato)stannate(IV)

Modou Sarr,^a Aminata Diasse-Sarr,^a ^* Waly Diallo,^a Laurent Plasseraud ^b and Hélène Cattey ^b ^*

^aLaboratoire de Chimie Minérale et Analytique (LACHIMIA), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bICMUB UMR 6302, Université de Bourgogne, Faculté des Sciences, 9 avenue Alain Savary, 21000 Dijon, France
^*Correspondence e-mail: diasseam@yahoo.fr, hcattey@u-bourgogne.fr

(Received 2 July 2013; accepted 12 July 2013; online 27 July 2013)

The title salt, (C₆H₁₄N)₂[Sn(C₂O₄)Cl₄], was obtained as a by-product from the reaction between 2C₆H₁₄N⁺·C₂O₄²⁻·1.5H₂O and SnCl₂·2H₂O. The cyclohexylammonium cation has a chair conformation. The complex anion consists of an oxalate anion chelating the SnCl₄ moiety, resulting in a distorted octahedral coordination sphere of the Sn^IV atom with the O atoms in equatorial cis positions. In the crystal, cations and anions are linked through N—H⋯O and N—H⋯Cl interactions into a layered arrangement parallel to (100).

Related literature

For applications of organotin(IV) compounds, see: Evans & Karpel (1985 ). For background to organotin(IV) chemistry, see: Ballmann et al. (2009 ); Meriem et al. (1989 ); Ng & Kumar Das (1997 ); Yin & Wang (2004 ); Zhang et al. (2006 ). For background to halogenidotin(IV) chemistry, see: Sarr & Diop (1990 ); Qamar-Kane & Diop (2010 ); Willey et al. (1998 ); Diallo et al. (2009 ). For related crystal structures with an oxalatotin(IV) moiety, see: Skapski et al. (1974 ); Gueye et al. (2012 ); Sow et al. (2010 , 2013 ).

Experimental

Crystal data

(C₆H₁₄N)₂[Sn(C₂O₄)Cl₄]
M_r = 548.87
Monoclinic, P 2₁ /c
a = 11.2293 (9) Å
b = 15.715 (1) Å
c = 12.8464 (10) Å
β = 93.238 (2)°
V = 2263.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 115 K
0.17 × 0.08 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.770, T_max = 0.953
9402 measured reflections
4979 independent reflections
4503 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.083
S = 1.12
4979 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.99 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O2	2.121 (2)
Sn1—O1	2.155 (2)
Sn1—Cl3	2.3547 (9)
Sn1—Cl2	2.3667 (9)
Sn1—Cl1	2.3794 (9)
Sn1—Cl4	2.4407 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.89	1.97	2.853 (3)	169
N1—H1B⋯O1ⁱ	0.89	2.18	3.038 (4)	163
N1—H1C⋯O3ⁱⁱ	0.89	2.01	2.875 (4)	162
N2—H2A⋯O4	0.89	2.25	2.887 (4)	129
N2—H2A⋯Cl4ⁱ	0.89	2.78	3.315 (3)	120
N2—H2B⋯Cl4ⁱⁱⁱ	0.89	2.38	3.262 (3)	169
N2—H2C⋯O3	0.89	2.02	2.869 (4)	158
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019284/wm2756sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019284/wm2756Isup2.hkl

checkCIF report

Comment top

Various applications of organotin(IV) compounds exist in many fields, e.g. related to agriculture, medicine, anti-fouling paints and wood preservatives (Evans & Karpel, 1985). Therefore new organotin compounds have been the research subject of many groups (Ballmann et al., 2009; Meriem et al., 1989; Ng & Kumar Das, 1997; Zhang et al., 2006). Our group has previously reported several halogenidotin(IV) derivatives (Diallo et al., 2009; Qamar-Kane & Diop, 2010). In this work, we report the results of the reaction between (C₆H₁₄N)₂(C₂O₄).1.5H₂O with SnCl₂.2H₂O leading to the formation of the title compound, (C₆H₁₄N)₂[Sn(C₂O₄)Cl₄], (I).

The asymmetric unit of (I) consists of an oxalate anion chelating a SnCl₄ moiety (Fig. 1). The C—O distances in the oxalate anion [C1—O3 = 1.227 (4) Å; C2—O4 = 1.217 (4) Å; C1—O1 = 1.286 (4) Å; C2—O2 = 1.290 (4) Å] indicate double and single bonds, respectively. The Sn—O distances [Sn1—O1 = 2.155 (2) Å; Sn1—O2 = 2.121 (2) Å] and the Sn—Cl distances [Sn1—Cl1 = 2.3794 (9) Å; Sn1—Cl2 = 2.3667 (9) Å, Sn1—Cl3 = 2.3547 (9) Å and Sn1—Cl4 = 2.4407 (8) Å] (Table 1) are in good agreement with those of previously reported Sn—O and Sn—Cl bonds of related compounds (Willey et al.,1998; Skapski et al., 1974; Sow et al., 2010, 2013). The coordination sphere around the Sn^IV atom can be described as a slightly distorted octahedron with the O atoms of the oxalate ligand occupying equatorial cis-positions. The greatest deviation from the ideal octahedral geometry is manifested in the contraction of the Cl2—Sn1—Cl4 angle to 171.25 (3) °.

The stannate(IV) anion interacts with the two distinct cyclohexylammonium cations (both with chair conformation) through N—H···O and N—H···Cl hydrogen bonds (Table 2), leading to a two-dimensional network extending parallel to (100) (Fig. 2).

Related literature top

For applications of organotin(IV) compounds, see: Evans & Karpel (1985). For background to organotin(IV) chemistry, see: Ballmann et al. (2009); Meriem et al. (1989); Ng & Kumar Das (1997); Yin & Wang (2004); Zhang et al. (2006). For background to halogenidotin(IV) chemistry, see: Sarr & Diop (1990); Qamar-Kane & Diop (2010); Willey et al. (1998); Diallo et al. (2009). For related crystal structures with an oxalatotin(IV) moiety, see: Skapski et al. (1974); Gueye et al. (2012); Sow et al. (2010, 2013).

Experimental top

Chemicals were purchased from Sigma-Aldrich, and used without further purification. The title compound was obtained by reacting (C₆H₁₄N)₂(C₂O₄).1.5H₂O (0.09 g, 0.286 mmol) with SnCl₂.2H₂O (0,20 g, 0.890 mmol) in 25 ml of ethanol (96%). After slow solvent evaporation of the solvent at room temperature, colourless crystals suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. A view of the molecular entities of compound (I) with atom labelling. Displacement ellipsoids are draw at the 30% probability level.
	Fig. 2. The crystal packing of compound (I) viewed approximately along [100]. Hydrogen atoms are omitted for clarity. Intermolecular hydrogen-bonding interactions of the types N—H···O and O—H···O are shown by dotted lines. Displacement ellipsoids are draw at the 30% probability level. Colour code: Sn dark grey, O red, N blue, Cl green, C grey.

Bis(cyclohexylammonium) tetrachlorido(oxalato)stannate(IV) top

Crystal data top

(C₆H₁₄N)₂[Sn(C₂O₄)Cl₄]	F(000) = 1104
M_r = 548.87	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 41791 reflections
a = 11.2293 (9) Å	θ = 1.0–27.5°
b = 15.715 (1) Å	µ = 1.62 mm⁻¹
c = 12.8464 (10) Å	T = 115 K
β = 93.238 (2)°	Prism, colourless
V = 2263.4 (3) Å³	0.17 × 0.08 × 0.03 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4979 independent reflections
Radiation source: fine-focus sealed tube	4503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ scans (κ = 0) + additional ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→10
T_min = 0.770, T_max = 0.953	k = −20→12
9402 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0196P)² + 5.6981P] where P = (F_o² + 2F_c²)/3
4979 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.99 e Å⁻³

Crystal data top

(C₆H₁₄N)₂[Sn(C₂O₄)Cl₄]	V = 2263.4 (3) Å³
M_r = 548.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2293 (9) Å	µ = 1.62 mm⁻¹
b = 15.715 (1) Å	T = 115 K
c = 12.8464 (10) Å	0.17 × 0.08 × 0.03 mm
β = 93.238 (2)°

Data collection top

Nonius KappaCCD diffractometer	4979 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	4503 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.953	R_int = 0.025
9402 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.12	Δρ_max = 1.03 e Å⁻³
4979 reflections	Δρ_min = −0.99 e Å⁻³
228 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.

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 > σ(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
Sn1	0.67656 (2)	0.922515 (13)	0.212827 (17)	0.02314 (7)
C1	0.5332 (3)	0.8427 (2)	0.3693 (2)	0.0240 (6)
C2	0.5332 (3)	0.77851 (19)	0.2768 (2)	0.0222 (6)
O1	0.5778 (2)	0.91628 (13)	0.35167 (16)	0.0231 (5)
O2	0.5826 (2)	0.80588 (14)	0.19492 (17)	0.0248 (5)
O3	0.4905 (2)	0.82201 (15)	0.45140 (17)	0.0326 (6)
O4	0.4875 (2)	0.70888 (14)	0.28564 (17)	0.0282 (5)
Cl1	0.74421 (8)	1.05949 (5)	0.26855 (7)	0.0349 (2)
Cl2	0.83254 (8)	0.84828 (6)	0.30516 (8)	0.0403 (2)
Cl3	0.75536 (10)	0.91018 (6)	0.04748 (8)	0.0428 (2)
Cl4	0.49591 (7)	0.98965 (5)	0.13685 (6)	0.02334 (16)
N1	0.5547 (2)	0.58436 (17)	0.1384 (2)	0.0254 (6)
H1A	0.5344	0.6179	0.1904	0.038*
H1B	0.5045	0.5406	0.1325	0.038*
H1C	0.5515	0.6138	0.0792	0.038*
C3	0.6796 (3)	0.5518 (2)	0.1610 (3)	0.0317 (7)
H3	0.6778	0.5129	0.2204	0.038*
C4	0.7205 (3)	0.5014 (2)	0.0690 (3)	0.0305 (7)
H4A	0.7208	0.5379	0.0081	0.037*
H4B	0.6654	0.4550	0.0536	0.037*
C5	0.8453 (4)	0.4659 (3)	0.0929 (3)	0.0397 (9)
H5A	0.8435	0.4252	0.1496	0.048*
H5B	0.8720	0.4365	0.0321	0.048*
C6	0.9310 (4)	0.5365 (3)	0.1229 (4)	0.0478 (11)
H6A	0.9388	0.5738	0.0636	0.057*
H6B	1.0088	0.5124	0.1415	0.057*
C7	0.8886 (4)	0.5888 (3)	0.2157 (3)	0.0439 (10)
H7A	0.8893	0.5532	0.2774	0.053*
H7B	0.9428	0.6360	0.2299	0.053*
C8	0.7630 (3)	0.6227 (3)	0.1914 (3)	0.0418 (9)
H8A	0.7352	0.6516	0.2522	0.050*
H8B	0.7641	0.6637	0.1349	0.050*
N2	0.3881 (3)	0.65674 (19)	0.4780 (2)	0.0357 (7)
H2A	0.3940	0.6415	0.4118	0.054*
H2B	0.4276	0.6197	0.5194	0.054*
H2C	0.4191	0.7084	0.4880	0.054*
C9	0.2600 (3)	0.6577 (2)	0.5030 (3)	0.0305 (7)
H9	0.2261	0.6012	0.4884	0.037*
C10	0.1935 (4)	0.7220 (3)	0.4339 (3)	0.0507 (12)
H10A	0.2013	0.7073	0.3613	0.061*
H10B	0.2274	0.7781	0.4459	0.061*
C11	0.0621 (5)	0.7226 (4)	0.4580 (4)	0.0613 (14)
H11A	0.0208	0.7657	0.4157	0.074*
H11B	0.0271	0.6679	0.4395	0.074*
C12	0.0451 (4)	0.7404 (3)	0.5710 (4)	0.0463 (10)
H12A	−0.0388	0.7354	0.5841	0.056*
H12B	0.0699	0.7983	0.5871	0.056*
C13	0.1164 (4)	0.6793 (3)	0.6413 (4)	0.0460 (10)
H13A	0.0836	0.6225	0.6326	0.055*
H13B	0.1095	0.6960	0.7134	0.055*
C14	0.2475 (3)	0.6780 (3)	0.6171 (3)	0.0357 (8)
H14A	0.2831	0.7330	0.6333	0.043*
H14B	0.2892	0.6355	0.6599	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02712 (12)	0.02014 (12)	0.02230 (12)	0.00106 (8)	0.00262 (8)	0.00254 (8)
C1	0.0337 (17)	0.0208 (15)	0.0172 (14)	0.0033 (13)	0.0001 (12)	0.0019 (11)
C2	0.0309 (17)	0.0183 (14)	0.0176 (14)	0.0010 (12)	0.0023 (12)	−0.0001 (11)
O1	0.0344 (12)	0.0175 (10)	0.0173 (10)	0.0006 (9)	0.0015 (9)	−0.0013 (8)
O2	0.0372 (13)	0.0199 (11)	0.0180 (10)	−0.0011 (9)	0.0073 (9)	−0.0024 (8)
O3	0.0566 (17)	0.0251 (12)	0.0170 (11)	−0.0004 (11)	0.0104 (11)	−0.0013 (9)
O4	0.0425 (14)	0.0202 (11)	0.0227 (11)	−0.0028 (10)	0.0078 (10)	−0.0031 (9)
Cl1	0.0358 (5)	0.0249 (4)	0.0430 (5)	−0.0060 (3)	−0.0077 (4)	0.0024 (3)
Cl2	0.0355 (5)	0.0359 (5)	0.0487 (5)	0.0104 (4)	−0.0055 (4)	0.0070 (4)
Cl3	0.0523 (6)	0.0416 (5)	0.0369 (5)	0.0105 (4)	0.0239 (4)	0.0083 (4)
Cl4	0.0294 (4)	0.0237 (4)	0.0168 (3)	0.0014 (3)	0.0000 (3)	0.0001 (3)
N1	0.0298 (15)	0.0261 (14)	0.0206 (13)	0.0021 (11)	0.0031 (11)	−0.0023 (10)
C3	0.0303 (18)	0.0380 (19)	0.0271 (17)	0.0054 (15)	0.0022 (14)	−0.0047 (14)
C4	0.0336 (18)	0.0315 (18)	0.0265 (17)	0.0019 (14)	0.0022 (14)	−0.0053 (14)
C5	0.037 (2)	0.039 (2)	0.043 (2)	0.0051 (17)	0.0044 (17)	−0.0049 (17)
C6	0.034 (2)	0.046 (2)	0.063 (3)	0.0009 (18)	0.004 (2)	−0.015 (2)
C7	0.034 (2)	0.049 (2)	0.047 (2)	−0.0044 (18)	−0.0078 (18)	−0.0111 (19)
C8	0.038 (2)	0.038 (2)	0.049 (2)	−0.0018 (17)	0.0006 (18)	−0.0200 (18)
N2	0.054 (2)	0.0232 (14)	0.0315 (15)	0.0092 (13)	0.0196 (14)	0.0088 (12)
C9	0.042 (2)	0.0235 (16)	0.0261 (16)	0.0048 (14)	0.0021 (15)	0.0010 (13)
C10	0.071 (3)	0.057 (3)	0.0249 (18)	0.030 (2)	0.0033 (19)	0.0093 (18)
C11	0.059 (3)	0.072 (3)	0.051 (3)	0.024 (3)	−0.022 (2)	0.000 (2)
C12	0.038 (2)	0.044 (2)	0.058 (3)	0.0096 (18)	0.0054 (19)	0.005 (2)
C13	0.042 (2)	0.049 (2)	0.048 (2)	0.0089 (19)	0.0129 (19)	0.012 (2)
C14	0.039 (2)	0.045 (2)	0.0228 (17)	0.0058 (17)	0.0025 (15)	0.0030 (15)

Geometric parameters (Å, º) top

Sn1—O2	2.121 (2)	C7—C8	1.524 (6)
Sn1—O1	2.155 (2)	C7—H7A	0.9700
Sn1—Cl3	2.3547 (9)	C7—H7B	0.9700
Sn1—Cl2	2.3667 (9)	C8—H8A	0.9700
Sn1—Cl1	2.3794 (9)	C8—H8B	0.9700
Sn1—Cl4	2.4407 (8)	N2—C9	1.491 (5)
C1—O3	1.227 (4)	N2—H2A	0.8900
C1—O1	1.286 (4)	N2—H2B	0.8900
C1—C2	1.559 (4)	N2—H2C	0.8900
C2—O4	1.217 (4)	C9—C10	1.514 (5)
C2—O2	1.290 (4)	C9—C14	1.514 (5)
N1—C3	1.505 (4)	C9—H9	0.9800
N1—H1A	0.8900	C10—C11	1.524 (7)
N1—H1B	0.8900	C10—H10A	0.9700
N1—H1C	0.8900	C10—H10B	0.9700
C3—C8	1.493 (5)	C11—C12	1.501 (7)
C3—C4	1.515 (5)	C11—H11A	0.9700
C3—H3	0.9800	C11—H11B	0.9700
C4—C5	1.524 (5)	C12—C13	1.515 (6)
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C6	1.504 (6)	C13—C14	1.521 (5)
C5—H5A	0.9700	C13—H13A	0.9700
C5—H5B	0.9700	C13—H13B	0.9700
C6—C7	1.544 (6)	C14—H14A	0.9700
C6—H6A	0.9700	C14—H14B	0.9700
C6—H6B	0.9700

O2—Sn1—O1	76.97 (8)	C8—C7—H7A	109.6
O2—Sn1—Cl3	92.35 (6)	C6—C7—H7A	109.6
O1—Sn1—Cl3	168.53 (7)	C8—C7—H7B	109.6
O2—Sn1—Cl2	88.73 (7)	C6—C7—H7B	109.6
O1—Sn1—Cl2	87.92 (6)	H7A—C7—H7B	108.1
Cl3—Sn1—Cl2	96.10 (4)	C3—C8—C7	110.6 (3)
O2—Sn1—Cl1	164.34 (6)	C3—C8—H8A	109.5
O1—Sn1—Cl1	87.86 (6)	C7—C8—H8A	109.5
Cl3—Sn1—Cl1	102.47 (4)	C3—C8—H8B	109.5
Cl2—Sn1—Cl1	94.62 (3)	C7—C8—H8B	109.5
O2—Sn1—Cl4	86.17 (7)	H8A—C8—H8B	108.1
O1—Sn1—Cl4	84.01 (6)	C9—N2—H2A	109.5
Cl3—Sn1—Cl4	91.21 (3)	C9—N2—H2B	109.5
Cl2—Sn1—Cl4	171.25 (3)	H2A—N2—H2B	109.5
Cl1—Sn1—Cl4	88.47 (3)	C9—N2—H2C	109.5
O3—C1—O1	124.4 (3)	H2A—N2—H2C	109.5
O3—C1—C2	120.1 (3)	H2B—N2—H2C	109.5
O1—C1—C2	115.5 (3)	N2—C9—C10	109.3 (3)
O4—C2—O2	125.4 (3)	N2—C9—C14	110.7 (3)
O4—C2—C1	119.5 (3)	C10—C9—C14	110.9 (3)
O2—C2—C1	115.1 (3)	N2—C9—H9	108.6
C1—O1—Sn1	114.25 (19)	C10—C9—H9	108.6
C2—O2—Sn1	115.71 (19)	C14—C9—H9	108.6
C3—N1—H1A	109.5	C9—C10—C11	109.7 (4)
C3—N1—H1B	109.5	C9—C10—H10A	109.7
H1A—N1—H1B	109.5	C11—C10—H10A	109.7
C3—N1—H1C	109.5	C9—C10—H10B	109.7
H1A—N1—H1C	109.5	C11—C10—H10B	109.7
H1B—N1—H1C	109.5	H10A—C10—H10B	108.2
C8—C3—N1	111.1 (3)	C12—C11—C10	112.0 (4)
C8—C3—C4	112.4 (3)	C12—C11—H11A	109.2
N1—C3—C4	110.4 (3)	C10—C11—H11A	109.2
C8—C3—H3	107.6	C12—C11—H11B	109.2
N1—C3—H3	107.6	C10—C11—H11B	109.2
C4—C3—H3	107.6	H11A—C11—H11B	107.9
C3—C4—C5	110.5 (3)	C11—C12—C13	111.5 (4)
C3—C4—H4A	109.6	C11—C12—H12A	109.3
C5—C4—H4A	109.6	C13—C12—H12A	109.3
C3—C4—H4B	109.6	C11—C12—H12B	109.3
C5—C4—H4B	109.6	C13—C12—H12B	109.3
H4A—C4—H4B	108.1	H12A—C12—H12B	108.0
C6—C5—C4	110.4 (3)	C12—C13—C14	111.8 (3)
C6—C5—H5A	109.6	C12—C13—H13A	109.3
C4—C5—H5A	109.6	C14—C13—H13A	109.3
C6—C5—H5B	109.6	C12—C13—H13B	109.3
C4—C5—H5B	109.6	C14—C13—H13B	109.3
H5A—C5—H5B	108.1	H13A—C13—H13B	107.9
C5—C6—C7	111.7 (4)	C9—C14—C13	110.2 (3)
C5—C6—H6A	109.3	C9—C14—H14A	109.6
C7—C6—H6A	109.3	C13—C14—H14A	109.6
C5—C6—H6B	109.3	C9—C14—H14B	109.6
C7—C6—H6B	109.3	C13—C14—H14B	109.6
H6A—C6—H6B	107.9	H14A—C14—H14B	108.1
C8—C7—C6	110.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.89	1.97	2.853 (3)	169
N1—H1B···O1ⁱ	0.89	2.18	3.038 (4)	163
N1—H1C···O3ⁱⁱ	0.89	2.01	2.875 (4)	162
N2—H2A···O4	0.89	2.25	2.887 (4)	129
N2—H2A···Cl4ⁱ	0.89	2.78	3.315 (3)	120
N2—H2B···Cl4ⁱⁱⁱ	0.89	2.38	3.262 (3)	169
N2—H2C···O3	0.89	2.02	2.869 (4)	158

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2.

Selected bond lengths (Å) top

Sn1—O2	2.121 (2)	Sn1—Cl2	2.3667 (9)
Sn1—O1	2.155 (2)	Sn1—Cl1	2.3794 (9)
Sn1—Cl3	2.3547 (9)	Sn1—Cl4	2.4407 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.89	1.97	2.853 (3)	169.4
N1—H1B···O1ⁱ	0.89	2.18	3.038 (4)	163.0
N1—H1C···O3ⁱⁱ	0.89	2.01	2.875 (4)	162.4
N2—H2A···O4	0.89	2.25	2.887 (4)	128.8
N2—H2A···Cl4ⁱ	0.89	2.78	3.315 (3)	120.3
N2—H2B···Cl4ⁱⁱⁱ	0.89	2.38	3.262 (3)	168.8
N2—H2C···O3	0.89	2.02	2.869 (4)	158.2

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2.

Acknowledgements

The authors gratefully acknowledge the Cheikh Anta Diop University of Dakar (Senegal), the Centre National de la Recherche Scientifique (CNRS, France) and the University of Burgundy (Dijon, France).

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