# Bis(L-leucinium) hexachloridostannate(IV) dihydrate

Rochdi Ghallab, Amina Kemmouche, Mehdi Boutebdja, Stéphane Golhen

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Rochdi Ghallab, Amina Kemmouche, Mehdi Boutebdja, Stéphane Golhen. Bis(L-leucinium) hexachloridostannate(IV) dihydrate. IUCrData, 2025, 10 (8), pp.x250676. 10.1107/s2414314625006765. hal-05230419

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# Bis(L-leucinium) hexachloridostannate(IV) dihydrate

Rochdi Ghallab,<sup>a*</sup> Amina Kemmouche,<sup>b</sup> Mehdi Boutebdja<sup>a</sup> and Stéphane Golhen<sup>c</sup>

Received 20 July 2025

Accepted 29 July 2025

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom

**Keywords:** crystal structure; X-ray diffraction; L-leucine; hexachlorostannate(IV).

CCDC reference: 2478499

**Structural data:** full structural data are available from iucrdata.iucr.org

The title compound, $(C_6H_{14}NO_2)_2[SnCl_6]·2H_2O$, features L-leucinium cations adopting extended conformations, which maximizes the separation between the methyl groups [–CH(CH$_3$)$_2$] and the polar $NH_3^+$ and COOH moieties. Additionally, an intramolecular hydrogen bond between the ammonium ($NH_3^+$) group and the carboxyl group induces a slight reduction in the C–C–N bond angles, with an average value of 106.5°, compared to the ideal tetrahedral angle of 109.5°. The $NH_3^+$ group is nearly coplanar with the C–C–C–C carbon chain in both fragments, whereas the carboxyl (COOH) group and the methyl group at the C5 position deviate significantly from this plane. The octahedral complex anion is close to regular. In the crystal, an extensive network of hydrogen bonds links the components into a three-dimensional network.

3D view

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Chemical scheme

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## Structure description

The title compound, $2(C_6H_{14}NO_2)^+·[SnCl_6]^{2-}·2H_2O$, crystallizes in the monoclinic space group $P2_1$. The asymmetric unit consists of two protonated L-leucinium cations, one hexachlorostannate(IV) anion, and two water molecules of crystallization (Fig. 1). Equivalent atoms in the cations are labelled C1A and C1B, etc.

During synthesis, the oxidation state of tin atom changed from +II to +IV, resulting in a tin(IV) atom hexacoordinated by chloride ions and forming a slightly distorted octahedral geometry. The Sn–Cl bond lengths range from 2.4045 (11) to 2.4387 (11) Å, while the Cl–Sn–Cl angles deviate by approximately $\pm 1°$ [88.62 (4)–91.38 (4)°] from the ideal 90° of a regular octahedron, indicating only minimal angular distortion. The absence of more significant distortions can likely be attributed to the fact that the hexachlorostannate(IV) anions are discrete; nevertheless, they accept numerous N–H···Cl and O–H···Cl hydrogen bonds from the organic cations and water molecules, as seen in related structures (Ghallab *et al.*, 2020; Gheribi *et al.*, 2022).

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<footnote><sup>a</sup>Laboratoire de Technologie des Matériaux Avancés, Ecole Nationale Polytechnique de Constantine, Algeria, <sup>b</sup>Ecole Nationale Supérieure de Biotechnologie de Constantine, Algeria, and <sup>c</sup>Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), 35042, Rennes, France. *Correspondence e-mail: rochdi.ghallab@gmail.com</footnote>
<figure><img src="image_8.png" /><figcaption>**Figure 1**</figcaption></figure>

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

The L-leucinium cations in the title compound adopt extended conformations, maximizing the separation between the methyl groups [-CH(CH₃)₂] and the polar NH₃⁺ and COOH groups. This arrangement results in C1–C2 bond lengths that are slightly longer than the median value typically observed for a single C–C bond, with measured values of 1.521 (6) and 1.517 (7) Å for the two cations. The C2–C3–C4 angles, at 115.2 (3) and 115.8 (3)°, are larger than the other C–C–C angles in the carbon backbone (mean: 109.5°), a difference attributed to steric hindrance between the methyl groups and the polar functions. Additionally, an intra-molecular hydrogen bond between the NH₃⁺ group and the carboxyl group slightly reduce the C1–C2–N1 angles, which average 106.5°, compared to the theoretical tetrahedral value of 109.5°.

The N atoms of the NH₃⁺ groups are nearly coplanar with the C2–C3–C4–C6 chains, as indicated by the torsion angles N1–C2–C3–C4 [−68.6 (4) and −62.0 (4)° for the A and B cations, respectively] and C2–C3–C4–C6 [168.7 (3) and 170.9 (4)°]. In contrast, the COOH group and the methyl group at C5 deviate significantly from this plane, with torsion angles of 170.1 (3) and 178.2 (3)° for C1–C2–C3–C4 and −68.7 (4) and −66.6 (4)° for C5–C4–C3–C2. This extended conformation is consistent with that observed for free L-leucine and its salts with inorganic acids (Zeghouan et al., 2012; Fleck et al., 2013; Janczak et al., 2007), with the notable exception of L-leucinium oxalate (Rajagopal et al., 2003) and L-leucinium picrate (Anitha et al., 2005), where the carboxyl group is nearly coplanar with the C2–C3–C4–C6 backbone.

The three-dimensional architecture of the extended structure of the title compound is consolidated by an extensive hydrogen-bonding network (Table 1). A central feature of this network is the R₂(10) graph-set motif formed by the N1B–H1BA···O2A and N1A–H1AC···O2B hydrogen bonds (Fig. 2). This motif organizes the cations into dimers,

<caption>**Table 1**</caption>

Hydrogen-bond geometry (Å, °).

<table><thead><tr><th>D–H···A</th><th>D–H</th><th>H···A</th><th>D···A</th><th>D–H···A</th></tr></thead><tbody><tr><td>N1A–H1AA···Cl3<sup>i</sup></td><td>0.91</td><td>2.78</td><td>3.470 (4)</td><td>133</td></tr><tr><td>N1A–H1AA···Cl5<sup>i</sup></td><td>0.91</td><td>2.58</td><td>3.342 (4)</td><td>142</td></tr><tr><td>N1A–H1AB···Cl4<sup>ii</sup></td><td>0.91</td><td>2.77</td><td>3.471 (4)</td><td>134</td></tr><tr><td>N1A–H1AB···Cl6<sup>ii</sup></td><td>0.91</td><td>2.65</td><td>3.452 (4)</td><td>148</td></tr><tr><td>N1A–H1AC···O2A</td><td>0.91</td><td>2.17</td><td>2.620 (5)</td><td>110</td></tr><tr><td>N1A–H1AC···O2B</td><td>0.91</td><td>2.26</td><td>2.959 (5)</td><td>133</td></tr><tr><td>N1B–H1BA···O2A</td><td>0.91</td><td>1.99</td><td>2.873 (5)</td><td>164</td></tr><tr><td>N1B–H1BA···O2B</td><td>0.91</td><td>2.27</td><td>2.626 (5)</td><td>103</td></tr><tr><td>N1B–H1BB···Cl2</td><td>0.91</td><td>2.47</td><td>3.352 (4)</td><td>164</td></tr><tr><td>N1B–H1BC···Cl1<sup>iii</sup></td><td>0.91</td><td>2.71</td><td>3.583 (4)</td><td>162</td></tr><tr><td>O1A–H1A···O1W</td><td>0.84</td><td>1.79</td><td>2.624 (5)</td><td>169</td></tr><tr><td>O1B–H1B···O2W</td><td>0.84</td><td>1.79</td><td>2.627 (6)</td><td>173</td></tr><tr><td>O1W–H1WA···Cl6<sup>iii</sup></td><td>0.87</td><td>2.69</td><td>3.440 (3)</td><td>145</td></tr><tr><td>O1W–H1WB···Cl1</td><td>0.87</td><td>2.44</td><td>3.283 (4)</td><td>162</td></tr><tr><td>O2W–H2WA···Cl3<sup>ii</sup></td><td>0.87</td><td>2.48</td><td>3.312 (4)</td><td>161</td></tr><tr><td>O2W–H2WB···Cl5<sup>i</sup></td><td>0.87</td><td>2.63</td><td>3.393 (3)</td><td>147</td></tr></tbody></table>

Symmetry codes: (i) $-x + 1, y - \frac{1}{2}, -z$; (ii) $x, y - 1, z$; (iii) $-x + 1, y - \frac{1}{2}, -z + 1$.

which propagate along the crystallographic *a*-axis to form hydrogen-bonded layers lying parallel to the *ac* plane.

The water molecules (O1W, O2W) act as critical structural mediators. Their participation in four key hydrogen bonds, viz., O1W–H1WA···Cl6, O1W–H1WB···Cl1, O2W–H2WA···Cl3 and O2W–H2WB···Cl5, anchors the anionic layer. Furthermore, the water molecules bridge the cationic and anionic layers via acceptor–donor interactions (O1A–H1A···O1W and O1B–H1B···O2W), effectively interconnecting the two substructures (Fig. 3). Additional consolidation arises from N–H···Cl hydrogen bonds, which reinforce the cohesion between adjacent layers. These interactions, combined with the water-mediated network, create a robust three-dimensional framework.

The synergy between dimer-forming R₂(10) motifs, water-mediated interlayer connectivity, and N–H···Cl interactions highlights the hierarchical role of hydrogen bonding in

<figure><img src="image_9.png" /><figcaption>**Figure 2**</figcaption></figure>

Projection onto the *ac* plane showing R₂(10) graph-set motifs that organize the molecules into dimers.
<figure><img src="image_10.png" /><figcaption>**Figure 3**</figcaption></figure>

Projection onto the *bc* plane showing the interconnection of the cationic and anionic sublayers mediated by water molecules.

directing the crystal packing. This architecture underscores the importance of solvent molecules in templating anion-cation organization in hybrid inorganic-organic systems.

## Synthesis and crystallization

A mixture of 1-leucine (0.262 g) and tin(II) chloride dihydrate (SnCl₂·2H₂O, 0.255 g) was dissolved in 20 ml of distilled water acidified with 3 drops of concentrated hydrochloric acid (HCl, 37%). The solution was stirred and heated at 60°C for 1 h. It was then left to slowly evaporate at room temperature. After 7 days, colourless single crystals suitable for X-ray diffraction analysis were obtained.

## Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

## Acknowledgements

Thanks are due to Thierry Roisnel du CDIFX, Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), 35042 Rennes, France. The authors thank the Cambridge Crystallographic Data Center (CCDC) for access to the Cambridge Structural Database (CSD) through the FAIRE program.

## Funding information

Funding for this research was provided by: Laboratoire de Technologie des Matériaux Avancés, Ecole Nationale Poly-technique de Constantine, Algérie; Unité de Recherche de Chimie de l'Environnement, Moléculaire et Structurale UR.CHEMS; DRSDT-Algeria.

<table><caption>**Table 2**</caption><caption>Experimental details.</caption><tbody><tr><td>Crystal data</td><td></td></tr><tr><td>Chemical formula</td><td>(C<sub>6</sub>H<sub>14</sub>NO<sub>2</sub>)<sub>2</sub>[SnCl<sub>6</sub>].2H<sub>2</sub>O</td></tr><tr><td>M<sub>r</sub></td><td>631.78</td></tr><tr><td>Crystal system, space group</td><td>Monoclinic, P2<sub>1</sub></td></tr><tr><td>Temperature (K)</td><td>150</td></tr><tr><td>a, b, c (Å)</td><td>10.9838 (11), 10.7837 (11),<br/>10.8556 (11)</td></tr><tr><td>β (°)</td><td>102.316 (4)</td></tr><tr><td>V (Å<sup>3</sup>)</td><td>1256.2 (2)</td></tr><tr><td>Z</td><td>2</td></tr><tr><td>Radiation type</td><td>Mo Kα</td></tr><tr><td>μ (mm<sup>-1</sup>)</td><td>1.68</td></tr><tr><td>Crystal size (mm)</td><td>0.17 × 0.13 × 0.11</td></tr><tr><td>Data collection</td><td></td></tr><tr><td>Diffractometer</td><td>D8 VENTURE Bruker AXS</td></tr><tr><td>Absorption correction</td><td>Multi-scan (SADABS; Krause et al., 2015)</td></tr><tr><td>T<sub>min</sub>, T<sub>max</sub></td><td>0.769, 0.831</td></tr><tr><td>No. of measured, independent and<br/>observed [I > 2σ(I)] reflections</td><td>13707, 5560, 5406</td></tr><tr><td>R<sub>int</sub></td><td>0.024</td></tr><tr><td>(sin θ/λ)<sub>max</sub> (Å<sup>-1</sup>)</td><td>0.649</td></tr><tr><td>Refinement</td><td></td></tr><tr><td>R[F<sup>2</sup> > 2σ(F<sup>2</sup>)], wR(F<sup>2</sup>), S</td><td>0.021, 0.052, 1.08</td></tr><tr><td>No. of reflections</td><td>5560</td></tr><tr><td>No. of parameters</td><td>255</td></tr><tr><td>No. of restraints</td><td>1</td></tr><tr><td>H-atom treatment</td><td>H-atom parameters constrained</td></tr><tr><td>Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>-3</sup>)</td><td>1.14, -0.96</td></tr><tr><td>Absolute structure</td><td>Flack x determined using 2423<br/>quotients [(I<sup>+</sup>)-(I<sup>-</sup>)]/[(I<sup>+</sup>)+(I<sup>-</sup>)]<br/>(Parsons et al., 2013)</td></tr><tr><td>Absolute structure parameter</td><td>-0.004 (10)</td></tr></tbody></table>

Computer programs: *APEX2* and *SAINT* (Bruker, 2014), *SHELXT20182* (Sheldrick, 2015a), *SHELXL20193* (Sheldrick, 2015b) and *OLEX2* (Dolomanov et al., 2009).

## References

Anitha, K., Athimoolam, S. & Rajaram, R. K. (2005). *Acta Cryst.* **E61**, o1604–o1606.

Bruker (2014). *APEX2* and *SAINT*. Bruker AXS Inc., Madison, Wisconsin, USA.

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). *J. Appl. Cryst.* **42**, 339–341.

Fleck, M., Ghazaryan, V. V. & Petrosyan, A. M. (2013). *Z. Kristallogr. Cryst. Mater.* **228**, 240–249.

Ghallab, R., Boutébdja, M., Dénès, G. & Merazig, H. (2020). *Acta Cryst.* **E76**, 1279–1283.

Gheribi, R., Hadji, D., Ghallab, R., Medjani, M., Benslimane, M., Trifa, C., Dénès, G. & Merazig, H. (2022). *J. Mol. Struct.* **1248**, 131–1392.

Janczak, J. & Perpétuo, G. J. (2007). *Acta Cryst.* **C63**, o117–o119.

Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). *J. Appl. Cryst.* **48**, 3–10.

Parsons, S., Flack, H. D. & Wagner, T. (2013). *Acta Cryst.* **B69**, 249–259.

Rajagopal, K., Krishnakumar, R. V., Subha Nandhini, M., Malathi, R., Rajan, S. S. & Natarajan, S. (2003). *Acta Cryst.* **E59**, o878–o880.

Sheldrick, G. M. (2015a). *Acta Cryst.* **A71**, 3–8.

Sheldrick, G. M. (2015b). *Acta Cryst.* **C71**, 3–8.

Zeghouan, O., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2012). *Acta Cryst.* **E68**, o2959–o2960.
full crystallographic data

IUCrData (2025). **10**, x250676 [https://doi.org/10.1107/S2414314625006765]

Bis(L-leucinium) hexachloridostannate(IV) dihydrate

Rochdi Ghallab, Amina Kemmouche, Mehdi Boutebdja and Stéphane Golhen

Bis(L-leucinium) hexachloridostannate(IV) dihydrate

Crystal data

(C₆H₁₄NO₂)₂[SnCl₆]·2H₂O

M_r = 631.78

Monoclinic, P2₁

Hall symbol: P2yb

a = 10.9838 (11) Å

b = 10.7837 (11) Å

c = 10.8556 (11) Å

β = 102.316 (4)°

V = 1256.2 (2) Å³

Z = 2

F(000) = 636

Dₓ = 1.670 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 5406 reflections

θ = 2.4–27.5°

μ = 1.68 mm⁻¹

T = 150 K

Block, white

0.17 × 0.13 × 0.11 mm

Data collection

D8 VENTURE Bruker AXS
diffractometer

Radiation source: Enraf Nonius FR590

CCD rotation images, thick slices scans

Absorption correction: multi-scan
(SADABS; Krause *et al.*, 2015)

T_min = 0.769, T_max = 0.831

13707 measured reflections

5560 independent reflections

5406 reflections with *I* > 2σ(*I*)

R_int = 0.024

θ_max = 27.5°, θ_min = 1.9°

h = -14→14

k = -12→13

l = -14→14

Refinement

Refinement on *F*²

Least-squares matrix: full

R[F² > 2σ(F²)] = 0.021

wR(F²) = 0.052

S = 1.08

5560 reflections

255 parameters

1 restraint

H-atom parameters constrained

w = 1/[σ²(F₀²) + (0.0152P)² + 0.9168P]

where P = (F₀² + 2F_c²)/3

(Δ/σ)max = 0.001

Δρmax = 1.14 e Å⁻³

Δρmin = -0.96 e Å⁻³

Absolute structure: Flack *x* determined using
2423 quotients [(I⁺)-(I)]/[(I⁺)+(I)] (Parsons *et al.*, 2013)

Absolute structure parameter: -0.004 (10)

Special details

**Geometry.** All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

**Refinement.** Hydrogen atom positions were located in the difference Fourier map, then placed in idealized positions and refined using a riding model, with their displacement parameters set relative to those of their parent atoms. Key experimental parameters and refinement details are provided in the accompanying table.
<table><caption>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)</caption><thead><tr><th></th><th>x</th><th>y</th><th>z</th><th>U<sub>iso</sub>*/U<sub>eq</sub></th></tr></thead><tbody><tr><td>Sn1</td><td>0.49452 (2)</td><td>0.82589 (8)</td><td>0.24933 (3)</td><td>0.01803 (6)</td></tr><tr><td>Cl5</td><td>0.50217 (10)</td><td>0.62101 (9)</td><td>0.15898 (10)</td><td>0.0274 (2)</td></tr><tr><td>Cl2</td><td>0.58501 (10)</td><td>0.74656 (10)</td><td>0.45596 (10)</td><td>0.0300 (2)</td></tr><tr><td>Cl4</td><td>0.40557 (10)</td><td>0.90459 (10)</td><td>0.04246 (10)</td><td>0.0279 (2)</td></tr><tr><td>Cl1</td><td>0.28821 (10)</td><td>0.78517 (11)</td><td>0.28989 (12)</td><td>0.0362 (3)</td></tr><tr><td>Cl6</td><td>0.48614 (11)</td><td>1.03090 (9)</td><td>0.33714 (10)</td><td>0.0285 (2)</td></tr><tr><td>Cl3</td><td>0.70110 (9)</td><td>0.86564 (11)</td><td>0.21024 (11)</td><td>0.0332 (3)</td></tr><tr><td>O2B</td><td>0.6272 (3)</td><td>0.2663 (3)</td><td>0.2471 (3)</td><td>0.0309 (7)</td></tr><tr><td>O1B</td><td>0.8180 (2)</td><td>0.3081 (4)</td><td>0.2165 (3)</td><td>0.0317 (7)</td></tr><tr><td>H1B</td><td>0.805837</td><td>0.244024</td><td>0.171470</td><td>0.048*</td></tr><tr><td>O2W</td><td>0.7671 (3)</td><td>0.1178 (4)</td><td>0.0630 (3)</td><td>0.0370 (8)</td></tr><tr><td>H2WA</td><td>0.741271</td><td>0.045743</td><td>0.083037</td><td>0.055*</td></tr><tr><td>H2WB</td><td>0.721040</td><td>0.133722</td><td>-0.010916</td><td>0.055*</td></tr><tr><td>O1A</td><td>0.1824 (3)</td><td>0.3717 (3)</td><td>0.2622 (3)</td><td>0.0356 (9)</td></tr><tr><td>H1A</td><td>0.201961</td><td>0.416162</td><td>0.327006</td><td>0.053*</td></tr><tr><td>N1B</td><td>0.6272 (3)</td><td>0.4429 (4)</td><td>0.4137 (3)</td><td>0.0211 (7)</td></tr><tr><td>H1BA</td><td>0.558359</td><td>0.422507</td><td>0.354275</td><td>0.025*</td></tr><tr><td>H1BB</td><td>0.618522</td><td>0.521155</td><td>0.442085</td><td>0.025*</td></tr><tr><td>H1BC</td><td>0.636197</td><td>0.388650</td><td>0.479181</td><td>0.025*</td></tr><tr><td>O1W</td><td>0.2364 (3)</td><td>0.5357 (4)</td><td>0.4443 (3)</td><td>0.0368 (8)</td></tr><tr><td>H1WA</td><td>0.295281</td><td>0.499525</td><td>0.498906</td><td>0.055*</td></tr><tr><td>H1WB</td><td>0.267860</td><td>0.596358</td><td>0.408457</td><td>0.055*</td></tr><tr><td>N1A</td><td>0.3796 (3)</td><td>0.2222 (4)</td><td>0.0820 (3)</td><td>0.0245 (8)</td></tr><tr><td>H1AA</td><td>0.375746</td><td>0.212276</td><td>-0.001998</td><td>0.029*</td></tr><tr><td>H1AB</td><td>0.399377</td><td>0.148537</td><td>0.122200</td><td>0.029*</td></tr><tr><td>H1AC</td><td>0.438963</td><td>0.279448</td><td>0.113534</td><td>0.029*</td></tr><tr><td>C4A</td><td>0.1241 (3)</td><td>0.0902 (4)</td><td>-0.0217 (4)</td><td>0.0235 (9)</td></tr><tr><td>H4A</td><td>0.199029</td><td>0.069140</td><td>-0.056190</td><td>0.028*</td></tr><tr><td>O2A</td><td>0.3855 (3)</td><td>0.3808 (4)</td><td>0.2660 (3)</td><td>0.0297 (7)</td></tr><tr><td>C1B</td><td>0.7214 (3)</td><td>0.3273 (7)</td><td>0.2674 (3)</td><td>0.0214 (7)</td></tr><tr><td>C5B</td><td>0.9132 (4)</td><td>0.6561 (5)</td><td>0.4828 (5)</td><td>0.0380 (11)</td></tr><tr><td>H5BA</td><td>0.924071</td><td>0.725335</td><td>0.542663</td><td>0.057*</td></tr><tr><td>H5BB</td><td>0.843498</td><td>0.673945</td><td>0.412213</td><td>0.057*</td></tr><tr><td>H5BC</td><td>0.989605</td><td>0.645129</td><td>0.451034</td><td>0.057*</td></tr><tr><td>C5A</td><td>0.0377 (4)</td><td>0.1692 (5)</td><td>-0.1179 (4)</td><td>0.0342 (10)</td></tr><tr><td>H5AA</td><td>0.015946</td><td>0.124339</td><td>-0.198095</td><td>0.051*</td></tr><tr><td>H5AB</td><td>0.079523</td><td>0.247040</td><td>-0.130280</td><td>0.051*</td></tr><tr><td>H5AC</td><td>-0.038261</td><td>0.187265</td><td>-0.087508</td><td>0.051*</td></tr><tr><td>C6B</td><td>0.9955 (4)</td><td>0.5050 (5)</td><td>0.6554 (4)</td><td>0.0411 (12)</td></tr><tr><td>H6BA</td><td>1.068981</td><td>0.487570</td><td>0.620531</td><td>0.062*</td></tr><tr><td>H6BB</td><td>0.974653</td><td>0.431433</td><td>0.699814</td><td>0.062*</td></tr><tr><td>H6BC</td><td>1.013350</td><td>0.574610</td><td>0.714509</td><td>0.062*</td></tr><tr><td>C6A</td><td>0.0592 (4)</td><td>-0.0310 (4)</td><td>0.0008 (5)</td><td>0.0313 (9)</td></tr><tr><td>H6AA</td><td>-0.014605</td><td>-0.012152</td><td>0.034615</td><td>0.047*</td></tr><tr><td>H6AB</td><td>0.116771</td><td>-0.082361</td><td>0.061285</td><td>0.047*</td></tr></tbody></table>
<table><tr><td>H6AC</td><td>0.034027</td><td>-0.075865</td><td>-0.079050</td><td>0.047*</td></tr><tr><td>C3A</td><td>0.1681 (3)</td><td>0.1569 (4)</td><td>0.1045 (3)</td><td>0.0240 (7)</td></tr><tr><td>H3AA</td><td>0.093960</td><td>0.187346</td><td>0.133558</td><td>0.029*</td></tr><tr><td>H3AB</td><td>0.210690</td><td>0.095956</td><td>0.167339</td><td>0.029*</td></tr><tr><td>C4B</td><td>0.8860 (4)</td><td>0.5380 (5)</td><td>0.5489 (4)</td><td>0.0274 (9)</td></tr><tr><td>H4B</td><td>0.811157</td><td>0.552556</td><td>0.585628</td><td>0.033*</td></tr><tr><td>C2A</td><td>0.2556 (3)</td><td>0.2656 (4)</td><td>0.1022 (3)</td><td>0.0219 (7)</td></tr><tr><td>H2A</td><td>0.217645</td><td>0.319994</td><td>0.029534</td><td>0.026*</td></tr><tr><td>C3B</td><td>0.8591 (3)</td><td>0.4281 (4)</td><td>0.4578 (3)</td><td>0.0235 (7)</td></tr><tr><td>H3BA</td><td>0.930140</td><td>0.418688</td><td>0.415750</td><td>0.028*</td></tr><tr><td>H3BB</td><td>0.854849</td><td>0.351957</td><td>0.507577</td><td>0.028*</td></tr><tr><td>C2B</td><td>0.7402 (3)</td><td>0.4372 (3)</td><td>0.3568 (3)</td><td>0.0198 (7)</td></tr><tr><td>H2B</td><td>0.743701</td><td>0.514475</td><td>0.306735</td><td>0.024*</td></tr><tr><td>C1A</td><td>0.2819 (3)</td><td>0.3453 (5)</td><td>0.2205 (4)</td><td>0.0206 (10)</td></tr></table>

Atomic displacement parameters (Å²)

<table><thead><tr><th></th><th>U<sup>11</sup></th><th>U<sup>22</sup></th><th>U<sup>33</sup></th><th>U<sup>12</sup></th><th>U<sup>13</sup></th><th>U<sup>23</sup></th></tr></thead><tbody><tr><td>Sn1</td><td>0.02014 (10)</td><td>0.01690 (10)</td><td>0.01714 (9)</td><td>0.00183 (9)</td><td>0.00416 (6)</td><td>0.00103 (6)</td></tr><tr><td>Cl5</td><td>0.0400 (5)</td><td>0.0191 (5)</td><td>0.0216 (5)</td><td>0.0049 (4)</td><td>0.0034 (4)</td><td>-0.0014 (4)</td></tr><tr><td>Cl2</td><td>0.0463 (6)</td><td>0.0236 (6)</td><td>0.0180 (5)</td><td>0.0054 (4)</td><td>0.0025 (4)</td><td>0.0018 (5)</td></tr><tr><td>Cl4</td><td>0.0347 (5)</td><td>0.0249 (6)</td><td>0.0208 (5)</td><td>0.0069 (4)</td><td>-0.0017 (4)</td><td>0.0037 (5)</td></tr><tr><td>Cl1</td><td>0.0262 (5)</td><td>0.0373 (7)</td><td>0.0479 (7)</td><td>-0.0030 (4)</td><td>0.0144 (4)</td><td>0.0040 (5)</td></tr><tr><td>Cl6</td><td>0.0451 (6)</td><td>0.0177 (5)</td><td>0.0243 (5)</td><td>0.0020 (4)</td><td>0.0108 (4)</td><td>-0.0003 (5)</td></tr><tr><td>Cl3</td><td>0.0214 (4)</td><td>0.0423 (8)</td><td>0.0365 (6)</td><td>-0.0018 (4)</td><td>0.0076 (4)</td><td>0.0016 (5)</td></tr><tr><td>O2B</td><td>0.0273 (14)</td><td>0.0302 (17)</td><td>0.0378 (17)</td><td>-0.0067 (13)</td><td>0.0124 (12)</td><td>-0.0103 (15)</td></tr><tr><td>O1B</td><td>0.0242 (12)</td><td>0.043 (2)</td><td>0.0310 (14)</td><td>-0.0022 (13)</td><td>0.0118 (10)</td><td>-0.0100 (15)</td></tr><tr><td>O2W</td><td>0.0369 (17)</td><td>0.040 (2)</td><td>0.0329 (18)</td><td>0.0103 (15)</td><td>0.0050 (14)</td><td>-0.0023 (17)</td></tr><tr><td>O1A</td><td>0.0240 (13)</td><td>0.045 (2)</td><td>0.0383 (17)</td><td>-0.0010 (12)</td><td>0.0077 (12)</td><td>-0.0157 (15)</td></tr><tr><td>N1B</td><td>0.0181 (14)</td><td>0.0225 (18)</td><td>0.0216 (16)</td><td>0.0006 (13)</td><td>0.0017 (12)</td><td>-0.0006 (15)</td></tr><tr><td>O1W</td><td>0.0373 (17)</td><td>0.040 (2)</td><td>0.0320 (18)</td><td>0.0051 (15)</td><td>0.0046 (14)</td><td>-0.0062 (17)</td></tr><tr><td>N1A</td><td>0.0205 (15)</td><td>0.028 (2)</td><td>0.0271 (18)</td><td>-0.0009 (14)</td><td>0.0086 (13)</td><td>-0.0004 (16)</td></tr><tr><td>C4A</td><td>0.0170 (16)</td><td>0.028 (2)</td><td>0.0248 (19)</td><td>0.0019 (14)</td><td>0.0029 (14)</td><td>-0.0025 (16)</td></tr><tr><td>O2A</td><td>0.0222 (13)</td><td>0.0346 (18)</td><td>0.0308 (16)</td><td>-0.0059 (12)</td><td>0.0022 (12)</td><td>-0.0057 (14)</td></tr><tr><td>C1B</td><td>0.0194 (14)</td><td>0.0223 (18)</td><td>0.0229 (16)</td><td>0.0035 (19)</td><td>0.0052 (12)</td><td>0.004 (2)</td></tr><tr><td>C5B</td><td>0.031 (2)</td><td>0.033 (3)</td><td>0.048 (3)</td><td>-0.0072 (18)</td><td>0.0033 (19)</td><td>-0.004 (2)</td></tr><tr><td>C5A</td><td>0.032 (2)</td><td>0.034 (2)</td><td>0.033 (2)</td><td>-0.0001 (18)</td><td>-0.0029 (17)</td><td>0.0020 (19)</td></tr><tr><td>C6B</td><td>0.028 (2)</td><td>0.059 (3)</td><td>0.033 (2)</td><td>0.001 (2)</td><td>-0.0021 (18)</td><td>-0.004 (2)</td></tr><tr><td>C6A</td><td>0.026 (2)</td><td>0.029 (2)</td><td>0.038 (2)</td><td>-0.0026 (17)</td><td>0.0049 (17)</td><td>-0.0039 (18)</td></tr><tr><td>C3A</td><td>0.0216 (17)</td><td>0.0269 (19)</td><td>0.0234 (16)</td><td>-0.0024 (14)</td><td>0.0042 (13)</td><td>0.0026 (15)</td></tr><tr><td>C4B</td><td>0.0179 (17)</td><td>0.035 (2)</td><td>0.028 (2)</td><td>-0.0027 (16)</td><td>0.0015 (14)</td><td>-0.0082 (18)</td></tr><tr><td>C2A</td><td>0.0180 (15)</td><td>0.0249 (19)</td><td>0.0224 (17)</td><td>0.0003 (14)</td><td>0.0033 (13)</td><td>0.0015 (15)</td></tr><tr><td>C3B</td><td>0.0169 (15)</td><td>0.0259 (19)</td><td>0.0264 (17)</td><td>0.0040 (13)</td><td>0.0016 (14)</td><td>0.0011 (14)</td></tr><tr><td>C2B</td><td>0.0151 (15)</td><td>0.0201 (18)</td><td>0.0243 (17)</td><td>0.0002 (13)</td><td>0.0038 (13)</td><td>0.0026 (14)</td></tr><tr><td>C1A</td><td>0.0209 (15)</td><td>0.020 (3)</td><td>0.0202 (16)</td><td>0.0003 (15)</td><td>0.0029 (12)</td><td>0.0044 (16)</td></tr></tbody></table>
Geometric parameters (Å, °)

<table><tr><td>Sn1—Cl5</td><td>2.4259 (13)</td><td>O2A—C1A</td><td>1.202 (5)</td></tr><tr><td>Sn1—Cl2</td><td>2.4084 (11)</td><td>C1B—C2B</td><td>1.517 (7)</td></tr><tr><td>Sn1—Cl4</td><td>2.4045 (11)</td><td>C5B—H5BA</td><td>0.9800</td></tr><tr><td>Sn1—Cl1</td><td>2.4387 (11)</td><td>C5B—H5BB</td><td>0.9800</td></tr><tr><td>Sn1—Cl6</td><td>2.4171 (14)</td><td>C5B—H5BC</td><td>0.9800</td></tr><tr><td>Sn1—Cl3</td><td>2.4338 (11)</td><td>C5B—C4B</td><td>1.523 (7)</td></tr><tr><td>O2B—C1B</td><td>1.206 (6)</td><td>C5A—H5AA</td><td>0.9800</td></tr><tr><td>O1B—H1B</td><td>0.8400</td><td>C5A—H5AB</td><td>0.9800</td></tr><tr><td>O1B—C1B</td><td>1.313 (4)</td><td>C5A—H5AC</td><td>0.9800</td></tr><tr><td>O2W—H2WA</td><td>0.8700</td><td>C6B—H6BA</td><td>0.9800</td></tr><tr><td>O2W—H2WB</td><td>0.8700</td><td>C6B—H6BB</td><td>0.9800</td></tr><tr><td>O1A—H1A</td><td>0.8400</td><td>C6B—H6BC</td><td>0.9800</td></tr><tr><td>O1A—C1A</td><td>1.301 (5)</td><td>C6B—C4B</td><td>1.522 (6)</td></tr><tr><td>N1B—H1BA</td><td>0.9100</td><td>C6A—H6AA</td><td>0.9800</td></tr><tr><td>N1B—H1BB</td><td>0.9100</td><td>C6A—H6AB</td><td>0.9800</td></tr><tr><td>N1B—H1BC</td><td>0.9100</td><td>C6A—H6AC</td><td>0.9800</td></tr><tr><td>N1B—C2B</td><td>1.502 (4)</td><td>C3A—H3AA</td><td>0.9900</td></tr><tr><td>O1W—H1WA</td><td>0.8704</td><td>C3A—H3AB</td><td>0.9900</td></tr><tr><td>O1W—H1WB</td><td>0.8696</td><td>C3A—C2A</td><td>1.519 (5)</td></tr><tr><td>N1A—H1AA</td><td>0.9100</td><td>C4B—H4B</td><td>1.0000</td></tr><tr><td>N1A—H1AB</td><td>0.9100</td><td>C4B—C3B</td><td>1.531 (6)</td></tr><tr><td>N1A—H1AC</td><td>0.9100</td><td>C2A—H2A</td><td>1.0000</td></tr><tr><td>N1A—C2A</td><td>1.500 (5)</td><td>C2A—C1A</td><td>1.521 (6)</td></tr><tr><td>C4A—H4A</td><td>1.0000</td><td>C3B—H3BA</td><td>0.9900</td></tr><tr><td>C4A—C5A</td><td>1.515 (6)</td><td>C3B—H3BB</td><td>0.9900</td></tr><tr><td>C4A—C6A</td><td>1.533 (6)</td><td>C3B—C2B</td><td>1.518 (5)</td></tr><tr><td>C4A—C3A</td><td>1.532 (5)</td><td>C2B—H2B</td><td>1.0000</td></tr><tr><td>Cl5—Sn1—Cl1</td><td>91.30 (5)</td><td>H5AA—C5A—H5AB</td><td>109.5</td></tr><tr><td>Cl5—Sn1—Cl3</td><td>88.62 (4)</td><td>H5AA—C5A—H5AC</td><td>109.5</td></tr><tr><td>Cl2—Sn1—Cl5</td><td>90.58 (5)</td><td>H5AB—C5A—H5AC</td><td>109.5</td></tr><tr><td>Cl2—Sn1—Cl1</td><td>89.00 (4)</td><td>H6BA—C6B—H6BB</td><td>109.5</td></tr><tr><td>Cl2—Sn1—Cl6</td><td>90.02 (4)</td><td>H6BA—C6B—H6BC</td><td>109.5</td></tr><tr><td>Cl2—Sn1—Cl3</td><td>90.58 (4)</td><td>H6BB—C6B—H6BC</td><td>109.5</td></tr><tr><td>Cl4—Sn1—Cl5</td><td>89.20 (4)</td><td>C4B—C6B—H6BA</td><td>109.5</td></tr><tr><td>Cl4—Sn1—Cl2</td><td>179.56 (5)</td><td>C4B—C6B—H6BB</td><td>109.5</td></tr><tr><td>Cl4—Sn1—Cl1</td><td>91.38 (4)</td><td>C4B—C6B—H6BC</td><td>109.5</td></tr><tr><td>Cl4—Sn1—Cl6</td><td>90.20 (5)</td><td>C4A—C6A—H6AA</td><td>109.5</td></tr><tr><td>Cl4—Sn1—Cl3</td><td>89.04 (4)</td><td>C4A—C6A—H6AB</td><td>109.5</td></tr><tr><td>Cl6—Sn1—Cl5</td><td>179.40 (5)</td><td>C4A—C6A—H6AC</td><td>109.5</td></tr><tr><td>Cl6—Sn1—Cl1</td><td>88.77 (4)</td><td>H6AA—C6A—H6AB</td><td>109.5</td></tr><tr><td>Cl6—Sn1—Cl3</td><td>91.32 (5)</td><td>H6AA—C6A—H6AC</td><td>109.5</td></tr><tr><td>Cl3—Sn1—Cl1</td><td>179.57 (6)</td><td>H6AB—C6A—H6AC</td><td>109.5</td></tr><tr><td>C1B—O1B—H1B</td><td>109.5</td><td>C4A—C3A—H3AA</td><td>108.4</td></tr><tr><td>H2WA—O2W—H2WB</td><td>104.5</td><td>C4A—C3A—H3AB</td><td>108.4</td></tr><tr><td>C1A—O1A—H1A</td><td>109.5</td><td>H3AA—C3A—H3AB</td><td>107.5</td></tr></table>
<table><caption>Hydrogen-bond geometry (Å, °)</caption><tbody><tr><td>H1BA—N1B—H1BB</td><td>109.5</td><td>C2A—C3A—C4A</td><td>115.3 (3)</td></tr><tr><td>H1BA—N1B—H1BC</td><td>109.5</td><td>C2A—C3A—H3AA</td><td>108.4</td></tr><tr><td>H1BB—N1B—H1BC</td><td>109.5</td><td>C2A—C3A—H3AB</td><td>108.4</td></tr><tr><td>C2B—N1B—H1BA</td><td>109.5</td><td>C5B—C4B—H4B</td><td>108.5</td></tr><tr><td>C2B—N1B—H1BB</td><td>109.5</td><td>C5B—C4B—C3B</td><td>111.9 (4)</td></tr><tr><td>C2B—N1B—H1BC</td><td>109.5</td><td>C6B—C4B—C5B</td><td>110.6 (4)</td></tr><tr><td>H1WA—O1W—H1WB</td><td>109.5</td><td>C6B—C4B—H4B</td><td>108.5</td></tr><tr><td>H1AA—N1A—H1AB</td><td>109.5</td><td>C6B—C4B—C3B</td><td>108.8 (4)</td></tr><tr><td>H1AA—N1A—H1AC</td><td>109.5</td><td>C3B—C4B—H4B</td><td>108.5</td></tr><tr><td>H1AB—N1A—H1AC</td><td>109.5</td><td>N1A—C2A—C3A</td><td>111.1 (3)</td></tr><tr><td>C2A—N1A—H1AA</td><td>109.5</td><td>N1A—C2A—H2A</td><td>107.9</td></tr><tr><td>C2A—N1A—H1AB</td><td>109.5</td><td>N1A—C2A—C1A</td><td>106.5 (3)</td></tr><tr><td>C2A—N1A—H1AC</td><td>109.5</td><td>C3A—C2A—H2A</td><td>107.9</td></tr><tr><td>C5A—C4A—H4A</td><td>108.3</td><td>C3A—C2A—C1A</td><td>115.4 (3)</td></tr><tr><td>C5A—C4A—C6A</td><td>110.2 (3)</td><td>C1A—C2A—H2A</td><td>107.9</td></tr><tr><td>C5A—C4A—C3A</td><td>112.6 (4)</td><td>C4B—C3B—H3BA</td><td>108.3</td></tr><tr><td>C6A—C4A—H4A</td><td>108.3</td><td>C4B—C3B—H3BB</td><td>108.3</td></tr><tr><td>C3A—C4A—H4A</td><td>108.3</td><td>H3BA—C3B—H3BB</td><td>107.4</td></tr><tr><td>C3A—C4A—C6A</td><td>109.1 (3)</td><td>C2B—C3B—C4B</td><td>115.8 (3)</td></tr><tr><td>O2B—C1B—O1B</td><td>125.1 (6)</td><td>C2B—C3B—H3BA</td><td>108.3</td></tr><tr><td>O2B—C1B—C2B</td><td>122.5 (3)</td><td>C2B—C3B—H3BB</td><td>108.3</td></tr><tr><td>O1B—C1B—C2B</td><td>112.4 (4)</td><td>N1B—C2B—C1B</td><td>106.5 (3)</td></tr><tr><td>H5BA—C5B—H5BB</td><td>109.5</td><td>N1B—C2B—C3B</td><td>111.4 (3)</td></tr><tr><td>H5BA—C5B—H5BC</td><td>109.5</td><td>N1B—C2B—H2B</td><td>108.6</td></tr><tr><td>H5BB—C5B—H5BC</td><td>109.5</td><td>C1B—C2B—C3B</td><td>113.0 (3)</td></tr><tr><td>C4B—C5B—H5BA</td><td>109.5</td><td>C1B—C2B—H2B</td><td>108.6</td></tr><tr><td>C4B—C5B—H5BB</td><td>109.5</td><td>C3B—C2B—H2B</td><td>108.6</td></tr><tr><td>C4B—C5B—H5BC</td><td>109.5</td><td>O1A—C1A—C2A</td><td>113.3 (3)</td></tr><tr><td>C4A—C5A—H5AA</td><td>109.5</td><td>O2A—C1A—O1A</td><td>125.4 (4)</td></tr><tr><td>C4A—C5A—H5AB</td><td>109.5</td><td>O2A—C1A—C2A</td><td>121.3 (4)</td></tr><tr><td>C4A—C5A—H5AC</td><td>109.5</td><td></td><td></td></tr><tr><td>O2B—C1B—C2B—N1B</td><td>3.6 (6)</td><td>C5B—C4B—C3B—C2B</td><td>-66.6 (4)</td></tr><tr><td>O2B—C1B—C2B—C3B</td><td>126.2 (5)</td><td>C5A—C4A—C3A—C2A</td><td>-68.7 (4)</td></tr><tr><td>O1B—C1B—C2B—N1B</td><td>-176.4 (4)</td><td>C6B—C4B—C3B—C2B</td><td>170.9 (4)</td></tr><tr><td>O1B—C1B—C2B—C3B</td><td>-53.9 (5)</td><td>C6A—C4A—C3A—C2A</td><td>168.7 (3)</td></tr><tr><td>N1A—C2A—C1A—O1A</td><td>-168.7 (4)</td><td>C3A—C2A—C1A—O1A</td><td>-44.9 (5)</td></tr><tr><td>N1A—C2A—C1A—O2A</td><td>13.0 (6)</td><td>C3A—C2A—C1A—O2A</td><td>136.8 (4)</td></tr><tr><td>C4A—C3A—C2A—N1A</td><td>-68.6 (4)</td><td>C4B—C3B—C2B—N1B</td><td>-62.0 (4)</td></tr><tr><td>C4A—C3A—C2A—C1A</td><td>170.1 (3)</td><td>C4B—C3B—C2B—C1B</td><td>178.2 (3)</td></tr></tbody></table>

<table><thead><tr><th>D—H···A</th><th>D—H</th><th>H···A</th><th>D···A</th><th>D—H···A</th></tr></thead><tbody><tr><td>N1A—H1AA···Cl3<sup>i</sup></td><td>0.91</td><td>2.78</td><td>3.470 (4)</td><td>133</td></tr><tr><td>N1A—H1AA···Cl5<sup>i</sup></td><td>0.91</td><td>2.58</td><td>3.342 (4)</td><td>142</td></tr><tr><td>N1A—H1AB···Cl4<sup>ii</sup></td><td>0.91</td><td>2.77</td><td>3.471 (4)</td><td>134</td></tr><tr><td>N1A—H1AB···Cl6<sup>ii</sup></td><td>0.91</td><td>2.65</td><td>3.452 (4)</td><td>148</td></tr></tbody></table>
<table><tr><td>N1A—H1AC···O2A</td><td>0.91</td><td>2.17</td><td>2.620 (5)</td><td>110</td></tr><tr><td>N1A—H1AC···O2B</td><td>0.91</td><td>2.26</td><td>2.959 (5)</td><td>133</td></tr><tr><td>N1B—H1BA···O2A</td><td>0.91</td><td>1.99</td><td>2.873 (5)</td><td>164</td></tr><tr><td>N1B—H1BA···O2B</td><td>0.91</td><td>2.27</td><td>2.626 (5)</td><td>103</td></tr><tr><td>N1B—H1BB···Cl2</td><td>0.91</td><td>2.47</td><td>3.352 (4)</td><td>164</td></tr><tr><td>N1B—H1BC···Cl1<sup>iii</sup></td><td>0.91</td><td>2.71</td><td>3.583 (4)</td><td>162</td></tr><tr><td>O1A—H1A···O1W</td><td>0.84</td><td>1.79</td><td>2.624 (5)</td><td>169</td></tr><tr><td>O1B—H1B···O2W</td><td>0.84</td><td>1.79</td><td>2.627 (6)</td><td>173</td></tr><tr><td>O1W—H1WA···Cl6<sup>iii</sup></td><td>0.87</td><td>2.69</td><td>3.440 (3)</td><td>145</td></tr><tr><td>O1W—H1WB···Cl1</td><td>0.87</td><td>2.44</td><td>3.283 (4)</td><td>162</td></tr><tr><td>O2W—H2WA···Cl3<sup>ii</sup></td><td>0.87</td><td>2.48</td><td>3.312 (4)</td><td>161</td></tr><tr><td>O2W—H2WB···Cl5<sup>i</sup></td><td>0.87</td><td>2.63</td><td>3.393 (3)</td><td>147</td></tr></table>

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