Bis(l-leucinium) hexa­chlorido­stannate(IV) dihydrate

Ghallab, R.; Kemmouche, A.; Boutebdja, M.; Golhen, S.

doi:10.1107/S2414314625006765

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 8| August 2025| x250676

https://doi.org/10.1107/S2414314625006765

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Bis(L-leucinium) hexachloridostannate(IV) dihydrate

Rochdi Ghallab,^a ^* Amina Kemmouche,^b Mehdi Boutebdja ^a and Stéphane Golhen ^c

^aLaboratoire de Technologie des Matériaux Avancés, Ecole Nationale Polytechnique de Constantine, Algeria, ^bEcole Nationale Superieure de Biotechnologie de Constantine, Algeria, and ^cUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), 35042, Rennes, France
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 20 July 2025; accepted 29 July 2025; online 15 August 2025)

The title compound, (C₆H₁₄NO₂)₂[SnCl₆]·2H₂O, features L-leucinium cations adopting extended conformations, which maximizes the separation between the methyl groups [–CH(CH₃)₂] and the polar NH₃⁺ and COOH moieties. Additionally, an intramolecular hydrogen bond between the ammonium (NH₃⁺) 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 NH₃⁺ 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.

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

CCDC reference: 2478499

Structure description

The title compound, 2(C₆H₁₄NO₂)⁺·[SnCl₆]^2–·2H₂O, crystallizes in the monoclinic space group P2₁. 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.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

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 ±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 ).

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 intramolecular 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 R₂²(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, which propagate along the crystallographic a-axis to form hydrogen-bonded layers lying parallel to the ac plane.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯Cl3ⁱ	0.91	2.78	3.470 (4)	133
N1A—H1AA⋯Cl5ⁱ	0.91	2.58	3.342 (4)	142
N1A—H1AB⋯Cl4ⁱⁱ	0.91	2.77	3.471 (4)	134
N1A—H1AB⋯Cl6ⁱⁱ	0.91	2.65	3.452 (4)	148
N1A—H1AC⋯O2A	0.91	2.17	2.620 (5)	110
N1A—H1AC⋯O2B	0.91	2.26	2.959 (5)	133
N1B—H1BA⋯O2A	0.91	1.99	2.873 (5)	164
N1B—H1BA⋯O2B	0.91	2.27	2.626 (5)	103
N1B—H1BB⋯Cl2	0.91	2.47	3.352 (4)	164
N1B—H1BC⋯Cl1ⁱⁱⁱ	0.91	2.71	3.583 (4)	162
O1A—H1A⋯O1W	0.84	1.79	2.624 (5)	169
O1B—H1B⋯O2W	0.84	1.79	2.627 (6)	173
O1W—H1WA⋯Cl6ⁱⁱⁱ	0.87	2.69	3.440 (3)	145
O1W—H1WB⋯Cl1	0.87	2.44	3.283 (4)	162
O2W—H2WA⋯Cl3ⁱⁱ	0.87	2.48	3.312 (4)	161
O2W—H2WB⋯Cl5ⁱ	0.87	2.63	3.393 (3)	147
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Figure 2
Projection onto the ac plane showing R₂²(10) graph-set motifs that organize the molecules into dimers.

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.

Figure 3
Projection onto the bc plane showing the interconnection of the cationic and anionic sublayers mediated by water molecules.

The synergy between dimer-forming R₂²(10) motifs, water-mediated interlayer connectivity, and N—H⋯Cl interactions highlights the hierarchical role of hydrogen bonding in 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 L-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.

Table 2
Experimental details

Crystal data
Chemical formula	(C₆H₁₄NO₂)₂[SnCl₆]·2H₂O
M_r	631.78
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	10.9838 (11), 10.7837 (11), 10.8556 (11)
β (°)	102.316 (4)
V (Å³)	1256.2 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.68
Crystal size (mm)	0.17 × 0.13 × 0.11

Data collection
Diffractometer	D8 VENTURE Bruker AXS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.769, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections	13707, 5560, 5406
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.052, 1.08
No. of reflections	5560
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.96
Absolute structure	Flack x determined using 2423 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.004 (10)
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2478499

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625006765/hb4529sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625006765/hb4529Isup2.hkl

checkCIF report

Computing details top

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

Crystal data top

(C₆H₁₄NO₂)₂[SnCl₆]·2H₂O	F(000) = 636
M_r = 631.78	D_x = 1.670 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 5406 reflections
a = 10.9838 (11) Å	θ = 2.4–27.5°
b = 10.7837 (11) Å	µ = 1.68 mm⁻¹
c = 10.8556 (11) Å	T = 150 K
β = 102.316 (4)°	Block, white
V = 1256.2 (2) Å³	0.17 × 0.13 × 0.11 mm
Z = 2

Data collection top

D8 VENTURE Bruker AXS diffractometer	5406 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	R_int = 0.024
CCD rotation images, thick slices scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
T_min = 0.769, T_max = 0.831	k = −12→13
13707 measured reflections	l = −14→14
5560 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0152P)² + 0.9168P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.021	(Δ/σ)_max = 0.001
wR(F²) = 0.052	Δρ_max = 1.14 e Å⁻³
S = 1.08	Δρ_min = −0.96 e Å⁻³
5560 reflections	Absolute structure: Flack x determined using 2423 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
255 parameters	Absolute structure parameter: −0.004 (10)
1 restraint

Special details top

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.

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

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

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02014 (10)	0.01690 (10)	0.01714 (9)	0.00183 (9)	0.00416 (6)	0.00103 (6)
Cl5	0.0400 (5)	0.0191 (5)	0.0216 (5)	0.0049 (4)	0.0034 (4)	−0.0014 (4)
Cl2	0.0463 (6)	0.0236 (6)	0.0180 (5)	0.0054 (4)	0.0025 (4)	0.0018 (5)
Cl4	0.0347 (5)	0.0249 (6)	0.0208 (5)	0.0069 (4)	−0.0017 (4)	0.0037 (5)
Cl1	0.0262 (5)	0.0373 (7)	0.0479 (7)	−0.0030 (4)	0.0144 (4)	0.0040 (5)
Cl6	0.0451 (6)	0.0177 (5)	0.0243 (5)	0.0020 (4)	0.0108 (4)	−0.0003 (5)
Cl3	0.0214 (4)	0.0423 (8)	0.0365 (6)	−0.0018 (4)	0.0076 (4)	0.0016 (5)
O2B	0.0273 (14)	0.0302 (17)	0.0378 (17)	−0.0067 (13)	0.0124 (12)	−0.0103 (15)
O1B	0.0242 (12)	0.043 (2)	0.0310 (14)	−0.0022 (13)	0.0118 (10)	−0.0100 (15)
O2W	0.0369 (17)	0.040 (2)	0.0329 (18)	0.0103 (15)	0.0050 (14)	−0.0023 (17)
O1A	0.0240 (13)	0.045 (2)	0.0383 (17)	−0.0010 (12)	0.0077 (12)	−0.0157 (15)
N1B	0.0181 (14)	0.0225 (18)	0.0216 (16)	0.0006 (13)	0.0017 (12)	−0.0006 (15)
O1W	0.0373 (17)	0.040 (2)	0.0320 (18)	0.0051 (15)	0.0046 (14)	−0.0062 (17)
N1A	0.0205 (15)	0.028 (2)	0.0271 (18)	−0.0009 (14)	0.0086 (13)	−0.0004 (16)
C4A	0.0170 (16)	0.028 (2)	0.0248 (19)	0.0019 (14)	0.0029 (14)	−0.0025 (16)
O2A	0.0222 (13)	0.0346 (18)	0.0308 (16)	−0.0059 (12)	0.0022 (12)	−0.0057 (14)
C1B	0.0194 (14)	0.0223 (18)	0.0229 (16)	0.0035 (19)	0.0052 (12)	0.004 (2)
C5B	0.031 (2)	0.033 (3)	0.048 (3)	−0.0072 (18)	0.0033 (19)	−0.004 (2)
C5A	0.032 (2)	0.034 (2)	0.033 (2)	−0.0001 (18)	−0.0029 (17)	0.0020 (19)
C6B	0.028 (2)	0.059 (3)	0.033 (2)	0.001 (2)	−0.0021 (18)	−0.004 (2)
C6A	0.026 (2)	0.029 (2)	0.038 (2)	−0.0026 (17)	0.0049 (17)	−0.0039 (18)
C3A	0.0216 (17)	0.0269 (19)	0.0234 (16)	−0.0024 (14)	0.0042 (13)	0.0026 (15)
C4B	0.0179 (17)	0.035 (2)	0.028 (2)	−0.0027 (16)	0.0015 (14)	−0.0082 (18)
C2A	0.0180 (15)	0.0249 (19)	0.0224 (17)	0.0003 (14)	0.0033 (13)	0.0015 (15)
C3B	0.0169 (15)	0.0259 (19)	0.0264 (17)	0.0040 (13)	0.0016 (14)	0.0011 (14)
C2B	0.0151 (15)	0.0201 (18)	0.0243 (17)	0.0002 (13)	0.0038 (13)	0.0026 (14)
C1A	0.0209 (15)	0.020 (3)	0.0202 (16)	0.0003 (15)	0.0029 (12)	0.0044 (16)

Geometric parameters (Å, º) top

Sn1—Cl5	2.4259 (13)	O2A—C1A	1.202 (5)
Sn1—Cl2	2.4084 (11)	C1B—C2B	1.517 (7)
Sn1—Cl4	2.4045 (11)	C5B—H5BA	0.9800
Sn1—Cl1	2.4387 (11)	C5B—H5BB	0.9800
Sn1—Cl6	2.4171 (14)	C5B—H5BC	0.9800
Sn1—Cl3	2.4338 (11)	C5B—C4B	1.523 (7)
O2B—C1B	1.206 (6)	C5A—H5AA	0.9800
O1B—H1B	0.8400	C5A—H5AB	0.9800
O1B—C1B	1.313 (4)	C5A—H5AC	0.9800
O2W—H2WA	0.8700	C6B—H6BA	0.9800
O2W—H2WB	0.8700	C6B—H6BB	0.9800
O1A—H1A	0.8400	C6B—H6BC	0.9800
O1A—C1A	1.301 (5)	C6B—C4B	1.522 (6)
N1B—H1BA	0.9100	C6A—H6AA	0.9800
N1B—H1BB	0.9100	C6A—H6AB	0.9800
N1B—H1BC	0.9100	C6A—H6AC	0.9800
N1B—C2B	1.502 (4)	C3A—H3AA	0.9900
O1W—H1WA	0.8704	C3A—H3AB	0.9900
O1W—H1WB	0.8696	C3A—C2A	1.519 (5)
N1A—H1AA	0.9100	C4B—H4B	1.0000
N1A—H1AB	0.9100	C4B—C3B	1.531 (6)
N1A—H1AC	0.9100	C2A—H2A	1.0000
N1A—C2A	1.500 (5)	C2A—C1A	1.521 (6)
C4A—H4A	1.0000	C3B—H3BA	0.9900
C4A—C5A	1.515 (6)	C3B—H3BB	0.9900
C4A—C6A	1.533 (6)	C3B—C2B	1.518 (5)
C4A—C3A	1.532 (5)	C2B—H2B	1.0000

Cl5—Sn1—Cl1	91.30 (5)	H5AA—C5A—H5AB	109.5
Cl5—Sn1—Cl3	88.62 (4)	H5AA—C5A—H5AC	109.5
Cl2—Sn1—Cl5	90.58 (5)	H5AB—C5A—H5AC	109.5
Cl2—Sn1—Cl1	89.00 (4)	H6BA—C6B—H6BB	109.5
Cl2—Sn1—Cl6	90.02 (4)	H6BA—C6B—H6BC	109.5
Cl2—Sn1—Cl3	90.58 (4)	H6BB—C6B—H6BC	109.5
Cl4—Sn1—Cl5	89.20 (4)	C4B—C6B—H6BA	109.5
Cl4—Sn1—Cl2	179.56 (5)	C4B—C6B—H6BB	109.5
Cl4—Sn1—Cl1	91.38 (4)	C4B—C6B—H6BC	109.5
Cl4—Sn1—Cl6	90.20 (5)	C4A—C6A—H6AA	109.5
Cl4—Sn1—Cl3	89.04 (4)	C4A—C6A—H6AB	109.5
Cl6—Sn1—Cl5	179.40 (5)	C4A—C6A—H6AC	109.5
Cl6—Sn1—Cl1	88.77 (4)	H6AA—C6A—H6AB	109.5
Cl6—Sn1—Cl3	91.32 (5)	H6AA—C6A—H6AC	109.5
Cl3—Sn1—Cl1	179.57 (6)	H6AB—C6A—H6AC	109.5
C1B—O1B—H1B	109.5	C4A—C3A—H3AA	108.4
H2WA—O2W—H2WB	104.5	C4A—C3A—H3AB	108.4
C1A—O1A—H1A	109.5	H3AA—C3A—H3AB	107.5
H1BA—N1B—H1BB	109.5	C2A—C3A—C4A	115.3 (3)
H1BA—N1B—H1BC	109.5	C2A—C3A—H3AA	108.4
H1BB—N1B—H1BC	109.5	C2A—C3A—H3AB	108.4
C2B—N1B—H1BA	109.5	C5B—C4B—H4B	108.5
C2B—N1B—H1BB	109.5	C5B—C4B—C3B	111.9 (4)
C2B—N1B—H1BC	109.5	C6B—C4B—C5B	110.6 (4)
H1WA—O1W—H1WB	109.5	C6B—C4B—H4B	108.5
H1AA—N1A—H1AB	109.5	C6B—C4B—C3B	108.8 (4)
H1AA—N1A—H1AC	109.5	C3B—C4B—H4B	108.5
H1AB—N1A—H1AC	109.5	N1A—C2A—C3A	111.1 (3)
C2A—N1A—H1AA	109.5	N1A—C2A—H2A	107.9
C2A—N1A—H1AB	109.5	N1A—C2A—C1A	106.5 (3)
C2A—N1A—H1AC	109.5	C3A—C2A—H2A	107.9
C5A—C4A—H4A	108.3	C3A—C2A—C1A	115.4 (3)
C5A—C4A—C6A	110.2 (3)	C1A—C2A—H2A	107.9
C5A—C4A—C3A	112.6 (4)	C4B—C3B—H3BA	108.3
C6A—C4A—H4A	108.3	C4B—C3B—H3BB	108.3
C3A—C4A—H4A	108.3	H3BA—C3B—H3BB	107.4
C3A—C4A—C6A	109.1 (3)	C2B—C3B—C4B	115.8 (3)
O2B—C1B—O1B	125.1 (6)	C2B—C3B—H3BA	108.3
O2B—C1B—C2B	122.5 (3)	C2B—C3B—H3BB	108.3
O1B—C1B—C2B	112.4 (4)	N1B—C2B—C1B	106.5 (3)
H5BA—C5B—H5BB	109.5	N1B—C2B—C3B	111.4 (3)
H5BA—C5B—H5BC	109.5	N1B—C2B—H2B	108.6
H5BB—C5B—H5BC	109.5	C1B—C2B—C3B	113.0 (3)
C4B—C5B—H5BA	109.5	C1B—C2B—H2B	108.6
C4B—C5B—H5BB	109.5	C3B—C2B—H2B	108.6
C4B—C5B—H5BC	109.5	O1A—C1A—C2A	113.3 (3)
C4A—C5A—H5AA	109.5	O2A—C1A—O1A	125.4 (4)
C4A—C5A—H5AB	109.5	O2A—C1A—C2A	121.3 (4)
C4A—C5A—H5AC	109.5

O2B—C1B—C2B—N1B	3.6 (6)	C5B—C4B—C3B—C2B	−66.6 (4)
O2B—C1B—C2B—C3B	126.2 (5)	C5A—C4A—C3A—C2A	−68.7 (4)
O1B—C1B—C2B—N1B	−176.4 (4)	C6B—C4B—C3B—C2B	170.9 (4)
O1B—C1B—C2B—C3B	−53.9 (5)	C6A—C4A—C3A—C2A	168.7 (3)
N1A—C2A—C1A—O1A	−168.7 (4)	C3A—C2A—C1A—O1A	−44.9 (5)
N1A—C2A—C1A—O2A	13.0 (6)	C3A—C2A—C1A—O2A	136.8 (4)
C4A—C3A—C2A—N1A	−68.6 (4)	C4B—C3B—C2B—N1B	−62.0 (4)
C4A—C3A—C2A—C1A	170.1 (3)	C4B—C3B—C2B—C1B	178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···Cl3ⁱ	0.91	2.78	3.470 (4)	133
N1A—H1AA···Cl5ⁱ	0.91	2.58	3.342 (4)	142
N1A—H1AB···Cl4ⁱⁱ	0.91	2.77	3.471 (4)	134
N1A—H1AB···Cl6ⁱⁱ	0.91	2.65	3.452 (4)	148
N1A—H1AC···O2A	0.91	2.17	2.620 (5)	110
N1A—H1AC···O2B	0.91	2.26	2.959 (5)	133
N1B—H1BA···O2A	0.91	1.99	2.873 (5)	164
N1B—H1BA···O2B	0.91	2.27	2.626 (5)	103
N1B—H1BB···Cl2	0.91	2.47	3.352 (4)	164
N1B—H1BC···Cl1ⁱⁱⁱ	0.91	2.71	3.583 (4)	162
O1A—H1A···O1W	0.84	1.79	2.624 (5)	169
O1B—H1B···O2W	0.84	1.79	2.627 (6)	173
O1W—H1WA···Cl6ⁱⁱⁱ	0.87	2.69	3.440 (3)	145
O1W—H1WB···Cl1	0.87	2.44	3.283 (4)	162
O2W—H2WA···Cl3ⁱⁱ	0.87	2.48	3.312 (4)	161
O2W—H2WB···Cl5ⁱ	0.87	2.63	3.393 (3)	147

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

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 Polytechnique de Constantine, Algérie ; Unité de Recherche de Chimie de l'Environnement, Moléculaire et Structurale UR.CHEMS ; DRSDT-Algeria .

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