Tris(cyclo­hexyl­ammonium) cis-di­chlorido­bis­(oxalato-κ2O1,O2)stann­ate(IV) chloride monohydrate

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

doi:10.1107/S1600536813026901

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages m581-m582

doi:10.1107/S1600536813026901

Open

access

Tris(cyclohexylammonium) cis-dichloridobis(oxalato-κ²O¹,O²)stannate(IV) chloride monohydrate

Modou Sarr,^a Waly Diallo,^a ^* Aminata Diasse-Sarr,^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: diallo_waly@yahoo.fr, hcattey@u-bourgogne.fr

(Received 13 September 2013; accepted 30 September 2013; online 5 October 2013)

The crystal structure of the title compound, (C₆H₁₄N)₃[Sn(C₂O₄)₂Cl₂]Cl·H₂O, contains three cyclohexylammonium cations, one stannate(IV) dianion, one isolated chloride anion and one lattice water molecule. The cyclohexylammonium cations adopt chair conformations. In the complex anion, two bidentate oxalate ligands and two chloride anions in cis positions coordinate octahedrally to the central Sn^IV atom. The cohesion of the molecular entities is ensured by the formation of N—H⋯O, O—H⋯O, O—H⋯Cl and N—H⋯Cl interactions involving cations, anions and the lattice water molecule, giving rise to a layer-like arrangement parallel to (010).

CCDC reference: 963857

Related literature

For general background on organotin(IV) chemistry and applications, see: Evans & Karpel (1985 ); Davies et al. (2008 ). For previous studies of tin(IV) derivatives with oxidoanions, see: Sarr & Diop (1990 ); Qamar-Kane & Diop (2010 ); Diallo et al. (2009 ). For crystal structures of halogenidotin(IV) compounds, see: Willey et al. (1998 ); Skapski et al. (1974 ); Gueye et al. (2011 ); Sow et al. (2013 ); Sarr et al. (2013 ).

Experimental

Crystal data

(C₆H₁₄N)₃[Sn(C₂O₄)₂Cl₂]Cl·H₂O
M_r = 719.64
Monoclinic, C 2/c
a = 27.9894 (10) Å
b = 12.3088 (5) Å
c = 19.3457 (7) Å
β = 105.542 (1)°
V = 6421.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 115 K
0.17 × 0.08 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
10624 measured reflections
7264 independent reflections
6028 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.095
S = 1.22
7264 reflections
346 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.89	2.11	2.957 (4)	160
N1—H1B⋯Cl3ⁱ	0.89	2.29	3.163 (4)	166
N1—H1C⋯O8	0.89	2.05	2.873 (4)	154
N1—H1C⋯O7	0.89	2.50	3.130 (5)	129
N2—H2A⋯O4ⁱⁱ	0.89	1.99	2.829 (4)	157
N2—H2A⋯O3ⁱⁱ	0.89	2.56	3.197 (4)	129
N2—H2B⋯Cl3ⁱ	0.89	2.41	3.209 (3)	150
N2—H2C⋯O6ⁱⁱⁱ	0.89	2.00	2.879 (4)	170
N3—H3A⋯Cl3	0.89	2.37	3.180 (3)	152
N3—H3A⋯O7	0.89	2.48	2.971 (4)	115
N3—H3B⋯O9	0.89	1.88	2.751 (5)	164
N3—H3C⋯O1^iv	0.89	2.08	2.957 (4)	167
O9—H1O⋯Cl3ⁱ	0.90	2.21	3.108 (3)	173
O9—H2O⋯O3^iv	0.87	2.28	2.950 (4)	135
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iv) $[x, -y, z+{\script{1\over 2}}]$ .

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 (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 963857

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813026901/wm2771sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026901/wm2771Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026901/wm2771Isup3.cdx

checkCIF report

Comment top

The interest to synthesize new organotin derivatives is related to their applications in numerous fields like agrochemicals, catalysis, medicine, surface disinfectants and marine antifouling paints (Evans & Karpel, 1985; Davies et al., 2008). Our group is involved from a long time in the synthetic quest of new organotin compounds, focusing in particular on the coordination affinity with oxoanions (Sarr & Diop, 1990; Diallo et al., 2009; Qamar-Kane & Diop, 2010; Gueye et al., 2011; Sow et al., 2013; Sarr et al., 2013). Thus, in the course of our ongoing studies on oxalato tin(IV) derivatives, we report herein the structure determination of the reaction product (C₆H₁₄N)₃[Sn(C₂O₄)₂Cl₂]Cl^.H₂O obtained from the reaction between [(C₆H₁₄N)]₂[C₂O₄]^.1.5H₂O and SnCl₂^.2H₂O. To the best of our knowledge, this is the first crystallographic report of a compound containing a [dihalogenido-bis(oxalato)stannate(IV)] anion.

The molecular entities of the title structure are shown in Fig. 1. The Sn(IV) atom of the stannate anion is six-coordinated by four oxalate oxygen atoms and two terminal chlorido anions in cis-position in a distorted octahedral geometry [Cl1–Sn–Cl2 = 97.37 (4)°, O1–Sn–O2 = 78.19 (10)°, O5–Sn–O6 = 79.99 (10)°]. The bidentate oxalato ligands are nearly planar with O1—C1—C2—O2 and O5—C3—C4—O6 torsion angles of 1.1 (6) and 2.7 (5)°, respectively. They form a dihedral angle of 86.62 (17)° between each other. The Sn—Cl distances [Sn–Cl1 = 2.3370 (11) Å, Sn–Cl2 = 2.3466 (10) Å] as well as the Sn–O distances [Sn–O1 = 2.097 (3) Å, Sn–O2 = 2.098 (3) Å, Sn–O5 = 2.060 (3) Å, Sn–O6 = 2.097 (3) Å] are in the typical range of Sn—Cl and Sn—O bonds reported previously in the literature (Willey et al., 1998; Skapski et al., 1974; Sow et al., 2013). The charges of the [Sn(C₂O₄)₂Cl₂]^2- dianion and the isolated Cl^- anion are compensated by three [(C₆H₁₁NH₃)]⁺ cations, all of which adopt in chair conformations. One uncoordinating water molecule is also present in the crystal lattice.

From a supramolecular view, three of the four oxygen atoms of each oxalato ligand are involved in hydrogen bonging interactions with the lattice water molecule and the surrounding cyclohexylammonium cations through O—H···O and N—H···O contacts, respectively (Table 1). The lattice water molecule is also involved in short contacts with the neighboring isolated Cl^- anion and a [(C₆H₁₁NH₃)]⁺ cation through O—H···Cl and N—H···O contacts, respectively. The isolated Cl^- anion is additionally hydrogen-bonded to the three cations through N—H···Cl interactions. The supramolecular contributions lead to the formation of layers extending parallel to (010) as shown in Fig. 2.

Related literature top

For general background on organotin(IV) chemistry and applications, see: Evans & Karpel (1985); Davies et al. (2008). For previous studies of tin(IV) derivatives with oxidoanions, see: Sarr & Diop (1990); Qamar-Kane & Diop (2010); Diallo et al. (2009). For crystal structures of halogenidotin(IV) compounds, see: Willey et al. (1998); Skapski et al. (1974); Gueye et al. (2011); Sow et al. (2013); Sarr et al. (2013).

Experimental top

All chemicals were purchased from Sigma-Aldrich or Merck and used without further purification. Crystals of the title compound were obtained by reacting [(C₆H₁₄N)]₂[C₂O₄]^.1.5H₂O (0.14 g, 0.44 mmol) with SnCl₂^.2H₂O (0.2 g, 0.88 mmol) in 75 ml of ethanol (96% purity) in an 1:2 molar ratio. The mixture was stirred during several hours at room temperature. Slow solvent evaporation yielded colorless crystals suitable for an X-ray crystallographic study.

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 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound with partial atom labelling. Colour code: Sn light grey, O red, N blue, Cl green. Displacement ellipsoids are draw at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis, showing the layer-like arrangement through intermolecular hydrogen bonding interactions N—H···O; O—H···Cl (dashed lines). Hydrogen atoms are omitted for clarity. Colour code: Sn pink, O red, N blue, Cl green, C grey.

Tris(cyclohexylammonium) cis-dichloridobis(oxalato-κ²O¹,O²)stannate(IV) chloride monohydrate top

Crystal data top

(C₆H₁₄N)₃[Sn(C₂O₄)₂Cl₂]Cl·H₂O	F(000) = 2960
M_r = 719.64	D_x = 1.489 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 59056 reflections
a = 27.9894 (10) Å	θ = 1.0–27.5°
b = 12.3088 (5) Å	µ = 1.09 mm⁻¹
c = 19.3457 (7) Å	T = 115 K
β = 105.542 (1)°	Prism, colourless
V = 6421.2 (4) Å³	0.17 × 0.08 × 0.03 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	6028 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ϕ scans (κ = 0) + additional ω scans	h = −36→36
10624 measured reflections	k = −15→10
7264 independent reflections	l = −25→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + 39.7649P] where P = (F_o² + 2F_c²)/3
7264 reflections	(Δ/σ)_max = 0.003
346 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

(C₆H₁₄N)₃[Sn(C₂O₄)₂Cl₂]Cl·H₂O	V = 6421.2 (4) Å³
M_r = 719.64	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.9894 (10) Å	µ = 1.09 mm⁻¹
b = 12.3088 (5) Å	T = 115 K
c = 19.3457 (7) Å	0.17 × 0.08 × 0.03 mm
β = 105.542 (1)°

Data collection top

Nonius KappaCCD diffractometer	6028 reflections with I > 2σ(I)
10624 measured reflections	R_int = 0.028
7264 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + 39.7649P] where P = (F_o² + 2F_c²)/3
7264 reflections	Δρ_max = 0.66 e Å⁻³
346 parameters	Δρ_min = −0.70 e Å⁻³

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. Intensities at low angles are poorly measured and three reflections with Error/e.s.d. greater than 4 have been omitted for convenience (respectively, 4.86, 4.84 and 4.24).

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

	x	y	z	U_iso*/U_eq
Sn	0.84481 (2)	−0.01264 (2)	0.08670 (2)	0.02266 (7)
O1	0.82137 (11)	−0.1343 (2)	0.00914 (14)	0.0275 (6)
O2	0.81693 (10)	−0.1304 (2)	0.14399 (14)	0.0247 (6)
O3	0.79899 (11)	−0.3092 (2)	−0.00137 (15)	0.0313 (6)
O4	0.79534 (11)	−0.3041 (2)	0.14046 (14)	0.0307 (6)
O5	0.84818 (10)	0.0972 (2)	0.16821 (14)	0.0277 (6)
O6	0.77157 (10)	0.0445 (2)	0.05761 (14)	0.0273 (6)
O8	0.72353 (11)	0.1682 (3)	0.08902 (16)	0.0366 (7)
O7	0.80129 (12)	0.2174 (2)	0.20695 (15)	0.0332 (7)
Cl1	0.92508 (4)	−0.08025 (10)	0.13280 (7)	0.0418 (3)
Cl2	0.86238 (5)	0.10594 (10)	0.00174 (6)	0.0429 (3)
C3	0.80701 (16)	0.1493 (3)	0.1644 (2)	0.0265 (8)
C4	0.76247 (15)	0.1196 (3)	0.0982 (2)	0.0256 (8)
C1	0.80865 (15)	−0.2263 (3)	0.0328 (2)	0.0244 (8)
C2	0.80675 (15)	−0.2225 (3)	0.1126 (2)	0.0240 (8)
N1	0.69051 (13)	0.2526 (3)	0.20683 (17)	0.0297 (8)
H1A	0.6955	0.2190	0.2489	0.045*
H1B	0.6989	0.3222	0.2140	0.045*
H1C	0.7090	0.2214	0.1815	0.045*
C5	0.63681 (15)	0.2442 (3)	0.1665 (2)	0.0273 (8)
H5	0.6318	0.2849	0.1215	0.033*
C6	0.62238 (16)	0.1271 (3)	0.1480 (2)	0.0331 (9)
H6A	0.6292	0.0841	0.1916	0.040*
H6B	0.6419	0.0980	0.1178	0.040*
C7	0.56753 (18)	0.1192 (4)	0.1089 (3)	0.0451 (12)
H7A	0.5616	0.1548	0.0627	0.054*
H7B	0.5584	0.0433	0.1005	0.054*
C8	0.53516 (18)	0.1710 (5)	0.1512 (3)	0.0493 (13)
H8A	0.5008	0.1685	0.1232	0.059*
H8B	0.5380	0.1303	0.1951	0.059*
C9	0.55019 (18)	0.2879 (4)	0.1696 (3)	0.0478 (13)
H9A	0.5303	0.3179	0.1991	0.057*
H9B	0.5440	0.3303	0.1258	0.057*
C10	0.60496 (16)	0.2953 (4)	0.2098 (2)	0.0346 (10)
H10A	0.6142	0.3709	0.2190	0.042*
H10B	0.6106	0.2584	0.2555	0.042*
N2	0.78665 (12)	0.4798 (3)	0.08874 (16)	0.0258 (7)
H2A	0.7910	0.5514	0.0931	0.039*
H2B	0.7694	0.4571	0.1185	0.039*
H2C	0.7702	0.4638	0.0438	0.039*
C11	0.83594 (14)	0.4248 (3)	0.10692 (19)	0.0241 (8)
H11	0.8307	0.3469	0.0971	0.029*
C12	0.86113 (15)	0.4396 (3)	0.1867 (2)	0.0279 (9)
H12A	0.8647	0.5166	0.1977	0.034*
H12B	0.8406	0.4080	0.2146	0.034*
C13	0.91179 (16)	0.3863 (4)	0.2071 (2)	0.0383 (11)
H13A	0.9277	0.3997	0.2574	0.046*
H13B	0.9080	0.3083	0.2002	0.046*
C14	0.94433 (17)	0.4298 (5)	0.1621 (2)	0.0453 (12)
H14A	0.9758	0.3915	0.1743	0.054*
H14B	0.9510	0.5062	0.1726	0.054*
C15	0.91917 (16)	0.4157 (4)	0.0819 (2)	0.0394 (11)
H15A	0.9397	0.4481	0.0543	0.047*
H15B	0.9159	0.3389	0.0705	0.047*
C16	0.86792 (15)	0.4688 (4)	0.0610 (2)	0.0314 (9)
H16A	0.8714	0.5469	0.0673	0.038*
H16B	0.8520	0.4544	0.0108	0.038*
N3	0.83237 (12)	0.1870 (3)	0.36505 (17)	0.0275 (7)
H3A	0.8182	0.1415	0.3298	0.041*
H3B	0.8172	0.2511	0.3573	0.041*
H3C	0.8299	0.1601	0.4067	0.041*
C17	0.88578 (15)	0.2008 (3)	0.3675 (2)	0.0291 (9)
H17	0.8875	0.2434	0.3255	0.035*
C18	0.91144 (17)	0.2645 (4)	0.4336 (2)	0.0428 (12)
H18A	0.9080	0.2269	0.4760	0.051*
H18B	0.8961	0.3355	0.4321	0.051*
C19	0.96627 (18)	0.2780 (5)	0.4377 (3)	0.0557 (15)
H19A	0.9697	0.3220	0.3978	0.067*
H19B	0.9827	0.3155	0.4818	0.067*
C20	0.9907 (2)	0.1698 (6)	0.4358 (4)	0.081 (2)
H20A	0.9896	0.1276	0.4777	0.097*
H20B	1.0252	0.1805	0.4367	0.097*
C21	0.9641 (2)	0.1080 (5)	0.3677 (5)	0.085 (2)
H21A	0.9674	0.1479	0.3259	0.103*
H21B	0.9796	0.0375	0.3676	0.103*
C22	0.90922 (19)	0.0926 (4)	0.3630 (4)	0.0556 (15)
H22A	0.8927	0.0574	0.3181	0.067*
H22B	0.9057	0.0464	0.4020	0.067*
Cl3	0.76656 (4)	−0.00855 (8)	0.28368 (5)	0.0305 (2)
O9	0.80156 (11)	0.3999 (2)	0.35850 (16)	0.0352 (7)
H1O	0.7804	0.4291	0.3195	0.042*
H2O	0.7911	0.4075	0.3965	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02068 (13)	0.02730 (13)	0.01990 (12)	−0.00111 (11)	0.00525 (9)	0.00308 (11)
O1	0.0342 (16)	0.0295 (14)	0.0206 (13)	−0.0004 (12)	0.0103 (12)	0.0007 (11)
O2	0.0285 (15)	0.0254 (13)	0.0212 (13)	−0.0018 (11)	0.0086 (11)	0.0002 (11)
O3	0.0387 (18)	0.0303 (15)	0.0258 (15)	0.0031 (13)	0.0102 (13)	−0.0038 (12)
O4	0.0421 (18)	0.0279 (14)	0.0241 (14)	−0.0028 (13)	0.0124 (13)	0.0019 (12)
O5	0.0299 (16)	0.0276 (14)	0.0259 (14)	0.0022 (12)	0.0082 (12)	0.0016 (11)
O6	0.0253 (15)	0.0298 (14)	0.0228 (13)	0.0025 (11)	−0.0007 (11)	−0.0039 (11)
O8	0.0314 (17)	0.0458 (18)	0.0323 (16)	0.0102 (14)	0.0080 (13)	−0.0029 (14)
O7	0.0456 (19)	0.0305 (15)	0.0239 (14)	−0.0047 (13)	0.0102 (13)	−0.0057 (12)
Cl1	0.0225 (5)	0.0539 (7)	0.0497 (7)	0.0053 (5)	0.0107 (5)	0.0141 (5)
Cl2	0.0541 (7)	0.0439 (6)	0.0339 (6)	−0.0059 (5)	0.0175 (5)	0.0134 (5)
C3	0.031 (2)	0.0275 (19)	0.0209 (19)	−0.0055 (16)	0.0071 (17)	0.0012 (16)
C4	0.026 (2)	0.0270 (19)	0.026 (2)	0.0059 (16)	0.0112 (17)	0.0080 (16)
C1	0.023 (2)	0.0279 (19)	0.0219 (19)	0.0056 (16)	0.0062 (16)	0.0025 (15)
C2	0.026 (2)	0.0256 (19)	0.0221 (19)	0.0021 (15)	0.0086 (16)	0.0042 (15)
N1	0.034 (2)	0.0362 (19)	0.0209 (16)	0.0000 (15)	0.0105 (15)	−0.0005 (14)
C5	0.027 (2)	0.034 (2)	0.0196 (19)	0.0017 (17)	0.0045 (16)	0.0037 (16)
C6	0.035 (2)	0.033 (2)	0.032 (2)	−0.0027 (18)	0.0093 (19)	−0.0007 (18)
C7	0.040 (3)	0.051 (3)	0.041 (3)	−0.007 (2)	0.004 (2)	−0.006 (2)
C8	0.026 (2)	0.079 (4)	0.039 (3)	−0.012 (2)	0.002 (2)	−0.003 (3)
C9	0.033 (3)	0.063 (3)	0.046 (3)	0.008 (2)	0.006 (2)	−0.006 (2)
C10	0.032 (2)	0.037 (2)	0.033 (2)	0.0022 (19)	0.0059 (19)	−0.0068 (19)
N2	0.0258 (17)	0.0314 (17)	0.0195 (15)	−0.0007 (14)	0.0048 (13)	−0.0006 (14)
C11	0.023 (2)	0.0265 (19)	0.0206 (18)	0.0025 (15)	0.0024 (15)	0.0011 (15)
C12	0.029 (2)	0.036 (2)	0.0187 (18)	−0.0034 (17)	0.0055 (16)	0.0026 (16)
C13	0.029 (2)	0.057 (3)	0.026 (2)	0.002 (2)	0.0027 (18)	0.009 (2)
C14	0.028 (2)	0.070 (3)	0.035 (2)	0.002 (2)	0.003 (2)	−0.001 (2)
C15	0.025 (2)	0.059 (3)	0.037 (2)	0.008 (2)	0.0132 (19)	−0.001 (2)
C16	0.031 (2)	0.041 (2)	0.0231 (19)	−0.0006 (19)	0.0096 (17)	0.0002 (17)
N3	0.0274 (18)	0.0340 (18)	0.0207 (16)	−0.0031 (14)	0.0057 (14)	−0.0012 (14)
C17	0.024 (2)	0.035 (2)	0.029 (2)	−0.0061 (17)	0.0088 (17)	0.0016 (17)
C18	0.033 (3)	0.060 (3)	0.034 (2)	−0.012 (2)	0.005 (2)	0.000 (2)
C19	0.030 (3)	0.072 (4)	0.057 (3)	−0.020 (3)	−0.001 (2)	0.006 (3)
C20	0.023 (3)	0.084 (5)	0.124 (6)	−0.001 (3)	0.002 (3)	0.039 (5)
C21	0.042 (4)	0.057 (4)	0.169 (8)	0.011 (3)	0.049 (5)	0.002 (5)
C22	0.036 (3)	0.049 (3)	0.085 (4)	0.003 (2)	0.023 (3)	−0.004 (3)
Cl3	0.0300 (5)	0.0338 (5)	0.0303 (5)	−0.0063 (4)	0.0126 (4)	−0.0057 (4)
O9	0.0339 (17)	0.0423 (17)	0.0297 (15)	0.0034 (14)	0.0091 (13)	0.0073 (13)

Geometric parameters (Å, º) top

Sn—O5	2.060 (3)	C11—C16	1.520 (5)
Sn—O6	2.097 (3)	C11—C12	1.526 (5)
Sn—O1	2.097 (3)	C11—H11	0.9800
Sn—O2	2.098 (3)	C12—C13	1.516 (6)
Sn—Cl1	2.3370 (11)	C12—H12A	0.9700
Sn—Cl2	2.3466 (10)	C12—H12B	0.9700
O1—C1	1.306 (5)	C13—C14	1.516 (6)
O2—C2	1.281 (5)	C13—H13A	0.9700
O3—C1	1.206 (5)	C13—H13B	0.9700
O4—C2	1.222 (4)	C14—C15	1.531 (6)
O5—C3	1.303 (5)	C14—H14A	0.9700
O6—C4	1.282 (5)	C14—H14B	0.9700
O8—C4	1.214 (5)	C15—C16	1.529 (6)
O7—C3	1.215 (5)	C15—H15A	0.9700
C3—C4	1.572 (6)	C15—H15B	0.9700
C1—C2	1.561 (5)	C16—H16A	0.9700
N1—C5	1.500 (5)	C16—H16B	0.9700
N1—H1A	0.8900	N3—C17	1.493 (5)
N1—H1B	0.8900	N3—H3A	0.8900
N1—H1C	0.8900	N3—H3B	0.8900
C5—C6	1.513 (6)	N3—H3C	0.8900
C5—C10	1.514 (6)	C17—C22	1.498 (6)
C5—H5	0.9800	C17—C18	1.508 (6)
C6—C7	1.522 (6)	C17—H17	0.9800
C6—H6A	0.9700	C18—C19	1.524 (7)
C6—H6B	0.9700	C18—H18A	0.9700
C7—C8	1.514 (7)	C18—H18B	0.9700
C7—H7A	0.9700	C19—C20	1.503 (9)
C7—H7B	0.9700	C19—H19A	0.9700
C8—C9	1.514 (7)	C19—H19B	0.9700
C8—H8A	0.9700	C20—C21	1.530 (10)
C8—H8B	0.9700	C20—H20A	0.9700
C9—C10	1.525 (6)	C20—H20B	0.9700
C9—H9A	0.9700	C21—C22	1.526 (7)
C9—H9B	0.9700	C21—H21A	0.9700
C10—H10A	0.9700	C21—H21B	0.9700
C10—H10B	0.9700	C22—H22A	0.9700
N2—C11	1.492 (5)	C22—H22B	0.9700
N2—H2A	0.8900	O9—H1O	0.8992
N2—H2B	0.8900	O9—H2O	0.8667
N2—H2C	0.8900

O5—Sn—O6	79.99 (10)	N2—C11—C16	110.6 (3)
O5—Sn—O1	163.31 (11)	N2—C11—C12	109.4 (3)
O6—Sn—O1	87.22 (10)	C16—C11—C12	111.3 (3)
O5—Sn—O2	89.79 (10)	N2—C11—H11	108.5
O6—Sn—O2	84.16 (11)	C16—C11—H11	108.5
O1—Sn—O2	78.19 (10)	C12—C11—H11	108.5
O5—Sn—Cl1	95.71 (8)	C13—C12—C11	111.0 (3)
O6—Sn—Cl1	173.10 (8)	C13—C12—H12A	109.4
O1—Sn—Cl1	95.93 (8)	C11—C12—H12A	109.4
O2—Sn—Cl1	90.46 (8)	C13—C12—H12B	109.4
O5—Sn—Cl2	98.78 (8)	C11—C12—H12B	109.4
O6—Sn—Cl2	88.65 (8)	H12A—C12—H12B	108.0
O1—Sn—Cl2	91.55 (8)	C14—C13—C12	111.2 (4)
O2—Sn—Cl2	167.72 (8)	C14—C13—H13A	109.4
Cl1—Sn—Cl2	97.37 (4)	C12—C13—H13A	109.4
C1—O1—Sn	115.6 (2)	C14—C13—H13B	109.4
C2—O2—Sn	115.3 (2)	C12—C13—H13B	109.4
C3—O5—Sn	114.9 (2)	H13A—C13—H13B	108.0
C4—O6—Sn	114.7 (2)	C13—C14—C15	110.9 (4)
O7—C3—O5	125.1 (4)	C13—C14—H14A	109.5
O7—C3—C4	119.5 (4)	C15—C14—H14A	109.5
O5—C3—C4	115.4 (3)	C13—C14—H14B	109.5
O8—C4—O6	125.7 (4)	C15—C14—H14B	109.5
O8—C4—C3	119.3 (4)	H14A—C14—H14B	108.0
O6—C4—C3	115.0 (3)	C16—C15—C14	111.4 (4)
O3—C1—O1	125.8 (4)	C16—C15—H15A	109.4
O3—C1—C2	120.4 (3)	C14—C15—H15A	109.4
O1—C1—C2	113.9 (3)	C16—C15—H15B	109.4
O4—C2—O2	124.7 (3)	C14—C15—H15B	109.4
O4—C2—C1	119.6 (3)	H15A—C15—H15B	108.0
O2—C2—C1	115.7 (3)	C11—C16—C15	110.5 (3)
C5—N1—H1A	109.5	C11—C16—H16A	109.6
C5—N1—H1B	109.5	C15—C16—H16A	109.6
H1A—N1—H1B	109.5	C11—C16—H16B	109.6
C5—N1—H1C	109.5	C15—C16—H16B	109.6
H1A—N1—H1C	109.5	H16A—C16—H16B	108.1
H1B—N1—H1C	109.5	C17—N3—H3A	109.5
N1—C5—C6	110.8 (3)	C17—N3—H3B	109.5
N1—C5—C10	109.8 (3)	H3A—N3—H3B	109.5
C6—C5—C10	111.5 (4)	C17—N3—H3C	109.5
N1—C5—H5	108.2	H3A—N3—H3C	109.5
C6—C5—H5	108.2	H3B—N3—H3C	109.5
C10—C5—H5	108.2	N3—C17—C22	110.3 (3)
C5—C6—C7	110.4 (4)	N3—C17—C18	109.4 (3)
C5—C6—H6A	109.6	C22—C17—C18	113.3 (4)
C7—C6—H6A	109.6	N3—C17—H17	107.9
C5—C6—H6B	109.6	C22—C17—H17	107.9
C7—C6—H6B	109.6	C18—C17—H17	107.9
H6A—C6—H6B	108.1	C17—C18—C19	110.2 (4)
C8—C7—C6	112.0 (4)	C17—C18—H18A	109.6
C8—C7—H7A	109.2	C19—C18—H18A	109.6
C6—C7—H7A	109.2	C17—C18—H18B	109.6
C8—C7—H7B	109.2	C19—C18—H18B	109.6
C6—C7—H7B	109.2	H18A—C18—H18B	108.1
H7A—C7—H7B	107.9	C20—C19—C18	111.1 (5)
C9—C8—C7	111.0 (4)	C20—C19—H19A	109.4
C9—C8—H8A	109.4	C18—C19—H19A	109.4
C7—C8—H8A	109.4	C20—C19—H19B	109.4
C9—C8—H8B	109.4	C18—C19—H19B	109.4
C7—C8—H8B	109.4	H19A—C19—H19B	108.0
H8A—C8—H8B	108.0	C19—C20—C21	110.1 (5)
C8—C9—C10	110.8 (4)	C19—C20—H20A	109.6
C8—C9—H9A	109.5	C21—C20—H20A	109.6
C10—C9—H9A	109.5	C19—C20—H20B	109.6
C8—C9—H9B	109.5	C21—C20—H20B	109.6
C10—C9—H9B	109.5	H20A—C20—H20B	108.2
H9A—C9—H9B	108.1	C22—C21—C20	111.2 (6)
C5—C10—C9	110.7 (4)	C22—C21—H21A	109.4
C5—C10—H10A	109.5	C20—C21—H21A	109.4
C9—C10—H10A	109.5	C22—C21—H21B	109.4
C5—C10—H10B	109.5	C20—C21—H21B	109.4
C9—C10—H10B	109.5	H21A—C21—H21B	108.0
H10A—C10—H10B	108.1	C17—C22—C21	109.6 (4)
C11—N2—H2A	109.5	C17—C22—H22A	109.8
C11—N2—H2B	109.5	C21—C22—H22A	109.8
H2A—N2—H2B	109.5	C17—C22—H22B	109.8
C11—N2—H2C	109.5	C21—C22—H22B	109.8
H2A—N2—H2C	109.5	H22A—C22—H22B	108.2
H2B—N2—H2C	109.5	H1O—O9—H2O	111.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	2.11	2.957 (4)	160
N1—H1B···Cl3ⁱ	0.89	2.29	3.163 (4)	166
N1—H1C···O8	0.89	2.05	2.873 (4)	154
N1—H1C···O7	0.89	2.50	3.130 (5)	129
N2—H2A···O4ⁱⁱ	0.89	1.99	2.829 (4)	157
N2—H2A···O3ⁱⁱ	0.89	2.56	3.197 (4)	129
N2—H2B···Cl3ⁱ	0.89	2.41	3.209 (3)	150
N2—H2C···O6ⁱⁱⁱ	0.89	2.00	2.879 (4)	170
N3—H3A···Cl3	0.89	2.37	3.180 (3)	152
N3—H3A···O7	0.89	2.48	2.971 (4)	115
N3—H3B···O9	0.89	1.88	2.751 (5)	164
N3—H3C···O1^iv	0.89	2.08	2.957 (4)	167
O9—H1O···Cl3ⁱ	0.90	2.21	3.108 (3)	173
O9—H2O···O3^iv	0.87	2.28	2.950 (4)	135

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	2.11	2.957 (4)	159.9
N1—H1B···Cl3ⁱ	0.89	2.29	3.163 (4)	166.1
N1—H1C···O8	0.89	2.05	2.873 (4)	154.3
N1—H1C···O7	0.89	2.50	3.130 (5)	128.6
N2—H2A···O4ⁱⁱ	0.89	1.99	2.829 (4)	156.7
N2—H2A···O3ⁱⁱ	0.89	2.56	3.197 (4)	129.2
N2—H2B···Cl3ⁱ	0.89	2.41	3.209 (3)	150.1
N2—H2C···O6ⁱⁱⁱ	0.89	2.00	2.879 (4)	169.5
N3—H3A···Cl3	0.89	2.37	3.180 (3)	151.8
N3—H3A···O7	0.89	2.48	2.971 (4)	115.4
N3—H3B···O9	0.89	1.88	2.751 (5)	164.0
N3—H3C···O1^iv	0.89	2.08	2.957 (4)	166.8
O9—H1O···Cl3ⁱ	0.90	2.21	3.108 (3)	173.4
O9—H2O···O3^iv	0.87	2.28	2.950 (4)	134.7

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

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Davies, A. G., Gielen, M., Pannell, K. H. & Tiekink, E. R. T. (2008). In Tin Chemistry, Fundamentals, Frontiers, and Applications. Chichester, UK: John Wiley & Sons Ltd. Google Scholar
Diallo, W., Diassé-Sarr, A., Diop, L., Mahieu, B., Biesemans, M., Willem, R., Kociok-Köhn, G. & Molloy, K. C. (2009). St. Cerc. St. CICBIA, 10, 207–212. CAS Google Scholar
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology. J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2011). Main Group Met. Chem. 34, 3–5. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Qamar-Kane, H. & Diop, L. (2010). St. Cerc. St. CICBIA, 11, 389–392. Google Scholar
Sarr, M., Diasse-Sarr, A., Diallo, W., Plasseraud, L. & Cattey, H. (2013). Acta Cryst. E69, m473–m474. CSD CrossRef CAS IUCr Journals Google Scholar
Sarr, O. & Diop, L. (1990). Spectrochim. Acta Part A, 46, 1239–1244. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skapski, A. C., Guerchais, J.-E. & Calves, J.-Y. (1974). C. R. Acad. Sci. Ser. C, 278, 1377–1379. CAS Google Scholar
Sow, Y., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2013). Acta Cryst. E69, m106–m107. CSD CrossRef CAS IUCr Journals Google Scholar
Willey, G. R., Woodman, T. J., Deeth, R. J. & Errington, W. (1998). Main Group Met. Chem. 21, 583–591. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.