Crystal structure of bis­(2-methyl-1H-imidazol-3-ium) μ-oxalato-bis­[n-butyl­tri­chlorido­stannate(IV)]

Diop, M.B.; Diop, L.; Oliver, A.G.

doi:10.1107/S2056989016008434

research communications

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ISSN: 2056-9890

Volume 72| Part 6| June 2016| Pages 858-860

https://doi.org/10.1107/S2056989016008434

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Crystal structure of bis(2-methyl-1H-imidazol-3-ium) μ-oxalato-bis[n-butyltrichloridostannate(IV)]

Mouhamadou Birame Diop,^a ^* Libasse Diop ^a and Allen G. Oliver ^b

^aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDepartment of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46557-5670, USA
^*Correspondence e-mail: mouhamadoubdiop@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 7 May 2016; accepted 24 May 2016; online 27 May 2016)

The Sn^IV atom in the centrosymmetric anion of the title salt, (C₄H₇N₂)₂[Sn₂(C₄H₉)₂(C₂O₄)Cl₆], is coordinated in a distorted octahedral mode by two O atoms of a bridging oxalate moiety, three Cl atoms and a C atom of an n-butyl group. The latter is disordered over two sets of sites in a 0.66:0.33 occupancy ratio. N—H⋯O and N—H⋯Cl hydrogen bonds involving the 2-methylimidazolium cation and neighbouring anions result in the formation of chains extending parallel to [001].

Keywords: crystal structure; organotin(IV) complex; oxalate; hydrogen bonds.

CCDC reference: 1481678

1. Chemical context

Ammonium salts of oxalatostannates(IV) with additional halogen atoms bonded within the anion are well known in the literature. Skapski et al. (1974 ) have reported the crystal structure of [(R₄N)₂][C₂O₄(SnCl₄)₂] (R = ethyl) while Le Floch et al. (1975 ) have published spectroscopic studies of [(R₄N)₂][C₂O₄(SnX₄)₂] (R = ethyl, X = Cl, Br, I; R = butyl, X = Br). Our group has investigated several complexes containing an oxalate group chelating an SnCl₄ moiety or an [SnCl₃·H₂O]⁺ fragment, resulting in framework structures (Sow et al., 2013 ; Diop et al., 2015 ). In all cases, the environment around the tin(IV) atom is distorted octahedral.

In the present communication we report on the reaction between 2-methyl-imidazolium hydrogenoxalate dihydrate and tin(IV) butyltrichloride that yielded the title compound, (C₄H₇N₂)₂[(Sn₂(C₄H₉)₂(C₂O₄)Cl₆].

2. Structural commentary

The distannate anion, [Sn₂(C₄H₉)₂(C₂O₄)Cl₆]²⁻, is located about a center of symmetry and thus only one half of the molecule is present in the asymmetric unit (Fig. 1). The full molecule consists of a central oxalate anion bridging two SnBuCl₃ moieties (Fig. 2) similar to the binuclear stannate(IV) anion reported for (Et₄N)₂[C₂O₄(SnCl₄)₂] (Skapski et al., 1974). In addition to the bis-chelating and bridging oxalate oxygen atoms, the octahedral coordination sphere is completed by three chlorine atoms and the C atom of a disordered n-butyl group (Fig. 1). The C—O distances (Table 1) are consistent with an almost perfect π delocalization within the oxalate anion, as expected for a centrosymmetric bis-chelation. The Sn—C length is consistent with previously reported values (Table 1; Diop et al., 2013 ). The Sn—Cl distances (Table 1) are also comparable with those in related compounds, e.g. in (Bu₄N)[SnBuCl₄] (Diop et al., 2013), (Me₄N)[C₂O₄SnCl₃(H₂O)] (Sow et al., 2013) or [(methyl-2-imidazolium)][C₂O₄SnCl₃(H₂O)] (Diop et al., 2015). The equatorial Sn—Cl1 bond that is coplanar with the oxalate anion is considerably shorter than the Sn—Cl2 and Sn—Cl3 bonds that are oriented axially (Fig. 2, Table 1). The Sn—O1 and Sn—O2 bond lengths are fully consistent with previously characterized examples (Sow et al., 2013; Gueye et al., 2014 ; Sarr et al., 2015 ). Distortions from an ideal octahedral coordination environment are reflected in the bond angles about the Sn^IV atom (Table 1). Notably, the O1—Sn—O2 angle is less than 90° and the axial Cl2—Sn—Cl3 bond angle deviates considerably from an ideal of 180°.

Table 1
Selected geometric parameters (Å, °)

Sn1—C2	2.122 (2)	O2—C1	1.243 (2)
Sn1—O1	2.1878 (13)	O2—Sn1ⁱ	2.2475 (13)
Sn1—O2ⁱ	2.2475 (13)	N1—C6	1.313 (3)
Sn1—Cl1	2.3731 (5)	N1—C7	1.354 (3)
Sn1—Cl3	2.4460 (6)	N2—C6	1.323 (3)
Sn1—Cl2	2.4536 (5)	N2—C8	1.356 (3)
O1—C1	1.248 (2)	C7—C8	1.336 (3)

C2—Sn1—O1	166.44 (7)	O2ⁱ—Sn1—Cl3	86.17 (4)
C2—Sn1—O2ⁱ	92.40 (7)	Cl1—Sn1—Cl3	92.40 (2)
O1—Sn1—O2ⁱ	74.04 (5)	C2—Sn1—Cl2	96.58 (7)
C2—Sn1—Cl1	108.24 (6)	O1—Sn1—Cl2	82.42 (4)
O1—Sn1—Cl1	85.32 (4)	O2ⁱ—Sn1—Cl2	84.14 (4)
O2ⁱ—Sn1—Cl1	159.27 (4)	Cl1—Sn1—Cl2	91.38 (2)
C2—Sn1—Cl3	98.81 (7)	Cl3—Sn1—Cl2	162.13 (2)
O1—Sn1—Cl3	80.48 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 1
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Disordered parts of the n-butyl chain are shown.

Figure 2
The full anion and two counter-cations in the title compound. Displacement ellipsoids are drawn at the 50% probability level. Only the major part of the disordered n-butyl chain is shown. [Symmetry code: (A) −x + 1, −y + 1, −z + 1.]

One methyl-2-imidazolium counter-cation is also present in the asymmetric unit. As expected, the lengths of the C—N and C7—C8 bonds indicate π-delocalization in this cation (Table 1).

3. Supramolecular features

The imidazolium cation bridges two neighbouring [Sn₂(C₄H₉)₂(C₂O₄)Cl₆]²⁻ anions through N—H⋯O and N—H⋯Cl hydrogen bonds, leading to the formation of chains extending parallel to [001] (Fig. 3, Table 2) whereby pairs of the cations are involved in this bridging motif, each alternating across the inversion center located between the cations. The chains are connected by additional C—H⋯Cl hydrogen bonds, giving a layer structure parallel to (100).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1	0.74 (3)	2.75 (3)	3.398 (2)	147 (3)
N1—H1N⋯O1	0.74 (3)	2.44 (3)	2.993 (2)	133 (3)
N2—H2N⋯Cl2ⁱⁱ	0.77 (2)	2.43 (3)	3.187 (2)	170 (2)
C7—H7⋯Cl3ⁱⁱⁱ	0.95	2.87	3.517 (2)	127
C9—H9A⋯Cl1	0.98	2.92	3.696 (3)	136
Symmetry codes: (ii) x, y, z-1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 3
The packing of the molecular components in a view approximately along [010]. N—H⋯O and N—H⋯Cl hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37 with one update; Groom et al., 2016 ) returned 51 different structures containing 2-methyl-1H-imidazol-3-ium cations and hundreds of those containing bis-chelating oxalate anions. Those of particular relevance to the title structure have been detailed above.

5. Synthesis and crystallization

Crystals of [2-methyl-1H-imidazol-3-ium][HC₂O₄·2H₂O] (L) were obtained by mixing equimolar amounts of 2-methyl-imidazole with oxalic acid in water, followed by forced evaporation of the solvent at 333 K. A molar 2:1 mixture of (L) with SnBuCl₃ in acetonitrile was allowed to react. Crystals of the title compound suitable for structural examination were obtained after slow evaporation of acetonitrile at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were included in geometrically calculated positions with C—H = 0.98 (methyl) and 0.99 Å (methylene), with U_iso(H) = 1.5U_eq(C) (methyl), and 1.2U_eq(C) (methylene). H atoms bound to N atoms within the cation were derived from difference maps and were refined freely. The n-butyl group was found to exhibit positional disorder, and was modelled with the peripheral three carbon atoms disordered over two sets of sites. Occupancies for these two sets were initially refined upon inspection of the refined occupancies. In the final model the occupancies were fixed at 2/3:1/3. Disordered pairs of carbon atoms (C3/C3A, C4/C4A, C5/C5A) were restrained to have similar atomic displacement parameters.

Table 3
Experimental details

Crystal data
Chemical formula	(C₄H₇N₂)₂[Sn₂(C₄H₉)₂(C₂O₄)Cl₆]
M_r	818.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	13.4674 (5), 11.4709 (4), 10.2030 (3)
β (°)	100.453 (1)
V (Å³)	1550.03 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.16
Crystal size (mm)	0.29 × 0.18 × 0.12

Data collection
Diffractometer	Bruker Kappa X8 APEXII
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.671, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	20211, 3868, 3490
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.06
No. of reflections	3868
No. of parameters	192
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.46
Computer programs: APEX2 and SAINT (Bruker, 2015 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), XP (Sheldrick, 2008 ), CIFTAB (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1481678

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989016008434/wm5293sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016008434/wm5293Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: CIFTAB (Sheldrick, 2008) and publCIF (Westrip, 2010).

Bis(2-methyl-1H-imidazol-3-ium) µ-oxalato-bis[n-butyltrichloridostannate(IV)] top

Crystal data top

(C₄H₇N₂)₂[Sn₂(C₄H₉)₂(C₂O₄)Cl₆]	F(000) = 804
M_r = 818.60	D_x = 1.754 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.4674 (5) Å	Cell parameters from 9885 reflections
b = 11.4709 (4) Å	θ = 2.7–28.3°
c = 10.2030 (3) Å	µ = 2.16 mm⁻¹
β = 100.453 (1)°	T = 200 K
V = 1550.03 (9) Å³	Block, colorless
Z = 2	0.29 × 0.18 × 0.12 mm

Data collection top

Bruker Kappa X8 APEXII diffractometer	3868 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
combination of ω and φ–scans	h = −17→13
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −14→15
T_min = 0.671, T_max = 0.811	l = −13→13
20211 measured reflections

Refinement top

Refinement on F²	Primary atom site location: real-space vector search
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.021	Hydrogen site location: mixed
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0236P)² + 0.9516P] where P = (F_o² + 2F_c²)/3
3868 reflections	(Δ/σ)_max = 0.022
192 parameters	Δρ_max = 0.69 e Å⁻³
18 restraints	Δρ_min = −0.46 e Å⁻³

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. Disorder in the n-butyl chain was modeled over two sites. Occupancies were initially refined and subsequently set to 0.66667:0.33333. Carbon atoms were refined with anisotropic atomic displacement parameters and the disordered carbon atoms were restrained to have similar displacement parameters.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.71591 (2)	0.52312 (2)	0.53372 (2)	0.03131 (5)
Cl1	0.81275 (4)	0.42161 (6)	0.39795 (5)	0.04767 (13)
Cl2	0.71227 (4)	0.35142 (5)	0.67619 (5)	0.04538 (12)
Cl3	0.66628 (5)	0.67332 (6)	0.36433 (6)	0.05395 (15)
O1	0.58579 (10)	0.43651 (13)	0.41329 (12)	0.0341 (3)
O2	0.41920 (10)	0.42053 (12)	0.38137 (13)	0.0339 (3)
C1	0.50131 (14)	0.45924 (16)	0.44091 (17)	0.0296 (4)
C2	0.81592 (17)	0.6238 (2)	0.6744 (2)	0.0465 (5)
H2A	0.7753	0.6723	0.7251	0.056*	0.6667
H2B	0.8569	0.5700	0.7383	0.056*	0.6667
H2C	0.7810	0.6968	0.6911	0.056*	0.3333
H2D	0.8300	0.5800	0.7594	0.056*	0.3333
C3	0.8844 (5)	0.7002 (5)	0.6182 (8)	0.0621 (16)	0.6667
H3A	0.8439	0.7537	0.5534	0.075*	0.6667
H3B	0.9263	0.6520	0.5689	0.075*	0.6667
C4	0.9514 (6)	0.7697 (7)	0.7186 (9)	0.096 (3)	0.6667
H4A	0.9091	0.8112	0.7734	0.115*	0.6667
H4B	0.9955	0.7154	0.7783	0.115*	0.6667
C5	1.0148 (5)	0.8544 (6)	0.6693 (11)	0.147 (4)	0.6667
H5A	1.0609	0.8144	0.6202	0.221*	0.6667
H5B	1.0539	0.8973	0.7444	0.221*	0.6667
H5C	0.9725	0.9090	0.6097	0.221*	0.6667
C3A	0.9164 (10)	0.6557 (15)	0.6353 (18)	0.089 (5)	0.3333
H3C	0.9050	0.7118	0.5603	0.107*	0.3333
H3D	0.9483	0.5850	0.6057	0.107*	0.3333
C4A	0.9967 (9)	0.7180 (13)	0.772 (2)	0.125 (6)	0.3333
H4C	0.9875	0.6829	0.8578	0.150*	0.3333
H4D	1.0686	0.7138	0.7634	0.150*	0.3333
C5A	0.9606 (11)	0.8257 (19)	0.7572 (18)	0.115 (5)	0.3333
H5D	1.0101	0.8801	0.8061	0.173*	0.3333
H5E	0.8976	0.8304	0.7921	0.173*	0.3333
H5F	0.9476	0.8462	0.6624	0.173*	0.3333
N1	0.61980 (17)	0.41626 (18)	0.13231 (19)	0.0462 (5)
H1N	0.644 (2)	0.434 (3)	0.201 (3)	0.059 (9)*
N2	0.60535 (16)	0.37133 (18)	−0.07045 (18)	0.0463 (5)
H2N	0.6237 (19)	0.366 (2)	−0.137 (2)	0.044 (7)*
C6	0.6683 (2)	0.4165 (2)	0.0316 (2)	0.0487 (5)
C7	0.52646 (18)	0.36986 (19)	0.0958 (2)	0.0438 (5)
H7	0.4773	0.3595	0.1508	0.053*
C8	0.51718 (18)	0.34151 (19)	−0.0328 (2)	0.0438 (5)
H8A	0.4600	0.3072	−0.0873	0.053*
C9	0.7714 (3)	0.4571 (4)	0.0320 (3)	0.0894 (12)
H9A	0.7993	0.4905	0.1193	0.134*
H9B	0.7707	0.5166	−0.0370	0.134*
H9C	0.8134	0.3913	0.0140	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02611 (7)	0.04132 (8)	0.02698 (7)	−0.00213 (5)	0.00611 (5)	−0.00174 (5)
Cl1	0.0358 (3)	0.0706 (4)	0.0385 (3)	0.0073 (2)	0.0116 (2)	−0.0100 (2)
Cl2	0.0549 (3)	0.0459 (3)	0.0359 (2)	−0.0024 (2)	0.0097 (2)	0.0052 (2)
Cl3	0.0489 (3)	0.0611 (4)	0.0522 (3)	0.0034 (3)	0.0101 (3)	0.0221 (3)
O1	0.0282 (7)	0.0459 (7)	0.0289 (6)	−0.0013 (6)	0.0074 (5)	−0.0078 (6)
O2	0.0286 (7)	0.0432 (8)	0.0304 (6)	−0.0032 (6)	0.0065 (5)	−0.0085 (6)
C1	0.0300 (9)	0.0354 (9)	0.0243 (8)	−0.0013 (7)	0.0073 (7)	−0.0005 (7)
C2	0.0365 (11)	0.0579 (14)	0.0445 (11)	−0.0075 (10)	0.0058 (9)	−0.0150 (10)
C3	0.045 (3)	0.059 (3)	0.078 (3)	−0.020 (2)	0.000 (3)	0.002 (3)
C4	0.077 (5)	0.080 (5)	0.121 (6)	−0.043 (4)	−0.009 (4)	−0.041 (4)
C5	0.061 (4)	0.082 (4)	0.283 (12)	−0.032 (3)	−0.009 (5)	−0.007 (6)
C3A	0.050 (8)	0.110 (13)	0.111 (12)	−0.031 (7)	0.024 (7)	−0.061 (10)
C4A	0.053 (7)	0.094 (10)	0.233 (19)	0.011 (6)	0.042 (9)	−0.020 (11)
C5A	0.058 (8)	0.169 (18)	0.122 (13)	−0.011 (10)	0.027 (8)	−0.018 (12)
N1	0.0598 (13)	0.0507 (11)	0.0279 (9)	−0.0053 (9)	0.0073 (8)	−0.0023 (8)
N2	0.0590 (12)	0.0515 (11)	0.0290 (9)	−0.0022 (9)	0.0097 (8)	−0.0031 (8)
C6	0.0551 (14)	0.0579 (14)	0.0330 (10)	−0.0088 (11)	0.0080 (9)	0.0010 (9)
C7	0.0513 (13)	0.0393 (11)	0.0425 (11)	0.0014 (9)	0.0132 (10)	0.0031 (9)
C8	0.0495 (12)	0.0363 (10)	0.0443 (11)	−0.0019 (9)	0.0050 (10)	−0.0012 (9)
C9	0.063 (2)	0.153 (4)	0.0526 (17)	−0.038 (2)	0.0123 (14)	−0.0002 (19)

Geometric parameters (Å, º) top

Sn1—C2	2.122 (2)	C5—H5C	0.9800
Sn1—O1	2.1878 (13)	C3A—C4A	1.76 (2)
Sn1—O2ⁱ	2.2475 (13)	C3A—H3C	0.9900
Sn1—Cl1	2.3731 (5)	C3A—H3D	0.9900
Sn1—Cl3	2.4460 (6)	C4A—C5A	1.33 (2)
Sn1—Cl2	2.4536 (5)	C4A—H4C	0.9900
O1—C1	1.248 (2)	C4A—H4D	0.9900
O2—C1	1.243 (2)	C5A—H5D	0.9800
O2—Sn1ⁱ	2.2475 (13)	C5A—H5E	0.9800
C1—C1ⁱ	1.531 (3)	C5A—H5F	0.9800
C2—C3	1.463 (7)	N1—C6	1.313 (3)
C2—C3A	1.524 (16)	N1—C7	1.354 (3)
C2—H2A	0.9900	N1—H1N	0.74 (3)
C2—H2B	0.9900	N2—C6	1.323 (3)
C2—H2C	0.9900	N2—C8	1.356 (3)
C2—H2D	0.9900	N2—H2N	0.77 (2)
C3—C4	1.471 (9)	C6—C9	1.465 (4)
C3—H3A	0.9900	C7—C8	1.336 (3)
C3—H3B	0.9900	C7—H7	0.9500
C4—C5	1.443 (11)	C8—H8A	0.9500
C4—H4A	0.9900	C9—H9A	0.9800
C4—H4B	0.9900	C9—H9B	0.9800
C5—H5A	0.9800	C9—H9C	0.9800
C5—H5B	0.9800

C2—Sn1—O1	166.44 (7)	C4—C5—H5B	109.5
C2—Sn1—O2ⁱ	92.40 (7)	H5A—C5—H5B	109.5
O1—Sn1—O2ⁱ	74.04 (5)	C4—C5—H5C	109.5
C2—Sn1—Cl1	108.24 (6)	H5A—C5—H5C	109.5
O1—Sn1—Cl1	85.32 (4)	H5B—C5—H5C	109.5
O2ⁱ—Sn1—Cl1	159.27 (4)	C2—C3A—C4A	109.7 (11)
C2—Sn1—Cl3	98.81 (7)	C2—C3A—H3C	109.7
O1—Sn1—Cl3	80.48 (4)	C4A—C3A—H3C	109.7
O2ⁱ—Sn1—Cl3	86.17 (4)	C2—C3A—H3D	109.7
Cl1—Sn1—Cl3	92.40 (2)	C4A—C3A—H3D	109.7
C2—Sn1—Cl2	96.58 (7)	H3C—C3A—H3D	108.2
O1—Sn1—Cl2	82.42 (4)	C5A—C4A—C3A	97.3 (16)
O2ⁱ—Sn1—Cl2	84.14 (4)	C5A—C4A—H4C	112.3
Cl1—Sn1—Cl2	91.38 (2)	C3A—C4A—H4C	112.3
Cl3—Sn1—Cl2	162.13 (2)	C5A—C4A—H4D	112.3
C1—O1—Sn1	116.64 (12)	C3A—C4A—H4D	112.3
C1—O2—Sn1ⁱ	114.80 (11)	H4C—C4A—H4D	109.9
O2—C1—O1	125.55 (17)	C4A—C5A—H5D	109.5
O2—C1—C1ⁱ	117.2 (2)	C4A—C5A—H5E	109.5
O1—C1—C1ⁱ	117.2 (2)	H5D—C5A—H5E	109.5
C3—C2—Sn1	115.4 (3)	C4A—C5A—H5F	109.5
C3A—C2—Sn1	116.0 (6)	H5D—C5A—H5F	109.5
C3—C2—H2A	108.4	H5E—C5A—H5F	109.5
Sn1—C2—H2A	108.4	C6—N1—C7	110.7 (2)
C3—C2—H2B	108.4	C6—N1—H1N	122 (2)
Sn1—C2—H2B	108.4	C7—N1—H1N	126 (2)
H2A—C2—H2B	107.5	C6—N2—C8	110.15 (19)
C3A—C2—H2C	108.3	C6—N2—H2N	117.8 (19)
Sn1—C2—H2C	108.3	C8—N2—H2N	132.1 (19)
C3A—C2—H2D	108.3	N1—C6—N2	106.0 (2)
Sn1—C2—H2D	108.3	N1—C6—C9	127.2 (2)
H2C—C2—H2D	107.4	N2—C6—C9	126.7 (2)
C2—C3—C4	113.7 (6)	C8—C7—N1	106.4 (2)
C2—C3—H3A	108.8	C8—C7—H7	126.8
C4—C3—H3A	108.8	N1—C7—H7	126.8
C2—C3—H3B	108.8	C7—C8—N2	106.6 (2)
C4—C3—H3B	108.8	C7—C8—H8A	126.7
H3A—C3—H3B	107.7	N2—C8—H8A	126.7
C5—C4—C3	116.7 (8)	C6—C9—H9A	109.5
C5—C4—H4A	108.1	C6—C9—H9B	109.5
C3—C4—H4A	108.1	H9A—C9—H9B	109.5
C5—C4—H4B	108.1	C6—C9—H9C	109.5
C3—C4—H4B	108.1	H9A—C9—H9C	109.5
H4A—C4—H4B	107.3	H9B—C9—H9C	109.5
C4—C5—H5A	109.5

Sn1ⁱ—O2—C1—O1	177.81 (15)	C7—N1—C6—N2	0.7 (3)
Sn1ⁱ—O2—C1—C1ⁱ	−1.5 (3)	C7—N1—C6—C9	−178.6 (3)
Sn1—O1—C1—O2	178.19 (15)	C8—N2—C6—N1	−0.6 (3)
Sn1—O1—C1—C1ⁱ	−2.5 (3)	C8—N2—C6—C9	178.7 (3)
Sn1—C2—C3—C4	179.1 (5)	C6—N1—C7—C8	−0.5 (3)
C2—C3—C4—C5	−174.8 (6)	N1—C7—C8—N2	0.1 (3)
Sn1—C2—C3A—C4A	−170.7 (8)	C6—N2—C8—C7	0.3 (3)
C2—C3A—C4A—C5A	−83.0 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.74 (3)	2.75 (3)	3.398 (2)	147 (3)
N1—H1N···O1	0.74 (3)	2.44 (3)	2.993 (2)	133 (3)
N2—H2N···Cl2ⁱⁱ	0.77 (2)	2.43 (3)	3.187 (2)	170 (2)
C7—H7···Cl3ⁱⁱⁱ	0.95	2.87	3.517 (2)	127
C9—H9A···Cl1	0.98	2.92	3.696 (3)	136

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

Acknowledgements

The authors acknowledge the Cheikh Anta Diop University of Dakar (Sénégal) and the University of Notre Dame (USA) for financial support.

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