
==== Front
IUCrdata
IUCrdata
IUCrData
IUCrData
2414-3146
International Union of Crystallography

tk4107
10.1107/S2414314624007429
IUCRBK
S2414314624007429
Data Reports
Diisobutyl­ammonium tri­phenyl(2-thiolato­acetato-κ2O,S)stannate(IV)
(C8H20N)[Sn(C6H5)3(C2H2O2S)]
Song Xueqing a*
Yeibyo Woldegebriel a
Li William a
Pike Robert D. b
a https://ror.org/037wegn60 University of the District of Columbia, Division of Sciences and Mathematics 4200 Connecticut Avenue NW 20008 Washington DC USA
b College of William & Mary, Department of Chemistry, 540 Landrum Drive, Williamsburg, VA 23185, USA
Tiekink E. R. T. Editor
Sunway University, Malaysia
Correspondence e-mail: xsong@udc.edu
8 2024
09 8 2024
09 8 2024
9 Pt 8 x240800 x24074222 7 2024
26 7 2024
© Song et al. 2024
2024
https://creativecommons.org/licenses/by/4.0/ 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.
A full version of this article is available from Crystallography Journals Online.
The title salt features a distorted cis-trigonal-bipyramid coordination geometry around the tin atom.

Crystals of the title salt, (C8H20N)[Sn(C6H5)3(C2H2O2S)], comprise diisobutyl­ammonium cations and mercapto­acetato­tri­phenyl­stannate(IV) anions. The bidentate binding mode of the mercapto­acetate ligand gives rise to a five-coordinated, ionic tri­phenyl­tin complex with a distorted cis-trigonal–bipyramidal geometry around the tin atom. In the crystal, charge-assisted ammonium-N—H⋯O(carboxyl­ate) hydrogen-bonding connects two cations and two anions into a four-ion aggregate. Two positions were resolved for one of the phenyl rings with the major component having a site occupancy factor of 0.60 (3).

crystal structure
hydrogen bonding
salt
cis-trigonal–bipyramid coordination
National Science Foundation 2117621 Freddie DixonXueqing Song National Science Foundation 1622811 Freddie Dixon National Science Foundation 1833656 Xueqing Song
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pmcStructure description

One of the authors has reported some ionic di- and triorganotin complexes (Song et al., 2005 ▸, 2005 ▸; Zhong et al., 2005 ▸) as part of efforts to modify structures of organotin complexes with the aim to increase their aqueous solubility (Gielen, 2002 ▸). The title salt is another example of an ionic tri­phenyl­tin complex of mercapto­acetic acid. The salt comprises a diisobutyl­ammonium cation and a mercapto­acetato­tri­phenyl­stannate anion, Fig. 1 ▸. This new species is similar to other reported ionic complexes like di-cyclo-hexyl­ammonium thiol­actatotri­phenyl­stannate (Song et al., 2006 ▸), tri­methyl­ammonium chlorido­diphenyl­mercapto­acetato­stannnate (Song et al., 2005 ▸) and 2-methyl­pyrimidium chlorido­diphenyl­mercaptostannate (Zhong et al., 2005 ▸). In the new salt, the Ph3Sn residue is covalently bound to a sulfur atom (Sn1—S1 2.423 (1) Å) and also to a less tightly bound carboxyl­ate-O atom as indicated by the relatively long Sn1—O1 bond length of 2.456 (2) Å. The coordination environment around the Sn atom is based on a distorted cis-trigonal–bipyramidal geometry with the O1 and C3 atoms in the axial positions, and the S1, C9 and C15 atoms in the equatorial plane. The axial axis is bent with the C3—Sn1—O1 angle being 168.74 (10)°. The S1—Sn1—O1 angle is significantly reduced [75.58 (6)°] from 90° due to the restricted bite distance of the mercapto­acetato ligand.

Charge-assisted hydrogen-bonding inter­actions (Table 1 ▸) between the di-iso-butyl­ammonium cations and the mercapto­acetato­tri­phenyl­stannate anions are observed in the crystal. As shown in Fig. 2 ▸, one ammonium-N—H atom forms a hydrogen bond to the carbonyl-O atom of one carboxyl­ate residue and the second ammonium-N—H atom bifurcates the carboxyl-O atom of a centrosymmetrically related carboxyl­ate residue. In this way, a four-ion aggregate is formed with a central twelve-membered {⋯HNH⋯OCO}2 synthon with the outer N—H⋯O hydrogen bonds lying above and below the encompassed eight-membered {⋯HNH⋯O}2 synthon. The hydrogen bonding substanti­ally affects the distribution of the electrons within the carboxyl­ate group, which can be seen by the observation of experimentally equivalent C—O bond lengths, i.e. 1.238 (4) Å for the C1—O1 bond and 1.241 (4) Å for the C1—O2 bond.

Synthesis and crystallization

The salt was prepared by the addition, with stirring, of mercapto­acetic acid (2 mmol) to an acetone solution (30 ml) containing tri­phenyl­tin hydroxide (2 mmol). To this solution was added, drop-wise, di-iso-butyl­amine (2 mmol) in acetone (20 ml). A cloudy solution formed immediately and after refluxing for 2 h, the solution became clear. The crude product was obtained as a solid by removing the solvent on a rotary evaporator. It was then recrystallized from 95% ethanol and upon slow evaporation crystals suitable for X-ray diffraction analysis were obtained. Yield 71%, m.p. 108–109 °C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Two positions, in a ratio 0.60 (3):0.40 (3), were resolved for the C15—C20 phenyl ring; all C atoms were refined with anisotropic displacement parameters.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624007429/tk4107sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624007429/tk4107Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314624007429/tk4107Isup3.mol

CCDC reference: 299548

Additional supporting information: crystallographic information; 3D view; checkCIF report

full crystallographic data

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Crystal data

(C8H20N)[Sn(C6H5)3(C2H2O2S)]	F(000) = 1176	
Mr = 570.33	Dx = 1.326 Mg m−3	
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å	
a = 10.4032 (1) Å	Cell parameters from 9852 reflections	
b = 18.8988 (3) Å	θ = 3.0–70.1°	
c = 14.8277 (2) Å	µ = 7.96 mm−1	
β = 101.382 (1)°	T = 296 K	
V = 2857.91 (7) Å3	Block, colourless	
Z = 4	0.39 × 0.25 × 0.18 mm	

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Data collection

Bruker APEXII CCD diffractometer	4767 reflections with I > 2σ(I)	
ω and Phi scans	Rint = 0.040	
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 70.6°, θmin = 3.8°	
Tmin = 0.439, Tmax = 0.753	h = −11→12	
35046 measured reflections	k = −22→22	
5313 independent reflections	l = −16→17	

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Refinement

Refinement on F2	Hydrogen site location: inferred from neighbouring sites	
Least-squares matrix: full	H-atom parameters constrained	
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0367P)2 + 1.6022P] where P = (Fo2 + 2Fc2)/3	
wR(F2) = 0.082	(Δ/σ)max = 0.001	
S = 1.09	Δρmax = 0.49 e Å−3	
5313 reflections	Δρmin = −0.45 e Å−3	
358 parameters	Extinction correction: SHELXL2019/3 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4	
287 restraints	Extinction coefficient: 0.00187 (8)	

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) 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.	

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

	x	y	z	Uiso*/Ueq	Occ. (<1)	
Sn1	0.29678 (2)	0.09786 (2)	0.24494 (2)	0.05419 (10)		
S1	0.45120 (9)	0.10232 (6)	0.39021 (6)	0.0876 (3)		
O1	0.1637 (2)	0.07224 (13)	0.36093 (16)	0.0666 (5)		
O2	0.1506 (3)	0.05058 (15)	0.50356 (18)	0.0860 (7)		
C1	0.2142 (3)	0.06407 (17)	0.4431 (2)	0.0631 (7)		
C2	0.3620 (4)	0.0666 (3)	0.4722 (3)	0.1027 (15)		
H2A	0.393128	0.018846	0.487275	0.123*		
H2B	0.383473	0.094437	0.528113	0.123*		
C3	0.4402 (3)	0.13121 (18)	0.1641 (2)	0.0588 (7)		
C4	0.5037 (4)	0.1952 (2)	0.1820 (3)	0.0813 (10)		
H4	0.485694	0.223468	0.229340	0.098*		
C5	0.5941 (5)	0.2185 (3)	0.1309 (4)	0.1038 (14)		
H5	0.635244	0.261967	0.144120	0.125*		
C6	0.6225 (4)	0.1781 (3)	0.0618 (3)	0.0991 (13)		
H6	0.683038	0.193809	0.027787	0.119*		
C7	0.5623 (4)	0.1147 (3)	0.0424 (3)	0.0944 (12)		
H7	0.581509	0.086972	−0.004996	0.113*		
C8	0.4714 (4)	0.0910 (2)	0.0936 (3)	0.0771 (10)		
H8	0.431091	0.047333	0.079869	0.093*		
C9	0.2351 (3)	−0.00545 (16)	0.1959 (2)	0.0563 (7)		
C10	0.1733 (4)	−0.0159 (2)	0.1058 (2)	0.0755 (9)		
H10	0.159273	0.022345	0.065598	0.091*		
C14	0.2544 (5)	−0.0634 (2)	0.2534 (3)	0.0848 (10)		
H14	0.296426	−0.057856	0.314441	0.102*		
C11	0.1315 (5)	−0.0834 (2)	0.0741 (3)	0.0971 (13)		
H11	0.090190	−0.090171	0.013162	0.117*		
C12	0.1517 (5)	−0.1389 (2)	0.1332 (4)	0.1092 (15)		
H12	0.123532	−0.183854	0.112612	0.131*		
C13	0.2123 (6)	−0.1294 (2)	0.2215 (4)	0.1142 (17)		
H13	0.225776	−0.167915	0.261307	0.137*		
C15A	0.160 (2)	0.1774 (13)	0.2172 (12)	0.057 (3)	0.60 (3)	
C16A	0.1154 (19)	0.1948 (9)	0.1277 (12)	0.071 (4)	0.60 (3)	
H16A	0.144453	0.168986	0.082169	0.086*	0.60 (3)	
C17A	0.0257 (18)	0.2514 (9)	0.1015 (11)	0.109 (5)	0.60 (3)	
H17A	0.000005	0.263945	0.039920	0.131*	0.60 (3)	
C18A	−0.0224 (17)	0.2872 (8)	0.1682 (13)	0.104 (4)	0.60 (3)	
H18A	−0.084414	0.322806	0.152316	0.125*	0.60 (3)	
C19A	0.0231 (17)	0.2694 (5)	0.2595 (11)	0.092 (4)	0.60 (3)	
H19A	−0.008020	0.293885	0.305199	0.110*	0.60 (3)	
C20A	0.1138 (17)	0.2160 (6)	0.2838 (10)	0.074 (3)	0.60 (3)	
H20A	0.144433	0.205754	0.345658	0.089*	0.60 (3)	
C15B	0.140 (3)	0.1803 (16)	0.197 (2)	0.050 (4)	0.40 (3)	
C16B	0.121 (3)	0.2043 (15)	0.1048 (16)	0.069 (4)	0.40 (3)	
H16B	0.176950	0.188357	0.067684	0.083*	0.40 (3)	
C17B	0.024 (2)	0.2491 (11)	0.0687 (17)	0.087 (5)	0.40 (3)	
H17B	0.011387	0.260865	0.006694	0.104*	0.40 (3)	
C18B	−0.0521 (18)	0.2767 (12)	0.120 (2)	0.102 (6)	0.40 (3)	
H18B	−0.119488	0.307409	0.095081	0.123*	0.40 (3)	
C19B	−0.032 (3)	0.2601 (14)	0.210 (2)	0.117 (9)	0.40 (3)	
H19B	−0.083472	0.281884	0.247046	0.141*	0.40 (3)	
C20B	0.064 (2)	0.2111 (12)	0.2513 (18)	0.083 (6)	0.40 (3)	
H20B	0.075348	0.199972	0.313465	0.100*	0.40 (3)	
N1	0.8901 (3)	0.04696 (15)	0.36359 (18)	0.0650 (6)		
H1A	0.853689	0.019449	0.400328	0.078*		
H1B	0.972417	0.054949	0.392118	0.078*		
C21	0.8199 (3)	0.11575 (19)	0.3547 (2)	0.0697 (8)		
H21A	0.726345	0.106843	0.345475	0.084*		
H21B	0.836613	0.140108	0.300649	0.084*		
C22	0.8592 (4)	0.16325 (19)	0.4370 (3)	0.0730 (9)		
H22	0.953152	0.173206	0.444635	0.088*		
C23	0.8347 (5)	0.1307 (2)	0.5254 (3)	0.0935 (12)		
H23A	0.743133	0.119985	0.518959	0.140*		
H23B	0.860454	0.163490	0.575101	0.140*		
H23C	0.884953	0.087993	0.538063	0.140*		
C24	0.7845 (5)	0.2333 (2)	0.4176 (4)	0.1104 (15)		
H24A	0.794891	0.251289	0.358927	0.166*		
H24B	0.818729	0.266898	0.464762	0.166*		
H24C	0.693144	0.225458	0.416926	0.166*		
C25	0.8944 (4)	0.0058 (2)	0.2778 (3)	0.0893 (11)		
H25A	0.941560	0.033477	0.239737	0.107*		
H25B	0.943907	−0.037271	0.294836	0.107*		
C26	0.7681 (5)	−0.0129 (3)	0.2235 (3)	0.1031 (14)		
H26	0.723996	0.031675	0.202671	0.124*		
C27	0.7886 (6)	−0.0520 (4)	0.1363 (4)	0.150 (2)		
H27A	0.838026	−0.022483	0.102841	0.225*		
H27B	0.704961	−0.062563	0.098270	0.225*		
H27C	0.835626	−0.095166	0.153432	0.225*		
C28	0.6779 (6)	−0.0524 (4)	0.2708 (4)	0.148 (3)		
H28A	0.714823	−0.097878	0.289587	0.222*		
H28B	0.595003	−0.058588	0.229658	0.222*		
H28C	0.665230	−0.026345	0.323974	0.222*		

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Atomic displacement parameters (Å2)

	U11	U22	U33	U12	U13	U23	
Sn1	0.05088 (14)	0.06135 (14)	0.05259 (14)	−0.00563 (8)	0.01566 (8)	−0.00136 (8)	
S1	0.0602 (5)	0.1427 (9)	0.0589 (5)	−0.0359 (5)	0.0091 (4)	0.0025 (5)	
O1	0.0582 (12)	0.0821 (14)	0.0624 (13)	−0.0099 (11)	0.0194 (10)	0.0025 (11)	
O2	0.0839 (17)	0.106 (2)	0.0791 (16)	0.0043 (14)	0.0415 (13)	0.0217 (14)	
C1	0.0700 (19)	0.0609 (18)	0.0635 (19)	−0.0077 (15)	0.0258 (15)	−0.0004 (14)	
C2	0.078 (2)	0.172 (4)	0.057 (2)	−0.034 (3)	0.0115 (18)	0.014 (2)	
C3	0.0458 (15)	0.0736 (19)	0.0594 (17)	0.0009 (13)	0.0162 (13)	0.0063 (14)	
C4	0.081 (2)	0.083 (2)	0.087 (3)	−0.0152 (19)	0.036 (2)	−0.0066 (19)	
C5	0.094 (3)	0.100 (3)	0.129 (4)	−0.030 (2)	0.051 (3)	0.000 (3)	
C6	0.082 (3)	0.126 (4)	0.103 (3)	−0.006 (2)	0.052 (2)	0.018 (3)	
C7	0.086 (3)	0.126 (3)	0.083 (3)	0.002 (2)	0.045 (2)	−0.005 (2)	
C8	0.074 (2)	0.090 (3)	0.073 (2)	−0.0051 (18)	0.0302 (18)	−0.0067 (17)	
C9	0.0525 (16)	0.0599 (16)	0.0597 (16)	0.0008 (13)	0.0190 (13)	−0.0039 (13)	
C10	0.080 (2)	0.077 (2)	0.068 (2)	−0.0079 (18)	0.0109 (17)	−0.0059 (17)	
C14	0.120 (3)	0.064 (2)	0.073 (2)	0.012 (2)	0.026 (2)	0.0054 (16)	
C11	0.100 (3)	0.098 (3)	0.093 (3)	−0.019 (2)	0.017 (2)	−0.034 (2)	
C12	0.142 (4)	0.067 (2)	0.132 (4)	−0.019 (3)	0.060 (3)	−0.029 (2)	
C13	0.188 (5)	0.055 (2)	0.113 (3)	0.004 (3)	0.063 (3)	0.000 (2)	
C15A	0.052 (6)	0.059 (6)	0.061 (7)	−0.001 (4)	0.018 (6)	0.004 (5)	
C16A	0.083 (5)	0.061 (7)	0.071 (8)	0.015 (5)	0.020 (6)	0.009 (5)	
C17A	0.132 (9)	0.105 (7)	0.087 (8)	0.053 (7)	0.011 (7)	0.013 (6)	
C18A	0.117 (9)	0.087 (7)	0.117 (9)	0.052 (7)	0.047 (7)	0.033 (6)	
C19A	0.120 (9)	0.069 (5)	0.103 (7)	0.031 (5)	0.064 (7)	0.019 (5)	
C20A	0.096 (9)	0.053 (4)	0.082 (6)	0.013 (5)	0.040 (5)	0.009 (4)	
C15B	0.052 (9)	0.041 (5)	0.060 (10)	−0.001 (5)	0.014 (8)	0.019 (7)	
C16B	0.076 (7)	0.072 (7)	0.057 (8)	−0.010 (5)	0.008 (6)	0.028 (6)	
C17B	0.081 (7)	0.086 (8)	0.085 (11)	−0.011 (6)	−0.002 (6)	0.031 (7)	
C18B	0.073 (8)	0.100 (11)	0.137 (14)	0.005 (7)	0.027 (8)	0.058 (11)	
C19B	0.106 (13)	0.121 (14)	0.144 (16)	0.059 (11)	0.072 (12)	0.068 (13)	
C20B	0.075 (10)	0.091 (10)	0.096 (11)	0.022 (8)	0.048 (8)	0.043 (9)	
N1	0.0616 (15)	0.0770 (17)	0.0565 (15)	−0.0099 (13)	0.0118 (12)	−0.0065 (12)	
C21	0.0609 (19)	0.082 (2)	0.0644 (19)	−0.0054 (16)	0.0091 (15)	0.0126 (16)	
C22	0.067 (2)	0.071 (2)	0.084 (2)	−0.0069 (16)	0.0229 (17)	−0.0045 (17)	
C23	0.112 (3)	0.098 (3)	0.075 (2)	−0.003 (2)	0.029 (2)	−0.009 (2)	
C24	0.124 (4)	0.082 (3)	0.136 (4)	0.011 (3)	0.051 (3)	0.008 (3)	
C25	0.084 (3)	0.112 (3)	0.075 (2)	−0.015 (2)	0.0233 (19)	−0.012 (2)	
C26	0.096 (3)	0.144 (4)	0.072 (2)	−0.034 (3)	0.021 (2)	−0.009 (2)	
C27	0.162 (5)	0.208 (7)	0.081 (3)	−0.039 (5)	0.025 (3)	−0.055 (4)	
C28	0.135 (5)	0.196 (7)	0.113 (4)	−0.088 (5)	0.025 (3)	−0.015 (4)	

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Geometric parameters (Å, º)

Sn1—S1	2.4212 (9)	C19A—H19A	0.9300	
Sn1—O1	2.459 (2)	C19A—C20A	1.381 (12)	
Sn1—C3	2.183 (3)	C20A—H20A	0.9300	
Sn1—C9	2.137 (3)	C15B—C16B	1.411 (19)	
Sn1—C15A	2.055 (19)	C15B—C20B	1.371 (18)	
Sn1—C15B	2.27 (2)	C16B—H16B	0.9300	
S1—C2	1.800 (4)	C16B—C17B	1.34 (3)	
O1—C1	1.238 (4)	C17B—H17B	0.9300	
O2—C1	1.241 (4)	C17B—C18B	1.32 (3)	
C1—C2	1.513 (5)	C18B—H18B	0.9300	
C2—H2A	0.9700	C18B—C19B	1.35 (2)	
C2—H2B	0.9700	C19B—H19B	0.9300	
C3—C4	1.379 (5)	C19B—C20B	1.409 (19)	
C3—C8	1.382 (5)	C20B—H20B	0.9300	
C4—H4	0.9300	N1—H1A	0.8900	
C4—C5	1.390 (5)	N1—H1B	0.8900	
C5—H5	0.9300	N1—C21	1.484 (4)	
C5—C6	1.356 (6)	N1—C25	1.499 (4)	
C6—H6	0.9300	C21—H21A	0.9700	
C6—C7	1.355 (6)	C21—H21B	0.9700	
C7—H7	0.9300	C21—C22	1.505 (5)	
C7—C8	1.397 (5)	C22—H22	0.9800	
C8—H8	0.9300	C22—C23	1.513 (5)	
C9—C10	1.378 (5)	C22—C24	1.533 (6)	
C9—C14	1.379 (5)	C23—H23A	0.9600	
C10—H10	0.9300	C23—H23B	0.9600	
C10—C11	1.399 (5)	C23—H23C	0.9600	
C14—H14	0.9300	C24—H24A	0.9600	
C14—C13	1.374 (6)	C24—H24B	0.9600	
C11—H11	0.9300	C24—H24C	0.9600	
C11—C12	1.355 (7)	C25—H25A	0.9700	
C12—H12	0.9300	C25—H25B	0.9700	
C12—C13	1.350 (7)	C25—C26	1.444 (6)	
C13—H13	0.9300	C26—H26	0.9800	
C15A—C16A	1.356 (14)	C26—C27	1.539 (6)	
C15A—C20A	1.388 (15)	C26—C28	1.480 (6)	
C16A—H16A	0.9300	C27—H27A	0.9600	
C16A—C17A	1.422 (19)	C27—H27B	0.9600	
C17A—H17A	0.9300	C27—H27C	0.9600	
C17A—C18A	1.372 (15)	C28—H28A	0.9600	
C18A—H18A	0.9300	C28—H28B	0.9600	
C18A—C19A	1.385 (13)	C28—H28C	0.9600	
				
S1—Sn1—O1	75.58 (6)	C15A—C20A—H20A	119.6	
C3—Sn1—S1	94.18 (8)	C19A—C20A—C15A	120.9 (10)	
C3—Sn1—O1	168.74 (10)	C19A—C20A—H20A	119.6	
C3—Sn1—C15B	98.9 (7)	C16B—C15B—Sn1	119.0 (17)	
C9—Sn1—S1	115.87 (9)	C20B—C15B—Sn1	124.6 (15)	
C9—Sn1—O1	83.40 (9)	C20B—C15B—C16B	116.4 (18)	
C9—Sn1—C3	105.62 (12)	C15B—C16B—H16B	118.6	
C9—Sn1—C15B	111.8 (10)	C17B—C16B—C15B	123 (2)	
C15A—Sn1—S1	117.7 (6)	C17B—C16B—H16B	118.6	
C15A—Sn1—O1	79.7 (5)	C16B—C17B—H17B	119.7	
C15A—Sn1—C3	101.6 (6)	C18B—C17B—C16B	120.5 (18)	
C15A—Sn1—C9	116.7 (8)	C18B—C17B—H17B	119.7	
C15B—Sn1—S1	124.5 (9)	C17B—C18B—H18B	120.3	
C15B—Sn1—O1	83.6 (7)	C17B—C18B—C19B	119.4 (16)	
C2—S1—Sn1	104.34 (13)	C19B—C18B—H18B	120.3	
C1—O1—Sn1	121.7 (2)	C18B—C19B—H19B	118.7	
O1—C1—O2	123.6 (3)	C18B—C19B—C20B	122.5 (16)	
O1—C1—C2	119.1 (3)	C20B—C19B—H19B	118.7	
O2—C1—C2	117.2 (3)	C15B—C20B—C19B	117.9 (16)	
S1—C2—H2A	108.1	C15B—C20B—H20B	121.0	
S1—C2—H2B	108.1	C19B—C20B—H20B	121.0	
C1—C2—S1	116.7 (3)	H1A—N1—H1B	107.1	
C1—C2—H2A	108.1	C21—N1—H1A	107.7	
C1—C2—H2B	108.1	C21—N1—H1B	107.7	
H2A—C2—H2B	107.3	C21—N1—C25	118.4 (3)	
C4—C3—Sn1	120.1 (2)	C25—N1—H1A	107.7	
C4—C3—C8	116.9 (3)	C25—N1—H1B	107.7	
C8—C3—Sn1	123.0 (3)	N1—C21—H21A	108.8	
C3—C4—H4	119.3	N1—C21—H21B	108.8	
C3—C4—C5	121.5 (4)	N1—C21—C22	113.6 (3)	
C5—C4—H4	119.3	H21A—C21—H21B	107.7	
C4—C5—H5	119.8	C22—C21—H21A	108.8	
C6—C5—C4	120.4 (4)	C22—C21—H21B	108.8	
C6—C5—H5	119.8	C21—C22—H22	108.2	
C5—C6—H6	120.1	C21—C22—C23	113.2 (3)	
C7—C6—C5	119.8 (4)	C21—C22—C24	108.4 (3)	
C7—C6—H6	120.1	C23—C22—H22	108.2	
C6—C7—H7	119.9	C23—C22—C24	110.4 (3)	
C6—C7—C8	120.1 (4)	C24—C22—H22	108.2	
C8—C7—H7	119.9	C22—C23—H23A	109.5	
C3—C8—C7	121.3 (4)	C22—C23—H23B	109.5	
C3—C8—H8	119.4	C22—C23—H23C	109.5	
C7—C8—H8	119.4	H23A—C23—H23B	109.5	
C10—C9—Sn1	120.8 (2)	H23A—C23—H23C	109.5	
C10—C9—C14	118.0 (3)	H23B—C23—H23C	109.5	
C14—C9—Sn1	121.2 (3)	C22—C24—H24A	109.5	
C9—C10—H10	119.6	C22—C24—H24B	109.5	
C9—C10—C11	120.7 (4)	C22—C24—H24C	109.5	
C11—C10—H10	119.6	H24A—C24—H24B	109.5	
C9—C14—H14	119.6	H24A—C24—H24C	109.5	
C13—C14—C9	120.7 (4)	H24B—C24—H24C	109.5	
C13—C14—H14	119.6	N1—C25—H25A	108.5	
C10—C11—H11	120.3	N1—C25—H25B	108.5	
C12—C11—C10	119.4 (4)	H25A—C25—H25B	107.5	
C12—C11—H11	120.3	C26—C25—N1	115.1 (3)	
C11—C12—H12	119.8	C26—C25—H25A	108.5	
C13—C12—C11	120.5 (4)	C26—C25—H25B	108.5	
C13—C12—H12	119.8	C25—C26—H26	106.4	
C14—C13—H13	119.6	C25—C26—C27	108.9 (4)	
C12—C13—C14	120.7 (4)	C25—C26—C28	116.9 (4)	
C12—C13—H13	119.6	C27—C26—H26	106.4	
C16A—C15A—Sn1	117.6 (11)	C28—C26—H26	106.4	
C16A—C15A—C20A	118.0 (12)	C28—C26—C27	111.3 (5)	
C20A—C15A—Sn1	124.4 (10)	C26—C27—H27A	109.5	
C15A—C16A—H16A	119.0	C26—C27—H27B	109.5	
C15A—C16A—C17A	121.9 (12)	C26—C27—H27C	109.5	
C17A—C16A—H16A	119.0	H27A—C27—H27B	109.5	
C16A—C17A—H17A	120.4	H27A—C27—H27C	109.5	
C18A—C17A—C16A	119.2 (11)	H27B—C27—H27C	109.5	
C18A—C17A—H17A	120.4	C26—C28—H28A	109.5	
C17A—C18A—H18A	120.6	C26—C28—H28B	109.5	
C17A—C18A—C19A	118.8 (10)	C26—C28—H28C	109.5	
C19A—C18A—H18A	120.6	H28A—C28—H28B	109.5	
C18A—C19A—H19A	119.4	H28A—C28—H28C	109.5	
C20A—C19A—C18A	121.1 (8)	H28B—C28—H28C	109.5	
C20A—C19A—H19A	119.4			
				
Sn1—S1—C2—C1	−17.7 (4)	C10—C11—C12—C13	−0.4 (8)	
Sn1—O1—C1—O2	−179.5 (3)	C14—C9—C10—C11	0.2 (6)	
Sn1—O1—C1—C2	−2.8 (5)	C11—C12—C13—C14	0.2 (8)	
Sn1—C3—C4—C5	−179.0 (3)	C15A—C16A—C17A—C18A	−3 (3)	
Sn1—C3—C8—C7	179.0 (3)	C16A—C15A—C20A—C19A	1 (3)	
Sn1—C9—C10—C11	−179.2 (3)	C16A—C17A—C18A—C19A	3 (3)	
Sn1—C9—C14—C13	178.9 (3)	C17A—C18A—C19A—C20A	−1 (2)	
Sn1—C15A—C16A—C17A	−176.8 (17)	C18A—C19A—C20A—C15A	−2 (2)	
Sn1—C15A—C20A—C19A	179.0 (13)	C20A—C15A—C16A—C17A	1 (3)	
Sn1—C15B—C16B—C17B	175 (2)	C15B—C16B—C17B—C18B	5 (4)	
Sn1—C15B—C20B—C19B	−178.2 (19)	C16B—C15B—C20B—C19B	4 (4)	
O1—C1—C2—S1	14.6 (6)	C16B—C17B—C18B—C19B	1 (3)	
O2—C1—C2—S1	−168.6 (3)	C17B—C18B—C19B—C20B	−3 (3)	
C3—C4—C5—C6	−0.3 (7)	C18B—C19B—C20B—C15B	1 (3)	
C4—C3—C8—C7	−0.6 (6)	C20B—C15B—C16B—C17B	−7 (4)	
C4—C5—C6—C7	0.1 (8)	N1—C21—C22—C23	−59.6 (4)	
C5—C6—C7—C8	−0.1 (7)	N1—C21—C22—C24	177.6 (3)	
C6—C7—C8—C3	0.3 (7)	N1—C25—C26—C27	177.7 (4)	
C8—C3—C4—C5	0.5 (6)	N1—C25—C26—C28	−55.2 (7)	
C9—C10—C11—C12	0.3 (7)	C21—N1—C25—C26	−58.7 (5)	
C9—C14—C13—C12	0.3 (7)	C25—N1—C21—C22	−160.1 (3)	
C10—C9—C14—C13	−0.5 (6)			

Diisobutylammonium triphenyl(2-thiolatoacetato-κ2O,S)stannate(IV) Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A	
N1—H1A···O2i	0.89	1.95	2.791 (4)	157	
N1—H1B···O1ii	0.89	2.16	2.894 (3)	140	
N1—H1B···O2ii	0.89	2.23	3.072 (4)	158	

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

Figure 1 The mol­ecular structures of the two ions comprising the asymmetric unit in the title salt showing the atom-labelling scheme and anisotropic displacement ellipsoids at the 50% probability level.

Figure 2 A view of the four-ion aggregate in the crystal of the title salt. Dashed lines indicate hydrogen bonds.

Table 1 Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A	
N1—H1A⋯O2i	0.89	1.95	2.791 (4)	157	
N1—H1B⋯O1ii	0.89	2.16	2.894 (3)	140	
N1—H1B⋯O2ii	0.89	2.23	3.072 (4)	158	
Symmetry codes: (i) ; (ii) .

Table 2 Experimental details

Crystal data	
Chemical formula	(C8H20N)[Sn(C6H5)3(C2H2O2S)]	
M r	570.33	
Crystal system, space group	Monoclinic, P21/n	
Temperature (K)	296	
a, b, c (Å)	10.4032 (1), 18.8988 (3), 14.8277 (2)	
β (°)	101.382 (1)	
V (Å3)	2857.91 (7)	
Z	4	
Radiation type	Cu Kα	
μ (mm−1)	7.96	
Crystal size (mm)	0.39 × 0.25 × 0.18	
 	
Data collection	
Diffractometer	Bruker APEXII CCD	
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)	
Tmin, Tmax	0.439, 0.753	
No. of measured, independent and observed [I > 2σ(I)] reflections	35046, 5313, 4767	
R int	0.040	
(sin θ/λ)max (Å−1)	0.612	
 	
Refinement	
R[F2 > 2σ(F2)], wR(F2), S	0.032, 0.082, 1.09	
No. of reflections	5313	
No. of parameters	358	
No. of restraints	287	
H-atom treatment	H-atom parameters constrained	
Δρmax, Δρmin (e Å−3)	0.49, −0.45	
Computer programs: APEX2 and SAINT-Plus (Bruker, 2004 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2019/3 (Sheldrick, 2015 ▸) and OLEX2 (Dolomanov et al., 2009 ▸).
==== Refs
References

Bruker (2004). APEX2 and SAINT-Plus. 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.
Gielen, M. (2002). Appl. Organomet. Chem. 16, 481–494.
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
Song, X., Koranteng, N., Borkowski, L., Cahill, C. & Eng, G. (2006). Main Group Met. Chem. 29, 263–265.
Song, X., Zhong, G., Xie, Q. & Eng, G. (2005). Inorg. Chem. Commun. 8, 725–728.
Zhong, G., Liu, Q., Song, X., Eng, G. & Xie, Q. (2005). J. Organomet. Chem. 690, 3405–3409.
