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

Song, X.; Yeibyo, W.; Li, W.; Pike, R.D.

doi:10.1107/S2414314624007429

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 8| August 2024| x240742

https://doi.org/10.1107/S2414314624007429

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

Xueqing Song,^a ^* Woldegebriel Yeibyo,^a William Li ^a and Robert D. Pike ^b

^aUniversity of the District of Columbia, Division of Sciences and Mathematics, 4200 Connecticut Avenue, NW 20008, Washington, DC, USA, and ^bCollege of William & Mary, Department of Chemistry, 540 Landrum Drive, Williamsburg, VA 23185, USA
^*Correspondence e-mail: xsong@udc.edu

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 22 July 2024; accepted 26 July 2024; online 9 August 2024)

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).

Keywords: crystal structure; hydrogen bonding; salt; cis-trigonal–bipyramid coordination.

CCDC reference: 299548

Structure 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.

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.

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.

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) .

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

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.

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 )
T_min, T_max	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
Δρ_max, Δρ_min (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 ).

Structural data

CCDC reference: 299548

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624007429/tk4107sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624007429/tk4107Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624007429/tk4107Isup3.mol

checkCIF report

Computing details top

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

Crystal data top

(C₈H₂₀N)[Sn(C₆H₅)₃(C₂H₂O₂S)]	F(000) = 1176
M_r = 570.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0367P)² + 1.6022P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.082	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.49 e Å⁻³
5313 reflections	Δρ_min = −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)

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.

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Funding information

Financial assistance from the National Science Foundation (NSF grants #2117621, #1622811 and #1833656) and the University of the District of Columbia (UDC) is gratefully acknowledged.

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