Synthesis of organotin(IV) heterocycles containing a xanthenyl group by a Barbier approach via ultrasound activation: synthesis, crystal structure and Hirshfeld surface analysis

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A series of organotin heterocycles of general formula [{Me₂C(C₆H₃CH₂)₂O}SnR₂] [R = methyl (Me, 4), n-butyl (n-Bu, 5), benzyl (Bn, 6) and phenyl (Ph, 7)] was easily synthesized by a Barbier-type reaction assisted by the sonochemical activation of metallic magnesium. The ¹¹⁹Sn{¹H} NMR data for all four com­pounds confirm the presence of a central Sn atom in a four-coordinated environment in solution. Single-crystal X-ray diffraction studies for 17,17-dimethyl-7,7-di­phenyl-15-oxa-7-stanna­tetra­cyclo­[11.3.1.0^5,16.0^9,14]hepta­deca-1,3,5(16),9(14),10,12-hexa­­ene, [Sn(C₆H₅)₂(C₁₇H₁₆O)], 7, at 100 and 295 K con­firmed the formation of a mono­nuclear eight-membered heterocycle, with a conformation depicted as boat–chair, resulting in a weak Sn⋯O inter­action. The Sn and O atoms are surrounded by hydro­phobic C—H bonds. A Hirshfeld surface analysis of 7 showed that the eight-membered heterocycles are linked by weak C—H⋯π, π–π and H⋯H noncovalent inter­actions. The pairwise inter­action energies showed that the cohesion between the heterocycles are mainly due to dispersion forces.

1. Introduction

The capability of tetra­valent organotin com­pounds to inter­act effectively with electron donors, such as N, S and O, leading to penta- hexa- and even hepta-coordinated structures via both inter- and intra­molecular inter­actions, is well known (Munguia et al., 2007; Vargas-Pineda et al., 2010). A very important aspect is to understand the role that the heteroatoms con­tained in these com­pounds play in the variations of the structural, electronic and reactivity properties (Fillion et al., 2016). Compounds where the Sn atom has the capacity to intra­molecularly inter­act with sulfur or oxygen are well investigated, for example, in di­thia­stannecine com­plexes (Martínez-Otero et al., 2012a,b). The extent of intra­molecular D⋯Sn bonding (D = donor atom) is usually determined by single-crystal X-ray diffraction, Mössbauer spectroscopy (Kárpáti et al., 2007) and, less extensively to date, solid-state ¹¹⁹Sn NMR spectroscopy (Lockhart et al., 1985; Kümmerlen et al., 1992; Munguia et al., 2007). The present series of com­pounds provides the capacity to understand the effect of changing the Lewis acidity at the central Sn atom upon the nature and magnitude of the intra­molecular D⋯Sn inter­actions.

On the other hand, in relation to the preparation of heterocycles with Sn atoms, the synthetic protocols are usually based on Grignard- (Blanda et al., 1989) or Wurtz-type (Zarl et al., 2009) reactions, where Sn—C bonds are formed. Nevertheless, another inter­esting and convenient approach to form these bonds is based on the less common Barbier-type reactions assisted by sonochemical activation of the metal surface, for instance, magnesium or copper (Lamandé-Langle et al., 2009; Ocampo et al., 2013; Cintas et al., 2011).

Herein we report the synthesis, by means of a Barbier-type ultrasound-assisted protocol, of a set of organotin heterocycles containing the skeleton derived from 4,5-bis­(bromo­meth­yl)-9,9-dimethyl-9H-xanthene and their structural char­acterization, as well as com­putational studies of 17,17-di­methyl-7,7-diphenyl-15-oxa-7-stanna­tetra­cyclo­[11.3.1.0^5,16.0^9,14]hepta­deca-1,3,5(16),9(14),10,12-hexa­ene, 7 (see Fig. 1), based on a Hirshfeld surface approach.

Figure 1 The synthesis of com­pounds 4–7. The numbering scheme for the NMR assignments is in green.

2. Experimental

The manipulations involving n-BuLi reagent and Barbier reactions were performed in a dry-nitro­gen atmosphere using standard Schlenk techniques. The solvents N,N,N′,N′-tetra­methyl­ethylenedi­amine (TMEDA) and N,N-di­methyl­form­am­ide (DMF) were purchased from Sigma–Aldrich, dried by standard methods and distilled prior to use. The reagents Ph₂SnCl₂ (95% purity), n-Bu₂SnCl₂ (96% purity) and Me₂SnBr₂ (97% purity) used in the syntheses were also purchased from Sigma–Aldrich and used without purification. Bn₂SnBr₂ was prepared according to a reported method (Sisido et al., 1961) from the reaction of tin powder, activated with a few drops of water, with benzyl bromide in toluene. Merck Kiesel gel 60 (0.063–0.40 mm) was used for column chromatography purification procedures.

Melting points were determined with a Mel–Temp II instrument. IR spectra were recorded in the 4000–650 cm⁻¹ range on a PerkinElmer System 2000 FT–IR spectrometer, in a solution of di­chloro­methane. ¹H, ¹³C{¹H} and ¹¹⁹Sn{¹H} NMR spectra were recorded in CDCl₃ on a Bruker Avance III 400 MHz spectrometer (400.1 MHz for ¹H, 100.0 MHz for ¹³C and 149.2 MHz for ¹¹⁹Sn) at 23 °C, and calibrated using the residual proton resonance of CDCl₃. Chemical shifts (δ) are reported in ppm and coupling constants (J) in Hz. For the assignments, 2D correlation experiments such as COSY (correlated spectroscopy), HSQC (heteronuclear sin­gle quantum correlation) and HMBC (heteronuclear multiple-bond correlation) were used.

The sequence of the reaction steps is summarized in Fig. 1. Compound 3 was prepared by minor modifications to the methodology reported by Besenyei et al. (2013). The 4, 5, 6 and 7 organotin(IV) heterocycles were prepared according to the approach reported by García-González et al. (2024), by the reaction of precursor 3 with an excess of magnesium turnings and the corresponding diorganodihalogenstannane(IV) (R₂SnX₂; X = Cl and Br) as limiting reagent in anhydrous tetra­hydro­furan (THF). The mixture was sonicated for 20 min at room temperature and was then stirred magnetically for 20 h. The mixture was treated according to the general method to yield the com­pounds of general formula [{Me₂C(C₆H₃CH₂)₂O}SnR₂] (See Fig. 1).

2.1. Synthesis and crystallization

2.1.1. Synthesis of the di­aldehyde Me₂C(C₆H₃CHO)₂O (1)

9,9-Dimethyl-9H-xanthene (5.0 g, 23.8 mmol) was dissolved in dry hexane (60 ml), under a nitro­gen atmosphere, and TMEDA (8.9 ml, 59.5 mmol) was added at 23 °C. A solution of n-butyl­lithium in hexa­nes (2.5 M, 21 ml, 52.4 mmol) was added dropwise to the mixture, forming a dark-red solution. This was refluxed for 30 min and cooled to 23 °C before dry DMF (7.0 ml, 83.3 mmol) was poured into the reaction mixture. The dark solution was stirred for 1 h whilst its colour became white. Aqueous hydro­chloric acid (90 ml, 2 M) was added and the mixture was stirred for 15 min. The precipitate was filtered off, washed sequentially with water and hexane, and dried to yield 1 as a yellow solid (yield: 5.7 g, 90%). The pro­duct crystallized by slow evaporation from ethyl acetate as yellow prisms. ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 10.69 (s, 2H, H1), 7.81 (dd, J = 7.60, 1.60 Hz, 2H, H5), 7.71 (dd, J = 7.80, 1.60 Hz, 2H, H7), 7.26 (dd, J = 7.60 Hz, 2H, H6), 1.69 (6H, s, H9). ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 188.7 (C1), 151.4 (C3), 132.5 (C5), 131.1 (C4), 127.8 (C7), 124.3(C2), 124.1 (C6), 34.0 (C8), 32.5 (C9).

2.1.2. Synthesis of the diol Me₂C(C₆H₃CH₂OH)₂O (2)

To an EtOH solution (50 ml) of di­aldehyde 1 (5.7 g, 21.4 mmol) was added NaBH₄ (2.4 g, 64.2 mmol) and the resulting mixture was stirred overnight at room temperature. It was then treated with water and acidified with dilute HCl, followed by extraction with di­chloro­methane. The combined organic phases were washed with water, dried (Na₂SO₄) and the volatiles were removed under reduced pressure to give 5.0 g (86%) of a light-green semi-solid. ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.40 (dd, 2H, J = 8.0, 1.50 Hz, H7), 7.16 (dd, 2H, J = 7.0, 1.0 Hz, H5), 7.05 (dd, 2H, J = 7.50 Hz, H6), 4.77 (s, 4H, H1), 1.63 (s, 6H, H9). ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 148.9 (C3), 130.4 (C4), 128.0 (C2), 127.8 (C5), 126.2 (C7), 123.0 (C6), 62.2 (C1), 34.2 (C8), 32.2 (C9).

2.1.3. Synthesis of dibrominated com­pound Me₂C(C₆H₃CH₂Br)₂O (3)

To a toluene solution (30 ml) of 2 (5 g, 18.5 mmol) was added HBr (6.4 ml, 55.5 mmol) dissolved in toluene (10 ml) dropwise, and the resulting mixture was refluxed for 22 h. A saturated aqueous NaHCO₃ solution (20 ml) was added carefully, followed by extraction with CHCl₃ (20 ml). The organic phase was separated, dried (Na₂SO₄) and evaporated to give a brown solid. The com­pound was purified by column chromatography using silica as the stationary phase and di­chloro­methane as eluent to give a white crystalline solid (yield: 6.67 g, 91%). The pro­duct crystallized by slow evaporation from di­chloro­methane as clear plates. ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.40 (dd, 2H, J = 7.50, 1.0 Hz, H7), 7.27 (dd, 2H, J = 7.50, 1.50 Hz, H5), 7.07 (dd, 2H, J = 8.0 Hz, H6), 4.83 (s, 4H, H1), 1.64 (s, 6H, H9). ¹³C{¹H} NMR (ppm) (CDCl₃, 400 MHz): δ 148.1 (C3), 130.4 (C4), 128.9 (C5), 127.2 (C7), 125.4 (C2), 123.4 (C6), 34.3, (C8), 32.7 (C9), 29.0 (C1).

2.1.4. Synthesis of organotin(IV) heterocycles [{Me₂C(C₆H₃CH₂)₂O}SnR₂] (4–7)

General method: a mixture of magnesium turnings, precursor 3 and R₂SnX₂ was mixed in freshly distilled anhydrous THF. The reaction was immersed in a commercial ultrasound bath (VMR 250D, working fre­quency: 35 kHz) for 20 min at 20 °C. Afterwards, the mixture was stirred at room temperature for 20 h. The mixture was vacuum evaporated and the addition of 30 ml of ethyl ether yielded a precipitate that was removed. The ethereal solution was washed with NaCl solution (20 ml, 5% w/v). The organic phase was separated and dried over Na₂SO₄ and the solvents were removed under reduced pressure to obtain the desired pro­duct.

Compound 4: Mg (0.037 g, 1.515 mmol); 3 (0.200 g, 0.505 mmol); Me₂SnBr₂ (0.153 g, 0.480 mmol); THF (15 ml). Colourless viscous liquid (0.172 g, 0.446 mmol, 93%). IR (DCM, cm⁻¹): 3062, 2970, 2924, 2667, 1689, 1615, 1434, 1261, 1210, 747; ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.11 (d, J = 7.05 Hz, 2H, H5), 7.04 (d, J = 6.75 Hz, 2H, H7), 6.99 (dd, J = 7.44 Hz, 2H, H6), 2.44 [s, ²J(¹H–¹¹⁹Sn) = 58.71 Hz, 4H, H1], 1.66 (s, 6H, H9), −0.35 [s, ²J(¹H–¹¹⁹Sn) = 49.14 Hz, 6H, H10]; ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 153.2 (C3), 134.8 (C4), 131.6 (C2), 126.5 (C7), 123.4 (C6), 119.8 (C5), 36.8 (C8), 26.7 (C9), 17.3 [¹J(¹³C–^119/117Sn) = 324.5/310.1 Hz, C1], −10.3 [¹J(¹³C–^119/117Sn) = 395.1/282.9, C10]; ¹¹⁹Sn{¹H} NMR (ppm) (CDCl₃, 149.2 MHz): δ 26.8.

Compound 5: Mg (0.074 g, 3.03 mmol); 3 (0.400g, 1.01 mmol); n-Bu₂SnCl₂ (0.307 g, 0.96 mmol); THF (20 ml). Colourless viscous liquid (0.414 g, 0.883 mmol, 92%). IR (DCM, cm⁻¹): 2955, 2923, 2869, 1615, 1581, 1434, 1261, 1206, 743; ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.09 (d, J = 7.38 Hz, 2H, H5), 7.04 (dd, J = 6.86 Hz, 2H, H7), 6.98 (d, J = 7.47 Hz, 2H, H6), 2.43 [s, ²J(¹H–¹¹⁹Sn) = 53.83 Hz, 4H, H1], 1.64 (s, 6H, H9), 1.17–1.03 (m, 4H, H11 and H12), 0.72 (t, J = 7.02 Hz, 6H, H13), 0.46 (t, J = 7.63 Hz, 4H, H10); ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 153.4 (C3), 134.9 (C4), 132.0 (C2), 126.4 (C7), 123.4 (C6), 119.7 (C5), 36.9 (C8), 28.7 (C11), 27.1 (C12), 26.7 (C9), 16.2 [¹J(¹³C–^119/117Sn) = 280.7/268.1 Hz, C1], 13.7 (C13), 10.7 [¹J(¹³C–^119/117Sn) = 304.8/291.2 Hz, C10]; ¹¹⁹Sn{¹H} NMR (ppm) (CDCl₃, 149.2 MHz): δ 14.4.

Compound 6: Mg (0.037 g, 1.515 mmol); 3 (0.200 g, 0.505 mmol); Bn₂SnBr₂ (0.221 g, 0.480 mmol); THF (15 ml). Colourless viscous liquid (0.235 g, 0.437 mmol, 91%). IR (DCM, cm⁻¹): 3026, 2968, 2920, 1598, 1434, 1264, 1209, 734, 696; ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.12 (dd, J = 6.70 Hz, 2.39 Hz, 2H, H5), 7.06 (dd, J = 7.59 Hz, 4H, H13), 7.02–6.97 (m, 4H, H7 and H14), 6.92 (dd, J = 7.45 Hz, 2H, H6), 6.61 (d, J = 8.20 Hz, 4H, H12), 2.34 [s, ²J(¹H–¹¹⁹Sn) = 57.07 Hz, 4H, H1], 1.87 [s, ²J(¹H–¹¹⁹Sn) = 55.95 Hz, 4H, H10], 1.62 (s, 6H, H9); ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 152.6 (C3), 141.9 (C11), 134.5 (C4), 130.2 (C2), 128.4 (C13), 127.1 (C12), 127.0 (C7), 123.6 (C14), 123.3 (C6), 120.3 (C5), 36.6 (C8), 26.8 (C9), 19.5 [¹J(¹³C–^119/117Sn) = 235.6/225.5 Hz, C1], 16.3 [¹J(¹³C–^119/117Sn) = 306.7/292.3 Hz, C10]; ¹¹⁹Sn{¹H} NMR (ppm) (CDCl₃, 149.2 MHz): δ −8.6.

Compound 7: Mg (0.074 g, 3.03 mmol); 3 (0.400 g, 1.01 mmol); Ph₂SnCl₂ (0.344 g, 0.96 mmol); THF (20 ml). White solid (0.463 g, 0.91 mmol, 95%); m.p. 79 °C. The pro­duct crystallized by slow evaporation from ethyl ether as clear prisms. IR (DCM, cm⁻¹): 3062, 2970, 2925, 1616, 1579, 1428, 1263, 1209, 726, 697; ¹H NMR (ppm) (CDCl₃, 400.1 MHz): δ 7.19–7.13 (m, 6H, H7 and H14), 7.12 (d, J = 2.07 Hz, 2H, H7), 7.10 (d, J = 3.29 Hz, 2H, H5), 7.06 (d, J = 7.44 Hz, 4H, H11), 6.97 (dd, J = 7.61 Hz, 2H, H6), 2.87 [s, ²J(¹H–¹¹⁹Sn) = 64.66 Hz, 4H, H1], 1.64 (s, 6H, H9); ¹³C{¹H} NMR (ppm) (CDCl₃, 100 MHz): δ 153.1 (C3), 140.9 (C10), 136.4 (C11), 134.9 (C4), 130.0 (C2), 128.6 (C13), 128.2 (C12), 127.1 (C7), 123.7 (C6), 120.5 (C5), 36.8 (C8), 26.8 (C9), 16.8 [¹J(¹³C–^119/117Sn) = 369.2/353.2 Hz, C1]; ¹¹⁹Sn{¹H} NMR (ppm) (CDCl₃, 149.2 MHz): δ −78.5.

2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms attached to C atoms were placed in geometrically idealized positions and refined as riding on their parent atoms, with C—H = 0.95–0.99 Å and U_iso(H) = 1.2U_eq(C) for aromatic and methyl­ene groups, and 1.5U_eq(C) for methyl groups.

Table 1
Experimental details

For both determinations: [Sn(C₆H₅)₂(C₁₇H₁₆O)], M_r = 509.19, monoclinic, P2₁/n, Z = 8. Experiments were carried out with Mo Kα radiation. Refinement was on 563 parameters. H-atom parameters were constrained.

	7 at 295 K	7 at 100 K
Crystal data
Temperature (K)	295	100
a, b, c (Å)	21.0215 (4), 9.1849 (2), 25.4833 (6)	20.7965 (4), 9.0831 (2), 25.2451 (5)
β (°)	108.497 (2)	107.898 (1)
V (Å^3)	4666.14 (18)	4537.93 (16)
μ (mm^−1)	1.11	1.15
Crystal size (mm)	0.5 × 0.4 × 0.3	0.49 × 0.37 × 0.18
Data collection
Diffractometer	Agilent Xcalibur/Gemini diffractometer with an Atlas detector	Bruker APEXII CCD
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014)	Multi-scan (SADABS; Bruker, 2016)
Tmin, Tmax	0.932, 1.000	0.024, 0.049
No. of measured, independent and observed [I > 2σ(I)] reflections	325733, 12850, 8417	73608, 12229, 11436
Rint	0.061	0.017
(sin θ/λ)max (Å^−1)	0.697	0.686
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.035, 0.080, 1.06	0.022, 0.061, 1.06
No. of reflections	12850	12229
Δρmax, Δρmin (e Å^−3)	0.85, −0.42	0.48, −0.27
Computer programs: CrysAlis PRO (Agilent, 2014), SAINT (Bruker, 2007), APEX2 (Bruker, 2007), SHELXT2018 (Sheldrick, 2015a), SHELXT2014 (Sheldrick, 2015a), SHELXL2018 (Sheldrick, 2015b) and OLEX2 (Dolomanov et al., 2009).

3. Results and discussion

The overall linear synthesis of the dibrominated com­pound Me₂C(C₆H₃CH₂Br)₂O were based on a regioselective double li­thia­tion of the corresponding 9,9-di­methylxanthene, fol­lowed by a formyl­ation reaction with DMF in situ. A reduction of the resulting –CHO groups was then carried out with NaBH₄. Afterwards, the synthesis of com­pound 3 was achieved by a substitution reaction of the hydroxyl groups using Br⁻ as a nucleophile.

Usually, a typical way to prepare organotin com­pounds is by a two-step method. In the first step, the Grignard com­pound RMgX is prepared in anhydrous ether. Once this com­pound is obtained, it is added to a solution of a tin com­pound such as R_nSnX_(4–n) (n = 3 to 0), also in an anhydrous ethereal solvent. In this vein, there are some classical examples of the pre­par­ation of cyclic and bicyclic organotin com­pounds (Jurkschat et al., 1985, 1988; Beuter et al., 1997). These protocols that have used di- and trihalogenate precursors, respectively, yielded mono­nuclear com­pounds that have eight-membered central rings. Thus, we carried out the reactions following an in situ method (Barbier approach), where a mixture of an excess of magnesium turnings with the precursor 3 and the corresponding diorganodihalogenstannane(IV) R₂SnX₂ (X = Cl and Br) in anhydrous THF was sonicated for 20 min at room temperature and then magnetically stirred for a further 20 h. Thus, we obtained heterocyclic mono­nuclear tin(IV) com­plexes of general formula [{Me₂C(C₆H₃CH₂)₂O}SnR₂] [R = Me (4), n-Bu (5), Bn (6) and Ph (7)] (Fig. 1) that were characterized by spectroscopic data (see below). It is noteworthy that we obtained these mono­nuclear com­plexes. For the sake of com­parison, with more flexible precursors, such as {Ch(C₆H₄CH₂Br)₂}, the pro­ducts are dinuclear macroheterocycles of general formula [R₂Sn{Ch(C₆H₄CH₂)₂}₂SnR₂] [Ch = O or S and R = n-Bu, Bn or Ph] (García-González et al., 2024).

3.1. NMR data and analysis of coupling constants

For com­pounds 1–3, the signals of the aromatic protons of the ligand skeleton were observed as an ABC pattern (Fig. S1.1 in the supporting information). In the ¹³C{¹H} NMR spectra (Fig. S1.2), six signals were observed for the different aromatic C atoms; the signals found at higher frequency correspond to the C atoms directly bonded to the heteroatom (oxygen), due to the electron-withdrawing effect. On the other hand, the –CH₂– signals were used to determine that the chemical transformations had been successful. The changes of these signals are clearly noticeable in the ¹³C{¹H} NMR spectrum. Thus, when the C atom corresponds to the –CHO functional group, the signal is at 188.7 ppm; when the reduction reaction is carried out for its transformation into the –CH₂–OH group, the carbon signal shifts to 62.2 ppm. Then the carbon resonances for –CH₂–Br were observed at 29.0 ppm.

The ¹H and ¹³C{¹H} NMR spectra in CDCl₃ solution of all the organotin heterocycles (4–7) showed that the {MeC(C₆H₃CH₂)SnR} moieties are magnetically equivalent (Figs. S2.1 and S2.2). In particular, the ²J(¹H–¹¹⁹Sn) and ¹J(¹³C–^119/117Sn) coupling constant data were fundamental in confirming the formation of the new Sn—CH₂ bonds; the ²J constants ranged from 53.8 to 64.7 Hz, while the second ¹J constants ranged from 225.5 to 369.2 Hz. These coupling data are smaller than those reported in two com­parable mono­nuclear com­pounds of general formula [{Ch(C₆H₄CH₂)₂}SnBr₂] (Ch = O or S), where five-coordinated Sn^IV atoms were observed [²J(¹H–^119/117Sn) = 83.3 and 82.4 Hz; ¹J(¹³C–^119/117Sn) = 461.4 and 482.6 Hz] (Mejía-Rivera et al., 2018). The ¹¹⁹Sn{¹H} NMR spectra of all com­pounds in the non­coordinating CDCl₃ solvent displayed an intense sharp resonance confirming the existence of one tin species (Fig. S2.3). These chemical shifts ranged from 26.8 to −78.5 ppm and are directly related to the nature of the R group in the sequence: Me > n-Bu > Bn > Ph. Hence, this trend is due to the electron density that these substituents donate to the central Sn atom, making it progressively more shielded and, therefore, causing the ¹¹⁹Sn chemical shift to move to lower frequencies (Holeček et al., 1983). All ¹¹⁹Sn{¹H} chemi­cal shifts agreed with a coordination number of four of the central Sn atom in all com­pounds in solution.

3.2. Structure analysis

3.2.1. Mol­ecular structural analysis for 7 at 100 and 298 K

Compound 7 displayed a relatively low melting point (79 °C); com­pounds 4, 5 and 6 were viscous liquids. We crystallized 7 by slow evaporation from an ethereal solution as colourless plates. Single-crystal X-ray diffraction studies were carried out at 100 and 295 K. In both cases, there are two crystallographically independent mol­ecules in the asymmetric unit (Z′ = 2), denoted hereinafter as 7a (Fig. 2, left) and 7b. Despite the different temperatures of the diffraction experiments, the conformations of both 7a and 7b mol­ecules are essentially the same, with an r.m.s. deviation of 0.268 Å (Fig. 2, right); the major difference is in a torsional variation of the arene pendant ring that is far away from the folded xanthenyl system (ca 28°, according to the O⋯Sn—C—C system). Now, in order to properly describe the mol­ecular structure, we envisage three main mol­ecular features in these systems: (i) the local geometry around the Sn atom, (ii) the Sn⋯O intra­molecular transannular distance and (iii) the conformation of the central eight-membered ring linked to the folded xanthenyl tricyclic moiety. Thus, for (i), the analysis of the mol­ecular structures revealed com­pounds with four-coordinated Sn atoms inserted in an eight-membered ring; the Sn—C bond distances reflect the different nature of the C(sp³) versus C(sp²) atoms (Cordero et al., 2008), i.e. the larger the s-character, the shorter the Sn—C bond distance. Considering the C—Sn—C bond angles in both com­pounds, these range from 120.2 to 103.7°, the largest being the –H₂C—Sn—CH₂– angle associated with the `bite ligand'. Then, for (ii), the presence of an electron donor, such as the O atom in this xanthenyl-type com­pound, opens the possibility of an Sn⋯O intra­molecular transannular inter­action. Thus, we observed that the corresponding distances are 2.969 (1)/2.957 (1) and 2.966 (2)/2.948 (2) Å for 7 at 100 and 295 K, respectively; they are larger than the covalent radii sum [Σr_cov(Sn,O) = 2.14 Å] but shorter than the van der Waals radii sum [Σr_vdW(Sn,O) = 3.69 Å] (Porterfield, 1993). Usually, when a donor–acceptor distance fulfils this criterion, secondary bonding is considered (Alcock, 1972). Lastly, a thorough discussion of point (iii) is crucial to consider a possible Sn⋯O intramolecular transannular inter­action. Firstly, we carried out a search for analogous tin(II) and tin(IV) com­pounds in the Cambridge Structural Database (CSD, Version 5.45, update of November 2023; Groom et al., 2016) based on the general formula [{E¹(C₆H_3–nR_nE²)₂O}Sn] (E¹ = any atom; E² = C, N, P, O, S or Se); we found just two phenoxathiin [{S(C₆H₃S)₂O}Sn] and four xanthenyl [{C(C₆H₃E)₂O}Sn] cores. We observed that these species display just two conformations of the dibenzo eight-membered ring, i.e. they present either boat–boat or boat–chair conformations. The first are associated with Sn⋯O distances shorter than 2.632 Å and the second has been observed when the Sn⋯O distance is close to 3.00 Å. In our case, the 7a and 7b mol­ecules display a boat–chair conformation; as a result, we consider that the Sn⋯O inter­action is very weak, despite the fact that it is shorter than the van der Waals radii sum because of the rigidity of the mirror-related eight-membered central ring.

Figure 2 Data at 100 K. (Left) The mol­ecular structure of 7a, with displacement ellipsoids drawn at the 50% probability level. (Right) Superposition of the 7a and 7b mol­ecules. Selected bond distance data (Å): Sn1—C1 2.1759 (14); Sn2—C31 2.1830 (14); Sn1—C8 2.1840 (14); Sn2–C38 2.1818 (14); Sn1—C18 2.1466 (13); Sn2–C48 2.1507 (14); Sn1—C24 2.1343 (14); Sn2—C54 2.1420 (14). Selected torsion (absolute) data (°): O1⋯Sn1—C18—C19 41.9; O2⋯Sn2—C48—C49 68.8.

3.2.2. Analysis of the inter­molecular inter­actions in 7 at 100 and 298 K

The Sn^IV atom, a common Lewis acid, and the O atom, a usual Lewis base, are practically in the inner part of the mol­ecules, i.e. they are hardly exposed to strong inter­molecular contacts. Thus, the large number of hydro­phobic C—H bonds surrounding the 7a and 7b mol­ecules prompts weak C—H⋯π and π–π aromatic shifted inter­actions. For example, we observed a π–π noncovalent inter­action between the arene rings in a centrosymmetric arrangement of either two 7a or 7b mol­ecules that points to the concavity of the folded xanthenyl tricyclic moiety (Fig. 3); it is noteworthy that this type of inter­action can also be observed in phenoxathiin com­pounds [{S(C₆H₃S)₂O}APh₂] [A = Ge (Flores-Chávez et al., 2008), Sn (Martínez-Otero et al., 2012b) and Pb (González-Montiel et al., 2009); Fig. 3, right], with just one mol­ecule per asymmetric unit (Z′ = 1). In all com­pounds, the inter­planar π–π distance (d₁) ranges from 3.345 to 3.591 Å, a typical distance observed for this inter­action. We also show the different shifts according to the centroid–centroid distances (d₂). Despite the presence of soft S atoms in these tetrel com­pounds, including different A—S covalent bonds, the persistence of this π–π noncovalent inter­action in all these systems containing {APh₂}²⁺ fragments indicate the importance of this dimeric association as a synthon for the cohesion and packing of the crystals.

Figure 3 Centrosymmetric arrangement of π-stacking inter­actions for 7a at 100 K (symmetry code: −x + 1, −y + 1, −z + 1) (left) and for analogous tetrel com­pounds [{S(C6H3S)2O}APh2] (A = Ge, Sn and Pb) (right). Structural data are for all com­pounds.

3.3. Hirshfeld surface analysis

The similarity of the conformations of the 7a and 7b mol­ecules at different temperatures and the observed inter­molecular arrangements prompted us to analyze the noncovalent inter­actions using a Hirshfeld surface approach. We used CrystalExplorer21 (Spackman et al., 2009, 2021) with a high standard surface resolution. The surfaces were mapped using a fixed colour scale, red–white–blue, where red highlights contacts shorter than van der Waals (vdW) radii sum, white contacts around the vdW separation and blue contacts longer than the vdW sum.

The surfaces based on the d_norm of 7a and 7b for the crystal data at 100 K mainly exhibit red spots in the vicinity of the aromatic rings, as well as in the methyl­enic H-atom zones; they correspond to the presence of close contacts due to C—H⋯π nonclassical hydrogen bonding and π–π aromatic inter­actions. On the other hand, the data for the two mol­ecules in the asymmetric unit at 295 K do not clearly display the red spots. Thus, it is evident that the shrinking of the unit-cell parameters due to the low-temperature conditions enhances the presence of these inter­molecular contacts; the Hirshfeld surface volumes underwent a 2.78% contraction, from 567.11/583.17 ų at 295 K to 551.29/566.90 ų at 100 K.

We plotted the 2D fingerprints of the corresponding Hirshfeld surfaces to assess the contribution of each inter­molecular contact; the main contributions are listed in Fig. 4 and some selected fingerprint plots are also displayed. As expected, they look very similar for each of 7a and 7b. The analysis of the inter­molecular contact contributions showed that H⋯H contacts are dominant, where the shortest are 2.211 (100 K) and 2.289 Å (295 K), observed between the aromatic H atoms C13—H13⋯H36—C36 of 7a and 7b, respectively. These facts are reflected in the slight shift of the spike positioned at the inter­section d_i ≃ 1.1/d_e ≃ 1.1 Å of the 2D fingerprints. The next predominant noncovalent contributions are the C⋯H/H⋯C due to the presence of the aromatic rings. The overall contribution change for these respective inter­actions is close to 1.0%; it is worth mentioning that the O⋯H/H⋯O nonclassical hydrogen bonding essentially remains the same at both temperatures.

Figure 4 Hirshfeld surfaces mapped over dnorm (−0.0400 to 1.2000 range), with relative contributions in percentages for the various inter­molecular contacts, and fragment patches for 7a and 7b at 100 and 295 K. Data in parentheses are the superficial area in Å^2 and the volume in Å^3, respectively. Italic data in curly brackets are the number of inter­acting surrounding fragments and the four major areas as percentages.

The fragment patch plots are useful for calculating the number of mol­ecules that inter­act with a central mol­ecule; also, the area data of these patches can be used to find the external major mol­ecular fragments that are closer to a given HS. In Fig. 4 are plotted the corresponding fragment patches over the HS; the numbers of inter­acting mol­ecules are 13 and 15 for mol­ecules 7a and 7b, respectively, regardless of the diffraction temperature. The four larger areas over the HS surfaces are 68.8, 57.5, 55.3 and 53.9 Ų that represent 52.8% of the superficial area for 7a at 100 K; 63.6, 55.4, 54.7 and 38.7 Ų (47.2% superficial area) for 7b at 100 K; 68.6, 57.3, 57.2 and 53.7 Ų (52.5% superficial area) for 7a at 295 K; and 63.9, 55.9, 55.8 and 39.1 Ų (47.2% superficial area) for 7b at 295 K. Overall, four inter­acting mol­ecules cover more than half of each HS, despite the difference in the number of surrounding mol­ecules. In particular, the major surface area represents the inter­action with another 7a mol­ecule, forming the centrosymmetric arrangement described in Fig. 3. Thus, we decided to analyze the mol­ecular electrostatic potential (MEP) pro­jec­ted onto the Hirshfeld surface to gain a deeper insight. The MEP was calculated with the TONTO quantum modelling package (Jayatilaka & Grimwood, 2003) implemented in CrystalExplorer21, using the Becke three-parameter Lee–Yang–Parr (B3LYP) hybrid functionals (Becke, 1993) with the DGDZVP basis set (Godbout et al., 1992; Sosa et al., 1992). The analysis of the MEP showed that the blue regions, corresponding to positive electrostatic potential, occur around the C—H zones, and faint red regions, corresponding to negative potentials, occur near the centres of the aromatic rings (Fig. 5). The inter­action of these negative potentials between the two arene groups prompted us to analyze the energies for the inter­molecular inter­actions; this analysis was carried out based on the energy framework approach (Mackenzie et al., 2017). We again used CrystalExplorer21, considering the four energy com­ponents: electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange–repulsion (E_rep). The energies were obtained using the B3LYP/DGDZVP level of theory; for the framework construction, we considered a default radius of 3.80 Å.

Figure 5 Electrostatic potential mapped on the Hirshfeld surface of 7a at 100 K. Only shown are the potentials at the points of C⋯H and π–π contacts around the concavity of the xanthenyl moiety and its inter­action with the arene group of a second 7a mol­ecule (symmetry code: −x + 1, −y + 1, −z + 1).

For the visual com­parison of the magnitudes of the inter­action energies for com­pound 7 at the two diffraction temperatures, they were adjusted to a cylinder scale of 100 with a cut-off value of 10 kJ mol⁻¹ within 2 × 2 × 2 unit cells (Fig. 6). We also show an energy framework for six inter­locked mol­ecules, where the 7a/7b pair (in black) is in a general position; for the four remaining mol­ecules we used red, green, pink and blue colours, with symmetry operators (−x + 1, −y + 2, −z + 2), (−x + 1, −y + 1, −z + 1), (−x + 1, −y + 2, −z + 1) and (x, y, z − 1), respectively. These six mol­ecules make three centrosymmetric dimers along the c axis; the corresponding centroid-to-centroid distances are 8.15, 8.03, 7.89, 6.76 and 8.15 Å. It is clear that the dispersion forces arising from the C—H⋯π inter­actions make a significant contribution to the supra­molecular architecture in the crystal [total energy data: −50.59 and −41.76 kJ mol⁻¹ for the 7a(green)/7b(pink) and 7a/7b pairs, respectively], as has been stated (Tiekink & Zukerman-Schpector, 2012). In addition, the π–π inter­actions between the arene groups, whose total energy data are −57.14 and −41.76 kJ mol⁻¹ for the 7a/7a(green) and 7b/7b(red) pairs, respectively, are also very important. Overall, the green cylinders joining the centroids of the different 7a and 7b mol­ecules are almost parallel in magnitude with the total energy (cylinders in blue). Finally, the energy frameworks were very useful for visualizing that there are more contributions at low temperature because of the shrinking of the lattice parameters (see, for example, the red cylinders in Fig. 6, upper and middle rows).

Figure 6 Energy frameworks for com­pound 7 at 100 (upper row) and 295 K (middle row), showing the electrostatic energy (in red), the dispersion energy (in green) and the total energy terms (in blue). The energy frameworks were adjusted to the same scale factor of 100 with a cut-off value of 10 kJ mol^−1 within 2 × 2 × 2 unit cells, along the b axis. Energy frameworks for the three centrosymmetric dimers along the c axis (bottom row; 100 K data).

4. Conclusions

We showed that an approach to form Sn—C bonds based on Barbier-type reactions assisted by sonochemical activation of the Mg surface is an easy and successful option to yield organotin mono­nuclear heterocyclic com­pounds when a xanthenyl moiety is used. From the Hirshfeld surface analysis, we also showed that one of the synthesized organotin heterocycles (com­pound 7) crystallized by means of weak C—H⋯π, π–π and H⋯H noncovalent inter­actions; this is related to the relatively low melting point observed for 7 and the absence of crystals for the other organotin heterocycles with either small groups, such as methyl, or more conformationally flexible groups, such as n-butyl or benzyl. In the crystal of 7, the energy frameworks showed that there are more contributions to the architecture of the crystal arrangement at low temperature and that the cohesion between the organotin heterocycles is mainly due to dispersion forces.

Supporting information

Computing details

17,17-Dimethyl-7,7-diphenyl-15-oxa-7-stannatetracyclo[11.3.1.0^5,16.0^9,14]heptadeca-1,3,5(16),9(14),10,12-hexaene (7_295K_02)

Crystal data

[Sn(C6H5)2(C17H16O)]	Dx = 1.450 Mg m^−3
Mr = 509.19	Melting point: 352 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 21.0215 (4) Å	Cell parameters from 56362 reflections
b = 9.1849 (2) Å	θ = 3.4–25.6°
c = 25.4833 (6) Å	µ = 1.11 mm^−1
β = 108.497 (2)°	T = 295 K
V = 4666.14 (18) Å^3	Block, clear colourless
Z = 8	0.5 × 0.4 × 0.3 mm
F(000) = 2064

Data collection

Agilent Xcalibur/Gemini diffractometer with an Atlas detector	12850 independent reflections
Radiation source: Enhance (Mo) X-ray Source	8417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 10.3659 pixels mm^-1	θmax = 29.7°, θmin = 3.0°
ω scans	h = −28→29
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→12
Tmin = 0.932, Tmax = 1.000	l = −35→35
325733 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0229P)^2 + 3.8253P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.004
12850 reflections	Δρmax = 0.85 e Å^−3
563 parameters	Δρmin = −0.42 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.55492 (2)	0.13987 (2)	0.63958 (2)	0.04645 (6)
O1	0.44023 (8)	0.26072 (18)	0.66952 (7)	0.0419 (4)
C1	0.57550 (13)	0.2853 (3)	0.71019 (11)	0.0516 (7)
H1A	0.569007	0.232493	0.741070	0.062*
H1B	0.622151	0.314973	0.720834	0.062*
C2	0.53233 (13)	0.4183 (3)	0.69952 (10)	0.0437 (6)
C3	0.46328 (12)	0.4033 (3)	0.67818 (9)	0.0397 (5)
C4	0.41792 (13)	0.5161 (3)	0.66182 (10)	0.0442 (6)
C5	0.44453 (16)	0.6558 (3)	0.66926 (12)	0.0564 (7)
H5	0.416103	0.735731	0.659231	0.068*
C6	0.51275 (17)	0.6768 (3)	0.69138 (13)	0.0619 (8)
H6	0.529704	0.771145	0.696389	0.074*
C7	0.55620 (15)	0.5611 (3)	0.70618 (11)	0.0553 (7)
H7	0.602062	0.578163	0.720812	0.066*
C8	0.45968 (13)	0.0233 (3)	0.61427 (12)	0.0523 (7)
H8A	0.461027	−0.050249	0.587347	0.063*
H8B	0.454423	−0.026324	0.646237	0.063*
C9	0.40007 (13)	0.1182 (3)	0.58983 (11)	0.0452 (6)
C10	0.39174 (12)	0.2411 (3)	0.61834 (10)	0.0402 (5)
C11	0.34225 (12)	0.3445 (3)	0.59897 (11)	0.0451 (6)
C12	0.29531 (14)	0.3169 (4)	0.54757 (12)	0.0592 (8)
H12	0.260531	0.382248	0.532419	0.071*
C13	0.30068 (15)	0.1909 (4)	0.51895 (12)	0.0673 (9)
H13	0.267980	0.171501	0.485324	0.081*
C14	0.35240 (14)	0.0948 (3)	0.53861 (12)	0.0597 (8)
H14	0.355640	0.013784	0.517692	0.072*
C15	0.34404 (13)	0.4773 (3)	0.63572 (11)	0.0493 (6)
C16	0.30323 (16)	0.6042 (3)	0.60286 (14)	0.0680 (9)
H16A	0.306432	0.686070	0.626971	0.102*
H16B	0.257122	0.575528	0.587441	0.102*
H16C	0.320535	0.630572	0.573543	0.102*
C17	0.31457 (15)	0.4332 (4)	0.68170 (13)	0.0639 (8)
H17A	0.338938	0.351328	0.701689	0.096*
H17B	0.268214	0.407310	0.665400	0.096*
H17C	0.318211	0.513449	0.706611	0.096*
C18	0.63054 (13)	−0.0258 (3)	0.66188 (12)	0.0515 (7)
C19	0.66470 (16)	−0.0575 (4)	0.71631 (15)	0.0746 (9)
H19	0.656191	−0.004502	0.744465	0.090*
C20	0.7125 (2)	−0.1699 (6)	0.7293 (2)	0.1015 (15)
H20	0.735364	−0.191855	0.766087	0.122*
C21	0.7253 (2)	−0.2466 (5)	0.6883 (3)	0.1049 (15)
H21	0.757960	−0.318961	0.697073	0.126*
C22	0.6914 (2)	−0.2190 (5)	0.6355 (2)	0.0966 (13)
H22	0.699358	−0.274584	0.607753	0.116*
C23	0.64469 (16)	−0.1085 (4)	0.62175 (16)	0.0728 (9)
H23	0.622211	−0.089373	0.584645	0.087*
C24	0.56121 (14)	0.2610 (3)	0.57022 (12)	0.0531 (7)
C25	0.60390 (17)	0.3788 (4)	0.57699 (15)	0.0715 (9)
H25	0.631121	0.404291	0.612294	0.086*
C26	0.60665 (19)	0.4599 (4)	0.53159 (18)	0.0854 (11)
H26	0.635899	0.538436	0.536738	0.102*
C27	0.5667 (2)	0.4246 (4)	0.47966 (17)	0.0818 (11)
H27	0.568599	0.479313	0.449477	0.098*
C28	0.5237 (2)	0.3087 (4)	0.47194 (14)	0.0809 (11)
H28	0.496475	0.284334	0.436523	0.097*
C29	0.52109 (18)	0.2280 (4)	0.51703 (13)	0.0681 (9)
H29	0.491650	0.149637	0.511458	0.082*
Sn2	0.41848 (2)	0.86546 (2)	0.80803 (2)	0.04785 (6)
O2	0.55601 (9)	0.7564 (2)	0.82774 (7)	0.0523 (5)
C31	0.48984 (14)	1.0059 (3)	0.78672 (11)	0.0545 (7)
H31A	0.493979	0.973464	0.751725	0.065*
H31B	0.471847	1.104042	0.781359	0.065*
C32	0.55847 (13)	1.0107 (3)	0.82865 (10)	0.0497 (7)
C33	0.59119 (13)	0.8822 (3)	0.84887 (11)	0.0487 (6)
C34	0.65260 (13)	0.8710 (4)	0.89000 (11)	0.0559 (7)
C35	0.68393 (16)	1.0022 (5)	0.91010 (13)	0.0714 (10)
H35	0.725861	1.001442	0.937056	0.086*
C36	0.65404 (17)	1.1324 (4)	0.89084 (14)	0.0703 (9)
H36	0.676240	1.218550	0.904783	0.084*
C37	0.59157 (16)	1.1387 (4)	0.85111 (12)	0.0617 (8)
H37	0.571616	1.228441	0.839360	0.074*
C38	0.43568 (14)	0.6322 (3)	0.81566 (13)	0.0578 (7)
H38A	0.396406	0.585613	0.820336	0.069*
H38B	0.441007	0.595880	0.781552	0.069*
C39	0.49584 (14)	0.5895 (3)	0.86282 (12)	0.0552 (7)
C40	0.55729 (14)	0.6545 (3)	0.86822 (12)	0.0522 (7)
C41	0.61563 (15)	0.6324 (3)	0.91170 (13)	0.0600 (7)
C42	0.61191 (18)	0.5344 (4)	0.95210 (15)	0.0776 (10)
H42	0.649921	0.515108	0.982023	0.093*
C43	0.55261 (19)	0.4658 (4)	0.94826 (17)	0.0861 (11)
H43	0.551104	0.400015	0.975598	0.103*
C44	0.49518 (17)	0.4925 (4)	0.90459 (15)	0.0736 (9)
H44	0.455543	0.445076	0.903048	0.088*
C45	0.67738 (15)	0.7186 (4)	0.91020 (14)	0.0692 (9)
C46	0.73074 (18)	0.7225 (5)	0.96749 (16)	0.0977 (13)
H46A	0.744485	0.624932	0.979310	0.147*
H46B	0.712330	0.767549	0.993464	0.147*
H46C	0.768796	0.777370	0.965573	0.147*
C47	0.70683 (19)	0.6450 (5)	0.86877 (19)	0.0999 (14)
H47A	0.745555	0.698134	0.867320	0.150*
H47B	0.673764	0.643995	0.832736	0.150*
H47C	0.719548	0.546828	0.880425	0.150*
C48	0.32719 (13)	0.8917 (3)	0.74027 (11)	0.0480 (6)
C49	0.32218 (14)	0.9925 (3)	0.69897 (12)	0.0599 (8)
H49	0.358076	1.054755	0.702005	0.072*
C50	0.26533 (16)	1.0038 (4)	0.65322 (13)	0.0706 (9)
H50	0.263179	1.072691	0.625965	0.085*
C51	0.21237 (16)	0.9128 (4)	0.64846 (14)	0.0738 (10)
H51	0.174093	0.919290	0.617717	0.089*
C52	0.21546 (15)	0.8123 (4)	0.68869 (15)	0.0720 (9)
H52	0.179121	0.751158	0.685362	0.086*
C53	0.27255 (13)	0.8010 (4)	0.73450 (12)	0.0567 (7)
H53	0.274231	0.731985	0.761610	0.068*
C54	0.41189 (13)	0.9403 (3)	0.88557 (11)	0.0514 (7)
C55	0.43133 (16)	1.0795 (4)	0.90461 (13)	0.0633 (8)
H55	0.446489	1.142831	0.882677	0.076*
C56	0.42884 (18)	1.1270 (4)	0.95513 (15)	0.0763 (10)
H56	0.441979	1.221390	0.966814	0.092*
C57	0.40715 (17)	1.0358 (5)	0.98809 (14)	0.0759 (10)
H57	0.405634	1.067662	1.022314	0.091*
C58	0.38765 (18)	0.8975 (5)	0.97062 (15)	0.0771 (10)
H58	0.372940	0.835067	0.993081	0.093*
C59	0.38967 (16)	0.8498 (4)	0.91960 (14)	0.0662 (8)
H59	0.375917	0.755587	0.908037	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.04473 (10)	0.04359 (10)	0.04977 (11)	0.00585 (8)	0.01320 (8)	0.00553 (8)
O1	0.0458 (9)	0.0361 (9)	0.0400 (9)	−0.0022 (7)	0.0084 (8)	0.0046 (7)
C1	0.0461 (14)	0.0581 (17)	0.0450 (14)	−0.0004 (12)	0.0066 (12)	0.0029 (13)
C2	0.0485 (14)	0.0464 (14)	0.0360 (12)	−0.0057 (11)	0.0133 (11)	−0.0029 (11)
C3	0.0505 (14)	0.0377 (13)	0.0334 (12)	−0.0055 (10)	0.0168 (11)	−0.0010 (10)
C4	0.0570 (15)	0.0383 (14)	0.0424 (13)	0.0014 (11)	0.0233 (12)	0.0023 (11)
C5	0.074 (2)	0.0383 (15)	0.0649 (18)	0.0032 (13)	0.0334 (16)	0.0017 (13)
C6	0.079 (2)	0.0427 (16)	0.069 (2)	−0.0135 (15)	0.0310 (17)	−0.0085 (14)
C7	0.0569 (16)	0.0557 (18)	0.0527 (16)	−0.0153 (14)	0.0166 (13)	−0.0096 (14)
C8	0.0555 (16)	0.0387 (14)	0.0606 (17)	0.0007 (12)	0.0155 (14)	−0.0017 (12)
C9	0.0440 (13)	0.0419 (15)	0.0480 (14)	−0.0049 (11)	0.0123 (11)	−0.0009 (11)
C10	0.0424 (13)	0.0392 (13)	0.0374 (12)	−0.0032 (10)	0.0104 (11)	0.0024 (10)
C11	0.0410 (13)	0.0476 (15)	0.0472 (14)	0.0014 (11)	0.0149 (11)	0.0072 (12)
C12	0.0466 (15)	0.067 (2)	0.0569 (17)	0.0051 (14)	0.0057 (13)	0.0104 (15)
C13	0.0514 (17)	0.092 (2)	0.0475 (17)	−0.0132 (17)	−0.0003 (14)	−0.0162 (17)
C14	0.0552 (17)	0.0602 (18)	0.0578 (17)	−0.0057 (14)	0.0095 (14)	−0.0154 (14)
C15	0.0513 (15)	0.0448 (15)	0.0564 (16)	0.0062 (12)	0.0236 (13)	0.0046 (12)
C16	0.0629 (19)	0.0579 (19)	0.083 (2)	0.0214 (15)	0.0231 (17)	0.0098 (16)
C17	0.0652 (19)	0.069 (2)	0.0695 (19)	−0.0009 (16)	0.0382 (16)	−0.0031 (16)
C18	0.0388 (13)	0.0482 (16)	0.0646 (18)	0.0022 (11)	0.0122 (13)	0.0072 (13)
C19	0.0593 (19)	0.081 (2)	0.074 (2)	0.0078 (17)	0.0077 (17)	0.0090 (19)
C20	0.068 (2)	0.117 (4)	0.101 (3)	0.018 (2)	0.001 (2)	0.045 (3)
C21	0.068 (2)	0.080 (3)	0.161 (5)	0.029 (2)	0.028 (3)	0.022 (3)
C22	0.073 (2)	0.083 (3)	0.134 (4)	0.023 (2)	0.032 (3)	−0.016 (3)
C23	0.0626 (19)	0.074 (2)	0.080 (2)	0.0159 (17)	0.0199 (17)	−0.0021 (18)
C24	0.0565 (16)	0.0488 (16)	0.0572 (17)	0.0090 (13)	0.0226 (14)	0.0079 (13)
C25	0.067 (2)	0.075 (2)	0.076 (2)	−0.0032 (17)	0.0277 (17)	0.0139 (18)
C26	0.081 (2)	0.081 (3)	0.109 (3)	−0.004 (2)	0.051 (2)	0.022 (2)
C27	0.113 (3)	0.072 (2)	0.085 (3)	0.031 (2)	0.066 (2)	0.028 (2)
C28	0.125 (3)	0.072 (2)	0.0535 (19)	0.024 (2)	0.040 (2)	0.0035 (17)
C29	0.097 (2)	0.0500 (18)	0.0590 (19)	0.0079 (17)	0.0264 (18)	−0.0003 (15)
Sn2	0.04183 (10)	0.05148 (11)	0.04543 (10)	−0.00470 (8)	0.00703 (8)	0.00517 (8)
O2	0.0509 (10)	0.0599 (12)	0.0420 (10)	−0.0066 (9)	0.0087 (8)	−0.0023 (9)
C31	0.0544 (16)	0.0576 (18)	0.0498 (15)	−0.0072 (13)	0.0141 (13)	0.0072 (13)
C32	0.0475 (14)	0.0655 (18)	0.0393 (13)	−0.0149 (13)	0.0183 (12)	−0.0011 (13)
C33	0.0464 (14)	0.0612 (18)	0.0402 (13)	−0.0116 (12)	0.0159 (12)	−0.0031 (12)
C34	0.0411 (14)	0.079 (2)	0.0459 (15)	−0.0091 (14)	0.0121 (12)	−0.0036 (14)
C35	0.0486 (17)	0.104 (3)	0.0556 (18)	−0.0227 (18)	0.0083 (14)	−0.0092 (19)
C36	0.067 (2)	0.082 (2)	0.0614 (19)	−0.0339 (18)	0.0196 (17)	−0.0131 (18)
C37	0.0663 (19)	0.068 (2)	0.0543 (17)	−0.0192 (16)	0.0240 (15)	−0.0008 (15)
C38	0.0510 (15)	0.0524 (17)	0.0629 (18)	−0.0106 (13)	0.0080 (14)	0.0001 (14)
C39	0.0537 (16)	0.0455 (15)	0.0627 (18)	0.0008 (12)	0.0132 (14)	0.0024 (13)
C40	0.0503 (15)	0.0528 (17)	0.0516 (16)	0.0036 (12)	0.0132 (13)	−0.0004 (13)
C41	0.0525 (16)	0.0649 (19)	0.0569 (17)	0.0085 (14)	0.0093 (14)	0.0010 (15)
C42	0.069 (2)	0.081 (2)	0.071 (2)	0.0197 (19)	0.0061 (18)	0.0193 (19)
C43	0.083 (2)	0.075 (2)	0.095 (3)	0.009 (2)	0.019 (2)	0.039 (2)
C44	0.066 (2)	0.063 (2)	0.087 (2)	0.0015 (16)	0.0180 (18)	0.0226 (18)
C45	0.0438 (16)	0.091 (3)	0.066 (2)	0.0054 (16)	0.0074 (15)	−0.0012 (18)
C46	0.059 (2)	0.122 (4)	0.088 (3)	0.001 (2)	−0.0105 (19)	0.015 (3)
C47	0.069 (2)	0.122 (4)	0.115 (3)	0.018 (2)	0.039 (2)	−0.011 (3)
C48	0.0408 (13)	0.0546 (17)	0.0468 (14)	0.0029 (11)	0.0113 (11)	−0.0026 (12)
C49	0.0483 (15)	0.0643 (19)	0.0606 (18)	0.0004 (14)	0.0081 (14)	0.0102 (15)
C50	0.0587 (19)	0.082 (2)	0.0623 (19)	0.0169 (17)	0.0071 (16)	0.0157 (17)
C51	0.0470 (17)	0.102 (3)	0.062 (2)	0.0202 (18)	0.0027 (15)	−0.006 (2)
C52	0.0405 (16)	0.096 (3)	0.077 (2)	−0.0099 (16)	0.0156 (16)	−0.017 (2)
C53	0.0481 (15)	0.0680 (19)	0.0566 (17)	−0.0009 (14)	0.0204 (13)	−0.0037 (15)
C54	0.0430 (14)	0.0604 (18)	0.0474 (15)	−0.0002 (12)	0.0095 (12)	0.0082 (13)
C55	0.0650 (19)	0.064 (2)	0.0621 (19)	−0.0037 (15)	0.0216 (15)	0.0023 (16)
C56	0.079 (2)	0.079 (2)	0.072 (2)	−0.0003 (19)	0.0240 (19)	−0.0150 (19)
C57	0.071 (2)	0.101 (3)	0.0572 (19)	0.020 (2)	0.0219 (17)	0.001 (2)
C58	0.073 (2)	0.100 (3)	0.067 (2)	0.009 (2)	0.0342 (18)	0.024 (2)
C59	0.0674 (19)	0.065 (2)	0.069 (2)	−0.0017 (16)	0.0254 (16)	0.0101 (16)

Geometric parameters (Å, º)

Sn1—C1	2.171 (3)	Sn2—C31	2.174 (3)
Sn1—C8	2.180 (3)	Sn2—C38	2.172 (3)
Sn1—C18	2.143 (3)	Sn2—C48	2.149 (3)
Sn1—C24	2.128 (3)	Sn2—C54	2.138 (3)
O1—C3	1.389 (3)	O2—C33	1.386 (3)
O1—C10	1.389 (3)	O2—C40	1.387 (3)
C1—H1A	0.9700	C31—H31A	0.9700
C1—H1B	0.9700	C31—H31B	0.9700
C1—C2	1.495 (4)	C31—C32	1.499 (4)
C2—C3	1.386 (3)	C32—C33	1.380 (4)
C2—C7	1.395 (4)	C32—C37	1.394 (4)
C3—C4	1.380 (3)	C33—C34	1.385 (4)
C4—C5	1.388 (4)	C34—C35	1.391 (5)
C4—C15	1.525 (4)	C34—C45	1.525 (5)
C5—H5	0.9300	C35—H35	0.9300
C5—C6	1.378 (4)	C35—C36	1.367 (5)
C6—H6	0.9300	C36—H36	0.9300
C6—C7	1.374 (4)	C36—C37	1.382 (4)
C7—H7	0.9300	C37—H37	0.9300
C8—H8A	0.9700	C38—H38A	0.9700
C8—H8B	0.9700	C38—H38B	0.9700
C8—C9	1.490 (4)	C38—C39	1.494 (4)
C9—C10	1.384 (4)	C39—C40	1.390 (4)
C9—C14	1.387 (4)	C39—C44	1.392 (4)
C10—C11	1.379 (3)	C40—C41	1.382 (4)
C11—C12	1.390 (4)	C41—C42	1.388 (5)
C11—C15	1.531 (4)	C41—C45	1.531 (5)
C12—H12	0.9300	C42—H42	0.9300
C12—C13	1.391 (4)	C42—C43	1.372 (5)
C13—H13	0.9300	C43—H43	0.9300
C13—C14	1.367 (4)	C43—C44	1.380 (5)
C14—H14	0.9300	C44—H44	0.9300
C15—C16	1.529 (4)	C45—C46	1.534 (4)
C15—C17	1.543 (4)	C45—C47	1.539 (5)
C16—H16A	0.9600	C46—H46A	0.9600
C16—H16B	0.9600	C46—H46B	0.9600
C16—H16C	0.9600	C46—H46C	0.9600
C17—H17A	0.9600	C47—H47A	0.9600
C17—H17B	0.9600	C47—H47B	0.9600
C17—H17C	0.9600	C47—H47C	0.9600
C18—C19	1.375 (4)	C48—C49	1.381 (4)
C18—C23	1.380 (4)	C48—C53	1.388 (4)
C19—H19	0.9300	C49—H49	0.9300
C19—C20	1.405 (5)	C49—C50	1.383 (4)
C20—H20	0.9300	C50—H50	0.9300
C20—C21	1.356 (6)	C50—C51	1.367 (5)
C21—H21	0.9300	C51—H51	0.9300
C21—C22	1.331 (6)	C51—C52	1.365 (5)
C22—H22	0.9300	C52—H52	0.9300
C22—C23	1.378 (5)	C52—C53	1.387 (4)
C23—H23	0.9300	C53—H53	0.9300
C24—C25	1.381 (4)	C54—C55	1.383 (4)
C24—C29	1.384 (4)	C54—C59	1.385 (4)
C25—H25	0.9300	C55—H55	0.9300
C25—C26	1.392 (5)	C55—C56	1.376 (5)
C26—H26	0.9300	C56—H56	0.9300
C26—C27	1.362 (5)	C56—C57	1.363 (5)
C27—H27	0.9300	C57—H57	0.9300
C27—C28	1.369 (6)	C57—C58	1.365 (5)
C28—H28	0.9300	C58—H58	0.9300
C28—C29	1.384 (5)	C58—C59	1.386 (5)
C29—H29	0.9300	C59—H59	0.9300
C1—Sn1—C8	118.03 (11)	C38—Sn2—C31	119.97 (12)
C18—Sn1—C1	106.32 (11)	C48—Sn2—C31	104.11 (10)
C18—Sn1—C8	105.32 (10)	C48—Sn2—C38	105.26 (11)
C24—Sn1—C1	108.57 (11)	C54—Sn2—C31	106.99 (11)
C24—Sn1—C8	107.71 (11)	C54—Sn2—C38	106.99 (12)
C24—Sn1—C18	110.81 (11)	C54—Sn2—C48	113.79 (10)
C10—O1—C3	112.74 (18)	C33—O2—C40	113.1 (2)
Sn1—C1—H1A	108.8	Sn2—C31—H31A	108.5
Sn1—C1—H1B	108.8	Sn2—C31—H31B	108.5
H1A—C1—H1B	107.7	H31A—C31—H31B	107.5
C2—C1—Sn1	113.72 (17)	C32—C31—Sn2	115.06 (18)
C2—C1—H1A	108.8	C32—C31—H31A	108.5
C2—C1—H1B	108.8	C32—C31—H31B	108.5
C3—C2—C1	119.3 (2)	C33—C32—C31	119.6 (3)
C3—C2—C7	115.7 (2)	C33—C32—C37	116.3 (3)
C7—C2—C1	124.9 (2)	C37—C32—C31	124.0 (3)
C2—C3—O1	115.2 (2)	C32—C33—O2	115.2 (2)
C4—C3—O1	119.1 (2)	C32—C33—C34	125.5 (3)
C4—C3—C2	125.5 (2)	C34—C33—O2	119.1 (3)
C3—C4—C5	116.3 (3)	C33—C34—C35	115.6 (3)
C3—C4—C15	117.8 (2)	C33—C34—C45	117.4 (3)
C5—C4—C15	125.9 (2)	C35—C34—C45	126.9 (3)
C4—C5—H5	119.8	C34—C35—H35	119.5
C6—C5—C4	120.5 (3)	C36—C35—C34	121.0 (3)
C6—C5—H5	119.8	C36—C35—H35	119.5
C5—C6—H6	119.4	C35—C36—H36	119.3
C7—C6—C5	121.2 (3)	C35—C36—C37	121.4 (3)
C7—C6—H6	119.4	C37—C36—H36	119.3
C2—C7—H7	119.6	C32—C37—H37	120.0
C6—C7—C2	120.8 (3)	C36—C37—C32	120.0 (3)
C6—C7—H7	119.6	C36—C37—H37	120.0
Sn1—C8—H8A	108.7	Sn2—C38—H38A	108.8
Sn1—C8—H8B	108.7	Sn2—C38—H38B	108.8
H8A—C8—H8B	107.6	H38A—C38—H38B	107.7
C9—C8—Sn1	114.10 (18)	C39—C38—Sn2	113.89 (19)
C9—C8—H8A	108.7	C39—C38—H38A	108.8
C9—C8—H8B	108.7	C39—C38—H38B	108.8
C10—C9—C8	119.2 (2)	C40—C39—C38	119.4 (3)
C10—C9—C14	116.5 (2)	C40—C39—C44	115.7 (3)
C14—C9—C8	124.3 (3)	C44—C39—C38	124.9 (3)
C9—C10—O1	114.9 (2)	O2—C40—C39	114.7 (2)
C11—C10—O1	119.5 (2)	C41—C40—O2	119.9 (3)
C11—C10—C9	125.5 (2)	C41—C40—C39	125.2 (3)
C10—C11—C12	116.2 (3)	C40—C41—C42	116.4 (3)
C10—C11—C15	117.4 (2)	C40—C41—C45	116.6 (3)
C12—C11—C15	126.4 (2)	C42—C41—C45	127.0 (3)
C11—C12—H12	120.2	C41—C42—H42	119.7
C11—C12—C13	119.6 (3)	C43—C42—C41	120.6 (3)
C13—C12—H12	120.2	C43—C42—H42	119.7
C12—C13—H13	118.9	C42—C43—H43	119.4
C14—C13—C12	122.2 (3)	C42—C43—C44	121.2 (3)
C14—C13—H13	118.9	C44—C43—H43	119.4
C9—C14—H14	120.1	C39—C44—H44	119.6
C13—C14—C9	119.9 (3)	C43—C44—C39	120.8 (3)
C13—C14—H14	120.1	C43—C44—H44	119.6
C4—C15—C11	106.1 (2)	C34—C45—C41	106.4 (2)
C4—C15—C16	112.2 (2)	C34—C45—C46	111.6 (3)
C4—C15—C17	109.2 (2)	C34—C45—C47	109.9 (3)
C11—C15—C17	108.5 (2)	C41—C45—C46	111.0 (3)
C16—C15—C11	111.8 (2)	C41—C45—C47	108.6 (3)
C16—C15—C17	109.0 (2)	C46—C45—C47	109.3 (3)
C15—C16—H16A	109.5	C45—C46—H46A	109.5
C15—C16—H16B	109.5	C45—C46—H46B	109.5
C15—C16—H16C	109.5	C45—C46—H46C	109.5
H16A—C16—H16B	109.5	H46A—C46—H46B	109.5
H16A—C16—H16C	109.5	H46A—C46—H46C	109.5
H16B—C16—H16C	109.5	H46B—C46—H46C	109.5
C15—C17—H17A	109.5	C45—C47—H47A	109.5
C15—C17—H17B	109.5	C45—C47—H47B	109.5
C15—C17—H17C	109.5	C45—C47—H47C	109.5
H17A—C17—H17B	109.5	H47A—C47—H47B	109.5
H17A—C17—H17C	109.5	H47A—C47—H47C	109.5
H17B—C17—H17C	109.5	H47B—C47—H47C	109.5
C19—C18—Sn1	121.6 (2)	C49—C48—Sn2	121.3 (2)
C19—C18—C23	117.7 (3)	C49—C48—C53	117.5 (3)
C23—C18—Sn1	120.7 (2)	C53—C48—Sn2	121.1 (2)
C18—C19—H19	120.1	C48—C49—H49	119.0
C18—C19—C20	119.9 (4)	C48—C49—C50	121.9 (3)
C20—C19—H19	120.1	C50—C49—H49	119.0
C19—C20—H20	119.9	C49—C50—H50	120.3
C21—C20—C19	120.2 (4)	C51—C50—C49	119.4 (3)
C21—C20—H20	119.9	C51—C50—H50	120.3
C20—C21—H21	119.8	C50—C51—H51	119.9
C22—C21—C20	120.4 (4)	C52—C51—C50	120.2 (3)
C22—C21—H21	119.8	C52—C51—H51	119.9
C21—C22—H22	119.7	C51—C52—H52	119.8
C21—C22—C23	120.5 (4)	C51—C52—C53	120.3 (3)
C23—C22—H22	119.7	C53—C52—H52	119.8
C18—C23—H23	119.3	C48—C53—H53	119.7
C22—C23—C18	121.4 (4)	C52—C53—C48	120.7 (3)
C22—C23—H23	119.3	C52—C53—H53	119.7
C25—C24—Sn1	121.0 (2)	C55—C54—Sn2	121.5 (2)
C25—C24—C29	117.6 (3)	C55—C54—C59	117.2 (3)
C29—C24—Sn1	121.3 (2)	C59—C54—Sn2	121.3 (2)
C24—C25—H25	119.6	C54—C55—H55	119.1
C24—C25—C26	120.8 (4)	C56—C55—C54	121.8 (3)
C26—C25—H25	119.6	C56—C55—H55	119.1
C25—C26—H26	119.8	C55—C56—H56	119.9
C27—C26—C25	120.3 (4)	C57—C56—C55	120.1 (4)
C27—C26—H26	119.8	C57—C56—H56	119.9
C26—C27—H27	120.0	C56—C57—H57	120.2
C26—C27—C28	120.0 (3)	C56—C57—C58	119.7 (3)
C28—C27—H27	120.0	C58—C57—H57	120.2
C27—C28—H28	120.1	C57—C58—H58	119.8
C27—C28—C29	119.7 (4)	C57—C58—C59	120.3 (3)
C29—C28—H28	120.1	C59—C58—H58	119.8
C24—C29—H29	119.2	C54—C59—C58	120.9 (3)
C28—C29—C24	121.6 (3)	C54—C59—H59	119.5
C28—C29—H29	119.2	C58—C59—H59	119.5
Sn1—C1—C2—C3	51.9 (3)	Sn2—C31—C32—C33	49.8 (3)
Sn1—C1—C2—C7	−123.8 (2)	Sn2—C31—C32—C37	−127.3 (2)
Sn1—C8—C9—C10	−51.4 (3)	Sn2—C38—C39—C40	−52.0 (3)
Sn1—C8—C9—C14	126.3 (3)	Sn2—C38—C39—C44	124.7 (3)
Sn1—C18—C19—C20	178.0 (3)	Sn2—C48—C49—C50	175.5 (2)
Sn1—C18—C23—C22	−177.6 (3)	Sn2—C48—C53—C52	−175.7 (2)
Sn1—C24—C25—C26	−178.4 (3)	Sn2—C54—C55—C56	−178.3 (3)
Sn1—C24—C29—C28	178.3 (3)	Sn2—C54—C59—C58	177.8 (2)
O1—C3—C4—C5	−177.1 (2)	O2—C33—C34—C35	−178.3 (2)
O1—C3—C4—C15	1.0 (3)	O2—C33—C34—C45	−0.8 (4)
O1—C10—C11—C12	−179.7 (2)	O2—C40—C41—C42	176.6 (3)
O1—C10—C11—C15	0.2 (3)	O2—C40—C41—C45	−3.3 (4)
C1—C2—C3—O1	1.2 (3)	C31—C32—C33—O2	−0.2 (4)
C1—C2—C3—C4	−174.0 (2)	C31—C32—C33—C34	−175.7 (3)
C1—C2—C7—C6	175.0 (3)	C31—C32—C37—C36	178.0 (3)
C2—C3—C4—C5	−2.1 (4)	C32—C33—C34—C35	−2.9 (4)
C2—C3—C4—C15	176.0 (2)	C32—C33—C34—C45	174.6 (3)
C3—O1—C10—C9	135.2 (2)	C33—O2—C40—C39	135.6 (3)
C3—O1—C10—C11	−42.0 (3)	C33—O2—C40—C41	−39.8 (4)
C3—C2—C7—C6	−0.9 (4)	C33—C32—C37—C36	0.8 (4)
C3—C4—C5—C6	0.6 (4)	C33—C34—C35—C36	1.7 (4)
C3—C4—C15—C11	−38.8 (3)	C33—C34—C45—C41	−38.5 (4)
C3—C4—C15—C16	−161.2 (2)	C33—C34—C45—C46	−159.7 (3)
C3—C4—C15—C17	77.9 (3)	C33—C34—C45—C47	78.8 (3)
C4—C5—C6—C7	0.6 (5)	C34—C35—C36—C37	0.5 (5)
C5—C4—C15—C11	139.1 (3)	C35—C34—C45—C41	138.6 (3)
C5—C4—C15—C16	16.7 (4)	C35—C34—C45—C46	17.5 (5)
C5—C4—C15—C17	−104.2 (3)	C35—C34—C45—C47	−104.0 (4)
C5—C6—C7—C2	−0.4 (5)	C35—C36—C37—C32	−1.8 (5)
C7—C2—C3—O1	177.4 (2)	C37—C32—C33—O2	177.2 (2)
C7—C2—C3—C4	2.2 (4)	C37—C32—C33—C34	1.6 (4)
C8—C9—C10—O1	−2.4 (3)	C38—C39—C40—O2	0.2 (4)
C8—C9—C10—C11	174.6 (2)	C38—C39—C40—C41	175.5 (3)
C8—C9—C14—C13	−177.7 (3)	C38—C39—C44—C43	−176.4 (3)
C9—C10—C11—C12	3.4 (4)	C39—C40—C41—C42	1.6 (5)
C9—C10—C11—C15	−176.7 (2)	C39—C40—C41—C45	−178.3 (3)
C10—O1—C3—C2	−134.2 (2)	C40—O2—C33—C32	−133.9 (2)
C10—O1—C3—C4	41.3 (3)	C40—O2—C33—C34	42.0 (3)
C10—C9—C14—C13	−0.1 (4)	C40—C39—C44—C43	0.5 (5)
C10—C11—C12—C13	−0.4 (4)	C40—C41—C42—C43	−0.6 (5)
C10—C11—C15—C4	38.1 (3)	C40—C41—C45—C34	40.5 (4)
C10—C11—C15—C16	160.7 (2)	C40—C41—C45—C46	162.0 (3)
C10—C11—C15—C17	−79.1 (3)	C40—C41—C45—C47	−77.7 (4)
C11—C12—C13—C14	−2.6 (5)	C41—C42—C43—C44	−0.4 (6)
C12—C11—C15—C4	−142.0 (3)	C42—C41—C45—C34	−139.4 (3)
C12—C11—C15—C16	−19.4 (4)	C42—C41—C45—C46	−17.9 (5)
C12—C11—C15—C17	100.8 (3)	C42—C41—C45—C47	102.3 (4)
C12—C13—C14—C9	2.9 (5)	C42—C43—C44—C39	0.4 (6)
C14—C9—C10—O1	179.8 (2)	C44—C39—C40—O2	−176.8 (3)
C14—C9—C10—C11	−3.2 (4)	C44—C39—C40—C41	−1.6 (5)
C15—C4—C5—C6	−177.3 (3)	C45—C34—C35—C36	−175.5 (3)
C15—C11—C12—C13	179.7 (3)	C45—C41—C42—C43	179.3 (4)
C18—C19—C20—C21	0.5 (6)	C48—C49—C50—C51	0.0 (5)
C19—C18—C23—C22	−0.1 (5)	C49—C48—C53—C52	0.2 (4)
C19—C20—C21—C22	−2.0 (7)	C49—C50—C51—C52	0.4 (5)
C20—C21—C22—C23	2.4 (7)	C50—C51—C52—C53	−0.5 (5)
C21—C22—C23—C18	−1.4 (6)	C51—C52—C53—C48	0.2 (5)
C23—C18—C19—C20	0.5 (5)	C53—C48—C49—C50	−0.3 (5)
C24—C25—C26—C27	0.5 (6)	C54—C55—C56—C57	0.4 (5)
C25—C24—C29—C28	0.6 (5)	C55—C54—C59—C58	−0.4 (5)
C25—C26—C27—C28	−0.2 (6)	C55—C56—C57—C58	−0.3 (5)
C26—C27—C28—C29	0.1 (6)	C56—C57—C58—C59	−0.2 (5)
C27—C28—C29—C24	−0.3 (5)	C57—C58—C59—C54	0.5 (5)
C29—C24—C25—C26	−0.7 (5)	C59—C54—C55—C56	0.0 (5)

17,17-Dimethyl-7,7-diphenyl-15-oxa-7-stannatetracyclo[11.3.1.0^5,16.0^9,14]heptadeca-1,3,5(16),9(14),10,12-hexaene (7_100K_02)

Crystal data

[Sn(C6H5)2(C17H16O)]	Dx = 1.491 Mg m^−3
Mr = 509.19	Melting point: 352 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 20.7965 (4) Å	Cell parameters from 9503 reflections
b = 9.0831 (2) Å	θ = 2.5–29.2°
c = 25.2451 (5) Å	µ = 1.15 mm^−1
β = 107.898 (1)°	T = 100 K
V = 4537.93 (16) Å^3	Plate, clear colourless
Z = 8	0.49 × 0.37 × 0.18 mm
F(000) = 2064

Data collection

Bruker APEXII CCD diffractometer	11436 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.017
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 29.2°, θmin = 2.2°
Tmin = 0.024, Tmax = 0.049	h = −28→28
73608 measured reflections	k = −12→12
12229 independent reflections	l = −34→34

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0339P)^2 + 1.9184P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.006
12229 reflections	Δρmax = 0.48 e Å^−3
563 parameters	Δρmin = −0.27 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.55556 (2)	0.13587 (2)	0.63865 (2)	0.02226 (3)
O1	0.43992 (5)	0.25792 (10)	0.67007 (4)	0.02197 (17)
C1	0.57713 (7)	0.28226 (15)	0.71021 (6)	0.0255 (3)
H1A	0.570630	0.227646	0.742114	0.031*
H1B	0.625077	0.312906	0.720537	0.031*
C2	0.53337 (7)	0.41707 (15)	0.69980 (5)	0.0234 (2)
C3	0.46337 (7)	0.40229 (15)	0.67882 (5)	0.0218 (2)
C4	0.41779 (7)	0.51754 (15)	0.66249 (5)	0.0232 (2)
C5	0.44480 (8)	0.65949 (15)	0.67001 (6)	0.0269 (3)
H5	0.415693	0.742359	0.660094	0.032*
C6	0.51422 (8)	0.67988 (16)	0.69198 (6)	0.0289 (3)
H6	0.531967	0.777043	0.697091	0.035*
C7	0.55802 (7)	0.56120 (16)	0.70658 (6)	0.0271 (3)
H7	0.605261	0.578020	0.721332	0.033*
C8	0.45942 (7)	0.01781 (15)	0.61405 (6)	0.0252 (3)
H8A	0.460837	−0.058769	0.586523	0.030*
H8B	0.453786	−0.032586	0.647112	0.030*
C9	0.39955 (7)	0.11456 (15)	0.58948 (6)	0.0230 (2)
C10	0.39110 (6)	0.23909 (14)	0.61867 (5)	0.0220 (2)
C11	0.34123 (7)	0.34448 (15)	0.59910 (6)	0.0234 (2)
C12	0.29395 (7)	0.31764 (17)	0.54735 (6)	0.0278 (3)
H12	0.258290	0.385678	0.532379	0.033*
C13	0.29885 (7)	0.19139 (18)	0.51754 (6)	0.0307 (3)
H13	0.265695	0.173210	0.482727	0.037*
C14	0.35137 (7)	0.09133 (17)	0.53774 (6)	0.0283 (3)
H14	0.354451	0.007149	0.516318	0.034*
C15	0.34302 (7)	0.47855 (15)	0.63638 (6)	0.0243 (2)
C16	0.30238 (8)	0.60764 (17)	0.60380 (7)	0.0307 (3)
H16A	0.305264	0.691369	0.628911	0.046*
H16B	0.255019	0.578278	0.587703	0.046*
H16C	0.320813	0.636004	0.573914	0.046*
C17	0.31286 (7)	0.43292 (16)	0.68283 (6)	0.0286 (3)
H17A	0.338517	0.349727	0.703695	0.043*
H17B	0.265535	0.403978	0.666131	0.043*
H17C	0.315412	0.516146	0.708102	0.043*
C18	0.63155 (7)	−0.03265 (15)	0.66032 (6)	0.0251 (3)
C19	0.66618 (8)	−0.06474 (18)	0.71576 (6)	0.0327 (3)
H19	0.656953	−0.009607	0.744571	0.039*
C20	0.71435 (8)	−0.1772 (2)	0.72940 (8)	0.0421 (4)
H20	0.737888	−0.197609	0.767321	0.051*
C21	0.72774 (8)	−0.2585 (2)	0.68792 (9)	0.0429 (4)
H21	0.760821	−0.334278	0.697197	0.051*
C22	0.69310 (8)	−0.22976 (19)	0.63301 (8)	0.0391 (4)
H22	0.701797	−0.286980	0.604455	0.047*
C23	0.64553 (8)	−0.11764 (17)	0.61914 (7)	0.0311 (3)
H23	0.622168	−0.098464	0.581089	0.037*
C24	0.56080 (7)	0.25977 (15)	0.56826 (6)	0.0256 (3)
C25	0.60485 (8)	0.37940 (17)	0.57436 (7)	0.0312 (3)
H25	0.633822	0.404738	0.610281	0.037*
C26	0.60667 (8)	0.46162 (18)	0.52835 (7)	0.0354 (3)
H26	0.637171	0.541940	0.533035	0.042*
C27	0.56438 (9)	0.42723 (18)	0.47586 (7)	0.0346 (3)
H27	0.565741	0.483987	0.444613	0.042*
C28	0.51995 (9)	0.30971 (18)	0.46888 (6)	0.0334 (3)
H28	0.490619	0.286101	0.432902	0.040*
C29	0.51853 (8)	0.22636 (16)	0.51491 (6)	0.0299 (3)
H29	0.488296	0.145454	0.509884	0.036*
Sn2	0.41715 (2)	0.86349 (2)	0.80709 (2)	0.02258 (3)
O2	0.55663 (5)	0.75512 (11)	0.82672 (4)	0.02531 (19)
C31	0.48892 (7)	1.00771 (16)	0.78501 (6)	0.0261 (3)
H31A	0.493885	0.973994	0.749185	0.031*
H31B	0.469948	1.108535	0.779304	0.031*
C32	0.55760 (7)	1.01383 (16)	0.82739 (5)	0.0252 (3)
C33	0.59131 (7)	0.88340 (16)	0.84793 (6)	0.0248 (3)
C34	0.65302 (7)	0.87400 (16)	0.88956 (6)	0.0272 (3)
C35	0.68430 (7)	1.00752 (19)	0.91004 (6)	0.0322 (3)
H35	0.727374	1.007219	0.937552	0.039*
C36	0.65318 (8)	1.14002 (17)	0.89065 (6)	0.0320 (3)
H36	0.675230	1.229596	0.905102	0.038*
C37	0.58998 (8)	1.14445 (16)	0.85026 (6)	0.0286 (3)
H37	0.568852	1.236520	0.838249	0.034*
C38	0.43515 (7)	0.62670 (15)	0.81500 (6)	0.0271 (3)
H38A	0.394688	0.577843	0.819684	0.033*
H38B	0.441662	0.589178	0.780187	0.033*
C39	0.49551 (7)	0.58613 (16)	0.86303 (6)	0.0263 (3)
C40	0.55741 (7)	0.65320 (15)	0.86797 (6)	0.0252 (3)
C41	0.61630 (7)	0.63241 (16)	0.91200 (6)	0.0279 (3)
C42	0.61261 (8)	0.53422 (18)	0.95359 (7)	0.0335 (3)
H42	0.651589	0.515877	0.984411	0.040*
C43	0.55245 (8)	0.46353 (18)	0.95012 (7)	0.0352 (3)
H43	0.550723	0.396710	0.978606	0.042*
C44	0.49432 (8)	0.48888 (17)	0.90545 (7)	0.0315 (3)
H44	0.453550	0.439390	0.903932	0.038*
C45	0.67862 (7)	0.71987 (18)	0.91043 (6)	0.0304 (3)
C46	0.73187 (8)	0.7258 (2)	0.96767 (7)	0.0395 (4)
H46A	0.771660	0.779234	0.964950	0.059*
H46B	0.744910	0.625389	0.980869	0.059*
H46C	0.713184	0.776486	0.993921	0.059*
C47	0.70899 (9)	0.6459 (2)	0.86867 (8)	0.0404 (4)
H47A	0.675718	0.647027	0.831499	0.061*
H47B	0.721068	0.543850	0.880082	0.061*
H47C	0.749526	0.699668	0.867850	0.061*
C48	0.32543 (7)	0.89014 (15)	0.73919 (6)	0.0238 (2)
C49	0.32167 (7)	0.99474 (16)	0.69762 (6)	0.0272 (3)
H49	0.358824	1.058882	0.701097	0.033*
C50	0.26437 (7)	1.00656 (17)	0.65116 (6)	0.0309 (3)
H50	0.262657	1.078089	0.623309	0.037*
C51	0.20992 (7)	0.91321 (19)	0.64589 (6)	0.0330 (3)
H51	0.170904	0.920382	0.614241	0.040*
C52	0.21241 (7)	0.80952 (18)	0.68677 (6)	0.0317 (3)
H52	0.174944	0.746239	0.683195	0.038*
C53	0.26966 (7)	0.79784 (16)	0.73304 (6)	0.0265 (3)
H53	0.270903	0.726326	0.760799	0.032*
C54	0.41128 (7)	0.93967 (16)	0.88577 (6)	0.0256 (3)
C55	0.43248 (7)	1.08196 (16)	0.90474 (6)	0.0281 (3)
H55	0.448484	1.146341	0.881923	0.034*
C56	0.43045 (8)	1.13034 (17)	0.95651 (7)	0.0319 (3)
H56	0.444524	1.227478	0.968608	0.038*
C57	0.40785 (7)	1.03659 (19)	0.99047 (6)	0.0324 (3)
H57	0.406795	1.069143	1.025958	0.039*
C58	0.38684 (8)	0.89540 (18)	0.97242 (6)	0.0322 (3)
H58	0.371306	0.831218	0.995592	0.039*
C59	0.38840 (8)	0.84728 (17)	0.92053 (6)	0.0295 (3)
H59	0.373745	0.750384	0.908531	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02178 (5)	0.02164 (5)	0.02300 (5)	0.00205 (3)	0.00636 (4)	0.00180 (3)
O1	0.0236 (4)	0.0197 (4)	0.0208 (4)	−0.0011 (3)	0.0040 (3)	0.0009 (3)
C1	0.0236 (6)	0.0275 (6)	0.0233 (6)	0.0005 (5)	0.0042 (5)	0.0011 (5)
C2	0.0250 (6)	0.0256 (6)	0.0195 (5)	−0.0010 (5)	0.0066 (5)	−0.0003 (5)
C3	0.0260 (6)	0.0205 (6)	0.0198 (5)	−0.0019 (5)	0.0083 (5)	−0.0002 (4)
C4	0.0268 (6)	0.0234 (6)	0.0217 (6)	0.0002 (5)	0.0108 (5)	0.0001 (5)
C5	0.0331 (7)	0.0208 (6)	0.0296 (7)	0.0011 (5)	0.0135 (6)	0.0006 (5)
C6	0.0359 (7)	0.0226 (6)	0.0306 (7)	−0.0058 (5)	0.0138 (6)	−0.0035 (5)
C7	0.0279 (6)	0.0278 (7)	0.0259 (6)	−0.0059 (5)	0.0088 (5)	−0.0030 (5)
C8	0.0262 (6)	0.0212 (6)	0.0275 (6)	0.0004 (5)	0.0070 (5)	−0.0008 (5)
C9	0.0231 (6)	0.0217 (6)	0.0238 (6)	−0.0011 (5)	0.0067 (5)	0.0009 (5)
C10	0.0216 (6)	0.0234 (6)	0.0202 (5)	−0.0016 (5)	0.0053 (4)	0.0016 (4)
C11	0.0228 (6)	0.0237 (6)	0.0246 (6)	0.0006 (5)	0.0089 (5)	0.0030 (5)
C12	0.0228 (6)	0.0318 (7)	0.0273 (6)	0.0026 (5)	0.0055 (5)	0.0049 (5)
C13	0.0267 (6)	0.0382 (8)	0.0231 (6)	−0.0024 (6)	0.0015 (5)	−0.0012 (6)
C14	0.0280 (7)	0.0295 (7)	0.0256 (6)	−0.0030 (5)	0.0057 (5)	−0.0041 (5)
C15	0.0246 (6)	0.0227 (6)	0.0269 (6)	0.0023 (5)	0.0097 (5)	0.0017 (5)
C16	0.0291 (7)	0.0280 (7)	0.0355 (7)	0.0071 (5)	0.0108 (6)	0.0058 (6)
C17	0.0297 (7)	0.0290 (7)	0.0310 (7)	0.0005 (5)	0.0148 (5)	0.0007 (5)
C18	0.0208 (6)	0.0242 (6)	0.0296 (6)	0.0001 (5)	0.0069 (5)	0.0028 (5)
C19	0.0277 (7)	0.0376 (8)	0.0306 (7)	0.0012 (6)	0.0057 (5)	0.0030 (6)
C20	0.0300 (8)	0.0504 (10)	0.0408 (9)	0.0069 (7)	0.0033 (6)	0.0161 (8)
C21	0.0300 (8)	0.0347 (8)	0.0621 (11)	0.0109 (6)	0.0115 (7)	0.0115 (8)
C22	0.0313 (7)	0.0347 (8)	0.0520 (10)	0.0056 (6)	0.0137 (7)	−0.0052 (7)
C23	0.0264 (7)	0.0337 (7)	0.0322 (7)	0.0031 (5)	0.0078 (6)	−0.0010 (6)
C24	0.0274 (6)	0.0243 (6)	0.0264 (6)	0.0048 (5)	0.0103 (5)	0.0026 (5)
C25	0.0287 (7)	0.0320 (7)	0.0334 (7)	0.0005 (5)	0.0104 (6)	0.0034 (6)
C26	0.0345 (8)	0.0324 (8)	0.0441 (8)	−0.0001 (6)	0.0192 (7)	0.0061 (6)
C27	0.0440 (8)	0.0329 (8)	0.0349 (7)	0.0118 (6)	0.0238 (7)	0.0094 (6)
C28	0.0441 (8)	0.0317 (7)	0.0262 (7)	0.0092 (6)	0.0132 (6)	0.0006 (6)
C29	0.0369 (7)	0.0253 (7)	0.0281 (7)	0.0019 (6)	0.0109 (6)	−0.0006 (5)
Sn2	0.02080 (5)	0.02382 (5)	0.02145 (5)	−0.00174 (3)	0.00404 (3)	0.00170 (3)
O2	0.0260 (5)	0.0275 (5)	0.0208 (4)	−0.0041 (4)	0.0047 (3)	−0.0006 (4)
C31	0.0253 (6)	0.0282 (7)	0.0232 (6)	−0.0033 (5)	0.0051 (5)	0.0022 (5)
C32	0.0244 (6)	0.0307 (7)	0.0213 (6)	−0.0048 (5)	0.0083 (5)	0.0013 (5)
C33	0.0239 (6)	0.0303 (7)	0.0210 (6)	−0.0049 (5)	0.0080 (5)	−0.0016 (5)
C34	0.0221 (6)	0.0367 (8)	0.0232 (6)	−0.0033 (5)	0.0077 (5)	0.0002 (5)
C35	0.0246 (6)	0.0443 (9)	0.0260 (6)	−0.0085 (6)	0.0056 (5)	−0.0017 (6)
C36	0.0305 (7)	0.0372 (8)	0.0282 (7)	−0.0133 (6)	0.0090 (6)	−0.0049 (5)
C37	0.0304 (7)	0.0306 (7)	0.0257 (6)	−0.0055 (5)	0.0102 (6)	−0.0002 (5)
C38	0.0249 (6)	0.0254 (7)	0.0281 (7)	−0.0029 (5)	0.0039 (5)	0.0012 (5)
C39	0.0252 (6)	0.0231 (6)	0.0289 (6)	0.0002 (5)	0.0056 (5)	0.0001 (5)
C40	0.0252 (6)	0.0253 (6)	0.0245 (6)	0.0014 (5)	0.0068 (5)	0.0013 (5)
C41	0.0237 (6)	0.0310 (7)	0.0280 (7)	0.0022 (5)	0.0062 (5)	0.0005 (5)
C42	0.0292 (7)	0.0355 (8)	0.0328 (7)	0.0065 (6)	0.0051 (6)	0.0071 (6)
C43	0.0349 (8)	0.0335 (8)	0.0358 (8)	0.0033 (6)	0.0091 (6)	0.0119 (6)
C44	0.0283 (7)	0.0286 (7)	0.0366 (7)	0.0005 (5)	0.0088 (6)	0.0067 (6)
C45	0.0216 (6)	0.0389 (8)	0.0290 (7)	0.0009 (6)	0.0052 (5)	0.0029 (6)
C46	0.0257 (7)	0.0499 (10)	0.0361 (8)	−0.0003 (7)	−0.0003 (6)	0.0070 (7)
C47	0.0305 (8)	0.0485 (10)	0.0446 (9)	0.0050 (7)	0.0150 (7)	−0.0008 (7)
C48	0.0216 (6)	0.0257 (6)	0.0236 (6)	0.0012 (5)	0.0064 (5)	−0.0014 (5)
C49	0.0248 (6)	0.0271 (7)	0.0282 (6)	0.0004 (5)	0.0059 (5)	0.0026 (5)
C50	0.0284 (7)	0.0338 (7)	0.0280 (7)	0.0056 (6)	0.0052 (5)	0.0038 (6)
C51	0.0219 (6)	0.0440 (9)	0.0295 (7)	0.0062 (6)	0.0024 (5)	−0.0037 (6)
C52	0.0216 (6)	0.0383 (8)	0.0352 (7)	−0.0025 (6)	0.0089 (5)	−0.0069 (6)
C53	0.0247 (6)	0.0282 (7)	0.0276 (6)	−0.0007 (5)	0.0097 (5)	−0.0022 (5)
C54	0.0223 (6)	0.0291 (7)	0.0235 (6)	0.0007 (5)	0.0044 (5)	0.0023 (5)
C55	0.0272 (6)	0.0285 (7)	0.0280 (6)	0.0000 (5)	0.0077 (5)	0.0016 (5)
C56	0.0307 (7)	0.0318 (8)	0.0322 (7)	0.0000 (5)	0.0081 (6)	−0.0037 (5)
C57	0.0275 (7)	0.0436 (8)	0.0258 (6)	0.0063 (6)	0.0078 (5)	−0.0002 (6)
C58	0.0304 (7)	0.0387 (8)	0.0292 (7)	0.0029 (6)	0.0118 (6)	0.0079 (6)
C59	0.0291 (7)	0.0301 (7)	0.0296 (7)	−0.0011 (5)	0.0092 (6)	0.0035 (5)

Geometric parameters (Å, º)

Sn1—C1	2.1759 (14)	Sn2—C31	2.1830 (14)
Sn1—C8	2.1840 (14)	Sn2—C38	2.1818 (14)
Sn1—C18	2.1466 (13)	Sn2—C48	2.1507 (14)
Sn1—C24	2.1343 (14)	Sn2—C54	2.1420 (14)
O1—C3	1.3929 (15)	O2—C33	1.3883 (16)
O1—C10	1.3906 (15)	O2—C40	1.3898 (17)
C1—H1A	0.9900	C31—H31A	0.9900
C1—H1B	0.9900	C31—H31B	0.9900
C1—C2	1.4998 (19)	C31—C32	1.4996 (18)
C2—C3	1.3942 (18)	C32—C33	1.393 (2)
C2—C7	1.3971 (19)	C32—C37	1.398 (2)
C3—C4	1.3872 (19)	C33—C34	1.3891 (19)
C4—C5	1.3958 (19)	C34—C35	1.398 (2)
C4—C15	1.5322 (19)	C34—C45	1.533 (2)
C5—H5	0.9500	C35—H35	0.9500
C5—C6	1.391 (2)	C35—C36	1.383 (2)
C6—H6	0.9500	C36—H36	0.9500
C6—C7	1.386 (2)	C36—C37	1.395 (2)
C7—H7	0.9500	C37—H37	0.9500
C8—H8A	0.9900	C38—H38A	0.9900
C8—H8B	0.9900	C38—H38B	0.9900
C8—C9	1.4942 (19)	C38—C39	1.4987 (19)
C9—C10	1.3904 (18)	C39—C40	1.395 (2)
C9—C14	1.3964 (19)	C39—C44	1.394 (2)
C10—C11	1.3860 (18)	C40—C41	1.391 (2)
C11—C12	1.3942 (19)	C41—C42	1.398 (2)
C11—C15	1.5324 (19)	C41—C45	1.531 (2)
C12—H12	0.9500	C42—H42	0.9500
C12—C13	1.392 (2)	C42—C43	1.385 (2)
C13—H13	0.9500	C43—H43	0.9500
C13—C14	1.392 (2)	C43—C44	1.396 (2)
C14—H14	0.9500	C44—H44	0.9500
C15—C16	1.5292 (19)	C45—C46	1.528 (2)
C15—C17	1.5469 (19)	C45—C47	1.540 (2)
C16—H16A	0.9800	C46—H46A	0.9800
C16—H16B	0.9800	C46—H46B	0.9800
C16—H16C	0.9800	C46—H46C	0.9800
C17—H17A	0.9800	C47—H47A	0.9800
C17—H17B	0.9800	C47—H47B	0.9800
C17—H17C	0.9800	C47—H47C	0.9800
C18—C19	1.394 (2)	C48—C49	1.3999 (19)
C18—C23	1.395 (2)	C48—C53	1.4006 (19)
C19—H19	0.9500	C49—H49	0.9500
C19—C20	1.398 (2)	C49—C50	1.3956 (19)
C20—H20	0.9500	C50—H50	0.9500
C20—C21	1.378 (3)	C50—C51	1.388 (2)
C21—H21	0.9500	C51—H51	0.9500
C21—C22	1.377 (3)	C51—C52	1.386 (2)
C22—H22	0.9500	C52—H52	0.9500
C22—C23	1.388 (2)	C52—C53	1.392 (2)
C23—H23	0.9500	C53—H53	0.9500
C24—C25	1.399 (2)	C54—C55	1.402 (2)
C24—C29	1.397 (2)	C54—C59	1.399 (2)
C25—H25	0.9500	C55—H55	0.9500
C25—C26	1.391 (2)	C55—C56	1.392 (2)
C26—H26	0.9500	C56—H56	0.9500
C26—C27	1.382 (2)	C56—C57	1.389 (2)
C27—H27	0.9500	C57—H57	0.9500
C27—C28	1.387 (2)	C57—C58	1.386 (2)
C28—H28	0.9500	C58—H58	0.9500
C28—C29	1.395 (2)	C58—C59	1.391 (2)
C29—H29	0.9500	C59—H59	0.9500
C1—Sn1—C8	118.25 (5)	C38—Sn2—C31	120.22 (6)
C18—Sn1—C1	106.05 (5)	C48—Sn2—C31	103.74 (5)
C18—Sn1—C8	105.08 (5)	C48—Sn2—C38	105.61 (5)
C24—Sn1—C1	108.59 (5)	C54—Sn2—C31	106.33 (5)
C24—Sn1—C8	107.38 (5)	C54—Sn2—C38	106.90 (6)
C24—Sn1—C18	111.48 (5)	C54—Sn2—C48	114.42 (5)
C10—O1—C3	112.55 (10)	C33—O2—C40	112.64 (10)
Sn1—C1—H1A	108.9	Sn2—C31—H31A	108.6
Sn1—C1—H1B	108.9	Sn2—C31—H31B	108.6
H1A—C1—H1B	107.7	H31A—C31—H31B	107.6
C2—C1—Sn1	113.23 (9)	C32—C31—Sn2	114.60 (9)
C2—C1—H1A	108.9	C32—C31—H31A	108.6
C2—C1—H1B	108.9	C32—C31—H31B	108.6
C3—C2—C1	119.63 (12)	C33—C32—C31	119.61 (13)
C3—C2—C7	115.96 (13)	C33—C32—C37	116.39 (13)
C7—C2—C1	124.30 (12)	C37—C32—C31	123.93 (13)
O1—C3—C2	115.13 (12)	O2—C33—C32	115.33 (12)
C4—C3—O1	119.30 (12)	O2—C33—C34	119.34 (13)
C4—C3—C2	125.35 (13)	C34—C33—C32	125.18 (13)
C3—C4—C5	116.55 (13)	C33—C34—C35	116.31 (14)
C3—C4—C15	117.63 (12)	C33—C34—C45	117.31 (13)
C5—C4—C15	125.79 (12)	C35—C34—C45	126.32 (13)
C4—C5—H5	119.9	C34—C35—H35	119.7
C6—C5—C4	120.15 (13)	C36—C35—C34	120.67 (13)
C6—C5—H5	119.9	C36—C35—H35	119.7
C5—C6—H6	119.4	C35—C36—H36	119.4
C7—C6—C5	121.28 (13)	C35—C36—C37	121.15 (14)
C7—C6—H6	119.4	C37—C36—H36	119.4
C2—C7—H7	119.7	C32—C37—H37	119.9
C6—C7—C2	120.65 (13)	C36—C37—C32	120.23 (14)
C6—C7—H7	119.7	C36—C37—H37	119.9
Sn1—C8—H8A	108.8	Sn2—C38—H38A	108.9
Sn1—C8—H8B	108.8	Sn2—C38—H38B	108.9
H8A—C8—H8B	107.7	H38A—C38—H38B	107.8
C9—C8—Sn1	113.73 (9)	C39—C38—Sn2	113.20 (9)
C9—C8—H8A	108.8	C39—C38—H38A	108.9
C9—C8—H8B	108.8	C39—C38—H38B	108.9
C10—C9—C8	118.90 (12)	C40—C39—C38	119.05 (13)
C10—C9—C14	116.58 (13)	C44—C39—C38	124.68 (13)
C14—C9—C8	124.49 (13)	C44—C39—C40	116.22 (13)
C9—C10—O1	114.81 (11)	O2—C40—C39	115.21 (12)
C11—C10—O1	119.96 (12)	O2—C40—C41	119.60 (13)
C11—C10—C9	125.14 (12)	C41—C40—C39	125.04 (13)
C10—C11—C12	116.63 (13)	C40—C41—C42	116.67 (14)
C10—C11—C15	117.11 (12)	C40—C41—C45	116.97 (13)
C12—C11—C15	126.26 (12)	C42—C41—C45	126.37 (13)
C11—C12—H12	119.9	C41—C42—H42	119.8
C13—C12—C11	120.19 (13)	C43—C42—C41	120.37 (14)
C13—C12—H12	119.9	C43—C42—H42	119.8
C12—C13—H13	119.4	C42—C43—H43	119.5
C14—C13—C12	121.28 (13)	C42—C43—C44	121.05 (14)
C14—C13—H13	119.4	C44—C43—H43	119.5
C9—C14—H14	120.0	C39—C44—C43	120.64 (14)
C13—C14—C9	120.06 (13)	C39—C44—H44	119.7
C13—C14—H14	120.0	C43—C44—H44	119.7
C4—C15—C11	106.13 (11)	C34—C45—C47	109.61 (13)
C4—C15—C17	109.28 (11)	C41—C45—C34	105.99 (11)
C11—C15—C17	108.28 (11)	C41—C45—C47	108.65 (13)
C16—C15—C4	111.98 (12)	C46—C45—C34	111.55 (14)
C16—C15—C11	111.96 (12)	C46—C45—C41	111.53 (13)
C16—C15—C17	109.10 (11)	C46—C45—C47	109.41 (13)
C15—C16—H16A	109.5	C45—C46—H46A	109.5
C15—C16—H16B	109.5	C45—C46—H46B	109.5
C15—C16—H16C	109.5	C45—C46—H46C	109.5
H16A—C16—H16B	109.5	H46A—C46—H46B	109.5
H16A—C16—H16C	109.5	H46A—C46—H46C	109.5
H16B—C16—H16C	109.5	H46B—C46—H46C	109.5
C15—C17—H17A	109.5	C45—C47—H47A	109.5
C15—C17—H17B	109.5	C45—C47—H47B	109.5
C15—C17—H17C	109.5	C45—C47—H47C	109.5
H17A—C17—H17B	109.5	H47A—C47—H47B	109.5
H17A—C17—H17C	109.5	H47A—C47—H47C	109.5
H17B—C17—H17C	109.5	H47B—C47—H47C	109.5
C19—C18—Sn1	121.19 (11)	C49—C48—Sn2	120.36 (10)
C19—C18—C23	118.07 (13)	C49—C48—C53	118.01 (13)
C23—C18—Sn1	120.69 (10)	C53—C48—Sn2	121.49 (10)
C18—C19—H19	119.7	C48—C49—H49	119.4
C18—C19—C20	120.69 (15)	C50—C49—C48	121.25 (13)
C20—C19—H19	119.7	C50—C49—H49	119.4
C19—C20—H20	120.0	C49—C50—H50	120.2
C21—C20—C19	120.10 (16)	C51—C50—C49	119.63 (14)
C21—C20—H20	120.0	C51—C50—H50	120.2
C20—C21—H21	120.1	C50—C51—H51	120.0
C22—C21—C20	119.87 (15)	C52—C51—C50	120.06 (14)
C22—C21—H21	120.1	C52—C51—H51	120.0
C21—C22—H22	119.8	C51—C52—H52	119.9
C21—C22—C23	120.34 (16)	C51—C52—C53	120.21 (14)
C23—C22—H22	119.8	C53—C52—H52	119.9
C18—C23—H23	119.5	C48—C53—H53	119.6
C22—C23—C18	120.92 (15)	C52—C53—C48	120.85 (14)
C22—C23—H23	119.5	C52—C53—H53	119.6
C25—C24—Sn1	121.15 (11)	C55—C54—Sn2	120.88 (10)
C29—C24—Sn1	120.68 (11)	C59—C54—Sn2	121.00 (11)
C29—C24—C25	118.14 (13)	C59—C54—C55	118.09 (13)
C24—C25—H25	119.7	C54—C55—H55	119.5
C26—C25—C24	120.67 (15)	C56—C55—C54	120.99 (14)
C26—C25—H25	119.7	C56—C55—H55	119.5
C25—C26—H26	119.8	C55—C56—H56	120.0
C27—C26—C25	120.44 (15)	C57—C56—C55	119.99 (14)
C27—C26—H26	119.8	C57—C56—H56	120.0
C26—C27—H27	120.1	C56—C57—H57	120.1
C26—C27—C28	119.89 (14)	C58—C57—C56	119.78 (14)
C28—C27—H27	120.1	C58—C57—H57	120.1
C27—C28—H28	120.1	C57—C58—H58	119.9
C27—C28—C29	119.72 (15)	C57—C58—C59	120.28 (14)
C29—C28—H28	120.1	C59—C58—H58	119.9
C24—C29—H29	119.4	C54—C59—H59	119.6
C28—C29—C24	121.14 (14)	C58—C59—C54	120.87 (14)
C28—C29—H29	119.4	C58—C59—H59	119.6
Sn1—C1—C2—C3	51.80 (14)	Sn2—C31—C32—C33	50.22 (16)
Sn1—C1—C2—C7	−124.16 (12)	Sn2—C31—C32—C37	−126.76 (12)
Sn1—C8—C9—C10	−52.23 (15)	Sn2—C38—C39—C40	−52.78 (16)
Sn1—C8—C9—C14	125.98 (13)	Sn2—C38—C39—C44	124.46 (14)
Sn1—C18—C19—C20	178.38 (13)	Sn2—C48—C49—C50	175.34 (11)
Sn1—C18—C23—C22	−177.96 (12)	Sn2—C48—C53—C52	−175.36 (11)
Sn1—C24—C25—C26	−178.41 (11)	Sn2—C54—C55—C56	−178.23 (11)
Sn1—C24—C29—C28	177.83 (11)	Sn2—C54—C59—C58	177.77 (11)
O1—C3—C4—C5	−177.10 (11)	O2—C33—C34—C35	−178.34 (12)
O1—C3—C4—C15	1.13 (17)	O2—C33—C34—C45	−1.07 (19)
O1—C10—C11—C12	−179.77 (12)	O2—C40—C41—C42	176.63 (13)
O1—C10—C11—C15	−0.10 (18)	O2—C40—C41—C45	−3.0 (2)
C1—C2—C3—O1	1.03 (17)	C31—C32—C33—O2	−0.43 (18)
C1—C2—C3—C4	−173.59 (12)	C31—C32—C33—C34	−175.85 (13)
C1—C2—C7—C6	175.01 (13)	C31—C32—C37—C36	178.22 (13)
C2—C3—C4—C5	−2.7 (2)	C32—C33—C34—C35	−3.1 (2)
C2—C3—C4—C15	175.54 (12)	C32—C33—C34—C45	174.17 (13)
C3—O1—C10—C9	135.12 (12)	C33—O2—C40—C39	135.25 (13)
C3—O1—C10—C11	−41.64 (16)	C33—O2—C40—C41	−40.53 (17)
C3—C2—C7—C6	−1.09 (19)	C33—C32—C37—C36	1.1 (2)
C3—C4—C5—C6	1.1 (2)	C33—C34—C35—C36	2.3 (2)
C3—C4—C15—C11	−39.08 (15)	C33—C34—C45—C41	−38.60 (17)
C3—C4—C15—C16	−161.52 (12)	C33—C34—C45—C46	−160.19 (13)
C3—C4—C15—C17	77.48 (15)	C33—C34—C45—C47	78.48 (16)
C4—C5—C6—C7	0.3 (2)	C34—C35—C36—C37	0.0 (2)
C5—C4—C15—C11	138.97 (13)	C35—C34—C45—C41	138.36 (15)
C5—C4—C15—C16	16.53 (19)	C35—C34—C45—C46	16.8 (2)
C5—C4—C15—C17	−104.47 (15)	C35—C34—C45—C47	−104.56 (17)
C5—C6—C7—C2	−0.3 (2)	C35—C36—C37—C32	−1.8 (2)
C7—C2—C3—O1	177.32 (11)	C37—C32—C33—O2	176.77 (12)
C7—C2—C3—C4	2.7 (2)	C37—C32—C33—C34	1.4 (2)
C8—C9—C10—O1	−1.93 (18)	C38—C39—C40—O2	0.52 (19)
C8—C9—C10—C11	174.63 (13)	C38—C39—C40—C41	176.04 (14)
C8—C9—C14—C13	−177.38 (14)	C38—C39—C44—C43	−176.65 (15)
C9—C10—C11—C12	3.8 (2)	C39—C40—C41—C42	1.3 (2)
C9—C10—C11—C15	−176.50 (12)	C39—C40—C41—C45	−178.29 (14)
C10—O1—C3—C2	−134.03 (12)	C40—O2—C33—C32	−133.05 (12)
C10—O1—C3—C4	40.94 (15)	C40—O2—C33—C34	42.65 (17)
C10—C9—C14—C13	0.9 (2)	C40—C39—C44—C43	0.7 (2)
C10—C11—C12—C13	−1.1 (2)	C40—C41—C42—C43	−0.4 (2)
C10—C11—C15—C4	38.47 (15)	C40—C41—C45—C34	40.52 (17)
C10—C11—C15—C16	160.92 (12)	C40—C41—C45—C46	162.12 (14)
C10—C11—C15—C17	−78.76 (15)	C40—C41—C45—C47	−77.20 (17)
C11—C12—C13—C14	−1.5 (2)	C41—C42—C43—C44	−0.3 (3)
C12—C11—C15—C4	−141.89 (14)	C42—C41—C45—C34	−139.02 (15)
C12—C11—C15—C16	−19.44 (19)	C42—C41—C45—C46	−17.4 (2)
C12—C11—C15—C17	100.88 (16)	C42—C41—C45—C47	103.26 (18)
C12—C13—C14—C9	1.6 (2)	C42—C43—C44—C39	0.1 (3)
C14—C9—C10—O1	179.72 (12)	C44—C39—C40—O2	−176.95 (13)
C14—C9—C10—C11	−3.7 (2)	C44—C39—C40—C41	−1.4 (2)
C15—C4—C5—C6	−177.01 (13)	C45—C34—C35—C36	−174.64 (14)
C15—C11—C12—C13	179.27 (13)	C45—C41—C42—C43	179.16 (15)
C18—C19—C20—C21	−0.5 (3)	C48—C49—C50—C51	0.1 (2)
C19—C18—C23—C22	−0.7 (2)	C49—C48—C53—C52	0.3 (2)
C19—C20—C21—C22	−0.6 (3)	C49—C50—C51—C52	0.4 (2)
C20—C21—C22—C23	1.1 (3)	C50—C51—C52—C53	−0.5 (2)
C21—C22—C23—C18	−0.4 (3)	C51—C52—C53—C48	0.1 (2)
C23—C18—C19—C20	1.1 (2)	C53—C48—C49—C50	−0.4 (2)
C24—C25—C26—C27	0.7 (2)	C54—C55—C56—C57	0.7 (2)
C25—C24—C29—C28	−0.1 (2)	C55—C54—C59—C58	−0.1 (2)
C25—C26—C27—C28	−0.2 (2)	C55—C56—C57—C58	−0.5 (2)
C26—C27—C28—C29	−0.4 (2)	C56—C57—C58—C59	0.1 (2)
C27—C28—C29—C24	0.5 (2)	C57—C58—C59—C54	0.2 (2)
C29—C24—C25—C26	−0.5 (2)	C59—C54—C55—C56	−0.4 (2)