Aqua­(tri­fluoro­acetato)­tri­phenyl­tin–15-crown-5 (2/1)

In the centrosymmetric title compound, [Sn(C₂F₃O₂)(C₆H₅)₃(H₂O)]₂·C₁₀H₂₀O₅, the 1,3–O atoms (positions 1 and 7) of the 1,4,7,10,13-pentaoxa­cyclo­penta­decane moiety are hydrogen bonded to the water mol­ecule of the trans-C₃SnO₂ trigonal-bipyramidal organotin moiety that lies on one side of the cyclic polyether [O(water)...O(crown ether) = 2.800 (4) and 2.837 (4) Å]; the 2,4-O atoms (positions 4 and 10) are hydrogen bonded to the inversion-related organotin moiety that lies on the other side [O(water)...O(crown ether) = 2.768 (3) and 2.881 (4) Å].

Key indicators

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.022
• wR factor = 0.056
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      50.00 Perc.

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.062
          Tmax scaled      0.883 Tmin scaled      0.607


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The reaction of triphenyltin trifluoroacetate with 18-crown-6 affords a dinuclear compound in which an aquatrifluoroacetatotin entity interacts with the polyether through its coordinated water. The compound, [(C₆H₅)₃SnO₂CCF₃)·H₂O]₂·C₁₂H₂₄O₆ [Sn← O(water) = 2.43 (1) Å], exists as a 1/3 co-crystal with [(C₆H₅)₃SnO₂CCF₃)·H₂O]·C₁₂H₂₄O₆·2H₂O (Amini et al., 2003). Disorder in [(C₆H₅)₃SnO₂CCF₃)·H₂O]₂·C₁₂H₂₄O₆, which lies on a threefold axis, precluded the elucidation of the nature of the hydrogen-bonding interaction. The aquatrifluoroacetatodiphenylmethyltin homolog, [[(C₆H₅)₂(CH₃)SnO₂CCF₃]·H₂O]₂·C₁₂H₂₄O₆ [Sn← O(water) = 2.483 (5) Å], is not disordered; the cyclic polyether uses its 1,3-substituents to interact with the aquatrifluoroacetatotriorganotin entity that is on one side of the ring, and its 4,6-substituents with the entity on the other side [O(water)···O(crown ether) = 2.901 (8), 2.983 (7) Å] (Amini, Yousefi & Ng, 2002).

The title compound, (I) (see Scheme 1), adopts a similar centrosymmetric structure (Fig. 1); as with the 18-crown-6 complex for which four of the six O atoms are involved in hydrogen-bonding interactions. In this 15-crown-5 complex, four of the five O atoms are linked to the coordinated water molecule by hydrogen bonds. The 15-membered cyclic polyether is disordered over a center-of-inversion, and the O atoms all point towards the middle of the ring (Fig. 2). On the other hand, in the only one other example of 15-crown-5 affording a complex with an organotin compound, the five O atoms point away from the middle, and there is no interaction with the diaquadichlorodimethyltin entity (Amini et al., 1994a; Yap et al., 1996). The tin–water bond distance [Sn← O(water) = 2.407 (1) Å] in the title compound is somewhat shorter than the distances found in the other aquacarboxylatotriorganotin complexes, but are much longer than those found in the diaquadichlorodiorganotin adducts of 18-crown-6, i.e. [(CH₃)₂SnCl₂]₂·C₁₂H₂₄O₆ (Amini et al., 1984), [(CH₃)(C₆H₅)SnCl₂]₂·C₁₂H₂₄O₆ (Amini et al., 1994b) and [(C₆H₅)₂SnCl₂]₂·C₁₂H₂₄O₆ (Amini, Amirreza et al., 2002) owing to the weaker Lewis acidity of the triorganotin acceptor.

S2. Experimental

Triphenyltin trifluoroacetate (2.31 g, 5.0 mmol) and 15-crown-5 (0.55 g, 2.5 mmol) were heated in a small volume of acetone. The solvent was removed and the product recrystallized from ethanol to afford the title complex (m.p. 412–414 K). The formulation was established by ¹H NMR spectral analysis [1^H in CDCl₃ (δ in p.p.m.): 4.07 (H₂O), 3.15 (–CH₂–), 7.35–7.79 (C₆H₅)].

S3. Refinement

The 15-crown-5 ring is disordered over a center-of-inversion (1/2,1/2,1/2), and it was refined as a 15-atom unit by making use of the PART −1 command in SHELXL97 (Sheldrick, 1997) subject to the following restraints: C—C = 1.53±0.01, C—O = 1.41±0.01 and C—O—C = C—C—O = 2.37±0.01 Å. The atoms are of half-site occupancy. The trifluromethyl group is disordered over two positions; as their occupancy refined to nearly 1/2, the occupancy was fixed as 0.5. The C—F distances were restrained to be approximately equal by SADI 0.01; the F···F lengths were similarly restrained by SADI 0.01. The displacement parameters of the primed and umprimed F atoms were set to equal each other.

Two pairs of water H atoms were located and refined; the occupancy factor of each of the four H atoms is 0.5. One pair (H1w1 and H1w2) interacts with two O atoms (O3 and O5) of the crown ether and the other pair (H1w3 and H1w4) with two symmetry-related O atoms [O4ⁱ and O6ⁱ; symmetry code: (i) 1 − x, 1 − y, 1 − z]. The O—H distance was restrained using the DFIX command subject to 0.85±0.01 Å and the H···H length as 1.39±0.01 Å. The displacement parameters of the H atoms were set to 1.2 times that of the equivalent isotropic displacement parameter of the O atom.

The carbon-bound H atoms were generated geometrically, with C—H = 0.95 Å for the aromatic H atoms and C—H = 0.99 Å for the aliphatic H atoms. Their displacement parameters were set to 1.2 times the equivalent isotropic displacement parameters of their parent C atoms.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEPII (Johnson, 1976) plot of (I), with ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. The unlabeled part of the dimer is related to the labeled part by the symmetry operation (1 − x, 1 − y, 1 − z).
	Fig. 2. ORTEPII (Johnson, 1976) plot of the 15-crown-5.2H2O portion of the title dinuclear complex [symmetry code: (i) 1 − x, 1 − y, 1 − z]. The ether O atom that is not involved in hydrogen bonding (O7) has a marginally larger equivalent isotropic displacement parameter than the other O atoms.

Bis(aquatrifluoroacetatotriphenyltin)–1,4,7,10,13-pentaoxacyclopentadecane (1/1)

Crystal data

[Sn(C2F3O2)(C6H5)3(H2O)]2·C10H20O5	Z = 1
Mr = 1182.31	F(000) = 596
Triclinic, P1	Dx = 1.512 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3917 (6) Å	Cell parameters from 6960 reflections
b = 11.1154 (7) Å	θ = 1.8–26.5°
c = 12.3300 (8) Å	µ = 1.04 mm^−1
α = 110.611 (1)°	T = 168 K
β = 97.621 (1)°	Plate, colorless
γ = 97.198 (1)°	0.50 × 0.13 × 0.12 mm
V = 1298.4 (1) Å^3

Data collection

Bruker AXS area-detector diffractometer	5179 independent reflections
Radiation source: fine-focus sealed tube	4618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ϕ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.571, Tmax = 0.831	k = −13→13
16310 measured reflections	l = −12→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0369P)^2] where P = (Fo^2 + 2Fc^2)/3
5179 reflections	(Δ/σ)max = 0.001
400 parameters	Δρmax = 0.69 e Å^−3
66 restraints	Δρmin = −0.57 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.31348 (1)	0.83004 (1)	0.72431 (1)	0.02718 (6)
F1	0.102 (5)	1.263 (5)	0.907 (5)	0.077 (3)	0.50
F2	0.083 (5)	1.118 (4)	0.980 (3)	0.115 (5)	0.50
F3	0.258 (3)	1.260 (4)	1.033 (3)	0.118 (5)	0.50
F1'	0.092 (5)	1.258 (5)	0.910 (5)	0.077 (3)	0.50
F2'	0.103 (5)	1.131 (4)	1.002 (3)	0.115 (5)	0.50
F3'	0.272 (3)	1.265 (5)	1.015 (3)	0.118 (5)	0.50
O1	0.2248 (2)	0.9801 (1)	0.8422 (1)	0.039 (1)
O2	0.2553 (2)	1.1362 (2)	0.7656 (2)	0.054 (1)
O3	0.5260 (4)	0.4818 (4)	0.6992 (4)	0.062 (1)	0.50
O4	0.6938 (3)	0.5884 (3)	0.5712 (3)	0.045 (1)	0.50
O5	0.5206 (3)	0.6486 (3)	0.4135 (3)	0.047 (1)	0.50
O6	0.3400 (4)	0.4068 (4)	0.3199 (4)	0.046 (1)	0.50
O7	0.3112 (5)	0.3440 (5)	0.5205 (4)	0.064 (1)	0.50
O1w	0.4079 (2)	0.6519 (2)	0.6083 (1)	0.037 (1)
C1	0.2804 (2)	0.7194 (2)	0.8316 (2)	0.033 (1)
C2	0.1521 (3)	0.6859 (2)	0.8479 (2)	0.046 (1)
C3	0.1275 (4)	0.6138 (3)	0.9178 (3)	0.069 (1)
C4	0.2304 (5)	0.5791 (3)	0.9751 (3)	0.080 (1)
C5	0.3583 (4)	0.6137 (3)	0.9629 (3)	0.081 (1)
C6	0.3843 (3)	0.6835 (3)	0.8907 (2)	0.056 (1)
C7	0.1690 (2)	0.7854 (2)	0.5685 (2)	0.030 (1)
C8	0.1040 (2)	0.6564 (2)	0.5060 (2)	0.043 (1)
C9	0.0106 (3)	0.6235 (3)	0.4028 (2)	0.055 (1)
C10	−0.0190 (2)	0.7186 (3)	0.3603 (2)	0.050 (1)
C11	0.0442 (2)	0.8464 (3)	0.4207 (2)	0.047 (1)
C12	0.1375 (2)	0.8802 (2)	0.5244 (2)	0.038 (1)
C13	0.4995 (2)	0.9507 (2)	0.7511 (2)	0.032 (1)
C14	0.5979 (2)	0.9754 (2)	0.8500 (2)	0.041 (1)
C15	0.7212 (2)	1.0520 (3)	0.8651 (2)	0.051 (1)
C16	0.7464 (2)	1.1054 (3)	0.7831 (2)	0.052 (1)
C17	0.6498 (2)	1.0835 (2)	0.6851 (2)	0.050 (1)
C18	0.5272 (2)	1.0067 (2)	0.6694 (2)	0.041 (1)
C19	0.2216 (2)	1.0927 (2)	0.8375 (2)	0.036 (1)
C20	0.1678 (2)	1.1837 (2)	0.9407 (2)	0.045 (1)
C21	0.6610 (8)	0.476 (1)	0.702 (1)	0.060 (4)	0.50
C22	0.7284 (6)	0.6005 (6)	0.6908 (5)	0.053 (2)	0.50
C23	0.7204 (9)	0.7099 (7)	0.5549 (7)	0.048 (2)	0.50
C24	0.6634 (6)	0.6796 (7)	0.4237 (7)	0.072 (3)	0.50
C25	0.4541 (5)	0.5912 (6)	0.2947 (4)	0.053 (1)	0.50
C26	0.3210 (7)	0.5133 (9)	0.286 (1)	0.045 (3)	0.50
C27	0.2213 (5)	0.3374 (6)	0.3310 (5)	0.052 (1)	0.50
C28	0.251 (1)	0.2579 (8)	0.4042 (7)	0.050 (2)	0.50
C29	0.3799 (7)	0.2791 (6)	0.5819 (5)	0.062 (2)	0.50
C30	0.4468 (8)	0.3698 (6)	0.7007 (6)	0.095 (3)	0.50
H1w1	0.415 (5)	0.587 (3)	0.627 (4)	0.044*	0.50
H1w2	0.443 (5)	0.648 (4)	0.550 (3)	0.044*	0.50
H1w3	0.369 (3)	0.579 (3)	0.555 (4)	0.044*	0.50
H1w4	0.486 (2)	0.647 (4)	0.633 (4)	0.044*	0.50
H2	0.0810	0.7125	0.8109	0.056*
H3	0.0395	0.5887	0.9258	0.083*
H4	0.2134	0.5309	1.0235	0.097*
H5	0.4291	0.5903	1.0036	0.097*
H6	0.4724	0.7064	0.8818	0.067*
H8	0.1236	0.5901	0.5341	0.051*
H9	−0.0329	0.5353	0.3615	0.066*
H10	−0.0826	0.6959	0.2901	0.060*
H11	0.0245	0.9120	0.3918	0.056*
H12	0.1801	0.9688	0.5655	0.046*
H14	0.5805	0.9397	0.9072	0.049*
H15	0.7875	1.0673	0.9318	0.061*
H16	0.8303	1.1574	0.7934	0.063*
H17	0.6675	1.1210	0.6290	0.060*
H18	0.4615	0.9921	0.6024	0.050*
H21a	0.6716	0.3977	0.6356	0.072*	0.50
H21b	0.7011	0.4699	0.7768	0.072*	0.50
H22a	0.6987	0.6777	0.7435	0.064*	0.50
H22b	0.8255	0.6122	0.7137	0.064*	0.50
H23a	0.8166	0.7438	0.5730	0.058*	0.50
H23b	0.6772	0.7758	0.6070	0.058*	0.50
H24a	0.6881	0.7564	0.4026	0.086*	0.50
H24b	0.6961	0.6044	0.3714	0.086*	0.50
H25a	0.5076	0.5332	0.2470	0.064*	0.50
H25b	0.4428	0.6605	0.2632	0.064*	0.50
H26a	0.2694	0.5694	0.3374	0.054*	0.50
H26b	0.2714	0.4805	0.2033	0.054*	0.50
H27a	0.1715	0.2790	0.2517	0.062*	0.50
H27b	0.1655	0.4002	0.3684	0.062*	0.50
H28a	0.1677	0.2043	0.4057	0.060*	0.50
H28b	0.3104	0.1984	0.3697	0.060*	0.50
H29a	0.4461	0.2389	0.5373	0.075*	0.50
H29b	0.3172	0.2082	0.5883	0.075*	0.50
H30a	0.3796	0.3973	0.7496	0.114*	0.50
H30b	0.5029	0.3237	0.7378	0.114*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03073 (8)	0.02856 (8)	0.02397 (8)	0.00790 (5)	0.00504 (5)	0.01114 (5)
F1	0.100 (6)	0.086 (3)	0.066 (2)	0.063 (4)	0.029 (3)	0.033 (2)
F2	0.20 (1)	0.077 (6)	0.12 (1)	0.069 (5)	0.12 (1)	0.052 (7)
F3	0.091 (5)	0.146 (3)	0.050 (7)	0.046 (3)	−0.017 (5)	−0.043 (5)
F1'	0.100 (6)	0.086 (3)	0.066 (2)	0.063 (4)	0.029 (3)	0.033 (2)
F2'	0.20 (1)	0.077 (6)	0.12 (1)	0.069 (5)	0.12 (1)	0.052 (7)
F3'	0.091 (5)	0.146 (3)	0.050 (7)	0.046 (3)	−0.017 (5)	−0.043 (5)
O1	0.049 (1)	0.034 (1)	0.036 (1)	0.016 (1)	0.013 (1)	0.013 (1)
O2	0.076 (1)	0.050 (2)	0.048 (1)	0.023 (1)	0.021 (1)	0.026 (1)
O3	0.056 (2)	0.057 (2)	0.072 (3)	0.001 (2)	−0.006 (2)	0.033 (2)
O4	0.053 (2)	0.033 (2)	0.039 (1)	0.006 (1)	0.007 (2)	0.003 (1)
O5	0.053 (2)	0.052 (2)	0.044 (2)	0.017 (2)	0.021 (2)	0.019 (2)
O6	0.046 (2)	0.056 (2)	0.043 (2)	0.022 (2)	0.009 (2)	0.023 (2)
O7	0.057 (3)	0.070 (4)	0.055 (3)	−0.015 (2)	−0.013 (2)	0.029 (3)
O1w	0.042 (1)	0.037 (1)	0.034 (1)	0.017 (1)	0.012 (1)	0.011 (1)
C1	0.048 (1)	0.030 (1)	0.024 (1)	0.011 (1)	0.010 (1)	0.010 (1)
C2	0.055 (2)	0.042 (1)	0.034 (1)	−0.006 (1)	0.006 (1)	0.010 (1)
C3	0.101 (2)	0.050 (2)	0.047 (2)	−0.017 (2)	0.026 (2)	0.015 (1)
C4	0.157 (4)	0.049 (2)	0.052 (2)	0.020 (2)	0.041 (2)	0.030 (1)
C5	0.138 (3)	0.081 (2)	0.058 (2)	0.066 (2)	0.032 (2)	0.048 (2)
C6	0.073 (2)	0.067 (2)	0.051 (2)	0.041 (2)	0.024 (1)	0.037 (1)
C7	0.030 (1)	0.036 (1)	0.025 (1)	0.010 (1)	0.007 (1)	0.012 (1)
C8	0.049 (1)	0.039 (1)	0.038 (1)	0.006 (1)	0.000 (1)	0.015 (1)
C9	0.056 (2)	0.052 (2)	0.042 (2)	−0.005 (1)	−0.008 (1)	0.012 (1)
C10	0.040 (1)	0.073 (2)	0.034 (1)	0.007 (1)	−0.003 (1)	0.021 (1)
C11	0.046 (1)	0.062 (2)	0.043 (1)	0.018 (1)	0.005 (1)	0.030 (1)
C12	0.040 (1)	0.041 (1)	0.036 (1)	0.010 (1)	0.004 (1)	0.016 (1)
C13	0.034 (1)	0.031 (1)	0.029 (1)	0.007 (1)	0.006 (1)	0.008 (1)
C14	0.043 (1)	0.046 (1)	0.028 (1)	0.005 (1)	0.003 (1)	0.010 (1)
C15	0.042 (1)	0.056 (2)	0.037 (1)	−0.001 (1)	−0.005 (1)	0.005 (1)
C16	0.041 (1)	0.049 (1)	0.053 (2)	−0.008 (1)	0.006 (1)	0.009 (1)
C17	0.048 (1)	0.053 (1)	0.051 (2)	−0.001 (1)	0.010 (1)	0.025 (1)
C18	0.039 (1)	0.048 (1)	0.039 (1)	0.004 (1)	0.003 (1)	0.021 (1)
C19	0.040 (1)	0.037 (1)	0.029 (1)	0.010 (1)	0.002 (1)	0.010 (1)
C20	0.059 (2)	0.041 (1)	0.035 (1)	0.022 (1)	0.010 (1)	0.012 (1)
C21	0.076 (7)	0.067 (7)	0.030 (5)	0.025 (5)	−0.011 (5)	0.013 (5)
C22	0.036 (4)	0.064 (4)	0.038 (3)	0.002 (4)	−0.006 (3)	0.002 (3)
C23	0.032 (5)	0.039 (4)	0.068 (7)	−0.003 (3)	0.004 (5)	0.017 (5)
C24	0.050 (4)	0.037 (4)	0.140 (9)	0.019 (3)	0.021 (5)	0.042 (5)
C25	0.075 (4)	0.054 (4)	0.048 (3)	0.027 (3)	0.025 (3)	0.032 (3)
C26	0.056 (5)	0.053 (6)	0.029 (5)	0.027 (4)	0.005 (4)	0.014 (4)
C27	0.033 (3)	0.062 (4)	0.048 (3)	0.011 (2)	0.000 (2)	0.009 (3)
C28	0.029 (4)	0.055 (5)	0.054 (5)	−0.004 (3)	−0.001 (3)	0.014 (4)
C29	0.104 (6)	0.041 (4)	0.047 (4)	0.002 (4)	0.034 (4)	0.019 (3)
C30	0.117 (7)	0.071 (5)	0.098 (6)	−0.015 (4)	−0.016 (5)	0.058 (5)

Geometric parameters (Å, º)

Sn1—C1	2.131 (2)	C23—C24	1.547 (7)
Sn1—C7	2.137 (2)	C25—C26	1.505 (7)
Sn1—C13	2.124 (2)	C27—C28	1.497 (7)
Sn1—O1	2.186 (2)	C29—C30	1.470 (7)
Sn1—O1w	2.407 (1)	O1w—H1w1	0.84 (1)
F1—C20	1.321 (7)	O1w—H1w2	0.85 (1)
F2—C20	1.318 (8)	O1w—H1w3	0.85 (1)
F3—C20	1.319 (8)	O1w—H1w4	0.85 (1)
F1'—C20	1.321 (7)	C2—H2	0.95
F2'—C20	1.316 (8)	C3—H3	0.95
F3'—C20	1.319 (7)	C4—H4	0.95
O1—C19	1.277 (3)	C5—H5	0.95
O2—C19	1.218 (3)	C6—H6	0.95
O3—C21	1.409 (8)	C8—H8	0.95
O3—C30	1.411 (6)	C9—H9	0.95
O4—C22	1.424 (6)	C10—H10	0.95
O4—C23	1.432 (6)	C11—H11	0.95
O5—C25	1.412 (5)	C12—H12	0.95
O5—C24	1.459 (6)	C14—H14	0.95
O6—C26	1.418 (7)	C15—H15	0.95
O6—C27	1.420 (5)	C16—H16	0.95
O7—C29	1.406 (6)	C17—H17	0.95
O7—C28	1.418 (6)	C18—H18	0.95
C1—C2	1.398 (3)	C21—H21a	0.99
C1—C6	1.400 (3)	C21—H21b	0.99
C2—C3	1.394 (4)	C22—H22a	0.99
C3—C4	1.374 (5)	C22—H22b	0.99
C4—C5	1.380 (5)	C23—H23a	0.99
C5—C6	1.402 (4)	C23—H23b	0.99
C7—C12	1.398 (3)	C24—H24a	0.99
C7—C8	1.395 (3)	C24—H24b	0.99
C8—C9	1.398 (3)	C25—H25a	0.99
C9—C10	1.383 (4)	C25—H25b	0.99
C10—C11	1.377 (4)	C26—H26a	0.99
C11—C12	1.400 (3)	C26—H26b	0.99
C13—C18	1.399 (3)	C27—H27a	0.99
C13—C14	1.404 (3)	C27—H27b	0.99
C14—C15	1.397 (3)	C28—H28a	0.99
C15—C16	1.377 (4)	C28—H28b	0.99
C16—C17	1.392 (4)	C29—H29a	0.99
C17—C18	1.391 (3)	C29—H29b	0.99
C19—C20	1.542 (3)	C30—H30a	0.99
C21—C22	1.532 (8)	C30—H30b	0.99
C1—Sn1—C7	117.4 (1)	C5—C4—H4	119.8
C1—Sn1—C13	120.9 (1)	C4—C5—H5	119.9
C1—Sn1—O1	87.6 (1)	C6—C5—H5	119.9
C1—Sn1—O1w	86.2 (1)	C5—C6—H6	120.0
C7—Sn1—C13	120.5 (1)	C1—C6—H6	120.0
C7—Sn1—O1	96.7 (1)	C9—C8—H8	119.6
C7—Sn1—O1w	86.4 (1)	C7—C8—H8	119.6
C13—Sn1—O1	96.5 (1)	C10—C9—H9	119.8
C13—Sn1—O1w	86.5 (1)	C8—C9—H9	119.8
O1—Sn1—O1w	173.8 (1)	C11—C10—H10	120.3
C19—O1—Sn1	124.4 (2)	C9—C10—H10	120.3
C21—O3—C30	115.1 (6)	C10—C11—H11	119.8
C22—O4—C23	113.6 (4)	C12—C11—H11	119.8
C25—O5—C24	112.1 (4)	C7—C12—H12	119.5
C26—O6—C27	113.5 (4)	C11—C12—H12	119.5
C29—O7—C28	111.4 (6)	C15—C14—H14	119.6
C2—C1—C6	118.6 (2)	C13—C14—H14	119.6
C2—C1—Sn1	119.4 (2)	C16—C15—H15	120.1
C6—C1—Sn1	121.9 (2)	C14—C15—H15	120.1
C3—C2—C1	120.7 (3)	C15—C16—H16	119.8
C4—C3—C2	120.0 (3)	C17—C16—H16	119.8
C3—C4—C5	120.4 (3)	C18—C17—H17	120.1
C4—C5—C6	120.2 (3)	C16—C17—H17	120.1
C5—C6—C1	119.9 (3)	C17—C18—H18	119.6
C12—C7—C8	117.9 (2)	C13—C18—H18	119.6
C12—C7—Sn1	122.7 (2)	O3—C21—H21a	110.2
C8—C7—Sn1	119.4 (2)	C22—C21—H21a	110.2
C9—C8—C7	120.9 (2)	O3—C21—H21b	110.2
C10—C9—C8	120.5 (2)	C22—C21—H21b	110.2
C11—C10—C9	119.5 (2)	H21a—C21—H21b	108.5
C10—C11—C12	120.4 (2)	O4—C22—H22a	110.1
C7—C12—C11	120.9 (2)	C21—C22—H22a	110.1
C18—C13—C14	118.3 (2)	O4—C22—H22b	110.1
C18—C13—Sn1	120.5 (2)	C21—C22—H22b	110.1
C14—C13—Sn1	121.2 (2)	H22a—C22—H22b	108.4
C15—C14—C13	120.7 (2)	O4—C23—H23a	110.5
C16—C15—C14	119.9 (2)	C24—C23—H23a	110.5
C15—C16—C17	120.4 (2)	O4—C23—H23b	110.5
C18—C17—C16	119.9 (2)	C24—C23—H23b	110.5
C17—C18—C13	120.8 (2)	H23a—C23—H23b	108.7
O2—C19—O1	129.6 (2)	O5—C24—H24a	110.8
O2—C19—C20	117.6 (2)	C23—C24—H24a	110.8
O1—C19—C20	112.8 (2)	O5—C24—H24b	110.8
F1'—C20—F2'	105.8 (6)	C23—C24—H24b	110.8
F1'—C20—F3'	105.9 (6)	H24a—C24—H24b	108.9
F2'—C20—F3'	106.5 (6)	O5—C25—H25a	109.6
F1—C20—F2	105.6 (6)	C26—C25—H25a	109.6
F1—C20—F3	105.8 (7)	O5—C25—H25b	109.6
F2—C20—F3	106.4 (6)	C26—C25—H25b	109.6
F2'—C20—C19	118 (2)	H25a—C25—H25b	108.1
F2—C20—C19	112 (2)	O6—C26—H26a	110.0
F3'—C20—C19	106 (2)	C25—C26—H26a	110.0
F3—C20—C19	115 (2)	O6—C26—H26b	110.0
F1'—C20—C19	114 (2)	C25—C26—H26b	110.0
F1—C20—C19	111 (2)	H26a—C26—H26b	108.3
O3—C21—C22	107.6 (7)	O6—C27—H27a	109.5
O4—C22—C21	108.2 (6)	C28—C27—H27a	109.5
O4—C23—C24	105.9 (5)	O6—C27—H27b	109.5
O5—C24—C23	104.6 (6)	C28—C27—H27b	109.5
O5—C25—C26	110.4 (5)	H27a—C27—H27b	108.1
O6—C26—C25	108.7 (6)	O7—C28—H28a	109.9
O6—C27—C28	110.7 (5)	C27—C28—H28a	109.9
O7—C28—C27	108.7 (6)	O7—C28—H28b	109.9
O7—C29—C30	111.2 (5)	C27—C28—H28b	109.9
O3—C30—C29	112.5 (5)	H28a—C28—H28b	108.3
Sn1—O1w—H1w1	122 (3)	O7—C29—H29a	109.4
Sn1—O1w—H1w2	127 (3)	C30—C29—H29a	109.4
H1w1—O1w—H1w2	111 (2)	O7—C29—H29b	109.4
Sn1—O1w—H1w3	129 (3)	C30—C29—H29b	109.4
Sn1—O1w—H1w4	119 (3)	H29a—C29—H29b	108.0
H1w3—O1w—H1w4	110 (2)	O3—C30—H30a	109.1
C3—C2—H2	119.6	C29—C30—H30a	109.1
C1—C2—H2	119.6	O3—C30—H30b	109.1
C4—C3—H3	120.0	C29—C30—H30b	109.1
C2—C3—H3	120.0	H30a—C30—H30b	107.8
C3—C4—H4	119.8
C13—Sn1—O1—C19	52.0 (2)	C7—Sn1—C13—C14	−176.7 (2)
C1—Sn1—O1—C19	172.8 (2)	O1—Sn1—C13—C14	81.6 (2)
C7—Sn1—O1—C19	−69.9 (2)	O1w—Sn1—C13—C14	−92.9 (2)
C13—Sn1—C1—C2	153.7 (2)	C18—C13—C14—C15	−1.2 (3)
C7—Sn1—C1—C2	−38.7 (2)	Sn1—C13—C14—C15	178.3 (2)
O1—Sn1—C1—C2	57.6 (2)	C13—C14—C15—C16	0.8 (4)
O1w—Sn1—C1—C2	−122.6 (2)	C14—C15—C16—C17	0.0 (4)
C13—Sn1—C1—C6	−23.6 (2)	C15—C16—C17—C18	−0.4 (4)
C7—Sn1—C1—C6	144.0 (2)	C16—C17—C18—C13	−0.1 (4)
O1—Sn1—C1—C6	−119.7 (2)	C14—C13—C18—C17	0.8 (3)
O1w—Sn1—C1—C6	60.1 (2)	Sn1—C13—C18—C17	−178.6 (2)
C6—C1—C2—C3	−2.5 (3)	Sn1—O1—C19—O2	6.2 (3)
Sn1—C1—C2—C3	−179.9 (2)	Sn1—O1—C19—C20	−173.1 (1)
C1—C2—C3—C4	2.4 (4)	O2—C19—C20—F2'	164 (3)
C2—C3—C4—C5	−0.8 (5)	O1—C19—C20—F2'	−17 (3)
C3—C4—C5—C6	−0.8 (5)	O2—C19—C20—F2	152 (3)
C4—C5—C6—C1	0.7 (5)	O1—C19—C20—F2	−29 (3)
C2—C1—C6—C5	0.9 (4)	O2—C19—C20—F3'	−77 (3)
Sn1—C1—C6—C5	178.3 (2)	O1—C19—C20—F3'	103 (3)
C13—Sn1—C7—C12	−45.6 (2)	O2—C19—C20—F3	−87 (3)
C1—Sn1—C7—C12	146.7 (2)	O1—C19—C20—F3	93 (3)
O1—Sn1—C7—C12	56.0 (2)	O2—C19—C20—F1'	39 (3)
O1w—Sn1—C7—C12	−129.5 (2)	O1—C19—C20—F1'	−142 (3)
C13—Sn1—C7—C8	133.3 (2)	O2—C19—C20—F1	34 (3)
C1—Sn1—C7—C8	−34.4 (2)	O1—C19—C20—F1	−147 (3)
O1—Sn1—C7—C8	−125.1 (2)	C30—O3—C21—C22	176.0 (7)
O1w—Sn1—C7—C8	49.5 (2)	C23—O4—C22—C21	164.3 (7)
C12—C7—C8—C9	0.0 (4)	O3—C21—C22—O4	−75 (1)
Sn1—C7—C8—C9	−179.0 (2)	C22—O4—C23—C24	−174.2 (6)
C7—C8—C9—C10	0.2 (4)	C25—O5—C24—C23	−167.1 (5)
C8—C9—C10—C11	−0.1 (4)	O4—C23—C24—O5	67.9 (8)
C9—C10—C11—C12	−0.2 (4)	C24—O5—C25—C26	157.3 (5)
C8—C7—C12—C11	−0.3 (3)	C27—O6—C26—C25	171.4 (6)
Sn1—C7—C12—C11	178.7 (2)	O5—C25—C26—O6	−65.1 (9)
C10—C11—C12—C7	0.4 (4)	C26—O6—C27—C28	−161.1 (7)
C1—Sn1—C13—C18	170.0 (2)	C29—O7—C28—C27	−160.3 (6)
C7—Sn1—C13—C18	2.7 (2)	O6—C27—C28—O7	64 (1)
O1—Sn1—C13—C18	−99.0 (2)	C28—O7—C29—C30	177.8 (7)
O1w—Sn1—C13—C18	86.5 (2)	C21—O3—C30—C29	−96 (1)
C1—Sn1—C13—C14	−9.4 (2)	O7—C29—C30—O3	−51.9 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O3	0.84 (1)	2.07 (3)	2.837 (4)	152 (5)
O1w—H1w2···O5	0.85 (1)	1.96 (1)	2.800 (4)	176 (4)
O1w—H1w3···O4^i	0.85 (1)	1.93 (1)	2.768 (3)	172 (4)
O1w—H1w4···O6^i	0.85 (1)	2.05 (2)	2.881 (4)	168 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.