Dimeth­yl(1,10-phenanthroline)­bis­(2,3,4,5-tetra­fluoro­benzoato)tin(IV)

The title compound, [Sn(CH₃)₂(C₇HF₄O₂)₂(C₁₂H₈N₂)], was synthesized by the reaction of dimethyl­tin(IV) dichloride and disodium 2,3,4,5-tetra­fluoro­benzoate in the presence of 1,10-phenanthroline. In the complex, the Sn^IV ion is coordinated by three O atoms of two tetra­fluoro­benzoate ligands, two N atoms of a 1,10-phenanthroline ligand and two methyl groups in a distorted penta­gonal–bipyramidal coordination. The axial positions are occupied by the methyl groups. In the crystal structure, C—H...F and C—H...O hydrogen bonds link the mol­ecules into cyclic centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.081
• wR factor = 0.222
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         16
PLAT432_ALERT_2_C Short Inter X...Y Contact  C13    ..  C22     ..       3.19 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Organotin carboxylate complexes have recently attracted much attention due to their biochemical and commercial applications (Narula et al., 1988). In order to explore the impact of the structure on properties of the complexes, as well as to analyze the structure–activity relationships, a large number of organotin carboxylates have been prepared and studied (Gielen, 2002). We report here the crystal structure of the title compound, Me₂Sn(C₆HF₄CO₂)₂(C₁₂H₈N₂), with 1,10-phenanthroline as a co-ligand.

The coordination geometry about the Sn atom is best described as distorted pentagonal bipyramidal with the axial positions occupied by methyl groups (Table 1). Three carboxylate O atoms (O1,O2,O3) from two tetrafluorobenzoate ligands and the two N atoms (N1,N2) of the 1,10-phenanthroline ligand occupy the basal plane (Fig. 1). The Sn—N distances (Table 1) are longer than the sum of the covalent radii of Sn and N atoms (2.15 Å), but much shorter than the sum of van der Waals radii of the two atoms (3.74 Å; Casas et al., 1997). The Sn1—O3 bond length of 2.146 (7) Å is close to the sum of the covalent radii of Sn and O atoms (2.13 Å), showing strong coordination interaction, which is in agreement with the monodentate coordination mode of the carboxylate group (Li et al., 2005). The Sn1—O2 [2.360 (7) Å] and Sn1—O1 [2.554 (8) Å] distances lie midway between the sums of the van der Waals and covalent radii of Sn and O atoms (2.13–3.68 Å; Ma et al., 2005).

In the crystal structure, C—H···F and C—H···O type hydrogen bonds link the molecules into cyclic centrosymmetric dimers (Table 2).

Related literature

For applications of organotin carboxylate complexes, see: Narula et al. (1988). For related structures, see: Gielen (2002); Li et al. (2005). For van der Waals radii and covalent radii data, see: Casas et al. (1997); Ma et al. (2005).

S2. Experimental

All reagents and solvents were used as obtained without further purification. The reaction was carried out under a nitrogen atmosphere. 2,3,4,5-Tetrafluorobenzoic acid (0.388 g, 2 mmol) was added to a solution of sodium ethoxide (0.272 g, 2 mmol) in benzene (30 ml) and the mixture was stirred for 10 min, after that dimethyltin dichloride (0.220 g, 1 mmol) and 1,10-phenanthroline (0.198 g, 1 mmol) were added. The reaction mixture was kept at 313 K for 12 h. After cooling to room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum. The solid residue was recrystallized from diethyl ether and colourless crystals of the title compound suitable for X-Ray diffraction studies were obtained (yield 0.724 g, 81%; m.p. 414 K). Analysis, calculated for C₂₈H₁₆N₂O₄Sn: C 59.72, H 2.86, N 4.97; found: C 59.53, H 2.68, N 5.17%.

S3. Refinement

H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl) and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.

Dimethyl(1,10-phenanthroline)bis(2,3,4,5-tetrafluorobenzoato)tin(IV)

Crystal data

[Sn(CH3)2(C7HF4O2)2(C12H8N2)]	Z = 2
Mr = 715.12	F(000) = 704
Triclinic, P1	Dx = 1.807 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.265 (4) Å	Cell parameters from 2191 reflections
b = 10.174 (6) Å	θ = 2.4–25.8°
c = 18.957 (11) Å	µ = 1.07 mm^−1
α = 90.519 (10)°	T = 298 K
β = 90.205 (9)°	Block, colourless
γ = 110.247 (8)°	0.18 × 0.13 × 0.09 mm
V = 1314.5 (13) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	4483 independent reflections
Radiation source: fine-focus sealed tube	3007 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.831, Tmax = 0.910	k = −12→11
6410 measured reflections	l = −22→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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.222	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.132P)^2] where P = (Fo^2 + 2Fc^2)/3
4483 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 1.64 e Å^−3
0 restraints	Δρmin = −2.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Sn1	0.23811 (11)	0.21428 (7)	0.24653 (4)	0.0428 (3)
F1	0.6709 (13)	0.3680 (8)	0.4720 (4)	0.089 (2)
F2	0.8879 (12)	0.5751 (8)	0.5510 (4)	0.079 (2)
F3	0.9354 (12)	0.8410 (7)	0.5194 (4)	0.085 (2)
F4	0.7645 (13)	0.8986 (7)	0.4031 (5)	0.095 (3)
F5	0.1948 (11)	0.5064 (7)	−0.0229 (3)	0.0693 (19)
F6	0.2542 (13)	0.7781 (8)	−0.0370 (4)	0.080 (2)
F7	0.3925 (12)	0.9560 (6)	0.0717 (4)	0.076 (2)
F8	0.4790 (11)	0.8624 (7)	0.1952 (4)	0.0697 (19)
N1	0.2041 (13)	−0.0126 (9)	0.3011 (4)	0.048 (2)
N2	0.0471 (13)	0.0191 (8)	0.1755 (5)	0.048 (2)
O1	0.4267 (13)	0.2843 (8)	0.3628 (4)	0.065 (2)
O2	0.4062 (12)	0.4435 (7)	0.2891 (4)	0.063 (2)
O3	0.1802 (11)	0.3414 (7)	0.1657 (4)	0.0480 (17)
O4	0.3100 (14)	0.3174 (8)	0.0624 (4)	0.068 (2)
C1	0.4652 (17)	0.4077 (12)	0.3462 (6)	0.052 (3)
C2	0.5966 (14)	0.5214 (10)	0.3913 (5)	0.042 (2)
C3	0.6878 (16)	0.4988 (10)	0.4510 (6)	0.048 (3)
C4	0.8018 (17)	0.6015 (12)	0.4933 (5)	0.054 (3)
C5	0.8270 (18)	0.7387 (12)	0.4780 (6)	0.063 (3)
C6	0.7380 (17)	0.7658 (10)	0.4181 (6)	0.053 (3)
C7	0.6231 (16)	0.6614 (11)	0.3753 (6)	0.052 (3)
H7	0.5626	0.6825	0.3359	0.062*
C8	0.2614 (17)	0.3861 (11)	0.1077 (6)	0.049 (3)
C9	0.2966 (14)	0.5365 (10)	0.0970 (5)	0.042 (2)
C10	0.2667 (15)	0.5912 (10)	0.0332 (5)	0.045 (2)
C11	0.2951 (18)	0.7302 (12)	0.0255 (6)	0.057 (3)
C12	0.3661 (18)	0.8207 (10)	0.0793 (6)	0.055 (3)
C13	0.4030 (15)	0.7691 (10)	0.1428 (6)	0.046 (2)
C14	0.3653 (15)	0.6309 (11)	0.1512 (6)	0.046 (2)
H14	0.3865	0.5986	0.1952	0.056*
C15	0.2854 (18)	−0.0276 (13)	0.3634 (6)	0.061 (3)
H15	0.3559	0.0518	0.3895	0.073*
C16	0.2661 (19)	−0.1588 (13)	0.3892 (7)	0.066 (3)
H16	0.3235	−0.1667	0.4322	0.079*
C17	0.1632 (18)	−0.2761 (13)	0.3516 (8)	0.069 (4)
H17	0.1506	−0.3639	0.3690	0.083*
C18	0.0780 (19)	−0.2653 (12)	0.2883 (7)	0.061 (3)
C19	0.1024 (14)	−0.1294 (9)	0.2646 (5)	0.040 (2)
C20	0.0178 (14)	−0.1119 (9)	0.1983 (6)	0.043 (2)
C21	−0.0894 (15)	−0.2316 (10)	0.1590 (6)	0.051 (3)
C22	−0.1680 (17)	−0.2121 (12)	0.0942 (6)	0.053 (3)
H22	−0.2387	−0.2886	0.0663	0.064*
C23	−0.1392 (16)	−0.0783 (12)	0.0726 (6)	0.057 (3)
H23	−0.1924	−0.0625	0.0302	0.068*
C24	−0.0302 (17)	0.0321 (12)	0.1148 (6)	0.058 (3)
H24	−0.0101	0.1223	0.0990	0.070*
C25	−0.0352 (18)	−0.3825 (11)	0.2462 (7)	0.064 (3)
H25	−0.0525	−0.4723	0.2619	0.076*
C26	−0.1164 (18)	−0.3679 (11)	0.1858 (7)	0.063 (3)
H26	−0.1917	−0.4470	0.1604	0.076*
C27	0.5007 (19)	0.2137 (12)	0.2044 (6)	0.066 (3)
H27A	0.5862	0.3085	0.1972	0.098*
H27B	0.4758	0.1641	0.1601	0.098*
H27C	0.5617	0.1684	0.2364	0.098*
C28	−0.0154 (18)	0.2079 (12)	0.3005 (6)	0.061 (3)
H28A	−0.0556	0.1281	0.3309	0.092*
H28B	−0.1182	0.2007	0.2672	0.092*
H28C	0.0114	0.2919	0.3283	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0444 (4)	0.0339 (4)	0.0483 (4)	0.0111 (3)	−0.0070 (3)	0.0040 (3)
F1	0.093 (6)	0.073 (5)	0.095 (6)	0.020 (4)	−0.019 (5)	0.006 (4)
F2	0.088 (5)	0.076 (5)	0.061 (4)	0.014 (4)	−0.027 (4)	0.001 (4)
F3	0.088 (6)	0.057 (4)	0.087 (5)	−0.004 (4)	−0.024 (4)	−0.021 (4)
F4	0.115 (7)	0.045 (4)	0.112 (6)	0.011 (4)	−0.020 (5)	0.005 (4)
F5	0.090 (5)	0.055 (4)	0.058 (4)	0.021 (4)	−0.019 (4)	−0.008 (3)
F6	0.110 (6)	0.066 (5)	0.073 (4)	0.043 (4)	−0.012 (4)	0.015 (4)
F7	0.098 (6)	0.038 (3)	0.095 (5)	0.026 (4)	0.015 (4)	0.011 (3)
F8	0.075 (5)	0.050 (4)	0.078 (4)	0.014 (3)	0.003 (4)	−0.017 (3)
N1	0.053 (5)	0.043 (5)	0.054 (5)	0.023 (4)	0.000 (4)	0.015 (4)
N2	0.051 (5)	0.035 (4)	0.060 (6)	0.016 (4)	−0.008 (4)	0.000 (4)
O1	0.072 (6)	0.041 (4)	0.076 (5)	0.013 (4)	−0.014 (4)	−0.002 (4)
O2	0.069 (5)	0.041 (4)	0.060 (5)	−0.002 (4)	−0.023 (4)	−0.002 (4)
O3	0.054 (4)	0.042 (4)	0.047 (4)	0.016 (3)	−0.001 (4)	0.009 (3)
O4	0.089 (6)	0.047 (5)	0.066 (5)	0.021 (4)	0.009 (5)	0.004 (4)
C1	0.055 (7)	0.051 (7)	0.048 (6)	0.017 (5)	−0.022 (5)	−0.005 (5)
C2	0.036 (5)	0.035 (5)	0.054 (6)	0.011 (4)	0.002 (5)	−0.006 (5)
C3	0.053 (6)	0.031 (5)	0.054 (6)	0.006 (5)	0.000 (5)	0.007 (5)
C4	0.057 (7)	0.060 (7)	0.041 (6)	0.014 (6)	−0.004 (5)	−0.002 (5)
C5	0.064 (8)	0.051 (7)	0.057 (7)	0.000 (6)	−0.004 (6)	−0.012 (6)
C6	0.054 (7)	0.029 (5)	0.068 (7)	0.003 (5)	0.003 (6)	0.004 (5)
C7	0.043 (6)	0.044 (6)	0.062 (7)	0.006 (5)	−0.003 (5)	0.001 (5)
C8	0.055 (7)	0.040 (6)	0.046 (6)	0.011 (5)	−0.012 (5)	−0.005 (5)
C9	0.037 (5)	0.042 (5)	0.047 (6)	0.012 (4)	−0.002 (5)	0.005 (5)
C10	0.044 (6)	0.044 (6)	0.045 (6)	0.014 (5)	0.004 (5)	0.001 (5)
C11	0.064 (7)	0.050 (7)	0.058 (7)	0.019 (6)	0.008 (6)	0.014 (6)
C12	0.063 (7)	0.031 (5)	0.071 (7)	0.016 (5)	0.010 (6)	0.009 (5)
C13	0.038 (6)	0.040 (5)	0.062 (7)	0.016 (5)	0.008 (5)	−0.004 (5)
C14	0.037 (5)	0.050 (6)	0.052 (6)	0.015 (5)	0.007 (5)	0.004 (5)
C15	0.055 (7)	0.069 (8)	0.072 (8)	0.037 (6)	−0.005 (6)	0.012 (6)
C16	0.063 (8)	0.065 (8)	0.081 (8)	0.037 (7)	0.006 (7)	0.026 (7)
C17	0.050 (7)	0.060 (8)	0.108 (11)	0.032 (6)	0.016 (7)	0.034 (7)
C18	0.066 (8)	0.044 (6)	0.071 (8)	0.015 (6)	0.018 (6)	0.021 (6)
C19	0.034 (5)	0.024 (4)	0.063 (6)	0.012 (4)	0.005 (5)	0.009 (4)
C20	0.032 (5)	0.023 (5)	0.065 (7)	0.000 (4)	0.008 (5)	0.006 (4)
C21	0.032 (5)	0.038 (6)	0.075 (8)	−0.001 (4)	0.016 (5)	−0.001 (5)
C22	0.049 (6)	0.048 (6)	0.056 (7)	0.010 (5)	0.005 (5)	−0.008 (5)
C23	0.046 (6)	0.051 (7)	0.057 (7)	−0.003 (5)	−0.004 (5)	−0.001 (5)
C24	0.064 (7)	0.040 (6)	0.055 (7)	0.000 (5)	−0.011 (6)	0.008 (5)
C25	0.065 (8)	0.031 (6)	0.098 (10)	0.021 (5)	0.015 (7)	0.013 (6)
C26	0.059 (7)	0.028 (5)	0.095 (9)	0.006 (5)	0.021 (7)	0.002 (6)
C27	0.072 (8)	0.050 (7)	0.070 (8)	0.016 (6)	−0.012 (7)	−0.010 (6)
C28	0.068 (8)	0.045 (6)	0.065 (7)	0.011 (6)	−0.004 (6)	0.009 (5)

Geometric parameters (Å, º)

Sn1—C27	2.072 (13)	C9—C10	1.382 (14)
Sn1—C28	2.092 (13)	C10—C11	1.366 (15)
Sn1—O3	2.146 (7)	C11—C12	1.344 (16)
Sn1—O2	2.360 (7)	C12—C13	1.380 (16)
Sn1—N2	2.389 (8)	C13—C14	1.348 (14)
Sn1—N1	2.472 (8)	C14—H14	0.93
Sn1—O1	2.554 (8)	C15—C16	1.388 (16)
F1—C3	1.356 (12)	C15—H15	0.93
F2—C4	1.332 (12)	C16—C17	1.361 (18)
F3—C5	1.317 (12)	C16—H16	0.93
F4—C6	1.331 (12)	C17—C18	1.371 (17)
F5—C10	1.347 (11)	C17—H17	0.93
F6—C11	1.355 (13)	C18—C19	1.410 (14)
F7—C12	1.332 (11)	C18—C25	1.426 (17)
F8—C13	1.345 (11)	C19—C20	1.436 (14)
N1—C19	1.346 (12)	C20—C21	1.403 (13)
N1—C15	1.351 (14)	C21—C22	1.397 (16)
N2—C24	1.307 (13)	C21—C26	1.430 (16)
N2—C20	1.350 (12)	C22—C23	1.370 (16)
O1—C1	1.232 (13)	C22—H22	0.93
O2—C1	1.265 (12)	C23—C24	1.376 (14)
O3—C8	1.261 (13)	C23—H23	0.93
O4—C8	1.229 (13)	C24—H24	0.93
C1—C2	1.481 (14)	C25—C26	1.319 (17)
C2—C3	1.371 (14)	C25—H25	0.93
C2—C7	1.406 (14)	C26—H26	0.93
C3—C4	1.343 (14)	C27—H27A	0.96
C4—C5	1.378 (16)	C27—H27B	0.96
C5—C6	1.380 (16)	C27—H27C	0.96
C6—C7	1.359 (14)	C28—H28A	0.96
C7—H7	0.93	C28—H28B	0.96
C8—C9	1.478 (14)	C28—H28C	0.96
C9—C14	1.370 (14)
C27—Sn1—C28	173.1 (4)	C12—C11—F6	119.5 (10)
C27—Sn1—O3	95.4 (4)	C12—C11—C10	120.4 (10)
C28—Sn1—O3	91.1 (4)	F6—C11—C10	120.1 (10)
C27—Sn1—O2	88.2 (4)	F7—C12—C11	120.2 (11)
C28—Sn1—O2	90.9 (4)	F7—C12—C13	121.3 (10)
O3—Sn1—O2	77.6 (3)	C11—C12—C13	118.4 (10)
C27—Sn1—N2	93.0 (4)	F8—C13—C14	121.8 (10)
C28—Sn1—N2	89.7 (4)	F8—C13—C12	117.3 (9)
O3—Sn1—N2	85.6 (3)	C14—C13—C12	120.9 (10)
O2—Sn1—N2	163.2 (3)	C13—C14—C9	121.9 (10)
C27—Sn1—N1	87.6 (4)	C13—C14—H14	119.0
C28—Sn1—N1	87.6 (4)	C9—C14—H14	119.0
O3—Sn1—N1	153.2 (3)	N1—C15—C16	121.5 (12)
O2—Sn1—N1	129.2 (3)	N1—C15—H15	119.3
N2—Sn1—N1	67.6 (3)	C16—C15—H15	119.3
C27—Sn1—O1	85.9 (4)	C17—C16—C15	119.9 (12)
C28—Sn1—O1	88.1 (4)	C17—C16—H16	120.0
O3—Sn1—O1	130.3 (3)	C15—C16—H16	120.0
O2—Sn1—O1	52.8 (2)	C16—C17—C18	120.4 (11)
N2—Sn1—O1	144.0 (3)	C16—C17—H17	119.8
N1—Sn1—O1	76.4 (3)	C18—C17—H17	119.8
C19—N1—C15	118.0 (9)	C17—C18—C19	117.3 (11)
C19—N1—Sn1	117.1 (6)	C17—C18—C25	124.1 (11)
C15—N1—Sn1	124.9 (8)	C19—C18—C25	118.6 (11)
C24—N2—C20	117.6 (9)	N1—C19—C18	123.0 (10)
C24—N2—Sn1	123.4 (7)	N1—C19—C20	117.3 (8)
C20—N2—Sn1	119.1 (7)	C18—C19—C20	119.7 (9)
C1—O1—Sn1	88.1 (6)	N2—C20—C21	122.4 (10)
C1—O2—Sn1	96.3 (7)	N2—C20—C19	118.9 (8)
C8—O3—Sn1	133.0 (7)	C21—C20—C19	118.7 (9)
O1—C1—O2	122.8 (10)	C22—C21—C20	117.8 (10)
O1—C1—C2	120.2 (9)	C22—C21—C26	122.2 (10)
O2—C1—C2	116.9 (10)	C20—C21—C26	120.0 (11)
C3—C2—C7	116.8 (9)	C23—C22—C21	118.9 (10)
C3—C2—C1	123.8 (9)	C23—C22—H22	120.6
C7—C2—C1	119.3 (10)	C21—C22—H22	120.6
C4—C3—F1	114.1 (9)	C22—C23—C24	118.8 (11)
C4—C3—C2	124.0 (10)	C22—C23—H23	120.6
F1—C3—C2	121.9 (9)	C24—C23—H23	120.6
F2—C4—C3	122.1 (11)	N2—C24—C23	124.6 (11)
F2—C4—C5	118.6 (10)	N2—C24—H24	117.7
C3—C4—C5	119.2 (10)	C23—C24—H24	117.7
F3—C5—C4	120.2 (11)	C26—C25—C18	122.3 (11)
F3—C5—C6	121.3 (11)	C26—C25—H25	118.9
C4—C5—C6	118.5 (10)	C18—C25—H25	118.9
F4—C6—C7	119.7 (11)	C25—C26—C21	120.6 (11)
F4—C6—C5	118.3 (10)	C25—C26—H26	119.7
C7—C6—C5	122.0 (10)	C21—C26—H26	119.7
C6—C7—C2	119.4 (10)	Sn1—C27—H27A	109.5
C6—C7—H7	120.3	Sn1—C27—H27B	109.5
C2—C7—H7	120.3	H27A—C27—H27B	109.5
O4—C8—O3	126.4 (10)	Sn1—C27—H27C	109.5
O4—C8—C9	120.3 (10)	H27A—C27—H27C	109.5
O3—C8—C9	113.2 (9)	H27B—C27—H27C	109.5
C14—C9—C10	116.1 (10)	Sn1—C28—H28A	109.5
C14—C9—C8	120.4 (9)	Sn1—C28—H28B	109.5
C10—C9—C8	123.5 (9)	H28A—C28—H28B	109.5
F5—C10—C11	117.2 (10)	Sn1—C28—H28C	109.5
F5—C10—C9	120.6 (9)	H28A—C28—H28C	109.5
C11—C10—C9	122.1 (10)	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···F5^i	0.93	2.48	3.217 (13)	136
C22—H22···O4^i	0.93	2.49	3.191 (14)	133

Symmetry code: (i) −x, −y, −z.