Di-n-butyl­bis(2′,4′-di­fluoro-4-hydroxy­bi­phenyl-3-carboxyl­ato-O,O′)­tin(IV)

The crystal structure of the title compound, [Sn(C₄H₉)₂(C₁₃H₇F₂O₃)₂], contains discrete mol­ecules in which the central Sn atoms are asymmetrically coordinated to two carboxyl­ates and by two C atoms of two n-butyl groups. The Sn—C distances are identical within 3σ limits [mean Sn—C 2.118 (2) Å]. The Sn—O distances are significantly different from each other, with the mean value for the shorter distances being 2.098 (3) Å, while the longer Sn—O distances are 2.570 (3) and 2.686 (3) Å. The geometry around the Sn atom is highly distorted octahedral, that may be best described as one based on skew-trapezoidal planar geometry. The hydroxyl groups and the carboxyl­ate O atoms are hydrogen bonded, forming six-membered rings and exhibit an S(6) pattern of hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.148
• Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Di-n-butylbis(2',4'-difluoro-4-hydroxybiphenyl-3-carboxylato-O,O')tin(IV)

Crystal data

[Sn(C4H9)2(C13H7F2O3)2]	F(000) = 1480
Mr = 731.29	Dx = 1.537 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3676 (1) Å	Cell parameters from 12703 reflections
b = 9.2278 (1) Å	θ = 1.0–27.4°
c = 33.3643 (5) Å	µ = 0.88 mm^−1
β = 98.0917 (6)°	T = 170 K
V = 3160.19 (7) Å^3	Block, colourless
Z = 4	0.15 × 0.13 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer	6945 independent reflections
Radiation source: fine-focus sealed tube	5776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 27.4°, θmin = 1.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
Tmin = 0.879, Tmax = 0.928	k = −11→11
12703 measured reflections	l = −42→42

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 5.5P] where P = (Fo^2 + 2Fc^2)/3
6945 reflections	(Δ/σ)max = 0.001
426 parameters	Δρmax = 0.83 e Å^−3
6 restraints	Δρmin = −0.67 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.67984 (3)	0.33183 (3)	0.071834 (8)	0.03496 (12)
O1	0.5688 (3)	0.3806 (4)	0.11788 (9)	0.0393 (7)
O2	0.4269 (3)	0.4063 (4)	0.06245 (9)	0.0459 (8)
O3	0.1926 (3)	0.5048 (5)	0.06815 (9)	0.0512 (9)
H3	0.2560	0.4847	0.0560	0.077*
O4	0.8196 (3)	0.3062 (3)	0.12343 (9)	0.0365 (7)
O5	0.9149 (3)	0.2445 (4)	0.07122 (9)	0.0439 (8)
O6	1.1496 (4)	0.1297 (5)	0.08294 (12)	0.0620 (11)
H6	1.0810	0.1611	0.0693	0.093*
F1	0.2407 (5)	0.7550 (5)	0.24465 (16)	0.0476 (14)	0.50
F1'	0.4536 (6)	0.3052 (5)	0.24164 (18)	0.0545 (15)	0.50
F2	0.4238 (3)	0.5263 (5)	0.36243 (9)	0.0779 (12)
F3	1.0329 (5)	0.4270 (5)	0.24355 (15)	0.0456 (13)	0.50
F3'	1.2614 (6)	−0.0120 (6)	0.27009 (19)	0.0616 (17)	0.50
F4	1.1577 (4)	0.2725 (5)	0.37427 (10)	0.0766 (10)
C1	0.6299 (5)	0.1230 (6)	0.04806 (14)	0.0430 (11)
H1A	0.6749	0.0488	0.0664	0.052*
H1B	0.5349	0.1082	0.0470	0.052*
C2	0.6670 (4)	0.1022 (5)	0.00557 (13)	0.0406 (10)
H2A	0.7618	0.1190	0.0067	0.049*
H2B	0.6492	0.0005	−0.0029	0.049*
C3	0.5949 (5)	0.2017 (5)	−0.02604 (14)	0.0459 (12)
H3A	0.6173	0.3034	−0.0186	0.055*
H3B	0.5001	0.1895	−0.0260	0.055*
C4	0.6265 (7)	0.1734 (7)	−0.06853 (16)	0.0599 (15)
H4A	0.5785	0.2422	−0.0875	0.090*
H4B	0.6010	0.0742	−0.0767	0.090*
H4C	0.7202	0.1855	−0.0688	0.090*
C5	0.7022 (4)	0.5391 (5)	0.04660 (14)	0.0428 (11)
H5A	0.6430	0.5453	0.0207	0.051*
H5B	0.6731	0.6125	0.0650	0.051*
C6	0.8383 (4)	0.5799 (5)	0.03869 (15)	0.0469 (12)
H6A	0.9007	0.5683	0.0638	0.056*
H6B	0.8657	0.5150	0.0178	0.056*
C7	0.8390 (5)	0.7360 (7)	0.02438 (18)	0.0610 (15)
H7A	0.7904	0.7422	−0.0033	0.073*
H7B	0.7929	0.7968	0.0423	0.073*
C8	0.9747 (6)	0.7957 (8)	0.0241 (3)	0.088 (2)
H8A	0.9690	0.8925	0.0119	0.132*
H8B	1.0235	0.7314	0.0083	0.132*
H8C	1.0195	0.8021	0.0520	0.132*
C9	0.4536 (4)	0.4167 (5)	0.10005 (13)	0.0382 (10)
C10	0.3590 (4)	0.4700 (5)	0.12576 (13)	0.0334 (9)
C11	0.2337 (4)	0.5136 (5)	0.10830 (13)	0.0377 (10)
C12	0.1497 (4)	0.5694 (5)	0.13323 (14)	0.0408 (10)
H12	0.0661	0.6031	0.1217	0.049*
C13	0.1856 (4)	0.5769 (5)	0.17433 (14)	0.0371 (10)
H13	0.1257	0.6138	0.1908	0.044*
C14	0.3095 (4)	0.5309 (4)	0.19248 (12)	0.0312 (9)
C15	0.3943 (4)	0.4785 (5)	0.16778 (12)	0.0320 (9)
H15	0.4786	0.4474	0.1795	0.038*
C16	0.3444 (4)	0.5313 (5)	0.23746 (12)	0.0318 (9)
C17	0.3069 (4)	0.6414 (5)	0.26151 (14)	0.0394 (10)
H17	0.2602	0.7207	0.2484	0.047*	0.50
C18	0.3325 (5)	0.6440 (6)	0.30303 (15)	0.0494 (13)
H18	0.3049	0.7224	0.3182	0.059*
C19	0.3990 (4)	0.5295 (7)	0.32144 (14)	0.0487 (13)
C20	0.4421 (4)	0.4160 (6)	0.30000 (15)	0.0470 (12)
H20	0.4894	0.3371	0.3132	0.056*
C21	0.4132 (4)	0.4225 (4)	0.25889 (14)	0.0375 (10)
H21	0.4434	0.3454	0.2438	0.045*	0.50
C22	0.9192 (4)	0.2558 (5)	0.10911 (14)	0.0371 (10)
C23	1.0330 (4)	0.2077 (5)	0.13726 (14)	0.0359 (10)
C24	1.1418 (5)	0.1451 (5)	0.12266 (16)	0.0439 (11)
C25	1.2464 (5)	0.0992 (6)	0.15055 (17)	0.0522 (13)
H25	1.3197	0.0559	0.1411	0.063*
C26	1.2455 (4)	0.1154 (6)	0.19142 (17)	0.0498 (13)
H26	1.3180	0.0823	0.2097	0.060*
C27	1.1398 (4)	0.1798 (5)	0.20687 (14)	0.0353 (9)
C28	1.0341 (4)	0.2237 (5)	0.17911 (13)	0.0325 (9)
H28	0.9607	0.2656	0.1888	0.039*
C29	1.1419 (4)	0.2016 (4)	0.25104 (14)	0.0339 (9)
C30	1.0871 (4)	0.3204 (4)	0.26718 (14)	0.0366 (10)
H30	1.0440	0.3893	0.2488	0.044*	0.50
C31	1.0900 (5)	0.3469 (6)	0.30785 (16)	0.0482 (12)
H31	1.0505	0.4306	0.3174	0.058*
C32	1.1525 (5)	0.2468 (7)	0.33397 (15)	0.0532 (14)
C33	1.2088 (5)	0.1258 (7)	0.32107 (17)	0.0568 (15)
H33	1.2517	0.0571	0.3396	0.068*
C34	1.2005 (5)	0.1078 (5)	0.28005 (16)	0.0456 (12)
H34	1.2388	0.0227	0.2708	0.055*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03349 (17)	0.0466 (2)	0.02440 (16)	0.01009 (13)	0.00265 (11)	−0.00081 (13)
O1	0.0328 (15)	0.058 (2)	0.0273 (14)	0.0129 (14)	0.0037 (12)	−0.0047 (14)
O2	0.0435 (17)	0.066 (2)	0.0267 (15)	0.0127 (16)	0.0000 (13)	−0.0045 (16)
O3	0.0389 (17)	0.076 (3)	0.0346 (17)	0.0122 (17)	−0.0074 (13)	−0.0064 (17)
O4	0.0306 (14)	0.0469 (19)	0.0303 (15)	0.0099 (13)	−0.0010 (11)	0.0005 (13)
O5	0.0422 (17)	0.056 (2)	0.0335 (16)	0.0121 (15)	0.0067 (13)	0.0047 (16)
O6	0.050 (2)	0.090 (3)	0.046 (2)	0.028 (2)	0.0093 (17)	−0.002 (2)
F1	0.063 (3)	0.037 (3)	0.044 (3)	0.023 (3)	0.007 (3)	−0.008 (2)
F1'	0.062 (4)	0.043 (3)	0.057 (4)	0.015 (3)	0.003 (3)	0.002 (3)
F2	0.063 (2)	0.140 (4)	0.0291 (15)	−0.015 (2)	0.0012 (13)	0.0067 (19)
F3	0.048 (3)	0.041 (3)	0.046 (3)	0.014 (2)	0.002 (2)	0.003 (3)
F3'	0.087 (4)	0.032 (3)	0.061 (4)	0.030 (3)	−0.005 (3)	0.005 (3)
F4	0.087 (3)	0.101 (3)	0.0403 (17)	−0.013 (2)	0.0031 (16)	0.0029 (19)
C1	0.049 (3)	0.046 (3)	0.033 (2)	0.003 (2)	0.0033 (19)	−0.009 (2)
C2	0.044 (2)	0.042 (3)	0.034 (2)	0.005 (2)	0.0022 (18)	−0.010 (2)
C3	0.066 (3)	0.038 (3)	0.033 (2)	0.002 (2)	0.005 (2)	0.001 (2)
C4	0.081 (4)	0.061 (4)	0.038 (3)	−0.011 (3)	0.009 (3)	−0.012 (3)
C5	0.056 (3)	0.038 (3)	0.032 (2)	0.013 (2)	0.0001 (19)	−0.002 (2)
C6	0.046 (3)	0.044 (3)	0.047 (3)	0.005 (2)	−0.008 (2)	0.010 (2)
C7	0.066 (4)	0.060 (4)	0.052 (3)	0.002 (3)	−0.007 (3)	0.011 (3)
C8	0.081 (5)	0.073 (5)	0.111 (6)	−0.001 (4)	0.020 (4)	0.037 (4)
C9	0.034 (2)	0.047 (3)	0.033 (2)	0.0065 (19)	0.0025 (17)	−0.001 (2)
C10	0.0281 (19)	0.039 (2)	0.033 (2)	0.0036 (17)	0.0030 (16)	−0.0029 (19)
C11	0.033 (2)	0.044 (3)	0.034 (2)	0.0039 (19)	−0.0018 (17)	0.001 (2)
C12	0.0257 (19)	0.051 (3)	0.045 (2)	0.0082 (19)	0.0014 (17)	0.001 (2)
C13	0.030 (2)	0.042 (3)	0.039 (2)	0.0042 (18)	0.0062 (17)	0.001 (2)
C14	0.0308 (19)	0.029 (2)	0.033 (2)	−0.0003 (16)	0.0029 (16)	0.0023 (17)
C15	0.0274 (19)	0.036 (2)	0.032 (2)	0.0049 (16)	0.0005 (15)	−0.0020 (18)
C16	0.0263 (18)	0.038 (2)	0.032 (2)	−0.0029 (16)	0.0050 (15)	−0.0019 (18)
C17	0.038 (2)	0.041 (3)	0.040 (2)	−0.0009 (19)	0.0083 (19)	−0.007 (2)
C18	0.038 (2)	0.072 (4)	0.040 (3)	−0.006 (2)	0.008 (2)	−0.018 (3)
C19	0.036 (2)	0.081 (4)	0.029 (2)	−0.017 (2)	0.0032 (18)	0.002 (2)
C20	0.030 (2)	0.064 (3)	0.045 (3)	−0.006 (2)	−0.0026 (19)	0.018 (3)
C21	0.029 (2)	0.036 (2)	0.047 (3)	0.0010 (18)	0.0030 (18)	0.001 (2)
C22	0.032 (2)	0.041 (3)	0.040 (2)	0.0038 (18)	0.0064 (17)	0.003 (2)
C23	0.029 (2)	0.037 (2)	0.041 (2)	0.0046 (17)	0.0032 (17)	0.0025 (19)
C24	0.041 (2)	0.043 (3)	0.048 (3)	0.010 (2)	0.006 (2)	0.000 (2)
C25	0.035 (2)	0.062 (3)	0.058 (3)	0.021 (2)	0.003 (2)	−0.007 (3)
C26	0.035 (2)	0.050 (3)	0.060 (3)	0.014 (2)	−0.011 (2)	−0.002 (3)
C27	0.031 (2)	0.029 (2)	0.043 (2)	0.0005 (17)	−0.0024 (17)	−0.0021 (19)
C28	0.0265 (18)	0.027 (2)	0.042 (2)	−0.0005 (16)	0.0009 (16)	0.0001 (19)
C29	0.0295 (19)	0.026 (2)	0.044 (2)	−0.0028 (15)	−0.0049 (17)	0.0020 (18)
C30	0.032 (2)	0.030 (2)	0.046 (3)	−0.0052 (17)	0.0002 (18)	0.005 (2)
C31	0.044 (3)	0.051 (3)	0.051 (3)	−0.004 (2)	0.009 (2)	−0.005 (2)
C32	0.051 (3)	0.067 (4)	0.039 (3)	−0.018 (3)	−0.001 (2)	0.005 (3)
C33	0.053 (3)	0.060 (4)	0.052 (3)	−0.001 (3)	−0.012 (2)	0.023 (3)
C34	0.045 (3)	0.032 (2)	0.055 (3)	0.002 (2)	−0.008 (2)	0.007 (2)

Geometric parameters (Å, º)

Sn1—O1	2.095 (3)	C8—H8C	0.9800
Sn1—O4	2.101 (3)	C9—C10	1.475 (6)
Sn1—C5	2.116 (5)	C10—C15	1.400 (6)
Sn1—C1	2.120 (5)	C10—C11	1.406 (5)
Sn1—O5	2.570 (3)	C11—C12	1.385 (6)
Sn1—O2	2.686 (3)	C12—C13	1.371 (6)
O1—C9	1.300 (5)	C12—H12	0.9500
O2—C9	1.250 (5)	C13—C14	1.406 (6)
O3—C11	1.350 (5)	C13—H13	0.9500
O3—H3	0.8400	C14—C15	1.375 (6)
O4—C22	1.285 (5)	C14—C16	1.493 (6)
O5—C22	1.263 (5)	C15—H15	0.9500
O6—C24	1.346 (6)	C16—C21	1.373 (6)
O6—H6	0.8400	C16—C17	1.384 (6)
F1—C17	1.334 (4)	C17—C18	1.373 (7)
F1'—C21	1.321 (4)	C17—H17	0.9498
F2—C19	1.356 (5)	C18—C19	1.361 (8)
F3—C30	1.334 (4)	C18—H18	0.9500
F3'—C34	1.338 (4)	C19—C20	1.378 (8)
F4—C32	1.359 (6)	C20—C21	1.363 (6)
C1—C2	1.532 (6)	C20—H20	0.9500
C1—H1A	0.9900	C21—H21	0.9491
C1—H1B	0.9900	C22—C23	1.469 (6)
C2—C3	1.514 (7)	C23—C28	1.403 (6)
C2—H2A	0.9900	C23—C24	1.414 (6)
C2—H2B	0.9900	C24—C25	1.392 (7)
C3—C4	1.521 (7)	C25—C26	1.373 (7)
C3—H3A	0.9900	C25—H25	0.9500
C3—H3B	0.9900	C26—C27	1.407 (7)
C4—H4A	0.9800	C26—H26	0.9500
C4—H4B	0.9800	C27—C28	1.392 (6)
C4—H4C	0.9800	C27—C29	1.484 (6)
C5—C6	1.518 (5)	C28—H28	0.9500
C5—H5A	0.9900	C29—C34	1.375 (6)
C5—H5B	0.9900	C29—C30	1.379 (6)
C6—C7	1.518 (8)	C30—C31	1.375 (7)
C6—H6A	0.9900	C30—H30	0.9496
C6—H6B	0.9900	C31—C32	1.368 (8)
C7—C8	1.513 (5)	C31—H31	0.9500
C7—H7A	0.9900	C32—C33	1.358 (9)
C7—H7B	0.9900	C33—C34	1.369 (8)
C8—H8A	0.9800	C33—H33	0.9500
C8—H8B	0.9800	C34—H34	0.9505
O1—Sn1—O4	79.05 (11)	C13—C12—C11	120.9 (4)
O1—Sn1—C5	101.55 (15)	C13—C12—H12	119.5
O4—Sn1—C5	109.03 (15)	C11—C12—H12	119.5
O1—Sn1—C1	109.83 (17)	C12—C13—C14	121.2 (4)
O4—Sn1—C1	107.93 (16)	C12—C13—H13	119.4
C5—Sn1—C1	135.04 (18)	C14—C13—H13	119.4
O1—Sn1—O5	133.88 (10)	C15—C14—C13	118.1 (4)
O4—Sn1—O5	54.97 (11)	C15—C14—C16	121.2 (4)
C5—Sn1—O5	97.07 (14)	C13—C14—C16	120.6 (4)
C1—Sn1—O5	83.90 (16)	C14—C15—C10	121.4 (4)
O1—Sn1—O2	53.28 (10)	C14—C15—H15	119.3
O4—Sn1—O2	132.33 (10)	C10—C15—H15	119.3
C5—Sn1—O2	83.23 (14)	C21—C16—C17	113.7 (4)
C1—Sn1—O2	90.36 (16)	C21—C16—C14	123.8 (4)
O5—Sn1—O2	172.17 (10)	C17—C16—C14	122.4 (4)
C9—O1—Sn1	106.5 (3)	F1—C17—C18	115.2 (5)
C9—O2—Sn1	80.1 (2)	F1—C17—C16	120.2 (4)
C11—O3—H3	109.5	C18—C17—C16	124.6 (4)
C22—O4—Sn1	103.5 (3)	C18—C17—H17	117.7
C22—O5—Sn1	82.3 (2)	C16—C17—H17	117.8
C24—O6—H6	109.5	C19—C18—C17	117.1 (5)
C2—C1—Sn1	112.3 (3)	C19—C18—H18	121.5
C2—C1—H1A	109.1	C17—C18—H18	121.5
Sn1—C1—H1A	109.1	F2—C19—C18	119.0 (5)
C2—C1—H1B	109.1	F2—C19—C20	118.6 (5)
Sn1—C1—H1B	109.1	C18—C19—C20	122.5 (4)
H1A—C1—H1B	107.9	C21—C20—C19	116.6 (5)
C3—C2—C1	113.9 (4)	C21—C20—H20	121.7
C3—C2—H2A	108.8	C19—C20—H20	121.7
C1—C2—H2A	108.8	F1'—C21—C20	111.3 (5)
C3—C2—H2B	108.8	F1'—C21—C16	123.1 (5)
C1—C2—H2B	108.8	C20—C21—C16	125.5 (4)
H2A—C2—H2B	107.7	C20—C21—H21	117.2
C2—C3—C4	113.3 (4)	C16—C21—H21	117.3
C2—C3—H3A	108.9	O5—C22—O4	119.0 (4)
C4—C3—H3A	108.9	O5—C22—C23	121.8 (4)
C2—C3—H3B	108.9	O4—C22—C23	119.1 (4)
C4—C3—H3B	108.9	C28—C23—C24	119.4 (4)
H3A—C3—H3B	107.7	C28—C23—C22	119.9 (4)
C3—C4—H4A	109.5	C24—C23—C22	120.7 (4)
C3—C4—H4B	109.5	O6—C24—C25	118.5 (4)
H4A—C4—H4B	109.5	O6—C24—C23	122.9 (4)
C3—C4—H4C	109.5	C25—C24—C23	118.6 (5)
H4A—C4—H4C	109.5	C26—C25—C24	121.1 (4)
H4B—C4—H4C	109.5	C26—C25—H25	119.4
C6—C5—Sn1	116.7 (3)	C24—C25—H25	119.4
C6—C5—H5A	108.1	C25—C26—C27	121.6 (4)
Sn1—C5—H5A	108.1	C25—C26—H26	119.2
C6—C5—H5B	108.1	C27—C26—H26	119.2
Sn1—C5—H5B	108.1	C28—C27—C26	117.4 (4)
H5A—C5—H5B	107.3	C28—C27—C29	121.4 (4)
C7—C6—C5	109.6 (4)	C26—C27—C29	121.2 (4)
C7—C6—H6A	109.8	C27—C28—C23	121.8 (4)
C5—C6—H6A	109.8	C27—C28—H28	119.1
C7—C6—H6B	109.8	C23—C28—H28	119.1
C5—C6—H6B	109.8	C34—C29—C30	113.0 (4)
H6A—C6—H6B	108.2	C34—C29—C27	123.9 (4)
C8—C7—C6	113.2 (5)	C30—C29—C27	123.1 (4)
C8—C7—H7A	108.9	F3—C30—C31	113.7 (5)
C6—C7—H7A	108.9	F3—C30—C29	121.2 (5)
C8—C7—H7B	108.9	C31—C30—C29	125.0 (4)
C6—C7—H7B	108.9	C31—C30—H30	117.4
H7A—C7—H7B	107.8	C29—C30—H30	117.5
C7—C8—H8A	109.5	C32—C31—C30	116.8 (5)
C7—C8—H8B	109.5	C32—C31—H31	121.6
H8A—C8—H8B	109.5	C30—C31—H31	121.6
C7—C8—H8C	109.5	C33—C32—F4	119.8 (5)
H8A—C8—H8C	109.5	C33—C32—C31	122.7 (5)
H8B—C8—H8C	109.5	F4—C32—C31	117.5 (6)
O2—C9—O1	119.9 (4)	C32—C33—C34	116.5 (5)
O2—C9—C10	122.6 (4)	C32—C33—H33	121.7
O1—C9—C10	117.5 (4)	C34—C33—H33	121.7
C15—C10—C11	119.6 (4)	F3'—C34—C33	112.5 (5)
C15—C10—C9	120.0 (4)	F3'—C34—C29	121.5 (5)
C11—C10—C9	120.4 (4)	C33—C34—C29	126.0 (5)
O3—C11—C12	118.8 (4)	C33—C34—H34	116.9
O3—C11—C10	122.5 (4)	C29—C34—H34	117.1
C12—C11—C10	118.7 (4)
O4—Sn1—O1—C9	177.2 (3)	C21—C16—C17—F1	179.2 (5)
C5—Sn1—O1—C9	69.7 (3)	C14—C16—C17—F1	−2.3 (7)
C1—Sn1—O1—C9	−77.6 (3)	C21—C16—C17—C18	−1.1 (7)
O5—Sn1—O1—C9	−178.5 (3)	C14—C16—C17—C18	177.5 (4)
O2—Sn1—O1—C9	−2.7 (3)	F1—C17—C18—C19	179.6 (5)
O1—Sn1—O2—C9	2.7 (3)	C16—C17—C18—C19	−0.2 (7)
O4—Sn1—O2—C9	2.5 (4)	C17—C18—C19—F2	−178.6 (4)
C5—Sn1—O2—C9	−107.2 (3)	C17—C18—C19—C20	1.2 (7)
C1—Sn1—O2—C9	117.4 (3)	F2—C19—C20—C21	179.0 (4)
O1—Sn1—O4—C22	173.7 (3)	C18—C19—C20—C21	−0.8 (7)
C5—Sn1—O4—C22	−87.8 (3)	C19—C20—C21—F1'	−177.0 (5)
C1—Sn1—O4—C22	66.2 (3)	C19—C20—C21—C16	−0.7 (7)
O5—Sn1—O4—C22	−2.5 (3)	C17—C16—C21—F1'	177.4 (5)
O2—Sn1—O4—C22	173.9 (3)	C14—C16—C21—F1'	−1.1 (7)
O1—Sn1—O5—C22	−2.7 (4)	C17—C16—C21—C20	1.6 (6)
O4—Sn1—O5—C22	2.5 (3)	C14—C16—C21—C20	−177.0 (4)
C5—Sn1—O5—C22	110.8 (3)	Sn1—O5—C22—O4	−3.8 (4)
C1—Sn1—O5—C22	−114.4 (3)	Sn1—O5—C22—C23	173.8 (4)
O1—Sn1—C1—C2	159.0 (3)	Sn1—O4—C22—O5	4.8 (5)
O4—Sn1—C1—C2	−116.5 (3)	Sn1—O4—C22—C23	−172.9 (4)
C5—Sn1—C1—C2	27.5 (5)	O5—C22—C23—C28	179.4 (4)
O5—Sn1—C1—C2	−66.4 (3)	O4—C22—C23—C28	−3.0 (7)
O2—Sn1—C1—C2	108.3 (3)	O5—C22—C23—C24	−0.7 (7)
Sn1—C1—C2—C3	−63.8 (5)	O4—C22—C23—C24	176.9 (4)
C1—C2—C3—C4	−176.4 (4)	C28—C23—C24—O6	−178.2 (5)
O1—Sn1—C5—C6	133.7 (3)	C22—C23—C24—O6	1.9 (8)
O4—Sn1—C5—C6	51.4 (4)	C28—C23—C24—C25	0.9 (7)
C1—Sn1—C5—C6	−92.3 (4)	C22—C23—C24—C25	−179.0 (5)
O5—Sn1—C5—C6	−3.9 (4)	O6—C24—C25—C26	178.4 (5)
O2—Sn1—C5—C6	−176.0 (4)	C23—C24—C25—C26	−0.8 (8)
Sn1—C5—C6—C7	−174.8 (3)	C24—C25—C26—C27	−0.5 (9)
C5—C6—C7—C8	168.0 (6)	C25—C26—C27—C28	1.5 (8)
Sn1—O2—C9—O1	−4.0 (4)	C25—C26—C27—C29	−177.7 (5)
Sn1—O2—C9—C10	175.6 (5)	C26—C27—C28—C23	−1.3 (7)
Sn1—O1—C9—O2	5.3 (6)	C29—C27—C28—C23	177.9 (4)
Sn1—O1—C9—C10	−174.3 (3)	C24—C23—C28—C27	0.1 (7)
O2—C9—C10—C15	179.6 (5)	C22—C23—C28—C27	−179.9 (4)
O1—C9—C10—C15	−0.8 (7)	C28—C27—C29—C34	146.3 (5)
O2—C9—C10—C11	−0.9 (7)	C26—C27—C29—C34	−34.4 (7)
O1—C9—C10—C11	178.7 (4)	C28—C27—C29—C30	−35.0 (6)
C15—C10—C11—O3	−178.3 (4)	C26—C27—C29—C30	144.3 (5)
C9—C10—C11—O3	2.2 (7)	C34—C29—C30—F3	175.9 (5)
C15—C10—C11—C12	2.5 (7)	C27—C29—C30—F3	−2.9 (7)
C9—C10—C11—C12	−177.0 (4)	C34—C29—C30—C31	0.7 (6)
O3—C11—C12—C13	178.2 (5)	C27—C29—C30—C31	−178.1 (4)
C10—C11—C12—C13	−2.6 (7)	F3—C30—C31—C32	−175.5 (5)
C11—C12—C13—C14	1.3 (7)	C29—C30—C31—C32	0.0 (7)
C12—C13—C14—C15	0.2 (7)	C30—C31—C32—C33	−0.5 (8)
C12—C13—C14—C16	−176.3 (4)	C30—C31—C32—F4	179.1 (4)
C13—C14—C15—C10	−0.3 (6)	F4—C32—C33—C34	−179.5 (5)
C16—C14—C15—C10	176.2 (4)	C31—C32—C33—C34	0.1 (8)
C11—C10—C15—C14	−1.0 (7)	C32—C33—C34—F3'	178.4 (6)
C9—C10—C15—C14	178.4 (4)	C32—C33—C34—C29	0.8 (8)
C15—C14—C16—C21	−37.7 (6)	C30—C29—C34—F3'	−178.6 (5)
C13—C14—C16—C21	138.8 (4)	C27—C29—C34—F3'	0.2 (8)
C15—C14—C16—C17	143.9 (4)	C30—C29—C34—C33	−1.1 (7)
C13—C14—C16—C17	−39.6 (6)	C27—C29—C34—C33	177.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	1.90	2.626 (4)	144
O6—H6···O5	0.84	1.89	2.631 (5)	146