Di-n-butyl­bis[(E)-2-(4-chloro­phenyl)-3-(3-fluoro­phenyl)prop-2-enoato-κ²O,O]tin(IV)

The mol­ecule of the title compound, [Sn(C₄H₉)₂(C₁₅H₉ClFO₂)₂], has a skewed-trapezoidal planar geometry, defined by four O donors from the carboxyl­ate ligands and two C atoms from the n-butyl groups. The C—Sn—C bond angle is 133.95 (12)°. The O atoms of the carboxyl­ate ligands are bonded asymmetrically to Sn, with significantly different Sn—O distances; the values for the shorter are 2.0914 (18) and 2.1134 (19) Å, while the longer Sn—O distances are 2.513 (2) and 2.650 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.085
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.24 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.78 Ratio

Alert level C
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.20 prolat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C3     -   C4     ...       1.43 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C20    -   C21    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C21    -   C22    ...       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C22    -   C23    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C34    -   C35    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C35    -   C36    ...       1.37 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 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
   9 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

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Computing details

Data collection: COLLECT (Nonius, 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.

Di-n-butylbis[(E)-3-(3-fluorophenyl)-2-(4-chlorophenyl)-2-propenoato-O,O]tin(IV)

Crystal data

[Sn(C15H9O2ClF)2(C4H9)2]	F(000) = 1592
Mr = 784.26	Dx = 1.459 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15031 reflections
a = 11.252 (2) Å	θ = 3.5–27.5°
b = 11.886 (2) Å	µ = 0.92 mm^−1
c = 26.932 (4) Å	T = 173 K
β = 97.470 (8)°	Block, colourless
V = 3571.4 (10) Å^3	0.24 × 0.18 × 0.16 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	8137 independent reflections
Radiation source: fine-focus sealed tube	5376 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω and φ scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −14→14
Tmin = 0.811, Tmax = 0.868	k = −15→15
15031 measured reflections	l = −34→34

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0335P)^2] where P = (Fo^2 + 2Fc^2)/3
8137 reflections	(Δ/σ)max = 0.001
434 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −0.79 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	Occ. (<1)
Sn1	−0.043169 (18)	0.717013 (15)	0.201251 (8)	0.02897 (8)
Cl1	−0.65384 (8)	1.17998 (10)	0.06139 (4)	0.0725 (3)
Cl2	0.53597 (10)	0.66065 (8)	0.03072 (4)	0.0686 (3)
O1	−0.03387 (18)	0.84165 (16)	0.14708 (7)	0.0363 (5)
O2	−0.22118 (18)	0.84994 (15)	0.16323 (7)	0.0350 (5)
O3	0.12335 (17)	0.67579 (15)	0.17760 (7)	0.0331 (5)
O4	0.10548 (18)	0.58228 (15)	0.24650 (8)	0.0378 (5)
C1	−0.1565 (3)	0.5850 (2)	0.17261 (12)	0.0413 (8)
H1A	−0.1439	0.5200	0.1957	0.050*
H1B	−0.2408	0.6096	0.1717	0.050*
C2	−0.1368 (4)	0.5482 (3)	0.12183 (14)	0.0730 (13)
H2A	−0.0519	0.5255	0.1227	0.088*
H2B	−0.1508	0.6131	0.0988	0.088*
C3	−0.2162 (4)	0.4511 (3)	0.10081 (15)	0.0760 (13)
H3A	−0.2036	0.3868	0.1243	0.091*
H3B	−0.3011	0.4745	0.0992	0.091*
C4	−0.1950 (6)	0.4142 (4)	0.05216 (17)	0.115 (2)
H4A	−0.2496	0.3522	0.0412	0.172*
H4B	−0.1119	0.3882	0.0536	0.172*
H4C	−0.2088	0.4768	0.0284	0.172*
C5	−0.0239 (3)	0.8096 (2)	0.26866 (12)	0.0403 (8)
H5A	0.0568	0.8443	0.2733	0.048*
H5B	−0.0834	0.8713	0.2654	0.048*
C6	−0.0395 (3)	0.7412 (3)	0.31580 (13)	0.0497 (9)
H6A	0.0319	0.6929	0.3243	0.060*
H6B	−0.0431	0.7939	0.3440	0.060*
C7	−0.1502 (3)	0.6675 (3)	0.31079 (13)	0.0520 (10)
H7A	−0.1538	0.6284	0.3430	0.062*
H7B	−0.1426	0.6094	0.2851	0.062*
C8	−0.2669 (4)	0.7307 (3)	0.29665 (17)	0.0687 (12)
H8A	−0.3340	0.6775	0.2935	0.103*
H8B	−0.2648	0.7693	0.2646	0.103*
H8C	−0.2773	0.7862	0.3227	0.103*
C9	−0.1406 (3)	0.8853 (2)	0.13991 (11)	0.0306 (7)
C10	−0.1630 (3)	0.9776 (2)	0.10204 (10)	0.0289 (7)
C11	−0.0732 (3)	1.0126 (2)	0.07783 (11)	0.0334 (7)
H11	0.0029	0.9797	0.0883	0.040*
C12	−0.2858 (3)	1.0252 (2)	0.09375 (10)	0.0286 (7)
C13	−0.3832 (3)	0.9628 (2)	0.07179 (10)	0.0334 (7)
H13	−0.3719	0.8863	0.0633	0.040*
C14	−0.4952 (3)	1.0092 (3)	0.06210 (11)	0.0426 (8)
H14	−0.5608	0.9653	0.0472	0.051*
C15	−0.5116 (3)	1.1208 (3)	0.07431 (12)	0.0423 (8)
C16	−0.4190 (3)	1.1840 (3)	0.09672 (13)	0.0449 (9)
H16	−0.4318	1.2601	0.1054	0.054*
C17	−0.3059 (3)	1.1367 (2)	0.10677 (11)	0.0375 (8)
H17	−0.2414	1.1806	0.1227	0.045*
C18	−0.0774 (3)	1.0960 (2)	0.03678 (11)	0.0329 (7)
C19	−0.1760 (3)	1.1089 (3)	0.00074 (11)	0.0408 (8)
H19	−0.2463	1.0659	0.0029	0.049*
C20	−0.1732 (3)	1.1842 (3)	−0.03858 (13)	0.0448 (8)
H20	−0.2416	1.1914	−0.0631	0.054*
C21	−0.0734 (4)	1.2483 (3)	−0.04262 (14)	0.0509 (10)
H21	−0.0715	1.3006	−0.0692	0.061*	0.934 (5)
C22	0.0227 (4)	1.2338 (3)	−0.00684 (16)	0.0614 (11)
H22	0.0923	1.2779	−0.0089	0.074*	0.066 (5)
C23	0.0244 (3)	1.1586 (3)	0.03215 (13)	0.0491 (9)
H23	0.0945	1.1497	0.0556	0.059*
C24	0.1670 (3)	0.6071 (2)	0.21278 (11)	0.0314 (7)
C25	0.2903 (3)	0.5637 (2)	0.21139 (10)	0.0270 (7)
C26	0.3440 (3)	0.5130 (2)	0.25274 (11)	0.0297 (7)
H26	0.2963	0.5048	0.2792	0.036*
C27	0.3506 (3)	0.5885 (2)	0.16612 (10)	0.0288 (7)
C28	0.3113 (3)	0.5388 (3)	0.12052 (11)	0.0415 (8)
H28	0.2440	0.4899	0.1176	0.050*
C29	0.3688 (3)	0.5593 (3)	0.07907 (12)	0.0481 (9)
H29	0.3423	0.5240	0.0480	0.058*
C30	0.4653 (3)	0.6319 (2)	0.08353 (12)	0.0426 (9)
C31	0.5058 (3)	0.6834 (2)	0.12803 (12)	0.0372 (8)
H31	0.5718	0.7338	0.1305	0.045*
C32	0.4481 (3)	0.6605 (2)	0.16933 (11)	0.0312 (7)
H32	0.4761	0.6948	0.2005	0.037*
C33	0.4664 (3)	0.4683 (2)	0.26283 (11)	0.0286 (7)
C34	0.5295 (3)	0.4201 (2)	0.22683 (11)	0.0341 (7)
H34	0.4936	0.4132	0.1930	0.041*
C35	0.6439 (3)	0.3828 (2)	0.24108 (13)	0.0387 (8)
H35	0.6854	0.3486	0.2165	0.046*	0.066 (5)
C36	0.7020 (3)	0.3922 (2)	0.28900 (13)	0.0427 (8)
H36	0.7824	0.3673	0.2974	0.051*
C37	0.6389 (3)	0.4391 (3)	0.32425 (13)	0.0460 (9)
H37	0.6766	0.4476	0.3577	0.055*	0.934 (5)
C38	0.5221 (3)	0.4740 (2)	0.31186 (11)	0.0365 (8)
H38	0.4791	0.5025	0.3373	0.044*
F1	0.1228 (2)	1.2950 (2)	−0.00998 (12)	0.1131 (14)	0.934 (5)
F1'	−0.251 (3)	1.188 (3)	−0.0698 (13)	0.070 (13)*	0.066 (5)
F2	0.7038 (2)	0.33224 (18)	0.20717 (9)	0.0561 (9)	0.859 (5)
F2'	0.7036 (15)	0.4453 (12)	0.3675 (6)	0.067 (6)*	0.141 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02173 (12)	0.02427 (11)	0.04086 (13)	−0.00101 (9)	0.00385 (9)	0.00450 (9)
Cl1	0.0268 (5)	0.1146 (8)	0.0769 (7)	0.0218 (5)	0.0102 (5)	0.0411 (6)
Cl2	0.1001 (9)	0.0656 (6)	0.0475 (5)	−0.0146 (6)	0.0378 (6)	0.0033 (5)
O1	0.0283 (13)	0.0339 (11)	0.0477 (13)	0.0076 (10)	0.0084 (10)	0.0130 (10)
O2	0.0332 (13)	0.0319 (11)	0.0412 (12)	−0.0010 (10)	0.0103 (11)	0.0051 (9)
O3	0.0231 (12)	0.0300 (10)	0.0454 (12)	0.0018 (9)	0.0009 (10)	0.0057 (9)
O4	0.0266 (13)	0.0342 (11)	0.0546 (14)	0.0029 (9)	0.0132 (11)	0.0085 (10)
C1	0.031 (2)	0.0286 (16)	0.062 (2)	−0.0029 (14)	−0.0029 (17)	0.0018 (16)
C2	0.099 (4)	0.071 (3)	0.050 (2)	−0.045 (3)	0.013 (2)	−0.008 (2)
C3	0.108 (4)	0.055 (2)	0.063 (3)	−0.032 (2)	0.008 (3)	−0.011 (2)
C4	0.185 (6)	0.097 (4)	0.062 (3)	−0.045 (4)	0.015 (4)	−0.027 (3)
C5	0.037 (2)	0.0332 (16)	0.051 (2)	−0.0033 (14)	0.0082 (17)	−0.0048 (15)
C6	0.049 (2)	0.054 (2)	0.044 (2)	0.0035 (18)	0.0009 (18)	−0.0036 (17)
C7	0.057 (3)	0.050 (2)	0.050 (2)	−0.0006 (19)	0.0116 (19)	0.0163 (18)
C8	0.052 (3)	0.061 (2)	0.097 (3)	0.005 (2)	0.023 (2)	0.023 (2)
C9	0.0293 (19)	0.0266 (15)	0.0360 (17)	0.0006 (13)	0.0043 (15)	−0.0018 (13)
C10	0.0256 (18)	0.0262 (14)	0.0346 (16)	0.0017 (13)	0.0026 (14)	0.0009 (13)
C11	0.0288 (19)	0.0290 (15)	0.0424 (18)	0.0043 (13)	0.0044 (15)	0.0051 (14)
C12	0.0262 (18)	0.0316 (15)	0.0285 (16)	0.0003 (13)	0.0054 (14)	0.0066 (13)
C13	0.034 (2)	0.0368 (16)	0.0292 (16)	−0.0068 (15)	0.0037 (15)	0.0012 (13)
C14	0.028 (2)	0.074 (2)	0.0245 (16)	−0.0106 (18)	−0.0001 (15)	0.0085 (17)
C15	0.0217 (19)	0.071 (2)	0.0346 (18)	0.0066 (17)	0.0050 (15)	0.0227 (17)
C16	0.034 (2)	0.0382 (18)	0.063 (2)	0.0105 (15)	0.0091 (19)	0.0080 (16)
C17	0.0279 (19)	0.0336 (16)	0.049 (2)	0.0003 (14)	−0.0007 (16)	0.0017 (15)
C18	0.0282 (19)	0.0326 (15)	0.0393 (18)	0.0061 (14)	0.0097 (15)	0.0052 (14)
C19	0.040 (2)	0.0462 (19)	0.0355 (18)	−0.0021 (16)	0.0027 (16)	0.0062 (16)
C20	0.041 (2)	0.054 (2)	0.0372 (19)	0.0085 (17)	−0.0020 (18)	0.0047 (16)
C21	0.049 (3)	0.053 (2)	0.052 (2)	0.0110 (18)	0.015 (2)	0.0222 (18)
C22	0.040 (2)	0.067 (2)	0.080 (3)	−0.003 (2)	0.019 (2)	0.035 (2)
C23	0.027 (2)	0.060 (2)	0.060 (2)	0.0039 (17)	0.0058 (17)	0.0286 (19)
C24	0.0300 (19)	0.0221 (14)	0.0423 (18)	−0.0011 (13)	0.0053 (16)	−0.0001 (14)
C25	0.0257 (18)	0.0250 (14)	0.0307 (16)	−0.0002 (12)	0.0046 (14)	0.0015 (12)
C26	0.0263 (18)	0.0300 (15)	0.0342 (17)	0.0004 (13)	0.0099 (14)	0.0017 (13)
C27	0.0248 (18)	0.0279 (14)	0.0337 (17)	0.0049 (13)	0.0030 (14)	0.0048 (13)
C28	0.041 (2)	0.0433 (18)	0.0393 (19)	−0.0073 (16)	0.0028 (17)	0.0052 (15)
C29	0.066 (3)	0.0473 (19)	0.0290 (18)	−0.0069 (19)	0.0000 (18)	−0.0001 (15)
C30	0.055 (2)	0.0381 (18)	0.0385 (19)	0.0019 (16)	0.0178 (18)	0.0074 (15)
C31	0.038 (2)	0.0317 (16)	0.0433 (19)	−0.0003 (14)	0.0106 (16)	0.0042 (14)
C32	0.0270 (18)	0.0310 (15)	0.0364 (17)	0.0024 (13)	0.0065 (14)	0.0017 (14)
C33	0.0281 (18)	0.0267 (14)	0.0312 (16)	0.0032 (13)	0.0052 (14)	0.0051 (13)
C34	0.033 (2)	0.0331 (16)	0.0373 (17)	0.0039 (14)	0.0081 (15)	0.0039 (14)
C35	0.031 (2)	0.0306 (16)	0.057 (2)	0.0056 (14)	0.0157 (18)	0.0054 (15)
C36	0.0263 (19)	0.0348 (17)	0.066 (2)	0.0083 (14)	0.0033 (18)	0.0171 (17)
C37	0.043 (2)	0.048 (2)	0.044 (2)	0.0052 (17)	−0.0050 (18)	0.0132 (17)
C38	0.033 (2)	0.0420 (17)	0.0349 (18)	0.0069 (15)	0.0060 (16)	0.0083 (15)
F1	0.0451 (18)	0.146 (3)	0.145 (3)	−0.0291 (17)	−0.0005 (17)	0.103 (2)
F2	0.0429 (16)	0.0607 (15)	0.0696 (17)	0.0203 (12)	0.0255 (13)	−0.0026 (12)

Geometric parameters (Å, º)

Sn1—O1	2.0914 (18)	C13—H13	0.9500
Sn1—C1	2.104 (3)	C14—C15	1.385 (4)
Sn1—C5	2.110 (3)	C14—H14	0.9500
Sn1—O3	2.1134 (19)	C15—C16	1.361 (5)
Sn1—O4	2.513 (2)	C16—C17	1.385 (4)
Sn1—O2	2.650 (2)	C16—H16	0.9500
Cl1—C15	1.742 (3)	C17—H17	0.9500
Cl2—C30	1.751 (3)	C18—C19	1.384 (4)
O1—C9	1.299 (3)	C18—C23	1.385 (4)
O2—C9	1.241 (3)	C19—C20	1.390 (4)
O3—C24	1.298 (3)	C19—H19	0.9500
O4—C24	1.247 (3)	C20—C21	1.373 (5)
C1—C2	1.480 (5)	C20—H20	0.9500
C1—H1A	0.9900	C21—C22	1.363 (5)
C1—H1B	0.9900	C21—H21	0.9500
C2—C3	1.523 (5)	C22—C23	1.377 (5)
C2—H2A	0.9900	C22—H22	0.9500
C2—H2B	0.9900	C23—H23	0.9500
C3—C4	1.431 (5)	C24—C25	1.485 (4)
C3—H3A	0.9900	C25—C26	1.339 (4)
C3—H3B	0.9900	C25—C27	1.500 (4)
C4—H4A	0.9800	C26—C33	1.468 (4)
C4—H4B	0.9800	C26—H26	0.9500
C4—H4C	0.9800	C27—C28	1.382 (4)
C5—C6	1.537 (4)	C27—C32	1.385 (4)
C5—H5A	0.9900	C28—C29	1.383 (4)
C5—H5B	0.9900	C28—H28	0.9500
C6—C7	1.514 (5)	C29—C30	1.379 (4)
C6—H6A	0.9900	C29—H29	0.9500
C6—H6B	0.9900	C30—C31	1.370 (4)
C7—C8	1.517 (5)	C31—C32	1.386 (4)
C7—H7A	0.9900	C31—H31	0.9500
C7—H7B	0.9900	C32—H32	0.9500
C8—H8A	0.9800	C33—C38	1.388 (4)
C8—H8B	0.9800	C33—C34	1.397 (4)
C8—H8C	0.9800	C34—C35	1.369 (4)
C9—C10	1.498 (4)	C34—H34	0.9500
C10—C11	1.337 (4)	C35—C36	1.373 (5)
C10—C12	1.483 (4)	C35—H35	0.9500
C11—C18	1.481 (4)	C36—C37	1.375 (4)
C11—H11	0.9500	C36—H36	0.9500
C12—C13	1.390 (4)	C37—C38	1.378 (4)
C12—C17	1.397 (4)	C37—H37	0.9500
C13—C14	1.368 (4)	C38—H38	0.9500
O1—Sn1—C1	110.82 (11)	C14—C13—C12	121.4 (3)
O1—Sn1—C5	102.83 (10)	C14—C13—H13	119.3
C1—Sn1—C5	133.95 (12)	C12—C13—H13	119.3
O1—Sn1—O3	80.05 (7)	C13—C14—C15	119.3 (3)
C1—Sn1—O3	103.61 (10)	C13—C14—H14	120.4
C5—Sn1—O3	112.59 (11)	C15—C14—H14	120.4
O1—Sn1—O4	134.35 (7)	C16—C15—C14	121.1 (3)
C1—Sn1—O4	92.06 (10)	C16—C15—Cl1	119.7 (3)
C5—Sn1—O4	85.84 (10)	C14—C15—Cl1	119.2 (3)
O3—Sn1—O4	55.82 (7)	C15—C16—C17	119.6 (3)
O1—Sn1—O2	53.99 (7)	C15—C16—H16	120.2
C1—Sn1—O2	84.92 (10)	C17—C16—H16	120.2
C5—Sn1—O2	90.56 (10)	C16—C17—C12	120.7 (3)
O3—Sn1—O2	132.60 (7)	C16—C17—H17	119.6
O4—Sn1—O2	171.52 (6)	C12—C17—H17	119.6
C9—O1—Sn1	104.89 (16)	C19—C18—C23	118.3 (3)
C9—O2—Sn1	80.33 (17)	C19—C18—C11	122.9 (3)
C24—O3—Sn1	101.06 (16)	C23—C18—C11	118.7 (3)
C24—O4—Sn1	83.88 (17)	C18—C19—C20	120.7 (3)
C2—C1—Sn1	113.7 (2)	C18—C19—H19	119.6
C2—C1—H1A	108.8	C20—C19—H19	119.6
Sn1—C1—H1A	108.8	C21—C20—C19	121.2 (4)
C2—C1—H1B	108.8	C21—C20—H20	119.4
Sn1—C1—H1B	108.8	C19—C20—H20	119.4
H1A—C1—H1B	107.7	C22—C21—C20	117.1 (3)
C1—C2—C3	114.6 (3)	C22—C21—H21	121.5
C1—C2—H2A	108.6	C20—C21—H21	121.5
C3—C2—H2A	108.6	C21—C22—C23	123.5 (3)
C1—C2—H2B	108.6	C21—C22—H22	118.2
C3—C2—H2B	108.6	C23—C22—H22	118.2
H2A—C2—H2B	107.6	C22—C23—C18	119.2 (3)
C4—C3—C2	114.4 (4)	C22—C23—H23	120.4
C4—C3—H3A	108.7	C18—C23—H23	120.4
C2—C3—H3A	108.7	O4—C24—O3	119.2 (3)
C4—C3—H3B	108.7	O4—C24—C25	123.0 (3)
C2—C3—H3B	108.7	O3—C24—C25	117.8 (2)
H3A—C3—H3B	107.6	C26—C25—C24	117.2 (2)
C3—C4—H4A	109.5	C26—C25—C27	124.2 (3)
C3—C4—H4B	109.5	C24—C25—C27	118.4 (2)
H4A—C4—H4B	109.5	C25—C26—C33	128.9 (3)
C3—C4—H4C	109.5	C25—C26—H26	115.6
H4A—C4—H4C	109.5	C33—C26—H26	115.6
H4B—C4—H4C	109.5	C28—C27—C32	118.6 (3)
C6—C5—Sn1	115.2 (2)	C28—C27—C25	120.8 (3)
C6—C5—H5A	108.5	C32—C27—C25	120.6 (3)
Sn1—C5—H5A	108.5	C27—C28—C29	120.9 (3)
C6—C5—H5B	108.5	C27—C28—H28	119.6
Sn1—C5—H5B	108.5	C29—C28—H28	119.6
H5A—C5—H5B	107.5	C30—C29—C28	119.0 (3)
C7—C6—C5	114.4 (3)	C30—C29—H29	120.5
C7—C6—H6A	108.7	C28—C29—H29	120.5
C5—C6—H6A	108.7	C31—C30—C29	121.6 (3)
C7—C6—H6B	108.7	C31—C30—Cl2	119.2 (3)
C5—C6—H6B	108.7	C29—C30—Cl2	119.1 (3)
H6A—C6—H6B	107.6	C30—C31—C32	118.5 (3)
C6—C7—C8	114.3 (3)	C30—C31—H31	120.8
C6—C7—H7A	108.7	C32—C31—H31	120.8
C8—C7—H7A	108.7	C27—C32—C31	121.4 (3)
C6—C7—H7B	108.7	C27—C32—H32	119.3
C8—C7—H7B	108.7	C31—C32—H32	119.3
H7A—C7—H7B	107.6	C38—C33—C34	118.2 (3)
C7—C8—H8A	109.5	C38—C33—C26	117.1 (3)
C7—C8—H8B	109.5	C34—C33—C26	124.7 (3)
H8A—C8—H8B	109.5	C35—C34—C33	118.9 (3)
C7—C8—H8C	109.5	C35—C34—H34	120.6
H8A—C8—H8C	109.5	C33—C34—H34	120.6
H8B—C8—H8C	109.5	C34—C35—C36	123.6 (3)
O2—C9—O1	120.8 (3)	C34—C35—H35	118.2
O2—C9—C10	121.5 (3)	C36—C35—H35	118.2
O1—C9—C10	117.7 (2)	C35—C36—C37	117.1 (3)
C11—C10—C12	123.8 (2)	C35—C36—H36	121.4
C11—C10—C9	119.3 (3)	C37—C36—H36	121.4
C12—C10—C9	116.9 (2)	C36—C37—C38	121.1 (3)
C10—C11—C18	128.2 (3)	C36—C37—H37	119.4
C10—C11—H11	115.9	C38—C37—H37	119.4
C18—C11—H11	115.9	C37—C38—C33	121.0 (3)
C13—C12—C17	117.9 (3)	C37—C38—H38	119.5
C13—C12—C10	121.9 (3)	C33—C38—H38	119.5
C17—C12—C10	120.1 (3)
C1—Sn1—O1—C9	67.0 (2)	C13—C14—C15—Cl1	179.4 (2)
C5—Sn1—O1—C9	−81.0 (2)	C14—C15—C16—C17	1.1 (5)
O3—Sn1—O1—C9	167.90 (18)	Cl1—C15—C16—C17	−179.8 (2)
O4—Sn1—O1—C9	−177.80 (15)	C15—C16—C17—C12	0.6 (5)
O2—Sn1—O1—C9	0.19 (16)	C13—C12—C17—C16	−1.8 (4)
O1—Sn1—O2—C9	−0.19 (16)	C10—C12—C17—C16	176.4 (3)
C1—Sn1—O2—C9	−120.58 (18)	C10—C11—C18—C19	−34.1 (5)
C5—Sn1—O2—C9	105.32 (18)	C10—C11—C18—C23	150.4 (3)
O3—Sn1—O2—C9	−16.74 (19)	C23—C18—C19—C20	−1.0 (5)
O1—Sn1—O3—C24	166.40 (17)	C11—C18—C19—C20	−176.5 (3)
C1—Sn1—O3—C24	−84.41 (19)	C18—C19—C20—C21	−0.5 (5)
C5—Sn1—O3—C24	66.54 (19)	C19—C20—C21—C22	0.8 (5)
O4—Sn1—O3—C24	−1.28 (15)	C20—C21—C22—C23	0.5 (6)
O2—Sn1—O3—C24	179.92 (15)	C21—C22—C23—C18	−2.0 (6)
O1—Sn1—O4—C24	−15.8 (2)	C19—C18—C23—C22	2.2 (5)
C1—Sn1—O4—C24	106.40 (18)	C11—C18—C23—C22	177.9 (3)
C5—Sn1—O4—C24	−119.68 (18)	Sn1—O4—C24—O3	−2.0 (2)
O3—Sn1—O4—C24	1.32 (16)	Sn1—O4—C24—C25	176.5 (3)
O1—Sn1—C1—C2	44.9 (3)	Sn1—O3—C24—O4	2.5 (3)
C5—Sn1—C1—C2	179.1 (3)	Sn1—O3—C24—C25	−176.1 (2)
O3—Sn1—C1—C2	−39.4 (3)	O4—C24—C25—C26	−12.3 (4)
O4—Sn1—C1—C2	−94.7 (3)	O3—C24—C25—C26	166.2 (2)
O2—Sn1—C1—C2	93.2 (3)	O4—C24—C25—C27	173.2 (3)
Sn1—C1—C2—C3	178.8 (3)	O3—C24—C25—C27	−8.3 (4)
C1—C2—C3—C4	−178.7 (4)	C24—C25—C26—C33	−176.3 (3)
O1—Sn1—C5—C6	174.2 (2)	C27—C25—C26—C33	−2.1 (5)
C1—Sn1—C5—C6	37.7 (3)	C26—C25—C27—C28	116.4 (3)
O3—Sn1—C5—C6	−101.3 (2)	C24—C25—C27—C28	−69.5 (3)
O4—Sn1—C5—C6	−51.2 (2)	C26—C25—C27—C32	−62.6 (4)
O2—Sn1—C5—C6	121.2 (2)	C24—C25—C27—C32	111.5 (3)
Sn1—C5—C6—C7	−48.6 (4)	C32—C27—C28—C29	0.7 (5)
C5—C6—C7—C8	−57.1 (4)	C25—C27—C28—C29	−178.3 (3)
Sn1—O2—C9—O1	0.3 (2)	C27—C28—C29—C30	−1.0 (5)
Sn1—O2—C9—C10	179.2 (3)	C28—C29—C30—C31	0.4 (5)
Sn1—O1—C9—O2	−0.4 (3)	C28—C29—C30—Cl2	−178.5 (2)
Sn1—O1—C9—C10	−179.31 (19)	C29—C30—C31—C32	0.6 (5)
O2—C9—C10—C11	−179.9 (3)	Cl2—C30—C31—C32	179.4 (2)
O1—C9—C10—C11	−1.0 (4)	C28—C27—C32—C31	0.3 (4)
O2—C9—C10—C12	0.1 (4)	C25—C27—C32—C31	179.3 (3)
O1—C9—C10—C12	179.0 (2)	C30—C31—C32—C27	−1.0 (4)
C12—C10—C11—C18	−4.8 (5)	C25—C26—C33—C38	147.1 (3)
C9—C10—C11—C18	175.2 (3)	C25—C26—C33—C34	−33.4 (5)
C11—C10—C12—C13	112.3 (3)	C38—C33—C34—C35	−1.3 (4)
C9—C10—C12—C13	−67.7 (4)	C26—C33—C34—C35	179.2 (3)
C11—C10—C12—C17	−65.8 (4)	C33—C34—C35—C36	−1.4 (4)
C9—C10—C12—C17	114.2 (3)	C34—C35—C36—C37	1.8 (5)
C17—C12—C13—C14	1.4 (4)	C35—C36—C37—C38	0.6 (5)
C10—C12—C13—C14	−176.8 (3)	C36—C37—C38—C33	−3.4 (5)
C12—C13—C14—C15	0.2 (4)	C34—C33—C38—C37	3.7 (4)
C13—C14—C15—C16	−1.4 (4)	C26—C33—C38—C37	−176.8 (3)