Bis(cyclo­pentenylacetato)tetra­methyl­distannoxane dimer

The crystal structure of the title compound, tetra-μ₂-(cyclopent-2-en­yl)acetato-1:2κ²O:O′;1:3κ²O:O′;2:4κ²O:O′;3:4κ²O:O′-octa­methyl-1κ²C,2κ²C,3κ²C,4κ²C-di-μ₃-oxo-1:2:3κ³O;2:3:4κ³O-tetra­tin(IV), [Sn₄(CH₃)₈(C₇H₉O₂)₄O₂], is composed of discrete centrosymmetric dimers lying about inversion centres. The cyclo­pentenylacetate ligand shows different modes of coordination with Sn, as a result of which the central Sn₂O₂ core is fused with two four-membered (Sn₂O₂) and two six-membered (Sn₂O₃C) rings. The endocyclic Sn atoms are six-coordinate in a skew-trapezoidal bipyramidal environment. The exocyclic Sn atoms are five-coordinate and show distorted trigonal–bipyramidal geometry. The Sn—C distances lie in a very narrow range [2.095 (4)–2.113 (4) Å], while the Sn—O distances range between 2.030 (3) and 2.280 (3) Å for strong bonds and a value of 2.654 (3) Å for the relatively weak Sn—O bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.084
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C18'

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C22'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C12    -   C13    ...       1.43 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  10 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
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: 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).

tetra-µ₂-(cyclopent-2-enyl)acetato- 1:2κ²O:O';1:3κ²O:O';2:4κ²O:O';3:4κ²O:O'-octamethyl- 1κ²C,2κ²C,3κ²C,4κ²C-di-µ₃-oxo-1:2:3κ³O;2:3:4κ³O-tetratin

Crystal data

[Sn4(CH3)8(C7H9O2)4O2]	Z = 1
Mr = 1127.60	F(000) = 556
Triclinic, P1	Dx = 1.714 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.572 (2) Å	Cell parameters from 9218 reflections
b = 11.154 (3) Å	θ = 3.5–27.5°
c = 13.387 (4) Å	µ = 2.31 mm^−1
α = 84.584 (9)°	T = 173 K
β = 76.014 (9)°	Prism, colourless
γ = 89.404 (15)°	0.10 × 0.09 × 0.08 mm
V = 1092.1 (5) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	4974 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.802, Tmax = 0.837	k = −14→14
9216 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0404P)^2] where P = (Fo^2 + 2Fc^2)/3
4974 reflections	(Δ/σ)max = 0.003
237 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.79 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.01104 (3)	0.44836 (2)	0.61638 (2)	0.02754 (10)
Sn2	0.00626 (3)	0.21358 (2)	0.44736 (2)	0.02822 (10)
C1	0.2889 (5)	0.4199 (4)	0.6087 (4)	0.0487 (12)
H1A	0.3565	0.4959	0.5853	0.073*
H1B	0.3353	0.3602	0.5599	0.073*
H1C	0.3042	0.3903	0.6773	0.073*
C3	−0.2578 (5)	0.4013 (4)	0.6989 (3)	0.0424 (11)
H3A	−0.3258	0.4745	0.7171	0.064*
H3B	−0.2550	0.3501	0.7621	0.064*
H3C	−0.3173	0.3575	0.6557	0.064*
C5	0.2830 (5)	0.1724 (4)	0.4014 (4)	0.0445 (12)
H5A	0.3547	0.2472	0.3802	0.067*
H5B	0.3028	0.1228	0.3432	0.067*
H5C	0.3209	0.1281	0.4593	0.067*
C7	−0.2727 (5)	0.1707 (4)	0.4812 (4)	0.0443 (12)
H7A	−0.3434	0.2448	0.4882	0.066*
H7B	−0.3061	0.1183	0.5460	0.066*
H7C	−0.2987	0.1289	0.4250	0.066*
O1	0.0050 (3)	0.3935 (2)	0.46921 (19)	0.0291 (6)
O2	−0.0210 (5)	0.4483 (3)	0.2460 (2)	0.0595 (9)
O3	0.0058 (5)	0.2544 (3)	0.2821 (2)	0.0595 (9)
C9	−0.0161 (5)	0.3426 (4)	0.2229 (3)	0.0313 (9)
C10	−0.0391 (5)	0.3232 (4)	0.1173 (3)	0.0367 (10)
H10A	−0.0496	0.2357	0.1123	0.044*
H10B	0.0709	0.3538	0.0649	0.044*
C11	−0.2043 (5)	0.3848 (4)	0.0926 (3)	0.0411 (11)
H11	−0.1925	0.4735	0.0957	0.049*
C12	−0.3831 (6)	0.3390 (6)	0.1665 (4)	0.0620 (15)
H12A	−0.3624	0.2629	0.2061	0.074*
H12B	−0.4300	0.3991	0.2161	0.074*
C13	−0.5127 (7)	0.3194 (6)	0.1072 (4)	0.0716 (17)
H13A	−0.6084	0.3813	0.1178	0.086*
H13B	−0.5711	0.2391	0.1285	0.086*
C14	−0.4113 (7)	0.3275 (6)	−0.0025 (4)	0.0740 (18)
H14	−0.4617	0.3109	−0.0582	0.089*
C15	−0.2345 (6)	0.3621 (5)	−0.0124 (3)	0.0535 (13)
H15	−0.1439	0.3707	−0.0757	0.064*
O4	0.0134 (4)	0.2107 (3)	0.6137 (2)	0.0362 (7)
O5	−0.0040 (4)	0.0159 (3)	0.6127 (3)	0.0586 (9)
C16	0.0052 (5)	0.1032 (4)	0.6598 (3)	0.0345 (10)
C17	0.0089 (7)	0.0896 (6)	0.7710 (4)	0.0719 (18)
H17A	−0.0958	0.1333	0.8102	0.086*	0.706 (11)
H17B	−0.0085	0.0032	0.7964	0.086*	0.706 (11)
C18	0.1690 (9)	0.1313 (7)	0.7934 (5)	0.047 (2)	0.706 (11)
H18	0.1858	0.2193	0.7704	0.056*	0.706 (11)
C19	0.3456 (7)	0.0633 (7)	0.7441 (4)	0.085 (2)
H19A	0.3141	−0.0173	0.7279	0.102*	0.706 (11)
H19B	0.4126	0.1091	0.6793	0.102*	0.706 (11)
C20	0.4567 (8)	0.0521 (7)	0.8190 (6)	0.100 (2)
H20A	0.5157	−0.0275	0.8192	0.120*
H20B	0.5523	0.1157	0.8027	0.120*
C21	0.3329 (9)	0.0652 (6)	0.9182 (5)	0.085 (2)
H21	0.3610	0.0448	0.9831	0.102*	0.706 (11)
C22	0.170 (3)	0.1107 (14)	0.9062 (13)	0.082 (5)	0.706 (11)
H22	0.0707	0.1271	0.9616	0.098*	0.706 (11)
H17C	−0.0124	0.1710	0.7949	0.086*	0.294 (11)
H17D	−0.1002	0.0406	0.8070	0.086*	0.294 (11)
C18'	0.150 (2)	0.0425 (18)	0.8111 (12)	0.047 (2)	0.294 (11)
H18'	0.1314	−0.0466	0.8149	0.056*	0.294 (11)
H19C	0.3782	0.0020	0.6941	0.102*	0.294 (11)
H19D	0.3597	0.1444	0.7058	0.102*	0.294 (11)
H21'	0.3702	0.0753	0.9798	0.102*	0.294 (11)
C22'	0.185 (7)	0.062 (4)	0.913 (4)	0.082 (5)	0.294 (11)
H22'	0.0878	0.0708	0.9718	0.098*	0.294 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03292 (17)	0.02655 (17)	0.02504 (16)	−0.00020 (12)	−0.01119 (12)	−0.00104 (12)
Sn2	0.03069 (16)	0.02551 (17)	0.02923 (17)	0.00312 (11)	−0.00784 (12)	−0.00516 (12)
C1	0.037 (2)	0.045 (3)	0.068 (4)	−0.001 (2)	−0.024 (2)	0.004 (3)
C3	0.041 (2)	0.041 (3)	0.039 (3)	0.000 (2)	0.002 (2)	−0.005 (2)
C5	0.034 (2)	0.040 (3)	0.052 (3)	0.0042 (19)	0.005 (2)	−0.004 (2)
C7	0.033 (2)	0.036 (3)	0.069 (3)	0.0009 (19)	−0.018 (2)	−0.014 (2)
O1	0.0400 (15)	0.0236 (15)	0.0254 (15)	0.0013 (12)	−0.0100 (12)	−0.0059 (12)
O2	0.112 (3)	0.042 (2)	0.0336 (19)	−0.0091 (19)	−0.0341 (19)	−0.0042 (16)
O3	0.108 (3)	0.044 (2)	0.0307 (19)	0.0124 (19)	−0.0258 (19)	−0.0055 (16)
C9	0.026 (2)	0.047 (3)	0.020 (2)	−0.0023 (18)	−0.0037 (16)	−0.003 (2)
C10	0.039 (2)	0.043 (3)	0.030 (2)	0.0016 (19)	−0.0099 (19)	−0.011 (2)
C11	0.045 (3)	0.055 (3)	0.024 (2)	0.000 (2)	−0.0094 (19)	−0.007 (2)
C12	0.041 (3)	0.103 (5)	0.040 (3)	0.000 (3)	−0.003 (2)	−0.014 (3)
C13	0.060 (3)	0.102 (5)	0.055 (4)	−0.018 (3)	−0.017 (3)	−0.005 (3)
C14	0.073 (4)	0.115 (5)	0.039 (3)	−0.026 (3)	−0.021 (3)	−0.008 (3)
C15	0.050 (3)	0.087 (4)	0.027 (2)	−0.006 (3)	−0.016 (2)	−0.005 (3)
O4	0.0435 (16)	0.0355 (18)	0.0312 (16)	0.0019 (13)	−0.0127 (13)	−0.0028 (14)
O5	0.068 (2)	0.032 (2)	0.075 (3)	0.0029 (16)	−0.0166 (19)	−0.0021 (18)
C16	0.028 (2)	0.037 (3)	0.035 (2)	0.0066 (19)	−0.0020 (18)	0.004 (2)
C17	0.057 (3)	0.123 (6)	0.030 (3)	0.027 (3)	−0.010 (2)	0.014 (3)
C18	0.063 (4)	0.047 (4)	0.035 (4)	−0.004 (4)	−0.021 (3)	0.001 (3)
C19	0.049 (3)	0.157 (7)	0.057 (4)	0.023 (4)	−0.019 (3)	−0.033 (4)
C20	0.068 (4)	0.141 (7)	0.103 (6)	0.021 (4)	−0.036 (4)	−0.033 (5)
C21	0.095 (5)	0.113 (6)	0.064 (4)	0.026 (4)	−0.052 (4)	−0.014 (4)
C22	0.094 (6)	0.124 (15)	0.039 (4)	0.054 (9)	−0.034 (4)	−0.026 (8)
C17'	0.057 (3)	0.123 (6)	0.030 (3)	0.027 (3)	−0.010 (2)	0.014 (3)
C18'	0.063 (4)	0.047 (4)	0.035 (4)	−0.004 (4)	−0.021 (3)	0.001 (3)
C19'	0.049 (3)	0.157 (7)	0.057 (4)	0.023 (4)	−0.019 (3)	−0.033 (4)
C20'	0.068 (4)	0.141 (7)	0.103 (6)	0.021 (4)	−0.036 (4)	−0.033 (5)
C21'	0.095 (5)	0.113 (6)	0.064 (4)	0.026 (4)	−0.052 (4)	−0.014 (4)
C22'	0.094 (6)	0.124 (15)	0.039 (4)	0.054 (9)	−0.034 (4)	−0.026 (8)

Geometric parameters (Å, º)

Sn1—O1^i	2.030 (3)	C11—C12	1.531 (6)
Sn1—C1	2.104 (4)	C11—H11	1.0000
Sn1—C3	2.113 (4)	C12—C13	1.433 (6)
Sn1—O1	2.128 (3)	C12—H12A	0.9900
Sn1—O2^i	2.280 (3)	C12—H12B	0.9900
Sn1—O4	2.654 (3)	C13—C14	1.478 (7)
Sn2—O1	2.054 (3)	C13—H13A	0.9900
Sn2—C5	2.095 (4)	C13—H13B	0.9900
Sn2—C7	2.101 (4)	C14—C15	1.369 (6)
Sn2—O3	2.218 (3)	C14—H14	0.9500
Sn2—O4	2.238 (3)	C15—H15	0.9500
C1—H1A	0.9800	O4—C16	1.291 (5)
C1—H1B	0.9800	O5—C16	1.220 (5)
C1—H1C	0.9800	C16—C17	1.489 (6)
C3—H3A	0.9800	C17—C18	1.411 (8)
C3—H3B	0.9800	C17—H17A	0.9900
C3—H3C	0.9800	C17—H17B	0.9900
C5—H5A	0.9800	C18—C22	1.508 (17)
C5—H5B	0.9800	C18—C19	1.564 (8)
C5—H5C	0.9800	C18—H18	1.0000
C7—H7A	0.9800	C19—C20	1.453 (8)
C7—H7B	0.9800	C19—H19A	0.9900
C7—H7C	0.9800	C19—H19B	0.9900
O1—Sn1^i	2.030 (3)	C20—C21	1.447 (8)
O2—C9	1.245 (5)	C20—H20A	0.9900
O2—Sn1^i	2.280 (3)	C20—H20B	0.9900
O3—C9	1.239 (5)	C21—C22	1.368 (16)
C9—C10	1.502 (6)	C21—H21	0.9500
C10—C11	1.511 (6)	C22—H22	0.9500
C10—H10A	0.9900	C18'—C22'	1.49 (5)
C10—H10B	0.9900	C18'—H18'	1.0000
C11—C15	1.522 (6)	C22'—H22'	0.9500
O1^i—Sn1—C1	106.63 (15)	C10—C11—C15	114.1 (4)
O1^i—Sn1—C3	106.36 (14)	C10—C11—C12	112.9 (4)
C1—Sn1—C3	145.21 (19)	C15—C11—C12	102.3 (3)
O1^i—Sn1—O1	76.74 (11)	C10—C11—H11	109.1
C1—Sn1—O1	98.32 (15)	C15—C11—H11	109.1
C3—Sn1—O1	99.69 (14)	C12—C11—H11	109.1
O1^i—Sn1—O2^i	89.75 (11)	C13—C12—C11	108.8 (4)
C1—Sn1—O2^i	84.06 (17)	C13—C12—H12A	109.9
C3—Sn1—O2^i	85.31 (15)	C11—C12—H12A	109.9
O1—Sn1—O2^i	166.42 (11)	C13—C12—H12B	109.9
O1^i—Sn1—O4	143.97 (10)	C11—C12—H12B	109.9
C1—Sn1—O4	81.41 (14)	H12A—C12—H12B	108.3
C3—Sn1—O4	78.49 (13)	C12—C13—C14	106.8 (4)
O1—Sn1—O4	67.29 (9)	C12—C13—H13A	110.4
O2^i—Sn1—O4	126.25 (10)	C14—C13—H13A	110.4
O1—Sn2—C5	104.20 (14)	C12—C13—H13B	110.4
O1—Sn2—C7	102.44 (14)	C14—C13—H13B	110.4
C5—Sn2—C7	153.34 (17)	H13A—C13—H13B	108.6
O1—Sn2—O3	91.70 (11)	C15—C14—C13	110.5 (4)
C5—Sn2—O3	88.71 (16)	C15—C14—H14	124.8
C7—Sn2—O3	89.67 (17)	C13—C14—H14	124.8
O1—Sn2—O4	77.33 (10)	C14—C15—C11	110.1 (4)
C5—Sn2—O4	92.66 (15)	C14—C15—H15	124.9
C7—Sn2—O4	93.96 (15)	C11—C15—H15	124.9
O3—Sn2—O4	168.95 (12)	C16—O4—Sn2	113.0 (3)
Sn1—C1—H1A	109.5	C16—O4—Sn1	151.5 (3)
Sn1—C1—H1B	109.5	Sn2—O4—Sn1	95.26 (10)
H1A—C1—H1B	109.5	O5—C16—O4	120.4 (4)
Sn1—C1—H1C	109.5	O5—C16—C17	121.5 (4)
H1A—C1—H1C	109.5	O4—C16—C17	118.1 (4)
H1B—C1—H1C	109.5	C18—C17—C16	115.5 (5)
Sn1—C3—H3A	109.5	C18—C17—H17A	108.4
Sn1—C3—H3B	109.5	C16—C17—H17A	108.4
H3A—C3—H3B	109.5	C18—C17—H17B	108.4
Sn1—C3—H3C	109.5	C16—C17—H17B	108.4
H3A—C3—H3C	109.5	H17A—C17—H17B	107.5
H3B—C3—H3C	109.5	C17—C18—C22	113.7 (10)
Sn2—C5—H5A	109.5	C17—C18—C19	114.7 (6)
Sn2—C5—H5B	109.5	C22—C18—C19	100.3 (7)
H5A—C5—H5B	109.5	C17—C18—H18	109.3
Sn2—C5—H5C	109.5	C22—C18—H18	109.3
H5A—C5—H5C	109.5	C19—C18—H18	109.3
H5B—C5—H5C	109.5	C20—C19—C18	107.3 (5)
Sn2—C7—H7A	109.5	C20—C19—H19A	110.3
Sn2—C7—H7B	109.5	C18—C19—H19A	110.3
H7A—C7—H7B	109.5	C20—C19—H19B	110.3
Sn2—C7—H7C	109.5	C18—C19—H19B	110.3
H7A—C7—H7C	109.5	H19A—C19—H19B	108.5
H7B—C7—H7C	109.5	C21—C20—C19	105.7 (5)
Sn1^i—O1—Sn2	136.57 (13)	C21—C20—H20A	110.6
Sn1^i—O1—Sn1	103.26 (11)	C19—C20—H20A	110.6
Sn2—O1—Sn1	120.12 (12)	C21—C20—H20B	110.6
C9—O2—Sn1^i	139.4 (3)	C19—C20—H20B	110.6
C9—O3—Sn2	138.3 (3)	H20A—C20—H20B	108.7
O3—C9—O2	123.6 (4)	C22—C21—C20	111.0 (9)
O3—C9—C10	119.3 (4)	C22—C21—H21	124.5
O2—C9—C10	117.1 (4)	C20—C21—H21	124.5
C9—C10—C11	113.2 (3)	C21—C22—C18	111.1 (12)
C9—C10—H10A	108.9	C21—C22—H22	124.5
C11—C10—H10A	108.9	C18—C22—H22	124.5
C9—C10—H10B	108.9	C22'—C18'—H18'	103.8
C11—C10—H10B	108.9	C18'—C22'—H22'	121.3
H10A—C10—H10B	107.7
C5—Sn2—O1—Sn1^i	93.6 (2)	C11—C12—C13—C14	11.3 (7)
C7—Sn2—O1—Sn1^i	−85.5 (2)	C12—C13—C14—C15	−5.9 (8)
O3—Sn2—O1—Sn1^i	4.5 (2)	C13—C14—C15—C11	−2.0 (7)
O4—Sn2—O1—Sn1^i	−176.9 (2)	C10—C11—C15—C14	130.7 (5)
O5—Sn2—O1—Sn1^i	−173.47 (14)	C12—C11—C15—C14	8.4 (6)
O2—Sn2—O1—Sn1^i	0.98 (14)	O1—Sn2—O4—C16	176.0 (3)
C5—Sn2—O1—Sn1	−89.47 (18)	C5—Sn2—O4—C16	−80.1 (3)
C7—Sn2—O1—Sn1	91.39 (18)	C7—Sn2—O4—C16	74.1 (3)
O3—Sn2—O1—Sn1	−178.57 (14)	O3—Sn2—O4—C16	−177.0 (5)
O4—Sn2—O1—Sn1	0.08 (11)	O5—Sn2—O4—C16	−0.2 (2)
O5—Sn2—O1—Sn1	3.46 (18)	O1—Sn2—O4—Sn1	−0.06 (7)
O2—Sn2—O1—Sn1	177.92 (16)	C5—Sn2—O4—Sn1	103.91 (14)
O1^i—Sn1—O1—Sn1^i	0.0	C7—Sn2—O4—Sn1	−101.93 (14)
C1—Sn1—O1—Sn1^i	−105.23 (15)	O3—Sn2—O4—Sn1	7.0 (6)
C3—Sn1—O1—Sn1^i	104.67 (15)	O1^i—Sn1—O4—C16	−168.5 (5)
O2^i—Sn1—O1—Sn1^i	−6.0 (5)	C1—Sn1—O4—C16	84.9 (5)
O4—Sn1—O1—Sn1^i	177.76 (13)	C3—Sn1—O4—C16	−66.5 (5)
O1^i—Sn1—O1—Sn2	−177.84 (19)	O1—Sn1—O4—C16	−172.2 (5)
C1—Sn1—O1—Sn2	76.94 (17)	O2^i—Sn1—O4—C16	8.9 (5)
C3—Sn1—O1—Sn2	−73.16 (17)	Sn1^i—Sn1—O4—C16	−170.8 (5)
O2^i—Sn1—O1—Sn2	176.1 (4)	O1^i—Sn1—O4—Sn2	3.8 (2)
O4—Sn1—O1—Sn2	−0.07 (10)	C1—Sn1—O4—Sn2	−102.76 (16)
Sn1^i—Sn1—O1—Sn2	−177.84 (19)	C3—Sn1—O4—Sn2	105.80 (15)
O1—Sn2—O3—C9	−10.9 (5)	O1—Sn1—O4—Sn2	0.06 (8)
C5—Sn2—O3—C9	−115.1 (5)	O2^i—Sn1—O4—Sn2	−178.84 (11)
C7—Sn2—O3—C9	91.5 (5)	Sn1^i—Sn1—O4—Sn2	1.46 (9)
O4—Sn2—O3—C9	−17.8 (10)	Sn2—O4—C16—O5	0.5 (5)
O5—Sn2—O3—C9	166.2 (4)	Sn1—O4—C16—O5	172.1 (3)
O2—Sn2—O3—C9	−5.7 (4)	Sn2—O4—C16—C17	−180.0 (3)
Sn2—O3—C9—O2	11.3 (7)	Sn1—O4—C16—C17	−8.3 (7)
Sn2—O3—C9—C10	−168.4 (3)	O5—C16—C17—C18	116.8 (6)
Sn1^i—O2—C9—O3	−3.2 (7)	O4—C16—C17—C18	−62.7 (7)
Sn2—O2—C9—O3	−5.2 (3)	C16—C17—C18—C22	−177.4 (7)
Sn1^i—O2—C9—C10	176.6 (3)	C16—C17—C18—C19	−62.9 (8)
Sn2—O2—C9—C10	174.6 (4)	C17—C18—C19—C20	−142.2 (6)
O3—C9—C10—C11	128.8 (4)	C22—C18—C19—C20	−20.0 (11)
O2—C9—C10—C11	−51.0 (5)	C18—C19—C20—C21	21.4 (8)
C9—C10—C11—C15	−177.6 (4)	C19—C20—C21—C22	−14.3 (12)
C9—C10—C11—C12	−61.4 (5)	C20—C21—C22—C18	0.9 (16)
C10—C11—C12—C13	−135.1 (5)	C17—C18—C22—C21	134.5 (12)
C15—C11—C12—C13	−12.0 (6)	C19—C18—C22—C21	11.7 (15)

Symmetry code: (i) −x, −y+1, −z+1.