Dichlorido{μ₃-6,6′-dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}octa­methyldi-μ₃-oxido-tetra­tin(IV)

Abstract

In the title tetra­nuclear tin(IV) complex, [Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂], there are three completely different tin-atom coordinations. One metal atom (site symmetry 2) adopts a distorted penta­gonal-bipyramidal SnC₂N₂O₃ coordination arising from the N,N′,O,O′-tetra­dentate deprotonated Schiff base, two methyl groups in the axial sites and a μ₃-O atom that also bonds to two further Sn atoms. Two symmetry-equivalent Sn atoms adopt very distorted SnC₂O₄ arrangements that could be described as penta­gonal-bipyramidal with one equatorial vertex missing and the C atoms in the axial site. The final Sn atom (site symmetry 2) adopts an SnC₂Cl₂O trigonal-bipyramidal arrangement, with Cl atoms in the axial sites. As well as the two Sn atoms, one O atom lies on a twofold rotation rotation axis, and another is disordered about the axis. The terminal eth­oxy group is disordered over two sets of sites with equal occupancy.

Related literature

For other organotin derivatives of 6,6′-dialk­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenol, see: Cunningham et al. (2004 ▶). For the crystal structure of 6,6′-dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenol, see: Ber­mejo et al. (2007 ▶).

Experimental

Crystal data

• [Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂]

• M _r = 1052.33

• Tetragonal,

• a = 9.8723 (1) Å

• c = 38.0217 (5) Å

• V = 3705.68 (6) ų

• Z = 4

• Mo Kα radiation

• μ = 2.85 mm⁻¹

• T = 100 K

• 0.20 × 0.18 × 0.15 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.863, T _max = 1.000 (expected range = 0.563–0.652)

• 68779 measured reflections

• 4259 independent reflections

• 4089 reflections with I > 2σ(I)

• R _int = 0.029

Refinement

• R[F ² > 2σ(F ²)] = 0.027

• wR(F ²) = 0.072

• S = 1.07

• 4259 reflections

• 198 parameters

• 10 restraints

• H-atom parameters constrained

• Δρ_max = 0.42 e Å⁻³

• Δρ_min = −0.69 e Å⁻³

• Absolute structure: Flack (1983 ▶), 1694 Friedel pairs

• Flack parameter: 0.00 (4)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

Sn1—O3	2.072 (4)
Sn1—C1	2.112 (5)
Sn1—O1	2.410 (3)
Sn1—N1	2.426 (4)
Sn2—O1	2.463 (3)
Sn2—O2	2.791 (4)
Sn2—O3	2.006 (2)
Sn2—C2	2.091 (5)
Sn2—C3	2.100 (5)
Sn2—O4	2.125 (17)
Sn3—O4	1.964 (5)
Sn3—C4	2.114 (5)
Sn3—Cl1	2.5829 (15)

C1i—Sn1—C1	173.9 (3)
C2—Sn2—C3	147.8 (2)
C4—Sn3—C4i	132.6 (3)

Symmetry code: (i) .

supplementary crystallographic information

Experimental

One mmol (0.36 g) of the Schiff base was synthesized in toluene according to a literature procedure (Bermejo et al., 2007) from 3-ethoxysalicylaldehyde and ethylenediamine. To the solution was added an excess of triethylamine (0.5 ml). A toluene solution of dimethyltin dichloride (0.20 g, 1 mmol) was added and the mixture heated. Yellow blocks of (I) were isolated from the cool filtered solution.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times U_eq(C).

The ethoxy group in disordered over two positions in respect of the carbon atoms. The occupancy could not be refined, and was arbitrarily regarded as 0.5 each. The C–O distances were restrained to 1.45±0.01 Å and the C–C distances to 1.50±0.01 Å. The displacement factors of the primed atoms were set of those of the umprimed ones, and the anisotropic temperature factors were restrained to be nearly isotropic by tight restraints.

Figures

Fig. 1.

View of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the ethyl groups are not shown. Unlabelled atoms are generated by the symmetry operation (y, x, –z).

Crystal data

[Sn4(CH3)8(C20H22N2O4)Cl2O2]	Dx = 1.886 Mg m−3
Mr = 1052.33	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 9779 reflections
Hall symbol: P4 nw 2abw	θ = 2.1–26.5°
a = 9.8723 (1) Å	µ = 2.85 mm−1
c = 38.0217 (5) Å	T = 100 K
V = 3705.68 (6) Å3	Block, yellow
Z = 4	0.20 × 0.18 × 0.15 mm
F(000) = 2040

Data collection

Bruker SMART APEX diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	4089 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.863, Tmax = 1.000	k = −12→12
68779 measured reflections	l = −49→48

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0361P)2 + 5.6973P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4259 reflections	Δρmax = 0.42 e Å−3
198 parameters	Δρmin = −0.69 e Å−3
10 restraints	Absolute structure: Flack (1983), 1694 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (4)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.17065 (3)	0.17065 (3)	0.0000	0.05087 (13)
Sn2	0.33507 (3)	0.46713 (3)	0.035901 (8)	0.04062 (9)
Sn3	0.64067 (3)	0.64067 (3)	0.0000	0.03517 (10)
Cl1	0.51581 (18)	0.74108 (17)	0.05370 (4)	0.0693 (4)
O1	0.1449 (3)	0.3159 (3)	0.05051 (8)	0.0476 (8)
O2	0.1753 (4)	0.5180 (4)	0.09499 (11)	0.0663 (11)
O3	0.3190 (3)	0.3190 (3)	0.0000	0.0383 (9)
O4	0.5075 (16)	0.4933 (15)	0.0032 (5)	0.027 (2)	0.50
N1	−0.0212 (4)	0.0806 (4)	0.03231 (12)	0.0486 (10)
C1	0.2924 (5)	0.0328 (5)	0.02834 (14)	0.0505 (12)
H1A	0.3582	−0.0091	0.0124	0.076*
H1B	0.2350	−0.0376	0.0387	0.076*
H1C	0.3406	0.0811	0.0471	0.076*
C2	0.4546 (6)	0.3956 (6)	0.07732 (13)	0.0564 (13)
H2A	0.5248	0.3352	0.0680	0.085*
H2B	0.3977	0.3457	0.0940	0.085*
H2C	0.4974	0.4723	0.0893	0.085*
C3	0.2074 (5)	0.6200 (5)	0.01652 (15)	0.0509 (12)
H3A	0.2616	0.7000	0.0105	0.076*
H3B	0.1406	0.6441	0.0345	0.076*
H3C	0.1606	0.5873	−0.0045	0.076*
C4	0.8115 (6)	0.5917 (6)	0.03104 (17)	0.0613 (15)
H4A	0.8022	0.4991	0.0400	0.092*
H4B	0.8177	0.6549	0.0508	0.092*
H4C	0.8936	0.5983	0.0167	0.092*
C5	−0.0612 (6)	−0.0545 (6)	0.01965 (15)	0.0645 (16)
H5A	−0.1547	−0.0747	0.0275	0.077*
H5B	−0.0002	−0.1237	0.0299	0.077*
C6	−0.0948 (5)	0.1346 (5)	0.05572 (13)	0.0465 (11)
H6	−0.1747	0.0862	0.0617	0.056*
C7	−0.0736 (5)	0.2594 (5)	0.07448 (12)	0.0418 (10)
C8	−0.1778 (5)	0.2942 (6)	0.09830 (14)	0.0509 (12)
H8	−0.2577	0.2406	0.0992	0.061*
C9	−0.1654 (6)	0.4048 (6)	0.12023 (14)	0.0575 (14)
H9	−0.2372	0.4286	0.1357	0.069*
C10	−0.0475 (6)	0.4810 (6)	0.11964 (12)	0.0551 (14)
H10	−0.0369	0.5548	0.1354	0.066*
C11	0.0529 (5)	0.4504 (5)	0.09661 (12)	0.0452 (11)
C12	0.0447 (5)	0.3385 (5)	0.07272 (11)	0.0399 (9)
C13	0.2125 (16)	0.6125 (10)	0.1229 (3)	0.061 (2)*	0.50
H13A	0.3109	0.6070	0.1276	0.073*	0.50
H13B	0.1633	0.5900	0.1448	0.073*	0.50
C14	0.1759 (17)	0.7520 (13)	0.1109 (4)	0.080 (3)*	0.50
H14A	0.0782	0.7565	0.1065	0.120*	0.50
H14B	0.2252	0.7734	0.0893	0.120*	0.50
H14C	0.2001	0.8174	0.1293	0.120*	0.50
C13'	0.1933 (14)	0.6412 (9)	0.1157 (3)	0.061 (2)*	0.50
H13C	0.2913	0.6628	0.1162	0.073*	0.50
H13D	0.1656	0.6214	0.1402	0.073*	0.50
C14'	0.1189 (16)	0.7656 (14)	0.1039 (5)	0.080 (3)*	0.50
H14D	0.1808	0.8246	0.0908	0.120*	0.50
H14E	0.0841	0.8141	0.1245	0.120*	0.50
H14F	0.0432	0.7393	0.0887	0.120*	0.50

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Sn1	0.03415 (14)	0.03415 (14)	0.0843 (3)	−0.00937 (17)	−0.01282 (18)	0.01282 (18)
Sn2	0.04630 (18)	0.03956 (16)	0.03599 (14)	0.01171 (13)	0.00052 (13)	−0.00805 (12)
Sn3	0.03041 (12)	0.03041 (12)	0.0447 (2)	−0.00586 (15)	−0.00722 (12)	0.00722 (12)
Cl1	0.0783 (10)	0.0730 (10)	0.0567 (8)	0.0163 (8)	−0.0115 (7)	−0.0226 (7)
O1	0.0442 (18)	0.0470 (19)	0.0516 (18)	−0.0007 (16)	0.0139 (15)	−0.0160 (15)
O2	0.066 (3)	0.068 (3)	0.065 (2)	−0.014 (2)	0.014 (2)	−0.035 (2)
O3	0.0332 (13)	0.0332 (13)	0.049 (2)	−0.0092 (17)	0.0115 (14)	−0.0115 (14)
O4	0.031 (4)	0.022 (3)	0.029 (5)	−0.004 (3)	−0.006 (3)	0.005 (3)
N1	0.048 (2)	0.039 (2)	0.059 (2)	−0.0105 (17)	0.012 (2)	−0.0063 (19)
C1	0.052 (3)	0.039 (2)	0.061 (3)	0.004 (2)	−0.007 (2)	0.008 (2)
C2	0.058 (3)	0.067 (3)	0.044 (2)	0.004 (3)	−0.007 (2)	0.013 (2)
C3	0.042 (3)	0.041 (3)	0.070 (3)	0.009 (2)	−0.003 (2)	−0.001 (2)
C4	0.044 (3)	0.061 (3)	0.079 (4)	−0.004 (2)	−0.027 (3)	0.011 (3)
C5	0.054 (3)	0.050 (3)	0.090 (4)	−0.023 (2)	0.024 (3)	−0.014 (3)
C6	0.040 (2)	0.049 (3)	0.051 (3)	−0.004 (2)	0.008 (2)	0.006 (2)
C7	0.046 (3)	0.044 (3)	0.035 (2)	0.0085 (19)	0.0034 (19)	0.0063 (19)
C8	0.044 (3)	0.058 (3)	0.051 (3)	0.007 (2)	0.008 (2)	0.008 (2)
C9	0.060 (3)	0.070 (4)	0.043 (3)	0.017 (3)	0.015 (3)	0.003 (2)
C10	0.070 (4)	0.059 (3)	0.036 (2)	0.018 (3)	0.006 (2)	−0.007 (2)
C11	0.051 (3)	0.049 (3)	0.035 (2)	0.009 (2)	0.006 (2)	−0.004 (2)
C12	0.041 (2)	0.048 (3)	0.0302 (19)	0.009 (2)	0.0041 (17)	0.0026 (19)

Geometric parameters (Å, °)

Sn1—O3	2.072 (4)	C2—H2B	0.9800
Sn1—C1i	2.112 (5)	C2—H2C	0.9800
Sn1—C1	2.112 (5)	C3—H3A	0.9800
Sn1—O1	2.410 (3)	C3—H3B	0.9800
Sn1—O1i	2.410 (3)	C3—H3C	0.9800
Sn1—N1i	2.426 (4)	C4—H4A	0.9800
Sn1—N1	2.426 (4)	C4—H4B	0.9800
Sn2—Cl1	3.310 (2)	C4—H4C	0.9800
Sn2—O1	2.463 (3)	C5—C5i	1.497 (12)
Sn2—O2	2.791 (4)	C5—H5A	0.9900
Sn2—O3	2.006 (2)	C5—H5B	0.9900
Sn2—C2	2.091 (5)	C6—C7	1.439 (7)
Sn2—C3	2.100 (5)	C6—H6	0.9500
Sn2—O4	2.125 (17)	C7—C12	1.406 (7)
Sn2—O4i	2.192 (16)	C7—C8	1.414 (7)
Sn2—Sn2i	3.2943 (6)	C8—C9	1.379 (8)
Sn3—O4	1.964 (5)	C8—H8	0.9500
Sn3—O4i	1.964 (5)	C9—C10	1.386 (9)
Sn3—C4	2.114 (5)	C9—H9	0.9500
Sn3—C4i	2.114 (5)	C10—C11	1.356 (7)
Sn3—Cl1	2.5829 (15)	C10—H10	0.9500
Sn3—Cl1i	2.5829 (15)	C11—C12	1.432 (7)
O1—C12	1.320 (5)	C13—C14	1.493 (9)
O2—C11	1.381 (7)	C13—H13A	0.9900
O2—C13	1.459 (8)	C13—H13B	0.9900
O2—C13'	1.460 (8)	C14—H14A	0.9800
O3—Sn2i	2.006 (2)	C14—H14B	0.9800
O4—O4i	0.31 (4)	C14—H14C	0.9800
O4—Sn2i	2.192 (16)	C13'—C14'	1.499 (9)
N1—C6	1.267 (6)	C13'—H13C	0.9900
N1—C5	1.472 (6)	C13'—H13D	0.9900
C1—H1A	0.9800	C14'—H14D	0.9800
C1—H1B	0.9800	C14'—H14E	0.9800
C1—H1C	0.9800	C14'—H14F	0.9800
C2—H2A	0.9800
O3—Sn1—C1i	93.05 (15)	C6—N1—Sn1	130.5 (3)
O3—Sn1—C1	93.04 (15)	C5—N1—Sn1	112.1 (3)
C1i—Sn1—C1	173.9 (3)	Sn1—C1—H1A	109.5
O3—Sn1—O1	69.76 (8)	Sn1—C1—H1B	109.5
C1i—Sn1—O1	89.99 (17)	H1A—C1—H1B	109.5
C1—Sn1—O1	92.12 (17)	Sn1—C1—H1C	109.5
O3—Sn1—O1i	69.76 (8)	H1A—C1—H1C	109.5
C1i—Sn1—O1i	92.12 (17)	H1B—C1—H1C	109.5
C1—Sn1—O1i	89.99 (17)	Sn2—C2—H2A	109.5
O1—Sn1—O1i	139.52 (16)	Sn2—C2—H2B	109.5
O3—Sn1—N1i	144.20 (10)	H2A—C2—H2B	109.5
C1i—Sn1—N1i	87.14 (19)	Sn2—C2—H2C	109.5
C1—Sn1—N1i	87.92 (18)	H2A—C2—H2C	109.5
O1—Sn1—N1i	146.01 (13)	H2B—C2—H2C	109.5
O1i—Sn1—N1i	74.46 (13)	Sn2—C3—H3A	109.5
O3—Sn1—N1	144.20 (10)	Sn2—C3—H3B	109.5
C1i—Sn1—N1	87.92 (18)	H3A—C3—H3B	109.5
C1—Sn1—N1	87.14 (19)	Sn2—C3—H3C	109.5
O1—Sn1—N1	74.46 (13)	H3A—C3—H3C	109.5
O1i—Sn1—N1	146.01 (13)	H3B—C3—H3C	109.5
N1i—Sn1—N1	71.6 (2)	Sn3—C4—H4A	109.5
O3—Sn2—C2	108.10 (17)	Sn3—C4—H4B	109.5
O3—Sn2—C3	103.75 (16)	H4A—C4—H4B	109.5
C2—Sn2—C3	147.8 (2)	Sn3—C4—H4C	109.5
O3—Sn2—O4	75.7 (4)	H4A—C4—H4C	109.5
C2—Sn2—O4	91.7 (5)	H4B—C4—H4C	109.5
C3—Sn2—O4	100.8 (5)	N1—C5—C5i	110.7 (4)
O3—Sn2—O4i	74.2 (4)	N1—C5—H5A	109.5
C2—Sn2—O4i	99.8 (5)	C5i—C5—H5A	109.5
C3—Sn2—O4i	93.4 (5)	N1—C5—H5B	109.5
O4—Sn2—O4i	8.1 (10)	C5i—C5—H5B	109.5
O3—Sn2—O1	69.60 (11)	H5A—C5—H5B	108.1
C2—Sn2—O1	93.19 (18)	N1—C6—C7	128.7 (5)
C3—Sn2—O1	93.30 (17)	N1—C6—H6	115.7
O4—Sn2—O1	144.8 (4)	C7—C6—H6	115.7
O4i—Sn2—O1	143.8 (4)	C12—C7—C8	120.0 (5)
O3—Sn2—Sn2i	34.82 (9)	C12—C7—C6	125.0 (4)
C2—Sn2—Sn2i	105.49 (17)	C8—C7—C6	114.8 (5)
C3—Sn2—Sn2i	103.37 (16)	C9—C8—C7	121.0 (5)
O4—Sn2—Sn2i	41.0 (4)	C9—C8—H8	119.5
O4i—Sn2—Sn2i	39.5 (4)	C7—C8—H8	119.5
O1—Sn2—Sn2i	104.40 (7)	C8—C9—C10	119.6 (5)
O4—Sn3—O4i	9.1 (10)	C8—C9—H9	120.2
O4—Sn3—C4	109.3 (6)	C10—C9—H9	120.2
O4i—Sn3—C4	118.2 (6)	C11—C10—C9	120.2 (5)
O4—Sn3—C4i	118.2 (6)	C11—C10—H10	119.9
O4i—Sn3—C4i	109.3 (6)	C9—C10—H10	119.9
C4—Sn3—C4i	132.6 (3)	C10—C11—O2	124.1 (5)
O4—Sn3—Cl1	85.2 (6)	C10—C11—C12	122.6 (5)
O4i—Sn3—Cl1	87.2 (6)	O2—C11—C12	113.2 (4)
C4—Sn3—Cl1	91.55 (19)	O1—C12—C7	124.0 (4)
C4i—Sn3—Cl1	91.49 (19)	O1—C12—C11	119.6 (4)
O4—Sn3—Cl1i	87.2 (6)	C7—C12—C11	116.4 (4)
O4i—Sn3—Cl1i	85.2 (6)	O2—C13—C14	108.0 (10)
C4—Sn3—Cl1i	91.49 (19)	O2—C13—H13A	110.1
C4i—Sn3—Cl1i	91.55 (19)	C14—C13—H13A	110.1
Cl1—Sn3—Cl1i	172.42 (8)	O2—C13—H13B	110.1
C12—O1—Sn1	133.6 (3)	C14—C13—H13B	110.1
C12—O1—Sn2	127.8 (3)	H13A—C13—H13B	108.4
Sn1—O1—Sn2	95.76 (11)	O2—C13'—C14'	117.5 (10)
C11—O2—C13	119.8 (7)	O2—C13'—H13C	107.9
C11—O2—C13'	119.0 (7)	C14'—C13'—H13C	107.9
Sn2—O3—Sn2i	110.36 (18)	O2—C13'—H13D	107.9
Sn2—O3—Sn1	124.82 (9)	C14'—C13'—H13D	107.9
Sn2i—O3—Sn1	124.82 (9)	H13C—C13'—H13D	107.2
O4i—O4—Sn3	85.4 (5)	C13'—C14'—H14D	109.5
O4i—O4—Sn2	98 (6)	C13'—C14'—H14E	109.5
Sn3—O4—Sn2	131.5 (10)	H14D—C14'—H14E	109.5
O4i—O4—Sn2i	73 (6)	C13'—C14'—H14F	109.5
Sn3—O4—Sn2i	127.4 (9)	H14D—C14'—H14F	109.5
Sn2—O4—Sn2i	99.5 (2)	H14E—C14'—H14F	109.5
C6—N1—C5	117.2 (4)
O3—Sn1—O1—C12	162.8 (4)	O3—Sn2—O4—O4i	78 (5)
C1i—Sn1—O1—C12	69.6 (4)	C2—Sn2—O4—O4i	−174 (6)
C1—Sn1—O1—C12	−104.7 (4)	C3—Sn2—O4—O4i	−23 (6)
O1i—Sn1—O1—C12	162.8 (4)	O1—Sn2—O4—O4i	88 (6)
N1i—Sn1—O1—C12	−15.3 (6)	Sn2i—Sn2—O4—O4i	75 (5)
N1—Sn1—O1—C12	−18.3 (4)	O3—Sn2—O4—Sn3	169.5 (13)
O3—Sn1—O1—Sn2	1.46 (6)	C2—Sn2—O4—Sn3	−82.3 (12)
C1i—Sn1—O1—Sn2	−91.79 (18)	C3—Sn2—O4—Sn3	67.9 (12)
C1—Sn1—O1—Sn2	93.93 (18)	O4i—Sn2—O4—Sn3	91 (6)
O1i—Sn1—O1—Sn2	1.46 (6)	O1—Sn2—O4—Sn3	179.8 (5)
N1i—Sn1—O1—Sn2	−176.7 (2)	Sn2i—Sn2—O4—Sn3	165.9 (17)
N1—Sn1—O1—Sn2	−179.63 (16)	O3—Sn2—O4—Sn2i	3.6 (5)
O3—Sn2—O1—C12	−164.5 (4)	C2—Sn2—O4—Sn2i	111.9 (6)
C2—Sn2—O1—C12	87.4 (4)	C3—Sn2—O4—Sn2i	−98.0 (6)
C3—Sn2—O1—C12	−61.0 (4)	O4i—Sn2—O4—Sn2i	−75 (5)
O4—Sn2—O1—C12	−175.1 (9)	O1—Sn2—O4—Sn2i	13.9 (13)
O4i—Sn2—O1—C12	−161.3 (9)	O3—Sn1—N1—C6	19.7 (6)
Sn2i—Sn2—O1—C12	−165.7 (3)	C1i—Sn1—N1—C6	−72.6 (5)
O3—Sn2—O1—Sn1	−1.51 (7)	C1—Sn1—N1—C6	110.9 (5)
C2—Sn2—O1—Sn1	−109.65 (19)	O1—Sn1—N1—C6	17.9 (5)
C3—Sn2—O1—Sn1	101.95 (18)	O1i—Sn1—N1—C6	−163.3 (4)
O4—Sn2—O1—Sn1	−12.1 (9)	N1i—Sn1—N1—C6	−160.3 (6)
O4i—Sn2—O1—Sn1	1.7 (9)	O3—Sn1—N1—C5	−165.8 (3)
Sn2i—Sn2—O1—Sn1	−2.76 (12)	C1i—Sn1—N1—C5	101.8 (4)
C2—Sn2—O3—Sn2i	−91.27 (17)	C1—Sn1—N1—C5	−74.6 (4)
C3—Sn2—O3—Sn2i	93.72 (16)	O1—Sn1—N1—C5	−167.6 (4)
O4—Sn2—O3—Sn2i	−4.2 (5)	O1i—Sn1—N1—C5	11.1 (5)
O4i—Sn2—O3—Sn2i	4.1 (5)	N1i—Sn1—N1—C5	14.2 (3)
O1—Sn2—O3—Sn2i	−177.87 (9)	C6—N1—C5—C5i	134.5 (6)
C2—Sn2—O3—Sn1	88.73 (17)	Sn1—N1—C5—C5i	−40.7 (7)
C3—Sn2—O3—Sn1	−86.28 (16)	C5—N1—C6—C7	174.7 (5)
O4—Sn2—O3—Sn1	175.8 (5)	Sn1—N1—C6—C7	−11.1 (8)
O4i—Sn2—O3—Sn1	−175.9 (5)	N1—C6—C7—C12	−7.7 (8)
O1—Sn2—O3—Sn1	2.13 (9)	N1—C6—C7—C8	177.8 (5)
Sn2i—Sn2—O3—Sn1	180.0	C12—C7—C8—C9	−0.4 (7)
C1i—Sn1—O3—Sn2	86.70 (15)	C6—C7—C8—C9	174.3 (5)
C1—Sn1—O3—Sn2	−93.30 (15)	C7—C8—C9—C10	−1.8 (8)
O1—Sn1—O3—Sn2	−2.17 (9)	C8—C9—C10—C11	2.7 (8)
O1i—Sn1—O3—Sn2	177.83 (9)	C9—C10—C11—O2	−177.8 (5)
N1i—Sn1—O3—Sn2	176.03 (19)	C9—C10—C11—C12	−1.5 (8)
N1—Sn1—O3—Sn2	−3.97 (19)	C13—O2—C11—C10	11.1 (9)
C1i—Sn1—O3—Sn2i	−93.30 (15)	C13'—O2—C11—C10	−8.6 (9)
C1—Sn1—O3—Sn2i	86.70 (15)	C13—O2—C11—C12	−165.5 (7)
O1—Sn1—O3—Sn2i	177.83 (9)	C13'—O2—C11—C12	174.7 (6)
O1i—Sn1—O3—Sn2i	−2.17 (9)	Sn1—O1—C12—C7	10.6 (7)
N1i—Sn1—O3—Sn2i	−3.97 (19)	Sn2—O1—C12—C7	166.8 (3)
N1—Sn1—O3—Sn2i	176.03 (19)	Sn1—O1—C12—C11	−168.7 (3)
C4—Sn3—O4—O4i	−167 (8)	Sn2—O1—C12—C11	−12.5 (6)
C4i—Sn3—O4—O4i	13 (9)	C8—C7—C12—O1	−177.7 (4)
Cl1—Sn3—O4—O4i	103 (8)	C6—C7—C12—O1	8.1 (7)
Cl1i—Sn3—O4—O4i	−77 (8)	C8—C7—C12—C11	1.6 (7)
O4i—Sn3—O4—Sn2	−97 (9)	C6—C7—C12—C11	−172.6 (5)
C4—Sn3—O4—Sn2	95.4 (12)	C10—C11—C12—O1	178.7 (5)
C4i—Sn3—O4—Sn2	−83.7 (12)	O2—C11—C12—O1	−4.6 (7)
Cl1—Sn3—O4—Sn2	5.4 (11)	C10—C11—C12—C7	−0.7 (7)
Cl1i—Sn3—O4—Sn2	−174.0 (11)	O2—C11—C12—C7	176.0 (4)
O4i—Sn3—O4—Sn2i	65 (8)	C11—O2—C13—C14	−96.5 (12)
C4—Sn3—O4—Sn2i	−102.3 (10)	C13'—O2—C13—C14	−4(3)
C4i—Sn3—O4—Sn2i	78.6 (13)	C11—O2—C13'—C14'	−71.7 (14)
Cl1—Sn3—O4—Sn2i	167.7 (11)	C13—O2—C13'—C14'	−169 (5)
Cl1i—Sn3—O4—Sn2i	−11.7 (11)

Symmetry codes: (i) y, x, −z.