Octa-methyldi-μ(3)-oxido-bis-(μ(2)-thio-phene-3-acetato-κO:O')(thio-phene-3-acetato-κO)tetra-tin(IV).

In the centrosymmetric title compound, [Sn(4)(CH(3))(8)(C(6)H(5)O(2)S)(4)O(2)], the central four-membered planar ring (Sn(2)O(2)) makes dihedral angles of 66.28 (12) and 77.43 (11)° with the heterocyclic rings of the bridging and monodentate ligands, respectively. One Sn(IV) atom adopts a distorted SnO(3)C(2) trigonal-bipyramidal geometry, with both C atoms in equatorial sites and the other a grossly distorted SnO(4)C(2) octa-hedral or irregular arrangement. In the crystal, the mol-ecules are connected into pillar-like polymeric units making R(2) (2)(12) ring motifs due to inter-molecular C-H⋯O inter-actions. C-H⋯π inter-actions are also present. The O atoms of the chelating ligands and the S atom of the monodentate ligand are disordered over two sets of sites in a 0.65 (6):0.35 (6) ratio.

Related literature

For related structures, see: Danish et al. (1995 ▶, 1996 ▶); Ng et al. (2001 ▶); Tahir et al. (1997a ▶,b ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Sn4(CH3)8(C6H5O2S)4O2]

M = 1191.79

Triclinic,

a = 9.7330 (5) Å

b = 9.7403 (5) Å

c = 12.0432 (6) Å

α = 85.407 (2)°

β = 85.259 (1)°

γ = 71.256 (2)°

V = 1075.74 (10) Å3

Z = 1

Mo Kα radiation

μ = 2.54 mm−1

T = 296 K

0.20 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.637, T max = 0.719

19310 measured reflections

4012 independent reflections

3441 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.04

4012 reflections

250 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015475/hb2953sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015475/hb2953Isup2.hkl

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

[Sn4(CH3)8(C6H5O2S)4O2]	Z = 1
Mr = 1191.79	F(000) = 580
Triclinic, P1	Dx = 1.840 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7330 (5) Å	Cell parameters from 3441 reflections
b = 9.7403 (5) Å	θ = 2.2–25.5°
c = 12.0432 (6) Å	µ = 2.54 mm−1
α = 85.407 (2)°	T = 296 K
β = 85.259 (1)°	Prism, colourless
γ = 71.256 (2)°	0.20 × 0.15 × 0.13 mm
V = 1075.74 (10) Å3

Bruker Kappa APEXII CCD diffractometer	4012 independent reflections
Radiation source: fine-focus sealed tube	3441 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.80 pixels mm-1	θmax = 25.5°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.637, Tmax = 0.719	l = −14→14
19310 measured reflections

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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0219P)2 + 1.4193P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4012 reflections	Δρmax = 0.84 e Å−3
250 parameters	Δρmin = −0.65 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00156 (19)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.18885 (2)	0.25808 (2)	0.45386 (2)	0.0444 (1)
Sn2	0.48666 (2)	−0.09190 (2)	0.39587 (2)	0.0446 (1)
S1	0.27895 (18)	−0.25877 (16)	−0.05837 (11)	0.0934 (5)
S2A	0.3409 (3)	0.25077 (19)	0.99888 (15)	0.1310 (8)	0.635
O1A	0.1177 (13)	0.137 (3)	0.333 (2)	0.076 (4)	0.65 (6)
O2A	0.3179 (12)	−0.023 (3)	0.2610 (14)	0.065 (4)	0.65 (6)
O3	0.3779 (2)	0.0937 (2)	0.47382 (18)	0.0410 (7)
O4	0.2813 (3)	0.3298 (3)	0.5913 (2)	0.0584 (9)
O5	0.0925 (4)	0.5232 (4)	0.5897 (3)	0.1044 (16)
C1	0.1856 (4)	0.0434 (4)	0.2645 (3)	0.0497 (12)
C2	0.0913 (4)	0.0161 (4)	0.1808 (3)	0.0562 (12)
C3	0.1613 (4)	−0.1092 (4)	0.1087 (3)	0.0532 (12)
C4	0.1850 (5)	−0.2556 (5)	0.1418 (4)	0.0771 (19)
C5	0.2468 (5)	−0.3522 (5)	0.0595 (4)	0.0719 (16)
C6	0.2094 (6)	−0.0968 (5)	0.0020 (4)	0.0756 (19)
C7	0.2415 (5)	0.4034 (5)	0.3342 (4)	0.0789 (17)
C8	0.0351 (4)	0.1981 (5)	0.5611 (4)	0.0822 (18)
C9	0.3936 (5)	−0.2493 (5)	0.4656 (5)	0.089 (2)
C10	0.6134 (5)	−0.0291 (5)	0.2633 (3)	0.0712 (16)
C11	0.2064 (5)	0.4535 (4)	0.6276 (3)	0.0628 (14)
C12	0.2698 (6)	0.5070 (5)	0.7194 (4)	0.0832 (19)
C13	0.2700 (5)	0.4165 (4)	0.8259 (3)	0.0607 (14)
C14	0.1451 (6)	0.4020 (6)	0.8834 (4)	0.0840 (19)
C15	0.1689 (6)	0.3121 (5)	0.9827 (4)	0.0761 (19)
C16	0.3894 (5)	0.3378 (6)	0.8800 (4)	0.0839 (19)
S2B	0.3409 (3)	0.25077 (19)	0.99888 (15)	0.1310 (8)	0.365
O2B	0.283 (5)	−0.0624 (18)	0.299 (4)	0.065 (7)	0.35 (6)
O1B	0.156 (5)	0.168 (2)	0.296 (3)	0.062 (7)	0.35 (6)
H2A	0.00668	0.00014	0.22101	0.0672*
H4	0.16091	−0.28575	0.21394	0.0921*
H5	0.26718	−0.45241	0.06791	0.0864*
H7A	0.19235	0.40649	0.26765	0.1183*
H7B	0.34458	0.37212	0.31712	0.1183*
H6A	0.20504	−0.00826	−0.03533	0.0906*
H2B	0.05705	0.10329	0.13256	0.0672*
H8B	0.05988	0.09419	0.56672	0.1230*
H8C	−0.05934	0.23970	0.53209	0.1230*
H9A	0.30262	−0.20216	0.50480	0.1329*
H9B	0.45826	−0.31449	0.51661	0.1329*
H9C	0.37745	−0.30285	0.40721	0.1329*
H10A	0.67382	0.01893	0.29210	0.1063*
H10B	0.55061	0.03594	0.21106	0.1063*
H10C	0.67335	−0.11358	0.22649	0.1063*
H12A	0.36857	0.50390	0.69644	0.0997*
H12B	0.21327	0.60710	0.73188	0.0997*
H14	0.05271	0.44812	0.85838	0.1013*
H15	0.09708	0.29176	1.03071	0.0912*
H16A	0.48440	0.33181	0.85601	0.1007*
H7C	0.21167	0.49849	0.36272	0.1183*
H8A	0.03409	0.23280	0.63361	0.1230*

	U11	U22	U33	U12	U13	U23
Sn1	0.0437 (1)	0.0386 (1)	0.0463 (2)	−0.0034 (1)	−0.0056 (1)	−0.0128 (1)
Sn2	0.0470 (1)	0.0397 (1)	0.0452 (2)	−0.0066 (1)	−0.0063 (1)	−0.0177 (1)
S1	0.1234 (11)	0.0908 (9)	0.0681 (8)	−0.0294 (8)	−0.0098 (7)	−0.0323 (7)
S2A	0.206 (2)	0.0932 (11)	0.0868 (11)	−0.0321 (12)	−0.0320 (12)	−0.0049 (9)
O1A	0.058 (4)	0.088 (8)	0.084 (8)	−0.016 (4)	−0.007 (4)	−0.050 (7)
O2A	0.054 (4)	0.091 (10)	0.051 (5)	−0.015 (4)	−0.010 (3)	−0.032 (5)
O3	0.0391 (11)	0.0368 (12)	0.0424 (12)	−0.0025 (9)	−0.0042 (9)	−0.0133 (9)
O4	0.0644 (16)	0.0503 (14)	0.0575 (16)	−0.0070 (12)	−0.0136 (12)	−0.0216 (12)
O5	0.099 (3)	0.078 (2)	0.108 (3)	0.0243 (19)	−0.031 (2)	−0.036 (2)
C1	0.056 (2)	0.051 (2)	0.047 (2)	−0.0207 (18)	−0.0110 (17)	−0.0073 (17)
C2	0.063 (2)	0.057 (2)	0.052 (2)	−0.0193 (18)	−0.0162 (18)	−0.0092 (17)
C3	0.061 (2)	0.057 (2)	0.049 (2)	−0.0237 (18)	−0.0167 (17)	−0.0112 (17)
C4	0.103 (4)	0.065 (3)	0.073 (3)	−0.041 (3)	0.002 (3)	−0.008 (2)
C5	0.095 (3)	0.052 (2)	0.077 (3)	−0.033 (2)	0.002 (2)	−0.019 (2)
C6	0.116 (4)	0.063 (3)	0.052 (3)	−0.030 (3)	−0.016 (2)	−0.010 (2)
C7	0.099 (3)	0.062 (3)	0.059 (3)	−0.006 (2)	0.000 (2)	0.008 (2)
C8	0.051 (2)	0.075 (3)	0.117 (4)	−0.019 (2)	0.014 (2)	−0.008 (3)
C9	0.066 (3)	0.067 (3)	0.143 (5)	−0.033 (2)	−0.002 (3)	−0.016 (3)
C10	0.088 (3)	0.065 (3)	0.047 (2)	−0.008 (2)	0.007 (2)	−0.0032 (19)
C11	0.083 (3)	0.049 (2)	0.054 (2)	−0.013 (2)	−0.009 (2)	−0.0174 (18)
C12	0.137 (4)	0.069 (3)	0.058 (3)	−0.047 (3)	−0.012 (3)	−0.021 (2)
C13	0.077 (3)	0.059 (2)	0.052 (2)	−0.024 (2)	−0.005 (2)	−0.0255 (19)
C14	0.076 (3)	0.085 (3)	0.095 (4)	−0.028 (3)	0.009 (3)	−0.032 (3)
C15	0.095 (4)	0.067 (3)	0.072 (3)	−0.037 (3)	0.017 (3)	−0.013 (2)
C16	0.076 (3)	0.098 (4)	0.079 (3)	−0.022 (3)	−0.008 (2)	−0.032 (3)
S2B	0.206 (2)	0.0932 (11)	0.0868 (11)	−0.0321 (12)	−0.0320 (12)	−0.0049 (9)
O2B	0.075 (12)	0.052 (7)	0.076 (15)	−0.021 (5)	−0.033 (12)	−0.012 (7)
O1B	0.076 (15)	0.047 (7)	0.062 (11)	−0.011 (6)	−0.025 (9)	−0.021 (6)

Sn1—O1A	2.23 (2)	C3—C6	1.341 (6)
Sn1—O3	2.031 (2)	C4—C5	1.384 (7)
Sn1—O4	2.207 (3)	C11—C12	1.512 (7)
Sn1—C7	2.088 (5)	C12—C13	1.497 (6)
Sn1—C8	2.091 (4)	C13—C16	1.355 (7)
Sn1—O1B	2.24 (4)	C13—C14	1.390 (8)
Sn2—O2A	2.312 (17)	C14—C15	1.414 (7)
Sn2—O3	2.0366 (19)	C2—H2A	0.9700
Sn2—C9	2.106 (5)	C2—H2B	0.9700
Sn2—C10	2.109 (4)	C4—H4	0.9300
Sn2—O3i	2.127 (2)	C5—H5	0.9300
Sn2—O4i	2.670 (3)	C6—H6A	0.9300
Sn2—O2B	2.31 (5)	C7—H7A	0.9600
Sn2—Sn2i	3.2694 (4)	C7—H7B	0.9600
S1—C5	1.686 (5)	C7—H7C	0.9600
S1—C6	1.701 (5)	C8—H8A	0.9600
S2A—C15	1.609 (7)	C8—H8B	0.9600
S2A—C16	1.715 (5)	C8—H8C	0.9600
S2B—C16	1.715 (5)	C9—H9A	0.9600
S2B—C15	1.609 (7)	C9—H9B	0.9600
O1A—C1	1.26 (3)	C9—H9C	0.9600
O1B—C1	1.24 (2)	C10—H10A	0.9600
O2A—C1	1.240 (19)	C10—H10B	0.9600
O2B—C1	1.23 (3)	C10—H10C	0.9600
O4—C11	1.281 (5)	C12—H12A	0.9700
O5—C11	1.204 (6)	C12—H12B	0.9700
C1—C2	1.511 (5)	C14—H14	0.9300
C2—C3	1.498 (5)	C15—H15	0.9300
C3—C4	1.399 (6)	C16—H16A	0.9300
O1A—Sn1—O3	91.9 (6)	C3—C4—C5	115.2 (4)
O1A—Sn1—O4	167.3 (7)	S1—C5—C4	109.0 (3)
O1A—Sn1—C7	95.5 (6)	S1—C6—C3	113.4 (3)
O1A—Sn1—C8	82.7 (5)	O4—C11—C12	116.3 (4)
O3—Sn1—O4	77.69 (9)	O4—C11—O5	121.5 (4)
O3—Sn1—C7	104.94 (15)	O5—C11—C12	122.2 (4)
O3—Sn1—C8	104.92 (14)	C11—C12—C13	111.4 (4)
O1B—Sn1—O3	90.8 (9)	C12—C13—C14	124.0 (5)
O4—Sn1—C7	94.25 (15)	C12—C13—C16	125.7 (5)
O4—Sn1—C8	92.93 (15)	C14—C13—C16	110.4 (4)
O1B—Sn1—O4	164.9 (12)	C13—C14—C15	115.1 (5)
C7—Sn1—C8	150.12 (18)	S2A—C15—C14	108.6 (4)
O1B—Sn1—C7	79.1 (9)	S2B—C15—C14	108.6 (4)
O1B—Sn1—C8	99.6 (11)	S2A—C16—C13	110.5 (4)
O2A—Sn2—O3	89.1 (6)	S2B—C16—C13	110.5 (4)
O2A—Sn2—C9	90.5 (6)	C1—C2—H2A	108.00
O2A—Sn2—C10	80.5 (4)	C1—C2—H2B	108.00
Sn2i—Sn2—O2A	128.1 (6)	C3—C2—H2A	108.00
O2A—Sn2—O3i	164.4 (7)	C3—C2—H2B	108.00
O2A—Sn2—O4i	128.2 (6)	H2A—C2—H2B	107.00
O3—Sn2—C9	105.78 (15)	C3—C4—H4	122.00
O3—Sn2—C10	105.39 (14)	C5—C4—H4	122.00
O2B—Sn2—O3	89.1 (7)	S1—C5—H5	126.00
Sn2i—Sn2—O3	39.25 (6)	C4—C5—H5	125.00
O3—Sn2—O3i	76.53 (8)	S1—C6—H6A	123.00
O3—Sn2—O4i	142.67 (8)	C3—C6—H6A	123.00
C9—Sn2—C10	147.33 (19)	Sn1—C7—H7A	109.00
O2B—Sn2—C9	73.5 (9)	Sn1—C7—H7B	110.00
Sn2i—Sn2—C9	105.84 (16)	Sn1—C7—H7C	109.00
O3i—Sn2—C9	99.16 (16)	H7A—C7—H7B	109.00
O4i—Sn2—C9	78.01 (15)	H7A—C7—H7C	109.00
O2B—Sn2—C10	97.5 (12)	H7B—C7—H7C	109.00
Sn2i—Sn2—C10	104.38 (12)	Sn1—C8—H8A	109.00
O3i—Sn2—C10	97.34 (14)	Sn1—C8—H8B	109.00
O4i—Sn2—C10	83.18 (14)	Sn1—C8—H8C	109.00
Sn2i—Sn2—O2B	127.4 (8)	H8A—C8—H8B	110.00
O2B—Sn2—O3i	161.6 (11)	H8A—C8—H8C	109.00
O2B—Sn2—O4i	126.4 (5)	H8B—C8—H8C	109.00
Sn2i—Sn2—O3i	37.29 (5)	Sn2—C9—H9A	109.00
Sn2i—Sn2—O4i	103.52 (6)	Sn2—C9—H9B	109.00
O3i—Sn2—O4i	66.28 (8)	Sn2—C9—H9C	109.00
C5—S1—C6	92.5 (2)	H9A—C9—H9B	109.00
C15—S2A—C16	95.4 (3)	H9A—C9—H9C	109.00
C15—S2B—C16	95.4 (3)	H9B—C9—H9C	110.00
Sn1—O1A—C1	133.2 (11)	Sn2—C10—H10A	109.00
Sn1—O1B—C1	134 (2)	Sn2—C10—H10B	109.00
Sn2—O2A—C1	132.8 (12)	Sn2—C10—H10C	109.00
Sn2—O2B—C1	134 (2)	H10A—C10—H10B	109.00
Sn2—O3—Sn2i	103.47 (9)	H10A—C10—H10C	110.00
Sn1—O3—Sn2i	120.70 (10)	H10B—C10—H10C	110.00
Sn1—O3—Sn2	135.83 (11)	C11—C12—H12A	109.00
Sn2i—O4—C11	149.5 (3)	C11—C12—H12B	109.00
Sn1—O4—Sn2i	95.14 (9)	C13—C12—H12A	109.00
Sn1—O4—C11	115.4 (3)	C13—C12—H12B	109.00
O1A—C1—O2A	125.9 (13)	H12A—C12—H12B	108.00
O1A—C1—C2	114.1 (9)	C13—C14—H14	122.00
O2A—C1—C2	120.0 (10)	C15—C14—H14	122.00
O1B—C1—O2B	125 (3)	S2A—C15—H15	126.00
O1B—C1—C2	118 (2)	C14—C15—H15	126.00
O2B—C1—C2	116.6 (18)	S2B—C15—H15	126.00
C1—C2—C3	116.3 (3)	S2A—C16—H16A	125.00
C2—C3—C4	125.4 (4)	C13—C16—H16A	125.00
C2—C3—C6	124.6 (4)	S2B—C16—H16A	125.00
C4—C3—C6	110.0 (4)
O3—Sn1—O1A—C1	−29 (2)	C10—Sn2—Sn2i—O2Ai	−90.9 (6)
C7—Sn1—O1A—C1	76 (2)	C10—Sn2—Sn2i—O3i	−83.16 (16)
C8—Sn1—O1A—C1	−134 (2)	C10—Sn2—Sn2i—C9i	12.55 (19)
O1A—Sn1—O3—Sn2	11.1 (6)	C10—Sn2—Sn2i—C10i	180.0 (2)
O1A—Sn1—O3—Sn2i	−168.5 (6)	O3i—Sn2—Sn2i—O3	180.00 (14)
O4—Sn1—O3—Sn2	−176.29 (17)	O3i—Sn2—Sn2i—O4	176.85 (11)
O4—Sn1—O3—Sn2i	4.13 (11)	O4i—Sn2—Sn2i—O3	−176.85 (11)
C7—Sn1—O3—Sn2	−85.1 (2)	O4i—Sn2—Sn2i—O4	180.00 (8)
C7—Sn1—O3—Sn2i	95.29 (17)	O3—Sn2—O3i—Sn1i	−179.70 (13)
C8—Sn1—O3—Sn2	94.0 (2)	O3—Sn2—O3i—Sn2i	0.00 (10)
C8—Sn1—O3—Sn2i	−85.63 (17)	C9—Sn2—O3i—Sn1i	76.14 (17)
O3—Sn1—O4—C11	178.3 (3)	C9—Sn2—O3i—Sn2i	−104.16 (16)
O3—Sn1—O4—Sn2i	−2.84 (8)	C10—Sn2—O3i—Sn1i	−75.56 (16)
C7—Sn1—O4—C11	73.9 (3)	C10—Sn2—O3i—Sn2i	104.14 (15)
C7—Sn1—O4—Sn2i	−107.23 (15)	O2A—Sn2—O4i—Sn1i	170.4 (6)
C8—Sn1—O4—C11	−77.1 (3)	O2A—Sn2—O4i—C11i	−7.7 (8)
C8—Sn1—O4—Sn2i	101.80 (14)	O3—Sn2—O4i—Sn1i	−8.27 (18)
O3—Sn2—O2A—C1	−35 (2)	O3—Sn2—O4i—C11i	173.7 (5)
C9—Sn2—O2A—C1	71 (2)	C9—Sn2—O4i—Sn1i	−108.63 (18)
C10—Sn2—O2A—C1	−140 (2)	C9—Sn2—O4i—C11i	73.3 (5)
Sn2i—Sn2—O2A—C1	−39 (2)	C10—Sn2—O4i—Sn1i	98.23 (15)
O4i—Sn2—O2A—C1	146.3 (19)	C10—Sn2—O4i—C11i	−79.9 (5)
O2A—Sn2—O3—Sn1	6.5 (5)	C6—S1—C5—C4	−0.7 (4)
O2A—Sn2—O3—Sn2i	−173.9 (5)	C5—S1—C6—C3	−0.3 (5)
C9—Sn2—O3—Sn1	−83.8 (2)	C16—S2A—C15—C14	0.2 (4)
C9—Sn2—O3—Sn2i	95.88 (17)	C15—S2A—C16—C13	0.0 (4)
C10—Sn2—O3—Sn1	86.34 (19)	Sn1—O1A—C1—O2A	13 (3)
C10—Sn2—O3—Sn2i	−94.03 (15)	Sn1—O1A—C1—C2	−166.7 (15)
Sn2i—Sn2—O3—Sn1	−179.6 (2)	Sn2—O2A—C1—O1A	29 (3)
O3i—Sn2—O3—Sn1	−179.63 (17)	Sn2—O2A—C1—C2	−152.2 (14)
O3i—Sn2—O3—Sn2i	0.00 (8)	Sn1—O4—C11—O5	1.2 (5)
O4i—Sn2—O3—Sn1	−174.57 (12)	Sn1—O4—C11—C12	−178.2 (3)
O4i—Sn2—O3—Sn2i	5.06 (18)	Sn2i—O4—C11—O5	−176.6 (3)
O2A—Sn2—Sn2i—O3	7.8 (6)	Sn2i—O4—C11—C12	4.0 (7)
O2A—Sn2—Sn2i—O4	4.6 (6)	O1A—C1—C2—C3	−171.2 (13)
O2A—Sn2—Sn2i—O2Ai	−180.0 (8)	O2A—C1—C2—C3	9.5 (13)
O2A—Sn2—Sn2i—O3i	−172.2 (6)	C1—C2—C3—C4	78.1 (5)
O2A—Sn2—Sn2i—C9i	−76.5 (6)	C1—C2—C3—C6	−102.5 (5)
O2A—Sn2—Sn2i—C10i	90.9 (6)	C2—C3—C4—C5	177.7 (4)
O3—Sn2—Sn2i—O4	−3.15 (11)	C6—C3—C4—C5	−1.7 (6)
O3—Sn2—Sn2i—O2Ai	172.2 (6)	C2—C3—C6—S1	−178.3 (3)
O3—Sn2—Sn2i—O3i	−180.00 (14)	C4—C3—C6—S1	1.2 (6)
O3—Sn2—Sn2i—C9i	−84.29 (17)	C3—C4—C5—S1	1.5 (6)
O3—Sn2—Sn2i—C10i	83.16 (16)	O4—C11—C12—C13	−68.4 (5)
C9—Sn2—Sn2i—O3	−95.71 (17)	O5—C11—C12—C13	112.2 (5)
C9—Sn2—Sn2i—O4	−98.86 (15)	C11—C12—C13—C14	−61.4 (6)
C9—Sn2—Sn2i—O2Ai	76.5 (6)	C11—C12—C13—C16	118.7 (5)
C9—Sn2—Sn2i—O3i	84.29 (17)	C12—C13—C14—C15	−179.6 (4)
C9—Sn2—Sn2i—C9i	−180.0 (2)	C16—C13—C14—C15	0.3 (6)
C9—Sn2—Sn2i—C10i	−12.55 (19)	C12—C13—C16—S2A	179.8 (4)
C10—Sn2—Sn2i—O3	96.85 (16)	C14—C13—C16—S2A	−0.2 (5)
C10—Sn2—Sn2i—O4	93.70 (15)	C13—C14—C15—S2A	−0.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O5ii	0.96	2.58	3.103 (6)	115
C5—H5···CgCiii	0.93	2.83	3.513 (5)	131
C10—H10C···CgCi	0.96	2.80	3.697 (5)	156

Table 1

Selected bond lengths (Å)

Sn1—O1A	2.23 (2)
Sn1—O3	2.031 (2)
Sn1—O4	2.207 (3)
Sn1—C7	2.088 (5)
Sn1—C8	2.091 (4)
Sn2—O2A	2.312 (17)
Sn2—O3	2.0366 (19)
Sn2—C9	2.106 (5)
Sn2—C10	2.109 (4)
Sn2—O3i	2.127 (2)
Sn2—O4i	2.670 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯O5ii	0.96	2.58	3.103 (6)	115
C5—H5⋯CgCiii	0.93	2.83	3.513 (5)	131
C10—H10C⋯CgCi	0.96	2.80	3.697 (5)	156

Symmetry codes: (i) ; (ii) ; (iii) . CgC is the centriod of the heterocyclic ring (C13–C16/S2A or C13–C16/S2B).