Isostructural or not? Adducts of some aryl­tin halides with (E)-1,2-bis(4-pyridyl)­ethene

The title complexes [μ-(E)-4,4′-(ethene-1,2-diyl)­di­pyridine-κ²N:N′]­bis­[halotris(4-methyl­phenyl)­tin(IV)], [Sn₂(C₇H₇)₆X₂(C₁₂H₁₀N₂)], where halo is chloro (X = Cl) and bromo (X = Br) are isostructural. In both crystals, the mol­ecules lie on inversion centers, and there are voids of ca 80 ų that could, but apparently do not, accommodate water mol­ecules. The corresponding iodo structure (X = I) is almost, but not quite, isostructural with the other two compounds; when Br is changed to I, the length of the c axis decreases by more than 1 Å and the voids are no longer large enough to accomodate any solvent mol­ecule. The related complex [μ-(E)-4,4′-(ethene-1,2-diyl)­di­pyridine-κ²N:N′]­bis­[chloro­tri­phenyl­tin(IV)], [Sn₂(C₆H₅)₆Cl₂(C₁₂H₁₀N₂)], crystallizes in a related structure, but the mol­ecules lie on general rather than on special positions. The molecular structures of the four complexes are similar, but the conformation of the phenyl derivative is approximately eclipsed rather than staggered.

S1. Comment

The structures of the four molecules shown in the Scheme below were determined as part of a study of Sn complexes (Bajue et al., 1992). The structures are interesting crystallographically because the members of the set R = Me/X = Cl, R = Me/X = Br, and R = Me/X = I are almost, but not quite, isostructural. The packing in the R = H/X = Cl crystal is similar even though the molecular volume is ca 13% smaller.

The molecular structures of the four compounds (see Fig. 1) are similar. The tolyl groups are staggered in the R = Me/X = Cl, R = Me/X = Br, and R = Me/X = I molecules, all of which lie on inversion centers. In the R = H/X = Cl molecule, which has no imposed crystallographic symmetry, the phenyl groups are approximately eclipsed [torsion angles 22.0 (1), 17.1 (1), and 15.0 (1)° for angles Cn—Sn1···Sn2—C(n+24), n = 7, 13, and 19]. While the R = Me/X = Cl and R = Me/X = Br molecules are nearly identical, the positions and orientations of the tolyl rings in the R = Me/X = I molecule are a little different. An important stilbene-like disorder (Bouwstra et al., 1984, and references therein) of the bridging trans-1,2-bis(4-pyridyl)ethene ligand (hereafter, the bpe ligand) in the iodo compound is obvious (see Fig. 1 and Experimental). This disorder is good evidence that the structure of the iodo compound differs in significant, if small, ways from the structures of the chloro and bromo compounds.

The bpe ligand is significantly non-planar in the R = Me/X = I molecule, but is essentially planar in the other three molecules. The torsion angles C2—C3—C6—C6' and C4—C3—C6—C6' for the major component of R = Me/X = I are −157.5 (7) and 23.2 (11)°, but are 0(1) and 179 (1)° for R = Me/X = Cl, and are 4(1) and 177 (1)° for R = Me/X = Br. For the two independent halves of the R = H/X = Cl, molecule, the corresponding angles are 6(1) and 174 (1)°, and 6(1) and 172 (1)°.

A quick look at the packing diagrams for the three R = Me structures (see Figs. 2 and 3) suggests that the compounds are isostructural, but a comparison of the cell constants indicates otherwise. The value of a increases by 0.095 (2) Å and by 0.431 (2) Å when Cl is changed to Br and then I; the corresponding pairs of changes for b are 0.041 (2) and 0.263 (2) Å. The changes for c, however, are +0.055 (3) Å when Cl is changed to Br but −1.074 (3) Å when Br is changed to I. The c axis is very significantly shorter in the I compound than in the Br compound. The volume per molecule increases by 19.9 (4) ų when Cl is changed to Br, but remains unchanged [ΔV is −0.1 (4) ų] when Br is changed to I. The structure of the I derivative is more closely packed than are the structures of the Br and Cl derivatives.

The free spaces in the R = Me/X = Cl and R = Me/X = Br structures are concentrated in regions classified by PLATON (Spek, 2003) as `solvent-accessible voids' (see Fig. 2). Although the empty spaces seemed large enough (81 and 83 ų) to accommodate small solvent molecules, a more detailed analysis (Spek, 2002) indicated that the spaces are too constricted (i.e., dumb-bell-shaped) to hold any molecule larger than water. Since no water was present during the synthesis or recrystallization, and since little electron density is found in the void regions (see Experimental), we conclude that the voids are empty. PLATON (Spek, 2003) identifies no void in the R = Me/X = I or R = H/X = Cl structure.

The crystal packing can be described in terms of planes that contain the real-space directions [101] and [010] (R = Me; see Fig. 3) or [001] and [010] (R = H; see bottom half of Fig. 4). Within these layers (Fig. 2 and the top half of Fig. 4) there are short X···H—C interactions (see Table 2) that involve atoms C4 and C6 and either their symmetry equivalents in the other half of the molecule (R = Me) or atoms C26 and C30 (R = H). These interactions are substantially weaker in the X = I structure than in the other three structures.

Drawings of these layers for the R = Me/X = Cl and R = Me/X = Br structures are nearly superimposable. There are very subtle differences, however, between the layers for the X = Br and X = I structures (see Fig. 2). The long molecular axes for the R = H/X = Cl compound make a smaller angle (see top half of Fig. 4) with the b axis, but the basic arrangement is the same.

No significiant difference between the stacking of these layers in the R = Me/X = Cl and R = Me/X = Br compounds can be identified, but the distance across x = z = 1/2, y = 0 between the I atoms in molecules related by the translation a+c is substantially shorter (6.46 Å) than the corresponding distances between the Br or Cl atoms (8.77 and 9.09 Å; all s.u. values < 0.002 Å). The shorter of the two X···X contacts across the inversion center at x = y = z = 1/2 are similar in the three structures (8.68, 8.42 and 8.27 Å for X = I, Br and Cl, respectively). All other X···X contacts are longer than 12 Å.

There is no question that the R = Me/X = Cl and R = Me/X = Br compounds should be considered isostructural. These crystals are so similar that the formation of mixed crystals (or solid solutions) seems likely and may even have been observed (see Experimental). The R = Me/X = I structure is very similar, but important differences in the molecular conformation, the intermolecular interactions, and the ratios of the cell constants can be identified. The choice of whether or not to describe the Br and I structures as isostructural would probably depend on the purpose of the comparison.

For the R = Me/X = Cl and R = H/X = Cl structures it is the similarities, rather than the structural differences, that are easily missed. The doubling of the asymmetric unit is a surprise, because most molecules and ions that can conform to inversion symmetry do (Yao et al., 2002). It looks as if (see Fig. 3) the methyl groups in the tolyl series prevent tighter packing of the layers. When the Me groups are replaced by H atoms, the structure collapses (see bottom half of Fig. 4) so that the `voids' are much smaller. The change in imposed symmetry and conformation means that the contacts on the two sides of the layer are different (see Fig. 4). The tighter packing is reflected in the melting point; T_fus rises by ca 50 K when R = Me/X = Cl is changed to R = H/X = Cl, even though the molar mass drops by 84 Da (see Experimental).

S2. Experimental

The adducts were prepared by refluxing the triorganotin halides with (E)-4,4'-(ethene-1,2-diyl)bis(pyridine) (bpe) in ethanol for about 1 h. Typically, a 0.001 mol sample of the tin compound was used. The reactions were carried out using various mole ratios of Sn-to-ligand, but only 2:1 adducts were obtained. The melting points are 409–410 (R = Me/X = Cl), 395–397 (R = Me/X = Br), 369–371 (R = Me/X = I), and 460–462 K (R = H/X = Cl).

S3. Refinement

For the R = Me/X = Cl compound, the position of the largest peak in the final difference Fourier map (0.72 e Å⁻³) suggests the possibility of minor disorder of atom C6 of the type known for stilbene (Bouwstra et al., 1984, and references therein). The second largest peak (0.38 e ų) lies 1.83 Å from the inversion center at 0, 1/2, 0 in a region that PLATON (Spek, 2003) identifies as a solvent-accessible void with a volume of 81 ų. Crystals had been grown from benzene, which has an approximate volume (Hofmann, 2002) of 114 ų, but ethanol (approximate volume 70 ų) may also have been present. In any event, no pattern of peaks corresponding to a localized solvent molecule could be identified. Other peaks in the difference map (0.36 e Å⁻³) are near the mid-points of bonds or suggest a set of alternate positions for the methyl H atoms. The deepest trough (−0.45 e Å⁻³) is 0.75 Å from the Sn atom.

For the R = Me/X = Br compound, the largest peak in the final difference Fourier map (0.52 e Å⁻³) is 0.68 Å from the Sn atom. The second largest peak (0.51 e Å⁻³) suggests a stilbene-like disorder of atom C6. The third largest peak ((0.37 e Å⁻³) is part of a cluster around the Br atom. The fourth largest peak (0.37 e Å⁻³) lies 1.76 Å from the inversion center at 0, 1/2, 0 in a solvent-accessible region of volume of 83 ų. Crystals had been grown from ethanol. The most important feature of the final difference map, however, is a set of three large troughs (−1.14 to −1.37 e Å⁻³) near the Br atom. It seems possible that some of the supposed Br atoms were actually Cl atoms.

For the R = Me/X = I compound, when the standard anisotropic refinement had converged the atomic ellipsoids showed clearly that the bpe ligand is disordered in the same way as stilbene (Bouwstra et al., 1984, and references therein). The final disorder model included two sites (see Fig. 1); the occupancy factor for the major site (N1/C1–C6) is 0.739 (7). The refinement included restraints to keep the pyridyl rings planar (FLAT 0.10) and to keep the distances and angles in the two BPE ligands similar (SAME and SADI 0.002). The two N atoms were required to have the same anisotropic displacement parameters; restraints (SIMU 0.012) kept the displacement parameters of atoms C1–C6 and C1A–C6A similar.

For the R = H/X = Cl compound, the atomic ellipsoids for the phenyl ring containing atoms C7—C12 suggest disorder between rings displaced by ca 0.6 Å. A number of disorder models were explored but we eventually decided they offered no advantage. The molecular geometry of this ring, which has C—C bonds that are a little shorter than average, is not accurate. The top five peaks in the final difference map (0.41 to 0.25 e Å⁻³) are associated with this ring. The deepest trough (−0.58 e Å⁻³) is 0.74 Å from the Sn atom.

The H atoms in all four structures were placed at calculated positions. The C—H distances in the methyl groups were fixed at 0.96 Å; all other C—H distances were fixed at 0.93 Å. The U_iso values for the methyl H atoms were set to 1.5 times the U_eq value for the attached C atom; the multiplicative factor was 1.2 for all other H atoms. The use of calculated positions for the methyl groups of the tolyl rings (HFIX/AFIX 33) in the X = Cl and X = Br structures is almost certainly a serious approximation; in the X = I structure there were contacts so short that the methyl groups were allowed to rotate (AFIX 137).

Computing details

For all compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in maXus (Mackay et al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990).

Figures

	Fig. 1. Perspective drawings of the molecules of the four different compounds; enough information is given about the atom-numbering schemes that the numbers of all atoms can be worked out. The schemes for the first three molecules, all of which lie on inversion centers, are the same except for the label of the halogen atom and the labels of the two independent N atoms (N1 and N1A) in the R = Me/X = I structure. The C atoms in the phenyl rings are numbered sequentially, with the lowest number assigned to the C atom attached to the Sn atom (see Table 1). The N atom (label not shown) of the bpe ligand is attached to the atoms Sn, C1, and C5. The numbering scheme for the fourth molecule, which lies on a general position, is similar. The shapes of the ellipsoids correspond to 50% probability contours of atomic displacement. H atoms have been omitted for clarity.
	Fig. 2. Slices of the R = Me/X = Br (upper drawing) and R = Me/X = I (lower drawing) structures viewed along −a*+c*. These slices are the layers described in the text. The vectors a+c are in the planes of the drawings and point vertically downwards; the centers of the drawings are at 1/2,1/2,1/2. The possible voids are located at, for example, 0,1/2,0 and at 1/2,0,1/2. The differences between the two structures are most easily seen in the regions of the drawing in which the phenyl rings appear most densely packed. In the R = Me/X = I structure, a single circle represents the disordered atoms C6 and C6A.
	Fig. 3. Slices of the R = Me/X = Cl (upper drawing) and R = Me/X = I (lower drawing) structures viewed along b; the centers of the drawings are at 1/2, 1/2, 1/2. The differences between the two structures are most easily seen around the central bond (C6—C6') of the bpe ligand. The layers described in the text are parallel to a+c and b and so are viewed edge-on; these layers extend from the lower left to the upper right of the drawings. In the X = I structure, a single circle represents the disordered atoms C6 and C6A.
	Fig. 4. Slices of the R = H/X = Cl structure drawn to maximize the similarities to the drawings shown in Figs. 2 and 3. The upper drawing shows a slice of the structure viewed along a*; the center of the drawing is at 1/4, 1, 1/4. The lower drawing shows a slice viewed along −b; the center of the drawing is at 1/2, 1/2, 1/2.

(I) [µ-(E)-4,4'-(1,2-ethenediyl)dipyridine-κ²-N:N']bis[chlorotris(4- methylphenyl)tin(IV)]

Crystal data

[Sn2(C7H7)6Cl2(C12H10N2)]	Dx = 1.385 Mg m^−3
Mr = 1037.26	Melting point: 136-137 C K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.641 (1) Å	Cell parameters from 50324 reflections
b = 12.019 (1) Å	θ = 2.0–25.0°
c = 17.999 (2) Å	µ = 1.15 mm^−1
β = 98.94 (1)°	T = 293 K
V = 2487.7 (4) Å^3	Block, colourless
Z = 2	0.32 × 0.32 × 0.24 mm
F(000) = 1048

Data collection

Nonius KappaCCD diffractometer	4372 independent reflections
Radiation source: fine-focus sealed tube	3781 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 2.1°
ϕ and ω scans with 1.0° steps	h = 0→13
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	k = −14→14
Tmin = 0.65, Tmax = 0.74	l = −21→21
8292 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 1.8P] where P = (Fo^2 + 2Fc^2)/3
4372 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 35 mm. Each frame was measured for 60 s. The number of scan sets measured was 5; the total number of frames measured was 756.

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

	x	y	z	Uiso*/Ueq
Sn	0.05018 (2)	0.27211 (2)	0.22573 (1)	0.0409 (1)
Cl	−0.13316 (6)	0.22531 (8)	0.13781 (4)	0.0589 (2)
N	0.22357 (19)	0.3280 (2)	0.31738 (12)	0.0453 (6)
C1	0.3092 (2)	0.3842 (2)	0.29343 (17)	0.0489 (7)
H1	0.3101	0.3871	0.2419	0.059*
C2	0.3963 (3)	0.4384 (2)	0.33977 (17)	0.0514 (7)
H2	0.4532	0.4770	0.3194	0.062*
C3	0.3993 (3)	0.4353 (2)	0.41603 (18)	0.0523 (8)
C4	0.3120 (3)	0.3753 (3)	0.44220 (16)	0.0655 (9)
H4	0.3115	0.3689	0.4936	0.079*
C5	0.2253 (3)	0.3247 (3)	0.39179 (16)	0.0582 (8)
H5	0.1661	0.2871	0.4105	0.070*
C6	0.4934 (3)	0.4971 (3)	0.46445 (17)	0.0613 (8)
H6	0.5471	0.5347	0.4405	0.074*
C7	0.1606 (2)	0.2387 (2)	0.14406 (15)	0.0410 (6)
C8	0.1281 (3)	0.2716 (3)	0.06996 (16)	0.0518 (7)
H8	0.0617	0.3147	0.0571	0.062*
C9	0.1926 (3)	0.2417 (3)	0.01470 (17)	0.0632 (9)
H9	0.1696	0.2660	−0.0344	0.076*
C10	0.2903 (3)	0.1762 (3)	0.03161 (18)	0.0607 (8)
C11	0.3246 (3)	0.1450 (3)	0.10523 (18)	0.0573 (8)
H11	0.3914	0.1022	0.1177	0.069*
C12	0.2616 (2)	0.1760 (3)	0.16110 (16)	0.0487 (7)
H12	0.2872	0.1547	0.2106	0.058*
C13	0.3577 (4)	0.1375 (4)	−0.0302 (2)	0.0950 (14)
H13A	0.3220	0.1675	−0.0776	0.142*
H13B	0.3567	0.0577	−0.0326	0.142*
H13C	0.4366	0.1630	−0.0190	0.142*
C14	0.0205 (2)	0.1449 (2)	0.30380 (15)	0.0428 (6)
C15	−0.0918 (3)	0.1205 (3)	0.31534 (18)	0.0548 (8)
H15	−0.1528	0.1648	0.2926	0.066*
C16	−0.1154 (3)	0.0321 (3)	0.35977 (18)	0.0597 (8)
H16	−0.1917	0.0188	0.3668	0.072*
C17	−0.0284 (3)	−0.0366 (3)	0.39364 (17)	0.0538 (8)
C18	0.0840 (3)	−0.0132 (3)	0.38281 (17)	0.0567 (8)
H18	0.1445	−0.0583	0.4053	0.068*
C19	0.1083 (3)	0.0761 (3)	0.33913 (16)	0.0502 (7)
H19	0.1849	0.0903	0.3333	0.060*
C20	−0.0554 (4)	−0.1354 (3)	0.4394 (2)	0.0768 (11)
H20A	0.0156	−0.1728	0.4594	0.115*
H20B	−0.1053	−0.1858	0.4079	0.115*
H20C	−0.0937	−0.1107	0.4799	0.115*
C21	−0.0030 (2)	0.4410 (2)	0.23193 (15)	0.0431 (6)
C22	−0.0762 (3)	0.4762 (3)	0.28066 (17)	0.0536 (8)
H22	−0.1004	0.4255	0.3141	0.064*
C23	−0.1143 (3)	0.5854 (3)	0.28079 (18)	0.0557 (8)
H23	−0.1637	0.6067	0.3142	0.067*
C24	−0.0803 (2)	0.6630 (3)	0.23218 (17)	0.0507 (7)
C25	−0.0077 (3)	0.6277 (3)	0.18252 (17)	0.0542 (8)
H25	0.0155	0.6782	0.1486	0.065*
C26	0.0307 (3)	0.5188 (3)	0.18261 (17)	0.0520 (7)
H26	0.0799	0.4973	0.1491	0.062*
C27	−0.1204 (3)	0.7816 (3)	0.2329 (2)	0.0695 (10)
H27A	−0.0883	0.8232	0.1955	0.104*
H27B	−0.0948	0.8134	0.2816	0.104*
H27C	−0.2038	0.7840	0.2221	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.03960 (12)	0.04651 (13)	0.03583 (12)	−0.00156 (8)	0.00365 (8)	−0.00526 (8)
Cl	0.0420 (4)	0.0840 (6)	0.0476 (4)	−0.0058 (4)	−0.0027 (3)	−0.0148 (4)
N	0.0452 (13)	0.0487 (14)	0.0394 (12)	−0.0090 (11)	−0.0016 (10)	−0.0014 (11)
C1	0.0491 (17)	0.0493 (17)	0.0467 (16)	−0.0052 (14)	0.0024 (13)	−0.0015 (14)
C2	0.0449 (16)	0.0459 (17)	0.0600 (19)	−0.0055 (13)	−0.0028 (14)	−0.0017 (14)
C3	0.0475 (17)	0.0378 (16)	0.064 (2)	−0.0013 (13)	−0.0134 (15)	0.0003 (14)
C4	0.092 (3)	0.065 (2)	0.0322 (15)	−0.0094 (19)	−0.0133 (16)	−0.0009 (15)
C5	0.072 (2)	0.063 (2)	0.0373 (15)	−0.0219 (17)	0.0009 (14)	0.0007 (15)
C6	0.065 (2)	0.0519 (19)	0.0619 (18)	0.0011 (16)	−0.0064 (17)	0.0031 (17)
C7	0.0385 (14)	0.0473 (16)	0.0369 (14)	−0.0040 (12)	0.0045 (11)	−0.0058 (12)
C8	0.0511 (17)	0.0621 (19)	0.0399 (16)	0.0046 (15)	−0.0006 (13)	−0.0030 (14)
C9	0.070 (2)	0.083 (3)	0.0361 (16)	−0.0015 (19)	0.0077 (16)	−0.0032 (16)
C10	0.062 (2)	0.069 (2)	0.0546 (19)	−0.0044 (18)	0.0201 (16)	−0.0162 (17)
C11	0.0445 (17)	0.061 (2)	0.068 (2)	0.0068 (15)	0.0128 (15)	−0.0077 (16)
C12	0.0457 (16)	0.0578 (18)	0.0405 (15)	−0.0007 (14)	0.0007 (12)	0.0016 (14)
C13	0.101 (3)	0.117 (4)	0.077 (3)	−0.004 (3)	0.046 (2)	−0.029 (3)
C14	0.0433 (15)	0.0452 (16)	0.0398 (14)	−0.0033 (13)	0.0059 (12)	−0.0090 (12)
C15	0.0469 (17)	0.0564 (19)	0.0598 (19)	0.0016 (15)	0.0044 (14)	0.0036 (16)
C16	0.0531 (19)	0.062 (2)	0.066 (2)	−0.0103 (16)	0.0154 (16)	0.0005 (17)
C17	0.067 (2)	0.0494 (18)	0.0447 (16)	−0.0070 (16)	0.0089 (15)	−0.0065 (14)
C18	0.065 (2)	0.0523 (19)	0.0508 (18)	0.0130 (16)	0.0034 (15)	0.0006 (15)
C19	0.0446 (16)	0.0586 (19)	0.0472 (16)	0.0014 (14)	0.0064 (13)	−0.0049 (15)
C20	0.103 (3)	0.061 (2)	0.066 (2)	−0.012 (2)	0.013 (2)	0.0088 (18)
C21	0.0413 (15)	0.0492 (17)	0.0373 (14)	−0.0014 (13)	0.0014 (12)	−0.0086 (12)
C22	0.0552 (18)	0.058 (2)	0.0492 (17)	0.0002 (15)	0.0131 (14)	−0.0023 (14)
C23	0.0509 (18)	0.062 (2)	0.0561 (18)	0.0035 (15)	0.0139 (15)	−0.0114 (16)
C24	0.0419 (16)	0.0487 (18)	0.0579 (18)	−0.0021 (13)	−0.0035 (14)	−0.0132 (15)
C25	0.0552 (18)	0.0518 (19)	0.0554 (18)	−0.0067 (15)	0.0081 (15)	−0.0018 (15)
C26	0.0524 (17)	0.0554 (19)	0.0499 (17)	−0.0001 (15)	0.0137 (14)	−0.0066 (15)
C27	0.064 (2)	0.051 (2)	0.093 (3)	−0.0019 (17)	0.0129 (19)	−0.0160 (19)

Geometric parameters (Å, º)

Sn—Cl	2.5152 (8)	C23—C24	1.378 (4)
Sn—N	2.492 (2)	C24—C25	1.388 (4)
Sn—C7	2.136 (3)	C24—C27	1.501 (4)
Sn—C14	2.141 (3)	C25—C26	1.383 (4)
Sn—C21	2.130 (3)	C1—H1	0.93
N—C1	1.330 (4)	C2—H2	0.93
N—C5	1.337 (4)	C4—H4	0.93
C1—C2	1.373 (4)	C5—H5	0.93
C2—C3	1.368 (4)	C6—H6	0.93
C3—C4	1.388 (5)	C8—H8	0.93
C3—C6	1.488 (4)	C9—H9	0.93
C4—C5	1.388 (4)	C11—H11	0.93
C6—C6^i	1.267 (6)	C12—H12	0.93
C7—C8	1.386 (4)	C13—H13A	0.96
C7—C12	1.390 (4)	C13—H13B	0.96
C8—C9	1.383 (4)	C13—H13C	0.96
C9—C10	1.379 (5)	C15—H15	0.93
C10—C11	1.375 (5)	C16—H16	0.93
C10—C13	1.529 (4)	C18—H18	0.93
C11—C12	1.385 (4)	C19—H19	0.93
C14—C15	1.387 (4)	C20—H20A	0.96
C14—C19	1.389 (4)	C20—H20B	0.96
C15—C16	1.384 (4)	C20—H20C	0.96
C16—C17	1.374 (4)	C22—H22	0.93
C17—C18	1.381 (4)	C23—H23	0.93
C17—C20	1.505 (4)	C25—H25	0.93
C18—C19	1.385 (4)	C26—H26	0.93
C21—C22	1.381 (4)	C27—H27A	0.96
C21—C26	1.387 (4)	C27—H27B	0.96
C22—C23	1.386 (4)	C27—H27C	0.96
N—Sn—N	175.92 (6)	C2—C1—H1	117.8
C7—Sn—C7	93.87 (7)	C1—C2—H2	120.1
C14—Sn—C14	92.61 (7)	C3—C2—H2	120.1
C21—Sn—C21	91.20 (7)	C3—C4—H4	119.9
N—Sn—C7	89.67 (9)	C5—C4—H4	119.9
N—Sn—C14	87.40 (9)	N—C5—H5	118.7
N—Sn—C21	85.45 (9)	C4—C5—H5	118.7
C7—Sn—C14	119.55 (10)	C3—C6—H6	117.2
C7—Sn—C21	115.22 (11)	C6^i—C6—H6	117.2
C14—Sn—C21	124.64 (10)	C7—C8—H8	119.3
Sn—N—C1	119.54 (18)	C9—C8—H8	119.3
Sn—N—C5	122.7 (2)	C8—C9—H9	119.6
C1—N—C5	116.4 (2)	C10—C9—H9	119.6
N—C1—C2	124.3 (3)	C10—C11—H11	119.4
C1—C2—C3	119.9 (3)	C12—C11—H11	119.4
C2—C3—C4	116.7 (3)	C7—C12—H12	119.6
C2—C3—C6	118.4 (3)	C11—C12—H12	119.6
C4—C3—C6	124.9 (3)	H13A—C13—H13B	109.5
C3—C4—C5	120.2 (3)	H13A—C13—H13C	109.5
N—C5—C4	122.6 (3)	H13B—C13—H13C	109.5
C3^i—C6—C6	125.6 (5)	C10—C13—H13A	109.5
Sn—C7—C8	120.4 (2)	C10—C13—H13B	109.5
Sn—C7—C12	121.9 (2)	C10—C13—H13C	109.5
C8—C7—C12	117.5 (3)	C14—C15—H15	119.1
C7—C8—C9	121.4 (3)	C16—C15—H15	119.1
C8—C9—C10	120.7 (3)	C15—C16—H16	119.4
C9—C10—C11	118.3 (3)	C17—C16—H16	119.4
C9—C10—C13	120.8 (3)	C17—C18—H18	119.3
C11—C10—C13	120.8 (3)	C19—C18—H18	119.3
C10—C11—C12	121.3 (3)	C14—C19—H19	119.3
C7—C12—C11	120.7 (3)	C18—C19—H19	119.3
Sn—C14—C15	120.1 (2)	H20A—C20—H20B	109.5
Sn—C14—C19	122.9 (2)	H20A—C20—H20C	109.5
C15—C14—C19	116.7 (3)	H20B—C20—H20C	109.5
C14—C15—C16	121.7 (3)	C17—C20—H20A	109.5
C15—C16—C17	121.3 (3)	C17—C20—H20B	109.5
C16—C17—C18	117.7 (3)	C17—C20—H20C	109.5
C16—C17—C20	120.9 (3)	C21—C22—H22	119.3
C18—C17—C20	121.4 (3)	C23—C22—H22	119.3
C17—C18—C19	121.3 (3)	C22—C23—H23	119.5
C14—C19—C18	121.4 (3)	C24—C23—H23	119.5
Sn—C21—C22	122.6 (2)	C24—C25—H25	119.4
Sn—C21—C26	119.7 (2)	C26—C25—H25	119.4
C22—C21—C26	117.7 (3)	C21—C26—H26	119.5
C21—C22—C23	121.4 (3)	C25—C26—H26	119.5
C22—C23—C24	121.1 (3)	H27A—C27—H27B	109.5
C23—C24—C25	117.8 (3)	H27A—C27—H27C	109.5
C23—C24—C27	121.1 (3)	H27B—C27—H27C	109.5
C25—C24—C27	121.1 (3)	C24—C27—H27A	109.5
C24—C25—C26	121.2 (3)	C24—C27—H27B	109.5
C21—C26—C25	121.0 (3)	C24—C27—H27C	109.5
N—C1—H1	117.8
C2—C3—C6—C6^i	179.2 (4)	C4—C3—C6—C6^i	0.2 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

(II) [µ-(E)-4,4'-(1,2-ethenediyl)dipyridine-κ²-N:N']bis[bromotris(4- methylphenyl)tin(IV)]

Crystal data

[Sn2Br2(C7H7)6(C12H10N2)]	Dx = 1.481 Mg m^−3
Mr = 1126.18	Melting point: 122-124 C K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.736 (1) Å	Cell parameters from 20962 reflections
b = 12.060 (1) Å	θ = 3.6–25.0°
c = 18.054 (2) Å	µ = 2.62 mm^−1
β = 98.76 (1)°	T = 295 K
V = 2525.5 (4) Å^3	Block, colourless
Z = 2	0.37 × 0.21 × 0.21 mm
F(000) = 1120

Data collection

Nonius KappaCCD diffractometer	4416 independent reflections
Radiation source: fine-focus sealed tube	3932 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.6°
ϕ and ω scans with 1.0° steps	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −14→14
Tmin = 0.50, Tmax = 0.58	l = −19→21
13805 measured reflections

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) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 4.2P] where P = (Fo^2 + 2Fc^2)/3
4416 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −1.37 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 25 mm. Each frame was measured for 180 s. The number of scan sets measured was 1; the total number of frames measured was 180.

Refinement. The presence of three large troughs (−1.37, −1.22, and −1.14 e/Å^{3) near the Br atom suggest that this site may be partially occupied by Cl atoms. Chlorine is often a contaminant of Br-containing reagents.}

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

	x	y	z	Uiso*/Ueq
Sn	0.05330 (2)	0.28466 (2)	0.22384 (2)	0.0404 (1)
Br	−0.13928 (4)	0.23964 (5)	0.13034 (3)	0.0695 (2)
N	0.2228 (3)	0.3410 (3)	0.31508 (18)	0.0441 (8)
C1	0.3086 (4)	0.3959 (3)	0.2913 (2)	0.0462 (10)
H1	0.3098	0.3991	0.2399	0.055*
C2	0.3957 (4)	0.4483 (3)	0.3381 (2)	0.0468 (10)
H2	0.4526	0.4867	0.3181	0.056*
C3	0.3986 (4)	0.4437 (3)	0.4145 (3)	0.0474 (10)
C4	0.3091 (4)	0.3856 (4)	0.4397 (2)	0.0597 (12)
H4	0.3072	0.3794	0.4909	0.072*
C5	0.2235 (4)	0.3374 (4)	0.3892 (2)	0.0563 (12)
H5	0.1637	0.3008	0.4074	0.068*
C6	0.4922 (4)	0.5007 (4)	0.4640 (3)	0.0539 (11)
H6	0.5445	0.5412	0.4411	0.065*
C7	0.1643 (3)	0.2487 (3)	0.1434 (2)	0.0407 (9)
C8	0.1333 (4)	0.2796 (4)	0.0687 (2)	0.0528 (11)
H8	0.0677	0.3225	0.0549	0.063*
C9	0.1982 (5)	0.2475 (5)	0.0149 (3)	0.0634 (13)
H9	0.1761	0.2700	−0.0345	0.076*
C10	0.2953 (4)	0.1825 (5)	0.0329 (3)	0.0599 (12)
C11	0.3267 (4)	0.1528 (4)	0.1069 (3)	0.0570 (12)
H11	0.3921	0.1094	0.1204	0.068*
C12	0.2633 (4)	0.1859 (4)	0.1616 (2)	0.0461 (10)
H12	0.2875	0.1658	0.2112	0.055*
C13	0.3619 (6)	0.1409 (6)	−0.0272 (4)	0.094 (2)
H13A	0.3279	0.1699	−0.0750	0.141*
H13B	0.3596	0.0613	−0.0286	0.141*
H13C	0.4406	0.1651	−0.0161	0.141*
C14	0.0231 (3)	0.1570 (3)	0.3011 (2)	0.0422 (9)
C15	−0.0883 (4)	0.1306 (4)	0.3113 (3)	0.0525 (11)
H15	−0.1495	0.1733	0.2880	0.063*
C16	−0.1103 (4)	0.0416 (4)	0.3556 (3)	0.0592 (12)
H16	−0.1859	0.0268	0.3622	0.071*
C17	−0.0231 (4)	−0.0258 (4)	0.3903 (3)	0.0541 (11)
C18	0.0884 (4)	0.0013 (4)	0.3798 (3)	0.0546 (11)
H18	0.1494	−0.0422	0.4025	0.066*
C19	0.1112 (4)	0.0901 (4)	0.3369 (2)	0.0492 (10)
H19	0.1871	0.1060	0.3317	0.059*
C20	−0.0487 (5)	−0.1247 (5)	0.4356 (3)	0.0731 (15)
H20A	0.0221	−0.1613	0.4553	0.110*
H20B	−0.0977	−0.1751	0.4043	0.110*
H20C	−0.0869	−0.1008	0.4763	0.110*
C21	0.0001 (3)	0.4525 (4)	0.2295 (2)	0.0432 (9)
C22	−0.0740 (4)	0.4872 (4)	0.2777 (2)	0.0517 (11)
H22	−0.0980	0.4365	0.3109	0.062*
C23	−0.1131 (4)	0.5955 (4)	0.2775 (3)	0.0543 (11)
H23	−0.1628	0.6163	0.3106	0.065*
C24	−0.0796 (4)	0.6728 (4)	0.2292 (3)	0.0515 (11)
C25	−0.0065 (4)	0.6386 (4)	0.1800 (3)	0.0558 (11)
H25	0.0161	0.6891	0.1461	0.067*
C26	0.0334 (4)	0.5298 (4)	0.1808 (3)	0.0519 (11)
H26	0.0833	0.5090	0.1479	0.062*
C27	−0.1207 (5)	0.7914 (4)	0.2286 (4)	0.0743 (16)
H27A	−0.0884	0.8324	0.1912	0.111*
H27B	−0.0965	0.8242	0.2769	0.111*
H27C	−0.2033	0.7932	0.2173	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.03584 (17)	0.04718 (19)	0.03681 (18)	−0.00080 (11)	0.00093 (11)	−0.00687 (11)
Br	0.0475 (3)	0.0967 (4)	0.0603 (3)	−0.0048 (3)	−0.0044 (2)	−0.0208 (3)
N	0.0409 (18)	0.051 (2)	0.0366 (18)	−0.0086 (16)	−0.0057 (14)	−0.0024 (15)
C1	0.047 (2)	0.047 (2)	0.042 (2)	−0.0068 (19)	−0.0026 (18)	−0.0008 (18)
C2	0.042 (2)	0.042 (2)	0.053 (3)	−0.0047 (18)	−0.0019 (18)	−0.0010 (19)
C3	0.043 (2)	0.039 (2)	0.055 (3)	−0.0010 (18)	−0.0120 (19)	0.0002 (19)
C4	0.074 (3)	0.069 (3)	0.030 (2)	−0.012 (3)	−0.011 (2)	0.000 (2)
C5	0.064 (3)	0.064 (3)	0.037 (2)	−0.022 (2)	−0.001 (2)	−0.004 (2)
C6	0.053 (3)	0.049 (2)	0.054 (2)	−0.005 (2)	−0.011 (2)	0.001 (2)
C7	0.037 (2)	0.047 (2)	0.036 (2)	−0.0034 (17)	0.0000 (16)	−0.0060 (17)
C8	0.048 (2)	0.066 (3)	0.042 (2)	0.009 (2)	−0.0026 (19)	−0.002 (2)
C9	0.068 (3)	0.085 (4)	0.037 (3)	−0.001 (3)	0.005 (2)	−0.003 (2)
C10	0.059 (3)	0.070 (3)	0.053 (3)	−0.003 (2)	0.015 (2)	−0.014 (2)
C11	0.045 (2)	0.057 (3)	0.069 (3)	0.007 (2)	0.008 (2)	−0.007 (2)
C12	0.042 (2)	0.052 (2)	0.042 (2)	0.0000 (19)	0.0003 (17)	0.0007 (19)
C13	0.098 (5)	0.116 (5)	0.078 (4)	0.005 (4)	0.044 (4)	−0.027 (4)
C14	0.041 (2)	0.044 (2)	0.041 (2)	−0.0038 (17)	0.0032 (16)	−0.0111 (18)
C15	0.039 (2)	0.055 (3)	0.062 (3)	0.003 (2)	0.005 (2)	0.001 (2)
C16	0.047 (3)	0.063 (3)	0.069 (3)	−0.010 (2)	0.012 (2)	−0.004 (2)
C17	0.064 (3)	0.051 (3)	0.047 (3)	−0.007 (2)	0.006 (2)	−0.007 (2)
C18	0.059 (3)	0.056 (3)	0.047 (3)	0.012 (2)	0.002 (2)	−0.001 (2)
C19	0.037 (2)	0.061 (3)	0.048 (2)	0.0015 (19)	0.0022 (18)	−0.004 (2)
C20	0.090 (4)	0.061 (3)	0.067 (3)	−0.010 (3)	0.009 (3)	0.006 (3)
C21	0.040 (2)	0.048 (2)	0.039 (2)	−0.0016 (18)	−0.0014 (17)	−0.0071 (18)
C22	0.050 (2)	0.058 (3)	0.048 (3)	0.000 (2)	0.009 (2)	−0.004 (2)
C23	0.045 (2)	0.060 (3)	0.059 (3)	0.004 (2)	0.012 (2)	−0.014 (2)
C24	0.040 (2)	0.048 (2)	0.063 (3)	−0.0022 (19)	−0.005 (2)	−0.012 (2)
C25	0.054 (3)	0.053 (3)	0.060 (3)	−0.007 (2)	0.008 (2)	−0.002 (2)
C26	0.049 (2)	0.057 (3)	0.051 (3)	−0.001 (2)	0.011 (2)	−0.009 (2)
C27	0.069 (3)	0.052 (3)	0.103 (5)	0.002 (2)	0.015 (3)	−0.019 (3)

Geometric parameters (Å, º)

Sn—Br	2.6629 (6)	C23—C24	1.375 (7)
Sn—N	2.477 (3)	C24—C25	1.387 (7)
Sn—C7	2.137 (4)	C24—C27	1.509 (7)
Sn—C14	2.142 (4)	C25—C26	1.393 (7)
Sn—C21	2.125 (4)	C1—H1	0.93
N—C1	1.329 (5)	C2—H2	0.93
N—C5	1.338 (5)	C4—H4	0.93
C1—C2	1.377 (6)	C5—H5	0.93
C2—C3	1.376 (6)	C6—H6	0.93
C3—C4	1.395 (7)	C8—H8	0.93
C3—C6	1.476 (6)	C9—H9	0.93
C4—C5	1.379 (6)	C11—H11	0.93
C6—C6^i	1.284 (9)	C12—H12	0.93
C7—C8	1.393 (6)	C13—H13A	0.96
C7—C12	1.384 (6)	C13—H13B	0.96
C8—C9	1.378 (7)	C13—H13C	0.96
C9—C10	1.381 (7)	C15—H15	0.93
C10—C11	1.377 (7)	C16—H16	0.93
C10—C13	1.516 (7)	C18—H18	0.93
C11—C12	1.383 (6)	C19—H19	0.93
C14—C15	1.385 (6)	C20—H20A	0.96
C14—C19	1.390 (6)	C20—H20B	0.96
C15—C16	1.387 (7)	C20—H20C	0.96
C16—C17	1.380 (7)	C22—H22	0.93
C17—C18	1.390 (7)	C23—H23	0.93
C17—C20	1.502 (7)	C25—H25	0.93
C18—C19	1.372 (7)	C26—H26	0.93
C21—C22	1.385 (6)	C27—H27A	0.96
C21—C26	1.378 (6)	C27—H27B	0.96
C22—C23	1.385 (7)	C27—H27C	0.96
Br—Sn—N	174.74 (8)	C2—C1—H1	118.0
Br—Sn—C7	94.24 (10)	C1—C2—H2	120.0
Br—Sn—C14	93.29 (10)	C3—C2—H2	120.0
Br—Sn—C21	89.84 (10)	C3—C4—H4	119.9
N—Sn—C7	89.81 (13)	C5—C4—H4	119.9
N—Sn—C14	87.72 (13)	N—C5—H5	118.6
N—Sn—C21	85.36 (13)	C4—C5—H5	118.6
C7—Sn—C14	118.33 (16)	C3—C6—H6	117.1
C7—Sn—C21	116.08 (16)	C6^i—C6—H6	117.1
C14—Sn—C21	125.05 (16)	C7—C8—H8	119.4
Sn—N—C1	119.5 (3)	C9—C8—H8	119.4
Sn—N—C5	122.6 (3)	C8—C9—H9	119.4
C1—N—C5	116.8 (4)	C10—C9—H9	119.4
N—C1—C2	123.9 (4)	C10—C11—H11	119.2
C1—C2—C3	120.0 (4)	C12—C11—H11	119.2
C2—C3—C4	116.3 (4)	C7—C12—H12	119.6
C2—C3—C6	119.4 (4)	C11—C12—H12	119.6
C4—C3—C6	124.3 (4)	H13A—C13—H13B	109.5
C3—C4—C5	120.3 (4)	H13A—C13—H13C	109.5
N—C5—C4	122.7 (4)	H13B—C13—H13C	109.5
C3^i—C6—C6	125.8 (6)	C10—C13—H13A	109.5
Sn—C7—C8	120.5 (3)	C10—C13—H13B	109.5
Sn—C7—C12	121.8 (3)	C10—C13—H13C	109.5
C8—C7—C12	117.5 (4)	C14—C15—H15	119.4
C7—C8—C9	121.1 (4)	C16—C15—H15	119.4
C8—C9—C10	121.2 (5)	C15—C16—H16	119.1
C9—C10—C11	117.8 (4)	C17—C16—H16	119.1
C9—C10—C13	121.0 (5)	C17—C18—H18	119.0
C11—C10—C13	121.1 (5)	C19—C18—H18	119.0
C10—C11—C12	121.6 (4)	C14—C19—H19	119.3
C7—C12—C11	120.9 (4)	C18—C19—H19	119.3
Sn—C14—C15	120.3 (3)	H20A—C20—H20B	109.5
Sn—C14—C19	122.3 (3)	H20A—C20—H20C	109.5
C15—C14—C19	117.0 (4)	H20B—C20—H20C	109.5
C14—C15—C16	121.1 (4)	C17—C20—H20A	109.5
C15—C16—C17	121.9 (4)	C17—C20—H20B	109.5
C16—C17—C18	116.6 (4)	C17—C20—H20C	109.5
C16—C17—C20	121.3 (5)	C21—C22—H22	119.2
C18—C17—C20	122.1 (5)	C23—C22—H22	119.2
C17—C18—C19	122.0 (4)	C22—C23—H23	119.5
C14—C19—C18	121.4 (4)	C24—C23—H23	119.5
Sn—C21—C22	122.4 (3)	C24—C25—H25	119.6
Sn—C21—C26	120.0 (3)	C26—C25—H25	119.6
C22—C21—C26	117.5 (4)	C21—C26—H26	119.4
C21—C22—C23	121.6 (5)	C25—C26—H26	119.4
C22—C23—C24	120.9 (4)	H27A—C27—H27B	109.5
C23—C24—C25	118.0 (4)	H27A—C27—H27C	109.5
C23—C24—C27	121.7 (5)	H27B—C27—H27C	109.5
C25—C24—C27	120.4 (5)	C24—C27—H27A	109.5
C24—C25—C26	120.9 (5)	C24—C27—H27B	109.5
C21—C26—C25	121.1 (4)	C24—C27—H27C	109.5
N—C1—H1	118.0
C2—C3—C6—C6^i	−177.0 (6)	C4—C3—C6—C6^i	4.3 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

(III) [µ-(E)-4,4'-(1,2-ethenediyl)dipyridine-κ²-N:N']bis[iodotris(4- methylphenyl)tin(IV)]

Crystal data

[Sn2(C7H7)6I2(C12H10N2)]	Dx = 1.605 Mg m^−3
Mr = 1220.16	Melting point: 96-98 C K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.167 (1) Å	Cell parameters from 20894 reflections
b = 12.323 (1) Å	θ = 3.2–25.0°
c = 16.980 (2) Å	µ = 2.25 mm^−1
β = 97.28 (1)°	T = 295 K
V = 2525.4 (4) Å^3	Block, pale yellow
Z = 2	0.45 × 0.40 × 0.30 mm
F(000) = 1192

Data collection

Nonius KappaCCD diffractometer	4428 independent reflections
Radiation source: fine-focus sealed tube	3862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
ϕ and ω scans with 1.0° steps	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −14→14
Tmin = 0.36, Tmax = 0.48	l = −20→20
13846 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 1.8P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
4428 reflections	Δρmax = 0.38 e Å^−3
303 parameters	Δρmin = −0.72 e Å^−3
60 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (2)

Special details

Experimental. The crystal-to-detector distance was 25 mm. Each frame was measured for 240 s. The number of scan sets measured was 1; the total number of frames measured was 180.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
I	−0.12712 (2)	0.30537 (2)	0.078547 (16)	0.06897 (11)
Sn	0.058115 (17)	0.343183 (18)	0.201584 (13)	0.04106 (9)
N1	0.2114 (5)	0.3966 (10)	0.3050 (3)	0.0421 (14)	0.739 (7)
C1	0.2990 (4)	0.4443 (6)	0.2803 (3)	0.0463 (15)	0.739 (7)
H1	0.3015	0.4496	0.2260	0.056*	0.739 (7)
C2	0.3864 (4)	0.4864 (4)	0.3309 (4)	0.0467 (12)	0.739 (7)
H2	0.4446	0.5210	0.3106	0.056*	0.739 (7)
C3	0.3867 (4)	0.4767 (4)	0.4122 (4)	0.0421 (12)	0.739 (7)
C4	0.2938 (5)	0.4321 (5)	0.4380 (3)	0.0526 (14)	0.739 (7)
H4	0.2883	0.4281	0.4921	0.063*	0.739 (7)
C5	0.2090 (5)	0.3935 (6)	0.3838 (3)	0.0485 (15)	0.739 (7)
H5	0.1471	0.3639	0.4027	0.058*	0.739 (7)
C6	0.4852 (4)	0.5157 (4)	0.4639 (2)	0.0573 (15)	0.739 (7)
H6	0.5295	0.5669	0.4429	0.069*	0.739 (7)
N1A	0.2014 (14)	0.407 (3)	0.3095 (6)	0.0421 (14)	0.261 (7)
C1A	0.3030 (12)	0.439 (2)	0.2991 (6)	0.050 (5)*	0.261 (7)
H1A	0.3211	0.4427	0.2476	0.060*	0.261 (7)
C2A	0.3832 (9)	0.4682 (13)	0.3606 (7)	0.037 (4)*	0.261 (7)
H2A	0.4534	0.4887	0.3501	0.045*	0.261 (7)
C3A	0.3582 (8)	0.4663 (12)	0.4378 (7)	0.032 (3)*	0.261 (7)
C4A	0.2533 (9)	0.4326 (15)	0.4490 (6)	0.047 (4)*	0.261 (7)
H4A	0.2337	0.4275	0.5000	0.056*	0.261 (7)
C5A	0.1774 (10)	0.4065 (16)	0.3846 (7)	0.042 (4)*	0.261 (7)
H5A	0.1061	0.3874	0.3934	0.051*	0.261 (7)
C6A	0.4480 (4)	0.4914 (9)	0.5020 (6)	0.031 (3)*	0.261 (7)
H6A	0.4267	0.4953	0.5526	0.037*	0.261 (7)
C7	0.1822 (3)	0.3003 (3)	0.12886 (18)	0.0420 (7)
C8	0.1782 (3)	0.3321 (3)	0.0499 (2)	0.0575 (10)
H8	0.1229	0.3794	0.0284	0.069*
C9	0.2548 (3)	0.2949 (3)	0.0032 (2)	0.0652 (11)
H9	0.2510	0.3187	−0.0491	0.078*
C10	0.3370 (3)	0.2230 (3)	0.0322 (2)	0.0566 (9)
C11	0.3418 (3)	0.1917 (3)	0.1106 (2)	0.0546 (9)
H11	0.3971	0.1441	0.1317	0.065*
C12	0.2663 (3)	0.2295 (3)	0.1582 (2)	0.0470 (8)
H12	0.2719	0.2072	0.2108	0.056*
C13	0.4203 (4)	0.1801 (4)	−0.0190 (3)	0.0888 (15)
H13A	0.4257	0.2294	−0.0621	0.133*
H13B	0.3966	0.1103	−0.0398	0.133*
H13C	0.4914	0.1734	0.0123	0.133*
C14	0.0210 (3)	0.2148 (2)	0.27950 (18)	0.0409 (7)
C15	−0.0860 (3)	0.1745 (3)	0.2766 (2)	0.0485 (8)
H15	−0.1436	0.2086	0.2446	0.058*
C16	−0.1083 (3)	0.0840 (3)	0.3208 (2)	0.0555 (9)
H16	−0.1810	0.0599	0.3188	0.067*
C17	−0.0255 (3)	0.0290 (3)	0.3674 (2)	0.0527 (9)
C18	0.0810 (3)	0.0696 (3)	0.3711 (2)	0.0526 (9)
H18	0.1384	0.0353	0.4031	0.063*
C19	0.1039 (3)	0.1606 (3)	0.3280 (2)	0.0488 (8)
H19	0.1764	0.1859	0.3316	0.059*
C20	−0.0493 (4)	−0.0735 (3)	0.4113 (3)	0.0789 (12)
H20A	0.0058	−0.0825	0.4566	0.118*
H20B	−0.0476	−0.1347	0.3766	0.118*
H20C	−0.1212	−0.0682	0.4287	0.118*
C21	0.0036 (3)	0.5063 (3)	0.20991 (19)	0.0431 (7)
C22	−0.0672 (3)	0.5371 (3)	0.2636 (2)	0.0529 (9)
H22	−0.0864	0.4872	0.3006	0.063*
C23	−0.1101 (3)	0.6423 (3)	0.2628 (2)	0.0601 (10)
H23	−0.1562	0.6619	0.3001	0.072*
C24	−0.0852 (3)	0.7171 (3)	0.2080 (3)	0.0605 (10)
C25	−0.0132 (4)	0.6870 (3)	0.1554 (3)	0.0669 (11)
H25	0.0065	0.7373	0.1189	0.080*
C26	0.0303 (3)	0.5832 (3)	0.1562 (2)	0.0577 (9)
H26	0.0785	0.5648	0.1199	0.069*
C27	−0.1378 (4)	0.8290 (3)	0.2038 (3)	0.0934 (16)
H27A	−0.1611	0.8476	0.1493	0.140*
H27B	−0.0846	0.8814	0.2268	0.140*
H27C	−0.2007	0.8290	0.2326	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.05117 (17)	0.0806 (2)	0.06762 (19)	0.00076 (12)	−0.02163 (12)	−0.01554 (14)
Sn	0.03433 (14)	0.04676 (14)	0.04044 (14)	−0.00097 (9)	−0.00162 (9)	−0.00021 (10)
N1	0.0382 (19)	0.047 (3)	0.0383 (16)	−0.007 (2)	−0.0074 (13)	0.0003 (14)
C1	0.042 (3)	0.057 (3)	0.038 (2)	−0.017 (2)	−0.005 (2)	0.006 (3)
C2	0.043 (3)	0.047 (3)	0.046 (3)	−0.015 (2)	−0.009 (2)	0.009 (3)
C3	0.038 (3)	0.041 (3)	0.043 (3)	−0.003 (2)	−0.011 (2)	−0.002 (2)
C4	0.054 (4)	0.067 (3)	0.032 (2)	−0.013 (3)	−0.011 (2)	0.002 (2)
C5	0.041 (3)	0.063 (4)	0.040 (3)	−0.008 (3)	−0.002 (2)	−0.002 (2)
C6	0.057 (3)	0.052 (3)	0.057 (3)	−0.011 (2)	−0.014 (3)	0.005 (2)
N1A	0.0382 (19)	0.047 (3)	0.0383 (16)	−0.007 (2)	−0.0074 (13)	0.0003 (14)
C7	0.0360 (17)	0.0513 (18)	0.0372 (17)	−0.0034 (14)	−0.0009 (14)	0.0004 (15)
C8	0.055 (2)	0.076 (3)	0.0391 (19)	0.0164 (19)	−0.0048 (16)	0.0040 (18)
C9	0.069 (3)	0.091 (3)	0.0366 (19)	0.013 (2)	0.0077 (18)	0.006 (2)
C10	0.054 (2)	0.065 (2)	0.051 (2)	0.0024 (18)	0.0108 (18)	−0.0092 (18)
C11	0.045 (2)	0.055 (2)	0.062 (2)	0.0084 (16)	0.0015 (18)	0.0070 (18)
C12	0.0429 (19)	0.055 (2)	0.0418 (18)	0.0028 (15)	0.0006 (15)	0.0096 (16)
C13	0.091 (4)	0.102 (4)	0.078 (3)	0.018 (3)	0.032 (3)	−0.012 (3)
C14	0.0390 (18)	0.0417 (17)	0.0418 (17)	0.0001 (14)	0.0045 (14)	−0.0067 (14)
C15	0.0376 (19)	0.0464 (19)	0.061 (2)	0.0013 (14)	0.0023 (16)	−0.0032 (16)
C16	0.044 (2)	0.055 (2)	0.069 (2)	−0.0128 (17)	0.0111 (18)	−0.0060 (19)
C17	0.060 (2)	0.052 (2)	0.048 (2)	−0.0043 (17)	0.0126 (17)	−0.0032 (16)
C18	0.052 (2)	0.062 (2)	0.0440 (19)	0.0049 (17)	0.0059 (16)	0.0068 (17)
C19	0.0382 (18)	0.062 (2)	0.0463 (19)	−0.0048 (16)	0.0045 (15)	0.0020 (17)
C20	0.093 (3)	0.070 (3)	0.074 (3)	−0.017 (2)	0.010 (2)	0.014 (2)
C21	0.0372 (18)	0.0464 (18)	0.0423 (17)	−0.0036 (14)	−0.0088 (14)	−0.0044 (15)
C22	0.050 (2)	0.057 (2)	0.051 (2)	−0.0037 (17)	−0.0010 (17)	−0.0006 (17)
C23	0.045 (2)	0.063 (2)	0.070 (3)	0.0012 (18)	−0.0029 (18)	−0.021 (2)
C24	0.057 (2)	0.045 (2)	0.073 (3)	−0.0036 (17)	−0.015 (2)	−0.014 (2)
C25	0.078 (3)	0.050 (2)	0.070 (3)	−0.007 (2)	−0.001 (2)	0.0061 (19)
C26	0.066 (2)	0.053 (2)	0.055 (2)	0.0009 (18)	0.0076 (18)	−0.0041 (18)
C27	0.095 (4)	0.049 (2)	0.130 (5)	0.009 (2)	−0.007 (3)	−0.014 (3)

Geometric parameters (Å, º)

Sn—I	2.9100 (5)	C21—C26	1.383 (5)
Sn—N1	2.482 (4)	C22—C23	1.396 (5)
Sn—N1A	2.493 (8)	C23—C24	1.371 (6)
Sn—C7	2.135 (3)	C24—C25	1.379 (6)
Sn—C14	2.147 (3)	C24—C27	1.519 (5)
Sn—C21	2.127 (3)	C25—C26	1.384 (5)
N1—C1	1.331 (5)	C1—H1	0.93
N1—C5	1.343 (4)	C2—H2	0.93
N1A—C1A	1.331 (5)	C4—H4	0.93
C1—C2	1.381 (6)	C5—H5	0.93
C2—C3	1.384 (7)	C6—H6	0.93
C3—C4	1.378 (8)	C1A—H1A	0.93
C3—C6	1.473 (5)	C2A—H2A	0.93
C4—C5	1.377 (6)	C4A—H4A	0.93
C6—C6^i	1.294 (7)	C5A—H5A	0.93
N1A—C5A	1.343 (5)	C6A—H6A	0.93
C1A—C2A	1.381 (6)	C8—H8	0.93
C2A—C3A	1.384 (7)	C9—H9	0.93
C3A—C4A	1.378 (8)	C11—H11	0.93
C3A—C6A	1.474 (6)	C12—H12	0.93
C4A—C5A	1.377 (6)	C13—H13A	0.96
C6A—C6A^i	1.294 (7)	C13—H13B	0.96
C7—C8	1.392 (4)	C13—H13C	0.96
C7—C12	1.388 (4)	C15—H15	0.93
C8—C9	1.376 (5)	C16—H16	0.93
C9—C10	1.381 (5)	C18—H18	0.93
C10—C11	1.379 (5)	C19—H19	0.93
C10—C13	1.512 (5)	C20—H20A	0.96
C11—C12	1.379 (5)	C20—H20B	0.96
C14—C15	1.388 (4)	C20—H20C	0.96
C14—C19	1.390 (5)	C22—H22	0.93
C15—C16	1.390 (5)	C23—H23	0.93
C16—C17	1.378 (5)	C25—H25	0.93
C17—C18	1.384 (5)	C26—H26	0.93
C17—C20	1.512 (5)	C27—H27A	0.96
C18—C19	1.386 (5)	C27—H27B	0.96
C21—C22	1.384 (5)	C27—H27C	0.96
I—Sn—N1	173.8 (3)	C24—C25—C26	121.4 (4)
I—Sn—N1A	169.9 (9)	C21—C26—C25	121.2 (4)
I—Sn—C7	94.89 (8)	N1—C1—H1	118.1
I—Sn—C14	96.89 (8)	C2—C1—H1	118.1
I—Sn—C21	88.81 (8)	C1—C2—H2	120.3
N1—Sn—C7	87.23 (18)	C3—C2—H2	120.3
N1—Sn—C14	87.6 (2)	C3—C4—H4	120.0
N1—Sn—C21	85.1 (3)	C5—C4—H4	120.0
N1A—Sn—C7	91.4 (5)	N1—C5—H5	118.4
N1A—Sn—C14	87.9 (6)	C4—C5—H5	118.4
N1A—Sn—C21	81.2 (9)	C3—C6—H6	117.4
C7—Sn—C14	113.16 (12)	C6^i—C6—H6	117.4
C7—Sn—C21	121.48 (12)	N1A—C1A—H1A	118.1
C14—Sn—C21	124.31 (12)	C2A—C1A—H1A	118.1
Sn—N1—C1	117.1 (4)	C1A—C2A—H2A	120.2
Sn—N1—C5	126.0 (3)	C3A—C2A—H2A	120.2
C1—N1—C5	116.4 (4)	C3A—C4A—H4A	120.0
Sn—N1A—C1A	124.9 (6)	C5A—C4A—H4A	120.0
Sn—N1A—C5A	118.6 (6)	N1A—C5A—H5A	118.4
C1A—N1A—C5A	116.4 (4)	C4A—C5A—H5A	118.4
N1—C1—C2	123.7 (5)	C3A—C6A—H6A	115.3
C1—C2—C3	119.5 (4)	C6A^i—C6A—H6A	115.3
C2—C3—C4	117.0 (3)	C7—C8—H8	119.4
C2—C3—C6	117.7 (5)	C9—C8—H8	119.4
C4—C3—C6	125.4 (5)	C8—C9—H9	119.3
C3—C4—C5	120.0 (4)	C10—C9—H9	119.3
N1—C5—C4	123.2 (5)	C10—C11—H11	119.3
C3^i—C6—C6	125.1 (5)	C12—C11—H11	119.3
N1A—C1A—C2A	123.7 (5)	C7—C12—H12	119.4
C1A—C2A—C3A	119.5 (5)	C11—C12—H12	119.4
C2A—C3A—C4A	117.0 (4)	H13A—C13—H13B	109.5
C2A—C3A—C6A	117.7 (6)	H13A—C13—H13C	109.5
C4A—C3A—C6A	125.0 (6)	H13B—C13—H13C	109.5
C3A—C4A—C5A	120.0 (5)	C10—C13—H13A	109.5
C3A^i—C6A—C6A	129.4 (10)	C10—C13—H13B	109.5
N1A—C5A—C4A	123.2 (5)	C10—C13—H13C	109.5
Sn—C7—C8	123.1 (2)	C14—C15—H15	119.5
Sn—C7—C12	119.5 (2)	C16—C15—H15	119.5
C8—C7—C12	117.2 (3)	C15—C16—H16	119.1
C7—C8—C9	121.2 (3)	C17—C16—H16	119.1
C8—C9—C10	121.4 (3)	C17—C18—H18	119.4
C9—C10—C11	117.6 (3)	C19—C18—H18	119.4
C9—C10—C13	121.8 (4)	C14—C19—H19	119.3
C11—C10—C13	120.5 (4)	C18—C19—H19	119.3
C10—C11—C12	121.4 (3)	H20A—C20—H20B	109.5
C7—C12—C11	121.2 (3)	H20A—C20—H20C	109.5
Sn—C14—C15	120.7 (2)	H20B—C20—H20C	109.5
Sn—C14—C19	121.7 (2)	C17—C20—H20A	109.5
C15—C14—C19	117.2 (3)	C17—C20—H20B	109.5
C14—C15—C16	120.9 (3)	C17—C20—H20C	109.5
C15—C16—C17	121.8 (3)	C21—C22—H22	119.6
C16—C17—C18	117.4 (3)	C23—C22—H22	119.6
C16—C17—C20	121.5 (3)	C22—C23—H23	119.5
C18—C17—C20	121.1 (4)	C24—C23—H23	119.5
C17—C18—C19	121.2 (3)	C24—C25—H25	119.5
C14—C19—C18	121.5 (3)	C26—C25—H25	119.5
Sn—C21—C22	121.9 (3)	C21—C26—H26	119.4
Sn—C21—C26	120.2 (2)	C25—C26—H26	119.4
C22—C21—C26	117.6 (3)	H27A—C27—H27B	109.5
C21—C22—C23	120.8 (4)	H27A—C27—H27C	109.5
C22—C23—C24	121.1 (4)	H27B—C27—H27C	109.5
C23—C24—C25	118.2 (3)	C24—C27—H27A	109.5
C23—C24—C27	121.0 (4)	C24—C27—H27B	109.5
C25—C24—C27	120.8 (4)	C24—C27—H27C	109.5
C2—C3—C6—C6^i	−157.5 (7)	C2A—C3A—C6A—C6A^i	−5 (3)
C4—C3—C6—C6^i	23.2 (11)	C4A—C3A—C6A—C6A^i	169.3 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

(IV) [µ-(E)-4,4'-(1,2-ethenediyl)dipyridine-κ²-N:N']bis[chlorotriphenyltin(IV)]

Crystal data

[Sn2(C6H5)6Cl2(C12H10N2)]	Dx = 1.466 Mg m^−3
Mr = 953.10	Melting point: 187-189 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.767 (2) Å	Cell parameters from 49334 reflections
b = 14.640 (2) Å	θ = 1.0–25.0°
c = 19.148 (3) Å	µ = 1.31 mm^−1
β = 102.34 (1)°	T = 293 K
V = 4317.8 (11) Å^3	Plate, colourless
Z = 4	0.32 × 0.21 × 0.16 mm
F(000) = 1904

Data collection

Nonius KappaCCD diffractometer	7585 independent reflections
Radiation source: fine-focus sealed tube	5778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
ϕ and ω scans with 1.0° steps	h = 0→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = 0→17
Tmin = 0.66, Tmax = 0.81	l = −22→21
10037 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2)]
7585 reflections	(Δ/σ)max = 0.003
487 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. The crystal-to-detector distance was 35 mm. Each frame was measured for 40 s. The number of scan sets measured was 2; the total number of frames measured was 339.

Refinement. The displacement ellipsoids of atoms C7—C12 suggest that the phenyl ligand that they compose can adopt a range of orientations. The refinement of a two-site disorder model was, however, unstable, even when constraints and/or restraints were applied. In the end we decided that the one-site model with its very eccentric ellipsoids was preferable.

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

	x	y	z	Uiso*/Ueq
Sn1	0.90650 (1)	0.77553 (1)	0.04902 (1)	0.0451 (1)
Sn2	0.64526 (1)	0.25033 (1)	0.59672 (1)	0.0446 (1)
Cl1	0.97577 (5)	0.86925 (5)	−0.03080 (4)	0.0602 (2)
Cl2	0.58979 (6)	0.15925 (6)	0.68908 (4)	0.0644 (2)
N1	0.84631 (15)	0.67614 (16)	0.13133 (12)	0.0463 (6)
N2	0.69884 (15)	0.33554 (15)	0.50291 (11)	0.0426 (6)
C1	0.7902 (2)	0.6082 (2)	0.11174 (15)	0.0514 (8)
H1	0.7688	0.5984	0.0632	0.062*
C2	0.76216 (19)	0.5517 (2)	0.15959 (14)	0.0487 (8)
H2	0.7235	0.5046	0.1431	0.058*
C3	0.79165 (18)	0.56517 (18)	0.23251 (13)	0.0391 (7)
C4	0.8508 (2)	0.6357 (2)	0.25269 (14)	0.0510 (8)
H4	0.8726	0.6478	0.3009	0.061*
C5	0.8767 (2)	0.6871 (2)	0.20148 (15)	0.0538 (8)
H5	0.9179	0.7325	0.2163	0.065*
C6	0.75999 (18)	0.50654 (18)	0.28323 (14)	0.0432 (7)
H6	0.7163	0.4651	0.2644	0.052*
C7	0.7986 (2)	0.7426 (2)	−0.03475 (17)	0.0594 (9)
C8	0.8078 (4)	0.6933 (3)	−0.0920 (3)	0.141 (2)
H8	0.8618	0.6686	−0.0933	0.169*
C9	0.7384 (5)	0.6787 (4)	−0.1493 (3)	0.178 (4)
H9	0.7465	0.6427	−0.1873	0.214*
C10	0.6615 (5)	0.7143 (6)	−0.1509 (3)	0.171 (4)
H10	0.6150	0.7026	−0.1887	0.205*
C11	0.6523 (4)	0.7685 (6)	−0.0962 (3)	0.220 (5)
H11	0.5992	0.7968	−0.0973	0.264*
C12	0.7204 (3)	0.7828 (5)	−0.0380 (2)	0.163 (3)
H12	0.7124	0.8205	−0.0009	0.195*
C13	1.01753 (19)	0.6884 (2)	0.07668 (14)	0.0449 (7)
C14	1.0106 (2)	0.5944 (2)	0.07987 (17)	0.0626 (9)
H14	0.9559	0.5675	0.0712	0.075*
C15	1.0833 (3)	0.5401 (2)	0.0956 (2)	0.0811 (11)
H15	1.0770	0.4770	0.0965	0.097*
C16	1.1648 (3)	0.5774 (3)	0.11018 (18)	0.0740 (11)
H16	1.2137	0.5401	0.1209	0.089*
C17	1.1731 (2)	0.6702 (3)	0.10864 (16)	0.0647 (9)
H17	1.2280	0.6966	0.1196	0.078*
C18	1.1003 (2)	0.7252 (2)	0.09078 (16)	0.0563 (8)
H18	1.1071	0.7881	0.0882	0.068*
C19	0.8867 (2)	0.8858 (2)	0.11742 (14)	0.0466 (7)
C20	0.8132 (2)	0.8918 (2)	0.14626 (17)	0.0625 (9)
H20	0.7713	0.8462	0.1364	0.075*
C21	0.8010 (3)	0.9642 (3)	0.18934 (18)	0.0756 (11)
H21	0.7512	0.9670	0.2080	0.091*
C22	0.8617 (3)	1.0316 (3)	0.20455 (17)	0.0762 (11)
H22	0.8541	1.0796	0.2344	0.091*
C23	0.9335 (3)	1.0283 (2)	0.17583 (18)	0.0752 (11)
H23	0.9744	1.0749	0.1855	0.090*
C24	0.9463 (2)	0.9565 (2)	0.13261 (15)	0.0563 (8)
H24	0.9957	0.9555	0.1133	0.068*
C25	0.7671 (2)	0.3907 (2)	0.52193 (14)	0.0523 (8)
H25	0.7959	0.3915	0.5697	0.063*
C26	0.79732 (19)	0.4464 (2)	0.47512 (13)	0.0487 (8)
H26	0.8455	0.4833	0.4912	0.058*
C27	0.75588 (18)	0.44740 (18)	0.40382 (13)	0.0387 (7)
C28	0.68605 (19)	0.3885 (2)	0.38354 (14)	0.0479 (8)
H28	0.6569	0.3853	0.3359	0.057*
C29	0.66016 (19)	0.3351 (2)	0.43373 (14)	0.0467 (7)
H29	0.6130	0.2963	0.4189	0.056*
C30	0.78769 (19)	0.50694 (19)	0.35342 (14)	0.0457 (7)
H30	0.8311	0.5485	0.3725	0.055*
C31	0.5699 (2)	0.1756 (2)	0.51025 (14)	0.0524 (8)
C32	0.6017 (3)	0.0951 (3)	0.48698 (18)	0.0812 (12)
H32	0.6554	0.0729	0.5106	0.097*
C33	0.5542 (4)	0.0475 (3)	0.4290 (2)	0.1070 (16)
H33	0.5755	−0.0068	0.4143	0.128*
C34	0.4766 (4)	0.0807 (4)	0.3938 (3)	0.1130 (19)
H34	0.4451	0.0488	0.3547	0.136*
C35	0.4438 (3)	0.1596 (4)	0.4144 (2)	0.1082 (16)
H35	0.3908	0.1820	0.3893	0.130*
C36	0.4906 (2)	0.2065 (3)	0.47367 (19)	0.0734 (10)
H36	0.4677	0.2598	0.4887	0.088*
C37	0.77627 (19)	0.20700 (19)	0.63366 (14)	0.0447 (7)
C38	0.8136 (2)	0.2014 (2)	0.70618 (15)	0.0543 (8)
H38	0.7817	0.2190	0.7396	0.065*
C39	0.8969 (2)	0.1701 (3)	0.72902 (18)	0.0702 (10)
H39	0.9208	0.1672	0.7778	0.084*
C40	0.9453 (2)	0.1430 (3)	0.6814 (2)	0.0757 (11)
H40	1.0016	0.1214	0.6974	0.091*
C41	0.9093 (2)	0.1483 (2)	0.60917 (19)	0.0749 (11)
H41	0.9414	0.1303	0.5761	0.090*
C42	0.8263 (2)	0.1802 (2)	0.58608 (16)	0.0621 (9)
H42	0.8030	0.1838	0.5373	0.075*
C43	0.60078 (19)	0.3782 (2)	0.63023 (15)	0.0507 (8)
C44	0.5816 (2)	0.4526 (2)	0.58515 (17)	0.0738 (11)
H44	0.5868	0.4472	0.5379	0.089*
C45	0.5552 (3)	0.5344 (3)	0.6085 (2)	0.0991 (15)
H45	0.5430	0.5834	0.5771	0.119*
C46	0.5466 (3)	0.5443 (3)	0.6772 (3)	0.0988 (15)
H46	0.5272	0.5994	0.6923	0.119*
C47	0.5663 (3)	0.4741 (3)	0.7232 (2)	0.0995 (15)
H47	0.5621	0.4815	0.7706	0.119*
C48	0.5931 (3)	0.3900 (3)	0.70038 (17)	0.0789 (12)
H48	0.6058	0.3418	0.7326	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.04754 (14)	0.04487 (13)	0.04482 (12)	−0.00070 (10)	0.01406 (10)	0.01163 (9)
Sn2	0.05314 (15)	0.04773 (13)	0.03361 (11)	0.00572 (10)	0.01081 (9)	0.00718 (8)
Cl1	0.0647 (6)	0.0594 (5)	0.0630 (5)	0.0019 (4)	0.0277 (4)	0.0262 (4)
Cl2	0.0651 (6)	0.0797 (6)	0.0513 (4)	0.0028 (4)	0.0192 (4)	0.0270 (4)
N1	0.0487 (16)	0.0496 (15)	0.0425 (13)	−0.0091 (12)	0.0140 (12)	0.0109 (11)
N2	0.0541 (16)	0.0455 (14)	0.0298 (12)	−0.0017 (12)	0.0126 (11)	0.0051 (10)
C1	0.058 (2)	0.060 (2)	0.0362 (15)	−0.0129 (17)	0.0107 (15)	0.0064 (14)
C2	0.058 (2)	0.0486 (18)	0.0393 (16)	−0.0155 (15)	0.0095 (14)	0.0019 (13)
C3	0.0439 (18)	0.0388 (16)	0.0369 (15)	−0.0021 (13)	0.0138 (13)	0.0039 (12)
C4	0.065 (2)	0.0505 (19)	0.0356 (15)	−0.0136 (16)	0.0059 (14)	0.0039 (13)
C5	0.059 (2)	0.0529 (19)	0.0483 (18)	−0.0201 (16)	0.0078 (15)	0.0078 (15)
C6	0.0513 (19)	0.0394 (16)	0.0405 (16)	−0.0109 (14)	0.0131 (14)	0.0029 (13)
C7	0.063 (2)	0.068 (2)	0.0455 (19)	−0.0127 (18)	0.0079 (17)	0.0148 (16)
C8	0.175 (5)	0.100 (4)	0.111 (4)	0.054 (4)	−0.050 (4)	−0.044 (3)
C9	0.245 (9)	0.119 (5)	0.120 (5)	0.009 (6)	−0.075 (6)	−0.047 (4)
C10	0.129 (6)	0.280 (10)	0.080 (4)	−0.098 (6)	−0.030 (4)	0.034 (5)
C11	0.063 (4)	0.522 (15)	0.069 (3)	−0.019 (6)	0.001 (3)	0.004 (6)
C12	0.059 (3)	0.366 (9)	0.062 (3)	0.010 (4)	0.010 (2)	−0.019 (4)
C13	0.0492 (19)	0.0477 (18)	0.0399 (15)	0.0012 (15)	0.0142 (14)	0.0099 (13)
C14	0.059 (2)	0.047 (2)	0.085 (2)	−0.0018 (17)	0.0211 (19)	0.0088 (17)
C15	0.079 (3)	0.050 (2)	0.120 (3)	0.012 (2)	0.035 (3)	0.018 (2)
C16	0.068 (3)	0.077 (3)	0.081 (3)	0.024 (2)	0.027 (2)	0.025 (2)
C17	0.050 (2)	0.085 (3)	0.061 (2)	−0.004 (2)	0.0156 (17)	0.0094 (19)
C18	0.057 (2)	0.055 (2)	0.060 (2)	−0.0041 (18)	0.0187 (17)	0.0084 (16)
C19	0.052 (2)	0.0469 (18)	0.0416 (16)	0.0037 (15)	0.0120 (14)	0.0148 (13)
C20	0.062 (2)	0.056 (2)	0.074 (2)	0.0007 (18)	0.0268 (19)	0.0109 (18)
C21	0.097 (3)	0.072 (3)	0.070 (2)	0.022 (2)	0.043 (2)	0.015 (2)
C22	0.119 (4)	0.064 (3)	0.045 (2)	0.014 (2)	0.015 (2)	0.0057 (17)
C23	0.095 (3)	0.065 (2)	0.058 (2)	−0.014 (2)	0.001 (2)	−0.0042 (19)
C24	0.058 (2)	0.060 (2)	0.0483 (18)	−0.0041 (17)	0.0072 (16)	0.0105 (16)
C25	0.067 (2)	0.056 (2)	0.0288 (14)	−0.0105 (17)	0.0008 (14)	0.0024 (13)
C26	0.057 (2)	0.0526 (19)	0.0353 (15)	−0.0137 (15)	0.0068 (14)	−0.0010 (13)
C27	0.0461 (18)	0.0391 (16)	0.0331 (14)	−0.0033 (13)	0.0137 (13)	0.0007 (12)
C28	0.053 (2)	0.063 (2)	0.0267 (14)	−0.0112 (16)	0.0066 (13)	0.0093 (13)
C29	0.0453 (19)	0.0553 (19)	0.0382 (16)	−0.0097 (15)	0.0057 (14)	0.0057 (13)
C30	0.051 (2)	0.0458 (17)	0.0414 (16)	−0.0101 (14)	0.0121 (14)	0.0017 (13)
C31	0.071 (2)	0.053 (2)	0.0367 (16)	−0.0124 (17)	0.0173 (16)	0.0057 (14)
C32	0.119 (4)	0.069 (3)	0.054 (2)	0.001 (2)	0.017 (2)	−0.0058 (19)
C33	0.151 (5)	0.096 (4)	0.081 (3)	−0.015 (4)	0.040 (3)	−0.028 (3)
C34	0.118 (5)	0.145 (5)	0.081 (3)	−0.052 (4)	0.031 (3)	−0.045 (3)
C35	0.067 (3)	0.165 (5)	0.088 (3)	−0.040 (3)	0.007 (2)	−0.021 (3)
C36	0.061 (3)	0.091 (3)	0.070 (2)	−0.023 (2)	0.017 (2)	−0.009 (2)
C37	0.0509 (19)	0.0435 (17)	0.0415 (16)	0.0042 (14)	0.0139 (14)	0.0083 (13)
C38	0.056 (2)	0.063 (2)	0.0455 (17)	0.0032 (17)	0.0141 (15)	0.0023 (15)
C39	0.059 (2)	0.093 (3)	0.054 (2)	0.006 (2)	0.0016 (18)	0.0052 (19)
C40	0.053 (2)	0.086 (3)	0.089 (3)	0.012 (2)	0.016 (2)	0.013 (2)
C41	0.074 (3)	0.090 (3)	0.070 (2)	0.027 (2)	0.036 (2)	0.014 (2)
C42	0.073 (3)	0.075 (2)	0.0417 (17)	0.0220 (19)	0.0206 (17)	0.0130 (16)
C43	0.0465 (19)	0.061 (2)	0.0446 (17)	0.0044 (15)	0.0097 (14)	−0.0019 (15)
C44	0.094 (3)	0.070 (2)	0.053 (2)	0.036 (2)	0.0048 (19)	−0.0015 (18)
C45	0.117 (4)	0.080 (3)	0.090 (3)	0.052 (3)	−0.001 (3)	−0.004 (2)
C46	0.092 (3)	0.095 (4)	0.108 (4)	0.029 (3)	0.019 (3)	−0.033 (3)
C47	0.123 (4)	0.112 (4)	0.078 (3)	−0.003 (3)	0.053 (3)	−0.035 (3)
C48	0.107 (3)	0.082 (3)	0.056 (2)	0.002 (2)	0.036 (2)	−0.0032 (19)

Geometric parameters (Å, º)

Sn1—Cl1	2.4748 (8)	C38—C39	1.371 (4)
Sn1—N1	2.478 (2)	C39—C40	1.368 (4)
Sn1—C7	2.130 (3)	C40—C41	1.380 (5)
Sn1—C13	2.139 (3)	C41—C42	1.371 (4)
Sn1—C19	2.143 (3)	C43—C44	1.382 (4)
Sn2—Cl2	2.5164 (8)	C43—C48	1.385 (4)
Sn2—N2	2.479 (2)	C44—C45	1.375 (5)
Sn2—C31	2.124 (3)	C45—C46	1.357 (5)
Sn2—C37	2.132 (3)	C46—C47	1.346 (6)
Sn2—C43	2.145 (3)	C47—C48	1.402 (5)
N1—C1	1.330 (3)	C1—H1	0.93
N1—C5	1.336 (3)	C2—H2	0.93
N2—C25	1.333 (3)	C4—H4	0.93
N2—C29	1.335 (3)	C5—H5	0.93
C1—C2	1.376 (4)	C6—H6	0.93
C2—C3	1.388 (3)	C8—H8	0.93
C3—C4	1.389 (4)	C9—H9	0.93
C3—C6	1.462 (3)	C10—H10	0.93
C4—C5	1.366 (4)	C11—H11	0.93
C6—C30	1.321 (3)	C12—H12	0.93
C7—C8	1.346 (5)	C14—H14	0.93
C7—C12	1.355 (6)	C15—H15	0.93
C8—C9	1.391 (7)	C16—H16	0.93
C9—C10	1.313 (9)	C17—H17	0.93
C10—C11	1.347 (10)	C18—H18	0.93
C11—C12	1.388 (7)	C20—H20	0.93
C13—C14	1.383 (4)	C21—H21	0.93
C13—C18	1.385 (4)	C22—H22	0.93
C14—C15	1.374 (4)	C23—H23	0.93
C15—C16	1.368 (5)	C24—H24	0.93
C16—C17	1.367 (5)	C25—H25	0.93
C17—C18	1.384 (4)	C26—H26	0.93
C19—C20	1.389 (4)	C28—H28	0.93
C19—C24	1.387 (4)	C29—H29	0.93
C20—C21	1.382 (4)	C30—H30	0.93
C21—C22	1.361 (5)	C32—H32	0.93
C22—C23	1.362 (5)	C33—H33	0.93
C23—C24	1.379 (4)	C34—H34	0.93
C25—C26	1.370 (4)	C35—H35	0.93
C26—C27	1.382 (3)	C36—H36	0.93
C27—C28	1.387 (4)	C38—H38	0.93
C27—C30	1.466 (3)	C39—H39	0.93
C28—C29	1.367 (4)	C40—H40	0.93
C31—C32	1.390 (4)	C41—H41	0.93
C31—C36	1.373 (4)	C42—H42	0.93
C32—C33	1.387 (5)	C44—H44	0.93
C33—C34	1.355 (6)	C45—H45	0.93
C34—C35	1.357 (6)	C46—H46	0.93
C35—C36	1.396 (5)	C47—H47	0.93
C37—C38	1.390 (4)	C48—H48	0.93
C37—C42	1.383 (4)
Cl1—Sn1—N1	176.22 (6)	C43—C44—C45	121.6 (3)
Cl1—Sn1—C7	92.73 (8)	C44—C45—C46	120.6 (4)
Cl1—Sn1—C13	92.17 (7)	C45—C46—C47	119.7 (4)
Cl1—Sn1—C19	95.79 (8)	C46—C47—C48	120.6 (4)
N1—Sn1—C7	89.60 (10)	C43—C48—C47	120.4 (4)
N1—Sn1—C13	84.07 (9)	N1—C1—H1	118.3
N1—Sn1—C19	85.87 (9)	C2—C1—H1	118.3
C7—Sn1—C13	122.10 (13)	C1—C2—H2	120.0
C7—Sn1—C19	115.70 (13)	C3—C2—H2	120.0
C13—Sn1—C19	121.07 (11)	C3—C4—H4	120.1
N2—Sn2—N2	178.04 (6)	C5—C4—H4	120.1
C31—Sn2—C31	93.10 (8)	N1—C5—H5	118.1
C37—Sn2—C37	93.83 (7)	C4—C5—H5	118.1
C43—Sn2—C43	93.85 (8)	C3—C6—H6	117.0
N2—Sn2—C31	85.12 (9)	C30—C6—H6	117.0
N2—Sn2—C37	86.22 (9)	C7—C8—H8	119.3
N2—Sn2—C43	87.79 (9)	C9—C8—H8	119.3
C31—Sn2—C37	116.50 (12)	C8—C9—H9	119.2
C31—Sn2—C43	121.25 (12)	C10—C9—H9	119.2
C37—Sn2—C43	121.07 (11)	C9—C10—H10	121.1
Sn1—N1—C1	125.55 (18)	C11—C10—H10	121.1
Sn1—N1—C5	117.71 (18)	C10—C11—H11	119.4
C1—N1—C5	116.6 (2)	C12—C11—H11	119.4
Sn2—N2—C25	119.17 (17)	C7—C12—H12	119.6
Sn2—N2—C29	124.22 (19)	C11—C12—H12	119.6
C25—N2—C29	116.4 (2)	C13—C14—H14	119.5
N1—C1—C2	123.4 (3)	C15—C14—H14	119.5
C1—C2—C3	119.9 (3)	C14—C15—H15	119.4
C2—C3—C4	116.5 (2)	C16—C15—H15	119.4
C2—C3—C6	119.8 (2)	C15—C16—H16	120.6
C4—C3—C6	123.8 (2)	C17—C16—H16	120.6
C3—C4—C5	119.7 (3)	C16—C17—H17	119.8
N1—C5—C4	123.9 (3)	C18—C17—H17	119.8
C3—C6—C30	126.0 (3)	C13—C18—H18	119.4
Sn1—C7—C8	121.7 (3)	C17—C18—H18	119.4
Sn1—C7—C12	120.6 (3)	C19—C20—H20	119.3
C8—C7—C12	116.8 (4)	C21—C20—H20	119.3
C7—C8—C9	121.3 (6)	C20—C21—H21	119.9
C8—C9—C10	121.6 (7)	C22—C21—H21	119.9
C9—C10—C11	117.9 (6)	C21—C22—H22	120.2
C10—C11—C12	121.3 (7)	C23—C22—H22	120.2
C7—C12—C11	120.8 (6)	C22—C23—H23	119.7
Sn1—C13—C14	122.4 (2)	C24—C23—H23	119.7
Sn1—C13—C18	120.2 (2)	C19—C24—H24	119.5
C14—C13—C18	117.3 (3)	C23—C24—H24	119.5
C13—C14—C15	121.0 (3)	N2—C25—H25	118.1
C14—C15—C16	121.1 (3)	C26—C25—H25	118.1
C15—C16—C17	118.8 (3)	C25—C26—H26	120.1
C16—C17—C18	120.4 (3)	C27—C26—H26	120.1
C13—C18—C17	121.3 (3)	C27—C28—H28	120.1
Sn1—C19—C20	122.3 (2)	C29—C28—H28	120.1
Sn1—C19—C24	120.7 (2)	N2—C29—H29	118.2
C20—C19—C24	117.0 (3)	C28—C29—H29	118.2
C19—C20—C21	121.4 (3)	C6—C30—H30	117.2
C20—C21—C22	120.2 (4)	C27—C30—H30	117.2
C21—C22—C23	119.7 (4)	C31—C32—H32	119.6
C22—C23—C24	120.7 (4)	C33—C32—H32	119.6
C19—C24—C23	121.0 (3)	C32—C33—H33	120.2
N2—C25—C26	123.7 (3)	C34—C33—H33	120.2
C25—C26—C27	119.7 (3)	C33—C34—H34	119.3
C26—C27—C28	116.7 (2)	C35—C34—H34	119.3
C26—C27—C30	120.0 (3)	C34—C35—H35	120.4
C28—C27—C30	123.2 (2)	C36—C35—H35	120.4
C27—C28—C29	119.8 (3)	C31—C36—H36	119.4
N2—C29—C28	123.6 (3)	C35—C36—H36	119.4
C6—C30—C27	125.6 (3)	C37—C38—H38	119.6
Sn2—C31—C32	120.4 (3)	C39—C38—H38	119.6
Sn2—C31—C36	121.6 (3)	C38—C39—H39	119.4
C32—C31—C36	117.9 (3)	C40—C39—H39	119.4
C31—C32—C33	120.8 (4)	C39—C40—H40	120.6
C32—C33—C34	119.6 (5)	C41—C40—H40	120.6
C33—C34—C35	121.3 (5)	C40—C41—H41	119.9
C34—C35—C36	119.1 (5)	C42—C41—H41	119.9
C31—C36—C35	121.2 (4)	C37—C42—H42	119.2
Sn2—C37—C38	121.5 (2)	C41—C42—H42	119.2
Sn2—C37—C42	121.0 (2)	C43—C44—H44	119.2
C38—C37—C42	117.5 (3)	C45—C44—H44	119.2
C37—C38—C39	120.7 (3)	C44—C45—H45	119.7
C38—C39—C40	121.2 (3)	C46—C45—H45	119.7
C39—C40—C41	118.9 (3)	C45—C46—H46	120.2
C40—C41—C42	120.2 (3)	C47—C46—H46	120.2
C37—C42—C41	121.6 (3)	C46—C47—H47	119.7
Sn2—C43—C44	122.9 (2)	C48—C47—H47	119.7
Sn2—C43—C48	120.1 (2)	C43—C48—H48	119.8
C44—C43—C48	117.0 (3)	C47—C48—H48	119.8
C2—C3—C6—C30	174.2 (3)	C7—Sn1—Sn2—C31	22.0 (1)
C4—C3—C6—C30	−6.0 (5)	C13—Sn1—Sn2—C37	17.1 (1)
C26—C27—C30—C6	172.0 (3)	C19—Sn1—Sn2—C43	15.0 (1)
C28—C27—C30—C6	−6.3 (5)