Flip-type disorder in 3-substituted 2,2′:5′,2′′-terthio­phenes

In the crystal structures of four thio­phene derivatives, (E)-3′-[2-(anthracen-9-yl)ethen­yl]-2,2′:5′,2′′-terthio­phene, C₂₈H₁₈S₃, (E)-3′-[2-(1-pyren­yl)ethen­yl]-2,2′:5′,2′′-terthio­phene, C₃₀H₁₈S₃, (E)-3′-[2-(3,4-dimethoxy­phen­yl)­ethen­yl]-2,2′:5′,2′′-terthio­phene, C₂₂H₁₈O₂S₃, and (E,E)-1,4-bis­[2-(2,2′:5′,2′′-terthio­phen-3′-yl)­ethen­yl]-2,5-dimethoxy­benzene, C₃₆H₂₆O₂S₆, at least one of the terminal thio­phene rings is disordered and the disorder is of the flip type. The terthio­phene fragments are far from being coplanar, contrary to terthio­phene itself. The central C—C=C—C fragments are almost planar but the bond lengths suggest slight delocalization within this fragment. The crystal packing is determined by van der Waals inter­actions and some weak, relatively short, C—H...S and C—H...π directional contacts.

S1. Comment

Since their discovery in 1977 (Chiang et al., 1977; Shirakawa et al., 1977), conjugated polymers and oligomers have been investigated extensively for use in applications such as solar cells, actuators, light emitting diodes and nonlinear optical materials (Skotheim & Reynolds, 2007). Prominent among the conjugated materials studied to date are the oligo- and polythiophenes. These materials have good chemical stability in both their oxidized and reduced states, and a wide variety of functionality can be readily built onto the monomers whether thiophene, bithiophene or terthiophene (for example Roncali, 1999; Grant et al., 2005, and references therein).

One of the ways in which the electronic properties of thiophene oligomers and polymers may be tuned is to introduce functionality to the polymer chain, typically in the form of aromatic substituents. Thus, poly(3-arylthiophenes) have improved doping capacity and cyclability compared with polythiophene (Ferraris et al., 1998; Villers et al., 2003), and fusing benzene to thiophene leads to poly(isothianaphthene), the prototypical small band gap polymer (Wudl et al., 1984). In contrast to the planar-fused benzene ring of the isothianaphthene, the 3-aryl substituents are twisted out of the plane of the polymer backbone, reducing their electronic impact as well as disrupting the polymer interchain interactions. The styryl group is an alternative and readily accessible aromatic functionality which should not have these disadvantages and may enhance a planar morphology.

Attempts to polymerize styrylthiophenes, however, have not been so successful. Electrochemical homopolymerization of 3-styrylthiophene resulted in a nonconductive material, presumably through side-chain polymerization, and other styryl derivatives showed similar behaviour (Smith et al., 1994). However, electrically conductive polymers have been obtained by copolymerization of styryl-substituted thiophenes with 3-methylthiophene (Welzel et al., 1997), and an improvement in the photoconductivity of polythiophene was accomplished on copolymerization of thiophene and 3-(4-nitrostyryl)thiophene (Greenwald et al., 1996). Copolymers of bithiophene and para-substituted (E)-3-styrylthiophenes have also been shown to produce photovoltaic responses in photoelectrochemical cells (Cutler et al., 2001). Whilst these copolymerizations undoubtedly lead to improvement in desirable polymer properties, their irregular and random structure makes it difficult to deconvolute the role of the substituent in these improvements.

An alternative approach to the formation of regioregular styryl-functionalized oligo- and polythiophenes is to polymerize styryl-substituted terthiophene monomers, and towards this end we have reported the syntheses of a range of terthiophenes functionalized at the 3'-position with styryl groups (for example, Collis et al., 2003; Grant & Officer, 2005). We have demonstrated that the styryl functionality can control oligomer regioregularity and provides advantages in some applications. However, styrylterthiophenes largely form dimers on oxidative polymerization as a result of `polaron trapping' (Clarke et al., 2007).

There are only a few structural determinations of simple terthiophene deivatives; we have therefore determined the X-ray crystal structures of four compounds, (E)-3'-[2-(anthracen-9-yl)ethenyl]-2,2':5',2''-terthiophene, (I), (E)-3'-[2-(1-pyrenyl)ethenyl]-2,2':5',2''-terthiophene, (II), (E)-3'-[2-(3,4-dimethoxyphenyl)ethenyl]-2,2':5',2''-terthiophene, (III), and (E,E)-1,4-bis[2-(2,2':5',2''-terthiophen-3'-yl)ethenyl]-2,5- dimethoxybenzene, (IV). In all these structures, the interesting cases of a flip disorder of (at least) one of the terminal thiophene rings can be found. The preliminary data of compounds (I)–(III) were reported by Wagner & Officer (2005).

Perspective views of the molecules of (I)–(IV) are shown in Figs. 1–4. In the structure of compound (III) there are two symmetry-independent molecules (Z' = 2); there are significant differences in the conformation of these two molecules but the bond lengths and bond angles are similar (according to the normal probability plot; International Tables for X-ray Crystallography (1969). Vol. IV, pp. 293–309; Abrahams & Keve, 1971).

In all six terthiophene fragments [the molecule of (IV) contains two such fragments, cf. Fig. 4] there is a flip disorder of one of the thiophene rings; in one of the fragments of (IV) even two rings are disordered. All the structures were refined successfully with some restraints on the displacement parameters of disordered C atoms. The disorder is connected to two statistically distributed orientations of the thiophene S atom. In practice, that means that there are two molecules in which the thiophene rings are rotated by 180° approximately along the line that bisects the S—C—C angle. These two orientations are not equivalent; the site occupation factors of the higher-occupancy group refined at 0.71 (1) in (I), 0.76 (1) in (II), 0.66 (1) in (IIIA), 0.73 (1) [0.77?] in (IIIB), 0.55 (1) [0.56?] in (IVA), and 0.55 (1) [0.54?] and 0.67 (1) in (IVB). A disorder of this kind is often observed in the structures of simple thiophene derivatives with one substituent, for example, in (E)-3'-[2-(4-cyanophenyl)ethenyl][2,2':5',2'']terthiophene (Collis et al., 2003) or in 3-[2-(anthracen-9-yl)ethenyl]thiophene (Wagner et al., 2006).

The terthiophene fragments are far from planarity (Table 1), contrary to the terthiophene itself (van Bolhus et al., 1989) or its 3-methyl derivatives 3-methyl-2,2':5',2''-terthiophene (Chaloner et al., 1997) and 3,3',4''-trimethyl-2,2':5',2''-terthiophene (Barbarella et al., 1994), in which the dihedral angles between the planes of the rings are not larger than 9°. Two different modes of folding can be recognized:

(1) The terminal rings are twisted in opposite senses with respect to the central one; in consequence, the dihedral angle between terminal rings is not far from the sum of the angles between the central and the terminal rings [this mode is observed in (I), (II) and (IIIB)].

(2) The terminal rings are twisted in the same sense with respect to the central ring; the dihedral angle between the terminal rings is smaller than the angles between the central and terminal rings (IIIA) and (IV). Fig 5 shows the comparison of these two modes for the two symmetry-independent molecules of (III).

The C—C═C—C fragments are almost planar [with a maximum deviation of up to 0.022 (3) Å], but the bond-length patterns suggest that there is only small delocalization within these systems. For (I) and (II), these C—C═ C—C planes are far more twisted with respect to the large aromatic ring planes than to the central thiophene rings; this is probably a manifestation of the tendency towards minimizing the H···H steric interactions. For (III) and (IV) the dihedral angles between the appropriate planes are comparable.

The large aromatic fragments in (I) and (II) are twisted significantly with respect to the central thiophene ring [the dihedral angles are 78.80 (8)° for anthracene in (I) and 64.99 (5)° for pyrene in (II)], while the twist of the phenyl ring in (III) and (IV) is significantly smaller [up to 10.4 (1)°; Table 1]. These conformations are probably a result of the balance between the steric stress caused by the vicinity of the vinyl and the aromatic H atoms and the tendency towards the flattening of the resonance fragment.

In the crystal structures, the van der Waals forces seem to determine the packing. Some weak specific C—H···S and C—H···π directional interactions also might be of some importance (Table 2). In the case of (III), the bifurcated C—H···O hydrogen bonds connect the molecules into `homomolecular' ···AAA··· and ···BBB··· chains. Interestingly, there are no short contacts between the ring centroids, which shows that the π–π interactions are meaningless in this class of compounds; this might be due to the complicated conformations of the molecules as a whole. The stacking interactions seem to be in conflict with the tendency towards the densest packing.

Related literature

For related literature, see: Abrahams & Keve (1971); Barbarella et al. (1994); Bolhus et al. (1989); Chaloner et al. (1997); Chiang et al. (1977); Clarke et al. (2007); Collis et al. (2001, 2003); Cutler et al. (2001); Ferraris et al. (1998); Grant & Officer (2005); Grant, Jolley, Officer, Gordon & Clarke (2005); Greenwald et al. (1996); Roncali (1999); Shirakawa et al. (1977); Skotheim & Reynolds (2007); Smith et al. (1994); Villers et al. (2003); Wagner & Officer (2005); Wagner et al. (2006); Welzel et al. (1997); Wudl et al. (1984).

S2. Experimental

The investigated compounds were synthesized in a similar fashion to other styryl terthiophenes (Collis et al., 2001, 2003). Crystals of (I)–(III) were obtained by slow evaporation of ethanol. The crystal of (IV) was grown by solvent diffusion techniques (THF/hexane).

S3. Refinement

H atoms were placed at calculated positions and treated as riding, with isotropic displacement parameters set at 1.2 (1.3 for methyl groups) times the U_eq values of appropriate carrier atoms. The disordered parts in (I) were refined without any restraints; in (II)–(IV) the C atoms of the disordered parts were constrained to have the same components of the displacement tensor as the S atoms occupying the same site. This flip disorder is responsible for the relatively large differences in displacement parameters of disordered and non-disordered parts.

Computing details

For all compounds, data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. Only the molecule with the greater occupancy is represented.
	Fig. 2. A view of the molecule of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. Only the molecule with the greater occupancy is represented.
	Fig. 3. A view of the molecule of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. Only the molecule with the greater occupancy is represented.
	Fig. 4. A view of the molecule of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. Only the molecule with the greater occupancy is represented.
	Fig. 5. A comparison of two different types of twist in the terthiophene fragment (see text); two symmetry-independent molecules of (III) are shown (IIIA: solid lines; IIIB: dashed lines); the central rings were fitted one onto another (Siemens, 1989).

(I) (E)-3'-[2-(anthracen-9-yl)ethenyl]-2,2':5',2''-terthiophene

Crystal data

C28H18S3	Z = 2
Mr = 450.60	F(000) = 468
Triclinic, P1	Dx = 1.366 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7668 (8) Å	Cell parameters from 25 reflections
b = 10.8005 (9) Å	θ = 3–20°
c = 12.0272 (10) Å	µ = 0.35 mm^−1
α = 68.417 (5)°	T = 153 K
β = 68.415 (5)°	Block, colourless
γ = 84.837 (6)°	0.3 × 0.2 × 0.1 mm
V = 1095.51 (17) Å^3

Data collection

Bruker P4 CCD diffractometer	2736 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −11→11
9448 measured reflections	k = −12→12
3831 independent reflections	l = −14→14

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)] = 0.054	Hydrogen site location: difference Fourier map
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0638P)^2 + 0.3839P] where P = (Fo^2 + 2Fc^2)/3
3831 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.26191 (9)	0.49076 (7)	0.98392 (7)	0.0361 (2)
C2	0.1997 (3)	0.3739 (3)	0.9429 (3)	0.0309 (7)
C3	0.1555 (3)	0.4345 (3)	0.8398 (3)	0.0317 (7)
C4	0.1737 (3)	0.5762 (3)	0.7945 (3)	0.0344 (7)
H4	0.1481	0.6337	0.7243	0.041*
C5	0.2308 (3)	0.6220 (3)	0.8606 (3)	0.0319 (7)
C6	0.2021 (4)	0.2322 (3)	1.0164 (3)	0.0322 (7)
S7	0.3514 (4)	0.1702 (3)	1.0582 (3)	0.0410 (7)	0.709 (6)
C7	0.304 (3)	0.166 (3)	1.066 (3)	0.065 (13)	0.291 (6)
H7	0.3888	0.2117	1.0558	0.078*	0.291 (6)
C8	0.2720 (4)	0.0185 (4)	1.1388 (3)	0.0520 (9)
H8	0.3180	−0.0531	1.1839	0.062*
C9	0.1399 (4)	0.0031 (3)	1.1368 (3)	0.0530 (10)
H9	0.0820	−0.0783	1.1772	0.064*
C10	0.099 (2)	0.1288 (15)	1.0634 (18)	0.057 (7)	0.709 (6)
H10	0.0082	0.1399	1.0492	0.069*	0.709 (6)
S10	0.0675 (16)	0.1229 (8)	1.0601 (12)	0.0450 (19)	0.291 (6)
C11	0.2694 (3)	0.7599 (3)	0.8354 (3)	0.0338 (7)
S12	0.27307 (11)	0.88442 (8)	0.69396 (9)	0.0479 (3)
C13	0.3199 (4)	1.0028 (3)	0.7362 (3)	0.0466 (9)
H13	0.3350	1.0948	0.6839	0.056*
C14	0.3334 (4)	0.9528 (3)	0.8520 (3)	0.0459 (8)
H14	0.3613	1.0067	0.8881	0.055*
C15	0.3021 (3)	0.8104 (3)	0.9168 (3)	0.0352 (7)
H15	0.3032	0.7594	0.9998	0.042*
C16	0.1057 (3)	0.3639 (3)	0.7774 (3)	0.0330 (7)
H16	0.1228	0.2715	0.7984	0.040*
C17	0.0385 (3)	0.4181 (3)	0.6938 (3)	0.0336 (7)
H17	0.0159	0.5091	0.6763	0.040*
C18	−0.0036 (3)	0.3468 (3)	0.6263 (3)	0.0315 (7)
C19	−0.1539 (3)	0.3348 (3)	0.6439 (3)	0.0333 (7)
C20	−0.2669 (4)	0.3893 (3)	0.7240 (3)	0.0394 (8)
H20	−0.2416	0.4358	0.7678	0.047*
C21	−0.4112 (4)	0.3766 (3)	0.7395 (3)	0.0482 (9)
H21	−0.4849	0.4143	0.7934	0.058*
C22	−0.4519 (4)	0.3070 (4)	0.6754 (3)	0.0504 (9)
H22	−0.5522	0.2999	0.6849	0.061*
C23	−0.3474 (4)	0.2508 (3)	0.6010 (3)	0.0458 (9)
H23	−0.3762	0.2017	0.5613	0.055*
C24	−0.1961 (4)	0.2632 (3)	0.5804 (3)	0.0354 (7)
C25	−0.0881 (4)	0.2049 (3)	0.5048 (3)	0.0390 (8)
H25	−0.1169	0.1530	0.4674	0.047*
C26	0.0615 (4)	0.2200 (3)	0.4821 (3)	0.0378 (7)
C27	0.1723 (4)	0.1659 (3)	0.3997 (3)	0.0527 (9)
H27	0.1438	0.1137	0.3625	0.063*
C28	0.3175 (4)	0.1866 (4)	0.3731 (4)	0.0558 (10)
H28	0.3895	0.1486	0.3184	0.067*
C29	0.3609 (4)	0.2652 (4)	0.4269 (3)	0.0509 (9)
H29	0.4629	0.2822	0.4058	0.061*
C30	0.2600 (4)	0.3167 (3)	0.5082 (3)	0.0409 (8)
H30	0.2925	0.3688	0.5433	0.049*
C31	0.1051 (3)	0.2944 (3)	0.5424 (3)	0.0334 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0459 (5)	0.0337 (4)	0.0380 (5)	0.0035 (3)	−0.0219 (4)	−0.0167 (3)
C2	0.0337 (16)	0.0326 (16)	0.0308 (16)	0.0012 (13)	−0.0129 (13)	−0.0149 (13)
C3	0.0309 (16)	0.0337 (16)	0.0327 (16)	0.0018 (13)	−0.0120 (13)	−0.0141 (13)
C4	0.0414 (18)	0.0295 (16)	0.0389 (17)	0.0040 (13)	−0.0219 (15)	−0.0128 (14)
C5	0.0343 (17)	0.0306 (16)	0.0368 (17)	0.0049 (13)	−0.0156 (14)	−0.0166 (13)
C6	0.0348 (18)	0.0327 (17)	0.0301 (16)	0.0007 (15)	−0.0117 (15)	−0.0123 (13)
S7	0.0452 (17)	0.0379 (10)	0.0428 (9)	0.0026 (9)	−0.0273 (9)	−0.0063 (7)
C7	0.06 (2)	0.073 (17)	0.072 (15)	−0.036 (14)	−0.033 (14)	−0.026 (11)
C8	0.059 (2)	0.045 (2)	0.040 (2)	0.0100 (18)	−0.0201 (18)	−0.0020 (16)
C9	0.058 (2)	0.0363 (19)	0.047 (2)	−0.0038 (17)	−0.0073 (18)	−0.0060 (16)
C10	0.035 (10)	0.073 (10)	0.059 (6)	0.017 (6)	−0.015 (5)	−0.023 (6)
S10	0.035 (4)	0.027 (3)	0.059 (3)	−0.0012 (18)	−0.016 (2)	−0.001 (2)
C11	0.0331 (17)	0.0334 (16)	0.0393 (17)	0.0046 (13)	−0.0148 (14)	−0.0169 (14)
S12	0.0631 (6)	0.0386 (5)	0.0490 (5)	0.0011 (4)	−0.0263 (5)	−0.0172 (4)
C13	0.053 (2)	0.0336 (18)	0.056 (2)	0.0017 (16)	−0.0221 (18)	−0.0168 (16)
C14	0.053 (2)	0.0426 (19)	0.053 (2)	−0.0002 (16)	−0.0221 (18)	−0.0253 (17)
C15	0.0361 (17)	0.0239 (15)	0.055 (2)	0.0004 (12)	−0.0234 (15)	−0.0167 (14)
C16	0.0380 (18)	0.0272 (15)	0.0383 (17)	−0.0004 (13)	−0.0162 (15)	−0.0139 (13)
C17	0.0409 (18)	0.0280 (15)	0.0380 (17)	0.0017 (13)	−0.0198 (15)	−0.0129 (13)
C18	0.0412 (18)	0.0244 (14)	0.0291 (15)	−0.0017 (13)	−0.0168 (14)	−0.0050 (12)
C19	0.0416 (18)	0.0282 (15)	0.0291 (16)	−0.0030 (13)	−0.0158 (14)	−0.0050 (13)
C20	0.046 (2)	0.0352 (17)	0.0361 (17)	0.0011 (14)	−0.0170 (15)	−0.0097 (14)
C21	0.044 (2)	0.048 (2)	0.046 (2)	0.0037 (16)	−0.0110 (17)	−0.0146 (17)
C22	0.039 (2)	0.055 (2)	0.055 (2)	−0.0056 (17)	−0.0206 (18)	−0.0125 (18)
C23	0.048 (2)	0.045 (2)	0.048 (2)	−0.0075 (16)	−0.0240 (18)	−0.0130 (17)
C24	0.0466 (19)	0.0286 (16)	0.0307 (16)	−0.0062 (14)	−0.0170 (15)	−0.0054 (13)
C25	0.055 (2)	0.0324 (17)	0.0369 (17)	−0.0039 (15)	−0.0237 (16)	−0.0113 (14)
C26	0.047 (2)	0.0336 (16)	0.0346 (17)	0.0011 (14)	−0.0167 (15)	−0.0121 (14)
C27	0.067 (3)	0.047 (2)	0.054 (2)	0.0098 (18)	−0.026 (2)	−0.0268 (18)
C28	0.053 (2)	0.069 (3)	0.053 (2)	0.018 (2)	−0.0177 (19)	−0.035 (2)
C29	0.044 (2)	0.058 (2)	0.048 (2)	0.0100 (17)	−0.0177 (18)	−0.0170 (19)
C30	0.044 (2)	0.0411 (18)	0.0380 (18)	0.0015 (15)	−0.0186 (16)	−0.0105 (15)
C31	0.0425 (18)	0.0272 (15)	0.0309 (16)	0.0010 (13)	−0.0181 (14)	−0.0059 (13)

Geometric parameters (Å, º)

S1—C5	1.734 (3)	C16—C17	1.330 (4)
S1—C2	1.739 (3)	C16—H16	0.9501
C2—C3	1.378 (4)	C17—C18	1.478 (4)
C2—C6	1.462 (4)	C17—H17	0.9500
C3—C4	1.427 (4)	C18—C31	1.411 (4)
C3—C16	1.462 (4)	C18—C19	1.414 (4)
C4—C5	1.360 (4)	C19—C20	1.418 (4)
C4—H4	0.9500	C19—C24	1.441 (4)
C5—C11	1.462 (4)	C20—C21	1.365 (5)
C6—C7	1.36 (3)	C20—H20	0.9499
C6—C10	1.380 (16)	C21—C22	1.422 (5)
C6—S10	1.646 (13)	C21—H21	0.9500
C6—S7	1.715 (4)	C22—C23	1.351 (5)
S7—C8	1.653 (5)	C22—H22	0.9500
C7—C8	1.51 (3)	C23—C24	1.415 (4)
C7—H7	0.9499	C23—H23	0.9500
C8—C9	1.325 (5)	C24—C25	1.391 (4)
C8—H8	0.9500	C25—C26	1.397 (4)
C9—C10	1.437 (16)	C25—H25	0.9501
C9—S10	1.569 (11)	C26—C27	1.421 (5)
C9—H9	0.9500	C26—C31	1.439 (4)
C10—H10	0.9500	C27—C28	1.354 (5)
C11—C15	1.418 (4)	C27—H27	0.9499
C11—S12	1.728 (3)	C28—C29	1.411 (5)
S12—C13	1.690 (3)	C28—H28	0.9501
C13—C14	1.348 (5)	C29—C30	1.352 (5)
C13—H13	0.9500	C29—H29	0.9499
C14—C15	1.447 (4)	C30—C31	1.432 (4)
C14—H14	0.9500	C30—H30	0.9499
C15—H15	0.9500
C5—S1—C2	91.86 (13)	C14—C15—H15	125.7
C3—C2—C6	129.8 (3)	C17—C16—C3	125.5 (3)
C3—C2—S1	111.4 (2)	C17—C16—H16	117.2
C6—C2—S1	118.9 (2)	C3—C16—H16	117.3
C2—C3—C4	111.7 (3)	C16—C17—C18	124.7 (3)
C2—C3—C16	124.8 (3)	C16—C17—H17	117.6
C4—C3—C16	123.4 (3)	C18—C17—H17	117.7
C5—C4—C3	114.2 (3)	C31—C18—C19	120.2 (3)
C5—C4—H4	122.9	C31—C18—C17	120.4 (3)
C3—C4—H4	122.8	C19—C18—C17	119.3 (3)
C4—C5—C11	128.0 (3)	C18—C19—C20	122.5 (3)
C4—C5—S1	110.8 (2)	C18—C19—C24	119.6 (3)
C11—C5—S1	121.1 (2)	C20—C19—C24	117.9 (3)
C7—C6—C2	129.5 (13)	C21—C20—C19	121.4 (3)
C10—C6—C2	130.7 (8)	C21—C20—H20	119.3
C7—C6—S10	107.3 (13)	C19—C20—H20	119.3
C2—C6—S10	123.1 (4)	C20—C21—C22	120.4 (3)
C10—C6—S7	108.6 (8)	C20—C21—H21	119.9
C2—C6—S7	120.6 (2)	C22—C21—H21	119.8
C8—S7—C6	92.4 (2)	C23—C22—C21	119.7 (3)
C6—C7—C8	116.2 (16)	C23—C22—H22	120.2
C6—C7—H7	121.5	C21—C22—H22	120.1
C8—C7—H7	122.3	C22—C23—C24	122.0 (3)
C9—C8—C7	101.0 (10)	C22—C23—H23	119.0
C9—C8—S7	115.8 (3)	C24—C23—H23	119.0
C9—C8—H8	122.1	C25—C24—C23	122.3 (3)
C7—C8—H8	136.8	C25—C24—C19	119.1 (3)
S7—C8—H8	122.1	C23—C24—C19	118.6 (3)
C8—C9—C10	109.3 (7)	C24—C25—C26	122.1 (3)
C8—C9—S10	120.9 (6)	C24—C25—H25	118.9
C8—C9—H9	125.3	C26—C25—H25	118.9
C10—C9—H9	125.4	C25—C26—C27	122.0 (3)
S10—C9—H9	113.8	C25—C26—C31	119.1 (3)
C6—C10—C9	113.8 (13)	C27—C26—C31	118.8 (3)
C6—C10—H10	123.1	C28—C27—C26	121.7 (3)
C9—C10—H10	123.1	C28—C27—H27	119.2
C9—S10—C6	94.4 (8)	C26—C27—H27	119.1
C15—C11—C5	127.9 (3)	C27—C28—C29	119.5 (3)
C15—C11—S12	112.2 (2)	C27—C28—H28	120.2
C5—C11—S12	119.9 (2)	C29—C28—H28	120.3
C13—S12—C11	92.00 (16)	C30—C29—C28	121.2 (3)
C14—C13—S12	112.8 (3)	C30—C29—H29	119.4
C14—C13—H13	123.6	C28—C29—H29	119.4
S12—C13—H13	123.6	C29—C30—C31	121.4 (3)
C13—C14—C15	114.5 (3)	C29—C30—H30	119.3
C13—C14—H14	122.7	C31—C30—H30	119.3
C15—C14—H14	122.8	C18—C31—C30	123.2 (3)
C11—C15—C14	108.5 (3)	C18—C31—C26	119.6 (3)
C11—C15—H15	125.8	C30—C31—C26	117.2 (3)
C5—S1—C2—C3	−0.8 (2)	C5—C11—C15—C14	−179.8 (3)
C5—S1—C2—C6	178.6 (2)	S12—C11—C15—C14	−1.8 (3)
C6—C2—C3—C4	−178.9 (3)	C13—C14—C15—C11	2.0 (4)
S1—C2—C3—C4	0.4 (3)	C2—C3—C16—C17	167.3 (3)
C6—C2—C3—C16	−3.0 (5)	C4—C3—C16—C17	−17.2 (5)
S1—C2—C3—C16	176.3 (2)	C3—C16—C17—C18	176.4 (3)
C2—C3—C4—C5	0.4 (4)	C16—C17—C18—C31	−62.2 (4)
C2—C3—C4—C5	0.4 (4)	C16—C17—C18—C19	119.6 (3)
C16—C3—C4—C5	−175.6 (3)	C31—C18—C19—C20	−178.0 (3)
C3—C4—C5—C11	176.8 (3)	C17—C18—C19—C20	0.2 (4)
C3—C4—C5—S1	−0.9 (4)	C31—C18—C19—C24	3.0 (4)
C2—S1—C5—C4	1.0 (3)	C17—C18—C19—C24	−178.8 (2)
C2—S1—C5—C11	−177.0 (3)	C18—C19—C20—C21	180.0 (3)
C3—C2—C6—C7	141 (2)	C24—C19—C20—C21	−0.9 (4)
S1—C2—C6—C7	−38 (2)	C19—C20—C21—C22	0.3 (5)
C3—C2—C6—C10	−43.9 (12)	C20—C21—C22—C23	1.4 (5)
S1—C2—C6—C10	136.8 (11)	C21—C22—C23—C24	−2.4 (5)
C3—C2—C6—S10	−42.0 (7)	C22—C23—C24—C25	179.5 (3)
S1—C2—C6—S10	138.7 (6)	C22—C23—C24—C19	1.7 (5)
C3—C2—C6—S7	136.1 (3)	C18—C19—C24—C25	1.2 (4)
S1—C2—C6—S7	−43.1 (4)	C20—C19—C24—C25	−177.9 (3)
C10—C6—S7—C8	−2.7 (9)	C18—C19—C24—C23	179.1 (3)
C2—C6—S7—C8	177.3 (3)	C20—C19—C24—C23	0.0 (4)
C2—C6—C7—C8	179.3 (11)	C23—C24—C25—C26	178.4 (3)
S10—C6—C7—C8	2 (3)	C19—C24—C25—C26	−3.9 (4)
C6—C7—C8—C9	−4 (3)	C24—C25—C26—C27	−176.8 (3)
C6—S7—C8—C9	2.2 (4)	C24—C25—C26—C31	2.2 (5)
S7—C8—C9—C10	−1.0 (9)	C25—C26—C27—C28	176.6 (3)
C7—C8—C9—S10	4.5 (16)	C31—C26—C27—C28	−2.4 (5)
C2—C6—C10—C9	−177.4 (6)	C26—C27—C28—C29	−0.8 (6)
S7—C6—C10—C9	2.6 (15)	C27—C28—C29—C30	2.3 (6)
C8—C9—C10—C6	−1.1 (16)	C28—C29—C30—C31	−0.4 (5)
C8—C9—S10—C6	−3.4 (9)	C19—C18—C31—C30	172.2 (3)
C7—C6—S10—C9	0.5 (18)	C17—C18—C31—C30	−6.0 (4)
C2—C6—S10—C9	−177.0 (4)	C19—C18—C31—C26	−4.6 (4)
C4—C5—C11—C15	166.9 (3)	C17—C18—C31—C26	177.2 (3)
S1—C5—C11—C15	−15.5 (5)	C29—C30—C31—C18	−179.7 (3)
C4—C5—C11—S12	−10.9 (5)	C29—C30—C31—C26	−2.8 (4)
S1—C5—C11—S12	166.70 (17)	C25—C26—C31—C18	2.1 (4)
C15—C11—S12—C13	1.0 (3)	C27—C26—C31—C18	−178.9 (3)
C5—C11—S12—C13	179.1 (3)	C25—C26—C31—C30	−175.0 (3)
C11—S12—C13—C14	0.2 (3)	C27—C26—C31—C30	4.1 (4)
S12—C13—C14—C15	−1.3 (4)

(II) (E)-3'-[2-(1-pyrenyl)ethenyl]-2,2':5',2''-terthiophene

Crystal data

C30H18S3	Z = 2
Mr = 474.62	F(000) = 492
Triclinic, P1	Dx = 1.400 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7382 (11) Å	Cell parameters from 25 reflections
b = 11.7143 (12) Å	θ = 5–22°
c = 11.8447 (12) Å	µ = 0.35 mm^−1
α = 61.244 (8)°	T = 153 K
β = 78.532 (8)°	Block, colourless
γ = 72.307 (7)°	0.3 × 0.2 × 0.1 mm
V = 1126.2 (2) Å^3

Data collection

Bruker P4 CCD diffractometer	3208 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −11→11
9796 measured reflections	k = −13→13
3938 independent reflections	l = −14→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 0.7448P] where P = (Fo^2 + 2Fc^2)/3
3938 reflections	(Δ/σ)max = 0.001
311 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.24256 (6)	0.53678 (6)	0.48230 (6)	0.03677 (17)
C2	0.1909 (2)	0.4319 (2)	0.6383 (2)	0.0316 (5)
C3	0.0562 (2)	0.4893 (2)	0.6776 (2)	0.0299 (5)
C4	−0.0034 (2)	0.6189 (2)	0.5783 (2)	0.0335 (5)
H4	−0.0961	0.6720	0.5881	0.040*
C5	0.0843 (2)	0.6597 (2)	0.4685 (2)	0.0331 (5)
C6	0.2882 (2)	0.3018 (2)	0.7071 (2)	0.0340 (5)
S7	0.47228 (10)	0.27632 (18)	0.67794 (17)	0.0403 (3)	0.759 (3)
C7	0.437 (2)	0.278 (3)	0.678 (3)	0.0403 (3)	0.241 (3)
H7	0.4900	0.3384	0.6122	0.048*	0.241 (3)
C8	0.5024 (3)	0.1177 (3)	0.7824 (3)	0.0610 (8)
H8	0.5968	0.0604	0.7972	0.073*
C9	0.3840 (3)	0.0745 (3)	0.8452 (3)	0.0574 (8)
H9	0.3850	−0.0137	0.9119	0.069*
C10	0.2493 (12)	0.1829 (13)	0.7988 (17)	0.046 (4)	0.759 (3)
H10	0.1534	0.1724	0.8252	0.056*	0.759 (3)
S10	0.2456 (13)	0.1715 (12)	0.8226 (18)	0.050 (2)	0.241 (3)
C11	0.0636 (2)	0.7864 (2)	0.3511 (2)	0.0348 (5)
S12	−0.06795 (8)	0.92613 (6)	0.34601 (6)	0.0513 (2)
C13	−0.0234 (3)	1.0197 (3)	0.1863 (2)	0.0476 (7)
H13	−0.0712	1.1106	0.1364	0.057*
C14	0.0866 (3)	0.9493 (2)	0.1402 (2)	0.0440 (6)
H14	0.1268	0.9854	0.0539	0.053*
C15	0.1369 (3)	0.8155 (2)	0.2336 (2)	0.0394 (6)
H15	0.2141	0.7523	0.2163	0.047*
C16	−0.0109 (2)	0.4297 (2)	0.8081 (2)	0.0323 (5)
H16	0.0515	0.3631	0.8740	0.039*
C17	−0.1506 (2)	0.4592 (2)	0.8440 (2)	0.0332 (5)
H17	−0.2160	0.5217	0.7791	0.040*
C18	−0.2091 (2)	0.4004 (2)	0.9792 (2)	0.0307 (5)
C19	−0.1328 (2)	0.3818 (2)	1.0770 (2)	0.0341 (5)
H19	−0.0438	0.4074	1.0547	0.041*
C20	−0.1822 (2)	0.3273 (2)	1.2050 (2)	0.0358 (5)
H20	−0.1285	0.3190	1.2684	0.043*
C21	−0.3100 (2)	0.2843 (2)	1.2427 (2)	0.0336 (5)
C22	−0.3634 (3)	0.2252 (3)	1.3756 (2)	0.0425 (6)
H22	−0.3120	0.2175	1.4402	0.051*
C23	−0.4850 (3)	0.1804 (3)	1.4101 (2)	0.0446 (6)
H23	−0.5167	0.1403	1.4987	0.053*
C24	−0.5669 (2)	0.1923 (2)	1.3156 (2)	0.0356 (5)
C25	−0.6916 (3)	0.1439 (2)	1.3492 (3)	0.0439 (6)
H25	−0.7224	0.0999	1.4376	0.053*
C26	−0.7708 (3)	0.1596 (3)	1.2561 (3)	0.0465 (7)
H26	−0.8560	0.1275	1.2810	0.056*
C27	−0.7268 (2)	0.2213 (2)	1.1270 (3)	0.0420 (6)
H27	−0.7823	0.2312	1.0640	0.050*
C28	−0.6016 (2)	0.2694 (2)	1.0877 (2)	0.0339 (5)
C29	−0.5524 (2)	0.3334 (2)	0.9556 (2)	0.0348 (5)
H29	−0.6075	0.3458	0.8910	0.042*
C30	−0.4294 (2)	0.3769 (2)	0.9193 (2)	0.0332 (5)
H30	−0.4005	0.4189	0.8302	0.040*
C31	−0.3413 (2)	0.3610 (2)	1.0128 (2)	0.0272 (5)
C32	−0.3900 (2)	0.3005 (2)	1.1458 (2)	0.0296 (5)
C33	−0.5201 (2)	0.2544 (2)	1.1826 (2)	0.0314 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0320 (3)	0.0396 (3)	0.0310 (3)	−0.0102 (2)	0.0055 (2)	−0.0119 (3)
C2	0.0312 (12)	0.0345 (12)	0.0281 (12)	−0.0121 (10)	0.0007 (9)	−0.0118 (10)
C3	0.0302 (11)	0.0316 (11)	0.0287 (12)	−0.0100 (9)	−0.0005 (9)	−0.0134 (10)
C4	0.0308 (12)	0.0350 (12)	0.0335 (13)	−0.0093 (10)	0.0012 (10)	−0.0150 (10)
C5	0.0346 (12)	0.0343 (12)	0.0297 (12)	−0.0108 (10)	0.0001 (10)	−0.0132 (10)
C6	0.0289 (12)	0.0409 (13)	0.0322 (13)	−0.0072 (10)	−0.0007 (10)	−0.0176 (11)
S7	0.0268 (7)	0.0516 (5)	0.0406 (5)	−0.0075 (6)	0.0046 (6)	−0.0229 (4)
C7	0.0268 (7)	0.0516 (5)	0.0406 (5)	−0.0075 (6)	0.0046 (6)	−0.0229 (4)
C8	0.0427 (16)	0.068 (2)	0.074 (2)	0.0127 (14)	−0.0121 (15)	−0.0456 (18)
C9	0.067 (2)	0.0373 (15)	0.0531 (18)	−0.0012 (14)	−0.0099 (15)	−0.0135 (13)
C10	0.027 (3)	0.045 (6)	0.047 (7)	0.009 (3)	−0.005 (3)	−0.015 (5)
S10	0.062 (4)	0.032 (3)	0.046 (4)	−0.020 (3)	−0.006 (2)	−0.005 (2)
C11	0.0362 (12)	0.0334 (12)	0.0320 (13)	−0.0112 (10)	0.0013 (10)	−0.0123 (10)
S12	0.0648 (5)	0.0362 (4)	0.0387 (4)	−0.0058 (3)	0.0104 (3)	−0.0147 (3)
C13	0.0634 (17)	0.0323 (13)	0.0361 (14)	−0.0160 (12)	0.0016 (12)	−0.0061 (11)
C14	0.0509 (15)	0.0434 (14)	0.0320 (13)	−0.0209 (12)	0.0064 (11)	−0.0103 (12)
C15	0.0389 (13)	0.0401 (13)	0.0332 (13)	−0.0103 (11)	0.0029 (10)	−0.0133 (11)
C16	0.0334 (12)	0.0293 (11)	0.0291 (12)	−0.0073 (9)	0.0004 (9)	−0.0102 (10)
C17	0.0354 (12)	0.0291 (11)	0.0284 (12)	−0.0064 (10)	−0.0005 (10)	−0.0093 (10)
C18	0.0316 (11)	0.0244 (11)	0.0295 (12)	−0.0040 (9)	0.0014 (9)	−0.0100 (9)
C19	0.0327 (12)	0.0328 (12)	0.0364 (13)	−0.0108 (10)	0.0003 (10)	−0.0145 (10)
C20	0.0385 (13)	0.0385 (13)	0.0334 (13)	−0.0100 (10)	−0.0051 (10)	−0.0170 (11)
C21	0.0381 (13)	0.0328 (12)	0.0285 (12)	−0.0059 (10)	−0.0003 (10)	−0.0150 (10)
C22	0.0524 (15)	0.0483 (15)	0.0267 (12)	−0.0139 (12)	−0.0009 (11)	−0.0163 (11)
C23	0.0523 (15)	0.0472 (15)	0.0264 (13)	−0.0132 (12)	0.0058 (11)	−0.0129 (11)
C24	0.0361 (12)	0.0322 (12)	0.0302 (12)	−0.0042 (10)	0.0065 (10)	−0.0131 (10)
C25	0.0373 (13)	0.0377 (13)	0.0426 (15)	−0.0075 (11)	0.0114 (11)	−0.0132 (12)
C26	0.0305 (13)	0.0442 (15)	0.0576 (17)	−0.0097 (11)	0.0070 (12)	−0.0206 (13)
C27	0.0289 (12)	0.0437 (14)	0.0516 (16)	−0.0045 (11)	−0.0025 (11)	−0.0225 (13)
C28	0.0276 (11)	0.0311 (12)	0.0402 (13)	−0.0008 (9)	−0.0014 (10)	−0.0178 (11)
C29	0.0305 (12)	0.0395 (13)	0.0345 (13)	−0.0014 (10)	−0.0059 (10)	−0.0195 (11)
C30	0.0334 (12)	0.0345 (12)	0.0262 (12)	−0.0020 (10)	−0.0002 (9)	−0.0135 (10)
C31	0.0279 (11)	0.0255 (11)	0.0255 (11)	−0.0025 (9)	0.0010 (9)	−0.0125 (9)
C32	0.0301 (11)	0.0262 (11)	0.0296 (12)	−0.0028 (9)	0.0001 (9)	−0.0135 (9)
C33	0.0291 (11)	0.0281 (11)	0.0317 (12)	−0.0018 (9)	0.0024 (9)	−0.0141 (10)

Geometric parameters (Å, º)

S1—C2	1.732 (2)	C16—H16	0.9500
S1—C5	1.732 (2)	C17—C18	1.476 (3)
C2—C3	1.383 (3)	C17—H17	0.9501
C2—C6	1.455 (3)	C18—C19	1.393 (3)
C3—C4	1.429 (3)	C18—C31	1.418 (3)
C3—C16	1.463 (3)	C19—C20	1.380 (3)
C4—C5	1.363 (3)	C19—H19	0.9499
C4—H4	0.9500	C20—C21	1.395 (3)
C5—C11	1.456 (3)	C20—H20	0.9499
C6—C7	1.394 (19)	C21—C32	1.420 (3)
C6—C10	1.401 (14)	C21—C22	1.439 (3)
C6—S10	1.588 (14)	C22—C23	1.350 (4)
C6—S7	1.718 (2)	C22—H22	0.9500
S7—C8	1.634 (4)	C23—C24	1.431 (4)
C7—C8	1.68 (3)	C23—H23	0.9500
C7—H7	0.9500	C24—C25	1.401 (3)
C8—C9	1.338 (4)	C24—C33	1.426 (3)
C8—H8	0.9500	C25—C26	1.379 (4)
C9—S10	1.449 (13)	C25—H25	0.9500
C9—C10	1.496 (12)	C26—C27	1.381 (4)
C9—H9	0.9500	C26—H26	0.9500
C10—H10	0.9500	C27—C28	1.400 (3)
C11—C15	1.363 (3)	C27—H27	0.9501
C11—S12	1.728 (2)	C28—C33	1.415 (3)
S12—C13	1.714 (3)	C28—C29	1.426 (3)
C13—C14	1.338 (4)	C29—C30	1.354 (3)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.415 (3)	C30—C31	1.442 (3)
C14—H14	0.9500	C30—H30	0.9499
C15—H15	0.9500	C31—C32	1.429 (3)
C16—C17	1.332 (3)	C32—C33	1.433 (3)
C2—S1—C5	92.18 (11)	C3—C16—H16	116.6
C3—C2—C6	129.9 (2)	C16—C17—C18	123.6 (2)
C3—C2—S1	111.40 (16)	C16—C17—H17	118.2
C6—C2—S1	118.74 (17)	C18—C17—H17	118.2
C2—C3—C4	111.51 (19)	C19—C18—C31	118.8 (2)
C2—C3—C16	124.0 (2)	C19—C18—C17	119.6 (2)
C4—C3—C16	124.3 (2)	C31—C18—C17	121.6 (2)
C5—C4—C3	114.2 (2)	C20—C19—C18	122.2 (2)
C5—C4—H4	122.9	C20—C19—H19	118.9
C3—C4—H4	122.9	C18—C19—H19	118.9
C4—C5—C11	129.8 (2)	C19—C20—C21	120.9 (2)
C4—C5—S1	110.67 (17)	C19—C20—H20	119.6
C11—C5—S1	119.56 (17)	C21—C20—H20	119.5
C7—C6—C2	122.0 (12)	C20—C21—C32	118.4 (2)
C10—C6—C2	126.9 (5)	C20—C21—C22	122.3 (2)
C7—C6—S10	111.1 (13)	C32—C21—C22	119.2 (2)
C2—C6—S10	127.0 (5)	C23—C22—C21	121.2 (2)
C10—C6—S7	111.3 (5)	C23—C22—H22	119.4
C2—C6—S7	121.76 (18)	C21—C22—H22	119.3
C8—S7—C6	93.37 (15)	C22—C23—C24	121.2 (2)
C6—C7—C8	104.7 (16)	C22—C23—H23	119.4
C6—C7—H7	128.1	C24—C23—H23	119.4
C8—C7—H7	127.2	C25—C24—C33	118.5 (2)
C9—C8—S7	115.0 (2)	C25—C24—C23	122.3 (2)
C9—C8—C7	103.8 (7)	C33—C24—C23	119.2 (2)
C9—C8—H8	122.6	C26—C25—C24	121.2 (2)
S7—C8—H8	122.5	C26—C25—H25	119.4
C7—C8—H8	133.6	C24—C25—H25	119.4
C8—C9—S10	118.4 (6)	C25—C26—C27	120.4 (2)
C8—C9—C10	111.6 (6)	C25—C26—H26	119.7
C8—C9—H9	124.4	C27—C26—H26	119.8
S10—C9—H9	116.7	C26—C27—C28	121.0 (2)
C10—C9—H9	124.0	C26—C27—H27	119.5
C6—C10—C9	108.7 (8)	C28—C27—H27	119.5
C6—C10—H10	125.6	C27—C28—C33	119.0 (2)
C9—C10—H10	125.7	C27—C28—C29	122.7 (2)
C9—S10—C6	101.5 (8)	C33—C28—C29	118.3 (2)
C15—C11—C5	128.5 (2)	C30—C29—C28	122.0 (2)
C15—C11—S12	110.07 (17)	C30—C29—H29	119.0
C5—C11—S12	121.43 (18)	C28—C29—H29	119.0
C13—S12—C11	91.88 (12)	C29—C30—C31	121.6 (2)
C14—C13—S12	111.89 (19)	C29—C30—H30	119.2
C14—C13—H13	124.1	C31—C30—H30	119.2
S12—C13—H13	124.0	C18—C31—C32	119.0 (2)
C13—C14—C15	112.8 (2)	C18—C31—C30	123.3 (2)
C13—C14—H14	123.6	C32—C31—C30	117.7 (2)
C15—C14—H14	123.6	C21—C32—C31	120.6 (2)
C11—C15—C14	113.3 (2)	C21—C32—C33	119.4 (2)
C11—C15—H15	123.3	C31—C32—C33	120.0 (2)
C14—C15—H15	123.4	C28—C33—C24	119.9 (2)
C17—C16—C3	126.7 (2)	C28—C33—C32	120.4 (2)
C17—C16—H16	116.6	C24—C33—C32	119.7 (2)
C5—S1—C2—C3	0.52 (19)	C16—C17—C18—C19	39.6 (3)
C5—S1—C2—C6	179.97 (19)	C16—C17—C18—C31	−139.8 (2)
C6—C2—C3—C4	−179.0 (2)	C31—C18—C19—C20	−0.6 (3)
S1—C2—C3—C4	0.3 (3)	C17—C18—C19—C20	180.0 (2)
C6—C2—C3—C16	5.9 (4)	C18—C19—C20—C21	2.1 (4)
S1—C2—C3—C16	−174.71 (18)	C19—C20—C21—C32	−1.4 (3)
C2—C3—C4—C5	−1.3 (3)	C19—C20—C21—C22	179.0 (2)
C16—C3—C4—C5	173.7 (2)	C20—C21—C22—C23	−177.9 (2)
C3—C4—C5—C11	−176.7 (2)	C32—C21—C22—C23	2.5 (4)
C3—C4—C5—S1	1.7 (3)	C21—C22—C23—C24	−1.2 (4)
C2—S1—C5—C4	−1.26 (19)	C22—C23—C24—C25	178.5 (2)
C2—S1—C5—C11	177.4 (2)	C22—C23—C24—C33	−1.0 (4)
C3—C2—C6—C7	−154.6 (14)	C33—C24—C25—C26	−2.1 (3)
S1—C2—C6—C7	26.1 (14)	C23—C24—C25—C26	178.3 (2)
C3—C2—C6—C10	31.9 (9)	C24—C25—C26—C27	1.3 (4)
S1—C2—C6—C10	−147.4 (9)	C25—C26—C27—C28	−0.1 (4)
C3—C2—C6—S10	24.1 (8)	C26—C27—C28—C33	−0.2 (3)
S1—C2—C6—S10	−155.2 (7)	C26—C27—C28—C29	179.9 (2)
C3—C2—C6—S7	−150.5 (2)	C27—C28—C29—C30	−178.6 (2)
S1—C2—C6—S7	30.1 (3)	C33—C28—C29—C30	1.5 (3)
C10—C6—S7—C8	−1.2 (7)	C28—C29—C30—C31	−0.1 (3)
C2—C6—S7—C8	−179.1 (2)	C19—C18—C31—C32	−1.5 (3)
C2—C6—C7—C8	179.2 (6)	C17—C18—C31—C32	177.91 (19)
S10—C6—C7—C8	0.3 (18)	C19—C18—C31—C30	179.4 (2)
C6—S7—C8—C9	−1.1 (3)	C17—C18—C31—C30	−1.2 (3)
C6—C7—C8—C9	4.1 (17)	C29—C30—C31—C18	177.5 (2)
C7—C8—C9—S10	−7.6 (13)	C29—C30—C31—C32	−1.6 (3)
S7—C8—C9—C10	2.8 (8)	C20—C21—C32—C31	−0.7 (3)
C2—C6—C10—C9	−179.4 (4)	C22—C21—C32—C31	178.9 (2)
S7—C6—C10—C9	2.8 (12)	C20—C21—C32—C33	178.7 (2)
C8—C9—C10—C6	−3.6 (12)	C22—C21—C32—C33	−1.7 (3)
C8—C9—S10—C6	7.7 (10)	C18—C31—C32—C21	2.2 (3)
C7—C6—S10—C9	−4.2 (15)	C30—C31—C32—C21	−178.7 (2)
C2—C6—S10—C9	177.0 (4)	C18—C31—C32—C33	−177.28 (19)
C4—C5—C11—C15	−165.1 (3)	C30—C31—C32—C33	1.8 (3)
S1—C5—C11—C15	16.5 (4)	C27—C28—C33—C24	−0.6 (3)
C4—C5—C11—S12	14.4 (4)	C29—C28—C33—C24	179.3 (2)
S1—C5—C11—S12	−163.89 (14)	C27—C28—C33—C32	178.9 (2)
C15—C11—S12—C13	0.7 (2)	C29—C28—C33—C32	−1.2 (3)
C5—C11—S12—C13	−178.9 (2)	C25—C24—C33—C28	1.8 (3)
C11—S12—C13—C14	−0.9 (2)	C23—C24—C33—C28	−178.7 (2)
S12—C13—C14—C15	0.9 (3)	C25—C24—C33—C32	−177.8 (2)
C5—C11—C15—C14	179.2 (2)	C23—C24—C33—C32	1.8 (3)
S12—C11—C15—C14	−0.3 (3)	C21—C32—C33—C28	−179.9 (2)
C13—C14—C15—C11	−0.3 (4)	C31—C32—C33—C28	−0.5 (3)
C2—C3—C16—C17	−161.5 (2)	C21—C32—C33—C24	−0.4 (3)
C4—C3—C16—C17	24.1 (4)	C31—C32—C33—C24	179.0 (2)
C3—C16—C17—C18	−176.2 (2)

(III) (E)-3'-[2-(3,4-dimethoxyphenyl)ethenyl]-2,2':5',2''-terthiophene

Crystal data

C22H18O2S3	F(000) = 1712
Mr = 410.54	Dx = 1.406 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 225 reflections
a = 18.934 (1) Å	θ = 4–22°
b = 27.268 (5) Å	µ = 0.40 mm^−1
c = 7.5192 (7) Å	T = 153 K
β = 91.84 (1)°	Block, colourless
V = 3880.4 (8) Å^3	0.3 × 0.2 × 0.1 mm
Z = 8

Data collection

Bruker P4 CCD diffractometer	5330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.0°, θmin = 1.3°
ω scans	h = −15→22
20681 measured reflections	k = −24→32
6812 independent reflections	l = −8→8

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0283P)^2 + 3.3853P] where P = (Fo^2 + 2Fc^2)/3
6812 reflections	(Δ/σ)max = 0.001
505 parameters	Δρmax = 0.42 e Å^−3
1 restraint	Δρmin = −0.52 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.28630 (3)	0.91992 (2)	0.09808 (9)	0.02253 (15)
C2A	0.28352 (13)	0.85639 (8)	0.1101 (3)	0.0191 (5)
C3A	0.22060 (12)	0.83824 (8)	0.0398 (3)	0.0185 (5)
C4A	0.17557 (13)	0.87673 (9)	−0.0258 (3)	0.0206 (5)
H4A	0.1300	0.8709	−0.0779	0.025*
C5A	0.20360 (12)	0.92255 (9)	−0.0070 (3)	0.0197 (5)
C6A	0.34504 (13)	0.83088 (9)	0.1863 (3)	0.0230 (6)
S7A	0.34118 (6)	0.77993 (9)	0.3148 (4)	0.0240 (4)	0.661 (3)
C7A	0.3496 (4)	0.7862 (8)	0.304 (3)	0.0240 (4)	0.339 (3)
H7A	0.3081	0.7695	0.3380	0.029*	0.339 (3)
C8A	0.42605 (19)	0.77636 (11)	0.3491 (4)	0.0438 (8)
H8A	0.4475	0.7513	0.4201	0.053*
C9A	0.46359 (16)	0.81107 (12)	0.2706 (4)	0.0438 (8)
H9A	0.5136	0.8139	0.2783	0.053*
C10A	0.4142 (8)	0.8459 (8)	0.165 (3)	0.0285 (10)	0.661 (3)
H10A	0.4288	0.8733	0.0975	0.034*	0.661 (3)
S10A	0.4272 (3)	0.8493 (3)	0.1671 (13)	0.0285 (10)	0.339 (3)
C11A	0.17358 (13)	0.96931 (9)	−0.0639 (3)	0.0220 (5)
S12A	0.08313 (3)	0.97675 (2)	−0.08965 (9)	0.02874 (17)
C13A	0.09188 (15)	1.03525 (9)	−0.1679 (4)	0.0308 (6)
H13A	0.0534	1.0556	−0.2044	0.037*
C14A	0.16063 (15)	1.04889 (9)	−0.1715 (4)	0.0304 (6)
H14A	0.1754	1.0803	−0.2105	0.036*
C15A	0.20844 (14)	1.01197 (9)	−0.1115 (3)	0.0248 (6)
H15A	0.2583	1.0159	−0.1048	0.030*
C16A	0.20430 (13)	0.78619 (8)	0.0246 (3)	0.0198 (5)
H16A	0.2383	0.7638	0.0725	0.024*
C17A	0.14547 (13)	0.76716 (9)	−0.0505 (3)	0.0204 (5)
H17A	0.1116	0.7898	−0.0974	0.024*
C18A	0.12814 (12)	0.71525 (8)	−0.0679 (3)	0.0190 (5)
C19A	0.16881 (13)	0.67779 (8)	0.0091 (3)	0.0212 (5)
H19A	0.2088	0.6859	0.0830	0.025*
C20A	0.15182 (13)	0.62887 (9)	−0.0209 (3)	0.0226 (5)
H20A	0.1802	0.6039	0.0328	0.027*
C21A	0.09410 (13)	0.61620 (9)	−0.1276 (3)	0.0219 (5)
C22A	0.05117 (13)	0.65351 (9)	−0.2033 (3)	0.0216 (5)
C23A	0.06861 (12)	0.70193 (9)	−0.1728 (3)	0.0201 (5)
H23A	0.0395	0.7269	−0.2239	0.024*
O24A	0.07240 (9)	0.56931 (6)	−0.1656 (2)	0.0279 (4)
C25A	0.11643 (16)	0.53063 (9)	−0.0962 (4)	0.0338 (7)
H25A	0.1635	0.5332	−0.1460	0.044*
H25B	0.0955	0.4989	−0.1289	0.044*
H25C	0.1204	0.5333	0.0337	0.044*
O26A	−0.00586 (9)	0.63788 (6)	−0.3042 (2)	0.0280 (4)
C27A	−0.05379 (14)	0.67501 (9)	−0.3690 (4)	0.0310 (6)
H27A	−0.0713	0.6938	−0.2685	0.040*
H27B	−0.0937	0.6595	−0.4335	0.040*
H27C	−0.0292	0.6970	−0.4494	0.040*
S1B	0.21362 (3)	0.25140 (2)	0.39267 (8)	0.02319 (15)
C2B	0.21276 (13)	0.18793 (9)	0.4027 (3)	0.0222 (5)
C3B	0.27634 (13)	0.16973 (9)	0.4696 (3)	0.0231 (6)
C4B	0.32491 (13)	0.20817 (9)	0.5123 (3)	0.0242 (6)
H4B	0.3713	0.2023	0.5595	0.029*
C5B	0.29910 (13)	0.25411 (9)	0.4799 (3)	0.0234 (6)
C6B	0.14931 (13)	0.16138 (9)	0.3463 (3)	0.0243 (6)
S7B	0.06742 (6)	0.18387 (7)	0.3868 (3)	0.0276 (4)	0.756 (4)
C7B	0.0835 (11)	0.1796 (10)	0.377 (4)	0.0276 (4)	0.244 (4)
H7B	0.0719	0.2103	0.4282	0.033*	0.244 (4)
C8B	0.02610 (15)	0.13599 (13)	0.2999 (4)	0.0415 (8)
H8B	−0.0239	0.1330	0.2942	0.050*
C9B	0.06935 (17)	0.10164 (11)	0.2378 (4)	0.0388 (7)
H9B	0.0544	0.0715	0.1860	0.047*
C10B	0.1422 (12)	0.1167 (5)	0.261 (3)	0.0319 (16)	0.756 (4)
H10B	0.1811	0.0980	0.2212	0.038*	0.756 (4)
S10B	0.1473 (9)	0.1069 (4)	0.260 (2)	0.0319 (16)	0.244 (4)
C11B	0.33365 (13)	0.30106 (9)	0.5082 (3)	0.0245 (6)
S12B	0.41497 (4)	0.30558 (3)	0.61577 (12)	0.0395 (2)
C13B	0.41699 (16)	0.36791 (10)	0.5926 (4)	0.0349 (7)
H13B	0.4547	0.3882	0.6346	0.042*
C14B	0.35897 (19)	0.38429 (11)	0.5081 (4)	0.0466 (8)
H14B	0.3507	0.4180	0.4835	0.056*
C15B	0.31071 (17)	0.34682 (10)	0.4587 (4)	0.0413 (8)
H15B	0.2669	0.3528	0.3971	0.050*
C16B	0.29040 (13)	0.11766 (9)	0.5005 (3)	0.0255 (6)
H16B	0.2511	0.0960	0.4936	0.031*
C17B	0.35387 (13)	0.09794 (9)	0.5377 (3)	0.0258 (6)
H17B	0.3933	0.1195	0.5379	0.031*
C18B	0.36834 (13)	0.04634 (9)	0.5782 (3)	0.0237 (6)
C19B	0.31966 (13)	0.00891 (9)	0.5437 (3)	0.0259 (6)
H19B	0.2755	0.0164	0.4866	0.031*
C20B	0.33508 (13)	−0.03934 (9)	0.5922 (3)	0.0255 (6)
H20B	0.3013	−0.0645	0.5680	0.031*
C21B	0.39905 (13)	−0.05093 (9)	0.6750 (3)	0.0225 (5)
C22B	0.44934 (13)	−0.01366 (9)	0.7072 (3)	0.0217 (5)
C23B	0.43372 (13)	0.03401 (9)	0.6588 (3)	0.0227 (6)
H23B	0.4679	0.0590	0.6805	0.027*
O24B	0.41955 (9)	−0.09682 (6)	0.7302 (2)	0.0273 (4)
C25B	0.37237 (15)	−0.13618 (9)	0.6848 (4)	0.0306 (6)
H25D	0.3274	−0.1312	0.7432	0.040*
H25E	0.3933	−0.1673	0.7245	0.040*
H25F	0.3640	−0.1370	0.5555	0.040*
O26B	0.51138 (9)	−0.02879 (6)	0.7876 (2)	0.0255 (4)
C27B	0.56452 (13)	0.00813 (9)	0.8179 (4)	0.0272 (6)
H27D	0.5761	0.0233	0.7043	0.035*
H27E	0.6070	−0.0070	0.8717	0.035*
H27F	0.5467	0.0332	0.8983	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0194 (3)	0.0160 (3)	0.0317 (4)	−0.0011 (2)	−0.0062 (3)	−0.0016 (3)
C2A	0.0195 (13)	0.0154 (12)	0.0222 (13)	−0.0007 (10)	−0.0016 (10)	−0.0020 (10)
C3A	0.0175 (12)	0.0189 (12)	0.0191 (13)	−0.0006 (10)	−0.0013 (10)	−0.0016 (10)
C4A	0.0168 (12)	0.0211 (13)	0.0237 (13)	−0.0017 (10)	−0.0026 (10)	−0.0024 (10)
C5A	0.0161 (12)	0.0221 (13)	0.0206 (13)	−0.0006 (10)	−0.0022 (10)	−0.0032 (10)
C6A	0.0248 (14)	0.0185 (13)	0.0252 (14)	0.0024 (10)	−0.0064 (11)	−0.0046 (10)
S7A	0.0215 (6)	0.0198 (9)	0.0304 (7)	−0.0022 (5)	−0.0023 (6)	0.0005 (6)
C7A	0.0215 (6)	0.0198 (9)	0.0304 (7)	−0.0022 (5)	−0.0023 (6)	0.0005 (6)
C8A	0.069 (2)	0.0281 (16)	0.0335 (17)	0.0258 (16)	−0.0159 (16)	−0.0045 (13)
C9A	0.0215 (15)	0.057 (2)	0.052 (2)	0.0081 (14)	−0.0093 (14)	−0.0186 (17)
C10A	0.013 (3)	0.0260 (15)	0.0453 (10)	−0.0017 (18)	−0.0074 (19)	0.0026 (9)
S10A	0.013 (3)	0.0260 (15)	0.0453 (10)	−0.0017 (18)	−0.0074 (19)	0.0026 (9)
C11A	0.0209 (13)	0.0194 (13)	0.0255 (14)	0.0023 (10)	−0.0007 (11)	−0.0014 (10)
S12A	0.0219 (3)	0.0245 (4)	0.0395 (4)	0.0034 (3)	−0.0034 (3)	0.0047 (3)
C13A	0.0368 (16)	0.0239 (14)	0.0313 (15)	0.0113 (12)	−0.0042 (12)	0.0028 (12)
C14A	0.0377 (16)	0.0186 (13)	0.0349 (16)	0.0013 (12)	0.0036 (13)	−0.0015 (11)
C15A	0.0231 (13)	0.0204 (13)	0.0307 (15)	0.0018 (11)	−0.0004 (11)	−0.0024 (11)
C16A	0.0200 (13)	0.0167 (12)	0.0227 (13)	0.0023 (10)	−0.0007 (10)	−0.0008 (10)
C17A	0.0205 (13)	0.0197 (13)	0.0208 (13)	0.0021 (10)	−0.0011 (10)	−0.0006 (10)
C18A	0.0183 (12)	0.0197 (12)	0.0190 (13)	−0.0019 (10)	0.0004 (10)	−0.0019 (10)
C19A	0.0192 (13)	0.0207 (13)	0.0236 (13)	−0.0009 (10)	−0.0023 (10)	−0.0007 (10)
C20A	0.0233 (13)	0.0218 (13)	0.0226 (13)	0.0036 (11)	0.0002 (10)	0.0016 (10)
C21A	0.0251 (14)	0.0161 (13)	0.0244 (14)	−0.0007 (10)	0.0004 (11)	−0.0014 (10)
C22A	0.0217 (13)	0.0227 (13)	0.0201 (13)	−0.0026 (10)	−0.0029 (10)	−0.0044 (10)
C23A	0.0183 (12)	0.0184 (13)	0.0234 (13)	0.0015 (10)	−0.0005 (10)	0.0015 (10)
O24A	0.0310 (10)	0.0151 (9)	0.0372 (11)	−0.0006 (7)	−0.0071 (8)	−0.0012 (8)
C25A	0.0473 (18)	0.0176 (14)	0.0357 (16)	0.0042 (12)	−0.0081 (14)	0.0011 (12)
O26A	0.0278 (10)	0.0179 (9)	0.0373 (11)	−0.0002 (7)	−0.0150 (8)	−0.0029 (8)
C27A	0.0322 (15)	0.0241 (14)	0.0357 (16)	0.0013 (12)	−0.0143 (12)	−0.0030 (12)
S1B	0.0214 (3)	0.0209 (3)	0.0271 (3)	0.0022 (3)	−0.0028 (3)	0.0026 (3)
C2B	0.0211 (13)	0.0211 (13)	0.0242 (13)	0.0002 (10)	−0.0004 (10)	0.0037 (10)
C3B	0.0209 (13)	0.0228 (13)	0.0255 (14)	0.0013 (10)	0.0002 (11)	0.0043 (11)
C4B	0.0185 (13)	0.0235 (14)	0.0303 (15)	−0.0003 (10)	−0.0028 (11)	0.0028 (11)
C5B	0.0205 (13)	0.0242 (14)	0.0254 (13)	−0.0005 (10)	0.0014 (10)	0.0020 (11)
C6B	0.0215 (13)	0.0248 (14)	0.0262 (14)	−0.0006 (11)	−0.0047 (11)	0.0078 (11)
S7B	0.0155 (8)	0.0350 (7)	0.0321 (6)	0.0014 (6)	−0.0002 (6)	−0.0036 (4)
C7B	0.0155 (8)	0.0350 (7)	0.0321 (6)	0.0014 (6)	−0.0002 (6)	−0.0036 (4)
C8B	0.0218 (15)	0.074 (2)	0.0285 (16)	−0.0110 (15)	−0.0033 (12)	0.0074 (15)
C9B	0.0490 (19)	0.0322 (16)	0.0344 (17)	−0.0163 (14)	−0.0116 (14)	0.0054 (13)
C10B	0.030 (2)	0.023 (4)	0.0422 (11)	0.006 (3)	−0.0090 (12)	−0.005 (3)
S10B	0.030 (2)	0.023 (4)	0.0422 (11)	0.006 (3)	−0.0090 (12)	−0.005 (3)
C11B	0.0238 (14)	0.0248 (14)	0.0249 (14)	−0.0014 (11)	−0.0001 (11)	0.0007 (11)
S12B	0.0216 (4)	0.0269 (4)	0.0696 (6)	−0.0023 (3)	−0.0036 (4)	−0.0018 (4)
C13B	0.0383 (17)	0.0255 (15)	0.0413 (17)	−0.0097 (13)	0.0058 (14)	−0.0061 (13)
C14B	0.064 (2)	0.0207 (15)	0.053 (2)	−0.0072 (15)	−0.0186 (17)	0.0028 (14)
C15B	0.0493 (19)	0.0225 (15)	0.0505 (19)	−0.0013 (13)	−0.0241 (15)	0.0029 (13)
C16B	0.0221 (14)	0.0202 (13)	0.0342 (15)	−0.0022 (11)	−0.0010 (11)	0.0027 (11)
C17B	0.0225 (14)	0.0202 (13)	0.0346 (15)	−0.0011 (11)	−0.0033 (11)	0.0028 (11)
C18B	0.0197 (13)	0.0227 (13)	0.0286 (14)	0.0012 (11)	−0.0008 (11)	0.0002 (11)
C19B	0.0173 (13)	0.0271 (15)	0.0330 (15)	0.0007 (11)	−0.0034 (11)	0.0006 (11)
C20B	0.0244 (14)	0.0216 (13)	0.0305 (15)	−0.0044 (11)	−0.0001 (11)	−0.0007 (11)
C21B	0.0259 (14)	0.0168 (13)	0.0249 (13)	0.0000 (10)	0.0013 (11)	0.0007 (10)
C22B	0.0209 (13)	0.0226 (13)	0.0215 (13)	0.0018 (11)	−0.0001 (10)	0.0010 (10)
C23B	0.0191 (13)	0.0186 (13)	0.0305 (14)	−0.0019 (10)	0.0004 (11)	−0.0012 (10)
O24B	0.0306 (10)	0.0142 (9)	0.0369 (11)	−0.0022 (7)	−0.0040 (8)	0.0031 (8)
C25B	0.0409 (17)	0.0169 (13)	0.0335 (15)	−0.0062 (12)	−0.0053 (13)	−0.0007 (11)
O26B	0.0215 (9)	0.0192 (9)	0.0352 (11)	−0.0014 (7)	−0.0063 (8)	0.0041 (8)
C27B	0.0212 (14)	0.0226 (14)	0.0374 (16)	−0.0039 (11)	−0.0056 (12)	0.0044 (11)

Geometric parameters (Å, º)

S1A—C5A	1.733 (2)	S1B—C5B	1.728 (3)
S1A—C2A	1.736 (2)	S1B—C2B	1.732 (2)
C2A—C3A	1.380 (3)	C2B—C3B	1.382 (3)
C2A—C6A	1.458 (3)	C2B—C6B	1.454 (3)
C3A—C4A	1.430 (3)	C3B—C4B	1.424 (3)
C3A—C16A	1.456 (3)	C3B—C16B	1.462 (3)
C4A—C5A	1.363 (3)	C4B—C5B	1.364 (3)
C4A—H4A	0.9499	C4B—H4B	0.9500
C5A—C11A	1.455 (3)	C5B—C11B	1.450 (3)
C6A—C10A	1.386 (15)	C6B—C7B	1.37 (2)
C6A—C7A	1.51 (2)	C6B—C10B	1.384 (16)
C6A—S10A	1.645 (6)	C6B—S10B	1.621 (13)
C6A—S7A	1.695 (3)	C6B—S7B	1.704 (3)
S7A—C8A	1.622 (4)	S7B—C8B	1.646 (4)
C7A—C8A	1.5001 (10)	C7B—C8B	1.70 (3)
C7A—H7A	0.9501	C7B—H7B	0.9500
C8A—C9A	1.333 (5)	C8B—C9B	1.338 (4)
C8A—H8A	0.9499	C8B—H8B	0.9501
C9A—S10A	1.459 (11)	C9B—C10B	1.44 (2)
C9A—C10A	1.53 (2)	C9B—S10B	1.488 (17)
C9A—H9A	0.9501	C9B—H9B	0.9499
C10A—H10A	0.9499	C10B—H10B	0.9498
C11A—C15A	1.390 (3)	C11B—C15B	1.369 (4)
C11A—S12A	1.729 (2)	C11B—S12B	1.721 (3)
S12A—C13A	1.710 (3)	S12B—C13B	1.709 (3)
C13A—C14A	1.355 (4)	C13B—C14B	1.329 (4)
C13A—H13A	0.9498	C13B—H13B	0.9499
C14A—C15A	1.418 (4)	C14B—C15B	1.413 (4)
C14A—H14A	0.9501	C14B—H14B	0.9498
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.338 (3)	C16B—C17B	1.338 (4)
C16A—H16A	0.9499	C16B—H16B	0.9500
C17A—C18A	1.458 (3)	C17B—C18B	1.464 (3)
C17A—H17A	0.9500	C17B—H17B	0.9499
C18A—C19A	1.394 (3)	C18B—C19B	1.394 (3)
C18A—C23A	1.403 (3)	C18B—C23B	1.402 (3)
C19A—C20A	1.389 (3)	C19B—C20B	1.394 (3)
C19A—H19A	0.9500	C19B—H19B	0.9501
C20A—C21A	1.379 (3)	C20B—C21B	1.381 (4)
C20A—H20A	0.9499	C20B—H20B	0.9500
C21A—O24A	1.371 (3)	C21B—O24B	1.371 (3)
C21A—C22A	1.411 (3)	C21B—C22B	1.408 (3)
C22A—O26A	1.368 (3)	C22B—O26B	1.367 (3)
C22A—C23A	1.378 (3)	C22B—C23B	1.379 (3)
C23A—H23A	0.9499	C23B—H23B	0.9501
O24A—C25A	1.432 (3)	O24B—C25B	1.431 (3)
C25A—H25A	0.9800	C25B—H25D	0.9800
C25A—H25B	0.9800	C25B—H25E	0.9800
C25A—H25C	0.9800	C25B—H25F	0.9800
O26A—C27A	1.435 (3)	O26B—C27B	1.436 (3)
C27A—H27A	0.9800	C27B—H27D	0.9800
C27A—H27B	0.9800	C27B—H27E	0.9800
C27A—H27C	0.9800	C27B—H27F	0.9800
C5A—S1A—C2A	92.10 (11)	C5B—S1B—C2B	92.07 (12)
C3A—C2A—C6A	130.4 (2)	C3B—C2B—C6B	129.0 (2)
C3A—C2A—S1A	111.44 (18)	C3B—C2B—S1B	111.44 (19)
C6A—C2A—S1A	118.12 (18)	C6B—C2B—S1B	119.56 (18)
C2A—C3A—C4A	111.5 (2)	C2B—C3B—C4B	111.5 (2)
C2A—C3A—C16A	123.9 (2)	C2B—C3B—C16B	124.0 (2)
C4A—C3A—C16A	124.5 (2)	C4B—C3B—C16B	124.5 (2)
C5A—C4A—C3A	114.3 (2)	C5B—C4B—C3B	114.3 (2)
C5A—C4A—H4A	122.9	C5B—C4B—H4B	122.9
C3A—C4A—H4A	122.9	C3B—C4B—H4B	122.9
C4A—C5A—C11A	128.7 (2)	C4B—C5B—C11B	128.9 (2)
C4A—C5A—S1A	110.64 (18)	C4B—C5B—S1B	110.75 (19)
C11A—C5A—S1A	120.62 (18)	C11B—C5B—S1B	120.38 (19)
C10A—C6A—C2A	124.1 (10)	C7B—C6B—C2B	121.3 (12)
C2A—C6A—C7A	130.3 (4)	C10B—C6B—C2B	129.9 (9)
C2A—C6A—S10A	124.5 (4)	C7B—C6B—S10B	113.0 (14)
C7A—C6A—S10A	105.1 (5)	C2B—C6B—S10B	125.5 (6)
C10A—C6A—S7A	111.4 (10)	C10B—C6B—S7B	109.0 (9)
C2A—C6A—S7A	124.50 (19)	C2B—C6B—S7B	121.1 (2)
C8A—S7A—C6A	94.55 (16)	C8B—S7B—C6B	93.85 (16)
C8A—C7A—C6A	108.4 (11)	C6B—C7B—C8B	105.4 (16)
C8A—C7A—H7A	130.8	C6B—C7B—H7B	127.7
C6A—C7A—H7A	120.9	C8B—C7B—H7B	126.9
C9A—C8A—C7A	107.3 (9)	C9B—C8B—S7B	113.9 (2)
C9A—C8A—S7A	115.2 (2)	C9B—C8B—C7B	102.5 (7)
C9A—C8A—H8A	122.3	C9B—C8B—H8B	123.0
C7A—C8A—H8A	130.5	S7B—C8B—H8B	123.1
S7A—C8A—H8A	122.5	C7B—C8B—H8B	134.5
C8A—C9A—S10A	119.6 (3)	C8B—C9B—C10B	110.7 (7)
C8A—C9A—C10A	110.1 (7)	C8B—C9B—S10B	120.6 (5)
C8A—C9A—H9A	125.1	C8B—C9B—H9B	124.9
S10A—C9A—H9A	115.3	C10B—C9B—H9B	124.4
C10A—C9A—H9A	124.9	S10B—C9B—H9B	114.3
C6A—C10A—C9A	108.7 (14)	C6B—C10B—C9B	112.5 (14)
C6A—C10A—H10A	125.8	C6B—C10B—H10B	123.5
C9A—C10A—H10A	125.5	C9B—C10B—H10B	124.0
C9A—S10A—C6A	99.6 (5)	C9B—S10B—C6B	98.3 (8)
C15A—C11A—C5A	128.7 (2)	C15B—C11B—C5B	128.9 (2)
C15A—C11A—S12A	110.46 (18)	C15B—C11B—S12B	109.5 (2)
C5A—C11A—S12A	120.80 (18)	C5B—C11B—S12B	121.65 (19)
C13A—S12A—C11A	92.38 (13)	C13B—S12B—C11B	92.64 (14)
C14A—C13A—S12A	111.5 (2)	C14B—C13B—S12B	111.2 (2)
C14A—C13A—H13A	124.3	C14B—C13B—H13B	124.4
S12A—C13A—H13A	124.2	S12B—C13B—H13B	124.4
C13A—C14A—C15A	113.8 (2)	C13B—C14B—C15B	113.6 (3)
C13A—C14A—H14A	123.1	C13B—C14B—H14B	123.2
C15A—C14A—H14A	123.1	C15B—C14B—H14B	123.2
C11A—C15A—C14A	111.9 (2)	C11B—C15B—C14B	113.0 (3)
C11A—C15A—H15A	124.0	C11B—C15B—H15B	123.5
C14A—C15A—H15A	124.1	C14B—C15B—H15B	123.5
C17A—C16A—C3A	125.6 (2)	C17B—C16B—C3B	125.6 (2)
C17A—C16A—H16A	117.1	C17B—C16B—H16B	117.2
C3A—C16A—H16A	117.2	C3B—C16B—H16B	117.2
C16A—C17A—C18A	126.6 (2)	C16B—C17B—C18B	126.2 (2)
C16A—C17A—H17A	116.7	C16B—C17B—H17B	116.9
C18A—C17A—H17A	116.7	C18B—C17B—H17B	116.9
C19A—C18A—C23A	117.8 (2)	C19B—C18B—C23B	118.3 (2)
C19A—C18A—C17A	123.7 (2)	C19B—C18B—C17B	123.2 (2)
C23A—C18A—C17A	118.5 (2)	C23B—C18B—C17B	118.5 (2)
C20A—C19A—C18A	121.0 (2)	C18B—C19B—C20B	120.7 (2)
C20A—C19A—H19A	119.5	C18B—C19B—H19B	119.6
C18A—C19A—H19A	119.5	C20B—C19B—H19B	119.7
C21A—C20A—C19A	120.7 (2)	C21B—C20B—C19B	120.5 (2)
C21A—C20A—H20A	119.7	C21B—C20B—H20B	119.7
C19A—C20A—H20A	119.7	C19B—C20B—H20B	119.8
O24A—C21A—C20A	125.6 (2)	O24B—C21B—C20B	125.5 (2)
O24A—C21A—C22A	115.1 (2)	O24B—C21B—C22B	115.1 (2)
C20A—C21A—C22A	119.3 (2)	C20B—C21B—C22B	119.4 (2)
O26A—C22A—C23A	124.9 (2)	O26B—C22B—C23B	125.1 (2)
O26A—C22A—C21A	115.7 (2)	O26B—C22B—C21B	115.1 (2)
C23A—C22A—C21A	119.5 (2)	C23B—C22B—C21B	119.8 (2)
C22A—C23A—C18A	121.7 (2)	C22B—C23B—C18B	121.3 (2)
C22A—C23A—H23A	119.1	C22B—C23B—H23B	119.4
C18A—C23A—H23A	119.1	C18B—C23B—H23B	119.3
C21A—O24A—C25A	116.4 (2)	C21B—O24B—C25B	116.4 (2)
O24A—C25A—H25A	109.5	O24B—C25B—H25D	109.5
O24A—C25A—H25B	109.5	O24B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
O24A—C25A—H25C	109.5	O24B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
C22A—O26A—C27A	116.62 (19)	C22B—O26B—C27B	116.49 (18)
O26A—C27A—H27A	109.5	O26B—C27B—H27D	109.5
O26A—C27A—H27B	109.5	O26B—C27B—H27E	109.5
H27A—C27A—H27B	109.5	H27D—C27B—H27E	109.5
O26A—C27A—H27C	109.5	O26B—C27B—H27F	109.5
H27A—C27A—H27C	109.5	H27D—C27B—H27F	109.5
H27B—C27A—H27C	109.5	H27E—C27B—H27F	109.5
C5A—S1A—C2A—C3A	−1.42 (19)	C5B—S1B—C2B—C3B	−0.5 (2)
C5A—S1A—C2A—C6A	177.7 (2)	C5B—S1B—C2B—C6B	178.7 (2)
C6A—C2A—C3A—C4A	−178.1 (2)	C6B—C2B—C3B—C4B	−178.9 (2)
S1A—C2A—C3A—C4A	0.8 (3)	S1B—C2B—C3B—C4B	0.2 (3)
C6A—C2A—C3A—C16A	−1.6 (4)	C6B—C2B—C3B—C16B	−1.7 (4)
S1A—C2A—C3A—C16A	177.28 (19)	S1B—C2B—C3B—C16B	177.4 (2)
C2A—C3A—C4A—C5A	0.4 (3)	C2B—C3B—C4B—C5B	0.3 (3)
C16A—C3A—C4A—C5A	−176.0 (2)	C16B—C3B—C4B—C5B	−176.8 (2)
C3A—C4A—C5A—C11A	177.7 (2)	C3B—C4B—C5B—C11B	179.7 (2)
C3A—C4A—C5A—S1A	−1.5 (3)	C3B—C4B—C5B—S1B	−0.7 (3)
C2A—S1A—C5A—C4A	1.65 (19)	C2B—S1B—C5B—C4B	0.6 (2)
C2A—S1A—C5A—C11A	−177.7 (2)	C2B—S1B—C5B—C11B	−179.7 (2)
C3A—C2A—C6A—C10A	143.4 (10)	C3B—C2B—C6B—C7B	143.1 (14)
S1A—C2A—C6A—C10A	−35.4 (10)	S1B—C2B—C6B—C7B	−35.9 (14)
C3A—C2A—C6A—C7A	−38.8 (14)	C3B—C2B—C6B—C10B	−36.3 (11)
S1A—C2A—C6A—C7A	142.3 (14)	S1B—C2B—C6B—C10B	144.7 (10)
C3A—C2A—C6A—S10A	145.3 (5)	C3B—C2B—C6B—S10B	−31.2 (8)
S1A—C2A—C6A—S10A	−33.6 (5)	S1B—C2B—C6B—S10B	149.8 (7)
C3A—C2A—C6A—S7A	−37.8 (4)	C3B—C2B—C6B—S7B	142.3 (2)
S1A—C2A—C6A—S7A	143.3 (2)	C10B—C6B—S7B—C8B	1.4 (9)
C10A—C6A—S7A—C8A	0.9 (9)	C2B—C6B—S7B—C8B	−177.5 (2)
C2A—C6A—S7A—C8A	−177.9 (2)	C2B—C6B—C7B—C8B	−177.1 (6)
C2A—C6A—C7A—C8A	−178.1 (6)	S10B—C6B—C7B—C8B	−2.1 (19)
S10A—C6A—C7A—C8A	−1.5 (18)	C6B—S7B—C8B—C9B	0.0 (3)
C6A—C7A—C8A—C9A	0.5 (18)	C6B—C7B—C8B—C9B	−1.1 (17)
C6A—S7A—C8A—C9A	−0.4 (3)	S7B—C8B—C9B—C10B	−1.3 (9)
C7A—C8A—C9A—S10A	1.0 (12)	C7B—C8B—C9B—S10B	4.4 (12)
S7A—C8A—C9A—C10A	−0.2 (8)	C2B—C6B—C10B—C9B	176.4 (5)
C2A—C6A—C10A—C9A	177.8 (5)	S7B—C6B—C10B—C9B	−2.3 (14)
S7A—C6A—C10A—C9A	−1.1 (14)	C8B—C9B—C10B—C6B	2.4 (15)
C8A—C9A—C10A—C6A	0.8 (14)	C8B—C9B—S10B—C6B	−5.4 (10)
C8A—C9A—S10A—C6A	−1.9 (7)	C7B—C6B—S10B—C9B	4.2 (16)
C2A—C6A—S10A—C9A	178.7 (3)	C2B—C6B—S10B—C9B	178.9 (4)
C7A—C6A—S10A—C9A	1.9 (12)	C4B—C5B—C11B—C15B	172.4 (3)
C4A—C5A—C11A—C15A	−151.6 (3)	S1B—C5B—C11B—C15B	−7.2 (4)
S1A—C5A—C11A—C15A	27.6 (4)	C4B—C5B—C11B—S12B	−7.3 (4)
C4A—C5A—C11A—S12A	25.4 (4)	S1B—C5B—C11B—S12B	173.13 (14)
S1A—C5A—C11A—S12A	−155.48 (14)	C15B—C11B—S12B—C13B	−0.1 (2)
C15A—C11A—S12A—C13A	1.4 (2)	C5B—C11B—S12B—C13B	179.6 (2)
C5A—C11A—S12A—C13A	−176.1 (2)	C11B—S12B—C13B—C14B	0.1 (3)
C11A—S12A—C13A—C14A	−1.0 (2)	S12B—C13B—C14B—C15B	−0.1 (4)
S12A—C13A—C14A—C15A	0.4 (3)	C5B—C11B—C15B—C14B	−179.6 (3)
C5A—C11A—C15A—C14A	175.8 (2)	S12B—C11B—C15B—C14B	0.1 (4)
S12A—C11A—C15A—C14A	−1.4 (3)	C13B—C14B—C15B—C11B	0.0 (4)
C13A—C14A—C15A—C11A	0.7 (3)	C2B—C3B—C16B—C17B	168.7 (3)
C2A—C3A—C16A—C17A	−176.5 (2)	C4B—C3B—C16B—C17B	−14.5 (4)
C4A—C3A—C16A—C17A	−0.5 (4)	C3B—C16B—C17B—C18B	176.6 (2)
C3A—C16A—C17A—C18A	179.7 (2)	C16B—C17B—C18B—C19B	15.2 (4)
C16A—C17A—C18A—C19A	6.6 (4)	C16B—C17B—C18B—C23B	−163.4 (3)
C16A—C17A—C18A—C23A	−171.1 (2)	C23B—C18B—C19B—C20B	1.5 (4)
C23A—C18A—C19A—C20A	1.6 (3)	C17B—C18B—C19B—C20B	−177.1 (2)
C17A—C18A—C19A—C20A	−176.2 (2)	C18B—C19B—C20B—C21B	−0.2 (4)
C18A—C19A—C20A—C21A	−0.1 (4)	C19B—C20B—C21B—O24B	179.3 (2)
C19A—C20A—C21A—O24A	−179.8 (2)	C19B—C20B—C21B—C22B	−1.2 (4)
C19A—C20A—C21A—C22A	−1.5 (4)	O24B—C21B—C22B—O26B	0.5 (3)
O24A—C21A—C22A—O26A	−0.2 (3)	C20B—C21B—C22B—O26B	−179.1 (2)
C20A—C21A—C22A—O26A	−178.6 (2)	O24B—C21B—C22B—C23B	−179.2 (2)
O24A—C21A—C22A—C23A	−180.0 (2)	C20B—C21B—C22B—C23B	1.2 (4)
C20A—C21A—C22A—C23A	1.6 (4)	O26B—C22B—C23B—C18B	−179.4 (2)
O26A—C22A—C23A—C18A	−179.8 (2)	C21B—C22B—C23B—C18B	0.2 (4)
C21A—C22A—C23A—C18A	−0.1 (4)	C19B—C18B—C23B—C22B	−1.5 (4)
C19A—C18A—C23A—C22A	−1.5 (4)	C17B—C18B—C23B—C22B	177.2 (2)
C17A—C18A—C23A—C22A	176.4 (2)	C20B—C21B—O24B—C25B	5.1 (4)
C20A—C21A—O24A—C25A	−3.9 (4)	C22B—C21B—O24B—C25B	−174.4 (2)
C22A—C21A—O24A—C25A	177.7 (2)	C23B—C22B—O26B—C27B	−2.0 (3)
C23A—C22A—O26A—C27A	−5.7 (4)	C21B—C22B—O26B—C27B	178.4 (2)
C21A—C22A—O26A—C27A	174.5 (2)

(IV) (E,E)-1,4-bis[2-(2,2':5',2''-terthiophen-3'-yl)ethenyl]-2,5- dimethoxybenzene

Crystal data

C36H26O2S6	F(000) = 1416
Mr = 682.93	Dx = 1.451 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 200 reflections
a = 9.341 (1) Å	θ = 3–20°
b = 36.688 (3) Å	µ = 0.47 mm^−1
c = 10.097 (2) Å	T = 150 K
β = 115.36 (1)°	Needle, colourless
V = 3126.8 (8) Å^3	0.3 × 0.1 × 0.1 mm
Z = 4

Data collection

Bruker P4 CCD diffractometer	3209 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.140
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω–scan	h = −11→11
26458 measured reflections	k = −43→43
5499 independent reflections	l = −11→12

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
5499 reflections	(Δ/σ)max = 0.001
420 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.26450 (14)	0.16221 (3)	0.53967 (13)	0.0249 (3)
C2A	0.3664 (5)	0.12203 (12)	0.6077 (5)	0.0199 (11)
C3A	0.4178 (5)	0.10605 (12)	0.5097 (5)	0.0199 (11)
C4A	0.3705 (5)	0.12795 (12)	0.3797 (5)	0.0211 (11)
H4A	0.3955	0.1216	0.3009	0.025*
C5A	0.2871 (5)	0.15849 (12)	0.3778 (5)	0.0208 (11)
C6A	0.3808 (5)	0.11000 (12)	0.7516 (5)	0.0240 (12)
S7A	0.54149 (15)	0.08528 (4)	0.87490 (14)	0.0298 (4)
C8A	0.4717 (5)	0.08741 (13)	1.0072 (5)	0.0264 (12)
H8A	0.5232	0.0766	1.1014	0.032*
C9A	0.3358 (6)	0.10623 (13)	0.9611 (5)	0.0273 (12)
H9A	0.2811	0.1103	1.0204	0.033*
C10A	0.2812 (5)	0.11949 (12)	0.8157 (5)	0.0220 (11)
H10A	0.1870	0.1334	0.7676	0.026*
C11A	0.2201 (5)	0.18650 (13)	0.2661 (5)	0.0250 (12)
S12A	0.2927 (14)	0.1957 (3)	0.1471 (13)	0.0254 (14)	0.445 (5)
C12A	0.278 (5)	0.1935 (11)	0.160 (4)	0.0254 (14)	0.555 (5)
H12A	0.3612	0.1810	0.1480	0.030*	0.555 (5)
C13A	0.1759 (7)	0.22616 (15)	0.0642 (6)	0.0435 (16)
H13A	0.1803	0.2379	−0.0178	0.052*
C14A	0.0654 (7)	0.23566 (15)	0.1128 (6)	0.0497 (18)
H14A	−0.0118	0.2544	0.0742	0.060*
C15A	0.091 (4)	0.2084 (10)	0.252 (4)	0.0278 (10)	0.445 (5)
H15A	0.0321	0.2078	0.3082	0.033*	0.445 (5)
S15A	0.0699 (8)	0.21426 (18)	0.2432 (8)	0.0278 (10)	0.555 (5)
C16A	0.5035 (5)	0.07211 (11)	0.5357 (5)	0.0188 (11)
H16A	0.5090	0.0582	0.6171	0.023*
C17A	0.5759 (5)	0.05798 (12)	0.4593 (5)	0.0196 (11)
H17A	0.5650	0.0707	0.3736	0.024*
C18A	0.6713 (5)	0.02443 (12)	0.4956 (5)	0.0201 (11)
C19A	0.7175 (5)	0.00735 (12)	0.3946 (5)	0.0198 (11)
O20A	0.6546 (4)	0.02225 (8)	0.2545 (3)	0.0236 (8)
C21A	0.7096 (6)	0.00671 (13)	0.1541 (5)	0.0276 (12)
H21A	0.8246	0.0098	0.1930	0.036*
H21B	0.6581	0.0190	0.0591	0.036*
H21C	0.6835	−0.0193	0.1417	0.036*
C22A	0.8145 (5)	−0.02281 (12)	0.4336 (5)	0.0213 (11)
H22A	0.8435	−0.0335	0.3629	0.026*
S1B	1.26821 (14)	−0.18012 (3)	0.55608 (13)	0.0265 (3)
C2B	1.1675 (5)	−0.14070 (12)	0.4753 (5)	0.0216 (11)
C3B	1.1277 (5)	−0.12030 (12)	0.5723 (5)	0.0201 (11)
C4B	1.1840 (5)	−0.13808 (12)	0.7116 (5)	0.0218 (11)
H4B	1.1699	−0.1280	0.7918	0.026*
C5B	1.2592 (5)	−0.17054 (12)	0.7215 (5)	0.0212 (11)
C6B	1.1305 (5)	−0.13442 (13)	0.3198 (5)	0.0217 (11)
S7B	1.0991 (4)	−0.17228 (5)	0.2096 (4)	0.0268 (8)	0.665 (4)
C7B	1.117 (4)	−0.1608 (6)	0.211 (3)	0.0268 (8)	0.335 (4)
H7B	1.1414	−0.1858	0.2338	0.032*	0.335 (4)
C8B	1.0693 (5)	−0.14525 (14)	0.0634 (5)	0.0307 (13)
H8B	1.0509	−0.1552	−0.0294	0.037*
C9B	1.0730 (5)	−0.10956 (14)	0.0856 (6)	0.0328 (13)
H9B	1.0524	−0.0913	0.0129	0.039*
C10B	1.117 (3)	−0.1027 (6)	0.251 (3)	0.0354 (19)	0.665 (4)
H10B	1.1310	−0.0793	0.2947	0.042*	0.665 (4)
S10B	1.0993 (15)	−0.0924 (2)	0.2277 (12)	0.0354 (19)	0.335 (4)
C11B	1.3367 (5)	−0.19553 (13)	0.8451 (5)	0.0287 (12)
S12B	1.3617 (13)	−0.23940 (17)	0.8344 (12)	0.0272 (13)	0.465 (5)
C12B	1.361 (4)	−0.2317 (7)	0.832 (5)	0.0272 (13)	0.535 (5)
H12B	1.3226	−0.2454	0.7432	0.033*	0.535 (5)
C13B	1.4645 (7)	−0.24712 (19)	0.9921 (9)	0.067 (2)
H13B	1.5079	−0.2706	1.0247	0.081*
C14B	1.4920 (7)	−0.2196 (2)	1.0839 (7)	0.067 (2)
H14B	1.5550	−0.2207	1.1867	0.080*
C15B	1.403 (5)	−0.1838 (15)	0.995 (4)	0.0312 (11)	0.465 (5)
H15B	1.3947	−0.1605	1.0322	0.037*	0.465 (5)
S15B	1.4211 (11)	−0.1830 (3)	1.0178 (9)	0.0312 (11)	0.535 (5)
C16B	1.0324 (5)	−0.08778 (12)	0.5339 (5)	0.0227 (11)
H16B	1.0076	−0.0778	0.4397	0.027*
C17B	0.9751 (5)	−0.07011 (12)	0.6163 (5)	0.0226 (11)
H17B	1.0049	−0.0793	0.7125	0.027*
C18B	0.8723 (5)	−0.03843 (12)	0.5749 (5)	0.0182 (11)
C19B	0.8235 (5)	−0.02138 (12)	0.6747 (5)	0.0216 (11)
O20B	0.8801 (4)	−0.03765 (8)	0.8132 (3)	0.0257 (8)
C21B	0.8140 (6)	−0.02441 (13)	0.9082 (5)	0.0290 (12)
H21D	0.8448	0.0011	0.9332	0.038*
H21E	0.8536	−0.0391	0.9979	0.038*
H21F	0.6982	−0.0262	0.8586	0.038*
C22B	0.7281 (5)	0.00897 (12)	0.6364 (5)	0.0189 (11)
H22B	0.6996	0.0198	0.7072	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0280 (7)	0.0261 (7)	0.0206 (7)	0.0044 (6)	0.0104 (6)	−0.0024 (6)
C2A	0.018 (2)	0.025 (3)	0.018 (3)	0.003 (2)	0.009 (2)	−0.002 (2)
C3A	0.020 (3)	0.020 (3)	0.017 (3)	−0.001 (2)	0.006 (2)	0.000 (2)
C4A	0.021 (3)	0.025 (3)	0.018 (3)	−0.004 (2)	0.009 (2)	−0.003 (2)
C5A	0.021 (3)	0.022 (3)	0.020 (3)	−0.004 (2)	0.010 (2)	−0.005 (2)
C6A	0.028 (3)	0.024 (3)	0.021 (3)	0.005 (2)	0.012 (2)	0.000 (2)
S7A	0.0342 (8)	0.0374 (8)	0.0237 (7)	0.0089 (6)	0.0180 (6)	0.0070 (6)
C8A	0.036 (3)	0.037 (3)	0.017 (3)	0.004 (2)	0.022 (2)	0.004 (2)
C9A	0.035 (3)	0.031 (3)	0.025 (3)	−0.006 (2)	0.021 (2)	−0.006 (2)
C10A	0.023 (3)	0.027 (3)	0.016 (3)	0.002 (2)	0.008 (2)	−0.002 (2)
C11A	0.023 (3)	0.025 (3)	0.020 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
S12A	0.029 (3)	0.030 (2)	0.022 (2)	−0.0023 (16)	0.0151 (14)	0.0055 (17)
C12A	0.029 (3)	0.030 (2)	0.022 (2)	−0.0023 (16)	0.0151 (14)	0.0055 (17)
C13A	0.056 (4)	0.043 (4)	0.023 (3)	−0.016 (3)	0.009 (3)	0.011 (3)
C14A	0.040 (4)	0.032 (3)	0.048 (4)	0.006 (3)	−0.009 (3)	−0.005 (3)
C15A	0.033 (2)	0.029 (3)	0.0204 (16)	0.0067 (16)	0.0100 (17)	−0.0004 (17)
S15A	0.033 (2)	0.029 (3)	0.0204 (16)	0.0067 (16)	0.0100 (17)	−0.0004 (17)
C16A	0.027 (3)	0.018 (3)	0.012 (3)	0.002 (2)	0.008 (2)	0.002 (2)
C17A	0.026 (3)	0.020 (3)	0.010 (2)	0.002 (2)	0.005 (2)	−0.002 (2)
C18A	0.020 (3)	0.025 (3)	0.016 (3)	−0.004 (2)	0.009 (2)	−0.002 (2)
C19A	0.017 (2)	0.025 (3)	0.017 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
O20A	0.0325 (19)	0.0294 (19)	0.0118 (18)	0.0091 (15)	0.0124 (15)	0.0001 (14)
C21A	0.035 (3)	0.035 (3)	0.013 (3)	0.012 (2)	0.011 (2)	0.002 (2)
C22A	0.022 (3)	0.033 (3)	0.014 (3)	0.001 (2)	0.013 (2)	−0.004 (2)
S1B	0.0282 (7)	0.0269 (7)	0.0267 (7)	0.0039 (6)	0.0139 (6)	−0.0017 (6)
C2B	0.024 (3)	0.025 (3)	0.020 (3)	0.000 (2)	0.013 (2)	0.001 (2)
C3B	0.020 (3)	0.023 (3)	0.019 (3)	−0.002 (2)	0.010 (2)	−0.003 (2)
C4B	0.023 (3)	0.025 (3)	0.022 (3)	0.000 (2)	0.013 (2)	−0.001 (2)
C5B	0.019 (2)	0.029 (3)	0.020 (3)	−0.001 (2)	0.011 (2)	−0.001 (2)
C6B	0.022 (3)	0.026 (3)	0.019 (3)	−0.002 (2)	0.010 (2)	−0.003 (2)
S7B	0.0381 (14)	0.0256 (17)	0.0153 (10)	0.0005 (13)	0.0100 (10)	−0.0071 (13)
C7B	0.0381 (14)	0.0256 (17)	0.0153 (10)	0.0005 (13)	0.0100 (10)	−0.0071 (13)
C8B	0.031 (3)	0.045 (4)	0.013 (3)	0.005 (3)	0.006 (2)	−0.003 (2)
C9B	0.027 (3)	0.036 (3)	0.040 (3)	0.005 (2)	0.019 (3)	0.001 (3)
C10B	0.039 (3)	0.052 (6)	0.020 (4)	−0.006 (4)	0.017 (3)	−0.004 (3)
S10B	0.039 (3)	0.052 (6)	0.020 (4)	−0.006 (4)	0.017 (3)	−0.004 (3)
C11B	0.028 (3)	0.030 (3)	0.029 (3)	0.001 (2)	0.012 (2)	0.010 (2)
S12B	0.0346 (15)	0.019 (3)	0.0320 (16)	0.003 (3)	0.0185 (13)	−0.001 (3)
C12B	0.0346 (15)	0.019 (3)	0.0320 (16)	0.003 (3)	0.0185 (13)	−0.001 (3)
C13B	0.031 (4)	0.050 (5)	0.118 (7)	0.010 (3)	0.029 (4)	0.055 (5)
C14B	0.040 (4)	0.118 (7)	0.031 (4)	−0.013 (4)	0.005 (3)	0.034 (4)
C15B	0.037 (3)	0.0341 (13)	0.024 (3)	0.0023 (18)	0.014 (2)	0.000 (2)
S15B	0.037 (3)	0.0341 (13)	0.024 (3)	0.0023 (18)	0.014 (2)	0.000 (2)
C16B	0.025 (3)	0.026 (3)	0.018 (3)	0.001 (2)	0.010 (2)	0.000 (2)
C17B	0.027 (3)	0.028 (3)	0.014 (3)	0.002 (2)	0.010 (2)	0.002 (2)
C18B	0.017 (2)	0.020 (3)	0.020 (3)	−0.003 (2)	0.011 (2)	−0.003 (2)
C19B	0.028 (3)	0.024 (3)	0.017 (3)	−0.002 (2)	0.014 (2)	−0.001 (2)
O20B	0.038 (2)	0.0297 (19)	0.0154 (19)	0.0100 (16)	0.0173 (16)	0.0031 (15)
C21B	0.036 (3)	0.043 (3)	0.018 (3)	0.005 (2)	0.020 (2)	0.002 (2)
C22B	0.026 (3)	0.026 (3)	0.012 (3)	0.002 (2)	0.015 (2)	−0.002 (2)

Geometric parameters (Å, º)

S1A—C2A	1.729 (4)	C2B—C6B	1.474 (6)
S1A—C5A	1.741 (5)	C3B—C4B	1.430 (6)
C2A—C3A	1.400 (6)	C3B—C16B	1.439 (6)
C2A—C6A	1.469 (6)	C4B—C5B	1.364 (6)
C3A—C4A	1.438 (6)	C4B—H4B	0.9499
C3A—C16A	1.442 (6)	C5B—C11B	1.465 (6)
C4A—C5A	1.360 (6)	C6B—C10B	1.333 (18)
C4A—H4A	0.9499	C6B—C7B	1.42 (3)
C5A—C11A	1.455 (6)	C6B—S7B	1.724 (5)
C6A—C10A	1.385 (6)	C6B—S10B	1.759 (9)
C6A—S7A	1.739 (4)	S7B—C8B	1.699 (6)
S7A—C8A	1.721 (5)	S7B—H7B	0.6157
C8A—C9A	1.341 (6)	C7B—C8B	1.48 (3)
C8A—H8A	0.9500	C7B—H7B	0.9501
C9A—C10A	1.418 (6)	C8B—C9B	1.326 (6)
C9A—H9A	0.9499	C8B—H8B	0.9501
C10A—H10A	0.9500	C9B—S10B	1.488 (14)
C11A—C15A	1.40 (3)	C9B—C10B	1.56 (3)
C11A—C12A	1.42 (3)	C9B—H9B	0.9501
C11A—S12A	1.648 (11)	C10B—H10B	0.9498
C11A—S15A	1.668 (8)	S10B—H10B	0.7766
S12A—C13A	1.535 (15)	C11B—C12B	1.36 (3)
C12A—C13A	1.58 (4)	C11B—C15B	1.43 (4)
C12A—H12A	0.9499	C11B—S12B	1.636 (9)
C13A—C14A	1.365 (8)	C11B—S15B	1.642 (10)
C13A—H13A	0.9500	S12B—C13B	1.493 (14)
C14A—S15A	1.517 (11)	C12B—C13B	1.59 (4)
C14A—C15A	1.65 (4)	C12B—H12B	0.9501
C14A—H14A	0.9499	C13B—C14B	1.319 (9)
C15A—H15A	0.9500	C13B—H13B	0.9502
C16A—C17A	1.329 (6)	C14B—S15B	1.520 (15)
C16A—H16A	0.9499	C14B—C15B	1.61 (5)
C17A—C18A	1.471 (6)	C14B—H14B	0.9501
C17A—H17A	0.9499	C15B—H15B	0.9502
C18A—C22B	1.407 (6)	C16B—C17B	1.335 (6)
C18A—C19A	1.412 (6)	C16B—H16B	0.9501
C19A—C22A	1.377 (6)	C17B—C18B	1.450 (6)
C19A—O20A	1.391 (5)	C17B—H17B	0.9500
O20A—C21A	1.436 (5)	C18B—C19B	1.417 (6)
C21A—H21A	0.9800	C19B—C22B	1.375 (6)
C21A—H21B	0.9800	C19B—O20B	1.399 (5)
C21A—H21C	0.9800	O20B—C21B	1.430 (5)
C22A—C18B	1.413 (6)	C21B—H21D	0.9800
C22A—H22A	0.9500	C21B—H21E	0.9800
S1B—C2B	1.728 (5)	C21B—H21F	0.9800
S1B—C5B	1.744 (5)	C22B—H22B	0.9501
C2B—C3B	1.403 (6)
C2A—S1A—C5A	92.2 (2)	C4B—C3B—C16B	124.6 (4)
C3A—C2A—C6A	131.3 (4)	C5B—C4B—C3B	115.6 (4)
C3A—C2A—S1A	111.9 (3)	C5B—C4B—H4B	122.2
C6A—C2A—S1A	116.7 (3)	C3B—C4B—H4B	122.2
C2A—C3A—C4A	110.3 (4)	C4B—C5B—C11B	131.3 (4)
C2A—C3A—C16A	124.4 (4)	C4B—C5B—S1B	109.9 (3)
C4A—C3A—C16A	125.3 (4)	C11B—C5B—S1B	118.7 (4)
C5A—C4A—C3A	115.1 (4)	C10B—C6B—C2B	128.3 (12)
C5A—C4A—H4A	122.4	C7B—C6B—C2B	128.0 (11)
C3A—C4A—H4A	122.5	C10B—C6B—S7B	114.4 (12)
C4A—C5A—C11A	130.3 (4)	C2B—C6B—S7B	117.3 (3)
C4A—C5A—S1A	110.5 (3)	C7B—C6B—S10B	104.4 (12)
C11A—C5A—S1A	119.2 (3)	C2B—C6B—S10B	127.6 (5)
C10A—C6A—C2A	126.3 (4)	C8B—S7B—C6B	90.6 (3)
C10A—C6A—S7A	110.1 (3)	C8B—S7B—H7B	130.8
C2A—C6A—S7A	123.3 (3)	C6B—S7B—H7B	119.3
C8A—S7A—C6A	91.9 (2)	C6B—C7B—C8B	113.9 (16)
C9A—C8A—S7A	111.8 (4)	C6B—C7B—H7B	122.7
C9A—C8A—H8A	124.1	C8B—C7B—H7B	123.4
S7A—C8A—H8A	124.1	C9B—C8B—C7B	103.5 (10)
C8A—C9A—C10A	113.7 (4)	C9B—C8B—S7B	116.5 (4)
C8A—C9A—H9A	123.1	C9B—C8B—H8B	121.8
C10A—C9A—H9A	123.2	C7B—C8B—H8B	134.3
C6A—C10A—C9A	112.4 (4)	S7B—C8B—H8B	121.7
C6A—C10A—H10A	123.8	C8B—C9B—S10B	124.2 (5)
C9A—C10A—H10A	123.8	C8B—C9B—C10B	108.4 (9)
C15A—C11A—C5A	123.4 (19)	C8B—C9B—H9B	125.6
C12A—C11A—C5A	122.5 (19)	S10B—C9B—H9B	110.0
C15A—C11A—S12A	114.2 (19)	C10B—C9B—H9B	126.0
C5A—C11A—S12A	122.4 (6)	C6B—C10B—C9B	110.0 (17)
C12A—C11A—S15A	110.9 (18)	C6B—C10B—H10B	125.5
C5A—C11A—S15A	126.6 (5)	C9B—C10B—H10B	124.5
C13A—S12A—C11A	97.4 (7)	C9B—S10B—C6B	93.5 (6)
C11A—C12A—C13A	106 (3)	C12B—C11B—C5B	124.6 (18)
C11A—C12A—H12A	127.1	C15B—C11B—C5B	123 (2)
C13A—C12A—H12A	127.2	C15B—C11B—S12B	111 (2)
C14A—C13A—S12A	117.4 (6)	C5B—C11B—S12B	126.3 (5)
C14A—C13A—C12A	109.2 (14)	C12B—C11B—S15B	110.7 (18)
C14A—C13A—H13A	121.3	C5B—C11B—S15B	124.5 (5)
S12A—C13A—H13A	121.3	C13B—S12B—C11B	99.3 (6)
C12A—C13A—H13A	129.5	C11B—C12B—C13B	107 (2)
C13A—C14A—S15A	115.8 (5)	C11B—C12B—H12B	126.4
C13A—C14A—C15A	107.0 (14)	C13B—C12B—H12B	126.1
C13A—C14A—H14A	126.5	C14B—C13B—S12B	116.6 (6)
S15A—C14A—H14A	117.7	C14B—C13B—H13B	121.7
C15A—C14A—H14A	126.5	S12B—C13B—H13B	121.7
C11A—C15A—C14A	104 (3)	C12B—C13B—H13B	131.1
C11A—C15A—H15A	128.3	C13B—C14B—S15B	116.8 (6)
C14A—C15A—H15A	127.7	C13B—C14B—C15B	109.5 (17)
C14A—S15A—C11A	98.4 (5)	C13B—C14B—H14B	125.4
C17A—C16A—C3A	127.7 (4)	S15B—C14B—H14B	117.8
C17A—C16A—H16A	116.1	C15B—C14B—H14B	125.2
C3A—C16A—H16A	116.1	C11B—C15B—C14B	103 (3)
C16A—C17A—C18A	125.9 (4)	C11B—C15B—H15B	128.3
C16A—C17A—H17A	117.0	C14B—C15B—H15B	128.4
C18A—C17A—H17A	117.1	C14B—S15B—C11B	98.0 (7)
C22B—C18A—C19A	116.8 (4)	C17B—C16B—C3B	127.0 (4)
C22B—C18A—C17A	121.0 (4)	C17B—C16B—H16B	116.5
C19A—C18A—C17A	122.1 (4)	C3B—C16B—H16B	116.5
C22A—C19A—O20A	123.1 (4)	C16B—C17B—C18B	127.0 (4)
C22A—C19A—C18A	121.2 (4)	C16B—C17B—H17B	116.5
O20A—C19A—C18A	115.7 (4)	C18B—C17B—H17B	116.5
C19A—O20A—C21A	116.0 (3)	C22A—C18B—C19B	116.0 (4)
O20A—C21A—H21A	109.5	C22A—C18B—C17B	122.4 (4)
O20A—C21A—H21B	109.5	C19B—C18B—C17B	121.6 (4)
H21A—C21A—H21B	109.5	C22B—C19B—O20B	123.3 (4)
O20A—C21A—H21C	109.5	C22B—C19B—C18B	121.7 (4)
H21A—C21A—H21C	109.5	O20B—C19B—C18B	115.1 (4)
H21B—C21A—H21C	109.5	C19B—O20B—C21B	116.0 (3)
C19A—C22A—C18B	122.3 (4)	O20B—C21B—H21D	109.5
C19A—C22A—H22A	118.8	O20B—C21B—H21E	109.5
C18B—C22A—H22A	118.8	H21D—C21B—H21E	109.5
C2B—S1B—C5B	92.5 (2)	O20B—C21B—H21F	109.5
C3B—C2B—C6B	130.4 (4)	H21D—C21B—H21F	109.5
C3B—C2B—S1B	111.7 (3)	H21E—C21B—H21F	109.5
C6B—C2B—S1B	117.7 (3)	C19B—C22B—C18A	122.0 (4)
C2B—C3B—C4B	110.3 (4)	C19B—C22B—H22B	119.0
C2B—C3B—C16B	124.9 (4)	C18A—C22B—H22B	119.0
C5A—S1A—C2A—C3A	0.3 (4)	C3B—C4B—C5B—C11B	177.3 (4)
C5A—S1A—C2A—C6A	−178.0 (4)	C3B—C4B—C5B—S1B	1.5 (5)
C6A—C2A—C3A—C4A	178.0 (4)	C2B—S1B—C5B—C4B	−1.0 (4)
S1A—C2A—C3A—C4A	0.1 (5)	C2B—S1B—C5B—C11B	−177.4 (4)
C6A—C2A—C3A—C16A	−1.0 (8)	C3B—C2B—C6B—C10B	33.7 (16)
S1A—C2A—C3A—C16A	−179.0 (3)	S1B—C2B—C6B—C10B	−149.7 (14)
C2A—C3A—C4A—C5A	−0.5 (6)	C3B—C2B—C6B—C7B	−153.4 (16)
C16A—C3A—C4A—C5A	178.5 (4)	S1B—C2B—C6B—C7B	23.3 (17)
C3A—C4A—C5A—C11A	−179.6 (4)	C3B—C2B—C6B—S7B	−145.9 (4)
C3A—C4A—C5A—S1A	0.8 (5)	S1B—C2B—C6B—S7B	30.8 (5)
C2A—S1A—C5A—C4A	−0.6 (4)	C3B—C2B—C6B—S10B	28.9 (9)
C2A—S1A—C5A—C11A	179.7 (4)	S1B—C2B—C6B—S10B	−154.4 (6)
C3A—C2A—C6A—C10A	−154.5 (5)	C10B—C6B—S7B—C8B	1.2 (13)
S1A—C2A—C6A—C10A	23.4 (6)	C2B—C6B—S7B—C8B	−179.3 (4)
C3A—C2A—C6A—S7A	32.9 (7)	C2B—C6B—C7B—C8B	176.7 (10)
S1A—C2A—C6A—S7A	−149.2 (3)	S10B—C6B—C7B—C8B	−5 (2)
C10A—C6A—S7A—C8A	1.0 (4)	C6B—C7B—C8B—C9B	7 (2)
C2A—C6A—S7A—C8A	174.6 (4)	C6B—S7B—C8B—C9B	−3.1 (4)
C6A—S7A—C8A—C9A	−0.9 (4)	C7B—C8B—C9B—S10B	−7.1 (15)
S7A—C8A—C9A—C10A	0.6 (5)	S7B—C8B—C9B—C10B	3.8 (11)
C2A—C6A—C10A—C9A	−174.3 (4)	C2B—C6B—C10B—C9B	−178.9 (7)
S7A—C6A—C10A—C9A	−0.8 (5)	S7B—C6B—C10B—C9B	1 (2)
C8A—C9A—C10A—C6A	0.2 (6)	C8B—C9B—C10B—C6B	−2.8 (19)
C4A—C5A—C11A—C15A	155 (2)	C8B—C9B—S10B—C6B	3.9 (9)
S1A—C5A—C11A—C15A	−25 (2)	C7B—C6B—S10B—C9B	1.2 (15)
C4A—C5A—C11A—C12A	−23.3 (19)	C2B—C6B—S10B—C9B	179.3 (5)
S1A—C5A—C11A—C12A	156.3 (18)	C4B—C5B—C11B—C12B	157.1 (19)
C4A—C5A—C11A—S12A	−26.0 (9)	S1B—C5B—C11B—C12B	−27 (2)
S1A—C5A—C11A—S12A	153.6 (6)	C4B—C5B—C11B—C15B	−26 (2)
C4A—C5A—C11A—S15A	156.7 (5)	S1B—C5B—C11B—C15B	150 (2)
S1A—C5A—C11A—S15A	−23.7 (6)	C4B—C5B—C11B—S12B	154.4 (6)
C15A—C11A—S12A—C13A	−1.1 (19)	S1B—C5B—C11B—S12B	−30.0 (7)
C5A—C11A—S12A—C13A	−179.9 (5)	C4B—C5B—C11B—S15B	−28.9 (8)
C5A—C11A—C12A—C13A	−178.6 (9)	S1B—C5B—C11B—S15B	146.7 (5)
C15A—C11A—C12A—C13A	1 (2)	C15B—C11B—S12B—C13B	−7 (2)
C11A—S12A—C13A—C14A	2.0 (8)	C5B—C11B—S12B—C13B	172.7 (5)
C11A—C12A—C13A—C14A	−2 (2)	C5B—C11B—C12B—C13B	174.0 (9)
C12A—C13A—C14A—S15A	1.5 (16)	S15B—C11B—C12B—C13B	−1 (2)
S12A—C13A—C14A—C15A	−2.1 (16)	C11B—S12B—C13B—C14B	4.2 (9)
C12A—C11A—C15A—C14A	−2 (3)	C11B—C12B—C13B—C14B	0 (2)
C5A—C11A—C15A—C14A	178.9 (8)	C12B—C13B—C14B—S15B	0.6 (16)
S12A—C11A—C15A—C14A	0 (3)	S12B—C13B—C14B—C15B	0 (2)
C13A—C14A—C15A—C11A	1 (2)	C12B—C11B—C15B—C14B	5 (4)
C13A—C14A—S15A—C11A	−0.6 (6)	C5B—C11B—C15B—C14B	−172.7 (11)
C12A—C11A—S15A—C14A	−0.6 (17)	S12B—C11B—C15B—C14B	7 (3)
C5A—C11A—S15A—C14A	179.4 (4)	C13B—C14B—C15B—C11B	−4 (3)
C2A—C3A—C16A—C17A	−169.2 (4)	C13B—C14B—S15B—C11B	−1.0 (9)
C4A—C3A—C16A—C17A	11.9 (7)	C12B—C11B—S15B—C14B	1.0 (18)
C3A—C16A—C17A—C18A	175.6 (4)	C5B—C11B—S15B—C14B	−173.8 (5)
C16A—C17A—C18A—C22B	−16.5 (7)	C2B—C3B—C16B—C17B	170.9 (5)
C16A—C17A—C18A—C19A	167.0 (4)	C4B—C3B—C16B—C17B	−3.5 (7)
C22B—C18A—C19A—C22A	−0.5 (6)	C3B—C16B—C17B—C18B	−176.6 (4)
C17A—C18A—C19A—C22A	176.1 (4)	C19A—C22A—C18B—C19B	0.5 (6)
C22B—C18A—C19A—O20A	177.5 (4)	C19A—C22A—C18B—C17B	−179.7 (4)
C17A—C18A—C19A—O20A	−5.9 (6)	C16B—C17B—C18B—C22A	2.3 (7)
C22A—C19A—O20A—C21A	−6.3 (6)	C16B—C17B—C18B—C19B	−177.9 (4)
C18A—C19A—O20A—C21A	175.8 (4)	C22A—C18B—C19B—C22B	−1.2 (6)
O20A—C19A—C22A—C18B	−177.5 (4)	C17B—C18B—C19B—C22B	179.0 (4)
C18A—C19A—C22A—C18B	0.3 (7)	C22A—C18B—C19B—O20B	179.0 (4)
C5B—S1B—C2B—C3B	0.3 (4)	C17B—C18B—C19B—O20B	−0.8 (6)
C5B—S1B—C2B—C6B	−177.0 (4)	C22B—C19B—O20B—C21B	9.2 (6)
C6B—C2B—C3B—C4B	177.3 (4)	C18B—C19B—O20B—C21B	−171.0 (4)
S1B—C2B—C3B—C4B	0.5 (5)	O20B—C19B—C22B—C18A	−179.1 (4)
C6B—C2B—C3B—C16B	2.2 (8)	C18B—C19B—C22B—C18A	1.1 (7)
S1B—C2B—C3B—C16B	−174.6 (4)	C19A—C18A—C22B—C19B	−0.2 (7)
C2B—C3B—C4B—C5B	−1.4 (6)	C17A—C18A—C22B—C19B	−176.9 (4)
C16B—C3B—C4B—C5B	173.7 (4)