Crystal chemistry of layered structures formed by linear rigid silyl-capped molecules

The crystallization behavior of methylthio- or methylsulfonyl-containing spacer extended Z,Z-bis-ene–yne molecules capped with trimethylsilyl groups obtained by (tandem) thiophene ring fragmentation and of two non-spacer extended analogs were investigated. The rigid and linear molecules generally crystallized in layers whereby the flexibility of the layer interfaces formed by the silyl groups leads to a remarkably rich crystal chemistry. The molecules with benzene and thiophene spacers both crystallized with C2/c symmetry and can be considered as merotypes. Increasing the steric bulk of the core by introduction of ethylenedioxythiophene (EDOT) gave a structure incommensurately modulated in the [010] direction. Further increase of steric demand in the case of a dimethoxythiophene restored periodicity along [010] but resulted in a doubling of the c vector. Two different polytypes were observed, which feature geometrically different layer interfaces (non-OD, order–disorder, polytypes), one with a high stacking fault probability. Oxidation of the methylthio groups of the benzene-based molecule to methylsulfonyl groups led to three polymorphs (two temperature-dependent), which were analyzed by Hirshfeld surface d_e/d_i fingerprint plots. The analogously oxidized EDOT-based molecule crystallized as systematic twins owing to its OD polytypism. Shortening of the backbone by removal of the aryl core resulted in an enantiomorphic structure and a further shortening by removal of a methylthio-ene fragment again in a systematically twinned OD polytype.

1. Introduction

The controlled formation of layers plays an important role in the design of materials. For example, hybrid organic–inorganic layered perovskites (Mitzi, 2001) are natural quantum well structures and can be tuned to specific electronic, magnetic and optical properties. The combination of layers with different properties enables the synthesis of multi-functional composites (Coronado et al., 2000). In the field of organic electronics the formation of layers has been shown to be a viable strategy to improve conductivity (Anthony et al., 2001). Efficient charge transport in organic materials is governed by nearest-neighbor electronic coupling. The intermolecular coupling is maximized when a face-to-face orientation of aromatic molecules is realized, as a consequence of enhanced interactions of the π-electron clouds of adjacent molecules (Mueller & Bunz, 2007).

Anthony et al. (2001) modified pentacene by connecting it at the central C atoms to triisopropylsilyl (TIPS) groups via rigid ethyne bridges. As opposed to plain pentacene, the resulting TIPS-pentacene molecules crystallized in layers (Fig. 1), whereby the pentacene cores are arranged in face-to-face orientation. As a result, a significantly lower resistivity perpendicular to the pentacene was reported (Anthony et al., 2001). Hence, TIPS-pentacene yielded promising solution-processed OFET (organic field effect transistor) devices (Park et al., 2007). In addition to the modified stacking arrangement the structures showed improved stability and solubility. On this basis a general molecular design for improved π-stacking was proposed by Anthony et al. (2002), and intense research in the field of substituted acene derivatives arose from these findings and is of ongoing interest (Anthony, 1994, 2008).

Figure 1 Crystal structure of TIPS-pentacene () featuring distinct layers of pentacene cores and TIPS groups connected by —C≡C—bridges viewed down [010]. Coordinates taken from Anthony et al. (2001). H atoms and disorder of the TIPS groups were omitted for clarity.

Besides technological importance, layered structures are interesting from a crystallographic point of view. Polymorphs (different crystal structures of the same composition) that crystallize in different arrangements of equivalent layers are called polytypes. Polytypes are ubiquitous in all classes of solid materials and are often the cause of crystallographically challenging problems, like twinning (the systematic association of equivalent macroscopic domains with different orientations; Hahn, 2006b) and stacking disorder. In order–disorder (OD) polytyes (Dornberger-Schiff & Grell-Niemann, 1961; Ferraris et al., 2008) pairs of layers are equivalent and therefore all polytypes are locally equivalent. The symmetry of a polytype is described by groupoids, a generalization of the group concept (Fichtner, 1986). For OD polytypes these groupoids are classified into OD groupoid families (Fichtner, 1977b), in analogy to space group types. These were tabulated for the special case of OD structures composed of layers of one kind with identical lattices (Fichtner, 1977a).

Nevertheless, many issues remain unsolved. For example, OD structures composed of layers with different lattices have received only a little attention. Yet in some structures, like K₂HAsO₄·2.5H₂O (Stöger, Weil & Zobetz, 2012), the different lattices of the layers are the decisive factor giving rise to OD polytypism. Moreover, we have discovered structures that follow the basic principle of OD theory, namely locally equivalent stacking possibilities, but do not follow the strict definition of OD theory (Stöger, Kautny et al., 2012; Stöger & Weil, 2013). Also, as we will show in this work, polytypes that are not locally equivalent must not be overlooked. The symmetry groupoids of these kinds of polytypes are virtually unexplored. Thus, to shed new light on OD theory and related kinds of polytypism, we are in search of suitable model compounds. A fundamental advantage of organic over in­organic compounds is the ease of introduction of systematic geometric and electronic modifications.

An ideal basis for the crystal engineering of layered structures seemed to be spacer-extended ene–yne molecules synthesized by tandem thiophene ring-fragmentation (TRF) reactions (Bobrovsky et al., 2008) owing to the generality and flexibility of the TRF protocol. The makeup of these mol­ecules resembles the TIPS-pentacene described above, though with smaller aromatic rings and a side chain extended by an ene fragment and a methylthio group (Fig. 2). An interesting aspect of these ene–yne scaffolds is the possibility to selectively oxidize the methylthio group to modify electronic properties, but also introduce structure-directing hydrogen-bond acceptors.

Figure 2 General structure of spacer-extended ene–yne molecules.

The first reports on controlled TRF reactions go back to Gronowitz & Torbjörn (1970) and Jakobsen (1970). They were explored in detail by Gronowitz & Frejd (1978), Iddon (1983) and Gilchrist (1987). This approach enables the selective yield of Z-isomers of ene–yne compounds as determined by the cyclic structure of thiophene. The exploration of tandem fragmentation reactions affording double-sided ring-opened (ene–yne) products was first reported by Fuller et al. (1999) on substituted thieno[3,2-b]thiophenes.

The first synthesized molecule of the class depicted in Fig. 2 was BSEM (1) [benzene spacer-extended with methylthio group; spacer = benzene, SiR₃ = trimethylsilyl (TMS)]. As expected, in analogy to TIPS-pentacene and related molecules (Anthony et al., 2001, 2002), BSEM (1) crystallizes in distinct molecular layers delimited by the bulky and flexible silyl groups. Therefore, this molecule was chosen as the starting point of the systematic crystallographic studies presented in this work.

It has to be noted that, in traditional crystal engineering, directed intermolecular interactions, notably via hydrogen bonding or, less commonly, halogen bonds, are used to induce controlled `self-assembly' of molecules (Aakeröy et al., 2010). In the case at hand, no such bonding exists, since the layer-delimiting moieties are trialkylsilyl groups. Nevertheless, the special makeup of the molecules clearly induces crystallization as layered structures, and therefore variations of the spacer-extended ene–yne compounds can be considered as a form of crystal engineering.

2. Results and discussion

2.1. Molecular modifications

The scope of molecular modifications and expected impacts on the layer structures are schematized in Fig. 3. The main focus is modification of the spacer to control the intermolecular spacing and width of the layer backbone, with special attention paid to the effects on the layer interface. The latter is also determined by the nature of the silyl groups. Finally, the possibility of introducing potential structure-directing hydrogen-bond acceptors by oxidation of the methylthio groups is used to create new kinds of layer structures.

Figure 3 Scope of molecular modifications (bottom) and expected impact on the structures (top).

2.1.1. Spacer modifications

The variations of the spacer unit are illustrated in Fig. 4. Firstly, the para-substituted benzene (mmm) spacer was replaced by the electron-rich 2,5-substituted thiophene (2mm) to TSEM (2). Thiophene is, from a technological point of view, an interesting core, since polythiophene has been successfully applied in the field of organic semiconductors.

Figure 4 Spacer-extended ene–yne molecules.

To analyze the effects of a bulkier spacer extending into the layer plane, we enlarged the spacer to a 3,4-ethyl­ene­dioxythiophene (EDOT) bicycle, which is, like thiophene, commonly used in the field of organic semiconductors, to give ESEM (3). Surprisingly, the resulting crystal structure was incommensurately modulated. Such a structure can be described by a periodic basic structure and periodic modulation functions, but since the periodicities are incommensurate, the overall structure is only quasi-periodic (Janssen et al., 2007; van Smaalen, 2007). A review of incommensurately modulated organic molecular structures was given by Schönleber (2011).

To better understand the reasons for the modulation, we synthesized the ring-opened 3,4-dimethoxythiophene compound DSEM (4) featuring even more steric bulk. After numerous failed crystallization attempts, we were able to obtain two non-incommensurate polymorphs, which can be considered as polytypes, from the same crystallization dish and which will be designated as polytype I and II, respectively.

2.1.2. Oxidation to sulfonyl compounds

The electronic makeup of the molecules was modified by oxidation of the thioether functionality to the corresponding sulfonyl functions (Lumpi et al., 2014). We obtained crystals of the disulfonyl analog of BSEM (1): oxBSEM (1b) and the fully oxidized trisulfonyl analog of ESEM (3): oxESEM (3b).

For oxBSEM (1b) we observed three polymorphs: polymorph I reversibly transforms into polymorph II upon cooling below ca 150 K. Polymorph III is unrelated to the former two and features no phase transition from 100 K up to the melting point. So far we were unable to determine the crystallization conditions needed to selectively obtain either polymorph.

2.1.3. Backbone modifications

An important argument of OD theory concerns the layer thickness: only for thick layers can interatomic interactions over a layer width be ignored. Thus, in a further modification we shortened the backbone (Fig. 5). At first the spacer was removed to NSEM (non-spacer-extended with methylthio group; Bobrovsky et al., 2008). We were unable to obtain single crystals suitable for structure determination of the TMS-containing molecule. Therefore, we synthesized and grew crystals of the corresponding tert-butyl-dimethylsilyl (TBDMS) compound NSEM-TBDMS (5).

Figure 5 Non-spacer-extended ene–yne molecules.

Finally, we shortened the backbone further by removing a —CH=C(SMe)— fragment to the single-sided ring-opened product ASYM (6). The name ASYM indicates a lack of symmetry in the direction of the main axis of the molecule. Despite the name, the molecule does not possess a stereogenic center and it can be considered as symmetric by reflection. Besides the short length, the compound seemed especially interesting in the light of OD theory, since the latter differentiates between polar and nonpolar layers. By growing crystals of a molecule that is polar with respect to the main axis, we were hoping to obtain polar layers, yet even ASYM (6) crystallized in nonpolar layers.

2.2. Molecular structures

The molecules presented in this work are essentially rigid, but possess three kinds of pivotal points, as depicted in Fig. 6. The main pivotal point is the connection of the side chains to the aromatic spacers (or the connection of the side chains in the case of non-spacer-extended molecules). Moreover, the methylthio (or methylsulfonyl) groups as well as the silyl groups can freely rotate. Nevertheless, the overall forms of the molecules feature little possibility for variation.

Figure 6 Rotational degrees of freedom in spacer-extended molecule.

In Table 1 the rotation angles about the freely rotatable bonds of the title compounds are compiled.

Table 1
Torsion angles in the title compounds (°)

For structures with two crystallographically different molecules each molecule is listed in a separate row. For the incommensurately modulated ESEM (3) minimum and maximum values are indicated. For thiophene spacers the S atom was used as terminal atom, for benzene spacers the C atom with a torsion angle > 90°. For the C—Si(—C≡C—)C=C torsion angle the atom with the angle closest to 0° or 180° was chosen.

Molecule	C=C—spacer	C=C(—spacer—)C=C	C=C—S—CH3	C—Si(—C≡C—)C=C
BSEM	144.26 (8)	180	138.00 (6)	30.09 (8)
TSEM	152.0 (3)	68.5 (5)	129.3 (3)	28.8 (4)
ESEM	156.36–165.31 (12)	47.4–52.4 (3)	149.81–162.53 (17)	149.81–162.53 (17)
DSEM, polytype I	156.66 (19), 163.93 (17)	50.2 (3)	121.71 (19), 111.17 (19)	160.0 (2), 158.9 (2)
DSEM, polytype II	157.1 (4), 162.7 (4)	51.4 (7)	124.7 (4), 111.2 (5)	160.8 (4), 22.1 (5)
oxBSEM, polymorph I	132.80 (11)	180	57.32 (11)	151.46 (10)
	131.49 (10)	180	62.46 (9)	24.84 (10)
oxBSEM, polymorph II	127.7 (4)	180	71.8 (4)	176.7 (5)
	128.5 (4)	180	109.2 (4)	29.9 (3)
oxBSEM, polymorph III	124.93 (17)	180	84.82 (15)	23.9 (18)
oxESEM	44.6 (3), 63.7 (3)	14.9 (3)	80.0 (2), 66.8 (2)	159.6 (2), 151.0 (2)
	46.2 (3), 64.2 (3)	17.2 (3)	78.8 (2), 67.8 (3)	159.6 (2), 153.4 (2)
NSEM-TBDMS	–	76.32 (12)	179.50 (7), 164.04 (8)	170.82 (7), 10.18 (8)
ASYM	–	–	179.3 (2)	166.7 (2), 178.4 (2)

In general, the geometries of the molecules are similar. The most notable trend is that in molecules with a benzene spacer the C=C(—spacer—)C=C torsion angle is 180° (all mol­ecules are symmetric by inversion), i.e. the methylthio or methylsulfonyl groups are located at opposite sides of the molecules (Fig. 7a). In molecules with a thiophene or a thiophene dioxide spacer, on the other hand, the torsion angle is small, i.e. the methylthio or methylsulfonyl groups face the same direction. Whereas in the methylthio/thiophene containing molecules [TSEM (2), ESEM (3) and DSEM (4)] the S atoms of the methylthio groups are in close vicinity to the S atom of the thiophene ring (Fig. 7b), in the oxidized trisulfone compound oxESEM (3b) the methylsulfonyl groups are located at the opposite side of the aromatic ring owing to steric repulsion (Fig. 7c).

Figure 7 Characteristic geometries of molecules featuring (a) a benzene spacer, (b) a thiophene spacer and methylthio groups, (c) a thiophene dioxide spacer and methylsulfonyl groups. C, O, S and Si atoms are represented by gray, red, yellow and orange ellipsoids drawn at 90% probability levels, H atoms by white spheres of arbitrary radius.

With the exception of the non-spacer-extended molecules [NSEM-TBDMS (5), ASYM (6)], the methylthio and methylsulfonyl groups feature a distinct inclination to the plane of the ene fragment. In contrast, in NSEM-TBDMS (5) and ASYM (6) one methylthio unit is nearly perfectly aligned with the ene fragment. Whereas the CH₃ unit of the methylthio groups is generally turned towards the spacer (C=C—S—CH₃ torsion angle > 90°), the methylsulfonyl groups face the side chain (C=C—SO₂—CH₃ torsion angle < 90°). An exception is polymorph II of oxBSEM (1b), whereby the two unique molecules show the two behaviors, respectively.

The silyl group is in most cases in a gauche conformation to the side chain with inclination angles of ∼ 10–30°. Only the TMS groups in one out of two molecules in polymorph II of oxBSEM (1b) and one out of two TMS groups in ASYM (6) are in a nearly perfect anti position (176.7 and 178.4°, respectively).

2.3. Layer stacking

With the exception of polymorph III of oxBSEM (1b), all structures crystallize in distinct crystallochemical layers, whereby the silyl groups are located at the layer interfaces. In Table 2 the symmetry of the layers and the operations relating adjacent layers are compiled. Here and in the following text, layer group types are designated with lower case Bravais symbols reflecting the two-dimensionality of the lattice (Kopsky & Litvin, 2006) and parentheses indicating the direction of missing translation symmetry as is customary in OD theory (Dornberger-Schiff & Grell-Niemann, 1961).

Table 2
Symmetry of the overall structures and the molecular layers and operations relating adjacent layers in the crystals under investigation

For the incommensurately modulated ESEM (3), symmetry and operations of the basic structure are listed. Pseudosymmetry of OD structures is not listed.

Structure	Space group	Layer group	Operations relating adjacent layers
BSEM	C2/c	p(1)2/c1	, , 21 [010], n [010]
TSEM	I2/c	p(1)2/c1	, , 21 [010], a [010]
ESEM, basic structure	I2/c	p(1)2/c1	, , 21 [010], a [010]
DSEM, polytype I	C2/c	p(1)21/c1	, , 21 [010], n [010]
DSEM, polytype II	Pccn	p(1)21/c1	21 [100], c [100], 2 [001], n [001]
oxBSEM, polymorph I			, tc
oxBSEM, polymorph II			, tc
oxESEM			, tc
NSEM-TBDMS	P212121	p121(1)	21 [100], 21 [001]
ASYM			, tb

The main axis of the molecules is in general distinctly inclined with respect to the stacking direction and the molecules in adjacent layers are inclined in the same direction as schematized in Fig. 8(a). In oxESEM (3b), on the other hand, the molecules feature only a little inclination, resulting in a layer stacking comparable to the scheme in Fig. 8(b). The layer stacking in polytype II of DSEM (4) and in NSEM-TBDMS (5) are exceptions: The molecules in adjacent layers are inclined in opposite directions (Fig. 8c). Indeed, these two are the only structures presented in this work that lack inversion symmetry relating adjacent layers (Table 2).

Figure 8 Scheme of the layer contacts of the title compounds observed in (a) the common case, (b) oxESEM (3b) and (c) polytype II of DSEM (4) and NSEM-TBDMS (5). Silyl groups are represented by rectangles, the yne fragments by lines and the center unit of the molecules (spacer, methylthio/methylsulfonyl and ene fragment) by ellipses.

2.4. Structural relationships

Before describing the individual crystal structures in detail (§2.5), here an overview of the structural relationships of the crystals under investigation is given. The relationships and interesting crytallographical features are summarized in Fig. 9. The 11 structures can be partitioned into two families and three unrelated structures.

Figure 9 Structural relationships of the crystals under investigation. Structures crystallizing as layers are marked by a yellow backdrop; those with same and opposite inclination in adjacent layers or little inclination (see Fig. 8) by green, blue and pink backdrops, respectively. Twinning or antiphase domains are indicated in cursive.

The first family is made up of the structures of BSEM (1) and of the analogs obtained by substitution of the aromatic spacer [TSEM (2), ESEM (3) and DSEM (4)]. BSEM (1) and TSEM (2) are merotypes, i.e. belong to a family of structures that possess layers common to all members, but also layers found only in certain members (Makovicky, 1997). Although the term originates from the crystallography of minerals, an interpretation of molecular organic structures in terms of merotypism has for example been given by our group (Stöger, Kautny et al., 2012).

Increase of the steric bulk of the thiophene spacer in TSEM (2) to EDOT in ESEM (3) leads to an incommensurately modulated structure with a basic structure isostructural (Kálmán et al., 1993) with TSEM (2). The modulation is a compromise between the need for additional space by the EDOT spacer and the retention of the structure of the interlayer contacts formed by the TMS groups.

On further increase of the steric bulk to dimethoxythiophene in DSEM (4), periodicity is restored. Although structurally related, the symmetries of TSEM (2) and DSEM (4) are not related by a group/subgroup relationship. Crystals of two DSEM (4) polytypes were grown in which layers connect in geometrically different ways (non-OD polytypes). Owing to these alternative stacking possibilities, the second polymorph crystallizes as antiphase domains (domains related by translation symmetry; Wondratschek, 1976), leading to weak diffraction intensities. Different possible kinds of connecting layers are also the likely reason for the non-OD twinning (the interface is geometrically different from the individuals) of TSEM (2).

Oxidation of the methylthio groups and removal of the spacer leads to unrelated structures. oxBSEM (1b) exists as three polymorphs making up the second family. Two polymorphs (I and II) are structurally related. Whereas the arrangement of the molecules is retained, one out of two molecules inverts orientation. Thus, although the term is usually reserved for inorganic structures, both polymorphs can be considered isopointal (same space group and Wyckoff positions of molecules; de Faria et al., 1990), but not isostructural. Polymorph III is structurally unrelated and the only analyzed structure that is not composed of layers.

Of the remaining three structures, oxESEM (3b) and ASYM (6) crystallize as OD twins, since their layers possess higher symmetry than adjacent layers. In these twins, the layer interface can be considered as a fragment of a different polytype that is locally equivalent to the twin individuals.

Finally, NSEM-TBDMS (5) is the only structure crystallizing in a Sohncke space group (the crystal is enantiomorphic).

2.5. Crystal structure details

2.5.1. BSEM (1) and TSEM (2)

In the structures of BSEM (1) and TSEM (2) the molecules are arranged in layers parallel to (100) with p(1)2/c1 symmetry (Figs. 10a and 10b). Yet, owing to the intrinsically different symmetries of the para-substituted benzene (mmm) and 2,5-substituted thiophene (mm2) rings, the molecules are located on different Wyckoff positions: Whereas the BSEM (1) molecules are symmetric by inversion, the TSEM (2) molecules are located on the twofold rotation axes. Adjacent BSEM (1) and TSEM (2) molecules are related by the mutual operation: twofold rotations for BSEM (1) and inversions for TSEM (2).

Figure 10 The crystal structures of (a) BSEM (1), (b) TSEM (2) and (c) the basic structure of ESEM (3) viewed down the monoclinic axis [010]. Color codes as in Fig. 7. H atoms have been omitted for clarity. Symmetry elements with the exception of the glide planes are indicated by the graphical symbols standardized in International Tables for Crystallography (Hahn, 2006a). Boundaries between the A and B layers are indicated by dashed lines.

Despite this difference, the outer parts of the layers are virtually identical in both structures. Moreover, adjacent layers connect in equivalent ways via 2₁ screws, n glides, inversions and the centering translations (Figs. 10a and 10b).

Thus, to relate their symmetry, the crystal structures of BSEM (1) and TSEM (2), are `sliced' into two kinds of layers, which do not correspond to layers in the chemical sense. The A layers [p(1)2₁/c1], which are composed of the —C≡C—TMS fragments of adjacent molecules, are equivalent in both structures. The B layers [p(1)2₁/c1] containing the center unit (aromatic rings, ene fragment and methylthio groups) on the other hand are fundamentally different (Figs. 10a and 10b).

Since the A and B layers of both structures crystallize in the same layer group type, BSEM (1) and TSEM (2) possess the same space-group symmetry. Yet, in a comparable cell setting, the B layers are translated along in TSEM (2) compared with BSEM (1), thus the former is described in the non-standard I2/c setting of C2/c.

The BSEM (1) molecule is slightly longer than the TSEM (2) molecule (Si–Si distance of 16.36 versus 16.07 Å). However, since the inclination of the BSEM (1) molecules with respect to the layer plane is slightly more pronounced, the molecular layer width is smaller (asinβ/2 = 16.89 versus 17.10 Å) and the packing in the [001] direction less dense [c = 10.3442 (18) versus 10.1978(8) Å]. The benzene rings require more space in the [010] direction compared with the thiophene rings, as observed by an increased lattice parameter b of 6.8690 (12) versus 6.7415 (4) Å. These small structural modifications have nearly no impact on the layer interface (Figs. 11a and 11b).

Figure 11 Contact of TMS groups in two adjacent layers of (a) BSEM (1), (b) TSEM (2) and (c) ESEM (3) projected on the layer plane (100). Groups of the lower layer are gray and blurred, other color codes as in Fig. 7. H atoms have been omitted for clarity. The extent of the unit cell [of the basic structure in the case of ESEM (3)] is indicated by black lines.

The crystal of TSEM (2) was twinned by reflection at (001). Often, OD theory is a convenient tool to understand twinning in layered structures (Stöger et al., 2013): the twin domain is interpreted as an alternative but locally equivalent stacking sequence. Application of OD theory to TSEM (2) did not lead to such a convincing interpretation, since no local pseudosymmetry is present. From a crystallochemical point of view, the only plausible twin interface is the boundary of the molecular layers. The molecule contact would then resemble more closely Fig. 8(c) than Fig. 8(a). Thus, the twin interface is geometrically different from the twin individuals. The possibility of such a twinning is demonstrated by the DSEM (4) polytypes (§2.5.3).

2.5.2. ESEM (3)

The basic structure of ESEM (3) is isostructual with TSEM (2) (Fig. 10c). Compared with TSEM (2), the ESEM (3) molecules are more strongly inclined with respect to the layer plane, resulting in a larger monoclinic angle of β = 102.301 (2)° versus β = 96.889 (5)° and smaller layer widths (asinβ = 31.72 versus 34.19 Å). As expected, the lattice parameter b increases significantly from 6.7415 (4) to 8.4003 (5) Å owing to the additional space needed by the ethyl­ene­di­oxy group.

The actual structure is incommensurately modulated with a modulation wavevector of q = σ₂b* with σ₂ = 0.6223 (1) ≃ 5/8. Although incommensurately modulated structures are non-periodic, they can be conveniently described by embedding into 3+n superspace (Janssen et al., 2007; van Smaalen, 2007). The superspace of ESEM (3) has 3+1-dimensional superspace group symmetry (van Smaalen et al., 2013; Stokes et al., 2011) , a non-standard setting of , No. 15.3 (Janssen et al., 2006).

Since q is parallel to the layer planes, the layers are equivalent. Adjacent layers are related by a 2₁ screw with intrinsic translation along a_s2/2 + a_s4/2, corresponding to an increase of the internal coordinate t by (σ₂ + 1)/2.

The twofold rotation of the molecules in the basic structure features an intrinsic translation along a_s4/2 in internal space. Thus, half of each molecule is completed by a second half located at t + 1/2. The individual molecules are therefore generally not symmetric by twofold rotation and the actual S1 atoms are not located on the twofold rotation axis.

In Figs. 12(b) and 12(c) the progression from the unmodulated chains of molecules along [010] in TSEM (2) to the modulated chains in ESEM (3) is depicted. On the one hand, the steric repulsion of the ethyl­ene­dioxy groups and the S atoms requires more space in the [010] direction, on the other hand the layer contacts via the TMS groups remain similar to those of TSEM (2) (Figs. 11b and 11c). To accommodate for both, the structure reacts by different rotations of adjacent molecules in an incommensurate way.

Figure 12 Chain of (a) TSEM (3), (b) ESEM (3) and (c) DSEM (4) molecules running along [010]. Color codes as in Fig. 7. In (b) intermolecular H⋯S contacts up to 2.91 Å are indicated by green rods to highlight the different types of intermolecular contacts. An arrow indicates a twofold rotation of the chain. If it is dashed it is valid only for the basic structure.

The distance of the equatorial H112 atoms of the ethyl­ene­dioxy group to the S atoms is plotted against the internal coordinate t in Fig. 13. Roughly two regions can be distinguished. For approximately half of the t values, marked by a gray backdrop in Fig. 13, an H112 atom is close to the thiophene S. Adjacent molecules are inclined to each other and the H112 atom protrudes into the cavity defined by the three S atoms. For the remaining t values, the molecules feature little inclination and the two H112 atoms connect only to the S atoms of the methylthio atom. In Fig. 12(b) H—S distances up to an arbitrary value of 2.91 Å are indicated to highlight the two kinds of contacts.

Figure 13 Distance of the equatorial H112 atoms of the ethylenedioxy bridge in ESEM (3) to the S atoms in the adjacent molecules plotted against t. The curves of the two H112 atoms are red and black, respectively. The distances to the S atoms of the methylthio groups and the thiophene ring are drawn using continuous and dashed lines, respectively. Gray backdrops mark the ranges where an H atom protrudes into the cavity formed by the three S atoms of the adjacent molecule.

Owing to the rigidity of the ESEM (3) molecules small rotations of the EDOT core translate into larger displacements of the TMS groups (Figs. 14a and 14b). Therefore, the connection of adjacent layers via the TMS groups features a wide variation of interatomic distances (Fig. 11). This surprising flexibility of the interlayer contacts enables incommensurate modulation.

Figure 14 Overlap of an ESEM (3) molecule at 24 equidistant t values (a, c) projected approximately on the molecular plane and (b, d) viewed down the twofold axis of the basic structure. In (a, b) the orientation of the molecules from the actual structure is unchanged; In (c, d) the molecules are rotated to minimize the interatomic distances of the thiophene rings. Bond colors with similar hue signify close t values, complementary colors a shift of t + 1/2.

The variation of the geometry of the ESEM (3) molecules is pictured in Figs. 14(c) and 14(d). The interatomic distances are close to constant (Fig. 15) and in good agreement with the expected values (Allen et al., 2006). Whereas the core of the molecule is virtually identical in all molecules, the side arms (yne fragment, TMS group) feature significant bending (Fig. 14c), needed to contact adjacent layers.

Figure 15 All intramolecular bond lengths in ESEM (3) involving non-H atoms plotted against t. Symmetry-equivalent distances located at t + 1/2 are not listed. Color codes: Si—C: black; C—S aliphatic: pink; C—S aromatic: green; C—C single bond (spacer to ene, ene to yne and yne to TMS): blue; C—O: red dashed; C—C aromatic: red; C—C double bond: blue dashed; C—C triple bond: black dashed.

2.5.3. DSEM (4)

Like in TSEM (2) and ESEM (3), the DSEM (4) molecules in both polytypes are arranged in rods running along the [010] direction (Fig. 12c). In contrast to ESEM (3), periodicity in the [010] direction is restored by rotating all molecules in a rod in the same direction (Fig. 12c). The symmetry of the rods is thus reduced from to . The rods form pairs which are related by inversion and adjacent pairs are related by 2₁ screws. As a consequence the c lattice vector is doubled compared with TSEM (2). Owing to the different arrangements of the rods the DSEM (4) layers cannot be considered as superstructures of the TSEM (2) layers and indeed, their symmetry groups (p(1)2₁/c1 with doubled c and p(1)2/c1) are not related by a group/subgroup relationship.

Although the DSEM (4) polytypes are non-OD polytypes, in the following discussion the naming conventions of OD theory will be used (Ferraris et al., 2008): the layers are designated as A_n, whereby the n is a serial index. a₀ is the vector normal to the layer planes with the length of one layer thickness.

Given an A_n layer, the adjacent A_n+1 layer can appear in two different orientations. A_n and A_n+1 are either related by the operations listed in Table 2, line 4, or those in line 5. The symmetry elements are indicated in Fig. 16.

Figure 16 The crystal structures of polytypes (a) I and (b) II of DSEM (4) viewed down [010]. Color codes and symbols as in Fig. 7. H atoms have been omitted for clarity. The An layers are indicated to the right by brackets.

Thus, the layers can be connected to an infinity of polytypes, which are not OD polytypes because (A_n, A_n+1) layer pairs are not necessarily equivalent [p(1)2/c1 and p(c)c2 symmetry, respectively]. The polytypes differ from other non-OD polytypes we discussed before (Stöger et al., 2012a; Stöger & Weil, 2013). In the latter, which we designated as `non-classic OD' polytypes, every polytype is at every point locally equivalent to all other polytypes, i.e. every point belongs to at least two equivalence regions (Grell, 1984). In DSEM (4), on the other hand, the contact plane of the layers differs geometrically among polytypes as depicted in Fig. 17. As in the case of ESEM (3) this demonstrates a remarkable flexibility of the layer contacts and confirms the assumption that the twinning of TSEM (2) is likewise caused by non-equivalent layer contacts.

Figure 17 Geometrically non-equivalent contacts of two layers in polytypes (a) I and (b) II of DSEM (4) projected on the layer plane (100). The TMS groups and the connecting sp^1 hybridized C atom are shown. Atoms of the lower layer are gray and blurred, color codes of the top layer as in Fig. 7. H atoms have been omitted for clarity.

Although the symmetry groupoids of these kind of non-OD polytypes were not elaborated up to now, the OD concept of polytypes with a maximum degree of order (MDO) (Dornberger-Schiff, 1982) can nevertheless be applied. There are two polytypes that cannot be decomposed into simpler polytypes. They are generated by continuous application of either set of operations relating the adjacent layers. The MDO₁ polytype has C2/c symmetry and lattice vector ; MDO₂ Pccn symmetry and lattice vector 2a₀.

The observed polytypes I and II are MDO₁ and MDO₂, respectively. Indeed, it is well documented for OD structures that ordered polytypes are in the vast majority of cases MDO. Fragments of the MDO₂ polytype in MDO₁ result in twinning by reflection at a plane normal to [001]. No such twinning was observed in the investigated crystal. Stacking faults in MDO₂, on the other hand, results in antiphase domains (Wondratschek, 1976), since the MDO₂ domains are related by translation. Although in principle not directly observable in diffraction patterns, we suspect that such stacking faults exist and cause the systematic low scattering power of the polytype II crystals.

As opposed to OD structures, where ordered polytypes usually feature desymmetrization of the layers compared to the idealized description (Ďurovič, 1979), the A layers in both MDO polytypes of DSEM (4) possess the p(1)2₁/c symmetry of the idealized description. A deviation from the idealized model is nevertheless observed by a slight variation of the lattice parameters and layer widths across structures [asinβ = 33.765 versus 33.630 (10) Å, b = 8.1665 (5) versus 8.271 (2) Å and c = 20.0791 (12) versus 19.717 (6) Å] and a small deviation of the molecular conformations (Fig. 18). As expected, the largest deviation is observed for the TMS groups, which are located in geometrically different environments in both polytypes.

Figure 18 Overlap of the DSEM (4) molecules in polytypes I and II, drawn in red and blue, respectively.

2.5.4. oxBSEM (1b), polymorphs I and II

Both polymorphs consist of two crystallographically different oxBSEM (1b) molecules (Fig. 19), called A and B, both located on centers of inversion (Z′ = 2/2). In both polymorphs, the crystallographically independent molecules feature different conformations: The molecules in polymorph I differ by the conformation of the TMS groups with respect to the remaining molecule, whereas in polymorph II the major difference pertains to the orientation of the methylsulfonyl groups (Fig. 19). Nevertheless, the torsion angle differences between all four conformations (Table 1) are too small for the molecules to be considered as conformers according to the criteria of Cruz-Cabeza & Bernstein (2014). Thus, the changes in these polymorphs are only conformational adjustments, though to a rather large degree in the molecule of polymorph II that has a different orientation of the methylsulfonyl groups.

Figure 19 Overlap of the independent oxBSEM (1b) molecules in (a) the high-temperature polymorph I and (b) the low-temperature polymorph II. The molecules are drawn in red and blue, respectively. H atoms have been omitted for clarity.

The molecules are arranged in layers parallel to (001) with symmetry, whereby the B molecules form rods along [100], connected by the A molecules (Fig. 20).

Figure 20 Layers in polymorphs (a) I and (b) II of oxBSEM (1b) viewed approximately along the main axis of the molecules. Color codes as in Fig. 7. H atoms have been omitted for clarity. C—H⋯O and C—H⋯C contacts are indicated by arrows originating from the `donor' C atoms, C—H⋯H—C contacts by double-sided arrows connecting the C atoms.

The most striking difference between the two polymorphs is the orientation of the A molecules, which are rotated by nearly 180°. In projection along [100], the S atoms of the methylsulfonyl groups are nearly superimposed in polymorph II, while in polymorph I the methylsulfonyl groups of subsequent molecules point in opposite directions (Fig. 21).

Figure 21 Crystal structures of the polymorphs (a, b) I and (c, d) II of oxBSEM (1b), viewed down (a, c) [010] and (b, d) [100]. Color codes as in Fig. 7. H atoms have been omitted for clarity.

Thus, the I II phase transition has to be considered reconstructive, which is consistent with the destruction of large single crystals on cooling. The transformation is accompanied by an inclination of the molecules with respect to the stacking direction (Figs. 21b and 21d). In consequence, the layer interfaces are fundamentally different in the two polytypes (Fig. 22), demonstrating again the flexibility in layer arrangements allowed by the TMS groups.

Figure 22 Layer contacts in the polymorphs (a) I and (b) of oxBSEM (1b) projected on the layer plane (100). Only the TMS groups are shown. Atoms of the lower layer are gray and blurred, color codes of the top layer as in Fig. 7. H atoms have been omitted for clarity.

Although methylsulfonyl groups are potential hydrogen bond acceptors, the oxBSEM (1b) molecules do not possess classical hydrogen-bond donors. Indeed, attempts to analyze the phase transition by listing the weak hydrogen bonds of the two polymorphs were inconclusive, since these lists depend on rather arbitrary distance and angle limits. A more holistic and unbiased approach for the description of molecular inter­actions in polymorphs, which was established in the last decade, is the analysis of molecular Hirshfeld surfaces (Spackman & Jayatilaka, 2009). The d_e/d_i fingerprint plots (Spackman & McKinnon, 2002) of the two molecules in both polymorphs are depicted in Fig. 23. As expected, contacts not involving H atoms, as well as those involving S and Si atoms, are negligible. First conclusions can be drawn from the shape of the plots: In both polymorphs, the individual plots are not symmetric by reflection at the d_e = d_i line, but the plots of the crystallographically independent molecules are approximately related by such an operation. Thus, the closest contacts are mostly between non-equivalent molecules along the [010] direction. An exception are the regions 1 and 2 in Fig. 23, which correspond to C=C—H⋯O and SC—H⋯C≡C contacts of equivalent molecules along [100] (Fig. 20).

Figure 23 di/de fingerprint plots of the oxBSEM (1b) molecules in polymorphs (a, b) I, (c, d) II and (e) III, calculated with CrystalExplorer (Wolff et al., 2012). Regions where H⋯H, H⋯O and H⋯C dominate are drawn in yellow, red and blue, respectively, other regions in gray. Brighter colors indicate a higher proportion of the surface. Regions discussed in the text connecting two B molecules or A and B molecules are marked by green and red ellipses, respectively.

Surprisingly, the fingerprint plot of the A molecule of polymorph I resembles the plot of the B molecule of polymorph II and vice versa. Thus, one could say that the roles of the donor and acceptor are reversed on phase transition, although overall the type of interatomic interaction remains similar. The most prominent interactions are indicated in Fig. 23 and correlated to the actual atoms in Fig. 20 and Table 3. A striking feature that is only observed in polymorph I is region 6, a very short C—H⋯H—C contact (2.30 Å) between two aromatic protons. Thus, although there is no definite proof, one might speculate that, on cooling, the structure contracts until these H atoms are too close and the structure becomes unstable. This conjecture would not have been insinuated without the analysis of fingerprint plots.

Table 3
Prominent intermolecular contacts in the d_i/d_e fingerprint plots of the I and II polymorphs of oxBSEM (1b) marked in Fig. 23

	Polymorph I		Polymorph II
Region	Atoms	Molecular groups	Atoms	Molecular groups
1	C5′—H5′⋯O2′	ene–sulfone
2	C11′—H112′⋯C7′	Methylsulfone–yne	C11′—H113′⋯C3′	Methylsulfone–benzene
3	C11—H111⋯C3′	Methylsufone–benzene	C11′—H112′⋯C2	Methylsulfone–benzene
4	C9′—H93′⋯O2	TMS–sulfone	C5—H5⋯O2′	Ene–sulfone
5	–	–	C5′—H5′⋯O1	Ene–sulfone
6	C3—H3′⋯H3—C3	Benzene–benzene	–	–

2.5.5. oxBSEM (1b), polymorph III

The molecules in polymorph III of oxBSEM (1b) are not arranged in distinct silyl-group delimited layers (Fig. 24). One crystallographically unique oxBSEM (1b) molecule is located on a center of inversion. It can again not be considered a different conformer. As expected, the Hirshfeld fingerprint plot (Fig. 21e) is nearly symmetric by reflection at d_e = d_i. It most closely resembles the plot of the A molecule in polymorph II, but the H⋯C contacts are distinctly less prominent, indicating an energetically more favorable packing. Indeed, polymorph III has higher symmetry (same space group type, but Z′ = 1/2 versus 2/2) and distinctly higher density (1.267 versus 1.229 g cm⁻³ at 100 K). Thus, the I II transition is an example of Ostwald's rule stating that a system does not change into the thermodynamically stable, but the nearest metastable state.

Figure 24 Crystal structure of polymorph III of oxBSEM (1b) viewed down [100]. Color codes as in Fig. 7.

2.5.6. oxESEM (3b)

The oxESEM (3b) molecules are arranged in layers parallel to (001) with (idealized) p2₁/b1(1) symmetry (Fig. 25), which are, despite possessing the same layer group type, structurally unrelated to the layers in BSEM (1), TSEM (2), the basic structure of ESEM (3) and DSEM (4).

Figure 25 The crystal structure of oxESEM (3b) viewed down (a) [010] and (b) [100]. The location of the An layers is indicated by brackets to the right. Color codes as in Fig. 7.

One crystallographically unique molecule is located on a general position. The layers are stacked in such a way that the b-glide planes do not overlap. In consequence oxESEM (3b) belongs to a category I OD family composed of layers of one kind. The OD groupoid family symbol reads according to the notation introduced by Dornberger-Schiff & Grell-Niemann (1961) as

It has to be noted that in this case c₀ is conveniently chosen not normal to the layer planes, to reflect the monoclinic point group 2/m11 of the OD family (Fichtner, 1979), whereby a second metric parameter describing the relative layer positions vanishes. In one possible arrangement of the (A_n, A_n+1) layer pair, A_n+1 is related to A_n by a 2_r screw with intrinsic translation along ra/2 or equivalently by an n_1,2 glide with intrinsic translation along (b/2) + c₀. The other geometrically equivalent arrangements are derived using the NFZ relationship (Ďurovič, 1997): Given an A_n layer, an adjacent layer can appear in Z = N/F = [p11(1):pb1(1)] = 2 orientations, related by the b glides of A_n. p11(1) and pb1(1) are the groups of those layer operations that do not invert the orientation of the layers with respect to the stacking direction [called λ-τ partial operations (POs) in the OD literature].

These stacking possibilities give rise to two MDO polytypes: MDO₁ {, c = c₀ + [(r − 1)/2]a} and MDO₂ (P2₁/n11, c = 2c₀), obtained by continuous application of the 2_r screws and n_1,2 glides, respectively. The symmetry of the two polytypes is schematized in Fig. 26.

Figure 26 Schematic representation of the symmetry of the (a) MDO1 and (b) MDO2 polytypes of oxESEM (3b). Triangles are black on one and white on the other side. (Partial) symmetry operations of a layer and relating adjacent layers are indicated by the graphical symbols standardized in International Tables for Crystallography (Hahn, 2006a). Additionally for operations with non-crystallographic intrinsic translations the printed symbol is given.

The major polytype of the crystals under investigation is the MDO₁ polytype. Fragments of the MDO₂ polytype were observed indirectly by systematic twinning. The twin element corresponds to the plane of the b glides of the A layers. This kind of twinning is fundamentally different from that in TSEM (2) or the polytypism of DSEM (4). The latter is only possible owing to the flexibility of the layer contacts, whereas in oxESEM (3b) the layer contacts are equivalent in all polytypes.

In the major MDO₁ polytype, the symmetry of the A layers is reduced by an index of 2 from p2₁/b1(1) to . This translates to a small deviation of γ = 89.771 (2)° from the ideal value of 90° imposed by the rectangular layer lattice and a small deviation of the atoms from the positions compared with the idealized p2₁/b1(1) layers. Significant deviations from ideal symmetry are limited to the TMS groups, which are located at the layer interfaces [deviations of 0.272 Å (Si2) up to 0.508 Å (C10)]. This is expected, since the layer interfaces are located in an environment which deviates from the ideal layer symmetry. The closer the atoms are located to the center of the layers, the smaller the deviation. The C atoms of the yne fragment connecting to the TMS group deviate by 0.130 Å (C8) and 0.138 Å (C16), all other atoms by less than 0.100 Å.

2.5.7. NSEM-TBDMS (5)

Although achiral, the NSEM-TBDMS (5) mol­ecules crystallize in the Sohncke group P 2₁ 2₁ 2₁. The crystal under investigation was enantiomerically pure [Flack parameter 0.03 (3)]. An estimation of the number of achiral molecules crystallizing in Sohncke groups was given by Pidcock (2005).

Whereas the central part of the molecule is nearly symmetric by twofold rotation, the TBDMS groups feature a distinctly different orientation with respect to the methylthio groups, resulting in molecules with 1 symmetry (Figs. 27a and 27b). The molecules are arranged in layers parallel to (001) with p 1 2₁ (1) symmetry. The layers in turn are connected by 2₁ screws with axes parallel to [100] and [010] (Fig. 27c).

Figure 27 (a, b) The NSEM-TBDMS (5) molecule viewed down two different directions, showing the different conformations of the methylthio group with respect to the TBDMS groups (top group: gauche, bottom group: eclipsed) and (c) crystal structure of NSEM-TBDMS (5) viewed down [100]. H atoms have been omitted for clarity. Color codes as in Fig. 7.

2.5.8. ASYM (6)

The ASYM (6) molecules are located on general positions. Despite being polar with respect to the main direction, they are arranged in nonpolar layers parallel to (010) with symmetry (Fig. 28).

Figure 28 The crystal structure of ASYM (6) viewed down (a) [100] and (b) [001]. The A^1 and A^2 OD layers are marked by a gray and white backdrop, respectively. The boundaries of the crystallochemical layers are indicated by dotted lines. Color codes as in Fig. 7.

In contrast to the other layered structures, the TMS groups are not as clearly located at the layer interface: every second group is moved away from the surface into the layers. This can be attributed to ASYM (6) being the shortest of the molecules under investigation.

The systematic twinning of ASYM (6) can be explained by local pseudosymmetry: With the exception of one TMS group, the molecules are practically symmetric by reflection at (100) (Fig. 28b). Thus the structure can be `sliced' into OD layers (Grell, 1984) of two kinds, which do not correspond to layers in the crystallochemical sense (Fig. 28). The A¹ layers contain the parts of the molecule that possess mirror symmetry, whereas the A² layers are made up of the remaining TMS groups.

As a consequence, the structure belongs to a category IV OD family composed of nonpolar layers of two kinds. The corresponding OD groupoid family symbol reads according to the notation introduced by Grell & Dornberger-Schiff (1982) as

Accordingly, the structure is made up of an alternating stacking of A¹ and A² layers, with p2₁/m(1)1 and symmetry, respectively. b₀ is chosen not normal to the layer planes so that one metric parameter vanishes. In one possible arrangement of the (A¹_n, A²_n+1) layer pair, the origin of A² is reached from the origin of A¹ by translation along (b₀/2) + sa.

According to the NFZ relationship, given an A¹_n layer, the adjacent layers can appear in Z = N/F = [pm(1)1:p1(1)1] = 2 orientations, related by the m operation of the A¹_n layer. For the A² layers on the other hand, there is only one way to connect to the A¹ layers, since all λ-τ POs of A² (p1(1)1) apply likewise to A¹.

These stacking possibilities give rise to two MDO polytypes: MDO₁ (, b = b₀ + 2sa) is obtained by continuous application of the inversion operations of the A¹ layers; MDO₂ (P2₁/b11, b = 2b₀) by application of the 2₁ screws. The symmetry of the two polytypes is schematized in Fig. 29.

Figure 29 Schematic representation of the symmetry of the (a) MDO1 and (b) MDO2 polytypes of ASYM (6). Symbols as in Fig. 26.

The bulk of the ASYM (6) crystals under investigation are made up of the MDO₁ polytype, whereas fragments of the MDO₂ polytype are located at the twin interface. A twin element corresponds to the mirror plane of the A¹ layers. Again, all polytypes are locally equivalent and no flexibility of the layer contact is needed for twinning.

In MDO₁, the symmetry of the A¹ layers is reduced by an index of 2 from p2₁/m(1)1 to . This is reflected by a deviation of β = 92.510 (2)° from the ideal value of 90° according to the rectangular layer lattice, and by a slight deviation of the molecules from their idealized positions. Under the assumption of β = 90°, the only non-negligible deviations (> 0.1 Å) of non-H atoms from the idealized positions of the A¹ layers are observed for the atoms of the TMS group that are not located on the mirror plane (C10, C11, deviation of 0.11 Å) and for the C3 atom, which connects to the TMS group in the A² layer (deviation of 0.12 Å).

The deviation of β from the ideal value of 90° by 2.51° is remarkably large and distinctly larger than in the case of oxESEM (3b). As a consequence, the lattices of the twin domains do not match (deviation of 5°) and the crystals are distinctly distorted at the twin interface. The orthorhombic MDO₂ fragment at the twin interface possesses an ideal angle of 90° and it therefore enables the passage of the two extremes of the MDO₁ domains.

In contrast to oxESEM (3b), the desymmetrization does not result in two crystallographically unique molecules, but rather in a desymmetrization of the A¹ parts of the molecule from m to 1 symmetry.

3. Experimental

Detailed syntheses and spectroscopic characterizations of all compounds are given by Lumpi (2013). Single crystals of BSEM (1) (i-PrOH, EtOH), oxBSEM (1b) (EtOH), ESEM (3) (EtOH, in a glove-box with N₂ atmosphere), oxESEM (3b) (MeOH) and DSEM (4) (EtOH) were obtained by slow evaporation at room temperature. Crystallization of TSEM (2) from solvents failed to give single crystals suitable for single-crystal diffraction. Tiny single crystals were instead afforded by crystallization of the oily sample at ∼293 K over a time period of several months.

Single-crystal data were collected and processed on a Bruker Kappa APEXII diffractometer system (Bruker, 2008). Data were reduced using the SAINT-Plus (Bruker, 2008) and EVAL (Duisenberg et al., 2003) suites and corrected for absorption effects with SADABS or TWINABS (Bruker, 2008). Structures were solved with SUPERFLIP (Palatinus & Chapuis, 2007) and refined with JANA2006 (Petříček et al., 2014). More details on single-crystal diffraction and structure refinement are available as supplementary materials.

4. Conclusion and outlook

We set out to create layered structures, expecting to obtain OD polytypes due to different local layer symmetry. We were indeed successful with the systematic twins oxESEM (3a) and ASYM (6). Surprisingly though, we observed numerous other crystallographic phenomena, which are not caused by local layer symmetry but by the remarkable flexibility of the layer contacts. On the one hand, a given layer contact can accommodate significant distortion leading to the incommensurate modulation of ESEM (3). On the other hand, identical layers can connect in fundamentally different ways as observed in the non-OD polytypism of TSEM (2) and DSEM (4) and the layer contacts can accomodate the different molecular arrangements observed in the temperature-dependent polymorphism of oxBSEM (1b).

These phenomena demonstrate the necessity of a generalization of space-group symmetry to local symmetry. These so-far unexplored groupoids are necessary not only for the description of polytypism, but also of structural relationships like the merotypism of BSEM (1) and TSEM (2).

Future synthetic work will focus on the core of the layers (alterations of the aromatic spacer and an elongation of the methylthio groups), as well as the application of other silyl groups like TBDMS or TIPS to induce different layer contacts as in NSEM-TBDMS (5). Besides studying crystallographic phenomena, the application of acene or polythiophene derivatives may also enable the application of the layer motifs in the field of functional organic materials. To achieve this goal an adjustment of the steric bulk of the cores and the size of the silyl groups will be needed to obtain an optimum face-to-face stacking of the extended aromatic cores. Moreover, the merotypism of BSEM (1) and TSEM (2) presents an opportunity for the controlled epitaxial growth of different kinds of molecules, a crucial point in the design of devices.

Supporting information

Computing details

(ASYM)

Crystal data

C13H22SSi2	Z = 2
Mr = 266.6	F(000) = 288
Triclinic, P1	Dx = 1.052 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.2016 (4) Å	Cell parameters from 8516 reflections
b = 9.7603 (4) Å	θ = 2.5–30.1°
c = 12.2829 (4) Å	µ = 0.31 mm^−1
α = 95.4952 (16)°	T = 100 K
β = 92.510 (2)°	Block, clear colourless
γ = 101.346 (2)°	0.82 × 0.61 × 0.20 mm
V = 840.86 (6) Å^3

Data collection

Bruker KAPPA APEX II CCD diffractometer	4622 independent reflections
Radiation source: X-ray tube	3651 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.035
ω– and φ–scans	θmax = 30.2°, θmin = 1.7°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.80, Tmax = 0.94	k = −13→13
21588 measured reflections	l = −17→17

Refinement

Refinement on F	88 constraints
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.055	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 2.27	(Δ/σ)max = 0.010
4622 reflections	Δρmax = 0.61 e Å^−3
146 parameters	Δρmin = −0.39 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
Si1	0.86915 (9)	0.88589 (6)	0.65955 (4)	0.02025 (19)
Si2	0.70091 (8)	0.30001 (6)	−0.04248 (4)	0.01583 (17)
S1	0.72090 (10)	0.39931 (6)	0.38295 (4)	0.02794 (19)
C1	0.7757 (3)	0.5774 (2)	0.35942 (15)	0.0154 (6)
C2	0.8091 (3)	0.6819 (2)	0.45166 (15)	0.0168 (6)
C3	0.8371 (3)	0.7643 (2)	0.53256 (16)	0.0204 (7)
C4	0.7861 (3)	0.6114 (2)	0.25543 (15)	0.0209 (7)
C5	0.7553 (3)	0.5109 (2)	0.16171 (16)	0.0203 (7)
C6	0.7310 (3)	0.4267 (2)	0.08120 (16)	0.0204 (7)
C7	0.7327 (4)	1.0237 (3)	0.6368 (2)	0.0398 (10)
C8	1.1260 (3)	0.9638 (2)	0.68819 (17)	0.0288 (8)
C9	0.7807 (4)	0.7832 (3)	0.77261 (18)	0.0387 (9)
C10	0.8896 (3)	0.1956 (3)	−0.03317 (18)	0.0250 (8)
C11	0.4620 (3)	0.1839 (3)	−0.04603 (19)	0.0268 (8)
C12	0.7230 (3)	0.4002 (2)	−0.16385 (16)	0.0251 (7)
C13	0.7202 (4)	0.4061 (2)	0.52981 (16)	0.0263 (7)
H4	0.815937	0.709181	0.244356	0.025*
H71	0.745287	1.088845	0.701696	0.0478*
H72	0.780703	1.072711	0.57652	0.0478*
H73	0.601278	0.981128	0.62038	0.0478*
H81	1.144251	1.02231	0.756769	0.0346*
H82	1.19586	0.889965	0.691999	0.0346*
H83	1.170417	1.019307	0.630586	0.0346*
H91	0.796553	0.844206	0.839921	0.0465*
H92	0.648659	0.742054	0.75704	0.0465*
H93	0.851126	0.710239	0.779451	0.0465*
H101	0.886881	0.136275	−0.100482	0.0299*
H102	1.011193	0.257987	−0.020558	0.0299*
H103	0.868292	0.138585	0.026337	0.0299*
H131	0.684179	0.312584	0.550388	0.0316*
H132	0.844828	0.448186	0.561784	0.0316*
H133	0.63121	0.461264	0.555624	0.0316*
H111	0.448178	0.112484	−0.106965	0.0322*
H112	0.448567	0.140468	0.020879	0.0322*
H113	0.366182	0.238678	−0.053835	0.0322*
H121	0.702722	0.335862	−0.229451	0.0302*
H122	0.630085	0.458479	−0.163632	0.0302*
H123	0.847798	0.458071	−0.161256	0.0302*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0271 (3)	0.0191 (3)	0.0123 (3)	0.0030 (3)	−0.0023 (3)	−0.0042 (2)
Si2	0.0135 (3)	0.0203 (3)	0.0122 (2)	0.0027 (3)	−0.0005 (2)	−0.0034 (2)
S1	0.0432 (4)	0.0181 (3)	0.0203 (3)	0.0044 (3)	−0.0039 (3)	−0.0024 (2)
C1	0.0106 (10)	0.0175 (10)	0.0172 (9)	0.0043 (9)	−0.0019 (8)	−0.0040 (8)
C2	0.0156 (10)	0.0182 (10)	0.0166 (9)	0.0037 (9)	−0.0010 (9)	0.0018 (8)
C3	0.0237 (11)	0.0193 (11)	0.0175 (9)	0.0034 (10)	−0.0005 (9)	0.0012 (8)
C4	0.0238 (11)	0.0183 (11)	0.0180 (10)	−0.0001 (10)	0.0005 (9)	−0.0016 (8)
C5	0.0190 (11)	0.0233 (11)	0.0178 (9)	0.0034 (10)	−0.0004 (9)	0.0009 (8)
C6	0.0145 (10)	0.0269 (12)	0.0186 (10)	0.0031 (10)	0.0002 (9)	−0.0012 (9)
C7	0.0490 (18)	0.0457 (18)	0.0272 (14)	0.0253 (15)	−0.0066 (13)	−0.0125 (12)
C8	0.0333 (13)	0.0221 (12)	0.0272 (12)	0.0002 (11)	−0.0041 (11)	−0.0036 (10)
C9	0.0467 (16)	0.0424 (16)	0.0178 (11)	−0.0116 (14)	−0.0010 (12)	0.0008 (11)
C10	0.0226 (12)	0.0310 (14)	0.0230 (12)	0.0120 (11)	−0.0009 (10)	−0.0011 (10)
C11	0.0180 (12)	0.0317 (14)	0.0278 (12)	−0.0006 (10)	−0.0006 (10)	0.0006 (10)
C12	0.0263 (13)	0.0304 (13)	0.0208 (10)	0.0099 (11)	0.0038 (10)	0.0033 (9)
C13	0.0327 (14)	0.0265 (12)	0.0218 (10)	0.0092 (12)	0.0002 (11)	0.0066 (9)

Geometric parameters (Å, º)

Si1—C3	1.844 (2)	C8—H81	0.96
Si1—C7	1.850 (3)	C8—H82	0.96
Si1—C8	1.861 (2)	C8—H83	0.96
Si1—C9	1.852 (3)	C9—H91	0.96
Si2—C6	1.841 (2)	C9—H92	0.96
Si2—C10	1.858 (3)	C9—H93	0.96
Si2—C11	1.861 (2)	C10—H101	0.96
Si2—C12	1.855 (2)	C10—H102	0.96
S1—C1	1.760 (2)	C10—H103	0.96
C1—C2	1.428 (3)	C11—H111	0.96
C1—C4	1.352 (3)	C11—H112	0.96
C2—C3	1.201 (3)	C11—H113	0.96
C4—C5	1.419 (3)	C12—H121	0.96
C4—H4	0.96	C12—H122	0.96
C5—C6	1.207 (3)	C12—H123	0.96
C7—H71	0.96	C13—H131	0.96
C7—H72	0.96	C13—H132	0.96
C7—H73	0.96	C13—H133	0.96
C3—Si1—C7	107.10 (11)	H81—C8—H82	109.47
C3—Si1—C8	109.19 (10)	H81—C8—H83	109.47
C3—Si1—C9	107.83 (10)	H82—C8—H83	109.47
C7—Si1—C8	110.81 (12)	Si1—C9—H91	109.47
C7—Si1—C9	112.10 (13)	Si1—C9—H92	109.47
C8—Si1—C9	109.70 (11)	Si1—C9—H93	109.47
C6—Si2—C10	107.63 (10)	H91—C9—H92	109.47
C6—Si2—C11	108.53 (10)	H91—C9—H93	109.47
C6—Si2—C12	108.15 (10)	H92—C9—H93	109.47
C10—Si2—C11	110.48 (11)	Si2—C10—H101	109.47
C10—Si2—C12	111.22 (11)	Si2—C10—H102	109.47
C11—Si2—C12	110.71 (11)	Si2—C10—H103	109.47
S1—C1—C2	118.56 (15)	H101—C10—H102	109.47
S1—C1—C4	119.45 (15)	H101—C10—H103	109.47
C2—C1—C4	121.99 (19)	H102—C10—H103	109.47
C1—C2—C3	176.7 (2)	Si2—C11—H111	109.47
Si1—C3—C2	177.07 (19)	Si2—C11—H112	109.47
C1—C4—C5	123.7 (2)	Si2—C11—H113	109.47
C1—C4—H4	118.15	H111—C11—H112	109.47
C5—C4—H4	118.14	H111—C11—H113	109.47
C4—C5—C6	179.0 (2)	H112—C11—H113	109.47
Si2—C6—C5	178.36 (19)	Si2—C12—H121	109.47
Si1—C7—H71	109.47	Si2—C12—H122	109.47
Si1—C7—H72	109.47	Si2—C12—H123	109.47
Si1—C7—H73	109.47	H121—C12—H122	109.47
H71—C7—H72	109.47	H121—C12—H123	109.47
H71—C7—H73	109.47	H122—C12—H123	109.47
H72—C7—H73	109.47	H131—C13—H132	109.47
Si1—C8—H81	109.47	H131—C13—H133	109.47
Si1—C8—H82	109.47	H132—C13—H133	109.47
Si1—C8—H83	109.47

(BSEM)

Crystal data

C22H30S2Si2	F(000) = 888
Mr = 414.8	Dx = 1.147 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18955 reflections
a = 34.148 (6) Å	θ = 2.4–34.9°
b = 6.8690 (12) Å	µ = 0.33 mm^−1
c = 10.3442 (18) Å	T = 100 K
β = 98.343 (8)°	Plate, clear yellow
V = 2400.7 (7) Å^3	0.77 × 0.25 × 0.03 mm
Z = 4

Data collection

Bruker KAPPA APEX II CCD diffractometer	5255 independent reflections
Radiation source: X-ray tube	4193 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.035
ω– and φ–scans	θmax = 35°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −54→54
Tmin = 0.91, Tmax = 0.99	k = −11→11
38270 measured reflections	l = −16→16

Refinement

Refinement on F	60 constraints
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.044	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 2.19	(Δ/σ)max = 0.004
5255 reflections	Δρmax = 0.43 e Å^−3
118 parameters	Δρmin = −0.22 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S	0.419611 (6)	0.11777 (3)	0.11095 (2)	0.01837 (6)
Si	0.321272 (7)	0.35715 (3)	0.43975 (2)	0.01769 (7)
C1	0.46995 (2)	0.42787 (11)	0.06768 (8)	0.01359 (19)
C2	0.49845 (2)	0.30281 (11)	0.02820 (8)	0.0156 (2)
C3	0.47204 (2)	0.62626 (11)	0.03738 (8)	0.0155 (2)
C4	0.43845 (2)	0.35546 (11)	0.13903 (8)	0.0140 (2)
C5	0.42532 (2)	0.46355 (12)	0.23315 (8)	0.0165 (2)
C6	0.39321 (2)	0.41453 (12)	0.30064 (8)	0.0171 (2)
C7	0.36568 (3)	0.38581 (12)	0.35998 (9)	0.0185 (2)
C8	0.30424 (3)	0.60690 (14)	0.47498 (11)	0.0328 (3)
C9	0.33321 (3)	0.21502 (14)	0.59275 (9)	0.0254 (3)
C10	0.28334 (3)	0.22535 (19)	0.32517 (11)	0.0366 (3)
C11	0.41142 (3)	0.09948 (12)	−0.06499 (9)	0.0220 (2)
H2	0.497455	0.166172	0.046963	0.0187*
H3	0.452654	0.714258	0.06259	0.0186*
H5	0.438836	0.583836	0.256514	0.0198*
H81	0.27977	0.598682	0.51013	0.0394*
H82	0.323867	0.669084	0.537266	0.0394*
H83	0.300301	0.681531	0.395692	0.0394*
H91	0.31118	0.219313	0.640727	0.0305*
H92	0.338531	0.082339	0.571889	0.0305*
H93	0.356114	0.269829	0.644875	0.0305*
H101	0.261133	0.194452	0.368688	0.044*
H102	0.274733	0.306195	0.25075	0.044*
H103	0.294552	0.107359	0.2969	0.044*
H111	0.397377	−0.018702	−0.090426	0.0264*
H112	0.396098	0.208936	−0.101064	0.0264*
H113	0.436429	0.098479	−0.097055	0.0264*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.02379 (11)	0.01330 (10)	0.01955 (11)	−0.00388 (7)	0.00835 (8)	−0.00053 (7)
Si	0.01397 (11)	0.02170 (12)	0.01876 (12)	0.00170 (8)	0.00695 (9)	0.00076 (9)
C1	0.0128 (3)	0.0140 (3)	0.0144 (3)	−0.0003 (2)	0.0034 (3)	−0.0015 (3)
C2	0.0162 (3)	0.0125 (3)	0.0188 (4)	0.0005 (3)	0.0050 (3)	−0.0004 (3)
C3	0.0146 (3)	0.0139 (3)	0.0188 (4)	0.0018 (3)	0.0057 (3)	−0.0022 (3)
C4	0.0129 (3)	0.0136 (3)	0.0160 (3)	−0.0006 (2)	0.0033 (3)	−0.0003 (3)
C5	0.0154 (3)	0.0168 (4)	0.0184 (4)	−0.0019 (3)	0.0062 (3)	−0.0018 (3)
C6	0.0180 (4)	0.0154 (3)	0.0186 (4)	0.0003 (3)	0.0051 (3)	−0.0019 (3)
C7	0.0180 (4)	0.0172 (4)	0.0213 (4)	0.0011 (3)	0.0058 (3)	−0.0007 (3)
C8	0.0359 (6)	0.0303 (5)	0.0355 (6)	0.0140 (4)	0.0166 (5)	0.0052 (4)
C9	0.0240 (4)	0.0279 (5)	0.0258 (5)	0.0029 (3)	0.0089 (4)	0.0055 (4)
C10	0.0225 (5)	0.0585 (7)	0.0293 (5)	−0.0116 (5)	0.0054 (4)	−0.0055 (5)
C11	0.0278 (4)	0.0176 (4)	0.0207 (4)	−0.0054 (3)	0.0038 (3)	−0.0039 (3)

Geometric parameters (Å, º)

S—C4	1.7634 (9)	C6—C7	1.2112 (13)
Si—C7	1.8391 (11)	C8—H81	0.96
Si—C8	1.8644 (12)	C8—H82	0.96
Si—C9	1.8539 (11)	C8—H83	0.96
Si—C10	1.8593 (12)	C9—H91	0.96
C1—C2	1.4025 (12)	C9—H92	0.96
C1—C3	1.4024 (12)	C9—H93	0.96
C1—C4	1.4765 (12)	C10—H101	0.96
C2—C3^i	1.3826 (12)	C10—H102	0.96
C2—H2	0.96	C10—H103	0.96
C3—H3	0.96	C11—H111	0.96
C4—C5	1.3516 (12)	C11—H112	0.96
C5—C6	1.4232 (13)	C11—H113	0.96
C5—H5	0.96
C7—Si—C8	106.87 (5)	Si—C7—C6	174.87 (7)
C7—Si—C9	110.24 (4)	Si—C8—H81	109.47
C7—Si—C10	108.04 (5)	Si—C8—H82	109.47
C8—Si—C9	110.72 (5)	Si—C8—H83	109.47
C8—Si—C10	111.37 (5)	H81—C8—H82	109.47
C9—Si—C10	109.54 (5)	H81—C8—H83	109.47
C2—C1—C3	118.05 (7)	H82—C8—H83	109.47
C2—C1—C4	121.73 (7)	Si—C9—H91	109.47
C3—C1—C4	120.22 (7)	Si—C9—H92	109.47
C1—C2—C3^i	120.86 (7)	Si—C9—H93	109.47
C1—C2—H2	119.57	H91—C9—H92	109.47
C3^i—C2—H2	119.57	H91—C9—H93	109.47
C1—C3—C2^i	121.09 (7)	H92—C9—H93	109.47
C1—C3—H3	119.46	Si—C10—H101	109.47
C2^i—C3—H3	119.46	Si—C10—H102	109.47
S—C4—C1	120.29 (6)	Si—C10—H103	109.47
S—C4—C5	118.43 (6)	H101—C10—H102	109.47
C1—C4—C5	121.12 (7)	H101—C10—H103	109.47
C4—C5—C6	125.66 (8)	H102—C10—H103	109.47
C4—C5—H5	117.17	H111—C11—H112	109.47
C6—C5—H5	117.17	H111—C11—H113	109.47
C5—C6—C7	175.65 (9)	H112—C11—H113	109.47

Symmetry code: (i) −x+1, −y+1, −z.

(BSEMOX1)

Crystal data

C22H30O4S2Si2	Z = 2
Mr = 478.8	F(000) = 508
Triclinic, P1	Dx = 1.212 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8197 (3) Å	Cell parameters from 9974 reflections
b = 12.1073 (5) Å	θ = 3.1–34.9°
c = 16.1123 (7) Å	µ = 0.32 mm^−1
α = 92.3607 (19)°	T = 150 K
β = 93.9781 (19)°	Plate, clear colourless
γ = 98.3425 (19)°	0.70 × 0.65 × 0.10 mm
V = 1311.34 (10) Å^3

Data collection

Bruker KAPPA APEX II CCD diffractometer	11485 independent reflections
Radiation source: X-ray tube	8331 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.030
ω– and φ–scans	θmax = 35.1°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −9→11
Tmin = 0.81, Tmax = 0.97	k = −19→19
57779 measured reflections	l = −26→25

Refinement

Refinement on F	120 constraints
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.044	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 2.15	(Δ/σ)max = 0.001
11485 reflections	Δρmax = 0.44 e Å^−3
271 parameters	Δρmin = −0.39 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
Si	0.21273 (5)	0.10115 (3)	0.383099 (19)	0.03221 (10)
S	0.09772 (3)	0.261886 (18)	0.087388 (15)	0.01803 (7)
O1	0.03695 (10)	0.29046 (6)	0.00453 (4)	0.0281 (2)
O2	−0.03105 (11)	0.27970 (6)	0.15188 (5)	0.0301 (2)
C1	0.42030 (13)	0.42138 (7)	0.05499 (6)	0.0179 (3)
C2	0.30773 (14)	0.50002 (7)	0.02378 (6)	0.0197 (3)
C3	0.61308 (14)	0.42241 (7)	0.03067 (6)	0.0200 (3)
C4	0.34126 (14)	0.33876 (7)	0.11406 (6)	0.0203 (3)
C5	0.44536 (17)	0.31828 (9)	0.18362 (7)	0.0317 (3)
C6	0.37894 (18)	0.24393 (10)	0.24546 (7)	0.0357 (4)
C7	0.32224 (19)	0.18517 (10)	0.30006 (7)	0.0381 (4)
C8	0.2319 (2)	−0.04684 (10)	0.35776 (9)	0.0480 (5)
C9	0.3553 (3)	0.15520 (13)	0.48198 (8)	0.0586 (6)
C10	−0.0514 (2)	0.12119 (13)	0.38208 (9)	0.0542 (5)
C11	0.13139 (14)	0.12060 (8)	0.08265 (7)	0.0237 (3)
Si'	0.14044 (5)	0.56394 (2)	0.354503 (17)	0.02587 (9)
S'	0.69783 (3)	0.830984 (19)	0.194600 (15)	0.01936 (7)
O1'	0.67601 (12)	0.84820 (7)	0.28160 (5)	0.0354 (3)
O2'	0.86046 (10)	0.89621 (6)	0.15839 (5)	0.0307 (2)
C1'	0.49096 (12)	0.92932 (7)	0.06724 (6)	0.0145 (2)
C2'	0.59696 (13)	1.03736 (7)	0.07734 (6)	0.0159 (2)
C3'	0.60477 (12)	1.10686 (7)	0.01088 (6)	0.0160 (2)
C4'	0.47361 (13)	0.85264 (7)	0.13667 (6)	0.0158 (2)
C5'	0.29722 (14)	0.79691 (8)	0.15367 (6)	0.0196 (3)
C6'	0.25949 (14)	0.71875 (8)	0.21631 (6)	0.0210 (3)
C7'	0.21260 (15)	0.65324 (8)	0.26845 (6)	0.0239 (3)
C8'	0.0676 (3)	0.65591 (11)	0.43712 (8)	0.0625 (6)
C9'	−0.0732 (2)	0.45820 (10)	0.31548 (8)	0.0413 (4)
C10'	0.3590 (2)	0.49934 (13)	0.39039 (10)	0.0619 (6)
C11'	0.71327 (15)	0.68927 (8)	0.17262 (7)	0.0274 (3)
H2	0.17503	0.500515	0.039994	0.0236*
H3	0.691979	0.368788	0.05186	0.024*
H5	0.578317	0.357665	0.192817	0.038*
H111	0.218118	0.108183	0.039861	0.0284*
H112	0.189286	0.102084	0.135334	0.0284*
H113	0.005155	0.074386	0.070168	0.0284*
H2'	0.66448	1.063553	0.130298	0.0191*
H3'	0.677173	1.181145	0.018639	0.0192*
H5'	0.183503	0.811471	0.119646	0.0235*
H111'	0.717696	0.676051	0.113671	0.0329*
H112'	0.831565	0.670526	0.200977	0.0329*
H113'	0.598979	0.643814	0.191213	0.0329*
H81	0.179929	−0.091938	0.401125	0.0576*
H82	0.156978	−0.07068	0.305862	0.0576*
H83	0.36877	−0.054855	0.353113	0.0576*
H101	−0.114106	0.078675	0.424545	0.0651*
H102	−0.059452	0.198977	0.392527	0.0651*
H103	−0.117673	0.096294	0.328635	0.0651*
H91	0.302317	0.114177	0.527176	0.0703*
H92	0.492287	0.146523	0.478792	0.0703*
H93	0.345111	0.232932	0.491257	0.0703*
H81'	0.013715	0.611465	0.480467	0.075*
H82'	0.182006	0.706625	0.45972	0.075*
H83'	−0.03095	0.697607	0.414249	0.075*
H91'	−0.115408	0.4123	0.360015	0.0496*
H92'	−0.180751	0.495113	0.294855	0.0496*
H93'	−0.034345	0.412303	0.271318	0.0496*
H101'	0.328104	0.456103	0.437656	0.0742*
H102'	0.392839	0.451549	0.346249	0.0742*
H103'	0.46938	0.556864	0.405874	0.0742*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0474 (2)	0.02372 (15)	0.02452 (16)	0.00038 (13)	0.00266 (14)	0.00738 (12)
S	0.01440 (10)	0.01724 (10)	0.02198 (12)	−0.00026 (8)	0.00287 (9)	0.00215 (8)
O1	0.0212 (4)	0.0321 (4)	0.0275 (4)	−0.0065 (3)	−0.0058 (3)	0.0089 (3)
O2	0.0268 (4)	0.0286 (4)	0.0365 (4)	0.0048 (3)	0.0138 (3)	−0.0012 (3)
C1	0.0179 (4)	0.0145 (4)	0.0196 (5)	−0.0021 (3)	−0.0016 (3)	0.0022 (3)
C2	0.0149 (4)	0.0173 (4)	0.0264 (5)	0.0007 (3)	0.0021 (4)	0.0017 (4)
C3	0.0170 (4)	0.0149 (4)	0.0275 (5)	0.0018 (3)	−0.0028 (4)	0.0048 (4)
C4	0.0200 (4)	0.0172 (4)	0.0215 (5)	−0.0037 (3)	−0.0004 (4)	0.0030 (3)
C5	0.0318 (6)	0.0302 (5)	0.0273 (6)	−0.0117 (4)	−0.0083 (5)	0.0092 (4)
C6	0.0398 (7)	0.0344 (6)	0.0272 (6)	−0.0098 (5)	−0.0109 (5)	0.0102 (5)
C7	0.0465 (7)	0.0346 (6)	0.0289 (6)	−0.0053 (5)	−0.0078 (5)	0.0083 (5)
C8	0.0614 (9)	0.0314 (6)	0.0534 (9)	0.0095 (6)	0.0109 (7)	0.0069 (6)
C9	0.0840 (12)	0.0576 (9)	0.0297 (7)	−0.0020 (8)	−0.0048 (7)	0.0087 (6)
C10	0.0599 (10)	0.0463 (8)	0.0582 (10)	0.0099 (7)	0.0142 (8)	−0.0004 (7)
C11	0.0175 (4)	0.0184 (4)	0.0347 (6)	0.0006 (3)	0.0045 (4)	−0.0013 (4)
Si'	0.03791 (17)	0.02103 (13)	0.01707 (14)	−0.00308 (12)	0.00359 (12)	0.00579 (10)
S'	0.01356 (10)	0.02294 (11)	0.02119 (12)	0.00154 (8)	−0.00222 (9)	0.00671 (9)
O1'	0.0328 (4)	0.0513 (5)	0.0204 (4)	0.0055 (4)	−0.0067 (3)	−0.0013 (3)
O2'	0.0133 (3)	0.0325 (4)	0.0463 (5)	−0.0002 (3)	0.0003 (3)	0.0186 (3)
C1'	0.0098 (4)	0.0165 (4)	0.0182 (4)	0.0029 (3)	0.0027 (3)	0.0052 (3)
C2'	0.0131 (4)	0.0176 (4)	0.0170 (4)	0.0022 (3)	0.0005 (3)	0.0017 (3)
C3'	0.0117 (4)	0.0151 (4)	0.0212 (5)	0.0010 (3)	0.0018 (3)	0.0030 (3)
C4'	0.0127 (4)	0.0182 (4)	0.0168 (4)	0.0023 (3)	0.0012 (3)	0.0047 (3)
C5'	0.0144 (4)	0.0238 (4)	0.0211 (5)	0.0021 (3)	0.0014 (3)	0.0086 (4)
C6'	0.0141 (4)	0.0269 (5)	0.0217 (5)	0.0010 (3)	0.0015 (4)	0.0063 (4)
C7'	0.0206 (5)	0.0272 (5)	0.0236 (5)	0.0009 (4)	0.0028 (4)	0.0061 (4)
C8'	0.1141 (14)	0.0335 (7)	0.0380 (8)	−0.0100 (8)	0.0372 (9)	−0.0008 (6)
C9'	0.0487 (8)	0.0344 (6)	0.0361 (7)	−0.0131 (5)	0.0096 (6)	0.0031 (5)
C10'	0.0665 (10)	0.0594 (10)	0.0596 (10)	0.0121 (8)	−0.0159 (8)	0.0275 (8)
C11'	0.0214 (5)	0.0264 (5)	0.0365 (6)	0.0081 (4)	0.0021 (4)	0.0104 (4)

Geometric parameters (Å, º)

Si—C7	1.8474 (13)	Si'—C7'	1.8431 (11)
Si—C8	1.8465 (13)	Si'—C8'	1.8409 (15)
Si—C9	1.8510 (14)	Si'—C9'	1.8501 (12)
Si—C10	1.8512 (17)	Si'—C10'	1.8501 (18)
S—O1	1.4410 (8)	S'—O1'	1.4298 (8)
S—O2	1.4354 (8)	S'—O2'	1.4380 (8)
S—C11	1.7579 (10)	S'—C11'	1.7572 (11)
C1—C2	1.3953 (13)	C1'—C2'	1.3971 (11)
C1—C3	1.3962 (14)	C1'—C3'^ii	1.4001 (12)
C1—C4	1.4798 (13)	C1'—C4'	1.4830 (13)
C2—C3^i	1.3892 (13)	C2'—C3'	1.3880 (13)
C2—H2	0.96	C2'—H2'	0.96
C3—H3	0.96	C3'—H3'	0.96
C4—C5	1.3361 (14)	C4'—C5'	1.3426 (12)
C5—C6	1.4236 (16)	C5'—C6'	1.4229 (14)
C5—H5	0.96	C5'—H5'	0.96
C6—C7	1.2035 (17)	C6'—C7'	1.2066 (14)
C8—H81	0.96	C8'—H81'	0.96
C8—H82	0.96	C8'—H82'	0.96
C8—H83	0.96	C8'—H83'	0.96
C9—H91	0.96	C9'—H91'	0.96
C9—H92	0.96	C9'—H92'	0.96
C9—H93	0.96	C9'—H93'	0.96
C10—H101	0.96	C10'—H101'	0.96
C10—H102	0.96	C10'—H102'	0.96
C10—H103	0.96	C10'—H103'	0.96
C11—H111	0.96	C11'—H111'	0.96
C11—H112	0.96	C11'—H112'	0.96
C11—H113	0.96	C11'—H113'	0.96
C7—Si—C8	107.97 (6)	C7'—Si'—C8'	106.73 (6)
C7—Si—C9	106.61 (6)	C7'—Si'—C9'	108.35 (5)
C7—Si—C10	106.81 (7)	C7'—Si'—C10'	107.73 (6)
C8—Si—C9	112.61 (7)	C8'—Si'—C9'	110.34 (7)
C8—Si—C10	110.27 (7)	C8'—Si'—C10'	111.35 (7)
C9—Si—C10	112.24 (7)	C9'—Si'—C10'	112.11 (6)
O1—S—O2	117.21 (5)	O1'—S'—O2'	118.76 (5)
O1—S—C11	107.78 (5)	O1'—S'—C11'	109.09 (5)
O2—S—C11	109.02 (5)	O2'—S'—C11'	107.64 (5)
C2—C1—C3	118.85 (8)	C2'—C1'—C3'^ii	118.67 (8)
C2—C1—C4	121.55 (9)	C2'—C1'—C4'	122.30 (8)
C3—C1—C4	119.60 (8)	C3'^ii—C1'—C4'	119.02 (7)
C1—C2—C3^i	120.27 (9)	C1'—C2'—C3'	120.08 (8)
C1—C2—H2	119.87	C1'—C2'—H2'	119.96
C3^i—C2—H2	119.87	C3'—C2'—H2'	119.96
C1—C3—C2^i	120.89 (9)	C1'^ii—C3'—C2'	121.24 (7)
C1—C3—H3	119.56	C1'^ii—C3'—H3'	119.38
C2^i—C3—H3	119.56	C2'—C3'—H3'	119.38
C1—C4—C5	122.64 (8)	C1'—C4'—C5'	121.44 (8)
C4—C5—C6	126.55 (10)	C4'—C5'—C6'	127.46 (9)
C4—C5—H5	116.72	C4'—C5'—H5'	116.27
C6—C5—H5	116.72	C6'—C5'—H5'	116.27
C5—C6—C7	177.07 (12)	C5'—C6'—C7'	175.09 (10)
Si—C7—C6	174.42 (12)	Si'—C7'—C6'	174.91 (9)
Si—C8—H81	109.47	Si'—C8'—H81'	109.47
Si—C8—H82	109.47	Si'—C8'—H82'	109.47
Si—C8—H83	109.47	Si'—C8'—H83'	109.47
H81—C8—H82	109.47	H81'—C8'—H82'	109.47
H81—C8—H83	109.47	H81'—C8'—H83'	109.47
H82—C8—H83	109.47	H82'—C8'—H83'	109.47
Si—C9—H91	109.47	Si'—C9'—H91'	109.47
Si—C9—H92	109.47	Si'—C9'—H92'	109.47
Si—C9—H93	109.47	Si'—C9'—H93'	109.47
H91—C9—H92	109.47	H91'—C9'—H92'	109.47
H91—C9—H93	109.47	H91'—C9'—H93'	109.47
H92—C9—H93	109.47	H92'—C9'—H93'	109.47
Si—C10—H101	109.47	Si'—C10'—H101'	109.47
Si—C10—H102	109.47	Si'—C10'—H102'	109.47
Si—C10—H103	109.47	Si'—C10'—H103'	109.47
H101—C10—H102	109.47	H101'—C10'—H102'	109.47
H101—C10—H103	109.47	H101'—C10'—H103'	109.47
H102—C10—H103	109.47	H102'—C10'—H103'	109.47
S—C11—H111	109.47	S'—C11'—H111'	109.47
S—C11—H112	109.47	S'—C11'—H112'	109.47
S—C11—H113	109.47	S'—C11'—H113'	109.47
H111—C11—H112	109.47	H111'—C11'—H112'	109.47
H111—C11—H113	109.47	H111'—C11'—H113'	109.47
H112—C11—H113	109.47	H112'—C11'—H113'	109.47

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···C6	0.96	2.56	3.2082 (15)	124.92
C5′—H5′···O1^iii	0.96	2.57	3.3290 (11)	135.63
C9′—H93′···O2	0.96	2.46	3.3938 (15)	164.69

Symmetry code: (iii) −x, −y+1, −z.

(BSEMOX2)

Crystal data

C22H30O4S2Si2	Z = 2
Mr = 478.8	F(000) = 508
Triclinic, P1	Dx = 1.229 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3096 (2) Å	Cell parameters from 9931 reflections
b = 11.3935 (3) Å	θ = 2.3–29.9°
c = 18.7425 (6) Å	µ = 0.32 mm^−1
α = 73.167 (2)°	T = 100 K
β = 105.319 (2)°	Plate, clear colourless
γ = 118.926 (2)°	0.70 × 0.65 × 0.10 mm
V = 1293.21 (7) Å^3

Data collection

Bruker KAPPA APEX II CCD diffractometer	7541 independent reflections
Radiation source: X-ray tube	5106 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.063
ω– and φ–scans	θmax = 30.2°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.81, Tmax = 0.97	k = −15→16
40880 measured reflections	l = −26→26

Refinement

Refinement on F	120 constraints
R[F^2 > 2σ(F^2)] = 0.074	H-atom parameters constrained
wR(F^2) = 0.093	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 3.05	(Δ/σ)max = 0.006
7541 reflections	Δρmax = 1.17 e Å^−3
271 parameters	Δρmin = −0.70 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S	0.05875 (11)	0.58519 (9)	0.84239 (5)	0.0137 (3)
Si	0.34677 (17)	1.07380 (11)	0.63991 (6)	0.0231 (5)
O1	−0.0402 (3)	0.4555 (2)	0.89127 (13)	0.0171 (10)
O2	−0.0238 (3)	0.6831 (3)	0.82836 (14)	0.0206 (11)
C1	0.4163 (4)	0.5774 (3)	0.94119 (17)	0.0113 (13)
C2	0.6701 (4)	0.4845 (3)	0.99142 (17)	0.0128 (13)
C3	0.5868 (4)	0.5601 (3)	0.93318 (18)	0.0123 (13)
C4	0.3333 (5)	0.6614 (3)	0.87911 (18)	0.0134 (14)
C5	0.4597 (5)	0.7892 (3)	0.84719 (18)	0.0160 (14)
C6	0.4023 (5)	0.8768 (4)	0.7835 (2)	0.0187 (15)
C7	0.3701 (6)	0.9539 (4)	0.7281 (2)	0.0233 (17)
C8	0.2741 (7)	0.9833 (5)	0.5612 (2)	0.039 (2)
C9	0.6075 (7)	1.2230 (4)	0.6347 (2)	0.035 (2)
C10	0.1367 (6)	1.1221 (4)	0.6386 (2)	0.0286 (18)
C11	0.0579 (5)	0.5521 (4)	0.75641 (18)	0.0188 (15)
S'	1.09914 (12)	1.14700 (9)	0.86315 (5)	0.0158 (4)
Si'	1.50574 (15)	1.60457 (11)	0.63339 (6)	0.0202 (4)
O1'	1.0614 (3)	1.2400 (3)	0.79758 (13)	0.0231 (12)
O2'	0.9548 (3)	1.0041 (3)	0.87028 (15)	0.0244 (11)
C1'	1.4276 (4)	1.0780 (3)	0.93697 (18)	0.0126 (14)
C2'	1.3188 (5)	0.9351 (3)	0.95048 (18)	0.0143 (14)
C3'	1.3920 (5)	0.8588 (3)	1.01280 (18)	0.0139 (14)
C4'	1.3610 (4)	1.1657 (3)	0.87148 (18)	0.0118 (13)
C5'	1.4969 (5)	1.2632 (3)	0.82560 (18)	0.0154 (14)
C6'	1.4746 (5)	1.3676 (4)	0.76498 (19)	0.0188 (15)
C7'	1.4862 (5)	1.4606 (4)	0.7130 (2)	0.0210 (16)
C8'	1.6173 (6)	1.7619 (4)	0.6715 (2)	0.033 (2)
C9'	1.2360 (6)	1.5639 (5)	0.5788 (2)	0.033 (2)
C10'	1.6873 (6)	1.6204 (5)	0.5738 (2)	0.032 (2)
C11'	1.1138 (5)	1.2016 (4)	0.94391 (19)	0.0218 (17)
H2	0.788055	0.474287	0.985616	0.0153*
H3	0.646088	0.600945	0.88705	0.0147*
H5	0.605389	0.82566	0.869832	0.0193*
H81	0.270082	1.044763	0.513949	0.0472*
H82	0.377132	0.951948	0.564554	0.0472*
H83	0.137507	0.906594	0.564396	0.0472*
H91	0.604537	1.283444	0.587005	0.0418*
H92	0.640576	1.27022	0.674662	0.0418*
H93	0.713139	1.192893	0.639684	0.0418*
H101	0.105561	1.169144	0.58903	0.0343*
H102	0.011481	1.041179	0.652106	0.0343*
H103	0.184341	1.180776	0.674151	0.0343*
H111	0.120822	0.491063	0.765705	0.0226*
H112	−0.084951	0.510848	0.731709	0.0226*
H113	0.137461	0.636208	0.724813	0.0226*
H2'	1.1942	0.889906	0.916885	0.0172*
H3'	1.317263	0.760925	1.021542	0.0166*
H5'	1.63238	1.262986	0.83506	0.0185*
H81'	1.64584	1.839397	0.630763	0.0397*
H82'	1.517826	1.756454	0.698495	0.0397*
H83'	1.746211	1.77159	0.705004	0.0397*
H91'	1.239708	1.640788	0.539683	0.0392*
H92'	1.189144	1.485903	0.556756	0.0392*
H93'	1.140157	1.544048	0.611915	0.0392*
H101'	1.674858	1.679182	0.526259	0.0387*
H102'	1.830199	1.658436	0.598964	0.0387*
H103'	1.65023	1.531745	0.565552	0.0387*
H111'	1.13093	1.137093	0.988028	0.0261*
H112'	1.232391	1.289552	0.946012	0.0261*
H113'	0.986229	1.207961	0.941841	0.0261*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0086 (3)	0.0072 (4)	0.0247 (4)	0.0029 (3)	0.0040 (3)	−0.0019 (3)
Si	0.0300 (5)	0.0123 (6)	0.0257 (5)	0.0111 (4)	0.0040 (4)	0.0013 (4)
O1	0.0088 (10)	0.0088 (14)	0.0300 (13)	0.0010 (9)	0.0074 (9)	0.0002 (10)
O2	0.0098 (10)	0.0112 (14)	0.0443 (15)	0.0079 (10)	0.0049 (10)	−0.0034 (11)
C1	0.0078 (12)	0.0024 (17)	0.0221 (16)	0.0007 (11)	0.0020 (12)	−0.0030 (12)
C2	0.0055 (12)	0.0074 (18)	0.0254 (17)	0.0005 (11)	0.0062 (12)	−0.0039 (13)
C3	0.0106 (13)	0.0046 (17)	0.0207 (16)	0.0012 (12)	0.0057 (12)	−0.0020 (13)
C4	0.0136 (14)	0.0080 (18)	0.0219 (17)	0.0060 (13)	0.0044 (12)	−0.0037 (13)
C5	0.0147 (14)	0.0078 (19)	0.0223 (17)	0.0024 (13)	0.0025 (13)	−0.0031 (13)
C6	0.0152 (15)	0.0092 (19)	0.0278 (19)	0.0012 (13)	0.0055 (13)	−0.0035 (14)
C7	0.0252 (18)	0.016 (2)	0.0271 (19)	0.0077 (15)	0.0035 (15)	−0.0039 (16)
C8	0.058 (3)	0.034 (3)	0.031 (2)	0.028 (2)	−0.004 (2)	−0.008 (2)
C9	0.042 (2)	0.023 (3)	0.038 (2)	0.0170 (19)	0.0097 (19)	0.0056 (18)
C10	0.0240 (18)	0.017 (2)	0.039 (2)	0.0080 (16)	0.0028 (16)	−0.0019 (17)
C11	0.0141 (15)	0.016 (2)	0.0253 (18)	0.0049 (14)	0.0030 (13)	−0.0056 (15)
S'	0.0087 (3)	0.0083 (5)	0.0290 (5)	0.0037 (3)	0.0036 (3)	−0.0010 (3)
Si'	0.0202 (5)	0.0150 (6)	0.0253 (5)	0.0099 (4)	0.0057 (4)	0.0023 (4)
O1'	0.0144 (11)	0.0189 (16)	0.0333 (14)	0.0096 (10)	0.0035 (10)	0.0031 (11)
O2'	0.0084 (10)	0.0076 (14)	0.0500 (17)	−0.0015 (9)	0.0042 (10)	−0.0048 (11)
C1'	0.0085 (13)	0.0088 (18)	0.0231 (17)	0.0049 (12)	0.0060 (12)	−0.0013 (13)
C2'	0.0121 (14)	0.0082 (18)	0.0236 (17)	0.0041 (12)	0.0037 (12)	−0.0042 (13)
C3'	0.0120 (14)	0.0038 (18)	0.0273 (18)	0.0031 (12)	0.0057 (13)	−0.0034 (13)
C4'	0.0060 (12)	0.0029 (17)	0.0245 (17)	−0.0011 (11)	0.0047 (12)	−0.0032 (13)
C5'	0.0076 (13)	0.0083 (19)	0.0273 (18)	0.0008 (12)	0.0042 (12)	−0.0027 (14)
C6'	0.0174 (15)	0.015 (2)	0.0237 (18)	0.0063 (14)	0.0047 (13)	−0.0029 (15)
C7'	0.0206 (16)	0.015 (2)	0.0262 (19)	0.0064 (15)	0.0050 (14)	−0.0033 (15)
C8'	0.035 (2)	0.016 (2)	0.043 (3)	0.0102 (18)	0.0093 (19)	0.0006 (18)
C9'	0.0269 (19)	0.039 (3)	0.034 (2)	0.0172 (19)	0.0058 (17)	−0.0029 (19)
C10'	0.029 (2)	0.033 (3)	0.037 (2)	0.0188 (19)	0.0155 (18)	0.0093 (19)
C11'	0.0203 (16)	0.017 (2)	0.034 (2)	0.0107 (15)	0.0090 (15)	−0.0044 (16)

Geometric parameters (Å, º)

S—O1	1.441 (2)	S'—O1'	1.435 (3)
S—O2	1.440 (3)	S'—O2'	1.438 (2)
S—C4	1.785 (3)	S'—C4'	1.789 (4)
S—C11	1.756 (4)	S'—C11'	1.756 (5)
Si—C7	1.843 (4)	Si'—C7'	1.845 (4)
Si—C8	1.860 (5)	Si'—C8'	1.846 (5)
Si—C9	1.844 (4)	Si'—C9'	1.864 (4)
Si—C10	1.858 (6)	Si'—C10'	1.864 (5)
C1—C2^i	1.402 (4)	C1'—C2'	1.401 (5)
C1—C3	1.404 (6)	C1'—C3'^ii	1.401 (4)
C1—C4	1.476 (5)	C1'—C4'	1.479 (5)
C2—C3	1.384 (5)	C2'—C3'	1.392 (5)
C2—H2	0.96	C2'—H2'	0.96
C3—H3	0.96	C3'—H3'	0.96
C4—C5	1.348 (4)	C4'—C5'	1.338 (4)
C5—C6	1.431 (5)	C5'—C6'	1.428 (5)
C5—H5	0.96	C5'—H5'	0.96
C6—C7	1.204 (5)	C6'—C7'	1.199 (5)
C8—H81	0.96	C8'—H81'	0.96
C8—H82	0.96	C8'—H82'	0.96
C8—H83	0.96	C8'—H83'	0.96
C9—H91	0.96	C9'—H91'	0.96
C9—H92	0.96	C9'—H92'	0.96
C9—H93	0.96	C9'—H93'	0.96
C10—H101	0.96	C10'—H101'	0.96
C10—H102	0.96	C10'—H102'	0.96
C10—H103	0.96	C10'—H103'	0.96
C11—H111	0.96	C11'—H111'	0.96
C11—H112	0.96	C11'—H112'	0.96
C11—H113	0.96	C11'—H113'	0.96
O1—S—O2	118.43 (17)	O1'—S'—O2'	118.59 (14)
O1—S—C4	107.75 (14)	O1'—S'—C4'	109.15 (15)
O1—S—C11	107.67 (17)	O1'—S'—C11'	108.9 (2)
O2—S—C4	109.27 (17)	O2'—S'—C4'	108.57 (18)
O2—S—C11	109.62 (18)	O2'—S'—C11'	108.30 (17)
C4—S—C11	102.99 (18)	C4'—S'—C11'	102.14 (17)
C7—Si—C8	106.9 (2)	C7'—Si'—C8'	108.49 (18)
C7—Si—C9	107.39 (17)	C7'—Si'—C9'	107.88 (16)
C7—Si—C10	110.0 (2)	C7'—Si'—C10'	107.6 (2)
C8—Si—C9	110.5 (2)	C8'—Si'—C9'	112.4 (3)
C8—Si—C10	109.8 (2)	C8'—Si'—C10'	109.8 (2)
C9—Si—C10	112.1 (2)	C9'—Si'—C10'	110.5 (2)
C2^i—C1—C3	119.0 (3)	C2'—C1'—C3'^ii	118.9 (3)
C2^i—C1—C4	121.4 (4)	C2'—C1'—C4'	122.8 (3)
C3—C1—C4	119.5 (3)	C3'^ii—C1'—C4'	118.3 (3)
C1^i—C2—C3	120.6 (4)	C1'—C2'—C3'	119.7 (3)
C1^i—C2—H2	119.72	C1'—C2'—H2'	120.14
C3—C2—H2	119.72	C3'—C2'—H2'	120.14
C1—C3—C2	120.4 (3)	C1'^ii—C3'—C2'	121.4 (3)
C1—C3—H3	119.8	C1'^ii—C3'—H3'	119.32
C2—C3—H3	119.8	C2'—C3'—H3'	119.32
S—C4—C1	118.0 (2)	S'—C4'—C1'	116.4 (2)
S—C4—C5	119.8 (3)	S'—C4'—C5'	121.9 (3)
C1—C4—C5	122.2 (3)	C1'—C4'—C5'	121.4 (3)
C4—C5—C6	127.6 (3)	C4'—C5'—C6'	130.9 (4)
C4—C5—H5	116.19	C4'—C5'—H5'	114.53
C6—C5—H5	116.19	C6'—C5'—H5'	114.53
C5—C6—C7	174.4 (4)	C5'—C6'—C7'	170.2 (4)
Si—C7—C6	173.6 (4)	Si'—C7'—C6'	179.6 (3)
Si—C8—H81	109.47	Si'—C8'—H81'	109.47
Si—C8—H82	109.47	Si'—C8'—H82'	109.47
Si—C8—H83	109.47	Si'—C8'—H83'	109.47
H81—C8—H82	109.47	H81'—C8'—H82'	109.47
H81—C8—H83	109.47	H81'—C8'—H83'	109.47
H82—C8—H83	109.47	H82'—C8'—H83'	109.47
Si—C9—H91	109.47	Si'—C9'—H91'	109.47
Si—C9—H92	109.47	Si'—C9'—H92'	109.47
Si—C9—H93	109.47	Si'—C9'—H93'	109.47
H91—C9—H92	109.47	H91'—C9'—H92'	109.47
H91—C9—H93	109.47	H91'—C9'—H93'	109.47
H92—C9—H93	109.47	H92'—C9'—H93'	109.47
Si—C10—H101	109.47	Si'—C10'—H101'	109.47
Si—C10—H102	109.47	Si'—C10'—H102'	109.47
Si—C10—H103	109.47	Si'—C10'—H103'	109.47
H101—C10—H102	109.47	H101'—C10'—H102'	109.47
H101—C10—H103	109.47	H101'—C10'—H103'	109.47
H102—C10—H103	109.47	H102'—C10'—H103'	109.47
S—C11—H111	109.47	S'—C11'—H111'	109.47
S—C11—H112	109.47	S'—C11'—H112'	109.47
S—C11—H113	109.47	S'—C11'—H113'	109.47
H111—C11—H112	109.47	H111'—C11'—H112'	109.47
H111—C11—H113	109.47	H111'—C11'—H113'	109.47
H112—C11—H113	109.47	H112'—C11'—H113'	109.47
C5—C4—C1—C2	−50.2 (7)	C5'—C4'—S'—C11'	−109.1 (4)
C5'—C4'—C1'—C2'	−128.5 (4)	C9—Si—C5—C4	−176.7 (5)
C5—C4—S—C11	71.8 (4)	C9'—Si'—C5'—C4'	−29.9 (5)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+3, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2′	0.96	2.37	3.239 (3)	149.82

(BSEMOX3)

Crystal data

C22H30O4S2Si2	Z = 1
Mr = 478.8	F(000) = 254
Triclinic, P1	Dx = 1.267 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7300 (3) Å	Cell parameters from 8294 reflections
b = 10.2961 (5) Å	θ = 3.8–25.5°
c = 10.9801 (6) Å	µ = 0.33 mm^−1
α = 85.9433 (17)°	T = 100 K
β = 79.7181 (16)°	Plate, clear colourless
γ = 80.1150 (15)°	0.45 × 0.15 × 0.03 mm
V = 627.39 (6) Å^3

Data collection

Bruker KAPPA APEX II CCD diffractometer	2909 independent reflections
Radiation source: X-ray tube	2371 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.024
ω– and φ–scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan SADABS	h = −6→7
Tmin = 0.89, Tmax = 0.98	k = −13→13
16087 measured reflections	l = −14→14

Refinement

Refinement on F	60 constraints
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.039	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 2.19	(Δ/σ)max = 0.015
2909 reflections	Δρmax = 0.31 e Å^−3
136 parameters	Δρmin = −0.26 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
Si1	−0.53335 (7)	0.61622 (4)	0.26340 (4)	0.01652 (14)
S1	0.00389 (7)	0.10973 (3)	0.30445 (4)	0.01720 (12)
O1	0.0623 (2)	−0.03183 (10)	0.30608 (11)	0.0327 (4)
O2	−0.24475 (19)	0.16738 (12)	0.33388 (11)	0.0309 (4)
C1	0.3167 (2)	0.07921 (13)	0.07667 (13)	0.0133 (4)
C2	0.5302 (2)	0.02428 (13)	0.11879 (14)	0.0165 (5)
C3	0.2893 (3)	0.05341 (13)	−0.04189 (13)	0.0161 (4)
C4	0.1243 (2)	0.16934 (13)	0.15372 (13)	0.0148 (4)
C5	0.0409 (3)	0.29002 (14)	0.10936 (15)	0.0208 (5)
C6	−0.1427 (3)	0.39013 (15)	0.16678 (15)	0.0234 (5)
C7	−0.2910 (3)	0.48169 (15)	0.20419 (16)	0.0256 (5)
C8	−0.7504 (3)	0.54336 (18)	0.38231 (19)	0.0375 (7)
C9	−0.3979 (3)	0.73712 (15)	0.33371 (16)	0.0277 (6)
C10	−0.6838 (3)	0.68750 (15)	0.13195 (16)	0.0266 (6)
C11	0.1590 (3)	0.17006 (18)	0.40562 (15)	0.0290 (6)
H81	−0.85684	0.612453	0.427929	0.045*
H82	−0.841896	0.494259	0.342845	0.045*
H83	−0.665055	0.485508	0.437918	0.045*
H91	−0.5212	0.807923	0.365168	0.0332*
H92	−0.321634	0.694388	0.400299	0.0332*
H93	−0.280639	0.771715	0.272118	0.0332*
H101	−0.807579	0.759634	0.15968	0.0319*
H102	−0.567884	0.718767	0.067262	0.0319*
H103	−0.753644	0.620997	0.100878	0.0319*
H111	0.327147	0.135155	0.385869	0.0348*
H112	0.136853	0.264631	0.397352	0.0348*
H113	0.098422	0.143559	0.489252	0.0348*
H2	0.551711	0.040378	0.200823	0.0198*
H3	0.142736	0.09003	−0.071188	0.0193*
H5	0.115514	0.312503	0.026929	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0148 (2)	0.0146 (2)	0.0183 (2)	0.00228 (15)	−0.00179 (17)	−0.00127 (16)
S1	0.0150 (2)	0.01967 (19)	0.0162 (2)	−0.00398 (14)	0.00180 (15)	−0.00414 (14)
O1	0.0459 (8)	0.0183 (6)	0.0282 (7)	−0.0075 (5)	0.0119 (6)	−0.0026 (5)
O2	0.0139 (6)	0.0483 (7)	0.0265 (7)	−0.0003 (5)	0.0043 (5)	−0.0060 (5)
C1	0.0118 (7)	0.0119 (6)	0.0146 (8)	−0.0009 (5)	0.0009 (6)	0.0006 (5)
C2	0.0155 (7)	0.0203 (7)	0.0130 (8)	−0.0007 (6)	−0.0018 (6)	−0.0024 (6)
C3	0.0121 (7)	0.0176 (7)	0.0173 (8)	0.0011 (5)	−0.0029 (6)	0.0008 (6)
C4	0.0114 (7)	0.0189 (7)	0.0134 (7)	−0.0011 (5)	−0.0007 (6)	−0.0038 (6)
C5	0.0187 (8)	0.0231 (8)	0.0179 (8)	0.0048 (6)	−0.0025 (7)	−0.0041 (6)
C6	0.0231 (8)	0.0231 (8)	0.0220 (9)	0.0045 (6)	−0.0058 (7)	−0.0025 (6)
C7	0.0245 (9)	0.0252 (8)	0.0260 (9)	0.0034 (7)	−0.0078 (7)	−0.0039 (7)
C8	0.0315 (10)	0.0414 (10)	0.0380 (12)	−0.0099 (8)	−0.0014 (8)	0.0074 (8)
C9	0.0323 (10)	0.0224 (8)	0.0304 (10)	−0.0037 (7)	−0.0122 (8)	0.0008 (7)
C10	0.0255 (9)	0.0256 (8)	0.0294 (10)	−0.0006 (7)	−0.0104 (7)	0.0008 (7)
C11	0.0290 (9)	0.0445 (10)	0.0162 (9)	−0.0151 (8)	−0.0012 (7)	−0.0040 (7)

Geometric parameters (Å, º)

Si1—C7	1.8478 (15)	C5—C6	1.432 (2)
Si1—C8	1.8482 (19)	C5—H5	0.96
Si1—C9	1.8519 (19)	C6—C7	1.198 (2)
Si1—C10	1.8552 (18)	C8—H81	0.96
S1—O1	1.4380 (11)	C8—H82	0.96
S1—O2	1.4349 (11)	C8—H83	0.96
S1—C4	1.7848 (14)	C9—H91	0.96
S1—C11	1.746 (2)	C9—H92	0.96
C1—C2	1.399 (2)	C9—H93	0.96
C1—C3	1.388 (2)	C10—H101	0.96
C1—C4	1.4898 (18)	C10—H102	0.96
C2—C3^i	1.3864 (18)	C10—H103	0.96
C2—H2	0.96	C11—H111	0.96
C3—H3	0.96	C11—H112	0.96
C4—C5	1.3427 (19)	C11—H113	0.96
C7—Si1—C8	107.82 (8)	C5—C6—C7	173.37 (17)
C7—Si1—C9	108.19 (8)	Si1—C7—C6	176.58 (16)
C7—Si1—C10	107.75 (7)	Si1—C8—H81	109.47
C8—Si1—C9	110.05 (9)	Si1—C8—H82	109.47
C8—Si1—C10	109.51 (8)	Si1—C8—H83	109.47
C9—Si1—C10	113.35 (8)	H81—C8—H82	109.47
O1—S1—O2	117.83 (7)	H81—C8—H83	109.47
O1—S1—C4	107.13 (7)	H82—C8—H83	109.47
O1—S1—C11	109.04 (8)	Si1—C9—H91	109.47
O2—S1—C4	108.86 (7)	Si1—C9—H92	109.47
O2—S1—C11	107.91 (8)	Si1—C9—H93	109.47
C4—S1—C11	105.39 (8)	H91—C9—H92	109.47
C2—C1—C3	118.89 (12)	H91—C9—H93	109.47
C2—C1—C4	121.53 (13)	H92—C9—H93	109.47
C3—C1—C4	119.51 (13)	Si1—C10—H101	109.47
C1—C2—C3^i	119.90 (14)	Si1—C10—H102	109.47
C1—C2—H2	120.05	Si1—C10—H103	109.47
C3^i—C2—H2	120.05	H101—C10—H102	109.47
C1—C3—C2^i	121.20 (13)	H101—C10—H103	109.47
C1—C3—H3	119.4	H102—C10—H103	109.47
C2^i—C3—H3	119.4	S1—C11—H111	109.47
S1—C4—C1	117.79 (10)	S1—C11—H112	109.47
S1—C4—C5	121.46 (10)	S1—C11—H113	109.47
C1—C4—C5	120.73 (13)	H111—C11—H112	109.47
C4—C5—C6	129.57 (14)	H111—C11—H113	109.47
C4—C5—H5	115.21	H112—C11—H113	109.47
C6—C5—H5	115.21

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H111···O2^ii	0.96	2.49	3.362 (2)	150.78

Symmetry code: (ii) x+1, y, z.

(DSEM1)

Crystal data

C22H32O2S3Si2	F(000) = 2048
Mr = 480.8	Dx = 1.153 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9911 reflections
a = 34.344 (2) Å	θ = 2.4–27.5°
b = 8.1665 (5) Å	µ = 0.37 mm^−1
c = 20.0791 (12) Å	T = 100 K
β = 100.532 (2)°	Rhombic prism, clear yellow
V = 5536.7 (6) Å^3	0.87 × 0.66 × 0.03 mm
Z = 8

Data collection

Bruker KAPPA APEX II CCD diffractometer	6397 independent reflections
Radiation source: X-ray tube	4903 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.038
ω– and φ–scans	θmax = 27.6°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −44→44
Tmin = 0.74, Tmax = 0.99	k = −10→10
77428 measured reflections	l = −26→26

Refinement

Refinement on F	128 constraints
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.059	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 3.02	(Δ/σ)max = 0.030
6397 reflections	Δρmax = 0.87 e Å^−3
262 parameters	Δρmin = −0.75 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.762685 (15)	−0.33644 (6)	0.15507 (3)	0.02279 (16)
S2	0.847992 (18)	−0.37717 (8)	0.11586 (3)	0.0353 (2)
S3	0.700129 (18)	−0.47388 (6)	0.23712 (3)	0.02868 (18)
Si1	0.93168 (2)	−0.24524 (14)	−0.06764 (4)	0.0623 (4)
Si2	0.576085 (19)	−0.28110 (10)	0.35009 (3)	0.0365 (2)
O1	0.75965 (4)	0.06737 (17)	0.05109 (7)	0.0245 (5)
O2	0.69334 (4)	0.04163 (17)	0.12397 (7)	0.0230 (5)
C1	0.77861 (6)	−0.1981 (2)	0.09999 (10)	0.0208 (6)
C2	0.75376 (6)	−0.0650 (2)	0.08999 (9)	0.0192 (6)
C3	0.72162 (6)	−0.0764 (2)	0.12477 (10)	0.0189 (6)
C4	0.72227 (6)	−0.2160 (2)	0.16354 (10)	0.0190 (6)
C5	0.81443 (6)	−0.2305 (3)	0.07343 (10)	0.0232 (6)
C6	0.82130 (6)	−0.1636 (3)	0.01512 (11)	0.0304 (7)
C7	0.85643 (7)	−0.1883 (3)	−0.01190 (12)	0.0388 (9)
C8	0.88601 (8)	−0.2089 (4)	−0.03517 (13)	0.0498 (10)
C9	0.69553 (6)	−0.2693 (2)	0.20742 (10)	0.0206 (6)
C10	0.66931 (6)	−0.1683 (3)	0.22935 (11)	0.0271 (7)
C11	0.64076 (6)	−0.2167 (3)	0.26906 (11)	0.0291 (7)
C12	0.61537 (7)	−0.2474 (3)	0.30132 (12)	0.0334 (8)
C13	0.92858 (8)	−0.4492 (5)	−0.10887 (16)	0.0694 (13)
C14	0.97377 (9)	−0.2385 (6)	0.00601 (18)	0.113 (2)
C15	0.93686 (10)	−0.0800 (5)	−0.12833 (17)	0.0798 (15)
C16	0.55161 (11)	−0.4795 (5)	0.3267 (2)	0.109 (2)
C17	0.59717 (11)	−0.2798 (5)	0.44071 (15)	0.0865 (16)
C18	0.54202 (12)	−0.1076 (6)	0.3313 (3)	0.141 (3)
C19	0.86345 (7)	−0.2835 (3)	0.19798 (12)	0.0383 (8)
C20	0.67977 (9)	−0.5825 (3)	0.16113 (13)	0.0438 (9)
C21	0.77523 (7)	0.2073 (3)	0.09102 (11)	0.0314 (7)
C22	0.67373 (7)	0.0962 (3)	0.05813 (11)	0.0364 (8)
H6	0.80111	−0.094723	−0.009835	0.0365*
H10	0.66994	−0.054804	0.217203	0.0326*
H131	0.95267	−0.470648	−0.125182	0.0833*
H132	0.924798	−0.531753	−0.076613	0.0833*
H133	0.906657	−0.450798	−0.146167	0.0833*
H141	0.998379	−0.246254	−0.010028	0.1353*
H142	0.972955	−0.137344	0.030044	0.1353*
H143	0.971574	−0.328613	0.035831	0.1353*
H151	0.961386	−0.093158	−0.144236	0.0958*
H152	0.915203	−0.085166	−0.166012	0.0958*
H153	0.936668	0.024229	−0.106262	0.0958*
H161	0.527972	−0.486943	0.345649	0.1314*
H162	0.54488	−0.487632	0.278223	0.1314*
H163	0.569264	−0.566984	0.343922	0.1314*
H171	0.577799	−0.3191	0.465791	0.1038*
H172	0.620051	−0.349537	0.449095	0.1038*
H173	0.604711	−0.170179	0.454735	0.1038*
H181	0.524557	−0.104784	0.363546	0.1688*
H182	0.556903	−0.007503	0.334015	0.1688*
H183	0.526759	−0.119462	0.286476	0.1688*
H191	0.885998	−0.341055	0.222371	0.0459*
H192	0.870413	−0.171204	0.192268	0.0459*
H193	0.842154	−0.288535	0.222935	0.0459*
H201	0.682899	−0.698138	0.168924	0.0526*
H202	0.652125	−0.55696	0.148318	0.0526*
H203	0.69337	−0.550594	0.125458	0.0526*
H211	0.775242	0.300712	0.061981	0.0377*
H212	0.758994	0.229827	0.124117	0.0377*
H213	0.801812	0.184658	0.113548	0.0377*
H221	0.650937	0.160286	0.062714	0.0437*
H222	0.691634	0.161728	0.037863	0.0437*
H223	0.66555	0.002922	0.029926	0.0437*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0233 (3)	0.0181 (3)	0.0288 (3)	0.0029 (2)	0.0096 (2)	0.0019 (2)
S2	0.0358 (3)	0.0429 (4)	0.0284 (3)	0.0181 (3)	0.0084 (3)	−0.0026 (3)
S3	0.0403 (3)	0.0202 (3)	0.0270 (3)	−0.0011 (2)	0.0098 (2)	0.0029 (2)
Si1	0.0251 (4)	0.1274 (9)	0.0379 (4)	−0.0045 (4)	0.0155 (3)	−0.0179 (5)
Si2	0.0225 (3)	0.0631 (5)	0.0256 (3)	−0.0034 (3)	0.0087 (3)	0.0024 (3)
O1	0.0343 (9)	0.0214 (8)	0.0185 (7)	−0.0011 (6)	0.0065 (6)	0.0015 (6)
O2	0.0272 (8)	0.0221 (7)	0.0199 (7)	0.0080 (6)	0.0050 (6)	0.0005 (6)
C1	0.0236 (11)	0.0210 (10)	0.0188 (10)	−0.0023 (8)	0.0065 (8)	−0.0018 (8)
C2	0.0230 (10)	0.0187 (10)	0.0158 (9)	−0.0017 (8)	0.0036 (8)	−0.0008 (7)
C3	0.0209 (10)	0.0167 (10)	0.0187 (10)	0.0028 (8)	0.0029 (8)	−0.0040 (7)
C4	0.0198 (10)	0.0157 (9)	0.0219 (10)	0.0013 (8)	0.0053 (8)	−0.0023 (8)
C5	0.0215 (10)	0.0260 (11)	0.0222 (10)	0.0021 (8)	0.0048 (8)	−0.0048 (8)
C6	0.0233 (11)	0.0416 (14)	0.0277 (12)	0.0035 (10)	0.0085 (9)	0.0025 (10)
C7	0.0333 (13)	0.0565 (17)	0.0287 (12)	0.0014 (12)	0.0114 (11)	0.0018 (11)
C8	0.0328 (14)	0.087 (2)	0.0324 (14)	0.0036 (14)	0.0133 (12)	0.0011 (14)
C9	0.0219 (10)	0.0182 (10)	0.0220 (10)	−0.0037 (8)	0.0044 (8)	−0.0019 (8)
C10	0.0263 (11)	0.0240 (11)	0.0334 (12)	−0.0017 (9)	0.0113 (10)	−0.0004 (9)
C11	0.0233 (11)	0.0330 (12)	0.0316 (12)	−0.0022 (9)	0.0064 (10)	−0.0033 (10)
C12	0.0257 (12)	0.0442 (14)	0.0315 (12)	−0.0034 (10)	0.0083 (10)	−0.0037 (10)
C13	0.0343 (16)	0.121 (3)	0.056 (2)	0.0095 (18)	0.0157 (15)	−0.010 (2)
C14	0.0346 (18)	0.230 (6)	0.070 (3)	0.016 (3)	−0.0005 (18)	−0.052 (3)
C15	0.063 (2)	0.120 (3)	0.068 (2)	−0.037 (2)	0.0413 (19)	−0.026 (2)
C16	0.092 (3)	0.161 (4)	0.095 (3)	−0.092 (3)	0.070 (3)	−0.069 (3)
C17	0.082 (3)	0.142 (4)	0.0323 (16)	−0.064 (2)	0.0018 (16)	0.014 (2)
C18	0.072 (3)	0.183 (5)	0.194 (5)	0.073 (3)	0.094 (3)	0.114 (4)
C19	0.0388 (14)	0.0396 (14)	0.0339 (13)	−0.0006 (11)	−0.0002 (11)	−0.0007 (11)
C20	0.0666 (19)	0.0259 (13)	0.0400 (15)	−0.0086 (13)	0.0129 (13)	−0.0067 (11)
C21	0.0432 (14)	0.0250 (12)	0.0254 (11)	−0.0099 (10)	0.0047 (10)	0.0032 (9)
C22	0.0367 (14)	0.0426 (14)	0.0267 (12)	0.0163 (11)	−0.0026 (10)	−0.0031 (11)

Geometric parameters (Å, º)

S1—C1	1.738 (2)	C13—H132	0.96
S1—C4	1.735 (2)	C13—H133	0.96
S2—C5	1.769 (2)	C14—H141	0.96
S3—C9	1.771 (2)	C14—H142	0.96
Si1—C8	1.830 (3)	C14—H143	0.96
Si1—C13	1.854 (4)	C15—H151	0.96
Si1—C14	1.870 (3)	C15—H152	0.96
Si1—C15	1.849 (4)	C15—H153	0.96
Si2—C12	1.827 (3)	C16—H161	0.96
Si2—C16	1.846 (4)	C16—H162	0.96
Si2—C17	1.831 (3)	C16—H163	0.96
Si2—C18	1.833 (5)	C17—H171	0.96
O1—C2	1.370 (2)	C17—H172	0.96
O1—C21	1.442 (2)	C17—H173	0.96
O2—C3	1.366 (2)	C18—H181	0.96
O2—C22	1.440 (2)	C18—H182	0.96
C1—C2	1.373 (3)	C18—H183	0.96
C1—C5	1.452 (3)	C19—H191	0.96
C2—C3	1.413 (3)	C19—H192	0.96
C3—C4	1.379 (3)	C19—H193	0.96
C4—C9	1.451 (3)	C20—H201	0.96
C5—C6	1.351 (3)	C20—H202	0.96
C6—C7	1.424 (4)	C20—H203	0.96
C6—H6	0.96	C21—H211	0.96
C7—C8	1.205 (4)	C21—H212	0.96
C9—C10	1.353 (3)	C21—H213	0.96
C10—C11	1.428 (3)	C22—H221	0.96
C10—H10	0.96	C22—H222	0.96
C11—C12	1.204 (4)	C22—H223	0.96
C13—H131	0.96
C1—S1—C4	92.54 (10)	Si1—C14—H141	109.47
C8—Si1—C13	108.78 (14)	Si1—C14—H142	109.47
C8—Si1—C14	107.60 (15)	Si1—C14—H143	109.47
C8—Si1—C15	107.96 (16)	H141—C14—H142	109.47
C13—Si1—C14	110.63 (19)	H141—C14—H143	109.47
C13—Si1—C15	111.47 (16)	H142—C14—H143	109.47
C14—Si1—C15	110.27 (18)	Si1—C15—H151	109.47
C12—Si2—C16	110.01 (16)	Si1—C15—H152	109.47
C12—Si2—C17	109.58 (14)	Si1—C15—H153	109.47
C12—Si2—C18	106.21 (18)	H151—C15—H152	109.47
C16—Si2—C17	109.70 (18)	H151—C15—H153	109.47
C16—Si2—C18	112.49 (18)	H152—C15—H153	109.47
C17—Si2—C18	108.8 (2)	Si2—C16—H161	109.47
C2—O1—C21	112.76 (15)	Si2—C16—H162	109.47
C3—O2—C22	116.18 (16)	Si2—C16—H163	109.47
S1—C1—C2	110.37 (16)	H161—C16—H162	109.47
S1—C1—C5	120.10 (15)	H161—C16—H163	109.47
C2—C1—C5	129.51 (19)	H162—C16—H163	109.47
O1—C2—C1	123.71 (19)	Si2—C17—H171	109.47
O1—C2—C3	122.93 (17)	Si2—C17—H172	109.47
C1—C2—C3	113.35 (18)	Si2—C17—H173	109.47
O2—C3—C2	124.45 (17)	H171—C17—H172	109.47
O2—C3—C4	121.89 (19)	H171—C17—H173	109.47
C2—C3—C4	113.57 (18)	H172—C17—H173	109.47
S1—C4—C3	110.14 (16)	Si2—C18—H181	109.47
S1—C4—C9	119.76 (14)	Si2—C18—H182	109.47
C3—C4—C9	130.10 (18)	Si2—C18—H183	109.47
S2—C5—C1	117.89 (15)	H181—C18—H182	109.47
S2—C5—C6	119.30 (17)	H181—C18—H183	109.47
C1—C5—C6	122.58 (18)	H182—C18—H183	109.47
C5—C6—C7	124.5 (2)	H191—C19—H192	109.47
C5—C6—H6	117.73	H191—C19—H193	109.47
C7—C6—H6	117.72	H192—C19—H193	109.47
C6—C7—C8	179.6 (2)	H201—C20—H202	109.47
Si1—C8—C7	177.8 (2)	H201—C20—H203	109.47
S3—C9—C4	117.38 (15)	H202—C20—H203	109.47
S3—C9—C10	119.28 (17)	O1—C21—H211	109.47
C4—C9—C10	123.23 (18)	O1—C21—H212	109.47
C9—C10—C11	125.4 (2)	O1—C21—H213	109.47
C9—C10—H10	117.3	H211—C21—H212	109.47
C11—C10—H10	117.3	H211—C21—H213	109.47
C10—C11—C12	175.5 (2)	H212—C21—H213	109.47
Si2—C12—C11	176.6 (2)	O2—C22—H221	109.47
Si1—C13—H131	109.47	O2—C22—H222	109.47
Si1—C13—H132	109.47	O2—C22—H223	109.47
Si1—C13—H133	109.47	H221—C22—H222	109.47
H131—C13—H132	109.47	H221—C22—H223	109.47
H131—C13—H133	109.47	H222—C22—H223	109.47
H132—C13—H133	109.47

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.96	2.43	3.020 (3)	119.35
C10—H10···O2	0.96	2.31	2.956 (3)	124.29
C20—H201···O2^i	0.96	2.36	3.213 (3)	147.47
C22—H222···O1	0.96	2.43	2.989 (3)	117.04

Symmetry code: (i) x, y−1, z.

(DSEM2)

Crystal data

C22H32O2S3Si2	Z = 8
Mr = 480.8	F(000) = 2048
Orthorhombic, Pccn	Dx = 1.164 Mg m^−3
Hall symbol: -P -2xac;-2ybc;-2zab	Mo Kα radiation, λ = 0.71073 Å
a = 33.63 (1) Å	µ = 0.37 mm^−1
b = 8.271 (2) Å	T = 100 K
c = 19.717 (6) Å	Plate, clear yellow
V = 5484 (3) Å^3	0.60 × 0.51 × 0.01 mm

Data collection

Bruker KAPPA APEX II CCD diffractometer	4671 independent reflections
Radiation source: X-ray tube	3185 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.079
ω– and φ–scans	θmax = 25.1°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −39→39
Tmin = 0.80, Tmax = 1.00	k = −9→9
48785 measured reflections	l = −22→23

Refinement

Refinement on F	128 constraints
R[F^2 > 2σ(F^2)] = 0.087	H-atom parameters constrained
wR(F^2) = 0.085	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 3.22	(Δ/σ)max = 0.033
4671 reflections	Δρmax = 0.75 e Å^−3
262 parameters	Δρmin = −0.74 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.48577 (4)	0.09321 (15)	0.14925 (7)	0.0273 (5)
S2	0.39846 (4)	0.12563 (17)	0.08590 (7)	0.0339 (5)
S3	0.54950 (4)	0.23657 (16)	0.24996 (7)	0.0324 (5)
Si1	0.31451 (5)	−0.0096 (2)	−0.12916 (9)	0.0483 (7)
Si2	0.67503 (5)	0.05745 (19)	0.40475 (8)	0.0338 (6)
O1	0.48893 (10)	−0.3104 (4)	0.04701 (16)	0.0250 (12)
O2	0.55614 (10)	−0.2785 (4)	0.14069 (17)	0.0252 (12)
C1	0.46915 (15)	−0.0466 (6)	0.0899 (2)	0.0244 (18)
C2	0.49443 (15)	−0.1789 (6)	0.0886 (3)	0.0231 (19)
C3	0.52739 (15)	−0.1644 (6)	0.1323 (3)	0.0210 (19)
C4	0.52700 (14)	−0.0247 (6)	0.1699 (3)	0.0211 (18)
C5	0.43223 (15)	−0.0187 (6)	0.0531 (3)	0.0226 (18)
C6	0.42494 (15)	−0.0889 (6)	−0.0068 (3)	0.029 (2)
C7	0.38874 (18)	−0.0660 (6)	−0.0455 (3)	0.033 (2)
C8	0.35965 (17)	−0.0468 (7)	−0.0796 (3)	0.041 (2)
C9	0.55396 (15)	0.0329 (6)	0.2232 (3)	0.0253 (18)
C10	0.58022 (15)	−0.0638 (6)	0.2547 (2)	0.0252 (18)
C11	0.60874 (17)	−0.0138 (6)	0.3044 (3)	0.028 (2)
C12	0.63440 (17)	0.0188 (6)	0.3452 (3)	0.030 (2)
C13	0.31924 (16)	0.1882 (8)	−0.1722 (3)	0.057 (3)
C14	0.27160 (19)	−0.0042 (10)	−0.0700 (3)	0.081 (3)
C15	0.3085 (2)	−0.1777 (9)	−0.1915 (3)	0.071 (3)
C16	0.69045 (17)	0.2734 (6)	0.4004 (3)	0.043 (2)
C17	0.6576 (2)	0.0090 (7)	0.4913 (3)	0.057 (3)
C18	0.71605 (17)	−0.0785 (7)	0.3798 (3)	0.053 (2)
C19	0.38635 (16)	0.0445 (6)	0.1687 (3)	0.037 (2)
C20	0.56987 (18)	0.3393 (6)	0.1773 (3)	0.041 (2)
C21	0.47467 (16)	−0.4503 (6)	0.0834 (3)	0.036 (2)
C22	0.57674 (17)	−0.3269 (6)	0.0804 (3)	0.038 (2)
H6	0.444962	−0.158871	−0.025243	0.0352*
H131	0.29571	0.208815	−0.19842	0.0687*
H132	0.322489	0.271836	−0.138951	0.0687*
H133	0.341961	0.186495	−0.201697	0.0687*
H141	0.268806	−0.10753	−0.048402	0.0977*
H142	0.275989	0.077494	−0.036251	0.0977*
H143	0.247792	0.020379	−0.094857	0.0977*
H151	0.309192	−0.279434	−0.168071	0.0856*
H152	0.283513	−0.166428	−0.214506	0.0856*
H153	0.329762	−0.173744	−0.223974	0.0856*
H161	0.695035	0.302993	0.35394	0.0514*
H162	0.669803	0.340267	0.418941	0.0514*
H163	0.714449	0.28839	0.425965	0.0514*
H171	0.651302	−0.103932	0.494065	0.0684*
H172	0.678226	0.034117	0.523378	0.0684*
H173	0.634383	0.0718	0.501474	0.0684*
H181	0.707294	−0.188755	0.382646	0.0635*
H182	0.723928	−0.054939	0.334007	0.0635*
H183	0.738255	−0.062471	0.409602	0.0635*
H191	0.361686	0.089953	0.184054	0.0448*
H192	0.383856	−0.07095	0.165723	0.0448*
H193	0.407105	0.071353	0.200161	0.0448*
H201	0.567032	0.453949	0.183172	0.0497*
H202	0.597534	0.312722	0.172904	0.0497*
H203	0.5559	0.305982	0.137253	0.0497*
H211	0.477335	−0.544569	0.055337	0.043*
H212	0.490003	−0.464345	0.124056	0.043*
H213	0.447206	−0.435164	0.095017	0.043*
H221	0.597893	−0.399644	0.092121	0.0456*
H222	0.558545	−0.380215	0.050274	0.0456*
H223	0.587583	−0.233208	0.058386	0.0456*
H10	0.579831	−0.17635	0.242934	0.0302*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0298 (8)	0.0185 (8)	0.0336 (9)	0.0032 (7)	−0.0037 (7)	−0.0017 (7)
S2	0.0384 (9)	0.0304 (9)	0.0330 (10)	0.0111 (7)	−0.0003 (8)	0.0023 (8)
S3	0.0471 (9)	0.0185 (8)	0.0317 (9)	0.0002 (7)	0.0002 (8)	−0.0018 (7)
Si1	0.0301 (10)	0.0838 (14)	0.0309 (11)	0.0011 (10)	−0.0020 (8)	0.0117 (11)
Si2	0.0290 (9)	0.0364 (10)	0.0359 (11)	−0.0023 (8)	−0.0040 (8)	−0.0022 (8)
O1	0.041 (2)	0.017 (2)	0.017 (2)	0.0019 (18)	−0.0016 (18)	−0.0042 (19)
O2	0.033 (2)	0.016 (2)	0.027 (2)	0.0061 (17)	0.0010 (18)	−0.0045 (17)
C1	0.030 (3)	0.026 (3)	0.017 (3)	0.001 (3)	0.000 (3)	0.000 (3)
C2	0.030 (3)	0.022 (3)	0.018 (3)	−0.002 (3)	−0.001 (3)	−0.004 (3)
C3	0.030 (3)	0.012 (3)	0.022 (3)	0.002 (3)	0.003 (3)	0.000 (3)
C4	0.023 (3)	0.019 (3)	0.021 (3)	0.002 (2)	−0.001 (2)	0.002 (3)
C5	0.032 (3)	0.016 (3)	0.020 (3)	0.004 (3)	0.001 (3)	−0.007 (3)
C6	0.030 (3)	0.031 (3)	0.027 (4)	0.007 (3)	−0.002 (3)	0.005 (3)
C7	0.044 (4)	0.034 (4)	0.020 (4)	0.003 (3)	0.002 (3)	−0.006 (3)
C8	0.029 (4)	0.055 (4)	0.039 (4)	0.005 (3)	−0.003 (3)	−0.003 (3)
C9	0.030 (3)	0.019 (3)	0.027 (3)	0.001 (3)	−0.001 (3)	−0.001 (3)
C10	0.036 (3)	0.022 (3)	0.018 (3)	−0.002 (3)	−0.002 (3)	−0.006 (3)
C11	0.036 (4)	0.021 (3)	0.026 (4)	−0.002 (3)	0.003 (3)	−0.003 (3)
C12	0.033 (3)	0.027 (3)	0.031 (4)	−0.001 (3)	0.000 (3)	0.002 (3)
C13	0.036 (4)	0.089 (5)	0.047 (5)	0.017 (4)	−0.001 (3)	−0.001 (4)
C14	0.044 (4)	0.145 (8)	0.056 (5)	0.012 (5)	0.009 (4)	0.017 (5)
C15	0.058 (5)	0.101 (6)	0.054 (5)	−0.027 (5)	−0.015 (4)	0.011 (4)
C16	0.033 (4)	0.052 (4)	0.043 (4)	−0.007 (3)	−0.004 (3)	0.002 (3)
C17	0.059 (5)	0.059 (4)	0.054 (4)	−0.019 (4)	−0.018 (4)	0.003 (4)
C18	0.047 (4)	0.051 (4)	0.061 (5)	0.013 (4)	−0.014 (4)	−0.011 (4)
C19	0.040 (4)	0.035 (4)	0.037 (4)	0.002 (3)	0.001 (3)	−0.006 (3)
C20	0.059 (4)	0.029 (3)	0.036 (4)	−0.002 (3)	−0.003 (3)	−0.001 (3)
C21	0.039 (4)	0.039 (4)	0.029 (4)	−0.012 (3)	0.006 (3)	−0.011 (3)
C22	0.039 (4)	0.037 (4)	0.038 (4)	0.011 (3)	0.006 (3)	0.001 (3)

Geometric parameters (Å, º)

S1—C1	1.742 (5)	C13—H132	0.96
S1—C4	1.747 (5)	C13—H133	0.96
S2—C5	1.774 (5)	C14—H141	0.96
S3—C9	1.777 (5)	C14—H142	0.96
Si1—C8	1.835 (6)	C14—H143	0.96
Si1—C13	1.855 (7)	C15—H151	0.96
Si1—C14	1.860 (7)	C15—H152	0.96
Si1—C15	1.870 (7)	C15—H153	0.96
Si2—C12	1.834 (6)	C16—H161	0.96
Si2—C16	1.867 (6)	C16—H162	0.96
Si2—C17	1.852 (6)	C16—H163	0.96
Si2—C18	1.852 (6)	C17—H171	0.96
O1—C2	1.378 (6)	C17—H172	0.96
O1—C21	1.447 (6)	C17—H173	0.96
O2—C3	1.364 (6)	C18—H181	0.96
O2—C22	1.435 (6)	C18—H182	0.96
C1—C2	1.390 (7)	C18—H183	0.96
C1—C5	1.460 (7)	C19—H191	0.96
C2—C3	1.412 (7)	C19—H192	0.96
C3—C4	1.375 (7)	C19—H193	0.96
C4—C9	1.470 (7)	C20—H201	0.96
C5—C6	1.341 (7)	C20—H202	0.96
C6—C7	1.452 (8)	C20—H203	0.96
C6—H6	0.96	C21—H211	0.96
C7—C8	1.200 (8)	C21—H212	0.96
C9—C10	1.347 (7)	C21—H213	0.96
C10—C11	1.435 (7)	C22—H221	0.96
C10—H10	0.96	C22—H222	0.96
C11—C12	1.212 (8)	C22—H223	0.96
C13—H131	0.96
C1—S1—C4	92.3 (2)	Si1—C14—H141	109.47
C8—Si1—C13	108.8 (3)	Si1—C14—H142	109.47
C8—Si1—C14	108.3 (3)	Si1—C14—H143	109.47
C8—Si1—C15	108.4 (3)	H141—C14—H142	109.47
C13—Si1—C14	109.4 (3)	H141—C14—H143	109.47
C13—Si1—C15	111.5 (3)	H142—C14—H143	109.47
C14—Si1—C15	110.5 (3)	Si1—C15—H151	109.47
C12—Si2—C16	110.2 (2)	Si1—C15—H152	109.47
C12—Si2—C17	108.6 (3)	Si1—C15—H153	109.47
C12—Si2—C18	106.3 (3)	H151—C15—H152	109.47
C16—Si2—C17	109.9 (3)	H151—C15—H153	109.47
C16—Si2—C18	111.4 (3)	H152—C15—H153	109.47
C17—Si2—C18	110.5 (3)	Si2—C16—H161	109.47
C2—O1—C21	112.5 (4)	Si2—C16—H162	109.47
C3—O2—C22	115.9 (4)	Si2—C16—H163	109.47
S1—C1—C2	109.9 (4)	H161—C16—H162	109.47
S1—C1—C5	120.2 (4)	H161—C16—H163	109.47
C2—C1—C5	129.8 (5)	H162—C16—H163	109.47
O1—C2—C1	123.5 (4)	Si2—C17—H171	109.47
O1—C2—C3	122.5 (4)	Si2—C17—H172	109.47
C1—C2—C3	113.9 (5)	Si2—C17—H173	109.47
O2—C3—C2	125.0 (4)	H171—C17—H172	109.47
O2—C3—C4	121.7 (4)	H171—C17—H173	109.47
C2—C3—C4	113.2 (4)	H172—C17—H173	109.47
S1—C4—C3	110.7 (4)	Si2—C18—H181	109.47
S1—C4—C9	118.5 (4)	Si2—C18—H182	109.47
C3—C4—C9	130.8 (5)	Si2—C18—H183	109.47
S2—C5—C1	118.2 (4)	H181—C18—H182	109.47
S2—C5—C6	119.8 (4)	H181—C18—H183	109.47
C1—C5—C6	121.8 (5)	H182—C18—H183	109.47
C5—C6—C7	124.2 (5)	H191—C19—H192	109.47
C5—C6—H6	117.92	H191—C19—H193	109.47
C7—C6—H6	117.91	H192—C19—H193	109.47
C6—C7—C8	177.6 (6)	H201—C20—H202	109.47
Si1—C8—C7	177.4 (5)	H201—C20—H203	109.47
S3—C9—C4	118.0 (4)	H202—C20—H203	109.47
S3—C9—C10	118.9 (4)	O1—C21—H211	109.47
C4—C9—C10	123.0 (4)	O1—C21—H212	109.47
C9—C10—C11	125.8 (5)	O1—C21—H213	109.47
C9—C10—H10	117.09	H211—C21—H212	109.47
C11—C10—H10	117.1	H211—C21—H213	109.47
C10—C11—C12	175.3 (6)	H212—C21—H213	109.47
Si2—C12—C11	176.4 (5)	O2—C22—H221	109.47
Si1—C13—H131	109.47	O2—C22—H222	109.47
Si1—C13—H132	109.47	O2—C22—H223	109.47
Si1—C13—H133	109.47	H221—C22—H222	109.47
H131—C13—H132	109.47	H221—C22—H223	109.47
H131—C13—H133	109.47	H222—C22—H223	109.47
H132—C13—H133	109.47
C6—C5—C1—S1	157.1 (4)	C15—Si1—C6—C5	−160.8 (4)
C10—C9—C4—S1	162.7 (4)	C10—C9—S3—C20	111.2 (5)
C6—C5—C9—C10	−51.4 (7)	C6—C5—S2—C19	124.7 (4)
C16—Si2—C10—C9	−22.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.96	2.41	3.026 (6)	121.42
C20—H201···O2^i	0.96	2.40	3.283 (6)	152.38
C22—H222···O1	0.96	2.42	3.035 (7)	121.43
C10—H10···O2	0.96	2.33	2.983 (6)	124.64

Symmetry code: (i) x, y+1, z.

(ESEM)

Crystal data

C22H30O2S3Si2	F(000) = 1016
Mr = 478.8	Dx = 1.185 Mg m^−3
Monoclinic, C2/c(0β0)s0†	Mo Kα radiation, λ = 0.71069 Å
q = 0.622100b*	Cell parameters from 9719 reflections
a = 31.8766 (8) Å	θ = 2.5–27.5°
b = 8.4003 (5) Å	µ = 0.38 mm^−1
c = 10.0737 (3) Å	T = 100 K
β = 95.684 (2)°	Plate, translucent colourless
V = 2684.20 (19) Å^3	0.45 × 0.30 × 0.02 mm
Z = 4

† Symmetry operations: (1) x₁, x₂, x₃, x₄; (2) −x₁, x₂, −x₃+1/2, x₄+1/2; (3) −x₁, −x₂, −x₃, −x₄; (4) x₁, −x₂, x₃+1/2, −x₄+1/2; (5) x₁+1/2, x₂+1/2, x₃, x₄; (6) −x₁+1/2, x₂+1/2, −x₃+1/2, x₄+1/2; (7) −x₁+1/2, −x₂+1/2, −x₃, −x₄; (8) x₁+1/2, −x₂+1/2, x₃+1/2, −x₄+1/2.

Data collection

Bruker KAPPA APEX II CCD diffractometer	15382 independent reflections
Radiation source: X-ray tube	9184 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.067
ω– and φ–scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan SADABS	h = −41→41
Tmin = 0.87, Tmax = 0.99	k = −11→11
55245 measured reflections	l = −13→12

Refinement

Refinement on F	0 restraints
R[F^2 > 2σ(F^2)] = 0.063	240 constraints
wR(F^2) = 0.067	H-atom parameters constrained
S = 2.36	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
15382 reflections	(Δ/σ)max = 0.038
510 parameters

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

	x	y	z	Uiso*/Ueq
S1	0	0.26212 (6)	0.25	0.01692 (15)
S2	−0.079300 (12)	0.15970 (5)	0.04835 (4)	0.02685 (13)
Si1	−0.178225 (14)	0.34532 (7)	−0.36777 (4)	0.0400 (2)
O1	−0.03133 (3)	0.68766 (10)	0.13596 (9)	0.0225 (3)
C1	−0.01556 (4)	0.55252 (15)	0.19492 (13)	0.0159 (4)
C2	−0.02805 (4)	0.40346 (15)	0.15338 (13)	0.0154 (4)
C3	−0.06011 (4)	0.35709 (16)	0.04821 (13)	0.0175 (4)
C4	−0.07411 (4)	0.45644 (17)	−0.05240 (13)	0.0206 (4)
C5	−0.10659 (4)	0.41709 (17)	−0.15475 (13)	0.0230 (5)
C6	−0.13386 (5)	0.38950 (18)	−0.24273 (14)	0.0291 (5)
C7	−0.20045 (5)	0.5371 (2)	−0.43255 (17)	0.0568 (7)
C8	−0.15937 (5)	0.2264 (2)	−0.50418 (16)	0.0416 (6)
C9	−0.21754 (6)	0.2311 (3)	−0.28318 (18)	0.0725 (9)
C10	−0.10471 (5)	0.15544 (18)	0.20176 (15)	0.0361 (6)
C11	−0.02212 (5)	0.82448 (17)	0.22074 (13)	0.0297 (6)
H41	−0.061396	0.559597	−0.055019	0.0247*
H71	−0.223724	0.516942	−0.498125	0.0681*
H72	−0.20993	0.597485	−0.360628	0.0681*
H73	−0.179162	0.595831	−0.472347	0.0681*
H81	−0.18251	0.203239	−0.569385	0.0499*
H82	−0.138361	0.285344	−0.545007	0.0499*
H83	−0.147471	0.128905	−0.468841	0.0499*
H91	−0.241198	0.206115	−0.345991	0.087*
H92	−0.204992	0.134626	−0.247784	0.087*
H93	−0.226776	0.293559	−0.21198	0.087*
H101	−0.116554	0.052132	0.212829	0.0434*
H102	−0.08439	0.178181	0.275932	0.0434*
H103	−0.126624	0.233744	0.197577	0.0434*
H111	−0.040197	0.824805	0.29104	0.0357*
H112	−0.02767	0.919093	0.169459	0.0357*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0241 (3)	0.0083 (2)	0.0167 (2)	0	−0.00617 (19)	0
S2	0.0371 (2)	0.0242 (2)	0.01787 (18)	−0.01195 (18)	−0.00438 (16)	0.00017 (16)
Si1	0.0195 (2)	0.0817 (5)	0.0177 (2)	−0.0028 (3)	−0.00384 (17)	0.0027 (3)
O1	0.0367 (6)	0.0095 (5)	0.0202 (5)	0.0052 (4)	−0.0019 (4)	0.0022 (4)
C1	0.0221 (7)	0.0097 (7)	0.0163 (7)	0.0039 (5)	0.0029 (5)	0.0027 (6)
C2	0.0184 (7)	0.0135 (7)	0.0138 (6)	0.0019 (5)	−0.0004 (5)	0.0034 (5)
C3	0.0192 (7)	0.0168 (7)	0.0162 (7)	0.0001 (6)	0.0000 (5)	0.0004 (5)
C4	0.0188 (7)	0.0227 (8)	0.0196 (7)	−0.0010 (6)	−0.0016 (6)	0.0037 (6)
C5	0.0222 (8)	0.0287 (9)	0.0179 (7)	0.0000 (6)	0.0014 (6)	0.0065 (6)
C6	0.0229 (8)	0.0435 (11)	0.0205 (8)	−0.0023 (7)	−0.0003 (6)	0.0074 (7)
C7	0.0401 (11)	0.0927 (16)	0.0353 (10)	0.0268 (11)	−0.0078 (8)	−0.0109 (10)
C8	0.0378 (11)	0.0533 (12)	0.0325 (9)	−0.0025 (9)	−0.0030 (8)	−0.0013 (8)
C9	0.0449 (12)	0.137 (2)	0.0352 (11)	−0.0458 (13)	0.0010 (9)	−0.0069 (12)
C10	0.0402 (10)	0.0370 (10)	0.0316 (9)	−0.0152 (8)	0.0056 (7)	0.0030 (7)
C11	0.0556 (12)	0.0091 (8)	0.0238 (8)	0.0060 (7)	0.0002 (7)	−0.0001 (6)

Geometric parameters (Å, º)

	Average	Minimum	Maximum
S1—C1	2.554 (4)	2.544 (4)	2.563 (4)
S1—C1^i	2.554 (4)	2.544 (4)	2.563 (4)
S1—C2	1.735 (4)	1.730 (4)	1.741 (4)
S1—C2^i	1.735 (4)	1.730 (4)	1.741 (4)
S1—C3	2.778 (4)	2.769 (4)	2.784 (4)
S1—C3^i	2.778 (4)	2.769 (4)	2.784 (4)
S1—H102	3(6)	3(6)	3(6)
S1—H102^i	3(6)	3(6)	3(6)
S1—H112^ii	3(2)	2.8 (18)	3(3)
S1—H112^iii	3(2)	2.8 (18)	3(3)
S2—C2	2.772 (4)	2.765 (4)	2.777 (4)
S2—C3	1.772 (4)	1.764 (4)	1.781 (4)
S2—C4	2.708 (5)	2.692 (5)	2.726 (5)
S2—C10	1.817 (5)	1.813 (5)	1.824 (5)
S2—H101	2(4)	2(4)	2(4)
S2—H102	2(2)	2(2)	2(2)
S2—H103	2(5)	2(5)	2(5)
S2—H111^iv	3(4)	3(3)	3(4)
S2—H112^ii	3(4)	3(4)	3(5)
Si1—C6	1.839 (4)	1.832 (4)	1.847 (4)
Si1—C7	1.858 (5)	1.841 (5)	1.873 (5)
Si1—C8	1.853 (5)	1.840 (5)	1.868 (5)
Si1—C9	1.854 (6)	1.839 (6)	1.879 (6)
Si1—H71	2(4)	2(4)	2(4)
Si1—H72	2(3)	2(3)	2(3)
Si1—H73	2.4 (18)	2.3 (18)	2.4 (18)
Si1—H81	2(2)	2.3 (19)	2.4 (19)
Si1—H82	2(4)	2(4)	2(4)
Si1—H83	2(3)	2(3)	2(3)
Si1—H91	2(6)	2(5)	2(6)
Si1—H92	2(3)	2(3)	2(3)
Si1—H93	2(5)	2(5)	2(5)
O1—O1^i	2.899 (4)	2.895 (4)	2.904 (4)
O1—C1	1.362 (5)	1.357 (5)	1.366 (5)
O1—C1^i	2.442 (5)	2.436 (5)	2.449 (5)
O1—C2	2.410 (4)	2.399 (4)	2.420 (4)
O1—C4	2.969 (5)	2.934 (5)	2.998 (5)
O1—C11	1.453 (4)	1.441 (4)	1.460 (4)
O1—C11^i	2.425 (4)	2.407 (4)	2.441 (4)
O1—H41	2(3)	2(3)	2(2)
O1—H111	2(2)	2(3)	2(2)
O1—H111^i	3(5)	3(5)	3(6)
O1—H112	2.0 (19)	2.0 (18)	2.0 (19)
C1—C1^i	1.418 (6)	1.405 (6)	1.430 (6)
C1—C2	1.374 (5)	1.358 (5)	1.387 (5)
C1—C2^i	2.336 (5)	2.322 (5)	2.352 (6)
C1—C3	2.556 (5)	2.543 (5)	2.566 (5)
C1—C11	2.329 (5)	2.321 (5)	2.335 (5)
C1—C11^i	2.698 (5)	2.689 (5)	2.712 (5)
C1—H41	3(3)	3(3)	3(3)
C1—H111	3(3)	3(3)	3(2)
C1—H111^i	3(4)	3(5)	3(4)
C2—C2^i	2.517 (5)	2.504 (5)	2.530 (5)
C2—C3	1.455 (5)	1.444 (5)	1.464 (5)
C2—C4	2.465 (6)	2.459 (6)	2.473 (6)
C2—H41	3(3)	3(3)	3(3)
C2—H102	3(4)	3(4)	3(5)
C3—C4	1.356 (6)	1.347 (6)	1.369 (6)
C3—C5	2.460 (6)	2.450 (6)	2.466 (6)
C3—C10	2.786 (6)	2.773 (6)	2.797 (6)
C3—H41	2.0 (18)	2.0 (18)	2.0 (18)
C3—H102	3(3)	3(3)	3(3)
C3—H103	3(5)	3(5)	3(5)
C4—C5	1.429 (6)	1.405 (6)	1.448 (6)
C4—C6	2.631 (6)	2.612 (5)	2.653 (5)
C4—H41	1(3)	1(3)	1(3)
C4—H82^v	3(5)	3(4)	3(5)
C5—C6	1.203 (6)	1.192 (6)	1.209 (6)
C5—H41	2(4)	2(5)	2(4)
C5—H82^v	3(3)	3(3)	3(3)
C5—H111^iv	3(5)	3(4)	3(5)
C6—C7	2.990 (6)	2.965 (6)	3.015 (6)
C6—C8	3.014 (6)	2.979 (6)	3.049 (6)
C6—C9	2.976 (6)	2.954 (7)	3.001 (6)
C6—H101^vi	4(2)	3(3)	4.8 (17)
C7—H71	1(5)	1(5)	1(5)
C7—H72	1(3)	1(3)	1(3)
C7—H73	1(5)	1(5)	1(5)
C8—H81	1(5)	1(5)	1(4)
C8—H82	1(5)	1(5)	1(5)
C8—H83	1(3)	1(2)	1(3)
C9—H72^vii	3(5)	3(5)	3(6)
C9—H91	1(5)	1(5)	1(5)
C9—H92	1(3)	1(3)	1(3)
C9—H93	1(3)	1(3)	1(3)
C10—H82^viii	3(3)	3(3)	3(4)
C10—H101	1(3)	1(3)	1(3)
C10—H102	1(4)	1(4)	1(4)
C10—H103	1(5)	1(5)	1(5)
C11—C11^i	1.483 (5)	1.481 (5)	1.485 (5)
C11—H111	1(5)	1(5)	1(5)
C11—H111^i	2(6)	2(6)	2(6)
C11—H112	1(2)	1.0 (18)	1.0 (18)
C11—H112^i	2(5)	2(5)	2(5)
H41—H82^v	2.8035	2.6414	3.0371
H41—H102^iv	2.8443	2.7612	2.9236
H71—H72	1.5677	1.5676	1.5677
H71—H73	1.5677	1.567	1.5683
H71—H91^ix	2.645	2.5594	2.7911
H71—H93^iv	2.689	2.5373	2.886
H72—H73	1.5677	1.5668	1.5685
H72—H91^x	2.9347	2.7266	3.1049
H72—H92^x	3.0988	2.8089	3.4242
H72—H93^x	2.8424	2.6068	3.1513
H72—H103^iv	3.0231	2.876	3.1317
H73—H93^iv	2.8883	2.8072	2.9751
H73—H103^iv	2.6896	2.5493	2.8225
H81—H82	1.5677	1.5674	1.568
H81—H83	1.5676	1.567	1.5683
H81—H91^ix	2.6201	2.417	2.8587
H81—H92^vi	3.4145	2.6698	4.3469
H82—H83	1.5677	1.5666	1.5687
H82—H102^xi	2.7836	2.6281	3.0182
H82—H103^xi	2.7104	2.5795	2.8997
H83—H101^vi	2.5982	2.4697	2.8256
H91—H92	1.5677	1.5668	1.5686
H91—H93	1.5677	1.5674	1.568
H92—H93	1.5677	1.5669	1.5685
H101—H102	1.5677	1.5672	1.5681
H101—H103	1.5677	1.5673	1.568
H101—H111^ii	3.1659	2.971	3.4335
H102—H103	1.5677	1.5673	1.568
H102—H111^ii	3.3031	2.9634	3.723
H111—H111^i	2.7901	2.7886	2.7917
H111—H112	1.5485	1.5424	1.5554
H111—H112^i	2.3192	2.3142	2.325
H112—H112^i	2.2847	2.2824	2.2871
C1—S1—C1^i	32.22 (13)	31.94 (13)	32.50 (13)
C1—S1—C2	30.39 (15)	30.02 (15)	30.67 (15)
C1—S1—C2^i	62.61 (16)	62.29 (16)	63.01 (16)
C1—S1—C3	57.10 (12)	56.72 (12)	57.39 (12)
C1—S1—C3^i	89.31 (12)	89.00 (12)	89.69 (12)
C1—S1—H102	95.36	94.28	96.52
C1—S1—H102^i	112.9	111.3	114.48
C1—S1—H112^ii	142.78	140.84	145.32
C1—S1—H112^iii	174.52	172.92	176.02
C1^i—S1—C2	62.61 (16)	62.29 (16)	63.01 (16)
C1^i—S1—C2^i	30.39 (15)	30.02 (15)	30.67 (15)
C1^i—S1—C3	89.31 (12)	89.00 (12)	89.69 (12)
C1^i—S1—C3^i	57.10 (12)	56.72 (12)	57.39 (12)
C1^i—S1—H102	112.89	111.3	114.48
C1^i—S1—H102^i	95.37	94.28	96.52
C1^i—S1—H112^ii	174.5	172.92	176.02
C1^i—S1—H112^iii	142.8	140.84	145.32
C2—S1—C2^i	93.00 (18)	92.67 (18)	93.33 (18)
C2—S1—C3	26.71 (15)	26.41 (15)	26.98 (15)
C2—S1—C3^i	119.70 (15)	119.43 (15)	119.98 (15)
C2—S1—H102	77.17	76.49	77.59
C2—S1—H102^i	124.59	122.64	126.32
C2—S1—H112^ii	112.41	110.74	114.83
C2—S1—H112^iii	154.49	151.95	156.57
C2^i—S1—C3	119.70 (15)	119.43 (15)	119.98 (15)
C2^i—S1—C3^i	26.71 (15)	26.41 (15)	26.98 (15)
C2^i—S1—H102	124.59	122.64	126.32
C2^i—S1—H102^i	77.18	76.49	77.59
C2^i—S1—H112^ii	154.51	151.95	156.57
C2^i—S1—H112^iii	112.43	110.74	114.83
C3—S1—C3^i	146.40 (11)	146.38 (11)	146.43 (11)
C3—S1—H102	62.67	61.96	63.37
C3—S1—H102^i	127.17	125.46	128.98
C3—S1—H112^ii	85.7	83.77	88.28
C3—S1—H112^iii	127.85	125.27	129.82
C3^i—S1—H102	127.18	125.46	128.98
C3^i—S1—H102^i	62.68	61.96	63.37
C3^i—S1—H112^ii	127.87	125.27	129.82
C3^i—S1—H112^iii	85.72	83.77	88.28
H102—S1—H102^i	150.84	150.66	151.02
H102—S1—H112^ii	62.97	61.73	64.72
H102—S1—H112^iii	89.17	87.69	90.26
H102^i—S1—H112^ii	89.16	87.69	90.26
H102^i—S1—H112^iii	62.96	61.73	64.72
H112^ii—S1—H112^iii	42.27	40.96	43.57
C2—S2—C3	27.58 (15)	27.33 (15)	27.77 (15)
C2—S2—C4	53.44 (12)	53.28 (12)	53.60 (12)
C2—S2—C10	89.36 (17)	88.44 (17)	90.61 (17)
C2—S2—H101	110.11	109.4	111.15
C2—S2—H102	70.81	70.11	71.81
C2—S2—H103	87.35	86.12	88.91
C2—S2—H111^iv	91.33	85.59	97.52
C2—S2—H112^ii	93.96	87.05	102.5
C3—S2—C4	25.89 (15)	25.57 (15)	26.24 (15)
C3—S2—C10	101.8 (2)	100.8 (2)	102.5 (2)
C3—S2—H101	124.79	123.76	125.5
C3—S2—H102	89.88	88.97	90.55
C3—S2—H103	89.88	88.96	90.54
C3—S2—H111^iv	78.01	74.77	82.11
C3—S2—H112^ii	119.21	111.74	128.27
C4—S2—C10	112.84 (18)	109.95 (18)	115.23 (18)
C4—S2—H101	133.17	130.2	135.63
C4—S2—H102	108.87	106.52	110.9
C4—S2—H103	93.7	90.73	96.07
C4—S2—H111^iv	66.25	65.48	67.53
C4—S2—H112^ii	140.52	133.17	149.75
C10—S2—H101	22.95	22.89	23
C10—S2—H102	22.95	22.89	23
C10—S2—H103	22.95	22.89	23
C10—S2—H111^iv	172.94	166.57	179.3
C10—S2—H112^ii	84.72	83.1	86.37
H101—S2—H102	39.48	39.38	39.56
H101—S2—H103	39.48	39.37	39.56
H101—S2—H111^iv	156.16	151.37	158.77
H101—S2—H112^ii	74.3	71.87	76.49
H102—S2—H103	39.48	39.37	39.56
H102—S2—H111^iv	158.48	148.51	169.02
H102—S2—H112^ii	73.43	69.6	77.99
H103—S2—H111^iv	154.59	145.91	161.36
H103—S2—H112^ii	107.54	105.88	109.27
H111^iv—S2—H112^ii	96.59	89.29	103.42
C6—Si1—C7	108.0 (2)	106.8 (2)	108.5 (2)
C6—Si1—C8	109.4 (2)	107.9 (2)	111.0 (2)
C6—Si1—C9	107.4 (2)	106.7 (2)	108.2 (2)
C6—Si1—H71	130.53	129.41	131.26
C6—Si1—H72	95.87	94.81	96.49
C6—Si1—H73	95.87	94.82	96.49
C6—Si1—H81	132.06	130.56	133.48
C6—Si1—H82	97.24	95.71	98.76
C6—Si1—H83	97.24	95.7	98.75
C6—Si1—H91	129.98	129.14	130.72
C6—Si1—H92	95.3	94.68	96.06
C6—Si1—H93	95.3	94.68	96.06
C7—Si1—C8	110.5 (2)	109.6 (2)	111.0 (2)
C7—Si1—C9	111.1 (2)	110.7 (2)	111.4 (2)
C7—Si1—H71	22.56	22.43	22.72
C7—Si1—H72	22.57	22.42	22.72
C7—Si1—H73	22.57	22.42	22.71
C7—Si1—H81	98.63	98.16	99.09
C7—Si1—H82	97.86	96.82	98.48
C7—Si1—H83	133.12	132.1	133.65
C7—Si1—H91	99.49	99.04	100.01
C7—Si1—H92	133.68	133.09	134.08
C7—Si1—H93	98.14	97.91	98.52
C8—Si1—C9	110.3 (2)	109.4 (2)	111.5 (2)
C8—Si1—H71	98.37	97.4	99.28
C8—Si1—H72	133.07	132.17	133.6
C8—Si1—H73	98.17	97.45	98.68
C8—Si1—H81	22.62	22.48	22.74
C8—Si1—H82	22.62	22.47	22.74
C8—Si1—H83	22.62	22.48	22.75
C8—Si1—H91	98.34	97.02	99.56
C8—Si1—H92	97.85	97.3	98.86
C8—Si1—H93	132.93	131.86	134.16
C9—Si1—H71	99.62	99.22	100
C9—Si1—H72	98.05	97.56	98.43
C9—Si1—H73	133.64	133.23	134.05
C9—Si1—H81	98.73	97.49	99.79
C9—Si1—H82	132.93	131.99	134.11
C9—Si1—H83	97.44	96.73	98.5
C9—Si1—H91	22.6	22.38	22.75
C9—Si1—H92	22.6	22.38	22.75
C9—Si1—H93	22.6	22.37	22.75
H71—Si1—H72	38.82	38.58	39.09
H71—Si1—H73	38.82	38.58	39.08
H71—Si1—H81	81.36	80.8	82.15
H71—Si1—H82	93.35	92.05	94.23
H71—Si1—H83	119.69	118.75	120.63
H71—Si1—H91	82.67	82.28	83.15
H71—Si1—H92	120.97	120.35	121.59
H71—Si1—H93	94.35	94	94.74
H72—Si1—H73	38.82	38.57	39.07
H72—Si1—H81	119.73	119.18	120.26
H72—Si1—H82	118.95	118	119.76
H72—Si1—H83	155.67	154.64	156.32
H72—Si1—H91	94.09	93.58	94.71
H72—Si1—H92	118.95	118.3	119.46
H72—Si1—H93	80.37	80.1	80.78
H73—Si1—H81	94.02	93.6	94.32
H73—Si1—H82	80.58	79.77	81.17
H73—Si1—H83	119.15	118.21	119.88
H73—Si1—H91	120.85	120.25	121.32
H73—Si1—H92	156.16	155.68	156.63
H73—Si1—H93	118.93	118.53	119.35
H81—Si1—H82	38.91	38.65	39.11
H81—Si1—H83	38.9	38.68	39.12
H81—Si1—H91	81.5	80.05	82.6
H81—Si1—H92	94	93.23	94.95
H81—Si1—H93	119.91	118.46	121.11
H82—Si1—H83	38.9	38.67	39.13
H82—Si1—H91	119.75	118.26	121.04
H82—Si1—H92	118.71	118.06	119.69
H82—Si1—H93	155.5	154.5	156.77
H83—Si1—H91	93.05	92.12	94.18
H83—Si1—H92	80.09	79.51	81.12
H83—Si1—H93	118.54	117.66	119.76
H91—Si1—H92	38.88	38.5	39.14
H91—Si1—H93	38.88	38.49	39.13
H92—Si1—H93	38.88	38.5	39.14
O1^i—O1—C1	57.0 (2)	56.6 (2)	57.5 (2)
O1^i—O1—C1^i	27.89 (11)	27.78 (10)	28.01 (11)
O1^i—O1—C2	85.43 (13)	85.22 (13)	85.72 (13)
O1^i—O1—C4	138.34 (13)	137.84 (13)	138.96 (13)
O1^i—O1—C11	56.62 (17)	56.04 (17)	57.33 (17)
O1^i—O1—C11^i	30.02 (10)	29.80 (10)	30.22 (10)
O1^i—O1—H41	148.21	145.32	150.84
O1^i—O1—H111	61.36	60.94	61.92
O1^i—O1—H111^i	41.93	41.66	42.2
O1^i—O1—H112	80.87	80.31	81.58
C1—O1—C1^i	29.2 (2)	28.8 (2)	29.5 (2)
C1—O1—C2	28.4 (2)	28.0 (2)	28.8 (2)
C1—O1—C4	81.6 (2)	81.0 (2)	82.4 (2)
C1—O1—C11	111.6 (3)	111.0 (3)	112.3 (3)
C1—O1—C11^i	86.1 (2)	85.5 (2)	86.7 (2)
C1—O1—H41	94.16	92.41	95.97
C1—O1—H111	102.92	102.14	103.72
C1—O1—H111^i	88.41	87.45	89.42
C1—O1—H112	137.67	137.11	138.58
C1^i—O1—C2	57.55 (14)	57.31 (14)	57.86 (14)
C1^i—O1—C4	110.56 (15)	110.19 (15)	111.16 (15)
C1^i—O1—C11	83.6 (2)	83.1 (2)	84.1 (2)
C1^i—O1—C11^i	57.16 (14)	56.81 (14)	57.48 (14)
C1^i—O1—H41	122.11	120.07	124.09
C1^i—O1—H111	81.51	81.2	81.78
C1^i—O1—H111^i	63.14	62.51	63.74
C1^i—O1—H112	108.71	108.17	109.39
C2—O1—C4	53.33 (14)	52.91 (14)	53.94 (14)
C2—O1—C11	138.4 (2)	138.0 (2)	138.8 (2)
C2—O1—C11^i	114.20 (17)	113.96 (16)	114.67 (17)
C2—O1—H41	66.8	65.73	67.94
C2—O1—H111	122.23	121.2	123.55
C2—O1—H111^i	113.07	112.18	114.1
C2—O1—H112	165.38	164.95	165.62
C4—O1—C11	163.1 (2)	162.5 (2)	163.6 (2)
C4—O1—C11^i	162.07 (17)	161.51 (18)	162.80 (17)
C4—O1—H41	15.82	15.31	16.26
C4—O1—H111	142.53	142.05	142.79
C4—O1—H111^i	144.23	143.53	144.93
C4—O1—H112	140.73	140.15	141.31
C11—O1—C11^i	34.73 (18)	34.35 (18)	35.24 (18)
C11—O1—H41	154.16	152.54	155.57
C11—O1—H111	27.04	26.95	27.2
C11—O1—H111^i	50.09	49.71	50.58
C11—O1—H112	27.05	26.95	27.2
C11^i—O1—H41	157.58	154.62	160.61
C11^i—O1—H111	53.28	52.98	53.73
C11^i—O1—H111^i	21.54	21.42	21.67
C11^i—O1—H112	53.28	52.98	53.74
H41—O1—H111	147	143.9	149.93
H41—O1—H111^i	136.08	133.09	139.15
H41—O1—H112	127.76	126.57	128.69
H111—O1—H111^i	73.18	72.8	73.71
H111—O1—H112	45.78	45.43	46.25
H111^i—O1—H112	58.63	58.42	58.92
S1—C1—O1	163.1 (3)	162.6 (3)	163.7 (3)
S1—C1—O1^i	101.78 (15)	101.59 (15)	101.98 (15)
S1—C1—C1^i	73.9 (2)	73.6 (2)	74.1 (2)
S1—C1—C2	39.68 (19)	39.5 (2)	39.83 (19)
S1—C1—C2^i	41.25 (11)	41.16 (11)	41.34 (11)
S1—C1—C3	65.86 (12)	65.36 (12)	66.26 (12)
S1—C1—C11	160.6 (2)	160.3 (2)	161.0 (2)
S1—C1—C11^i	132.79 (18)	131.92 (17)	133.34 (18)
S1—C1—H41	106.71	105.24	107.86
S1—C1—H111	144.57	143.63	145.17
S1—C1—H111^i	130.04	128.78	131.1
O1—C1—O1^i	95.1 (2)	94.6 (2)	95.5 (2)
O1—C1—C1^i	122.9 (3)	122.6 (3)	123.4 (3)
O1—C1—C2	123.5 (4)	122.8 (4)	124.1 (4)
O1—C1—C2^i	155.5 (3)	155.0 (3)	156.1 (3)
O1—C1—C3	97.3 (2)	96.8 (2)	98.2 (3)
O1—C1—C11	35.46 (17)	34.95 (17)	35.76 (17)
O1—C1—C11^i	63.7 (2)	63.00 (19)	64.3 (2)
O1—C1—H41	56.74	54.96	58.61
O1—C1—H111	47.04	46.64	47.51
O1—C1—H111^i	63.74	62.81	64.66
O1^i—C1—C1^i	27.90 (18)	27.81 (18)	28.04 (18)
O1^i—C1—C2	141.4 (3)	141.3 (3)	141.7 (3)
O1^i—C1—C2^i	60.54 (15)	60.41 (15)	60.66 (15)
O1^i—C1—C3	167.4 (2)	166.8 (2)	168.0 (2)
O1^i—C1—C11	61.06 (14)	60.37 (13)	61.58 (14)
O1^i—C1—C11^i	32.35 (10)	31.93 (10)	32.61 (10)
O1^i—C1—H41	148.73	147.83	149.65
O1^i—C1—H111	61.61	60.89	62.21
O1^i—C1—H111^i	42.51	42.19	42.68
C1^i—C1—C2	113.6 (3)	113.3 (3)	113.9 (3)
C1^i—C1—C2^i	32.64 (19)	32.39 (19)	32.8 (2)
C1^i—C1—C3	139.7 (3)	139.2 (3)	140.2 (3)
C1^i—C1—C11	88.7 (2)	88.1 (2)	89.1 (2)
C1^i—C1—C11^i	59.6 (2)	59.1 (2)	59.9 (2)
C1^i—C1—H41	167.13	164.19	170.59
C1^i—C1—H111	85.82	85.25	86.16
C1^i—C1—H111^i	65.16	64.6	65.63
C2—C1—C2^i	80.9 (3)	80.7 (3)	81.1 (3)
C2—C1—C3	26.2 (2)	25.6 (2)	26.7 (2)
C2—C1—C11	155.9 (3)	155.1 (3)	157.0 (3)
C2—C1—C11^i	170.3 (3)	169.3 (3)	171.2 (3)
C2—C1—H41	68.28	67.38	69.14
C2—C1—H111	145	143.73	146.18
C2—C1—H111^i	154.01	152.9	155.21
C2^i—C1—C3	107.11 (18)	106.52 (18)	107.54 (18)
C2^i—C1—C11	121.0 (2)	120.3 (2)	121.4 (2)
C2^i—C1—C11^i	91.91 (17)	91.19 (17)	92.39 (17)
C2^i—C1—H41	145.94	143.65	147.73
C2^i—C1—H111	114.29	114.02	114.6
C2^i—C1—H111^i	93.97	93	94.78
C3—C1—C11	130.7 (2)	129.9 (2)	131.9 (2)
C3—C1—C11^i	160.1 (2)	159.5 (2)	161.0 (2)
C3—C1—H41	43.54	43.26	43.95
C3—C1—H111	127.05	125.95	128.28
C3—C1—H111^i	147.63	146.98	148.02
C11—C1—C11^i	33.30 (12)	33.12 (12)	33.46 (12)
C11—C1—H41	92.18	90.52	93.73
C11—C1—H111	20.96	20.77	21.14
C11—C1—H111^i	43.51	43.36	43.73
C11^i—C1—H41	116.7	115.57	117.67
C11^i—C1—H111	44.3	44.06	44.56
C11^i—C1—H111^i	19.2	19.13	19.31
H41—C1—H111	99.45	97.15	101.97
H41—C1—H111^i	107.29	106	109.16
H111—C1—H111^i	59.96	59.73	60.16
S1—C2—S2	87.65 (15)	86.23 (15)	88.74 (15)
S1—C2—O1	138.0 (2)	137.4 (2)	138.6 (2)
S1—C2—C1	109.9 (3)	109.5 (3)	110.4 (3)
S1—C2—C1^i	76.14 (17)	75.80 (17)	76.39 (17)
S1—C2—C2^i	43.50 (12)	43.29 (12)	43.67 (12)
S1—C2—C3	120.9 (3)	120.3 (3)	121.4 (3)
S1—C2—C4	146.1 (2)	145.3 (2)	146.8 (2)
S1—C2—H41	160.79	157.57	163.86
S1—C2—H102	68.15	67.55	68.88
S2—C2—O1	133.64 (17)	132.23 (17)	135.84 (17)
S2—C2—C1	159.8 (3)	157.8 (3)	162.4 (3)
S2—C2—C1^i	160.4 (2)	159.8 (2)	161.2 (2)
S2—C2—C2^i	130.24 (17)	129.00 (17)	131.07 (17)
S2—C2—C3	34.33 (17)	34.02 (17)	34.80 (18)
S2—C2—C4	61.95 (14)	61.52 (14)	62.35 (14)
S2—C2—H41	83.42	82.98	83.73
S2—C2—H102	47.49	47.18	47.67
O1—C2—C1	28.1 (2)	27.7 (2)	28.5 (2)
O1—C2—C1^i	61.91 (15)	61.57 (15)	62.27 (15)
O1—C2—C2^i	94.54 (17)	94.08 (17)	94.95 (17)
O1—C2—C3	101.1 (2)	100.5 (2)	102.0 (2)
O1—C2—C4	75.01 (17)	74.19 (17)	75.63 (17)
O1—C2—H41	55.32	54.05	56.84
O1—C2—H102	130.15	128.81	131.6
C1—C2—C1^i	33.8 (2)	33.4 (2)	34.2 (2)
C1—C2—C2^i	66.4 (2)	66.2 (2)	66.9 (2)
C1—C2—C3	129.2 (4)	128.4 (4)	130.0 (4)
C1—C2—C4	102.9 (3)	102.4 (3)	103.3 (3)
C1—C2—H41	82.5	81.8	83.37
C1—C2—H102	129.12	127.31	130.65
C1^i—C2—C2^i	32.64 (13)	32.34 (13)	32.80 (14)
C1^i—C2—C3	162.9 (3)	162.3 (3)	163.4 (3)
C1^i—C2—C4	136.4 (2)	135.9 (2)	136.9 (2)
C1^i—C2—H41	115.26	114.65	115.74
C1^i—C2—H102	114.96	113.16	116.39
C2^i—C2—C3	164.3 (3)	163.7 (3)	164.7 (3)
C2^i—C2—C4	166.9 (2)	165.9 (2)	168.2 (2)
C2^i—C2—H41	145.69	144.82	147
C2^i—C2—H102	95.44	93.94	96.6
C3—C2—C4	27.7 (2)	27.4 (2)	28.0 (2)
C3—C2—H41	49.17	48.82	49.45
C3—C2—H102	73.55	71.81	74.86
C4—C2—H41	21.52	21.4	21.6
C4—C2—H102	97.32	94.86	99.31
H41—C2—H102	115.97	112.71	118.72
S1—C3—S2	86.75 (14)	85.38 (14)	87.76 (14)
S1—C3—C1	57.04 (12)	56.83 (11)	57.28 (11)
S1—C3—C2	32.41 (17)	32.18 (17)	32.82 (17)
S1—C3—C4	151.6 (3)	150.3 (3)	153.9 (3)
S1—C3—C5	170.6 (2)	169.4 (2)	172.0 (2)
S1—C3—C10	76.85 (13)	76.14 (13)	77.59 (13)
S1—C3—H41	127.31	126.07	129.45
S1—C3—H102	59.55	58.61	60.58
S1—C3—H103	90.38	89.12	91.8
S2—C3—C1	141.1 (2)	140.8 (2)	141.3 (2)
S2—C3—C2	118.1 (3)	117.6 (3)	118.5 (3)
S2—C3—C4	119.3 (3)	118.5 (3)	120.0 (3)
S2—C3—C5	90.71 (19)	90.36 (19)	91.07 (19)
S2—C3—C10	39.67 (13)	39.29 (13)	40.09 (13)
S2—C3—H41	144.3	143.5	144.95
S2—C3—H102	52.71	52.3	53.18
S2—C3—H103	52.71	52.3	53.18
C1—C3—C2	24.63 (19)	24.30 (18)	25.01 (19)
C1—C3—C4	99.2 (3)	98.4 (3)	99.9 (3)
C1—C3—C5	127.3 (2)	126.7 (2)	127.8 (2)
C1—C3—C10	111.1 (2)	109.2 (2)	113.8 (2)
C1—C3—H41	74.53	73.9	75.3
C1—C3—H102	93.26	91.77	95.31
C1—C3—H103	109.05	106.1	112.87
C2—C3—C4	122.5 (3)	121.8 (3)	123.3 (3)
C2—C3—C5	151.2 (3)	150.5 (3)	151.7 (3)
C2—C3—C10	97.1 (3)	95.7 (3)	99.2 (3)
C2—C3—H41	97.36	96.8	98.17
C2—C3—H102	77.87	76.59	79.92
C2—C3—H103	102.61	100.39	105.91
C4—C3—C5	28.8 (2)	27.9 (2)	29.5 (2)
C4—C3—C10	130.0 (3)	126.7 (3)	132.2 (3)
C4—C3—H41	25.14	24.87	25.38
C4—C3—H102	144.47	140.46	147.69
C4—C3—H103	113.72	109.79	116.73
C5—C3—C10	106.65 (19)	104.29 (19)	108.73 (19)
C5—C3—H41	53.9	53.28	54.5
C5—C3—H102	125.06	122.39	127.34
C5—C3—H103	95.2	91.85	97.97
C10—C3—H41	145.68	142.11	149.05
C10—C3—H102	19.2	19.1	19.32
C10—C3—H103	19.2	19.11	19.32
H41—C3—H102	149.25	145.52	153.17
H41—C3—H103	126.55	122.81	130.07
H102—C3—H103	31.18	31.01	31.37
S2—C4—O1	114.10 (15)	113.04 (15)	114.68 (16)
S2—C4—C2	64.60 (14)	64.13 (14)	64.93 (14)
S2—C4—C3	34.8 (2)	34.3 (2)	35.3 (2)
S2—C4—C5	89.4 (3)	88.7 (3)	90.4 (3)
S2—C4—C6	90.53 (16)	88.86 (16)	92.69 (17)
S2—C4—H41	152.41	151.92	152.7
S2—C4—H82^v	125.88	122.13	129.53
O1—C4—C2	51.66 (13)	51.42 (13)	51.90 (13)
O1—C4—C3	80.2 (2)	79.0 (2)	81.1 (2)
O1—C4—C5	150.6 (3)	147.9 (3)	152.9 (3)
O1—C4—C6	149.7 (2)	145.5 (2)	152.2 (2)
O1—C4—H41	41.67	39.9	44.38
O1—C4—H82^v	77.12	63.48	90.53
C2—C4—C3	29.9 (2)	29.2 (2)	30.3 (2)
C2—C4—C5	153.9 (4)	153.2 (4)	154.8 (4)
C2—C4—C6	154.9 (2)	153.6 (2)	156.9 (2)
C2—C4—H41	88.12	87.77	88.52
C2—C4—H82^v	117.43	105.73	128.01
C3—C4—C5	124.1 (4)	122.9 (4)	125.4 (4)
C3—C4—C6	125.2 (3)	123.2 (3)	127.4 (3)
C3—C4—H41	117.96	117.32	118.53
C3—C4—H82^v	126.79	118.42	133.96
C5—C4—C6	1.3 (2)	0.3 (2)	2.6 (2)
C5—C4—H41	117.96	117.33	118.53
C5—C4—H82^v	74.8	64.08	85.3
C6—C4—H41	116.88	115.16	118.27
C6—C4—H82^v	74.13	63.43	84.39
H41—C4—H82^v	68.9	63.65	76.05
C3—C5—C4	27.2 (2)	26.7 (2)	27.7 (2)
C3—C5—C6	155.1 (4)	152.9 (4)	158.1 (4)
C3—C5—H41	51.46	51.15	51.98
C3—C5—H82^v	93.75	83.43	104.52
C3—C5—H111^iv	68.78	63.98	74.46
C4—C5—C6	177.2 (5)	174.2 (5)	179.3 (5)
C4—C5—H41	24.29	23.89	24.68
C4—C5—H82^v	77.74	67.97	89.12
C4—C5—H111^iv	79.58	72.42	87.14
C6—C5—H41	153.32	150.23	155.75
C6—C5—H82^v	100.79	89.41	111.38
C6—C5—H111^iv	101.59	94.31	111.91
H41—C5—H82^v	65.04	56.86	75.52
H41—C5—H111^iv	90.95	83.2	99.25
H82^v—C5—H111^iv	155.5	139.84	172.79
Si1—C6—C4	174.6 (2)	171.9 (2)	178.1 (2)
Si1—C6—C5	174.5 (4)	173.0 (4)	177.6 (4)
Si1—C6—C7	36.23 (14)	35.76 (13)	36.86 (14)
Si1—C6—C8	35.43 (12)	34.82 (12)	36.08 (13)
Si1—C6—C9	36.48 (13)	36.13 (13)	37.01 (13)
Si1—C6—H101^vi	81.19	74.01	89.88
C4—C6—C5	1.5 (3)	0.4 (3)	3.1 (3)
C4—C6—C7	142.8 (2)	137.6 (2)	149.4 (2)
C4—C6—C8	148.0 (2)	141.6 (2)	152.9 (2)
C4—C6—C9	140.5 (2)	139.5 (2)	141.3 (2)
C4—C6—H101^vi	100.34	96	103.91
C5—C6—C7	144.0 (4)	140.0 (4)	150.7 (4)
C5—C6—C8	147.7 (4)	141.1 (4)	151.9 (4)
C5—C6—C9	139.6 (4)	138.2 (4)	140.8 (4)
C5—C6—H101^vi	99.22	93.11	103.29
C7—C6—C8	61.03 (15)	60.83 (15)	61.41 (15)
C7—C6—C9	61.73 (16)	61.48 (16)	62.05 (16)
C7—C6—H101^vi	116.55	109.18	125.4
C8—C6—C9	61.06 (15)	60.36 (15)	61.67 (15)
C8—C6—H101^vi	59.25	52.37	66.55
C9—C6—H101^vi	72.49	66.75	80.63
Si1—C7—C6	35.80 (13)	35.37 (13)	36.31 (13)
Si1—C7—H71	109.47	109.46	109.48
Si1—C7—H72	109.47	109.46	109.48
Si1—C7—H73	109.47	109.46	109.48
C6—C7—H71	145.27	144.83	145.78
C6—C7—H72	89.69	89.38	89.93
C6—C7—H73	89.69	89.4	89.93
H71—C7—H72	109.47	109.44	109.51
H71—C7—H73	109.47	109.44	109.5
H72—C7—H73	109.47	109.45	109.49
Si1—C8—C6	35.13 (12)	34.17 (12)	36.05 (12)
Si1—C8—H81	109.47	109.46	109.48
Si1—C8—H82	109.47	109.45	109.49
Si1—C8—H83	109.47	109.46	109.49
C6—C8—H81	144.6	143.64	145.52
C6—C8—H82	90.08	89.55	90.65
C6—C8—H83	90.08	89.54	90.63
H81—C8—H82	109.47	109.43	109.51
H81—C8—H83	109.47	109.44	109.5
H82—C8—H83	109.47	109.45	109.49
Si1—C9—C6	36.14 (13)	35.63 (13)	36.44 (13)
Si1—C9—H72^vii	165.17	153.06	179.56
Si1—C9—H91	109.47	109.46	109.48
Si1—C9—H92	109.47	109.47	109.48
Si1—C9—H93	109.47	109.46	109.48
C6—C9—H72^vii	142.38	137.88	145.73
C6—C9—H91	145.61	145.12	145.92
C6—C9—H92	89.5	89.32	89.79
C6—C9—H93	89.5	89.31	89.78
H72^vii—C9—H91	69.53	65.1	75.6
H72^vii—C9—H92	79.78	58.49	96.83
H72^vii—C9—H93	63.84	53.88	78.54
H91—C9—H92	109.47	109.45	109.49
H91—C9—H93	109.47	109.45	109.5
H92—C9—H93	109.47	109.47	109.48
S2—C10—C3	38.50 (13)	38.10 (12)	39.08 (13)
S2—C10—H82^viii	155.98	153.7	158.59
S2—C10—H101	109.47	109.46	109.48
S2—C10—H102	109.47	109.46	109.48
S2—C10—H103	109.47	109.47	109.47
C3—C10—H82^viii	118.4	117.16	120.35
C3—C10—H101	147.97	147.58	148.56
C3—C10—H102	88.13	87.81	88.37
C3—C10—H103	88.13	87.8	88.36
H82^viii—C10—H101	93.31	91.8	94.06
H82^viii—C10—H102	62.95	52.84	72.62
H82^viii—C10—H103	58.45	48.71	68.2
H101—C10—H102	109.47	109.46	109.49
H101—C10—H103	109.47	109.46	109.48
H102—C10—H103	109.47	109.47	109.48
O1—C11—O1^i	93.4 (2)	92.9 (2)	93.8 (2)
O1—C11—C1	32.94 (17)	32.72 (17)	33.22 (17)
O1—C11—C1^i	64.07 (19)	63.87 (19)	64.28 (19)
O1—C11—C11^i	111.4 (3)	110.7 (3)	111.9 (3)
O1—C11—H111	109.47	109.47	109.48
O1—C11—H111^i	96.39	95.95	96.81
O1—C11—H112	109.47	109.47	109.47
O1—C11—H112^i	137.95	137.27	138.53
O1^i—C11—C1	61.79 (14)	61.58 (14)	62.16 (15)
O1^i—C11—C1^i	30.23 (11)	30.00 (11)	30.38 (11)
O1^i—C11—C11^i	33.91 (17)	33.70 (17)	34.07 (17)
O1^i—C11—H111	90.39	90.32	90.52
O1^i—C11—H111^i	52.26	52.16	52.34
O1^i—C11—H112	143.3	143.12	143.45
O1^i—C11—H112^i	52.26	52.16	52.34
C1—C11—C1^i	31.68 (14)	31.43 (14)	32.01 (14)
C1—C11—C11^i	87.2 (2)	86.9 (2)	87.5 (2)
C1—C11—H111	98.82	98.1	99.72
C1—C11—H111^i	83.88	83.43	84.17
C1—C11—H112	141.13	140.78	141.5
C1—C11—H112^i	112.21	112.01	112.55
C1^i—C11—C11^i	59.5 (2)	59.3 (2)	59.8 (2)
C1^i—C11—H111	93.19	92.4	93.85
C1^i—C11—H111^i	66.61	66.26	66.95
C1^i—C11—H112	159.16	158.89	159.47
C1^i—C11—H112^i	81.93	81.7	82.16
C11^i—C11—H111	109.47	109.47	109.47
C11^i—C11—H111^i	26.65	26.63	26.68
C11^i—C11—H112	109.47	109.46	109.48
C11^i—C11—H112^i	26.65	26.62	26.68
H111—C11—H111^i	136.12	136.1	136.15
H111—C11—H112	107.51	106.9	108.21
H111—C11—H112^i	95.72	95.39	96.01
H111^i—C11—H112	95.72	95.39	96.01
H111^i—C11—H112^i	45.13	44.9	45.33
H112—C11—H112^i	93.37	93.3	93.43
O1—H41—C1	29.11	28.77	29.45
O1—H41—C2	57.87	57.43	58.14
O1—H41—C3	88.87	87.09	89.78
O1—H41—C4	122.51	119.36	124.69
O1—H41—C5	152.21	146.56	156.97
O1—H41—H82^v	92.36	75.69	107.54
O1—H41—H102^iv	100.95	94.21	106.96
C1—H41—C2	29.22	29.05	29.33
C1—H41—C3	61.93	61.43	62.32
C1—H41—C4	98.22	97.7	98.6
C1—H41—C5	135.19	134.46	135.81
C1—H41—H82^v	110.92	96.54	123.34
C1—H41—H102^iv	129.43	122.52	135.11
C2—H41—C3	33.48	32.95	33.83
C2—H41—C4	70.36	70.09	70.66
C2—H41—C5	108.1	107.63	108.62
C2—H41—H82^v	119.19	109.53	127.41
C2—H41—H102^iv	158.55	151.65	164.04
C3—H41—C4	36.89	36.54	37.32
C3—H41—C5	74.64	74.12	75.3
C3—H41—H82^v	110.22	107.2	115.05
C3—H41—H102^iv	164.55	162.81	166.93
C4—H41—C5	37.75	37.51	38
C4—H41—H82^v	92.5	86.05	97.35
C4—H41—H102^iv	129.28	125.86	133.08
C5—H41—H82^v	73.5	63.78	82.84
C5—H41—H102^iv	91.91	88.31	96.11
H82^v—H41—H102^iv	58.99	56.81	61.22
Si1—H71—C7	47.96	47.81	48.11
Si1—H71—H72	70.59	70.45	70.7
Si1—H71—H73	70.59	70.45	70.7
Si1—H71—H91^ix	95.66	89.03	101.15
Si1—H71—H93^iv	140.86	134.15	148.68
C7—H71—H72	35.26	35.24	35.28
C7—H71—H73	35.26	35.24	35.29
C7—H71—H91^ix	142.45	135.72	148.44
C7—H71—H93^iv	114.22	106.06	121.17
H72—H71—H73	60	59.97	60.03
H72—H71—H91^ix	154.51	151.91	157.4
H72—H71—H93^iv	116.21	104	126.83
H73—H71—H91^ix	136.51	132.03	142.03
H73—H71—H93^iv	80.88	74.18	86.94
H91^ix—H71—H93^iv	87.77	76.34	103.79
Si1—H72—C7	47.96	47.81	48.11
Si1—H72—C9^x	133.04	119.81	150.52
Si1—H72—H71	70.59	70.46	70.72
Si1—H72—H73	70.59	70.46	70.72
Si1—H72—H91^x	123.96	113.85	137.26
Si1—H72—H92^x	120.97	106.12	142.37
Si1—H72—H93^x	148.61	132.9	167.74
Si1—H72—H103^iv	93.11	90.88	94.83
C7—H72—C9^x	148.23	136.48	162.11
C7—H72—H71	35.26	35.25	35.28
C7—H72—H73	35.26	35.25	35.28
C7—H72—H91^x	160.81	146.94	179.43
C7—H72—H92^x	133.46	121.62	149.64
C7—H72—H93^x	141.73	131.88	153.22
C7—H72—H103^iv	93.17	92.29	94.1
C9^x—H72—H71	114.69	103.43	127.89
C9^x—H72—H73	152.19	137.87	163.75
C9^x—H72—H91^x	17.83	17.27	18.9
C9^x—H72—H92^x	17.26	16.19	18.76
C9^x—H72—H93^x	17.45	16.45	18.8
C9^x—H72—H103^iv	114.81	94.43	130.39
H71—H72—H73	60	59.97	60.03
H71—H72—H91^x	130.52	118.44	144.44
H71—H72—H92^x	101.05	90.96	114.37
H71—H72—H93^x	109.61	96.63	123.64
H71—H72—H103^iv	122.49	121.5	124.3
H73—H72—H91^x	160.84	141.2	175.54
H73—H72—H92^x	151.93	145.03	160.8
H73—H72—H93^x	135.16	120.21	147.47
H73—H72—H103^iv	62.58	61.59	64.32
H91^x—H72—H92^x	29.53	27.15	32.06
H91^x—H72—H93^x	31.46	29.03	34.03
H91^x—H72—H103^iv	103.66	84.52	118.75
H92^x—H72—H93^x	29.38	26.61	32.12
H92^x—H72—H103^iv	131.46	111.41	145.46
H93^x—H72—H103^iv	108.97	85.17	128.3
Si1—H73—C7	47.96	47.81	48.11
Si1—H73—H71	70.59	70.47	70.72
Si1—H73—H72	70.59	70.47	70.72
Si1—H73—H93^iv	130.11	120.85	141.45
Si1—H73—H103^iv	102.21	98.84	104.44
C7—H73—H71	35.26	35.25	35.28
C7—H73—H72	35.26	35.25	35.28
C7—H73—H93^iv	100.35	95.42	106.51
C7—H73—H103^iv	115.54	113.76	116.72
H71—H73—H72	60	59.97	60.03
H71—H73—H93^iv	66.81	61.07	74.22
H71—H73—H103^iv	146.08	144.77	147.28
H72—H73—H93^iv	106.42	99.68	112.23
H72—H73—H103^iv	86.23	85.08	87.34
H93^iv—H73—H103^iv	127.29	118.24	135.46
Si1—H81—C8	47.91	47.8	48.05
Si1—H81—H82	70.55	70.45	70.68
Si1—H81—H83	70.55	70.45	70.66
Si1—H81—H91^ix	96.35	93.85	99.03
Si1—H81—H92^vi	151.78	146.94	158.38
C8—H81—H82	35.26	35.24	35.29
C8—H81—H83	35.27	35.24	35.29
C8—H81—H91^ix	142.84	140.51	146.37
C8—H81—H92^vi	129.79	127.41	133.21
H82—H81—H83	60	59.96	60.04
H82—H81—H91^ix	136.07	131.85	141.36
H82—H81—H92^vi	125.48	120.27	129.22
H83—H81—H91^ix	155.73	153.05	159.62
H83—H81—H92^vi	96.57	93.38	100.09
H91^ix—H81—H92^vi	85.59	79.09	89.75
Si1—H82—C4^iv	106.34	102.91	108.92
Si1—H82—C5^iv	109.11	106.84	111.1
Si1—H82—C8	47.91	47.78	48.04
Si1—H82—C10^xi	163.37	155.38	168.35
Si1—H82—H41^iv	117.83	111.05	123.98
Si1—H82—H81	70.55	70.43	70.67
Si1—H82—H83	70.55	70.43	70.66
Si1—H82—H102^xi	167.57	157.57	174.78
Si1—H82—H103^xi	154.72	141.1	168.96
C4^iv—H82—C5^iv	27.46	26.64	28.24
C4^iv—H82—C8	152.99	147.85	156.91
C4^iv—H82—C10^xi	86.18	84.34	88.83
C4^iv—H82—H41^iv	18.59	17.85	19.01
C4^iv—H82—H81	156.97	149.92	163.27
C4^iv—H82—H83	141.65	133.68	149.7
C4^iv—H82—H102^xi	75.19	71.44	78.11
C4^iv—H82—H103^xi	85.62	82.46	88.53
C5^iv—H82—C8	151.03	145.59	156.17
C5^iv—H82—C10^xi	79.83	76.73	82.12
C5^iv—H82—H41^iv	41.47	40.08	42.83
C5^iv—H82—H81	130.75	123.42	139.49
C5^iv—H82—H83	168.84	160.32	175.77
C5^iv—H82—H102^xi	76.51	75.09	77.61
C5^iv—H82—H103^xi	71.81	66.88	76.04
C8—H82—C10^xi	118.88	116.37	121.62
C8—H82—H41^iv	155.97	145.59	167.02
C8—H82—H81	35.26	35.24	35.29
C8—H82—H83	35.26	35.25	35.28
C8—H82—H102^xi	127.54	126.08	128.89
C8—H82—H103^xi	119.6	115.54	123.85
C10^xi—H82—H41^iv	75.41	72.87	79.35
C10^xi—H82—H81	95.44	87.06	104.78
C10^xi—H82—H83	101.72	96.65	107.52
C10^xi—H82—H102^xi	17.74	16.78	18.59
C10^xi—H82—H103^xi	17.42	15.91	18.42
H41^iv—H82—H81	168.53	157.68	178.23
H41^iv—H82—H83	128.34	119.76	137.66
H41^iv—H82—H102^xi	61.33	57.61	64.98
H41^iv—H82—H103^xi	79.87	76.77	84.22
H81—H82—H83	60	59.97	60.03
H81—H82—H102^xi	110.91	101.53	120.4
H81—H82—H103^xi	89.41	81.61	98.61
H83—H82—H102^xi	101.71	97.11	107.4
H83—H82—H103^xi	112.39	106.54	118.13
H102^xi—H82—H103^xi	32.81	31.27	34.24
Si1—H83—C8	47.91	47.79	48.06
Si1—H83—H81	70.55	70.43	70.67
Si1—H83—H82	70.55	70.44	70.67
Si1—H83—H101^vi	107.15	90.23	125.57
C8—H83—H81	35.27	35.24	35.29
C8—H83—H82	35.26	35.25	35.28
C8—H83—H101^vi	152.83	133.08	170.69
H81—H83—H82	60	59.96	60.04
H81—H83—H101^vi	153.14	140.76	160.85
H82—H83—H101^vi	140.33	122.12	154.25
Si1—H91—C9	47.93	47.78	48.16
Si1—H91—H71^ix	127.62	121.8	133.1
Si1—H91—H72^vii	137.41	133.76	140.27
Si1—H91—H81^ix	126.94	118.34	135.69
Si1—H91—H92	70.56	70.44	70.76
Si1—H91—H93	70.56	70.44	70.76
C9—H91—H71^ix	144.51	135.58	154.25
C9—H91—H72^vii	92.63	86.95	97.29
C9—H91—H81^ix	143.05	137.62	148.85
C9—H91—H92	35.26	35.26	35.27
C9—H91—H93	35.26	35.25	35.28
H71^ix—H91—H72^vii	87.51	77.18	94.7
H71^ix—H91—H81^ix	71.29	67.72	74.19
H71^ix—H91—H92	110.64	102.14	119.66
H71^ix—H91—H93	156.94	153.82	160.17
H72^vii—H91—H81^ix	76.24	64.74	89.07
H72^vii—H91—H92	81.31	64.95	95.1
H72^vii—H91—H93	70.97	67.25	77.62
H81^ix—H91—H92	157.24	151.65	161.97
H81^ix—H91—H93	109.45	105.86	113.94
H92—H91—H93	60	59.99	60.01
Si1—H92—C9	47.93	47.77	48.15
Si1—H92—H72^vii	130.72	114.46	152.43
Si1—H92—H81^xii	145.88	140.28	151.67
Si1—H92—H91	70.56	70.42	70.74
Si1—H92—H93	70.56	70.43	70.75
C9—H92—H72^vii	82.94	66.84	104.64
C9—H92—H81^xii	162.51	152.15	170.75
C9—H92—H91	35.26	35.25	35.28
C9—H92—H93	35.26	35.25	35.27
H72^vii—H92—H81^xii	81.17	66.79	89
H72^vii—H92—H91	69.15	57.48	84.83
H72^vii—H92—H93	65.74	50.75	86.92
H81^xii—H92—H91	138.8	136.52	142.51
H81^xii—H92—H93	130.8	118.08	143.25
H91—H92—H93	60	59.98	60.02
Si1—H93—C9	47.93	47.77	48.15
Si1—H93—H71^v	116.85	110.89	123.45
Si1—H93—H72^vii	143.94	131.15	151.46
Si1—H93—H73^v	99.78	97.95	102.01
Si1—H93—H91	70.56	70.43	70.75
Si1—H93—H92	70.56	70.43	70.75
C9—H93—H71^v	158.98	156.91	161.56
C9—H93—H72^vii	98.7	84.06	109.46
C9—H93—H73^v	128.71	125.46	130.73
C9—H93—H91	35.26	35.25	35.28
C9—H93—H92	35.26	35.26	35.27
H71^v—H93—H72^vii	96.25	86.84	109.03
H71^v—H93—H73^v	32.31	31.44	33.53
H71^v—H93—H91	162.93	159.8	166.12
H71^v—H93—H92	134.91	128.92	140.11
H72^vii—H93—H73^v	107.88	100.16	114.09
H72^vii—H93—H91	77.53	72.88	80.72
H72^vii—H93—H92	84.86	63.28	102.46
H73^v—H93—H91	163.45	159.25	165.92
H73^v—H93—H92	104.9	99.45	109.21
H91—H93—H92	60	59.98	60.02
S2—H101—C6^xii	123.84	117.58	130.19
S2—H101—C10	47.57	47.54	47.65
S2—H101—H83^xii	83.79	76.39	91.85
S2—H101—H102	70.26	70.22	70.31
S2—H101—H103	70.26	70.22	70.32
S2—H101—H111^ii	88.57	87.41	89.73
C6^xii—H101—C10	165.37	153.67	177.23
C6^xii—H101—H83^xii	55.65	39.62	69.62
C6^xii—H101—H102	135.99	125.94	147.61
C6^xii—H101—H103	158.73	143.99	170.78
C6^xii—H101—H111^ii	60.68	42.72	80.87
C10—H101—H83^xii	124.47	107.42	139.17
C10—H101—H102	35.26	35.25	35.27
C10—H101—H103	35.26	35.26	35.27
C10—H101—H111^ii	105.66	100.63	111.2
H83^xii—H101—H102	148.84	142.12	154.19
H83^xii—H101—H103	116.63	92.37	139.66
H83^xii—H101—H111^ii	93.34	64.57	122.66
H102—H101—H103	60	59.99	60.01
H102—H101—H111^ii	80.89	74.4	88
H103—H101—H111^ii	139.6	133.73	145.95
S1—H102—S2	76.36	74.63	77.84
S1—H102—C2	34.67	34.38	35.05
S1—H102—C3	57.78	57.45	58.05
S1—H102—C10	123.81	122.19	125.15
S1—H102—H41^v	70.73	68.97	71.9
S1—H102—H82^viii	129.02	123.26	133.22
S1—H102—H101	136.57	134.13	138.63
S1—H102—H103	131.35	131.19	131.54
S1—H102—H111^ii	79.36	78.59	80.23
S2—H102—C2	61.7	60.94	62.22
S2—H102—C3	37.4	37.09	37.86
S2—H102—C10	47.57	47.53	47.64
S2—H102—H41^v	127.11	121.19	132.5
S2—H102—H82^viii	140.99	130.58	152.41
S2—H102—H101	70.26	70.22	70.31
S2—H102—H103	70.26	70.22	70.32
S2—H102—H111^ii	85.32	82.05	88.66
C2—H102—C3	28.57	28.23	28.83
C2—H102—C10	101.21	101.09	101.4
C2—H102—H41^v	67.72	62.98	72.06
C2—H102—H82^viii	119.57	117.37	121.31
C2—H102—H101	131.65	131.05	132
C2—H102—H103	97.25	96.44	97.98
C2—H102—H111^ii	108.56	107.84	109.36
C3—H102—C10	72.66	72.52	72.88
C3—H102—H41^v	89.73	83.4	95.23
C3—H102—H82^viii	124.7	118.36	130.32
C3—H102—H101	104.25	104.04	104.59
C3—H102—H103	74.41	74.32	74.49
C3—H102—H111^ii	110.95	109.39	112.41
C10—H102—H41^v	137.12	134.1	139.66
C10—H102—H82^viii	99.31	89.67	110.36
C10—H102—H101	35.26	35.26	35.27
C10—H102—H103	35.26	35.26	35.27
C10—H102—H111^ii	96.81	92.38	101.19
H41^v—H102—H82^viii	59.69	57.86	61.65
H41^v—H102—H101	152.51	149.47	156.43
H41^v—H102—H103	103.02	100.52	104.99
H41^v—H102—H111^ii	125.87	119.94	132
H82^viii—H102—H101	93.85	88.11	100.82
H82^viii—H102—H103	71	60.56	82.61
H82^viii—H102—H111^ii	124.15	119.46	129.22
H101—H102—H103	60	60	60
H101—H102—H111^ii	71.09	67.09	74.97
H103—H102—H111^ii	130.1	125.81	134.31
S2—H103—C3	37.4	37.09	37.86
S2—H103—C10	47.57	47.53	47.64
S2—H103—H72^v	128.13	123.72	133.32
S2—H103—H73^v	97.74	94.37	102.33
S2—H103—H82^viii	146.15	134.94	157.87
S2—H103—H101	70.26	70.22	70.31
S2—H103—H102	70.26	70.22	70.32
C3—H103—C10	72.66	72.53	72.89
C3—H103—H72^v	113.84	109.31	119.21
C3—H103—H73^v	85.49	80.55	90.77
C3—H103—H82^viii	127.61	120.39	133.67
C3—H103—H101	104.25	104.04	104.6
C3—H103—H102	74.41	74.31	74.5
C10—H103—H72^v	162.64	159.87	165.47
C10—H103—H73^v	143.03	140.81	147.07
C10—H103—H82^viii	104.13	93.88	115.37
C10—H103—H101	35.26	35.26	35.27
C10—H103—H102	35.26	35.26	35.27
H72^v—H103—H73^v	31.19	29.95	32.89
H72^v—H103—H82^viii	84.46	74.91	92.25
H72^v—H103—H101	130.21	126.01	132.63
H72^v—H103—H102	159.23	155.11	162.08
H73^v—H103—H82^viii	112.71	102.93	119.25
H73^v—H103—H101	133.66	129.32	136.01
H73^v—H103—H102	158.74	153.78	164.17
H82^viii—H103—H101	96.68	90.91	103.59
H82^viii—H103—H102	76.2	64.95	88.13
H101—H103—H102	60	59.99	60.01
S2^v—H111—O1	143.35	136.93	148.77
S2^v—H111—O1^i	101.42	94.88	107.06
S2^v—H111—C1	120.49	118.33	121.87
S2^v—H111—C1^i	106.73	103.46	108.77
S2^v—H111—C5^v	60.44	57.79	62.73
S2^v—H111—C11	167.03	158.12	174.93
S2^v—H111—C11^i	123.4	114.65	131.45
S2^v—H111—H101^xiii	79.02	71.34	86.52
S2^v—H111—H102^xiii	77.42	71.31	82.61
S2^v—H111—H111^i	137.16	128.36	145.23
S2^v—H111—H112	145.98	144.23	147.4
S2^v—H111—H112^i	107.69	98.68	116.37
O1—H111—O1^i	76.72	76.42	76.93
O1—H111—C1	30.04	29.63	30.35
O1—H111—C1^i	55.99	55.8	56.27
O1—H111—C5^v	84.51	79.74	89.28
O1—H111—C11	43.48	43.33	43.58
O1—H111—C11^i	74.46	74.01	74.85
O1—H111—H101^xiii	108.1	97.69	116.47
O1—H111—H102^xiii	124.66	119.37	127.7
O1—H111—H111^i	63.75	63.37	64.09
O1—H111—H112	67.11	66.88	67.29
O1—H111—H112^i	97.43	96.89	97.92
O1^i—H111—C1	55.26	55.1	55.39
O1^i—H111—C1^i	27.85	27.75	27.99
O1^i—H111—C5^v	104.69	101.46	107.06
O1^i—H111—C11	68.06	67.8	68.24
O1^i—H111—C11^i	33.52	33.46	33.58
O1^i—H111—H101^xiii	164.88	148.53	179.6
O1^i—H111—H102^xiii	141.18	124.13	158.81
O1^i—H111—H111^i	43.07	42.92	43.17
O1^i—H111—H112	99.27	99.15	99.34
O1^i—H111—H112^i	47.12	47.06	47.18
C1—H111—C1^i	29.03	28.75	29.3
C1—H111—C5^v	73.52	71.74	75.21
C1—H111—C11	60.22	59.49	60.78
C1—H111—C11^i	69.09	68.77	69.26
C1—H111—H101^xiii	132.47	116.41	145.86
C1—H111—H102^xiii	152.96	144.81	157.7
C1—H111—H111^i	64.7	64.25	65.03
C1—H111—H112	92.78	92.32	93.09
C1—H111—H112^i	92.97	92.69	93.17
C1^i—H111—C5^v	83.68	82.06	84.71
C1^i—H111—C11	67.61	67	68.34
C1^i—H111—C11^i	52.61	52.38	52.85
C1^i—H111—H101^xiii	159.31	142.84	170.96
C1^i—H111—H102^xiii	165.51	150.53	178.18
C1^i—H111—H111^i	55.35	54.93	55.74
C1^i—H111—H112	103.82	103.51	104.24
C1^i—H111—H112^i	72.58	72.41	72.79
C5^v—H111—C11	127.92	123.29	132.39
C5^v—H111—C11^i	135.99	133.96	137.23
C5^v—H111—H101^xiii	85.14	63.62	107.01
C5^v—H111—H102^xiii	107.86	90.08	124.96
C5^v—H111—H111^i	137.09	135.89	138.19
C5^v—H111—H112	137.2	131.38	143.61
C5^v—H111—H112^i	149.21	144.24	153.06
C11—H111—C11^i	43.88	43.85	43.9
C11—H111—H101^xiii	108.31	100.57	114.07
C11—H111—H102^xiii	104.65	95.35	113.31
C11—H111—H111^i	30.08	30.05	30.11
C11—H111—H112	36.24	35.89	36.55
C11—H111—H112^i	59.96	59.75	60.22
C11^i—H111—H101^xiii	136.92	118.88	153.37
C11^i—H111—H102^xiii	115.24	98.27	132.72
C11^i—H111—H111^i	13.8	13.79	13.8
C11^i—H111—H112	67.43	67.34	67.55
C11^i—H111—H112^i	24.32	24.25	24.39
H101^xiii—H111—H102^xiii	28.01	24.88	30.64
H101^xiii—H111—H111^i	129.19	114.26	141.79
H101^xiii—H111—H112	75.32	64.69	85.94
H101^xiii—H111—H112^i	122.03	101.58	142.65
H102^xiii—H111—H111^i	113.16	97.71	128.7
H102^xiii—H111—H112	69.45	62.45	77.21
H102^xiii—H111—H112^i	95.44	77.99	113.68
H111^i—H111—H112	56.22	56.05	56.39
H111^i—H111—H112^i	33.71	33.54	33.87
H112—H111—H112^i	69.15	68.98	69.41
S1^xiii—H112—S2^xiii	64.86	58.98	68.52
S1^xiii—H112—O1	164.36	149.24	177.41
S1^xiii—H112—C11	126.37	116.09	135.86
S1^xiii—H112—C11^i	92.27	77.01	108.73
S1^xiii—H112—H111	110.49	108.82	111.72
S1^xiii—H112—H111^i	92.42	75.36	111
S1^xiii—H112—H112^i	68.78	54.8	84.24
S2^xiii—H112—O1	127.26	107.64	146.11
S2^xiii—H112—C11	153.33	135.65	167.95
S2^xiii—H112—C11^i	156.62	135.35	175.44
S2^xiii—H112—H111	121.5	109.58	133.03
S2^xiii—H112—H111^i	143.86	124.42	159.66
S2^xiii—H112—H112^i	133.23	113.68	151.67
O1—H112—C11	43.48	43.33	43.58
O1—H112—C11^i	74.46	74	74.85
O1—H112—H111	67.11	66.87	67.28
O1—H112—H111^i	74.25	74	74.48
O1—H112—H112^i	98.56	98.1	98.88
C11—H112—C11^i	43.88	43.85	43.91
C11—H112—H111	36.24	35.89	36.55
C11—H112—H111^i	59.96	59.75	60.23
C11—H112—H112^i	61.83	61.78	61.88
C11^i—H112—H111	67.43	67.33	67.55
C11^i—H112—H111^i	24.32	24.24	24.39
C11^i—H112—H112^i	24.8	24.77	24.83
H111—H112—H111^i	90.07	90.05	90.09
H111—H112—H112^i	71.55	71.42	71.65
H111^i—H112—H112^i	39.3	39.14	39.43

Symmetry codes: (i) −x₁, x₂, −x₃+1/2, x₄+1/2; (ii) x₁, x₂−1, x₃, x₄; (iii) −x₁, x₂−1, −x₃+1/2, x₄+1/2; (iv) x₁, −x₂+1, x₃−1/2, −x₄+1/2; (v) x₁, −x₂+1, x₃+1/2, −x₄+1/2; (vi) x₁, −x₂, x₃−1/2, −x₄+1/2; (vii) −x₁−1/2, x₂−1/2, −x₃−1/2, x₄+1/2; (viii) x₁, x₂, x₃+1, x₄; (ix) −x₁−1/2, −x₂+1/2, −x₃−1, −x₄; (x) −x₁−1/2, x₂+1/2, −x₃−1/2, x₄+1/2; (xi) x₁, x₂, x₃−1, x₄; (xii) x₁, −x₂, x₃+1/2, −x₄+1/2; (xiii) x₁, x₂+1, x₃, x₄.

(ESEMOX)

Crystal data

C22H30O8S3Si2	Z = 4
Mr = 574.8	F(000) = 1208
Triclinic, P1	Dx = 1.336 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.5399 (4) Å	Cell parameters from 9905 reflections
b = 13.8276 (5) Å	θ = 2.4–30.0°
c = 19.9987 (8) Å	µ = 0.39 mm^−1
α = 79.940 (2)°	T = 100 K
β = 84.589 (2)°	Block, clear yellow
γ = 89.771 (2)°	0.63 × 0.45 × 0.28 mm
V = 2856.81 (19) Å^3

Data collection

Bruker KAPPA APEX II CCD diffractometer	13689 independent reflections
Radiation source: X-ray tube	11291 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.035
ω– and φ–scans	θmax = 30.1°, θmin = 1.0°
Absorption correction: multi-scan TWINABS	h = −14→14
Tmin = 0.81, Tmax = 0.90	k = −19→19
57022 measured reflections	l = −28→28

Refinement

Refinement on F	240 constraints
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.042	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 1.96	(Δ/σ)max = 0.017
13689 reflections	Δρmax = 0.45 e Å^−3
632 parameters	Δρmin = −0.60 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
S1	0.77446 (6)	0.50526 (5)	0.50468 (3)	0.00908 (17)
S2	0.72955 (6)	0.28490 (5)	0.68127 (3)	0.01225 (18)
S3	0.70884 (6)	0.45411 (5)	0.31639 (3)	0.01340 (19)
Si1	0.73015 (8)	0.46365 (6)	0.88964 (4)	0.0215 (2)
Si2	0.77675 (7)	0.78808 (5)	0.13862 (4)	0.0174 (2)
O1	0.63794 (16)	0.50577 (13)	0.50937 (9)	0.0139 (5)
O2	0.83646 (17)	0.59553 (12)	0.51035 (9)	0.0136 (5)
O3	0.69837 (18)	0.22703 (13)	0.63194 (9)	0.0190 (6)
O4	0.63009 (18)	0.30754 (14)	0.73025 (9)	0.0208 (6)
O5	0.68168 (19)	0.35776 (13)	0.35553 (9)	0.0181 (6)
O6	0.7624 (2)	0.46391 (13)	0.24688 (8)	0.0225 (6)
O7	0.94381 (17)	0.26061 (13)	0.55024 (9)	0.0133 (5)
O8	0.94873 (17)	0.32328 (13)	0.40531 (8)	0.0134 (5)
C1	0.8278 (2)	0.40505 (17)	0.56135 (11)	0.0096 (7)
C2	0.8891 (2)	0.34330 (18)	0.52422 (12)	0.0104 (7)
C3	0.8917 (2)	0.37629 (18)	0.44905 (11)	0.0099 (7)
C4	0.8360 (2)	0.46291 (17)	0.43038 (11)	0.0101 (7)
C5	0.7977 (2)	0.39934 (18)	0.63469 (12)	0.0107 (7)
C6	0.8094 (3)	0.4775 (2)	0.66580 (12)	0.0158 (8)
C7	0.7792 (3)	0.47980 (19)	0.73616 (13)	0.0174 (8)
C8	0.7581 (3)	0.4822 (2)	0.79588 (13)	0.0216 (8)
C9	0.6975 (3)	0.5826 (2)	0.91799 (14)	0.0308 (10)
C10	0.8774 (3)	0.4057 (2)	0.92168 (14)	0.0353 (11)
C11	0.5893 (3)	0.3807 (3)	0.91452 (16)	0.0477 (13)
C12	0.8555 (3)	0.22896 (19)	0.72503 (13)	0.0185 (8)
C13	0.8121 (2)	0.51567 (19)	0.36293 (12)	0.0120 (7)
C14	0.8550 (3)	0.60775 (19)	0.33840 (12)	0.0159 (8)
C16	0.8149 (3)	0.7163 (2)	0.22126 (14)	0.0203 (8)
C17	0.7621 (3)	0.6986 (2)	0.08047 (13)	0.0318 (10)
C18	0.6251 (3)	0.8519 (2)	0.15529 (15)	0.0347 (11)
C19	0.9085 (3)	0.8763 (2)	0.10448 (14)	0.0306 (10)
C20	0.5678 (3)	0.5227 (2)	0.31944 (16)	0.0240 (10)
C21	1.0181 (2)	0.20990 (18)	0.50112 (12)	0.0126 (8)
C22	0.9577 (2)	0.22063 (18)	0.43555 (12)	0.0134 (8)
S1'	0.27679 (6)	−0.00255 (5)	0.49149 (3)	0.00893 (17)
S2'	0.28833 (6)	0.21795 (5)	0.31683 (3)	0.01156 (18)
S3'	0.14566 (6)	0.04680 (5)	0.68106 (3)	0.01244 (18)
Si1'	0.30584 (7)	0.03475 (6)	0.11211 (4)	0.0203 (2)
Si2'	0.19676 (7)	−0.27944 (5)	0.86443 (4)	0.0167 (2)
O1'	0.14226 (16)	−0.00283 (13)	0.48582 (9)	0.0136 (5)
O2'	0.34163 (17)	−0.09336 (12)	0.48609 (8)	0.0132 (5)
O3'	0.24510 (19)	0.27617 (13)	0.36705 (9)	0.0186 (6)
O4'	0.19992 (19)	0.19658 (13)	0.27087 (9)	0.0215 (6)
O5'	0.12938 (18)	0.14279 (13)	0.64233 (9)	0.0173 (6)
O6'	0.17568 (19)	0.03684 (14)	0.75025 (9)	0.0216 (6)
O7'	0.46459 (17)	0.24060 (13)	0.44665 (9)	0.0123 (5)
O8'	0.41642 (17)	0.17646 (13)	0.59155 (8)	0.0121 (5)
C1'	0.3515 (2)	0.09766 (17)	0.43512 (11)	0.0102 (7)
C2'	0.3993 (2)	0.15833 (17)	0.47250 (12)	0.0090 (7)
C3'	0.3739 (2)	0.12513 (17)	0.54768 (11)	0.0095 (7)
C4'	0.3107 (2)	0.03982 (18)	0.56544 (11)	0.0104 (7)
C5'	0.3440 (2)	0.10389 (19)	0.36218 (12)	0.0112 (7)
C6'	0.3662 (3)	0.0254 (2)	0.33070 (13)	0.0139 (8)
C8'	0.3400 (3)	0.01869 (19)	0.20214 (13)	0.0184 (8)
C9'	0.2865 (3)	−0.0869 (2)	0.08727 (14)	0.0324 (10)
C10'	0.4417 (3)	0.1055 (2)	0.06023 (14)	0.0364 (11)
C11'	0.1554 (3)	0.1050 (2)	0.10728 (16)	0.0371 (11)
C12'	0.4254 (3)	0.2734 (2)	0.26954 (13)	0.0213 (9)
C13'	0.2651 (2)	−0.01347 (18)	0.63340 (12)	0.0109 (7)
C14'	0.3040 (3)	−0.10497 (19)	0.65748 (12)	0.0145 (8)
C15'	0.2663 (3)	−0.16141 (19)	0.72263 (13)	0.0167 (8)
C16'	0.2406 (3)	−0.21094 (19)	0.77773 (13)	0.0181 (8)
C17'	0.1849 (3)	−0.1861 (2)	0.92211 (13)	0.0292 (10)
C18'	0.0430 (3)	−0.3425 (2)	0.86290 (14)	0.0296 (10)
C19'	0.3258 (3)	−0.3678 (2)	0.88686 (13)	0.0271 (9)
C20'	0.0072 (3)	−0.0226 (2)	0.67931 (15)	0.0235 (10)
C21'	0.5206 (2)	0.29058 (18)	0.49552 (11)	0.0115 (8)
C22'	0.4373 (2)	0.27986 (18)	0.56154 (13)	0.0137 (8)
C7'	0.3514 (3)	0.02275 (19)	0.26087 (13)	0.0169 (8)
C15	0.8318 (3)	0.66538 (19)	0.27472 (13)	0.0177 (8)
H61	0.841285	0.537395	0.637558	0.0189*
H121	0.926349	0.220674	0.692785	0.0222*
H122	0.880999	0.269743	0.755765	0.0222*
H123	0.827683	0.165972	0.750415	0.0222*
H141	0.906227	0.637434	0.366711	0.019*
H201	0.534594	0.520181	0.366104	0.0288*
H202	0.586028	0.589768	0.298533	0.0288*
H203	0.505954	0.495661	0.295344	0.0288*
H211	1.023673	0.141481	0.520172	0.0151*
H212	1.103068	0.236833	0.492465	0.0151*
H221	1.007512	0.186769	0.404393	0.016*
H222	0.873963	0.191396	0.443939	0.016*
H61'	0.394411	−0.033582	0.35779	0.0167*
H121'	0.463513	0.229615	0.241257	0.0256*
H122'	0.402895	0.333308	0.241373	0.0256*
H123'	0.485085	0.287515	0.300081	0.0256*
H141'	0.36283	−0.134707	0.627706	0.0174*
H201'	−0.0173	−0.013174	0.6336	0.0282*
H202'	0.023536	−0.09093	0.694391	0.0282*
H203'	−0.060429	−0.001739	0.708979	0.0282*
H211'	0.532612	0.359005	0.476564	0.0138*
H212'	0.602894	0.263686	0.503921	0.0138*
H221'	0.476744	0.312748	0.592833	0.0165*
H222'	0.356767	0.310281	0.553566	0.0165*
H91	0.676202	0.571441	0.966485	0.037*
H92	0.771835	0.62422	0.906554	0.037*
H93	0.627525	0.613724	0.895642	0.037*
H101	0.879333	0.410797	0.968831	0.0424*
H102	0.877985	0.337667	0.917178	0.0424*
H103	0.950736	0.438592	0.895583	0.0424*
H111	0.575696	0.364792	0.963355	0.0572*
H112	0.515403	0.412816	0.896921	0.0572*
H113	0.603799	0.321493	0.896143	0.0572*
H171	0.724472	0.729983	0.040514	0.0382*
H172	0.845087	0.675226	0.067404	0.0382*
H173	0.709163	0.644199	0.103419	0.0382*
H181	0.593011	0.879047	0.112733	0.0416*
H182	0.563911	0.805922	0.18177	0.0416*
H183	0.639853	0.903725	0.180012	0.0416*
H191	0.890664	0.912029	0.060798	0.0367*
H192	0.91644	0.921436	0.135342	0.0367*
H193	0.986682	0.8413	0.099588	0.0367*
H91'	0.264627	−0.078175	0.041095	0.0389*
H92'	0.364978	−0.122158	0.090774	0.0389*
H93'	0.219983	−0.123507	0.117068	0.0389*
H101'	0.426218	0.116377	0.01297	0.0437*
H102'	0.450149	0.167507	0.07479	0.0437*
H103'	0.518702	0.069011	0.066156	0.0437*
H111'	0.126984	0.108764	0.062697	0.0445*
H112'	0.091431	0.072418	0.140939	0.0445*
H113'	0.170095	0.170079	0.115716	0.0445*
H171'	0.167002	−0.21871	0.968521	0.035*
H172'	0.264118	−0.150412	0.91741	0.035*
H173'	0.117599	−0.141383	0.909996	0.035*
H181'	0.011375	−0.371645	0.90854	0.0355*
H182'	−0.017356	−0.295848	0.843937	0.0355*
H183'	0.055108	−0.392828	0.835427	0.0355*
H191'	0.30482	−0.404461	0.931921	0.0325*
H192'	0.33473	−0.412095	0.854745	0.0325*
H193'	0.404552	−0.33255	0.885491	0.0325*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0082 (3)	0.0069 (3)	0.0123 (3)	0.0004 (3)	−0.0026 (2)	−0.0011 (2)
S2	0.0105 (3)	0.0123 (3)	0.0131 (3)	−0.0007 (3)	−0.0001 (3)	−0.0004 (2)
S3	0.0142 (3)	0.0129 (3)	0.0141 (3)	−0.0003 (3)	−0.0040 (3)	−0.0037 (2)
Si1	0.0241 (4)	0.0273 (4)	0.0132 (3)	−0.0038 (4)	0.0017 (3)	−0.0055 (3)
Si2	0.0196 (4)	0.0175 (3)	0.0143 (3)	−0.0006 (3)	−0.0055 (3)	0.0017 (3)
O1	0.0041 (8)	0.0140 (9)	0.0240 (9)	0.0020 (8)	−0.0034 (8)	−0.0031 (7)
O2	0.0133 (10)	0.0071 (8)	0.0204 (9)	−0.0018 (8)	−0.0025 (8)	−0.0016 (7)
O3	0.0216 (11)	0.0170 (10)	0.0182 (9)	−0.0098 (9)	−0.0031 (8)	−0.0020 (8)
O4	0.0146 (10)	0.0205 (10)	0.0245 (10)	−0.0014 (8)	0.0068 (8)	−0.0010 (8)
O5	0.0228 (11)	0.0120 (9)	0.0196 (9)	−0.0031 (8)	−0.0046 (8)	−0.0015 (7)
O6	0.0341 (12)	0.0215 (10)	0.0126 (9)	−0.0048 (10)	−0.0009 (9)	−0.0057 (8)
O7	0.0140 (10)	0.0107 (9)	0.0147 (9)	0.0063 (7)	−0.0014 (7)	−0.0011 (7)
O8	0.0165 (10)	0.0097 (9)	0.0139 (8)	0.0019 (7)	−0.0010 (7)	−0.0025 (7)
C1	0.0078 (12)	0.0091 (12)	0.0114 (11)	0.0002 (10)	−0.0008 (9)	−0.0008 (9)
C2	0.0071 (12)	0.0107 (12)	0.0131 (11)	−0.0021 (11)	−0.0013 (10)	−0.0009 (10)
C3	0.0066 (12)	0.0123 (12)	0.0107 (11)	−0.0018 (10)	0.0010 (9)	−0.0025 (9)
C4	0.0095 (12)	0.0099 (12)	0.0111 (11)	−0.0010 (10)	−0.0024 (10)	−0.0016 (9)
C5	0.0081 (13)	0.0110 (12)	0.0123 (11)	0.0013 (10)	−0.0002 (10)	−0.0004 (10)
C6	0.0187 (15)	0.0156 (14)	0.0119 (12)	0.0018 (12)	−0.0011 (11)	0.0003 (10)
C7	0.0212 (15)	0.0123 (12)	0.0191 (12)	−0.0006 (11)	−0.0018 (11)	−0.0034 (10)
C8	0.0268 (16)	0.0190 (14)	0.0198 (13)	0.0000 (12)	−0.0025 (12)	−0.0058 (11)
C9	0.0236 (17)	0.0444 (18)	0.0283 (14)	−0.0001 (14)	−0.0011 (13)	−0.0175 (13)
C10	0.043 (2)	0.0359 (17)	0.0242 (14)	0.0092 (16)	−0.0048 (14)	0.0036 (13)
C11	0.048 (2)	0.057 (2)	0.0379 (18)	−0.022 (2)	0.0061 (17)	−0.0127 (17)
C12	0.0165 (14)	0.0170 (13)	0.0201 (13)	0.0006 (12)	−0.0039 (11)	0.0032 (11)
C13	0.0090 (13)	0.0146 (13)	0.0116 (11)	−0.0010 (11)	−0.0011 (10)	−0.0002 (10)
C14	0.0145 (14)	0.0181 (14)	0.0152 (12)	−0.0020 (11)	−0.0058 (11)	−0.0011 (11)
C16	0.0185 (15)	0.0179 (14)	0.0231 (13)	−0.0019 (11)	−0.0037 (11)	0.0013 (11)
C17	0.0358 (19)	0.0321 (16)	0.0303 (15)	−0.0038 (14)	−0.0126 (14)	−0.0079 (13)
C18	0.0338 (18)	0.0419 (19)	0.0302 (16)	0.0131 (15)	−0.0118 (14)	−0.0068 (14)
C19	0.040 (2)	0.0295 (16)	0.0210 (13)	−0.0088 (15)	0.0023 (13)	−0.0031 (12)
C20	0.0155 (16)	0.0200 (16)	0.0405 (18)	0.0039 (13)	−0.0129 (14)	−0.0112 (14)
C21	0.0103 (14)	0.0078 (12)	0.0195 (13)	0.0002 (10)	0.0012 (10)	−0.0037 (10)
C22	0.0142 (14)	0.0088 (13)	0.0175 (12)	0.0000 (10)	−0.0008 (10)	−0.0036 (10)
S1'	0.0083 (3)	0.0072 (3)	0.0114 (3)	−0.0013 (3)	−0.0017 (2)	−0.0015 (2)
S2'	0.0110 (3)	0.0109 (3)	0.0123 (3)	0.0004 (3)	−0.0018 (2)	−0.0003 (2)
S3'	0.0135 (3)	0.0121 (3)	0.0119 (3)	−0.0001 (3)	0.0004 (3)	−0.0035 (2)
Si1'	0.0197 (4)	0.0289 (4)	0.0131 (3)	0.0019 (3)	−0.0031 (3)	−0.0052 (3)
Si2'	0.0176 (4)	0.0172 (4)	0.0135 (3)	−0.0007 (3)	0.0002 (3)	0.0013 (3)
O1'	0.0078 (9)	0.0107 (9)	0.0225 (9)	−0.0030 (8)	0.0002 (7)	−0.0043 (7)
O2'	0.0152 (10)	0.0076 (8)	0.0167 (8)	0.0003 (8)	−0.0002 (8)	−0.0028 (7)
O3'	0.0215 (11)	0.0159 (10)	0.0183 (9)	0.0072 (9)	−0.0011 (8)	−0.0038 (8)
O4'	0.0227 (11)	0.0187 (10)	0.0252 (10)	0.0003 (9)	−0.0143 (9)	−0.0031 (8)
O5'	0.0175 (10)	0.0154 (10)	0.0186 (9)	0.0053 (8)	−0.0021 (8)	−0.0018 (8)
O6'	0.0308 (12)	0.0210 (10)	0.0139 (9)	0.0016 (9)	−0.0019 (9)	−0.0055 (8)
O7'	0.0144 (10)	0.0076 (9)	0.0144 (8)	−0.0061 (7)	−0.0014 (7)	−0.0005 (7)
O8'	0.0137 (9)	0.0106 (9)	0.0130 (8)	−0.0024 (7)	−0.0035 (7)	−0.0031 (7)
C1'	0.0087 (12)	0.0087 (12)	0.0120 (11)	0.0005 (10)	0.0000 (9)	0.0011 (9)
C2'	0.0070 (12)	0.0051 (11)	0.0139 (11)	−0.0006 (10)	0.0000 (10)	0.0005 (9)
C3'	0.0086 (12)	0.0073 (12)	0.0130 (11)	0.0010 (10)	−0.0009 (10)	−0.0033 (9)
C4'	0.0109 (13)	0.0116 (12)	0.0096 (10)	0.0006 (10)	−0.0016 (9)	−0.0040 (9)
C5'	0.0083 (13)	0.0124 (12)	0.0121 (11)	−0.0022 (10)	−0.0003 (10)	−0.0005 (10)
C6'	0.0141 (14)	0.0131 (13)	0.0153 (12)	−0.0019 (11)	−0.0031 (11)	−0.0037 (11)
C8'	0.0184 (14)	0.0195 (14)	0.0179 (12)	0.0007 (11)	−0.0023 (11)	−0.0046 (11)
C9'	0.0312 (18)	0.0427 (18)	0.0288 (15)	0.0016 (15)	−0.0054 (14)	−0.0198 (13)
C10'	0.0320 (18)	0.048 (2)	0.0264 (15)	−0.0043 (16)	0.0001 (14)	−0.0016 (14)
C11'	0.0339 (19)	0.0437 (19)	0.0346 (17)	0.0162 (16)	−0.0095 (15)	−0.0063 (15)
C12'	0.0174 (15)	0.0194 (14)	0.0226 (14)	−0.0034 (12)	0.0044 (11)	0.0058 (11)
C13'	0.0092 (12)	0.0115 (12)	0.0122 (11)	−0.0038 (11)	−0.0011 (10)	−0.0029 (10)
C14'	0.0131 (14)	0.0147 (13)	0.0148 (12)	−0.0006 (11)	−0.0003 (10)	−0.0010 (10)
C15'	0.0149 (14)	0.0159 (13)	0.0188 (12)	0.0038 (11)	−0.0020 (11)	−0.0016 (10)
C16'	0.0189 (14)	0.0163 (13)	0.0186 (12)	0.0047 (11)	−0.0031 (11)	−0.0013 (10)
C17'	0.0358 (19)	0.0260 (15)	0.0252 (14)	0.0029 (14)	0.0013 (13)	−0.0052 (12)
C18'	0.0283 (17)	0.0285 (16)	0.0302 (15)	−0.0098 (14)	0.0054 (13)	−0.0043 (13)
C19'	0.0341 (18)	0.0287 (15)	0.0166 (12)	0.0083 (14)	−0.0052 (13)	0.0025 (11)
C20'	0.0135 (16)	0.0235 (17)	0.0342 (17)	−0.0015 (13)	0.0042 (13)	−0.0105 (14)
C21'	0.0097 (13)	0.0095 (13)	0.0163 (12)	−0.0043 (10)	−0.0031 (10)	−0.0032 (10)
C22'	0.0145 (14)	0.0067 (12)	0.0211 (13)	0.0001 (10)	−0.0046 (11)	−0.0042 (10)
C7'	0.0165 (14)	0.0141 (13)	0.0210 (13)	−0.0011 (11)	−0.0004 (11)	−0.0060 (11)
C15	0.0190 (15)	0.0119 (13)	0.0224 (13)	−0.0039 (11)	−0.0074 (12)	−0.0002 (11)

Geometric parameters (Å, º)

S1—O1	1.4333 (19)	S1'—O1'	1.433 (2)
S1—O2	1.438 (2)	S1'—O2'	1.443 (2)
S1—C1	1.757 (2)	S1'—C1'	1.763 (2)
S1—C4	1.758 (3)	S1'—C4'	1.750 (3)
S2—O3	1.435 (2)	S2'—O3'	1.434 (2)
S2—O4	1.438 (2)	S2'—O4'	1.435 (2)
S2—C12	1.761 (3)	S2'—C12'	1.752 (3)
S3—O5	1.4374 (18)	S3'—O5'	1.4335 (19)
S3—O6	1.4341 (19)	S3'—O6'	1.432 (2)
S3—C20	1.762 (3)	S3'—C20'	1.757 (3)
Si1—C8	1.843 (3)	Si1'—C8'	1.845 (3)
Si1—C9	1.852 (4)	Si1'—C9'	1.853 (4)
Si1—C10	1.860 (4)	Si1'—C10'	1.860 (3)
Si1—C11	1.856 (4)	Si1'—C11'	1.857 (4)
Si2—C16	1.851 (3)	Si2'—C16'	1.843 (3)
Si2—C17	1.857 (3)	Si2'—C17'	1.872 (3)
Si2—C18	1.853 (4)	Si2'—C18'	1.849 (3)
Si2—C19	1.851 (3)	Si2'—C19'	1.859 (3)
O7—C2	1.324 (3)	O7'—C2'	1.330 (3)
O7—C21	1.470 (3)	O7'—C21'	1.459 (3)
O8—C3	1.336 (3)	O8'—C3'	1.330 (3)
O8—C22	1.449 (3)	O8'—C22'	1.460 (3)
C1—C2	1.351 (4)	C1'—C2'	1.345 (4)
C1—C5	1.460 (3)	C1'—C5'	1.456 (4)
C2—C3	1.490 (3)	C2'—C3'	1.492 (3)
C3—C4	1.341 (4)	C3'—C4'	1.333 (4)
C4—C13	1.461 (3)	C4'—C13'	1.467 (3)
C5—C6	1.349 (4)	C5'—C6'	1.356 (4)
C6—C7	1.419 (4)	C6'—C7'	1.426 (4)
C6—H61	0.96	C6'—H61'	0.96
C7—C8	1.200 (4)	C8'—C7'	1.203 (4)
C9—H91	0.96	C9'—H91'	0.96
C9—H92	0.96	C9'—H92'	0.96
C9—H93	0.96	C9'—H93'	0.96
C10—H101	0.96	C10'—H101'	0.96
C10—H102	0.96	C10'—H102'	0.96
C10—H103	0.96	C10'—H103'	0.96
C11—H111	0.96	C11'—H111'	0.96
C11—H112	0.96	C11'—H112'	0.96
C11—H113	0.96	C11'—H113'	0.96
C12—H121	0.96	C12'—H121'	0.96
C12—H122	0.96	C12'—H122'	0.96
C12—H123	0.96	C12'—H123'	0.96
C13—C14	1.345 (4)	C13'—C14'	1.350 (4)
C14—C15	1.421 (4)	C14'—C15'	1.419 (3)
C14—H141	0.96	C14'—H141'	0.96
C16—C15	1.201 (4)	C15'—C16'	1.199 (3)
C17—H171	0.96	C17'—H171'	0.96
C17—H172	0.96	C17'—H172'	0.96
C17—H173	0.96	C17'—H173'	0.96
C18—H181	0.96	C18'—H181'	0.96
C18—H182	0.96	C18'—H182'	0.96
C18—H183	0.96	C18'—H183'	0.96
C19—H191	0.96	C19'—H191'	0.96
C19—H192	0.96	C19'—H192'	0.96
C19—H193	0.96	C19'—H193'	0.96
C20—H201	0.96	C20'—H201'	0.96
C20—H202	0.96	C20'—H202'	0.96
C20—H203	0.96	C20'—H203'	0.96
C21—C22	1.495 (4)	C21'—C22'	1.500 (4)
C21—H211	0.96	C21'—H211'	0.96
C21—H212	0.96	C21'—H212'	0.96
C22—H221	0.96	C22'—H221'	0.96
C22—H222	0.96	C22'—H222'	0.96
O1—S1—O2	116.42 (12)	O1'—S1'—C1'	110.53 (12)
O1—S1—C1	110.31 (12)	O1'—S1'—C4'	110.90 (13)
O1—S1—C4	110.39 (13)	O2'—S1'—C1'	111.69 (12)
O2—S1—C1	111.83 (12)	O2'—S1'—C4'	110.76 (12)
O2—S1—C4	110.71 (12)	C1'—S1'—C4'	94.75 (12)
C1—S1—C4	95.17 (12)	O3'—S2'—O4'	118.08 (13)
O3—S2—O4	118.76 (13)	O3'—S2'—C12'	108.80 (14)
O3—S2—C12	109.02 (13)	O4'—S2'—C12'	109.15 (13)
O4—S2—C12	108.88 (13)	O5'—S3'—O6'	119.58 (12)
O5—S3—O6	119.41 (12)	O5'—S3'—C20'	107.93 (14)
O5—S3—C20	107.94 (13)	O6'—S3'—C20'	108.57 (14)
O6—S3—C20	109.03 (14)	C8'—Si1'—C9'	109.81 (13)
C8—Si1—C9	110.18 (13)	C8'—Si1'—C10'	107.19 (14)
C8—Si1—C10	105.49 (14)	C8'—Si1'—C11'	105.60 (15)
C8—Si1—C11	106.89 (16)	C9'—Si1'—C10'	111.42 (16)
C9—Si1—C10	112.38 (16)	C9'—Si1'—C11'	111.00 (17)
C9—Si1—C11	109.87 (17)	C10'—Si1'—C11'	111.58 (15)
C10—Si1—C11	111.81 (16)	C16'—Si2'—C17'	106.21 (13)
C16—Si2—C17	106.58 (14)	C16'—Si2'—C18'	107.20 (14)
C16—Si2—C18	106.93 (14)	C16'—Si2'—C19'	108.07 (13)
C16—Si2—C19	109.15 (14)	C17'—Si2'—C18'	112.52 (15)
C17—Si2—C18	112.31 (17)	C17'—Si2'—C19'	110.59 (15)
C17—Si2—C19	110.09 (14)	C18'—Si2'—C19'	111.93 (14)
C18—Si2—C19	111.56 (15)	C2'—O7'—C21'	116.25 (19)
C2—O7—C21	116.02 (19)	C3'—O8'—C22'	112.02 (19)
C3—O8—C22	112.17 (19)	S1'—C1'—C2'	108.18 (18)
S1—C1—C2	108.17 (18)	S1'—C1'—C5'	118.7 (2)
S1—C1—C5	119.7 (2)	C2'—C1'—C5'	133.0 (2)
C2—C1—C5	132.1 (2)	O7'—C2'—C1'	124.6 (2)
O7—C2—C1	124.7 (2)	O7'—C2'—C3'	121.4 (2)
O7—C2—C3	121.3 (2)	C1'—C2'—C3'	113.9 (2)
C1—C2—C3	113.9 (2)	O8'—C3'—C2'	121.2 (2)
O8—C3—C2	121.3 (2)	O8'—C3'—C4'	124.5 (2)
O8—C3—C4	124.2 (2)	C2'—C3'—C4'	114.2 (2)
C2—C3—C4	114.5 (2)	S1'—C4'—C3'	108.92 (18)
S1—C4—C3	108.19 (18)	S1'—C4'—C13'	121.3 (2)
S1—C4—C13	120.9 (2)	C3'—C4'—C13'	129.7 (3)
C3—C4—C13	130.7 (2)	C1'—C5'—C6'	122.0 (2)
C1—C5—C6	122.3 (2)	C5'—C6'—C7'	125.8 (3)
C5—C6—C7	126.4 (2)	C5'—C6'—H61'	117.1
C5—C6—H61	116.79	C7'—C6'—H61'	117.11
C7—C6—H61	116.79	Si1'—C8'—C7'	169.0 (3)
C6—C7—C8	177.7 (3)	Si1'—C9'—H91'	109.47
Si1—C8—C7	170.4 (3)	Si1'—C9'—H92'	109.47
Si1—C9—H91	109.47	Si1'—C9'—H93'	109.47
Si1—C9—H92	109.47	H91'—C9'—H92'	109.47
Si1—C9—H93	109.47	H91'—C9'—H93'	109.47
H91—C9—H92	109.47	H92'—C9'—H93'	109.47
H91—C9—H93	109.47	Si1'—C10'—H101'	109.47
H92—C9—H93	109.47	Si1'—C10'—H102'	109.47
Si1—C10—H101	109.47	Si1'—C10'—H103'	109.47
Si1—C10—H102	109.47	H101'—C10'—H102'	109.47
Si1—C10—H103	109.47	H101'—C10'—H103'	109.47
H101—C10—H102	109.47	H102'—C10'—H103'	109.47
H101—C10—H103	109.47	Si1'—C11'—H111'	109.47
H102—C10—H103	109.47	Si1'—C11'—H112'	109.47
Si1—C11—H111	109.47	Si1'—C11'—H113'	109.47
Si1—C11—H112	109.47	H111'—C11'—H112'	109.47
Si1—C11—H113	109.47	H111'—C11'—H113'	109.47
H111—C11—H112	109.47	H112'—C11'—H113'	109.47
H111—C11—H113	109.47	S2'—C12'—H121'	109.47
H112—C11—H113	109.47	S2'—C12'—H122'	109.47
S2—C12—H121	109.47	S2'—C12'—H123'	109.47
S2—C12—H122	109.47	H121'—C12'—H122'	109.47
S2—C12—H123	109.47	H121'—C12'—H123'	109.47
H121—C12—H122	109.47	H122'—C12'—H123'	109.47
H121—C12—H123	109.47	C4'—C13'—C14'	122.4 (2)
H122—C12—H123	109.47	C13'—C14'—C15'	126.2 (3)
C4—C13—C14	122.9 (3)	C13'—C14'—H141'	116.9
C13—C14—C15	126.4 (3)	C15'—C14'—H141'	116.9
C13—C14—H141	116.79	C14'—C15'—C16'	176.7 (3)
C15—C14—H141	116.79	Si2'—C16'—C15'	176.1 (3)
Si2—C16—C15	175.1 (3)	Si2'—C17'—H171'	109.47
Si2—C17—H171	109.47	Si2'—C17'—H172'	109.47
Si2—C17—H172	109.47	Si2'—C17'—H173'	109.47
Si2—C17—H173	109.47	H171'—C17'—H172'	109.47
H171—C17—H172	109.47	H171'—C17'—H173'	109.47
H171—C17—H173	109.47	H172'—C17'—H173'	109.47
H172—C17—H173	109.47	Si2'—C18'—H181'	109.47
Si2—C18—H181	109.47	Si2'—C18'—H182'	109.47
Si2—C18—H182	109.47	Si2'—C18'—H183'	109.47
Si2—C18—H183	109.47	H181'—C18'—H182'	109.47
H181—C18—H182	109.47	H181'—C18'—H183'	109.47
H181—C18—H183	109.47	H182'—C18'—H183'	109.47
H182—C18—H183	109.47	Si2'—C19'—H191'	109.47
Si2—C19—H191	109.47	Si2'—C19'—H192'	109.47
Si2—C19—H192	109.47	Si2'—C19'—H193'	109.47
Si2—C19—H193	109.47	H191'—C19'—H192'	109.47
H191—C19—H192	109.47	H191'—C19'—H193'	109.47
H191—C19—H193	109.47	H192'—C19'—H193'	109.47
H192—C19—H193	109.47	S3'—C20'—H201'	109.47
S3—C20—H201	109.47	S3'—C20'—H202'	109.47
S3—C20—H202	109.47	S3'—C20'—H203'	109.47
S3—C20—H203	109.47	H201'—C20'—H202'	109.47
H201—C20—H202	109.47	H201'—C20'—H203'	109.47
H201—C20—H203	109.47	H202'—C20'—H203'	109.47
H202—C20—H203	109.47	O7'—C21'—C22'	111.2 (2)
O7—C21—C22	110.9 (2)	O7'—C21'—H211'	109.47
O7—C21—H211	109.47	O7'—C21'—H212'	109.47
O7—C21—H212	109.47	C22'—C21'—H211'	109.47
C22—C21—H211	109.47	C22'—C21'—H212'	109.47
C22—C21—H212	109.47	H211'—C21'—H212'	107.65
H211—C21—H212	107.97	O8'—C22'—C21'	110.9 (2)
O8—C22—C21	110.7 (2)	O8'—C22'—H221'	109.47
O8—C22—H221	109.47	O8'—C22'—H222'	109.47
O8—C22—H222	109.47	C21'—C22'—H221'	109.47
C21—C22—H221	109.47	C21'—C22'—H222'	109.47
C21—C22—H222	109.47	H221'—C22'—H222'	108.04
H221—C22—H222	108.17	C6'—C7'—C8'	178.7 (3)
O1'—S1'—O2'	116.19 (12)	C14—C15—C16	177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H212···O2^i	0.96	2.40	3.065 (3)	126.36
C21′—H212′···O2′^ii	0.96	2.40	3.066 (3)	125.84

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1.

(NSEM)

Crystal data

C22H38S2Si2	F(000) = 920
Mr = 422.8	Dx = 1.097 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2xab;2ybc;2zac	Cell parameters from 80665 reflections
a = 7.7849 (4) Å	θ = 2.5–35.0°
b = 10.5146 (5) Å	µ = 0.31 mm^−1
c = 31.2712 (14) Å	T = 100 K
V = 2559.7 (2) Å^3	Block, clear colourless
Z = 4	0.70 × 0.56 × 0.50 mm

Data collection

Bruker KAPPA APEX II CCD diffractometer	11125 independent reflections
Radiation source: X-ray tube	10833 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.024
ω– and φ–scans	θmax = 35.1°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −12→11
Tmin = 0.78, Tmax = 0.81	k = −16→16
101389 measured reflections	l = −48→50

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.027	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
wR(F^2) = 0.040	(Δ/σ)max = 0.005
S = 2.72	Δρmax = 0.33 e Å^−3
11125 reflections	Δρmin = −0.28 e Å^−3
236 parameters	Absolute structure: 4896 of Friedel pairs used in the refinement
0 restraints	Absolute structure parameter: 0.03 (3)
152 constraints

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

	x	y	z	Uiso*/Ueq
S1	0.31980 (3)	0.13191 (2)	0.966480 (8)	0.01959 (6)
S2	0.42766 (4)	−0.18580 (2)	1.013392 (7)	0.01960 (6)
Si1	0.62095 (3)	0.36183 (2)	0.852907 (7)	0.01126 (6)
Si2	0.58464 (3)	−0.26250 (2)	1.167524 (7)	0.01138 (6)
C1	0.51165 (12)	0.05694 (8)	0.98191 (3)	0.0137 (2)
C2	0.65741 (12)	0.08312 (8)	0.96038 (3)	0.0156 (2)
C3	0.66058 (11)	0.16972 (8)	0.92544 (3)	0.0149 (2)
C4	0.65625 (11)	0.24438 (8)	0.89564 (3)	0.0150 (2)
C5	0.57399 (15)	0.51746 (9)	0.87892 (3)	0.0210 (2)
C6	0.81656 (12)	0.37560 (9)	0.81894 (3)	0.0198 (2)
C7	0.43273 (12)	0.30347 (8)	0.82011 (3)	0.0149 (2)
C8	0.27671 (13)	0.28141 (10)	0.84927 (4)	0.0238 (3)
C9	0.47868 (15)	0.17811 (10)	0.79778 (4)	0.0246 (3)
C10	0.38554 (15)	0.40383 (10)	0.78635 (4)	0.0267 (3)
C11	0.15980 (13)	0.07253 (10)	1.00315 (3)	0.0217 (3)
C12	0.51395 (11)	−0.03211 (8)	1.01867 (3)	0.0132 (2)
C13	0.57667 (13)	0.00640 (8)	1.05691 (3)	0.0150 (2)
C14	0.58212 (12)	−0.07488 (8)	1.09330 (3)	0.0140 (2)
C15	0.58584 (12)	−0.14501 (8)	1.12401 (3)	0.01438 (19)
C16	0.81091 (13)	−0.31039 (10)	1.17887 (4)	0.0228 (3)
C17	0.48757 (15)	−0.18925 (9)	1.21607 (3)	0.0217 (3)
C18	0.45279 (11)	−0.40215 (7)	1.14844 (3)	0.0134 (2)
C19	0.53857 (13)	−0.46278 (9)	1.10924 (3)	0.0197 (2)
C20	0.27156 (12)	−0.35929 (10)	1.13670 (4)	0.0243 (3)
C21	0.44214 (14)	−0.50147 (9)	1.18440 (3)	0.0223 (3)
C22	0.42036 (16)	−0.20946 (10)	0.95631 (3)	0.0237 (3)
H2	0.762168	0.042114	0.968871	0.0187*
H13	0.619086	0.091762	1.0596	0.018*
H51	0.560229	0.581693	0.857371	0.0252*
H52	0.470165	0.510688	0.895325	0.0252*
H53	0.667379	0.540164	0.897454	0.0252*
H61	0.789393	0.42229	0.793441	0.0237*
H62	0.904823	0.419436	0.834508	0.0237*
H63	0.856308	0.292157	0.811361	0.0237*
H161	0.811641	−0.378246	1.199413	0.0273*
H162	0.864564	−0.338637	1.152913	0.0273*
H163	0.872941	−0.238937	1.190129	0.0273*
H171	0.470166	−0.253531	1.237433	0.026*
H172	0.563276	−0.124994	1.227042	0.026*
H173	0.379227	−0.15146	1.208749	0.026*
H81	0.237255	0.361474	0.860279	0.0285*
H82	0.186324	0.241879	0.833161	0.0285*
H83	0.30906	0.22708	0.872592	0.0285*
H91	0.512649	0.116444	0.818784	0.0295*
H92	0.380463	0.147189	0.782405	0.0295*
H93	0.571674	0.192246	0.778193	0.0295*
H101	0.364474	0.483854	0.800171	0.0321*
H102	0.478628	0.412947	0.76645	0.0321*
H103	0.28406	0.377381	0.771349	0.0321*
H191	0.652662	−0.48963	1.116601	0.0236*
H192	0.472625	−0.535	1.100119	0.0236*
H193	0.544073	−0.401631	1.086486	0.0236*
H201	0.217415	−0.322156	1.16129	0.0292*
H202	0.277349	−0.297454	1.114156	0.0292*
H203	0.205911	−0.431296	1.127256	0.0292*
H211	0.556005	−0.52461	1.19325	0.0268*
H212	0.38075	−0.466276	1.208248	0.0268*
H213	0.383	−0.575577	1.174157	0.0268*
H111	0.054953	0.119323	0.999468	0.0261*
H112	0.139313	−0.015933	0.997516	0.0261*
H113	0.200019	0.082599	1.031971	0.0261*
H221	0.348167	−0.280987	0.949901	0.0285*
H222	0.374774	−0.134702	0.942833	0.0285*
H223	0.534249	−0.225307	0.945816	0.0285*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01709 (9)	0.02357 (11)	0.01810 (11)	0.00327 (8)	−0.00015 (8)	0.00759 (8)
S2	0.03032 (12)	0.01448 (9)	0.01399 (10)	−0.00688 (9)	−0.00140 (9)	0.00100 (7)
Si1	0.01318 (10)	0.00958 (9)	0.01102 (10)	0.00007 (7)	−0.00039 (8)	0.00175 (8)
Si2	0.01431 (10)	0.01065 (9)	0.00919 (10)	0.00030 (8)	−0.00048 (8)	0.00210 (7)
C1	0.0176 (4)	0.0137 (3)	0.0099 (4)	−0.0009 (3)	−0.0020 (3)	0.0016 (3)
C2	0.0169 (4)	0.0168 (4)	0.0131 (4)	0.0005 (3)	−0.0004 (3)	0.0052 (3)
C3	0.0148 (3)	0.0173 (3)	0.0125 (4)	0.0001 (3)	0.0002 (3)	0.0027 (3)
C4	0.0159 (4)	0.0152 (3)	0.0137 (4)	0.0006 (3)	−0.0002 (3)	0.0012 (3)
C5	0.0248 (4)	0.0150 (4)	0.0233 (5)	0.0021 (3)	−0.0049 (4)	−0.0041 (3)
C6	0.0196 (4)	0.0187 (4)	0.0210 (4)	−0.0022 (3)	0.0036 (3)	0.0047 (3)
C7	0.0169 (4)	0.0120 (3)	0.0159 (4)	0.0008 (3)	−0.0039 (3)	0.0000 (3)
C8	0.0149 (4)	0.0263 (4)	0.0301 (5)	−0.0034 (3)	−0.0017 (4)	−0.0008 (4)
C9	0.0280 (5)	0.0192 (4)	0.0266 (5)	0.0025 (4)	−0.0054 (4)	−0.0087 (4)
C10	0.0303 (5)	0.0252 (5)	0.0248 (5)	0.0013 (4)	−0.0134 (4)	0.0062 (4)
C11	0.0190 (4)	0.0255 (4)	0.0207 (5)	0.0012 (4)	0.0038 (3)	−0.0009 (3)
C12	0.0151 (3)	0.0131 (3)	0.0114 (4)	−0.0009 (3)	−0.0011 (3)	0.0024 (3)
C13	0.0202 (4)	0.0133 (3)	0.0116 (4)	−0.0031 (3)	−0.0027 (3)	0.0026 (3)
C14	0.0173 (3)	0.0139 (3)	0.0109 (4)	−0.0016 (3)	−0.0020 (3)	0.0004 (3)
C15	0.0181 (3)	0.0130 (3)	0.0121 (4)	−0.0014 (3)	−0.0004 (3)	0.0006 (3)
C16	0.0165 (4)	0.0246 (4)	0.0272 (5)	0.0001 (3)	−0.0052 (4)	0.0052 (4)
C17	0.0346 (5)	0.0179 (4)	0.0125 (4)	0.0003 (4)	0.0022 (4)	−0.0003 (3)
C18	0.0138 (3)	0.0102 (3)	0.0163 (4)	0.0001 (2)	0.0021 (3)	0.0007 (3)
C19	0.0241 (4)	0.0169 (4)	0.0180 (4)	−0.0016 (3)	0.0037 (3)	−0.0049 (3)
C20	0.0156 (4)	0.0189 (4)	0.0385 (6)	0.0005 (3)	−0.0049 (4)	−0.0026 (4)
C21	0.0287 (5)	0.0143 (4)	0.0239 (5)	−0.0016 (3)	0.0082 (4)	0.0047 (3)
C22	0.0323 (5)	0.0214 (4)	0.0175 (4)	−0.0024 (4)	−0.0050 (4)	−0.0054 (3)

Geometric parameters (Å, º)

S1—C1	1.7564 (9)	C10—H102	0.96
S2—C12	1.7578 (9)	C10—H103	0.96
Si1—C4	1.8401 (9)	C11—H111	0.96
Si1—C5	1.8636 (10)	C11—H112	0.96
Si1—C6	1.8623 (10)	C11—H113	0.96
Si1—C7	1.8909 (9)	C12—C13	1.3536 (12)
Si2—C15	1.8379 (9)	C13—C14	1.4237 (12)
Si2—C16	1.8662 (11)	C13—H13	0.96
Si2—C17	1.8624 (10)	C14—C15	1.2111 (12)
Si2—C18	1.8883 (8)	C16—H161	0.96
C1—C2	1.3479 (13)	C16—H162	0.96
C1—C12	1.4828 (12)	C16—H163	0.96
C2—C3	1.4225 (12)	C17—H171	0.96
C2—H2	0.96	C17—H172	0.96
C3—C4	1.2190 (12)	C17—H173	0.96
C5—H51	0.96	C18—C19	1.5345 (13)
C5—H52	0.96	C18—C20	1.5259 (13)
C5—H53	0.96	C18—C21	1.5369 (13)
C6—H61	0.96	C19—H191	0.96
C6—H62	0.96	C19—H192	0.96
C6—H63	0.96	C19—H193	0.96
C7—C8	1.5364 (14)	C20—H201	0.96
C7—C9	1.5338 (13)	C20—H202	0.96
C7—C10	1.5372 (14)	C20—H203	0.96
C8—H81	0.96	C21—H211	0.96
C8—H82	0.96	C21—H212	0.96
C8—H83	0.96	C21—H213	0.96
C9—H91	0.96	C22—H221	0.96
C9—H92	0.96	C22—H222	0.96
C9—H93	0.96	C22—H223	0.96
C10—H101	0.96
C4—Si1—C5	107.56 (4)	H101—C10—H102	109.47
C4—Si1—C6	110.13 (4)	H101—C10—H103	109.47
C4—Si1—C7	106.96 (4)	H102—C10—H103	109.47
C5—Si1—C6	109.94 (5)	H111—C11—H112	109.47
C5—Si1—C7	111.69 (4)	H111—C11—H113	109.47
C6—Si1—C7	110.46 (4)	H112—C11—H113	109.47
C15—Si2—C16	108.50 (5)	S2—C12—C1	120.20 (6)
C15—Si2—C17	109.12 (4)	S2—C12—C13	119.73 (7)
C15—Si2—C18	106.95 (4)	C1—C12—C13	120.02 (8)
C16—Si2—C17	109.85 (5)	C12—C13—C14	122.49 (8)
C16—Si2—C18	111.31 (4)	C12—C13—H13	118.76
C17—Si2—C18	111.02 (4)	C14—C13—H13	118.76
S1—C1—C2	119.14 (7)	C13—C14—C15	179.31 (9)
S1—C1—C12	120.44 (7)	Si2—C15—C14	175.00 (8)
C2—C1—C12	120.41 (8)	Si2—C16—H161	109.47
C1—C2—C3	121.94 (8)	Si2—C16—H162	109.47
C1—C2—H2	119.03	Si2—C16—H163	109.47
C3—C2—H2	119.03	H161—C16—H162	109.47
C2—C3—C4	177.41 (9)	H161—C16—H163	109.47
Si1—C4—C3	172.52 (8)	H162—C16—H163	109.47
Si1—C5—H51	109.47	Si2—C17—H171	109.47
Si1—C5—H52	109.47	Si2—C17—H172	109.47
Si1—C5—H53	109.47	Si2—C17—H173	109.47
H51—C5—H52	109.47	H171—C17—H172	109.47
H51—C5—H53	109.47	H171—C17—H173	109.47
H52—C5—H53	109.47	H172—C17—H173	109.47
Si1—C6—H61	109.47	Si2—C18—C19	109.81 (6)
Si1—C6—H62	109.47	Si2—C18—C20	110.42 (6)
Si1—C6—H63	109.47	Si2—C18—C21	109.06 (6)
H61—C6—H62	109.47	C19—C18—C20	109.44 (8)
H61—C6—H63	109.47	C19—C18—C21	109.00 (7)
H62—C6—H63	109.47	C20—C18—C21	109.08 (8)
Si1—C7—C8	109.86 (6)	C18—C19—H191	109.47
Si1—C7—C9	110.18 (7)	C18—C19—H192	109.47
Si1—C7—C10	109.56 (6)	C18—C19—H193	109.47
C8—C7—C9	108.95 (8)	H191—C19—H192	109.47
C8—C7—C10	108.81 (8)	H191—C19—H193	109.47
C9—C7—C10	109.46 (8)	H192—C19—H193	109.47
C7—C8—H81	109.47	C18—C20—H201	109.47
C7—C8—H82	109.47	C18—C20—H202	109.47
C7—C8—H83	109.47	C18—C20—H203	109.47
H81—C8—H82	109.47	H201—C20—H202	109.47
H81—C8—H83	109.47	H201—C20—H203	109.47
H82—C8—H83	109.47	H202—C20—H203	109.47
C7—C9—H91	109.47	C18—C21—H211	109.47
C7—C9—H92	109.47	C18—C21—H212	109.47
C7—C9—H93	109.47	C18—C21—H213	109.47
H91—C9—H92	109.47	H211—C21—H212	109.47
H91—C9—H93	109.47	H211—C21—H213	109.47
H92—C9—H93	109.47	H212—C21—H213	109.47
C7—C10—H101	109.47	H221—C22—H222	109.47
C7—C10—H102	109.47	H221—C22—H223	109.47
C7—C10—H103	109.47	H222—C22—H223	109.47

(TSEM)

Crystal data

C20H28S3Si2	F(000) = 896
Mr = 420.8	Dx = 1.189 Mg m^−3
Monoclinic, I2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -I	Cell parameters from 5646 reflections
a = 34.443 (3) Å	θ = 2.4–30.1°
b = 6.7415 (4) Å	µ = 0.42 mm^−1
c = 10.1978 (8) Å	T = 100 K
β = 96.889 (5)°	Fragment, clear yellow
V = 2350.8 (3) Å^3	0.09 × 0.07 × 0.01 mm
Z = 4

Data collection

Bruker KAPPA APEX II CCD diffractometer	3045 independent reflections
Radiation source: X-ray tube	2366 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.064
ω– and φ–scans	θmax = 30.2°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −45→48
Tmin = 0.97, Tmax = 1.00	k = −9→0
29932 measured reflections	l = −14→0

Refinement

Refinement on F	56 constraints
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.063	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
S = 2.56	(Δ/σ)max = 0.027
3045 reflections	Δρmax = 1.53 e Å^−3
115 parameters	Δρmin = −1.41 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
Si1	−0.17864 (4)	−0.36480 (15)	0.68787 (12)	0.0154 (3)
S1	0	−0.22083 (19)	0.25	0.0152 (4)
S2	−0.08137 (3)	−0.10021 (14)	0.35864 (10)	0.0170 (3)
C1	−0.02870 (12)	−0.3979 (6)	0.3133 (4)	0.0123 (12)
C2	−0.01647 (11)	−0.5848 (6)	0.2847 (4)	0.0151 (12)
C3	−0.06067 (12)	−0.3398 (5)	0.3859 (4)	0.0122 (11)
C4	−0.07320 (11)	−0.4556 (6)	0.4803 (4)	0.0154 (13)
C5	−0.10600 (12)	−0.4149 (5)	0.5489 (4)	0.0155 (12)
C6	−0.13393 (12)	−0.3922 (6)	0.6078 (4)	0.0149 (12)
C7	−0.19606 (13)	−0.6184 (6)	0.7226 (5)	0.0300 (16)
C8	−0.16822 (12)	−0.2209 (6)	0.8438 (4)	0.0208 (13)
C9	−0.21539 (14)	−0.2299 (8)	0.5731 (5)	0.0333 (17)
C10	−0.09552 (13)	−0.0950 (6)	0.1823 (4)	0.0235 (14)
H2	−0.029085	−0.703636	0.309605	0.0181*
H4	−0.058824	−0.575155	0.503069	0.0185*
H71	−0.220878	−0.60969	0.756175	0.0361*
H72	−0.198861	−0.694786	0.64255	0.0361*
H73	−0.177451	−0.681535	0.786874	0.0361*
H81	−0.191167	−0.217735	0.888635	0.0249*
H82	−0.147198	−0.282719	0.899423	0.0249*
H83	−0.160904	−0.087883	0.823657	0.0249*
H91	−0.237127	−0.193175	0.618695	0.0399*
H92	−0.203698	−0.112647	0.541497	0.0399*
H93	−0.224351	−0.314004	0.499707	0.0399*
H101	−0.108871	0.027068	0.158395	0.0282*
H102	−0.072614	−0.104701	0.137528	0.0282*
H103	−0.112592	−0.204705	0.15728	0.0282*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0132 (6)	0.0181 (5)	0.0160 (6)	−0.0025 (5)	0.0065 (6)	−0.0005 (5)
S1	0.0179 (8)	0.0113 (6)	0.0184 (7)	0	0.0101 (8)	0
S2	0.0253 (6)	0.0114 (5)	0.0160 (5)	0.0038 (5)	0.0095 (5)	0.0006 (4)
C1	0.013 (2)	0.016 (2)	0.0083 (18)	0.0002 (18)	0.0018 (17)	0.0011 (17)
C2	0.013 (2)	0.015 (2)	0.017 (2)	−0.0028 (16)	0.0019 (16)	0.0011 (16)
C3	0.015 (2)	0.0075 (17)	0.014 (2)	−0.0009 (16)	0.0017 (17)	−0.0026 (15)
C4	0.013 (2)	0.016 (2)	0.019 (2)	0.0015 (16)	0.0065 (18)	0.0000 (18)
C5	0.020 (2)	0.0131 (19)	0.014 (2)	−0.0021 (18)	0.0060 (19)	0.0020 (16)
C6	0.020 (2)	0.0089 (19)	0.016 (2)	−0.0018 (17)	0.0042 (18)	−0.0007 (16)
C7	0.033 (3)	0.025 (2)	0.035 (3)	−0.015 (2)	0.017 (2)	−0.007 (2)
C8	0.019 (2)	0.024 (2)	0.020 (2)	−0.0024 (19)	0.0071 (19)	−0.0006 (18)
C9	0.022 (3)	0.053 (3)	0.026 (3)	0.009 (2)	0.007 (2)	0.000 (2)
C10	0.027 (3)	0.025 (2)	0.019 (2)	0.009 (2)	0.0055 (18)	0.0035 (18)

Geometric parameters (Å, º)

Si1—C6	1.837 (5)	C5—C6	1.204 (6)
Si1—C7	1.860 (4)	C7—H71	0.96
Si1—C8	1.860 (4)	C7—H72	0.96
Si1—C9	1.856 (5)	C7—H73	0.96
S1—C1	1.724 (4)	C8—H81	0.96
S1—C1^i	1.724 (4)	C8—H82	0.96
S2—C3	1.774 (4)	C8—H83	0.96
C1—C2	1.371 (6)	C9—H91	0.96
C1—C3	1.452 (6)	C9—H92	0.96
C2—C2^i	1.408 (6)	C9—H93	0.96
C2—H2	0.96	C10—H101	0.96
C3—C4	1.349 (6)	C10—H102	0.96
C4—C5	1.425 (6)	C10—H103	0.96
C4—H4	0.96
C6—Si1—C7	107.41 (19)	Si1—C7—H71	109.47
C6—Si1—C8	110.26 (19)	Si1—C7—H72	109.47
C6—Si1—C9	108.3 (2)	Si1—C7—H73	109.47
C7—Si1—C8	110.5 (2)	H71—C7—H72	109.47
C7—Si1—C9	111.1 (2)	H71—C7—H73	109.47
C8—Si1—C9	109.3 (2)	H72—C7—H73	109.47
C1—S1—C1^i	92.4 (2)	Si1—C8—H81	109.47
S1—C1—C2	110.6 (3)	Si1—C8—H82	109.47
S1—C1—C3	120.6 (3)	Si1—C8—H83	109.47
C2—C1—C3	128.8 (4)	H81—C8—H82	109.47
C1—C2—C2^i	113.2 (4)	H81—C8—H83	109.47
C1—C2—H2	123.41	H82—C8—H83	109.47
C2^i—C2—H2	123.41	Si1—C9—H91	109.47
S2—C3—C1	118.7 (3)	Si1—C9—H92	109.47
S2—C3—C4	118.8 (3)	Si1—C9—H93	109.47
C1—C3—C4	122.3 (3)	H91—C9—H92	109.47
C3—C4—C5	125.4 (4)	H91—C9—H93	109.47
C3—C4—H4	117.3	H92—C9—H93	109.47
C5—C4—H4	117.3	H101—C10—H102	109.47
C4—C5—C6	176.2 (4)	H101—C10—H103	109.47
Si1—C6—C5	176.1 (4)	H102—C10—H103	109.47

Symmetry code: (i) −x, y, −z+1/2.