research papers
Crystal chemistry of layered structures formed by linear rigid silyl-capped molecules
aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria, and bInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Vienna, Austria
*Correspondence e-mail: bstoeger@mail.tuwien.ac.at
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 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 were observed, which feature geometrically different layer interfaces (non-OD, order–disorder, polytypes), one with a high 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 de/di fingerprint plots. The analogously oxidized EDOT-based molecule crystallized as systematic twins owing to its OD 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.
Keywords: arene spacers; incommensurately modulated structures; layer interfaces; order–disorder polytypes; Hirshfeld surface fingerprint plots.
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 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 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).
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 b) 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 are locally equivalent. The symmetry of a polytype is described by groupoids, a generalization of the group concept (Fichtner, 1986). For OD these groupoids are classified into OD families (Fichtner, 1977b), in analogy to types. These were tabulated for the special case of OD structures composed of layers of one kind with identical lattices (Fichtner, 1977a).
are ubiquitous in all classes of solid materials and are often the cause of crystallographically challenging problems, like (the systematic association of equivalent macroscopic domains with different orientations; Hahn, 2006Nevertheless, 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 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, that are not locally equivalent must not be overlooked. The symmetry groupoids of these kinds of are virtually unexplored. Thus, to shed new light on OD theory and related kinds of 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.
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 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 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.
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.
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 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 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 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 of the TMS-containing molecule. Therefore, we synthesized and grew crystals of the corresponding tert-butyl-dimethylsilyl (TBDMS) compound NSEM-TBDMS (5).
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 can freely rotate. Nevertheless, the overall forms of the molecules feature little possibility for variation.
In Table 1 the rotation angles about the freely rotatable bonds of the title compounds are compiled.
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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).
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 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).
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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).
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.
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) 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 (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 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 (the crystal is enantiomorphic).
2.5. 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).
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).
The crystal of TSEM (2) was twinned by reflection at (001). Often, OD theory is a convenient tool to understand 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 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 is demonstrated by the DSEM (4) (§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 (Janssen et al., 2007; van Smaalen, 2007). The of ESEM (3) has 3+1-dimensional 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 as2/2 + as4/2, 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 as4/2 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.
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.
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.
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.
2.5.3. DSEM (4)
Like in TSEM (2) and ESEM (3), the DSEM (4) molecules in both 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) are non-OD in the following discussion the naming conventions of OD theory will be used (Ferraris et al., 2008): the layers are designated as An, 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 An layer, the adjacent An+1 layer can appear in two different orientations. An and An+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.
Thus, the layers can be connected to an infinity of An, An+1) layer pairs are not necessarily equivalent [p(1)2/c1 and p(c)c2 symmetry, respectively]. The differ from other non-OD we discussed before (Stöger et al., 2012a; Stöger & Weil, 2013). In the latter, which we designated as `non-classic OD' every polytype is at every point locally equivalent to all other 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 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 of TSEM (2) is likewise caused by non-equivalent layer contacts.
which are not OD because (Although the symmetry groupoids of these kind of non-OD maximum degree of order (MDO) (Dornberger-Schiff, 1982) can nevertheless be applied. There are two that cannot be decomposed into simpler 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.
were not elaborated up to now, the OD concept of with aThe observed 1 and MDO2, respectively. Indeed, it is well documented for OD structures that ordered are in the vast majority of cases MDO. Fragments of the MDO2 polytype in MDO1 result in by reflection at a plane normal to [001]. No such 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.
I and II are MDOAs opposed to OD structures, where ordered ), the A layers in both MDO 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.
usually feature of the layers compared to the idealized description (Ďurovič, 19792.5.4. 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.
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).
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).
Thus, the I II b and 21d). In consequence, the layer interfaces are fundamentally different in the two (Fig. 22), demonstrating again the flexibility in layer arrangements allowed by the TMS groups.
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. 21Although methylsulfonyl groups are potential hydrogen bond acceptors, the oxBSEM (1b) molecules do not possess classical hydrogen-bond donors. Indeed, attempts to analyze the 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 de/di 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 de = di 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).
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 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.
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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 de = di. 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 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.
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).
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 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 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 (An, An+1) layer pair, An+1 is related to An by a 2r screw with intrinsic translation along ra/2 or equivalently by an n1,2 glide with intrinsic translation along (b/2) + c0. The other geometrically equivalent arrangements are derived using the NFZ relationship (Ďurovič, 1997): Given an An layer, an adjacent layer can appear in Z = N/F = [p11(1):pb1(1)] = 2 orientations, related by the b glides of An. 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 1 {, c = c0 + [(r − 1)/2]a} and MDO2 (P21/n11, c = 2c0), obtained by continuous application of the 2r screws and n1,2 glides, respectively. The symmetry of the two is schematized in Fig. 26.
MDOThe major polytype of the crystals under investigation is the MDO1 polytype. Fragments of the MDO2 polytype were observed indirectly by systematic The corresponds to the plane of the b glides of the A layers. This kind of is fundamentally different from that in TSEM (2) or the 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 P 21 21 21. The crystal under investigation was [Flack parameter 0.03 (3)]. An estimation of the number of achiral molecules crystallizing in 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).
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).
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 6) can be explained by local 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.
of ASYM (As a consequence, the structure belongs to a category IV OD family composed of nonpolar layers of two kinds. The corresponding OD ) as
family symbol reads according to the notation introduced by Grell & Dornberger-Schiff (1982Accordingly, 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 (A1n, A2n+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 A1n 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 A1n 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 1 (, 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 is schematized in Fig. 29.
MDOThe 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 corresponds to the mirror plane of the A1 layers. Again, all 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 does not result in two crystallographically unique molecules, but rather in a 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 are available as supplementary materials.
4. Conclusion and outlook
We set out to create layered structures, expecting to obtain OD 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 of TSEM (2) and DSEM (4) and the layer contacts can accomodate the different molecular arrangements observed in the temperature-dependent of oxBSEM (1b).
due to different local layer symmetry. We were indeed successful with the systematic twins oxESEM (These phenomena demonstrate the necessity of a generalization of space-group symmetry to 1) and TSEM (2).
These so-far unexplored groupoids are necessary not only for the description of but also of structural relationships like the merotypism of BSEM (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 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 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.
like TBDMS or TIPS to induce different layer contacts as in NSEM-TBDMS (Supporting information
https://doi.org/10.1107/S2052252515011665/yc5004sup1.cif
contains datablocks ASYM, BSEM, BSEMOX1, BSEMOX2, BSEMOX3, DSEM1, DSEM2, ESEM, ESEMOX, NSEM, TSEM. DOI:Structure factors: contains datablock ASYM. DOI: https://doi.org/10.1107/S2052252515011665/yc5004ASYMsup2.hkl
Structure factors: contains datablock BSEM. DOI: https://doi.org/10.1107/S2052252515011665/yc5004BSEMsup3.hkl
Structure factors: contains datablock BSEMOX1. DOI: https://doi.org/10.1107/S2052252515011665/yc5004BSEMOX1sup4.hkl
Structure factors: contains datablock BSEMOX2. DOI: https://doi.org/10.1107/S2052252515011665/yc5004BSEMOX2sup5.hkl
Structure factors: contains datablock BSEMOX3. DOI: https://doi.org/10.1107/S2052252515011665/yc5004BSEMOX3sup6.hkl
Structure factors: contains datablock DSEM1. DOI: https://doi.org/10.1107/S2052252515011665/yc5004DSEM1sup7.hkl
Structure factors: contains datablock DSEM2. DOI: https://doi.org/10.1107/S2052252515011665/yc5004DSEM2sup8.hkl
Structure factors: contains datablock ESEMOX. DOI: https://doi.org/10.1107/S2052252515011665/yc5004ESEMOXsup9.hkl
Structure factors: contains datablock NSEM. DOI: https://doi.org/10.1107/S2052252515011665/yc5004NSEMsup10.hkl
Structure factors: contains datablock TSEM. DOI: https://doi.org/10.1107/S2052252515011665/yc5004TSEMsup11.hkl
Structure factors: contains datablock ESEM. DOI: https://doi.org/10.1107/S2052252515011665/yc5004ESEMsup13.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2052252515011665/yc5004sup12.pdf
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) Å3 |
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 on F | 88 constraints |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.055 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
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) Å3 | 0.77 × 0.25 × 0.03 mm |
Z = 4 |
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 on F | 60 constraints |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.044 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C3i | 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—C3i | 120.86 (7) | Si—C9—H93 | 109.47 |
C1—C2—H2 | 119.57 | H91—C9—H92 | 109.47 |
C3i—C2—H2 | 119.57 | H91—C9—H93 | 109.47 |
C1—C3—C2i | 121.09 (7) | H92—C9—H93 | 109.47 |
C1—C3—H3 | 119.46 | Si—C10—H101 | 109.47 |
C2i—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. |
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) Å3 |
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 on F | 120 constraints |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.044 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C3i | 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—C3i | 120.27 (9) | C1'—C2'—C3' | 120.08 (8) |
C1—C2—H2 | 119.87 | C1'—C2'—H2' | 119.96 |
C3i—C2—H2 | 119.87 | C3'—C2'—H2' | 119.96 |
C1—C3—C2i | 120.89 (9) | C1'ii—C3'—C2' | 121.24 (7) |
C1—C3—H3 | 119.56 | C1'ii—C3'—H3' | 119.38 |
C2i—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. |
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′···O1iii | 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. |
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) Å3 |
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 on F | 120 constraints |
R[F2 > 2σ(F2)] = 0.074 | H-atom parameters constrained |
wR(F2) = 0.093 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C2i | 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) |
C2i—C1—C3 | 119.0 (3) | C2'—C1'—C3'ii | 118.9 (3) |
C2i—C1—C4 | 121.4 (4) | C2'—C1'—C4' | 122.8 (3) |
C3—C1—C4 | 119.5 (3) | C3'ii—C1'—C4' | 118.3 (3) |
C1i—C2—C3 | 120.6 (4) | C1'—C2'—C3' | 119.7 (3) |
C1i—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. |
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) Å3 |
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 on F | 60 constraints |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.039 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C3i | 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—C3i | 119.90 (14) | Si1—C10—H102 | 109.47 |
C1—C2—H2 | 120.05 | Si1—C10—H103 | 109.47 |
C3i—C2—H2 | 120.05 | H101—C10—H102 | 109.47 |
C1—C3—C2i | 121.20 (13) | H101—C10—H103 | 109.47 |
C1—C3—H3 | 119.4 | H102—C10—H103 | 109.47 |
C2i—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. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H111···O2ii | 0.96 | 2.49 | 3.362 (2) | 150.78 |
Symmetry code: (ii) x+1, y, z. |
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) Å3 | 0.87 × 0.66 × 0.03 mm |
Z = 8 |
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 on F | 128 constraints |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.059 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
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···O2i | 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. |
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) Å3 | 0.60 × 0.51 × 0.01 mm |
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 on F | 128 constraints |
R[F2 > 2σ(F2)] = 0.087 | H-atom parameters constrained |
wR(F2) = 0.085 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O2i | 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. |
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) Å3 | 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. |
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 on F | 0 restraints |
R[F2 > 2σ(F2)] = 0.063 | 240 constraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 2.36 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
15382 reflections | (Δ/σ)max = 0.038 |
510 parameters |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Average | Minimum | Maximum | |
S1—C1 | 2.554 (4) | 2.544 (4) | 2.563 (4) |
S1—C1i | 2.554 (4) | 2.544 (4) | 2.563 (4) |
S1—C2 | 1.735 (4) | 1.730 (4) | 1.741 (4) |
S1—C2i | 1.735 (4) | 1.730 (4) | 1.741 (4) |
S1—C3 | 2.778 (4) | 2.769 (4) | 2.784 (4) |
S1—C3i | 2.778 (4) | 2.769 (4) | 2.784 (4) |
S1—H102 | 3(6) | 3(6) | 3(6) |
S1—H102i | 3(6) | 3(6) | 3(6) |
S1—H112ii | 3(2) | 2.8 (18) | 3(3) |
S1—H112iii | 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—H111iv | 3(4) | 3(3) | 3(4) |
S2—H112ii | 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—O1i | 2.899 (4) | 2.895 (4) | 2.904 (4) |
O1—C1 | 1.362 (5) | 1.357 (5) | 1.366 (5) |
O1—C1i | 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—C11i | 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—H111i | 3(5) | 3(5) | 3(6) |
O1—H112 | 2.0 (19) | 2.0 (18) | 2.0 (19) |
C1—C1i | 1.418 (6) | 1.405 (6) | 1.430 (6) |
C1—C2 | 1.374 (5) | 1.358 (5) | 1.387 (5) |
C1—C2i | 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—C11i | 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—H111i | 3(4) | 3(5) | 3(4) |
C2—C2i | 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—H82v | 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—H82v | 3(3) | 3(3) | 3(3) |
C5—H111iv | 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—H101vi | 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—H72vii | 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—H82viii | 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—C11i | 1.483 (5) | 1.481 (5) | 1.485 (5) |
C11—H111 | 1(5) | 1(5) | 1(5) |
C11—H111i | 2(6) | 2(6) | 2(6) |
C11—H112 | 1(2) | 1.0 (18) | 1.0 (18) |
C11—H112i | 2(5) | 2(5) | 2(5) |
H41—H82v | 2.8035 | 2.6414 | 3.0371 |
H41—H102iv | 2.8443 | 2.7612 | 2.9236 |
H71—H72 | 1.5677 | 1.5676 | 1.5677 |
H71—H73 | 1.5677 | 1.567 | 1.5683 |
H71—H91ix | 2.645 | 2.5594 | 2.7911 |
H71—H93iv | 2.689 | 2.5373 | 2.886 |
H72—H73 | 1.5677 | 1.5668 | 1.5685 |
H72—H91x | 2.9347 | 2.7266 | 3.1049 |
H72—H92x | 3.0988 | 2.8089 | 3.4242 |
H72—H93x | 2.8424 | 2.6068 | 3.1513 |
H72—H103iv | 3.0231 | 2.876 | 3.1317 |
H73—H93iv | 2.8883 | 2.8072 | 2.9751 |
H73—H103iv | 2.6896 | 2.5493 | 2.8225 |
H81—H82 | 1.5677 | 1.5674 | 1.568 |
H81—H83 | 1.5676 | 1.567 | 1.5683 |
H81—H91ix | 2.6201 | 2.417 | 2.8587 |
H81—H92vi | 3.4145 | 2.6698 | 4.3469 |
H82—H83 | 1.5677 | 1.5666 | 1.5687 |
H82—H102xi | 2.7836 | 2.6281 | 3.0182 |
H82—H103xi | 2.7104 | 2.5795 | 2.8997 |
H83—H101vi | 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—H111ii | 3.1659 | 2.971 | 3.4335 |
H102—H103 | 1.5677 | 1.5673 | 1.568 |
H102—H111ii | 3.3031 | 2.9634 | 3.723 |
H111—H111i | 2.7901 | 2.7886 | 2.7917 |
H111—H112 | 1.5485 | 1.5424 | 1.5554 |
H111—H112i | 2.3192 | 2.3142 | 2.325 |
H112—H112i | 2.2847 | 2.2824 | 2.2871 |
C1—S1—C1i | 32.22 (13) | 31.94 (13) | 32.50 (13) |
C1—S1—C2 | 30.39 (15) | 30.02 (15) | 30.67 (15) |
C1—S1—C2i | 62.61 (16) | 62.29 (16) | 63.01 (16) |
C1—S1—C3 | 57.10 (12) | 56.72 (12) | 57.39 (12) |
C1—S1—C3i | 89.31 (12) | 89.00 (12) | 89.69 (12) |
C1—S1—H102 | 95.36 | 94.28 | 96.52 |
C1—S1—H102i | 112.9 | 111.3 | 114.48 |
C1—S1—H112ii | 142.78 | 140.84 | 145.32 |
C1—S1—H112iii | 174.52 | 172.92 | 176.02 |
C1i—S1—C2 | 62.61 (16) | 62.29 (16) | 63.01 (16) |
C1i—S1—C2i | 30.39 (15) | 30.02 (15) | 30.67 (15) |
C1i—S1—C3 | 89.31 (12) | 89.00 (12) | 89.69 (12) |
C1i—S1—C3i | 57.10 (12) | 56.72 (12) | 57.39 (12) |
C1i—S1—H102 | 112.89 | 111.3 | 114.48 |
C1i—S1—H102i | 95.37 | 94.28 | 96.52 |
C1i—S1—H112ii | 174.5 | 172.92 | 176.02 |
C1i—S1—H112iii | 142.8 | 140.84 | 145.32 |
C2—S1—C2i | 93.00 (18) | 92.67 (18) | 93.33 (18) |
C2—S1—C3 | 26.71 (15) | 26.41 (15) | 26.98 (15) |
C2—S1—C3i | 119.70 (15) | 119.43 (15) | 119.98 (15) |
C2—S1—H102 | 77.17 | 76.49 | 77.59 |
C2—S1—H102i | 124.59 | 122.64 | 126.32 |
C2—S1—H112ii | 112.41 | 110.74 | 114.83 |
C2—S1—H112iii | 154.49 | 151.95 | 156.57 |
C2i—S1—C3 | 119.70 (15) | 119.43 (15) | 119.98 (15) |
C2i—S1—C3i | 26.71 (15) | 26.41 (15) | 26.98 (15) |
C2i—S1—H102 | 124.59 | 122.64 | 126.32 |
C2i—S1—H102i | 77.18 | 76.49 | 77.59 |
C2i—S1—H112ii | 154.51 | 151.95 | 156.57 |
C2i—S1—H112iii | 112.43 | 110.74 | 114.83 |
C3—S1—C3i | 146.40 (11) | 146.38 (11) | 146.43 (11) |
C3—S1—H102 | 62.67 | 61.96 | 63.37 |
C3—S1—H102i | 127.17 | 125.46 | 128.98 |
C3—S1—H112ii | 85.7 | 83.77 | 88.28 |
C3—S1—H112iii | 127.85 | 125.27 | 129.82 |
C3i—S1—H102 | 127.18 | 125.46 | 128.98 |
C3i—S1—H102i | 62.68 | 61.96 | 63.37 |
C3i—S1—H112ii | 127.87 | 125.27 | 129.82 |
C3i—S1—H112iii | 85.72 | 83.77 | 88.28 |
H102—S1—H102i | 150.84 | 150.66 | 151.02 |
H102—S1—H112ii | 62.97 | 61.73 | 64.72 |
H102—S1—H112iii | 89.17 | 87.69 | 90.26 |
H102i—S1—H112ii | 89.16 | 87.69 | 90.26 |
H102i—S1—H112iii | 62.96 | 61.73 | 64.72 |
H112ii—S1—H112iii | 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—H111iv | 91.33 | 85.59 | 97.52 |
C2—S2—H112ii | 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—H111iv | 78.01 | 74.77 | 82.11 |
C3—S2—H112ii | 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—H111iv | 66.25 | 65.48 | 67.53 |
C4—S2—H112ii | 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—H111iv | 172.94 | 166.57 | 179.3 |
C10—S2—H112ii | 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—H111iv | 156.16 | 151.37 | 158.77 |
H101—S2—H112ii | 74.3 | 71.87 | 76.49 |
H102—S2—H103 | 39.48 | 39.37 | 39.56 |
H102—S2—H111iv | 158.48 | 148.51 | 169.02 |
H102—S2—H112ii | 73.43 | 69.6 | 77.99 |
H103—S2—H111iv | 154.59 | 145.91 | 161.36 |
H103—S2—H112ii | 107.54 | 105.88 | 109.27 |
H111iv—S2—H112ii | 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 |
O1i—O1—C1 | 57.0 (2) | 56.6 (2) | 57.5 (2) |
O1i—O1—C1i | 27.89 (11) | 27.78 (10) | 28.01 (11) |
O1i—O1—C2 | 85.43 (13) | 85.22 (13) | 85.72 (13) |
O1i—O1—C4 | 138.34 (13) | 137.84 (13) | 138.96 (13) |
O1i—O1—C11 | 56.62 (17) | 56.04 (17) | 57.33 (17) |
O1i—O1—C11i | 30.02 (10) | 29.80 (10) | 30.22 (10) |
O1i—O1—H41 | 148.21 | 145.32 | 150.84 |
O1i—O1—H111 | 61.36 | 60.94 | 61.92 |
O1i—O1—H111i | 41.93 | 41.66 | 42.2 |
O1i—O1—H112 | 80.87 | 80.31 | 81.58 |
C1—O1—C1i | 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—C11i | 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—H111i | 88.41 | 87.45 | 89.42 |
C1—O1—H112 | 137.67 | 137.11 | 138.58 |
C1i—O1—C2 | 57.55 (14) | 57.31 (14) | 57.86 (14) |
C1i—O1—C4 | 110.56 (15) | 110.19 (15) | 111.16 (15) |
C1i—O1—C11 | 83.6 (2) | 83.1 (2) | 84.1 (2) |
C1i—O1—C11i | 57.16 (14) | 56.81 (14) | 57.48 (14) |
C1i—O1—H41 | 122.11 | 120.07 | 124.09 |
C1i—O1—H111 | 81.51 | 81.2 | 81.78 |
C1i—O1—H111i | 63.14 | 62.51 | 63.74 |
C1i—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—C11i | 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—H111i | 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—C11i | 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—H111i | 144.23 | 143.53 | 144.93 |
C4—O1—H112 | 140.73 | 140.15 | 141.31 |
C11—O1—C11i | 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—H111i | 50.09 | 49.71 | 50.58 |
C11—O1—H112 | 27.05 | 26.95 | 27.2 |
C11i—O1—H41 | 157.58 | 154.62 | 160.61 |
C11i—O1—H111 | 53.28 | 52.98 | 53.73 |
C11i—O1—H111i | 21.54 | 21.42 | 21.67 |
C11i—O1—H112 | 53.28 | 52.98 | 53.74 |
H41—O1—H111 | 147 | 143.9 | 149.93 |
H41—O1—H111i | 136.08 | 133.09 | 139.15 |
H41—O1—H112 | 127.76 | 126.57 | 128.69 |
H111—O1—H111i | 73.18 | 72.8 | 73.71 |
H111—O1—H112 | 45.78 | 45.43 | 46.25 |
H111i—O1—H112 | 58.63 | 58.42 | 58.92 |
S1—C1—O1 | 163.1 (3) | 162.6 (3) | 163.7 (3) |
S1—C1—O1i | 101.78 (15) | 101.59 (15) | 101.98 (15) |
S1—C1—C1i | 73.9 (2) | 73.6 (2) | 74.1 (2) |
S1—C1—C2 | 39.68 (19) | 39.5 (2) | 39.83 (19) |
S1—C1—C2i | 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—C11i | 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—H111i | 130.04 | 128.78 | 131.1 |
O1—C1—O1i | 95.1 (2) | 94.6 (2) | 95.5 (2) |
O1—C1—C1i | 122.9 (3) | 122.6 (3) | 123.4 (3) |
O1—C1—C2 | 123.5 (4) | 122.8 (4) | 124.1 (4) |
O1—C1—C2i | 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—C11i | 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—H111i | 63.74 | 62.81 | 64.66 |
O1i—C1—C1i | 27.90 (18) | 27.81 (18) | 28.04 (18) |
O1i—C1—C2 | 141.4 (3) | 141.3 (3) | 141.7 (3) |
O1i—C1—C2i | 60.54 (15) | 60.41 (15) | 60.66 (15) |
O1i—C1—C3 | 167.4 (2) | 166.8 (2) | 168.0 (2) |
O1i—C1—C11 | 61.06 (14) | 60.37 (13) | 61.58 (14) |
O1i—C1—C11i | 32.35 (10) | 31.93 (10) | 32.61 (10) |
O1i—C1—H41 | 148.73 | 147.83 | 149.65 |
O1i—C1—H111 | 61.61 | 60.89 | 62.21 |
O1i—C1—H111i | 42.51 | 42.19 | 42.68 |
C1i—C1—C2 | 113.6 (3) | 113.3 (3) | 113.9 (3) |
C1i—C1—C2i | 32.64 (19) | 32.39 (19) | 32.8 (2) |
C1i—C1—C3 | 139.7 (3) | 139.2 (3) | 140.2 (3) |
C1i—C1—C11 | 88.7 (2) | 88.1 (2) | 89.1 (2) |
C1i—C1—C11i | 59.6 (2) | 59.1 (2) | 59.9 (2) |
C1i—C1—H41 | 167.13 | 164.19 | 170.59 |
C1i—C1—H111 | 85.82 | 85.25 | 86.16 |
C1i—C1—H111i | 65.16 | 64.6 | 65.63 |
C2—C1—C2i | 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—C11i | 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—H111i | 154.01 | 152.9 | 155.21 |
C2i—C1—C3 | 107.11 (18) | 106.52 (18) | 107.54 (18) |
C2i—C1—C11 | 121.0 (2) | 120.3 (2) | 121.4 (2) |
C2i—C1—C11i | 91.91 (17) | 91.19 (17) | 92.39 (17) |
C2i—C1—H41 | 145.94 | 143.65 | 147.73 |
C2i—C1—H111 | 114.29 | 114.02 | 114.6 |
C2i—C1—H111i | 93.97 | 93 | 94.78 |
C3—C1—C11 | 130.7 (2) | 129.9 (2) | 131.9 (2) |
C3—C1—C11i | 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—H111i | 147.63 | 146.98 | 148.02 |
C11—C1—C11i | 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—H111i | 43.51 | 43.36 | 43.73 |
C11i—C1—H41 | 116.7 | 115.57 | 117.67 |
C11i—C1—H111 | 44.3 | 44.06 | 44.56 |
C11i—C1—H111i | 19.2 | 19.13 | 19.31 |
H41—C1—H111 | 99.45 | 97.15 | 101.97 |
H41—C1—H111i | 107.29 | 106 | 109.16 |
H111—C1—H111i | 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—C1i | 76.14 (17) | 75.80 (17) | 76.39 (17) |
S1—C2—C2i | 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—C1i | 160.4 (2) | 159.8 (2) | 161.2 (2) |
S2—C2—C2i | 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—C1i | 61.91 (15) | 61.57 (15) | 62.27 (15) |
O1—C2—C2i | 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—C1i | 33.8 (2) | 33.4 (2) | 34.2 (2) |
C1—C2—C2i | 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 |
C1i—C2—C2i | 32.64 (13) | 32.34 (13) | 32.80 (14) |
C1i—C2—C3 | 162.9 (3) | 162.3 (3) | 163.4 (3) |
C1i—C2—C4 | 136.4 (2) | 135.9 (2) | 136.9 (2) |
C1i—C2—H41 | 115.26 | 114.65 | 115.74 |
C1i—C2—H102 | 114.96 | 113.16 | 116.39 |
C2i—C2—C3 | 164.3 (3) | 163.7 (3) | 164.7 (3) |
C2i—C2—C4 | 166.9 (2) | 165.9 (2) | 168.2 (2) |
C2i—C2—H41 | 145.69 | 144.82 | 147 |
C2i—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—H82v | 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—H82v | 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—H82v | 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—H82v | 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—H82v | 74.8 | 64.08 | 85.3 |
C6—C4—H41 | 116.88 | 115.16 | 118.27 |
C6—C4—H82v | 74.13 | 63.43 | 84.39 |
H41—C4—H82v | 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—H82v | 93.75 | 83.43 | 104.52 |
C3—C5—H111iv | 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—H82v | 77.74 | 67.97 | 89.12 |
C4—C5—H111iv | 79.58 | 72.42 | 87.14 |
C6—C5—H41 | 153.32 | 150.23 | 155.75 |
C6—C5—H82v | 100.79 | 89.41 | 111.38 |
C6—C5—H111iv | 101.59 | 94.31 | 111.91 |
H41—C5—H82v | 65.04 | 56.86 | 75.52 |
H41—C5—H111iv | 90.95 | 83.2 | 99.25 |
H82v—C5—H111iv | 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—H101vi | 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—H101vi | 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—H101vi | 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—H101vi | 116.55 | 109.18 | 125.4 |
C8—C6—C9 | 61.06 (15) | 60.36 (15) | 61.67 (15) |
C8—C6—H101vi | 59.25 | 52.37 | 66.55 |
C9—C6—H101vi | 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—H72vii | 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—H72vii | 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 |
H72vii—C9—H91 | 69.53 | 65.1 | 75.6 |
H72vii—C9—H92 | 79.78 | 58.49 | 96.83 |
H72vii—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—H82viii | 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—H82viii | 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 |
H82viii—C10—H101 | 93.31 | 91.8 | 94.06 |
H82viii—C10—H102 | 62.95 | 52.84 | 72.62 |
H82viii—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—O1i | 93.4 (2) | 92.9 (2) | 93.8 (2) |
O1—C11—C1 | 32.94 (17) | 32.72 (17) | 33.22 (17) |
O1—C11—C1i | 64.07 (19) | 63.87 (19) | 64.28 (19) |
O1—C11—C11i | 111.4 (3) | 110.7 (3) | 111.9 (3) |
O1—C11—H111 | 109.47 | 109.47 | 109.48 |
O1—C11—H111i | 96.39 | 95.95 | 96.81 |
O1—C11—H112 | 109.47 | 109.47 | 109.47 |
O1—C11—H112i | 137.95 | 137.27 | 138.53 |
O1i—C11—C1 | 61.79 (14) | 61.58 (14) | 62.16 (15) |
O1i—C11—C1i | 30.23 (11) | 30.00 (11) | 30.38 (11) |
O1i—C11—C11i | 33.91 (17) | 33.70 (17) | 34.07 (17) |
O1i—C11—H111 | 90.39 | 90.32 | 90.52 |
O1i—C11—H111i | 52.26 | 52.16 | 52.34 |
O1i—C11—H112 | 143.3 | 143.12 | 143.45 |
O1i—C11—H112i | 52.26 | 52.16 | 52.34 |
C1—C11—C1i | 31.68 (14) | 31.43 (14) | 32.01 (14) |
C1—C11—C11i | 87.2 (2) | 86.9 (2) | 87.5 (2) |
C1—C11—H111 | 98.82 | 98.1 | 99.72 |
C1—C11—H111i | 83.88 | 83.43 | 84.17 |
C1—C11—H112 | 141.13 | 140.78 | 141.5 |
C1—C11—H112i | 112.21 | 112.01 | 112.55 |
C1i—C11—C11i | 59.5 (2) | 59.3 (2) | 59.8 (2) |
C1i—C11—H111 | 93.19 | 92.4 | 93.85 |
C1i—C11—H111i | 66.61 | 66.26 | 66.95 |
C1i—C11—H112 | 159.16 | 158.89 | 159.47 |
C1i—C11—H112i | 81.93 | 81.7 | 82.16 |
C11i—C11—H111 | 109.47 | 109.47 | 109.47 |
C11i—C11—H111i | 26.65 | 26.63 | 26.68 |
C11i—C11—H112 | 109.47 | 109.46 | 109.48 |
C11i—C11—H112i | 26.65 | 26.62 | 26.68 |
H111—C11—H111i | 136.12 | 136.1 | 136.15 |
H111—C11—H112 | 107.51 | 106.9 | 108.21 |
H111—C11—H112i | 95.72 | 95.39 | 96.01 |
H111i—C11—H112 | 95.72 | 95.39 | 96.01 |
H111i—C11—H112i | 45.13 | 44.9 | 45.33 |
H112—C11—H112i | 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—H82v | 92.36 | 75.69 | 107.54 |
O1—H41—H102iv | 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—H82v | 110.92 | 96.54 | 123.34 |
C1—H41—H102iv | 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—H82v | 119.19 | 109.53 | 127.41 |
C2—H41—H102iv | 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—H82v | 110.22 | 107.2 | 115.05 |
C3—H41—H102iv | 164.55 | 162.81 | 166.93 |
C4—H41—C5 | 37.75 | 37.51 | 38 |
C4—H41—H82v | 92.5 | 86.05 | 97.35 |
C4—H41—H102iv | 129.28 | 125.86 | 133.08 |
C5—H41—H82v | 73.5 | 63.78 | 82.84 |
C5—H41—H102iv | 91.91 | 88.31 | 96.11 |
H82v—H41—H102iv | 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—H91ix | 95.66 | 89.03 | 101.15 |
Si1—H71—H93iv | 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—H91ix | 142.45 | 135.72 | 148.44 |
C7—H71—H93iv | 114.22 | 106.06 | 121.17 |
H72—H71—H73 | 60 | 59.97 | 60.03 |
H72—H71—H91ix | 154.51 | 151.91 | 157.4 |
H72—H71—H93iv | 116.21 | 104 | 126.83 |
H73—H71—H91ix | 136.51 | 132.03 | 142.03 |
H73—H71—H93iv | 80.88 | 74.18 | 86.94 |
H91ix—H71—H93iv | 87.77 | 76.34 | 103.79 |
Si1—H72—C7 | 47.96 | 47.81 | 48.11 |
Si1—H72—C9x | 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—H91x | 123.96 | 113.85 | 137.26 |
Si1—H72—H92x | 120.97 | 106.12 | 142.37 |
Si1—H72—H93x | 148.61 | 132.9 | 167.74 |
Si1—H72—H103iv | 93.11 | 90.88 | 94.83 |
C7—H72—C9x | 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—H91x | 160.81 | 146.94 | 179.43 |
C7—H72—H92x | 133.46 | 121.62 | 149.64 |
C7—H72—H93x | 141.73 | 131.88 | 153.22 |
C7—H72—H103iv | 93.17 | 92.29 | 94.1 |
C9x—H72—H71 | 114.69 | 103.43 | 127.89 |
C9x—H72—H73 | 152.19 | 137.87 | 163.75 |
C9x—H72—H91x | 17.83 | 17.27 | 18.9 |
C9x—H72—H92x | 17.26 | 16.19 | 18.76 |
C9x—H72—H93x | 17.45 | 16.45 | 18.8 |
C9x—H72—H103iv | 114.81 | 94.43 | 130.39 |
H71—H72—H73 | 60 | 59.97 | 60.03 |
H71—H72—H91x | 130.52 | 118.44 | 144.44 |
H71—H72—H92x | 101.05 | 90.96 | 114.37 |
H71—H72—H93x | 109.61 | 96.63 | 123.64 |
H71—H72—H103iv | 122.49 | 121.5 | 124.3 |
H73—H72—H91x | 160.84 | 141.2 | 175.54 |
H73—H72—H92x | 151.93 | 145.03 | 160.8 |
H73—H72—H93x | 135.16 | 120.21 | 147.47 |
H73—H72—H103iv | 62.58 | 61.59 | 64.32 |
H91x—H72—H92x | 29.53 | 27.15 | 32.06 |
H91x—H72—H93x | 31.46 | 29.03 | 34.03 |
H91x—H72—H103iv | 103.66 | 84.52 | 118.75 |
H92x—H72—H93x | 29.38 | 26.61 | 32.12 |
H92x—H72—H103iv | 131.46 | 111.41 | 145.46 |
H93x—H72—H103iv | 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—H93iv | 130.11 | 120.85 | 141.45 |
Si1—H73—H103iv | 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—H93iv | 100.35 | 95.42 | 106.51 |
C7—H73—H103iv | 115.54 | 113.76 | 116.72 |
H71—H73—H72 | 60 | 59.97 | 60.03 |
H71—H73—H93iv | 66.81 | 61.07 | 74.22 |
H71—H73—H103iv | 146.08 | 144.77 | 147.28 |
H72—H73—H93iv | 106.42 | 99.68 | 112.23 |
H72—H73—H103iv | 86.23 | 85.08 | 87.34 |
H93iv—H73—H103iv | 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—H91ix | 96.35 | 93.85 | 99.03 |
Si1—H81—H92vi | 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—H91ix | 142.84 | 140.51 | 146.37 |
C8—H81—H92vi | 129.79 | 127.41 | 133.21 |
H82—H81—H83 | 60 | 59.96 | 60.04 |
H82—H81—H91ix | 136.07 | 131.85 | 141.36 |
H82—H81—H92vi | 125.48 | 120.27 | 129.22 |
H83—H81—H91ix | 155.73 | 153.05 | 159.62 |
H83—H81—H92vi | 96.57 | 93.38 | 100.09 |
H91ix—H81—H92vi | 85.59 | 79.09 | 89.75 |
Si1—H82—C4iv | 106.34 | 102.91 | 108.92 |
Si1—H82—C5iv | 109.11 | 106.84 | 111.1 |
Si1—H82—C8 | 47.91 | 47.78 | 48.04 |
Si1—H82—C10xi | 163.37 | 155.38 | 168.35 |
Si1—H82—H41iv | 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—H102xi | 167.57 | 157.57 | 174.78 |
Si1—H82—H103xi | 154.72 | 141.1 | 168.96 |
C4iv—H82—C5iv | 27.46 | 26.64 | 28.24 |
C4iv—H82—C8 | 152.99 | 147.85 | 156.91 |
C4iv—H82—C10xi | 86.18 | 84.34 | 88.83 |
C4iv—H82—H41iv | 18.59 | 17.85 | 19.01 |
C4iv—H82—H81 | 156.97 | 149.92 | 163.27 |
C4iv—H82—H83 | 141.65 | 133.68 | 149.7 |
C4iv—H82—H102xi | 75.19 | 71.44 | 78.11 |
C4iv—H82—H103xi | 85.62 | 82.46 | 88.53 |
C5iv—H82—C8 | 151.03 | 145.59 | 156.17 |
C5iv—H82—C10xi | 79.83 | 76.73 | 82.12 |
C5iv—H82—H41iv | 41.47 | 40.08 | 42.83 |
C5iv—H82—H81 | 130.75 | 123.42 | 139.49 |
C5iv—H82—H83 | 168.84 | 160.32 | 175.77 |
C5iv—H82—H102xi | 76.51 | 75.09 | 77.61 |
C5iv—H82—H103xi | 71.81 | 66.88 | 76.04 |
C8—H82—C10xi | 118.88 | 116.37 | 121.62 |
C8—H82—H41iv | 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—H102xi | 127.54 | 126.08 | 128.89 |
C8—H82—H103xi | 119.6 | 115.54 | 123.85 |
C10xi—H82—H41iv | 75.41 | 72.87 | 79.35 |
C10xi—H82—H81 | 95.44 | 87.06 | 104.78 |
C10xi—H82—H83 | 101.72 | 96.65 | 107.52 |
C10xi—H82—H102xi | 17.74 | 16.78 | 18.59 |
C10xi—H82—H103xi | 17.42 | 15.91 | 18.42 |
H41iv—H82—H81 | 168.53 | 157.68 | 178.23 |
H41iv—H82—H83 | 128.34 | 119.76 | 137.66 |
H41iv—H82—H102xi | 61.33 | 57.61 | 64.98 |
H41iv—H82—H103xi | 79.87 | 76.77 | 84.22 |
H81—H82—H83 | 60 | 59.97 | 60.03 |
H81—H82—H102xi | 110.91 | 101.53 | 120.4 |
H81—H82—H103xi | 89.41 | 81.61 | 98.61 |
H83—H82—H102xi | 101.71 | 97.11 | 107.4 |
H83—H82—H103xi | 112.39 | 106.54 | 118.13 |
H102xi—H82—H103xi | 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—H101vi | 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—H101vi | 152.83 | 133.08 | 170.69 |
H81—H83—H82 | 60 | 59.96 | 60.04 |
H81—H83—H101vi | 153.14 | 140.76 | 160.85 |
H82—H83—H101vi | 140.33 | 122.12 | 154.25 |
Si1—H91—C9 | 47.93 | 47.78 | 48.16 |
Si1—H91—H71ix | 127.62 | 121.8 | 133.1 |
Si1—H91—H72vii | 137.41 | 133.76 | 140.27 |
Si1—H91—H81ix | 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—H71ix | 144.51 | 135.58 | 154.25 |
C9—H91—H72vii | 92.63 | 86.95 | 97.29 |
C9—H91—H81ix | 143.05 | 137.62 | 148.85 |
C9—H91—H92 | 35.26 | 35.26 | 35.27 |
C9—H91—H93 | 35.26 | 35.25 | 35.28 |
H71ix—H91—H72vii | 87.51 | 77.18 | 94.7 |
H71ix—H91—H81ix | 71.29 | 67.72 | 74.19 |
H71ix—H91—H92 | 110.64 | 102.14 | 119.66 |
H71ix—H91—H93 | 156.94 | 153.82 | 160.17 |
H72vii—H91—H81ix | 76.24 | 64.74 | 89.07 |
H72vii—H91—H92 | 81.31 | 64.95 | 95.1 |
H72vii—H91—H93 | 70.97 | 67.25 | 77.62 |
H81ix—H91—H92 | 157.24 | 151.65 | 161.97 |
H81ix—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—H72vii | 130.72 | 114.46 | 152.43 |
Si1—H92—H81xii | 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—H72vii | 82.94 | 66.84 | 104.64 |
C9—H92—H81xii | 162.51 | 152.15 | 170.75 |
C9—H92—H91 | 35.26 | 35.25 | 35.28 |
C9—H92—H93 | 35.26 | 35.25 | 35.27 |
H72vii—H92—H81xii | 81.17 | 66.79 | 89 |
H72vii—H92—H91 | 69.15 | 57.48 | 84.83 |
H72vii—H92—H93 | 65.74 | 50.75 | 86.92 |
H81xii—H92—H91 | 138.8 | 136.52 | 142.51 |
H81xii—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—H71v | 116.85 | 110.89 | 123.45 |
Si1—H93—H72vii | 143.94 | 131.15 | 151.46 |
Si1—H93—H73v | 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—H71v | 158.98 | 156.91 | 161.56 |
C9—H93—H72vii | 98.7 | 84.06 | 109.46 |
C9—H93—H73v | 128.71 | 125.46 | 130.73 |
C9—H93—H91 | 35.26 | 35.25 | 35.28 |
C9—H93—H92 | 35.26 | 35.26 | 35.27 |
H71v—H93—H72vii | 96.25 | 86.84 | 109.03 |
H71v—H93—H73v | 32.31 | 31.44 | 33.53 |
H71v—H93—H91 | 162.93 | 159.8 | 166.12 |
H71v—H93—H92 | 134.91 | 128.92 | 140.11 |
H72vii—H93—H73v | 107.88 | 100.16 | 114.09 |
H72vii—H93—H91 | 77.53 | 72.88 | 80.72 |
H72vii—H93—H92 | 84.86 | 63.28 | 102.46 |
H73v—H93—H91 | 163.45 | 159.25 | 165.92 |
H73v—H93—H92 | 104.9 | 99.45 | 109.21 |
H91—H93—H92 | 60 | 59.98 | 60.02 |
S2—H101—C6xii | 123.84 | 117.58 | 130.19 |
S2—H101—C10 | 47.57 | 47.54 | 47.65 |
S2—H101—H83xii | 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—H111ii | 88.57 | 87.41 | 89.73 |
C6xii—H101—C10 | 165.37 | 153.67 | 177.23 |
C6xii—H101—H83xii | 55.65 | 39.62 | 69.62 |
C6xii—H101—H102 | 135.99 | 125.94 | 147.61 |
C6xii—H101—H103 | 158.73 | 143.99 | 170.78 |
C6xii—H101—H111ii | 60.68 | 42.72 | 80.87 |
C10—H101—H83xii | 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—H111ii | 105.66 | 100.63 | 111.2 |
H83xii—H101—H102 | 148.84 | 142.12 | 154.19 |
H83xii—H101—H103 | 116.63 | 92.37 | 139.66 |
H83xii—H101—H111ii | 93.34 | 64.57 | 122.66 |
H102—H101—H103 | 60 | 59.99 | 60.01 |
H102—H101—H111ii | 80.89 | 74.4 | 88 |
H103—H101—H111ii | 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—H41v | 70.73 | 68.97 | 71.9 |
S1—H102—H82viii | 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—H111ii | 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—H41v | 127.11 | 121.19 | 132.5 |
S2—H102—H82viii | 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—H111ii | 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—H41v | 67.72 | 62.98 | 72.06 |
C2—H102—H82viii | 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—H111ii | 108.56 | 107.84 | 109.36 |
C3—H102—C10 | 72.66 | 72.52 | 72.88 |
C3—H102—H41v | 89.73 | 83.4 | 95.23 |
C3—H102—H82viii | 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—H111ii | 110.95 | 109.39 | 112.41 |
C10—H102—H41v | 137.12 | 134.1 | 139.66 |
C10—H102—H82viii | 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—H111ii | 96.81 | 92.38 | 101.19 |
H41v—H102—H82viii | 59.69 | 57.86 | 61.65 |
H41v—H102—H101 | 152.51 | 149.47 | 156.43 |
H41v—H102—H103 | 103.02 | 100.52 | 104.99 |
H41v—H102—H111ii | 125.87 | 119.94 | 132 |
H82viii—H102—H101 | 93.85 | 88.11 | 100.82 |
H82viii—H102—H103 | 71 | 60.56 | 82.61 |
H82viii—H102—H111ii | 124.15 | 119.46 | 129.22 |
H101—H102—H103 | 60 | 60 | 60 |
H101—H102—H111ii | 71.09 | 67.09 | 74.97 |
H103—H102—H111ii | 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—H72v | 128.13 | 123.72 | 133.32 |
S2—H103—H73v | 97.74 | 94.37 | 102.33 |
S2—H103—H82viii | 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—H72v | 113.84 | 109.31 | 119.21 |
C3—H103—H73v | 85.49 | 80.55 | 90.77 |
C3—H103—H82viii | 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—H72v | 162.64 | 159.87 | 165.47 |
C10—H103—H73v | 143.03 | 140.81 | 147.07 |
C10—H103—H82viii | 104.13 | 93.88 | 115.37 |
C10—H103—H101 | 35.26 | 35.26 | 35.27 |
C10—H103—H102 | 35.26 | 35.26 | 35.27 |
H72v—H103—H73v | 31.19 | 29.95 | 32.89 |
H72v—H103—H82viii | 84.46 | 74.91 | 92.25 |
H72v—H103—H101 | 130.21 | 126.01 | 132.63 |
H72v—H103—H102 | 159.23 | 155.11 | 162.08 |
H73v—H103—H82viii | 112.71 | 102.93 | 119.25 |
H73v—H103—H101 | 133.66 | 129.32 | 136.01 |
H73v—H103—H102 | 158.74 | 153.78 | 164.17 |
H82viii—H103—H101 | 96.68 | 90.91 | 103.59 |
H82viii—H103—H102 | 76.2 | 64.95 | 88.13 |
H101—H103—H102 | 60 | 59.99 | 60.01 |
S2v—H111—O1 | 143.35 | 136.93 | 148.77 |
S2v—H111—O1i | 101.42 | 94.88 | 107.06 |
S2v—H111—C1 | 120.49 | 118.33 | 121.87 |
S2v—H111—C1i | 106.73 | 103.46 | 108.77 |
S2v—H111—C5v | 60.44 | 57.79 | 62.73 |
S2v—H111—C11 | 167.03 | 158.12 | 174.93 |
S2v—H111—C11i | 123.4 | 114.65 | 131.45 |
S2v—H111—H101xiii | 79.02 | 71.34 | 86.52 |
S2v—H111—H102xiii | 77.42 | 71.31 | 82.61 |
S2v—H111—H111i | 137.16 | 128.36 | 145.23 |
S2v—H111—H112 | 145.98 | 144.23 | 147.4 |
S2v—H111—H112i | 107.69 | 98.68 | 116.37 |
O1—H111—O1i | 76.72 | 76.42 | 76.93 |
O1—H111—C1 | 30.04 | 29.63 | 30.35 |
O1—H111—C1i | 55.99 | 55.8 | 56.27 |
O1—H111—C5v | 84.51 | 79.74 | 89.28 |
O1—H111—C11 | 43.48 | 43.33 | 43.58 |
O1—H111—C11i | 74.46 | 74.01 | 74.85 |
O1—H111—H101xiii | 108.1 | 97.69 | 116.47 |
O1—H111—H102xiii | 124.66 | 119.37 | 127.7 |
O1—H111—H111i | 63.75 | 63.37 | 64.09 |
O1—H111—H112 | 67.11 | 66.88 | 67.29 |
O1—H111—H112i | 97.43 | 96.89 | 97.92 |
O1i—H111—C1 | 55.26 | 55.1 | 55.39 |
O1i—H111—C1i | 27.85 | 27.75 | 27.99 |
O1i—H111—C5v | 104.69 | 101.46 | 107.06 |
O1i—H111—C11 | 68.06 | 67.8 | 68.24 |
O1i—H111—C11i | 33.52 | 33.46 | 33.58 |
O1i—H111—H101xiii | 164.88 | 148.53 | 179.6 |
O1i—H111—H102xiii | 141.18 | 124.13 | 158.81 |
O1i—H111—H111i | 43.07 | 42.92 | 43.17 |
O1i—H111—H112 | 99.27 | 99.15 | 99.34 |
O1i—H111—H112i | 47.12 | 47.06 | 47.18 |
C1—H111—C1i | 29.03 | 28.75 | 29.3 |
C1—H111—C5v | 73.52 | 71.74 | 75.21 |
C1—H111—C11 | 60.22 | 59.49 | 60.78 |
C1—H111—C11i | 69.09 | 68.77 | 69.26 |
C1—H111—H101xiii | 132.47 | 116.41 | 145.86 |
C1—H111—H102xiii | 152.96 | 144.81 | 157.7 |
C1—H111—H111i | 64.7 | 64.25 | 65.03 |
C1—H111—H112 | 92.78 | 92.32 | 93.09 |
C1—H111—H112i | 92.97 | 92.69 | 93.17 |
C1i—H111—C5v | 83.68 | 82.06 | 84.71 |
C1i—H111—C11 | 67.61 | 67 | 68.34 |
C1i—H111—C11i | 52.61 | 52.38 | 52.85 |
C1i—H111—H101xiii | 159.31 | 142.84 | 170.96 |
C1i—H111—H102xiii | 165.51 | 150.53 | 178.18 |
C1i—H111—H111i | 55.35 | 54.93 | 55.74 |
C1i—H111—H112 | 103.82 | 103.51 | 104.24 |
C1i—H111—H112i | 72.58 | 72.41 | 72.79 |
C5v—H111—C11 | 127.92 | 123.29 | 132.39 |
C5v—H111—C11i | 135.99 | 133.96 | 137.23 |
C5v—H111—H101xiii | 85.14 | 63.62 | 107.01 |
C5v—H111—H102xiii | 107.86 | 90.08 | 124.96 |
C5v—H111—H111i | 137.09 | 135.89 | 138.19 |
C5v—H111—H112 | 137.2 | 131.38 | 143.61 |
C5v—H111—H112i | 149.21 | 144.24 | 153.06 |
C11—H111—C11i | 43.88 | 43.85 | 43.9 |
C11—H111—H101xiii | 108.31 | 100.57 | 114.07 |
C11—H111—H102xiii | 104.65 | 95.35 | 113.31 |
C11—H111—H111i | 30.08 | 30.05 | 30.11 |
C11—H111—H112 | 36.24 | 35.89 | 36.55 |
C11—H111—H112i | 59.96 | 59.75 | 60.22 |
C11i—H111—H101xiii | 136.92 | 118.88 | 153.37 |
C11i—H111—H102xiii | 115.24 | 98.27 | 132.72 |
C11i—H111—H111i | 13.8 | 13.79 | 13.8 |
C11i—H111—H112 | 67.43 | 67.34 | 67.55 |
C11i—H111—H112i | 24.32 | 24.25 | 24.39 |
H101xiii—H111—H102xiii | 28.01 | 24.88 | 30.64 |
H101xiii—H111—H111i | 129.19 | 114.26 | 141.79 |
H101xiii—H111—H112 | 75.32 | 64.69 | 85.94 |
H101xiii—H111—H112i | 122.03 | 101.58 | 142.65 |
H102xiii—H111—H111i | 113.16 | 97.71 | 128.7 |
H102xiii—H111—H112 | 69.45 | 62.45 | 77.21 |
H102xiii—H111—H112i | 95.44 | 77.99 | 113.68 |
H111i—H111—H112 | 56.22 | 56.05 | 56.39 |
H111i—H111—H112i | 33.71 | 33.54 | 33.87 |
H112—H111—H112i | 69.15 | 68.98 | 69.41 |
S1xiii—H112—S2xiii | 64.86 | 58.98 | 68.52 |
S1xiii—H112—O1 | 164.36 | 149.24 | 177.41 |
S1xiii—H112—C11 | 126.37 | 116.09 | 135.86 |
S1xiii—H112—C11i | 92.27 | 77.01 | 108.73 |
S1xiii—H112—H111 | 110.49 | 108.82 | 111.72 |
S1xiii—H112—H111i | 92.42 | 75.36 | 111 |
S1xiii—H112—H112i | 68.78 | 54.8 | 84.24 |
S2xiii—H112—O1 | 127.26 | 107.64 | 146.11 |
S2xiii—H112—C11 | 153.33 | 135.65 | 167.95 |
S2xiii—H112—C11i | 156.62 | 135.35 | 175.44 |
S2xiii—H112—H111 | 121.5 | 109.58 | 133.03 |
S2xiii—H112—H111i | 143.86 | 124.42 | 159.66 |
S2xiii—H112—H112i | 133.23 | 113.68 | 151.67 |
O1—H112—C11 | 43.48 | 43.33 | 43.58 |
O1—H112—C11i | 74.46 | 74 | 74.85 |
O1—H112—H111 | 67.11 | 66.87 | 67.28 |
O1—H112—H111i | 74.25 | 74 | 74.48 |
O1—H112—H112i | 98.56 | 98.1 | 98.88 |
C11—H112—C11i | 43.88 | 43.85 | 43.91 |
C11—H112—H111 | 36.24 | 35.89 | 36.55 |
C11—H112—H111i | 59.96 | 59.75 | 60.23 |
C11—H112—H112i | 61.83 | 61.78 | 61.88 |
C11i—H112—H111 | 67.43 | 67.33 | 67.55 |
C11i—H112—H111i | 24.32 | 24.24 | 24.39 |
C11i—H112—H112i | 24.8 | 24.77 | 24.83 |
H111—H112—H111i | 90.07 | 90.05 | 90.09 |
H111—H112—H112i | 71.55 | 71.42 | 71.65 |
H111i—H112—H112i | 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. |
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) Å3 |
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 on F | 240 constraints |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.042 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H212···O2i | 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. |
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) Å3 | Block, clear colourless |
Z = 4 | 0.70 × 0.56 × 0.50 mm |
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 on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.027 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
wR(F2) = 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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
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) Å3 | 0.09 × 0.07 × 0.01 mm |
Z = 4 |
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 on F | 56 constraints |
R[F2 > 2σ(F2)] = 0.078 | H-atom parameters constrained |
wR(F2) = 0.063 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
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 |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C1i | 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—C2i | 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—C1i | 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—C2i | 113.2 (4) | H81—C8—H83 | 109.47 |
C1—C2—H2 | 123.41 | H82—C8—H83 | 109.47 |
C2i—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. |
Acknowledgements
The authors are indebted to V. Carl, D. Koch, J. Steindl and D. Wurm for supporting the synthetic experiments. The authors also thank W. Skranc for preliminary work on the discussed topic. The help of Martin Lutz with the use of the EVAL software package is highly appreciated. The X-ray centre of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer. This publication was supported by TU Vienna research funds.
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