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Polymorphism and pseudosymmetry of 10,10′-oxybis(9-thia-10-hydro-10-boraanthracene)

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aInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

Edited by A. J. Lough, University of Toronto, Canada (Received 4 April 2019; accepted 16 April 2019; online 25 April 2019)

We have encountered two polymorphs of the title compound, C24H16B2OS2, both of which display almost the same unit-cell parameters. Compound (I) crystallizes in the non-centrosymmetric space group P21 with four mol­ecules in the asymmetric unit. These mol­ecules are related by pseudosymmetry. As a result, the space group looks like P21/c, but the structure cannot be refined successfully in that space group. Compound (II) on the other hand crystallizes in the centrosymmetric space group P21/c with only two mol­ecules in the asymmetric unit. The crystals studied for (I) and (II) were both non-merohedral twins.

1. Chemical context

Extended, conjugated π-systems are of great inter­est for both fundamental as well as applied materials research. They are typically utilized as key components for optoelectronic devices, such as organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs), and organic photovoltaics (OPVs), or as electrode materials in lithium batteries, often acting as the functional layer within these devices (Wu et al., 2007[Wu, J., Pisula, W. & Müllen, K. (2007). Chem. Rev. 107, 718-747.]; Harvey, 1997[Harvey, R. G. (1997). Polycyclic Aromatic Hydrocarbons. New York: Wiley and Sons.]). Archetypal examples from this class of compounds are polycyclic aromatic hydro­carbons (PAHs), which can be considered as well-defined cutouts of graphene with adjustable mol­ecular structure design and predictable supra­molecular arrangements (Rieger & Müllen, 2010[Rieger, R. & Müllen, K. (2010). J. Phys. Org. Chem. 23, 315-325.]). The properties of these all-carbon compounds can be further improved by substitutional doping with main-group elements, which has long been known for elements such as nitro­gen, phospho­rous, or sulfur (Stępień et al., 2017[Stępień, M., Gońka, E., Żyła, M. & Sprutta, N. (2017). Chem. Rev. 117, 3479-3716.]). However, only a few boron-doped PAHs have been synthesized to date, mainly because of synthetic difficulties (von Grotthuss et al., 2018[Grotthuss, E. von, John, A., Kaese, T. & Wagner, M. (2018). Asia. J. Org. Chem. 7, 37-53.]).

[Scheme 1]

The three-coordinate boron centre can be regarded as an equivalent to a carbenium ion due to its vacant pz orbital, and therefore acts as both a π-electron acceptor and σ-electron donor. The combination of electron-deficient boron centres with pnictogens or chalcogens, respectively, leads to compounds isoelectronic to the all-carbon systems (Liu & Marder, 2008[Liu, Z. & Marder, T. B. (2008). Angew. Chem. Int. Ed. 47, 242-244.]). Thus, we set out to design extended, conjugated π-systems, which also incorporate sulfur atoms in addition to boron centres.

2. Structural commentary

Mol­ecules of the title compounds (Figs. 1[link]–4[link][link][link]) feature two 9-thia-10-bora-anthracene moieties connected by an oxygen bridge. The dihedral angles between the two 9-thia-10-bora-anthracene moieties in (I)[link] are 86.26 (6)° for mol­ecule A, 88.07 (5)° for mol­ecule B, 85.82 (5)° for mol­ecule C, 89.69 (6)° for mol­ecule D.

[Figure 1]
Figure 1
A perspective view of one mol­ecule in the asymmetric unit of (I)[link]. H atoms are omitted for clarity.
[Figure 2]
Figure 2
A perspective view of the four mol­ecules in the asymmetric unit of (I)[link]. H atoms are omitted for clarity. Only B, O and S atoms are labelled.
[Figure 3]
Figure 3
A perspective view of one mol­ecule in the asymmetric unit of (II)[link]. H atoms are omitted for clarity.
[Figure 4]
Figure 4
A perspective view of both mol­ecules in the asymmetric unit of (II)[link]. H atoms are omitted for clarity. Only B, O and S atoms are labelled.

The dihedral angles between the two 9-thia-10-bora-anthracene moieties in (II)[link] are 84.03 (9)° for mol­ecule 1 and 87.19 (9)° for mol­ecule A.

Mol­ecules A and C of (I)[link] show a similar dihedral angle as mol­ecule 1 of (II)[link] and mol­ecules B and D of (I)[link] have a dihedral angle close to the one of mol­ecule A of (II)[link].

The B—O—B angles are significantly widened in both structures [(I): B2A—O1A—B1A 146.0 (6)°, B1B—O1B—B2B 164.8 (7)°, B2C—O1C—B1C 166.0 (7)°, B1D—O1D—B2D 165.9 (7)°; (II)[link]: B2—O1—B1 172.0 (7)° B1A—O1A—B2A 159.5 (7)°].

3. Supra­molecular features

The mol­ecular packing in both structures is very similar. In Figs. 5[link] and 6[link], mol­ecules that occupy a similar position in both structures are drawn with the same colour in order to illustrate the similarities between the structures.

[Figure 5]
Figure 5
Crystal packing of (I)[link]. Mol­ecules occupying similar positions in (I)[link] and (II)[link] are drawn with the same colour to illustrate the similarities between (I)[link] and (II)[link].
[Figure 6]
Figure 6
Crystal packing of (II)[link]. Mol­ecules occupying similar positions in (I)[link] and (II)[link] are drawn with the same colour to illustrate the similarities between (I)[link] and (II)[link].

In (I)[link], there are three C—H⋯π inter­actions with H⋯centroid (Cg) distances less than 3.0 Å [C4D—H4DCg(C21A–C26A)i: H⋯Cg = 2.90 Å, C—H⋯Cg = 137°; C14C—H14CCg(C1C–C6C)ii: H⋯Cg = 2.93 Å, C—H⋯Cg = 139°; C5B—H5BCg(C1D–C6D)iii: H⋯Cg = 2.78 Å, C—H⋯Cg = 139°; symmetry codes: (i) 1 − x, [{1\over 2}] + y, 1 − z; (ii) 1 − x, −[{1\over 2}] + y, 1 − z; (iii) 1 − x, [{1\over 2}] + y, 1 − z] and there is a ππ inter­action between the thia-boraanthracene fragment of mol­ecule B with the thia-boraanthracene fragment of mol­ecule C (transformed by x, y + 1, z) with an approximate distance of 3.8 Å between the thia-boraanthracene planes (Fig. 7[link]).

[Figure 7]
Figure 7
Partial packing diagram of (I)[link]. The mol­ecules containing O1A, O1B, O1C and O1D are the four symmetry-independent mol­ecules in the asymmetric unit. The mol­ecule containing O1E was generated by the symmetry operator 1 − x, [{1\over 2}] + y, 1 − z, that containing O1F by the symmetry operator 1 − x, −[{1\over 2}] + y, 1 − z, that containing O1G by the symmetry operator 1 − x, [{1\over 2}] + y, 1 − z and that containing O1H by the symmetry operator x, 1 + y, z. This mol­ecule is drawn with open bonds in order to show the ππ inter­action. Only the H atoms involved in a C—H⋯π inter­action are shown and labelled.

In (II)[link], there are two C—H⋯π inter­actions with H⋯Cg less than 3.0 Å [C4A—H4ACg(C11A–C16A)i: H⋯Cg = 2.77 Å, C—H⋯Cg = 147°; C15A—H15ACg(C31–C36)ii: H⋯Cg = 2.91 Å, C—H⋯Cg = 138°; symmetry codes: (i) x, [{1\over 2}] − y, [{1\over 2}] + z; (ii) 1 − x, 1 − y, −z] and there is a ππ inter­action between two thia-boraanthracene fragment related by a centre of inversion (−x + 1, −y + 1, −z + 1) with an approximate distance of 3.8 Å between the thia-boraanthracene planes (Fig. 8[link]).

[Figure 8]
Figure 8
Partial packing diagram of (II)[link]. The mol­ecules containing O1 and O1A are the two symmetry-independent mol­ecules in the asymmetric unit. The mol­ecule containing O1B was generated by the symmetry operator x, [{1\over 2}] − y, [{1\over 2}] + z, that containing O1C by the symmetry operator 1 − x, 1 − y, −z and that containing O1D by the symmetry operator 1 − x, 1 − y, 1 − z. This mol­ecule is drawn with open bonds in order to show the ππ inter­action. Only the H atoms involved in a C—H⋯π inter­action are shown and labelled.

4. Database survey

There are structures in the CSD (version 5.40 of November 2018; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) in which the thia-boraanthracene scaffold is comparable with the title compound, namely 2,9-di-t-butyl-7,14-dimesityl-7,14-di­hydro-5,12-di­thia-7,16-dibora­penta­cene (LIPFAS; Agou et al., 2007[Agou, T., Kobayashi, J. & Kawashima, T. (2007). Chem. Eur. J. 13, 8051-8060.]), 10-mesityl-10H-9-thia-10-boraanthracene (LIPFEW; Agou et al., 2007[Agou, T., Kobayashi, J. & Kawashima, T. (2007). Chem. Eur. J. 13, 8051-8060.]) and 10-mesityl-2,3,7,8-tetra­meth­oxy-10H-pheno­thia­borine (QONKAG; Kobayashi et al., 2009[Kobayashi, J., Kato, K., Agou, T. & Kawashima, T. (2009). Chem. Asian J. 4, 42-49.]). The B—C and S—C bond lengths as well as the C—B—C and C—S—C bond angles do not vary markedly between (I)[link], (II)[link] and the three comparable structures retrieved from the CSD (see Table 1[link]).

Table 1
Comparison of B—C and S—S bond lengths and C—B—C and C—S—C bond angles (Å, °)

  B—C C—B—C S—C C—S—C
LIPFAS 1.533 119.6 1.745 105.9
LIPFEW 1.546 119.4 1.745 106.5
QONKAG 1.534 119.6 1.740 106.2
(I) 1.539 121.8 1.758 106.4
(II) 1.548 120.2 1.746 106.3
Mean values of bond lengths [Å] and angles [°] in I and II and three structures (REFCODES given) from the CSD.

5. Synthesis and crystallization

10-Bromo-9-thia-10-hydro-10-borananthracene was synthesized according to a literature known procedure (Solé & Gabbaï, 2004[Solé, S. & Gabbaï, F. P. (2004). Chem. Commun. pp. 1284-1285.]). 2-Amino­ethanol (60 mg, 0.98 mmol) was added to a solution of 10-bromo-9-thia-boraanthracene (90 mg, 0.33 mmol) in 10 mL of toluene at room temperature. The yellow solution turned colorless overnight and a fluffy precipitate formed. The solvent was removed and the obtained white solid was dissolved in 5 mL of ethanol without further purification. 1 mL of 6N HCl was added to this clear solution at 273 K, after which the reaction mixture turned opaque, further addition of 5 mL of 1N HCl caused the formation of a voluminous precipitate. After stirring for 90 minutes at 273 K, the reaction mixture was filtered, and the residue was washed with ice-cold water (3 × 3 mL). The remaining white solid was dried under vacuum at 333 K to remove traces of water and was afterwards sublimated under vacuum at 503 K to give 10,10′-oxybis[9-thia-10-hydro-10-boraanthracene] as crystalline material. Yield: 53 mg (0.13 mmol, 80%).

Note: Crystals of polymorph (I)[link] were obtained via slow evaporation of a saturated solution of 10,10′-oxybis[9-thia-10-hydro-10-boraanthracene] in CH2Cl2 at room temperature. Crystals of polymorph (II)[link] were obtained via sublimation of 10,10′-oxybis[9-thia-10-hydro-10-boraanthracene].

1H NMR (500.18 MHz, CD2Cl2): δ = 8.02 (dd, 3JH-H = 7.6 Hz, 4JH-H = 0.8 Hz, 2H, H-4,5), 7.69 (d, 3JH-H = 8.0 Hz, 2H, H-1,8), 7.60–7.55 (m, 2H, H-2,7), 7.25 ppm (t, 3JH-H = 7.5 Hz, 2H, H-3,6).

13C{1H} NMR (125.78 MHz, CD2Cl2): δ = 125.2 (C-3,6), 126.0 (C-1,8), 129.0 (C-4a,10a), 132.1 (C-2,7), 135.0 (C-4,5), 145.9 ppm (C-8a,9a)

11B NMR (160.5 MHz, CD2Cl2): δ = 39.2 ppm

EA (%): Calculated for C24H16B2OS2 [406.14]: C 70.98, H 3.97, S 15.79; found: C 70.14, H 4.09, S 16.06

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The H atoms for both structures were refined using a riding model with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C). The fractional contribution of the minor twin domain refined to 0.4753 (7) for (I)[link] and 0.4547 (15) for (II)[link]. The absolute structure of (I)[link] could not be reliably determined, the Flack x parameter (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]) refined to 0.28 (3).

Table 2
Experimental details

  (I) (II)
Crystal data
Chemical formula C24H16B2OS2 C24H16B2OS2
Mr 406.11 406.11
Crystal system, space group Monoclinic, P21 Monoclinic, P21/c
Temperature (K) 173 173
a, b, c (Å) 13.2989 (11), 12.7097 (7), 23.3300 (16) 23.2471 (18), 12.5949 (16), 13.3561 (11)
β (°) 93.727 (6) 92.217 (6)
V3) 3935.0 (5) 3907.7 (7)
Z 8 8
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.28 0.29
Crystal size (mm) 0.26 × 0.25 × 0.25 0.19 × 0.12 × 0.09
 
Data collection
Diffractometer Stoe IPDS II two-circle Stoe IPDS II two-circle
Absorption correction Multi-scan (X-AREA; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]) Multi-scan (X-AREA; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.787, 1.000 0.677, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 48969, 48969, 39838 32689, 32689, 13195
(sin θ/λ)max−1) 0.615 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.082, 0.90 0.079, 0.184, 0.86
No. of reflections 48969 32689
No. of parameters 1046 524
No. of restraints 1 0
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.32, −0.25 0.48, −0.28
Absolute structure Flack x determined using 5084 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.28 (3)
Computer programs: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]), SHELXS97 and XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

It is remarkable that (I)[link] and (II)[link] show almost the same cell parameters. The a and c axes of (II)[link] were chosen in order to refine the structure in the conventional setting for P21/c. Compound (I)[link] crystallizes in the monoclinic non-centrosymmetric space group P21 with four mol­ecules in the asymmetric unit. A search for higher symmetry with the program PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) reveals that 97% of the structure complies with a centre of inversion and PLATON suggests a space group change to P21/c. However, the structure cannot be refined successfully in this space group. The displacement parameters of two atoms go NPD and the figures of merit are rather bad (R1 = 0.339, wR2 = 0.722). On the other hand, compound (II)[link] can be refined in the centrosymmetric space group P21/c with just two mol­ecules in the asymmetric unit. A closer look at the systematic absence exceptions for (I)[link] (Table 3[link]) and (II)[link] (Table 4[link]) reveals a remarkable difference between the two. For (I)[link], the reflections which should be extinct for an a glide plane are weaker than those for a c or an n glide plane. Nevertheless, they are definitely observed. For (II)[link], on the other hand, the reflections which should be extinct for a c glide plane are doubtlessly extinct. In (II)[link], the dis­place­ment ellipsoids of some C atoms in the outer positions of the aromatic rings are enlarged, which is most probably due to slight disorder. This disorder can be explained by a rotation of the thia-boraanthracene moiety about an axis perpendicular to the mean plane of this fragment running through the center of the central ring.

Table 3
Systematic absence exceptions for (I)[link] (space group P21)

  -21- -a- -c- -n-
N 54 2011 1973 1994
N[I>3σ(I)] 0 1185 1270 1219
mean intensity 0.3 2.8 5.6 5.6
mean I/σ(I) 1.0 7.4 11.6 11.5
N: number of reflection per group; N[I>3σ(I)]: number of reflections with I greater than 3σ(I).

Table 4
Systematic absence exceptions for (II)[link] (space group P21/c)

  -21- -a- -c- -n-
N 14 1687 1697 1694
N(I>3σ(I)) 0 330 103 350
mean intensity 0.3 5.0 0.7 5.1
mean I/σ(I) 0.9 5.0 1.5 5.1
N: number of reflection per group; N[I>3σ(I)]: number of reflections with I greater than 3σ(I).

Supporting information


Computing details top

For both structures, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008)' and Mercury (Macrae et al., 2008) for (I); XP in SHELXTL-Plus (Sheldrick, 2008) for (II). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010) for (I); SHELXL2014 (Sheldrick, 2014) for (II).

10,10'-Oxybis(9-thia-10-hydro-10-boraanthracene) (I) top
Crystal data top
C24H16B2OS2F(000) = 1680
Mr = 406.11Dx = 1.371 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 13.2989 (11) ÅCell parameters from 16197 reflections
b = 12.7097 (7) Åθ = 3.3–25.9°
c = 23.3300 (16) ŵ = 0.28 mm1
β = 93.727 (6)°T = 173 K
V = 3935.0 (5) Å3Block, colourless
Z = 80.26 × 0.25 × 0.25 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
48969 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source39838 reflections with I > 2σ(I)
ω scansθmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan
(X-Area; Stoe & Cie, 2001)
h = 1616
Tmin = 0.787, Tmax = 1.000k = 1515
48969 measured reflectionsl = 2828
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0272P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max = 0.001
S = 0.90Δρmax = 0.32 e Å3
48969 reflectionsΔρmin = 0.25 e Å3
1046 parametersAbsolute structure: Flack x determined using 5084 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.28 (3)
Primary atom site location: structure-invariant direct methods
Special details top

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

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.89147 (14)0.21177 (14)0.06026 (6)0.0298 (4)
S2A0.90496 (15)0.13029 (17)0.31658 (7)0.0455 (5)
O1A0.8426 (3)0.2439 (4)0.13221 (17)0.0336 (11)
B1A0.8609 (6)0.2311 (6)0.0747 (3)0.0265 (17)
B2A0.8614 (6)0.2077 (7)0.1862 (3)0.0274 (17)
C1A0.9542 (5)0.2799 (5)0.0503 (3)0.0257 (15)
C2A0.9708 (5)0.2760 (5)0.0082 (3)0.0252 (15)
C3A1.0560 (5)0.3245 (5)0.0302 (3)0.0312 (16)
H3A1.06540.32280.07020.037*
C4A1.1257 (6)0.3745 (6)0.0075 (3)0.0401 (19)
H4A1.18380.40620.00680.048*
C5A1.1114 (6)0.3785 (6)0.0656 (3)0.0429 (19)
H5A1.15900.41330.09110.052*
C6A1.0284 (6)0.3320 (6)0.0861 (3)0.0366 (18)
H6A1.02010.33470.12620.044*
C11A0.7812 (5)0.1704 (5)0.0356 (3)0.0258 (15)
C12A0.7920 (5)0.1584 (5)0.0237 (3)0.0242 (15)
C13A0.7216 (5)0.1003 (5)0.0577 (3)0.0307 (16)
H13A0.72990.09280.09760.037*
C14A0.6403 (6)0.0536 (6)0.0341 (3)0.0333 (17)
H14A0.59340.01370.05770.040*
C15A0.6268 (6)0.0650 (6)0.0244 (3)0.0399 (19)
H15A0.57070.03370.04100.048*
C16A0.6963 (6)0.1224 (6)0.0575 (3)0.0349 (17)
H16A0.68660.13000.09730.042*
C21A0.8145 (5)0.2684 (6)0.2350 (3)0.0291 (16)
C22A0.8274 (5)0.2385 (6)0.2936 (3)0.0341 (17)
C23A0.7834 (6)0.2916 (7)0.3374 (3)0.048 (2)
H23A0.79150.26690.37590.058*
C24A0.7280 (6)0.3800 (7)0.3245 (3)0.050 (2)
H24A0.69950.41860.35430.059*
C25A0.7132 (6)0.4136 (7)0.2684 (3)0.048 (2)
H25A0.67390.47460.25980.058*
C26A0.7551 (6)0.3594 (6)0.2245 (3)0.0405 (19)
H26A0.74360.38400.18620.049*
C31A0.9257 (5)0.1074 (6)0.1989 (3)0.0317 (17)
C32A0.9480 (5)0.0728 (6)0.2551 (3)0.0385 (18)
C33A1.0096 (6)0.0163 (6)0.2661 (3)0.047 (2)
H33A1.02460.03900.30450.057*
C34A1.0479 (6)0.0704 (6)0.2214 (4)0.048 (2)
H34A1.08970.13010.22900.058*
C35A1.0260 (5)0.0385 (6)0.1655 (3)0.0402 (17)
H35A1.05170.07650.13460.048*
C36A0.9669 (5)0.0486 (5)0.1548 (3)0.0331 (16)
H36A0.95310.07020.11610.040*
S1B0.88729 (15)0.68772 (15)0.17437 (7)0.0365 (4)
S2B0.89332 (14)0.73517 (14)0.56106 (6)0.0332 (4)
O1B0.8427 (4)0.7147 (5)0.36589 (19)0.0488 (14)
B1B0.8557 (6)0.7069 (7)0.3093 (3)0.034 (2)
B2B0.8564 (6)0.7241 (6)0.4239 (3)0.0273 (18)
C1B0.8059 (5)0.7855 (5)0.2684 (3)0.0302 (16)
C2B0.8154 (5)0.7830 (6)0.2089 (3)0.0280 (15)
C3B0.7685 (5)0.8556 (6)0.1712 (3)0.0380 (18)
H3B0.77690.85160.13120.046*
C4B0.7088 (6)0.9345 (6)0.1934 (3)0.050 (2)
H4B0.67580.98410.16820.060*
C5B0.6977 (6)0.9405 (6)0.2510 (4)0.048 (2)
H5B0.65720.99430.26590.057*
C6B0.7454 (5)0.8684 (6)0.2878 (3)0.0379 (18)
H6B0.73730.87460.32780.046*
C11B0.9194 (5)0.6136 (6)0.2870 (3)0.0307 (16)
C12B0.9361 (5)0.6028 (6)0.2288 (3)0.0299 (16)
C13B0.9929 (6)0.5182 (6)0.2077 (3)0.042 (2)
H13B1.00170.51150.16780.050*
C14B1.0352 (6)0.4457 (6)0.2466 (4)0.047 (2)
H14B1.07490.38990.23320.056*
C15B1.0206 (6)0.4534 (7)0.3044 (3)0.049 (2)
H15B1.04870.40220.33050.059*
C16B0.9645 (6)0.5363 (6)0.3242 (3)0.042 (2)
H16B0.95600.54150.36420.050*
C21B0.9479 (5)0.7871 (5)0.4509 (3)0.0312 (16)
C22B0.9658 (6)0.7958 (5)0.5104 (3)0.0325 (17)
C23B1.0491 (6)0.8539 (6)0.5348 (3)0.0416 (19)
H23B1.06040.85930.57530.050*
C24B1.1135 (7)0.9023 (7)0.4989 (4)0.054 (2)
H24B1.16970.94100.51490.065*
C25B1.0967 (7)0.8947 (7)0.4397 (4)0.052 (2)
H25B1.14150.92840.41540.062*
C26B1.0157 (6)0.8390 (6)0.4160 (3)0.0418 (19)
H26B1.00510.83520.37540.050*
C31B0.7808 (5)0.6710 (5)0.4614 (3)0.0273 (15)
C32B0.7926 (5)0.6726 (5)0.5221 (3)0.0256 (15)
C33B0.7230 (6)0.6218 (6)0.5553 (3)0.0355 (17)
H33B0.73220.62330.59600.043*
C34B0.6418 (6)0.5701 (6)0.5294 (3)0.043 (2)
H34B0.59520.53540.55220.051*
C35B0.6275 (6)0.5686 (6)0.4695 (4)0.044 (2)
H35B0.57080.53350.45160.052*
C36B0.6952 (6)0.6177 (6)0.4365 (3)0.0388 (18)
H36B0.68430.61600.39590.047*
S1C0.61092 (14)0.08919 (13)0.43175 (7)0.0313 (4)
S2C0.61166 (15)0.07447 (15)0.82018 (7)0.0362 (4)
O1C0.6394 (4)0.0556 (4)0.62671 (18)0.0512 (15)
B1C0.6362 (7)0.0753 (6)0.5685 (3)0.033 (2)
B2C0.6316 (7)0.0595 (7)0.6850 (3)0.0325 (19)
C1C0.7171 (5)0.0266 (5)0.5336 (3)0.0275 (15)
C2C0.7105 (5)0.0304 (5)0.4736 (3)0.0271 (15)
C3C0.7844 (6)0.0170 (6)0.4420 (3)0.0341 (17)
H3C0.77870.01480.40120.041*
C4C0.8645 (6)0.0663 (6)0.4698 (4)0.044 (2)
H4C0.91420.09850.44810.053*
C5C0.8743 (6)0.0702 (7)0.5290 (4)0.046 (2)
H5C0.93070.10410.54810.056*
C6C0.8022 (6)0.0247 (6)0.5602 (3)0.0398 (19)
H6C0.80960.02760.60090.048*
C11C0.5500 (5)0.1443 (5)0.5403 (3)0.0318 (17)
C12C0.5356 (5)0.1519 (5)0.4804 (3)0.0312 (17)
C13C0.4552 (6)0.2107 (6)0.4545 (4)0.046 (2)
H13C0.44590.21530.41380.055*
C14C0.3899 (6)0.2619 (7)0.4892 (4)0.058 (3)
H14C0.33500.30080.47200.070*
C15C0.4034 (7)0.2571 (7)0.5487 (4)0.061 (3)
H15C0.35980.29440.57210.073*
C16C0.4809 (7)0.1974 (6)0.5730 (3)0.043 (2)
H16C0.48820.19180.61370.052*
C21C0.5655 (5)0.0208 (5)0.7130 (3)0.0269 (15)
C22C0.5540 (5)0.0191 (6)0.7728 (3)0.0268 (15)
C23C0.4943 (6)0.0924 (6)0.7988 (3)0.0392 (19)
H23C0.48630.08850.83890.047*
C24C0.4466 (6)0.1711 (6)0.7663 (3)0.0421 (19)
H24C0.40630.22160.78410.051*
C25C0.4575 (6)0.1763 (7)0.7077 (3)0.046 (2)
H25C0.42430.22970.68520.056*
C26C0.5166 (6)0.1037 (6)0.6825 (3)0.0379 (19)
H26C0.52490.10960.64250.045*
C31C0.6902 (5)0.1460 (5)0.7193 (3)0.0310 (16)
C32C0.6835 (6)0.1562 (6)0.7788 (3)0.0326 (17)
C33C0.7360 (6)0.2369 (6)0.8093 (3)0.0399 (18)
H33C0.72990.24390.84950.048*
C34C0.7967 (6)0.3063 (6)0.7813 (3)0.0452 (19)
H34C0.83240.36020.80230.054*
C35C0.8051 (5)0.2969 (6)0.7224 (3)0.0433 (19)
H35C0.84630.34420.70290.052*
C36C0.7533 (5)0.2187 (6)0.6925 (3)0.0387 (18)
H36C0.76000.21300.65240.046*
S1D0.63335 (16)0.46013 (16)0.67962 (7)0.0452 (5)
S2D0.61249 (14)0.39294 (14)1.06599 (7)0.0303 (4)
O1D0.6197 (4)0.3876 (4)0.87045 (18)0.0462 (14)
B1D0.6239 (6)0.4121 (7)0.8135 (3)0.034 (2)
B2D0.6190 (7)0.3891 (6)0.9298 (3)0.033 (2)
C1D0.5722 (5)0.5107 (6)0.7887 (3)0.0312 (16)
C2D0.5717 (6)0.5347 (6)0.7307 (3)0.0344 (17)
C3D0.5199 (6)0.6228 (6)0.7067 (3)0.0444 (19)
H3D0.52000.63660.66670.053*
C4D0.4701 (6)0.6873 (7)0.7412 (4)0.054 (2)
H4D0.43490.74650.72510.065*
C5D0.4695 (6)0.6687 (7)0.7998 (4)0.049 (2)
H5D0.43490.71500.82360.059*
C6D0.5197 (6)0.5820 (6)0.8230 (3)0.043 (2)
H6D0.51930.56970.86320.051*
C11D0.6837 (5)0.3374 (6)0.7754 (3)0.0329 (17)
C12D0.6906 (5)0.3549 (5)0.7170 (3)0.0316 (16)
C13D0.7470 (6)0.2852 (6)0.6844 (3)0.048 (2)
H13D0.75360.29820.64470.057*
C14D0.7923 (6)0.1980 (8)0.7104 (5)0.062 (3)
H14D0.82920.15060.68830.075*
C15D0.7844 (6)0.1798 (7)0.7673 (4)0.065 (3)
H15D0.81600.11960.78470.078*
C16D0.7318 (6)0.2466 (6)0.7997 (4)0.050 (2)
H16D0.72720.23220.83940.060*
C21D0.7042 (5)0.4460 (5)0.9650 (3)0.0276 (15)
C22D0.7055 (5)0.4490 (5)1.0250 (3)0.0275 (15)
C23D0.7831 (5)0.5002 (6)1.0585 (3)0.0340 (17)
H23D0.78230.50191.09920.041*
C24D0.8602 (6)0.5480 (6)1.0311 (3)0.042 (2)
H24D0.91410.58061.05320.051*
C25D0.8598 (6)0.5488 (6)0.9715 (4)0.045 (2)
H25D0.91190.58380.95310.054*
C26D0.7835 (6)0.4986 (6)0.9391 (3)0.0370 (18)
H26D0.78430.49930.89840.044*
C31D0.5335 (5)0.3302 (5)0.9571 (3)0.0244 (14)
C32D0.5271 (5)0.3300 (5)1.0169 (3)0.0276 (15)
C33D0.4481 (6)0.2760 (6)1.0413 (3)0.0365 (18)
H33D0.44490.27511.08180.044*
C34D0.3754 (6)0.2244 (6)1.0073 (3)0.0414 (19)
H34D0.32240.18821.02440.050*
C35D0.3796 (6)0.2255 (7)0.9479 (3)0.046 (2)
H35D0.32940.19060.92400.055*
C36D0.4572 (6)0.2774 (6)0.9242 (3)0.0390 (18)
H36D0.45930.27770.88360.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0306 (10)0.0384 (11)0.0207 (7)0.0028 (8)0.0032 (7)0.0001 (7)
S2A0.0469 (12)0.0640 (13)0.0254 (8)0.0038 (11)0.0011 (8)0.0113 (8)
O1A0.037 (3)0.040 (3)0.024 (2)0.005 (2)0.0031 (19)0.002 (2)
B1A0.035 (4)0.020 (4)0.025 (3)0.011 (4)0.002 (3)0.006 (3)
B2A0.021 (4)0.032 (4)0.030 (4)0.010 (4)0.004 (3)0.001 (3)
C1A0.032 (4)0.023 (4)0.022 (3)0.003 (3)0.002 (3)0.004 (3)
C2A0.020 (4)0.024 (4)0.031 (3)0.003 (3)0.001 (3)0.001 (3)
C3A0.030 (4)0.030 (4)0.034 (3)0.000 (3)0.002 (3)0.003 (3)
C4A0.028 (4)0.038 (4)0.055 (4)0.004 (3)0.007 (3)0.002 (4)
C5A0.037 (4)0.041 (5)0.049 (4)0.016 (4)0.004 (4)0.007 (3)
C6A0.054 (5)0.032 (4)0.024 (3)0.000 (4)0.001 (3)0.006 (3)
C11A0.030 (4)0.022 (4)0.026 (3)0.004 (3)0.007 (3)0.003 (3)
C12A0.023 (4)0.022 (4)0.028 (3)0.003 (3)0.002 (3)0.003 (3)
C13A0.038 (4)0.029 (4)0.025 (3)0.005 (3)0.000 (3)0.003 (3)
C14A0.028 (4)0.025 (4)0.046 (4)0.001 (3)0.001 (3)0.002 (3)
C15A0.035 (4)0.031 (4)0.056 (5)0.007 (4)0.019 (4)0.003 (4)
C16A0.043 (4)0.031 (4)0.033 (3)0.004 (4)0.018 (3)0.002 (3)
C21A0.020 (3)0.034 (4)0.033 (3)0.005 (3)0.003 (3)0.001 (3)
C22A0.027 (4)0.045 (4)0.031 (3)0.010 (4)0.006 (3)0.002 (3)
C23A0.059 (5)0.061 (6)0.026 (3)0.021 (5)0.013 (3)0.005 (3)
C24A0.054 (5)0.049 (5)0.048 (4)0.017 (4)0.022 (4)0.022 (4)
C25A0.039 (5)0.044 (5)0.064 (5)0.001 (4)0.015 (4)0.012 (4)
C26A0.042 (4)0.050 (5)0.030 (3)0.010 (4)0.005 (3)0.001 (3)
C31A0.030 (4)0.040 (4)0.026 (3)0.010 (3)0.005 (3)0.003 (3)
C32A0.030 (4)0.039 (4)0.046 (4)0.012 (4)0.004 (3)0.011 (3)
C33A0.038 (5)0.046 (5)0.057 (5)0.001 (4)0.004 (4)0.025 (4)
C34A0.029 (4)0.031 (4)0.084 (6)0.000 (3)0.004 (4)0.013 (4)
C35A0.025 (4)0.033 (4)0.063 (5)0.004 (3)0.007 (3)0.005 (4)
C36A0.026 (4)0.032 (4)0.042 (4)0.006 (3)0.004 (3)0.008 (3)
S1B0.0484 (12)0.0391 (10)0.0226 (7)0.0079 (10)0.0063 (8)0.0007 (7)
S2B0.0355 (10)0.0422 (11)0.0218 (7)0.0020 (9)0.0019 (7)0.0033 (7)
O1B0.052 (3)0.069 (4)0.026 (2)0.008 (3)0.005 (2)0.003 (2)
B1B0.028 (4)0.045 (5)0.027 (4)0.015 (4)0.001 (3)0.006 (4)
B2B0.030 (4)0.028 (4)0.024 (3)0.007 (4)0.007 (3)0.000 (3)
C1B0.025 (4)0.032 (4)0.034 (3)0.009 (3)0.007 (3)0.005 (3)
C2B0.026 (4)0.031 (4)0.028 (3)0.008 (3)0.005 (3)0.001 (3)
C3B0.029 (4)0.047 (5)0.039 (4)0.001 (4)0.007 (3)0.011 (3)
C4B0.040 (5)0.044 (5)0.067 (5)0.003 (4)0.013 (4)0.016 (4)
C5B0.031 (4)0.030 (5)0.084 (6)0.001 (3)0.019 (4)0.003 (4)
C6B0.036 (4)0.044 (5)0.035 (4)0.011 (4)0.011 (3)0.014 (3)
C11B0.029 (4)0.036 (4)0.027 (3)0.003 (3)0.005 (3)0.007 (3)
C12B0.024 (4)0.032 (4)0.034 (4)0.003 (3)0.001 (3)0.000 (3)
C13B0.043 (5)0.041 (5)0.042 (4)0.004 (4)0.004 (4)0.002 (4)
C14B0.039 (5)0.031 (5)0.070 (5)0.002 (4)0.001 (4)0.001 (4)
C15B0.048 (5)0.040 (5)0.058 (5)0.003 (4)0.011 (4)0.018 (4)
C16B0.046 (5)0.047 (5)0.032 (4)0.013 (4)0.003 (3)0.007 (3)
C21B0.037 (4)0.027 (4)0.031 (3)0.004 (3)0.006 (3)0.006 (3)
C22B0.032 (4)0.026 (4)0.040 (4)0.006 (3)0.006 (3)0.003 (3)
C23B0.033 (4)0.047 (5)0.043 (4)0.003 (4)0.006 (3)0.015 (4)
C24B0.038 (5)0.041 (5)0.084 (6)0.013 (4)0.007 (4)0.012 (4)
C25B0.046 (5)0.048 (5)0.062 (5)0.008 (5)0.013 (4)0.005 (4)
C26B0.044 (5)0.043 (5)0.040 (4)0.003 (4)0.011 (4)0.007 (3)
C31B0.034 (4)0.022 (4)0.026 (3)0.002 (3)0.001 (3)0.001 (3)
C32B0.026 (4)0.023 (4)0.028 (3)0.001 (3)0.005 (3)0.003 (3)
C33B0.043 (4)0.035 (4)0.029 (3)0.000 (4)0.008 (3)0.000 (3)
C34B0.048 (5)0.031 (5)0.050 (5)0.005 (4)0.016 (4)0.008 (3)
C35B0.039 (5)0.032 (4)0.060 (5)0.007 (4)0.002 (4)0.002 (4)
C36B0.042 (4)0.037 (4)0.037 (4)0.000 (4)0.003 (4)0.002 (3)
S1C0.0368 (10)0.0352 (10)0.0222 (7)0.0077 (8)0.0049 (7)0.0031 (7)
S2C0.0479 (12)0.0405 (11)0.0206 (7)0.0075 (9)0.0053 (8)0.0008 (7)
O1C0.072 (4)0.059 (4)0.024 (2)0.010 (3)0.010 (2)0.001 (2)
B1C0.049 (5)0.035 (5)0.017 (3)0.014 (4)0.013 (3)0.004 (3)
B2C0.036 (5)0.040 (5)0.021 (3)0.007 (4)0.003 (3)0.005 (3)
C1C0.029 (4)0.027 (4)0.027 (3)0.003 (3)0.001 (3)0.000 (3)
C2C0.029 (4)0.024 (4)0.028 (3)0.001 (3)0.002 (3)0.003 (3)
C3C0.038 (4)0.029 (4)0.035 (4)0.003 (3)0.007 (3)0.003 (3)
C4C0.038 (5)0.036 (5)0.058 (5)0.009 (4)0.002 (4)0.006 (4)
C5C0.035 (5)0.041 (5)0.062 (5)0.016 (4)0.012 (4)0.002 (4)
C6C0.045 (5)0.041 (5)0.031 (4)0.002 (4)0.012 (3)0.005 (3)
C11C0.036 (4)0.021 (4)0.040 (4)0.009 (3)0.018 (3)0.010 (3)
C12C0.031 (4)0.025 (4)0.038 (4)0.002 (3)0.005 (3)0.001 (3)
C13C0.042 (5)0.035 (4)0.060 (5)0.005 (4)0.007 (4)0.007 (4)
C14C0.034 (5)0.032 (5)0.109 (7)0.012 (4)0.014 (5)0.011 (5)
C15C0.056 (6)0.035 (5)0.096 (7)0.003 (5)0.039 (5)0.006 (5)
C16C0.051 (5)0.032 (4)0.050 (4)0.005 (4)0.024 (4)0.011 (4)
C21C0.020 (3)0.032 (4)0.029 (3)0.000 (3)0.003 (3)0.000 (3)
C22C0.021 (4)0.033 (4)0.026 (3)0.002 (3)0.001 (3)0.003 (3)
C23C0.043 (5)0.043 (5)0.031 (3)0.007 (4)0.001 (3)0.006 (3)
C24C0.036 (4)0.039 (4)0.051 (4)0.007 (4)0.000 (3)0.011 (4)
C25C0.046 (5)0.037 (5)0.055 (4)0.009 (4)0.005 (4)0.004 (4)
C26C0.041 (4)0.046 (5)0.026 (3)0.001 (4)0.000 (3)0.007 (3)
C31C0.032 (4)0.032 (4)0.029 (3)0.003 (3)0.007 (3)0.009 (3)
C32C0.028 (4)0.031 (4)0.039 (4)0.000 (3)0.005 (3)0.003 (3)
C33C0.038 (4)0.045 (5)0.036 (4)0.001 (4)0.003 (3)0.004 (3)
C34C0.033 (4)0.038 (4)0.064 (5)0.008 (4)0.002 (4)0.006 (4)
C35C0.029 (4)0.039 (5)0.063 (5)0.008 (4)0.010 (4)0.009 (4)
C36C0.035 (4)0.041 (5)0.040 (4)0.004 (4)0.007 (3)0.012 (3)
S1D0.0579 (13)0.0541 (13)0.0248 (8)0.0059 (11)0.0120 (8)0.0061 (8)
S2D0.0324 (10)0.0351 (11)0.0235 (8)0.0040 (8)0.0041 (7)0.0005 (7)
O1D0.050 (3)0.061 (3)0.028 (2)0.010 (3)0.004 (2)0.009 (2)
B1D0.034 (5)0.051 (5)0.016 (3)0.015 (4)0.003 (3)0.001 (3)
B2D0.047 (5)0.031 (5)0.021 (3)0.010 (4)0.002 (4)0.005 (3)
C1D0.023 (4)0.032 (4)0.039 (4)0.003 (3)0.008 (3)0.000 (3)
C2D0.035 (4)0.032 (4)0.037 (4)0.007 (3)0.007 (3)0.007 (3)
C3D0.046 (5)0.036 (4)0.052 (4)0.005 (4)0.004 (4)0.015 (4)
C4D0.032 (4)0.035 (5)0.096 (6)0.000 (4)0.000 (4)0.016 (5)
C5D0.033 (4)0.041 (5)0.074 (5)0.002 (4)0.014 (4)0.013 (4)
C6D0.038 (4)0.045 (5)0.047 (4)0.010 (4)0.013 (4)0.007 (4)
C11D0.023 (4)0.030 (4)0.045 (4)0.004 (3)0.005 (3)0.010 (3)
C12D0.024 (4)0.033 (4)0.038 (4)0.004 (3)0.006 (3)0.003 (3)
C13D0.045 (5)0.050 (5)0.050 (5)0.013 (4)0.011 (4)0.017 (4)
C14D0.035 (5)0.043 (5)0.110 (8)0.007 (4)0.013 (5)0.024 (6)
C15D0.037 (5)0.043 (5)0.116 (8)0.009 (4)0.001 (5)0.006 (6)
C16D0.040 (4)0.040 (5)0.067 (5)0.002 (4)0.010 (4)0.006 (4)
C21D0.026 (4)0.019 (3)0.039 (3)0.006 (3)0.011 (3)0.001 (3)
C22D0.025 (4)0.020 (4)0.039 (4)0.005 (3)0.008 (3)0.001 (3)
C23D0.036 (4)0.031 (4)0.036 (4)0.003 (3)0.005 (3)0.002 (3)
C24D0.036 (4)0.035 (5)0.056 (5)0.000 (4)0.008 (4)0.007 (4)
C25D0.034 (4)0.037 (5)0.065 (5)0.008 (4)0.019 (4)0.000 (4)
C26D0.044 (5)0.032 (4)0.037 (4)0.002 (4)0.013 (3)0.001 (3)
C31D0.024 (3)0.019 (3)0.031 (3)0.001 (3)0.000 (3)0.005 (3)
C32D0.028 (4)0.015 (3)0.040 (4)0.002 (3)0.005 (3)0.002 (3)
C33D0.040 (4)0.036 (4)0.035 (4)0.000 (4)0.012 (3)0.001 (3)
C34D0.030 (4)0.032 (4)0.063 (4)0.007 (3)0.011 (4)0.002 (4)
C35D0.039 (5)0.042 (5)0.055 (4)0.016 (4)0.003 (4)0.008 (4)
C36D0.038 (4)0.037 (4)0.042 (4)0.006 (4)0.006 (4)0.001 (3)
Geometric parameters (Å, º) top
S1A—C12A1.756 (6)S1C—C12C1.753 (7)
S1A—C2A1.757 (7)S1C—C2C1.760 (7)
S2A—C32A1.739 (8)S2C—C32C1.745 (7)
S2A—C22A1.781 (8)S2C—C22C1.765 (7)
O1A—B2A1.349 (8)O1C—B2C1.372 (8)
O1A—B1A1.388 (8)O1C—B1C1.378 (8)
B1A—C1A1.530 (10)B1C—C1C1.523 (10)
B1A—C11A1.557 (10)B1C—C11C1.555 (11)
B2A—C21A1.542 (10)B2C—C21C1.521 (10)
B2A—C31A1.552 (11)B2C—C31C1.540 (11)
C1A—C2A1.397 (8)C1C—C2C1.397 (8)
C1A—C6A1.416 (10)C1C—C6C1.415 (10)
C2A—C3A1.414 (10)C2C—C3C1.403 (9)
C3A—C4A1.390 (10)C3C—C4C1.363 (11)
C3A—H3A0.9500C3C—H3C0.9500
C4A—C5A1.382 (9)C4C—C5C1.382 (11)
C4A—H4A0.9500C4C—H4C0.9500
C5A—C6A1.366 (10)C5C—C6C1.368 (11)
C5A—H5A0.9500C5C—H5C0.9500
C6A—H6A0.9500C6C—H6C0.9500
C11A—C16A1.407 (9)C11C—C12C1.401 (9)
C11A—C12A1.411 (8)C11C—C16C1.406 (9)
C12A—C13A1.397 (9)C12C—C13C1.409 (11)
C13A—C14A1.379 (10)C13C—C14C1.387 (11)
C13A—H13A0.9500C13C—H13C0.9500
C14A—C15A1.395 (10)C14C—C15C1.389 (12)
C14A—H14A0.9500C14C—H14C0.9500
C15A—C16A1.376 (11)C15C—C16C1.372 (13)
C15A—H15A0.9500C15C—H15C0.9500
C16A—H16A0.9500C16C—H16C0.9500
C21A—C26A1.413 (10)C21C—C26C1.408 (10)
C21A—C22A1.417 (9)C21C—C22C1.412 (8)
C22A—C23A1.387 (9)C22C—C23C1.389 (10)
C23A—C24A1.366 (11)C23C—C24C1.384 (10)
C23A—H23A0.9500C23C—H23C0.9500
C24A—C25A1.378 (11)C24C—C25C1.386 (10)
C24A—H24A0.9500C24C—H24C0.9500
C25A—C26A1.380 (10)C25C—C26C1.368 (10)
C25A—H25A0.9500C25C—H25C0.9500
C26A—H26A0.9500C26C—H26C0.9500
C31A—C32A1.398 (9)C31C—C32C1.403 (9)
C31A—C36A1.410 (9)C31C—C36C1.419 (9)
C32A—C33A1.411 (10)C32C—C33C1.409 (10)
C33A—C34A1.375 (11)C33C—C34C1.387 (10)
C33A—H33A0.9500C33C—H33C0.9500
C34A—C35A1.377 (10)C34C—C35C1.391 (10)
C34A—H34A0.9500C34C—H34C0.9500
C35A—C36A1.371 (9)C35C—C36C1.373 (10)
C35A—H35A0.9500C35C—H35C0.9500
C36A—H36A0.9500C36C—H36C0.9500
S1B—C12B1.758 (7)S1D—C12D1.744 (7)
S1B—C2B1.770 (7)S1D—C2D1.765 (7)
S2B—C22B1.752 (7)S2D—C32D1.753 (7)
S2B—C32B1.759 (7)S2D—C22D1.763 (7)
O1B—B1B1.346 (8)O1D—B1D1.370 (8)
O1B—B2B1.358 (8)O1D—B2D1.386 (8)
B1B—C1B1.506 (11)B1D—C1D1.525 (11)
B1B—C11B1.567 (11)B1D—C11D1.553 (11)
B2B—C31B1.534 (10)B2D—C31D1.533 (11)
B2B—C21B1.555 (11)B2D—C21D1.536 (11)
C1B—C2B1.401 (8)C1D—C2D1.387 (9)
C1B—C6B1.418 (10)C1D—C6D1.422 (10)
C2B—C3B1.394 (10)C2D—C3D1.410 (10)
C3B—C4B1.399 (10)C3D—C4D1.352 (11)
C3B—H3B0.9500C3D—H3D0.9500
C4B—C5B1.364 (10)C4D—C5D1.387 (10)
C4B—H4B0.9500C4D—H4D0.9500
C5B—C6B1.381 (11)C5D—C6D1.380 (11)
C5B—H5B0.9500C5D—H5D0.9500
C6B—H6B0.9500C6D—H6D0.9500
C11B—C12B1.397 (9)C11D—C12D1.391 (9)
C11B—C16B1.418 (10)C11D—C16D1.419 (10)
C12B—C13B1.419 (11)C12D—C13D1.414 (10)
C13B—C14B1.386 (11)C13D—C14D1.383 (12)
C13B—H13B0.9500C13D—H13D0.9500
C14B—C15B1.379 (10)C14D—C15D1.358 (12)
C14B—H14B0.9500C14D—H14D0.9500
C15B—C16B1.388 (11)C15D—C16D1.360 (12)
C15B—H15B0.9500C15D—H15D0.9500
C16B—H16B0.9500C16D—H16D0.9500
C21B—C22B1.398 (9)C21D—C22D1.398 (9)
C21B—C26B1.416 (10)C21D—C26D1.416 (10)
C22B—C23B1.418 (10)C22D—C23D1.413 (10)
C23B—C24B1.380 (11)C23D—C24D1.385 (10)
C23B—H23B0.9500C23D—H23D0.9500
C24B—C25B1.387 (11)C24D—C25D1.388 (11)
C24B—H24B0.9500C24D—H24D0.9500
C25B—C26B1.375 (12)C25D—C26D1.381 (11)
C25B—H25B0.9500C25D—H25D0.9500
C26B—H26B0.9500C26D—H26D0.9500
C31B—C32B1.415 (8)C31D—C36D1.403 (10)
C31B—C36B1.416 (10)C31D—C32D1.403 (8)
C32B—C33B1.402 (9)C32D—C33D1.407 (10)
C33B—C34B1.371 (11)C33D—C34D1.376 (10)
C33B—H33B0.9500C33D—H33D0.9500
C34B—C35B1.398 (10)C34D—C35D1.391 (10)
C34B—H34B0.9500C34D—H34D0.9500
C35B—C36B1.372 (10)C35D—C36D1.371 (10)
C35B—H35B0.9500C35D—H35D0.9500
C36B—H36B0.9500C36D—H36D0.9500
C12A—S1A—C2A106.4 (3)C12C—S1C—C2C105.9 (3)
C32A—S2A—C22A106.9 (3)C32C—S2C—C22C106.6 (3)
B2A—O1A—B1A146.0 (6)B2C—O1C—B1C166.0 (7)
O1A—B1A—C1A120.7 (6)O1C—B1C—C1C118.4 (7)
O1A—B1A—C11A117.9 (6)O1C—B1C—C11C119.7 (6)
C1A—B1A—C11A121.4 (5)C1C—B1C—C11C121.9 (5)
O1A—B2A—C21A117.4 (7)O1C—B2C—C21C119.0 (7)
O1A—B2A—C31A121.7 (6)O1C—B2C—C31C118.1 (7)
C21A—B2A—C31A121.0 (6)C21C—B2C—C31C122.9 (5)
C2A—C1A—C6A116.4 (6)C2C—C1C—C6C116.8 (6)
C2A—C1A—B1A122.2 (6)C2C—C1C—B1C121.5 (6)
C6A—C1A—B1A121.3 (6)C6C—C1C—B1C121.7 (6)
C1A—C2A—C3A121.3 (6)C1C—C2C—C3C120.7 (6)
C1A—C2A—S1A124.4 (5)C1C—C2C—S1C124.5 (5)
C3A—C2A—S1A114.3 (5)C3C—C2C—S1C114.8 (5)
C4A—C3A—C2A119.2 (6)C4C—C3C—C2C120.1 (7)
C4A—C3A—H3A120.4C4C—C3C—H3C120.0
C2A—C3A—H3A120.4C2C—C3C—H3C120.0
C5A—C4A—C3A120.5 (7)C3C—C4C—C5C120.8 (8)
C5A—C4A—H4A119.7C3C—C4C—H4C119.6
C3A—C4A—H4A119.7C5C—C4C—H4C119.6
C6A—C5A—C4A119.6 (7)C6C—C5C—C4C119.5 (7)
C6A—C5A—H5A120.2C6C—C5C—H5C120.2
C4A—C5A—H5A120.2C4C—C5C—H5C120.2
C5A—C6A—C1A122.9 (6)C5C—C6C—C1C122.1 (7)
C5A—C6A—H6A118.5C5C—C6C—H6C119.0
C1A—C6A—H6A118.5C1C—C6C—H6C119.0
C16A—C11A—C12A116.4 (6)C12C—C11C—C16C117.2 (7)
C16A—C11A—B1A122.3 (6)C12C—C11C—B1C120.7 (6)
C12A—C11A—B1A121.3 (6)C16C—C11C—B1C122.0 (7)
C13A—C12A—C11A120.4 (6)C11C—C12C—C13C121.0 (7)
C13A—C12A—S1A115.3 (5)C11C—C12C—S1C124.6 (5)
C11A—C12A—S1A124.3 (5)C13C—C12C—S1C114.4 (6)
C14A—C13A—C12A121.0 (6)C14C—C13C—C12C119.0 (8)
C14A—C13A—H13A119.5C14C—C13C—H13C120.5
C12A—C13A—H13A119.5C12C—C13C—H13C120.5
C13A—C14A—C15A119.9 (7)C13C—C14C—C15C121.2 (8)
C13A—C14A—H14A120.0C13C—C14C—H14C119.4
C15A—C14A—H14A120.0C15C—C14C—H14C119.4
C16A—C15A—C14A118.7 (7)C16C—C15C—C14C118.9 (8)
C16A—C15A—H15A120.6C16C—C15C—H15C120.6
C14A—C15A—H15A120.6C14C—C15C—H15C120.6
C15A—C16A—C11A123.5 (6)C15C—C16C—C11C122.7 (8)
C15A—C16A—H16A118.3C15C—C16C—H16C118.7
C11A—C16A—H16A118.3C11C—C16C—H16C118.7
C26A—C21A—C22A114.7 (6)C26C—C21C—C22C115.8 (6)
C26A—C21A—B2A122.0 (6)C26C—C21C—B2C123.1 (6)
C22A—C21A—B2A123.3 (7)C22C—C21C—B2C121.1 (6)
C23A—C22A—C21A123.3 (7)C23C—C22C—C21C121.5 (6)
C23A—C22A—S2A114.7 (6)C23C—C22C—S2C114.6 (5)
C21A—C22A—S2A122.0 (5)C21C—C22C—S2C123.9 (5)
C24A—C23A—C22A119.0 (7)C24C—C23C—C22C120.0 (7)
C24A—C23A—H23A120.5C24C—C23C—H23C120.0
C22A—C23A—H23A120.5C22C—C23C—H23C120.0
C23A—C24A—C25A120.4 (7)C23C—C24C—C25C120.1 (7)
C23A—C24A—H24A119.8C23C—C24C—H24C120.0
C25A—C24A—H24A119.8C25C—C24C—H24C120.0
C24A—C25A—C26A120.7 (8)C26C—C25C—C24C119.4 (7)
C24A—C25A—H25A119.7C26C—C25C—H25C120.3
C26A—C25A—H25A119.7C24C—C25C—H25C120.3
C25A—C26A—C21A121.8 (7)C25C—C26C—C21C123.1 (6)
C25A—C26A—H26A119.1C25C—C26C—H26C118.4
C21A—C26A—H26A119.1C21C—C26C—H26C118.4
C32A—C31A—C36A116.6 (7)C32C—C31C—C36C116.9 (7)
C32A—C31A—B2A121.2 (6)C32C—C31C—B2C121.1 (6)
C36A—C31A—B2A122.1 (6)C36C—C31C—B2C122.0 (6)
C31A—C32A—C33A120.6 (7)C31C—C32C—C33C120.5 (6)
C31A—C32A—S2A125.5 (6)C31C—C32C—S2C124.4 (6)
C33A—C32A—S2A114.0 (6)C33C—C32C—S2C115.1 (5)
C34A—C33A—C32A120.2 (7)C34C—C33C—C32C120.6 (6)
C34A—C33A—H33A119.9C34C—C33C—H33C119.7
C32A—C33A—H33A119.9C32C—C33C—H33C119.7
C33A—C34A—C35A120.3 (7)C33C—C34C—C35C119.8 (7)
C33A—C34A—H34A119.9C33C—C34C—H34C120.1
C35A—C34A—H34A119.9C35C—C34C—H34C120.1
C36A—C35A—C34A119.6 (7)C36C—C35C—C34C119.6 (7)
C36A—C35A—H35A120.2C36C—C35C—H35C120.2
C34A—C35A—H35A120.2C34C—C35C—H35C120.2
C35A—C36A—C31A122.7 (7)C35C—C36C—C31C122.7 (7)
C35A—C36A—H36A118.6C35C—C36C—H36C118.7
C31A—C36A—H36A118.6C31C—C36C—H36C118.7
C12B—S1B—C2B106.0 (3)C12D—S1D—C2D106.4 (3)
C22B—S2B—C32B106.5 (3)C32D—S2D—C22D106.1 (3)
B1B—O1B—B2B164.8 (7)B1D—O1D—B2D165.9 (7)
O1B—B1B—C1B119.6 (7)O1D—B1D—C1D120.6 (7)
O1B—B1B—C11B119.3 (7)O1D—B1D—C11D118.0 (7)
C1B—B1B—C11B121.1 (6)C1D—B1D—C11D121.4 (6)
O1B—B2B—C31B118.6 (7)O1D—B2D—C31D117.4 (7)
O1B—B2B—C21B120.0 (6)O1D—B2D—C21D119.2 (7)
C31B—B2B—C21B121.3 (6)C31D—B2D—C21D123.3 (6)
C2B—C1B—C6B115.0 (6)C2D—C1D—C6D116.0 (7)
C2B—C1B—B1B123.2 (6)C2D—C1D—B1D121.6 (6)
C6B—C1B—B1B121.7 (6)C6D—C1D—B1D122.4 (6)
C3B—C2B—C1B123.0 (7)C1D—C2D—C3D122.1 (7)
C3B—C2B—S1B113.5 (5)C1D—C2D—S1D124.6 (6)
C1B—C2B—S1B123.6 (5)C3D—C2D—S1D113.3 (5)
C2B—C3B—C4B118.8 (6)C4D—C3D—C2D119.4 (7)
C2B—C3B—H3B120.6C4D—C3D—H3D120.3
C4B—C3B—H3B120.6C2D—C3D—H3D120.3
C5B—C4B—C3B120.3 (7)C3D—C4D—C5D121.1 (8)
C5B—C4B—H4B119.8C3D—C4D—H4D119.5
C3B—C4B—H4B119.8C5D—C4D—H4D119.5
C4B—C5B—C6B120.1 (7)C6D—C5D—C4D119.4 (7)
C4B—C5B—H5B120.0C6D—C5D—H5D120.3
C6B—C5B—H5B120.0C4D—C5D—H5D120.3
C5B—C6B—C1B122.8 (6)C5D—C6D—C1D122.0 (7)
C5B—C6B—H6B118.6C5D—C6D—H6D119.0
C1B—C6B—H6B118.6C1D—C6D—H6D119.0
C12B—C11B—C16B116.1 (7)C12D—C11D—C16D117.6 (7)
C12B—C11B—B1B121.4 (6)C12D—C11D—B1D122.1 (6)
C16B—C11B—B1B122.5 (6)C16D—C11D—B1D120.3 (7)
C11B—C12B—C13B122.1 (7)C11D—C12D—C13D119.9 (7)
C11B—C12B—S1B124.6 (5)C11D—C12D—S1D123.9 (5)
C13B—C12B—S1B113.3 (5)C13D—C12D—S1D116.2 (5)
C14B—C13B—C12B118.7 (7)C14D—C13D—C12D119.8 (7)
C14B—C13B—H13B120.6C14D—C13D—H13D120.1
C12B—C13B—H13B120.6C12D—C13D—H13D120.1
C15B—C14B—C13B121.1 (8)C15D—C14D—C13D120.5 (8)
C15B—C14B—H14B119.5C15D—C14D—H14D119.8
C13B—C14B—H14B119.5C13D—C14D—H14D119.8
C14B—C15B—C16B119.5 (7)C14D—C15D—C16D120.7 (9)
C14B—C15B—H15B120.3C14D—C15D—H15D119.6
C16B—C15B—H15B120.3C16D—C15D—H15D119.6
C15B—C16B—C11B122.5 (7)C15D—C16D—C11D121.4 (8)
C15B—C16B—H16B118.7C15D—C16D—H16D119.3
C11B—C16B—H16B118.7C11D—C16D—H16D119.3
C22B—C21B—C26B117.4 (7)C22D—C21D—C26D116.9 (7)
C22B—C21B—B2B121.4 (6)C22D—C21D—B2D120.5 (6)
C26B—C21B—B2B121.2 (6)C26D—C21D—B2D122.6 (6)
C21B—C22B—C23B121.2 (7)C21D—C22D—C23D121.9 (6)
C21B—C22B—S2B124.7 (6)C21D—C22D—S2D124.7 (5)
C23B—C22B—S2B114.1 (5)C23D—C22D—S2D113.5 (5)
C24B—C23B—C22B119.2 (7)C24D—C23D—C22D118.8 (7)
C24B—C23B—H23B120.4C24D—C23D—H23D120.6
C22B—C23B—H23B120.4C22D—C23D—H23D120.6
C23B—C24B—C25B120.4 (8)C23D—C24D—C25D120.8 (8)
C23B—C24B—H24B119.8C23D—C24D—H24D119.6
C25B—C24B—H24B119.8C25D—C24D—H24D119.6
C26B—C25B—C24B120.5 (7)C26D—C25D—C24D120.0 (7)
C26B—C25B—H25B119.8C26D—C25D—H25D120.0
C24B—C25B—H25B119.8C24D—C25D—H25D120.0
C25B—C26B—C21B121.3 (7)C25D—C26D—C21D121.7 (7)
C25B—C26B—H26B119.3C25D—C26D—H26D119.2
C21B—C26B—H26B119.3C21D—C26D—H26D119.2
C32B—C31B—C36B116.9 (6)C36D—C31D—C32D117.0 (6)
C32B—C31B—B2B122.1 (6)C36D—C31D—B2D122.5 (6)
C36B—C31B—B2B121.0 (6)C32D—C31D—B2D120.5 (6)
C33B—C32B—C31B120.8 (6)C31D—C32D—C33D119.9 (7)
C33B—C32B—S2B115.5 (5)C31D—C32D—S2D124.8 (5)
C31B—C32B—S2B123.7 (5)C33D—C32D—S2D115.3 (5)
C34B—C33B—C32B120.5 (7)C34D—C33D—C32D121.0 (7)
C34B—C33B—H33B119.8C34D—C33D—H33D119.5
C32B—C33B—H33B119.8C32D—C33D—H33D119.5
C33B—C34B—C35B119.9 (7)C33D—C34D—C35D119.8 (7)
C33B—C34B—H34B120.0C33D—C34D—H34D120.1
C35B—C34B—H34B120.0C35D—C34D—H34D120.1
C36B—C35B—C34B120.2 (8)C36D—C35D—C34D119.1 (7)
C36B—C35B—H35B119.9C36D—C35D—H35D120.5
C34B—C35B—H35B119.9C34D—C35D—H35D120.5
C35B—C36B—C31B121.7 (7)C35D—C36D—C31D123.2 (7)
C35B—C36B—H36B119.1C35D—C36D—H36D118.4
C31B—C36B—H36B119.1C31D—C36D—H36D118.4
B2A—O1A—B1A—C1A85.0 (12)B2C—O1C—B1C—C1C151 (3)
B2A—O1A—B1A—C11A97.8 (11)B2C—O1C—B1C—C11C30 (3)
B1A—O1A—B2A—C21A177.5 (9)B1C—O1C—B2C—C21C116 (3)
B1A—O1A—B2A—C31A3.8 (14)B1C—O1C—B2C—C31C64 (3)
O1A—B1A—C1A—C2A174.7 (6)O1C—B1C—C1C—C2C170.6 (6)
C11A—B1A—C1A—C2A2.5 (10)C11C—B1C—C1C—C2C8.2 (10)
O1A—B1A—C1A—C6A5.1 (10)O1C—B1C—C1C—C6C9.3 (10)
C11A—B1A—C1A—C6A177.8 (6)C11C—B1C—C1C—C6C171.8 (6)
C6A—C1A—C2A—C3A1.8 (10)C6C—C1C—C2C—C3C1.5 (9)
B1A—C1A—C2A—C3A178.0 (6)B1C—C1C—C2C—C3C178.5 (7)
C6A—C1A—C2A—S1A177.7 (5)C6C—C1C—C2C—S1C179.5 (6)
B1A—C1A—C2A—S1A2.6 (9)B1C—C1C—C2C—S1C0.5 (9)
C12A—S1A—C2A—C1A0.7 (7)C12C—S1C—C2C—C1C6.9 (7)
C12A—S1A—C2A—C3A179.9 (5)C12C—S1C—C2C—C3C175.0 (5)
C1A—C2A—C3A—C4A1.7 (10)C1C—C2C—C3C—C4C0.9 (11)
S1A—C2A—C3A—C4A177.8 (6)S1C—C2C—C3C—C4C179.1 (6)
C2A—C3A—C4A—C5A1.1 (11)C2C—C3C—C4C—C5C0.2 (12)
C3A—C4A—C5A—C6A0.6 (12)C3C—C4C—C5C—C6C0.6 (13)
C4A—C5A—C6A—C1A0.8 (12)C4C—C5C—C6C—C1C0.0 (12)
C2A—C1A—C6A—C5A1.3 (11)C2C—C1C—C6C—C5C1.1 (11)
B1A—C1A—C6A—C5A178.4 (7)B1C—C1C—C6C—C5C178.9 (8)
O1A—B1A—C11A—C16A4.7 (10)O1C—B1C—C11C—C12C169.8 (6)
C1A—B1A—C11A—C16A178.1 (7)C1C—B1C—C11C—C12C9.0 (10)
O1A—B1A—C11A—C12A177.0 (6)O1C—B1C—C11C—C16C7.3 (10)
C1A—B1A—C11A—C12A0.2 (9)C1C—B1C—C11C—C16C173.9 (7)
C16A—C11A—C12A—C13A0.8 (9)C16C—C11C—C12C—C13C0.1 (10)
B1A—C11A—C12A—C13A177.6 (6)B1C—C11C—C12C—C13C177.4 (7)
C16A—C11A—C12A—S1A179.8 (5)C16C—C11C—C12C—S1C178.3 (6)
B1A—C11A—C12A—S1A1.8 (9)B1C—C11C—C12C—S1C1.1 (9)
C2A—S1A—C12A—C13A177.8 (5)C2C—S1C—C12C—C11C6.0 (7)
C2A—S1A—C12A—C11A1.6 (6)C2C—S1C—C12C—C13C175.5 (5)
C11A—C12A—C13A—C14A0.1 (10)C11C—C12C—C13C—C14C0.2 (11)
S1A—C12A—C13A—C14A179.5 (5)S1C—C12C—C13C—C14C178.8 (6)
C12A—C13A—C14A—C15A0.6 (11)C12C—C13C—C14C—C15C0.9 (12)
C13A—C14A—C15A—C16A0.6 (11)C13C—C14C—C15C—C16C2.3 (13)
C14A—C15A—C16A—C11A0.2 (12)C14C—C15C—C16C—C11C2.7 (13)
C12A—C11A—C16A—C15A0.9 (11)C12C—C11C—C16C—C15C1.6 (11)
B1A—C11A—C16A—C15A177.5 (7)B1C—C11C—C16C—C15C178.8 (7)
O1A—B2A—C21A—C26A0.9 (10)O1C—B2C—C21C—C26C4.1 (11)
C31A—B2A—C21A—C26A179.6 (7)C31C—B2C—C21C—C26C176.1 (7)
O1A—B2A—C21A—C22A179.5 (6)O1C—B2C—C21C—C22C179.2 (7)
C31A—B2A—C21A—C22A0.8 (10)C31C—B2C—C21C—C22C0.6 (11)
C26A—C21A—C22A—C23A1.8 (10)C26C—C21C—C22C—C23C2.7 (10)
B2A—C21A—C22A—C23A178.5 (7)B2C—C21C—C22C—C23C179.6 (7)
C26A—C21A—C22A—S2A176.6 (5)C26C—C21C—C22C—S2C177.8 (6)
B2A—C21A—C22A—S2A3.0 (9)B2C—C21C—C22C—S2C0.9 (10)
C32A—S2A—C22A—C23A177.8 (5)C32C—S2C—C22C—C23C179.2 (6)
C32A—S2A—C22A—C21A3.6 (7)C32C—S2C—C22C—C21C1.4 (7)
C21A—C22A—C23A—C24A2.9 (11)C21C—C22C—C23C—C24C1.7 (11)
S2A—C22A—C23A—C24A175.7 (6)S2C—C22C—C23C—C24C178.8 (6)
C22A—C23A—C24A—C25A2.3 (12)C22C—C23C—C24C—C25C0.6 (12)
C23A—C24A—C25A—C26A0.8 (12)C23C—C24C—C25C—C26C0.7 (12)
C24A—C25A—C26A—C21A0.2 (12)C24C—C25C—C26C—C21C1.9 (12)
C22A—C21A—C26A—C25A0.3 (10)C22C—C21C—C26C—C25C2.8 (11)
B2A—C21A—C26A—C25A179.9 (7)B2C—C21C—C26C—C25C179.7 (8)
O1A—B2A—C31A—C32A177.5 (6)O1C—B2C—C31C—C32C178.3 (7)
C21A—B2A—C31A—C32A3.8 (10)C21C—B2C—C31C—C32C1.4 (11)
O1A—B2A—C31A—C36A0.7 (10)O1C—B2C—C31C—C36C1.8 (11)
C21A—B2A—C31A—C36A178.0 (6)C21C—B2C—C31C—C36C178.5 (7)
C36A—C31A—C32A—C33A0.6 (10)C36C—C31C—C32C—C33C1.3 (10)
B2A—C31A—C32A—C33A177.7 (7)B2C—C31C—C32C—C33C178.8 (7)
C36A—C31A—C32A—S2A179.0 (5)C36C—C31C—C32C—S2C179.2 (5)
B2A—C31A—C32A—S2A2.8 (10)B2C—C31C—C32C—S2C0.7 (10)
C22A—S2A—C32A—C31A0.7 (7)C22C—S2C—C32C—C31C0.5 (7)
C22A—S2A—C32A—C33A178.8 (5)C22C—S2C—C32C—C33C179.9 (6)
C31A—C32A—C33A—C34A0.4 (11)C31C—C32C—C33C—C34C1.2 (11)
S2A—C32A—C33A—C34A179.2 (6)S2C—C32C—C33C—C34C179.2 (6)
C32A—C33A—C34A—C35A0.4 (12)C32C—C33C—C34C—C35C0.6 (11)
C33A—C34A—C35A—C36A1.0 (11)C33C—C34C—C35C—C36C0.1 (11)
C34A—C35A—C36A—C31A0.8 (10)C34C—C35C—C36C—C31C0.3 (11)
C32A—C31A—C36A—C35A0.0 (10)C32C—C31C—C36C—C35C0.8 (11)
B2A—C31A—C36A—C35A178.2 (6)B2C—C31C—C36C—C35C179.2 (7)
B2B—O1B—B1B—C1B122 (2)B2D—O1D—B1D—C1D41 (3)
B2B—O1B—B1B—C11B60 (3)B2D—O1D—B1D—C11D138 (3)
B1B—O1B—B2B—C31B149 (2)B1D—O1D—B2D—C31D132 (3)
B1B—O1B—B2B—C21B30 (3)B1D—O1D—B2D—C21D50 (3)
O1B—B1B—C1B—C2B179.8 (7)O1D—B1D—C1D—C2D177.2 (7)
C11B—B1B—C1B—C2B2.1 (11)C11D—B1D—C1D—C2D3.5 (11)
O1B—B1B—C1B—C6B0.2 (11)O1D—B1D—C1D—C6D1.3 (11)
C11B—B1B—C1B—C6B177.9 (6)C11D—B1D—C1D—C6D178.0 (7)
C6B—C1B—C2B—C3B0.5 (10)C6D—C1D—C2D—C3D1.9 (10)
B1B—C1B—C2B—C3B179.6 (7)B1D—C1D—C2D—C3D176.8 (7)
C6B—C1B—C2B—S1B179.7 (5)C6D—C1D—C2D—S1D178.7 (6)
B1B—C1B—C2B—S1B0.3 (10)B1D—C1D—C2D—S1D2.7 (10)
C12B—S1B—C2B—C3B178.3 (5)C12D—S1D—C2D—C1D0.4 (7)
C12B—S1B—C2B—C1B1.6 (7)C12D—S1D—C2D—C3D179.1 (6)
C1B—C2B—C3B—C4B0.3 (11)C1D—C2D—C3D—C4D1.1 (12)
S1B—C2B—C3B—C4B179.5 (6)S1D—C2D—C3D—C4D179.4 (6)
C2B—C3B—C4B—C5B0.6 (11)C2D—C3D—C4D—C5D0.3 (12)
C3B—C4B—C5B—C6B0.1 (12)C3D—C4D—C5D—C6D0.7 (12)
C4B—C5B—C6B—C1B0.8 (11)C4D—C5D—C6D—C1D0.2 (11)
C2B—C1B—C6B—C5B1.0 (10)C2D—C1D—C6D—C5D1.4 (10)
B1B—C1B—C6B—C5B179.0 (7)B1D—C1D—C6D—C5D177.2 (7)
O1B—B1B—C11B—C12B179.3 (7)O1D—B1D—C11D—C12D178.9 (7)
C1B—B1B—C11B—C12B3.0 (11)C1D—B1D—C11D—C12D1.8 (11)
O1B—B1B—C11B—C16B0.1 (11)O1D—B1D—C11D—C16D0.1 (11)
C1B—B1B—C11B—C16B177.9 (7)C1D—B1D—C11D—C16D179.5 (7)
C16B—C11B—C12B—C13B1.4 (10)C16D—C11D—C12D—C13D2.0 (10)
B1B—C11B—C12B—C13B179.5 (7)B1D—C11D—C12D—C13D179.2 (7)
C16B—C11B—C12B—S1B179.4 (5)C16D—C11D—C12D—S1D178.2 (6)
B1B—C11B—C12B—S1B1.5 (10)B1D—C11D—C12D—S1D0.6 (10)
C2B—S1B—C12B—C11B0.7 (7)C2D—S1D—C12D—C11D1.2 (7)
C2B—S1B—C12B—C13B177.5 (5)C2D—S1D—C12D—C13D178.6 (5)
C11B—C12B—C13B—C14B1.7 (11)C11D—C12D—C13D—C14D2.0 (11)
S1B—C12B—C13B—C14B179.9 (6)S1D—C12D—C13D—C14D178.1 (6)
C12B—C13B—C14B—C15B1.7 (12)C12D—C13D—C14D—C15D1.0 (12)
C13B—C14B—C15B—C16B1.5 (12)C13D—C14D—C15D—C16D0.1 (14)
C14B—C15B—C16B—C11B1.2 (12)C14D—C15D—C16D—C11D0.1 (13)
C12B—C11B—C16B—C15B1.1 (11)C12D—C11D—C16D—C15D1.1 (11)
B1B—C11B—C16B—C15B179.7 (7)B1D—C11D—C16D—C15D179.8 (7)
O1B—B2B—C21B—C22B178.2 (7)O1D—B2D—C21D—C22D179.9 (6)
C31B—B2B—C21B—C22B1.4 (10)C31D—B2D—C21D—C22D2.0 (10)
O1B—B2B—C21B—C26B2.6 (10)O1D—B2D—C21D—C26D0.8 (11)
C31B—B2B—C21B—C26B177.9 (7)C31D—B2D—C21D—C26D178.9 (7)
C26B—C21B—C22B—C23B0.4 (10)C26D—C21D—C22D—C23D1.1 (10)
B2B—C21B—C22B—C23B179.7 (7)B2D—C21D—C22D—C23D179.7 (7)
C26B—C21B—C22B—S2B178.2 (6)C26D—C21D—C22D—S2D177.8 (6)
B2B—C21B—C22B—S2B2.5 (9)B2D—C21D—C22D—S2D1.4 (9)
C32B—S2B—C22B—C21B4.3 (7)C32D—S2D—C22D—C21D3.1 (6)
C32B—S2B—C22B—C23B177.8 (5)C32D—S2D—C22D—C23D177.9 (5)
C21B—C22B—C23B—C24B0.1 (11)C21D—C22D—C23D—C24D0.5 (10)
S2B—C22B—C23B—C24B177.9 (6)S2D—C22D—C23D—C24D179.6 (6)
C22B—C23B—C24B—C25B0.3 (12)C22D—C23D—C24D—C25D2.2 (11)
C23B—C24B—C25B—C26B0.0 (13)C23D—C24D—C25D—C26D2.1 (12)
C24B—C25B—C26B—C21B0.6 (13)C24D—C25D—C26D—C21D0.3 (12)
C22B—C21B—C26B—C25B0.8 (11)C22D—C21D—C26D—C25D1.2 (11)
B2B—C21B—C26B—C25B180.0 (7)B2D—C21D—C26D—C25D179.6 (7)
O1B—B2B—C31B—C32B176.8 (6)O1D—B2D—C31D—C36D0.9 (10)
C21B—B2B—C31B—C32B2.8 (10)C21D—B2D—C31D—C36D179.0 (7)
O1B—B2B—C31B—C36B3.3 (10)O1D—B2D—C31D—C32D178.9 (6)
C21B—B2B—C31B—C36B177.2 (7)C21D—B2D—C31D—C32D3.0 (10)
C36B—C31B—C32B—C33B1.1 (10)C36D—C31D—C32D—C33D1.6 (10)
B2B—C31B—C32B—C33B178.9 (7)B2D—C31D—C32D—C33D179.8 (7)
C36B—C31B—C32B—S2B179.6 (5)C36D—C31D—C32D—S2D178.7 (6)
B2B—C31B—C32B—S2B0.3 (9)B2D—C31D—C32D—S2D0.6 (9)
C22B—S2B—C32B—C33B177.9 (5)C22D—S2D—C32D—C31D2.1 (7)
C22B—S2B—C32B—C31B2.8 (6)C22D—S2D—C32D—C33D177.6 (5)
C31B—C32B—C33B—C34B0.4 (11)C31D—C32D—C33D—C34D1.1 (11)
S2B—C32B—C33B—C34B179.7 (6)S2D—C32D—C33D—C34D179.2 (6)
C32B—C33B—C34B—C35B0.5 (11)C32D—C33D—C34D—C35D0.1 (12)
C33B—C34B—C35B—C36B0.7 (12)C33D—C34D—C35D—C36D0.6 (12)
C34B—C35B—C36B—C31B0.0 (12)C34D—C35D—C36D—C31D0.0 (12)
C32B—C31B—C36B—C35B0.9 (11)C32D—C31D—C36D—C35D1.1 (11)
B2B—C31B—C36B—C35B179.1 (7)B2D—C31D—C36D—C35D179.2 (7)
10,10'-Oxybis(9-thia-10-hydro-10-boraanthracene) (II) top
Crystal data top
C24H16B2OS2F(000) = 1680
Mr = 406.11Dx = 1.381 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 23.2471 (18) ÅCell parameters from 6545 reflections
b = 12.5949 (16) Åθ = 2.3–23.9°
c = 13.3561 (11) ŵ = 0.29 mm1
β = 92.217 (6)°T = 173 K
V = 3907.7 (7) Å3Needle, colourless
Z = 80.19 × 0.12 × 0.09 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
32689 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source13195 reflections with I > 2σ(I)
ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(X-Area; Stoe & Cie, 2001)
h = 2727
Tmin = 0.677, Tmax = 1.000k = 1414
32689 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.184 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max < 0.001
32689 reflectionsΔρmax = 0.48 e Å3
524 parametersΔρmin = 0.28 e Å3
0 restraints
Special details top

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

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.43516 (7)0.40888 (17)0.35977 (14)0.0626 (5)
S20.82281 (8)0.37484 (16)0.36230 (15)0.0662 (5)
B10.5722 (3)0.4025 (8)0.3877 (7)0.062 (2)
B20.6871 (4)0.3869 (9)0.3866 (8)0.074 (3)
O10.6303 (2)0.3935 (6)0.3941 (5)0.111 (2)
C10.5359 (3)0.3507 (6)0.4647 (6)0.0570 (19)
C20.4763 (3)0.3519 (5)0.4574 (5)0.0520 (18)
C30.4441 (3)0.3024 (6)0.5317 (5)0.0613 (19)
H30.40330.30310.52580.074*
C40.4704 (4)0.2541 (6)0.6109 (6)0.070 (2)
H40.44800.22070.65990.084*
C50.5290 (4)0.2531 (7)0.6210 (6)0.077 (2)
H50.54720.21920.67730.092*
C60.5616 (3)0.3000 (7)0.5514 (7)0.072 (2)
H60.60240.29930.56040.087*
C110.5436 (3)0.4650 (6)0.2981 (6)0.060 (2)
C120.4842 (3)0.4719 (6)0.2839 (6)0.0580 (19)
C130.4584 (4)0.5294 (6)0.2030 (6)0.074 (2)
H130.41770.53380.19440.089*
C140.4934 (5)0.5785 (7)0.1376 (7)0.091 (3)
H140.47700.61550.08150.109*
C150.5524 (5)0.5751 (7)0.1520 (8)0.089 (3)
H150.57600.61340.10810.107*
C160.5768 (4)0.5181 (7)0.2273 (7)0.076 (2)
H160.61760.51340.23300.092*
C210.7261 (3)0.4665 (6)0.4404 (6)0.065 (2)
C220.7854 (3)0.4663 (6)0.4341 (6)0.0612 (19)
C230.8199 (4)0.5424 (7)0.4834 (6)0.081 (2)
H230.86040.54220.47670.098*
C240.7940 (7)0.6184 (8)0.5424 (8)0.114 (4)
H240.81720.67020.57630.137*
C250.7353 (7)0.6198 (10)0.5525 (7)0.120 (5)
H250.71790.67040.59450.144*
C260.7032 (5)0.5474 (9)0.5011 (7)0.093 (3)
H260.66260.55080.50590.111*
C310.7129 (3)0.2958 (6)0.3196 (5)0.0561 (19)
C320.7713 (3)0.2881 (6)0.3083 (5)0.0490 (17)
C330.7945 (3)0.2069 (7)0.2520 (6)0.070 (2)
H330.83490.20250.24540.084*
C340.7590 (5)0.1329 (7)0.2057 (7)0.082 (3)
H340.77520.07860.16630.098*
C350.7018 (5)0.1363 (8)0.2154 (8)0.088 (3)
H350.67770.08490.18290.106*
C360.6780 (4)0.2161 (8)0.2737 (7)0.080 (3)
H360.63770.21690.28270.096*
O1A0.1319 (2)0.4253 (5)0.1099 (5)0.0859 (18)
B1A0.1859 (4)0.3986 (7)0.1160 (6)0.057 (2)
B2A0.0740 (4)0.4187 (7)0.1190 (7)0.060 (2)
S1A0.32048 (9)0.3448 (2)0.1355 (2)0.0927 (8)
S2A0.06322 (7)0.40963 (15)0.13954 (14)0.0575 (5)
C1A0.2075 (3)0.2985 (6)0.1766 (6)0.0607 (19)
C2A0.2660 (3)0.2748 (6)0.1860 (6)0.070 (2)
C3A0.2841 (6)0.1879 (9)0.2445 (8)0.110 (4)
H3A0.32410.17370.25360.132*
C4A0.2448 (9)0.1223 (11)0.2894 (9)0.146 (7)
H4A0.25720.06150.32640.175*
C5A0.1879 (7)0.1474 (9)0.2791 (7)0.118 (4)
H5A0.16080.10380.31110.142*
C6A0.1685 (4)0.2315 (8)0.2253 (7)0.085 (3)
H6A0.12840.24590.21990.102*
C11A0.2300 (3)0.4673 (6)0.0636 (5)0.0581 (19)
C12A0.2880 (3)0.4474 (7)0.0666 (5)0.064 (2)
C13A0.3269 (5)0.5114 (12)0.0160 (10)0.117 (4)
H13A0.36670.49390.01860.140*
C14A0.3094 (10)0.5935 (16)0.0338 (11)0.165 (9)
H14A0.33640.63620.06710.198*
C15A0.2528 (9)0.6196 (11)0.0393 (9)0.139 (6)
H15A0.24070.68140.07500.167*
C16A0.2125 (5)0.5574 (8)0.0061 (7)0.096 (3)
H16A0.17290.57500.00110.115*
C21A0.0463 (3)0.4731 (5)0.2099 (5)0.0517 (17)
C22A0.0127 (3)0.4733 (5)0.2212 (5)0.0510 (17)
C23A0.0368 (3)0.5254 (6)0.3030 (6)0.063 (2)
H23A0.07730.52540.30980.076*
C24A0.0018 (4)0.5758 (6)0.3724 (6)0.072 (2)
H24A0.01840.61170.42690.086*
C25A0.0569 (4)0.5755 (6)0.3645 (6)0.073 (2)
H25A0.08130.60940.41350.087*
C26A0.0794 (3)0.5247 (6)0.2839 (7)0.072 (2)
H26A0.12000.52490.27840.086*
C31A0.0356 (3)0.3593 (5)0.0389 (5)0.0499 (17)
C32A0.0237 (3)0.3539 (5)0.0422 (5)0.0466 (16)
C33A0.0569 (3)0.3003 (6)0.0300 (6)0.0596 (19)
H33A0.09760.29690.02550.072*
C34A0.0305 (4)0.2526 (6)0.1077 (6)0.065 (2)
H34A0.05300.21690.15810.078*
C35A0.0280 (4)0.2555 (7)0.1138 (6)0.072 (2)
H35A0.04610.22050.16710.087*
C36A0.0601 (3)0.3090 (6)0.0425 (7)0.067 (2)
H36A0.10070.31220.04850.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0533 (11)0.0670 (13)0.0674 (13)0.0100 (9)0.0028 (8)0.0037 (11)
S20.0521 (11)0.0658 (13)0.0808 (14)0.0020 (9)0.0062 (8)0.0091 (11)
B10.052 (5)0.063 (6)0.072 (6)0.008 (4)0.005 (4)0.008 (5)
B20.054 (6)0.089 (8)0.080 (7)0.017 (5)0.014 (4)0.041 (6)
O10.049 (3)0.160 (7)0.126 (6)0.033 (4)0.019 (3)0.036 (5)
C10.053 (4)0.053 (5)0.065 (5)0.006 (3)0.001 (3)0.006 (4)
C20.054 (4)0.041 (4)0.061 (5)0.008 (3)0.002 (3)0.000 (3)
C30.070 (5)0.055 (5)0.058 (5)0.009 (4)0.002 (3)0.015 (4)
C40.075 (6)0.056 (5)0.080 (6)0.009 (4)0.008 (4)0.003 (4)
C50.098 (7)0.065 (5)0.066 (5)0.006 (5)0.011 (4)0.022 (5)
C60.060 (5)0.062 (6)0.094 (7)0.011 (4)0.013 (4)0.000 (5)
C110.058 (5)0.055 (5)0.069 (5)0.008 (4)0.022 (4)0.015 (4)
C120.063 (5)0.041 (5)0.071 (5)0.003 (3)0.006 (3)0.009 (4)
C130.090 (6)0.056 (5)0.076 (6)0.008 (4)0.000 (4)0.003 (5)
C140.129 (9)0.061 (6)0.083 (7)0.007 (6)0.009 (5)0.011 (5)
C150.121 (8)0.060 (6)0.088 (7)0.007 (6)0.032 (6)0.000 (5)
C160.073 (5)0.064 (6)0.094 (7)0.007 (4)0.019 (4)0.001 (5)
C210.076 (6)0.060 (5)0.059 (5)0.017 (4)0.007 (4)0.014 (4)
C220.077 (5)0.048 (5)0.058 (5)0.000 (4)0.007 (4)0.010 (4)
C230.111 (7)0.074 (6)0.058 (5)0.022 (5)0.001 (4)0.003 (5)
C240.228 (13)0.058 (7)0.057 (6)0.021 (8)0.006 (7)0.011 (5)
C250.241 (15)0.079 (9)0.041 (6)0.053 (9)0.028 (8)0.010 (5)
C260.132 (8)0.090 (8)0.058 (6)0.052 (6)0.022 (5)0.009 (5)
C310.046 (4)0.076 (6)0.045 (4)0.007 (4)0.009 (3)0.020 (4)
C320.054 (4)0.047 (4)0.046 (4)0.000 (3)0.005 (3)0.010 (3)
C330.070 (5)0.057 (6)0.082 (6)0.009 (4)0.002 (4)0.004 (4)
C340.123 (8)0.056 (6)0.066 (6)0.003 (6)0.010 (5)0.009 (4)
C350.116 (8)0.062 (7)0.085 (7)0.032 (6)0.022 (5)0.002 (5)
C360.066 (5)0.093 (7)0.081 (6)0.024 (5)0.013 (4)0.037 (6)
O1A0.047 (3)0.097 (5)0.113 (5)0.014 (3)0.000 (3)0.017 (4)
B1A0.054 (5)0.060 (6)0.057 (5)0.002 (4)0.002 (4)0.020 (4)
B2A0.064 (6)0.043 (5)0.072 (6)0.010 (4)0.005 (4)0.010 (4)
S1A0.0523 (13)0.109 (2)0.116 (2)0.0165 (12)0.0001 (11)0.0204 (16)
S2A0.0587 (11)0.0531 (12)0.0611 (12)0.0003 (9)0.0078 (8)0.0040 (10)
C1A0.067 (5)0.054 (5)0.062 (5)0.007 (4)0.004 (3)0.010 (4)
C2A0.078 (6)0.055 (5)0.075 (6)0.015 (4)0.000 (4)0.020 (4)
C3A0.177 (11)0.057 (7)0.092 (8)0.044 (7)0.031 (7)0.009 (6)
C4A0.31 (2)0.051 (8)0.070 (8)0.040 (11)0.040 (11)0.016 (6)
C5A0.256 (16)0.060 (8)0.039 (5)0.036 (9)0.017 (7)0.006 (5)
C6A0.124 (7)0.071 (7)0.063 (5)0.031 (5)0.029 (5)0.021 (5)
C11A0.083 (6)0.055 (5)0.036 (4)0.002 (4)0.002 (3)0.002 (3)
C12A0.065 (5)0.079 (6)0.048 (4)0.015 (4)0.010 (3)0.009 (4)
C13A0.119 (9)0.130 (11)0.103 (9)0.056 (8)0.037 (7)0.041 (8)
C14A0.29 (2)0.134 (16)0.079 (10)0.109 (18)0.047 (13)0.040 (10)
C15A0.294 (19)0.057 (7)0.065 (8)0.037 (12)0.014 (11)0.014 (6)
C16A0.135 (8)0.071 (7)0.080 (7)0.002 (6)0.010 (6)0.012 (6)
C21A0.056 (5)0.042 (4)0.057 (4)0.004 (3)0.009 (3)0.003 (3)
C22A0.066 (5)0.037 (4)0.050 (4)0.005 (3)0.001 (3)0.001 (3)
C23A0.078 (5)0.052 (5)0.061 (5)0.007 (4)0.015 (4)0.002 (4)
C24A0.119 (7)0.052 (5)0.045 (5)0.011 (5)0.010 (4)0.019 (4)
C25A0.107 (7)0.052 (5)0.058 (5)0.014 (5)0.008 (4)0.020 (4)
C26A0.062 (5)0.056 (6)0.095 (6)0.012 (4)0.013 (4)0.007 (5)
C31A0.064 (4)0.035 (4)0.051 (4)0.006 (3)0.015 (3)0.002 (3)
C32A0.050 (4)0.039 (4)0.051 (4)0.008 (3)0.007 (3)0.002 (3)
C33A0.059 (4)0.051 (5)0.070 (5)0.002 (3)0.003 (3)0.004 (4)
C34A0.086 (6)0.057 (5)0.054 (5)0.005 (4)0.009 (4)0.002 (4)
C35A0.093 (7)0.058 (5)0.067 (6)0.002 (5)0.026 (4)0.006 (4)
C36A0.061 (5)0.047 (5)0.095 (7)0.004 (4)0.023 (4)0.004 (4)
Geometric parameters (Å, º) top
S1—C121.744 (8)O1A—B1A1.300 (9)
S1—C21.742 (7)O1A—B2A1.357 (9)
S2—C221.751 (8)B1A—C11A1.531 (11)
S2—C321.755 (7)B1A—C1A1.571 (12)
B1—O11.356 (9)B2A—C21A1.556 (11)
B1—C11.504 (12)B2A—C31A1.559 (12)
B1—C111.559 (12)S1A—C2A1.704 (9)
B2—O11.330 (9)S1A—C12A1.743 (9)
B2—C211.515 (14)S2A—C22A1.764 (7)
B2—C311.586 (13)S2A—C32A1.766 (6)
C1—C21.385 (8)C1A—C2A1.392 (9)
C1—C61.432 (11)C1A—C6A1.416 (11)
C2—C31.411 (10)C2A—C3A1.400 (13)
C3—C41.345 (10)C3A—C4A1.385 (18)
C3—H30.9500C3A—H3A0.9500
C4—C51.365 (10)C4A—C5A1.363 (16)
C4—H40.9500C4A—H4A0.9500
C5—C61.357 (11)C5A—C6A1.348 (15)
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C11—C121.391 (9)C11A—C12A1.370 (9)
C11—C161.413 (11)C11A—C16A1.421 (12)
C12—C131.416 (11)C12A—C13A1.405 (13)
C13—C141.366 (12)C13A—C14A1.29 (2)
C13—H130.9500C13A—H13A0.9500
C14—C151.377 (12)C14A—C15A1.357 (19)
C14—H140.9500C14A—H14A0.9500
C15—C161.343 (12)C15A—C16A1.378 (17)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C21—C221.384 (9)C21A—C22A1.385 (8)
C21—C261.419 (12)C21A—C26A1.390 (10)
C22—C231.398 (11)C22A—C23A1.409 (10)
C23—C241.392 (14)C23A—C24A1.366 (10)
C23—H230.9500C23A—H23A0.9500
C24—C251.375 (14)C24A—C25A1.373 (10)
C24—H240.9500C24A—H24A0.9500
C25—C261.349 (15)C25A—C26A1.373 (11)
C25—H250.9500C25A—H25A0.9500
C26—H260.9500C26A—H26A0.9500
C31—C321.375 (8)C31A—C32A1.382 (8)
C31—C361.415 (12)C31A—C36A1.399 (10)
C32—C331.391 (10)C32A—C33A1.387 (10)
C33—C341.375 (11)C33A—C34A1.366 (10)
C33—H330.9500C33A—H33A0.9500
C34—C351.340 (11)C34A—C35A1.365 (10)
C34—H340.9500C34A—H34A0.9500
C35—C361.400 (13)C35A—C36A1.365 (11)
C35—H350.9500C35A—H35A0.9500
C36—H360.9500C36A—H36A0.9500
C12—S1—C2105.7 (3)B1A—O1A—B2A159.5 (7)
C22—S2—C32106.8 (4)O1A—B1A—C11A119.2 (8)
O1—B1—C1120.3 (8)O1A—B1A—C1A122.0 (7)
O1—B1—C11118.9 (7)C11A—B1A—C1A118.8 (7)
C1—B1—C11120.7 (6)O1A—B2A—C21A119.0 (7)
O1—B2—C21120.0 (9)O1A—B2A—C31A120.8 (7)
O1—B2—C31119.1 (9)C21A—B2A—C31A120.2 (7)
C21—B2—C31120.9 (7)C2A—S1A—C12A106.2 (4)
B2—O1—B1172.0 (7)C22A—S2A—C32A106.4 (3)
C2—C1—C6116.6 (6)C2A—C1A—C6A118.1 (8)
C2—C1—B1122.2 (7)C2A—C1A—B1A120.7 (6)
C6—C1—B1121.2 (7)C6A—C1A—B1A121.1 (8)
C1—C2—C3120.1 (6)C1A—C2A—C3A119.4 (9)
C1—C2—S1125.2 (5)C1A—C2A—S1A126.2 (6)
C3—C2—S1114.7 (5)C3A—C2A—S1A114.4 (8)
C4—C3—C2121.0 (7)C4A—C3A—C2A121.2 (12)
C4—C3—H3119.5C4A—C3A—H3A119.4
C2—C3—H3119.5C2A—C3A—H3A119.4
C3—C4—C5120.3 (7)C5A—C4A—C3A118.2 (12)
C3—C4—H4119.9C5A—C4A—H4A120.9
C5—C4—H4119.9C3A—C4A—H4A120.9
C6—C5—C4120.7 (8)C6A—C5A—C4A122.7 (12)
C6—C5—H5119.7C6A—C5A—H5A118.7
C4—C5—H5119.7C4A—C5A—H5A118.7
C5—C6—C1121.4 (7)C5A—C6A—C1A120.4 (10)
C5—C6—H6119.3C5A—C6A—H6A119.8
C1—C6—H6119.3C1A—C6A—H6A119.8
C12—C11—C16116.5 (8)C12A—C11A—C16A114.9 (7)
C12—C11—B1121.8 (6)C12A—C11A—B1A124.0 (7)
C16—C11—B1121.7 (7)C16A—C11A—B1A121.1 (8)
C11—C12—C13121.7 (7)C11A—C12A—C13A122.2 (10)
C11—C12—S1124.1 (6)C11A—C12A—S1A123.9 (6)
C13—C12—S1114.2 (6)C13A—C12A—S1A113.9 (9)
C14—C13—C12118.3 (8)C14A—C13A—C12A120.8 (15)
C14—C13—H13120.9C14A—C13A—H13A119.6
C12—C13—H13120.9C12A—C13A—H13A119.6
C13—C14—C15120.8 (9)C13A—C14A—C15A120.6 (17)
C13—C14—H14119.6C13A—C14A—H14A119.7
C15—C14—H14119.6C15A—C14A—H14A119.7
C16—C15—C14120.7 (8)C14A—C15A—C16A120.8 (15)
C16—C15—H15119.7C14A—C15A—H15A119.6
C14—C15—H15119.7C16A—C15A—H15A119.6
C15—C16—C11121.9 (8)C15A—C16A—C11A120.5 (11)
C15—C16—H16119.1C15A—C16A—H16A119.8
C11—C16—H16119.1C11A—C16A—H16A119.8
C22—C21—C26115.6 (8)C22A—C21A—C26A116.4 (7)
C22—C21—B2123.3 (7)C22A—C21A—B2A121.8 (6)
C26—C21—B2121.1 (8)C26A—C21A—B2A121.8 (7)
C21—C22—C23121.6 (8)C21A—C22A—C23A120.6 (6)
C21—C22—S2123.5 (6)C21A—C22A—S2A124.8 (5)
C23—C22—S2114.9 (6)C23A—C22A—S2A114.6 (5)
C24—C23—C22119.1 (9)C24A—C23A—C22A120.0 (7)
C24—C23—H23120.5C24A—C23A—H23A120.0
C22—C23—H23120.5C22A—C23A—H23A120.0
C25—C24—C23121.1 (10)C23A—C24A—C25A120.9 (7)
C25—C24—H24119.4C23A—C24A—H24A119.6
C23—C24—H24119.4C25A—C24A—H24A119.6
C26—C25—C24118.2 (10)C26A—C25A—C24A118.1 (7)
C26—C25—H25120.9C26A—C25A—H25A120.9
C24—C25—H25120.9C24A—C25A—H25A120.9
C25—C26—C21124.4 (10)C25A—C26A—C21A124.0 (8)
C25—C26—H26117.8C25A—C26A—H26A118.0
C21—C26—H26117.8C21A—C26A—H26A118.0
C32—C31—C36117.0 (8)C32A—C31A—C36A116.1 (6)
C32—C31—B2120.6 (7)C32A—C31A—B2A123.2 (6)
C36—C31—B2122.3 (7)C36A—C31A—B2A120.7 (7)
C31—C32—C33121.0 (7)C31A—C32A—C33A122.1 (6)
C31—C32—S2124.9 (6)C31A—C32A—S2A123.5 (5)
C33—C32—S2114.1 (5)C33A—C32A—S2A114.4 (5)
C34—C33—C32120.3 (8)C34A—C33A—C32A119.1 (7)
C34—C33—H33119.9C34A—C33A—H33A120.4
C32—C33—H33119.9C32A—C33A—H33A120.4
C35—C34—C33120.9 (9)C33A—C34A—C35A120.8 (7)
C35—C34—H34119.5C33A—C34A—H34A119.6
C33—C34—H34119.5C35A—C34A—H34A119.6
C34—C35—C36119.5 (8)C36A—C35A—C34A119.4 (7)
C34—C35—H35120.3C36A—C35A—H35A120.3
C36—C35—H35120.3C34A—C35A—H35A120.3
C35—C36—C31121.2 (8)C35A—C36A—C31A122.5 (7)
C35—C36—H36119.4C35A—C36A—H36A118.8
C31—C36—H36119.4C31A—C36A—H36A118.8
O1—B1—C1—C2175.6 (7)B1A—O1A—B2A—C21A97.4 (18)
C11—B1—C1—C22.9 (11)B1A—O1A—B2A—C31A83.6 (19)
O1—B1—C1—C66.4 (12)O1A—B1A—C1A—C2A176.8 (6)
C11—B1—C1—C6175.2 (7)C11A—B1A—C1A—C2A2.5 (10)
C6—C1—C2—C31.7 (10)O1A—B1A—C1A—C6A1.6 (11)
B1—C1—C2—C3179.8 (7)C11A—B1A—C1A—C6A179.1 (7)
C6—C1—C2—S1179.7 (6)C6A—C1A—C2A—C3A1.5 (11)
B1—C1—C2—S11.6 (10)B1A—C1A—C2A—C3A176.9 (8)
C12—S1—C2—C15.4 (7)C6A—C1A—C2A—S1A179.2 (6)
C12—S1—C2—C3176.0 (5)B1A—C1A—C2A—S1A0.8 (10)
C1—C2—C3—C40.5 (11)C12A—S1A—C2A—C1A2.3 (7)
S1—C2—C3—C4179.3 (6)C12A—S1A—C2A—C3A179.9 (7)
C2—C3—C4—C50.5 (12)C1A—C2A—C3A—C4A3.0 (14)
C3—C4—C5—C60.3 (12)S1A—C2A—C3A—C4A179.0 (8)
C4—C5—C6—C10.9 (13)C2A—C3A—C4A—C5A3.0 (16)
C2—C1—C6—C51.9 (11)C3A—C4A—C5A—C6A1.6 (16)
B1—C1—C6—C5179.9 (8)C4A—C5A—C6A—C1A0.2 (14)
O1—B1—C11—C12176.1 (7)C2A—C1A—C6A—C5A0.1 (11)
C1—B1—C11—C122.4 (11)B1A—C1A—C6A—C5A178.3 (8)
O1—B1—C11—C164.3 (12)O1A—B1A—C11A—C12A178.9 (6)
C1—B1—C11—C16177.3 (8)C1A—B1A—C11A—C12A0.5 (10)
C16—C11—C12—C130.2 (10)O1A—B1A—C11A—C16A2.0 (11)
B1—C11—C12—C13179.4 (7)C1A—B1A—C11A—C16A178.7 (7)
C16—C11—C12—S1177.8 (6)C16A—C11A—C12A—C13A0.3 (11)
B1—C11—C12—S12.5 (10)B1A—C11A—C12A—C13A178.9 (8)
C2—S1—C12—C115.8 (7)C16A—C11A—C12A—S1A177.6 (6)
C2—S1—C12—C13176.1 (6)B1A—C11A—C12A—S1A3.2 (10)
C11—C12—C13—C140.3 (12)C2A—S1A—C12A—C11A4.3 (7)
S1—C12—C13—C14177.9 (7)C2A—S1A—C12A—C13A177.6 (7)
C12—C13—C14—C152.2 (13)C11A—C12A—C13A—C14A1.6 (16)
C13—C14—C15—C164.0 (14)S1A—C12A—C13A—C14A176.5 (11)
C14—C15—C16—C113.9 (14)C12A—C13A—C14A—C15A1 (2)
C12—C11—C16—C152.0 (12)C13A—C14A—C15A—C16A2 (2)
B1—C11—C16—C15177.6 (8)C14A—C15A—C16A—C11A2.9 (17)
O1—B2—C21—C22178.3 (7)C12A—C11A—C16A—C15A1.8 (12)
C31—B2—C21—C220.9 (11)B1A—C11A—C16A—C15A178.9 (9)
O1—B2—C21—C261.5 (12)O1A—B2A—C21A—C22A177.1 (6)
C31—B2—C21—C26179.4 (7)C31A—B2A—C21A—C22A2.0 (10)
C26—C21—C22—C231.0 (10)O1A—B2A—C21A—C26A2.4 (11)
B2—C21—C22—C23178.8 (8)C31A—B2A—C21A—C26A178.5 (7)
C26—C21—C22—S2179.2 (6)C26A—C21A—C22A—C23A1.1 (10)
B2—C21—C22—S20.6 (10)B2A—C21A—C22A—C23A178.4 (7)
C32—S2—C22—C211.8 (7)C26A—C21A—C22A—S2A177.9 (6)
C32—S2—C22—C23179.9 (6)B2A—C21A—C22A—S2A2.6 (9)
C21—C22—C23—C241.7 (12)C32A—S2A—C22A—C21A2.6 (7)
S2—C22—C23—C24179.9 (7)C32A—S2A—C22A—C23A178.4 (5)
C22—C23—C24—C250.2 (14)C21A—C22A—C23A—C24A0.3 (11)
C23—C24—C25—C262.0 (15)S2A—C22A—C23A—C24A178.8 (6)
C24—C25—C26—C212.9 (15)C22A—C23A—C24A—C25A0.9 (12)
C22—C21—C26—C251.4 (13)C23A—C24A—C25A—C26A1.2 (12)
B2—C21—C26—C25178.8 (9)C24A—C25A—C26A—C21A0.4 (12)
O1—B2—C31—C32178.5 (6)C22A—C21A—C26A—C25A0.8 (11)
C21—B2—C31—C320.7 (10)B2A—C21A—C26A—C25A178.7 (8)
O1—B2—C31—C365.0 (11)O1A—B2A—C31A—C32A177.2 (6)
C21—B2—C31—C36175.8 (7)C21A—B2A—C31A—C32A1.8 (10)
C36—C31—C32—C331.6 (9)O1A—B2A—C31A—C36A1.8 (11)
B2—C31—C32—C33178.3 (7)C21A—B2A—C31A—C36A179.2 (7)
C36—C31—C32—S2177.5 (6)C36A—C31A—C32A—C33A1.0 (10)
B2—C31—C32—S20.9 (9)B2A—C31A—C32A—C33A180.0 (7)
C22—S2—C32—C311.9 (6)C36A—C31A—C32A—S2A178.7 (5)
C22—S2—C32—C33177.2 (6)B2A—C31A—C32A—S2A2.2 (9)
C31—C32—C33—C340.5 (11)C22A—S2A—C32A—C31A2.3 (6)
S2—C32—C33—C34179.7 (7)C22A—S2A—C32A—C33A179.8 (5)
C32—C33—C34—C351.2 (13)C31A—C32A—C33A—C34A0.9 (10)
C33—C34—C35—C360.2 (13)S2A—C32A—C33A—C34A178.8 (6)
C34—C35—C36—C312.4 (13)C32A—C33A—C34A—C35A1.2 (11)
C32—C31—C36—C353.1 (11)C33A—C34A—C35A—C36A1.6 (12)
B2—C31—C36—C35179.7 (8)C34A—C35A—C36A—C31A1.8 (12)
B2A—O1A—B1A—C11A171.1 (16)C32A—C31A—C36A—C35A1.4 (11)
B2A—O1A—B1A—C1A10 (2)B2A—C31A—C36A—C35A179.5 (7)
Comparison of B—C and S—S bond lengths and C—B—C and C—S—C bond angles (Å, °) top
B—CC—B—CS—CC—S—C
LIPFAS1.533119.61.745105.9
LIPFIW1.546119.41.745106.5
QONKAG1.534119.61.740106.2
(I)1.539121.81.758106.4
(II)1.548120.21.746106.3
Mean values of bond lengths [Å] and angles [°] in I and II and three structures (REFCODES given) from the CSD.
Systematic absence exceptions for (I) (space group P21) top
-21--a--c--n-
N54201119731994
N(I>3σ(I))0118512701219
mean intensity0.32.85.65.6
mean I/σ(I)1.07.411.611.5
N: number of reflection per group; N[I>3σ(I)]: number of reflections with I greater than 3σ(I).
Systematic absence exceptions for (II) (space group P21/c) top
-21--a--c--n-
N14168716971694
N(I>3σ(I))0330103350
mean intensity0.35.00.75.1
mean I/σ(I)0.95.01.55.1
N: number of reflection per group; N[I>3σ(I)]: number of reflections with I greater than 3σ(I).
 

References

First citationAgou, T., Kobayashi, J. & Kawashima, T. (2007). Chem. Eur. J. 13, 8051–8060.  CrossRef PubMed CAS Google Scholar
First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CrossRef IUCr Journals Google Scholar
First citationGrotthuss, E. von, John, A., Kaese, T. & Wagner, M. (2018). Asia. J. Org. Chem. 7, 37–53.  Google Scholar
First citationHarvey, R. G. (1997). Polycyclic Aromatic Hydrocarbons. New York: Wiley and Sons.  Google Scholar
First citationKobayashi, J., Kato, K., Agou, T. & Kawashima, T. (2009). Chem. Asian J. 4, 42–49.  CrossRef PubMed CAS Google Scholar
First citationLiu, Z. & Marder, T. B. (2008). Angew. Chem. Int. Ed. 47, 242–244.  CrossRef CAS Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationRieger, R. & Müllen, K. (2010). J. Phys. Org. Chem. 23, 315–325.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSolé, S. & Gabbaï, F. P. (2004). Chem. Commun. pp. 1284–1285.  Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStępień, M., Gońka, E., Żyła, M. & Sprutta, N. (2017). Chem. Rev. 117, 3479–3716.  PubMed Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, J., Pisula, W. & Müllen, K. (2007). Chem. Rev. 107, 718–747.  CrossRef PubMed CAS Google Scholar

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