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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2317.
Published online 2008 November 13. doi:  10.1107/S1600536808036210
PMCID: PMC2959856

The cocrystal 10-(2-methyl-4-phenyl-1H-inden-6-yl)-10H-phenothia­zine–10-(2-methyl-7-phenyl-1H-inden-5-yl)-10H-phenothia­zine (0.54/0.46)

Abstract

The title compound, 0.535C28H21NS.0.465C28H21NS, was synthesized by palladium-catalysed amination. The structure is composed of two isomeric mol­ecules, viz. 10-(2-methyl-4-phenyl-1H-inden-6-yl)-10H-phenothia­zine, and 10-(2-methyl-7-phenyl-1H-inden-5-yl)-10H-phenothia­zine, in the refined ratio 0.535 (12):0.465 (12). The isomers differ by the localization of the double bond in the cyclo­penta­diene ring. There are two sites in the structure that are occupied by the isomers. The respective isomers are occupationally disordered in each site, the refined proportions being 0.640 (6):0.360 (6) and 0.43 (1):0.57 (1). Moreover, each isomeric mol­ecule is chiral; due to the crystallographic centres of symmetry, the mol­ecules are also present in enanti­omeric pairs. The crystal structure is stabilized by weak π–π [C(...)C = 3.389 (2) Å] inter­actions.

Related literature

The title product was used to obtain the pertinent ansa-zirconocene for isotactic olefin polymerization study, see: Voskoboynikov et al. (2006). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For bond-lengths data, see: Allen et al. (1987 [triangle]). For details of the Buchwald–Hartwig amination protocol used in the synthesis, see: Yang & Buchwald (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2317-scheme1.jpg

Experimental

Crystal data

  • 0.535C28H21NS·0.465C28H21NS
  • M r = 403.52
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2317-efi1.jpg
  • a = 12.6480 (6) Å
  • b = 12.6654 (6) Å
  • c = 14.6970 (7) Å
  • α = 77.4920 (10)°
  • β = 64.8070 (10)°
  • γ = 82.9690 (10)°
  • V = 2078.62 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 100 (2) K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (APEX2; Bruker, 2005 [triangle]) T min = 0.961, T max = 0.983
  • 25507 measured reflections
  • 10999 independent reflections
  • 7713 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.105
  • S = 1.01
  • 10999 reflections
  • 569 parameters
  • 44 restraints
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036210/fb2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036210/fb2115Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the ExxonMobil Chemical Company and by the Russian and Moldova Foundation for Basic Research (grant No. 08-03-90103).

supplementary crystallographic information

Comment

The title product was used to obtain the pertinent ansa-zirconocene for isotactic olefin polymerization study (Voskoboynikov et al., (YEAR?)). Herein we report the crystal structure which was synthesized by Buchwald–Hartwig amination protocol (Yang & Buchwald, 1999) from the mixture of the 6-chloro-2-methyl-4-phenyl-1H-indene and 5-chloro-2-methyl-7-phenyl-1H-indene, and 10H-phenothiazine in the presence of lithium tert-butoxide and Pd(PtBu3)2 in toluene at reflux.

The title structure consists of two independent isomers (Fig. 1): 10-(2-methyl-4-phenyl-1H-inden-6-yl)-10H-phenothiazine (Ia), and 10-(2-methyl-7-phenyl-1H-inden-5-yl)-10H-phenothiazine (Ib). These molecules are situated in two sites (A and A') in the structure. In each site, the isomeric molecules are occupationally disordered. In the site A, the isomers (Ia) and (Ib) superimpose in the ratio of 0.640 (6):0.360 (6), respectively, while for the site A' the nearly reverse proportion 0.43 (1):0.57 (1) is observed. Therefore the total ratio of two isomers in the crystal structure is 0.535 (12):0.465 (12) which is in the reasonable agreement with the data of a 1H NMR study which showed 1:1 ratio.

In the title structure, all the bond lengths and angles show normal values (Allen et al., 1987; Allen, 2002; CSD (2007), version 5.29). In both isomers, the phenothiazine fragment is bent relative to the line connecting S1(S1') and N1(N1') atoms; the corresponding interplanar angles equal to 147.72 (3) and 147.69 (4)° for A and A' site, respectively. In each isomer, the six-membered 1,4-thiazine ring adopts the boat conformation. In each isomer, the indene ring is nearly planar (the mean deviations are 0.025° and 0.043Å for A and A', respectively). The indene rings are nearly perpendicular to the mean planes of the phenothiazine fragments (the interplanar angles are 84.24 (12) and 86.49 (12)° for A and A', respectively). The phenyl substituent at C5 (C5') atoms is rotated out of the plane of the indene ring (the interplanar angles are 41.96 (13) and 42.8 (2)° for A and A', respectively). The relative orientations of the molecular fragments are plausibly influenced by the steric repulsions of the closest hydrogen atoms. The molecules at the site A' form dimers by means of weak π–π interactions (C4'···C15'(-x, 2-y, -z), 3.389 (2) Å).

Experimental

Under argon atmosphere, a mixture of 9.63 g (40.0 mmol) of 6-chloro-2-methyl-4-phenyl-1H-indene and 5-chloro-2-methyl-7-phenyl-1H-indene, 9.60 g (120 mmol) of tBuOLi, 7.97 g (40.0 mmol) of 10H-phenothiazine, 460 mg (0.80 mmol) of Pd(dba)2, 320 mg (1.60 mmol) of tris(tert-butyl)phosphine, and 80 ml of toluene was refluxed for 10 h. The resulting mixture was cooled to room temperature, passed through a short column with silica gel 60 (40–63 µm, d 80 mm, l 50 mm). The silica gel layer was additionally washed by 300 ml of methyltert-butyl ether. The combined elute was evaporated to dryness. The crude product was purified by flash-chromatography on silica gel 60 (40–63 µm, d 60 mm, l 500 mm; eluent: hexane/methyltert-butyl ether 20:1, vol.). Yield 10.7 g (66%) of approx. 1:1 mixture of 10-(2-methyl-4-phenyl-1H-inden-6-yl)-10H-phenothiazine (the isomer (Ia)) and 10-(2-methyl-7-phenyl-1H-inden-5-yl)-10H-phenothiazine (the isomer (Ib)). The yellow single crystals suitable for the X-ray analysis (in the form of prisms and with the size of 0.20 × 0.15 × 0.10 mm) were grown from toluene after a few days.

1H NMR (CDCl3): δ 6.74–7.59 (m, 7-H in indenyl of the isomer (Ib) and 3,7- H in indenyl of the isomer (Ia), Ph and phenothiazine of the isomers (Ia) and (Ib)), 6.59 (m, 3-H in indenyl of the isomer (Ib)), 6.35 (d, J= 7.7 Hz, 5-H in indenyl of the isomer (Ib)), 6.32 (d, J= 7.7 Hz, 5-H in indenyl of the isomer (Ia)), 3.50 (s, 2H, CH2 of the isomer (Ib)), 3.46 (s, CH2 of the isomer (Ia)), 2.17 (m, 2-Me of the isomers (Ia) and (Ib)).

13C{1H} NMR (CDCl3): 6 149.0, 148.4, 148.3, 147.9, 146.5, 144.6, 144.5, 143.5, 140.6, 140.2, 139.7, 139.5, 136.7, 135.7, 129.4, 128.7, 128.5*, 128.3, 127.5, 127.2, 127.0, 126.8*, 126.5*, 126.0, 124.7, 122.2, 121.2*, 119.6, 115.87, 115.81, 43.1, 42.7, 17.0, 16.8 (* two resonances).

Refinement

All the H atoms except some of them in the disordered region could be distinguished in the difference electron density map. However, they were situated into the idealized positions and refined in the riding motion approximation with C—H distances equal to 0.98Å for the methyl groups, 0.95Å for the aryl carbon atoms, and 0.99Å for the carbon atoms of the cyclopentadiene ring in the sp3 state. Uiso(H)=1.5Ueq(parent atom) for the methyls and Uiso(H)=1.2Ueq(parent atom) for the remaining atoms. For the methyl hydrogen atoms, AFIX 137 command was used (Sheldrick, 2008). In the A and A' sites, the molecules are occupatioanlly disordered, being a superposition of the isomers (Ia) and (Ib). The proportions of (Ia) to (Ib) in the sites A and A' were refined with isotropic thermal displacement parameters using EADP command to equalize thermal parameters for the corresponding atomic pairs: C1A and C1B; C1' and C1"; C2A and C2B; C2' and C2"; C3A and C3B; C3' and C3"; C10A and C1B; C10' C10". These proportions were fixed in further refinement. In the next step all the disordered carbon atoms were refined unisotropically. The disordered fragments of the sites A and A' were refined using the command SAME 0.005 0.005 for (C3A C2A C1A C10A), (C1B C2B C3B C10B), (C1' C2' C3' C10'), (C3" C2" C1" C10"). In addition, the following commands were used: DFIX 1.492 0.005 C9 C1A C4 C3B C4' C3' C9' C1"; DFIX 1.464 0.005 C4 C3A C9 C1B C9' C1' C4' C3". (The target distances were retrieved from the Cambridge Crystallographic Database (2007 Version; Allen, 2002). Moreover, the above mentioned EADP commands were also applied.

Figures

Fig. 1.
The view of the title molecules, showing the atom-numbering scheme and the displacement ellipsoids drawn at 50% probability level. The hydrogen atoms are shown as spheres of arbitrary radius. The major-occupied parts at the sites A and A' correspond to ...

Crystal data

0.535C28H21NS·0.465C28H21NSZ = 4
Mr = 403.52F000 = 848
Triclinic, P1Dx = 1.289 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 12.6480 (6) ÅCell parameters from 5458 reflections
b = 12.6654 (6) Åθ = 2.4–28.8º
c = 14.6970 (7) ŵ = 0.17 mm1
α = 77.4920 (10)ºT = 100 (2) K
β = 64.8070 (10)ºPrism, yellow
γ = 82.9690 (10)º0.20 × 0.15 × 0.10 mm
V = 2078.62 (17) Å3

Data collection

Bruker SMART APEXII CCD diffractometer10999 independent reflections
Radiation source: fine-focus sealed tube7713 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
T = 100(2) Kθmax = 29.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(APEX2; Bruker, 2005)h = −17→17
Tmin = 0.961, Tmax = 0.983k = −17→17
25507 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.105  w = 1/[σ2(Fo2) + (0.0417P)2 + 0.4032P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
10999 reflectionsΔρmax = 0.35 e Å3
569 parametersΔρmin = −0.34 e Å3
44 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S1−0.38737 (4)0.28779 (4)0.38391 (4)0.03348 (11)
N1−0.14054 (11)0.36876 (10)0.28600 (10)0.0213 (3)
C3A0.3165 (4)0.5267 (8)0.0573 (4)0.0219 (11)0.64
H3AA0.36910.55860.07350.026*0.64
C2A0.3355 (5)0.5131 (4)−0.0372 (3)0.0231 (9)0.64
C1A0.2319 (5)0.4617 (9)−0.0324 (3)0.0246 (11)0.64
H1AA0.25520.3920−0.05690.030*0.64
H1AB0.19560.5100−0.07460.030*0.64
C10A0.4377 (3)0.5458 (3)−0.1361 (3)0.0311 (9)0.64
H10A0.49390.5814−0.12410.047*0.64
H10B0.41100.5960−0.18360.047*0.64
H10C0.47520.4814−0.16560.047*0.64
C1B0.2296 (9)0.4449 (17)−0.0275 (5)0.0246 (11)0.36
H1BA0.21440.4198−0.07710.030*0.36
C2B0.3296 (8)0.4872 (10)−0.0430 (6)0.0231 (9)0.36
C3B0.3226 (8)0.5107 (17)0.0555 (7)0.0219 (11)0.36
H3BA0.38060.46520.07670.026*0.36
H3BB0.33740.58780.04790.026*0.36
C10B0.4380 (6)0.5083 (6)−0.1393 (5)0.0311 (9)0.36
H10D0.42140.5032−0.19760.047*0.36
H10E0.49930.4546−0.13530.047*0.36
H10F0.46430.5810−0.14840.047*0.36
C40.20140 (13)0.48447 (12)0.13178 (11)0.0206 (3)
C50.14160 (13)0.48424 (11)0.23689 (11)0.0191 (3)
C60.02849 (14)0.44463 (11)0.28549 (12)0.0205 (3)
H6A−0.01470.44430.35660.025*
C7−0.02250 (13)0.40571 (12)0.23245 (12)0.0209 (3)
C80.03690 (14)0.40435 (12)0.12884 (12)0.0226 (3)
H8A0.00230.37690.09310.027*
C90.14855 (14)0.44441 (12)0.07904 (11)0.0224 (3)
C110.19072 (13)0.52333 (12)0.29924 (11)0.0194 (3)
C120.25058 (13)0.61938 (12)0.26471 (12)0.0218 (3)
H12A0.26290.66040.19890.026*
C130.29250 (14)0.65589 (13)0.32554 (13)0.0253 (3)
H13A0.33280.72170.30140.030*
C140.27550 (14)0.59619 (13)0.42142 (12)0.0259 (3)
H14A0.30400.62120.46300.031*
C150.21710 (14)0.50040 (13)0.45646 (12)0.0261 (3)
H15A0.20630.45900.52180.031*
C160.17419 (14)0.46467 (13)0.39630 (12)0.0230 (3)
H16A0.13290.39930.42140.028*
C17−0.23058 (14)0.45087 (12)0.30246 (12)0.0222 (3)
C18−0.20467 (14)0.56058 (12)0.26732 (12)0.0239 (3)
H18A−0.12540.58100.23240.029*
C19−0.29344 (15)0.63977 (14)0.28299 (14)0.0302 (4)
H19A−0.27430.71370.25740.036*
C20−0.40919 (16)0.61252 (15)0.33534 (15)0.0366 (4)
H20A−0.46960.66720.34720.044*
C21−0.43612 (15)0.50402 (15)0.37037 (15)0.0349 (4)
H21A−0.51550.48430.40720.042*
C22−0.34799 (14)0.42418 (13)0.35195 (13)0.0254 (3)
C23−0.26889 (14)0.22643 (12)0.41132 (12)0.0241 (3)
C24−0.28651 (16)0.13143 (13)0.48368 (12)0.0293 (4)
H24A−0.36320.10540.52270.035*
C25−0.19306 (17)0.07471 (14)0.49914 (13)0.0339 (4)
H25A−0.20490.00960.54820.041*
C26−0.08275 (17)0.11414 (14)0.44232 (13)0.0329 (4)
H26A−0.01780.07440.45090.039*
C27−0.06447 (15)0.21071 (13)0.37273 (13)0.0269 (3)
H27A0.01230.23710.33550.032*
C28−0.15795 (14)0.26952 (12)0.35684 (11)0.0212 (3)
S1'0.52340 (4)0.90861 (4)0.22623 (3)0.03033 (11)
N1'0.29876 (11)0.95936 (10)0.19830 (10)0.0224 (3)
C1'−0.1142 (6)0.8341 (9)0.3848 (8)0.0280 (9)0.57
H1'A−0.11060.77720.43750.034*0.57
C2'−0.2113 (5)0.8666 (9)0.3686 (9)0.0234 (17)0.57
C3'−0.1847 (4)0.9641 (10)0.2835 (9)0.0274 (7)0.57
H3'A−0.20600.95250.22900.033*0.57
H3'B−0.22721.02980.30960.033*0.57
C10'−0.3346 (6)0.8357 (13)0.4355 (11)0.0367 (7)0.57
H10G−0.33510.76760.48260.055*0.57
H10H−0.37390.82640.39310.055*0.57
H10I−0.37580.89280.47490.055*0.57
C3"−0.1803 (5)0.9560 (14)0.2818 (12)0.0274 (7)0.43
H3"C−0.22800.98890.24720.033*0.43
C2"−0.2181 (6)0.8864 (14)0.3722 (13)0.0234 (17)0.43
C1"−0.1148 (8)0.8372 (13)0.3937 (10)0.0280 (9)0.43
H1"A−0.12350.84690.46160.034*0.43
H1"B−0.10460.75900.39090.034*0.43
C10"−0.3371 (7)0.8421 (17)0.4344 (15)0.0367 (7)0.43
H10J−0.38800.87030.39890.055*0.43
H10K−0.36990.86400.50140.055*0.43
H10L−0.33170.76290.44370.055*0.43
C4'−0.05486 (13)0.97368 (13)0.24479 (12)0.0231 (3)
C5'0.02241 (13)1.04173 (12)0.16016 (12)0.0218 (3)
C6'0.14048 (14)1.03393 (12)0.14479 (12)0.0230 (3)
H6'A0.19541.07850.08750.028*
C7'0.17846 (14)0.96234 (12)0.21175 (12)0.0225 (3)
C8'0.10177 (14)0.89287 (12)0.29435 (12)0.0239 (3)
H8'A0.12840.84270.33900.029*
C9'−0.01475 (13)0.89899 (12)0.30968 (11)0.0239 (3)
C11'−0.01489 (14)1.11879 (12)0.08630 (12)0.0229 (3)
C12'−0.11953 (15)1.17980 (13)0.11959 (14)0.0283 (4)
H12B−0.16731.17360.19070.034*
C13'−0.15425 (17)1.24937 (14)0.04968 (15)0.0360 (4)
H13B−0.22591.29000.07320.043*
C14'−0.08514 (17)1.25996 (14)−0.05407 (15)0.0368 (4)
H14B−0.10951.3074−0.10170.044*
C15'0.01959 (17)1.20117 (13)−0.08826 (14)0.0319 (4)
H15B0.06771.2087−0.15940.038*
C16'0.05434 (15)1.13104 (13)−0.01829 (13)0.0269 (4)
H16B0.12631.0909−0.04220.032*
C17'0.33336 (13)1.04156 (12)0.23036 (11)0.0204 (3)
C18'0.26413 (14)1.13481 (13)0.25307 (12)0.0249 (3)
H18B0.19171.14380.24680.030*
C19'0.29908 (16)1.21455 (13)0.28463 (12)0.0288 (4)
H19B0.25021.27720.30030.035*
C20'0.40464 (16)1.20386 (14)0.29361 (13)0.0316 (4)
H20B0.42891.25900.31460.038*
C21'0.47437 (15)1.11155 (14)0.27160 (12)0.0291 (4)
H21B0.54731.10390.27690.035*
C22'0.43907 (13)1.03023 (13)0.24200 (12)0.0231 (3)
C23'0.49271 (14)0.87210 (13)0.13113 (12)0.0251 (3)
C24'0.57445 (16)0.80923 (14)0.06501 (13)0.0333 (4)
H24B0.64900.79340.06670.040*
C25'0.54849 (17)0.76935 (14)−0.00342 (13)0.0363 (4)
H25B0.60400.7249−0.04740.044*
C26'0.44052 (17)0.79525 (13)−0.00680 (13)0.0341 (4)
H26B0.42230.7686−0.05390.041*
C27'0.35867 (15)0.85936 (13)0.05747 (12)0.0275 (4)
H27B0.28550.87720.05320.033*
C28'0.38264 (14)0.89814 (12)0.12854 (12)0.0226 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0311 (2)0.0292 (2)0.0475 (3)−0.00855 (18)−0.0236 (2)−0.00198 (19)
N10.0246 (7)0.0195 (6)0.0234 (7)−0.0014 (5)−0.0139 (6)−0.0025 (5)
C3A0.0209 (9)0.023 (3)0.0244 (8)0.0050 (12)−0.0120 (7)−0.0066 (9)
C2A0.0276 (10)0.024 (3)0.0216 (10)0.0081 (13)−0.0133 (9)−0.0097 (11)
C1A0.0295 (9)0.025 (3)0.0244 (9)0.0058 (10)−0.0153 (8)−0.0097 (11)
C10A0.0300 (10)0.039 (3)0.0222 (10)0.0123 (16)−0.0091 (8)−0.0133 (14)
C1B0.0295 (9)0.025 (3)0.0244 (9)0.0058 (10)−0.0153 (8)−0.0097 (11)
C2B0.0276 (10)0.024 (3)0.0216 (10)0.0081 (13)−0.0133 (9)−0.0097 (11)
C3B0.0209 (9)0.023 (3)0.0244 (8)0.0050 (12)−0.0120 (7)−0.0066 (9)
C10B0.0300 (10)0.039 (3)0.0222 (10)0.0123 (16)−0.0091 (8)−0.0133 (14)
C40.0241 (8)0.0189 (7)0.0235 (8)0.0047 (6)−0.0153 (7)−0.0045 (6)
C50.0254 (8)0.0150 (7)0.0215 (8)0.0031 (6)−0.0151 (7)−0.0034 (6)
C60.0280 (8)0.0175 (7)0.0191 (7)0.0012 (6)−0.0135 (7)−0.0028 (6)
C70.0253 (8)0.0160 (7)0.0239 (8)−0.0002 (6)−0.0139 (7)−0.0013 (6)
C80.0302 (8)0.0213 (8)0.0233 (8)0.0012 (6)−0.0174 (7)−0.0057 (6)
C90.0294 (8)0.0210 (7)0.0217 (8)0.0061 (6)−0.0157 (7)−0.0068 (6)
C110.0197 (7)0.0218 (7)0.0199 (7)0.0043 (6)−0.0110 (6)−0.0067 (6)
C120.0239 (8)0.0227 (8)0.0213 (8)0.0014 (6)−0.0123 (7)−0.0041 (6)
C130.0243 (8)0.0250 (8)0.0313 (9)−0.0009 (6)−0.0141 (7)−0.0084 (7)
C140.0270 (8)0.0322 (9)0.0275 (8)0.0057 (7)−0.0178 (7)−0.0136 (7)
C150.0320 (9)0.0300 (9)0.0203 (8)0.0060 (7)−0.0153 (7)−0.0072 (7)
C160.0281 (8)0.0215 (8)0.0216 (8)0.0018 (6)−0.0123 (7)−0.0058 (6)
C170.0283 (8)0.0231 (8)0.0224 (8)0.0009 (6)−0.0176 (7)−0.0047 (6)
C180.0281 (8)0.0233 (8)0.0260 (8)−0.0015 (7)−0.0174 (7)−0.0025 (6)
C190.0373 (10)0.0228 (8)0.0377 (10)0.0017 (7)−0.0238 (8)−0.0037 (7)
C200.0335 (10)0.0311 (10)0.0543 (12)0.0086 (8)−0.0280 (9)−0.0106 (9)
C210.0259 (9)0.0397 (10)0.0446 (11)0.0006 (8)−0.0199 (8)−0.0082 (8)
C220.0285 (8)0.0254 (8)0.0299 (9)−0.0031 (7)−0.0197 (7)−0.0027 (7)
C230.0320 (9)0.0224 (8)0.0232 (8)−0.0015 (7)−0.0147 (7)−0.0071 (6)
C240.0403 (10)0.0238 (8)0.0222 (8)−0.0071 (7)−0.0101 (8)−0.0035 (7)
C250.0537 (12)0.0218 (8)0.0239 (9)−0.0022 (8)−0.0160 (9)0.0007 (7)
C260.0423 (11)0.0258 (9)0.0331 (10)0.0061 (8)−0.0207 (9)−0.0034 (7)
C270.0306 (9)0.0228 (8)0.0288 (9)0.0018 (7)−0.0143 (8)−0.0051 (7)
C280.0299 (8)0.0187 (7)0.0188 (7)−0.0015 (6)−0.0129 (7)−0.0045 (6)
S1'0.0272 (2)0.0343 (2)0.0333 (2)0.00648 (18)−0.01859 (19)−0.00491 (18)
N1'0.0209 (6)0.0239 (7)0.0257 (7)0.0022 (5)−0.0122 (6)−0.0071 (5)
C1'0.0333 (9)0.0284 (11)0.0237 (15)−0.0090 (8)−0.0120 (9)−0.0028 (12)
C2'0.0287 (10)0.019 (4)0.0246 (11)−0.0039 (16)−0.0081 (10)−0.013 (2)
C3'0.0242 (9)0.0370 (17)0.0240 (9)−0.0053 (9)−0.0111 (8)−0.0068 (10)
C10'0.0325 (10)0.048 (2)0.0277 (10)−0.0138 (10)−0.0077 (8)−0.0067 (10)
C3"0.0242 (9)0.0370 (17)0.0240 (9)−0.0053 (9)−0.0111 (8)−0.0068 (10)
C2"0.0287 (10)0.019 (4)0.0246 (11)−0.0039 (16)−0.0081 (10)−0.013 (2)
C1"0.0333 (9)0.0284 (11)0.0237 (15)−0.0090 (8)−0.0120 (9)−0.0028 (12)
C10"0.0325 (10)0.048 (2)0.0277 (10)−0.0138 (10)−0.0077 (8)−0.0067 (10)
C4'0.0243 (8)0.0273 (8)0.0218 (8)−0.0023 (6)−0.0118 (7)−0.0068 (6)
C5'0.0251 (8)0.0218 (8)0.0235 (8)−0.0016 (6)−0.0137 (7)−0.0058 (6)
C6'0.0245 (8)0.0234 (8)0.0223 (8)−0.0042 (6)−0.0111 (7)−0.0019 (6)
C7'0.0240 (8)0.0229 (8)0.0249 (8)−0.0004 (6)−0.0127 (7)−0.0077 (6)
C8'0.0298 (9)0.0218 (8)0.0233 (8)0.0005 (7)−0.0146 (7)−0.0032 (6)
C9'0.0281 (8)0.0241 (8)0.0210 (8)−0.0048 (7)−0.0106 (7)−0.0039 (6)
C11'0.0266 (8)0.0215 (8)0.0275 (8)−0.0038 (6)−0.0173 (7)−0.0035 (6)
C12'0.0301 (9)0.0283 (9)0.0344 (9)0.0000 (7)−0.0187 (8)−0.0104 (7)
C13'0.0390 (10)0.0280 (9)0.0530 (12)0.0066 (8)−0.0310 (10)−0.0102 (8)
C14'0.0543 (12)0.0235 (9)0.0482 (12)−0.0013 (8)−0.0393 (10)0.0009 (8)
C15'0.0462 (11)0.0235 (8)0.0322 (9)−0.0066 (8)−0.0235 (9)0.0009 (7)
C16'0.0327 (9)0.0229 (8)0.0287 (9)−0.0021 (7)−0.0170 (8)−0.0024 (7)
C17'0.0222 (8)0.0215 (8)0.0177 (7)−0.0021 (6)−0.0093 (6)−0.0008 (6)
C18'0.0276 (8)0.0252 (8)0.0231 (8)0.0018 (7)−0.0124 (7)−0.0043 (6)
C19'0.0386 (10)0.0253 (8)0.0241 (8)0.0009 (7)−0.0142 (8)−0.0060 (7)
C20'0.0441 (11)0.0300 (9)0.0269 (9)−0.0099 (8)−0.0187 (8)−0.0039 (7)
C21'0.0293 (9)0.0364 (10)0.0265 (9)−0.0075 (7)−0.0168 (8)−0.0007 (7)
C22'0.0228 (8)0.0269 (8)0.0196 (8)−0.0012 (6)−0.0102 (7)−0.0008 (6)
C23'0.0266 (8)0.0228 (8)0.0224 (8)−0.0009 (6)−0.0089 (7)0.0004 (6)
C24'0.0298 (9)0.0283 (9)0.0302 (9)0.0027 (7)−0.0046 (8)−0.0002 (7)
C25'0.0443 (11)0.0242 (9)0.0248 (9)0.0006 (8)−0.0005 (8)−0.0036 (7)
C26'0.0534 (12)0.0229 (8)0.0227 (9)−0.0068 (8)−0.0122 (8)−0.0015 (7)
C27'0.0359 (9)0.0226 (8)0.0237 (8)−0.0035 (7)−0.0128 (8)−0.0007 (6)
C28'0.0274 (8)0.0173 (7)0.0203 (8)−0.0020 (6)−0.0090 (7)0.0008 (6)

Geometric parameters (Å, °)

S1—C231.7621 (16)S1'—C23'1.7617 (17)
S1—C221.7643 (16)S1'—C22'1.7624 (16)
N1—C281.4206 (19)N1'—C28'1.412 (2)
N1—C171.4217 (19)N1'—C17'1.4132 (19)
N1—C71.442 (2)N1'—C7'1.4453 (19)
C3A—C2A1.351 (6)C1'—C2'1.348 (6)
C3A—C41.478 (3)C1'—C9'1.467 (4)
C3A—H3AA0.9500C1'—H1'A0.9500
C2A—C10A1.492 (3)C2'—C10'1.493 (3)
C2A—C1A1.502 (6)C2'—C3'1.510 (7)
C1A—C91.507 (3)C3'—C4'1.503 (4)
C1A—H1AA0.9900C3'—H3'A0.9900
C1A—H1AB0.9900C3'—H3'B0.9900
C10A—H10A0.9800C10'—H10G0.9800
C10A—H10B0.9800C10'—H10H0.9800
C10A—H10C0.9800C10'—H10I0.9800
C1B—C2B1.345 (7)C3"—C2"1.352 (7)
C1B—C91.461 (5)C3"—C4'1.471 (4)
C1B—H1BA0.9500C3"—H3"C0.9500
C2B—C10B1.493 (3)C2"—C10"1.493 (3)
C2B—C3B1.504 (8)C2"—C1"1.503 (8)
C3B—C41.489 (5)C1"—C9'1.494 (4)
C3B—H3BA0.9900C1"—H1"A0.9900
C3B—H3BB0.9900C1"—H1"B0.9900
C10B—H10D0.9800C10"—H10J0.9800
C10B—H10E0.9800C10"—H10K0.9800
C10B—H10F0.9800C10"—H10L0.9800
C4—C51.401 (2)C4'—C5'1.397 (2)
C4—C91.414 (2)C4'—C9'1.402 (2)
C5—C61.400 (2)C5'—C6'1.406 (2)
C5—C111.493 (2)C5'—C11'1.489 (2)
C6—C71.393 (2)C6'—C7'1.389 (2)
C6—H6A0.9500C6'—H6'A0.9500
C7—C81.385 (2)C7'—C8'1.390 (2)
C8—C91.386 (2)C8'—C9'1.388 (2)
C8—H8A0.9500C8'—H8'A0.9500
C11—C121.393 (2)C11'—C16'1.392 (2)
C11—C161.398 (2)C11'—C12'1.397 (2)
C12—C131.392 (2)C12'—C13'1.386 (2)
C12—H12A0.9500C12'—H12B0.9500
C13—C141.387 (2)C13'—C14'1.383 (3)
C13—H13A0.9500C13'—H13B0.9500
C14—C151.381 (2)C14'—C15'1.384 (3)
C14—H14A0.9500C14'—H14B0.9500
C15—C161.387 (2)C15'—C16'1.390 (2)
C15—H15A0.9500C15'—H15B0.9500
C16—H16A0.9500C16'—H16B0.9500
C17—C221.395 (2)C17'—C18'1.394 (2)
C17—C181.401 (2)C17'—C22'1.405 (2)
C18—C191.387 (2)C18'—C19'1.385 (2)
C18—H18A0.9500C18'—H18B0.9500
C19—C201.380 (3)C19'—C20'1.384 (2)
C19—H19A0.9500C19'—H19B0.9500
C20—C211.389 (3)C20'—C21'1.385 (2)
C20—H20A0.9500C20'—H20B0.9500
C21—C221.387 (2)C21'—C22'1.386 (2)
C21—H21A0.9500C21'—H21B0.9500
C23—C241.392 (2)C23'—C24'1.388 (2)
C23—C281.396 (2)C23'—C28'1.406 (2)
C24—C251.384 (2)C24'—C25'1.384 (3)
C24—H24A0.9500C24'—H24B0.9500
C25—C261.375 (3)C25'—C26'1.384 (3)
C25—H25A0.9500C25'—H25B0.9500
C26—C271.386 (2)C26'—C27'1.385 (2)
C26—H26A0.9500C26'—H26B0.9500
C27—C281.397 (2)C27'—C28'1.397 (2)
C27—H27A0.9500C27'—H27B0.9500
C23—S1—C2299.26 (7)C23—C28—C27117.81 (14)
C28—N1—C17120.20 (13)C23—C28—N1120.99 (14)
C28—N1—C7116.80 (12)C27—C28—N1121.19 (14)
C17—N1—C7115.94 (12)C23'—S1'—C22'99.80 (7)
C2A—C3A—C4109.6 (3)C28'—N1'—C17'120.76 (13)
C2A—C3A—H3AA125.2C28'—N1'—C7'118.85 (12)
C4—C3A—H3AA125.2C17'—N1'—C7'117.57 (12)
C3A—C2A—C10A128.7 (4)C2'—C1'—C9'110.6 (4)
C3A—C2A—C1A109.7 (2)C2'—C1'—H1'A124.7
C10A—C2A—C1A121.6 (4)C9'—C1'—H1'A124.7
C2A—C1A—C9104.8 (3)C1'—C2'—C10'128.5 (5)
C2A—C1A—H1AA110.8C1'—C2'—C3'109.2 (3)
C9—C1A—H1AA110.8C10'—C2'—C3'120.7 (5)
C2A—C1A—H1AB110.8C4'—C3'—C2'103.4 (4)
C9—C1A—H1AB110.8C4'—C3'—H3'A111.1
H1AA—C1A—H1AB108.9C2'—C3'—H3'A111.1
C2B—C1B—C9107.7 (5)C4'—C3'—H3'B111.1
C2B—C1B—H1BA126.1C2'—C3'—H3'B111.1
C9—C1B—H1BA126.1H3'A—C3'—H3'B109.1
C1B—C2B—C10B128.7 (6)C2"—C3"—C4'110.2 (5)
C1B—C2B—C3B110.3 (3)C2"—C3"—H3"C124.9
C10B—C2B—C3B121.0 (6)C4'—C3"—H3"C124.9
C4—C3B—C2B105.2 (4)C3"—C2"—C10"128.3 (7)
C4—C3B—H3BA110.7C3"—C2"—C1"109.4 (3)
C2B—C3B—H3BA110.7C10"—C2"—C1"121.1 (6)
C4—C3B—H3BB110.7C9'—C1"—C2"103.1 (5)
C2B—C3B—H3BB110.7C9'—C1"—H1"A111.2
H3BA—C3B—H3BB108.8C2"—C1"—H1"A111.2
C2B—C10B—H10D109.5C9'—C1"—H1"B111.2
C2B—C10B—H10E109.5C2"—C1"—H1"B111.2
H10D—C10B—H10E109.5H1"A—C1"—H1"B109.1
C2B—C10B—H10F109.5C5'—C4'—C9'120.86 (14)
H10D—C10B—H10F109.5C5'—C4'—C3"132.4 (5)
H10E—C10B—H10F109.5C9'—C4'—C3"106.6 (5)
C5—C4—C9120.40 (13)C5'—C4'—C3'130.3 (4)
C5—C4—C3A130.8 (3)C9'—C4'—C3'108.8 (4)
C9—C4—C3A108.7 (2)C4'—C5'—C6'117.28 (14)
C5—C4—C3B133.7 (4)C4'—C5'—C11'122.90 (14)
C9—C4—C3B105.6 (4)C6'—C5'—C11'119.81 (14)
C6—C5—C4117.16 (13)C7'—C6'—C5'121.33 (15)
C6—C5—C11118.59 (13)C7'—C6'—H6'A119.3
C4—C5—C11124.26 (13)C5'—C6'—H6'A119.3
C7—C6—C5121.77 (14)C6'—C7'—C8'121.13 (14)
C7—C6—H6A119.1C6'—C7'—N1'120.77 (14)
C5—C6—H6A119.1C8'—C7'—N1'118.10 (13)
C8—C7—C6121.28 (14)C9'—C8'—C7'118.05 (14)
C8—C7—N1119.44 (13)C9'—C8'—H8'A121.0
C6—C7—N1119.26 (14)C7'—C8'—H8'A121.0
C7—C8—C9117.84 (14)C8'—C9'—C4'121.29 (14)
C7—C8—H8A121.1C8'—C9'—C1'131.1 (4)
C9—C8—H8A121.1C4'—C9'—C1'107.5 (4)
C8—C9—C4121.55 (13)C8'—C9'—C1"128.8 (5)
C8—C9—C1B127.3 (4)C4'—C9'—C1"109.9 (5)
C4—C9—C1B111.0 (4)C16'—C11'—C12'118.44 (14)
C8—C9—C1A131.1 (3)C16'—C11'—C5'120.28 (14)
C4—C9—C1A107.2 (2)C12'—C11'—C5'121.27 (15)
C12—C11—C16118.30 (14)C13'—C12'—C11'120.54 (17)
C12—C11—C5121.74 (13)C13'—C12'—H12B119.7
C16—C11—C5119.94 (13)C11'—C12'—H12B119.7
C13—C12—C11120.71 (14)C14'—C13'—C12'120.39 (17)
C13—C12—H12A119.6C14'—C13'—H13B119.8
C11—C12—H12A119.6C12'—C13'—H13B119.8
C14—C13—C12120.02 (15)C13'—C14'—C15'119.79 (16)
C14—C13—H13A120.0C13'—C14'—H14B120.1
C12—C13—H13A120.0C15'—C14'—H14B120.1
C15—C14—C13119.98 (14)C14'—C15'—C16'119.91 (17)
C15—C14—H14A120.0C14'—C15'—H15B120.0
C13—C14—H14A120.0C16'—C15'—H15B120.0
C14—C15—C16119.97 (15)C15'—C16'—C11'120.92 (16)
C14—C15—H15A120.0C15'—C16'—H16B119.5
C16—C15—H15A120.0C11'—C16'—H16B119.5
C15—C16—C11121.01 (15)C18'—C17'—C22'117.86 (14)
C15—C16—H16A119.5C18'—C17'—N1'121.80 (13)
C11—C16—H16A119.5C22'—C17'—N1'120.33 (14)
C22—C17—C18117.88 (14)C19'—C18'—C17'121.14 (15)
C22—C17—N1120.76 (14)C19'—C18'—H18B119.4
C18—C17—N1121.34 (14)C17'—C18'—H18B119.4
C19—C18—C17120.71 (15)C20'—C19'—C18'120.61 (16)
C19—C18—H18A119.6C20'—C19'—H19B119.7
C17—C18—H18A119.6C18'—C19'—H19B119.7
C20—C19—C18120.84 (16)C19'—C20'—C21'118.99 (15)
C20—C19—H19A119.6C19'—C20'—H20B120.5
C18—C19—H19A119.6C21'—C20'—H20B120.5
C19—C20—C21119.03 (16)C20'—C21'—C22'120.84 (15)
C19—C20—H20A120.5C20'—C21'—H21B119.6
C21—C20—H20A120.5C22'—C21'—H21B119.6
C22—C21—C20120.46 (17)C21'—C22'—C17'120.51 (15)
C22—C21—H21A119.8C21'—C22'—S1'119.53 (12)
C20—C21—H21A119.8C17'—C22'—S1'119.85 (12)
C21—C22—C17120.98 (15)C24'—C23'—C28'120.54 (16)
C21—C22—S1118.54 (13)C24'—C23'—S1'119.08 (13)
C17—C22—S1120.31 (12)C28'—C23'—S1'120.12 (12)
C24—C23—C28120.85 (15)C25'—C24'—C23'120.71 (17)
C24—C23—S1118.92 (13)C25'—C24'—H24B119.6
C28—C23—S1120.13 (12)C23'—C24'—H24B119.6
C25—C24—C23120.47 (16)C24'—C25'—C26'119.03 (17)
C25—C24—H24A119.8C24'—C25'—H25B120.5
C23—C24—H24A119.8C26'—C25'—H25B120.5
C26—C25—C24118.89 (15)C25'—C26'—C27'120.99 (17)
C26—C25—H25A120.6C25'—C26'—H26B119.5
C24—C25—H25A120.6C27'—C26'—H26B119.5
C25—C26—C27121.25 (16)C26'—C27'—C28'120.61 (16)
C25—C26—H26A119.4C26'—C27'—H27B119.7
C27—C26—H26A119.4C28'—C27'—H27B119.7
C26—C27—C28120.59 (16)C27'—C28'—C23'118.09 (15)
C26—C27—H27A119.7C27'—C28'—N1'121.81 (14)
C28—C27—H27A119.7C23'—C28'—N1'120.08 (14)
C4—C3A—C2A—C10A178.3 (6)C9'—C1'—C2'—C10'−169.4 (14)
C4—C3A—C2A—C1A1.0 (10)C9'—C1'—C2'—C3'−4.3 (16)
C3A—C2A—C1A—C9−1.0 (10)C1'—C2'—C3'—C4'6.9 (14)
C10A—C2A—C1A—C9−178.6 (5)C10'—C2'—C3'—C4'173.4 (13)
C9—C1B—C2B—C10B−178.0 (12)C4'—C3"—C2"—C10"−177.0 (19)
C9—C1B—C2B—C3B4(2)C4'—C3"—C2"—C1"−10 (2)
C1B—C2B—C3B—C4−4(2)C3"—C2"—C1"—C9'7(2)
C10B—C2B—C3B—C4177.5 (11)C10"—C2"—C1"—C9'175.3 (17)
C2A—C3A—C4—C5−177.1 (4)C2"—C3"—C4'—C5'−175.7 (10)
C2A—C3A—C4—C9−0.5 (8)C2"—C3"—C4'—C9'8.5 (16)
C2A—C3A—C4—C3B69 (5)C2"—C3"—C4'—C3'−114 (15)
C2B—C3B—C4—C5176.8 (7)C2'—C3'—C4'—C5'172.9 (6)
C2B—C3B—C4—C92.7 (15)C2'—C3'—C4'—C9'−7.1 (10)
C2B—C3B—C4—C3A−111 (6)C2'—C3'—C4'—C3"51 (14)
C9—C4—C5—C6−0.9 (2)C9'—C4'—C5'—C6'−1.6 (2)
C3A—C4—C5—C6175.3 (6)C3"—C4'—C5'—C6'−176.9 (11)
C3B—C4—C5—C6−174.3 (12)C3'—C4'—C5'—C6'178.3 (8)
C9—C4—C5—C11179.11 (13)C9'—C4'—C5'—C11'177.11 (14)
C3A—C4—C5—C11−4.6 (6)C3"—C4'—C5'—C11'1.9 (11)
C3B—C4—C5—C115.7 (12)C3'—C4'—C5'—C11'−3.0 (8)
C4—C5—C6—C70.8 (2)C4'—C5'—C6'—C7'−0.7 (2)
C11—C5—C6—C7−179.27 (13)C11'—C5'—C6'—C7'−179.51 (14)
C5—C6—C7—C80.1 (2)C5'—C6'—C7'—C8'2.4 (2)
C5—C6—C7—N1−178.26 (13)C5'—C6'—C7'—N1'−176.53 (14)
C28—N1—C7—C8109.96 (16)C28'—N1'—C7'—C6'−83.26 (18)
C17—N1—C7—C8−99.29 (16)C17'—N1'—C7'—C6'77.90 (18)
C28—N1—C7—C6−71.64 (17)C28'—N1'—C7'—C8'97.75 (17)
C17—N1—C7—C679.11 (17)C17'—N1'—C7'—C8'−101.09 (16)
C6—C7—C8—C9−0.8 (2)C6'—C7'—C8'—C9'−1.7 (2)
N1—C7—C8—C9177.53 (13)N1'—C7'—C8'—C9'177.33 (14)
C7—C8—C9—C40.7 (2)C7'—C8'—C9'—C4'−0.7 (2)
C7—C8—C9—C1B175.9 (11)C7'—C8'—C9'—C1'176.1 (8)
C7—C8—C9—C1A−175.1 (6)C7'—C8'—C9'—C1"−177.6 (11)
C5—C4—C9—C80.2 (2)C5'—C4'—C9'—C8'2.4 (2)
C3A—C4—C9—C8−176.8 (4)C3"—C4'—C9'—C8'178.7 (8)
C3B—C4—C9—C8175.3 (9)C3'—C4'—C9'—C8'−177.5 (6)
C5—C4—C9—C1B−175.7 (9)C5'—C4'—C9'—C1'−175.1 (6)
C3A—C4—C9—C1B7.3 (10)C3"—C4'—C9'—C1'1.2 (11)
C3B—C4—C9—C1B−0.6 (13)C3'—C4'—C9'—C1'4.9 (9)
C5—C4—C9—C1A176.9 (5)C5'—C4'—C9'—C1"179.8 (9)
C3A—C4—C9—C1A−0.2 (6)C3"—C4'—C9'—C1"−3.8 (12)
C3B—C4—C9—C1A−8.1 (10)C3'—C4'—C9'—C1"−0.1 (11)
C2B—C1B—C9—C8−177.5 (9)C2'—C1'—C9'—C8'−177.6 (8)
C2B—C1B—C9—C4−1.9 (17)C2'—C1'—C9'—C4'−0.4 (13)
C2B—C1B—C9—C1A61 (5)C2'—C1'—C9'—C1"117 (12)
C2A—C1A—C9—C8176.9 (4)C2"—C1"—C9'—C8'175.6 (9)
C2A—C1A—C9—C40.7 (8)C2"—C1"—C9'—C4'−1.6 (15)
C2A—C1A—C9—C1B−119 (6)C2"—C1"—C9'—C1'−66 (10)
C6—C5—C11—C12−135.67 (15)C4'—C5'—C11'—C16'−138.00 (16)
C4—C5—C11—C1244.3 (2)C6'—C5'—C11'—C16'40.7 (2)
C6—C5—C11—C1642.5 (2)C4'—C5'—C11'—C12'41.7 (2)
C4—C5—C11—C16−137.61 (15)C6'—C5'—C11'—C12'−139.62 (16)
C16—C11—C12—C13−0.1 (2)C16'—C11'—C12'—C13'1.1 (2)
C5—C11—C12—C13178.02 (14)C5'—C11'—C12'—C13'−178.54 (15)
C11—C12—C13—C140.4 (2)C11'—C12'—C13'—C14'−0.5 (3)
C12—C13—C14—C150.1 (2)C12'—C13'—C14'—C15'−0.3 (3)
C13—C14—C15—C16−0.8 (2)C13'—C14'—C15'—C16'0.6 (3)
C14—C15—C16—C111.1 (2)C14'—C15'—C16'—C11'0.0 (2)
C12—C11—C16—C15−0.6 (2)C12'—C11'—C16'—C15'−0.9 (2)
C5—C11—C16—C15−178.78 (14)C5'—C11'—C16'—C15'178.79 (15)
C28—N1—C17—C22−31.4 (2)C28'—N1'—C17'—C18'146.99 (15)
C7—N1—C17—C22178.91 (13)C7'—N1'—C17'—C18'−13.8 (2)
C28—N1—C17—C18150.34 (14)C28'—N1'—C17'—C22'−34.1 (2)
C7—N1—C17—C180.6 (2)C7'—N1'—C17'—C22'165.08 (14)
C22—C17—C18—C191.0 (2)C22'—C17'—C18'—C19'0.9 (2)
N1—C17—C18—C19179.33 (14)N1'—C17'—C18'—C19'179.85 (14)
C17—C18—C19—C201.3 (2)C17'—C18'—C19'—C20'0.5 (2)
C18—C19—C20—C21−1.5 (3)C18'—C19'—C20'—C21'−0.7 (2)
C19—C20—C21—C22−0.8 (3)C19'—C20'—C21'—C22'−0.7 (2)
C20—C21—C22—C173.2 (3)C20'—C21'—C22'—C17'2.2 (2)
C20—C21—C22—S1−172.20 (14)C20'—C21'—C22'—S1'−174.09 (13)
C18—C17—C22—C21−3.2 (2)C18'—C17'—C22'—C21'−2.3 (2)
N1—C17—C22—C21178.44 (15)N1'—C17'—C22'—C21'178.80 (14)
C18—C17—C22—S1172.04 (11)C18'—C17'—C22'—S1'173.97 (12)
N1—C17—C22—S1−6.3 (2)N1'—C17'—C22'—S1'−4.9 (2)
C23—S1—C22—C21−150.44 (14)C23'—S1'—C22'—C21'−150.37 (13)
C23—S1—C22—C1734.16 (14)C23'—S1'—C22'—C17'33.35 (14)
C22—S1—C23—C24149.48 (13)C22'—S1'—C23'—C24'152.87 (13)
C22—S1—C23—C28−34.10 (14)C22'—S1'—C23'—C28'−32.85 (14)
C28—C23—C24—C25−3.4 (2)C28'—C23'—C24'—C25'−1.2 (2)
S1—C23—C24—C25172.94 (13)S1'—C23'—C24'—C25'173.09 (13)
C23—C24—C25—C260.4 (3)C23'—C24'—C25'—C26'1.6 (3)
C24—C25—C26—C272.0 (3)C24'—C25'—C26'—C27'−0.5 (3)
C25—C26—C27—C28−1.4 (3)C25'—C26'—C27'—C28'−1.0 (2)
C24—C23—C28—C273.9 (2)C26'—C27'—C28'—C23'1.4 (2)
S1—C23—C28—C27−172.41 (12)C26'—C27'—C28'—N1'−176.94 (14)
C24—C23—C28—N1−177.39 (14)C24'—C23'—C28'—C27'−0.3 (2)
S1—C23—C28—N16.3 (2)S1'—C23'—C28'—C27'−174.49 (12)
C26—C27—C28—C23−1.5 (2)C24'—C23'—C28'—N1'178.03 (14)
C26—C27—C28—N1179.80 (15)S1'—C23'—C28'—N1'3.8 (2)
C17—N1—C28—C2331.4 (2)C17'—N1'—C28'—C27'−147.03 (14)
C7—N1—C28—C23−179.11 (13)C7'—N1'—C28'—C27'13.5 (2)
C17—N1—C28—C27−149.93 (14)C17'—N1'—C28'—C23'34.7 (2)
C7—N1—C28—C27−0.5 (2)C7'—N1'—C28'—C23'−164.74 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2115).

References

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  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2005). APEX2 andSAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Voskoboynikov, A. Z., Lebedev, A. Y., Izmer, V. V., Ryabov, A. N., Nikulin, M. V. & Canish, J. M. (2006). (ExxonMobil Chemical Patents Inc., USA.) PCT Int. Appl. WO 2 005 105 864.
  • Yang, B. H. & Buchwald, S. L. (1999). J. Organomet. Chem.576, 125–146.

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