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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o605.
Published online 2009 February 25. doi:  10.1107/S1600536809005935
PMCID: PMC2968567

4-(4-Methoxy­phen­yl)-4-methyl-2,6-diphenyl-4H-thio­pyran

Abstract

The asymmetric unit of the title compound, C25H22OS, comprises two similar 4-(4-methoxy­phen­yl)-4-methyl-2,6-diphenyl-4H-thio­pyran mol­ecules. In each, the six-membered thio­pyran ring adopts a planar conformation (r.m.s. deviation of 0.041Å for the ring in one mol­ecule and 0.008 Å in the other). The methoxy­phenyl substituent is in a pseudo-axial position. The crystal studied is an inversion twin, with a domain ratio of 0.39 (6).

Related literature

For the background to 4-alkyl-2,4,6-triaryl-4H-thio­pyrans, see: Rahmani et al. (2009 [triangle]). For the general synthesis from a Grignard reaction, see: Suld & Price (1962 [triangle]).

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Object name is e-65-0o605-scheme1.jpg

Experimental

Crystal data

  • C25H22OS
  • M r = 370.49
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o605-efi1.jpg
  • a = 14.1567 (2) Å
  • b = 7.6138 (1) Å
  • c = 36.1457 (6) Å
  • V = 3896.0 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 115 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.919, T max = 0.982
  • 35118 measured reflections
  • 8811 independent reflections
  • 7499 reflections with I > 2˘I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.106
  • S = 1.04
  • 8811 reflections
  • 492 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.26 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4271 Friedel pairs
  • Flack parameter: 0.39 (6)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005935/sj2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005935/sj2580Isup2.hkl

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

Acknowledgments

We thank the Iranian Research Organization for Science and Technology and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The compound was synthesized by the reaction of methyl magnesium bromide and 4-(4-anisyl)-2,6-diphenyl thiopyrylium perchlorate in dry ether under an argon atmosphere according to a reported method (Suld & Price, 1962). The product was isolated by TLC on neutral alumina (petroleum ether 40–60 °C) and purified by recrystalization from ethanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The final difference Fourier map had a large peak/deep hole in the vicinity of the bromine. The crystal studied is an inversion, with a twin component of 0.39 (6).

Figures

Fig. 1.
Thermal ellisoid plot (Barbour, 2001) of C24H19BrS; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

Crystal data

C25H22OSF(000) = 1568
Mr = 370.49Dx = 1.263 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6600 reflections
a = 14.1567 (2) Åθ = 2.7–25.9°
b = 7.6138 (1) ŵ = 0.18 mm1
c = 36.1457 (6) ÅT = 115 K
V = 3896.0 (1) Å3Prism, pale yellow
Z = 80.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer8811 independent reflections
Radiation source: fine-focus sealed tube7499 reflections with I > 2˘I)
graphiteRint = 0.048
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.919, Tmax = 0.982k = −9→9
35118 measured reflectionsl = −46→46

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.106w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3658P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
8811 reflectionsΔρmax = 0.27 e Å3
492 parametersΔρmin = −0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 4271 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.39 (6)

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

xyzUiso*/Ueq
S10.74555 (4)0.75526 (7)0.500000 (18)0.02190 (12)
S20.48342 (4)0.25554 (7)0.150501 (17)0.02188 (12)
O10.93417 (12)0.9368 (3)0.30170 (5)0.0335 (4)
O20.68606 (14)0.6061 (3)0.34833 (5)0.0456 (5)
C10.66819 (14)0.8115 (3)0.46382 (6)0.0190 (5)
C20.67887 (15)0.9498 (3)0.44191 (7)0.0213 (5)
H20.62960.96910.42450.026*
C30.75898 (15)1.0807 (3)0.44093 (6)0.0198 (5)
C40.82518 (15)1.0587 (3)0.47343 (6)0.0206 (5)
H40.87231.14650.47610.025*
C50.82586 (14)0.9317 (3)0.49885 (6)0.0188 (4)
C60.71782 (18)1.2682 (3)0.44237 (7)0.0274 (5)
H6A0.67491.28560.42140.041*
H6B0.76931.35390.44100.041*
H6C0.68311.28410.46560.041*
C70.58948 (14)0.6828 (3)0.45931 (6)0.0196 (5)
C80.54589 (16)0.6034 (3)0.48994 (7)0.0234 (5)
H80.56610.63200.51430.028*
C90.47374 (17)0.4837 (3)0.48484 (8)0.0271 (6)
H90.44490.43030.50570.033*
C100.44330 (17)0.4411 (3)0.44995 (8)0.0304 (6)
H100.39310.35970.44670.036*
C110.48646 (17)0.5181 (4)0.41938 (8)0.0305 (6)
H110.46610.48800.39520.037*
C120.55884 (16)0.6381 (3)0.42407 (7)0.0252 (5)
H120.58780.69020.40300.030*
C130.81171 (15)1.0511 (3)0.40405 (6)0.0190 (5)
C140.76714 (17)1.0842 (3)0.37024 (7)0.0279 (5)
H140.70551.13360.37030.033*
C150.80995 (17)1.0473 (3)0.33695 (7)0.0298 (5)
H150.77801.07180.31440.036*
C160.89975 (17)0.9743 (3)0.33624 (7)0.0252 (5)
C170.94639 (16)0.9416 (3)0.36914 (7)0.0248 (5)
H171.00820.89280.36900.030*
C180.90181 (16)0.9809 (3)0.40252 (7)0.0226 (5)
H180.93440.95870.42500.027*
C191.0242 (2)0.8520 (4)0.29948 (8)0.0426 (7)
H19A1.03960.82880.27350.064*
H19B1.02200.74080.31310.064*
H19C1.07260.92820.31030.064*
C200.89736 (15)0.9209 (3)0.52889 (6)0.0195 (5)
C210.99097 (17)0.9677 (3)0.52196 (7)0.0244 (5)
H211.00851.00780.49800.029*
C221.05849 (18)0.9563 (3)0.54949 (8)0.0314 (6)
H221.12190.98920.54440.038*
C231.03454 (18)0.8975 (3)0.58441 (7)0.0283 (5)
H231.08100.89070.60330.034*
C240.94234 (18)0.8488 (3)0.59161 (7)0.0284 (5)
H240.92560.80730.61550.034*
C250.87397 (16)0.8599 (3)0.56422 (6)0.0242 (5)
H250.81080.82590.56950.029*
C260.40910 (15)0.3075 (3)0.18818 (6)0.0188 (5)
C270.42127 (16)0.4450 (3)0.21015 (7)0.0219 (5)
H270.37620.45740.22940.026*
C280.49713 (16)0.5847 (3)0.20873 (6)0.0205 (5)
C290.56616 (16)0.5548 (3)0.17759 (6)0.0205 (5)
H290.61650.63680.17600.025*
C300.56606 (14)0.4290 (3)0.15210 (6)0.0182 (4)
C310.44897 (18)0.7633 (3)0.20161 (7)0.0284 (5)
H31A0.40110.78450.22070.043*
H31B0.41880.76190.17720.043*
H31C0.49640.85700.20240.043*
C320.33001 (15)0.1805 (3)0.19254 (6)0.0207 (5)
C330.28735 (16)0.1024 (3)0.16188 (7)0.0232 (5)
H330.30980.12880.13770.028*
C340.21227 (17)−0.0137 (3)0.16624 (7)0.0266 (6)
H340.1841−0.06670.14520.032*
C350.17863 (17)−0.0519 (3)0.20120 (8)0.0299 (6)
H350.1272−0.13060.20420.036*
C360.22024 (18)0.0251 (4)0.23171 (8)0.0312 (6)
H360.1968−0.00010.25580.037*
C370.29591 (17)0.1387 (3)0.22755 (7)0.0266 (5)
H370.32480.18860.24880.032*
C380.54983 (16)0.5857 (3)0.24607 (6)0.0200 (5)
C390.50873 (17)0.6610 (4)0.27743 (7)0.0308 (6)
H390.44760.71180.27570.037*
C400.55541 (19)0.6629 (4)0.31089 (7)0.0364 (6)
H400.52580.71400.33190.044*
C410.64487 (17)0.5912 (3)0.31433 (7)0.0292 (5)
C420.68627 (16)0.5117 (3)0.28390 (7)0.0252 (5)
H420.74670.45850.28600.030*
C430.63812 (16)0.5107 (3)0.25018 (7)0.0220 (5)
H430.66700.45670.22940.026*
C440.78270 (19)0.5650 (4)0.35186 (7)0.0374 (6)
H44A0.80470.59870.37660.056*
H44B0.81880.62940.33310.056*
H44C0.79180.43850.34840.056*
C450.63793 (16)0.4168 (3)0.12220 (6)0.0202 (5)
C460.73151 (17)0.4634 (3)0.12934 (7)0.0244 (5)
H460.74900.50210.15340.029*
C470.79934 (18)0.4539 (4)0.10169 (7)0.0304 (6)
H470.86270.48690.10690.036*
C480.77508 (18)0.3966 (3)0.06668 (7)0.0297 (6)
H480.82150.39070.04770.036*
C490.68272 (18)0.3478 (3)0.05938 (7)0.0285 (5)
H490.66580.30770.03540.034*
C500.61485 (17)0.3571 (3)0.08691 (6)0.0241 (5)
H500.55180.32240.08170.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0191 (2)0.0190 (3)0.0276 (3)−0.0019 (2)−0.0007 (2)0.0044 (2)
S20.0198 (2)0.0198 (3)0.0260 (3)−0.0011 (2)−0.0004 (2)−0.0050 (2)
O10.0322 (9)0.0453 (11)0.0229 (9)−0.0017 (8)0.0060 (8)−0.0056 (8)
O20.0370 (11)0.0760 (16)0.0238 (10)0.0019 (10)−0.0068 (8)−0.0092 (9)
C10.0156 (10)0.0206 (11)0.0208 (11)0.0011 (9)0.0047 (9)−0.0027 (9)
C20.0184 (10)0.0237 (12)0.0219 (12)0.0008 (9)0.0012 (9)0.0003 (10)
C30.0180 (10)0.0183 (11)0.0233 (12)−0.0007 (8)0.0035 (9)0.0005 (9)
C40.0215 (11)0.0188 (12)0.0214 (12)−0.0015 (9)0.0031 (9)−0.0009 (9)
C50.0180 (10)0.0186 (11)0.0197 (11)0.0003 (8)0.0056 (9)−0.0034 (9)
C60.0264 (12)0.0222 (12)0.0337 (14)0.0043 (9)0.0030 (11)−0.0009 (10)
C70.0149 (10)0.0173 (11)0.0267 (12)0.0031 (8)0.0031 (9)−0.0004 (9)
C80.0216 (11)0.0216 (12)0.0271 (13)0.0030 (9)0.0048 (10)0.0009 (9)
C90.0249 (12)0.0214 (13)0.0350 (15)0.0005 (9)0.0101 (11)0.0043 (10)
C100.0235 (12)0.0225 (13)0.0451 (17)−0.0063 (10)0.0025 (11)−0.0030 (11)
C110.0257 (12)0.0321 (14)0.0338 (15)−0.0052 (11)−0.0018 (11)−0.0032 (11)
C120.0232 (12)0.0260 (13)0.0265 (13)−0.0012 (10)0.0031 (10)0.0025 (10)
C130.0195 (11)0.0188 (11)0.0189 (11)−0.0030 (9)0.0028 (8)0.0030 (9)
C140.0216 (11)0.0339 (14)0.0281 (13)0.0048 (10)−0.0008 (10)0.0029 (11)
C150.0272 (12)0.0404 (15)0.0219 (12)−0.0008 (11)−0.0014 (10)0.0065 (11)
C160.0294 (12)0.0261 (12)0.0200 (11)−0.0078 (10)0.0042 (10)−0.0044 (10)
C170.0202 (11)0.0281 (13)0.0259 (13)0.0024 (9)0.0016 (10)−0.0008 (11)
C180.0206 (11)0.0262 (13)0.0209 (13)−0.0029 (9)−0.0024 (9)0.0028 (9)
C190.0370 (15)0.0504 (19)0.0404 (16)0.0009 (13)0.0151 (13)−0.0112 (14)
C200.0234 (11)0.0150 (11)0.0200 (11)0.0001 (9)0.0019 (9)−0.0028 (9)
C210.0231 (11)0.0241 (11)0.0260 (13)−0.0042 (10)0.0012 (10)0.0031 (10)
C220.0269 (13)0.0298 (14)0.0373 (15)−0.0076 (11)−0.0041 (11)0.0039 (12)
C230.0354 (13)0.0214 (12)0.0280 (13)0.0005 (10)−0.0106 (11)−0.0005 (10)
C240.0414 (15)0.0255 (13)0.0182 (12)0.0045 (11)0.0002 (11)0.0013 (10)
C250.0262 (12)0.0243 (13)0.0223 (12)0.0006 (9)0.0051 (10)−0.0007 (9)
C260.0173 (11)0.0179 (11)0.0211 (11)0.0027 (8)−0.0044 (8)−0.0006 (9)
C270.0216 (11)0.0218 (12)0.0224 (12)0.0019 (9)−0.0024 (9)−0.0013 (10)
C280.0229 (11)0.0196 (11)0.0189 (11)−0.0016 (9)−0.0022 (9)−0.0033 (9)
C290.0224 (11)0.0200 (12)0.0191 (12)−0.0043 (9)−0.0038 (9)0.0043 (9)
C300.0195 (10)0.0181 (10)0.0170 (11)0.0001 (8)−0.0043 (9)0.0031 (9)
C310.0303 (13)0.0225 (13)0.0324 (14)0.0029 (10)−0.0022 (11)0.0004 (10)
C320.0176 (11)0.0177 (11)0.0267 (12)0.0024 (8)−0.0045 (9)−0.0010 (9)
C330.0223 (11)0.0206 (12)0.0266 (13)0.0004 (9)−0.0035 (10)−0.0003 (9)
C340.0258 (12)0.0190 (12)0.0350 (15)−0.0029 (10)−0.0075 (11)−0.0029 (10)
C350.0225 (12)0.0252 (13)0.0420 (16)−0.0041 (10)−0.0053 (11)0.0055 (11)
C360.0252 (13)0.0359 (14)0.0324 (15)−0.0058 (11)−0.0006 (11)0.0044 (11)
C370.0242 (12)0.0289 (13)0.0266 (12)−0.0009 (10)−0.0045 (10)−0.0007 (10)
C380.0227 (11)0.0149 (10)0.0223 (12)−0.0030 (8)0.0008 (9)−0.0010 (9)
C390.0251 (12)0.0380 (15)0.0294 (13)0.0074 (11)−0.0023 (10)−0.0100 (12)
C400.0354 (14)0.0490 (17)0.0246 (13)0.0040 (12)0.0019 (11)−0.0118 (12)
C410.0304 (13)0.0367 (14)0.0206 (12)−0.0034 (11)−0.0006 (10)−0.0021 (10)
C420.0191 (11)0.0310 (13)0.0254 (12)0.0006 (9)0.0008 (9)0.0029 (10)
C430.0239 (11)0.0218 (12)0.0204 (12)−0.0005 (9)0.0018 (10)−0.0018 (10)
C440.0370 (15)0.0446 (17)0.0305 (14)−0.0059 (12)−0.0127 (12)0.0014 (12)
C450.0257 (11)0.0155 (11)0.0196 (11)0.0007 (9)−0.0016 (9)0.0027 (9)
C460.0274 (12)0.0227 (12)0.0230 (13)−0.0034 (10)−0.0026 (10)−0.0021 (10)
C470.0248 (12)0.0324 (14)0.0338 (15)−0.0054 (11)0.0032 (11)−0.0012 (11)
C480.0343 (14)0.0244 (13)0.0303 (14)0.0001 (11)0.0065 (12)0.0008 (10)
C490.0400 (15)0.0241 (13)0.0214 (12)0.0008 (11)0.0008 (11)−0.0018 (10)
C500.0277 (12)0.0221 (12)0.0226 (12)−0.0011 (9)−0.0042 (10)0.0006 (9)

Geometric parameters (Å, °)

S1—C11.759 (2)C23—H230.9500
S1—C51.761 (2)C24—C251.387 (3)
S2—C301.766 (2)C24—H240.9500
S2—C261.766 (2)C25—H250.9500
O1—C161.370 (3)C26—C271.325 (3)
O1—C191.431 (3)C26—C321.488 (3)
O2—C411.365 (3)C27—C281.513 (3)
O2—C441.409 (3)C27—H270.9500
C1—C21.326 (3)C28—C291.508 (3)
C1—C71.493 (3)C28—C381.542 (3)
C2—C31.510 (3)C28—C311.543 (3)
C2—H20.9500C29—C301.328 (3)
C3—C41.512 (3)C29—H290.9500
C3—C61.542 (3)C30—C451.487 (3)
C3—C131.544 (3)C31—H31A0.9800
C4—C51.334 (3)C31—H31B0.9800
C4—H40.9500C31—H31C0.9800
C5—C201.487 (3)C32—C371.391 (3)
C6—H6A0.9800C32—C331.395 (3)
C6—H6B0.9800C33—C341.391 (3)
C6—H6C0.9800C33—H330.9500
C7—C121.388 (3)C34—C351.381 (4)
C7—C81.405 (3)C34—H340.9500
C8—C91.381 (3)C35—C361.381 (4)
C8—H80.9500C35—H350.9500
C9—C101.372 (4)C36—C371.385 (3)
C9—H90.9500C36—H360.9500
C10—C111.392 (4)C37—H370.9500
C10—H100.9500C38—C431.382 (3)
C11—C121.383 (3)C38—C391.397 (3)
C11—H110.9500C39—C401.378 (4)
C12—H120.9500C39—H390.9500
C13—C181.384 (3)C40—C411.385 (4)
C13—C141.398 (3)C40—H400.9500
C14—C151.376 (3)C41—C421.385 (3)
C14—H140.9500C42—C431.397 (3)
C15—C161.388 (3)C42—H420.9500
C15—H150.9500C43—H430.9500
C16—C171.383 (3)C44—H44A0.9800
C17—C181.394 (3)C44—H44B0.9800
C17—H170.9500C44—H44C0.9800
C18—H180.9500C45—C501.393 (3)
C19—H19A0.9800C45—C461.396 (3)
C19—H19B0.9800C46—C471.388 (4)
C19—H19C0.9800C46—H460.9500
C20—C211.395 (3)C47—C481.382 (4)
C20—C251.398 (3)C47—H470.9500
C21—C221.383 (4)C48—C491.385 (3)
C21—H210.9500C48—H480.9500
C22—C231.381 (4)C49—C501.385 (3)
C22—H220.9500C49—H490.9500
C23—C241.382 (4)C50—H500.9500
C1—S1—C5101.46 (11)C24—C25—H25119.8
C30—S2—C26101.64 (11)C20—C25—H25119.8
C16—O1—C19117.5 (2)C27—C26—C32123.2 (2)
C41—O2—C44118.5 (2)C27—C26—S2124.19 (19)
C2—C1—C7122.7 (2)C32—C26—S2112.61 (16)
C2—C1—S1124.50 (18)C26—C27—C28128.9 (2)
C7—C1—S1112.72 (16)C26—C27—H27115.6
C1—C2—C3128.6 (2)C28—C27—H27115.6
C1—C2—H2115.7C29—C28—C27112.27 (19)
C3—C2—H2115.7C29—C28—C38109.90 (18)
C2—C3—C4111.95 (19)C27—C28—C38108.47 (18)
C2—C3—C6109.04 (19)C29—C28—C31107.18 (19)
C4—C3—C6108.10 (19)C27—C28—C31108.18 (19)
C2—C3—C13106.66 (18)C38—C28—C31110.84 (18)
C4—C3—C13110.78 (18)C30—C29—C28128.8 (2)
C6—C3—C13110.31 (19)C30—C29—H29115.6
C5—C4—C3128.3 (2)C28—C29—H29115.6
C5—C4—H4115.8C29—C30—C45123.3 (2)
C3—C4—H4115.8C29—C30—S2124.23 (18)
C4—C5—C20123.3 (2)C45—C30—S2112.48 (16)
C4—C5—S1124.38 (18)C28—C31—H31A109.5
C20—C5—S1112.33 (16)C28—C31—H31B109.5
C3—C6—H6A109.5H31A—C31—H31B109.5
C3—C6—H6B109.5C28—C31—H31C109.5
H6A—C6—H6B109.5H31A—C31—H31C109.5
C3—C6—H6C109.5H31B—C31—H31C109.5
H6A—C6—H6C109.5C37—C32—C33118.3 (2)
H6B—C6—H6C109.5C37—C32—C26120.4 (2)
C12—C7—C8118.7 (2)C33—C32—C26121.2 (2)
C12—C7—C1119.7 (2)C34—C33—C32120.8 (2)
C8—C7—C1121.6 (2)C34—C33—H33119.6
C9—C8—C7120.3 (2)C32—C33—H33119.6
C9—C8—H8119.9C35—C34—C33120.1 (2)
C7—C8—H8119.9C35—C34—H34120.0
C10—C9—C8120.7 (2)C33—C34—H34120.0
C10—C9—H9119.6C36—C35—C34119.6 (2)
C8—C9—H9119.6C36—C35—H35120.2
C9—C10—C11119.5 (2)C34—C35—H35120.2
C9—C10—H10120.2C35—C36—C37120.5 (3)
C11—C10—H10120.2C35—C36—H36119.7
C12—C11—C10120.4 (3)C37—C36—H36119.7
C12—C11—H11119.8C36—C37—C32120.7 (2)
C10—C11—H11119.8C36—C37—H37119.7
C11—C12—C7120.4 (2)C32—C37—H37119.7
C11—C12—H12119.8C43—C38—C39117.3 (2)
C7—C12—H12119.8C43—C38—C28122.0 (2)
C18—C13—C14116.8 (2)C39—C38—C28120.7 (2)
C18—C13—C3122.4 (2)C40—C39—C38121.1 (2)
C14—C13—C3120.7 (2)C40—C39—H39119.4
C15—C14—C13121.9 (2)C38—C39—H39119.4
C15—C14—H14119.0C39—C40—C41120.9 (2)
C13—C14—H14119.0C39—C40—H40119.6
C14—C15—C16120.1 (2)C41—C40—H40119.6
C14—C15—H15120.0O2—C41—C40116.0 (2)
C16—C15—H15120.0O2—C41—C42124.8 (2)
O1—C16—C17125.2 (2)C40—C41—C42119.2 (2)
O1—C16—C15115.2 (2)C41—C42—C43119.3 (2)
C17—C16—C15119.6 (2)C41—C42—H42120.4
C16—C17—C18119.3 (2)C43—C42—H42120.4
C16—C17—H17120.3C38—C43—C42122.2 (2)
C18—C17—H17120.3C38—C43—H43118.9
C13—C18—C17122.3 (2)C42—C43—H43118.9
C13—C18—H18118.8O2—C44—H44A109.5
C17—C18—H18118.8O2—C44—H44B109.5
O1—C19—H19A109.5H44A—C44—H44B109.5
O1—C19—H19B109.5O2—C44—H44C109.5
H19A—C19—H19B109.5H44A—C44—H44C109.5
O1—C19—H19C109.5H44B—C44—H44C109.5
H19A—C19—H19C109.5C50—C45—C46118.4 (2)
H19B—C19—H19C109.5C50—C45—C30121.7 (2)
C21—C20—C25118.3 (2)C46—C45—C30119.9 (2)
C21—C20—C5120.1 (2)C47—C46—C45120.7 (2)
C25—C20—C5121.6 (2)C47—C46—H46119.7
C22—C21—C20120.8 (2)C45—C46—H46119.7
C22—C21—H21119.6C48—C47—C46120.3 (2)
C20—C21—H21119.6C48—C47—H47119.9
C23—C22—C21120.6 (2)C46—C47—H47119.9
C23—C22—H22119.7C47—C48—C49119.6 (2)
C21—C22—H22119.7C47—C48—H48120.2
C22—C23—C24119.4 (2)C49—C48—H48120.2
C22—C23—H23120.3C48—C49—C50120.3 (2)
C24—C23—H23120.3C48—C49—H49119.9
C23—C24—C25120.5 (2)C50—C49—H49119.9
C23—C24—H24119.7C49—C50—C45120.8 (2)
C25—C24—H24119.7C49—C50—H50119.6
C24—C25—C20120.5 (2)C45—C50—H50119.6
C5—S1—C1—C23.5 (2)C30—S2—C26—C27−0.8 (2)
C5—S1—C1—C7−178.39 (15)C30—S2—C26—C32178.67 (15)
C7—C1—C2—C3−174.0 (2)C32—C26—C27—C28−179.3 (2)
S1—C1—C2—C34.0 (4)S2—C26—C27—C280.2 (4)
C1—C2—C3—C4−9.7 (3)C26—C27—C28—C29−0.5 (3)
C1—C2—C3—C6−129.3 (3)C26—C27—C28—C38−122.1 (3)
C1—C2—C3—C13111.6 (3)C26—C27—C28—C31117.6 (3)
C2—C3—C4—C57.7 (3)C27—C28—C29—C302.0 (3)
C6—C3—C4—C5127.8 (3)C38—C28—C29—C30122.8 (2)
C13—C3—C4—C5−111.2 (3)C31—C28—C29—C30−116.6 (3)
C3—C4—C5—C20177.6 (2)C28—C29—C30—C45178.7 (2)
C3—C4—C5—S1−0.3 (3)C28—C29—C30—S2−3.1 (3)
C1—S1—C5—C4−5.2 (2)C26—S2—C30—C292.2 (2)
C1—S1—C5—C20176.71 (15)C26—S2—C30—C45−179.44 (15)
C2—C1—C7—C1236.8 (3)C27—C26—C32—C37−34.2 (3)
S1—C1—C7—C12−141.36 (19)S2—C26—C32—C37146.29 (19)
C2—C1—C7—C8−144.0 (2)C27—C26—C32—C33144.9 (2)
S1—C1—C7—C837.8 (3)S2—C26—C32—C33−34.6 (3)
C12—C7—C8—C9−0.3 (3)C37—C32—C33—C340.3 (3)
C1—C7—C8—C9−179.5 (2)C26—C32—C33—C34−178.8 (2)
C7—C8—C9—C10−0.3 (4)C32—C33—C34—C350.5 (4)
C8—C9—C10—C110.7 (4)C33—C34—C35—C36−0.3 (4)
C9—C10—C11—C12−0.7 (4)C34—C35—C36—C37−0.6 (4)
C10—C11—C12—C70.2 (4)C35—C36—C37—C321.5 (4)
C8—C7—C12—C110.3 (4)C33—C32—C37—C36−1.3 (4)
C1—C7—C12—C11179.5 (2)C26—C32—C37—C36177.8 (2)
C2—C3—C13—C18−110.6 (2)C29—C28—C38—C43−20.2 (3)
C4—C3—C13—C1811.5 (3)C27—C28—C38—C43102.9 (2)
C6—C3—C13—C18131.1 (2)C31—C28—C38—C43−138.4 (2)
C2—C3—C13—C1465.2 (3)C29—C28—C38—C39160.8 (2)
C4—C3—C13—C14−172.7 (2)C27—C28—C38—C39−76.1 (3)
C6—C3—C13—C14−53.1 (3)C31—C28—C38—C3942.5 (3)
C18—C13—C14—C150.7 (4)C43—C38—C39—C401.1 (4)
C3—C13—C14—C15−175.3 (2)C28—C38—C39—C40−179.8 (2)
C13—C14—C15—C160.3 (4)C38—C39—C40—C410.5 (4)
C19—O1—C16—C172.1 (4)C44—O2—C41—C40−168.6 (2)
C19—O1—C16—C15−176.5 (2)C44—O2—C41—C4211.0 (4)
C14—C15—C16—O1177.6 (2)C39—C40—C41—O2177.6 (3)
C14—C15—C16—C17−1.0 (4)C39—C40—C41—C42−2.1 (4)
O1—C16—C17—C18−177.8 (2)O2—C41—C42—C43−177.6 (2)
C15—C16—C17—C180.7 (3)C40—C41—C42—C432.0 (4)
C14—C13—C18—C17−1.0 (3)C39—C38—C43—C42−1.2 (3)
C3—C13—C18—C17174.9 (2)C28—C38—C43—C42179.8 (2)
C16—C17—C18—C130.4 (4)C41—C42—C43—C38−0.4 (4)
C4—C5—C20—C21−37.1 (3)C29—C30—C45—C50−144.9 (2)
S1—C5—C20—C21141.01 (19)S2—C30—C45—C5036.7 (3)
C4—C5—C20—C25144.6 (2)C29—C30—C45—C4636.0 (3)
S1—C5—C20—C25−37.3 (3)S2—C30—C45—C46−142.44 (19)
C25—C20—C21—C22−0.9 (4)C50—C45—C46—C471.3 (4)
C5—C20—C21—C22−179.2 (2)C30—C45—C46—C47−179.6 (2)
C20—C21—C22—C230.3 (4)C45—C46—C47—C48−0.5 (4)
C21—C22—C23—C240.4 (4)C46—C47—C48—C49−0.3 (4)
C22—C23—C24—C25−0.6 (4)C47—C48—C49—C500.3 (4)
C23—C24—C25—C20−0.1 (4)C48—C49—C50—C450.5 (4)
C21—C20—C25—C240.8 (3)C46—C45—C50—C49−1.3 (3)
C5—C20—C25—C24179.1 (2)C30—C45—C50—C49179.6 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2580).

References

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