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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Feb 25;65(Pt 3):o605. doi: 10.1107/S1600536809005935

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

Hossein Rahmani a, Hooshang Pirelahi b, Seik Weng Ng c,*
PMCID: PMC2968567  PMID: 21582259

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 ▶). For the general synthesis from a Grignard reaction, see: Suld & Price (1962 ▶).graphic file with name e-65-0o605-scheme1.jpg

Experimental

Crystal data

  • C25H22OS

  • M r = 370.49

  • Orthorhombic, Inline graphic

  • 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 ▶) 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 ▶), 4271 Friedel pairs

  • Flack parameter: 0.39 (6)

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

Supplementary Material

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

e-65-0o605-sup1.cif (30.4KB, cif)

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

e-65-0o605-Isup2.hkl (431KB, 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.

Fig. 1.

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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

C25H22OS F(000) = 1568
Mr = 370.49 Dx = 1.263 Mg m−3
Orthorhombic, Pca21 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac Cell parameters from 6600 reflections
a = 14.1567 (2) Å θ = 2.7–25.9°
b = 7.6138 (1) Å µ = 0.18 mm−1
c = 36.1457 (6) Å T = 115 K
V = 3896.0 (1) Å3 Prism, pale yellow
Z = 8 0.30 × 0.20 × 0.10 mm
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Data collection

Bruker SMART APEX diffractometer 8811 independent reflections
Radiation source: fine-focus sealed tube 7499 reflections with I > 2˘I)
graphite Rint = 0.048
ω scans θmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −18→18
Tmin = 0.919, Tmax = 0.982 k = −9→9
35118 measured reflections l = −46→46
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040 H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3658P] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max = 0.001
8811 reflections Δρmax = 0.27 e Å−3
492 parameters Δρmin = −0.25 e Å−3
1 restraint Absolute structure: Flack (1983), 4271 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.39 (6)
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.74555 (4) 0.75526 (7) 0.500000 (18) 0.02190 (12)
S2 0.48342 (4) 0.25554 (7) 0.150501 (17) 0.02188 (12)
O1 0.93417 (12) 0.9368 (3) 0.30170 (5) 0.0335 (4)
O2 0.68606 (14) 0.6061 (3) 0.34833 (5) 0.0456 (5)
C1 0.66819 (14) 0.8115 (3) 0.46382 (6) 0.0190 (5)
C2 0.67887 (15) 0.9498 (3) 0.44191 (7) 0.0213 (5)
H2 0.6296 0.9691 0.4245 0.026*
C3 0.75898 (15) 1.0807 (3) 0.44093 (6) 0.0198 (5)
C4 0.82518 (15) 1.0587 (3) 0.47343 (6) 0.0206 (5)
H4 0.8723 1.1465 0.4761 0.025*
C5 0.82586 (14) 0.9317 (3) 0.49885 (6) 0.0188 (4)
C6 0.71782 (18) 1.2682 (3) 0.44237 (7) 0.0274 (5)
H6A 0.6749 1.2856 0.4214 0.041*
H6B 0.7693 1.3539 0.4410 0.041*
H6C 0.6831 1.2841 0.4656 0.041*
C7 0.58948 (14) 0.6828 (3) 0.45931 (6) 0.0196 (5)
C8 0.54589 (16) 0.6034 (3) 0.48994 (7) 0.0234 (5)
H8 0.5661 0.6320 0.5143 0.028*
C9 0.47374 (17) 0.4837 (3) 0.48484 (8) 0.0271 (6)
H9 0.4449 0.4303 0.5057 0.033*
C10 0.44330 (17) 0.4411 (3) 0.44995 (8) 0.0304 (6)
H10 0.3931 0.3597 0.4467 0.036*
C11 0.48646 (17) 0.5181 (4) 0.41938 (8) 0.0305 (6)
H11 0.4661 0.4880 0.3952 0.037*
C12 0.55884 (16) 0.6381 (3) 0.42407 (7) 0.0252 (5)
H12 0.5878 0.6902 0.4030 0.030*
C13 0.81171 (15) 1.0511 (3) 0.40405 (6) 0.0190 (5)
C14 0.76714 (17) 1.0842 (3) 0.37024 (7) 0.0279 (5)
H14 0.7055 1.1336 0.3703 0.033*
C15 0.80995 (17) 1.0473 (3) 0.33695 (7) 0.0298 (5)
H15 0.7780 1.0718 0.3144 0.036*
C16 0.89975 (17) 0.9743 (3) 0.33624 (7) 0.0252 (5)
C17 0.94639 (16) 0.9416 (3) 0.36914 (7) 0.0248 (5)
H17 1.0082 0.8928 0.3690 0.030*
C18 0.90181 (16) 0.9809 (3) 0.40252 (7) 0.0226 (5)
H18 0.9344 0.9587 0.4250 0.027*
C19 1.0242 (2) 0.8520 (4) 0.29948 (8) 0.0426 (7)
H19A 1.0396 0.8288 0.2735 0.064*
H19B 1.0220 0.7408 0.3131 0.064*
H19C 1.0726 0.9282 0.3103 0.064*
C20 0.89736 (15) 0.9209 (3) 0.52889 (6) 0.0195 (5)
C21 0.99097 (17) 0.9677 (3) 0.52196 (7) 0.0244 (5)
H21 1.0085 1.0078 0.4980 0.029*
C22 1.05849 (18) 0.9563 (3) 0.54949 (8) 0.0314 (6)
H22 1.1219 0.9892 0.5444 0.038*
C23 1.03454 (18) 0.8975 (3) 0.58441 (7) 0.0283 (5)
H23 1.0810 0.8907 0.6033 0.034*
C24 0.94234 (18) 0.8488 (3) 0.59161 (7) 0.0284 (5)
H24 0.9256 0.8073 0.6155 0.034*
C25 0.87397 (16) 0.8599 (3) 0.56422 (6) 0.0242 (5)
H25 0.8108 0.8259 0.5695 0.029*
C26 0.40910 (15) 0.3075 (3) 0.18818 (6) 0.0188 (5)
C27 0.42127 (16) 0.4450 (3) 0.21015 (7) 0.0219 (5)
H27 0.3762 0.4574 0.2294 0.026*
C28 0.49713 (16) 0.5847 (3) 0.20873 (6) 0.0205 (5)
C29 0.56616 (16) 0.5548 (3) 0.17759 (6) 0.0205 (5)
H29 0.6165 0.6368 0.1760 0.025*
C30 0.56606 (14) 0.4290 (3) 0.15210 (6) 0.0182 (4)
C31 0.44897 (18) 0.7633 (3) 0.20161 (7) 0.0284 (5)
H31A 0.4011 0.7845 0.2207 0.043*
H31B 0.4188 0.7619 0.1772 0.043*
H31C 0.4964 0.8570 0.2024 0.043*
C32 0.33001 (15) 0.1805 (3) 0.19254 (6) 0.0207 (5)
C33 0.28735 (16) 0.1024 (3) 0.16188 (7) 0.0232 (5)
H33 0.3098 0.1288 0.1377 0.028*
C34 0.21227 (17) −0.0137 (3) 0.16624 (7) 0.0266 (6)
H34 0.1841 −0.0667 0.1452 0.032*
C35 0.17863 (17) −0.0519 (3) 0.20120 (8) 0.0299 (6)
H35 0.1272 −0.1306 0.2042 0.036*
C36 0.22024 (18) 0.0251 (4) 0.23171 (8) 0.0312 (6)
H36 0.1968 −0.0001 0.2558 0.037*
C37 0.29591 (17) 0.1387 (3) 0.22755 (7) 0.0266 (5)
H37 0.3248 0.1886 0.2488 0.032*
C38 0.54983 (16) 0.5857 (3) 0.24607 (6) 0.0200 (5)
C39 0.50873 (17) 0.6610 (4) 0.27743 (7) 0.0308 (6)
H39 0.4476 0.7118 0.2757 0.037*
C40 0.55541 (19) 0.6629 (4) 0.31089 (7) 0.0364 (6)
H40 0.5258 0.7140 0.3319 0.044*
C41 0.64487 (17) 0.5912 (3) 0.31433 (7) 0.0292 (5)
C42 0.68627 (16) 0.5117 (3) 0.28390 (7) 0.0252 (5)
H42 0.7467 0.4585 0.2860 0.030*
C43 0.63812 (16) 0.5107 (3) 0.25018 (7) 0.0220 (5)
H43 0.6670 0.4567 0.2294 0.026*
C44 0.78270 (19) 0.5650 (4) 0.35186 (7) 0.0374 (6)
H44A 0.8047 0.5987 0.3766 0.056*
H44B 0.8188 0.6294 0.3331 0.056*
H44C 0.7918 0.4385 0.3484 0.056*
C45 0.63793 (16) 0.4168 (3) 0.12220 (6) 0.0202 (5)
C46 0.73151 (17) 0.4634 (3) 0.12934 (7) 0.0244 (5)
H46 0.7490 0.5021 0.1534 0.029*
C47 0.79934 (18) 0.4539 (4) 0.10169 (7) 0.0304 (6)
H47 0.8627 0.4869 0.1069 0.036*
C48 0.77508 (18) 0.3966 (3) 0.06668 (7) 0.0297 (6)
H48 0.8215 0.3907 0.0477 0.036*
C49 0.68272 (18) 0.3478 (3) 0.05938 (7) 0.0285 (5)
H49 0.6658 0.3077 0.0354 0.034*
C50 0.61485 (17) 0.3571 (3) 0.08691 (6) 0.0241 (5)
H50 0.5518 0.3224 0.0817 0.029*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0191 (2) 0.0190 (3) 0.0276 (3) −0.0019 (2) −0.0007 (2) 0.0044 (2)
S2 0.0198 (2) 0.0198 (3) 0.0260 (3) −0.0011 (2) −0.0004 (2) −0.0050 (2)
O1 0.0322 (9) 0.0453 (11) 0.0229 (9) −0.0017 (8) 0.0060 (8) −0.0056 (8)
O2 0.0370 (11) 0.0760 (16) 0.0238 (10) 0.0019 (10) −0.0068 (8) −0.0092 (9)
C1 0.0156 (10) 0.0206 (11) 0.0208 (11) 0.0011 (9) 0.0047 (9) −0.0027 (9)
C2 0.0184 (10) 0.0237 (12) 0.0219 (12) 0.0008 (9) 0.0012 (9) 0.0003 (10)
C3 0.0180 (10) 0.0183 (11) 0.0233 (12) −0.0007 (8) 0.0035 (9) 0.0005 (9)
C4 0.0215 (11) 0.0188 (12) 0.0214 (12) −0.0015 (9) 0.0031 (9) −0.0009 (9)
C5 0.0180 (10) 0.0186 (11) 0.0197 (11) 0.0003 (8) 0.0056 (9) −0.0034 (9)
C6 0.0264 (12) 0.0222 (12) 0.0337 (14) 0.0043 (9) 0.0030 (11) −0.0009 (10)
C7 0.0149 (10) 0.0173 (11) 0.0267 (12) 0.0031 (8) 0.0031 (9) −0.0004 (9)
C8 0.0216 (11) 0.0216 (12) 0.0271 (13) 0.0030 (9) 0.0048 (10) 0.0009 (9)
C9 0.0249 (12) 0.0214 (13) 0.0350 (15) 0.0005 (9) 0.0101 (11) 0.0043 (10)
C10 0.0235 (12) 0.0225 (13) 0.0451 (17) −0.0063 (10) 0.0025 (11) −0.0030 (11)
C11 0.0257 (12) 0.0321 (14) 0.0338 (15) −0.0052 (11) −0.0018 (11) −0.0032 (11)
C12 0.0232 (12) 0.0260 (13) 0.0265 (13) −0.0012 (10) 0.0031 (10) 0.0025 (10)
C13 0.0195 (11) 0.0188 (11) 0.0189 (11) −0.0030 (9) 0.0028 (8) 0.0030 (9)
C14 0.0216 (11) 0.0339 (14) 0.0281 (13) 0.0048 (10) −0.0008 (10) 0.0029 (11)
C15 0.0272 (12) 0.0404 (15) 0.0219 (12) −0.0008 (11) −0.0014 (10) 0.0065 (11)
C16 0.0294 (12) 0.0261 (12) 0.0200 (11) −0.0078 (10) 0.0042 (10) −0.0044 (10)
C17 0.0202 (11) 0.0281 (13) 0.0259 (13) 0.0024 (9) 0.0016 (10) −0.0008 (11)
C18 0.0206 (11) 0.0262 (13) 0.0209 (13) −0.0029 (9) −0.0024 (9) 0.0028 (9)
C19 0.0370 (15) 0.0504 (19) 0.0404 (16) 0.0009 (13) 0.0151 (13) −0.0112 (14)
C20 0.0234 (11) 0.0150 (11) 0.0200 (11) 0.0001 (9) 0.0019 (9) −0.0028 (9)
C21 0.0231 (11) 0.0241 (11) 0.0260 (13) −0.0042 (10) 0.0012 (10) 0.0031 (10)
C22 0.0269 (13) 0.0298 (14) 0.0373 (15) −0.0076 (11) −0.0041 (11) 0.0039 (12)
C23 0.0354 (13) 0.0214 (12) 0.0280 (13) 0.0005 (10) −0.0106 (11) −0.0005 (10)
C24 0.0414 (15) 0.0255 (13) 0.0182 (12) 0.0045 (11) 0.0002 (11) 0.0013 (10)
C25 0.0262 (12) 0.0243 (13) 0.0223 (12) 0.0006 (9) 0.0051 (10) −0.0007 (9)
C26 0.0173 (11) 0.0179 (11) 0.0211 (11) 0.0027 (8) −0.0044 (8) −0.0006 (9)
C27 0.0216 (11) 0.0218 (12) 0.0224 (12) 0.0019 (9) −0.0024 (9) −0.0013 (10)
C28 0.0229 (11) 0.0196 (11) 0.0189 (11) −0.0016 (9) −0.0022 (9) −0.0033 (9)
C29 0.0224 (11) 0.0200 (12) 0.0191 (12) −0.0043 (9) −0.0038 (9) 0.0043 (9)
C30 0.0195 (10) 0.0181 (10) 0.0170 (11) 0.0001 (8) −0.0043 (9) 0.0031 (9)
C31 0.0303 (13) 0.0225 (13) 0.0324 (14) 0.0029 (10) −0.0022 (11) 0.0004 (10)
C32 0.0176 (11) 0.0177 (11) 0.0267 (12) 0.0024 (8) −0.0045 (9) −0.0010 (9)
C33 0.0223 (11) 0.0206 (12) 0.0266 (13) 0.0004 (9) −0.0035 (10) −0.0003 (9)
C34 0.0258 (12) 0.0190 (12) 0.0350 (15) −0.0029 (10) −0.0075 (11) −0.0029 (10)
C35 0.0225 (12) 0.0252 (13) 0.0420 (16) −0.0041 (10) −0.0053 (11) 0.0055 (11)
C36 0.0252 (13) 0.0359 (14) 0.0324 (15) −0.0058 (11) −0.0006 (11) 0.0044 (11)
C37 0.0242 (12) 0.0289 (13) 0.0266 (12) −0.0009 (10) −0.0045 (10) −0.0007 (10)
C38 0.0227 (11) 0.0149 (10) 0.0223 (12) −0.0030 (8) 0.0008 (9) −0.0010 (9)
C39 0.0251 (12) 0.0380 (15) 0.0294 (13) 0.0074 (11) −0.0023 (10) −0.0100 (12)
C40 0.0354 (14) 0.0490 (17) 0.0246 (13) 0.0040 (12) 0.0019 (11) −0.0118 (12)
C41 0.0304 (13) 0.0367 (14) 0.0206 (12) −0.0034 (11) −0.0006 (10) −0.0021 (10)
C42 0.0191 (11) 0.0310 (13) 0.0254 (12) 0.0006 (9) 0.0008 (9) 0.0029 (10)
C43 0.0239 (11) 0.0218 (12) 0.0204 (12) −0.0005 (9) 0.0018 (10) −0.0018 (10)
C44 0.0370 (15) 0.0446 (17) 0.0305 (14) −0.0059 (12) −0.0127 (12) 0.0014 (12)
C45 0.0257 (11) 0.0155 (11) 0.0196 (11) 0.0007 (9) −0.0016 (9) 0.0027 (9)
C46 0.0274 (12) 0.0227 (12) 0.0230 (13) −0.0034 (10) −0.0026 (10) −0.0021 (10)
C47 0.0248 (12) 0.0324 (14) 0.0338 (15) −0.0054 (11) 0.0032 (11) −0.0012 (11)
C48 0.0343 (14) 0.0244 (13) 0.0303 (14) 0.0001 (11) 0.0065 (12) 0.0008 (10)
C49 0.0400 (15) 0.0241 (13) 0.0214 (12) 0.0008 (11) 0.0008 (11) −0.0018 (10)
C50 0.0277 (12) 0.0221 (12) 0.0226 (12) −0.0011 (9) −0.0042 (10) 0.0006 (9)
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Geometric parameters (Å, °)

S1—C1 1.759 (2) C23—H23 0.9500
S1—C5 1.761 (2) C24—C25 1.387 (3)
S2—C30 1.766 (2) C24—H24 0.9500
S2—C26 1.766 (2) C25—H25 0.9500
O1—C16 1.370 (3) C26—C27 1.325 (3)
O1—C19 1.431 (3) C26—C32 1.488 (3)
O2—C41 1.365 (3) C27—C28 1.513 (3)
O2—C44 1.409 (3) C27—H27 0.9500
C1—C2 1.326 (3) C28—C29 1.508 (3)
C1—C7 1.493 (3) C28—C38 1.542 (3)
C2—C3 1.510 (3) C28—C31 1.543 (3)
C2—H2 0.9500 C29—C30 1.328 (3)
C3—C4 1.512 (3) C29—H29 0.9500
C3—C6 1.542 (3) C30—C45 1.487 (3)
C3—C13 1.544 (3) C31—H31A 0.9800
C4—C5 1.334 (3) C31—H31B 0.9800
C4—H4 0.9500 C31—H31C 0.9800
C5—C20 1.487 (3) C32—C37 1.391 (3)
C6—H6A 0.9800 C32—C33 1.395 (3)
C6—H6B 0.9800 C33—C34 1.391 (3)
C6—H6C 0.9800 C33—H33 0.9500
C7—C12 1.388 (3) C34—C35 1.381 (4)
C7—C8 1.405 (3) C34—H34 0.9500
C8—C9 1.381 (3) C35—C36 1.381 (4)
C8—H8 0.9500 C35—H35 0.9500
C9—C10 1.372 (4) C36—C37 1.385 (3)
C9—H9 0.9500 C36—H36 0.9500
C10—C11 1.392 (4) C37—H37 0.9500
C10—H10 0.9500 C38—C43 1.382 (3)
C11—C12 1.383 (3) C38—C39 1.397 (3)
C11—H11 0.9500 C39—C40 1.378 (4)
C12—H12 0.9500 C39—H39 0.9500
C13—C18 1.384 (3) C40—C41 1.385 (4)
C13—C14 1.398 (3) C40—H40 0.9500
C14—C15 1.376 (3) C41—C42 1.385 (3)
C14—H14 0.9500 C42—C43 1.397 (3)
C15—C16 1.388 (3) C42—H42 0.9500
C15—H15 0.9500 C43—H43 0.9500
C16—C17 1.383 (3) C44—H44A 0.9800
C17—C18 1.394 (3) C44—H44B 0.9800
C17—H17 0.9500 C44—H44C 0.9800
C18—H18 0.9500 C45—C50 1.393 (3)
C19—H19A 0.9800 C45—C46 1.396 (3)
C19—H19B 0.9800 C46—C47 1.388 (4)
C19—H19C 0.9800 C46—H46 0.9500
C20—C21 1.395 (3) C47—C48 1.382 (4)
C20—C25 1.398 (3) C47—H47 0.9500
C21—C22 1.383 (4) C48—C49 1.385 (3)
C21—H21 0.9500 C48—H48 0.9500
C22—C23 1.381 (4) C49—C50 1.385 (3)
C22—H22 0.9500 C49—H49 0.9500
C23—C24 1.382 (4) C50—H50 0.9500
C1—S1—C5 101.46 (11) C24—C25—H25 119.8
C30—S2—C26 101.64 (11) C20—C25—H25 119.8
C16—O1—C19 117.5 (2) C27—C26—C32 123.2 (2)
C41—O2—C44 118.5 (2) C27—C26—S2 124.19 (19)
C2—C1—C7 122.7 (2) C32—C26—S2 112.61 (16)
C2—C1—S1 124.50 (18) C26—C27—C28 128.9 (2)
C7—C1—S1 112.72 (16) C26—C27—H27 115.6
C1—C2—C3 128.6 (2) C28—C27—H27 115.6
C1—C2—H2 115.7 C29—C28—C27 112.27 (19)
C3—C2—H2 115.7 C29—C28—C38 109.90 (18)
C2—C3—C4 111.95 (19) C27—C28—C38 108.47 (18)
C2—C3—C6 109.04 (19) C29—C28—C31 107.18 (19)
C4—C3—C6 108.10 (19) C27—C28—C31 108.18 (19)
C2—C3—C13 106.66 (18) C38—C28—C31 110.84 (18)
C4—C3—C13 110.78 (18) C30—C29—C28 128.8 (2)
C6—C3—C13 110.31 (19) C30—C29—H29 115.6
C5—C4—C3 128.3 (2) C28—C29—H29 115.6
C5—C4—H4 115.8 C29—C30—C45 123.3 (2)
C3—C4—H4 115.8 C29—C30—S2 124.23 (18)
C4—C5—C20 123.3 (2) C45—C30—S2 112.48 (16)
C4—C5—S1 124.38 (18) C28—C31—H31A 109.5
C20—C5—S1 112.33 (16) C28—C31—H31B 109.5
C3—C6—H6A 109.5 H31A—C31—H31B 109.5
C3—C6—H6B 109.5 C28—C31—H31C 109.5
H6A—C6—H6B 109.5 H31A—C31—H31C 109.5
C3—C6—H6C 109.5 H31B—C31—H31C 109.5
H6A—C6—H6C 109.5 C37—C32—C33 118.3 (2)
H6B—C6—H6C 109.5 C37—C32—C26 120.4 (2)
C12—C7—C8 118.7 (2) C33—C32—C26 121.2 (2)
C12—C7—C1 119.7 (2) C34—C33—C32 120.8 (2)
C8—C7—C1 121.6 (2) C34—C33—H33 119.6
C9—C8—C7 120.3 (2) C32—C33—H33 119.6
C9—C8—H8 119.9 C35—C34—C33 120.1 (2)
C7—C8—H8 119.9 C35—C34—H34 120.0
C10—C9—C8 120.7 (2) C33—C34—H34 120.0
C10—C9—H9 119.6 C36—C35—C34 119.6 (2)
C8—C9—H9 119.6 C36—C35—H35 120.2
C9—C10—C11 119.5 (2) C34—C35—H35 120.2
C9—C10—H10 120.2 C35—C36—C37 120.5 (3)
C11—C10—H10 120.2 C35—C36—H36 119.7
C12—C11—C10 120.4 (3) C37—C36—H36 119.7
C12—C11—H11 119.8 C36—C37—C32 120.7 (2)
C10—C11—H11 119.8 C36—C37—H37 119.7
C11—C12—C7 120.4 (2) C32—C37—H37 119.7
C11—C12—H12 119.8 C43—C38—C39 117.3 (2)
C7—C12—H12 119.8 C43—C38—C28 122.0 (2)
C18—C13—C14 116.8 (2) C39—C38—C28 120.7 (2)
C18—C13—C3 122.4 (2) C40—C39—C38 121.1 (2)
C14—C13—C3 120.7 (2) C40—C39—H39 119.4
C15—C14—C13 121.9 (2) C38—C39—H39 119.4
C15—C14—H14 119.0 C39—C40—C41 120.9 (2)
C13—C14—H14 119.0 C39—C40—H40 119.6
C14—C15—C16 120.1 (2) C41—C40—H40 119.6
C14—C15—H15 120.0 O2—C41—C40 116.0 (2)
C16—C15—H15 120.0 O2—C41—C42 124.8 (2)
O1—C16—C17 125.2 (2) C40—C41—C42 119.2 (2)
O1—C16—C15 115.2 (2) C41—C42—C43 119.3 (2)
C17—C16—C15 119.6 (2) C41—C42—H42 120.4
C16—C17—C18 119.3 (2) C43—C42—H42 120.4
C16—C17—H17 120.3 C38—C43—C42 122.2 (2)
C18—C17—H17 120.3 C38—C43—H43 118.9
C13—C18—C17 122.3 (2) C42—C43—H43 118.9
C13—C18—H18 118.8 O2—C44—H44A 109.5
C17—C18—H18 118.8 O2—C44—H44B 109.5
O1—C19—H19A 109.5 H44A—C44—H44B 109.5
O1—C19—H19B 109.5 O2—C44—H44C 109.5
H19A—C19—H19B 109.5 H44A—C44—H44C 109.5
O1—C19—H19C 109.5 H44B—C44—H44C 109.5
H19A—C19—H19C 109.5 C50—C45—C46 118.4 (2)
H19B—C19—H19C 109.5 C50—C45—C30 121.7 (2)
C21—C20—C25 118.3 (2) C46—C45—C30 119.9 (2)
C21—C20—C5 120.1 (2) C47—C46—C45 120.7 (2)
C25—C20—C5 121.6 (2) C47—C46—H46 119.7
C22—C21—C20 120.8 (2) C45—C46—H46 119.7
C22—C21—H21 119.6 C48—C47—C46 120.3 (2)
C20—C21—H21 119.6 C48—C47—H47 119.9
C23—C22—C21 120.6 (2) C46—C47—H47 119.9
C23—C22—H22 119.7 C47—C48—C49 119.6 (2)
C21—C22—H22 119.7 C47—C48—H48 120.2
C22—C23—C24 119.4 (2) C49—C48—H48 120.2
C22—C23—H23 120.3 C48—C49—C50 120.3 (2)
C24—C23—H23 120.3 C48—C49—H49 119.9
C23—C24—C25 120.5 (2) C50—C49—H49 119.9
C23—C24—H24 119.7 C49—C50—C45 120.8 (2)
C25—C24—H24 119.7 C49—C50—H50 119.6
C24—C25—C20 120.5 (2) C45—C50—H50 119.6
C5—S1—C1—C2 3.5 (2) C30—S2—C26—C27 −0.8 (2)
C5—S1—C1—C7 −178.39 (15) C30—S2—C26—C32 178.67 (15)
C7—C1—C2—C3 −174.0 (2) C32—C26—C27—C28 −179.3 (2)
S1—C1—C2—C3 4.0 (4) S2—C26—C27—C28 0.2 (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—C13 111.6 (3) C26—C27—C28—C31 117.6 (3)
C2—C3—C4—C5 7.7 (3) C27—C28—C29—C30 2.0 (3)
C6—C3—C4—C5 127.8 (3) C38—C28—C29—C30 122.8 (2)
C13—C3—C4—C5 −111.2 (3) C31—C28—C29—C30 −116.6 (3)
C3—C4—C5—C20 177.6 (2) C28—C29—C30—C45 178.7 (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—C29 2.2 (2)
C1—S1—C5—C20 176.71 (15) C26—S2—C30—C45 −179.44 (15)
C2—C1—C7—C12 36.8 (3) C27—C26—C32—C37 −34.2 (3)
S1—C1—C7—C12 −141.36 (19) S2—C26—C32—C37 146.29 (19)
C2—C1—C7—C8 −144.0 (2) C27—C26—C32—C33 144.9 (2)
S1—C1—C7—C8 37.8 (3) S2—C26—C32—C33 −34.6 (3)
C12—C7—C8—C9 −0.3 (3) C37—C32—C33—C34 0.3 (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—C35 0.5 (4)
C8—C9—C10—C11 0.7 (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—C7 0.2 (4) C35—C36—C37—C32 1.5 (4)
C8—C7—C12—C11 0.3 (4) C33—C32—C37—C36 −1.3 (4)
C1—C7—C12—C11 179.5 (2) C26—C32—C37—C36 177.8 (2)
C2—C3—C13—C18 −110.6 (2) C29—C28—C38—C43 −20.2 (3)
C4—C3—C13—C18 11.5 (3) C27—C28—C38—C43 102.9 (2)
C6—C3—C13—C18 131.1 (2) C31—C28—C38—C43 −138.4 (2)
C2—C3—C13—C14 65.2 (3) C29—C28—C38—C39 160.8 (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—C39 42.5 (3)
C18—C13—C14—C15 0.7 (4) C43—C38—C39—C40 1.1 (4)
C3—C13—C14—C15 −175.3 (2) C28—C38—C39—C40 −179.8 (2)
C13—C14—C15—C16 0.3 (4) C38—C39—C40—C41 0.5 (4)
C19—O1—C16—C17 2.1 (4) C44—O2—C41—C40 −168.6 (2)
C19—O1—C16—C15 −176.5 (2) C44—O2—C41—C42 11.0 (4)
C14—C15—C16—O1 177.6 (2) C39—C40—C41—O2 177.6 (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—C18 0.7 (3) C40—C41—C42—C43 2.0 (4)
C14—C13—C18—C17 −1.0 (3) C39—C38—C43—C42 −1.2 (3)
C3—C13—C18—C17 174.9 (2) C28—C38—C43—C42 179.8 (2)
C16—C17—C18—C13 0.4 (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—C21 141.01 (19) S2—C30—C45—C50 36.7 (3)
C4—C5—C20—C25 144.6 (2) C29—C30—C45—C46 36.0 (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—C47 1.3 (4)
C5—C20—C21—C22 −179.2 (2) C30—C45—C46—C47 −179.6 (2)
C20—C21—C22—C23 0.3 (4) C45—C46—C47—C48 −0.5 (4)
C21—C22—C23—C24 0.4 (4) C46—C47—C48—C49 −0.3 (4)
C22—C23—C24—C25 −0.6 (4) C47—C48—C49—C50 0.3 (4)
C23—C24—C25—C20 −0.1 (4) C48—C49—C50—C45 0.5 (4)
C21—C20—C25—C24 0.8 (3) C46—C45—C50—C49 −1.3 (3)
C5—C20—C25—C24 179.1 (2) C30—C45—C50—C49 179.6 (2)
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Footnotes

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

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  4. Rahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603. [DOI] [PMC free article] [PubMed]
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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  7. Suld, G. & Price, C. C. (1962). J. Am. Chem. Soc.84, 2090–2094.
  8. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-0o605-sup1.cif (30.4KB, cif)

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

e-65-0o605-Isup2.hkl (431KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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