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The crystal structure of the title compound, C48H26S2, has been determined in the monoclinic space group C2 at 123 K. The compound possesses C2 symmetry, the crystallographic twofold axis passing through the mid-point of the bond connecting the two naphthyl moieties. The dihedral angle between the two naphthyl groups is 69.3 (3)°, the dihedral angle between the phenyl and thienyl­ene groups is 83.2 (3)°, and the dihedral angle between the thienyl­ene and naphthyl groups is 8.7 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007116/wn6142sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007116/wn6142Isup2.hkl
Contains datablock I

CCDC reference: 214591

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.094
  • Data-to-parameter ratio = 8.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
PLAT_734 Alert A Contact Calc 1.0085(17), Rep 1.00803(6) .... 9.90 su-Ratio C3 -H1 1.555 1.555 PLAT_734 Alert A Contact Calc 1.0121(17), Rep 1.01153(6) .... 9.90 su-Ratio C22 -H11 1.555 1.555 PLAT_734 Alert A Contact Calc 1.0053(17), Rep 1.00601(5) .... 9.90 su-Ratio C20 -H9 1.555 1.555 PLAT_734 Alert A Contact Calc 1.0526(16), Rep 1.05254(7) .... 9.90 su-Ratio C14 -H7 1.555 1.555
Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(10) - C(11) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(12) - C(13) = 1.42 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(16) - C(17) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(18) - C(19) = 1.43 Ang. PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 31.00 A   3 PLAT_744 Alert C Contact Calc 1.0038(18), Rep 1.00400 .... Missing su C21 -H10 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 3505 Count of symmetry unique reflns 2092 Completeness (_total/calc) 167.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1413 Fraction of Friedel pairs measured 0.675 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
4 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
6 Alert Level C = Please check

Comment top

Phenylene–ethynylenes have received great attention as organic photoluminescent (Kokil et al., 2002) and electroluminescent compounds (Kraft et al., 1998) and a number of phenylene–ethynylenes have been prepared (Bunz et al., 2001). We have been intrigued by such features of phenylene–ethynylenes, and we have successfully prepared acetylenes bearing various substituents (Orita et al., 1999), a highly strained acetylenic cyclophane (Orita, Hasegawa, Nakano & Otera, 2002) and optically active acetylenic cyclophanes (Orita, Hasegawa, An et al., 2002). Furthermore, it is recognized that thiophene derivatives serve as conducting organic materials and various types of oligo- and polythiophenes have been reported (Miller & Mann, 1996). We have prepared an optically active phenylene–ethynylene-bearing thiophenylene, (I), in expectation of a new function of phenylene–ethynylene derivatives as a new category of photo- and electroluminescent compounds. We describe here the structural features of (I) in the solid state.

(R)-1,1'-Binaphthyl was employed as a chiral center and, in the crystal structure, the dihedral angle between the two naphthyl groups is 69.3 (3)°. The title compound shows C2 symmetry, the crystallographic twofold axis passing through the mid-point of the C1—C1' bond (Fig. 1). The two arylene–ethynylenes are oriented in opposite directions, showing no intramolecular interaction with each other. Although both types of acetylenes are conjugated to arenes, the bond lengths C17—C18 and C11—C12, 1.201 (2) and 1.2018 (17) Å, respectively, are in good agreement with values observed in cyclic acetylenes which we have prepared earlier (Orita, Jiang et al., 2002). The dihedral angles between phenyl and thienylene and between thienylene and naphthylene are 83.2 (3) and 8.7 (3)°, respectively, showing that the three aromatic ring systems are not completely conjugated.

Experimental top

A mixture of Pd(PPh3)4 (91.3 mg, 0.079 mmol), CuI (15.0 mg, 0.079 mmol), 2-bromo-5-(phenylethylyne)thiophene (500 mg, 1.90 mmol), (R)-2,2'-ethynyl-1,1'-binaphthyl (240 mg, 0.791 mmol) and iPr2NH (3 ml) in toluene (20 ml) was heated under an argon atmosphere at 318 K for 15 h. After the usual work-up with NH4Cl/CHCl3, the organic layer was dried over MgSO4, and the solvents were removed under reduced pressure. The resulting residue was purified by chromatography on silica gel (hexane–CH2Cl2 4:1, RF = 0.23) to give 429.3 mg of the title compound, (I), as a yellow solid (81% yield); 1H NMR (300 MHz, CDCl3): δ 6.51 (d, J = 3.8 Hz, 2H), 6.94 (d, J = 3.8 Hz, 2H), 7.40–7.30 (m, 10H), 7.48–7.46 (m, 4H), 7.54–7.51 (m, 2H), 7.76 (d, J = 8.2 Hz, 2H), 7.99 (dd, J = 8.2, J = 6.7 Hz, 4H); 13C NMR (125 MHz, CDCl3): δ 82.4, 86.4, 93.9, 94.2, 121.1, 122. 6, 124.4, 124.5, 126.5, 126.8, 127.0, 127.6, 128.1, 128.2, 128.3, 128.6, 131.4, 131.5, 131.6, 132.5, 133.1, 140.0; elemental analysis calculated (%) for C48H26S2: C 86.45, H 3.93, found: C 86.29 H 3.66.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Rigaku, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Molecular Structure Corporation and Rigaku, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
(I) top
Crystal data top
C48H26S2F(000) = 692.00
Mr = 666.85Dx = 1.272 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.7107 Å
a = 12.2484 (1) ÅCell parameters from 3933 reflections
b = 12.6553 (1) Åθ = 2.3–25.0°
c = 11.5031 (9) ŵ = 0.19 mm1
β = 102.407 (5)°T = 123 K
V = 1741.4 (1) Å3Cube, yellow
Z = 20.30 × 0.20 × 0.20 mm
Data collection top
Rigaku RAXIS-IV
diffractometer
3501 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.022
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1515
Tmin = 0.963, Tmax = 1.000k = 1615
6879 measured reflectionsl = 1414
3505 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0016Fo2 + σ2(Fo) + 0.5]/(4Fo2)
R[F2 > 2σ(F2)] = 0.030(Δ/σ)max < 0.001
wR(F2) = 0.094Δρmax = 0.33 e Å3
S = 1.18Δρmin = 0.44 e Å3
2081 reflectionsAbsolute structure: Flack (1983), 1592 Friedel pairs
240 parametersAbsolute structure parameter: 0.07 (4)
All H-atom parameters refined
Crystal data top
C48H26S2V = 1741.4 (1) Å3
Mr = 666.85Z = 2
Monoclinic, C2Mo Kα radiation
a = 12.2484 (1) ŵ = 0.19 mm1
b = 12.6553 (1) ÅT = 123 K
c = 11.5031 (9) Å0.30 × 0.20 × 0.20 mm
β = 102.407 (5)°
Data collection top
Rigaku RAXIS-IV
diffractometer
3505 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3501 reflections with F2 > 2σ(F2)
Tmin = 0.963, Tmax = 1.000Rint = 0.022
6879 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030All H-atom parameters refined
wR(F2) = 0.094Δρmax = 0.33 e Å3
S = 1.18Δρmin = 0.44 e Å3
2081 reflectionsAbsolute structure: Flack (1983), 1592 Friedel pairs
240 parametersAbsolute structure parameter: 0.07 (4)
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.37680 (3)0.42883 (3)0.32626 (2)0.02704 (8)
C120.1920 (1)0.5298 (1)0.1934 (1)0.0200 (3)
C20.14344 (9)0.72572 (9)0.0161 (1)0.0166 (2)
C130.3049 (1)0.49753 (9)0.2037 (1)0.0215 (3)
C110.0985 (1)0.5642 (1)0.1776 (1)0.0191 (3)
C30.1777 (1)0.78498 (9)0.0896 (1)0.0198 (3)
C50.3524 (1)0.8286 (1)0.0333 (1)0.0313 (3)
C160.4972 (1)0.4273 (1)0.2708 (1)0.0278 (3)
C40.2798 (1)0.8360 (1)0.1143 (1)0.0269 (3)
C10.03821 (9)0.67186 (9)0.04333 (9)0.0149 (2)
C70.2165 (1)0.7201 (1)0.0982 (1)0.0218 (3)
C90.0812 (1)0.6121 (1)0.2315 (1)0.0239 (3)
C190.7758 (1)0.3014 (1)0.4801 (1)0.0309 (3)
C170.5960 (1)0.3808 (1)0.3401 (1)0.0334 (3)
C100.0077 (1)0.61592 (9)0.1495 (1)0.0178 (2)
C150.4822 (1)0.4775 (1)0.1623 (1)0.0328 (3)
C220.9587 (1)0.2154 (1)0.6403 (1)0.0353 (3)
C60.3218 (1)0.7734 (1)0.0690 (1)0.0293 (3)
C210.8836 (1)0.1502 (1)0.5637 (1)0.0369 (4)
C80.1828 (1)0.6617 (1)0.2053 (1)0.0269 (3)
C230.9422 (1)0.3223 (1)0.6358 (1)0.0357 (4)
C200.7927 (1)0.1918 (1)0.4848 (1)0.0338 (3)
C240.8515 (1)0.3667 (1)0.5558 (1)0.0365 (4)
C180.6790 (1)0.3447 (1)0.4024 (1)0.0353 (3)
C140.3719 (1)0.5174 (1)0.1242 (1)0.0275 (3)
H60.0676 (1)0.5699 (1)0.2937 (1)0.029 (1)*
H10.1330 (1)0.78611 (9)0.1537 (1)0.024 (1)*
H20.2909 (1)0.8782 (1)0.1878 (1)0.032 (1)*
H80.5358 (1)0.4780 (1)0.1081 (1)0.040 (1)*
H70.3413 (1)0.5591 (1)0.0447 (1)0.033 (1)*
H130.8367 (1)0.4368 (1)0.5564 (1)0.041 (1)*
H120.9922 (1)0.3616 (1)0.6866 (1)0.041 (1)*
H111.0232 (1)0.1810 (1)0.6976 (1)0.041 (1)*
H100.8952 (1)0.0720 (1)0.5746 (1)0.043 (1)*
H90.7423 (1)0.1466 (1)0.4241 (1)0.039 (1)*
H50.2373 (1)0.6537 (1)0.2581 (1)0.033 (1)*
H40.3660 (1)0.7750 (1)0.1299 (1)0.036 (1)*
H30.4217 (1)0.8716 (1)0.0526 (1)0.038 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0280 (2)0.0312 (2)0.0183 (1)0.0138 (1)0.0030 (1)0.0012 (1)
C120.0211 (6)0.0209 (5)0.0167 (5)0.0034 (5)0.0006 (4)0.0003 (4)
C20.0116 (5)0.0193 (5)0.0183 (5)0.0015 (4)0.0020 (4)0.0049 (4)
C130.0204 (6)0.0228 (6)0.0180 (5)0.0076 (5)0.0030 (4)0.0014 (4)
C110.0209 (5)0.0208 (5)0.0153 (5)0.0017 (5)0.0032 (4)0.0018 (4)
C30.0143 (5)0.0214 (5)0.0227 (5)0.0002 (4)0.0015 (4)0.0007 (4)
C50.0128 (5)0.0413 (7)0.0374 (7)0.0087 (6)0.0002 (5)0.0101 (6)
C160.0244 (6)0.0330 (6)0.0216 (5)0.0154 (6)0.0052 (4)0.0096 (5)
C40.0202 (6)0.0297 (6)0.0276 (6)0.0048 (5)0.0019 (5)0.0008 (5)
C10.0102 (4)0.0186 (5)0.0165 (5)0.0011 (4)0.0039 (4)0.0028 (4)
C70.0123 (5)0.0319 (6)0.0220 (5)0.0009 (5)0.0053 (4)0.0095 (5)
C90.0231 (6)0.0332 (6)0.0169 (5)0.0015 (5)0.0075 (4)0.0033 (4)
C190.0255 (6)0.0395 (8)0.0231 (6)0.0180 (6)0.0052 (5)0.0098 (5)
C170.0303 (7)0.0411 (7)0.0232 (6)0.0175 (6)0.0064 (5)0.0122 (5)
C100.0148 (5)0.0211 (5)0.0174 (5)0.0006 (4)0.0034 (4)0.0005 (4)
C150.0251 (7)0.0463 (8)0.0251 (6)0.0146 (6)0.0017 (5)0.0038 (5)
C220.0270 (6)0.0531 (9)0.0222 (6)0.0194 (7)0.0027 (5)0.0021 (6)
C60.0136 (5)0.0440 (8)0.0319 (6)0.0019 (6)0.0081 (5)0.0126 (6)
C210.0342 (7)0.0381 (8)0.0347 (7)0.0167 (7)0.0005 (6)0.0015 (6)
C80.0184 (5)0.0421 (7)0.0225 (6)0.0019 (6)0.0095 (4)0.0046 (5)
C230.0270 (7)0.0465 (9)0.0271 (7)0.0129 (6)0.0084 (6)0.0096 (6)
C200.0321 (7)0.0353 (7)0.0285 (6)0.0118 (6)0.0056 (5)0.0081 (5)
C240.0331 (7)0.0373 (8)0.0321 (7)0.0174 (6)0.0083 (6)0.0106 (6)
C180.0329 (7)0.0419 (8)0.0250 (6)0.0186 (7)0.0072 (5)0.0127 (6)
C140.0229 (6)0.0369 (7)0.0207 (5)0.0098 (6)0.0001 (5)0.0003 (5)
Geometric parameters (Å, º) top
S1—C131.7274 (12)C7—C61.4303 (17)
S1—C161.7282 (13)C7—C81.4202 (18)
C10—C111.4302 (17)C9—C101.4379 (14)
C11—C121.2018 (17)C9—C81.3675 (18)
C12—C131.4220 (16)C9—H60.880 (2)
C13—C141.3768 (18)C19—C201.401 (2)
C14—C151.4206 (18)C19—C241.398 (2)
C15—C161.377 (2)C15—H80.998 (2)
C16—C171.4252 (17)C22—C211.398 (2)
C17—C181.201 (2)C22—C231.368 (2)
C18—C191.4314 (18)C22—H111.012 (3)
C2—C31.4134 (16)C6—H40.973 (2)
C2—C11.4321 (15)C21—C201.381 (2)
C2—C71.4358 (13)C21—H101.004 (2)
C3—C41.3808 (16)C8—H51.000 (2)
C3—H11.008 (2)C23—C241.3986 (19)
C5—C41.4226 (19)C23—H120.901 (3)
C5—C61.350 (2)C20—H91.006 (3)
C5—H30.992 (2)C24—H130.905 (2)
C4—H20.985 (2)C14—H71.053 (2)
C1—C101.3910 (15)
S1···C122.7578 (13)C1···C82.8354 (14)
S1···C131.7274 (12)C1···H63.2450 (15)
S1···C161.7282 (13)C1···H12.7284 (15)
S1···C19i3.5846 (13)C1···H1iv2.6375 (17)
S1···C172.7243 (15)C7···C92.4235 (18)
S1···C152.5782 (16)C7···C102.8250 (17)
S1···C24i3.4501 (16)C7···C61.4303 (17)
S1···C18i3.5018 (14)C7···C81.4202 (18)
S1···C142.5691 (14)C7···H63.1992 (18)
S1···H83.5459 (15)C7···H13.3777 (17)
S1···H73.5761 (14)C7···H7iv2.8483 (17)
S1···H13i3.1920 (17)C7···H52.0870 (17)
S1···H11ii3.4508 (17)C7···H42.0628 (16)
S1···H10iii3.3492 (16)C7···H33.3348 (19)
S1···H10ii3.3184 (15)C9···C101.4379 (14)
S1···H9iii3.5169 (14)C9···C81.3675 (18)
C12···C2iv3.4191 (17)C9···H60.880 (2)
C12···C131.4220 (16)C9···H2vi3.3374 (19)
C12···C111.2018 (17)C9···H12i3.418 (2)
C12···C3iv3.4342 (17)C9···H52.0679 (17)
C12···C13.4743 (17)C19···C172.6320 (19)
C12···C1iv3.4628 (16)C19···C222.797 (2)
C12···C102.6261 (17)C19···C212.405 (2)
C12···C6v3.5349 (18)C19···C232.4209 (17)
C12···C142.5029 (18)C19···C201.401 (2)
C12···H1iv3.3331 (17)C19···C241.398 (2)
C12···H72.7834 (17)C19···C181.4314 (18)
C12···H13i3.1987 (19)C19···H2x3.542 (2)
C12···H12i3.5868 (19)C19···H131.995 (2)
C12···H9iii2.9838 (18)C19···H123.2479 (18)
C12···H4v3.3490 (19)C19···H103.327 (2)
C12···H3v3.5017 (19)C19···H92.076 (2)
C2···C11iv3.1579 (15)C17···C152.530 (2)
C2···C31.4134 (16)C17···C21ii3.577 (2)
C2···C52.8179 (16)C17···C203.545 (2)
C2···C42.4307 (16)C17···C243.556 (2)
C2···C11.4321 (15)C17···C181.201 (2)
C2···C1iv2.5564 (15)C17···H1x2.5800 (17)
C2···C71.4358 (13)C17···H2x3.249 (2)
C2···C92.8238 (18)C17···H82.887 (2)
C2···C102.4398 (16)C17···H133.497 (2)
C2···C10iv3.2402 (15)C17···H10ii2.605 (2)
C2···C62.4663 (15)C17···H93.491 (2)
C2···C82.4650 (15)C10···C82.4366 (16)
C2···H12.1260 (16)C10···H62.0374 (14)
C2···H1iv3.5005 (17)C10···H1iv2.7526 (17)
C2···H23.2656 (16)C10···H53.3476 (15)
C2···H7iv3.1751 (17)C10···H3vi3.337 (2)
C2···H53.3581 (15)C15···C141.4206 (18)
C2···H43.3271 (15)C15···H1x3.0611 (18)
C13···C112.6203 (17)C15···H80.998 (2)
C13···C162.4808 (17)C15···H8xi3.072 (3)
C13···C152.3348 (18)C15···H72.2072 (18)
C13···C6v3.4379 (19)C15···H11ii3.046 (2)
C13···C141.3768 (18)C15···H10ii3.299 (2)
C13···H83.2563 (19)C22···C211.398 (2)
C13···H72.1218 (17)C22···C21xii3.444 (2)
C13···H11ii3.176 (2)C22···C231.368 (2)
C13···H9iii3.3769 (18)C22···C202.420 (2)
C13···H4v3.5034 (19)C22···C242.406 (2)
C11···C3iv3.1931 (17)C22···H133.224 (2)
C11···C12.4362 (15)C22···H121.946 (3)
C11···C1iv2.8380 (16)C22···H111.0115 (1)
C11···C92.4869 (16)C22···H102.053 (2)
C11···C101.4302 (17)C22···H93.337 (2)
C11···C143.5808 (18)C22···H5xiii3.270 (2)
C11···H62.6635 (16)C22···H4xiii3.184 (2)
C11···H1iv2.8624 (17)C6···C82.4923 (19)
C11···H13i3.3987 (18)C6···H23.3337 (19)
C11···H12i3.3151 (18)C6···H7iv2.999 (2)
C11···H9iii3.1754 (19)C6···H52.6704 (19)
C11···H3v3.5683 (18)C6···H40.973 (2)
C11···H3vi3.3708 (19)C6···H32.064 (2)
C3···C52.4279 (17)C6···H3ix3.3457 (19)
C3···C41.3808 (16)C21···C232.385 (2)
C3···C12.4871 (15)C21···C201.381 (2)
C3···C1iv2.9535 (16)C21···C242.767 (2)
C3···C72.4510 (17)C21···H123.182 (2)
C3···C17vii3.4656 (18)C21···H112.077 (2)
C3···C10iv3.2988 (16)C21···H11xii3.459 (2)
C3···C62.8021 (16)C21···H101.004
C3···H11.0080 (1)C21···H10xii3.564 (3)
C3···H21.9784 (17)C21···H92.093 (2)
C3···H8vii3.0326 (18)C21···H5xiii2.999 (2)
C3···H7iv3.5915 (18)C8···H61.9380 (19)
C3···H33.2946 (16)C8···H7iv3.3654 (18)
C5···C41.4226 (19)C8···H51.000 (2)
C5···C72.4203 (19)C8···H42.6478 (18)
C5···C61.350 (2)C23···C202.780 (2)
C5···H13.3198 (17)C23···C241.3986 (19)
C5···H22.167 (2)C23···H6i3.508 (2)
C5···H7iv3.418 (2)C23···H2xiv3.5300 (19)
C5···H12viii3.398 (2)C23···H132.023 (2)
C5···H42.036 (2)C23···H120.901 (3)
C5···H4ix3.4563 (19)C23···H112.094 (2)
C5···H30.992 (2)C23···H103.269 (2)
C5···H3ix3.180 (3)C23···H4xiii3.095 (2)
C16···C171.4252 (17)C20···C242.414 (2)
C16···C151.377 (2)C20···C182.452 (2)
C16···C21ii3.538 (2)C20···H133.223 (2)
C16···C182.6253 (18)C20···H13xv3.582 (2)
C16···C142.3216 (17)C20···H113.318 (2)
C16···H1x2.9558 (16)C20···H11xii3.397 (2)
C16···H82.126 (2)C20···H102.095 (2)
C16···H73.3259 (17)C20···H91.0060 (1)
C16···H11ii3.248 (2)C20···H5xiii3.2099 (19)
C16···H10ii2.692 (2)C24···C182.460 (2)
C4···C72.8125 (19)C24···H130.905 (2)
C4···C62.4097 (19)C24···H122.0313 (19)
C4···H12.0452 (17)C24···H113.336 (2)
C4···H20.985 (2)C24···H93.313 (2)
C4···H8vii3.475 (2)C18···H1x2.8913 (18)
C4···H7iii3.514 (2)C18···H2x3.098 (2)
C4···H12viii3.2251 (18)C18···H132.599 (2)
C4···H11viii3.480 (2)C18···H10ii3.045 (2)
C4···H43.2982 (18)C18···H92.620 (2)
C4···H32.0632 (18)C14···H82.1146 (19)
C1···C72.4767 (14)C14···H8xi3.1576 (19)
C1···C92.4539 (14)C14···H71.0525 (1)
C1···C101.3910 (15)C14···H11ii3.002 (2)
C1···C10iv2.5042 (15)
S1—C13—C12121.95 (9)C2—C7—C8119.3 (1)
S1—C13—C14111.21 (9)C6—C7—C8121.9 (1)
C13—S1—C1691.76 (6)C10—C9—C8120.55 (11)
S1—C16—C17119.22 (11)C10—C9—H6121.2 (2)
S1—C16—C15111.74 (9)C8—C9—H6117.5 (2)
C9—C10—C11120.24 (11)C20—C19—C24119.23 (13)
C10—C11—C12172.28 (13)C16—C15—H8126.3 (2)
C11—C12—C13173.98 (13)C14—C15—H8121.0 (2)
C12—C13—C14126.82 (11)C21—C22—C23119.22 (13)
C13—C14—C15113.15 (12)C21—C22—H11118.2 (2)
C14—C15—C16112.13 (12)C23—C22—H11122.5 (2)
C15—C16—C17128.99 (13)C5—C6—C7120.99 (11)
C16—C17—C18177.12 (13)C5—C6—H4121.6 (2)
C17—C18—C19177.94 (17)C7—C6—H4117.0 (2)
C18—C19—C20119.91 (14)C22—C21—C20121.14 (15)
C18—C19—C24120.79 (13)C22—C21—H10116.5 (2)
C1—C10—C9120.3 (1)C20—C21—H10122.1 (2)
C1—C10—C11119.4 (1)C7—C8—C9120.8 (1)
C3—C2—C1121.87 (9)C7—C8—H5118.1 (1)
C3—C2—C7118.7 (1)C9—C8—H5121.0 (1)
C1—C2—C7119.4 (1)C22—C23—C24120.84 (14)
C2—C3—C4120.90 (11)C22—C23—H12116.6 (2)
C2—C3—H1121.9 (1)C24—C23—H12122.6 (2)
C4—C3—H1116.9 (1)C19—C20—C21119.66 (14)
C4—C5—C6120.68 (12)C19—C20—H9118.2 (2)
C4—C5—H3116.2 (2)C21—C20—H9121.8 (2)
C6—C5—H3122.8 (2)C19—C24—C23119.91 (14)
C3—C4—C5120.00 (12)C19—C24—H13118.5 (2)
C3—C4—H2112.4 (1)C23—C24—H13121.4 (2)
C5—C4—H2127.5 (2)C13—C14—H7121.1 (1)
C2—C1—C10119.59 (9)C15—C14—H7125.7 (2)
C2—C7—C6118.74 (11)
C16—S1—C13—C12178.1 (1)C1—C2—C7—C6179.3 (1)
C16—S1—C13—C140.2 (1)C1—C2—C7—C80.3 (2)
C13—S1—C16—C17177.6 (1)C2—C3—C4—C50.5 (2)
C13—S1—C16—C150.1 (1)C6—C5—C4—C31.1 (2)
S1—C13—C14—C150.3 (1)C4—C5—C6—C70.7 (2)
C12—C13—C14—C15177.9 (1)C2—C1—C10—C90.0 (2)
S1—C16—C15—C140.1 (1)C2—C7—C6—C50.3 (2)
C17—C16—C15—C14177.5 (2)C8—C7—C6—C5180.0 (1)
C2—C1—C10—C11178.6 (1)C2—C7—C8—C90.9 (2)
C8—C9—C10—C11179.8 (1)C6—C7—C8—C9179.5 (1)
C8—C9—C10—C11.3 (2)C10—C9—C8—C71.7 (2)
C18—C19—C20—C21177.2 (1)C24—C19—C20—C210.2 (2)
C16—C15—C14—C130.3 (2)C20—C19—C24—C230.5 (2)
C1—C2—C3—C4179.8 (1)C18—C19—C24—C23176.5 (1)
C7—C2—C3—C40.5 (2)C23—C22—C21—C200.8 (2)
C3—C2—C1—C10179.0 (1)C21—C22—C23—C240.1 (2)
C7—C2—C1—C100.7 (2)C22—C21—C20—C190.8 (2)
C3—C2—C7—C60.9 (2)C22—C23—C24—C190.6 (2)
C3—C2—C7—C8179.4 (1)
Symmetry codes: (i) x1, y, z1; (ii) x3/2, y1/2, z1; (iii) x+1/2, y1/2, z; (iv) x, y, z; (v) x1/2, y+1/2, z; (vi) x+1/2, y+1/2, z; (vii) x1/2, y1/2, z; (viii) x+3/2, y1/2, z+1; (ix) x+1, y, z; (x) x1/2, y+1/2, z; (xi) x1, y, z; (xii) x2, y, z1; (xiii) x1/2, y+1/2, z1; (xiv) x3/2, y+1/2, z1; (xv) x3/2, y+1/2, z1.

Experimental details

Crystal data
Chemical formulaC48H26S2
Mr666.85
Crystal system, space groupMonoclinic, C2
Temperature (K)123
a, b, c (Å)12.2484 (1), 12.6553 (1), 11.5031 (9)
β (°) 102.407 (5)
V3)1741.4 (1)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerRigaku RAXIS-IV
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.963, 1.000
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
6879, 3505, 3501
Rint0.022
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.094, 1.18
No. of reflections2081
No. of parameters240
No. of restraints?
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.33, 0.44
Absolute structureFlack (1983), 1592 Friedel pairs
Absolute structure parameter0.07 (4)

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Rigaku, 1999), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Molecular Structure Corporation and Rigaku, 2001).

Selected geometric parameters (Å, º) top
S1—C131.7274 (12)C14—C151.4206 (18)
S1—C161.7282 (13)C15—C161.377 (2)
C10—C111.4302 (17)C16—C171.4252 (17)
C11—C121.2018 (17)C17—C181.201 (2)
C12—C131.4220 (16)C18—C191.4314 (18)
C13—C141.3768 (18)
S1—C13—C12121.95 (9)C13—C14—C15113.15 (12)
S1—C13—C14111.21 (9)C14—C15—C16112.13 (12)
C13—S1—C1691.76 (6)C15—C16—C17128.99 (13)
S1—C16—C17119.22 (11)C16—C17—C18177.12 (13)
S1—C16—C15111.74 (9)C17—C18—C19177.94 (17)
C9—C10—C11120.24 (11)C18—C19—C20119.91 (14)
C10—C11—C12172.28 (13)C18—C19—C24120.79 (13)
C11—C12—C13173.98 (13)C1—C10—C9120.3 (1)
C12—C13—C14126.82 (11)C1—C10—C11119.4 (1)
C16—S1—C13—C12178.1 (1)C17—C16—C15—C14177.5 (2)
C16—S1—C13—C140.2 (1)C2—C1—C10—C11178.6 (1)
C13—S1—C16—C17177.6 (1)C8—C9—C10—C11179.8 (1)
C13—S1—C16—C150.1 (1)C8—C9—C10—C11.3 (2)
S1—C13—C14—C150.3 (1)C18—C19—C20—C21177.2 (1)
C12—C13—C14—C15177.9 (1)C16—C15—C14—C130.3 (2)
S1—C16—C15—C140.1 (1)
 

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