organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3,4,5-Tri­methyl-2,4,6-tri­phenyl-4H-thio­pyran

aInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, bDepartment of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iran, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 18 February 2009; accepted 19 February 2009; online 25 February 2009)

The six-membered thio­pyran ring in the title compound, C26H24S, adopts a boat conformation, with the S atom displaced by 0.478 (2) Å and the 3-methyl­ene C atom by 0.644 (2) Å from the plane of the other four sp2-hydridized C atoms. The methyl group on the methyl­ene carbon lies in a pseudo-equatorial position and the phenyl ring in a pseudo-axial position.

Related literature

For a similar compound, see: Rahmani et al. (2009[Rahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603.]). For the synthesis, see: Rahmani & Pirelahi (1997[Rahmani, H. & Pirelahi, H. (1997). Sulfur Lett. 20, 159-163.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24S

  • Mr = 368.51

  • Monoclinic, P 21 /n

  • a = 8.4525 (1) Å

  • b = 14.4732 (2) Å

  • c = 16.2971 (3) Å

  • β = 103.156 (1)°

  • V = 1941.37 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 115 K

  • 0.35 × 0.35 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.840, Tmax = 0.966

  • 17659 measured reflections

  • 4445 independent reflections

  • 3576 reflections with I > σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.123

  • S = 1.05

  • 4445 reflections

  • 247 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For a similar compound, see: Rahmani et al. (2009). For the synthesis, see: Rahmani & Pirelahi (1997).

Experimental top

4-Methyl-2,4,6-triphenyl-4H-thiopyran was was synthesized by the reaction of methyl magnesium bromide and 3,5-dimethyl-2,4,6triphenyl thiopyrylium perchlorate in dry ether under an argon atmosphere according to a reported method (Rahmani & Pirelahi, 1997). The product was isolated by TLC on neutral alumina (petroleum ether 40–60 °C) and purified by recrystalization from ethanol.

Refinement top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C26H24S; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.
3,4,5-Trimethyl-2,4,6-triphenyl-4H-thiopyran top
Crystal data top
C26H24SF(000) = 784
Mr = 368.51Dx = 1.261 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5510 reflections
a = 8.4525 (1) Åθ = 2.5–28.2°
b = 14.4732 (2) ŵ = 0.17 mm1
c = 16.2971 (3) ÅT = 115 K
β = 103.156 (1)°Block, colorless
V = 1941.37 (5) Å30.35 × 0.35 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
4445 independent reflections
Radiation source: fine-focus sealed tube3576 reflections with I > σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.840, Tmax = 0.966k = 1818
17659 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.059P)2 + 1.0605P]
where P = (Fo2 + 2Fc2)/3
4445 reflections(Δ/σ)max = 0.001
247 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C26H24SV = 1941.37 (5) Å3
Mr = 368.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.4525 (1) ŵ = 0.17 mm1
b = 14.4732 (2) ÅT = 115 K
c = 16.2971 (3) Å0.35 × 0.35 × 0.20 mm
β = 103.156 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4445 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3576 reflections with I > σ(I)
Tmin = 0.840, Tmax = 0.966Rint = 0.037
17659 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.05Δρmax = 0.39 e Å3
4445 reflectionsΔρmin = 0.36 e Å3
247 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.66266 (5)0.60193 (3)0.30451 (3)0.01781 (12)
C10.56658 (19)0.69496 (11)0.34341 (10)0.0168 (3)
C20.4182 (2)0.68372 (11)0.35910 (10)0.0170 (3)
C30.32243 (19)0.59530 (11)0.32806 (11)0.0165 (3)
C40.4297 (2)0.51230 (12)0.36251 (10)0.0174 (3)
C50.5796 (2)0.50682 (11)0.34781 (10)0.0166 (3)
C60.3438 (2)0.75486 (13)0.40643 (12)0.0231 (4)
H6A0.42240.80450.42570.035*
H6B0.31450.72570.45520.035*
H6C0.24620.78060.36920.035*
C70.1580 (2)0.59255 (13)0.35402 (12)0.0223 (4)
H7A0.17680.59430.41560.033*
H7B0.10020.53560.33290.033*
H7C0.09240.64600.33000.033*
C80.3661 (2)0.43945 (13)0.41291 (11)0.0224 (4)
H8A0.45400.39660.43740.034*
H8B0.27770.40530.37590.034*
H8C0.32530.46910.45810.034*
C90.6879 (2)0.42489 (11)0.36408 (10)0.0173 (3)
C100.6295 (2)0.33811 (12)0.33442 (11)0.0228 (4)
H100.52000.33200.30380.027*
C110.7283 (2)0.26059 (13)0.34882 (12)0.0281 (4)
H110.68590.20190.32890.034*
C120.8894 (2)0.26882 (13)0.39231 (13)0.0287 (4)
H120.95770.21590.40210.034*
C130.9494 (2)0.35449 (14)0.42122 (12)0.0261 (4)
H131.05950.36020.45100.031*
C140.8508 (2)0.43231 (13)0.40722 (11)0.0202 (4)
H140.89410.49090.42700.024*
C150.27841 (19)0.59420 (11)0.23067 (11)0.0165 (3)
C160.2352 (2)0.67542 (12)0.18567 (12)0.0240 (4)
H160.24200.73250.21510.029*
C170.1825 (2)0.67490 (13)0.09868 (12)0.0270 (4)
H170.15340.73120.06920.032*
C180.1722 (2)0.59257 (12)0.05465 (11)0.0219 (4)
H180.13640.59210.00500.026*
C190.2142 (2)0.51143 (12)0.09817 (11)0.0219 (4)
H190.20740.45460.06840.026*
C200.2667 (2)0.51212 (12)0.18537 (11)0.0201 (4)
H200.29510.45550.21450.024*
C210.6639 (2)0.78164 (11)0.35383 (10)0.0178 (3)
C220.8276 (2)0.78257 (12)0.39556 (11)0.0201 (4)
H220.87940.72680.41780.024*
C230.9153 (2)0.86471 (13)0.40479 (12)0.0237 (4)
H231.02610.86470.43420.028*
C240.8427 (2)0.94655 (13)0.37156 (12)0.0251 (4)
H240.90321.00250.37790.030*
C250.6807 (2)0.94582 (13)0.32899 (11)0.0240 (4)
H250.62981.00160.30610.029*
C260.5927 (2)0.86423 (12)0.31960 (11)0.0207 (4)
H260.48240.86450.28950.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0159 (2)0.0162 (2)0.0235 (2)0.00008 (15)0.00897 (16)0.00014 (16)
C10.0155 (8)0.0169 (8)0.0175 (8)0.0015 (6)0.0030 (6)0.0009 (6)
C20.0155 (8)0.0177 (8)0.0174 (8)0.0014 (6)0.0034 (6)0.0006 (6)
C30.0118 (7)0.0179 (8)0.0207 (8)0.0009 (6)0.0054 (6)0.0014 (6)
C40.0168 (8)0.0188 (8)0.0163 (8)0.0016 (6)0.0030 (6)0.0007 (6)
C50.0166 (8)0.0163 (8)0.0170 (8)0.0015 (6)0.0037 (6)0.0009 (6)
C60.0193 (9)0.0250 (9)0.0262 (9)0.0004 (7)0.0077 (7)0.0062 (7)
C70.0153 (8)0.0278 (9)0.0254 (9)0.0012 (7)0.0082 (7)0.0013 (7)
C80.0193 (9)0.0247 (9)0.0244 (9)0.0028 (7)0.0075 (7)0.0031 (7)
C90.0164 (8)0.0189 (8)0.0177 (8)0.0008 (6)0.0062 (6)0.0019 (6)
C100.0217 (9)0.0229 (9)0.0237 (9)0.0003 (7)0.0050 (7)0.0012 (7)
C110.0338 (11)0.0217 (9)0.0317 (10)0.0018 (8)0.0133 (9)0.0009 (8)
C120.0294 (10)0.0257 (10)0.0351 (10)0.0113 (8)0.0160 (8)0.0091 (8)
C130.0177 (9)0.0349 (11)0.0267 (9)0.0053 (8)0.0069 (7)0.0094 (8)
C140.0161 (8)0.0244 (9)0.0210 (8)0.0016 (7)0.0058 (7)0.0023 (7)
C150.0092 (7)0.0202 (8)0.0207 (8)0.0001 (6)0.0044 (6)0.0002 (6)
C160.0274 (9)0.0162 (8)0.0263 (9)0.0046 (7)0.0016 (7)0.0038 (7)
C170.0314 (10)0.0194 (9)0.0271 (10)0.0042 (7)0.0000 (8)0.0032 (7)
C180.0181 (8)0.0265 (9)0.0200 (8)0.0004 (7)0.0019 (7)0.0008 (7)
C190.0207 (8)0.0186 (8)0.0251 (9)0.0001 (7)0.0027 (7)0.0044 (7)
C200.0188 (8)0.0167 (8)0.0239 (9)0.0007 (6)0.0030 (7)0.0014 (7)
C210.0177 (8)0.0193 (8)0.0177 (8)0.0010 (6)0.0067 (6)0.0012 (6)
C220.0172 (8)0.0211 (9)0.0221 (8)0.0012 (6)0.0050 (7)0.0000 (7)
C230.0160 (8)0.0286 (10)0.0267 (9)0.0041 (7)0.0050 (7)0.0019 (7)
C240.0271 (10)0.0227 (9)0.0277 (10)0.0061 (7)0.0106 (8)0.0022 (7)
C250.0274 (10)0.0195 (9)0.0256 (9)0.0002 (7)0.0070 (8)0.0038 (7)
C260.0188 (8)0.0223 (9)0.0207 (8)0.0004 (7)0.0039 (7)0.0005 (7)
Geometric parameters (Å, º) top
S1—C11.7631 (17)C12—C131.381 (3)
S1—C51.7638 (16)C12—H120.9500
C1—C21.346 (2)C13—C141.389 (3)
C1—C211.488 (2)C13—H130.9500
C2—C61.507 (2)C14—H140.9500
C2—C31.537 (2)C15—C161.390 (2)
C3—C41.532 (2)C15—C201.390 (2)
C3—C71.543 (2)C16—C171.386 (3)
C3—C151.546 (2)C16—H160.9500
C4—C51.345 (2)C17—C181.383 (2)
C4—C81.509 (2)C17—H170.9500
C5—C91.485 (2)C18—C191.376 (2)
C6—H6A0.9800C18—H180.9500
C6—H6B0.9800C19—C201.389 (2)
C6—H6C0.9800C19—H190.9500
C7—H7A0.9800C20—H200.9500
C7—H7B0.9800C21—C261.396 (2)
C7—H7C0.9800C21—C221.397 (2)
C8—H8A0.9800C22—C231.391 (2)
C8—H8B0.9800C22—H220.9500
C8—H8C0.9800C23—C241.386 (3)
C9—C101.395 (2)C23—H230.9500
C9—C141.400 (2)C24—C251.387 (3)
C10—C111.387 (3)C24—H240.9500
C10—H100.9500C25—C261.386 (2)
C11—C121.389 (3)C25—H250.9500
C11—H110.9500C26—H260.9500
C1—S1—C5101.20 (8)C13—C12—C11119.49 (17)
C2—C1—C21126.50 (15)C13—C12—H12120.3
C2—C1—S1120.10 (13)C11—C12—H12120.3
C21—C1—S1113.39 (12)C12—C13—C14120.77 (17)
C1—C2—C6122.02 (15)C12—C13—H13119.6
C1—C2—C3118.81 (14)C14—C13—H13119.6
C6—C2—C3119.17 (14)C13—C14—C9120.34 (17)
C4—C3—C2107.98 (13)C13—C14—H14119.8
C4—C3—C7111.96 (14)C9—C14—H14119.8
C2—C3—C7111.78 (13)C16—C15—C20117.66 (16)
C4—C3—C15110.63 (13)C16—C15—C3120.41 (15)
C2—C3—C15109.40 (13)C20—C15—C3121.70 (15)
C7—C3—C15105.07 (13)C17—C16—C15121.32 (16)
C5—C4—C8121.52 (15)C17—C16—H16119.3
C5—C4—C3118.93 (14)C15—C16—H16119.3
C8—C4—C3119.54 (14)C18—C17—C16120.20 (17)
C4—C5—C9125.67 (15)C18—C17—H17119.9
C4—C5—S1120.16 (13)C16—C17—H17119.9
C9—C5—S1114.17 (12)C19—C18—C17119.29 (17)
C2—C6—H6A109.5C19—C18—H18120.4
C2—C6—H6B109.5C17—C18—H18120.4
H6A—C6—H6B109.5C18—C19—C20120.40 (16)
C2—C6—H6C109.5C18—C19—H19119.8
H6A—C6—H6C109.5C20—C19—H19119.8
H6B—C6—H6C109.5C19—C20—C15121.13 (16)
C3—C7—H7A109.5C19—C20—H20119.4
C3—C7—H7B109.5C15—C20—H20119.4
H7A—C7—H7B109.5C26—C21—C22118.38 (16)
C3—C7—H7C109.5C26—C21—C1119.97 (15)
H7A—C7—H7C109.5C22—C21—C1121.63 (15)
H7B—C7—H7C109.5C23—C22—C21120.38 (16)
C4—C8—H8A109.5C23—C22—H22119.8
C4—C8—H8B109.5C21—C22—H22119.8
H8A—C8—H8B109.5C24—C23—C22120.70 (17)
C4—C8—H8C109.5C24—C23—H23119.6
H8A—C8—H8C109.5C22—C23—H23119.6
H8B—C8—H8C109.5C23—C24—C25119.19 (17)
C10—C9—C14118.23 (16)C23—C24—H24120.4
C10—C9—C5120.13 (15)C25—C24—H24120.4
C14—C9—C5121.62 (15)C26—C25—C24120.39 (17)
C11—C10—C9121.18 (17)C26—C25—H25119.8
C11—C10—H10119.4C24—C25—H25119.8
C9—C10—H10119.4C25—C26—C21120.93 (16)
C10—C11—C12119.97 (18)C25—C26—H26119.5
C10—C11—H11120.0C21—C26—H26119.5
C12—C11—H11120.0
C5—S1—C1—C229.19 (15)C10—C11—C12—C130.3 (3)
C5—S1—C1—C21151.99 (12)C11—C12—C13—C140.1 (3)
C21—C1—C2—C612.4 (3)C12—C13—C14—C90.6 (3)
S1—C1—C2—C6168.91 (13)C10—C9—C14—C131.3 (2)
C21—C1—C2—C3167.85 (15)C5—C9—C14—C13179.74 (16)
S1—C1—C2—C310.8 (2)C4—C3—C15—C16156.56 (15)
C1—C2—C3—C454.54 (19)C2—C3—C15—C1637.7 (2)
C6—C2—C3—C4125.18 (16)C7—C3—C15—C1682.42 (18)
C1—C2—C3—C7178.12 (15)C4—C3—C15—C2029.1 (2)
C6—C2—C3—C71.6 (2)C2—C3—C15—C20147.93 (15)
C1—C2—C3—C1565.93 (19)C7—C3—C15—C2091.92 (18)
C6—C2—C3—C15114.35 (16)C20—C15—C16—C170.1 (3)
C2—C3—C4—C554.04 (19)C3—C15—C16—C17174.63 (16)
C7—C3—C4—C5177.52 (15)C15—C16—C17—C180.1 (3)
C15—C3—C4—C565.65 (19)C16—C17—C18—C190.2 (3)
C2—C3—C4—C8125.17 (16)C17—C18—C19—C200.1 (3)
C7—C3—C4—C81.7 (2)C18—C19—C20—C150.1 (3)
C15—C3—C4—C8115.13 (16)C16—C15—C20—C190.2 (3)
C8—C4—C5—C911.4 (3)C3—C15—C20—C19174.69 (15)
C3—C4—C5—C9169.35 (15)C2—C1—C21—C2649.4 (2)
C8—C4—C5—S1169.24 (13)S1—C1—C21—C26129.31 (14)
C3—C4—C5—S110.0 (2)C2—C1—C21—C22132.24 (18)
C1—S1—C5—C429.71 (15)S1—C1—C21—C2249.03 (19)
C1—S1—C5—C9150.90 (12)C26—C21—C22—C232.0 (2)
C4—C5—C9—C1050.0 (2)C1—C21—C22—C23179.63 (16)
S1—C5—C9—C10129.34 (15)C21—C22—C23—C241.1 (3)
C4—C5—C9—C14131.58 (18)C22—C23—C24—C250.2 (3)
S1—C5—C9—C1449.07 (19)C23—C24—C25—C260.2 (3)
C14—C9—C10—C111.5 (3)C24—C25—C26—C211.1 (3)
C5—C9—C10—C11179.99 (16)C22—C21—C26—C252.0 (3)
C9—C10—C11—C121.0 (3)C1—C21—C26—C25179.61 (16)

Experimental details

Crystal data
Chemical formulaC26H24S
Mr368.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)115
a, b, c (Å)8.4525 (1), 14.4732 (2), 16.2971 (3)
β (°) 103.156 (1)
V3)1941.37 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.35 × 0.35 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.840, 0.966
No. of measured, independent and
observed [I > σ(I)] reflections
17659, 4445, 3576
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.123, 1.05
No. of reflections4445
No. of parameters247
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationRahmani, H. & Pirelahi, H. (1997). Sulfur Lett. 20, 159–163.  CAS
First citationRahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2009). publCIF. In preparation.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds