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Acta Crystallogr Sect E Struct Rep OnlineActa Cryst. EActa Crystallographica Section E: Structure Reports Online1600-5368International Union of Crystallography sj257910.1107/S1600536809005923ACSEBHS1600536809005923Organic Papers3,4,5-Trimethyl-2,4,6-triphenyl-4H-thio­pyran C26H24SRahmani Hossein aPirelahi Hooshang bNg Seik Weng c*a Institute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iranb Department of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iranc Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaCorrespondence e-mail: gina17@example.net 3 2009 25 2 2009 25 2 2009 65 Pt 3 e090300o604 o604 18 2 2009 19 2 2009 © Rahmani et al. 20092009This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.A full version of this article is available from Crystallography Journals Online.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 sp
               2-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.
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Related literature
For a similar compound, see: Rahmani et al. (2009 ▶). For the synthesis, see: Rahmani & Pirelahi (1997 ▶).
         

Experimental

Crystal data

                  C26H24S


                           M
                           r = 368.51

Monoclinic, 
                        


                           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 ▶) T
                           min = 0.840, T
                           max = 0.966

17659 measured reflections

4445 independent reflections

3576 reflections with I > σ(I)


                           R
                           int = 0.037


               

Refinement

                  
                           R[F
                           2 > 2σ(F
                           2)] = 0.046


                           wR(F
                           2) = 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 ▶); 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/S1600536809005923/sj2579sup1.cif
            

 Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005923/sj2579Isup2.hkl
            

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

 Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2579).

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

supplementary crystallographic 
information

Experimental 
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 
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).

Figures
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.

Crystal data
C26H24S	F(000) = 784	
Mr = 368.51	Dx = 1.261 Mg m−3	
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å	
Hall symbol:  -P 2yn	Cell parameters from 5510 reflections	
a = 8.4525 (1) Å	θ = 2.5–28.2°	
b = 14.4732 (2) Å	µ = 0.17 mm−1	
c = 16.2971 (3) Å	T = 115 K	
β = 103.156 (1)°	Block, colorless	
V = 1941.37 (5)  Å3	0.35 × 0.35 × 0.20 mm	
Z = 4		
Data collection
Bruker SMART APEX diffractometer	4445 independent reflections	
Radiation source: fine-focus sealed tube	3576 reflections with I > σ(I)	
graphite	Rint = 0.037	
ω scans	θmax = 27.5°, θmin = 1.9°	
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10	
Tmin = 0.840, Tmax = 0.966	k = −18→18	
17659 measured reflections	l = −21→21	
Refinement
Refinement on F2	Primary atom site location: structure-invariant direct methods	
Least-squares matrix: full	Secondary atom site location: difference Fourier map	
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites	
wR(F2) = 0.123	H-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 parameters	Δρmax = 0.39 e Å−3	
0 restraints	Δρmin = −0.36 e Å−3	
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
	x	y	z	Uiso*/Ueq		
S1	0.66266 (5)	0.60193 (3)	0.30451 (3)	0.01781 (12)		
C1	0.56658 (19)	0.69496 (11)	0.34341 (10)	0.0168 (3)		
C2	0.4182 (2)	0.68372 (11)	0.35910 (10)	0.0170 (3)		
C3	0.32243 (19)	0.59530 (11)	0.32806 (11)	0.0165 (3)		
C4	0.4297 (2)	0.51230 (12)	0.36251 (10)	0.0174 (3)		
C5	0.5796 (2)	0.50682 (11)	0.34781 (10)	0.0166 (3)		
C6	0.3438 (2)	0.75486 (13)	0.40643 (12)	0.0231 (4)		
H6A	0.4224	0.8045	0.4257	0.035*		
H6B	0.3145	0.7257	0.4552	0.035*		
H6C	0.2462	0.7806	0.3692	0.035*		
C7	0.1580 (2)	0.59255 (13)	0.35402 (12)	0.0223 (4)		
H7A	0.1768	0.5943	0.4156	0.033*		
H7B	0.1002	0.5356	0.3329	0.033*		
H7C	0.0924	0.6460	0.3300	0.033*		
C8	0.3661 (2)	0.43945 (13)	0.41291 (11)	0.0224 (4)		
H8A	0.4540	0.3966	0.4374	0.034*		
H8B	0.2777	0.4053	0.3759	0.034*		
H8C	0.3253	0.4691	0.4581	0.034*		
C9	0.6879 (2)	0.42489 (11)	0.36408 (10)	0.0173 (3)		
C10	0.6295 (2)	0.33811 (12)	0.33442 (11)	0.0228 (4)		
H10	0.5200	0.3320	0.3038	0.027*		
C11	0.7283 (2)	0.26059 (13)	0.34882 (12)	0.0281 (4)		
H11	0.6859	0.2019	0.3289	0.034*		
C12	0.8894 (2)	0.26882 (13)	0.39231 (13)	0.0287 (4)		
H12	0.9577	0.2159	0.4021	0.034*		
C13	0.9494 (2)	0.35449 (14)	0.42122 (12)	0.0261 (4)		
H13	1.0595	0.3602	0.4510	0.031*		
C14	0.8508 (2)	0.43231 (13)	0.40722 (11)	0.0202 (4)		
H14	0.8941	0.4909	0.4270	0.024*		
C15	0.27841 (19)	0.59420 (11)	0.23067 (11)	0.0165 (3)		
C16	0.2352 (2)	0.67542 (12)	0.18567 (12)	0.0240 (4)		
H16	0.2420	0.7325	0.2151	0.029*		
C17	0.1825 (2)	0.67490 (13)	0.09868 (12)	0.0270 (4)		
H17	0.1534	0.7312	0.0692	0.032*		
C18	0.1722 (2)	0.59257 (12)	0.05465 (11)	0.0219 (4)		
H18	0.1364	0.5921	−0.0050	0.026*		
C19	0.2142 (2)	0.51143 (12)	0.09817 (11)	0.0219 (4)		
H19	0.2074	0.4546	0.0684	0.026*		
C20	0.2667 (2)	0.51212 (12)	0.18537 (11)	0.0201 (4)		
H20	0.2951	0.4555	0.2145	0.024*		
C21	0.6639 (2)	0.78164 (11)	0.35383 (10)	0.0178 (3)		
C22	0.8276 (2)	0.78257 (12)	0.39556 (11)	0.0201 (4)		
H22	0.8794	0.7268	0.4178	0.024*		
C23	0.9153 (2)	0.86471 (13)	0.40479 (12)	0.0237 (4)		
H23	1.0261	0.8647	0.4342	0.028*		
C24	0.8427 (2)	0.94655 (13)	0.37156 (12)	0.0251 (4)		
H24	0.9032	1.0025	0.3779	0.030*		
C25	0.6807 (2)	0.94582 (13)	0.32899 (11)	0.0240 (4)		
H25	0.6298	1.0016	0.3061	0.029*		
C26	0.5927 (2)	0.86423 (12)	0.31960 (11)	0.0207 (4)		
H26	0.4824	0.8645	0.2895	0.025*		
Atomic displacement parameters (Å2)
	U11	U22	U33	U12	U13	U23	
S1	0.0159 (2)	0.0162 (2)	0.0235 (2)	0.00008 (15)	0.00897 (16)	0.00014 (16)	
C1	0.0155 (8)	0.0169 (8)	0.0175 (8)	0.0015 (6)	0.0030 (6)	−0.0009 (6)	
C2	0.0155 (8)	0.0177 (8)	0.0174 (8)	0.0014 (6)	0.0034 (6)	−0.0006 (6)	
C3	0.0118 (7)	0.0179 (8)	0.0207 (8)	−0.0009 (6)	0.0054 (6)	−0.0014 (6)	
C4	0.0168 (8)	0.0188 (8)	0.0163 (8)	−0.0016 (6)	0.0030 (6)	−0.0007 (6)	
C5	0.0166 (8)	0.0163 (8)	0.0170 (8)	−0.0015 (6)	0.0037 (6)	0.0009 (6)	
C6	0.0193 (9)	0.0250 (9)	0.0262 (9)	−0.0004 (7)	0.0077 (7)	−0.0062 (7)	
C7	0.0153 (8)	0.0278 (9)	0.0254 (9)	−0.0012 (7)	0.0082 (7)	−0.0013 (7)	
C8	0.0193 (9)	0.0247 (9)	0.0244 (9)	−0.0028 (7)	0.0075 (7)	0.0031 (7)	
C9	0.0164 (8)	0.0189 (8)	0.0177 (8)	0.0008 (6)	0.0062 (6)	0.0019 (6)	
C10	0.0217 (9)	0.0229 (9)	0.0237 (9)	−0.0003 (7)	0.0050 (7)	−0.0012 (7)	
C11	0.0338 (11)	0.0217 (9)	0.0317 (10)	0.0018 (8)	0.0133 (9)	0.0009 (8)	
C12	0.0294 (10)	0.0257 (10)	0.0351 (10)	0.0113 (8)	0.0160 (8)	0.0091 (8)	
C13	0.0177 (9)	0.0349 (11)	0.0267 (9)	0.0053 (8)	0.0069 (7)	0.0094 (8)	
C14	0.0161 (8)	0.0244 (9)	0.0210 (8)	−0.0016 (7)	0.0058 (7)	0.0023 (7)	
C15	0.0092 (7)	0.0202 (8)	0.0207 (8)	−0.0001 (6)	0.0044 (6)	0.0002 (6)	
C16	0.0274 (9)	0.0162 (8)	0.0263 (9)	0.0046 (7)	0.0016 (7)	−0.0038 (7)	
C17	0.0314 (10)	0.0194 (9)	0.0271 (10)	0.0042 (7)	0.0000 (8)	0.0032 (7)	
C18	0.0181 (8)	0.0265 (9)	0.0200 (8)	0.0004 (7)	0.0019 (7)	−0.0008 (7)	
C19	0.0207 (8)	0.0186 (8)	0.0251 (9)	−0.0001 (7)	0.0027 (7)	−0.0044 (7)	
C20	0.0188 (8)	0.0167 (8)	0.0239 (9)	−0.0007 (6)	0.0030 (7)	0.0014 (7)	
C21	0.0177 (8)	0.0193 (8)	0.0177 (8)	−0.0010 (6)	0.0067 (6)	−0.0012 (6)	
C22	0.0172 (8)	0.0211 (9)	0.0221 (8)	0.0012 (6)	0.0050 (7)	0.0000 (7)	
C23	0.0160 (8)	0.0286 (10)	0.0267 (9)	−0.0041 (7)	0.0050 (7)	−0.0019 (7)	
C24	0.0271 (10)	0.0227 (9)	0.0277 (10)	−0.0061 (7)	0.0106 (8)	−0.0022 (7)	
C25	0.0274 (10)	0.0195 (9)	0.0256 (9)	−0.0002 (7)	0.0070 (8)	0.0038 (7)	
C26	0.0188 (8)	0.0223 (9)	0.0207 (8)	0.0004 (7)	0.0039 (7)	−0.0005 (7)	
Geometric parameters (Å, °)
S1—C1	1.7631 (17)	C12—C13	1.381 (3)	
S1—C5	1.7638 (16)	C12—H12	0.9500	
C1—C2	1.346 (2)	C13—C14	1.389 (3)	
C1—C21	1.488 (2)	C13—H13	0.9500	
C2—C6	1.507 (2)	C14—H14	0.9500	
C2—C3	1.537 (2)	C15—C16	1.390 (2)	
C3—C4	1.532 (2)	C15—C20	1.390 (2)	
C3—C7	1.543 (2)	C16—C17	1.386 (3)	
C3—C15	1.546 (2)	C16—H16	0.9500	
C4—C5	1.345 (2)	C17—C18	1.383 (2)	
C4—C8	1.509 (2)	C17—H17	0.9500	
C5—C9	1.485 (2)	C18—C19	1.376 (2)	
C6—H6A	0.9800	C18—H18	0.9500	
C6—H6B	0.9800	C19—C20	1.389 (2)	
C6—H6C	0.9800	C19—H19	0.9500	
C7—H7A	0.9800	C20—H20	0.9500	
C7—H7B	0.9800	C21—C26	1.396 (2)	
C7—H7C	0.9800	C21—C22	1.397 (2)	
C8—H8A	0.9800	C22—C23	1.391 (2)	
C8—H8B	0.9800	C22—H22	0.9500	
C8—H8C	0.9800	C23—C24	1.386 (3)	
C9—C10	1.395 (2)	C23—H23	0.9500	
C9—C14	1.400 (2)	C24—C25	1.387 (3)	
C10—C11	1.387 (3)	C24—H24	0.9500	
C10—H10	0.9500	C25—C26	1.386 (2)	
C11—C12	1.389 (3)	C25—H25	0.9500	
C11—H11	0.9500	C26—H26	0.9500	
				
C1—S1—C5	101.20 (8)	C13—C12—C11	119.49 (17)	
C2—C1—C21	126.50 (15)	C13—C12—H12	120.3	
C2—C1—S1	120.10 (13)	C11—C12—H12	120.3	
C21—C1—S1	113.39 (12)	C12—C13—C14	120.77 (17)	
C1—C2—C6	122.02 (15)	C12—C13—H13	119.6	
C1—C2—C3	118.81 (14)	C14—C13—H13	119.6	
C6—C2—C3	119.17 (14)	C13—C14—C9	120.34 (17)	
C4—C3—C2	107.98 (13)	C13—C14—H14	119.8	
C4—C3—C7	111.96 (14)	C9—C14—H14	119.8	
C2—C3—C7	111.78 (13)	C16—C15—C20	117.66 (16)	
C4—C3—C15	110.63 (13)	C16—C15—C3	120.41 (15)	
C2—C3—C15	109.40 (13)	C20—C15—C3	121.70 (15)	
C7—C3—C15	105.07 (13)	C17—C16—C15	121.32 (16)	
C5—C4—C8	121.52 (15)	C17—C16—H16	119.3	
C5—C4—C3	118.93 (14)	C15—C16—H16	119.3	
C8—C4—C3	119.54 (14)	C18—C17—C16	120.20 (17)	
C4—C5—C9	125.67 (15)	C18—C17—H17	119.9	
C4—C5—S1	120.16 (13)	C16—C17—H17	119.9	
C9—C5—S1	114.17 (12)	C19—C18—C17	119.29 (17)	
C2—C6—H6A	109.5	C19—C18—H18	120.4	
C2—C6—H6B	109.5	C17—C18—H18	120.4	
H6A—C6—H6B	109.5	C18—C19—C20	120.40 (16)	
C2—C6—H6C	109.5	C18—C19—H19	119.8	
H6A—C6—H6C	109.5	C20—C19—H19	119.8	
H6B—C6—H6C	109.5	C19—C20—C15	121.13 (16)	
C3—C7—H7A	109.5	C19—C20—H20	119.4	
C3—C7—H7B	109.5	C15—C20—H20	119.4	
H7A—C7—H7B	109.5	C26—C21—C22	118.38 (16)	
C3—C7—H7C	109.5	C26—C21—C1	119.97 (15)	
H7A—C7—H7C	109.5	C22—C21—C1	121.63 (15)	
H7B—C7—H7C	109.5	C23—C22—C21	120.38 (16)	
C4—C8—H8A	109.5	C23—C22—H22	119.8	
C4—C8—H8B	109.5	C21—C22—H22	119.8	
H8A—C8—H8B	109.5	C24—C23—C22	120.70 (17)	
C4—C8—H8C	109.5	C24—C23—H23	119.6	
H8A—C8—H8C	109.5	C22—C23—H23	119.6	
H8B—C8—H8C	109.5	C23—C24—C25	119.19 (17)	
C10—C9—C14	118.23 (16)	C23—C24—H24	120.4	
C10—C9—C5	120.13 (15)	C25—C24—H24	120.4	
C14—C9—C5	121.62 (15)	C26—C25—C24	120.39 (17)	
C11—C10—C9	121.18 (17)	C26—C25—H25	119.8	
C11—C10—H10	119.4	C24—C25—H25	119.8	
C9—C10—H10	119.4	C25—C26—C21	120.93 (16)	
C10—C11—C12	119.97 (18)	C25—C26—H26	119.5	
C10—C11—H11	120.0	C21—C26—H26	119.5	
C12—C11—H11	120.0			
				
C5—S1—C1—C2	−29.19 (15)	C10—C11—C12—C13	0.3 (3)	
C5—S1—C1—C21	151.99 (12)	C11—C12—C13—C14	−0.1 (3)	
C21—C1—C2—C6	−12.4 (3)	C12—C13—C14—C9	0.6 (3)	
S1—C1—C2—C6	168.91 (13)	C10—C9—C14—C13	−1.3 (2)	
C21—C1—C2—C3	167.85 (15)	C5—C9—C14—C13	−179.74 (16)	
S1—C1—C2—C3	−10.8 (2)	C4—C3—C15—C16	−156.56 (15)	
C1—C2—C3—C4	54.54 (19)	C2—C3—C15—C16	−37.7 (2)	
C6—C2—C3—C4	−125.18 (16)	C7—C3—C15—C16	82.42 (18)	
C1—C2—C3—C7	178.12 (15)	C4—C3—C15—C20	29.1 (2)	
C6—C2—C3—C7	−1.6 (2)	C2—C3—C15—C20	147.93 (15)	
C1—C2—C3—C15	−65.93 (19)	C7—C3—C15—C20	−91.92 (18)	
C6—C2—C3—C15	114.35 (16)	C20—C15—C16—C17	−0.1 (3)	
C2—C3—C4—C5	−54.04 (19)	C3—C15—C16—C17	−174.63 (16)	
C7—C3—C4—C5	−177.52 (15)	C15—C16—C17—C18	−0.1 (3)	
C15—C3—C4—C5	65.65 (19)	C16—C17—C18—C19	0.2 (3)	
C2—C3—C4—C8	125.17 (16)	C17—C18—C19—C20	−0.1 (3)	
C7—C3—C4—C8	1.7 (2)	C18—C19—C20—C15	−0.1 (3)	
C15—C3—C4—C8	−115.13 (16)	C16—C15—C20—C19	0.2 (3)	
C8—C4—C5—C9	11.4 (3)	C3—C15—C20—C19	174.69 (15)	
C3—C4—C5—C9	−169.35 (15)	C2—C1—C21—C26	−49.4 (2)	
C8—C4—C5—S1	−169.24 (13)	S1—C1—C21—C26	129.31 (14)	
C3—C4—C5—S1	10.0 (2)	C2—C1—C21—C22	132.24 (18)	
C1—S1—C5—C4	29.71 (15)	S1—C1—C21—C22	−49.03 (19)	
C1—S1—C5—C9	−150.90 (12)	C26—C21—C22—C23	2.0 (2)	
C4—C5—C9—C10	50.0 (2)	C1—C21—C22—C23	−179.63 (16)	
S1—C5—C9—C10	−129.34 (15)	C21—C22—C23—C24	−1.1 (3)	
C4—C5—C9—C14	−131.58 (18)	C22—C23—C24—C25	0.2 (3)	
S1—C5—C9—C14	49.07 (19)	C23—C24—C25—C26	−0.2 (3)	
C14—C9—C10—C11	1.5 (3)	C24—C25—C26—C21	1.1 (3)	
C5—C9—C10—C11	179.99 (16)	C22—C21—C26—C25	−2.0 (3)	
C9—C10—C11—C12	−1.0 (3)	C1—C21—C26—C25	179.61 (16)
==== Refs
References
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Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Rahmani, H. & Pirelahi, H. (1997). Sulfur Lett.20, 159–163.
Rahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603.
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2009). publCIF In preparation.


{'source': 'PubMedDataset'}