4-Methyl-2,4,6-triphenyl-4H-thio-pyran.

The six-membered thio-pyran ring in the title compound, C(24)H(20)S, adopts a flattened boat conformation, with the S atom displaced by 0.273 (2) Å and the 3-methyl-ene C atom by 0.294 (3) Å from the plane of the other four sp(2)-hydridized C atoms. The methyl group on the methyl-ene carbon lies in a axial position with the phenyl equatorial.

Related literature

2,4,4,6-Tetraaryl- or 4-alkyl-2,4,6-triaryl-4H-thio­pyrans undergo UV-induced isomerization to form aryl-migrated 2H-thio­pyrans; for a discussion of the photoisomerization mechanism, see: Pirelahi et al. (2004 ▶); Pirelahi & Rahmani (1997 ▶). 4-Methyl-2,4,6-triphenyl-4H-thio­pyran does not react in the solid state, but in solution is converted to 4-methyl-2,3,6-triphenyl-2H-thio­pyran; see: Mori & Maeda (1991 ▶). For the synthesis, see: Suld & Price (1962 ▶).

Experimental

Crystal data

C24H20S

M = 340.46

Monoclinic,

a = 9.8737 (2) Å

b = 22.5282 (4) Å

c = 9.2288 (2) Å

β = 118.987 (1)°

V = 1795.67 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 115 K

0.35 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.917, T max = 0.982

8464 measured reflections

3883 independent reflections

3698 reflections with I > σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.072

S = 1.03

3883 reflections

227 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1825 Friedel pairs

Flack parameter: 0.00 (5)

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005911/sj2578sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005911/sj2578Isup2.hkl

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

C24H20S	F(000) = 720
Mr = 340.46	Dx = 1.259 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4067 reflections
a = 9.8737 (2) Å	θ = 2.5–28.0°
b = 22.5282 (4) Å	µ = 0.18 mm−1
c = 9.2288 (2) Å	T = 115 K
β = 118.987 (1)°	Prism, colorless
V = 1795.67 (6) Å3	0.35 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	3883 independent reflections
Radiation source: fine-focus sealed tube	3698 reflections with I > σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.917, Tmax = 0.982	k = −29→29
8464 measured reflections	l = −11→11

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.2571P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3883 reflections	Δρmax = 0.28 e Å−3
227 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 1825 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (5)

	x	y	z	Uiso*/Ueq
S1	0.49977 (4)	0.892322 (17)	0.49963 (4)	0.01993 (9)
C1	0.48277 (17)	0.87133 (6)	0.67575 (18)	0.0169 (3)
C2	0.37550 (18)	0.83350 (7)	0.66660 (19)	0.0197 (3)
H2	0.3740	0.8259	0.7671	0.024*
C3	0.25547 (17)	0.80107 (7)	0.51476 (19)	0.0187 (3)
C4	0.22225 (18)	0.83423 (7)	0.35828 (18)	0.0180 (3)
H4	0.1228	0.8283	0.2651	0.022*
C5	0.31709 (16)	0.87086 (6)	0.33675 (17)	0.0156 (3)
C6	0.3178 (2)	0.73921 (7)	0.5054 (2)	0.0252 (4)
H6A	0.3487	0.7178	0.6092	0.038*
H6B	0.4075	0.7437	0.4879	0.038*
H6C	0.2366	0.7168	0.4131	0.038*
C7	0.59735 (17)	0.90088 (7)	0.83149 (19)	0.0174 (3)
C8	0.55816 (18)	0.91435 (7)	0.95401 (19)	0.0210 (3)
H8	0.4585	0.9041	0.9379	0.025*
C9	0.66275 (19)	0.94253 (7)	1.0990 (2)	0.0241 (3)
H9	0.6341	0.9517	1.1810	0.029*
C10	0.8091 (2)	0.95738 (7)	1.1249 (2)	0.0236 (4)
H10	0.8809	0.9766	1.2245	0.028*
C11	0.84996 (18)	0.94407 (7)	1.0045 (2)	0.0237 (3)
H11	0.9503	0.9540	1.0221	0.028*
C12	0.74509 (18)	0.91643 (7)	0.85877 (19)	0.0207 (3)
H12	0.7738	0.9079	0.7765	0.025*
C13	0.10640 (17)	0.79667 (7)	0.52855 (18)	0.0183 (3)
C14	0.0894 (2)	0.75238 (8)	0.6233 (2)	0.0255 (3)
H14	0.1679	0.7231	0.6742	0.031*
C15	−0.0402 (2)	0.75009 (8)	0.6451 (2)	0.0294 (4)
H15	−0.0487	0.7198	0.7118	0.035*
C16	−0.1572 (2)	0.79169 (8)	0.5702 (2)	0.0284 (4)
H16	−0.2465	0.7899	0.5836	0.034*
C17	−0.14174 (19)	0.83609 (8)	0.47516 (19)	0.0257 (4)
H17	−0.2212	0.8649	0.4232	0.031*
C18	−0.01103 (19)	0.83879 (7)	0.45533 (18)	0.0222 (3)
H18	−0.0016	0.8698	0.3910	0.027*
C19	0.27339 (17)	0.89872 (7)	0.17441 (18)	0.0165 (3)
C20	0.18705 (18)	0.86626 (7)	0.02926 (18)	0.0191 (3)
H20	0.1658	0.8255	0.0359	0.023*
C21	0.13179 (19)	0.89302 (7)	−0.1250 (2)	0.0222 (3)
H21	0.0729	0.8706	−0.2230	0.027*
C22	0.16242 (19)	0.95233 (8)	−0.1358 (2)	0.0238 (4)
H22	0.1232	0.9708	−0.2412	0.029*
C23	0.25068 (19)	0.98482 (7)	0.0078 (2)	0.0242 (3)
H23	0.2722	1.0255	0.0005	0.029*
C24	0.30752 (18)	0.95805 (7)	0.16187 (18)	0.0192 (3)
H24	0.3700	0.9802	0.2594	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.01477 (16)	0.02749 (19)	0.01650 (17)	−0.00309 (16)	0.00676 (13)	−0.00013 (15)
C1	0.0159 (7)	0.0177 (7)	0.0151 (7)	0.0022 (6)	0.0060 (6)	0.0015 (6)
C2	0.0202 (7)	0.0213 (8)	0.0151 (7)	0.0008 (6)	0.0067 (6)	0.0030 (6)
C3	0.0183 (7)	0.0174 (7)	0.0179 (7)	−0.0021 (6)	0.0069 (6)	0.0014 (5)
C4	0.0177 (7)	0.0189 (7)	0.0146 (7)	−0.0021 (6)	0.0056 (6)	−0.0022 (6)
C5	0.0144 (7)	0.0154 (7)	0.0151 (7)	0.0006 (5)	0.0056 (6)	−0.0027 (5)
C6	0.0260 (9)	0.0207 (8)	0.0305 (9)	0.0010 (7)	0.0150 (7)	0.0016 (7)
C7	0.0144 (7)	0.0168 (7)	0.0159 (7)	0.0014 (6)	0.0032 (6)	0.0022 (5)
C8	0.0149 (7)	0.0237 (8)	0.0219 (8)	−0.0006 (6)	0.0070 (6)	−0.0016 (6)
C9	0.0233 (8)	0.0294 (8)	0.0197 (8)	0.0019 (7)	0.0105 (6)	−0.0021 (6)
C10	0.0203 (8)	0.0216 (8)	0.0206 (8)	−0.0008 (7)	0.0034 (6)	−0.0044 (6)
C11	0.0167 (7)	0.0261 (8)	0.0250 (8)	−0.0027 (6)	0.0075 (6)	−0.0014 (6)
C12	0.0201 (8)	0.0237 (8)	0.0190 (8)	−0.0008 (6)	0.0100 (6)	0.0002 (6)
C13	0.0172 (7)	0.0187 (7)	0.0153 (7)	−0.0034 (6)	0.0048 (6)	−0.0022 (5)
C14	0.0258 (8)	0.0221 (8)	0.0262 (8)	−0.0006 (7)	0.0107 (7)	0.0051 (6)
C15	0.0318 (9)	0.0282 (9)	0.0302 (9)	−0.0090 (7)	0.0167 (8)	0.0027 (7)
C16	0.0208 (8)	0.0378 (10)	0.0267 (9)	−0.0079 (7)	0.0115 (7)	−0.0065 (7)
C17	0.0198 (8)	0.0340 (9)	0.0182 (8)	0.0035 (7)	0.0050 (6)	−0.0011 (6)
C18	0.0246 (8)	0.0228 (8)	0.0166 (8)	−0.0005 (6)	0.0079 (7)	0.0008 (5)
C19	0.0140 (7)	0.0203 (7)	0.0165 (8)	0.0010 (6)	0.0084 (6)	−0.0008 (6)
C20	0.0188 (7)	0.0198 (7)	0.0202 (8)	−0.0007 (6)	0.0106 (6)	−0.0012 (6)
C21	0.0184 (8)	0.0318 (9)	0.0166 (8)	−0.0006 (6)	0.0086 (6)	−0.0019 (6)
C22	0.0195 (8)	0.0346 (9)	0.0197 (8)	0.0068 (7)	0.0113 (7)	0.0079 (7)
C23	0.0262 (8)	0.0216 (8)	0.0314 (9)	−0.0006 (7)	0.0191 (7)	0.0027 (6)
C24	0.0182 (7)	0.0222 (8)	0.0192 (8)	−0.0019 (6)	0.0106 (6)	−0.0027 (6)

S1—C5	1.7661 (14)	C11—H11	0.9500
S1—C1	1.7772 (15)	C12—H12	0.9500
C1—C2	1.330 (2)	C13—C14	1.390 (2)
C1—C7	1.488 (2)	C13—C18	1.393 (2)
C2—C3	1.514 (2)	C14—C15	1.390 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.514 (2)	C15—C16	1.384 (3)
C3—C13	1.541 (2)	C15—H15	0.9500
C3—C6	1.543 (2)	C16—C17	1.386 (3)
C4—C5	1.333 (2)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.390 (2)
C5—C19	1.483 (2)	C17—H17	0.9500
C6—H6A	0.9800	C18—H18	0.9500
C6—H6B	0.9800	C19—C20	1.396 (2)
C6—H6C	0.9800	C19—C24	1.397 (2)
C7—C8	1.394 (2)	C20—C21	1.391 (2)
C7—C12	1.399 (2)	C20—H20	0.9500
C8—C9	1.386 (2)	C21—C22	1.384 (2)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.387 (3)	C22—C23	1.390 (2)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.386 (2)	C23—C24	1.388 (2)
C10—H10	0.9500	C23—H23	0.9500
C11—C12	1.386 (2)	C24—H24	0.9500
C5—S1—C1	101.27 (7)	C11—C12—C7	120.71 (15)
C2—C1—C7	123.89 (14)	C11—C12—H12	119.6
C2—C1—S1	122.53 (12)	C7—C12—H12	119.6
C7—C1—S1	113.57 (11)	C14—C13—C18	117.92 (14)
C1—C2—C3	127.59 (14)	C14—C13—C3	120.65 (14)
C1—C2—H2	116.2	C18—C13—C3	121.32 (14)
C3—C2—H2	116.2	C15—C14—C13	121.22 (16)
C4—C3—C2	110.82 (12)	C15—C14—H14	119.4
C4—C3—C13	109.66 (12)	C13—C14—H14	119.4
C2—C3—C13	107.77 (13)	C16—C15—C14	120.43 (16)
C4—C3—C6	107.47 (13)	C16—C15—H15	119.8
C2—C3—C6	109.47 (13)	C14—C15—H15	119.8
C13—C3—C6	111.67 (12)	C15—C16—C17	118.94 (16)
C5—C4—C3	127.18 (13)	C15—C16—H16	120.5
C5—C4—H4	116.4	C17—C16—H16	120.5
C3—C4—H4	116.4	C16—C17—C18	120.56 (16)
C4—C5—C19	122.09 (13)	C16—C17—H17	119.7
C4—C5—S1	122.96 (11)	C18—C17—H17	119.7
C19—C5—S1	114.91 (11)	C17—C18—C13	120.92 (15)
C3—C6—H6A	109.5	C17—C18—H18	119.5
C3—C6—H6B	109.5	C13—C18—H18	119.5
H6A—C6—H6B	109.5	C20—C19—C24	118.78 (14)
C3—C6—H6C	109.5	C20—C19—C5	119.41 (13)
H6A—C6—H6C	109.5	C24—C19—C5	121.68 (13)
H6B—C6—H6C	109.5	C21—C20—C19	120.60 (15)
C8—C7—C12	118.32 (14)	C21—C20—H20	119.7
C8—C7—C1	120.06 (14)	C19—C20—H20	119.7
C12—C7—C1	121.62 (14)	C22—C21—C20	120.09 (15)
C9—C8—C7	120.86 (15)	C22—C21—H21	120.0
C9—C8—H8	119.6	C20—C21—H21	120.0
C7—C8—H8	119.6	C21—C22—C23	119.82 (15)
C8—C9—C10	120.22 (15)	C21—C22—H22	120.1
C8—C9—H9	119.9	C23—C22—H22	120.1
C10—C9—H9	119.9	C24—C23—C22	120.22 (15)
C11—C10—C9	119.59 (15)	C24—C23—H23	119.9
C11—C10—H10	120.2	C22—C23—H23	119.9
C9—C10—H10	120.2	C23—C24—C19	120.44 (14)
C12—C11—C10	120.30 (15)	C23—C24—H24	119.8
C12—C11—H11	119.9	C19—C24—H24	119.8
C10—C11—H11	119.9
C5—S1—C1—C2	17.61 (15)	C4—C3—C13—C14	157.18 (14)
C5—S1—C1—C7	−161.33 (11)	C2—C3—C13—C14	−82.11 (17)
C7—C1—C2—C3	−179.48 (15)	C6—C3—C13—C14	38.2 (2)
S1—C1—C2—C3	1.7 (2)	C4—C3—C13—C18	−26.78 (19)
C1—C2—C3—C4	−24.4 (2)	C2—C3—C13—C18	93.93 (16)
C1—C2—C3—C13	−144.35 (16)	C6—C3—C13—C18	−145.80 (14)
C1—C2—C3—C6	94.01 (19)	C18—C13—C14—C15	−0.2 (2)
C2—C3—C4—C5	26.5 (2)	C3—C13—C14—C15	175.99 (16)
C13—C3—C4—C5	145.30 (15)	C13—C14—C15—C16	1.0 (3)
C6—C3—C4—C5	−93.12 (19)	C14—C15—C16—C17	−0.9 (3)
C3—C4—C5—C19	177.18 (14)	C15—C16—C17—C18	0.0 (3)
C3—C4—C5—S1	−5.5 (2)	C16—C17—C18—C13	0.8 (2)
C1—S1—C5—C4	−15.81 (15)	C14—C13—C18—C17	−0.7 (2)
C1—S1—C5—C19	161.67 (11)	C3—C13—C18—C17	−176.85 (14)
C2—C1—C7—C8	−31.3 (2)	C4—C5—C19—C20	−37.1 (2)
S1—C1—C7—C8	147.59 (12)	S1—C5—C19—C20	145.37 (12)
C2—C1—C7—C12	149.37 (16)	C4—C5—C19—C24	138.58 (16)
S1—C1—C7—C12	−31.71 (19)	S1—C5—C19—C24	−38.92 (19)
C12—C7—C8—C9	0.1 (2)	C24—C19—C20—C21	−2.1 (2)
C1—C7—C8—C9	−179.21 (15)	C5—C19—C20—C21	173.78 (14)
C7—C8—C9—C10	−0.5 (3)	C19—C20—C21—C22	0.1 (2)
C8—C9—C10—C11	0.2 (3)	C20—C21—C22—C23	1.0 (2)
C9—C10—C11—C12	0.4 (3)	C21—C22—C23—C24	−0.3 (2)
C10—C11—C12—C7	−0.8 (3)	C22—C23—C24—C19	−1.7 (2)
C8—C7—C12—C11	0.5 (2)	C20—C19—C24—C23	2.8 (2)
C1—C7—C12—C11	179.82 (15)	C5—C19—C24—C23	−172.93 (14)