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

Rahmani, H.; Pirelahi, H.; Ng, S.W.

doi:10.1107/S1600536809005935

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o605

doi:10.1107/S1600536809005935

Open

access

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

Hossein Rahmani,^a Hooshang Pirelahi ^b and Seik Weng Ng ^c ^*

^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 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 ).

Experimental

Crystal data

C₂₅H₂₂OS
M_r = 370.49
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.04
8811 reflections
492 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Related literature top

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).

Experimental top

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.

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

Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C₂₄H₁₉BrS; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₂₅H₂₂OS	F(000) = 1568
M_r = 370.49	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	8811 independent reflections
Radiation source: fine-focus sealed tube	7499 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.919, T_max = 0.982	k = −9→9
35118 measured reflections	l = −46→46

Refinement top

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(F_o²) + (0.0584P)² + 0.3658P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
8811 reflections	Δρ_max = 0.27 e Å⁻³
492 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 4271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.39 (6)

Crystal data top

C₂₅H₂₂OS	V = 3896.0 (1) Å³
M_r = 370.49	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.1567 (2) Å	µ = 0.18 mm⁻¹
b = 7.6138 (1) Å	T = 115 K
c = 36.1457 (6) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	8811 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7499 reflections with I > 2˘I)
T_min = 0.919, T_max = 0.982	R_int = 0.048
35118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.27 e Å⁻³
S = 1.04	Δρ_min = −0.26 e Å⁻³
8811 reflections	Absolute structure: Flack (1983), 4271 Friedel pairs
492 parameters	Absolute structure parameter: 0.39 (6)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂OS
M_r	370.49
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	115
a, b, c (Å)	14.1567 (2), 7.6138 (1), 36.1457 (6)
V (Å³)	3896.0 (1)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.919, 0.982
No. of measured, independent and observed [I > 2˘I)] reflections	35118, 8811, 7499
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.04
No. of reflections	8811
No. of parameters	492
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26
Absolute structure	Flack (1983), 4271 Friedel pairs
Absolute structure parameter	0.39 (6)

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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suld, G. & Price, C. C. (1962). J. Am. Chem. Soc. 84, 2090–2094. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar