1,2-Bis(2-methyl-5-phenyl-3-thien­yl)benzene

Miao, W.-J.; Li, L.-H.; Lu, S.; Liu, G.; Fan, C.-B.

doi:10.1107/S1600536809045917

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3003

doi:10.1107/S1600536809045917

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1,2-Bis(2-methyl-5-phenyl-3-thienyl)benzene

Wen-Juan Miao,^a Liang-Hua Li,^b Shan Lu,^c Gang Liu ^a and Cong-Bin Fan ^a ^*

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China, ^bEast China Jiaotong University, School of Physical Education, Nanchang 330013, People's Republic of China, and ^cDepartment of Control Science and Engineering, Zhejiang University Zhejiang 310027, People's Republic of China
^*Correspondence e-mail: congbinfan@yahoo.com.cn

(Received 29 October 2009; accepted 2 November 2009; online 7 November 2009)

In the molecule of the title compound, C₂₈H₂₂S₂, the two thiophene rings are twisted with respect to the central benzene ring, making dihedral angles of 71.59 (12) and 50.71 (12)°. The two terminal benzene rings are oriented at dihedral angles of 37.59 (11) and 20.12 (11)° to their bonded thiophene rings.

Related literature

For the synthesis of the precursor, see: Irie et al. (2000 ). For applications of photochromic molecules, see: Irie et al. (2001 ). For diarylethenes with four different bridging units, see: Peters et al. (2003 ); Yamaguchi et al. (1997 ); Lucas et al. (1998 ); Chen & Zeng (2004 ). For ring-closure reactions, see: Ramamurthy & Venkatesan (1987 ). For a related structure, see: Pu et al. (2005 ).

Experimental

Crystal data

C₂₈H₂₂S₂
M_r = 422.58
Triclinic, $[P \overline 1]$
a = 10.0934 (12) Å
b = 10.0945 (12) Å
c = 11.9565 (15) Å
α = 83.803 (1)°
β = 67.769 (1)°
γ = 86.362 (1)°
V = 1120.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.40 × 0.24 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.907, T_max = 0.964
8610 measured reflections
4136 independent reflections
2920 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.02
4136 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045917/xu2660sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045917/xu2660Isup2.hkl

checkCIF report

Comment top

The design and synthesis of photochromic molecules is an area of intense research because of the widespread use in photonic device applications such as memory media and optical switching (Irie et al. 2001). To date, four kinds of diarylethenes with different bridge units have been reported, that is diarylethenes with a perfluorocyclopentene moiety (Peters et al. 2003), diarylethenes with maleic anhydride and maleimide moieties (Yamaguchi et al. 1997), diarylethenes with a cyclopentene moiety (Lucas et al. 1998), and diarylethenes with a 2,5-dihydrothiphene moiety (Chen & Zeng, 2004). One of our research goals is to develop a novel diarylethene derivative with the inexpensive benzene ring as bridge unit. In this paper, the ORTEP drawing of the single-crystal shows the title compound, i.e. 1,2-(2-methyl-5-phenyl-3-thienyl)benzene, packed in a parallel conformation which is very rare in other diarylethene system. The two independent planar thiophene ring systems have essentially identical geometries, and the dihedral angles between the central benzene-ring and these of the two thiophene rings, S1/C7—C10, and S2/ C18—C21 are 71.6 (4)° and 50.5 (7)°. The two thiophene groups are linked by the central benzene-ring, with both of them attached to the ethylene group via the 2-position. The distance between the two C atoms (C8···C19) is 4.06 (7) Å, which is short enough, theoretically, for the ring-closure reaction to take place in the crystalline phase (Ramamurthy & Venkatesan, 1987), but the crystals of the title compound is parallel thiophene-ring, so, the crystals cannot show photochromism.

Related literature top

For the synthesis of the precursor, see: Irie et al. (2000). For applications of photochromic molecules, see: Irie et al. (2001). For diarylethenes with four different bridging units, see: Peters et al. (2003); Yamaguchi et al. (1997); Lucas et al. (1998); Chen & Zeng (2004). For ring-closure reactions, see: Ramamurthy & Venkatesan (1987). For a related structure, see: Pu et al. (2005).

Experimental top

2-Methyl-5-phenylthiophen-3-yl-3-boronic acid, (2) in Fig 2, was obtained in the presence of compound 3-bromo-2-methyl-5-phenylthiophene, (1), (Irie et al., 2000) (2.53 g, 10.00 mmol) in a n-BuLi/hexane solution (2.50 mol/L, 12.00 mmol) and tri-n-butylborate (2.76 g, 12.00 mmol) at 195 K under a nitrogen atmosphere.

The title compound was prepared by adding compound (2) (0.88 g, 4.05 mmol) with Na₂CO₃ (2.00 mol/L, 60.00 mmol) to a stirred THF solution (50 ml) containing 1,2-dibromobenzene (0.48 g, 2.03 mmol) and Pd(PPh₃)₄ (0.27 g) at 293 K under a nitrogen atmosphere. After reflux for 16 h, the reaction mixture was extracted with ether, evaporated in vacuo and purified by column chromatography on SiO₂ using petroleum ether as the eluent to obtain the title compound. Single crystals of the title compound (1a) were grown from a chloroform solution by slow evaporation (m.p. 404.8–405.2 K).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view the atom-labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The preparation of the title compound.

1,2-Bis(2-methyl-5-phenyl-3-thienyl)benzene top

Crystal data top

C₂₈H₂₂S₂	Z = 2
M_r = 422.58	F(000) = 444
Triclinic, P1	D_x = 1.252 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0934 (12) Å	Cell parameters from 2224 reflections
b = 10.0945 (12) Å	θ = 2.6–22.8°
c = 11.9565 (15) Å	µ = 0.25 mm⁻¹
α = 83.803 (1)°	T = 296 K
β = 67.769 (1)°	Block, colourless
γ = 86.362 (1)°	0.40 × 0.24 × 0.15 mm
V = 1120.7 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4136 independent reflections
Radiation source: fine-focus sealed tube	2920 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.907, T_max = 0.964	k = −12→12
8610 measured reflections	l = −14→14

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0442P)² + 0.2296P] where P = (F_o² + 2F_c²)/3
4136 reflections	(Δ/σ)_max = 0.006
273 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₂₂S₂	γ = 86.362 (1)°
M_r = 422.58	V = 1120.7 (2) Å³
Triclinic, P1	Z = 2
a = 10.0934 (12) Å	Mo Kα radiation
b = 10.0945 (12) Å	µ = 0.25 mm⁻¹
c = 11.9565 (15) Å	T = 296 K
α = 83.803 (1)°	0.40 × 0.24 × 0.15 mm
β = 67.769 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4136 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2920 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.964	R_int = 0.021
8610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
4136 reflections	Δρ_min = −0.18 e Å⁻³
273 parameters

Special details top

Experimental. ¹HNMR (400 MHz, CDCl₃, TMS): δ 2.17 (s, 3H, -CH₃), 6.92 (s, 1H, thienyl-H), 7.20 (t, 1H, J=7.2 Hz,phenyl-H), 7.29 (t, 2H, J=7.4 Hz, phenyl-H), 7.42–7.44 (m, 4H, phenyl-H). ¹³C NMR (100 MHz, CDCl₃): δ 13.93, 125.51, 126.00, 127.00, 127.26, 128.76, 130.61, 134.60, 135.03, 136.09, 139.01, 139.45. IR (KBr, cm^-1): 756, 766, 849, 908, 946, 1001, 1029, 1073, 1153, 1184, 1227, 1377, 1462, 1479, 1505, 1596, 1629, 2854, 2924, 3014, 3053, 3254, 3443, 3529, 3676.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.8690 (3)	0.1761 (2)	0.33341 (19)	0.0593 (6)
C2	1.0178 (3)	0.1571 (2)	0.27841 (19)	0.0632 (6)
C3	1.0724 (3)	0.0279 (3)	0.2524 (2)	0.0837 (8)
H3	1.1708	0.0137	0.2160	0.100*
C4	0.9833 (5)	−0.0781 (3)	0.2798 (3)	0.1002 (11)
H4	1.0217	−0.1633	0.2634	0.120*
C5	0.8382 (5)	−0.0587 (3)	0.3312 (3)	0.0994 (11)
H5	0.7780	−0.1303	0.3478	0.119*
C6	0.7806 (3)	0.0679 (2)	0.3587 (2)	0.0803 (7)
H6	0.6819	0.0803	0.3944	0.096*
C7	0.8057 (2)	0.3112 (2)	0.36380 (18)	0.0534 (5)
C8	0.8183 (2)	0.3757 (2)	0.45372 (19)	0.0564 (5)
C9	0.6907 (2)	0.5132 (2)	0.33745 (18)	0.0517 (5)
C10	0.7318 (2)	0.3902 (2)	0.29899 (19)	0.0563 (5)
H10	0.7133	0.3602	0.2357	0.068*
C11	0.8878 (3)	0.3254 (3)	0.5415 (2)	0.0791 (7)
H11A	0.9079	0.2315	0.5370	0.119*
H11B	0.8245	0.3414	0.6223	0.119*
H11C	0.9755	0.3712	0.5214	0.119*
C12	0.6259 (2)	0.6253 (2)	0.28537 (19)	0.0535 (5)
C13	0.6640 (2)	0.6476 (2)	0.1601 (2)	0.0626 (6)
H13	0.7277	0.5890	0.1095	0.075*
C14	0.6079 (3)	0.7558 (3)	0.1111 (3)	0.0798 (7)
H14	0.6339	0.7703	0.0274	0.096*
C15	0.5132 (3)	0.8426 (3)	0.1857 (3)	0.0821 (8)
H15	0.4765	0.9163	0.1523	0.099*
C16	0.4735 (3)	0.8211 (3)	0.3071 (3)	0.0855 (8)
H16	0.4077	0.8791	0.3568	0.103*
C17	0.5293 (2)	0.7141 (2)	0.3585 (2)	0.0692 (6)
H17	0.5022	0.7013	0.4424	0.083*
C18	1.1146 (2)	0.2710 (2)	0.24104 (19)	0.0586 (6)
C19	1.2360 (3)	0.2804 (2)	0.2660 (2)	0.0659 (6)
C20	1.1898 (2)	0.4834 (2)	0.14581 (18)	0.0552 (5)
C21	1.0915 (2)	0.3879 (2)	0.17170 (18)	0.0554 (5)
H21	1.0148	0.3978	0.1462	0.066*
C22	1.2975 (3)	0.1831 (3)	0.3393 (3)	0.0933 (9)
H22A	1.2255	0.1213	0.3891	0.140*
H22B	1.3286	0.2306	0.3899	0.140*
H22C	1.3775	0.1354	0.2855	0.140*
C23	1.1947 (2)	0.6143 (2)	0.07776 (19)	0.0567 (5)
C24	1.3183 (3)	0.6851 (3)	0.0253 (3)	0.0844 (8)
H24	1.4020	0.6492	0.0327	0.101*
C25	1.3216 (4)	0.8071 (3)	−0.0376 (3)	0.1023 (10)
H25	1.4068	0.8529	−0.0719	0.123*
C26	1.2003 (4)	0.8618 (3)	−0.0504 (2)	0.0908 (9)
H26	1.2025	0.9452	−0.0926	0.109*
C27	1.0761 (4)	0.7937 (3)	−0.0010 (2)	0.0833 (8)
H27	0.9936	0.8298	−0.0108	0.100*
C28	1.0726 (3)	0.6706 (2)	0.0638 (2)	0.0664 (6)
H28	0.9871	0.6252	0.0984	0.080*
S1	0.74075 (6)	0.53246 (6)	0.45767 (5)	0.06329 (19)
S2	1.31728 (6)	0.43038 (7)	0.20603 (6)	0.0720 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0884 (17)	0.0445 (12)	0.0466 (12)	−0.0012 (11)	−0.0277 (12)	−0.0017 (9)
C2	0.0946 (18)	0.0483 (13)	0.0484 (12)	0.0156 (12)	−0.0301 (12)	−0.0083 (10)
C3	0.131 (2)	0.0569 (16)	0.0672 (16)	0.0299 (16)	−0.0444 (16)	−0.0162 (13)
C4	0.188 (4)	0.0461 (16)	0.081 (2)	0.021 (2)	−0.068 (2)	−0.0143 (14)
C5	0.184 (4)	0.0475 (16)	0.080 (2)	−0.023 (2)	−0.066 (2)	0.0057 (14)
C6	0.118 (2)	0.0591 (16)	0.0649 (16)	−0.0183 (15)	−0.0345 (15)	0.0021 (12)
C7	0.0589 (13)	0.0478 (12)	0.0491 (12)	−0.0035 (10)	−0.0159 (10)	−0.0009 (9)
C8	0.0610 (13)	0.0558 (13)	0.0527 (12)	0.0030 (10)	−0.0217 (10)	−0.0075 (10)
C9	0.0501 (11)	0.0513 (12)	0.0501 (12)	−0.0015 (9)	−0.0141 (9)	−0.0067 (10)
C10	0.0634 (13)	0.0543 (13)	0.0525 (12)	−0.0050 (10)	−0.0219 (11)	−0.0085 (10)
C11	0.0984 (19)	0.0797 (17)	0.0720 (16)	0.0163 (15)	−0.0466 (15)	−0.0164 (13)
C12	0.0456 (11)	0.0528 (12)	0.0599 (13)	−0.0046 (9)	−0.0166 (10)	−0.0054 (10)
C13	0.0586 (13)	0.0684 (15)	0.0603 (14)	0.0055 (11)	−0.0224 (11)	−0.0072 (11)
C14	0.0778 (17)	0.0892 (19)	0.0730 (17)	−0.0020 (15)	−0.0326 (14)	0.0068 (15)
C15	0.0871 (19)	0.0654 (16)	0.090 (2)	0.0093 (14)	−0.0358 (16)	0.0098 (15)
C16	0.0881 (19)	0.0652 (17)	0.091 (2)	0.0222 (14)	−0.0230 (16)	−0.0115 (15)
C17	0.0703 (15)	0.0608 (15)	0.0668 (15)	0.0054 (12)	−0.0164 (12)	−0.0032 (12)
C18	0.0679 (14)	0.0547 (13)	0.0486 (12)	0.0163 (11)	−0.0177 (11)	−0.0113 (10)
C19	0.0751 (15)	0.0671 (15)	0.0543 (13)	0.0249 (12)	−0.0247 (12)	−0.0144 (11)
C20	0.0573 (13)	0.0598 (13)	0.0472 (12)	0.0106 (11)	−0.0181 (10)	−0.0116 (10)
C21	0.0596 (13)	0.0561 (13)	0.0490 (12)	0.0106 (11)	−0.0195 (10)	−0.0081 (10)
C22	0.115 (2)	0.0891 (19)	0.0877 (19)	0.0411 (17)	−0.0562 (18)	−0.0157 (15)
C23	0.0633 (14)	0.0582 (13)	0.0478 (12)	0.0019 (11)	−0.0185 (11)	−0.0124 (10)
C24	0.0715 (17)	0.0837 (19)	0.092 (2)	−0.0104 (14)	−0.0261 (15)	0.0034 (16)
C25	0.107 (2)	0.086 (2)	0.100 (2)	−0.0264 (19)	−0.025 (2)	0.0139 (18)
C26	0.149 (3)	0.0630 (17)	0.0606 (16)	−0.011 (2)	−0.0398 (19)	0.0025 (13)
C27	0.114 (2)	0.0696 (17)	0.0803 (18)	0.0118 (17)	−0.0540 (18)	−0.0101 (14)
C28	0.0756 (16)	0.0585 (14)	0.0708 (15)	0.0037 (12)	−0.0347 (13)	−0.0059 (12)
S1	0.0722 (4)	0.0584 (4)	0.0657 (4)	0.0089 (3)	−0.0312 (3)	−0.0185 (3)
S2	0.0651 (4)	0.0846 (5)	0.0711 (4)	0.0146 (3)	−0.0318 (3)	−0.0135 (3)

Geometric parameters (Å, º) top

C1—C6	1.389 (3)	C14—H14	0.9300
C1—C2	1.403 (3)	C15—C16	1.348 (4)
C1—C7	1.490 (3)	C15—H15	0.9300
C2—C3	1.403 (3)	C16—C17	1.380 (3)
C2—C18	1.475 (3)	C16—H16	0.9300
C3—C4	1.373 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.377 (3)
C4—C5	1.367 (4)	C18—C21	1.427 (3)
C4—H4	0.9300	C19—C22	1.505 (3)
C5—C6	1.390 (4)	C19—S2	1.720 (3)
C5—H5	0.9300	C20—C21	1.354 (3)
C6—H6	0.9300	C20—C23	1.468 (3)
C7—C8	1.364 (3)	C20—S2	1.730 (2)
C7—C10	1.422 (3)	C21—H21	0.9300
C8—C11	1.500 (3)	C22—H22A	0.9600
C8—S1	1.718 (2)	C22—H22B	0.9600
C9—C10	1.356 (3)	C22—H22C	0.9600
C9—C12	1.469 (3)	C23—C24	1.373 (3)
C9—S1	1.727 (2)	C23—C28	1.384 (3)
C10—H10	0.9300	C24—C25	1.367 (4)
C11—H11A	0.9600	C24—H24	0.9300
C11—H11B	0.9600	C25—C26	1.366 (4)
C11—H11C	0.9600	C25—H25	0.9300
C12—C17	1.390 (3)	C26—C27	1.362 (4)
C12—C13	1.394 (3)	C26—H26	0.9300
C13—C14	1.375 (3)	C27—C28	1.388 (3)
C13—H13	0.9300	C27—H27	0.9300
C14—C15	1.376 (4)	C28—H28	0.9300

C6—C1—C2	119.4 (2)	C16—C15—H15	119.9
C6—C1—C7	120.1 (2)	C14—C15—H15	119.9
C2—C1—C7	120.50 (19)	C15—C16—C17	120.8 (2)
C1—C2—C3	118.4 (2)	C15—C16—H16	119.6
C1—C2—C18	121.09 (18)	C17—C16—H16	119.6
C3—C2—C18	120.4 (2)	C16—C17—C12	120.1 (2)
C4—C3—C2	121.2 (3)	C16—C17—H17	119.9
C4—C3—H3	119.4	C12—C17—H17	119.9
C2—C3—H3	119.4	C19—C18—C21	111.2 (2)
C5—C4—C3	120.2 (3)	C19—C18—C2	126.3 (2)
C5—C4—H4	119.9	C21—C18—C2	122.4 (2)
C3—C4—H4	119.9	C18—C19—C22	129.2 (2)
C4—C5—C6	120.1 (3)	C18—C19—S2	111.29 (17)
C4—C5—H5	120.0	C22—C19—S2	119.5 (2)
C6—C5—H5	120.0	C21—C20—C23	127.9 (2)
C1—C6—C5	120.7 (3)	C21—C20—S2	109.85 (16)
C1—C6—H6	119.7	C23—C20—S2	122.28 (18)
C5—C6—H6	119.7	C20—C21—C18	114.9 (2)
C8—C7—C10	112.25 (19)	C20—C21—H21	122.5
C8—C7—C1	123.57 (19)	C18—C21—H21	122.5
C10—C7—C1	124.11 (19)	C19—C22—H22A	109.5
C7—C8—C11	128.1 (2)	C19—C22—H22B	109.5
C7—C8—S1	110.85 (16)	H22A—C22—H22B	109.5
C11—C8—S1	121.04 (16)	C19—C22—H22C	109.5
C10—C9—C12	129.5 (2)	H22A—C22—H22C	109.5
C10—C9—S1	109.77 (16)	H22B—C22—H22C	109.5
C12—C9—S1	120.54 (15)	C24—C23—C28	117.4 (2)
C9—C10—C7	114.25 (19)	C24—C23—C20	122.3 (2)
C9—C10—H10	122.9	C28—C23—C20	120.3 (2)
C7—C10—H10	122.9	C25—C24—C23	121.8 (3)
C8—C11—H11A	109.5	C25—C24—H24	119.1
C8—C11—H11B	109.5	C23—C24—H24	119.1
H11A—C11—H11B	109.5	C26—C25—C24	120.3 (3)
C8—C11—H11C	109.5	C26—C25—H25	119.9
H11A—C11—H11C	109.5	C24—C25—H25	119.9
H11B—C11—H11C	109.5	C27—C26—C25	119.6 (3)
C17—C12—C13	118.3 (2)	C27—C26—H26	120.2
C17—C12—C9	121.3 (2)	C25—C26—H26	120.2
C13—C12—C9	120.39 (19)	C26—C27—C28	120.0 (3)
C14—C13—C12	120.4 (2)	C26—C27—H27	120.0
C14—C13—H13	119.8	C28—C27—H27	120.0
C12—C13—H13	119.8	C23—C28—C27	120.9 (2)
C13—C14—C15	120.0 (2)	C23—C28—H28	119.6
C13—C14—H14	120.0	C27—C28—H28	119.6
C15—C14—H14	120.0	C8—S1—C9	92.87 (10)
C16—C15—C14	120.3 (2)	C19—S2—C20	92.73 (11)

C6—C1—C2—C3	−1.0 (3)	C9—C12—C17—C16	177.9 (2)
C7—C1—C2—C3	179.48 (19)	C1—C2—C18—C19	131.3 (2)
C6—C1—C2—C18	175.0 (2)	C3—C2—C18—C19	−52.8 (3)
C7—C1—C2—C18	−4.6 (3)	C1—C2—C18—C21	−48.9 (3)
C1—C2—C3—C4	0.0 (3)	C3—C2—C18—C21	126.9 (2)
C18—C2—C3—C4	−176.0 (2)	C21—C18—C19—C22	177.8 (2)
C2—C3—C4—C5	1.3 (4)	C2—C18—C19—C22	−2.4 (4)
C3—C4—C5—C6	−1.6 (4)	C21—C18—C19—S2	0.5 (2)
C2—C1—C6—C5	0.7 (3)	C2—C18—C19—S2	−179.78 (16)
C7—C1—C6—C5	−179.8 (2)	C23—C20—C21—C18	−179.37 (19)
C4—C5—C6—C1	0.6 (4)	S2—C20—C21—C18	0.6 (2)
C6—C1—C7—C8	110.3 (3)	C19—C18—C21—C20	−0.7 (3)
C2—C1—C7—C8	−70.1 (3)	C2—C18—C21—C20	179.54 (18)
C6—C1—C7—C10	−73.0 (3)	C21—C20—C23—C24	−159.5 (2)
C2—C1—C7—C10	106.6 (2)	S2—C20—C23—C24	20.6 (3)
C10—C7—C8—C11	179.6 (2)	C21—C20—C23—C28	20.2 (3)
C1—C7—C8—C11	−3.3 (4)	S2—C20—C23—C28	−159.79 (17)
C10—C7—C8—S1	−0.4 (2)	C28—C23—C24—C25	0.5 (4)
C1—C7—C8—S1	176.70 (17)	C20—C23—C24—C25	−179.8 (3)
C12—C9—C10—C7	173.27 (19)	C23—C24—C25—C26	−0.3 (5)
S1—C9—C10—C7	−1.0 (2)	C24—C25—C26—C27	−0.6 (5)
C8—C7—C10—C9	0.9 (3)	C25—C26—C27—C28	1.2 (4)
C1—C7—C10—C9	−176.1 (2)	C24—C23—C28—C27	0.1 (3)
C10—C9—C12—C17	147.8 (2)	C20—C23—C28—C27	−179.5 (2)
S1—C9—C12—C17	−38.5 (3)	C26—C27—C28—C23	−1.0 (4)
C10—C9—C12—C13	−34.4 (3)	C7—C8—S1—C9	−0.15 (17)
S1—C9—C12—C13	139.39 (18)	C11—C8—S1—C9	179.88 (19)
C17—C12—C13—C14	0.7 (3)	C10—C9—S1—C8	0.66 (17)
C9—C12—C13—C14	−177.3 (2)	C12—C9—S1—C8	−174.21 (17)
C12—C13—C14—C15	−0.2 (4)	C18—C19—S2—C20	−0.12 (17)
C13—C14—C15—C16	−0.9 (4)	C22—C19—S2—C20	−177.74 (19)
C14—C15—C16—C17	1.6 (4)	C21—C20—S2—C19	−0.27 (16)
C15—C16—C17—C12	−1.1 (4)	C23—C20—S2—C19	179.69 (17)
C13—C12—C17—C16	0.0 (3)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂S₂
M_r	422.58
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.0934 (12), 10.0945 (12), 11.9565 (15)
α, β, γ (°)	83.803 (1), 67.769 (1), 86.362 (1)
V (Å³)	1120.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.907, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	8610, 4136, 2920
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.02
No. of reflections	4136
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi (GJJ09306, GJJ09302) and the Youth Science Fund of the Education Office of Jiangxi (GJJ09572).

References

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