1,2-Bis(2-methyl-5-phenyl-3-thien-yl)benzene.

In the mol-ecule of the title compound, C(28)H(22)S(2), the two thio-phene 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 thio-phene 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 = 422.58

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.02

4136 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −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.

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

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

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

C28H22S2	Z = 2
Mr = 422.58	F(000) = 444
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0442P)2 + 0.2296P] where P = (Fo2 + 2Fc2)/3
4136 reflections	(Δ/σ)max = 0.006
273 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)