2,5-Bis(9H-carbazol-9-yl)thio­phene

Jiang, X.-L.; Huang, E.-F.; Rao, G.-W.

doi:10.1107/S1600536808039767

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2502

doi:10.1107/S1600536808039767

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2,5-Bis(9H-carbazol-9-yl)thiophene

Xu-Liang Jiang,^a Er-Fang Huang ^a and Guo-Wu Rao ^b ^*

^aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China, and ^bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, People's Republic of China
^*Correspondence e-mail: rgw@zjut.edu.cn

(Received 21 November 2008; accepted 25 November 2008; online 29 November 2008)

The molecules of the title compound, C₂₈H₁₈N₂S, are built up from two triply-fused rings and one five-membered ring, with dihedral angles of 66.12 (8) and 70.96 (7)° between the central thiophene ring and the two triply-fused rings.

Related literature

For dicarbazolyl derivatives as potential blue-emitting hole-transporting materials, see: Wu et al. (2000 , 2001 ).

Experimental

Crystal data

C₂₈H₁₈N₂S
M_r = 414.50
Orthorhombic, P b c a
a = 7.8760 (16) Å
b = 16.098 (3) Å
c = 33.986 (7) Å
V = 4309.1 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS-IV diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.963, T_max = 0.977
12051 measured reflections
3931 independent reflections
3230 reflections with I > 2σ(I)
R_int = 0.091
3 standard reflections frequency: 60 min intensity decay: 0.3%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.152
S = 1.13
3931 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: R-AXIS (Rigaku, 1996 ); cell refinement: R-AXIS; data reduction: R-AXIS program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039767/dn2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039767/dn2409Isup2.hkl

checkCIF report

Comment top

Due to the great potential in flat-panel displays, organic light-emitting diodes (OLEDs) have been received continuous attention for years. Dicarbazolyl derivatives bridged by various aromatic spacers could emit blue light in solution, and could be used as excellent blue-emitting hole-transporting materials (Wu et al., 2000, 2001). As dicarbazolyl derivatives are of great importance in electroluminescent devices, we have undertaken the crystal structure determination of the title compound.

The molecular (I) is built up from two three-fused rings and one five-membered ring. (Fig. 1). The three fused rings are coplanar within 0.0306 (27) and 0.0288 (26) Å, respectively. The five-membered ring is coplanar within 0.0027 (18) Å. The dihedral angles between the thiophene ring and the three-fused rings are 66.12 (8) and 70.96 (7)°, respectively.

Related literature top

For dicarbazolyl derivatives as potential blue-emitting hole-transporting materials, see: Wu et al. (2000, 2001).

Experimental top

2,5-dibromothiophene (4.84 g, 20.0 mmol), 9H-carbazole (6.69 g, 40.0 mmol), sodium tert-butoxide (4.61 g, 48.0 mmol), Pd(OAc)₂ (90 mg, 0.4 mmol), P(t—Bu)₃ (0.4 ml, 1.6 mmol, 0.81 M in o-xylene) and dry o-xylene (60 ml) were placed in a round-bottomed flask, and the solution was stirred at reflux for 72 h. After cooling, 2 ml of water was added, and the solution was then pumped dry, and the residue was extracted with dichloromethane/water, filtered and dried over magnesium sulfate. The pure product (m. p. 250–252°C) was obtained through silica gel chromatography (eluant: petroleum ether). A solution of the compound in n-hexane/dichloromethane (v/v=5/1) was concentrated gradually at room temperature to afford colorless prisms.

Computing details top

Data collection: R-AXIS (Rigaku, 1996); cell refinement: R-AXIS (Rigaku, 1996); data reduction: R-AXIS (Rigaku, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of (I), showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level.

2,5-Bis(9H-carbazol-9-yl)thiophene top

Crystal data top

C₂₈H₁₈N₂S	F(000) = 1728
M_r = 414.50	D_x = 1.278 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 398 reflections
a = 7.8760 (16) Å	θ = 2–25.1°
b = 16.098 (3) Å	µ = 0.17 mm⁻¹
c = 33.986 (7) Å	T = 298 K
V = 4309.1 (15) Å³	Prismatic, colorless
Z = 8	0.20 × 0.18 × 0.16 mm

Data collection top

Rigaku R-AXIS-IV diffractometer	3230 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.091
Graphite monochromator	θ_max = 25.5°, θ_min = 1.2°
Oscillation frames scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→0
T_min = 0.963, T_max = 0.977	l = −41→41
12051 measured reflections	3 standard reflections every 60 min
3931 independent reflections	intensity decay: 0.3%

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0561P)² + 1.4309P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.005
3931 reflections	Δρ_max = 0.22 e Å⁻³
281 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (8)

Crystal data top

C₂₈H₁₈N₂S	V = 4309.1 (15) Å³
M_r = 414.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.8760 (16) Å	µ = 0.17 mm⁻¹
b = 16.098 (3) Å	T = 298 K
c = 33.986 (7) Å	0.20 × 0.18 × 0.16 mm

Data collection top

Rigaku R-AXIS-IV diffractometer	3230 reflections with I > 2σ(I)
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	R_int = 0.091
T_min = 0.963, T_max = 0.977	3 standard reflections every 60 min
12051 measured reflections	intensity decay: 0.3%
3931 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.13	Δρ_max = 0.22 e Å⁻³
3931 reflections	Δρ_min = −0.24 e Å⁻³
281 parameters

Special details top

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
S1	0.42510 (9)	0.38837 (4)	0.134571 (19)	0.0563 (2)
N1	0.1144 (3)	0.45028 (13)	0.15532 (6)	0.0547 (5)
N2	0.5972 (3)	0.31480 (13)	0.07385 (6)	0.0528 (5)
C1	0.1385 (3)	0.52907 (16)	0.17188 (8)	0.0549 (6)
C2	0.2565 (4)	0.5891 (2)	0.16243 (11)	0.0778 (9)
H2A	0.3375	0.5804	0.1429	0.093*
C3	0.2491 (5)	0.6626 (2)	0.18321 (12)	0.0908 (11)
H3A	0.3271	0.7043	0.1776	0.109*
C4	0.1297 (6)	0.6760 (2)	0.21206 (12)	0.0935 (12)
H4A	0.1285	0.7264	0.2254	0.112*
C5	0.0140 (5)	0.6171 (2)	0.22129 (9)	0.0756 (9)
H5A	−0.0666	0.6270	0.2407	0.091*
C6	0.0166 (3)	0.54065 (17)	0.20123 (7)	0.0552 (6)
C7	−0.0844 (3)	0.46647 (17)	0.20323 (7)	0.0536 (6)
C8	−0.2183 (4)	0.4410 (2)	0.22699 (8)	0.0706 (8)
H8A	−0.2620	0.4764	0.2461	0.085*
C9	−0.2852 (4)	0.3632 (2)	0.22198 (9)	0.0797 (9)
H9A	−0.3736	0.3454	0.2381	0.096*
C10	−0.2226 (4)	0.3107 (2)	0.19319 (9)	0.0717 (8)
H10A	−0.2705	0.2582	0.1902	0.086*
C11	−0.0908 (4)	0.33396 (17)	0.16874 (8)	0.0595 (7)
H11A	−0.0508	0.2988	0.1491	0.071*
C12	−0.0208 (3)	0.41184 (15)	0.17466 (7)	0.0484 (6)
C13	0.2153 (3)	0.41352 (16)	0.12579 (7)	0.0518 (6)
C14	0.1618 (4)	0.3893 (2)	0.08962 (8)	0.0721 (9)
H14A	0.0525	0.3978	0.0801	0.087*
C15	0.2932 (4)	0.3495 (2)	0.06807 (8)	0.0737 (9)
H15A	0.2791	0.3287	0.0427	0.088*
C16	0.4400 (3)	0.34488 (16)	0.08817 (7)	0.0517 (6)
C17	0.6898 (3)	0.35122 (15)	0.04319 (7)	0.0484 (6)
C18	0.6625 (4)	0.42622 (17)	0.02422 (8)	0.0626 (7)
H18A	0.5728	0.4608	0.0312	0.075*
C19	0.7746 (4)	0.44742 (19)	−0.00553 (9)	0.0710 (8)
H19A	0.7599	0.4975	−0.0187	0.085*
C20	0.9084 (4)	0.3958 (2)	−0.01618 (9)	0.0715 (8)
H20A	0.9806	0.4114	−0.0365	0.086*
C21	0.9348 (3)	0.32234 (19)	0.00301 (8)	0.0625 (7)
H21A	1.0244	0.2879	−0.0042	0.075*
C22	0.8259 (3)	0.29954 (16)	0.03348 (7)	0.0511 (6)
C23	0.8173 (3)	0.22830 (16)	0.05942 (7)	0.0520 (6)
C24	0.9152 (4)	0.1575 (2)	0.06395 (9)	0.0711 (8)
H24A	1.0113	0.1493	0.0486	0.085*
C25	0.8682 (5)	0.0997 (2)	0.09146 (10)	0.0838 (10)
H25A	0.9330	0.0518	0.0945	0.101*
C26	0.7258 (5)	0.1112 (2)	0.11483 (9)	0.0814 (9)
H26A	0.6974	0.0710	0.1333	0.098*
C27	0.6255 (4)	0.18089 (18)	0.11129 (8)	0.0673 (8)
H27A	0.5297	0.1884	0.1269	0.081*
C28	0.6737 (3)	0.23931 (16)	0.08351 (7)	0.0518 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0515 (4)	0.0642 (4)	0.0531 (4)	0.0098 (3)	0.0019 (3)	−0.0067 (3)
N1	0.0541 (12)	0.0513 (12)	0.0586 (12)	0.0035 (10)	0.0152 (10)	−0.0071 (10)
N2	0.0474 (11)	0.0548 (12)	0.0564 (12)	0.0049 (10)	0.0114 (9)	−0.0021 (10)
C1	0.0545 (15)	0.0498 (15)	0.0604 (15)	0.0060 (12)	−0.0023 (12)	−0.0032 (12)
C2	0.068 (2)	0.0620 (19)	0.103 (2)	−0.0023 (16)	0.0013 (17)	−0.0029 (17)
C3	0.083 (3)	0.0552 (19)	0.134 (3)	−0.0055 (17)	−0.020 (2)	−0.005 (2)
C4	0.098 (3)	0.064 (2)	0.119 (3)	0.017 (2)	−0.036 (2)	−0.027 (2)
C5	0.080 (2)	0.073 (2)	0.074 (2)	0.0289 (18)	−0.0145 (16)	−0.0226 (16)
C6	0.0568 (15)	0.0560 (15)	0.0529 (14)	0.0156 (13)	−0.0088 (12)	−0.0073 (12)
C7	0.0528 (15)	0.0630 (16)	0.0451 (13)	0.0201 (13)	−0.0010 (11)	−0.0001 (11)
C8	0.0618 (18)	0.096 (2)	0.0544 (16)	0.0204 (17)	0.0139 (13)	−0.0022 (15)
C9	0.0617 (19)	0.106 (3)	0.071 (2)	0.0008 (19)	0.0196 (15)	0.0159 (19)
C10	0.0631 (18)	0.0702 (19)	0.082 (2)	−0.0038 (15)	0.0063 (15)	0.0152 (16)
C11	0.0583 (16)	0.0564 (16)	0.0638 (16)	0.0087 (13)	0.0070 (12)	−0.0001 (12)
C12	0.0459 (13)	0.0514 (14)	0.0481 (13)	0.0100 (11)	0.0048 (10)	0.0005 (11)
C13	0.0488 (14)	0.0532 (14)	0.0533 (14)	0.0030 (12)	0.0089 (11)	−0.0029 (11)
C14	0.0489 (15)	0.107 (2)	0.0605 (17)	0.0097 (16)	0.0022 (12)	−0.0179 (16)
C15	0.0494 (16)	0.112 (3)	0.0594 (17)	0.0088 (17)	0.0050 (13)	−0.0236 (17)
C16	0.0455 (14)	0.0553 (15)	0.0542 (14)	0.0021 (11)	0.0094 (11)	−0.0036 (11)
C17	0.0457 (13)	0.0510 (14)	0.0486 (13)	−0.0043 (11)	0.0042 (10)	−0.0095 (11)
C18	0.0665 (18)	0.0560 (16)	0.0652 (17)	−0.0013 (14)	0.0058 (13)	−0.0043 (13)
C19	0.077 (2)	0.0639 (18)	0.0724 (18)	−0.0182 (16)	0.0076 (16)	0.0036 (15)
C20	0.0661 (19)	0.084 (2)	0.0645 (17)	−0.0250 (17)	0.0170 (14)	−0.0064 (16)
C21	0.0470 (15)	0.0776 (19)	0.0629 (16)	−0.0076 (14)	0.0120 (12)	−0.0205 (15)
C22	0.0447 (13)	0.0586 (15)	0.0501 (13)	−0.0056 (11)	0.0025 (10)	−0.0168 (12)
C23	0.0495 (14)	0.0572 (15)	0.0494 (13)	0.0041 (12)	−0.0014 (11)	−0.0134 (12)
C24	0.0687 (19)	0.077 (2)	0.0676 (18)	0.0213 (16)	−0.0006 (14)	−0.0157 (16)
C25	0.105 (3)	0.071 (2)	0.076 (2)	0.0317 (19)	−0.0114 (19)	−0.0026 (17)
C26	0.109 (3)	0.069 (2)	0.0669 (19)	0.0126 (19)	0.0003 (19)	0.0067 (16)
C27	0.0769 (19)	0.0672 (18)	0.0579 (16)	0.0052 (15)	0.0090 (14)	0.0010 (14)
C28	0.0528 (14)	0.0536 (15)	0.0490 (14)	0.0038 (12)	0.0012 (11)	−0.0067 (11)

Geometric parameters (Å, º) top

S1—C13	1.727 (3)	C11—H11A	0.9300
S1—C16	1.729 (3)	C13—C14	1.356 (4)
N1—C12	1.396 (3)	C14—C15	1.421 (4)
N1—C1	1.401 (3)	C14—H14A	0.9300
N1—C13	1.410 (3)	C15—C16	1.345 (4)
N2—C28	1.396 (3)	C15—H15A	0.9300
N2—C17	1.401 (3)	C17—C18	1.385 (4)
N2—C16	1.415 (3)	C17—C22	1.396 (3)
C1—C2	1.379 (4)	C18—C19	1.385 (4)
C1—C6	1.397 (4)	C18—H18A	0.9300
C2—C3	1.379 (5)	C19—C20	1.390 (4)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.376 (6)	C20—C21	1.366 (4)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.352 (5)	C21—C22	1.394 (4)
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.407 (4)	C22—C23	1.448 (4)
C5—H5A	0.9300	C23—C24	1.385 (4)
C6—C7	1.437 (4)	C23—C28	1.408 (3)
C7—C8	1.390 (4)	C24—C25	1.370 (5)
C7—C12	1.403 (3)	C24—H24A	0.9300
C8—C9	1.370 (5)	C25—C26	1.387 (5)
C8—H8A	0.9300	C25—H25A	0.9300
C9—C10	1.384 (4)	C26—C27	1.377 (4)
C9—H9A	0.9300	C26—H26A	0.9300
C10—C11	1.381 (4)	C27—C28	1.386 (4)
C10—H10A	0.9300	C27—H27A	0.9300
C11—C12	1.384 (4)

C13—S1—C16	90.13 (12)	C13—C14—C15	111.8 (3)
C12—N1—C1	108.4 (2)	C13—C14—H14A	124.1
C12—N1—C13	125.4 (2)	C15—C14—H14A	124.1
C1—N1—C13	126.1 (2)	C16—C15—C14	112.9 (3)
C28—N2—C17	108.34 (19)	C16—C15—H15A	123.6
C28—N2—C16	126.5 (2)	C14—C15—H15A	123.6
C17—N2—C16	124.6 (2)	C15—C16—N2	126.6 (2)
C2—C1—C6	122.4 (3)	C15—C16—S1	112.49 (19)
C2—C1—N1	129.2 (3)	N2—C16—S1	120.76 (18)
C6—C1—N1	108.3 (2)	C18—C17—C22	121.9 (2)
C3—C2—C1	117.0 (3)	C18—C17—N2	129.1 (2)
C3—C2—H2A	121.5	C22—C17—N2	109.0 (2)
C1—C2—H2A	121.5	C19—C18—C17	117.1 (3)
C4—C3—C2	121.9 (4)	C19—C18—H18A	121.5
C4—C3—H3A	119.0	C17—C18—H18A	121.5
C2—C3—H3A	119.0	C18—C19—C20	121.7 (3)
C5—C4—C3	121.1 (3)	C18—C19—H19A	119.1
C5—C4—H4A	119.5	C20—C19—H19A	119.1
C3—C4—H4A	119.5	C21—C20—C19	120.5 (3)
C4—C5—C6	119.4 (3)	C21—C20—H20A	119.7
C4—C5—H5A	120.3	C19—C20—H20A	119.7
C6—C5—H5A	120.3	C20—C21—C22	119.3 (3)
C1—C6—C5	118.2 (3)	C20—C21—H21A	120.4
C1—C6—C7	107.7 (2)	C22—C21—H21A	120.4
C5—C6—C7	134.1 (3)	C21—C22—C17	119.4 (3)
C8—C7—C12	119.2 (3)	C21—C22—C23	133.6 (2)
C8—C7—C6	133.8 (3)	C17—C22—C23	107.0 (2)
C12—C7—C6	106.9 (2)	C24—C23—C28	119.1 (3)
C9—C8—C7	119.3 (3)	C24—C23—C22	133.9 (2)
C9—C8—H8A	120.4	C28—C23—C22	107.0 (2)
C7—C8—H8A	120.4	C25—C24—C23	119.0 (3)
C8—C9—C10	120.6 (3)	C25—C24—H24A	120.5
C8—C9—H9A	119.7	C23—C24—H24A	120.5
C10—C9—H9A	119.7	C24—C25—C26	121.2 (3)
C11—C10—C9	121.8 (3)	C24—C25—H25A	119.4
C11—C10—H10A	119.1	C26—C25—H25A	119.4
C9—C10—H10A	119.1	C27—C26—C25	121.5 (3)
C10—C11—C12	117.2 (3)	C27—C26—H26A	119.2
C10—C11—H11A	121.4	C25—C26—H26A	119.2
C12—C11—H11A	121.4	C26—C27—C28	117.1 (3)
C11—C12—N1	129.6 (2)	C26—C27—H27A	121.5
C11—C12—C7	121.7 (2)	C28—C27—H27A	121.5
N1—C12—C7	108.7 (2)	C27—C28—N2	129.3 (2)
C14—C13—N1	126.2 (2)	C27—C28—C23	122.1 (2)
C14—C13—S1	112.72 (19)	N2—C28—C23	108.6 (2)
N1—C13—S1	120.95 (19)

C12—N1—C1—C2	179.9 (3)	C14—C15—C16—N2	−174.8 (3)
C13—N1—C1—C2	3.4 (5)	C14—C15—C16—S1	0.4 (4)
C12—N1—C1—C6	−0.9 (3)	C28—N2—C16—C15	−106.6 (4)
C13—N1—C1—C6	−177.4 (2)	C17—N2—C16—C15	63.8 (4)
C6—C1—C2—C3	−0.4 (5)	C28—N2—C16—S1	78.6 (3)
N1—C1—C2—C3	178.6 (3)	C17—N2—C16—S1	−111.0 (2)
C1—C2—C3—C4	−0.1 (5)	C13—S1—C16—C15	−0.4 (3)
C2—C3—C4—C5	0.1 (6)	C13—S1—C16—N2	175.1 (2)
C3—C4—C5—C6	0.4 (5)	C28—N2—C17—C18	−179.5 (3)
C2—C1—C6—C5	0.9 (4)	C16—N2—C17—C18	8.6 (4)
N1—C1—C6—C5	−178.3 (2)	C28—N2—C17—C22	−0.5 (3)
C2—C1—C6—C7	180.0 (3)	C16—N2—C17—C22	−172.3 (2)
N1—C1—C6—C7	0.8 (3)	C22—C17—C18—C19	1.2 (4)
C4—C5—C6—C1	−0.9 (4)	N2—C17—C18—C19	−179.9 (3)
C4—C5—C6—C7	−179.6 (3)	C17—C18—C19—C20	0.3 (4)
C1—C6—C7—C8	177.8 (3)	C18—C19—C20—C21	−0.9 (5)
C5—C6—C7—C8	−3.4 (5)	C19—C20—C21—C22	0.0 (4)
C1—C6—C7—C12	−0.3 (3)	C20—C21—C22—C17	1.4 (4)
C5—C6—C7—C12	178.6 (3)	C20—C21—C22—C23	−179.8 (3)
C12—C7—C8—C9	0.0 (4)	C18—C17—C22—C21	−2.1 (4)
C6—C7—C8—C9	−177.9 (3)	N2—C17—C22—C21	178.8 (2)
C7—C8—C9—C10	−1.0 (5)	C18—C17—C22—C23	178.8 (2)
C8—C9—C10—C11	0.4 (5)	N2—C17—C22—C23	−0.3 (3)
C9—C10—C11—C12	1.3 (4)	C21—C22—C23—C24	1.2 (5)
C10—C11—C12—N1	178.2 (3)	C17—C22—C23—C24	−179.9 (3)
C10—C11—C12—C7	−2.4 (4)	C21—C22—C23—C28	−178.0 (3)
C1—N1—C12—C11	−179.8 (3)	C17—C22—C23—C28	0.9 (3)
C13—N1—C12—C11	−3.2 (4)	C28—C23—C24—C25	0.8 (4)
C1—N1—C12—C7	0.7 (3)	C22—C23—C24—C25	−178.3 (3)
C13—N1—C12—C7	177.2 (2)	C23—C24—C25—C26	−0.4 (5)
C8—C7—C12—C11	1.8 (4)	C24—C25—C26—C27	0.3 (6)
C6—C7—C12—C11	−179.8 (2)	C25—C26—C27—C28	−0.4 (5)
C8—C7—C12—N1	−178.7 (2)	C26—C27—C28—N2	−179.7 (3)
C6—C7—C12—N1	−0.3 (3)	C26—C27—C28—C23	0.8 (4)
C12—N1—C13—C14	64.9 (4)	C17—N2—C28—C27	−178.5 (3)
C1—N1—C13—C14	−119.2 (3)	C16—N2—C28—C27	−6.8 (4)
C12—N1—C13—S1	−110.7 (3)	C17—N2—C28—C23	1.1 (3)
C1—N1—C13—S1	65.2 (3)	C16—N2—C28—C23	172.7 (2)
C16—S1—C13—C14	0.3 (2)	C24—C23—C28—C27	−0.9 (4)
C16—S1—C13—N1	176.5 (2)	C22—C23—C28—C27	178.4 (2)
N1—C13—C14—C15	−176.0 (3)	C24—C23—C28—N2	179.4 (2)
S1—C13—C14—C15	−0.1 (4)	C22—C23—C28—N2	−1.2 (3)
C13—C14—C15—C16	−0.2 (4)

Experimental details

Crystal data
Chemical formula	C₂₈H₁₈N₂S
M_r	414.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	7.8760 (16), 16.098 (3), 33.986 (7)
V (Å³)	4309.1 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS-IV diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.963, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	12051, 3931, 3230
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.152, 1.13
No. of reflections	3931
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: R-AXIS (Rigaku, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

We are grateful to the Top Key Discipline of Pharmaceutics in Zhejiang Provincial Colleges (grant No. 20060611), the Department of Education of Zhejiang Province of China (grant No. 20060806) and the Creative High Level Personal Project of Zhejiang University of Technology (grant No. 071058) for financial support.

References

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