organic compounds
2,5-Bis(9H-carbazol-9-yl)thiophene
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
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
|
Data collection: R-AXIS (Rigaku, 1996); cell 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
10.1107/S1600536808039767/dn2409sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039767/dn2409Isup2.hkl
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
(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.H atoms were included in calculated positions and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2 times the equivalent isotropic displacement parameters of their parent atoms and C—H distances were restrained to 0.93 Å.
Data collection: R-AXIS (Rigaku, 1996); cell
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).Fig. 1. The structure of (I), showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. |
C28H18N2S | F(000) = 1728 |
Mr = 414.50 | Dx = 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 |
Rigaku R-AXIS-IV diffractometer | 3230 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.091 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
Oscillation frames scans | h = −9→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −19→0 |
Tmin = 0.963, Tmax = 0.977 | l = −41→41 |
12051 measured reflections | 3 standard reflections every 60 min |
3931 independent reflections | intensity decay: 0.3% |
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(Fo2) + (0.0561P)2 + 1.4309P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.005 |
3931 reflections | Δρmax = 0.22 e Å−3 |
281 parameters | Δρmin = −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) |
C28H18N2S | V = 4309.1 (15) Å3 |
Mr = 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 |
Rigaku R-AXIS-IV diffractometer | 3230 reflections with I > 2σ(I) |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | Rint = 0.091 |
Tmin = 0.963, Tmax = 0.977 | 3 standard reflections every 60 min |
12051 measured reflections | intensity decay: 0.3% |
3931 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.22 e Å−3 |
3931 reflections | Δρmin = −0.24 e Å−3 |
281 parameters |
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 | ||
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.963, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12051, 3931, 3230 |
Rint | 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 |
Δρmax, Δρmin (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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1996). R-AXIS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, I. Y., Lin, J. T., Tao, Y. T. & Balasubramaniam, E. (2000). Adv. Mater. 12, 668–669. CrossRef CAS Google Scholar
Wu, I.-Y., Lin, J. T., Tao, Y.-T., Balasubramaniam, E., Su, Y. Z. & Ko, C.-W. (2001). Chem. Mater. 13, 2626–2631. Web of Science CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.