organic compounds
3,6-Di-tert-butyl-9-(quinolin-6-yl)-9H-carbazole
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: guan@njut.edu.cn
In the title compound, C29H30N2, the dihedral angle between the mean planes of the carbazole and the quinoline systems is 52.41 (6)°. Molecules are linked into dimers by pairs of intermolecular C—H⋯N hydrogen bonds and into a three-dimensional network by C—H⋯π interactions.
Related literature
The title compound is an important intermediate in manufacturing materials such as organic light-emitting devices. For background to this class of compounds, see: Owczarczyk (2005). For the synthesis of the title compound, see: Muci & Buchwald (2002). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812030723/zq2170sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812030723/zq2170Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812030723/zq2170Isup3.cml
The title compound was prepared by a literature method (Muci & Buchwald, 2002). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.41 g, 0.1 mmol) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.
All H atoms were placed geometricallyand refined as riding with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).C29H30N2 | Z = 2 |
Mr = 406.55 | F(000) = 436 |
Triclinic, P1 | Dx = 1.164 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9140 (12) Å | Cell parameters from 25 reflections |
b = 13.133 (3) Å | θ = 9–13° |
c = 16.285 (3) Å | µ = 0.07 mm−1 |
α = 69.30 (3)° | T = 293 K |
β = 83.28 (3)° | Acicular, colourless |
γ = 79.11 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 1160.1 (4) Å3 |
Enraf–Nonius CAD-4 diffractometer | 2838 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.4°, θmin = 1.3° |
ω/2θ scans | h = 0→7 |
Absorption correction: ψ scan (North et al., 1968) | k = −15→15 |
Tmin = 0.980, Tmax = 0.993 | l = −19→19 |
4710 measured reflections | 3 standard reflections every 200 reflections |
4260 independent reflections | intensity decay: 1% |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4260 reflections | Δρmax = 0.18 e Å−3 |
281 parameters | Δρmin = −0.19 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: 0.094 (8) |
C29H30N2 | γ = 79.11 (3)° |
Mr = 406.55 | V = 1160.1 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.9140 (12) Å | Mo Kα radiation |
b = 13.133 (3) Å | µ = 0.07 mm−1 |
c = 16.285 (3) Å | T = 293 K |
α = 69.30 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 83.28 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2838 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.980, Tmax = 0.993 | 3 standard reflections every 200 reflections |
4710 measured reflections | intensity decay: 1% |
4260 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.18 e Å−3 |
4260 reflections | Δρmin = −0.19 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 | ||
N1 | 0.6826 (3) | 0.28889 (14) | 0.32604 (12) | 0.0430 (5) | |
C1 | 0.6135 (4) | 0.20305 (17) | 0.30806 (14) | 0.0386 (5) | |
N2 | 1.2433 (3) | 0.27066 (16) | 0.58530 (13) | 0.0488 (5) | |
C2 | 0.6628 (4) | 0.08984 (18) | 0.34991 (15) | 0.0448 (6) | |
H2B | 0.7574 | 0.0598 | 0.3972 | 0.054* | |
C3 | 0.5675 (4) | 0.02372 (18) | 0.31929 (15) | 0.0456 (6) | |
H3A | 0.6011 | −0.0523 | 0.3466 | 0.055* | |
C4 | 0.4209 (4) | 0.06508 (17) | 0.24845 (14) | 0.0394 (5) | |
C5 | 0.3708 (4) | 0.17821 (17) | 0.20890 (14) | 0.0378 (5) | |
H5A | 0.2732 | 0.2081 | 0.1625 | 0.045* | |
C6 | 0.4661 (4) | 0.24780 (16) | 0.23841 (13) | 0.0359 (5) | |
C7 | 0.4423 (4) | 0.36640 (16) | 0.21274 (14) | 0.0371 (5) | |
C8 | 0.3217 (4) | 0.45393 (17) | 0.14801 (14) | 0.0386 (5) | |
H8A | 0.2291 | 0.4396 | 0.1123 | 0.046* | |
C9 | 0.3386 (4) | 0.56156 (17) | 0.13664 (14) | 0.0379 (5) | |
C10 | 0.4805 (4) | 0.57927 (18) | 0.19202 (15) | 0.0448 (6) | |
H10A | 0.4941 | 0.6515 | 0.1844 | 0.054* | |
C11 | 0.6006 (4) | 0.49529 (18) | 0.25698 (15) | 0.0456 (6) | |
H11A | 0.6935 | 0.5100 | 0.2924 | 0.055* | |
C12 | 0.5782 (4) | 0.38803 (17) | 0.26771 (14) | 0.0404 (6) | |
C13 | 0.3314 (4) | −0.01504 (18) | 0.21547 (16) | 0.0458 (6) | |
C14 | 0.5381 (5) | −0.0732 (2) | 0.1730 (2) | 0.0707 (9) | |
H14A | 0.6057 | −0.0193 | 0.1245 | 0.106* | |
H14B | 0.4863 | −0.1243 | 0.1522 | 0.106* | |
H14C | 0.6511 | −0.1122 | 0.2158 | 0.106* | |
C15 | 0.2244 (5) | −0.1018 (2) | 0.29260 (19) | 0.0657 (8) | |
H15A | 0.0963 | −0.0660 | 0.3196 | 0.099* | |
H15B | 0.3380 | −0.1413 | 0.3350 | 0.099* | |
H15C | 0.1719 | −0.1524 | 0.2714 | 0.099* | |
C16 | 0.1486 (5) | 0.0432 (2) | 0.1483 (2) | 0.0692 (9) | |
H16A | 0.2121 | 0.0976 | 0.0990 | 0.104* | |
H16B | 0.0186 | 0.0784 | 0.1749 | 0.104* | |
H16C | 0.1000 | −0.0098 | 0.1287 | 0.104* | |
C17 | 0.2100 (4) | 0.66163 (17) | 0.06702 (14) | 0.0420 (6) | |
C18 | 0.0785 (5) | 0.6271 (2) | 0.00882 (18) | 0.0705 (9) | |
H18A | 0.1842 | 0.5838 | −0.0201 | 0.106* | |
H18B | 0.0028 | 0.6915 | −0.0344 | 0.106* | |
H18C | −0.0346 | 0.5840 | 0.0443 | 0.106* | |
C19 | 0.0372 (5) | 0.7300 (2) | 0.11289 (18) | 0.0647 (8) | |
H19A | −0.0719 | 0.6854 | 0.1496 | 0.097* | |
H19B | −0.0428 | 0.7927 | 0.0695 | 0.097* | |
H19C | 0.1182 | 0.7546 | 0.1483 | 0.097* | |
C20 | 0.3835 (5) | 0.7328 (2) | 0.00850 (17) | 0.0672 (8) | |
H20A | 0.4914 | 0.6903 | −0.0204 | 0.101* | |
H20B | 0.4649 | 0.7573 | 0.0439 | 0.101* | |
H20C | 0.3033 | 0.7957 | −0.0348 | 0.101* | |
C21 | 0.8180 (4) | 0.27973 (17) | 0.39558 (14) | 0.0379 (5) | |
C22 | 0.7372 (4) | 0.33765 (17) | 0.45071 (14) | 0.0405 (6) | |
H22A | 0.5888 | 0.3776 | 0.4455 | 0.049* | |
C23 | 0.8755 (4) | 0.33782 (16) | 0.51539 (14) | 0.0368 (5) | |
C24 | 0.8046 (4) | 0.39882 (19) | 0.57257 (15) | 0.0478 (6) | |
H24A | 0.6586 | 0.4410 | 0.5694 | 0.057* | |
C25 | 0.9498 (5) | 0.3956 (2) | 0.63199 (16) | 0.0523 (7) | |
H25A | 0.9061 | 0.4359 | 0.6697 | 0.063* | |
C26 | 1.1674 (5) | 0.3302 (2) | 0.63553 (16) | 0.0523 (7) | |
H26A | 1.2655 | 0.3290 | 0.6766 | 0.063* | |
C27 | 1.0984 (4) | 0.27437 (17) | 0.52467 (14) | 0.0383 (5) | |
C28 | 1.1730 (4) | 0.2113 (2) | 0.46923 (15) | 0.0471 (6) | |
H28A | 1.3166 | 0.1667 | 0.4763 | 0.056* | |
C29 | 1.0385 (4) | 0.21466 (19) | 0.40572 (15) | 0.0452 (6) | |
H29A | 1.0922 | 0.1739 | 0.3689 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0558 (12) | 0.0340 (10) | 0.0408 (11) | −0.0017 (9) | −0.0206 (9) | −0.0117 (8) |
C1 | 0.0461 (14) | 0.0355 (12) | 0.0361 (12) | −0.0047 (10) | −0.0069 (10) | −0.0138 (10) |
N2 | 0.0479 (12) | 0.0545 (12) | 0.0479 (12) | −0.0061 (10) | −0.0150 (10) | −0.0194 (10) |
C2 | 0.0548 (15) | 0.0363 (12) | 0.0413 (13) | 0.0005 (11) | −0.0176 (11) | −0.0101 (10) |
C3 | 0.0544 (15) | 0.0311 (12) | 0.0492 (14) | −0.0012 (10) | −0.0117 (12) | −0.0111 (10) |
C4 | 0.0435 (13) | 0.0344 (12) | 0.0415 (12) | −0.0049 (10) | −0.0041 (10) | −0.0146 (10) |
C5 | 0.0449 (13) | 0.0355 (12) | 0.0336 (12) | −0.0074 (10) | −0.0081 (10) | −0.0103 (10) |
C6 | 0.0420 (13) | 0.0325 (11) | 0.0321 (11) | −0.0040 (9) | −0.0060 (10) | −0.0094 (9) |
C7 | 0.0437 (13) | 0.0335 (12) | 0.0358 (12) | −0.0052 (10) | −0.0083 (10) | −0.0124 (10) |
C8 | 0.0449 (13) | 0.0379 (12) | 0.0357 (12) | −0.0079 (10) | −0.0107 (10) | −0.0126 (10) |
C9 | 0.0430 (13) | 0.0346 (12) | 0.0364 (12) | −0.0066 (10) | −0.0069 (10) | −0.0108 (9) |
C10 | 0.0583 (15) | 0.0306 (11) | 0.0470 (14) | −0.0095 (11) | −0.0118 (12) | −0.0111 (10) |
C11 | 0.0550 (15) | 0.0392 (13) | 0.0485 (14) | −0.0099 (11) | −0.0203 (12) | −0.0155 (11) |
C12 | 0.0485 (14) | 0.0339 (12) | 0.0395 (12) | −0.0038 (10) | −0.0118 (11) | −0.0119 (10) |
C13 | 0.0513 (15) | 0.0328 (12) | 0.0564 (15) | −0.0094 (10) | −0.0099 (12) | −0.0152 (11) |
C14 | 0.078 (2) | 0.0668 (18) | 0.087 (2) | −0.0156 (16) | 0.0004 (17) | −0.0499 (17) |
C15 | 0.0677 (19) | 0.0491 (15) | 0.0773 (19) | −0.0214 (14) | −0.0127 (15) | −0.0088 (14) |
C16 | 0.086 (2) | 0.0496 (15) | 0.079 (2) | −0.0136 (15) | −0.0397 (17) | −0.0181 (14) |
C17 | 0.0491 (14) | 0.0353 (12) | 0.0403 (13) | −0.0048 (10) | −0.0117 (11) | −0.0093 (10) |
C18 | 0.099 (2) | 0.0450 (15) | 0.0674 (18) | −0.0024 (15) | −0.0489 (18) | −0.0091 (13) |
C19 | 0.0633 (18) | 0.0584 (17) | 0.0654 (18) | 0.0094 (14) | −0.0124 (15) | −0.0196 (14) |
C20 | 0.0714 (19) | 0.0586 (17) | 0.0534 (16) | −0.0104 (14) | −0.0081 (14) | 0.0048 (13) |
C21 | 0.0425 (13) | 0.0364 (12) | 0.0355 (12) | −0.0047 (10) | −0.0106 (10) | −0.0111 (10) |
C22 | 0.0407 (13) | 0.0366 (12) | 0.0421 (13) | 0.0019 (10) | −0.0115 (10) | −0.0121 (10) |
C23 | 0.0440 (13) | 0.0315 (11) | 0.0335 (11) | −0.0066 (10) | −0.0056 (10) | −0.0077 (9) |
C24 | 0.0556 (15) | 0.0439 (13) | 0.0465 (14) | 0.0009 (11) | −0.0088 (12) | −0.0212 (11) |
C25 | 0.0711 (18) | 0.0500 (14) | 0.0427 (14) | −0.0105 (13) | −0.0072 (13) | −0.0224 (12) |
C26 | 0.0613 (17) | 0.0558 (15) | 0.0473 (14) | −0.0158 (13) | −0.0147 (13) | −0.0198 (12) |
C27 | 0.0388 (13) | 0.0387 (12) | 0.0378 (12) | −0.0084 (10) | −0.0053 (10) | −0.0111 (10) |
C28 | 0.0387 (13) | 0.0548 (15) | 0.0492 (14) | 0.0040 (11) | −0.0104 (11) | −0.0229 (12) |
C29 | 0.0465 (14) | 0.0512 (14) | 0.0423 (13) | 0.0004 (11) | −0.0043 (11) | −0.0248 (11) |
N1—C12 | 1.392 (3) | C15—H15B | 0.9600 |
N1—C1 | 1.400 (3) | C15—H15C | 0.9600 |
N1—C21 | 1.420 (3) | C16—H16A | 0.9600 |
C1—C2 | 1.388 (3) | C16—H16B | 0.9600 |
C1—C6 | 1.399 (3) | C16—H16C | 0.9600 |
N2—C26 | 1.310 (3) | C17—C18 | 1.523 (3) |
N2—C27 | 1.364 (3) | C17—C20 | 1.530 (3) |
C2—C3 | 1.370 (3) | C17—C19 | 1.535 (3) |
C2—H2B | 0.9300 | C18—H18A | 0.9600 |
C3—C4 | 1.411 (3) | C18—H18B | 0.9600 |
C3—H3A | 0.9300 | C18—H18C | 0.9600 |
C4—C5 | 1.383 (3) | C19—H19A | 0.9600 |
C4—C13 | 1.534 (3) | C19—H19B | 0.9600 |
C5—C6 | 1.397 (3) | C19—H19C | 0.9600 |
C5—H5A | 0.9300 | C20—H20A | 0.9600 |
C6—C7 | 1.446 (3) | C20—H20B | 0.9600 |
C7—C8 | 1.397 (3) | C20—H20C | 0.9600 |
C7—C12 | 1.401 (3) | C21—C22 | 1.363 (3) |
C8—C9 | 1.381 (3) | C21—C29 | 1.410 (3) |
C8—H8A | 0.9300 | C22—C23 | 1.408 (3) |
C9—C10 | 1.404 (3) | C22—H22A | 0.9300 |
C9—C17 | 1.537 (3) | C23—C24 | 1.412 (3) |
C10—C11 | 1.377 (3) | C23—C27 | 1.413 (3) |
C10—H10A | 0.9300 | C24—C25 | 1.352 (3) |
C11—C12 | 1.387 (3) | C24—H24A | 0.9300 |
C11—H11A | 0.9300 | C25—C26 | 1.401 (4) |
C13—C16 | 1.524 (3) | C25—H25A | 0.9300 |
C13—C15 | 1.533 (3) | C26—H26A | 0.9300 |
C13—C14 | 1.543 (4) | C27—C28 | 1.412 (3) |
C14—H14A | 0.9600 | C28—C29 | 1.361 (3) |
C14—H14B | 0.9600 | C28—H28A | 0.9300 |
C14—H14C | 0.9600 | C29—H29A | 0.9300 |
C15—H15A | 0.9600 | ||
C12—N1—C1 | 107.81 (17) | C13—C16—H16A | 109.5 |
C12—N1—C21 | 124.67 (18) | C13—C16—H16B | 109.5 |
C1—N1—C21 | 127.31 (18) | H16A—C16—H16B | 109.5 |
C2—C1—C6 | 120.8 (2) | C13—C16—H16C | 109.5 |
C2—C1—N1 | 130.0 (2) | H16A—C16—H16C | 109.5 |
C6—C1—N1 | 109.11 (18) | H16B—C16—H16C | 109.5 |
C26—N2—C27 | 116.8 (2) | C18—C17—C20 | 108.3 (2) |
C3—C2—C1 | 117.8 (2) | C18—C17—C19 | 108.5 (2) |
C3—C2—H2B | 121.1 | C20—C17—C19 | 109.4 (2) |
C1—C2—H2B | 121.1 | C18—C17—C9 | 111.84 (18) |
C2—C3—C4 | 123.3 (2) | C20—C17—C9 | 109.40 (19) |
C2—C3—H3A | 118.3 | C19—C17—C9 | 109.40 (19) |
C4—C3—H3A | 118.3 | C17—C18—H18A | 109.5 |
C5—C4—C3 | 117.8 (2) | C17—C18—H18B | 109.5 |
C5—C4—C13 | 122.3 (2) | H18A—C18—H18B | 109.5 |
C3—C4—C13 | 119.84 (19) | C17—C18—H18C | 109.5 |
C4—C5—C6 | 120.2 (2) | H18A—C18—H18C | 109.5 |
C4—C5—H5A | 119.9 | H18B—C18—H18C | 109.5 |
C6—C5—H5A | 119.9 | C17—C19—H19A | 109.5 |
C5—C6—C1 | 120.00 (19) | C17—C19—H19B | 109.5 |
C5—C6—C7 | 133.03 (19) | H19A—C19—H19B | 109.5 |
C1—C6—C7 | 106.96 (18) | C17—C19—H19C | 109.5 |
C8—C7—C12 | 119.73 (19) | H19A—C19—H19C | 109.5 |
C8—C7—C6 | 133.6 (2) | H19B—C19—H19C | 109.5 |
C12—C7—C6 | 106.66 (18) | C17—C20—H20A | 109.5 |
C9—C8—C7 | 120.6 (2) | C17—C20—H20B | 109.5 |
C9—C8—H8A | 119.7 | H20A—C20—H20B | 109.5 |
C7—C8—H8A | 119.7 | C17—C20—H20C | 109.5 |
C8—C9—C10 | 117.7 (2) | H20A—C20—H20C | 109.5 |
C8—C9—C17 | 123.27 (19) | H20B—C20—H20C | 109.5 |
C10—C9—C17 | 119.00 (19) | C22—C21—C29 | 119.9 (2) |
C11—C10—C9 | 123.4 (2) | C22—C21—N1 | 119.58 (19) |
C11—C10—H10A | 118.3 | C29—C21—N1 | 120.43 (19) |
C9—C10—H10A | 118.3 | C21—C22—C23 | 120.9 (2) |
C10—C11—C12 | 117.7 (2) | C21—C22—H22A | 119.6 |
C10—C11—H11A | 121.2 | C23—C22—H22A | 119.6 |
C12—C11—H11A | 121.2 | C22—C23—C24 | 123.6 (2) |
C11—C12—N1 | 129.6 (2) | C22—C23—C27 | 119.3 (2) |
C11—C12—C7 | 120.9 (2) | C24—C23—C27 | 117.1 (2) |
N1—C12—C7 | 109.45 (18) | C25—C24—C23 | 119.7 (2) |
C16—C13—C15 | 107.9 (2) | C25—C24—H24A | 120.1 |
C16—C13—C4 | 112.41 (19) | C23—C24—H24A | 120.1 |
C15—C13—C4 | 110.1 (2) | C24—C25—C26 | 118.6 (2) |
C16—C13—C14 | 109.3 (2) | C24—C25—H25A | 120.7 |
C15—C13—C14 | 109.1 (2) | C26—C25—H25A | 120.7 |
C4—C13—C14 | 107.97 (19) | N2—C26—C25 | 124.9 (2) |
C13—C14—H14A | 109.5 | N2—C26—H26A | 117.5 |
C13—C14—H14B | 109.5 | C25—C26—H26A | 117.5 |
H14A—C14—H14B | 109.5 | N2—C27—C28 | 118.7 (2) |
C13—C14—H14C | 109.5 | N2—C27—C23 | 122.9 (2) |
H14A—C14—H14C | 109.5 | C28—C27—C23 | 118.4 (2) |
H14B—C14—H14C | 109.5 | C29—C28—C27 | 121.1 (2) |
C13—C15—H15A | 109.5 | C29—C28—H28A | 119.4 |
C13—C15—H15B | 109.5 | C27—C28—H28A | 119.4 |
H15A—C15—H15B | 109.5 | C28—C29—C21 | 120.2 (2) |
C13—C15—H15C | 109.5 | C28—C29—H29A | 119.9 |
H15A—C15—H15C | 109.5 | C21—C29—H29A | 119.9 |
H15B—C15—H15C | 109.5 | ||
C12—N1—C1—C2 | −177.2 (2) | C6—C7—C12—N1 | −0.4 (3) |
C21—N1—C1—C2 | −2.3 (4) | C5—C4—C13—C16 | −11.1 (3) |
C12—N1—C1—C6 | 0.1 (3) | C3—C4—C13—C16 | 171.5 (2) |
C21—N1—C1—C6 | 175.0 (2) | C5—C4—C13—C15 | −131.5 (2) |
C6—C1—C2—C3 | 1.7 (3) | C3—C4—C13—C15 | 51.1 (3) |
N1—C1—C2—C3 | 178.7 (2) | C5—C4—C13—C14 | 109.5 (3) |
C1—C2—C3—C4 | −0.7 (4) | C3—C4—C13—C14 | −67.9 (3) |
C2—C3—C4—C5 | −0.5 (4) | C8—C9—C17—C18 | −4.2 (3) |
C2—C3—C4—C13 | 177.0 (2) | C10—C9—C17—C18 | 175.9 (2) |
C3—C4—C5—C6 | 0.8 (3) | C8—C9—C17—C20 | −124.2 (2) |
C13—C4—C5—C6 | −176.7 (2) | C10—C9—C17—C20 | 55.9 (3) |
C4—C5—C6—C1 | 0.2 (3) | C8—C9—C17—C19 | 116.0 (2) |
C4—C5—C6—C7 | −178.1 (2) | C10—C9—C17—C19 | −63.9 (3) |
C2—C1—C6—C5 | −1.5 (3) | C12—N1—C21—C22 | 48.2 (3) |
N1—C1—C6—C5 | −179.06 (19) | C1—N1—C21—C22 | −125.9 (2) |
C2—C1—C6—C7 | 177.2 (2) | C12—N1—C21—C29 | −129.4 (2) |
N1—C1—C6—C7 | −0.4 (2) | C1—N1—C21—C29 | 56.5 (3) |
C5—C6—C7—C8 | −2.2 (4) | C29—C21—C22—C23 | 3.1 (3) |
C1—C6—C7—C8 | 179.4 (2) | N1—C21—C22—C23 | −174.45 (19) |
C5—C6—C7—C12 | 178.9 (2) | C21—C22—C23—C24 | 177.9 (2) |
C1—C6—C7—C12 | 0.5 (2) | C21—C22—C23—C27 | −1.9 (3) |
C12—C7—C8—C9 | 1.2 (3) | C22—C23—C24—C25 | −179.0 (2) |
C6—C7—C8—C9 | −177.6 (2) | C27—C23—C24—C25 | 0.8 (3) |
C7—C8—C9—C10 | 0.1 (3) | C23—C24—C25—C26 | −0.6 (4) |
C7—C8—C9—C17 | −179.8 (2) | C27—N2—C26—C25 | 0.8 (4) |
C8—C9—C10—C11 | −0.6 (4) | C24—C25—C26—N2 | −0.2 (4) |
C17—C9—C10—C11 | 179.2 (2) | C26—N2—C27—C28 | −179.9 (2) |
C9—C10—C11—C12 | −0.2 (4) | C26—N2—C27—C23 | −0.6 (3) |
C10—C11—C12—N1 | 178.4 (2) | C22—C23—C27—N2 | 179.6 (2) |
C10—C11—C12—C7 | 1.5 (4) | C24—C23—C27—N2 | −0.2 (3) |
C1—N1—C12—C11 | −177.0 (2) | C22—C23—C27—C28 | −1.0 (3) |
C21—N1—C12—C11 | 8.0 (4) | C24—C23—C27—C28 | 179.1 (2) |
C1—N1—C12—C7 | 0.2 (3) | N2—C27—C28—C29 | −177.9 (2) |
C21—N1—C12—C7 | −174.9 (2) | C23—C27—C28—C29 | 2.8 (3) |
C8—C7—C12—C11 | −2.1 (3) | C27—C28—C29—C21 | −1.6 (4) |
C6—C7—C12—C11 | 177.0 (2) | C22—C21—C29—C28 | −1.4 (4) |
C8—C7—C12—N1 | −179.5 (2) | N1—C21—C29—C28 | 176.1 (2) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···N2i | 0.93 | 2.70 | 3.625 (3) | 172 |
C15—H15B···N2i | 0.96 | 2.87 | 3.807 (4) | 162 |
C29—H29A···Cg1ii | 0.93 | 2.81 | 3.525 (3) | 134 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C29H30N2 |
Mr | 406.55 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.9140 (12), 13.133 (3), 16.285 (3) |
α, β, γ (°) | 69.30 (3), 83.28 (3), 79.11 (3) |
V (Å3) | 1160.1 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.980, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4710, 4260, 2838 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.171, 1.00 |
No. of reflections | 4260 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.19 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···N2i | 0.93 | 2.70 | 3.625 (3) | 172.1 |
C15—H15B···N2i | 0.96 | 2.87 | 3.807 (4) | 162 |
C29—H29A···Cg1ii | 0.93 | 2.81 | 3.525 (3) | 134 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, y, z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Harms, K. & Wocadlo, S. (1995). CAD-4 EXPRESS. University of Marburg, Germany. Google Scholar
Muci, A. R. & Buchwald, S. L. (2002). Top. Curr. Chem. 219, 131–209. CrossRef CAS Google Scholar
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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.
The title compound is an important intermediate for a kind of manufacturing material, such organic light-emitting devices (Owczarczyk, 2005) and particularly in the synthesis of (Z)-6-(3,6-di-tert-butyl-9H-carbazol-9-yl)-N-[6-(2,7-di-tert-butyl-9H-carbazol-9-yl)quinolin-2(1H)-ylidene]quinolin-2-amine.
In the title compound, C29H30N2, the dihedral angle between the mean planes of the carbazole and the quinoline rings is 52.41 (6)°. The bond lengths and angles are in normal ranges (Allen et al., 1987). The molecules are linked into a dimer by pairs of intermolecular C—H···N hydrogen bonds (Table 1) and into a three-dimensional network by C–H···π interactions [ C29–H29A···Cg1ii = 2.81 Å, C25–H25A···Cg2iii = 3.19 Å; Cg1 and Cg2 are the centroids of the C1/C6 and C7/C12 rings, respectively; symmetry codes: ii = 1+x, y, z, iii = 1-x, 1-y, 1-z).