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ISSN: 2056-9890

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

(Received 30 May 2012; accepted 5 July 2012; online 1 August 2012)

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[Owczarczyk, Z. R. (2005). US Patent No. 2005/0131234 A1.]). For the synthesis of the title compound, see: Muci & Buchwald (2002[Muci, A. R. & Buchwald, S. L. (2002). Top. Curr. Chem. 219, 131-209.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C29H30N2

  • Mr = 406.55

  • Triclinic, [P \overline 1]

  • a = 5.9140 (12) Å

  • b = 13.133 (3) Å

  • c = 16.285 (3) Å

  • α = 69.30 (3)°

  • β = 83.28 (3)°

  • γ = 79.11 (3)°

  • V = 1160.1 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.980, Tmax = 0.993

  • 4710 measured reflections

  • 4260 independent reflections

  • 2838 reflections with I > 2σ(I)

  • Rint = 0.025

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.171

  • S = 1.00

  • 4260 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA 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—H29ACg1ii 0.93 2.81 3.525 (3) 134
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x+1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). CAD-4 EXPRESS. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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).

Related literature top

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 top

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.

Refinement top

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.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound viewed along the b axis.
3,6-Di-tert-butyl-9-(quinolin-6-yl)-9H-carbazole top
Crystal data top
C29H30N2Z = 2
Mr = 406.55F(000) = 436
Triclinic, P1Dx = 1.164 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9140 (12) ÅCell parameters from 25 reflections
b = 13.133 (3) Åθ = 9–13°
c = 16.285 (3) ŵ = 0.07 mm1
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
Data collection top
Enraf–Nonius CAD-4
diffractometer
2838 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.4°, θmin = 1.3°
ω/2θ scansh = 07
Absorption correction: ψ scan
(North et al., 1968)
k = 1515
Tmin = 0.980, Tmax = 0.993l = 1919
4710 measured reflections3 standard reflections every 200 reflections
4260 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 0.18 e Å3
281 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.094 (8)
Crystal data top
C29H30N2γ = 79.11 (3)°
Mr = 406.55V = 1160.1 (4) Å3
Triclinic, P1Z = 2
a = 5.9140 (12) ÅMo Kα radiation
b = 13.133 (3) ŵ = 0.07 mm1
c = 16.285 (3) ÅT = 293 K
α = 69.30 (3)°0.30 × 0.20 × 0.10 mm
β = 83.28 (3)°
Data collection top
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 = 0.9933 standard reflections every 200 reflections
4710 measured reflections intensity decay: 1%
4260 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.00Δρmax = 0.18 e Å3
4260 reflectionsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
N10.6826 (3)0.28889 (14)0.32604 (12)0.0430 (5)
C10.6135 (4)0.20305 (17)0.30806 (14)0.0386 (5)
N21.2433 (3)0.27066 (16)0.58530 (13)0.0488 (5)
C20.6628 (4)0.08984 (18)0.34991 (15)0.0448 (6)
H2B0.75740.05980.39720.054*
C30.5675 (4)0.02372 (18)0.31929 (15)0.0456 (6)
H3A0.60110.05230.34660.055*
C40.4209 (4)0.06508 (17)0.24845 (14)0.0394 (5)
C50.3708 (4)0.17821 (17)0.20890 (14)0.0378 (5)
H5A0.27320.20810.16250.045*
C60.4661 (4)0.24780 (16)0.23841 (13)0.0359 (5)
C70.4423 (4)0.36640 (16)0.21274 (14)0.0371 (5)
C80.3217 (4)0.45393 (17)0.14801 (14)0.0386 (5)
H8A0.22910.43960.11230.046*
C90.3386 (4)0.56156 (17)0.13664 (14)0.0379 (5)
C100.4805 (4)0.57927 (18)0.19202 (15)0.0448 (6)
H10A0.49410.65150.18440.054*
C110.6006 (4)0.49529 (18)0.25698 (15)0.0456 (6)
H11A0.69350.51000.29240.055*
C120.5782 (4)0.38803 (17)0.26771 (14)0.0404 (6)
C130.3314 (4)0.01504 (18)0.21547 (16)0.0458 (6)
C140.5381 (5)0.0732 (2)0.1730 (2)0.0707 (9)
H14A0.60570.01930.12450.106*
H14B0.48630.12430.15220.106*
H14C0.65110.11220.21580.106*
C150.2244 (5)0.1018 (2)0.29260 (19)0.0657 (8)
H15A0.09630.06600.31960.099*
H15B0.33800.14130.33500.099*
H15C0.17190.15240.27140.099*
C160.1486 (5)0.0432 (2)0.1483 (2)0.0692 (9)
H16A0.21210.09760.09900.104*
H16B0.01860.07840.17490.104*
H16C0.10000.00980.12870.104*
C170.2100 (4)0.66163 (17)0.06702 (14)0.0420 (6)
C180.0785 (5)0.6271 (2)0.00882 (18)0.0705 (9)
H18A0.18420.58380.02010.106*
H18B0.00280.69150.03440.106*
H18C0.03460.58400.04430.106*
C190.0372 (5)0.7300 (2)0.11289 (18)0.0647 (8)
H19A0.07190.68540.14960.097*
H19B0.04280.79270.06950.097*
H19C0.11820.75460.14830.097*
C200.3835 (5)0.7328 (2)0.00850 (17)0.0672 (8)
H20A0.49140.69030.02040.101*
H20B0.46490.75730.04390.101*
H20C0.30330.79570.03480.101*
C210.8180 (4)0.27973 (17)0.39558 (14)0.0379 (5)
C220.7372 (4)0.33765 (17)0.45071 (14)0.0405 (6)
H22A0.58880.37760.44550.049*
C230.8755 (4)0.33782 (16)0.51539 (14)0.0368 (5)
C240.8046 (4)0.39882 (19)0.57257 (15)0.0478 (6)
H24A0.65860.44100.56940.057*
C250.9498 (5)0.3956 (2)0.63199 (16)0.0523 (7)
H25A0.90610.43590.66970.063*
C261.1674 (5)0.3302 (2)0.63553 (16)0.0523 (7)
H26A1.26550.32900.67660.063*
C271.0984 (4)0.27437 (17)0.52467 (14)0.0383 (5)
C281.1730 (4)0.2113 (2)0.46923 (15)0.0471 (6)
H28A1.31660.16670.47630.056*
C291.0385 (4)0.21466 (19)0.40572 (15)0.0452 (6)
H29A1.09220.17390.36890.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0558 (12)0.0340 (10)0.0408 (11)0.0017 (9)0.0206 (9)0.0117 (8)
C10.0461 (14)0.0355 (12)0.0361 (12)0.0047 (10)0.0069 (10)0.0138 (10)
N20.0479 (12)0.0545 (12)0.0479 (12)0.0061 (10)0.0150 (10)0.0194 (10)
C20.0548 (15)0.0363 (12)0.0413 (13)0.0005 (11)0.0176 (11)0.0101 (10)
C30.0544 (15)0.0311 (12)0.0492 (14)0.0012 (10)0.0117 (12)0.0111 (10)
C40.0435 (13)0.0344 (12)0.0415 (12)0.0049 (10)0.0041 (10)0.0146 (10)
C50.0449 (13)0.0355 (12)0.0336 (12)0.0074 (10)0.0081 (10)0.0103 (10)
C60.0420 (13)0.0325 (11)0.0321 (11)0.0040 (9)0.0060 (10)0.0094 (9)
C70.0437 (13)0.0335 (12)0.0358 (12)0.0052 (10)0.0083 (10)0.0124 (10)
C80.0449 (13)0.0379 (12)0.0357 (12)0.0079 (10)0.0107 (10)0.0126 (10)
C90.0430 (13)0.0346 (12)0.0364 (12)0.0066 (10)0.0069 (10)0.0108 (9)
C100.0583 (15)0.0306 (11)0.0470 (14)0.0095 (11)0.0118 (12)0.0111 (10)
C110.0550 (15)0.0392 (13)0.0485 (14)0.0099 (11)0.0203 (12)0.0155 (11)
C120.0485 (14)0.0339 (12)0.0395 (12)0.0038 (10)0.0118 (11)0.0119 (10)
C130.0513 (15)0.0328 (12)0.0564 (15)0.0094 (10)0.0099 (12)0.0152 (11)
C140.078 (2)0.0668 (18)0.087 (2)0.0156 (16)0.0004 (17)0.0499 (17)
C150.0677 (19)0.0491 (15)0.0773 (19)0.0214 (14)0.0127 (15)0.0088 (14)
C160.086 (2)0.0496 (15)0.079 (2)0.0136 (15)0.0397 (17)0.0181 (14)
C170.0491 (14)0.0353 (12)0.0403 (13)0.0048 (10)0.0117 (11)0.0093 (10)
C180.099 (2)0.0450 (15)0.0674 (18)0.0024 (15)0.0489 (18)0.0091 (13)
C190.0633 (18)0.0584 (17)0.0654 (18)0.0094 (14)0.0124 (15)0.0196 (14)
C200.0714 (19)0.0586 (17)0.0534 (16)0.0104 (14)0.0081 (14)0.0048 (13)
C210.0425 (13)0.0364 (12)0.0355 (12)0.0047 (10)0.0106 (10)0.0111 (10)
C220.0407 (13)0.0366 (12)0.0421 (13)0.0019 (10)0.0115 (10)0.0121 (10)
C230.0440 (13)0.0315 (11)0.0335 (11)0.0066 (10)0.0056 (10)0.0077 (9)
C240.0556 (15)0.0439 (13)0.0465 (14)0.0009 (11)0.0088 (12)0.0212 (11)
C250.0711 (18)0.0500 (14)0.0427 (14)0.0105 (13)0.0072 (13)0.0224 (12)
C260.0613 (17)0.0558 (15)0.0473 (14)0.0158 (13)0.0147 (13)0.0198 (12)
C270.0388 (13)0.0387 (12)0.0378 (12)0.0084 (10)0.0053 (10)0.0111 (10)
C280.0387 (13)0.0548 (15)0.0492 (14)0.0040 (11)0.0104 (11)0.0229 (12)
C290.0465 (14)0.0512 (14)0.0423 (13)0.0004 (11)0.0043 (11)0.0248 (11)
Geometric parameters (Å, º) top
N1—C121.392 (3)C15—H15B0.9600
N1—C11.400 (3)C15—H15C0.9600
N1—C211.420 (3)C16—H16A0.9600
C1—C21.388 (3)C16—H16B0.9600
C1—C61.399 (3)C16—H16C0.9600
N2—C261.310 (3)C17—C181.523 (3)
N2—C271.364 (3)C17—C201.530 (3)
C2—C31.370 (3)C17—C191.535 (3)
C2—H2B0.9300C18—H18A0.9600
C3—C41.411 (3)C18—H18B0.9600
C3—H3A0.9300C18—H18C0.9600
C4—C51.383 (3)C19—H19A0.9600
C4—C131.534 (3)C19—H19B0.9600
C5—C61.397 (3)C19—H19C0.9600
C5—H5A0.9300C20—H20A0.9600
C6—C71.446 (3)C20—H20B0.9600
C7—C81.397 (3)C20—H20C0.9600
C7—C121.401 (3)C21—C221.363 (3)
C8—C91.381 (3)C21—C291.410 (3)
C8—H8A0.9300C22—C231.408 (3)
C9—C101.404 (3)C22—H22A0.9300
C9—C171.537 (3)C23—C241.412 (3)
C10—C111.377 (3)C23—C271.413 (3)
C10—H10A0.9300C24—C251.352 (3)
C11—C121.387 (3)C24—H24A0.9300
C11—H11A0.9300C25—C261.401 (4)
C13—C161.524 (3)C25—H25A0.9300
C13—C151.533 (3)C26—H26A0.9300
C13—C141.543 (4)C27—C281.412 (3)
C14—H14A0.9600C28—C291.361 (3)
C14—H14B0.9600C28—H28A0.9300
C14—H14C0.9600C29—H29A0.9300
C15—H15A0.9600
C12—N1—C1107.81 (17)C13—C16—H16A109.5
C12—N1—C21124.67 (18)C13—C16—H16B109.5
C1—N1—C21127.31 (18)H16A—C16—H16B109.5
C2—C1—C6120.8 (2)C13—C16—H16C109.5
C2—C1—N1130.0 (2)H16A—C16—H16C109.5
C6—C1—N1109.11 (18)H16B—C16—H16C109.5
C26—N2—C27116.8 (2)C18—C17—C20108.3 (2)
C3—C2—C1117.8 (2)C18—C17—C19108.5 (2)
C3—C2—H2B121.1C20—C17—C19109.4 (2)
C1—C2—H2B121.1C18—C17—C9111.84 (18)
C2—C3—C4123.3 (2)C20—C17—C9109.40 (19)
C2—C3—H3A118.3C19—C17—C9109.40 (19)
C4—C3—H3A118.3C17—C18—H18A109.5
C5—C4—C3117.8 (2)C17—C18—H18B109.5
C5—C4—C13122.3 (2)H18A—C18—H18B109.5
C3—C4—C13119.84 (19)C17—C18—H18C109.5
C4—C5—C6120.2 (2)H18A—C18—H18C109.5
C4—C5—H5A119.9H18B—C18—H18C109.5
C6—C5—H5A119.9C17—C19—H19A109.5
C5—C6—C1120.00 (19)C17—C19—H19B109.5
C5—C6—C7133.03 (19)H19A—C19—H19B109.5
C1—C6—C7106.96 (18)C17—C19—H19C109.5
C8—C7—C12119.73 (19)H19A—C19—H19C109.5
C8—C7—C6133.6 (2)H19B—C19—H19C109.5
C12—C7—C6106.66 (18)C17—C20—H20A109.5
C9—C8—C7120.6 (2)C17—C20—H20B109.5
C9—C8—H8A119.7H20A—C20—H20B109.5
C7—C8—H8A119.7C17—C20—H20C109.5
C8—C9—C10117.7 (2)H20A—C20—H20C109.5
C8—C9—C17123.27 (19)H20B—C20—H20C109.5
C10—C9—C17119.00 (19)C22—C21—C29119.9 (2)
C11—C10—C9123.4 (2)C22—C21—N1119.58 (19)
C11—C10—H10A118.3C29—C21—N1120.43 (19)
C9—C10—H10A118.3C21—C22—C23120.9 (2)
C10—C11—C12117.7 (2)C21—C22—H22A119.6
C10—C11—H11A121.2C23—C22—H22A119.6
C12—C11—H11A121.2C22—C23—C24123.6 (2)
C11—C12—N1129.6 (2)C22—C23—C27119.3 (2)
C11—C12—C7120.9 (2)C24—C23—C27117.1 (2)
N1—C12—C7109.45 (18)C25—C24—C23119.7 (2)
C16—C13—C15107.9 (2)C25—C24—H24A120.1
C16—C13—C4112.41 (19)C23—C24—H24A120.1
C15—C13—C4110.1 (2)C24—C25—C26118.6 (2)
C16—C13—C14109.3 (2)C24—C25—H25A120.7
C15—C13—C14109.1 (2)C26—C25—H25A120.7
C4—C13—C14107.97 (19)N2—C26—C25124.9 (2)
C13—C14—H14A109.5N2—C26—H26A117.5
C13—C14—H14B109.5C25—C26—H26A117.5
H14A—C14—H14B109.5N2—C27—C28118.7 (2)
C13—C14—H14C109.5N2—C27—C23122.9 (2)
H14A—C14—H14C109.5C28—C27—C23118.4 (2)
H14B—C14—H14C109.5C29—C28—C27121.1 (2)
C13—C15—H15A109.5C29—C28—H28A119.4
C13—C15—H15B109.5C27—C28—H28A119.4
H15A—C15—H15B109.5C28—C29—C21120.2 (2)
C13—C15—H15C109.5C28—C29—H29A119.9
H15A—C15—H15C109.5C21—C29—H29A119.9
H15B—C15—H15C109.5
C12—N1—C1—C2177.2 (2)C6—C7—C12—N10.4 (3)
C21—N1—C1—C22.3 (4)C5—C4—C13—C1611.1 (3)
C12—N1—C1—C60.1 (3)C3—C4—C13—C16171.5 (2)
C21—N1—C1—C6175.0 (2)C5—C4—C13—C15131.5 (2)
C6—C1—C2—C31.7 (3)C3—C4—C13—C1551.1 (3)
N1—C1—C2—C3178.7 (2)C5—C4—C13—C14109.5 (3)
C1—C2—C3—C40.7 (4)C3—C4—C13—C1467.9 (3)
C2—C3—C4—C50.5 (4)C8—C9—C17—C184.2 (3)
C2—C3—C4—C13177.0 (2)C10—C9—C17—C18175.9 (2)
C3—C4—C5—C60.8 (3)C8—C9—C17—C20124.2 (2)
C13—C4—C5—C6176.7 (2)C10—C9—C17—C2055.9 (3)
C4—C5—C6—C10.2 (3)C8—C9—C17—C19116.0 (2)
C4—C5—C6—C7178.1 (2)C10—C9—C17—C1963.9 (3)
C2—C1—C6—C51.5 (3)C12—N1—C21—C2248.2 (3)
N1—C1—C6—C5179.06 (19)C1—N1—C21—C22125.9 (2)
C2—C1—C6—C7177.2 (2)C12—N1—C21—C29129.4 (2)
N1—C1—C6—C70.4 (2)C1—N1—C21—C2956.5 (3)
C5—C6—C7—C82.2 (4)C29—C21—C22—C233.1 (3)
C1—C6—C7—C8179.4 (2)N1—C21—C22—C23174.45 (19)
C5—C6—C7—C12178.9 (2)C21—C22—C23—C24177.9 (2)
C1—C6—C7—C120.5 (2)C21—C22—C23—C271.9 (3)
C12—C7—C8—C91.2 (3)C22—C23—C24—C25179.0 (2)
C6—C7—C8—C9177.6 (2)C27—C23—C24—C250.8 (3)
C7—C8—C9—C100.1 (3)C23—C24—C25—C260.6 (4)
C7—C8—C9—C17179.8 (2)C27—N2—C26—C250.8 (4)
C8—C9—C10—C110.6 (4)C24—C25—C26—N20.2 (4)
C17—C9—C10—C11179.2 (2)C26—N2—C27—C28179.9 (2)
C9—C10—C11—C120.2 (4)C26—N2—C27—C230.6 (3)
C10—C11—C12—N1178.4 (2)C22—C23—C27—N2179.6 (2)
C10—C11—C12—C71.5 (4)C24—C23—C27—N20.2 (3)
C1—N1—C12—C11177.0 (2)C22—C23—C27—C281.0 (3)
C21—N1—C12—C118.0 (4)C24—C23—C27—C28179.1 (2)
C1—N1—C12—C70.2 (3)N2—C27—C28—C29177.9 (2)
C21—N1—C12—C7174.9 (2)C23—C27—C28—C292.8 (3)
C8—C7—C12—C112.1 (3)C27—C28—C29—C211.6 (4)
C6—C7—C12—C11177.0 (2)C22—C21—C29—C281.4 (4)
C8—C7—C12—N1179.5 (2)N1—C21—C29—C28176.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3A···N2i0.932.703.625 (3)172
C15—H15B···N2i0.962.873.807 (4)162
C29—H29A···Cg1ii0.932.813.525 (3)134
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC29H30N2
Mr406.55
Crystal system, space groupTriclinic, 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)
V3)1160.1 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.980, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
4710, 4260, 2838
Rint0.025
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.171, 1.00
No. of reflections4260
No. of parameters281
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3A···N2i0.932.703.625 (3)172.1
C15—H15B···N2i0.962.873.807 (4)162
C29—H29A···Cg1ii0.932.813.525 (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

First citationAllen, 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
First citationEnraf–Nonius (1994). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). CAD-4 EXPRESS. University of Marburg, Germany.
First citationMuci, A. R. & Buchwald, S. L. (2002). Top. Curr. Chem. 219, 131–209.  CrossRef CAS
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationOwczarczyk, Z. R. (2005). US Patent No. 2005/0131234 A1.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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