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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2093
https://doi.org/10.1107/S1600536812025962

6,7,15,16-Tetra­hydro-5,14-di­butyl­benzo[1,2-c:4,5-c′]diacridine

Xin-hua Lua* and Jin Hub

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and bDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
*Correspondence e-mail: jennydaocaoren@126.com

(Received 27 May 2012; accepted 7 June 2012; online 13 June 2012)

The unit cell of the title compound, C36H36N2, contains two independent mol­ecules which are located about inversion centers. In each molecule the quinoline rings are almost planar, with mean deviations of 0.0302 (1) and 0.0173 (1) Å. In the crystal, mol­ecules are linked by C—H⋯π inter­actions into a three-dimensional network.

Related literature

For background to the applications of the title compound, an important organic synthesis inter­mediate, see: Kolosov et al. (2002[Kolosov, S., Adamovich, V., Djurovich, P., Thompson, M. E. & Adachi, C. (2002). J. Am. Chem. Soc. 124, 9945-9954.]); Antoniadis et al. (1994[Antoniadis, H., Hsieh, B. R., Abkowitz, M. A., Jenekhe, S. A. & Stolka, M. (1994). Synth. Met. 62, 265-271.]); Tonzola et al. (2003[Tonzola, C. J., Alam, M. M., Kaminsky, W. & Jenekhe, S. A. (2003). J. Am. Chem. Soc. 125, 13548-13558.]). For the synthesis of the title compound, see: Crivello & Lam 1976[Crivello, J. V. & Lam, J. H. W. (1976). J. Polym. Sci. Polym. Symp. 56, 383-385.]).

[Scheme 1]
Scheme faint, resolution poor

Experimental

Crystal data

  • C36H36N2

  • Mr = 496.67

  • Triclinic, [P \overline 1]

  • a = 9.6010 (19) Å

  • b = 10.386 (2) Å

  • c = 14.625 (3) Å

  • α = 77.44 (3)°

  • β = 78.43 (3)°

  • γ = 73.92 (3)°

  • V = 1352.4 (5) 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 = 0.979, Tmax = 0.993

  • 5301 measured reflections

  • 4978 independent reflections

  • 2825 reflections with I > 2σ(I)

  • Rint = 0.046

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

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.147

  • S = 1.01

  • 4978 reflections

  • 344 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg23, Cg4 and Cg2 are the centroids of the of ring containing N2, the ring containing C15 and the ring containing C2, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C17—H17B⋯Cg23 0.97 2.79 3.688 (3) 155
C31—H31A⋯Cg4i 0.97 2.70 3.630 (3) 160
C34—H34B⋯Cg2ii 0.97 2.81 3.669 (3) 148
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025962/go2057sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025962/go2057Isup2.hkl

checkCIF report


Comment top

The title compound is an new compound, which can be utilized to synthesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for applications in electronic and optoelectronic devices including light-emitting diodes (Kolosov et al., 2002), thin film transistors, and photovoltaic cells (Antoniadis et al., 1994).

The molecular structure of (I) is shown in Fig. 1. The asymmetric unit contains two distinct title molecules of C36H36N2. In the molecules of C36H36N2, the quinoline rings are almost planar. The values of the mean deviation for quinoline rings are 0.0302 (1) Å and 0.0173 (1) Å respectively. The molecules are linked into a three-dimensional network by C—H···π interactions, C17–H17B···Cg23 links the two molecules in the asymmetric unit, C31–H31A···Cg4(-1+x,y,z) and C34–H34B···Cg2(1-x,-y,1-z), where Cg23, Cg4 and Cg2 contain atoms N2, C15 and C2 respectively.

Related literature top

For background to the applications of the title compound, an important organic synthesis intermediate, see: Kolosov et al. (2002); Antoniadis et al. (1994); Tonzola et al. (2003). For the synthesis of the title compound, see: Crivello & Lam 1976).

Experimental top

The title compound, (I) was prepared by a method reported in literature (Crivello & Lam, 1976). The crystals were obtained by dissolving (I) (0.1 g) in methanol (30 ml) and evaporating the solvent slowly at room temperature for about 15 d.

Refinement top

All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H(aromatic) = 0.93, Å C—H(CH2) 0.97Å with Uiso= 1.2Ueq(C) and C—H(methyl), 0.96Å with Uiso = 1.5Ueq(C).

Structure description top

The title compound is an new compound, which can be utilized to synthesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for applications in electronic and optoelectronic devices including light-emitting diodes (Kolosov et al., 2002), thin film transistors, and photovoltaic cells (Antoniadis et al., 1994).

The molecular structure of (I) is shown in Fig. 1. The asymmetric unit contains two distinct title molecules of C36H36N2. In the molecules of C36H36N2, the quinoline rings are almost planar. The values of the mean deviation for quinoline rings are 0.0302 (1) Å and 0.0173 (1) Å respectively. The molecules are linked into a three-dimensional network by C—H···π interactions, C17–H17B···Cg23 links the two molecules in the asymmetric unit, C31–H31A···Cg4(-1+x,y,z) and C34–H34B···Cg2(1-x,-y,1-z), where Cg23, Cg4 and Cg2 contain atoms N2, C15 and C2 respectively.

For background to the applications of the title compound, an important organic synthesis intermediate, see: Kolosov et al. (2002); Antoniadis et al. (1994); Tonzola et al. (2003). For the synthesis of the title compound, see: Crivello & Lam 1976).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The second molecule in the asymmetric unit.
6,7,15,16-Tetrahydro-5,14-dibutylbenzo[1,2-c:4,5-c']diacridine top
Crystal data top
C36H36N2Z = 2
Mr = 496.67F(000) = 532
Triclinic, P1Dx = 1.220 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6010 (19) ÅCell parameters from 25 reflections
b = 10.386 (2) Åθ = 9–13°
c = 14.625 (3) ŵ = 0.07 mm−1
α = 77.44 (3)°T = 293 K
β = 78.43 (3)°Block, colourless
γ = 73.92 (3)°0.30 × 0.20 × 0.10 mm
V = 1352.4 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer		2825 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 25.4°, θmin = 1.4°
ω/2θ scansh = 0→11
Absorption correction: ψ scan
(North et al., 1968)		k = −12→12
Tmin = 0.979, Tmax = 0.993l = −17→17
5301 measured reflections3 standard reflections every 200 reflections
4978 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)] = 0.058H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.2931P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4978 reflectionsΔρmax = 0.17 e Å−3
344 parametersΔρmin = −0.18 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0129 (14)
Crystal data top
C36H36N2γ = 73.92 (3)°
Mr = 496.67V = 1352.4 (5) Å3
Triclinic, P1Z = 2
a = 9.6010 (19) ÅMo Kα radiation
b = 10.386 (2) ŵ = 0.07 mm−1
c = 14.625 (3) ÅT = 293 K
α = 77.44 (3)°0.30 × 0.20 × 0.10 mm
β = 78.43 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2825 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.046
Tmin = 0.979, Tmax = 0.9933 standard reflections every 200 reflections
5301 measured reflections intensity decay: 1%
4978 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å−3
4978 reflectionsΔρmin = −0.18 e Å−3
344 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
N10.2438 (2)−0.0834 (2)0.71474 (14)0.0489 (5)
C10.1692 (3)−0.1557 (3)0.78803 (17)0.0484 (6)
C20.0806 (3)−0.0862 (3)0.86002 (19)0.0602 (8)
H20.07210.00640.85490.072*
C30.0073 (3)−0.1526 (3)0.9370 (2)0.0677 (8)
H3−0.0506−0.10550.98410.081*
C40.0192 (3)−0.2912 (3)0.9450 (2)0.0706 (9)
H4−0.0291−0.33680.99840.085*
C50.1004 (3)−0.3604 (3)0.8759 (2)0.0643 (8)
H50.1044−0.45230.88180.077*
C60.1794 (3)−0.2955 (3)0.79478 (18)0.0501 (7)
C70.2692 (3)−0.3633 (3)0.72059 (19)0.0513 (7)
C80.3490 (3)−0.2911 (3)0.64949 (18)0.0492 (7)
C90.3325 (3)−0.1503 (3)0.64924 (17)0.0463 (6)
C100.2797 (3)−0.5116 (3)0.7225 (2)0.0587 (7)
H10A0.2959−0.52800.65800.070*
H10B0.1873−0.53230.75360.070*
C110.4033 (3)−0.6070 (3)0.7741 (2)0.0696 (9)
H11A0.4951−0.58350.74510.084*
H11B0.3846−0.59400.83960.084*
C120.4181 (4)−0.7567 (3)0.7716 (2)0.0849 (10)
H12A0.4283−0.76820.70630.102*
H12B0.5064−0.81110.79650.102*
C130.2909 (4)−0.8070 (4)0.8270 (3)0.1278 (16)
H13A0.3046−0.90050.82210.192*
H13B0.2030−0.75360.80270.192*
H13C0.2826−0.79950.89230.192*
C140.4177 (3)−0.0722 (3)0.57196 (16)0.0453 (6)
C150.3755 (3)0.0684 (3)0.55122 (17)0.0478 (6)
H150.29130.11440.58570.057*
C160.4559 (3)0.1419 (2)0.48028 (17)0.0470 (6)
C170.4119 (3)0.2944 (3)0.45672 (19)0.0560 (7)
H17A0.34950.33060.51080.067*
H17B0.35660.32160.40410.067*
C180.4536 (3)−0.3526 (3)0.56941 (19)0.0582 (7)
H18A0.4042−0.33390.51450.070*
H18B0.4838−0.45050.58840.070*
N20.0362 (2)0.3476 (2)0.39887 (14)0.0527 (6)
C190.0721 (3)0.4580 (3)0.33770 (18)0.0516 (7)
C200.0175 (3)0.5861 (3)0.3663 (2)0.0633 (8)
H20−0.03810.59220.42580.076*
C210.0446 (3)0.7013 (3)0.3081 (2)0.0721 (9)
H210.00710.78530.32760.087*
C220.1296 (3)0.6918 (3)0.2190 (2)0.0778 (9)
H220.14770.77020.17900.093*
C230.1860 (3)0.5692 (3)0.1901 (2)0.0698 (9)
H230.24280.56530.13080.084*
C240.1601 (3)0.4472 (3)0.24841 (18)0.0540 (7)
C250.2160 (3)0.3153 (3)0.22227 (17)0.0514 (7)
C260.1829 (3)0.2053 (3)0.28583 (17)0.0484 (6)
C270.0882 (3)0.2267 (3)0.37299 (17)0.0462 (6)
C280.0434 (3)0.1101 (3)0.43810 (17)0.0474 (6)
C29−0.0784 (3)0.1306 (3)0.50862 (18)0.0504 (7)
H29−0.13150.21890.51420.060*
C30−0.1223 (3)0.0226 (3)0.57047 (17)0.0484 (7)
C31−0.2556 (3)0.0434 (3)0.64468 (18)0.0549 (7)
H31A−0.33940.03720.61970.066*
H31B−0.27580.13380.65990.066*
C320.3110 (3)0.3004 (3)0.12746 (17)0.0576 (7)
H32A0.27350.37690.08020.069*
H32B0.30540.21810.10880.069*
C330.4715 (3)0.2940 (3)0.12995 (18)0.0614 (8)
H33A0.47610.37420.15190.074*
H33B0.50990.21500.17520.074*
C340.5678 (3)0.2860 (3)0.03419 (19)0.0687 (9)
H34A0.52320.3593−0.01260.082*
H34B0.66240.29950.03800.082*
C350.5909 (4)0.1531 (4)0.0016 (3)0.1012 (12)
H35A0.65190.1544−0.05910.152*
H35B0.49790.1398−0.00360.152*
H35C0.63750.08020.04660.152*
C360.2353 (3)0.0614 (3)0.26561 (18)0.0593 (7)
H36A0.32780.05240.22310.071*
H36B0.16470.04360.23400.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0501 (13)0.0521 (13)0.0426 (12)−0.0117 (11)−0.0038 (11)−0.0076 (10)
C10.0457 (15)0.0557 (17)0.0456 (15)−0.0160 (13)−0.0072 (13)−0.0074 (13)
C20.0566 (18)0.070 (2)0.0517 (17)−0.0150 (15)−0.0016 (15)−0.0124 (15)
C30.0606 (19)0.086 (2)0.0555 (19)−0.0249 (17)0.0058 (15)−0.0136 (16)
C40.065 (2)0.092 (3)0.0564 (19)−0.0374 (18)0.0008 (16)−0.0008 (17)
C50.0598 (18)0.073 (2)0.0630 (19)−0.0289 (16)−0.0078 (16)−0.0025 (16)
C60.0418 (15)0.0609 (18)0.0508 (16)−0.0178 (13)−0.0134 (13)−0.0032 (14)
C70.0474 (16)0.0526 (17)0.0568 (17)−0.0140 (13)−0.0164 (14)−0.0049 (13)
C80.0522 (16)0.0496 (17)0.0484 (15)−0.0128 (13)−0.0114 (13)−0.0097 (13)
C90.0475 (15)0.0490 (16)0.0416 (15)−0.0081 (12)−0.0097 (13)−0.0079 (12)
C100.0562 (17)0.0561 (18)0.0684 (19)−0.0200 (14)−0.0146 (15)−0.0077 (14)
C110.0596 (19)0.065 (2)0.082 (2)−0.0155 (16)−0.0184 (17)−0.0023 (16)
C120.089 (3)0.064 (2)0.088 (2)0.0050 (19)−0.014 (2)−0.0139 (18)
C130.112 (3)0.079 (3)0.188 (5)−0.042 (2)−0.032 (3)0.019 (3)
C140.0476 (15)0.0481 (16)0.0382 (14)−0.0074 (12)−0.0065 (12)−0.0082 (12)
C150.0446 (15)0.0498 (17)0.0446 (15)−0.0033 (12)−0.0035 (12)−0.0124 (12)
C160.0498 (16)0.0461 (16)0.0424 (15)−0.0069 (13)−0.0067 (13)−0.0085 (12)
C170.0567 (17)0.0493 (17)0.0553 (17)−0.0038 (13)−0.0042 (14)−0.0108 (13)
C180.0668 (19)0.0489 (17)0.0585 (17)−0.0105 (14)−0.0090 (15)−0.0132 (13)
N20.0486 (13)0.0589 (15)0.0485 (13)−0.0124 (11)−0.0039 (11)−0.0091 (12)
C190.0442 (15)0.0585 (18)0.0492 (16)−0.0112 (13)−0.0075 (13)−0.0046 (14)
C200.0628 (19)0.067 (2)0.0569 (18)−0.0148 (16)−0.0050 (15)−0.0095 (16)
C210.075 (2)0.062 (2)0.075 (2)−0.0171 (16)−0.0064 (18)−0.0061 (17)
C220.074 (2)0.065 (2)0.081 (2)−0.0166 (18)−0.0017 (19)0.0054 (18)
C230.0600 (19)0.077 (2)0.0582 (19)−0.0126 (17)0.0006 (15)0.0039 (17)
C240.0426 (15)0.068 (2)0.0486 (16)−0.0159 (14)−0.0062 (13)−0.0008 (14)
C250.0377 (15)0.070 (2)0.0446 (15)−0.0127 (13)−0.0071 (12)−0.0056 (14)
C260.0424 (15)0.0599 (18)0.0438 (15)−0.0132 (13)−0.0066 (12)−0.0095 (13)
C270.0374 (14)0.0602 (18)0.0417 (15)−0.0123 (13)−0.0043 (12)−0.0109 (13)
C280.0380 (14)0.0615 (18)0.0430 (15)−0.0135 (13)−0.0029 (12)−0.0107 (13)
C290.0417 (15)0.0557 (17)0.0513 (16)−0.0086 (12)−0.0031 (13)−0.0118 (13)
C300.0371 (14)0.0607 (18)0.0459 (15)−0.0109 (13)0.0005 (12)−0.0139 (13)
C310.0429 (15)0.0649 (18)0.0529 (16)−0.0107 (13)0.0026 (13)−0.0135 (14)
C320.0470 (16)0.080 (2)0.0444 (16)−0.0184 (14)−0.0050 (13)−0.0061 (14)
C330.0485 (17)0.084 (2)0.0507 (17)−0.0206 (15)−0.0019 (14)−0.0096 (15)
C340.0504 (17)0.098 (3)0.0561 (18)−0.0258 (17)0.0003 (15)−0.0065 (17)
C350.088 (3)0.117 (3)0.094 (3)−0.018 (2)0.010 (2)−0.042 (2)
C360.0523 (17)0.078 (2)0.0473 (16)−0.0182 (15)0.0034 (13)−0.0170 (15)
Geometric parameters (Å, º) top
N1—C91.327 (3)N2—C271.324 (3)
N1—C11.366 (3)N2—C191.373 (3)
C1—C21.409 (3)C19—C201.409 (4)
C1—C61.410 (3)C19—C241.414 (3)
C2—C31.360 (4)C20—C211.366 (4)
C2—H20.9300C20—H200.9300
C3—C41.393 (4)C21—C221.399 (4)
C3—H30.9300C21—H210.9300
C4—C51.355 (4)C22—C231.362 (4)
C4—H40.9300C22—H220.9300
C5—C61.419 (4)C23—C241.419 (4)
C5—H50.9300C23—H230.9300
C6—C71.427 (4)C24—C251.431 (4)
C7—C81.375 (3)C25—C261.376 (3)
C7—C101.509 (3)C25—C321.512 (3)
C8—C91.426 (3)C26—C271.431 (3)
C8—C181.512 (3)C26—C361.513 (4)
C9—C141.484 (3)C27—C281.476 (3)
C10—C111.530 (4)C28—C30ii1.396 (3)
C10—H10A0.9700C28—C291.397 (3)
C10—H10B0.9700C29—C301.386 (3)
C11—C121.529 (4)C29—H290.9300
C11—H11A0.9700C30—C28ii1.396 (3)
C11—H11B0.9700C30—C311.502 (3)
C12—C131.481 (4)C31—C36ii1.519 (4)
C12—H12A0.9700C31—H31A0.9700
C12—H12B0.9700C31—H31B0.9700
C13—H13A0.9600C32—C331.531 (3)
C13—H13B0.9600C32—H32A0.9700
C13—H13C0.9600C32—H32B0.9700
C14—C151.384 (3)C33—C341.521 (3)
C14—C16i1.401 (3)C33—H33A0.9700
C15—C161.384 (3)C33—H33B0.9700
C15—H150.9300C34—C351.502 (4)
C16—C14i1.401 (3)C34—H34A0.9700
C16—C171.502 (3)C34—H34B0.9700
C17—C18i1.520 (3)C35—H35A0.9600
C17—H17A0.9700C35—H35B0.9600
C17—H17B0.9700C35—H35C0.9600
C18—C17i1.520 (3)C36—C31ii1.519 (4)
C18—H18A0.9700C36—H36A0.9700
C18—H18B0.9700C36—H36B0.9700
C9—N1—C1117.5 (2)C27—N2—C19118.1 (2)
N1—C1—C2117.6 (2)N2—C19—C20117.7 (2)
N1—C1—C6122.9 (2)N2—C19—C24122.5 (2)
C2—C1—C6119.5 (2)C20—C19—C24119.8 (3)
C3—C2—C1120.9 (3)C21—C20—C19121.1 (3)
C3—C2—H2119.5C21—C20—H20119.4
C1—C2—H2119.5C19—C20—H20119.4
C2—C3—C4119.8 (3)C20—C21—C22119.4 (3)
C2—C3—H3120.1C20—C21—H21120.3
C4—C3—H3120.1C22—C21—H21120.3
C5—C4—C3120.7 (3)C23—C22—C21120.8 (3)
C5—C4—H4119.6C23—C22—H22119.6
C3—C4—H4119.6C21—C22—H22119.6
C4—C5—C6121.3 (3)C22—C23—C24121.5 (3)
C4—C5—H5119.4C22—C23—H23119.2
C6—C5—H5119.4C24—C23—H23119.2
C1—C6—C5117.6 (3)C19—C24—C23117.3 (3)
C1—C6—C7118.4 (2)C19—C24—C25118.4 (2)
C5—C6—C7124.0 (3)C23—C24—C25124.3 (3)
C8—C7—C6118.2 (2)C26—C25—C24118.3 (2)
C8—C7—C10121.2 (2)C26—C25—C32122.1 (3)
C6—C7—C10120.6 (2)C24—C25—C32119.6 (2)
C7—C8—C9119.2 (2)C25—C26—C27119.4 (2)
C7—C8—C18123.5 (2)C25—C26—C36122.9 (2)
C9—C8—C18117.3 (2)C27—C26—C36117.7 (2)
N1—C9—C8123.6 (2)N2—C27—C26123.2 (2)
N1—C9—C14117.2 (2)N2—C27—C28117.2 (2)
C8—C9—C14119.2 (2)C26—C27—C28119.5 (2)
C7—C10—C11112.8 (2)C30ii—C28—C29119.0 (2)
C7—C10—H10A109.0C30ii—C28—C27120.2 (2)
C11—C10—H10A109.0C29—C28—C27120.8 (2)
C7—C10—H10B109.0C30—C29—C28121.7 (2)
C11—C10—H10B109.0C30—C29—H29119.1
H10A—C10—H10B107.8C28—C29—H29119.1
C12—C11—C10112.5 (2)C29—C30—C28ii119.3 (2)
C12—C11—H11A109.1C29—C30—C31122.1 (2)
C10—C11—H11A109.1C28ii—C30—C31118.6 (2)
C12—C11—H11B109.1C30—C31—C36ii111.8 (2)
C10—C11—H11B109.1C30—C31—H31A109.3
H11A—C11—H11B107.8C36ii—C31—H31A109.3
C13—C12—C11112.8 (3)C30—C31—H31B109.3
C13—C12—H12A109.0C36ii—C31—H31B109.3
C11—C12—H12A109.0H31A—C31—H31B107.9
C13—C12—H12B109.0C25—C32—C33112.3 (2)
C11—C12—H12B109.0C25—C32—H32A109.1
H12A—C12—H12B107.8C33—C32—H32A109.1
C12—C13—H13A109.5C25—C32—H32B109.1
C12—C13—H13B109.5C33—C32—H32B109.1
H13A—C13—H13B109.5H32A—C32—H32B107.9
C12—C13—H13C109.5C34—C33—C32113.3 (2)
H13A—C13—H13C109.5C34—C33—H33A108.9
H13B—C13—H13C109.5C32—C33—H33A108.9
C15—C14—C16i119.4 (2)C34—C33—H33B108.9
C15—C14—C9121.3 (2)C32—C33—H33B108.9
C16i—C14—C9119.4 (2)H33A—C33—H33B107.7
C16—C15—C14121.5 (2)C35—C34—C33113.4 (3)
C16—C15—H15119.2C35—C34—H34A108.9
C14—C15—H15119.2C33—C34—H34A108.9
C15—C16—C14i119.1 (2)C35—C34—H34B108.9
C15—C16—C17122.3 (2)C33—C34—H34B108.9
C14i—C16—C17118.6 (2)H34A—C34—H34B107.7
C16—C17—C18i110.7 (2)C34—C35—H35A109.5
C16—C17—H17A109.5C34—C35—H35B109.5
C18i—C17—H17A109.5H35A—C35—H35B109.5
C16—C17—H17B109.5C34—C35—H35C109.5
C18i—C17—H17B109.5H35A—C35—H35C109.5
H17A—C17—H17B108.1H35B—C35—H35C109.5
C8—C18—C17i110.8 (2)C26—C36—C31ii112.2 (2)
C8—C18—H18A109.5C26—C36—H36A109.2
C17i—C18—H18A109.5C31ii—C36—H36A109.2
C8—C18—H18B109.5C26—C36—H36B109.2
C17i—C18—H18B109.5C31ii—C36—H36B109.2
H18A—C18—H18B108.1H36A—C36—H36B107.9
C9—N1—C1—C2176.9 (2)C27—N2—C19—C20−179.4 (2)
C9—N1—C1—C6−2.1 (3)C27—N2—C19—C240.9 (4)
N1—C1—C2—C3−177.6 (2)N2—C19—C20—C21−178.0 (3)
C6—C1—C2—C31.5 (4)C24—C19—C20—C211.8 (4)
C1—C2—C3—C4−0.2 (4)C19—C20—C21—C22−0.7 (4)
C2—C3—C4—C5−1.6 (5)C20—C21—C22—C23−0.5 (5)
C3—C4—C5—C62.0 (4)C21—C22—C23—C240.5 (5)
N1—C1—C6—C5177.9 (2)N2—C19—C24—C23178.1 (2)
C2—C1—C6—C5−1.0 (4)C20—C19—C24—C23−1.6 (4)
N1—C1—C6—C7−1.4 (4)N2—C19—C24—C25−1.4 (4)
C2—C1—C6—C7179.6 (2)C20—C19—C24—C25178.9 (2)
C4—C5—C6—C1−0.7 (4)C22—C23—C24—C190.5 (4)
C4—C5—C6—C7178.6 (3)C22—C23—C24—C25179.9 (3)
C1—C6—C7—C84.3 (3)C19—C24—C25—C26−0.8 (4)
C5—C6—C7—C8−175.0 (2)C23—C24—C25—C26179.7 (2)
C1—C6—C7—C10−177.8 (2)C19—C24—C25—C32−179.7 (2)
C5—C6—C7—C102.9 (4)C23—C24—C25—C320.9 (4)
C6—C7—C8—C9−3.8 (4)C24—C25—C26—C273.3 (3)
C10—C7—C8—C9178.3 (2)C32—C25—C26—C27−177.8 (2)
C6—C7—C8—C18177.0 (2)C24—C25—C26—C36179.7 (2)
C10—C7—C8—C18−0.8 (4)C32—C25—C26—C36−1.5 (4)
C1—N1—C9—C82.7 (4)C19—N2—C27—C261.8 (4)
C1—N1—C9—C14−177.6 (2)C19—N2—C27—C28−177.6 (2)
C7—C8—C9—N10.3 (4)C25—C26—C27—N2−4.0 (4)
C18—C8—C9—N1179.5 (2)C36—C26—C27—N2179.5 (2)
C7—C8—C9—C14−179.4 (2)C25—C26—C27—C28175.4 (2)
C18—C8—C9—C14−0.2 (3)C36—C26—C27—C28−1.2 (3)
C8—C7—C10—C1188.0 (3)N2—C27—C28—C30ii−162.5 (2)
C6—C7—C10—C11−89.8 (3)C26—C27—C28—C30ii18.1 (3)
C7—C10—C11—C12−177.2 (3)N2—C27—C28—C2917.8 (3)
C10—C11—C12—C13−67.4 (4)C26—C27—C28—C29−161.6 (2)
N1—C9—C14—C15−19.7 (3)C30ii—C28—C29—C300.4 (4)
C8—C9—C14—C15160.1 (2)C27—C28—C29—C30−180.0 (2)
N1—C9—C14—C16i159.6 (2)C28—C29—C30—C28ii−0.4 (4)
C8—C9—C14—C16i−20.7 (3)C28—C29—C30—C31−178.2 (2)
C16i—C14—C15—C16−0.3 (4)C29—C30—C31—C36ii−145.6 (2)
C9—C14—C15—C16178.9 (2)C28ii—C30—C31—C36ii36.6 (3)
C14—C15—C16—C14i0.3 (4)C26—C25—C32—C33−96.0 (3)
C14—C15—C16—C17180.0 (2)C24—C25—C32—C3382.8 (3)
C15—C16—C17—C18i143.2 (2)C25—C32—C33—C34−177.2 (2)
C14i—C16—C17—C18i−37.2 (3)C32—C33—C34—C35−69.2 (3)
C7—C8—C18—C17i−142.9 (3)C25—C26—C36—C31ii150.5 (2)
C9—C8—C18—C17i38.0 (3)C27—C26—C36—C31ii−33.1 (3)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg23, Cg4 and Cg2 are the centroids of the of ring containing N2, the ring containing C15 and the ring containing C2, respectively.
D—H···AD—HH···AD···AD—H···A
C17—H17B···Cg230.972.793.688 (3)155
C31—H31A···Cg4iii0.972.703.630 (3)160
C34—H34B···Cg2i0.972.813.669 (3)148
Symmetry codes: (i) −x+1, −y, −z+1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC36H36N2
Mr496.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.6010 (19), 10.386 (2), 14.625 (3)
α, β, γ (°)77.44 (3), 78.43 (3), 73.92 (3)
V (Å3)1352.4 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.979, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections		5301, 4978, 2825
Rint0.046
(sin θ/λ)max (Å−1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.147, 1.01
No. of reflections4978
No. of parameters344
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.17, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg23, Cg4 and Cg2 are the centroids of the of ring containing N2, the ring containing C15 and the ring containing C2, respectively.
D—H···AD—HH···AD···AD—H···A
C17—H17B···Cg230.972.793.688 (3)155
C31—H31A···Cg4i0.972.703.630 (3)160
C34—H34B···Cg2ii0.972.813.669 (3)148
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

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 First citationCrivello, J. V. & Lam, J. H. W. (1976). J. Polym. Sci. Polym. Symp. 56, 383–385.  CAS Google Scholar
 First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
 First citationKolosov, S., Adamovich, V., Djurovich, P., Thompson, M. E. & Adachi, C. (2002). J. Am. Chem. Soc. 124, 9945–9954.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTonzola, C. J., Alam, M. M., Kaminsky, W. & Jenekhe, S. A. (2003). J. Am. Chem. Soc. 125, 13548–13558.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2093
https://doi.org/10.1107/S1600536812025962
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