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

Xin-hua Lu; Jin Hu

doi:10.1107/S1600536812025962

. 2012 Jun 13;68(Pt 7):o2093. doi: 10.1107/S1600536812025962

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

Xin-hua Lu ^a,^*, Jin Hu ^b

PMCID: PMC3393907 PMID: 22798772

Abstract

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 ▶); Antoniadis et al. (1994 ▶); Tonzola et al. (2003 ▶). For the synthesis of the title compound, see: Crivello & Lam 1976 ▶). Scheme faint, resolution poor

Experimental

Crystal data

C₃₆H₃₆N₂
M _r = 496.67
Triclinic,
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 ▶) T _min = 0.979, T _max = 0.993
5301 measured reflections
4978 independent reflections
2825 reflections with I > 2σ(I)
R _int = 0.046
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.147
S = 1.01
4978 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025962/go2057sup1.cif

e-68-o2093-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025962/go2057Isup2.hkl

e-68-o2093-Isup2.hkl^{(243.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.