N-(4,5-Diaza­fluoren-9-yl­idene)-4-methyl­aniline

Hui Cang; Dong Jin; Si-Qing Wang; Bin Xu; Jin-Tang Wang

doi:10.1107/S1600536808039627

. 2008 Dec 3;65(Pt 1):o6. doi: 10.1107/S1600536808039627

N-(4,5-Diazafluoren-9-ylidene)-4-methylaniline

Hui Cang ^a, Dong Jin ^b, Si-Qing Wang ^a, Bin Xu ^a, Jin-Tang Wang ^a,^*

PMCID: PMC2967858 PMID: 21581701

Abstract

In the molecule of the title compound, C₁₈H₁₃N₃, the 4,5-diazafluorenylidene unit is nearly planar and is oriented at a dihedral angle of 66.31 (1)° with respect to the benzene ring. In the crystal structure, molecules are stacked regularly along the c axis.

Related literature

For the photochemical properties of 4-methyl-N-(4,5-diazafluorenylidene)benzenamine, see: Wang & Rillema (1997 ▶). For related structures, see: Glagovich et al. (2004a ▶,b ▶); Peters et al. (1998 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C₁₈H₁₃N₃
M _r = 271.31
Triclinic,
a = 7.5970 (15) Å
b = 8.6100 (17) Å
c = 10.998 (2) Å
α = 77.11 (3)°
β = 87.48 (3)°
γ = 85.79 (3)°
V = 699.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.977, T _max = 0.985
2742 measured reflections
2534 independent reflections
1829 reflections with I > 2σ(I)
R _int = 0.025
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.167
S = 1.00
2534 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.28 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 datablocks I, global. DOI: 10.1107/S1600536808039627/bx2187sup1.cif

e-65-000o6-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039627/bx2187Isup2.hkl

e-65-000o6-Isup2.hkl^{(124.4KB, hkl)}

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

Acknowledgments

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

supplementary crystallographic information

Comment

4-Methyl-N-(4,5-diazafluorenylidene)benzenamine, is one of the important ligands, being utilized to synthesize complexes with interesting photochemical properties (Wang & Rillema, 1997). The crystal structure of 4-methyl-N-(4,5-diazafluorenylidene)benzenamine monohydrate, (II) (Wang et al., 2006) was reported, previously. We report herein the crystal structure of the title compound, (I), Fig. 1.The bond lengths and angles are comparable with the solvated form (II), and with other fluorenylidene compounds : N-fluorenylidene-aniline-benzene (4/1) (III) (Peters et al., 1998), N-(9H-fluoren-9-ylidene)-N-(4-methoxyphenyl)amine, (IV) (Glagovich et al., 2004a) and N-9H-fluoren-9-ylidene-3,4-dimethyl- aniline, (V) (Glagovich et al., 2004b). The coplanar ring system is oriented with respect to benzene ring at a dihedral angle of 66.31 (1)°.In the crystal of the title compound, no obvious hydrogen bond is observed, and molecules are stacked regularly along c axis, Fig. 2.

Experimental

The title compound was synthesized by a method reported in literature (Wang & Rillema, 1997). The crystals were obtained by dissolving compound (I) (2.0 g, 6.3 mmol) into solution of acetic ether (50 ml, 1.0 mol/L), and evaporating the solvent slowly at room temperature for about 5 d.