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

Hui Cang; Dong Jin; Si-Qing Wang; Shan Liu; Jin-Tang Wang

doi:10.1107/S1600536808016668

. 2008 Jun 7;64(Pt 7):o1221. doi: 10.1107/S1600536808016668

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

Hui Cang ^a, Dong Jin ^b, Si-Qing Wang ^a, Shan Liu ^a, Jin-Tang Wang ^a,^*

PMCID: PMC2961656 PMID: 21202858

Abstract

In the molecule of the title compound, C₁₇H₁₁N₃, the 4,5-diazafluorenylidene unit is nearly planar and is oriented with respect to the phenyl ring at a dihedral angle of 75.75 (3)°. In the crystal structure, the molecules are aligned in the [100] direction in such a way that neighbouring 4,5-diazafluorenylidene planes face each other in an antiparallel fashion.

Related literature

For related literature, see: Wang & Rillema (1997 ▶); Wang et al. (2006 ▶); Peters et al. (1998 ▶); Glagovich et al. (2004a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₁N₃
M _r = 257.29
Triclinic,
a = 7.1950 (14) Å
b = 8.5860 (17) Å
c = 11.876 (2) Å
α = 80.63 (3)°
β = 74.78 (3)°
γ = 66.46 (3)°
V = 647.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.984, T _max = 0.996
2529 measured reflections
2326 independent reflections
1642 reflections with I > 2σ(I)
R _int = 0.057
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.178
S = 1.02
2326 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); 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/S1600536808016668/hk2468sup1.cif

e-64-o1221-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016668/hk2468Isup2.hkl

e-64-o1221-Isup2.hkl^{(114.3KB, 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

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).

In the molecule of (I) (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges, which are comparable with the corresponding values in other fluorenylidene compounds (II), 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). Rings A (C1–C6), B (N2/C8–C12), C (C7/C8/C12/C13/C17) and D (N3/C13–C17) are, of course, planar. In the 4,5-diazafluorenylidene unit, the dihedral angles between the rings are B/C = 0.29 (3)°, C/D = 2.30 (3)° and B/D = 2.15 (3)°. So, rings B, C and D are nearly coplanar. The coplanar ring system is oriented with respect to ring A at a dihedral angle of 75.75 (3)°, in which it is reported as 65.1 (1)° in (II).

In the crystal structure, the molecules are aligned in the [100] direction, in such a way that neighbouring 4,5-diazafluorenylidene planes face in anti-parallel fashion (Fig. 2), as in (II).

Experimental

The title compound, (I), was prepared according to the literature method (Wang & Rillema, 1997). Crystals suitable for X-ray analysis were obtained by dissolving (I) (2.0 g, 6.3 mmol) in acetate ester solution (50 ml, 1.0 mol/L) and evaporating the solvent slowly at room temperature for about 5 d.