N-(9H-Fluoren-9-yl­idene)-4-methyl­aniline

Su-Zhen Bai; Xin-Hua Lou; Hong-Mei Li; Hui Shi

doi:10.1107/S1600536809020765

. 2009 Jun 10;65(Pt 7):o1545. doi: 10.1107/S1600536809020765

N-(9H-Fluoren-9-ylidene)-4-methylaniline

Su-Zhen Bai ^a, Xin-Hua Lou ^b,^*, Hong-Mei Li ^c, Hui Shi ^a

PMCID: PMC2969441 PMID: 21582831

Abstract

In the title compound, C₂₀H₁₅N, the fluorene unit is essentially planar [r.m.s. deviation 0.0334 Å] and the benzene ring bound to the imine N atom bears a methyl group which is nearly coplanar [dihedral angle 0.5 (1)°]. The dihedral angle between the substituent benzene ring and the 9H-fluoren-9-imine unit is 71.1 (3)°. Intermolecular π–π interactions between the benzene rings of adjacent fluorene units [centroid–centroid distance 3.8081 (13) Å] are present in the crystal structure, resulting in a one-dimensional supramolecular architecture.

Related literature

For the properties of Schiff bases, see: Xu et al. (2007 ▶); Tanaka et al. (2006 ▶). For the properties of fluorene derivatives, see: Saragi et al. (2004 ▶). For related structures, see: Glagovich et al. (2004 ▶); Peters et al. (1998 ▶); Pierre et al. (1997 ▶).

Experimental

Crystal data

C₂₀H₁₅N
M _r = 269.33
Monoclinic,
a = 5.6423 (10) Å
b = 12.187 (2) Å
c = 21.310 (4) Å
β = 94.441 (2)°
V = 1460.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 K
0.35 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.994
10793 measured reflections
2711 independent reflections
1779 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.115
S = 1.01
2711 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809020765/si2179sup1.cif

e-65-o1545-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020765/si2179Isup2.hkl

e-65-o1545-Isup2.hkl^{(133.1KB, hkl)}

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

Acknowledgments

This work was supported by the High-Level Personnel to Start Research Fund of Pingdingshan University (No. 2006044).

supplementary crystallographic information

Comment

Schiff bases have received much attention during the past decades because of their strong coordination capability and diverse biological activities (Xu et al., 2007; Tanaka et al., 2006). In addition, fluorene derivatives have found many applications in chemistry, especially in the optoelectronic area (Saragi et al., 2004). In view of these important properties, the crystal structure of the title compond has been determined.

In the title compound (Fig.1), the C12—N1—C14 angle of 120.76 (15)° and the N1—C12 bond distance of 1.278 (2)Å are in close agreement with the similar Nfluorenylideneaniline (Glagovich et al., 2004; Peters et al., 1998; Pierre et al., 1997). The fluorene unit is essentially planar and the benzene ring bound to the imine N atom bears a methyl that is nearly coplanar. The dihedral angle between the substituent benzene ring and the 9H-fluoren-9-imine unit is 108.9 (3)°. Intermolecular π···π interactions between the benzene rings of adjacent fluorene units [centroid-centroid distance is 3.8081 (13) Å, the average perpendicular distance is 3.469 Å, the dihedral angle between the rings is 3.7°, symmetry code = -1 + x, y, z] are present in the crystal structure, resulting in a one-dimensional supramolecular architecture (Fig. 2).

Experimental

The title compound was obtained from the condensation reaction of 9-fluorenone and 4-methylaniline as described in literature (Glagovich et al., 2004) and recrystallized from ethanol solution at room temperature to give the desired product as yellow crystals suitable for single-crystal X-ray diffraction.