N-(Anthracen-9-ylmeth­yl)adamantan-1-amine

Wei-Qiang Fan; Fu-Xiao Chen

doi:10.1107/S1600536812022106

. 2012 May 19;68(Pt 6):o1831. doi: 10.1107/S1600536812022106

N-(Anthracen-9-ylmethyl)adamantan-1-amine

Wei-Qiang Fan ^a,^*, Fu-Xiao Chen ^b

PMCID: PMC3379404 PMID: 22719602

Abstract

In the crystal stucture of the of the title compound, C₂₅H₂₇N, stong π–π interactions are found between adjacent anthracene fragments, with a shortest centroid–centroid distance of 3.5750 (9) Å.

Related literature

Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH sensors, see: Bernhardt et al. (2001 ▶), Chen & Chen (2004 ▶); Gunnlaugsson et al. (2003 ▶); Kim & Yoon (2002 ▶)

Experimental

Crystal data

C₂₅H₂₇N
M _r = 341.26
Orthorhombic,
a = 9.9546 (4) Å
b = 42.1921 (19) Å
c = 8.6133 (4) Å
V = 3617.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.35 × 0.24 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.975, T _max = 0.998
18689 measured reflections
3594 independent reflections
3089 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.104
S = 1.03
3594 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022106/aa2056sup1.cif

e-68-o1831-sup1.cif^{(22KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022106/aa2056Isup2.hkl

e-68-o1831-Isup2.hkl^{(172.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022106/aa2056Isup3.cml

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

Acknowledgments

We thank the Start-up Foundation for Advanced Professionals of Jiangsu University (11JDG105) for support.

supplementary crystallographic information

Comment

Anthracene derivatives have been widely used in the field of anion recognition, metal ionfluorescent sensors, as well as pH sensors (Gunnlaugsson et al., 2003; Chen & Chen, 2004; Kim & Yoon, 2002; Bernhardt et al. 2001) because of their excellent photophysical properties and high fluorescence.

In the crystals of the title compound (Fig. 1), there are two π–π interactions between benzene rings of the ajacent anthracene fragments with the distances Cg1···Cg2ⁱ = 3.5750 (9) Å and Cg1···Cg3ⁱ = 4.0043 (10) Å. (Cg1, Cg2 and Cg3 are the centroids of the rings [C1/C5 and C14], [C5/C7 and C12/C14] and [C7/C12], respectively; symmetry code: (i) 1/2 - x, y, z + 1/2) forming one-dimensional supramolecular chains along c axis direction (Fig. 2).

Experimental

9-Anthracenecarboxaldehyde (2.06 g, 10 mmol) was added into a solution of amantadine (1.51 g, 10 mmol) in ethanol. Yellow precipitate was formed atfer string for 1 h. The yellow Schiff base was filtrated and dryed. NaBH₄ (7.56 g, 20 mmol) was added into a solution of the Schiff base in anhydrous methanol (120 ml). After 3 h, the white solid, 9-[(adamantan-1-ylamino)methyl]anthracene, was obtained by reduced pressure distillation, extraction and drying. The colourless block-shaped crystals of the title compound suitable for X-ray analysis were obtained by recrystallization from ethanol.