(E)-N-(Anthracen-9-yl­methyl­idene)-4-nitro­aniline

K Geetha; D K Andrew Prasanna Kumar; D Lakshmanan; R Savitha; S Murugavel

doi:10.1107/S1600536811035859

. 2011 Sep 14;67(Pt 10):o2577. doi: 10.1107/S1600536811035859

(E)-N-(Anthracen-9-ylmethylidene)-4-nitroaniline

K Geetha ^a,^*, D K Andrew Prasanna Kumar ^b, D Lakshmanan ^c, R Savitha ^a, S Murugavel ^d,^*

PMCID: PMC3201478 PMID: 22058743

Abstract

In the title molecule, C₂₁H₁₄N₂O₂, the anthracenyl system is approximately planar [maximum deviation = 0.056 (4) Å] and is oriented at a dihedral angle of 73.6 (1)° with respect to the benzene ring. An intramolecular C—H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C—H⋯π and π–π interactions [centroid–centroid distances of 3.688 (2), 3.656 (1) and 3.716 (2) Å].

Related literature

For applications of anthracene derivatives, see: de Silva et al. (1997 ▶); Klarner et al. (1998 ▶); Han et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Arumugam et al. (2011 ▶); Villalpando et al. (2010 ▶).

Experimental

Crystal data

C₂₁H₁₄N₂O₂
M _r = 326.34
Triclinic,
a = 8.3634 (4) Å
b = 8.9045 (4) Å
c = 11.5119 (6) Å
α = 75.235 (2)°
β = 84.544 (3)°
γ = 75.054 (2)°
V = 800.56 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T _min = 0.924, T _max = 0.991
15391 measured reflections
2983 independent reflections
1870 reflections with I > 2σ(I)
R _int = 0.151

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.306
S = 1.12
2983 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035859/im2315sup1.cif

e-67-o2577-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035859/im2315Isup2.hkl

e-67-o2577-Isup2.hkl^{(146.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N1	0.93	2.37	2.980 (4)	123
C20—H20⋯Cg1ⁱ	0.93	2.86	3.717 (3)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

SM and KG thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Anthracene is an attractive material in its photochemical and electrochemical properties and is used as a potential medium for photoconductive (de Silva et al., 1997) and electroluminescence (Klarner et al., 1998) devices. Furthermore, anthracene derivatives exhibited anticancer activity has also been reported recently (Han et al., 2009). Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound have been carried out.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The anthracene moiety (C1-C14) is essentially planar [maximum deviation = -0.056 (4) Å for the C11 atom] and shows a dihedral angle of 73.6 (1)° with respect to the (C16-C21) benzene ring. The nitro group is slightly twisted away from the plane of the attached benzene ring [C20-C19-N2-O1 = -4.9 (5) ° and C18-C19-N2-O2 = -6.7 (5) °]. The geometric parameters of the title molecule agrees well with those reported for similar structures (Arumugam et al., 2011, Villalpando et al., 2010).

In addition to van der Waals interactions, the crystal packing is stabilized by C-H···N and C-H···π hydrogen bonds as well as by π-π interactions. The intramolecular C12-H12···N1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The crystal packing (Fig. 2) is stabilized by C-H···π interactions between H20 and the neighbouring C1-C6 benzene ring, with a C20-H20···Cg1ⁱ separation of 2.86 Å (Fig. 2, Table 1; Cg1 is the centroid of the C1-C6 benzene ring, symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by π-π interactions with Cg1···Cg3ⁱⁱ, Cg2···Cg2ⁱⁱ and Cg2···Cg3ⁱⁱ separations of 3.688 (2) Å, 3.656 (1) Å and 3.716 (2) Å, respectively (Fig. 2; Cg1, Cg2 and Cg3 are the centroids of the C1-C6 benzene ring,C1/C6/C7/C8/C13/C14 benzene ring and C8-C13 benzene ring , respectively, symmetry code as in Fig. 2).

Experimental

Equimolar amounts of p-nitroaniline and 9-anthracenecarboxaldehyde were suspended in ethanol at a concentration of 0.1 M and the reaction mixture was refluxed overnight under vigorous stirring. Afterwards the mixture was cooled down and filtered. Recrystallization of the crude product from hexane : CHCl₃ (1 : 1) yielded orange crystals of title compound (Yield 74 %).