7-(4-Meth­oxy­phen­yl)-4,9-dimethyl-N-(4-methyl­phen­yl)-5,12-diaza­tetra­phen-6-amine

Vennila, K.N.; Prabha, K.; Prasad, K.J.R.; Velmurugan, D.

doi:10.1107/S1600536811006209

Volume 67
Part 4
Pages o762-o763
April 2011

Received 3 January 2011
Accepted 18 February 2011
Online 2 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.053
wR = 0.181
Data-to-parameter ratio = 19.0
Details

7-(4-Methoxyphenyl)-4,9-dimethyl-N-(4-methylphenyl)-5,12-diazatetraphen-6-amine

K. N. Vennila,^a K. Prabha,^b K. J. Rajendra Prasad ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, India
Correspondence e-mail: dvelmurugan@unom.ac.in

In the title compound, C₃₂H₂₇N₃O, the fused tetracycilc ring system is essentially planar [r.m.s. deviation = 0.07 (7) Å]. An intramolecular N-H [pi] (arene) interaction and a weak intramolecular C-HN hydrogen bond may influence the molecular conformation. In the crystal, weak intermolecular C-HN hydrogen bonds link the molecules into centrosymmetric dimers, forming R₂²(14) motifs. In addition, weak [pi] - [pi] stacking interactions with centroid-centroid distances in the range 3.578 (1)-3.739 (1) Å provide further stabilization.

Related literature

For the biological activity of naphthyridine derivatives, see: Gopalsamy et al. (2007); Kim et al. (2009); Nittoli et al. (2010); Bedard et al. (2000). For the structures of related naphthrydine derivatives, see: Peng et al. (2009); Seebacher et al . (2010); Vennila et al. (2010a,b). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₃₂H₂₇N₃O
M_r = 469.57
Monoclinic, P 2₁ /c
a = 8.3816 (6) Å
b = 23.1651 (13) Å
c = 12.8548 (7) Å
= 91.171 (3)°
V = 2495.4 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.29 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.978, T_max = 0.983
24206 measured reflections
6239 independent reflections
3904 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.181
S = 0.95
6239 reflections
329 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17-C22 ring.

D-HA	D-H	HA	DA	D-HA
N3-H3Cg	0.86	2.48	3.336 (3)	176
C28-H28N1	0.93	2.37	2.927 (3)	118
C18-H18N2ⁱ	0.93	2.55	3.435 (2)	159
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 data and figures for this paper are available from the IUCr electronic archives (Reference: LH5193 ).

Acknowledgements

KNV thanks the CSIR, New Delhi, for financial assistance in the form of a Senior Research Fellowship. DV acknowledges the Department of Science and Technology (DST) for providing data-collection facilities under the TBI program and also thanks the DST for financial support under the UGC-SAP and DST-FIST programs.

References

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organic compounds