N-(1-Naphth­yl)-10H-9-oxa-1,3-diaza­anthracen-4-amine

Fun, H.-K.; Chantrapromma, S.; Rai, S.; Shetty, P.; Isloor, A.M.

doi:10.1107/S1600536809004693

Volume 65
Part 3
Pages o523-o524
March 2009

Received 4 February 2009
Accepted 9 February 2009
Online 13 February 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.142
Data-to-parameter ratio = 20.3
Details

N-(1-Naphthyl)-10H-9-oxa-1,3-diazaanthracen-4-amine

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ⁺ Sankappa Rai,^c Prakash Shetty ^d and Arun M. Isloor ^e

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,^cSyngene International Ltd, Biocon Park, Plot Nos. 2 and 3, Bommasandra 4th Phase, Jigani Link Road, Bangalore 560 100, India,^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and ^eDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
Correspondence e-mail: hkfun@usm.my

In the molecule of the title compound, C₂₁H₁₅N₃O, the 10H-9-oxa-1,3-diazaanthracene ring system is slightly bent, with dihedral angles of 3.99 (6) and 4.80 (6)° between the pyran ring and the pyrimidine and benzene rings, respectively. This ring system makes a dihedral angle of 85.23 (3)° with the naphthalene plane. In the crystal packing, molecules are linked by N-HN hydrogen bonds into chains along the a axis and these chains are stacked along the b axis. The crystal is further stabilized by weak C-HN and C-H [pi] interactions.

Related literature

For values of bond lengths, see Allen et al. (1987). For background to the bioactivity and applications of naphthyrimidines, see, for example: Bedard et al. (2000); Bohme & Haake (1976); Erian (1993); Falardeau et al. (2000); Martinez & Marco (1997); Tandon et al. (1991); Taylor & McKillop (1970). For the stability of the temperature controller, see Cosier & Glazer (1986).

Experimental

Crystal data

C₂₁H₁₅N₃O
M_r = 325.36
Orthorhombic, P b c a
a = 13.2762 (3) Å
b = 8.8700 (2) Å
c = 27.1997 (5) Å
V = 3203.03 (12) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.57 × 0.38 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.901, T_max = 0.997
27104 measured reflections
4673 independent reflections
3649 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.142
S = 1.08
4673 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C3/C11/N1/N2 and C4-C9 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N3-H1N3N2ⁱ	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13-H13AN2ⁱⁱ	0.93	2.62	3.4791 (16)	154
C20-H20AN3	0.93	2.60	2.9077 (15)	100
C20-H20AN1ⁱⁱⁱ	0.93	2.48	3.3232 (17)	150
C10-H10ACg1ⁱⁱⁱ	0.97	2.76	3.5855 (14)	143
C10-H10BCg2ⁱⁱ	0.97	2.96	3.6792 (14)	132
C13-H13ACg1ⁱⁱ	0.93	2.63	3.3503 (14)	135
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2571 ).

Acknowledgements

AMI is grateful to the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das, Syngene International Ltd, Bangalore, India, for allocation of research resources. The authors also thank the Universiti Sains Malaysia for Research University Golden Goose Grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bedard, J., May, S., Heureux, L., Stamminger, T., Copsey, A., Drach, J., Huffman, J., Chan, L., Jin, H. & Rando, R. F. (2000). Antimicrob. Agents Chemother. 44, 929-932.
Bohme, H. & Haake, M. (1976). Advances in Organic Chemistry, edited by E. C. Taylor, p. 107. New York: John Wiley and Sons.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Erian, A. W. (1993). Chem. Rev. 93, 1991-2005.
Falardeau, G., Chan, L., Stefanac, T., May, S., Jin, H. & Lavallee, J. F. (2000). Bioorg. Med. Chem. Lett. 18, 2769-2770.
Martinez, A. G. & Marco, L. J. (1997). Bioorg. Med. Chem. Lett. 24, 3165-3170.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Tandon, V. K., Vaish, M., Jain, S., Bhakuni, D. S. & Srimal, R. C. (1991). Indian J. Pharm. Sci. 53, 22-23.
Taylor, E. C. & McKillop, A. (1970). The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles, p. 415. New York: Interscience.

organic compounds