(IUCr) 1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine

Volume 64
Part 3
Page o573
March 2008

Received 18 January 2008
Accepted 5 February 2008
Online 13 February 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.092
Data-to-parameter ratio = 12.2
Details

1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine

Betül Sen,^a ^* Zuhal Turgut,^b Emel Pelit ^b and Muhittin Aygün ^a

^aDepartment of Physics, Dokuz Eylül University, 35160 Buca-Izmir, Turkey, and ^bDepartment of Chemistry, Y [iota] ld [iota] z Technical University, 34210 Davutpasa Campus-Istanbul, Turkey
Correspondence e-mail: betul.sen@deu.edu.tr

In the crystal structure of the title compound, C₂₂H₁₇N₃O, the oxazine ring has a half-chair conformation. The dihedral angles between the best least-squares plane through the pyridine rings and the planar part (O-C-C-C-N) of the oxazine ring are 72.14 (6) and 35.44 (7)°, the smaller angle involving the pyridine ring adjacent to the oxazine O atom. The molecule has two stereogenic centers at the oxazine carbons, RS and SR. The crystal packing reveals that symmetry-related molecules are linked by intermolecular N-HN hydrogen bonds to form chains parallel to the b axis.

Related literature

For related literature, see: Kurz et al. (2005); Turgut et al. (2007); Szatmari et al. (2003, 2004); Bernstein et al. (1995); Cremer & Pople (1975).

Experimental

Crystal data

C₂₂H₁₇N₃O
M_r = 339.39
Monoclinic, P 2₁ /c
a = 12.1720 (8) Å
b = 8.0444 (6) Å
c = 18.7716 (15) Å
= 112.615 (5)°
V = 1696.7 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.28 × 0.22 × 0.12 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: none
15207 measured reflections
3703 independent reflections
1786 reflections with I > 2(I)
R_int = 0.124

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.092
S = 0.80
3703 reflections
304 parameters
All H-atom parameters refined
_max = 0.12 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N3ⁱ	0.98 (2)	2.04 (2)	3.009 (2)	170.7 (17)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2043 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F.279 of the University Research Fund), and Dokuz Eylül University Research Funds (Project No. 04.KB.FEN.100).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Burnett, M. N. & Johnson, C. K. (1996). Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, U.SA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kurz, T. (2005). Tetrahedron, 61, 3091-3096.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Szatmari, I., Martinek, T. A., Lazar, L. & Fülop, F. (2003). Tetrahedron, 59, 2877-2884.
Szatmari, I., Martinek, T. A., Lazar, L. & Fülop, F. (2004). Eur. J. Org. Chem. pp. 2231-2238.
Turgut, Z., Pelit, E. & Köycü, A. (2007). Molecules, 12, 345-352.

organic compounds