1-Phenyl-1H-naphtho­[1,2-e][1,3]oxazin-3(2H)-one

Humaira Y Gondal; Misbah Bhatti; Azra Gohar; Muhammad Ali; M Nawaz Tahir

doi:10.1107/S1600536810035841

. 2010 Sep 11;66(Pt 10):o2555. doi: 10.1107/S1600536810035841

1-Phenyl-1H-naphtho[1,2-e][1,3]oxazin-3(2H)-one

Humaira Y Gondal ^a, Misbah Bhatti ^a, Azra Gohar ^a, Muhammad Ali ^a, M Nawaz Tahir ^b,^*

PMCID: PMC2983264 PMID: 21587542

Abstract

In the title compound, C₁₈H₁₃NO₂, the naphthalene (r.m.s. deviation = 0.025 Å) and benzaldehyde (r.m.s. deviation = 0.006 Å) groups are oriented at a dihedral angle of 89.48 (4)°. The oxazine group is oriented at dihedral angles of 13.36 (4) and 85.08 (5)°, respectively, with respect to the naphthalene and benzaldehyde fragments. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R ₂ ²(8) loops. The dimers are linked into [010] chains via N—H⋯O hydrogen bonds. Weak C—H⋯π links and aromatic π–π stacking between the centroids of the naphthalene phenyl rings [centroid–centroid separation = 3.5977 (8) Å] help to consolidate the packing.

Related literature

For background to oxazinones, see: Patel et al. (1999 ▶); Waxman & Darke (2000 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₃NO₂
M _r = 275.29
Monoclinic,
a = 11.5625 (4) Å
b = 16.9228 (5) Å
c = 7.2394 (2) Å
β = 98.155 (1)°
V = 1402.21 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.982
9236 measured reflections
2533 independent reflections
1961 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.03
2533 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035841/hb5635sup1.cif

e-66-o2555-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035841/hb5635Isup2.hkl

e-66-o2555-Isup2.hkl^{(121.9KB, hkl)}

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

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

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.07	2.8698 (17)	155
C8—H8⋯O1ⁱⁱ	0.93	2.58	3.4725 (18)	161
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.92	3.722 (2)	145

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

Oxazinones are an important class of heterocyclic compounds with a diverse range of biological activities (Patel et al., 1999; Waxman & Darke, 2000). During recent studies for the search of efficient, simple and green method for the preparation of naphthalene-condensed 1,3-oxazin-3-one derivatives, we have obtained the title compound (I, Fig. 1).

In the title compound, the naphthalene group A (C1—C10) and moiety B (C11—C17) of benzaldehyde group are planar with r. m. s. deviations of 0.0252 and 0.0056 Å, respectively. The dihedral angle between A/B is 89.48 (4)°. The fused group C (O1/C18/O2/N1) is also planar with r. m. s. deviation of 0.0037 Å. The dihedral angle between A/C and B/C is 13.36 (4) and 85.08 (5)°, respectively. The title compound is dimerized due to H-bonding of C—H···O type (Table 1, Fig. 2) with R₂²(8) ring motifs (Bernstein et al., 1995). The dimers are interlinked due to N—H···O type of H-bondings (Table 1, Fig. 2). There exists π–π interaction between the centroids of phenyl rings (C1/C6—C10) at a distance of 3.5977 (8) Å [symmetry code: 2 - x, - y, 1 - z]. The molecules are stabilized in the form of infinite one dimensional polymeric chains extending along the c axis.

Experimental

A mixture of β-naphthol (1.0 mmol), benzaldehyde (1.0 mmol), urea (1.0 mmol) and CuCl₂ (0.1 mm mol) as a catalyst, were heated at 393 K in a round bottom flask for 3 h. The reaction was monitored through TLC. After completion of the reaction, the mixture was cooled to room temperature and washed thoroughly with distilled water. The crude product obtained was recrystallized from petroleum ether:ethyl acetate (1:5) to affoard colourless rods of (I) after 24 h.