Received 12 October 2005
In the title compound, C25H19NO6, the molecular structure is stabilized by intra- and intermolecular C-HO hydrogen bonds. The intermolecular hydrogen bonds link the molecules into a herringbone-like dimer.
Oxazine derivatives have been shown to be antimicrobial agents (Bayomi et al., 1985), fungicides (Player et al., 1993), and also to exhibit some cytotoxic or antitumour activity (Eger & Frey, 1992; Mordarski et al., 1970; Mordarski & Chylinska, 1971, 1972). In the light of this, we have synthesized and characterized the title compound, (2), and have determined its structure by X-ray analysis.
The molecular structure of (2) is illustrated in Fig. 1. The rings (A, B, C and D) are each essentially planar, with r.m.s. deviations of 0.031 (2), 0.019 (2), 0.017 (2) and 0.006 (2) Å, respectively. The dihedral angles between the rings are A/B = 64.31 (9)°, A/C = 19.49 (16)°, A/D = 82.31 (8)°, B/C = 62.22 (9)°, B/D = 61.61 (9)° and C/D = 63.73 (8)°. The bond lengths and angles are in agreement with reported literature values (Allen et al., 1987).
The structure is stabilized by intra- and intermolecular C-HO hydrogen bonds (Table 1). In the crystal structure, the C-HO intermolecular hydrogen bonds link the molecules into herringbone-like dimers which are stacked along the b axis (Fig. 2).
| || Figure 1 |
The molecular structure of (2), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted.
| || Figure 2 |
Packing diagram of (2); C-HO hydrogen bonds are indicated by dashed lines.
Compound (1) was prepared from the cyclocondensation reaction that occurs between p,p'-dimethoxydibenzoylketene and oxalyl chloride (Hökelek et al., 2002). Compound (2) was obtained from 1.0 g (2.96 mmol) (1) and 0.35 g (2.96 mmol) phenyl isocyanate in a 25 ml round-bottomed flask equipped with a calcium chloride tube. The mixture was heated at 393 K for 1 h. The cooled reaction mixture was triturated with dry diethyl ether and then recrystallized from n-butanol (yield 0.83 g, 65%, m.p. 480 K). IR (KBr, cm-1): 1774 (C5-O4), 1690 (C4-O1), 1646 (C1-O2). 1H NMR (CDCl3): 7.95-6.81 (m, 13H, Ar-H), 3.84, 3.79 (s, 6H, CH3O); 13C NMR (CDCl3): 190.80 (C5-O4), 166.60 (C4-O1), 165.04 (C1-O2), 162.36-113.47 (C=C, aromatic and aliphatic), 57.52, 57.44 (CH3O). Analysis calculated for C40H35N3O5: C 69.93, H 4.42, N 3.26%; found: C 69.80, H 4.51, N 3.14%.
H atoms were positioned geometrically [C-H = 0.95 (CH) and 0.98 Å (CH3)] and constrained to ride on their parent atoms, with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
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