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Volume 61 
Part 11 
Pages o3910-o3911  
November 2005  

Received 12 October 2005
Accepted 25 October 2005
Online 31 October 2005

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
R = 0.055
wR = 0.154
Data-to-parameter ratio = 11.9
Details

5-(4-Methoxybenzoyl)-6-(4-methoxyphenyl)-3-phenyl-3,4-dihydro-2H-1,3-oxazine-2,4-dione

aDepartment of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, England, and bDepartment of Chemistry, Yozgat Faculty of Arts and Sciences, Erciyes University, 66200 Yozgat, Turkey
Correspondence e-mail: h.adams@sheffield.ac.uk

In the title compound, C25H19NO6, the molecular structure is stabilized by intra- and intermolecular C-H...O hydrogen bonds. The intermolecular hydrogen bonds link the molecules into a herringbone-like dimer.

Comment

Oxazine derivatives have been shown to be antimicrobial agents (Bayomi et al., 1985[Bayomi, S. M., Price, K. E. & Sowell, J. W. Sr (1985). J. Heterocycl. Chem. 22, 729-734.]), fungicides (Player et al., 1993[Player, M. R., Sowell, J. W., Sr., Williams, G. R. & Cowley, G. T. (1993). J. Heterocycl. Chem. 30, 125-128.]), and also to exhibit some cytotoxic or antitumour activity (Eger & Frey, 1992[Eger, K. & Frey, M. (1992). Arch. Pharm. 325, 551-556.]; Mordarski et al., 1970[Mordarski, M., Chylinska, B. & Urbanski, T. (1970). Arch. Immunol. Ther. Exp. 18, 679-699.]; Mordarski & Chylinska, 1971[Mordarski, M. & Chylinska, J. B. (1971). Arch. Immunol. Ther. Exp. 19, 533-545.], 1972[Mordarski, M. & Chylinska, B. (1972). Arch. Immunol. Ther. Exp. 20, 607-617.]). In the light of this, we have synthesized and characterized the title compound, (2), and have determined its structure by X-ray analysis.

[Scheme 1]

The molecular structure of (2) is illustrated in Fig. 1[link]. 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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L. & Orpen, A. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

The structure is stabilized by intra- and intermolecular C-H...O hydrogen bonds (Table 1[link]). In the crystal structure, the C-H...O intermolecular hydrogen bonds link the molecules into herringbone-like dimers which are stacked along the b axis (Fig. 2[link]).

[Figure 1]
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]
Figure 2
Packing diagram of (2); C-H...O hydrogen bonds are indicated by dashed lines.

Experimental

Compound (1) was prepared from the cyclocondensation reaction that occurs between p,p'-dimethoxydibenzoylketene and oxalyl chloride (Hökelek et al., 2002[Hökelek, T., Saripinar, E., Yildirim, I., Akkurt, M. & Akçamur, Y. (2002). Acta Cryst. E58, o30-o32.]). 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): [nu] 1774 (C5-O4), 1690 (C4-O1), 1646 (C1-O2). 1H NMR (CDCl3): [delta] 7.95-6.81 (m, 13H, Ar-H), 3.84, 3.79 (s, 6H, CH3O); 13C NMR (CDCl3): [delta] 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%.

Crystal data
  • C25H19NO6

  • Mr = 429.41

  • Monoclinic, P 21 /c

  • a = 10.950 (2) Å

  • b = 5.8163 (12) Å

  • c = 30.968 (6) Å

  • [beta] = 91.010 (4)°

  • V = 1972.0 (7) Å3

  • Z = 4

  • Dx = 1.446 Mg m-3

  • Mo K[alpha] radiation

  • Cell parameters from 1626 reflections

  • [theta] = 4.5-50.4°

  • [mu] = 0.10 mm-1

  • T = 150 (2) K

  • Needle, colourless

  • 0.32 × 0.12 × 0.12 mm

Data collection
  • Bruker SMART1000 CCD area-detector diffractometer

  • [omega] scans

  • Absorption correction: multi-scan(SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.967, Tmax = 0.988

  • 13592 measured reflections

  • 3456 independent reflections

  • 2069 reflections with I > 2[sigma](I)

  • Rint = 0.089

  • [theta]max = 25.0°

  • h = -13 [rightwards arrow] 13

  • k = -6 [rightwards arrow] 6

  • l = -36 [rightwards arrow] 36

Refinement
  • Refinement on F2

  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.154

  • S = 0.98

  • 3456 reflections

  • 291 parameters

  • H-atom parameters constrained

  • w = 1/[[sigma]2(Fo2) + (0.0743P)2] where P = (Fo2 + 2Fc2)/3

  • ([Delta]/[sigma])max < 0.001

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)[link]

D-H...A D-H H...A D...A D-H...A
C13-H13...O3 0.95 2.33 2.665 (4) 100
C14-H14...O2i 0.95 2.45 3.384 (4) 168
C19-H19...O1ii 0.95 2.47 3.231 (4) 137
C24-H24A...O2iii 0.98 2.52 3.225 (4) 128
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x, y-1, z; (iii) -x+2, -y+2, -z.

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[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SHELXTL (Bruker, 1997[Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L. & Orpen, A. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bayomi, S. M., Price, K. E. & Sowell, J. W. Sr (1985). J. Heterocycl. Chem. 22, 729-734. [CrossRef] [ChemPort]
Bruker (1997). SMART, SAINT, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Eger, K. & Frey, M. (1992). Arch. Pharm. 325, 551-556. [CrossRef] [ChemPort]
Hökelek, T., Saripinar, E., Yildirim, I., Akkurt, M. & Akçamur, Y. (2002). Acta Cryst. E58, o30-o32. [details]
Mordarski, M. & Chylinska, J. B. (1971). Arch. Immunol. Ther. Exp. 19, 533-545. [ChemPort]
Mordarski, M. & Chylinska, B. (1972). Arch. Immunol. Ther. Exp. 20, 607-617. [ChemPort]
Mordarski, M., Chylinska, B. & Urbanski, T. (1970). Arch. Immunol. Ther. Exp. 18, 679-699. [ChemPort]
Player, M. R., Sowell, J. W., Sr., Williams, G. R. & Cowley, G. T. (1993). J. Heterocycl. Chem. 30, 125-128. [CrossRef] [ChemPort]
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.


Acta Cryst (2005). E61, o3910-o3911   [ doi:10.1107/S1600536805034719 ]