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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

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© International Union of Crystallography 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

Harry Adams,a* Samuel M. Hawxwell,a Mustafa Saçmaci,b Sevket Hakan Üngoren,b Yunus Akçamurb and Recep Sahingozb

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 ]