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Acta Cryst. (2009). E65, o127    [ doi:10.1107/S1600536808042050 ]

2-Phenyl-4H-3,1-benzoxazin-4-one

R. Thilagavathy, H. P. Kavitha, R. Arulmozhi, J. P. Vennila and V. Manivannan

Abstract top

The title molecule, C14H9NO2, is nearly planar with a dihedral angle of 3.72 (4)° beteewn the plane of the phenyl ring and the 3,1-benzoxazin-4-one fragment. The molecules are arranged into stacks parallel to the b axis via [pi]-[pi] stacking interactions [centroid-centroid distance = 4.2789 (11) Å] and the crystal packing is additionally stabilized by weak intermolecular C-H...O interactions.

Comment top

Oxazin-4-one derivatives are used as inhibitors of the alpha/beta hydrolases, cholesterol esterase and acetylcholinesterase (Pietsch & Gütschow, 2005) and are potent inhibitors of the endocannabinoid-deactivating enzyme, monoacylglycerol lipase (Tarzia et al., 2007).

The geometric parameters of the title molecule (Fig. 1) agree well with the earlier reported structures (Crane & Rogerson, 2004; Khan et al., 2007). The plane of the phenyl ring forms a dihedral angle of 3.72 (4)° with the benzo[d][1,3]oxazin-4-one moiety. The molecular structure is stabilized by weak intramolecular C–H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O and π-π stacking interactions.

Related literature top

For the biological activity of oxazin-4-ones, see: Pietsch & Gütschow (2005); Tarzia et al. (2007). For similar structures, see: Crane & Rogerson (2004); Khan et al. (2007).

Experimental top

To a stirred solution of anthranilic acid (0.01 mol) in pyridine (60 ml), benzoyl chloride (0.01 mol) was added dropwise maintaining the temperature near 8° C for one hour. The reaction mixture was stirred for another 2 h at room temperature. While stirring, a solid product separated out. The whole reaction mixture was neutralized with NaHCO3 solution. A pale yellow solid deposited was filtered, washed with water and recrystallized from ethanol to get diffraction quality crystals; yYield 78%.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing viewed down the b axis. C-H···O hydrogen bonds are shown as dashed lines.
2-Phenyl-4H-3,1-benzoxazin-4-one top
Crystal data top
C14H9NO2F(000) = 464
Mr = 223.22Dx = 1.405 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2312 reflections
a = 13.3055 (16) Åθ = 1.7–29.5°
b = 3.8930 (4) ŵ = 0.10 mm−1
c = 20.445 (2) ÅT = 295 K
β = 94.946 (3)°Block, pale yellow
V = 1055.1 (2) Å30.20 × 0.16 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer		3034 independent reflections
Radiation source: fine-focus sealed tube1800 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 0 pixels mm-1θmax = 29.8°, θmin = 1.8°
ω and φ scansh = −18→17
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −5→5
Tmin = 0.981, Tmax = 0.985l = −28→28
13688 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0948P)2]
where P = (Fo2 + 2Fc2)/3
3034 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C14H9NO2V = 1055.1 (2) Å3
Mr = 223.22Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.3055 (16) ŵ = 0.10 mm−1
b = 3.8930 (4) ÅT = 295 K
c = 20.445 (2) Å0.20 × 0.16 × 0.16 mm
β = 94.946 (3)°
Data collection top
Bruker Kappa APEXII
diffractometer		3034 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1800 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.985Rint = 0.036
13688 measured reflectionsθmax = 29.8°
Refinement top
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.187Δρmax = 0.24 e Å−3
S = 1.08Δρmin = −0.28 e Å−3
3034 reflectionsAbsolute structure: ?
154 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.54301 (13)0.4961 (4)0.20378 (8)0.0439 (4)
C20.48811 (15)0.6405 (4)0.15009 (9)0.0533 (5)
H20.42270.71750.15390.064*
C30.52987 (17)0.6703 (5)0.09133 (10)0.0663 (6)
H30.49240.76390.05510.080*
C40.62706 (19)0.5616 (6)0.08600 (11)0.0718 (6)
H40.65540.58440.04620.086*
C50.68254 (16)0.4204 (5)0.13861 (12)0.0680 (6)
H50.74820.34720.13450.082*
C60.64107 (13)0.3866 (5)0.19766 (10)0.0549 (5)
H60.67870.29040.23350.066*
C70.49642 (12)0.4637 (4)0.26569 (8)0.0412 (4)
C80.52751 (12)0.2379 (4)0.37481 (8)0.0466 (4)
C90.42925 (12)0.3731 (4)0.38655 (8)0.0412 (4)
C100.39216 (13)0.3387 (4)0.44755 (9)0.0489 (4)
H100.43070.23120.48170.059*
C110.29830 (14)0.4643 (5)0.45710 (9)0.0534 (5)
H110.27330.44450.49800.064*
C120.24090 (14)0.6201 (5)0.40597 (10)0.0535 (5)
H120.17710.70270.41280.064*
C130.27615 (12)0.6554 (4)0.34535 (9)0.0479 (4)
H130.23640.75990.31130.057*
C140.37202 (12)0.5334 (4)0.33502 (8)0.0404 (4)
N10.40839 (10)0.5770 (3)0.27363 (7)0.0441 (4)
O10.55759 (8)0.2978 (3)0.31294 (6)0.0495 (3)
O20.58392 (10)0.0790 (4)0.41188 (6)0.0698 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0438 (9)0.0438 (8)0.0439 (10)−0.0068 (7)0.0027 (7)−0.0010 (7)
C20.0560 (11)0.0553 (10)0.0484 (11)−0.0045 (8)0.0033 (9)0.0046 (8)
C30.0816 (16)0.0675 (12)0.0503 (12)−0.0070 (10)0.0083 (11)0.0089 (9)
C40.0859 (17)0.0717 (13)0.0618 (14)−0.0187 (11)0.0290 (12)−0.0008 (10)
C50.0567 (12)0.0758 (13)0.0743 (15)−0.0074 (10)0.0225 (11)−0.0052 (11)
C60.0443 (10)0.0630 (11)0.0578 (12)−0.0049 (8)0.0065 (9)0.0011 (8)
C70.0384 (9)0.0414 (8)0.0422 (10)−0.0032 (6)−0.0053 (7)0.0008 (6)
C80.0404 (9)0.0546 (9)0.0440 (10)0.0025 (7)−0.0012 (8)0.0069 (7)
C90.0391 (9)0.0418 (8)0.0415 (9)−0.0023 (6)−0.0027 (7)−0.0003 (6)
C100.0496 (10)0.0531 (9)0.0431 (10)−0.0017 (7)−0.0018 (8)0.0040 (7)
C110.0542 (11)0.0592 (10)0.0476 (11)−0.0037 (8)0.0100 (9)−0.0048 (8)
C120.0424 (10)0.0569 (10)0.0618 (13)0.0010 (7)0.0071 (9)−0.0099 (8)
C130.0393 (9)0.0531 (9)0.0499 (11)0.0030 (7)−0.0047 (8)−0.0020 (7)
C140.0370 (8)0.0408 (8)0.0423 (9)−0.0020 (6)−0.0019 (7)−0.0022 (6)
N10.0399 (8)0.0495 (7)0.0421 (8)0.0008 (6)−0.0018 (6)0.0033 (6)
O10.0387 (7)0.0644 (7)0.0447 (7)0.0069 (5)0.0003 (5)0.0075 (5)
O20.0532 (8)0.0981 (10)0.0576 (9)0.0236 (7)0.0018 (7)0.0257 (7)
Geometric parameters (Å, °) top
C1—C21.384 (2)C8—O21.1926 (19)
C1—C61.388 (2)C8—O11.3791 (19)
C1—C71.462 (2)C8—C91.448 (2)
C2—C31.371 (2)C9—C101.387 (2)
C2—H20.9300C9—C141.393 (2)
C3—C41.374 (3)C10—C111.371 (2)
C3—H30.9300C10—H100.9300
C4—C51.367 (3)C11—C121.381 (3)
C4—H40.9300C11—H110.9300
C5—C61.376 (3)C12—C131.369 (2)
C5—H50.9300C12—H120.9300
C6—H60.9300C13—C141.394 (2)
C7—N11.275 (2)C13—H130.9300
C7—O11.3702 (18)C14—N11.394 (2)
C2—C1—C6119.27 (17)O2—C8—C9127.66 (16)
C2—C1—C7119.16 (15)O1—C8—C9115.34 (14)
C6—C1—C7121.56 (16)C10—C9—C14120.63 (15)
C3—C2—C1120.20 (18)C10—C9—C8120.68 (15)
C3—C2—H2119.9C14—C9—C8118.68 (15)
C1—C2—H2119.9C11—C10—C9119.55 (16)
C2—C3—C4119.9 (2)C11—C10—H10120.2
C2—C3—H3120.0C9—C10—H10120.2
C4—C3—H3120.0C10—C11—C12120.00 (17)
C5—C4—C3120.64 (19)C10—C11—H11120.0
C5—C4—H4119.7C12—C11—H11120.0
C3—C4—H4119.7C13—C12—C11121.27 (16)
C4—C5—C6119.9 (2)C13—C12—H12119.4
C4—C5—H5120.0C11—C12—H12119.4
C6—C5—H5120.0C12—C13—C14119.49 (16)
C5—C6—C1120.05 (19)C12—C13—H13120.3
C5—C6—H6120.0C14—C13—H13120.3
C1—C6—H6120.0C9—C14—N1121.73 (14)
N1—C7—O1124.73 (15)C9—C14—C13119.05 (15)
N1—C7—C1122.90 (15)N1—C14—C13119.22 (15)
O1—C7—C1112.37 (14)C7—N1—C14117.80 (14)
O2—C8—O1117.00 (15)C7—O1—C8121.64 (12)
C6—C1—C2—C30.9 (2)C9—C10—C11—C120.8 (3)
C7—C1—C2—C3−179.33 (15)C10—C11—C12—C13−0.6 (3)
C1—C2—C3—C4−1.0 (3)C11—C12—C13—C14−0.3 (3)
C2—C3—C4—C50.7 (3)C10—C9—C14—N1178.74 (14)
C3—C4—C5—C6−0.1 (3)C8—C9—C14—N1−2.3 (2)
C4—C5—C6—C10.0 (3)C10—C9—C14—C13−0.8 (2)
C2—C1—C6—C5−0.4 (3)C8—C9—C14—C13178.16 (14)
C7—C1—C6—C5179.88 (15)C12—C13—C14—C91.0 (2)
C2—C1—C7—N1−3.3 (2)C12—C13—C14—N1−178.56 (14)
C6—C1—C7—N1176.50 (15)O1—C7—N1—C140.9 (2)
C2—C1—C7—O1176.31 (13)C1—C7—N1—C14−179.59 (12)
C6—C1—C7—O1−3.9 (2)C9—C14—N1—C70.2 (2)
O2—C8—C9—C103.1 (3)C13—C14—N1—C7179.81 (15)
O1—C8—C9—C10−177.93 (14)N1—C7—O1—C80.1 (2)
O2—C8—C9—C14−175.84 (17)C1—C7—O1—C8−179.43 (13)
O1—C8—C9—C143.1 (2)O2—C8—O1—C7176.92 (16)
C14—C9—C10—C11−0.1 (2)C9—C8—O1—C7−2.1 (2)
C8—C9—C10—C11−179.02 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.392.713 (2)101
C10—H10···O2i0.932.513.294 (2)142
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.392.713 (2)101
C10—H10···O2i0.932.513.294 (2)142
Symmetry codes: (i) −x+1, −y, −z+1.
Acknowledgements top

The authors acknowledge the management of SRM University for providing financial assistance for the pilot project.

references
References top

Bruker (2004). APEX2 andSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Crane, J. D. & Rogerson, E. (2004). Acta Cryst. E60, o669–o670.

Khan, Z. A., Khan, K. M. & Anjum, S. (2007). Acta Cryst. E63, o4226–o4227.

Pietsch, M. & Gütschow, M. (2005). J. Med. Chem. 48, 8270-8288.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Tarzia, G., Antonietti, F., Duranti, A., Tontini, A., Mor, M., Rivara, S., Traldi, P., Astarita, G., King, A., Clapper, J. R. & Piomelli, D. (2007). Ann. Chim. 97, 887–894.