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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o127.
Published online 2008 December 17. doi:  10.1107/S1600536808042050
PMCID: PMC2968047

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

Abstract

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 π–π stacking inter­actions [centroid-centroid distance = 4.2789 (11) Å] and the crystal packing is additionally stabilized by weak inter­molecular C—H(...)O inter­actions.

Related literature

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

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Object name is e-65-0o127-scheme1.jpg

Experimental

Crystal data

  • C14H9NO2
  • M r = 223.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o127-efi1.jpg
  • a = 13.3055 (16) Å
  • b = 3.8930 (4) Å
  • c = 20.445 (2) Å
  • β = 94.946 (3)°
  • V = 1055.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 (2) K
  • 0.20 × 0.16 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.985
  • 13688 measured reflections
  • 3034 independent reflections
  • 1800 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.187
  • S = 1.08
  • 3034 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042050/gk2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042050/gk2180Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The crystal packing viewed down the b axis. C-H···O hydrogen bonds are shown as dashed lines.

Crystal data

C14H9NO2F(000) = 464
Mr = 223.22Dx = 1.405 Mg m3
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 mm1
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

Bruker Kappa APEXII diffractometer3034 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 [var phi] 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

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 = 1.08w = 1/[σ2(Fo2) + (0.0948P)2] where P = (Fo2 + 2Fc2)/3
3034 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.28 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2180).

References

  • 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. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography