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

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

doi:10.1107/S1600536808042050

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o127

doi:10.1107/S1600536808042050

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

R. Thilagavathy,^a Helen P. Kavitha,^a R. Arulmozhi,^b Jasmine P. Vennila ^c and V. Manivannan ^d ^*

^aDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, ^bDepartment of Chemistry, SRM University, Kattankulathur Campus, Kanchipuram, India, ^cDepartment of Physics, Panimalar Institute of Technology, Chennai, India, and ^dDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 3 December 2008; accepted 10 December 2008; online 17 December 2008)

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 ); Tarzia et al. (2007 ). For similar structures, see: Crane & Rogerson (2004 ); Khan et al. (2007 ).

Experimental

Crystal data

C₁₄H₉NO₂
M_r = 223.22
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.187
S = 1.08
3034 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.51	3.294 (2)	142
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

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%.

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

	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.

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

Crystal data top

C₁₄H₉NO₂	F(000) = 464
M_r = 223.22	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2312 reflections
a = 13.3055 (16) Å	θ = 1.7–29.5°
b = 3.8930 (4) Å	µ = 0.10 mm⁻¹
c = 20.445 (2) Å	T = 295 K
β = 94.946 (3)°	Block, pale yellow
V = 1055.1 (2) Å³	0.20 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	3034 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 0 pixels mm^-1	θ_max = 29.8°, θ_min = 1.8°
ω and ϕ scans	h = −18→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→5
T_min = 0.981, T_max = 0.985	l = −28→28
13688 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0948P)²] where P = (F_o² + 2F_c²)/3
3034 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₉NO₂	V = 1055.1 (2) Å³
M_r = 223.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.3055 (16) Å	µ = 0.10 mm⁻¹
b = 3.8930 (4) Å	T = 295 K
c = 20.445 (2) Å	0.20 × 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)
T_min = 0.981, T_max = 0.985	R_int = 0.036
13688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.08	Δρ_max = 0.24 e Å⁻³
3034 reflections	Δρ_min = −0.28 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.54301 (13)	0.4961 (4)	0.20378 (8)	0.0439 (4)
C2	0.48811 (15)	0.6405 (4)	0.15009 (9)	0.0533 (5)
H2	0.4227	0.7175	0.1539	0.064*
C3	0.52987 (17)	0.6703 (5)	0.09133 (10)	0.0663 (6)
H3	0.4924	0.7639	0.0551	0.080*
C4	0.62706 (19)	0.5616 (6)	0.08600 (11)	0.0718 (6)
H4	0.6554	0.5844	0.0462	0.086*
C5	0.68254 (16)	0.4204 (5)	0.13861 (12)	0.0680 (6)
H5	0.7482	0.3472	0.1345	0.082*
C6	0.64107 (13)	0.3866 (5)	0.19766 (10)	0.0549 (5)
H6	0.6787	0.2904	0.2335	0.066*
C7	0.49642 (12)	0.4637 (4)	0.26569 (8)	0.0412 (4)
C8	0.52751 (12)	0.2379 (4)	0.37481 (8)	0.0466 (4)
C9	0.42925 (12)	0.3731 (4)	0.38655 (8)	0.0412 (4)
C10	0.39216 (13)	0.3387 (4)	0.44755 (9)	0.0489 (4)
H10	0.4307	0.2312	0.4817	0.059*
C11	0.29830 (14)	0.4643 (5)	0.45710 (9)	0.0534 (5)
H11	0.2733	0.4445	0.4980	0.064*
C12	0.24090 (14)	0.6201 (5)	0.40597 (10)	0.0535 (5)
H12	0.1771	0.7027	0.4128	0.064*
C13	0.27615 (12)	0.6554 (4)	0.34535 (9)	0.0479 (4)
H13	0.2364	0.7599	0.3113	0.057*
C14	0.37202 (12)	0.5334 (4)	0.33502 (8)	0.0404 (4)
N1	0.40839 (10)	0.5770 (3)	0.27363 (7)	0.0441 (4)
O1	0.55759 (8)	0.2978 (3)	0.31294 (6)	0.0495 (3)
O2	0.58392 (10)	0.0790 (4)	0.41188 (6)	0.0698 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (9)	0.0438 (8)	0.0439 (10)	−0.0068 (7)	0.0027 (7)	−0.0010 (7)
C2	0.0560 (11)	0.0553 (10)	0.0484 (11)	−0.0045 (8)	0.0033 (9)	0.0046 (8)
C3	0.0816 (16)	0.0675 (12)	0.0503 (12)	−0.0070 (10)	0.0083 (11)	0.0089 (9)
C4	0.0859 (17)	0.0717 (13)	0.0618 (14)	−0.0187 (11)	0.0290 (12)	−0.0008 (10)
C5	0.0567 (12)	0.0758 (13)	0.0743 (15)	−0.0074 (10)	0.0225 (11)	−0.0052 (11)
C6	0.0443 (10)	0.0630 (11)	0.0578 (12)	−0.0049 (8)	0.0065 (9)	0.0011 (8)
C7	0.0384 (9)	0.0414 (8)	0.0422 (10)	−0.0032 (6)	−0.0053 (7)	0.0008 (6)
C8	0.0404 (9)	0.0546 (9)	0.0440 (10)	0.0025 (7)	−0.0012 (8)	0.0069 (7)
C9	0.0391 (9)	0.0418 (8)	0.0415 (9)	−0.0023 (6)	−0.0027 (7)	−0.0003 (6)
C10	0.0496 (10)	0.0531 (9)	0.0431 (10)	−0.0017 (7)	−0.0018 (8)	0.0040 (7)
C11	0.0542 (11)	0.0592 (10)	0.0476 (11)	−0.0037 (8)	0.0100 (9)	−0.0048 (8)
C12	0.0424 (10)	0.0569 (10)	0.0618 (13)	0.0010 (7)	0.0071 (9)	−0.0099 (8)
C13	0.0393 (9)	0.0531 (9)	0.0499 (11)	0.0030 (7)	−0.0047 (8)	−0.0020 (7)
C14	0.0370 (8)	0.0408 (8)	0.0423 (9)	−0.0020 (6)	−0.0019 (7)	−0.0022 (6)
N1	0.0399 (8)	0.0495 (7)	0.0421 (8)	0.0008 (6)	−0.0018 (6)	0.0033 (6)
O1	0.0387 (7)	0.0644 (7)	0.0447 (7)	0.0069 (5)	0.0003 (5)	0.0075 (5)
O2	0.0532 (8)	0.0981 (10)	0.0576 (9)	0.0236 (7)	0.0018 (7)	0.0257 (7)

Geometric parameters (Å, º) top

C1—C2	1.384 (2)	C8—O2	1.1926 (19)
C1—C6	1.388 (2)	C8—O1	1.3791 (19)
C1—C7	1.462 (2)	C8—C9	1.448 (2)
C2—C3	1.371 (2)	C9—C10	1.387 (2)
C2—H2	0.9300	C9—C14	1.393 (2)
C3—C4	1.374 (3)	C10—C11	1.371 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.367 (3)	C11—C12	1.381 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.376 (3)	C12—C13	1.369 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—C14	1.394 (2)
C7—N1	1.275 (2)	C13—H13	0.9300
C7—O1	1.3702 (18)	C14—N1	1.394 (2)

C2—C1—C6	119.27 (17)	O2—C8—C9	127.66 (16)
C2—C1—C7	119.16 (15)	O1—C8—C9	115.34 (14)
C6—C1—C7	121.56 (16)	C10—C9—C14	120.63 (15)
C3—C2—C1	120.20 (18)	C10—C9—C8	120.68 (15)
C3—C2—H2	119.9	C14—C9—C8	118.68 (15)
C1—C2—H2	119.9	C11—C10—C9	119.55 (16)
C2—C3—C4	119.9 (2)	C11—C10—H10	120.2
C2—C3—H3	120.0	C9—C10—H10	120.2
C4—C3—H3	120.0	C10—C11—C12	120.00 (17)
C5—C4—C3	120.64 (19)	C10—C11—H11	120.0
C5—C4—H4	119.7	C12—C11—H11	120.0
C3—C4—H4	119.7	C13—C12—C11	121.27 (16)
C4—C5—C6	119.9 (2)	C13—C12—H12	119.4
C4—C5—H5	120.0	C11—C12—H12	119.4
C6—C5—H5	120.0	C12—C13—C14	119.49 (16)
C5—C6—C1	120.05 (19)	C12—C13—H13	120.3
C5—C6—H6	120.0	C14—C13—H13	120.3
C1—C6—H6	120.0	C9—C14—N1	121.73 (14)
N1—C7—O1	124.73 (15)	C9—C14—C13	119.05 (15)
N1—C7—C1	122.90 (15)	N1—C14—C13	119.22 (15)
O1—C7—C1	112.37 (14)	C7—N1—C14	117.80 (14)
O2—C8—O1	117.00 (15)	C7—O1—C8	121.64 (12)

C6—C1—C2—C3	0.9 (2)	C9—C10—C11—C12	0.8 (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—C5	0.7 (3)	C10—C9—C14—N1	178.74 (14)
C3—C4—C5—C6	−0.1 (3)	C8—C9—C14—N1	−2.3 (2)
C4—C5—C6—C1	0.0 (3)	C10—C9—C14—C13	−0.8 (2)
C2—C1—C6—C5	−0.4 (3)	C8—C9—C14—C13	178.16 (14)
C7—C1—C6—C5	179.88 (15)	C12—C13—C14—C9	1.0 (2)
C2—C1—C7—N1	−3.3 (2)	C12—C13—C14—N1	−178.56 (14)
C6—C1—C7—N1	176.50 (15)	O1—C7—N1—C14	0.9 (2)
C2—C1—C7—O1	176.31 (13)	C1—C7—N1—C14	−179.59 (12)
C6—C1—C7—O1	−3.9 (2)	C9—C14—N1—C7	0.2 (2)
O2—C8—C9—C10	3.1 (3)	C13—C14—N1—C7	179.81 (15)
O1—C8—C9—C10	−177.93 (14)	N1—C7—O1—C8	0.1 (2)
O2—C8—C9—C14	−175.84 (17)	C1—C7—O1—C8	−179.43 (13)
O1—C8—C9—C14	3.1 (2)	O2—C8—O1—C7	176.92 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.39	2.713 (2)	101
C10—H10···O2ⁱ	0.93	2.51	3.294 (2)	142

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₉NO₂
M_r	223.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	13.3055 (16), 3.8930 (4), 20.445 (2)
β (°)	94.946 (3)
V (Å³)	1055.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.16 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	13688, 3034, 1800
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.187, 1.08
No. of reflections	3034
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.39	2.713 (2)	101
C10—H10···O2ⁱ	0.93	2.51	3.294 (2)	142

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

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

References

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