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

The title mol-ecule, C(14)H(9)NO(2), 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 mol-ecules are arranged into stacks parallel to the b axis via π-π stacking inter-actions [centroid-centroid distance = 4.2789 (11) Å] and the crystal packing is additionally stabilized by weak inter-molecular C-H⋯O inter-actions.

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 = 223.22

Monoclinic,

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[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 ▶); 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.

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

C14H9NO2	F(000) = 464
Mr = 223.22	Dx = 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

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

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(Fo2) + (0.0948P)2] where P = (Fo2 + 2Fc2)/3
3034 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .