2-(2-Nitro­phenyl)-4,5-benz-1,3-oxazin-6-one

In the title compound, C₁₄H₈N₂O₄, the planar benzoxazinone moiety forms a dihedral angle of 54.54 (8)° with the phenyl ring. The crystal structure is stabilized by weak C—H...O hydrogen bonds and van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 11.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.867
          Tmax scaled      0.867 Tmin scaled      0.840

---

S1. Comment

The preparation of several new 2-phenyl substituted phenyl benzoxinones and evaluation of their biological activity against some pathogenic fungi and bacteria have been reported (Kumar et al., 1997). A project has been undertaken by us to study the crystal structures of some of these benzoxinones to establish their stereochemistry. The present paper reports the structure of the title compound, C₁₄H₈N₂O₄ (I), a benzoxinone derivative.

A displacement ellipsoid plot of the title molecule is shown in Fig. 1. The benzoxinone moiety is essentially planar, with O2 deviating a maximum of 0.037 (1) Å and it forms a dihedral angle of 54.54 (8)° with the phenyl ring. The nitro group is twisted out of the phenyl ring plane by 19.63 (11)°. Although there is no —NH or —OH group available in the structure to form strong hydrogen bonds, the C atoms are involved in the formation of weak C—H···O hydrogen bonds with the oxygen atoms O3 and O4 of the nitro group (Table 2 and Fig. 2). Some other short intermolecular contacts are listed in Table 3.

S2. Experimental

The title compound was obtained by the reaction of o-nitrobenzoyl chloride on anthralinic acid in cold (273 K) (Kumar et al., 1997). The precipitate was recrystallized from EtOH/H₂O (4:1) as pale yellow crystals.

S3. Refinement

After checking their presence in a difference map, all the hydrogen atoms were fixed and geometrically were treated as riding on their aromatic parent C atoms, with C—H = 0.93 Å.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair,1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. An ORTEP-3 plot (Farrugia, 1997) of the molecule, with 50% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. A view of the weak C—H···O hydrogen bonds in the title compound. Symmetry codes: (i) −x, −y, −z, (ii) x, 1/2 − y, −1/2 + z (iii) = 1 + x, 1/2 − y, −1/2 + z and (iv) = 1 − x, 1/2 + y, 1/2 − z.

2-(2'-Nitrophenyl)-4,5-benz-1,3-oxazin-6-one

Crystal data

C14H8N2O4	F(000) = 552
Mr = 268.22	Dx = 1.506 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.1824 (6) Å	θ = 11.2–35.2°
b = 22.191 (2) Å	µ = 0.96 mm^−1
c = 12.767 (1) Å	T = 293 K
β = 93.26 (1)°	Needles, light yellow
V = 1183.0 (2) Å^3	0.36 × 0.24 × 0.15 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	1739 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 67.7°, θmin = 4.0°
ω–2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = 0→26
Tmin = 0.968, Tmax = 0.999	l = −15→15
2438 measured reflections	3 standard reflections every 60 min
2130 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 0.4728P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2130 reflections	Δρmax = 0.24 e Å^−3
182 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.3229 (5)	−0.01215 (9)	0.13071 (15)	0.0488 (5)
H1	0.2493	−0.0088	0.0608	0.063*
C2	0.5058 (6)	−0.06047 (9)	0.16334 (17)	0.0550 (5)
H2	0.5558	−0.0902	0.1156	0.069*
C3	0.6167 (5)	−0.06517 (8)	0.26742 (17)	0.0525 (5)
H3	0.7425	−0.0980	0.2887	0.068*
C4	0.5443 (5)	−0.02231 (8)	0.33934 (15)	0.0454 (4)
H4	0.6196	−0.0262	0.4090	0.054*
C5	0.3573 (4)	0.02718 (7)	0.30789 (13)	0.0369 (4)
C6	0.2473 (4)	0.03215 (7)	0.20292 (13)	0.0379 (4)
C7	0.0492 (5)	0.08343 (8)	0.17082 (13)	0.0425 (4)
C8	0.1188 (4)	0.11534 (7)	0.35014 (13)	0.0361 (4)
C9	0.0280 (4)	0.16375 (7)	0.42316 (13)	0.0364 (4)
C10	−0.1239 (5)	0.14748 (9)	0.51246 (14)	0.0468 (5)
H10	−0.1578	0.1069	0.5265	0.056*
C11	−0.2260 (5)	0.19071 (10)	0.58126 (16)	0.0553 (5)
H11	−0.3282	0.1789	0.6408	0.065*
C12	−0.1777 (5)	0.25082 (10)	0.56230 (16)	0.0553 (5)
H12	−0.2487	0.2796	0.6086	0.064*
C13	−0.0248 (5)	0.26852 (8)	0.47518 (15)	0.0474 (5)
H13	0.0099	0.3092	0.4622	0.065*
C14	0.0768 (4)	0.22512 (8)	0.40701 (13)	0.0383 (4)
N1	0.2876 (4)	0.07100 (6)	0.38216 (11)	0.0390 (4)
N2	0.2595 (4)	0.24605 (7)	0.31904 (12)	0.0469 (4)
O1	−0.0650 (4)	0.09470 (7)	0.08535 (10)	0.0645 (5)
O2	−0.0164 (3)	0.12322 (5)	0.25113 (9)	0.0440 (3)
O3	0.4312 (4)	0.21035 (7)	0.27731 (11)	0.0570 (4)
O4	0.2345 (6)	0.29876 (7)	0.29373 (14)	0.0860 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0628 (13)	0.0459 (11)	0.0380 (10)	−0.0012 (9)	0.0051 (9)	−0.0068 (8)
C2	0.0688 (14)	0.0393 (10)	0.0577 (12)	0.0042 (9)	0.0120 (10)	−0.0132 (9)
C3	0.0607 (13)	0.0354 (10)	0.0618 (12)	0.0068 (9)	0.0058 (10)	−0.0006 (9)
C4	0.0556 (12)	0.0363 (9)	0.0439 (10)	−0.0002 (8)	0.0000 (8)	0.0037 (8)
C5	0.0429 (10)	0.0309 (8)	0.0369 (9)	−0.0056 (7)	0.0038 (7)	−0.0021 (7)
C6	0.0455 (10)	0.0325 (8)	0.0359 (9)	−0.0044 (7)	0.0052 (7)	−0.0012 (7)
C7	0.0573 (12)	0.0370 (9)	0.0329 (9)	−0.0019 (8)	0.0011 (8)	−0.0027 (7)
C8	0.0455 (10)	0.0312 (8)	0.0315 (8)	−0.0064 (7)	0.0001 (7)	0.0011 (7)
C9	0.0397 (10)	0.0358 (9)	0.0335 (8)	−0.0009 (7)	−0.0003 (7)	−0.0032 (7)
C10	0.0542 (12)	0.0444 (10)	0.0419 (10)	−0.0074 (9)	0.0045 (8)	0.0007 (8)
C11	0.0569 (12)	0.0687 (14)	0.0418 (10)	−0.0086 (10)	0.0148 (9)	−0.0085 (9)
C12	0.0584 (13)	0.0575 (12)	0.0509 (11)	0.0016 (10)	0.0101 (9)	−0.0200 (9)
C13	0.0560 (12)	0.0371 (10)	0.0489 (11)	0.0010 (8)	0.0023 (9)	−0.0110 (8)
C14	0.0421 (10)	0.0379 (9)	0.0349 (9)	−0.0009 (7)	0.0022 (7)	−0.0026 (7)
N1	0.0508 (9)	0.0321 (7)	0.0339 (7)	−0.0008 (6)	0.0005 (6)	−0.0004 (6)
N2	0.0602 (10)	0.0383 (8)	0.0420 (8)	−0.0057 (7)	0.0023 (7)	0.0011 (7)
O1	0.0994 (12)	0.0560 (9)	0.0362 (7)	0.0131 (8)	−0.0125 (7)	−0.0019 (6)
O2	0.0592 (8)	0.0386 (7)	0.0335 (6)	0.0087 (6)	−0.0047 (5)	−0.0040 (5)
O3	0.0596 (9)	0.0585 (9)	0.0548 (8)	0.0009 (7)	0.0200 (7)	−0.0002 (7)
O4	0.1446 (18)	0.0398 (9)	0.0768 (12)	−0.0022 (9)	0.0351 (12)	0.0139 (7)

Geometric parameters (Å, º)

C1—C2	1.368 (3)	C8—O2	1.366 (2)
C1—C6	1.396 (2)	C8—C9	1.486 (2)
C1—H1	0.93	C9—C10	1.384 (2)
C2—C3	1.386 (3)	C9—C14	1.394 (2)
C2—H2	0.93	C10—C11	1.385 (3)
C3—C4	1.368 (3)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.373 (3)
C4—C5	1.394 (2)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.371 (3)
C5—C6	1.396 (2)	C12—H12	0.93
C5—N1	1.401 (2)	C13—C14	1.381 (2)
C6—C7	1.453 (3)	C13—H13	0.93
C7—O1	1.193 (2)	C14—N2	1.469 (2)
C7—O2	1.392 (2)	N2—O3	1.213 (2)
C8—N1	1.265 (2)	N2—O4	1.216 (2)
N1···C10^i	3.353 (3)	O3···C9^i	3.200 (3)
O2···O3^ii	3.045 (3)	O3···C14^i	3.103 (3)
O2···C5^ii	3.485 (3)	O4···C11^iii	3.245 (3)
C2—C1—C6	119.63 (18)	C10—C9—C14	117.03 (16)
C2—C1—H1	120.2	C10—C9—C8	118.28 (15)
C6—C1—H1	120.2	C14—C9—C8	124.66 (15)
C1—C2—C3	120.10 (18)	C9—C10—C11	120.95 (18)
C1—C2—H2	119.9	C9—C10—H10	119.5
C3—C2—H2	119.9	C11—C10—H10	119.5
C4—C3—C2	121.09 (18)	C12—C11—C10	120.51 (18)
C4—C3—H3	119.5	C12—C11—H11	119.7
C2—C3—H3	119.5	C10—C11—H11	119.7
C3—C4—C5	119.77 (18)	C13—C12—C11	120.09 (18)
C3—C4—H4	120.1	C13—C12—H12	120.0
C5—C4—H4	120.1	C11—C12—H12	120.0
C4—C5—C6	119.18 (16)	C12—C13—C14	119.06 (18)
C4—C5—N1	119.14 (16)	C12—C13—H13	120.5
C6—C5—N1	121.67 (15)	C14—C13—H13	120.5
C5—C6—C1	120.22 (17)	C13—C14—C9	122.35 (17)
C5—C6—C7	118.96 (15)	C13—C14—N2	116.96 (16)
C1—C6—C7	120.81 (16)	C9—C14—N2	120.58 (15)
O1—C7—O2	117.08 (17)	C8—N1—C5	117.07 (14)
O1—C7—C6	127.93 (17)	O3—N2—O4	123.76 (17)
O2—C7—C6	114.98 (14)	O3—N2—C14	118.43 (15)
N1—C8—O2	126.33 (15)	O4—N2—C14	117.79 (17)
N1—C8—C9	121.15 (15)	C8—O2—C7	120.76 (14)
O2—C8—C9	112.39 (14)
C6—C1—C2—C3	−0.4 (3)	C9—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	0.6 (3)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	−0.3 (3)	C11—C12—C13—C14	0.5 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—C9	0.4 (3)
C3—C4—C5—N1	−179.40 (17)	C12—C13—C14—N2	−175.73 (18)
C4—C5—C6—C1	0.3 (3)	C10—C9—C14—C13	−1.1 (3)
N1—C5—C6—C1	179.57 (16)	C8—C9—C14—C13	177.09 (17)
C4—C5—C6—C7	179.26 (17)	C10—C9—C14—N2	174.90 (16)
N1—C5—C6—C7	−1.5 (3)	C8—C9—C14—N2	−6.9 (3)
C2—C1—C6—C5	−0.1 (3)	O2—C8—N1—C5	3.6 (3)
C2—C1—C6—C7	−179.00 (18)	C9—C8—N1—C5	179.14 (15)
C5—C6—C7—O1	−179.8 (2)	C4—C5—N1—C8	179.57 (16)
C1—C6—C7—O1	−0.9 (3)	C6—C5—N1—C8	0.3 (2)
C5—C6—C7—O2	−0.9 (2)	C13—C14—N2—O3	158.17 (18)
C1—C6—C7—O2	178.02 (16)	C9—C14—N2—O3	−18.0 (3)
N1—C8—C9—C10	−54.3 (2)	C13—C14—N2—O4	−20.3 (3)
O2—C8—C9—C10	121.85 (18)	C9—C14—N2—O4	163.51 (19)
N1—C8—C9—C14	127.61 (19)	N1—C8—O2—C7	−6.3 (3)
O2—C8—C9—C14	−56.3 (2)	C9—C8—O2—C7	177.87 (15)
C14—C9—C10—C11	0.9 (3)	O1—C7—O2—C8	−176.52 (17)
C8—C9—C10—C11	−177.32 (18)	C6—C7—O2—C8	4.4 (2)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^iv	0.93	2.75	3.434 (2)	131
C12—H12···O1^v	0.93	2.91	3.470 (3)	120
C13—H13···O1^v	0.93	2.68	3.353 (2)	130
C12—H12···O3^vi	0.93	2.61	3.386 (2)	141
C11—H11···O4^vi	0.93	2.79	3.633 (3)	151
C2—H2···O4^vii	0.93	2.84	3.342 (3)	115
C3—H3···O4^vii	0.93	2.53	3.189 (2)	129

Symmetry codes: (iv) −x, −y, −z; (v) x, −y+1/2, z+1/2; (vi) x−1, −y+1/2, z+1/2; (vii) −x+1, y−1/2, −z+1/2.