6-Chloro-2H-1,4-benzoxazin-3(4H)-one.

In the title compound, C(8)H(6)ClNO(2), the conformation of the six-membered heterocyclic ring is close to screw boat and the mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds along the b axis.

Related literature

For biological activities of 1,4-benzoxazin-3(4H)-one derivatives, see: Huang et al. (2005 ▶); Macchiarulo et al. (2002 ▶). For a related structure, see: Pang et al. (2006 ▶).

Experimental

Crystal data

C8H6ClNO2

M = 183.59

Orthorhombic,

a = 4.5359 (6) Å

b = 7.700 (1) Å

c = 21.281 (3) Å

V = 743.28 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 273 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.878, T max = 0.973

3857 measured reflections

1314 independent reflections

1143 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.088

S = 1.07

1314 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 500 Friedel pairs

Flack parameter: 0.06 (11)

Data collection: SMART (Bruker 2002 ▶); cell refinement: SAINT (Bruker 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035599/wn2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035599/wn2285Isup2.hkl

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

C8H6ClNO2	Dx = 1.641 Mg m−3
Mr = 183.59	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1287 reflections
a = 4.5359 (6) Å	θ = 3.3–24.4º
b = 7.700 (1) Å	µ = 0.46 mm−1
c = 21.281 (3) Å	T = 273 (2) K
V = 743.28 (17) Å3	Plate, colourless
Z = 4	0.12 × 0.10 × 0.06 mm
F000 = 376

Bruker SMART CCD area-detector diffractometer	1314 independent reflections
Radiation source: fine-focus sealed tube	1143 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −5→4
Tmin = 0.878, Tmax = 0.973	k = −8→9
3857 measured reflections	l = −25→23

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.16 e Å−3
1314 reflections	Δρmin = −0.20 e Å−3
109 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 500 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (11)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.59509 (18)	0.16633 (10)	0.92672 (4)	0.0538 (3)
O1	1.5486 (5)	0.7552 (2)	0.74891 (10)	0.0488 (6)
O2	1.1177 (4)	0.8424 (2)	0.88354 (9)	0.0466 (6)
N1	1.2830 (5)	0.5732 (3)	0.80882 (10)	0.0347 (6)
H1	1.3651	0.4842	0.7918	0.042*
C1	1.3640 (6)	0.7302 (3)	0.79030 (14)	0.0350 (7)
C2	1.2111 (7)	0.8777 (3)	0.82142 (15)	0.0448 (8)
H2A	1.3430	0.9768	0.8222	0.054*
H2B	1.0404	0.9094	0.7965	0.054*
C3	0.9870 (6)	0.6859 (3)	0.89160 (13)	0.0346 (7)
C4	1.0683 (6)	0.5467 (3)	0.85521 (12)	0.0295 (6)
C5	0.9496 (6)	0.3866 (3)	0.86535 (13)	0.0339 (6)
H5	1.0043	0.2924	0.8406	0.041*
C6	0.7466 (6)	0.3675 (3)	0.91299 (13)	0.0369 (7)
C7	0.6661 (6)	0.5045 (4)	0.94990 (13)	0.0408 (7)
H7	0.5317	0.4889	0.9824	0.049*
C8	0.7839 (6)	0.6642 (4)	0.93876 (13)	0.0402 (7)
H8	0.7267	0.7586	0.9631	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0588 (5)	0.0489 (4)	0.0537 (5)	−0.0086 (4)	0.0042 (4)	0.0129 (4)
O1	0.0582 (14)	0.0464 (11)	0.0420 (13)	−0.0049 (10)	0.0170 (12)	0.0038 (9)
O2	0.0600 (14)	0.0389 (10)	0.0410 (13)	−0.0064 (12)	0.0119 (11)	−0.0098 (9)
N1	0.0375 (13)	0.0348 (12)	0.0319 (14)	0.0014 (11)	0.0068 (11)	−0.0017 (10)
C1	0.0401 (17)	0.0378 (14)	0.0272 (16)	−0.0022 (13)	−0.0029 (14)	−0.0005 (12)
C2	0.0532 (19)	0.0390 (15)	0.0423 (19)	−0.0032 (14)	0.0061 (16)	0.0019 (14)
C3	0.0362 (16)	0.0372 (14)	0.0305 (16)	−0.0012 (13)	−0.0001 (12)	−0.0028 (12)
C4	0.0291 (14)	0.0372 (14)	0.0221 (14)	0.0016 (13)	0.0002 (13)	−0.0008 (11)
C5	0.0370 (15)	0.0365 (14)	0.0282 (15)	0.0021 (13)	−0.0049 (13)	−0.0006 (11)
C6	0.0357 (15)	0.0424 (15)	0.0327 (17)	−0.0011 (13)	−0.0026 (13)	0.0083 (13)
C7	0.0392 (18)	0.0534 (17)	0.0297 (17)	−0.0007 (15)	0.0057 (13)	0.0011 (15)
C8	0.0425 (16)	0.0464 (15)	0.0315 (17)	0.0058 (16)	0.0041 (13)	−0.0052 (14)

Cl1—C6	1.720 (3)	C3—C8	1.373 (4)
O1—C1	1.231 (3)	C3—C4	1.373 (4)
O2—C3	1.354 (3)	C4—C5	1.362 (4)
O2—C2	1.414 (4)	C5—C6	1.377 (4)
N1—C1	1.324 (3)	C5—H5	0.9300
N1—C4	1.402 (3)	C6—C7	1.365 (4)
N1—H1	0.8600	C7—C8	1.362 (4)
C1—C2	1.486 (4)	C7—H7	0.9300
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700
C3—O2—C2	114.9 (2)	C5—C4—C3	120.7 (3)
C1—N1—C4	122.4 (2)	C5—C4—N1	121.2 (2)
C1—N1—H1	118.8	C3—C4—N1	118.0 (2)
C4—N1—H1	118.8	C4—C5—C6	118.5 (3)
O1—C1—N1	123.0 (3)	C4—C5—H5	120.7
O1—C1—C2	121.1 (2)	C6—C5—H5	120.7
N1—C1—C2	115.8 (3)	C7—C6—C5	121.3 (3)
O2—C2—C1	114.2 (2)	C7—C6—Cl1	119.4 (2)
O2—C2—H2A	108.7	C5—C6—Cl1	119.2 (2)
C1—C2—H2A	108.7	C8—C7—C6	119.5 (3)
O2—C2—H2B	108.7	C8—C7—H7	120.2
C1—C2—H2B	108.7	C6—C7—H7	120.2
H2A—C2—H2B	107.6	C7—C8—C3	120.1 (3)
O2—C3—C8	119.7 (2)	C7—C8—H8	120.0
O2—C3—C4	120.4 (2)	C3—C8—H8	120.0
C8—C3—C4	119.8 (3)
C4—N1—C1—O1	−178.8 (2)	C1—N1—C4—C5	167.7 (3)
C4—N1—C1—C2	−0.5 (4)	C1—N1—C4—C3	−14.2 (4)
C3—O2—C2—C1	−44.4 (3)	C3—C4—C5—C6	−0.1 (4)
O1—C1—C2—O2	−152.3 (3)	N1—C4—C5—C6	177.9 (2)
N1—C1—C2—O2	29.4 (4)	C4—C5—C6—C7	−0.5 (4)
C2—O2—C3—C8	−152.6 (3)	C4—C5—C6—Cl1	−179.8 (2)
C2—O2—C3—C4	31.1 (3)	C5—C6—C7—C8	1.3 (4)
O2—C3—C4—C5	176.3 (3)	Cl1—C6—C7—C8	−179.4 (2)
C8—C3—C4—C5	0.0 (4)	C6—C7—C8—C3	−1.4 (4)
O2—C3—C4—N1	−1.7 (4)	O2—C3—C8—C7	−175.6 (2)
C8—C3—C4—N1	−178.1 (2)	C4—C3—C8—C7	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.00	2.844 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.00	2.844 (3)	166

Symmetry code: (i) .