6-Chloro-8-methyl-4H-3,1-benzoxazine-2,4(1H)-dione.

The two mol-ecules in the asymmetric unit of the title compound, C(9)H(6)ClNO(3), are nearly planar, with r.m.s. deviations of 0.034 and 0.037 Å. The crystal structure is stabilized by two weak inter-molecular N-H⋯O inter-actions.

Related literature

For background to isatoic anhydrides, see: Miyamae (1996 ▶); Nawrot et al. (1997 ▶); Nawrot & Sprinz (1998 ▶); Deifel et al. (2010 ▶); Ren et al. (1996 ▶). For the preparation, see: Coppola (1980 ▶).

Experimental

Crystal data

C9H6ClNO3

M = 211.60

Monoclinic,

a = 8.3019 (12) Å

b = 13.1322 (18) Å

c = 15.742 (2) Å

β = 99.675 (9)°

V = 1691.8 (4) Å3

Z = 8

Cu Kα radiation

μ = 3.85 mm−1

T = 173 K

0.22 × 0.22 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.485, T max = 0.596

11524 measured reflections

3050 independent reflections

2280 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.01

3050 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.29 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536810013346/vm2022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013346/vm2022Isup2.hkl

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

C9H6ClNO3	F(000) = 864
Mr = 211.60	Dx = 1.661 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54186 Å
Hall symbol: -P 2yn	Cell parameters from 687 reflections
a = 8.3019 (12) Å	θ = 3.1–68.2°
b = 13.1322 (18) Å	µ = 3.85 mm−1
c = 15.742 (2) Å	T = 173 K
β = 99.675 (9)°	Plate, colorless
V = 1691.8 (4) Å3	0.22 × 0.22 × 0.15 mm
Z = 8

Rigaku R-AXIS RAPID IP area-detector diffractometer	3050 independent reflections
Radiation source: rotating anode	2280 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 68.2°, θmin = 4.4°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −10→9
Tmin = 0.485, Tmax = 0.596	k = −15→15
11524 measured reflections	l = −18→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3050 reflections	Δρmax = 0.49 e Å−3
256 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.74255 (7)	0.37308 (4)	0.31233 (4)	0.03722 (19)
Cl2	0.15868 (6)	0.36329 (4)	0.20423 (3)	0.03096 (18)
O1	0.15834 (17)	0.35341 (10)	0.42141 (10)	0.0352 (4)
O2	0.21462 (17)	0.36049 (9)	0.56311 (10)	0.0292 (4)
O3	0.25940 (17)	0.36009 (10)	0.70532 (10)	0.0343 (4)
O4	0.74385 (17)	0.36875 (10)	0.09544 (10)	0.0325 (4)
O5	0.68671 (17)	0.37641 (10)	−0.04621 (9)	0.0281 (4)
O6	0.64195 (17)	0.37865 (10)	−0.18829 (10)	0.0342 (4)
N1	0.4795 (2)	0.37337 (11)	0.63750 (11)	0.0263 (4)
H1A	0.5472	0.3789	0.6867	0.032*
N2	0.4212 (2)	0.38050 (11)	−0.12090 (11)	0.0248 (4)
H2A	0.3531	0.3836	−0.1701	0.030*
C1	0.6645 (3)	0.37491 (14)	0.40801 (14)	0.0287 (5)
C2	0.4986 (3)	0.36648 (13)	0.40569 (14)	0.0265 (5)
H2B	0.4261	0.3607	0.3524	0.032*
C3	0.4396 (3)	0.36668 (13)	0.48353 (14)	0.0251 (5)
C4	0.5457 (3)	0.37476 (13)	0.56177 (13)	0.0232 (5)
C5	0.7156 (3)	0.38488 (13)	0.56459 (14)	0.0255 (5)
C6	0.7711 (3)	0.38478 (13)	0.48592 (14)	0.0270 (5)
H6A	0.8849	0.3916	0.4854	0.032*
C7	0.2637 (3)	0.35950 (14)	0.48294 (14)	0.0262 (5)
C8	0.3186 (3)	0.36409 (14)	0.64046 (15)	0.0277 (5)
C9	0.8305 (2)	0.39789 (15)	0.64787 (13)	0.0297 (5)
H9A	0.9427	0.4032	0.6365	0.045*
H9B	0.8217	0.3390	0.6851	0.045*
H9C	0.8023	0.4600	0.6766	0.045*
C10	0.2366 (3)	0.37177 (13)	0.10859 (14)	0.0260 (5)
C11	0.4028 (2)	0.36882 (13)	0.11139 (14)	0.0250 (5)
H11A	0.4754	0.3641	0.1648	0.030*
C12	0.4623 (3)	0.37296 (13)	0.03310 (14)	0.0245 (5)
C13	0.3552 (3)	0.37864 (12)	−0.04491 (13)	0.0226 (5)
C14	0.1853 (2)	0.38394 (14)	−0.04755 (14)	0.0248 (5)
C15	0.1296 (3)	0.38043 (12)	0.03084 (14)	0.0249 (5)
H15A	0.0155	0.3841	0.0313	0.030*
C16	0.6380 (3)	0.37193 (13)	0.03436 (14)	0.0252 (5)
C17	0.5828 (3)	0.37785 (14)	−0.12356 (15)	0.0278 (5)
C18	0.0708 (2)	0.39453 (15)	−0.13148 (14)	0.0299 (5)
H18A	−0.0421	0.3958	−0.1208	0.045*
H18B	0.0852	0.3367	−0.1688	0.045*
H18C	0.0944	0.4580	−0.1597	0.045*

	U11	U22	U33	U12	U13	U23
Cl1	0.0344 (3)	0.0529 (4)	0.0255 (3)	0.0024 (2)	0.0083 (3)	−0.0006 (2)
Cl2	0.0292 (3)	0.0399 (3)	0.0246 (3)	−0.0011 (2)	0.0072 (2)	0.0001 (2)
O1	0.0251 (8)	0.0467 (9)	0.0321 (10)	−0.0004 (7)	−0.0004 (8)	0.0003 (7)
O2	0.0202 (7)	0.0424 (9)	0.0244 (9)	−0.0006 (6)	0.0020 (7)	0.0030 (6)
O3	0.0242 (8)	0.0540 (10)	0.0252 (9)	−0.0013 (7)	0.0053 (7)	0.0004 (7)
O4	0.0222 (8)	0.0449 (9)	0.0287 (9)	0.0000 (6)	−0.0012 (8)	0.0026 (7)
O5	0.0178 (7)	0.0407 (8)	0.0252 (9)	−0.0001 (6)	0.0019 (7)	−0.0038 (6)
O6	0.0220 (8)	0.0575 (10)	0.0240 (9)	−0.0022 (6)	0.0062 (7)	−0.0037 (7)
N1	0.0210 (9)	0.0348 (10)	0.0225 (10)	−0.0011 (7)	0.0016 (8)	−0.0008 (7)
N2	0.0177 (9)	0.0349 (9)	0.0209 (10)	−0.0006 (7)	0.0007 (8)	0.0000 (7)
C1	0.0324 (12)	0.0304 (11)	0.0236 (13)	0.0030 (9)	0.0059 (10)	0.0010 (8)
C2	0.0259 (11)	0.0275 (11)	0.0250 (12)	0.0030 (8)	0.0007 (10)	0.0010 (8)
C3	0.0236 (11)	0.0251 (10)	0.0257 (12)	0.0007 (8)	0.0015 (10)	0.0004 (8)
C4	0.0228 (11)	0.0213 (10)	0.0249 (12)	0.0001 (7)	0.0025 (10)	0.0008 (8)
C5	0.0244 (11)	0.0245 (10)	0.0268 (13)	0.0015 (8)	0.0021 (10)	−0.0015 (8)
C6	0.0222 (11)	0.0300 (11)	0.0289 (13)	0.0005 (8)	0.0047 (10)	−0.0005 (9)
C7	0.0232 (11)	0.0278 (11)	0.0258 (13)	−0.0001 (8)	−0.0015 (10)	0.0006 (8)
C8	0.0247 (11)	0.0280 (11)	0.0292 (13)	0.0015 (8)	0.0009 (10)	0.0037 (9)
C9	0.0222 (11)	0.0388 (12)	0.0272 (13)	−0.0023 (9)	0.0019 (10)	−0.0019 (9)
C10	0.0275 (11)	0.0256 (10)	0.0253 (13)	−0.0024 (8)	0.0060 (10)	−0.0020 (8)
C11	0.0230 (11)	0.0282 (11)	0.0230 (12)	0.0003 (8)	0.0012 (10)	0.0004 (8)
C12	0.0206 (10)	0.0240 (10)	0.0284 (13)	−0.0015 (8)	0.0028 (10)	−0.0013 (8)
C13	0.0231 (11)	0.0223 (10)	0.0224 (12)	−0.0011 (8)	0.0037 (10)	0.0001 (8)
C14	0.0206 (10)	0.0240 (10)	0.0288 (13)	−0.0004 (8)	0.0011 (10)	−0.0003 (8)
C15	0.0197 (10)	0.0259 (10)	0.0286 (13)	−0.0006 (8)	0.0030 (9)	−0.0007 (8)
C16	0.0219 (11)	0.0261 (10)	0.0265 (13)	0.0006 (8)	0.0012 (10)	−0.0006 (8)
C17	0.0250 (11)	0.0300 (11)	0.0277 (13)	−0.0018 (8)	0.0022 (10)	−0.0039 (9)
C18	0.0205 (11)	0.0381 (12)	0.0304 (13)	0.0020 (9)	0.0020 (10)	0.0008 (9)

Cl1—C1	1.737 (2)	C3—C7	1.462 (3)
Cl2—C10	1.739 (2)	C4—C5	1.410 (3)
O1—C7	1.194 (2)	C5—C6	1.392 (3)
O2—C8	1.370 (3)	C5—C9	1.496 (3)
O2—C7	1.390 (3)	C6—H6A	0.9500
O3—C8	1.206 (2)	C9—H9A	0.9800
O4—C16	1.189 (3)	C9—H9B	0.9800
O5—C17	1.369 (3)	C9—H9C	0.9800
O5—C16	1.396 (3)	C10—C11	1.374 (3)
O6—C17	1.203 (2)	C10—C15	1.391 (3)
N1—C8	1.350 (3)	C11—C12	1.403 (3)
N1—C4	1.394 (3)	C11—H11A	0.9500
N1—H1A	0.8800	C12—C13	1.392 (3)
N2—C17	1.349 (3)	C12—C16	1.456 (3)
N2—C13	1.397 (3)	C13—C14	1.406 (3)
N2—H2A	0.8800	C14—C15	1.389 (3)
C1—C2	1.376 (3)	C14—C18	1.499 (3)
C1—C6	1.393 (3)	C15—H15A	0.9500
C2—C3	1.394 (3)	C18—H18A	0.9800
C2—H2B	0.9500	C18—H18B	0.9800
C3—C4	1.393 (3)	C18—H18C	0.9800
C8—O2—C7	124.77 (17)	H9A—C9—H9B	109.5
C17—O5—C16	124.97 (17)	C5—C9—H9C	109.5
C8—N1—C4	124.42 (19)	H9A—C9—H9C	109.5
C8—N1—H1A	117.8	H9B—C9—H9C	109.5
C4—N1—H1A	117.8	C11—C10—C15	121.3 (2)
C17—N2—C13	124.13 (18)	C11—C10—Cl2	119.22 (17)
C17—N2—H2A	117.9	C15—C10—Cl2	119.45 (17)
C13—N2—H2A	117.9	C10—C11—C12	118.0 (2)
C2—C1—C6	121.1 (2)	C10—C11—H11A	121.0
C2—C1—Cl1	119.58 (18)	C12—C11—H11A	121.0
C6—C1—Cl1	119.34 (17)	C13—C12—C11	120.68 (19)
C1—C2—C3	118.3 (2)	C13—C12—C16	120.2 (2)
C1—C2—H2B	120.8	C11—C12—C16	119.14 (19)
C3—C2—H2B	120.8	C12—C13—N2	118.17 (19)
C4—C3—C2	120.9 (2)	C12—C13—C14	121.2 (2)
C4—C3—C7	119.6 (2)	N2—C13—C14	120.65 (19)
C2—C3—C7	119.51 (19)	C15—C14—C13	116.99 (19)
C3—C4—N1	118.26 (19)	C15—C14—C18	121.99 (19)
C3—C4—C5	121.1 (2)	C13—C14—C18	121.01 (19)
N1—C4—C5	120.68 (19)	C14—C15—C10	121.7 (2)
C6—C5—C4	116.81 (19)	C14—C15—H15A	119.1
C6—C5—C9	121.48 (19)	C10—C15—H15A	119.1
C4—C5—C9	121.69 (19)	O4—C16—O5	116.66 (19)
C5—C6—C1	121.8 (2)	O4—C16—C12	127.9 (2)
C5—C6—H6A	119.1	O5—C16—C12	115.46 (18)
C1—C6—H6A	119.1	O6—C17—N2	125.1 (2)
O1—C7—O2	116.79 (19)	O6—C17—O5	117.84 (19)
O1—C7—C3	127.2 (2)	N2—C17—O5	117.00 (19)
O2—C7—C3	116.02 (18)	C14—C18—H18A	109.5
O3—C8—N1	125.4 (2)	C14—C18—H18B	109.5
O3—C8—O2	117.74 (19)	H18A—C18—H18B	109.5
N1—C8—O2	116.9 (2)	C14—C18—H18C	109.5
C5—C9—H9A	109.5	H18A—C18—H18C	109.5
C5—C9—H9B	109.5	H18B—C18—H18C	109.5
C6—C1—C2—C3	−0.8 (3)	C15—C10—C11—C12	−1.1 (3)
Cl1—C1—C2—C3	179.08 (13)	Cl2—C10—C11—C12	178.26 (12)
C1—C2—C3—C4	−0.3 (3)	C10—C11—C12—C13	−0.7 (3)
C1—C2—C3—C7	179.00 (16)	C10—C11—C12—C16	178.83 (16)
C2—C3—C4—N1	−179.29 (15)	C11—C12—C13—N2	−178.74 (15)
C7—C3—C4—N1	1.4 (2)	C16—C12—C13—N2	1.7 (2)
C2—C3—C4—C5	1.2 (3)	C11—C12—C13—C14	2.2 (3)
C7—C3—C4—C5	−178.09 (17)	C16—C12—C13—C14	−177.37 (16)
C8—N1—C4—C3	0.4 (3)	C17—N2—C13—C12	−0.5 (3)
C8—N1—C4—C5	179.93 (17)	C17—N2—C13—C14	178.58 (16)
C3—C4—C5—C6	−0.9 (3)	C12—C13—C14—C15	−1.7 (3)
N1—C4—C5—C6	179.55 (15)	N2—C13—C14—C15	179.27 (15)
C3—C4—C5—C9	177.47 (16)	C12—C13—C14—C18	177.37 (16)
N1—C4—C5—C9	−2.0 (3)	N2—C13—C14—C18	−1.7 (3)
C4—C5—C6—C1	−0.2 (3)	C13—C14—C15—C10	−0.2 (3)
C9—C5—C6—C1	−178.58 (16)	C18—C14—C15—C10	−179.25 (16)
C2—C1—C6—C5	1.1 (3)	C11—C10—C15—C14	1.6 (3)
Cl1—C1—C6—C5	−178.84 (14)	Cl2—C10—C15—C14	−177.76 (13)
C8—O2—C7—O1	178.00 (15)	C17—O5—C16—O4	178.23 (15)
C8—O2—C7—C3	−2.3 (2)	C17—O5—C16—C12	−2.5 (2)
C4—C3—C7—O1	179.09 (18)	C13—C12—C16—O4	178.89 (18)
C2—C3—C7—O1	−0.2 (3)	C11—C12—C16—O4	−0.7 (3)
C4—C3—C7—O2	−0.5 (2)	C13—C12—C16—O5	−0.3 (2)
C2—C3—C7—O2	−179.82 (15)	C11—C12—C16—O5	−179.91 (14)
C4—N1—C8—O3	177.97 (17)	C13—N2—C17—O6	179.44 (17)
C4—N1—C8—O2	−3.1 (3)	C13—N2—C17—O5	−2.1 (3)
C7—O2—C8—O3	−176.85 (16)	C16—O5—C17—O6	−177.76 (16)
C7—O2—C8—N1	4.1 (2)	C16—O5—C17—N2	3.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6i	0.88	1.99	2.846 (3)	163
N2—H2A···O3ii	0.88	2.01	2.850 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6i	0.88	1.99	2.846 (3)	163
N2—H2A⋯O3ii	0.88	2.01	2.850 (2)	160

Symmetry codes: (i) ; (ii) .