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

Yan-Ling Zhou; Hua Wang; Min Zhao

doi:10.1107/S1600536810013346

. 2010 Apr 21;66(Pt 5):o1127. doi: 10.1107/S1600536810013346

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

Yan-Ling Zhou ^a, Hua Wang ^b, Min Zhao ^a,^*

PMCID: PMC2979130 PMID: 21579176

Abstract

The two molecules in the asymmetric unit of the title compound, C₉H₆ClNO₃, are nearly planar, with r.m.s. deviations of 0.034 and 0.037 Å. The crystal structure is stabilized by two weak intermolecular N—H⋯O interactions.

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 _r = 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
Δρ_max = 0.49 e Å⁻³
Δρ_min = −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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013346/vm2022sup1.cif

e-66-o1127-sup1.cif^{(20.2KB, cif)}

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

e-66-o1127-Isup2.hkl^{(149.7KB, hkl)}

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

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

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Northeast Forestry University Youth Research Fund (09054).

supplementary crystallographic information

Comment

Isatoic anhydride derivatives are generally used as intermediates in the synthesis of heterocyclic compounds, such as agricultural chemicals, medicines, pharmaceuticals, quinazolinones, quinazolones, benzimidazolones, phthalimides, pyrroloquinazolones, quinazolinediones and in the fluorescent labeling of mRNAand tRNA (Miyamae, 1996; Nawrot et al., 1997; Nawrot et al., 1998; Deifel et al., 2010; Ren et al., 1996).

The title compound is a nearly planar molecule (Fig. 1). The bond distances are consistent with an aromatic system. There are two molecules in the asymmetric unit of the title compound. The molecular structure is stabilized by two weak intermolecular N–H···O interactions resulting in the formation of dimers.

Experimental

The isatoic anhydride was prepared by reaction of anthranilic acid with triphosgene in good yield (Coppola, 1980). The title compound (0.2 g) was dissolved in ethanol (50 ml) at room temperature. Colourless blocks of (I) were obtained through slow evaporation after two weeks.