(2Z)-N-(4-Meth­oxy­phen­yl)-2-(4-meth­oxy­phenyl­imino)-2H-1,4-benzoxazin-3-amine

Morteza Mehrdad; Mohammad Ghanbari; Khosrow Jadidi; Amir Salemi; Hamid Reza Khavasi

doi:10.1107/S1600536810050294

. 2010 Dec 8;67(Pt 1):o49. doi: 10.1107/S1600536810050294

(2Z)-N-(4-Methoxyphenyl)-2-(4-methoxyphenylimino)-2H-1,4-benzoxazin-3-amine

Morteza Mehrdad ^a,^*, Mohammad Ghanbari ^b, Khosrow Jadidi ^b, Amir Salemi ^a, Hamid Reza Khavasi ^b

PMCID: PMC3050339 PMID: 21522758

Abstract

In the crystal structure of the title compound, C₂₂H₁₉N₃O₃, intermolecular C—H⋯O hydrogen bonds link the molecules into a zigzag chain parallel to the face diagonal of the ac plane. The methoxy phenyl rings make a dihdral angle of 32.38 (7)° and form dihedral angles of 0.66 (8) and 24.17 (7)° with the fused benzooxazine ring system.

Related literature

For the Baeyer–Villiger oxidation of 1-alkyl-3-arylimino-2-indolinone with m-chloroperbenzoic acid to afford 1-alkyl-4-(arylimino)-1H benzo[d][1,3]oxazin-2(4H)-one, see: Mehrdad et al. (2011 ▶); Azizian et al. (2000 ▶); Jadidi et al. (2008 ▶). For a related structure, see: Asgari et al. (2011 ▶).

Experimental

Crystal data

C₂₂H₁₉N₃O₃
M _r = 373.40
Monoclinic,
a = 14.4225 (14) Å
b = 8.0836 (5) Å
c = 16.2749 (14) Å
β = 107.263 (7)°
V = 1811.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.60 × 0.13 × 0.04 mm

Data collection

Stoe IPDS II diffractometer
21467 measured reflections
4893 independent reflections
3190 reflections with I > 2σ(I)
R _int = 0.111

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.195
S = 1.15
4893 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050294/bt5425sup1.cif

e-67-00o49-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050294/bt5425Isup2.hkl

e-67-00o49-Isup2.hkl^{(234.8KB, 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
C7—H7⋯O3ⁱ	0.93	2.59	3.423 (3)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Vice President of Research Affairs at Shahid Beheshti University, General Campus, for financial support.

supplementary crystallographic information

Comment

Recently, we reported a Baeyer–Villiger oxidation of 1-alkyl-3-arylimino-2-indolinone with m-chloroperbenzoic acid to afford 1-alkyl-4-(arylimino)-1H benzo[d][1,3]oxazin-2(4H)-one (Azizian et al., 2000; Jadidi et al., 2008). As a continuation of this work, 2-arylimino-N-aryl-2H-benzo[b][1,4]oxazin-3-amines (2) or N-aryl-N-(2-arylamino-3H-indol-3-ylidene)amine N-oxides (3) were obtained in two different temperatures by Baeyer-Villiger oxidation reaction (Fig. 1) of N-aryl-3-(arylimino)-3H-indol-2-amines (1) (Mehrdad et al., 2011). In this paper, we report the structure of (2Z)-2-(4-methoxyphenylimino)-N-(4-methoxyphenyl)- 2H-benzo[b][1,4]oxazin-3-amine (2a). The molecular structure of the title compound is shown in Fig. 2.

The methoxy phenyl rings, A (C2—C7) and B (C16—C21) and benzooxazine ring C (C9—C14/C8/O2/N2/C15) enclose the dihedral angles: A/B = 32.38 (7)°, A/C = 10.66 (8)° and B/C = 24.17 (7)°. Intermolecular C—H···O interactions (Table 1) stabilize the crystal structure.

Experimental

The solution of N-Aryl-3-(Arylimino)-3H-indol-2-amine (1a) (1.0 mmol) in 25 ml CH₂Cl₂ was cooled to 253K. Then, m-CPBA (1.5 mmol) dissolved in 25 ml CH₂Cl₂ was added dropwise to the stirred solution of (1a). After stirring for 6 h at 253K, product (2a) was formed (monitoring by TLC). The crude product was poured into water and extracted with CH₂Cl₂ (60 ml). The organic layer was dried over Na₂SO₄, and evaporation of the solvent afforded the crude product (2a), which was purified on silica gel by column chromatography using 90:10 n-hexane:ethyl acetate as eluent to afford (2a) as a light yellow solid (90%); m.p. = 169–171°C (Mehrdad et al., 2011).