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

Mehrdad, M.; Ghanbari, M.; Jadidi, K.; Salemi, A.; Khavasi, H.R.

doi:10.1107/S1600536810050294

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o49

https://doi.org/10.1107/S1600536810050294

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(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 and Hamid Reza Khavasi ^b

^aDepartment of Environmental Pollution, Environmental Sciences Research Institute, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: m_mehrdad4@yahoo.com

(Received 29 November 2010; accepted 1 December 2010; online 8 December 2010)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.083
wR(F²) = 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

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
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050294/bt5425Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Structure description top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. Reaction scheme.
	Fig. 2. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. Unit-cell packing diagram for (I).

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

Crystal data top

C₂₂H₁₉N₃O₃	F(000) = 784
M_r = 373.40	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 21467 reflections
a = 14.4225 (14) Å	θ = 1.7–29.3°
b = 8.0836 (5) Å	µ = 0.09 mm⁻¹
c = 16.2749 (14) Å	T = 298 K
β = 107.263 (7)°	Needle, yellow
V = 1811.9 (3) Å³	0.60 × 0.13 × 0.04 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	3190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.111
Graphite monochromator	θ_max = 29.3°, θ_min = 1.7°
Detector resolution: 0.15 mm pixels mm^-1	h = −18→19
rotation method scans	k = −10→11
21467 measured reflections	l = −22→22
4893 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0578P)² + 0.8502P] where P = (F_o² + 2F_c²)/3
4893 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₂H₁₉N₃O₃	V = 1811.9 (3) Å³
M_r = 373.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.4225 (14) Å	µ = 0.09 mm⁻¹
b = 8.0836 (5) Å	T = 298 K
c = 16.2749 (14) Å	0.60 × 0.13 × 0.04 mm
β = 107.263 (7)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.15	Δρ_max = 0.24 e Å⁻³
4893 reflections	Δρ_min = −0.28 e Å⁻³
253 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.0070 (3)	0.2134 (5)	0.0453 (2)	0.0719 (9)
H1A	−0.0208	0.3142	0.0707	0.086*
H1B	0.0435	0.1542	0.0866	0.086*
H1C	−0.0645	0.1464	0.0281	0.086*
C2	0.1045 (2)	0.3483 (3)	−0.01638 (17)	0.0497 (6)
C3	0.1271 (2)	0.3897 (3)	−0.09054 (17)	0.0521 (7)
H3	0.0870	0.3551	−0.1437	0.063*
C4	0.2088 (2)	0.4820 (3)	−0.08625 (16)	0.0476 (6)
H4	0.2224	0.5109	−0.1368	0.057*
C5	0.27136 (19)	0.5328 (3)	−0.00716 (16)	0.0459 (6)
C6	0.2465 (2)	0.4957 (4)	0.06647 (17)	0.0557 (7)
H6	0.2861	0.5319	0.1196	0.067*
C7	0.1629 (2)	0.4047 (4)	0.06239 (18)	0.0570 (7)
H7	0.1465	0.3822	0.1124	0.068*
C8	0.43609 (19)	0.6338 (3)	0.05119 (16)	0.0446 (6)
C9	0.54000 (18)	0.5791 (3)	0.18936 (16)	0.0436 (6)
C10	0.5543 (2)	0.5004 (4)	0.26776 (18)	0.0518 (6)
H10	0.5058	0.4342	0.2773	0.062*
C11	0.6412 (2)	0.5210 (4)	0.33167 (17)	0.0536 (7)
H11	0.6514	0.4685	0.3844	0.064*
C12	0.7131 (2)	0.6199 (4)	0.31721 (18)	0.0554 (7)
H12	0.7713	0.6340	0.3606	0.066*
C13	0.6990 (2)	0.6979 (4)	0.23896 (17)	0.0525 (7)
H13	0.7476	0.7644	0.2298	0.063*
C14	0.61137 (18)	0.6767 (3)	0.17343 (15)	0.0428 (6)
C15	0.5157 (2)	0.7295 (3)	0.03396 (16)	0.0447 (6)
C16	0.55436 (18)	0.8817 (3)	−0.08379 (15)	0.0435 (6)
C17	0.6539 (2)	0.9088 (4)	−0.04862 (17)	0.0536 (7)
H17	0.6862	0.8660	0.0053	0.064*
C18	0.7048 (2)	0.9990 (4)	−0.09332 (18)	0.0578 (7)
H18	0.7713	1.0150	−0.0693	0.069*
C19	0.6583 (2)	1.0656 (3)	−0.17326 (17)	0.0487 (6)
C20	0.5592 (2)	1.0388 (4)	−0.20832 (17)	0.0548 (7)
H20	0.5268	1.0827	−0.2620	0.066*
C21	0.5087 (2)	0.9484 (4)	−0.16457 (16)	0.0505 (6)
H21	0.4425	0.9312	−0.1894	0.061*
C22	0.8046 (2)	1.1618 (5)	−0.1983 (2)	0.0777 (10)
H22A	0.8289	1.0517	−0.1997	0.093*
H22B	0.8296	1.2060	−0.1412	0.093*
H22C	0.8250	1.2305	−0.2379	0.093*
N1	0.35461 (16)	0.6221 (3)	−0.01063 (14)	0.0499 (5)
N2	0.59911 (15)	0.7521 (3)	0.09392 (12)	0.0413 (5)
N3	0.49602 (16)	0.7909 (3)	−0.04487 (13)	0.0494 (5)
H3A	0.4381	0.7720	−0.0774	0.059*
O1	0.02353 (17)	0.2511 (3)	−0.02758 (14)	0.0700 (6)
O2	0.45078 (13)	0.5596 (3)	0.12731 (12)	0.0556 (5)
O3	0.70194 (16)	1.1580 (3)	−0.22196 (13)	0.0655 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.066 (2)	0.077 (2)	0.076 (2)	−0.0097 (17)	0.0262 (17)	0.0031 (18)
C2	0.0490 (15)	0.0481 (15)	0.0498 (14)	0.0023 (12)	0.0114 (12)	−0.0024 (12)
C3	0.0606 (17)	0.0492 (15)	0.0416 (13)	−0.0021 (13)	0.0074 (12)	−0.0070 (12)
C4	0.0567 (16)	0.0476 (15)	0.0367 (12)	0.0030 (12)	0.0111 (11)	−0.0008 (11)
C5	0.0479 (14)	0.0464 (14)	0.0405 (12)	0.0063 (11)	0.0088 (11)	−0.0015 (11)
C6	0.0488 (15)	0.075 (2)	0.0393 (13)	−0.0014 (14)	0.0072 (11)	−0.0043 (13)
C7	0.0549 (17)	0.075 (2)	0.0414 (13)	−0.0001 (15)	0.0143 (12)	0.0018 (13)
C8	0.0438 (13)	0.0448 (14)	0.0420 (13)	0.0052 (11)	0.0077 (11)	−0.0031 (11)
C9	0.0378 (13)	0.0457 (14)	0.0445 (13)	0.0027 (10)	0.0079 (10)	0.0008 (11)
C10	0.0464 (14)	0.0535 (16)	0.0554 (15)	0.0022 (12)	0.0147 (12)	0.0093 (13)
C11	0.0533 (16)	0.0587 (17)	0.0434 (13)	0.0080 (13)	0.0061 (12)	0.0054 (13)
C12	0.0479 (15)	0.0627 (18)	0.0486 (14)	−0.0022 (13)	0.0035 (12)	−0.0079 (13)
C13	0.0467 (15)	0.0584 (17)	0.0499 (15)	−0.0085 (12)	0.0104 (12)	−0.0057 (13)
C14	0.0438 (13)	0.0431 (13)	0.0414 (12)	0.0015 (11)	0.0125 (10)	−0.0020 (10)
C15	0.0531 (15)	0.0393 (13)	0.0443 (13)	0.0065 (11)	0.0186 (11)	−0.0017 (10)
C16	0.0440 (13)	0.0461 (14)	0.0400 (12)	0.0054 (11)	0.0119 (11)	−0.0026 (10)
C17	0.0440 (14)	0.0676 (18)	0.0433 (14)	0.0022 (13)	0.0036 (12)	0.0082 (13)
C18	0.0421 (14)	0.075 (2)	0.0497 (14)	−0.0037 (14)	0.0041 (12)	0.0031 (15)
C19	0.0533 (15)	0.0501 (15)	0.0423 (13)	0.0014 (12)	0.0136 (12)	−0.0018 (11)
C20	0.0530 (16)	0.0699 (19)	0.0372 (12)	0.0059 (14)	0.0068 (12)	0.0054 (13)
C21	0.0422 (13)	0.0640 (18)	0.0408 (13)	0.0028 (12)	0.0052 (11)	−0.0016 (12)
C22	0.0560 (19)	0.095 (3)	0.084 (2)	−0.0101 (18)	0.0233 (18)	0.012 (2)
N1	0.0459 (12)	0.0551 (14)	0.0447 (11)	−0.0003 (10)	0.0071 (10)	−0.0023 (10)
N2	0.0417 (11)	0.0446 (12)	0.0361 (10)	−0.0024 (9)	0.0095 (8)	−0.0002 (9)
N3	0.0446 (12)	0.0576 (14)	0.0431 (11)	0.0033 (10)	0.0087 (9)	0.0008 (10)
O1	0.0668 (14)	0.0815 (15)	0.0617 (13)	−0.0229 (12)	0.0193 (11)	−0.0067 (11)
O2	0.0446 (10)	0.0604 (12)	0.0558 (11)	−0.0025 (9)	0.0058 (9)	0.0078 (9)
O3	0.0595 (13)	0.0817 (15)	0.0544 (11)	−0.0078 (11)	0.0157 (10)	0.0101 (11)

Geometric parameters (Å, º) top

C1—O1	1.416 (4)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.381 (4)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.402 (4)
C2—O1	1.374 (3)	C13—H13	0.9300
C2—C3	1.382 (4)	C14—N2	1.393 (3)
C2—C7	1.386 (4)	C15—N2	1.318 (3)
C3—C4	1.378 (4)	C15—N3	1.325 (3)
C3—H3	0.9300	C16—C21	1.393 (4)
C4—C5	1.397 (3)	C16—C17	1.396 (4)
C4—H4	0.9300	C16—N3	1.401 (3)
C5—C6	1.382 (4)	C17—C18	1.385 (4)
C5—N1	1.417 (4)	C17—H17	0.9300
C6—C7	1.397 (4)	C18—C19	1.384 (4)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—O3	1.370 (3)
C8—N1	1.304 (3)	C19—C20	1.390 (4)
C8—O2	1.336 (3)	C20—C21	1.371 (4)
C8—C15	1.479 (4)	C20—H20	0.9300
C9—C14	1.381 (4)	C21—H21	0.9300
C9—C10	1.385 (4)	C22—O3	1.415 (4)
C9—O2	1.389 (3)	C22—H22A	0.9600
C10—C11	1.381 (4)	C22—H22B	0.9600
C10—H10	0.9300	C22—H22C	0.9600
C11—C12	1.384 (4)	N3—H3A	0.8600

O1—C1—H1A	109.5	C12—C13—H13	120.1
O1—C1—H1B	109.5	C14—C13—H13	120.1
H1A—C1—H1B	109.5	C9—C14—N2	121.9 (2)
O1—C1—H1C	109.5	C9—C14—C13	118.8 (2)
H1A—C1—H1C	109.5	N2—C14—C13	119.4 (2)
H1B—C1—H1C	109.5	N2—C15—N3	123.5 (2)
O1—C2—C3	115.8 (2)	N2—C15—C8	121.4 (2)
O1—C2—C7	124.8 (3)	N3—C15—C8	115.1 (2)
C3—C2—C7	119.5 (3)	C21—C16—C17	117.8 (2)
C4—C3—C2	120.5 (2)	C21—C16—N3	116.8 (2)
C4—C3—H3	119.8	C17—C16—N3	125.4 (2)
C2—C3—H3	119.8	C18—C17—C16	120.6 (2)
C3—C4—C5	121.0 (2)	C18—C17—H17	119.7
C3—C4—H4	119.5	C16—C17—H17	119.7
C5—C4—H4	119.5	C19—C18—C17	120.9 (3)
C6—C5—C4	118.2 (3)	C19—C18—H18	119.5
C6—C5—N1	125.9 (2)	C17—C18—H18	119.5
C4—C5—N1	115.9 (2)	O3—C19—C18	125.3 (3)
C5—C6—C7	121.0 (3)	O3—C19—C20	116.1 (2)
C5—C6—H6	119.5	C18—C19—C20	118.5 (3)
C7—C6—H6	119.5	C21—C20—C19	120.7 (2)
C2—C7—C6	119.8 (3)	C21—C20—H20	119.7
C2—C7—H7	120.1	C19—C20—H20	119.7
C6—C7—H7	120.1	C20—C21—C16	121.4 (2)
N1—C8—O2	122.8 (2)	C20—C21—H21	119.3
N1—C8—C15	117.7 (2)	C16—C21—H21	119.3
O2—C8—C15	119.5 (2)	O3—C22—H22A	109.5
C14—C9—C10	121.3 (2)	O3—C22—H22B	109.5
C14—C9—O2	120.6 (2)	H22A—C22—H22B	109.5
C10—C9—O2	118.1 (2)	O3—C22—H22C	109.5
C11—C10—C9	119.5 (3)	H22A—C22—H22C	109.5
C11—C10—H10	120.3	H22B—C22—H22C	109.5
C9—C10—H10	120.3	C8—N1—C5	125.9 (2)
C10—C11—C12	120.0 (3)	C15—N2—C14	117.6 (2)
C10—C11—H11	120.0	C15—N3—C16	130.4 (2)
C12—C11—H11	120.0	C15—N3—H3A	114.8
C13—C12—C11	120.6 (3)	C16—N3—H3A	114.8
C13—C12—H12	119.7	C2—O1—C1	118.4 (2)
C11—C12—H12	119.7	C8—O2—C9	118.8 (2)
C12—C13—C14	119.9 (3)	C19—O3—C22	118.5 (2)

O1—C2—C3—C4	−177.7 (3)	C17—C18—C19—O3	179.2 (3)
C7—C2—C3—C4	2.0 (4)	C17—C18—C19—C20	−0.6 (5)
C2—C3—C4—C5	1.3 (4)	O3—C19—C20—C21	−179.8 (3)
C3—C4—C5—C6	−3.4 (4)	C18—C19—C20—C21	0.0 (4)
C3—C4—C5—N1	177.9 (2)	C19—C20—C21—C16	0.5 (5)
C4—C5—C6—C7	2.3 (4)	C17—C16—C21—C20	−0.4 (4)
N1—C5—C6—C7	−179.3 (3)	N3—C16—C21—C20	−179.8 (3)
O1—C2—C7—C6	176.6 (3)	O2—C8—N1—C5	0.2 (4)
C3—C2—C7—C6	−3.2 (4)	C15—C8—N1—C5	178.3 (2)
C5—C6—C7—C2	1.0 (5)	C6—C5—N1—C8	25.8 (4)
C14—C9—C10—C11	0.6 (4)	C4—C5—N1—C8	−155.7 (3)
O2—C9—C10—C11	−178.2 (3)	N3—C15—N2—C14	−178.2 (2)
C9—C10—C11—C12	0.1 (4)	C8—C15—N2—C14	2.6 (3)
C10—C11—C12—C13	−0.4 (5)	C9—C14—N2—C15	1.1 (4)
C11—C12—C13—C14	−0.1 (4)	C13—C14—N2—C15	−179.9 (2)
C10—C9—C14—N2	177.9 (2)	N2—C15—N3—C16	3.1 (4)
O2—C9—C14—N2	−3.4 (4)	C8—C15—N3—C16	−177.7 (2)
C10—C9—C14—C13	−1.1 (4)	C21—C16—N3—C15	−171.6 (3)
O2—C9—C14—C13	177.7 (2)	C17—C16—N3—C15	9.0 (5)
C12—C13—C14—C9	0.9 (4)	C3—C2—O1—C1	−176.0 (3)
C12—C13—C14—N2	−178.1 (3)	C7—C2—O1—C1	4.3 (5)
N1—C8—C15—N2	177.6 (2)	N1—C8—O2—C9	−180.0 (2)
O2—C8—C15—N2	−4.3 (4)	C15—C8—O2—C9	2.0 (3)
N1—C8—C15—N3	−1.7 (3)	C14—C9—O2—C8	1.6 (4)
O2—C8—C15—N3	176.5 (2)	C10—C9—O2—C8	−179.6 (2)
C21—C16—C17—C18	−0.2 (4)	C18—C19—O3—C22	12.6 (5)
N3—C16—C17—C18	179.2 (3)	C20—C19—O3—C22	−167.6 (3)
C16—C17—C18—C19	0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	0.93	2.59	3.423 (3)	149

Symmetry code: (i) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉N₃O₃
M_r	373.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.4225 (14), 8.0836 (5), 16.2749 (14)
β (°)	107.263 (7)
V (Å³)	1811.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.13 × 0.04

Data collection
Diffractometer	Stoe IPDS II
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21467, 4893, 3190
R_int	0.111
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.195, 1.15
No. of reflections	4893
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	0.93	2.59	3.423 (3)	149

Symmetry code: (i) x−1/2, −y+3/2, z+1/2.

Acknowledgements

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

References

Asgari, D., Mehrdad, M., Ghanbari, M., Jadidi, K., Behzad, S. K. & Khavasi, H. R. (2011). Acta Cryst. E67. Submitted [BT5429] Google Scholar
Azizian, J., Mehrdad, M., Jadidi, K. & Sarrafi, Y. (2000). Tetrahedron Lett. 41, 5265–5268. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jadidi, K., Ghahremanzadeh, R., Mehrdad, M., Ghanbari, M. & Arvin-Nezhad, H. (2008). Monatsh. Chem. 139, 277–280. Web of Science CSD CrossRef CAS Google Scholar
Mehrdad, M., Ghanbari, M., Jadidi, K., Asgari, D. & Khavasi, H. R. (2011). In preparation. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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organic compounds

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