3-(1,3-Benzodioxol-5-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Yang, Y.-F.; Yang, L.-R.; Yin, Z.-G.; Qian, H.-Y.

doi:10.1107/S1600536807063192

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o147

https://doi.org/10.1107/S1600536807063192

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3-(1,3-Benzodioxol-5-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Yu-Feng Yang,^a Liang-Ru Yang,^b Zhi-Gang Yin ^c ^* and Heng-Yu Qian ^c

^aDepartment of Chemistry, Henan Institute of Education, Zhengzhou 450014, People's Republic of China, ^bSchool of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450052, People's Republic of China, and ^cKey Laboratory of Surface and Interface Science of Henan, School of Materials & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: yinzhigang3141@yahoo.com.cn

(Received 24 November 2007; accepted 25 November 2007; online 6 December 2007)

In the title compound, C₂₅H₁₉NO₃, the oxazine ring displays a half-chair conformation. The fused benzene ring is nearly parallel to the naphthyl ring system, the dihedral angle between this benzene ring and the naphthyl system being 8.52 (11)°. The imino group is not involved in hydrogen bonding in the crystal structure.

Related literature

For general background, see: Katayama & Oshiyama (1997 ); Mahajan et al. (1991 ); Mishra et al. (1998 ).

Experimental

Crystal data

C₂₅H₁₉NO₃
M_r = 381.41
Monoclinic, P 2₁
a = 9.180 (3) Å
b = 5.7585 (18) Å
c = 17.320 (5) Å
β = 97.707 (4)°
V = 907.3 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.97, T_max = 0.98
5964 measured reflections
2412 independent reflections
1824 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.134
S = 1.18
2412 reflections
265 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063192/xu2388sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063192/xu2388Isup2.hkl

checkCIF report

Comment top

The oxazine derivatives display various applications and widespresd potential biological and pharmacological activities such as antimicrobial (Mahajan et al., 1991), antitumor (Katayama & Oshiyama, 1997) and antihistaminic (Mishra et al., 1998). In view of these important properties, we reported the crystal strucutre of the tilte compound.

The oxazine ring in the molecular is not planar. The 1,3-benzodioxole ring makes the dihedral angles of 68.24 (11)° and 8.52 (11)° with the benzene ring and the naphthyl ring, respectively, while the plane O1/C1/C10/C11 is co-planar with the naphthalene ring with the dihedral angle 1.43 (11)°. The dihedral angle between the benzene ring and the naphthalene ring is 71.48 (16)°.

Related literature top

For general background, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998).

Experimental top

1-(Amino(phenyl)methyl)naphthalen-2-ol (1 mmol, 0.249 g) was dissolved in anhydrous methanol, the mixture was stirred for several minitutes, 1,3-benzodioxole-5-carbaldehyde (1 mmol, 0.150 g) in methanol (6 ml) was added dropwise and the mixture was stirred at room temperature for 2 h. The product was isolated and recrystallized in dichloromethane. Colorless single crystals of (I) was obtained after 4 d.

Structure description top

For general background, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. The ORTEP plot of (I). Displacement ellipsoids are drawn at the 30% probability level.

3-(1,3-Benzodioxol-5-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine top

Crystal data top

C₂₅H₁₉NO₃	F(000) = 400
M_r = 381.41	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 912 reflections
a = 9.180 (3) Å	θ = 2.1–25.1°
b = 5.7585 (18) Å	µ = 0.09 mm⁻¹
c = 17.320 (5) Å	T = 291 K
β = 97.707 (4)°	Block, colorless
V = 907.3 (5) Å³	0.30 × 0.26 × 0.24 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2412 independent reflections
Radiation source: sealed tube	1824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
T_min = 0.97, T_max = 0.98	k = −7→7
5964 measured reflections	l = −15→22

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0517P)² + 0.1645P] where P = (F_o² + 2F_c²)/3
2412 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₅H₁₉NO₃	V = 907.3 (5) Å³
M_r = 381.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.180 (3) Å	µ = 0.09 mm⁻¹
b = 5.7585 (18) Å	T = 291 K
c = 17.320 (5) Å	0.30 × 0.26 × 0.24 mm
β = 97.707 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2412 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1824 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.98	R_int = 0.041
5964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	1 restraint
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.21 e Å⁻³
2412 reflections	Δρ_min = −0.20 e Å⁻³
265 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	0.4757 (4)	1.2105 (7)	0.2026 (2)	0.0336 (8)
C2	0.5763 (4)	1.3803 (7)	0.1817 (2)	0.0357 (9)
H2	0.5449	1.4902	0.1438	0.043*
C3	0.7154 (4)	1.3826 (8)	0.2163 (2)	0.0394 (9)
H3	0.7794	1.4958	0.2026	0.047*
C4	0.7663 (4)	1.2181 (7)	0.2729 (2)	0.0333 (8)
C5	0.9118 (4)	1.2228 (7)	0.3104 (2)	0.0366 (9)
H5	0.9719	1.3457	0.2999	0.044*
C6	0.9709 (5)	1.0510 (8)	0.3631 (2)	0.0407 (10)
H6	1.0664	1.0603	0.3888	0.049*
C7	0.8740 (4)	0.8566 (8)	0.3752 (2)	0.0402 (9)
H7	0.9091	0.7295	0.4052	0.048*
C8	0.7357 (4)	0.8655 (8)	0.3425 (2)	0.0386 (9)
H8	0.6735	0.7503	0.3568	0.046*
C9	0.6719 (4)	1.0330 (7)	0.2877 (2)	0.0321 (8)
C10	0.5191 (4)	1.0343 (8)	0.2527 (2)	0.0376 (9)
C11	0.4128 (4)	0.8432 (8)	0.2724 (2)	0.0400 (9)
H11	0.4613	0.6936	0.2670	0.048*
C12	0.3653 (4)	0.8494 (7)	0.3526 (2)	0.0362 (8)
C13	0.4046 (4)	1.0273 (7)	0.4006 (2)	0.0328 (8)
H13	0.4569	1.1531	0.3849	0.039*
C14	0.3628 (4)	1.0156 (8)	0.4770 (2)	0.0421 (10)
H14	0.3893	1.1363	0.5118	0.051*
C15	0.2837 (5)	0.8292 (9)	0.5011 (3)	0.0461 (10)
H15	0.2581	0.8223	0.5512	0.055*
C16	0.2441 (4)	0.6531 (8)	0.4472 (2)	0.0395 (9)
H16	0.1881	0.5293	0.4613	0.047*
C17	0.2874 (4)	0.6570 (9)	0.3703 (3)	0.0441 (10)
H17	0.2642	0.5369	0.3349	0.053*
C18	0.2306 (4)	1.0885 (7)	0.2003 (2)	0.0378 (9)
H18	0.2162	1.1499	0.2515	0.045*
C19	0.0807 (5)	1.1079 (8)	0.1429 (2)	0.0411 (9)
C20	0.0568 (4)	1.2985 (8)	0.0972 (2)	0.0368 (9)
H20	0.1311	1.4084	0.0973	0.044*
C21	−0.0776 (4)	1.3335 (8)	0.0497 (2)	0.0360 (8)
H21	−0.0999	1.4701	0.0219	0.043*
C22	−0.1737 (4)	1.1502 (7)	0.0475 (2)	0.0326 (8)
C23	−0.1516 (5)	0.9640 (8)	0.0947 (2)	0.0427 (10)
C24	−0.0182 (4)	0.9259 (8)	0.1459 (2)	0.0360 (9)
H24	0.0002	0.7955	0.1773	0.043*
C25	−0.3700 (5)	0.9157 (8)	0.0285 (2)	0.0459 (11)
H25A	−0.4622	0.9372	0.0491	0.055*
H25B	−0.3875	0.8163	−0.0170	0.055*
N1	0.2826 (4)	0.8559 (7)	0.2088 (2)	0.0388 (8)
H1	0.246 (5)	0.740 (9)	0.182 (3)	0.047*
O1	0.3362 (3)	1.2333 (5)	0.16696 (15)	0.0380 (7)
O2	−0.3139 (3)	1.1315 (6)	0.00830 (16)	0.0414 (7)
O3	−0.2657 (3)	0.8142 (5)	0.08500 (15)	0.0392 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.030 (2)	0.0311 (18)	0.0063 (17)	0.0014 (15)	−0.0124 (15)
C2	0.0389 (19)	0.037 (2)	0.0284 (16)	−0.0056 (18)	−0.0063 (14)	−0.0042 (17)
C3	0.0299 (17)	0.043 (2)	0.047 (2)	0.0083 (18)	0.0127 (16)	0.0024 (19)
C4	0.0272 (17)	0.034 (2)	0.0397 (19)	0.0003 (16)	0.0071 (15)	−0.0007 (16)
C5	0.045 (2)	0.038 (2)	0.0265 (17)	−0.0072 (18)	0.0017 (16)	−0.0114 (16)
C6	0.040 (2)	0.041 (2)	0.038 (2)	0.0099 (19)	−0.0060 (17)	−0.0057 (18)
C7	0.0345 (19)	0.041 (2)	0.044 (2)	0.0158 (19)	0.0009 (16)	0.0089 (19)
C8	0.0339 (18)	0.043 (2)	0.041 (2)	0.0136 (18)	0.0123 (16)	0.0105 (19)
C9	0.0268 (17)	0.033 (2)	0.0381 (18)	0.0110 (16)	0.0101 (14)	−0.0079 (17)
C10	0.0371 (19)	0.043 (2)	0.0286 (17)	−0.0135 (19)	−0.0113 (15)	−0.0011 (17)
C11	0.0356 (18)	0.040 (2)	0.044 (2)	−0.001 (2)	0.0023 (16)	−0.0123 (19)
C12	0.0419 (19)	0.0265 (19)	0.0380 (19)	0.0106 (17)	−0.0025 (16)	−0.0006 (17)
C13	0.0241 (16)	0.034 (2)	0.0412 (19)	0.0112 (15)	0.0079 (14)	−0.0127 (16)
C14	0.046 (2)	0.045 (2)	0.0308 (18)	0.007 (2)	−0.0139 (16)	0.0014 (19)
C15	0.044 (2)	0.048 (3)	0.044 (2)	0.011 (2)	−0.0022 (18)	0.001 (2)
C16	0.0318 (18)	0.042 (2)	0.044 (2)	0.0108 (18)	0.0020 (16)	0.012 (2)
C17	0.037 (2)	0.044 (2)	0.052 (2)	0.0013 (19)	0.0081 (17)	0.007 (2)
C18	0.045 (2)	0.035 (2)	0.0345 (18)	0.0014 (19)	0.0093 (16)	0.0072 (17)
C19	0.046 (2)	0.035 (2)	0.040 (2)	0.0108 (19)	−0.0046 (17)	−0.0032 (18)
C20	0.0304 (17)	0.045 (2)	0.0375 (19)	−0.0078 (18)	0.0136 (15)	0.0042 (19)
C21	0.0363 (18)	0.037 (2)	0.0359 (18)	−0.0073 (18)	0.0113 (15)	0.0153 (17)
C22	0.0390 (19)	0.0253 (18)	0.0303 (16)	0.0039 (17)	−0.0076 (14)	−0.0012 (16)
C23	0.047 (2)	0.036 (2)	0.042 (2)	−0.0057 (19)	−0.0068 (18)	0.0018 (18)
C24	0.0367 (19)	0.039 (2)	0.0338 (18)	0.0135 (17)	0.0096 (15)	−0.0067 (17)
C25	0.039 (2)	0.049 (3)	0.045 (2)	−0.007 (2)	−0.0106 (18)	−0.001 (2)
N1	0.0329 (16)	0.0346 (19)	0.0460 (18)	−0.0174 (15)	−0.0059 (13)	0.0043 (16)
O1	0.0395 (14)	0.0368 (15)	0.0384 (14)	0.0117 (13)	0.0078 (11)	0.0163 (13)
O2	0.0378 (14)	0.0425 (17)	0.0416 (14)	−0.0021 (14)	−0.0035 (12)	0.0058 (14)
O3	0.0398 (14)	0.0368 (16)	0.0396 (13)	0.0003 (13)	−0.0003 (11)	0.0185 (13)

Geometric parameters (Å, º) top

C1—O1	1.351 (4)	C14—H14	0.9300
C1—C10	1.359 (6)	C15—C16	1.393 (7)
C1—C2	1.425 (6)	C15—H15	0.9300
C2—C3	1.336 (5)	C16—C17	1.440 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.398 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—N1	1.424 (6)
C4—C5	1.405 (5)	C18—O1	1.456 (5)
C4—C9	1.419 (5)	C18—C19	1.589 (6)
C5—C6	1.405 (6)	C18—H18	0.9800
C5—H5	0.9300	C19—C20	1.354 (6)
C6—C7	1.462 (6)	C19—C24	1.392 (6)
C6—H6	0.9300	C20—C21	1.403 (5)
C7—C8	1.320 (5)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.373 (5)
C8—C9	1.423 (5)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.347 (6)
C9—C10	1.452 (5)	C22—O2	1.376 (4)
C10—C11	1.539 (6)	C23—O3	1.350 (5)
C11—C12	1.511 (5)	C23—C24	1.429 (5)
C11—N1	1.514 (5)	C24—H24	0.9300
C11—H11	0.9800	C25—O3	1.401 (5)
C12—C13	1.339 (5)	C25—O2	1.408 (6)
C12—C17	1.375 (6)	C25—H25A	0.9700
C13—C14	1.428 (5)	C25—H25B	0.9700
C13—H13	0.9300	N1—H1	0.86 (5)
C14—C15	1.391 (7)

O1—C1—C10	122.9 (4)	C14—C15—C16	117.4 (4)
O1—C1—C2	115.1 (3)	C14—C15—H15	121.3
C10—C1—C2	122.0 (3)	C16—C15—H15	121.3
C3—C2—C1	120.4 (4)	C15—C16—C17	121.9 (4)
C3—C2—H2	119.8	C15—C16—H16	119.0
C1—C2—H2	119.8	C17—C16—H16	119.0
C2—C3—C4	121.2 (4)	C12—C17—C16	115.8 (4)
C2—C3—H3	119.4	C12—C17—H17	122.1
C4—C3—H3	119.4	C16—C17—H17	122.1
C3—C4—C5	121.3 (4)	N1—C18—O1	110.3 (3)
C3—C4—C9	118.7 (3)	N1—C18—C19	112.4 (3)
C5—C4—C9	119.8 (4)	O1—C18—C19	106.2 (3)
C4—C5—C6	123.2 (4)	N1—C18—H18	109.3
C4—C5—H5	118.4	O1—C18—H18	109.3
C6—C5—H5	118.4	C19—C18—H18	109.3
C5—C6—C7	116.3 (3)	C20—C19—C24	125.2 (4)
C5—C6—H6	121.9	C20—C19—C18	118.8 (4)
C7—C6—H6	121.9	C24—C19—C18	116.0 (4)
C8—C7—C6	118.5 (4)	C19—C20—C21	121.3 (4)
C8—C7—H7	120.7	C19—C20—H20	119.3
C6—C7—H7	120.7	C21—C20—H20	119.3
C7—C8—C9	126.8 (4)	C22—C21—C20	114.6 (4)
C7—C8—H8	116.6	C22—C21—H21	122.7
C9—C8—H8	116.6	C20—C21—H21	122.7
C4—C9—C8	115.0 (3)	C23—C22—C21	123.5 (3)
C4—C9—C10	120.0 (3)	C23—C22—O2	107.0 (3)
C8—C9—C10	124.8 (4)	C21—C22—O2	128.9 (3)
C1—C10—C9	117.0 (4)	C22—C23—O3	112.5 (3)
C1—C10—C11	122.3 (3)	C22—C23—C24	123.0 (4)
C9—C10—C11	120.6 (3)	O3—C23—C24	124.4 (4)
C12—C11—N1	111.8 (3)	C19—C24—C23	111.7 (4)
C12—C11—C10	117.1 (3)	C19—C24—H24	124.1
N1—C11—C10	105.4 (3)	C23—C24—H24	124.1
C12—C11—H11	107.3	O3—C25—O2	107.7 (3)
N1—C11—H11	107.3	O3—C25—H25A	110.2
C10—C11—H11	107.3	O2—C25—H25A	110.2
C13—C12—C17	125.6 (4)	O3—C25—H25B	110.2
C13—C12—C11	120.2 (4)	O2—C25—H25B	110.2
C17—C12—C11	114.2 (4)	H25A—C25—H25B	108.5
C12—C13—C14	117.2 (4)	C18—N1—C11	110.0 (3)
C12—C13—H13	121.4	C18—N1—H1	125 (3)
C14—C13—H13	121.4	C11—N1—H1	125 (3)
C15—C14—C13	122.0 (4)	C1—O1—C18	113.8 (3)
C15—C14—H14	119.0	C22—O2—C25	107.2 (3)
C13—C14—H14	119.0	C23—O3—C25	105.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉NO₃
M_r	381.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	9.180 (3), 5.7585 (18), 17.320 (5)
β (°)	97.707 (4)
V (Å³)	907.3 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.97, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	5964, 2412, 1824
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.134, 1.18
No. of reflections	2412
No. of parameters	265
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Acknowledgements

The authors express their deep appreciation to the Startup Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry, China (No.2005001).

References

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