organic compounds
3-(1,3-Benzodioxol-5-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
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
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
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Data collection: SMART (Bruker, 2000); cell 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
https://doi.org/10.1107/S1600536807063192/xu2388sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063192/xu2388Isup2.hkl
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.
Imino H atom was located in a difference Fourier map and positional parameters were refined, Uiso(H) = 1.2Ueq(N). Other H atoms were placed in calculated positions, with C—H = 0.93 Å (aromatic) and 0.97 Å (methylene), and refined in riding mode with Uiso(H)=1.2Ueq(C). In absence of significant
Friedel pairs were merged.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)°.
For general background, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998).
Data collection: SMART (Bruker, 2000); cell
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).Fig. 1. The ORTEP plot of (I). Displacement ellipsoids are drawn at the 30% probability level. |
C25H19NO3 | F(000) = 400 |
Mr = 381.41 | Dx = 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 |
Bruker SMART APEX CCD area-detector diffractometer | 2412 independent reflections |
Radiation source: sealed tube | 1824 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 28.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −12→12 |
Tmin = 0.97, Tmax = 0.98 | k = −7→7 |
5964 measured reflections | l = −15→22 |
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(Fo2) + (0.0517P)2 + 0.1645P] where P = (Fo2 + 2Fc2)/3 |
2412 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
C25H19NO3 | V = 907.3 (5) Å3 |
Mr = 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)° |
Bruker SMART APEX CCD area-detector diffractometer | 2412 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1824 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.98 | Rint = 0.041 |
5964 measured reflections |
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 | Δρmax = 0.21 e Å−3 |
2412 reflections | Δρmin = −0.20 e Å−3 |
265 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.97, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5964, 2412, 1824 |
Rint | 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 |
Δρmax, Δρmin (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
Bruker (2000). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913–919. CrossRef CAS Web of Science Google Scholar
Mahajan, R. N., Havaldar, F. H. & Femandes, P. S. (1991). J. Indian Chem. Soc. 68, 245–249. CAS Google Scholar
Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199–200. Google Scholar
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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)°.