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Acta Cryst. (2008). E64, o1972    [ doi:10.1107/S1600536808029383 ]

2-Butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Y. H. Li, M. M. Zhao and Y. Zhang

Abstract top

In the title compound, C28H27NO, the oxazine ring adopts a half-chair conformation. The dihedral angles between the phenyl rings and the naphthyl ring system are 15.34 (1) and 76.51 (1)°.

Comment top

Continuing efforts have been made to synthesize oxazine compounds because they are widely used as antipsychotic agents (Barker et al., 2006), antimalarial agents (Ren et al., 2001) and serotonin, dopamine receptors agonists (Petterson et al., 1990; Peglion et al., 1997). We have prepared a novel compound, 2-butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine, (I), by the reaction of 2-naphthol, benzaldehyde and n-butylamine. In this paper, we present the synthesis and crystal structure of (I). The structures of some closely related compounds have been reported (Alfonsov et al., 2007; Ji et al. 2005).

In the molecule of the title compound (Fig. 1), the oxazine ring adopts a half chair conformation. An intra-molecular interaction, C17—H15···O1, is observed in the crystal structure, but no inter-molecular hydrogen bonding was present. The dihedral angle between the C16–C21 phenyl ring and naphthyl system is 15.34 (1)° and the dihedral angle between the C23–C28 phenyl ring and naphthyl system is 76.51 (1)°.

Related literature top

For general background on oxazine compounds, see: Barker et al. (2006); Ren et al. (2001); Petterson et al. (1990); Peglion et al. (1997). For related structures, see: Alfonsov et al. (2007); Ji et al. (2005).

Experimental top

The title compound was one of the products of the reaction between 2-naphthol, n-butylamine and an excess amount of benzaldehyde. Benzaldehyde (22.05 g, 0.208 mol) was added to a solution of 2-naphthol (15 g, 0.104 mol) in 20 ml 95% ethanol. n-Butylamine (7.65 g, 0.104 mol) was added dropwise with cooling to 273 K to this solution. The mixture was stirred at room temperature for 6 days and the precipitate was filtrated and washed with a small amount of 95% ethanol. The title compound was isolated using column chromatography (petroleum ether: ethyl acetate - 30:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of an ethanol solution.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl groups, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
2-Butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine top
Crystal data top
C28H27NOZ = 2
Mr = 393.51F(000) = 420
Triclinic, P1Dx = 1.185 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8959 (15) ÅCell parameters from 2254 reflections
b = 10.7589 (16) Åθ = 2.3–27.5°
c = 11.8401 (18) ŵ = 0.07 mm−1
α = 96.219 (1)°T = 293 K
β = 98.366 (2)°Prism, colourless
γ = 97.274 (2)°0.20 × 0.18 × 0.15 mm
V = 1102.8 (3) Å3
Data collection top
Rigaku SCXmini
diffractometer		4302 independent reflections
Radiation source: fine-focus sealed tube2352 reflections with I > 2σ(I)
graphiteRint = 0.041
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scanh = −10→10
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −13→13
Tmin = 0.965, Tmax = 0.977l = −14→14
10108 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.262H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1501P)2]
where P = (Fo2 + 2Fc2)/3
4302 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C28H27NOγ = 97.274 (2)°
Mr = 393.51V = 1102.8 (3) Å3
Triclinic, P1Z = 2
a = 8.8959 (15) ÅMo Kα radiation
b = 10.7589 (16) ŵ = 0.07 mm−1
c = 11.8401 (18) ÅT = 293 K
α = 96.219 (1)°0.20 × 0.18 × 0.15 mm
β = 98.366 (2)°
Data collection top
Rigaku SCXmini
diffractometer		4302 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2352 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.977Rint = 0.041
10108 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.072H-atom parameters constrained
wR(F2) = 0.262Δρmax = 0.26 e Å−3
S = 1.02Δρmin = −0.34 e Å−3
4302 reflectionsAbsolute structure: ?
272 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C1−0.0487 (3)0.6705 (3)0.1444 (2)0.0520 (7)
C10−0.0728 (3)0.7223 (3)0.2512 (2)0.0486 (7)
C160.3447 (3)0.8083 (3)0.1275 (2)0.0489 (7)
C9−0.2156 (3)0.6833 (3)0.2883 (3)0.0551 (7)
C110.0504 (3)0.8228 (3)0.3234 (2)0.0522 (7)
H5−0.00160.89260.35050.063*
C2−0.1621 (3)0.5819 (3)0.0713 (3)0.0604 (8)
H6−0.14390.5486−0.00040.073*
C220.2099 (3)0.7704 (3)0.1862 (2)0.0505 (7)
H70.24220.71240.24020.061*
C4−0.3288 (3)0.5932 (3)0.2146 (3)0.0599 (8)
C230.1350 (3)0.7789 (3)0.4296 (2)0.0517 (7)
C120.1042 (3)0.9693 (3)0.1822 (2)0.0571 (7)
H10A−0.00480.94500.15460.069*
H10B0.15610.97110.11560.069*
C210.4792 (3)0.8709 (3)0.1948 (3)0.0621 (8)
H110.48110.89260.27320.074*
C3−0.2976 (3)0.5457 (3)0.1064 (3)0.0689 (9)
H12−0.37190.48800.05750.083*
C8−0.2484 (4)0.7299 (3)0.3967 (3)0.0677 (9)
H13−0.17620.78900.44600.081*
C240.1235 (3)0.6555 (3)0.4499 (2)0.0560 (7)
H140.05830.59410.39770.067*
C170.3449 (4)0.7784 (3)0.0112 (3)0.0641 (8)
H150.25620.7370−0.03620.077*
C5−0.4699 (3)0.5539 (4)0.2525 (4)0.0777 (10)
H16−0.54510.49590.20460.093*
C130.1311 (4)1.1005 (3)0.2498 (3)0.0712 (9)
H17A0.08641.09660.31960.085*
H17B0.24081.12670.27240.085*
C190.6094 (4)0.8710 (3)0.0332 (3)0.0733 (10)
H180.69790.89140.00180.088*
C180.4781 (4)0.8101 (4)−0.0357 (3)0.0799 (10)
H190.47730.7898−0.11410.096*
C7−0.3862 (4)0.6891 (4)0.4304 (3)0.0834 (11)
H20−0.40620.72090.50210.100*
C200.6101 (4)0.9016 (3)0.1482 (3)0.0717 (9)
H210.69910.94340.19520.086*
C140.0657 (5)1.1976 (4)0.1856 (3)0.0914 (12)
H4−0.04461.17330.16610.110*
H22B0.10671.19860.11410.110*
C250.2064 (4)0.6200 (4)0.5459 (3)0.0716 (9)
H230.19570.53540.55740.086*
C6−0.4955 (4)0.6004 (4)0.3579 (4)0.0896 (12)
H24−0.58740.57260.38210.108*
C280.2381 (4)0.8682 (3)0.5083 (3)0.0834 (11)
H250.25240.95240.49600.100*
C260.3032 (5)0.7066 (4)0.6236 (3)0.0845 (11)
H260.35790.68210.68850.101*
C270.3192 (5)0.8298 (4)0.6054 (3)0.1023 (14)
H270.38530.88960.65850.123*
C150.0978 (6)1.3295 (4)0.2499 (4)0.1108 (15)
H30.05021.33140.31770.166*
H20.05701.38720.20130.166*
H10.20671.35390.27160.166*
N10.1605 (2)0.8740 (2)0.25219 (18)0.0489 (6)
O10.0848 (2)0.69988 (18)0.10138 (16)0.0578 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0460 (15)0.0516 (17)0.0593 (16)0.0120 (12)0.0086 (13)0.0048 (13)
C100.0449 (14)0.0492 (16)0.0540 (15)0.0082 (11)0.0119 (12)0.0108 (12)
C160.0508 (15)0.0450 (15)0.0544 (15)0.0123 (11)0.0143 (13)0.0080 (12)
C90.0489 (16)0.0567 (18)0.0652 (18)0.0162 (13)0.0125 (14)0.0187 (14)
C110.0547 (16)0.0477 (16)0.0566 (16)0.0118 (12)0.0161 (13)0.0024 (12)
C20.0490 (17)0.0607 (19)0.0671 (18)0.0078 (13)0.0032 (14)−0.0033 (15)
C220.0513 (16)0.0473 (16)0.0521 (15)0.0100 (12)0.0067 (13)0.0010 (12)
C40.0422 (15)0.0596 (19)0.082 (2)0.0098 (13)0.0107 (15)0.0226 (16)
C230.0565 (16)0.0527 (17)0.0462 (14)0.0079 (12)0.0123 (13)0.0020 (12)
C120.0645 (17)0.0514 (17)0.0589 (17)0.0157 (13)0.0144 (14)0.0083 (13)
C210.0573 (18)0.066 (2)0.0652 (18)0.0055 (14)0.0170 (15)0.0125 (15)
C30.0478 (17)0.060 (2)0.093 (2)0.0083 (14)−0.0060 (17)0.0046 (17)
C80.0602 (18)0.075 (2)0.075 (2)0.0158 (15)0.0238 (16)0.0203 (17)
C240.0505 (16)0.0596 (19)0.0590 (17)0.0018 (13)0.0138 (13)0.0127 (14)
C170.0610 (18)0.070 (2)0.0643 (18)0.0091 (15)0.0206 (15)0.0082 (15)
C50.0448 (17)0.081 (2)0.112 (3)0.0058 (15)0.0152 (19)0.033 (2)
C130.090 (2)0.0544 (19)0.073 (2)0.0154 (16)0.0162 (18)0.0122 (15)
C190.063 (2)0.071 (2)0.098 (3)0.0118 (16)0.041 (2)0.0249 (19)
C180.094 (3)0.088 (3)0.067 (2)0.018 (2)0.038 (2)0.0108 (18)
C70.068 (2)0.107 (3)0.094 (3)0.025 (2)0.044 (2)0.036 (2)
C200.0578 (19)0.069 (2)0.090 (2)0.0049 (15)0.0180 (18)0.0160 (18)
C140.125 (3)0.066 (2)0.097 (3)0.034 (2)0.033 (3)0.024 (2)
C250.070 (2)0.082 (2)0.069 (2)0.0103 (17)0.0176 (18)0.0276 (18)
C60.054 (2)0.112 (3)0.118 (3)0.020 (2)0.029 (2)0.048 (3)
C280.111 (3)0.062 (2)0.068 (2)0.0097 (19)−0.001 (2)−0.0060 (17)
C260.101 (3)0.098 (3)0.057 (2)0.021 (2)0.008 (2)0.021 (2)
C270.130 (4)0.096 (3)0.064 (2)0.018 (3)−0.024 (2)−0.015 (2)
C150.165 (4)0.064 (3)0.117 (3)0.037 (3)0.050 (3)0.012 (2)
N10.0543 (13)0.0453 (13)0.0494 (12)0.0119 (10)0.0120 (10)0.0063 (10)
O10.0514 (11)0.0605 (13)0.0576 (12)0.0002 (9)0.0120 (9)−0.0051 (9)
Geometric parameters (Å, °) top
C1—O11.373 (3)C24—C251.379 (4)
C1—C101.383 (4)C24—H140.9300
C1—C21.414 (4)C17—C181.399 (4)
C10—C91.432 (4)C17—H150.9300
C10—C111.526 (4)C5—C61.355 (5)
C16—C171.379 (4)C5—H160.9300
C16—C211.386 (4)C13—C141.485 (5)
C16—C221.506 (4)C13—H17A0.9700
C9—C81.411 (4)C13—H17B0.9700
C9—C41.425 (4)C19—C201.364 (5)
C11—N11.477 (3)C19—C181.368 (5)
C11—C231.520 (4)C19—H180.9300
C11—H50.9800C18—H190.9300
C2—C31.356 (4)C7—C61.392 (5)
C2—H60.9300C7—H200.9300
C22—N11.443 (3)C20—H210.9300
C22—O11.456 (3)C14—C151.508 (5)
C22—H70.9800C14—H40.9700
C4—C31.406 (5)C14—H22B0.9700
C4—C51.424 (4)C25—C261.356 (5)
C23—C241.369 (4)C25—H230.9300
C23—C281.402 (4)C6—H240.9300
C12—N11.477 (3)C28—C271.396 (5)
C12—C131.519 (4)C28—H250.9300
C12—H10A0.9700C26—C271.358 (6)
C12—H10B0.9700C26—H260.9300
C21—C201.379 (4)C27—H270.9300
C21—H110.9300C15—H30.9600
C3—H120.9300C15—H20.9600
C8—C71.378 (4)C15—H10.9600
C8—H130.9300
O1—C1—C10123.4 (2)C18—C17—H15119.8
O1—C1—C2115.1 (2)C6—C5—C4120.4 (4)
C10—C1—C2121.5 (3)C6—C5—H16119.8
C1—C10—C9118.7 (3)C4—C5—H16119.8
C1—C10—C11119.1 (2)C14—C13—C12114.1 (3)
C9—C10—C11122.1 (2)C14—C13—H17A108.7
C17—C16—C21117.9 (3)C12—C13—H17A108.7
C17—C16—C22123.8 (3)C14—C13—H17B108.7
C21—C16—C22118.3 (2)C12—C13—H17B108.7
C8—C9—C4118.2 (3)H17A—C13—H17B107.6
C8—C9—C10122.3 (3)C20—C19—C18119.7 (3)
C4—C9—C10119.4 (3)C20—C19—H18120.1
N1—C11—C23110.4 (2)C18—C19—H18120.1
N1—C11—C10110.7 (2)C19—C18—C17120.4 (3)
C23—C11—C10114.3 (2)C19—C18—H19119.8
N1—C11—H5107.0C17—C18—H19119.8
C23—C11—H5107.0C8—C7—C6120.3 (4)
C10—C11—H5107.0C8—C7—H20119.8
C3—C2—C1119.6 (3)C6—C7—H20119.8
C3—C2—H6120.2C19—C20—C21120.1 (3)
C1—C2—H6120.2C19—C20—H21120.0
N1—C22—O1111.8 (2)C21—C20—H21120.0
N1—C22—C16114.3 (2)C13—C14—C15114.6 (4)
O1—C22—C16109.3 (2)C13—C14—H4108.6
N1—C22—H7107.0C15—C14—H4108.6
O1—C22—H7107.0C13—C14—H22B108.6
C16—C22—H7107.0C15—C14—H22B108.6
C3—C4—C5122.0 (3)H4—C14—H22B107.6
C3—C4—C9118.9 (3)C26—C25—C24120.9 (3)
C5—C4—C9119.2 (3)C26—C25—H23119.5
C24—C23—C28117.5 (3)C24—C25—H23119.5
C24—C23—C11123.8 (2)C5—C6—C7121.0 (3)
C28—C23—C11118.6 (3)C5—C6—H24119.5
N1—C12—C13112.2 (2)C7—C6—H24119.5
N1—C12—H10A109.2C27—C28—C23119.6 (3)
C13—C12—H10A109.2C27—C28—H25120.2
N1—C12—H10B109.2C23—C28—H25120.2
C13—C12—H10B109.2C25—C26—C27119.1 (3)
H10A—C12—H10B107.9C25—C26—H26120.4
C20—C21—C16121.6 (3)C27—C26—H26120.4
C20—C21—H11119.2C26—C27—C28121.2 (4)
C16—C21—H11119.2C26—C27—H27119.4
C2—C3—C4121.8 (3)C28—C27—H27119.4
C2—C3—H12119.1C14—C15—H3109.5
C4—C3—H12119.1C14—C15—H2109.5
C7—C8—C9120.9 (3)H3—C15—H2109.5
C7—C8—H13119.6C14—C15—H1109.5
C9—C8—H13119.6H3—C15—H1109.5
C23—C24—C25121.6 (3)H2—C15—H1109.5
C23—C24—H14119.2C22—N1—C11109.0 (2)
C25—C24—H14119.2C22—N1—C12113.8 (2)
C16—C17—C18120.3 (3)C11—N1—C12113.8 (2)
C16—C17—H15119.8C1—O1—C22113.8 (2)
O1—C1—C10—C9−179.0 (2)C11—C23—C24—C25178.0 (3)
C2—C1—C10—C90.9 (4)C21—C16—C17—C180.5 (5)
O1—C1—C10—C113.4 (4)C22—C16—C17—C18−176.0 (3)
C2—C1—C10—C11−176.7 (2)C3—C4—C5—C6179.2 (3)
C1—C10—C9—C8178.9 (3)C9—C4—C5—C6−0.8 (5)
C11—C10—C9—C8−3.6 (4)N1—C12—C13—C14−175.6 (3)
C1—C10—C9—C4−0.3 (4)C20—C19—C18—C17−0.5 (5)
C11—C10—C9—C4177.2 (2)C16—C17—C18—C190.0 (5)
C1—C10—C11—N115.7 (3)C9—C8—C7—C60.2 (5)
C9—C10—C11—N1−161.8 (2)C18—C19—C20—C210.3 (5)
C1—C10—C11—C23−109.8 (3)C16—C21—C20—C190.2 (5)
C9—C10—C11—C2372.7 (3)C12—C13—C14—C15−177.4 (3)
O1—C1—C2—C3179.4 (2)C23—C24—C25—C26−0.3 (5)
C10—C1—C2—C3−0.5 (4)C4—C5—C6—C71.2 (6)
C17—C16—C22—N1−126.3 (3)C8—C7—C6—C5−0.9 (6)
C21—C16—C22—N157.3 (3)C24—C23—C28—C27−2.6 (5)
C17—C16—C22—O1−0.2 (4)C11—C23—C28—C27−178.9 (3)
C21—C16—C22—O1−176.6 (2)C24—C25—C26—C27−0.6 (6)
C8—C9—C4—C3−179.9 (3)C25—C26—C27—C28−0.1 (7)
C10—C9—C4—C3−0.6 (4)C23—C28—C27—C261.8 (6)
C8—C9—C4—C50.1 (4)O1—C22—N1—C1166.5 (3)
C10—C9—C4—C5179.4 (3)C16—C22—N1—C11−168.7 (2)
N1—C11—C23—C24−114.6 (3)O1—C22—N1—C12−61.7 (3)
C10—C11—C23—C2411.1 (4)C16—C22—N1—C1263.1 (3)
N1—C11—C23—C2861.4 (3)C23—C11—N1—C2279.0 (3)
C10—C11—C23—C28−172.9 (3)C10—C11—N1—C22−48.7 (3)
C17—C16—C21—C20−0.6 (4)C23—C11—N1—C12−152.9 (2)
C22—C16—C21—C20176.0 (3)C10—C11—N1—C1279.5 (3)
C1—C2—C3—C4−0.5 (5)C13—C12—N1—C22−150.4 (3)
C5—C4—C3—C2−179.0 (3)C13—C12—N1—C1184.0 (3)
C9—C4—C3—C21.1 (5)C10—C1—O1—C2211.7 (4)
C4—C9—C8—C70.2 (4)C2—C1—O1—C22−168.2 (2)
C10—C9—C8—C7−179.1 (3)N1—C22—O1—C1−47.0 (3)
C28—C23—C24—C251.9 (4)C16—C22—O1—C1−174.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H15···O10.932.422.762 (4)102
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H15···O10.932.422.762 (4)102
references
References top

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