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

In the title mol­ecule, C₁₉H₁₇NO, the dihedral angle between the naphthyl fused-ring system and the phenyl ring is 17.4 (1)°. In the absence of hydrogen-bonding inter­actions and π–π stacking inter­actions, the crystal structure is stabilized by van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.197
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.07 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Contuning efforts have been made to synthesize oxazine compounds because of their wide applications in agonist triggers, antipsychotic agents (Barker et al., 2006), antimalarial agents (Ren et al., 2001) and serotonin, dopamine receptors (Gentles et al., 1991; Petterson et al., 1990; Peglion et al., 1997). The title compound was prepared by reaction of 2-naphthol, formaldehyde and benzyl amine, The crystal structure of has been determined herein.

In the molecule (Fig. 1.), the dihedral angle between the C14—C19 phenyl ring and naphthyl system is 17.4 (1)°. The four atoms N1/C11/C13/C14 are essentially planar with a C14—C13—N1—C11 torsion angle of -176.5 (2)°.

Related literature

For background information, see: Barker et al. (2006); Ren et al. (2001); Gentles et al. (1991); Petterson et al. (1990); Peglion et al. (1997).

S2. Experimental

Formaldehyde (8 mL, 40%, 0.1 mol) was added slowly with stirring to a mixture of methanol (35 mL), benzylamine (10.7 g, 0.1 mol) and 2-naphthol (14.4 g, 0.1 mol) over 2 h. The mixture was stirred for additional 60 h at room temperature. The resulting bright yellow solid was filtered and washed with methanol. The solid residue was recrystallized from methanol to give colorless crystals of the title compound in a yield of 85%, which were suitable for X-ray analysis. ¹HNMR(CDCl₃, 400 MHz), 7.79(m, 11H, aromatic), 4.95(s, 2H, N—CH₂—O), 4.33(s, 2H, N—CH₂-heterocyclic), 3.99 (s,2H, N—CH₂-benzyl).

S3. Refinement

All H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and included in the riding model approximation, with U_iso (H) = 1.2U_iso (C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

Fig. 1. View of the molecular structure with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data

C19H17NO	F(000) = 584
Mr = 275.34	Dx = 1.284 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1051 reflections
a = 9.8645 (11) Å	θ = 2.3–20.8°
b = 5.2515 (6) Å	µ = 0.08 mm^−1
c = 27.811 (3) Å	T = 292 K
β = 98.716 (1)°	Block, colorless
V = 1424.1 (3) Å^3	0.30 × 0.20 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2643 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.977, Tmax = 0.997	k = −6→6
10025 measured reflections	l = −27→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1062P)^2] where P = (Fo^2 + 2Fc^2)/3
2643 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5579 (3)	0.0173 (5)	0.15827 (10)	0.0455 (7)
C2	0.6084 (3)	−0.1653 (6)	0.12911 (12)	0.0591 (9)
H2	0.6904	−0.2484	0.1403	0.071*
C3	0.5382 (4)	−0.2223 (6)	0.08429 (12)	0.0674 (9)
H3	0.5714	−0.3472	0.0654	0.081*
C4	0.4149 (3)	−0.0924 (6)	0.06629 (11)	0.0546 (8)
C5	0.3421 (4)	−0.1401 (7)	0.01905 (12)	0.0749 (10)
H5	0.3744	−0.2625	−0.0006	0.090*
C6	0.2262 (4)	−0.0094 (8)	0.00225 (12)	0.0783 (11)
H6	0.1797	−0.0424	−0.0288	0.094*
C7	0.1763 (3)	0.1742 (7)	0.03115 (11)	0.0685 (10)
H7	0.0968	0.2634	0.0193	0.082*
C8	0.2435 (3)	0.2240 (6)	0.07684 (10)	0.0541 (8)
H8	0.2089	0.3472	0.0957	0.065*
C9	0.3647 (3)	0.0921 (5)	0.09599 (10)	0.0433 (7)
C10	0.4370 (2)	0.1433 (5)	0.14333 (9)	0.0415 (7)
C11	0.3827 (3)	0.3277 (5)	0.17737 (10)	0.0491 (7)
H11A	0.3955	0.5003	0.1665	0.059*
H11B	0.2851	0.2997	0.1763	0.059*
C12	0.5964 (3)	0.2834 (6)	0.22732 (11)	0.0526 (8)
H12A	0.6431	0.2825	0.2606	0.063*
H12B	0.6258	0.4342	0.2116	0.063*
C13	0.3999 (3)	0.0799 (5)	0.25237 (10)	0.0501 (7)
H13A	0.4184	−0.0749	0.2355	0.060*
H13B	0.3012	0.0954	0.2506	0.060*
C14	0.4638 (2)	0.0594 (5)	0.30480 (10)	0.0416 (7)
C15	0.5551 (3)	−0.1322 (5)	0.32051 (11)	0.0513 (8)
H15	0.5765	−0.2517	0.2982	0.062*
C16	0.6160 (3)	−0.1521 (6)	0.36869 (11)	0.0578 (8)
H16	0.6778	−0.2828	0.3783	0.069*
C17	0.5844 (3)	0.0220 (6)	0.40200 (11)	0.0568 (8)
H17	0.6248	0.0108	0.4344	0.068*
C18	0.4927 (3)	0.2132 (6)	0.38710 (11)	0.0582 (8)
H18	0.4704	0.3313	0.4096	0.070*
C19	0.4331 (3)	0.2312 (5)	0.33884 (11)	0.0530 (8)
H19	0.3713	0.3619	0.3293	0.064*
N1	0.4517 (2)	0.2993 (4)	0.22774 (8)	0.0462 (6)
O1	0.63734 (17)	0.0607 (4)	0.20267 (7)	0.0559 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0412 (14)	0.0474 (17)	0.0483 (18)	−0.0014 (13)	0.0081 (13)	0.0047 (14)
C2	0.0561 (17)	0.061 (2)	0.064 (2)	0.0178 (15)	0.0220 (16)	0.0074 (17)
C3	0.086 (2)	0.061 (2)	0.061 (2)	0.0145 (19)	0.0320 (19)	−0.0080 (17)
C4	0.0670 (19)	0.0519 (19)	0.0462 (19)	−0.0040 (15)	0.0128 (15)	−0.0013 (15)
C5	0.105 (3)	0.071 (2)	0.051 (2)	−0.004 (2)	0.019 (2)	−0.0146 (19)
C6	0.098 (3)	0.091 (3)	0.041 (2)	−0.012 (2)	−0.0062 (19)	−0.003 (2)
C7	0.068 (2)	0.083 (3)	0.050 (2)	−0.0060 (18)	−0.0037 (17)	0.0089 (19)
C8	0.0578 (17)	0.058 (2)	0.0448 (18)	−0.0015 (14)	0.0019 (15)	0.0035 (14)
C9	0.0466 (14)	0.0425 (16)	0.0416 (17)	−0.0062 (13)	0.0094 (13)	0.0005 (13)
C10	0.0418 (14)	0.0422 (16)	0.0413 (17)	−0.0004 (11)	0.0093 (12)	0.0013 (13)
C11	0.0512 (16)	0.0508 (18)	0.0435 (17)	0.0044 (13)	0.0021 (13)	−0.0063 (14)
C12	0.0436 (15)	0.064 (2)	0.0500 (19)	−0.0144 (14)	0.0058 (14)	0.0012 (15)
C13	0.0448 (14)	0.0532 (18)	0.0523 (19)	−0.0089 (14)	0.0074 (13)	−0.0071 (15)
C14	0.0445 (14)	0.0410 (16)	0.0393 (16)	−0.0093 (12)	0.0069 (12)	−0.0042 (13)
C15	0.0569 (17)	0.0454 (18)	0.0542 (19)	0.0016 (14)	0.0164 (15)	−0.0071 (15)
C16	0.0576 (18)	0.054 (2)	0.062 (2)	0.0038 (15)	0.0093 (16)	0.0069 (17)
C17	0.0672 (19)	0.060 (2)	0.0418 (18)	−0.0149 (17)	0.0024 (15)	0.0076 (16)
C18	0.0680 (19)	0.056 (2)	0.052 (2)	−0.0050 (16)	0.0118 (16)	−0.0121 (16)
C19	0.0540 (17)	0.0450 (17)	0.060 (2)	0.0016 (14)	0.0080 (16)	−0.0050 (15)
N1	0.0503 (13)	0.0430 (14)	0.0441 (14)	−0.0078 (10)	0.0034 (11)	−0.0029 (11)
O1	0.0383 (10)	0.0755 (15)	0.0523 (13)	0.0054 (10)	0.0019 (9)	0.0024 (11)

Geometric parameters (Å, º)

C1—C10	1.372 (3)	C11—H11B	0.9700
C1—O1	1.377 (3)	C12—N1	1.431 (3)
C1—C2	1.396 (4)	C12—O1	1.444 (3)
C2—C3	1.364 (4)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.418 (4)	C13—N1	1.471 (3)
C3—H3	0.9300	C13—C14	1.502 (3)
C4—C9	1.411 (4)	C13—H13A	0.9700
C4—C5	1.421 (4)	C13—H13B	0.9700
C5—C6	1.354 (5)	C14—C19	1.374 (4)
C5—H5	0.9300	C14—C15	1.376 (4)
C6—C7	1.392 (5)	C15—C16	1.387 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.367 (4)	C16—C17	1.371 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.414 (4)	C17—C18	1.373 (4)
C8—H8	0.9300	C17—H17	0.9300
C9—C10	1.425 (3)	C18—C19	1.384 (4)
C10—C11	1.508 (4)	C18—H18	0.9300
C11—N1	1.469 (3)	C19—H19	0.9300
C11—H11A	0.9700
C10—C1—O1	122.8 (2)	H11A—C11—H11B	107.9
C10—C1—C2	121.7 (3)	N1—C12—O1	113.7 (2)
O1—C1—C2	115.5 (2)	N1—C12—H12A	108.8
C3—C2—C1	120.3 (3)	O1—C12—H12A	108.8
C3—C2—H2	119.8	N1—C12—H12B	108.8
C1—C2—H2	119.8	O1—C12—H12B	108.8
C2—C3—C4	120.4 (3)	H12A—C12—H12B	107.7
C2—C3—H3	119.8	N1—C13—C14	112.6 (2)
C4—C3—H3	119.8	N1—C13—H13A	109.1
C9—C4—C3	118.8 (3)	C14—C13—H13A	109.1
C9—C4—C5	119.3 (3)	N1—C13—H13B	109.1
C3—C4—C5	121.9 (3)	C14—C13—H13B	109.1
C6—C5—C4	120.8 (3)	H13A—C13—H13B	107.8
C6—C5—H5	119.6	C19—C14—C15	117.6 (3)
C4—C5—H5	119.6	C19—C14—C13	121.2 (3)
C5—C6—C7	120.4 (3)	C15—C14—C13	121.3 (3)
C5—C6—H6	119.8	C14—C15—C16	121.9 (3)
C7—C6—H6	119.8	C14—C15—H15	119.0
C8—C7—C6	120.3 (3)	C16—C15—H15	119.0
C8—C7—H7	119.8	C17—C16—C15	119.6 (3)
C6—C7—H7	119.8	C17—C16—H16	120.2
C7—C8—C9	121.3 (3)	C15—C16—H16	120.2
C7—C8—H8	119.3	C16—C17—C18	119.4 (3)
C9—C8—H8	119.3	C16—C17—H17	120.3
C4—C9—C8	117.9 (3)	C18—C17—H17	120.3
C4—C9—C10	119.9 (2)	C17—C18—C19	120.4 (3)
C8—C9—C10	122.1 (3)	C17—C18—H18	119.8
C1—C10—C9	118.6 (2)	C19—C18—H18	119.8
C1—C10—C11	119.7 (2)	C14—C19—C18	121.2 (3)
C9—C10—C11	121.7 (2)	C14—C19—H19	119.4
N1—C11—C10	112.1 (2)	C18—C19—H19	119.4
N1—C11—H11A	109.2	C12—N1—C11	108.5 (2)
C10—C11—H11A	109.2	C12—N1—C13	112.1 (2)
N1—C11—H11B	109.2	C11—N1—C13	112.3 (2)
C10—C11—H11B	109.2	C1—O1—C12	113.4 (2)
C10—C1—C2—C3	0.4 (4)	C8—C9—C10—C11	4.7 (4)
O1—C1—C2—C3	−179.7 (3)	C1—C10—C11—N1	−14.5 (4)
C1—C2—C3—C4	1.6 (5)	C9—C10—C11—N1	164.3 (2)
C2—C3—C4—C9	−1.5 (5)	N1—C13—C14—C19	70.5 (3)
C2—C3—C4—C5	177.5 (3)	N1—C13—C14—C15	−109.6 (3)
C9—C4—C5—C6	0.5 (5)	C19—C14—C15—C16	−0.7 (4)
C3—C4—C5—C6	−178.5 (3)	C13—C14—C15—C16	179.3 (2)
C4—C5—C6—C7	−0.1 (5)	C14—C15—C16—C17	0.4 (4)
C5—C6—C7—C8	−0.1 (5)	C15—C16—C17—C18	0.2 (4)
C6—C7—C8—C9	0.0 (5)	C16—C17—C18—C19	−0.4 (4)
C3—C4—C9—C8	178.4 (3)	C15—C14—C19—C18	0.5 (4)
C5—C4—C9—C8	−0.7 (4)	C13—C14—C19—C18	−179.6 (2)
C3—C4—C9—C10	−0.5 (4)	C17—C18—C19—C14	0.1 (4)
C5—C4—C9—C10	−179.6 (3)	O1—C12—N1—C11	−64.4 (3)
C7—C8—C9—C4	0.4 (4)	O1—C12—N1—C13	60.2 (3)
C7—C8—C9—C10	179.3 (3)	C10—C11—N1—C12	45.9 (3)
O1—C1—C10—C9	177.7 (2)	C10—C11—N1—C13	−78.4 (3)
C2—C1—C10—C9	−2.4 (4)	C14—C13—N1—C12	61.2 (3)
O1—C1—C10—C11	−3.5 (4)	C14—C13—N1—C11	−176.5 (2)
C2—C1—C10—C11	176.4 (2)	C10—C1—O1—C12	−11.7 (3)
C4—C9—C10—C1	2.5 (4)	C2—C1—O1—C12	168.4 (2)
C8—C9—C10—C1	−176.4 (2)	N1—C12—O1—C1	46.8 (3)
C4—C9—C10—C11	−176.4 (2)