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

In the title compound, C(31)H(25)NO, the oxazine ring adopts a half-chair conformation. The dihedral angles between the phenyl rings and the naphthyl ring system are 70.89 (8), 37.34 (10) and 9.42 (10)°. The crystal structure is stabilized by an aromatic π-π stacking inter-action, with a centroid-centroid distance of 3.879 (3) Å.

Related literature

For the synthesis and crystal structures of oxazines, see: Alfonsov et al. (2007 ▶); Li et al. (2008 ▶). For pharmaceutical applications of oxazines, see: Peglion et al. (1997 ▶); Xu et al. (2004 ▶).

Experimental

Crystal data

C31H25NO

M = 427.52

Monoclinic,

a = 9.0605 (18) Å

b = 23.475 (5) Å

c = 10.634 (2) Å

β = 97.53 (3)°

V = 2242.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.984, T max = 0.985

18548 measured reflections

4392 independent reflections

2913 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.118

S = 1.00

4392 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025811/rz2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025811/rz2345Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H25NO	F(000) = 904
Mr = 427.52	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4392 reflections
a = 9.0605 (18) Å	θ = 2.0–26.0°
b = 23.475 (5) Å	µ = 0.08 mm−1
c = 10.634 (2) Å	T = 293 K
β = 97.53 (3)°	Block, colourless
V = 2242.2 (8) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	4392 independent reflections
Radiation source: fine-focus sealed tube	2913 reflections with I > 2σ(I)
graphite	Rint = 0.078
CCD_Profile_fitting scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.984, Tmax = 0.985	k = −28→28
18548 measured reflections	l = −13→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0185P)2 + 1.004P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4392 reflections	Δρmax = 0.16 e Å−3
299 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (6)

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
O1	0.56752 (15)	0.05364 (6)	0.18725 (13)	0.0433 (4)
C25	0.6744 (2)	0.09254 (9)	0.25499 (19)	0.0357 (5)
H25A	0.6940	0.1227	0.1957	0.043*
C26	0.8189 (2)	0.06072 (9)	0.29206 (19)	0.0368 (5)
N1	0.61811 (18)	0.11912 (7)	0.36044 (15)	0.0339 (4)
C1	0.3834 (2)	0.12590 (8)	0.21580 (19)	0.0355 (5)
C9	0.2345 (2)	0.14567 (9)	0.18089 (19)	0.0381 (5)
C11	0.4930 (2)	0.15723 (8)	0.31138 (19)	0.0354 (5)
H11A	0.4405	0.1672	0.3832	0.043*
C2	0.4255 (2)	0.07585 (9)	0.16309 (19)	0.0381 (5)
C3	0.3247 (2)	0.04280 (10)	0.0810 (2)	0.0446 (6)
H3A	0.3553	0.0086	0.0489	0.054*
C12	0.5533 (2)	0.21233 (8)	0.2623 (2)	0.0365 (5)
C8	0.1826 (2)	0.19750 (9)	0.2272 (2)	0.0479 (6)
H8A	0.2459	0.2190	0.2846	0.058*
C10	0.1337 (2)	0.11330 (10)	0.0960 (2)	0.0415 (5)
C20	0.7137 (2)	0.13377 (9)	0.6347 (2)	0.0444 (6)
H20A	0.7814	0.1453	0.5811	0.053*
C19	0.5928 (2)	0.10047 (8)	0.58716 (18)	0.0342 (5)
C5	−0.0124 (2)	0.13407 (11)	0.0593 (2)	0.0521 (6)
H5A	−0.0790	0.1129	0.0039	0.062*
C31	0.8413 (2)	0.00538 (9)	0.2547 (2)	0.0453 (6)
H31A	0.7636	−0.0147	0.2089	0.054*
C4	0.1826 (2)	0.06123 (10)	0.0491 (2)	0.0463 (6)
H4A	0.1163	0.0392	−0.0046	0.056*
C28	1.0728 (3)	0.06368 (11)	0.3912 (2)	0.0540 (6)
H28A	1.1506	0.0834	0.4378	0.065*
C27	0.9361 (2)	0.08953 (10)	0.3615 (2)	0.0444 (6)
H27A	0.9223	0.1266	0.3883	0.053*
C18	0.5762 (2)	0.07786 (8)	0.45383 (19)	0.0383 (5)
H18A	0.6375	0.0441	0.4518	0.046*
H18B	0.4734	0.0666	0.4294	0.046*
C22	0.6355 (3)	0.13384 (11)	0.8404 (2)	0.0562 (7)
H22A	0.6495	0.1452	0.9249	0.067*
C17	0.5268 (2)	0.22873 (10)	0.1367 (2)	0.0468 (6)
H17A	0.4695	0.2055	0.0785	0.056*
C7	0.0414 (3)	0.21641 (10)	0.1892 (2)	0.0556 (7)
H7A	0.0099	0.2508	0.2202	0.067*
C29	1.0949 (3)	0.00892 (11)	0.3522 (2)	0.0567 (7)
H29A	1.1876	−0.0083	0.3712	0.068*
C24	0.4939 (2)	0.08446 (9)	0.6690 (2)	0.0451 (6)
H24A	0.4115	0.0624	0.6390	0.054*
C23	0.5154 (3)	0.10079 (11)	0.7951 (2)	0.0559 (7)
H23A	0.4483	0.0893	0.8493	0.067*
C30	0.9789 (3)	−0.02034 (11)	0.2850 (2)	0.0554 (6)
H30A	0.9930	−0.0577	0.2598	0.067*
C6	−0.0562 (3)	0.18458 (11)	0.1040 (2)	0.0579 (7)
H6A	−0.1517	0.1981	0.0778	0.069*
C13	0.6384 (3)	0.24804 (10)	0.3467 (2)	0.0526 (6)
H13A	0.6572	0.2379	0.4319	0.063*
C21	0.7349 (3)	0.15011 (10)	0.7604 (2)	0.0516 (6)
H21A	0.8169	0.1722	0.7910	0.062*
C16	0.5843 (3)	0.27926 (11)	0.0957 (3)	0.0605 (7)
H16A	0.5658	0.2897	0.0108	0.073*
C14	0.6956 (3)	0.29827 (11)	0.3065 (3)	0.0687 (8)
H14A	0.7526	0.3217	0.3644	0.082*
C15	0.6686 (3)	0.31363 (11)	0.1813 (3)	0.0690 (8)
H15A	0.7075	0.3475	0.1542	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0346 (8)	0.0491 (9)	0.0444 (9)	0.0029 (7)	−0.0015 (7)	−0.0122 (7)
C25	0.0343 (12)	0.0402 (12)	0.0318 (12)	−0.0006 (9)	0.0013 (10)	0.0008 (9)
C26	0.0339 (12)	0.0455 (13)	0.0312 (12)	0.0038 (9)	0.0049 (9)	0.0031 (10)
N1	0.0352 (10)	0.0362 (10)	0.0301 (10)	0.0026 (7)	0.0036 (8)	0.0017 (7)
C1	0.0319 (12)	0.0409 (12)	0.0338 (12)	−0.0016 (9)	0.0043 (9)	−0.0002 (9)
C9	0.0306 (12)	0.0461 (13)	0.0376 (12)	−0.0002 (9)	0.0049 (10)	0.0052 (10)
C11	0.0329 (12)	0.0384 (12)	0.0349 (12)	0.0037 (9)	0.0042 (10)	−0.0016 (9)
C2	0.0316 (12)	0.0482 (13)	0.0336 (12)	0.0016 (10)	0.0010 (10)	−0.0002 (10)
C3	0.0443 (14)	0.0490 (14)	0.0397 (13)	−0.0019 (10)	0.0024 (11)	−0.0081 (10)
C12	0.0321 (12)	0.0360 (11)	0.0416 (13)	0.0047 (9)	0.0055 (10)	−0.0007 (10)
C8	0.0348 (13)	0.0492 (14)	0.0592 (16)	0.0011 (10)	0.0040 (11)	0.0008 (12)
C10	0.0321 (12)	0.0559 (14)	0.0362 (13)	−0.0023 (10)	0.0033 (10)	0.0064 (10)
C20	0.0430 (14)	0.0494 (14)	0.0402 (13)	−0.0030 (10)	0.0026 (11)	0.0015 (11)
C19	0.0358 (12)	0.0346 (11)	0.0318 (12)	0.0047 (9)	0.0028 (10)	0.0020 (9)
C5	0.0346 (13)	0.0691 (17)	0.0504 (15)	−0.0039 (12)	−0.0023 (11)	0.0095 (13)
C31	0.0417 (13)	0.0490 (14)	0.0453 (14)	0.0050 (10)	0.0063 (11)	−0.0025 (11)
C4	0.0402 (14)	0.0597 (15)	0.0374 (13)	−0.0096 (11)	−0.0015 (11)	−0.0062 (11)
C28	0.0372 (14)	0.0750 (18)	0.0477 (15)	0.0006 (12)	−0.0022 (11)	0.0039 (13)
C27	0.0371 (13)	0.0496 (14)	0.0456 (14)	0.0006 (10)	0.0016 (11)	−0.0013 (11)
C18	0.0405 (12)	0.0369 (12)	0.0365 (12)	−0.0019 (9)	0.0015 (10)	0.0018 (9)
C22	0.0662 (18)	0.0647 (17)	0.0356 (14)	0.0103 (13)	−0.0016 (13)	−0.0081 (12)
C17	0.0411 (14)	0.0502 (14)	0.0482 (15)	0.0033 (11)	0.0026 (11)	0.0053 (11)
C7	0.0411 (14)	0.0532 (15)	0.0726 (18)	0.0067 (11)	0.0084 (13)	0.0016 (13)
C29	0.0434 (15)	0.0744 (18)	0.0518 (16)	0.0189 (13)	0.0039 (13)	0.0139 (14)
C24	0.0407 (13)	0.0502 (14)	0.0449 (14)	−0.0008 (10)	0.0073 (11)	0.0007 (11)
C23	0.0603 (17)	0.0700 (17)	0.0393 (15)	0.0053 (13)	0.0133 (13)	0.0032 (12)
C30	0.0577 (16)	0.0529 (15)	0.0556 (16)	0.0176 (12)	0.0071 (13)	0.0022 (12)
C6	0.0342 (13)	0.0682 (17)	0.0700 (18)	0.0065 (12)	0.0023 (13)	0.0140 (14)
C13	0.0593 (16)	0.0478 (14)	0.0493 (15)	−0.0060 (12)	0.0017 (12)	−0.0028 (11)
C21	0.0534 (15)	0.0517 (15)	0.0460 (15)	−0.0009 (11)	−0.0074 (12)	−0.0062 (12)
C16	0.0573 (17)	0.0621 (17)	0.0625 (18)	0.0062 (13)	0.0096 (14)	0.0234 (14)
C14	0.074 (2)	0.0496 (16)	0.081 (2)	−0.0176 (14)	0.0049 (16)	−0.0066 (15)
C15	0.0667 (19)	0.0464 (16)	0.095 (2)	−0.0081 (13)	0.0134 (17)	0.0165 (15)

O1—C2	1.381 (2)	C31—C30	1.385 (3)
O1—C25	1.452 (2)	C31—H31A	0.9300
C25—N1	1.434 (2)	C4—H4A	0.9300
C25—C26	1.514 (3)	C28—C29	1.373 (3)
C25—H25A	0.9800	C28—C27	1.379 (3)
C26—C31	1.381 (3)	C28—H28A	0.9300
C26—C27	1.387 (3)	C27—H27A	0.9300
N1—C18	1.472 (2)	C18—H18A	0.9700
N1—C11	1.484 (2)	C18—H18B	0.9700
C1—C2	1.377 (3)	C22—C23	1.371 (3)
C1—C9	1.429 (3)	C22—C21	1.372 (3)
C1—C11	1.515 (3)	C22—H22A	0.9300
C9—C8	1.416 (3)	C17—C16	1.388 (3)
C9—C10	1.418 (3)	C17—H17A	0.9300
C11—C12	1.523 (3)	C7—C6	1.396 (3)
C11—H11A	0.9800	C7—H7A	0.9300
C2—C3	1.411 (3)	C29—C30	1.375 (3)
C3—C4	1.358 (3)	C29—H29A	0.9300
C3—H3A	0.9300	C24—C23	1.383 (3)
C12—C17	1.381 (3)	C24—H24A	0.9300
C12—C13	1.386 (3)	C23—H23A	0.9300
C8—C7	1.364 (3)	C30—H30A	0.9300
C8—H8A	0.9300	C6—H6A	0.9300
C10—C4	1.413 (3)	C13—C14	1.378 (3)
C10—C5	1.417 (3)	C13—H13A	0.9300
C20—C21	1.379 (3)	C21—H21A	0.9300
C20—C19	1.386 (3)	C16—C15	1.371 (4)
C20—H20A	0.9300	C16—H16A	0.9300
C19—C24	1.381 (3)	C14—C15	1.370 (4)
C19—C18	1.503 (3)	C14—H14A	0.9300
C5—C6	1.356 (3)	C15—H15A	0.9300
C5—H5A	0.9300
C2—O1—C25	113.55 (15)	C3—C4—H4A	119.4
N1—C25—O1	112.28 (16)	C10—C4—H4A	119.4
N1—C25—C26	113.27 (16)	C29—C28—C27	120.3 (2)
O1—C25—C26	108.46 (16)	C29—C28—H28A	119.8
N1—C25—H25A	107.5	C27—C28—H28A	119.8
O1—C25—H25A	107.5	C28—C27—C26	120.6 (2)
C26—C25—H25A	107.5	C28—C27—H27A	119.7
C31—C26—C27	118.7 (2)	C26—C27—H27A	119.7
C31—C26—C25	122.93 (19)	N1—C18—C19	113.65 (16)
C27—C26—C25	118.26 (19)	N1—C18—H18A	108.8
C25—N1—C18	113.00 (16)	C19—C18—H18A	108.8
C25—N1—C11	108.72 (15)	N1—C18—H18B	108.8
C18—N1—C11	112.38 (15)	C19—C18—H18B	108.8
C2—C1—C9	118.28 (19)	H18A—C18—H18B	107.7
C2—C1—C11	119.68 (18)	C23—C22—C21	119.7 (2)
C9—C1—C11	122.01 (18)	C23—C22—H22A	120.2
C8—C9—C10	117.80 (19)	C21—C22—H22A	120.2
C8—C9—C1	122.3 (2)	C12—C17—C16	121.1 (2)
C10—C9—C1	119.92 (19)	C12—C17—H17A	119.5
N1—C11—C1	110.28 (16)	C16—C17—H17A	119.5
N1—C11—C12	109.90 (16)	C8—C7—C6	120.5 (2)
C1—C11—C12	114.56 (17)	C8—C7—H7A	119.7
N1—C11—H11A	107.3	C6—C7—H7A	119.7
C1—C11—H11A	107.3	C28—C29—C30	119.5 (2)
C12—C11—H11A	107.3	C28—C29—H29A	120.2
O1—C2—C1	123.19 (18)	C30—C29—H29A	120.2
O1—C2—C3	114.81 (18)	C19—C24—C23	121.0 (2)
C1—C2—C3	122.00 (19)	C19—C24—H24A	119.5
C4—C3—C2	119.7 (2)	C23—C24—H24A	119.5
C4—C3—H3A	120.2	C22—C23—C24	120.1 (2)
C2—C3—H3A	120.2	C22—C23—H23A	120.0
C17—C12—C13	118.0 (2)	C24—C23—H23A	120.0
C17—C12—C11	122.93 (19)	C29—C30—C31	120.4 (2)
C13—C12—C11	119.07 (19)	C29—C30—H30A	119.8
C7—C8—C9	121.2 (2)	C31—C30—H30A	119.8
C7—C8—H8A	119.4	C5—C6—C7	120.4 (2)
C9—C8—H8A	119.4	C5—C6—H6A	119.8
C4—C10—C5	121.7 (2)	C7—C6—H6A	119.8
C4—C10—C9	118.9 (2)	C14—C13—C12	121.1 (2)
C5—C10—C9	119.4 (2)	C14—C13—H13A	119.5
C21—C20—C19	120.9 (2)	C12—C13—H13A	119.5
C21—C20—H20A	119.6	C22—C21—C20	120.3 (2)
C19—C20—H20A	119.6	C22—C21—H21A	119.9
C24—C19—C20	118.1 (2)	C20—C21—H21A	119.9
C24—C19—C18	120.37 (19)	C15—C16—C17	119.6 (2)
C20—C19—C18	121.34 (19)	C15—C16—H16A	120.2
C6—C5—C10	120.7 (2)	C17—C16—H16A	120.2
C6—C5—H5A	119.7	C15—C14—C13	120.0 (3)
C10—C5—H5A	119.7	C15—C14—H14A	120.0
C26—C31—C30	120.3 (2)	C13—C14—H14A	120.0
C26—C31—H31A	119.8	C14—C15—C16	120.2 (2)
C30—C31—H31A	119.8	C14—C15—H15A	119.9
C3—C4—C10	121.2 (2)	C16—C15—H15A	119.9