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

In the title compound, C(28)H(27)NO, 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)°.

Related literature

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

Crystal data

C28H27NO

M = 393.51

Triclinic,

a = 8.8959 (15) Å

b = 10.7589 (16) Å

c = 11.8401 (18) Å

α = 96.219 (1)°

β = 98.366 (2)°

γ = 97.274 (2)°

V = 1102.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.965, T max = 0.977

10108 measured reflections

4302 independent reflections

2352 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.262

S = 1.02

4302 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.34 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/S1600536808029383/pv2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029383/pv2101Isup2.hkl

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

C28H27NO	Z = 2
Mr = 393.51	F(000) = 420
Triclinic, P1	Dx = 1.185 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8959 (15) Å	Cell parameters from 2254 reflections
b = 10.7589 (16) Å	θ = 2.3–27.5°
c = 11.8401 (18) Å	µ = 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

Rigaku SCXmini diffractometer	4302 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scan	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.965, Tmax = 0.977	l = −14→14
10108 measured reflections

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.262	H-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 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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	−0.0487 (3)	0.6705 (3)	0.1444 (2)	0.0520 (7)
C10	−0.0728 (3)	0.7223 (3)	0.2512 (2)	0.0486 (7)
C16	0.3447 (3)	0.8083 (3)	0.1275 (2)	0.0489 (7)
C9	−0.2156 (3)	0.6833 (3)	0.2883 (3)	0.0551 (7)
C11	0.0504 (3)	0.8228 (3)	0.3234 (2)	0.0522 (7)
H5	−0.0016	0.8926	0.3505	0.063*
C2	−0.1621 (3)	0.5819 (3)	0.0713 (3)	0.0604 (8)
H6	−0.1439	0.5486	−0.0004	0.073*
C22	0.2099 (3)	0.7704 (3)	0.1862 (2)	0.0505 (7)
H7	0.2422	0.7124	0.2402	0.061*
C4	−0.3288 (3)	0.5932 (3)	0.2146 (3)	0.0599 (8)
C23	0.1350 (3)	0.7789 (3)	0.4296 (2)	0.0517 (7)
C12	0.1042 (3)	0.9693 (3)	0.1822 (2)	0.0571 (7)
H10A	−0.0048	0.9450	0.1546	0.069*
H10B	0.1561	0.9711	0.1156	0.069*
C21	0.4792 (3)	0.8709 (3)	0.1948 (3)	0.0621 (8)
H11	0.4811	0.8926	0.2732	0.074*
C3	−0.2976 (3)	0.5457 (3)	0.1064 (3)	0.0689 (9)
H12	−0.3719	0.4880	0.0575	0.083*
C8	−0.2484 (4)	0.7299 (3)	0.3967 (3)	0.0677 (9)
H13	−0.1762	0.7890	0.4460	0.081*
C24	0.1235 (3)	0.6555 (3)	0.4499 (2)	0.0560 (7)
H14	0.0583	0.5941	0.3977	0.067*
C17	0.3449 (4)	0.7784 (3)	0.0112 (3)	0.0641 (8)
H15	0.2562	0.7370	−0.0362	0.077*
C5	−0.4699 (3)	0.5539 (4)	0.2525 (4)	0.0777 (10)
H16	−0.5451	0.4959	0.2046	0.093*
C13	0.1311 (4)	1.1005 (3)	0.2498 (3)	0.0712 (9)
H17A	0.0864	1.0966	0.3196	0.085*
H17B	0.2408	1.1267	0.2724	0.085*
C19	0.6094 (4)	0.8710 (3)	0.0332 (3)	0.0733 (10)
H18	0.6979	0.8914	0.0018	0.088*
C18	0.4781 (4)	0.8101 (4)	−0.0357 (3)	0.0799 (10)
H19	0.4773	0.7898	−0.1141	0.096*
C7	−0.3862 (4)	0.6891 (4)	0.4304 (3)	0.0834 (11)
H20	−0.4062	0.7209	0.5021	0.100*
C20	0.6101 (4)	0.9016 (3)	0.1482 (3)	0.0717 (9)
H21	0.6991	0.9434	0.1952	0.086*
C14	0.0657 (5)	1.1976 (4)	0.1856 (3)	0.0914 (12)
H4	−0.0446	1.1733	0.1661	0.110*
H22B	0.1067	1.1986	0.1141	0.110*
C25	0.2064 (4)	0.6200 (4)	0.5459 (3)	0.0716 (9)
H23	0.1957	0.5354	0.5574	0.086*
C6	−0.4955 (4)	0.6004 (4)	0.3579 (4)	0.0896 (12)
H24	−0.5874	0.5726	0.3821	0.108*
C28	0.2381 (4)	0.8682 (3)	0.5083 (3)	0.0834 (11)
H25	0.2524	0.9524	0.4960	0.100*
C26	0.3032 (5)	0.7066 (4)	0.6236 (3)	0.0845 (11)
H26	0.3579	0.6821	0.6885	0.101*
C27	0.3192 (5)	0.8298 (4)	0.6054 (3)	0.1023 (14)
H27	0.3853	0.8896	0.6585	0.123*
C15	0.0978 (6)	1.3295 (4)	0.2499 (4)	0.1108 (15)
H3	0.0502	1.3314	0.3177	0.166*
H2	0.0570	1.3872	0.2013	0.166*
H1	0.2067	1.3539	0.2716	0.166*
N1	0.1605 (2)	0.8740 (2)	0.25219 (18)	0.0489 (6)
O1	0.0848 (2)	0.69988 (18)	0.10138 (16)	0.0578 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0460 (15)	0.0516 (17)	0.0593 (16)	0.0120 (12)	0.0086 (13)	0.0048 (13)
C10	0.0449 (14)	0.0492 (16)	0.0540 (15)	0.0082 (11)	0.0119 (12)	0.0108 (12)
C16	0.0508 (15)	0.0450 (15)	0.0544 (15)	0.0123 (11)	0.0143 (13)	0.0080 (12)
C9	0.0489 (16)	0.0567 (18)	0.0652 (18)	0.0162 (13)	0.0125 (14)	0.0187 (14)
C11	0.0547 (16)	0.0477 (16)	0.0566 (16)	0.0118 (12)	0.0161 (13)	0.0024 (12)
C2	0.0490 (17)	0.0607 (19)	0.0671 (18)	0.0078 (13)	0.0032 (14)	−0.0033 (15)
C22	0.0513 (16)	0.0473 (16)	0.0521 (15)	0.0100 (12)	0.0067 (13)	0.0010 (12)
C4	0.0422 (15)	0.0596 (19)	0.082 (2)	0.0098 (13)	0.0107 (15)	0.0226 (16)
C23	0.0565 (16)	0.0527 (17)	0.0462 (14)	0.0079 (12)	0.0123 (13)	0.0020 (12)
C12	0.0645 (17)	0.0514 (17)	0.0589 (17)	0.0157 (13)	0.0144 (14)	0.0083 (13)
C21	0.0573 (18)	0.066 (2)	0.0652 (18)	0.0055 (14)	0.0170 (15)	0.0125 (15)
C3	0.0478 (17)	0.060 (2)	0.093 (2)	0.0083 (14)	−0.0060 (17)	0.0046 (17)
C8	0.0602 (18)	0.075 (2)	0.075 (2)	0.0158 (15)	0.0238 (16)	0.0203 (17)
C24	0.0505 (16)	0.0596 (19)	0.0590 (17)	0.0018 (13)	0.0138 (13)	0.0127 (14)
C17	0.0610 (18)	0.070 (2)	0.0643 (18)	0.0091 (15)	0.0206 (15)	0.0082 (15)
C5	0.0448 (17)	0.081 (2)	0.112 (3)	0.0058 (15)	0.0152 (19)	0.033 (2)
C13	0.090 (2)	0.0544 (19)	0.073 (2)	0.0154 (16)	0.0162 (18)	0.0122 (15)
C19	0.063 (2)	0.071 (2)	0.098 (3)	0.0118 (16)	0.041 (2)	0.0249 (19)
C18	0.094 (3)	0.088 (3)	0.067 (2)	0.018 (2)	0.038 (2)	0.0108 (18)
C7	0.068 (2)	0.107 (3)	0.094 (3)	0.025 (2)	0.044 (2)	0.036 (2)
C20	0.0578 (19)	0.069 (2)	0.090 (2)	0.0049 (15)	0.0180 (18)	0.0160 (18)
C14	0.125 (3)	0.066 (2)	0.097 (3)	0.034 (2)	0.033 (3)	0.024 (2)
C25	0.070 (2)	0.082 (2)	0.069 (2)	0.0103 (17)	0.0176 (18)	0.0276 (18)
C6	0.054 (2)	0.112 (3)	0.118 (3)	0.020 (2)	0.029 (2)	0.048 (3)
C28	0.111 (3)	0.062 (2)	0.068 (2)	0.0097 (19)	−0.001 (2)	−0.0060 (17)
C26	0.101 (3)	0.098 (3)	0.057 (2)	0.021 (2)	0.008 (2)	0.021 (2)
C27	0.130 (4)	0.096 (3)	0.064 (2)	0.018 (3)	−0.024 (2)	−0.015 (2)
C15	0.165 (4)	0.064 (3)	0.117 (3)	0.037 (3)	0.050 (3)	0.012 (2)
N1	0.0543 (13)	0.0453 (13)	0.0494 (12)	0.0119 (10)	0.0120 (10)	0.0063 (10)
O1	0.0514 (11)	0.0605 (13)	0.0576 (12)	0.0002 (9)	0.0120 (9)	−0.0051 (9)

C1—O1	1.373 (3)	C24—C25	1.379 (4)
C1—C10	1.383 (4)	C24—H14	0.9300
C1—C2	1.414 (4)	C17—C18	1.399 (4)
C10—C9	1.432 (4)	C17—H15	0.9300
C10—C11	1.526 (4)	C5—C6	1.355 (5)
C16—C17	1.379 (4)	C5—H16	0.9300
C16—C21	1.386 (4)	C13—C14	1.485 (5)
C16—C22	1.506 (4)	C13—H17A	0.9700
C9—C8	1.411 (4)	C13—H17B	0.9700
C9—C4	1.425 (4)	C19—C20	1.364 (5)
C11—N1	1.477 (3)	C19—C18	1.368 (5)
C11—C23	1.520 (4)	C19—H18	0.9300
C11—H5	0.9800	C18—H19	0.9300
C2—C3	1.356 (4)	C7—C6	1.392 (5)
C2—H6	0.9300	C7—H20	0.9300
C22—N1	1.443 (3)	C20—H21	0.9300
C22—O1	1.456 (3)	C14—C15	1.508 (5)
C22—H7	0.9800	C14—H4	0.9700
C4—C3	1.406 (5)	C14—H22B	0.9700
C4—C5	1.424 (4)	C25—C26	1.356 (5)
C23—C24	1.369 (4)	C25—H23	0.9300
C23—C28	1.402 (4)	C6—H24	0.9300
C12—N1	1.477 (3)	C28—C27	1.396 (5)
C12—C13	1.519 (4)	C28—H25	0.9300
C12—H10A	0.9700	C26—C27	1.358 (6)
C12—H10B	0.9700	C26—H26	0.9300
C21—C20	1.379 (4)	C27—H27	0.9300
C21—H11	0.9300	C15—H3	0.9600
C3—H12	0.9300	C15—H2	0.9600
C8—C7	1.378 (4)	C15—H1	0.9600
C8—H13	0.9300
O1—C1—C10	123.4 (2)	C18—C17—H15	119.8
O1—C1—C2	115.1 (2)	C6—C5—C4	120.4 (4)
C10—C1—C2	121.5 (3)	C6—C5—H16	119.8
C1—C10—C9	118.7 (3)	C4—C5—H16	119.8
C1—C10—C11	119.1 (2)	C14—C13—C12	114.1 (3)
C9—C10—C11	122.1 (2)	C14—C13—H17A	108.7
C17—C16—C21	117.9 (3)	C12—C13—H17A	108.7
C17—C16—C22	123.8 (3)	C14—C13—H17B	108.7
C21—C16—C22	118.3 (2)	C12—C13—H17B	108.7
C8—C9—C4	118.2 (3)	H17A—C13—H17B	107.6
C8—C9—C10	122.3 (3)	C20—C19—C18	119.7 (3)
C4—C9—C10	119.4 (3)	C20—C19—H18	120.1
N1—C11—C23	110.4 (2)	C18—C19—H18	120.1
N1—C11—C10	110.7 (2)	C19—C18—C17	120.4 (3)
C23—C11—C10	114.3 (2)	C19—C18—H19	119.8
N1—C11—H5	107.0	C17—C18—H19	119.8
C23—C11—H5	107.0	C8—C7—C6	120.3 (4)
C10—C11—H5	107.0	C8—C7—H20	119.8
C3—C2—C1	119.6 (3)	C6—C7—H20	119.8
C3—C2—H6	120.2	C19—C20—C21	120.1 (3)
C1—C2—H6	120.2	C19—C20—H21	120.0
N1—C22—O1	111.8 (2)	C21—C20—H21	120.0
N1—C22—C16	114.3 (2)	C13—C14—C15	114.6 (4)
O1—C22—C16	109.3 (2)	C13—C14—H4	108.6
N1—C22—H7	107.0	C15—C14—H4	108.6
O1—C22—H7	107.0	C13—C14—H22B	108.6
C16—C22—H7	107.0	C15—C14—H22B	108.6
C3—C4—C5	122.0 (3)	H4—C14—H22B	107.6
C3—C4—C9	118.9 (3)	C26—C25—C24	120.9 (3)
C5—C4—C9	119.2 (3)	C26—C25—H23	119.5
C24—C23—C28	117.5 (3)	C24—C25—H23	119.5
C24—C23—C11	123.8 (2)	C5—C6—C7	121.0 (3)
C28—C23—C11	118.6 (3)	C5—C6—H24	119.5
N1—C12—C13	112.2 (2)	C7—C6—H24	119.5
N1—C12—H10A	109.2	C27—C28—C23	119.6 (3)
C13—C12—H10A	109.2	C27—C28—H25	120.2
N1—C12—H10B	109.2	C23—C28—H25	120.2
C13—C12—H10B	109.2	C25—C26—C27	119.1 (3)
H10A—C12—H10B	107.9	C25—C26—H26	120.4
C20—C21—C16	121.6 (3)	C27—C26—H26	120.4
C20—C21—H11	119.2	C26—C27—C28	121.2 (4)
C16—C21—H11	119.2	C26—C27—H27	119.4
C2—C3—C4	121.8 (3)	C28—C27—H27	119.4
C2—C3—H12	119.1	C14—C15—H3	109.5
C4—C3—H12	119.1	C14—C15—H2	109.5
C7—C8—C9	120.9 (3)	H3—C15—H2	109.5
C7—C8—H13	119.6	C14—C15—H1	109.5
C9—C8—H13	119.6	H3—C15—H1	109.5
C23—C24—C25	121.6 (3)	H2—C15—H1	109.5
C23—C24—H14	119.2	C22—N1—C11	109.0 (2)
C25—C24—H14	119.2	C22—N1—C12	113.8 (2)
C16—C17—C18	120.3 (3)	C11—N1—C12	113.8 (2)
C16—C17—H15	119.8	C1—O1—C22	113.8 (2)
O1—C1—C10—C9	−179.0 (2)	C11—C23—C24—C25	178.0 (3)
C2—C1—C10—C9	0.9 (4)	C21—C16—C17—C18	0.5 (5)
O1—C1—C10—C11	3.4 (4)	C22—C16—C17—C18	−176.0 (3)
C2—C1—C10—C11	−176.7 (2)	C3—C4—C5—C6	179.2 (3)
C1—C10—C9—C8	178.9 (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—C4	177.2 (2)	C16—C17—C18—C19	0.0 (5)
C1—C10—C11—N1	15.7 (3)	C9—C8—C7—C6	0.2 (5)
C9—C10—C11—N1	−161.8 (2)	C18—C19—C20—C21	0.3 (5)
C1—C10—C11—C23	−109.8 (3)	C16—C21—C20—C19	0.2 (5)
C9—C10—C11—C23	72.7 (3)	C12—C13—C14—C15	−177.4 (3)
O1—C1—C2—C3	179.4 (2)	C23—C24—C25—C26	−0.3 (5)
C10—C1—C2—C3	−0.5 (4)	C4—C5—C6—C7	1.2 (6)
C17—C16—C22—N1	−126.3 (3)	C8—C7—C6—C5	−0.9 (6)
C21—C16—C22—N1	57.3 (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—C26	1.8 (6)
C8—C9—C4—C5	0.1 (4)	O1—C22—N1—C11	66.5 (3)
C10—C9—C4—C5	179.4 (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—C24	11.1 (4)	C16—C22—N1—C12	63.1 (3)
N1—C11—C23—C28	61.4 (3)	C23—C11—N1—C22	79.0 (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—C20	176.0 (3)	C10—C11—N1—C12	79.5 (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—C11	84.0 (3)
C9—C4—C3—C2	1.1 (5)	C10—C1—O1—C22	11.7 (4)
C4—C9—C8—C7	0.2 (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—C25	1.9 (4)	C16—C22—O1—C1	−174.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H15···O1	0.93	2.42	2.762 (4)	102