(1S*,4aR*,5S*,6S*,8aR*)-3-Benzyl-1-methyl-5,6-diphenyl-3,4,4a,5,6,8a-hexa-hydro-1H-2,3-benzoxazin-4-one.

In the title compound, C(28)H(27)NO(2), the oxazinone ring adopts a twist-boat conformation and the cyclo-hexene ring has a twisted envelope conformation. The crystal structure is stabilized by weak non-classical inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis of 1H-benzo[d][1,2]oxazin-4-ones by intra­molecular Diels–Alder (IMDA) cyclo­addition, see: Ishikawa et al. (2001 ▶). For microwave-assisted IMDA cyclo­addition, see: Dai & Shi (2007 ▶). For cyclo­addition of ester-tethered 1,3,8-nona­trienes, see: Wu et al. (2006 ▶), of sorbate-related 1,3,8-nona­trienes, see: Wu et al. (2007 ▶) and of hydroxamate-tethered 1,3,9-deca­trienes, see: Wang et al. (2009 ▶).

Experimental

Crystal data

C28H27NO2

M = 409.51

Triclinic,

a = 7.9721 (5) Å

b = 11.0649 (7) Å

c = 13.578 (1) Å

α = 78.168 (2)°

β = 73.178 (2)°

γ = 82.819 (1)°

V = 1119.35 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.41 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.970, T max = 0.985

8442 measured reflections

3780 independent reflections

2761 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.00

3780 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044195/lx2119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044195/lx2119Isup2.hkl

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

C28H27NO2	Z = 2
Mr = 409.51	F(000) = 436
Triclinic, P1	Dx = 1.215 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9721 (5) Å	Cell parameters from 6812 reflections
b = 11.0649 (7) Å	θ = 3.0–27.4°
c = 13.578 (1) Å	µ = 0.08 mm−1
α = 78.168 (2)°	T = 296 K
β = 73.178 (2)°	Block, colorless
γ = 82.819 (1)°	0.41 × 0.22 × 0.20 mm
V = 1119.35 (13) Å3

Rigaku R-AXIS RAPID diffractometer	3780 independent reflections
Radiation source: rolling anode	2761 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.00 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −8→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.970, Tmax = 0.985	l = −16→16
8442 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.035P)2 + 0.520P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3780 reflections	Δρmax = 0.14 e Å−3
282 parameters	Δρmin = −0.16 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: 0.029 (2)

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	0.31521 (17)	0.51064 (13)	0.10452 (11)	0.0527 (4)
O2	0.52969 (18)	0.30895 (13)	0.27091 (11)	0.0566 (4)
N1	0.4262 (2)	0.34429 (15)	0.19925 (14)	0.0521 (4)
C1	0.4170 (2)	0.46717 (18)	0.15722 (14)	0.0430 (5)
C2	0.5572 (2)	0.53344 (17)	0.17483 (14)	0.0398 (4)
H2	0.5323	0.5327	0.2500	0.048*
C3	0.5745 (2)	0.66685 (17)	0.11789 (14)	0.0423 (4)
H3	0.6124	0.6640	0.0429	0.051*
C4	0.7261 (2)	0.72170 (18)	0.14317 (15)	0.0477 (5)
H4	0.7563	0.7967	0.0909	0.057*
C5	0.8884 (2)	0.6345 (2)	0.12960 (15)	0.0516 (5)
H5	0.9952	0.6667	0.1207	0.062*
C6	0.8889 (2)	0.5157 (2)	0.12950 (15)	0.0487 (5)
H6	0.9953	0.4685	0.1222	0.058*
C7	0.7277 (2)	0.45197 (17)	0.14044 (15)	0.0425 (4)
H7	0.7338	0.4351	0.0714	0.051*
C8	0.7139 (3)	0.32775 (19)	0.21604 (17)	0.0522 (5)
H8	0.7741	0.3327	0.2685	0.063*
C9	0.2941 (3)	0.2601 (2)	0.21231 (18)	0.0568 (6)
H9A	0.3504	0.1772	0.2120	0.068*
H9B	0.2461	0.2817	0.1525	0.068*
C10	0.1442 (3)	0.2581 (2)	0.31043 (16)	0.0527 (5)
C11	0.0603 (3)	0.1503 (2)	0.3554 (2)	0.0759 (7)
H11	0.1029	0.0782	0.3286	0.091*
C12	−0.0877 (4)	0.1488 (3)	0.4408 (2)	0.0945 (9)
H12	−0.1452	0.0763	0.4694	0.113*
C13	−0.1489 (4)	0.2533 (4)	0.4827 (2)	0.0920 (9)
H13	−0.2469	0.2519	0.5402	0.110*
C14	−0.0652 (3)	0.3601 (3)	0.4396 (2)	0.0801 (8)
H14	−0.1060	0.4312	0.4683	0.096*
C15	0.0799 (3)	0.3628 (2)	0.35354 (18)	0.0649 (6)
H15	0.1347	0.4362	0.3243	0.078*
C16	0.4076 (2)	0.75084 (17)	0.13603 (15)	0.0453 (5)
C17	0.2782 (3)	0.7394 (2)	0.23037 (17)	0.0536 (5)
H17	0.2919	0.6763	0.2850	0.064*
C18	0.1290 (3)	0.8199 (2)	0.2451 (2)	0.0653 (6)
H18	0.0439	0.8107	0.3091	0.078*
C19	0.1071 (3)	0.9132 (2)	0.1653 (2)	0.0748 (7)
H19	0.0068	0.9672	0.1748	0.090*
C20	0.2332 (4)	0.9266 (2)	0.0717 (2)	0.0797 (8)
H20	0.2187	0.9901	0.0175	0.096*
C21	0.3824 (3)	0.8461 (2)	0.05714 (19)	0.0632 (6)
H21	0.4672	0.8564	−0.0069	0.076*
C22	0.6757 (3)	0.7609 (2)	0.24998 (17)	0.0519 (5)
C23	0.6937 (3)	0.6795 (2)	0.33864 (18)	0.0639 (6)
H23	0.7340	0.5977	0.3341	0.077*
C24	0.6525 (4)	0.7179 (3)	0.4344 (2)	0.0852 (8)
H24	0.6639	0.6617	0.4936	0.102*
C25	0.5950 (4)	0.8386 (4)	0.4419 (3)	0.1007 (11)
H25	0.5697	0.8649	0.5058	0.121*
C26	0.5751 (4)	0.9202 (3)	0.3550 (3)	0.0956 (10)
H26	0.5346	1.0019	0.3600	0.115*
C27	0.6148 (3)	0.8819 (2)	0.2602 (2)	0.0708 (7)
H27	0.6006	0.9383	0.2017	0.085*
C28	0.8005 (3)	0.2201 (2)	0.1641 (2)	0.0756 (7)
H28A	0.7915	0.1457	0.2156	0.091*
H28B	0.9221	0.2336	0.1308	0.091*
H28C	0.7434	0.2121	0.1127	0.091*

	U11	U22	U33	U12	U13	U23
O1	0.0413 (7)	0.0654 (9)	0.0550 (9)	−0.0001 (7)	−0.0218 (7)	−0.0085 (7)
O2	0.0507 (8)	0.0596 (9)	0.0558 (9)	−0.0015 (7)	−0.0195 (7)	0.0036 (7)
N1	0.0412 (9)	0.0519 (10)	0.0642 (11)	−0.0073 (8)	−0.0211 (8)	−0.0006 (8)
C1	0.0341 (9)	0.0524 (12)	0.0409 (11)	0.0023 (9)	−0.0082 (8)	−0.0106 (9)
C2	0.0350 (9)	0.0482 (11)	0.0372 (10)	0.0006 (8)	−0.0114 (8)	−0.0099 (8)
C3	0.0393 (10)	0.0500 (11)	0.0366 (10)	−0.0024 (9)	−0.0083 (8)	−0.0083 (8)
C4	0.0430 (11)	0.0506 (11)	0.0469 (12)	−0.0077 (9)	−0.0058 (9)	−0.0096 (9)
C5	0.0352 (10)	0.0675 (14)	0.0532 (13)	−0.0053 (10)	−0.0067 (9)	−0.0196 (10)
C6	0.0332 (10)	0.0633 (13)	0.0501 (12)	0.0055 (9)	−0.0101 (8)	−0.0184 (10)
C7	0.0360 (10)	0.0511 (11)	0.0441 (11)	0.0010 (9)	−0.0137 (8)	−0.0156 (9)
C8	0.0436 (11)	0.0542 (12)	0.0620 (13)	0.0027 (10)	−0.0221 (10)	−0.0100 (10)
C9	0.0505 (12)	0.0551 (13)	0.0665 (14)	−0.0087 (10)	−0.0123 (10)	−0.0165 (11)
C10	0.0487 (12)	0.0586 (13)	0.0517 (13)	−0.0069 (10)	−0.0165 (10)	−0.0055 (10)
C11	0.0760 (17)	0.0662 (16)	0.0793 (18)	−0.0168 (13)	−0.0170 (14)	0.0020 (13)
C12	0.087 (2)	0.101 (2)	0.079 (2)	−0.0365 (18)	−0.0093 (17)	0.0198 (17)
C13	0.0741 (18)	0.139 (3)	0.0548 (17)	−0.019 (2)	−0.0074 (13)	−0.0057 (18)
C14	0.0695 (16)	0.110 (2)	0.0634 (16)	−0.0016 (16)	−0.0143 (13)	−0.0298 (15)
C15	0.0595 (14)	0.0739 (16)	0.0606 (15)	−0.0108 (12)	−0.0099 (11)	−0.0159 (12)
C16	0.0440 (11)	0.0445 (11)	0.0491 (12)	−0.0005 (9)	−0.0153 (9)	−0.0098 (9)
C17	0.0474 (11)	0.0563 (12)	0.0544 (13)	0.0043 (10)	−0.0104 (10)	−0.0135 (10)
C18	0.0496 (13)	0.0676 (15)	0.0789 (17)	0.0035 (12)	−0.0091 (11)	−0.0298 (13)
C19	0.0594 (15)	0.0570 (15)	0.113 (2)	0.0169 (12)	−0.0304 (15)	−0.0284 (15)
C20	0.0811 (18)	0.0561 (15)	0.096 (2)	0.0101 (14)	−0.0330 (16)	0.0051 (13)
C21	0.0598 (14)	0.0567 (13)	0.0653 (15)	0.0028 (12)	−0.0150 (11)	−0.0002 (11)
C22	0.0401 (10)	0.0617 (13)	0.0571 (13)	−0.0076 (10)	−0.0083 (9)	−0.0228 (10)
C23	0.0598 (14)	0.0803 (16)	0.0576 (14)	−0.0005 (12)	−0.0188 (11)	−0.0240 (12)
C24	0.0789 (18)	0.124 (2)	0.0601 (16)	−0.0048 (17)	−0.0195 (13)	−0.0333 (16)
C25	0.093 (2)	0.139 (3)	0.084 (2)	−0.013 (2)	−0.0077 (18)	−0.071 (2)
C26	0.097 (2)	0.090 (2)	0.104 (2)	−0.0098 (18)	−0.0022 (19)	−0.059 (2)
C27	0.0675 (15)	0.0639 (15)	0.0812 (18)	−0.0098 (12)	−0.0069 (13)	−0.0299 (13)
C28	0.0642 (15)	0.0576 (14)	0.107 (2)	0.0089 (12)	−0.0245 (14)	−0.0250 (14)

O1—C1	1.224 (2)	C12—H12	0.9300
O2—N1	1.417 (2)	C13—C14	1.368 (4)
O2—C8	1.461 (2)	C13—H13	0.9300
N1—C1	1.364 (2)	C14—C15	1.385 (3)
N1—C9	1.441 (3)	C14—H14	0.9300
C1—C2	1.508 (3)	C15—H15	0.9300
C2—C3	1.522 (3)	C16—C21	1.381 (3)
C2—C7	1.542 (2)	C16—C17	1.386 (3)
C2—H2	0.9800	C17—C18	1.385 (3)
C3—C16	1.513 (3)	C17—H17	0.9300
C3—C4	1.567 (3)	C18—C19	1.370 (3)
C3—H3	0.9800	C18—H18	0.9300
C4—C5	1.504 (3)	C19—C20	1.367 (4)
C4—C22	1.526 (3)	C19—H19	0.9300
C4—H4	0.9800	C20—C21	1.385 (3)
C5—C6	1.315 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.497 (3)	C22—C23	1.380 (3)
C6—H6	0.9300	C22—C27	1.386 (3)
C7—C8	1.533 (3)	C23—C24	1.387 (3)
C7—H7	0.9800	C23—H23	0.9300
C8—C28	1.500 (3)	C24—C25	1.371 (4)
C8—H8	0.9800	C24—H24	0.9300
C9—C10	1.509 (3)	C25—C26	1.367 (4)
C9—H9A	0.9700	C25—H25	0.9300
C9—H9B	0.9700	C26—C27	1.375 (4)
C10—C11	1.381 (3)	C26—H26	0.9300
C10—C15	1.380 (3)	C27—H27	0.9300
C11—C12	1.393 (4)	C28—H28A	0.9600
C11—H11	0.9300	C28—H28B	0.9600
C12—C13	1.367 (4)	C28—H28C	0.9600
N1—O2—C8	109.53 (14)	C13—C12—C11	120.3 (3)
C1—N1—O2	115.87 (15)	C13—C12—H12	119.9
C1—N1—C9	125.17 (16)	C11—C12—H12	119.9
O2—N1—C9	114.00 (16)	C12—C13—C14	119.7 (3)
O1—C1—N1	121.51 (18)	C12—C13—H13	120.2
O1—C1—C2	126.71 (18)	C14—C13—H13	120.2
N1—C1—C2	111.46 (15)	C13—C14—C15	120.3 (3)
C1—C2—C3	115.43 (15)	C13—C14—H14	119.9
C1—C2—C7	104.30 (14)	C15—C14—H14	119.9
C3—C2—C7	111.71 (15)	C10—C15—C14	121.0 (2)
C1—C2—H2	108.4	C10—C15—H15	119.5
C3—C2—H2	108.4	C14—C15—H15	119.5
C7—C2—H2	108.4	C21—C16—C17	117.39 (19)
C16—C3—C2	115.82 (15)	C21—C16—C3	119.58 (18)
C16—C3—C4	111.53 (15)	C17—C16—C3	123.01 (17)
C2—C3—C4	109.12 (15)	C18—C17—C16	121.5 (2)
C16—C3—H3	106.6	C18—C17—H17	119.2
C2—C3—H3	106.6	C16—C17—H17	119.2
C4—C3—H3	106.6	C19—C18—C17	119.9 (2)
C5—C4—C22	111.07 (17)	C19—C18—H18	120.1
C5—C4—C3	110.91 (16)	C17—C18—H18	120.1
C22—C4—C3	114.42 (15)	C20—C19—C18	119.7 (2)
C5—C4—H4	106.6	C20—C19—H19	120.1
C22—C4—H4	106.6	C18—C19—H19	120.1
C3—C4—H4	106.6	C19—C20—C21	120.3 (2)
C6—C5—C4	124.13 (18)	C19—C20—H20	119.8
C6—C5—H5	117.9	C21—C20—H20	119.8
C4—C5—H5	117.9	C16—C21—C20	121.2 (2)
C5—C6—C7	123.75 (18)	C16—C21—H21	119.4
C5—C6—H6	118.1	C20—C21—H21	119.4
C7—C6—H6	118.1	C23—C22—C27	117.6 (2)
C6—C7—C8	113.55 (15)	C23—C22—C4	121.82 (19)
C6—C7—C2	112.49 (16)	C27—C22—C4	120.5 (2)
C8—C7—C2	108.48 (15)	C22—C23—C24	121.0 (2)
C6—C7—H7	107.3	C22—C23—H23	119.5
C8—C7—H7	107.3	C24—C23—H23	119.5
C2—C7—H7	107.3	C25—C24—C23	120.1 (3)
O2—C8—C28	111.25 (18)	C25—C24—H24	120.0
O2—C8—C7	109.67 (15)	C23—C24—H24	120.0
C28—C8—C7	113.35 (19)	C26—C25—C24	119.7 (3)
O2—C8—H8	107.4	C26—C25—H25	120.2
C28—C8—H8	107.4	C24—C25—H25	120.2
C7—C8—H8	107.4	C25—C26—C27	120.2 (3)
N1—C9—C10	115.45 (18)	C25—C26—H26	119.9
N1—C9—H9A	108.4	C27—C26—H26	119.9
C10—C9—H9A	108.4	C26—C27—C22	121.4 (3)
N1—C9—H9B	108.4	C26—C27—H27	119.3
C10—C9—H9B	108.4	C22—C27—H27	119.3
H9A—C9—H9B	107.5	C8—C28—H28A	109.5
C11—C10—C15	118.3 (2)	C8—C28—H28B	109.5
C11—C10—C9	119.4 (2)	H28A—C28—H28B	109.5
C15—C10—C9	122.2 (2)	C8—C28—H28C	109.5
C10—C11—C12	120.6 (3)	H28A—C28—H28C	109.5
C10—C11—H11	119.7	H28B—C28—H28C	109.5
C12—C11—H11	119.7
C8—O2—N1—C1	−66.3 (2)	N1—C9—C10—C11	−150.2 (2)
C8—O2—N1—C9	137.27 (17)	N1—C9—C10—C15	34.1 (3)
O2—N1—C1—O1	−171.05 (16)	C15—C10—C11—C12	1.3 (4)
C9—N1—C1—O1	−17.6 (3)	C9—C10—C11—C12	−174.5 (2)
O2—N1—C1—C2	15.0 (2)	C10—C11—C12—C13	−1.7 (4)
C9—N1—C1—C2	168.44 (18)	C11—C12—C13—C14	0.8 (5)
O1—C1—C2—C3	−1.8 (3)	C12—C13—C14—C15	0.5 (4)
N1—C1—C2—C3	171.77 (15)	C11—C10—C15—C14	−0.1 (3)
O1—C1—C2—C7	−124.77 (19)	C9—C10—C15—C14	175.7 (2)
N1—C1—C2—C7	48.8 (2)	C13—C14—C15—C10	−0.9 (4)
C1—C2—C3—C16	53.8 (2)	C2—C3—C16—C21	−148.07 (19)
C7—C2—C3—C16	172.73 (15)	C4—C3—C16—C21	86.3 (2)
C1—C2—C3—C4	−179.38 (15)	C2—C3—C16—C17	33.9 (3)
C7—C2—C3—C4	−60.46 (19)	C4—C3—C16—C17	−91.7 (2)
C16—C3—C4—C5	177.36 (16)	C21—C16—C17—C18	0.3 (3)
C2—C3—C4—C5	48.1 (2)	C3—C16—C17—C18	178.32 (19)
C16—C3—C4—C22	50.8 (2)	C16—C17—C18—C19	0.1 (3)
C2—C3—C4—C22	−78.5 (2)	C17—C18—C19—C20	−0.3 (4)
C22—C4—C5—C6	108.5 (2)	C18—C19—C20—C21	0.2 (4)
C3—C4—C5—C6	−19.9 (3)	C17—C16—C21—C20	−0.4 (3)
C4—C5—C6—C7	1.5 (3)	C3—C16—C21—C20	−178.5 (2)
C5—C6—C7—C8	−135.8 (2)	C19—C20—C21—C16	0.1 (4)
C5—C6—C7—C2	−12.1 (3)	C5—C4—C22—C23	−37.7 (3)
C1—C2—C7—C6	167.33 (15)	C3—C4—C22—C23	88.8 (2)
C3—C2—C7—C6	42.0 (2)	C5—C4—C22—C27	140.3 (2)
C1—C2—C7—C8	−66.20 (18)	C3—C4—C22—C27	−93.2 (2)
C3—C2—C7—C8	168.46 (15)	C27—C22—C23—C24	−0.1 (3)
N1—O2—C8—C28	−83.2 (2)	C4—C22—C23—C24	177.9 (2)
N1—O2—C8—C7	43.0 (2)	C22—C23—C24—C25	−0.8 (4)
C6—C7—C8—O2	145.60 (16)	C23—C24—C25—C26	1.3 (5)
C2—C7—C8—O2	19.7 (2)	C24—C25—C26—C27	−0.9 (5)
C6—C7—C8—C28	−89.4 (2)	C25—C26—C27—C22	−0.1 (4)
C2—C7—C8—C28	144.74 (17)	C23—C22—C27—C26	0.6 (4)
C1—N1—C9—C10	−84.5 (3)	C4—C22—C27—C26	−177.5 (2)
O2—N1—C9—C10	69.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.58	3.311 (2)	135
C7—H7···O1ii	0.98	2.47	3.378 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.58	3.311 (2)	135
C7—H7⋯O1ii	0.98	2.47	3.378 (2)	154

Symmetry codes: (i) ; (ii) .