8-Phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo-[2,1-c][1,4]oxazin-6-one.

In the title compound, C(13)H(15)NO(2), the hexa-hydro-pyrrolo-[2,1-c][1,4]oxazine fragment is disordered over two conformations (A and B) in a 0.656 (5):0.344 (5) ratio. The five-membered ring is similarly disordered and adopts an envelope conformation in A, while in B this ring is nearly planar [maximum deviation = 0.088 (1) Å]. The six-membered rings in both A and B exhibit chair conformations. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into ribbons propagating in [010].

Related literature

For the synthesis, see: Leśniak et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the biological properties of similar structures, see: Nicolaou et al. (2002 ▶). For related structures, see: Chaume et al. (2008 ▶); Dorsey et al. (2003 ▶); Harwood et al. (1997 ▶).

Experimental

Crystal data

C13H15NO2

M = 217.27

Monoclinic,

a = 13.2737 (12) Å

b = 7.1066 (4) Å

c = 11.9233 (10) Å

β = 103.917 (7)°

V = 1091.72 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.36 × 0.21 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

6960 measured reflections

2301 independent reflections

1200 reflections with I > 2σ(I)

R int = 0.108

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.109

S = 0.81

2301 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2000 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032806/cv5138sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032806/cv5138Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032806/cv5138Isup3.cml

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

C13H15NO2	F(000) = 464
Mr = 217.27	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2762 reflections
a = 13.2737 (12) Å	θ = 1.6–27.1°
b = 7.1066 (4) Å	µ = 0.09 mm−1
c = 11.9233 (10) Å	T = 100 K
β = 103.917 (7)°	Plate, colourless
V = 1091.72 (15) Å3	0.36 × 0.21 × 0.03 mm
Z = 4

Stoe IPDS 2 diffractometer	1200 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.108
planar graphite	θmax = 26.8°, θmin = 1.6°
Detector resolution: 6.67 pixels mm-1	h = −16→16
rotation method scans	k = −8→8
6960 measured reflections	l = −14→15
2301 independent 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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0509P)2] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max < 0.001
2301 reflections	Δρmax = 0.21 e Å−3
196 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (4)

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	Occ. (<1)
C6A	0.6366 (3)	0.7343 (6)	0.8977 (3)	0.0425 (9)	0.656 (5)
H6A	0.6341	0.8221	0.8348	0.051*	0.656 (5)
H6B	0.5799	0.7624	0.9333	0.051*	0.656 (5)
C6B	0.6801 (6)	0.6628 (11)	0.8736 (5)	0.0464 (18)	0.344 (5)
H6C	0.7183	0.5561	0.8543	0.056*	0.344 (5)
H6D	0.6709	0.7541	0.8115	0.056*	0.344 (5)
C5A	0.7290 (3)	0.6480 (5)	1.0830 (3)	0.0409 (9)	0.656 (5)
H5A	0.6657	0.6814	1.1054	0.049*	0.656 (5)
H5B	0.7878	0.6762	1.1466	0.049*	0.656 (5)
C5B	0.7692 (5)	0.5623 (12)	1.0597 (6)	0.0437 (17)	0.344 (5)
H5C	0.7980	0.4684	1.0172	0.052*	0.344 (5)
H5D	0.8204	0.5922	1.1304	0.052*	0.344 (5)
C7A	0.6287 (3)	0.5338 (5)	0.8537 (3)	0.0410 (9)	0.656 (5)
H7A	0.5612	0.5128	0.8019	0.049*	0.656 (5)
H7B	0.6814	0.5110	0.8112	0.049*	0.656 (5)
C7B	0.5784 (6)	0.6015 (11)	0.8900 (6)	0.051 (2)	0.344 (5)
H7C	0.5428	0.7067	0.9152	0.061*	0.344 (5)
H7D	0.5356	0.5545	0.8178	0.061*	0.344 (5)
N1A	0.6434 (2)	0.4075 (4)	0.9511 (2)	0.0353 (7)	0.656 (5)
N1B	0.5961 (5)	0.4532 (9)	0.9771 (5)	0.0411 (15)	0.344 (5)
C4A	0.7283 (3)	0.4418 (5)	1.0511 (2)	0.0364 (9)	0.656 (5)
H4A	0.7948	0.4042	1.0360	0.044*	0.656 (5)
C4B	0.6714 (5)	0.4927 (9)	1.0858 (5)	0.0407 (18)	0.344 (5)
H4B	0.6440	0.5817	1.1339	0.049*	0.344 (5)
O1	0.52984 (10)	0.1832 (2)	0.86955 (11)	0.0594 (5)
O2	0.73644 (10)	0.7476 (2)	0.98285 (11)	0.0568 (4)
C36	0.81951 (14)	0.3636 (3)	1.33444 (16)	0.0453 (5)
H36	0.7745	0.4576	1.3464	0.054*
C2	0.64430 (14)	0.1486 (3)	1.06256 (15)	0.0448 (5)
H2B	0.6954	0.0592	1.0491	0.054*
H2A	0.5935	0.0820	1.0940	0.054*
C32	0.86314 (15)	0.1182 (3)	1.22000 (16)	0.0459 (5)
H32	0.8476	0.0445	1.1536	0.055*
C35	0.91025 (14)	0.3310 (3)	1.41661 (16)	0.0514 (6)
H35	0.9259	0.4034	1.4835	0.062*
C33	0.95397 (15)	0.0859 (3)	1.30222 (18)	0.0516 (6)
H33	0.9991	−0.0083	1.2908	0.062*
C34	0.97791 (15)	0.1928 (3)	1.40096 (17)	0.0523 (6)
H34	1.0392	0.1719	1.4566	0.063*
C3	0.69621 (18)	0.3034 (3)	1.14461 (17)	0.0513 (6)
C31	0.79475 (13)	0.2572 (3)	1.23386 (14)	0.0408 (5)
C1	0.59269 (15)	0.2476 (3)	0.95258 (16)	0.0505 (5)
H7	0.6478 (17)	0.348 (4)	1.1835 (19)	0.074 (8)*

	U11	U22	U33	U12	U13	U23
C6A	0.0416 (19)	0.041 (2)	0.0405 (18)	0.0053 (17)	0.0014 (14)	0.0030 (16)
C6B	0.060 (5)	0.038 (4)	0.039 (4)	0.002 (4)	0.008 (3)	−0.004 (3)
C5A	0.0446 (19)	0.043 (2)	0.0316 (16)	0.0039 (16)	0.0017 (14)	0.0012 (15)
C5B	0.040 (4)	0.040 (5)	0.046 (4)	−0.001 (3)	0.002 (3)	0.002 (3)
C7A	0.0405 (18)	0.047 (2)	0.0323 (17)	0.0032 (16)	0.0021 (13)	0.0030 (16)
C7B	0.052 (4)	0.061 (5)	0.033 (3)	0.003 (4)	−0.004 (3)	0.009 (3)
N1A	0.0368 (15)	0.0380 (16)	0.0278 (14)	0.0003 (12)	0.0012 (12)	0.0004 (11)
N1B	0.041 (3)	0.051 (4)	0.027 (3)	−0.006 (3)	0.000 (2)	0.004 (2)
C4A	0.0326 (17)	0.041 (2)	0.0320 (16)	0.0001 (15)	0.0012 (13)	−0.0001 (14)
C4B	0.039 (4)	0.046 (4)	0.034 (3)	−0.001 (3)	0.003 (3)	−0.003 (3)
O1	0.0560 (8)	0.0739 (11)	0.0405 (8)	−0.0204 (8)	−0.0034 (7)	−0.0059 (7)
O2	0.0596 (8)	0.0651 (10)	0.0396 (8)	−0.0191 (7)	0.0001 (6)	0.0087 (7)
C36	0.0479 (10)	0.0486 (12)	0.0393 (11)	−0.0088 (9)	0.0103 (8)	−0.0029 (9)
C2	0.0427 (10)	0.0501 (12)	0.0392 (11)	−0.0101 (9)	0.0052 (8)	−0.0007 (9)
C32	0.0566 (12)	0.0460 (13)	0.0338 (10)	−0.0097 (9)	0.0082 (9)	−0.0034 (9)
C35	0.0500 (12)	0.0702 (16)	0.0325 (11)	−0.0172 (11)	0.0070 (9)	−0.0101 (10)
C33	0.0476 (11)	0.0527 (14)	0.0522 (13)	−0.0031 (9)	0.0073 (10)	0.0005 (11)
C34	0.0449 (11)	0.0690 (16)	0.0389 (11)	−0.0107 (11)	0.0019 (9)	0.0050 (11)
C3	0.0674 (14)	0.0440 (13)	0.0347 (11)	−0.0032 (10)	−0.0031 (10)	0.0024 (10)
C31	0.0493 (10)	0.0421 (11)	0.0287 (10)	−0.0098 (9)	0.0050 (8)	0.0019 (9)
C1	0.0506 (11)	0.0627 (15)	0.0345 (11)	−0.0167 (10)	0.0027 (9)	0.0008 (10)

C6A—O2	1.466 (3)	N1B—C4B	1.461 (7)
C6A—C7A	1.513 (6)	N1B—C1	1.489 (7)
C6A—H6A	0.9700	C4A—C3	1.618 (4)
C6A—H6B	0.9700	C4A—H4A	0.9800
C6B—O2	1.466 (7)	C4B—C3	1.516 (6)
C6B—C7B	1.476 (12)	C4B—H4B	0.9800
C6B—H6C	0.9700	O1—C1	1.220 (2)
C6B—H6D	0.9700	C36—C35	1.377 (2)
C5A—O2	1.411 (3)	C36—C31	1.389 (3)
C5A—C4A	1.513 (5)	C36—H36	0.9300
C5A—H5A	0.9700	C2—C1	1.500 (3)
C5A—H5B	0.9700	C2—C3	1.522 (3)
C5B—C4B	1.491 (10)	C2—H2B	0.9700
C5B—O2	1.603 (7)	C2—H2A	0.9700
C5B—H5C	0.9700	C32—C33	1.378 (3)
C5B—H5D	0.9700	C32—C31	1.378 (3)
C7A—N1A	1.444 (4)	C32—H32	0.9300
C7A—H7A	0.9700	C35—C34	1.373 (3)
C7A—H7B	0.9700	C35—H35	0.9300
C7B—N1B	1.459 (8)	C33—C34	1.373 (3)
C7B—H7C	0.9700	C33—H33	0.9300
C7B—H7D	0.9700	C34—H34	0.9300
N1A—C1	1.324 (3)	C3—C31	1.511 (3)
N1A—C4A	1.450 (4)	C3—H7	0.93 (2)
O2—C6A—C7A	106.0 (3)	C5B—C4B—C3	106.7 (6)
O2—C6A—H6A	110.5	N1B—C4B—H4B	111.9
C7A—C6A—H6A	110.5	C5B—C4B—H4B	111.9
O2—C6A—H6B	110.5	C3—C4B—H4B	111.9
C7A—C6A—H6B	110.5	C5A—O2—C6B	114.9 (3)
H6A—C6A—H6B	108.7	C5A—O2—C6A	108.5 (2)
O2—C6B—C7B	106.9 (6)	C6B—O2—C6A	34.4 (3)
O2—C6B—H6C	110.3	C5A—O2—C5B	33.9 (3)
C7B—C6B—H6C	110.3	C6B—O2—C5B	100.4 (4)
O2—C6B—H6D	110.3	C6A—O2—C5B	114.8 (3)
C7B—C6B—H6D	110.3	C35—C36—C31	120.5 (2)
H6C—C6B—H6D	108.6	C35—C36—H36	119.8
O2—C5A—C4A	105.7 (3)	C31—C36—H36	119.7
O2—C5A—H5A	110.6	C1—C2—C3	105.31 (17)
C4A—C5A—H5A	110.6	C1—C2—H2B	110.7
O2—C5A—H5B	110.6	C3—C2—H2B	110.7
C4A—C5A—H5B	110.6	C1—C2—H2A	110.7
H5A—C5A—H5B	108.7	C3—C2—H2A	110.7
C4B—C5B—O2	105.2 (5)	H2B—C2—H2A	108.8
C4B—C5B—H5C	110.7	C33—C32—C31	121.53 (18)
O2—C5B—H5C	110.7	C33—C32—H32	119.2
C4B—C5B—H5D	110.7	C31—C32—H32	119.2
O2—C5B—H5D	110.7	C34—C35—C36	120.81 (19)
H5C—C5B—H5D	108.8	C34—C35—H35	119.6
N1A—C7A—C6A	108.7 (3)	C36—C35—H35	119.6
N1A—C7A—H7A	109.9	C34—C33—C32	120.0 (2)
C6A—C7A—H7A	109.9	C34—C33—H33	120.0
N1A—C7A—H7B	109.9	C32—C33—H33	120.0
C6A—C7A—H7B	109.9	C33—C34—C35	119.22 (18)
H7A—C7A—H7B	108.3	C33—C34—H34	120.4
N1B—C7B—C6B	108.1 (5)	C35—C34—H34	120.4
N1B—C7B—H7C	110.1	C31—C3—C4B	125.0 (3)
C6B—C7B—H7C	110.1	C31—C3—C2	118.49 (18)
N1B—C7B—H7D	110.1	C4B—C3—C2	109.2 (2)
C6B—C7B—H7D	110.1	C31—C3—C4A	106.91 (19)
H7C—C7B—H7D	108.4	C4B—C3—C4A	37.5 (2)
C1—N1A—C7A	125.0 (2)	C2—C3—C4A	98.62 (18)
C1—N1A—C4A	115.5 (2)	C31—C3—H7	107.8 (14)
C7A—N1A—C4A	119.0 (3)	C4B—C3—H7	80.2 (16)
C7B—N1B—C4B	116.9 (5)	C2—C3—H7	107.7 (15)
C7B—N1B—C1	125.3 (5)	C4A—C3—H7	117.6 (16)
C4B—N1B—C1	110.2 (4)	C32—C31—C36	117.90 (17)
N1A—C4A—C5A	109.0 (2)	C32—C31—C3	123.72 (17)
N1A—C4A—C3	100.6 (2)	C36—C31—C3	118.36 (19)
C5A—C4A—C3	113.8 (3)	O1—C1—N1A	124.2 (2)
N1A—C4A—H4A	111.0	O1—C1—N1B	120.7 (3)
C5A—C4A—H4A	111.0	N1A—C1—N1B	33.7 (2)
C3—C4A—H4A	111.0	O1—C1—C2	127.8 (2)
N1B—C4B—C5B	108.8 (5)	N1A—C1—C2	106.68 (17)
N1B—C4B—C3	105.4 (4)	N1B—C1—C2	107.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2i	0.97	2.46	3.329 (3)	149
C7A—H7A···O1ii	0.97	2.43	3.154 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2i	0.97	2.46	3.329 (3)	149
C7A—H7A⋯O1ii	0.97	2.43	3.154 (4)	131

Symmetry codes: (i) ; (ii) .