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

Magdalena Małecka; Beata Pasternak; Stanisław Leśniak

doi:10.1107/S1600536811032806

. 2011 Aug 27;67(Pt 9):o2390. doi: 10.1107/S1600536811032806

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

Magdalena Małecka ^a,^*, Beata Pasternak ^b, Stanisław Leśniak ^b

PMCID: PMC3200730 PMID: 22058987

Abstract

In the title compound, C₁₃H₁₅NO₂, the hexahydropyrrolo[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 intermolecular C—H⋯O hydrogen bonds link the molecules 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 _r = 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
Δρ_max = 0.21 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-67-o2390-sup1.cif^{(18.2KB, cif)}

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

e-67-o2390-Isup2.hkl^{(113.1KB, hkl)}

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

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

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Financial support from University of Łódź (grant No. 505/721/R to MM) is gratefully acknowledged. The authors thank Dr Klaus Harms from Philipps University in Marburg (Germany) for collecting the data.

supplementary crystallographic information

Comment

In this paper we provide a new oxazin-6-on derivative prepared in one step synthesis in FVT (Leśniak et al., 2009). The title compound (Fig. 1) represents an important structural unit found in biologically active compounds (Nicolaou et al., 2002). The hexahydro-pyrrolo[2,1-c][1,4] oxazine fragment is disordered over two conformations - A and B, respectively - in a ratio 0.656 (5):0.344 (5). Disordered five-membered ring adopts an envelope conformation in A, while in B this ring is nearly planar. Six-membered ring in A and B exhibits a chair conformation. Bond lengths (Allen et al., 1987) and angles are normal and correspond well to those observed in related structures (Chaume et al., 2008; Dorsey et al., 2003; Harwood et al., 1997).

The packing of the molecules in the crystal lattice is stabilized via weak intermolecular C—H···O hydrogen bonds (Table 1), which link the molecules into ribbons propagated in [010].

Experimental

General procedure. The flash vacuum thermolysis reactions were carried out in a 30x2.5 cm electrically heated horizontally oriented quartz tube packed with quartz rings, at 1.5x10^-3 Torr. The synthetic precursor (E)-1-morpholin-4-yl-3-phenylprop-2-en-1-one (2 mmol) was slowly sublimed at 80–100°C from a flask held into thermolysis preheated to 950–1000°C. The product thereby obtain was collected in a CO₂ acetone trap. After thermolysis, the whole system was brought to atmospheric pressure, allowing slow warming up to room temperature and the products were dissolved in CHCl₃. The solvent was removed under reduced pressure and 8-phenyl-hexahydro- pyrrolo[2,1-c][1,4]oxazin-6-one was purified chromatographically on SiO₂ and recrystallized from the hexane/CH₂Cl₂ (1:1) mixture.