tert-Butyl 6-acetamido-3,4-dihydro-2H-1,4-benzoxazine-4-carboxyl­ate

Xiao-Bo Gu

doi:10.1107/S1600536810036937

. 2010 Sep 25;66(Pt 10):o2600. doi: 10.1107/S1600536810036937

tert-Butyl 6-acetamido-3,4-dihydro-2H-1,4-benzoxazine-4-carboxylate

Xiao-Bo Gu ^a,^*

PMCID: PMC2983301 PMID: 21587577

Abstract

The title molecule, C₁₅H₂₀N₂O₄, contains a benzene ring fused to an oxazine ring and one tert-butoxycarbonyl group bound to the N atom. An intramolecular C—H⋯O interaction occurs. In the crystal, molecules are linked through intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the pharmacological properties of phenylmorpholine derivatives, see: Bourlot et al. (1998 ▶); Albanese et al. (2003 ▶); La et al. (2008 ▶). For structures, see: Chen et al. (2003 ▶); Olmstead et al. (2003 ▶); Vergeer et al. (1999 ▶).

Experimental

Crystal data

C₁₅H₂₀N₂O₄
M _r = 292.33
Orthorhombic,
a = 9.675 (2) Å
b = 13.137 (3) Å
c = 23.128 (5) Å
V = 2939.7 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 103 K
0.43 × 0.40 × 0.18 mm

Data collection

Rigaku SPIDER diffractometer
20907 measured reflections
3367 independent reflections
3005 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.114
S = 1.00
3367 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036937/jh2200sup1.cif

e-66-o2600-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036937/jh2200Isup2.hkl

e-66-o2600-Isup2.hkl^{(165.2KB, hkl)}

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
N2—H2N⋯O4ⁱ	0.879 (19)	2.051 (19)	2.9251 (17)	173.1 (16)
C5—H5⋯O4	0.95	2.27	2.8771 (19)	121
C11—H11B⋯O3ⁱⁱ	0.98	2.49	3.456 (2)	168

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

Acknowledgments

This work was supported financially by Jiangsu Province ’s Key Medical Talents Program (No. RC2007097).

supplementary crystallographic information

Comment

The stucture of the title compound, (I), is an important phenylmorpholine product. Phenylmorpholine compounds are used as α2 C adrenergic receptor agonists. Numerous phenylmorpholine derivatives possess various pharmacological properties (Bourlot, et al., 1998; Albanese, et al., 2003; La et al., 2008).

We report here the crystal structure of the title compound. (Fig. 1). The title molecule of (I) contains a benzene ring fused to an oxazine ring and one tert-butoxycarbonyl bound to the N atom. The N1—C8 bond distance is 1.4208 (18) Å and agrees with literature values (Vergeer, et al., 1999; Chen, et al., 2003; Olmstead, et al., 2003). The conformation of the six-membered heterocyclic ring shows that C1 and C2 are out of the plane of the remaining four atoms by 0.5950 (16) and -0.0818 (16) Å, respectively.

The molecules are linked through hydrogen-bonding interactions of types N—H···O and C—H···O (Table 1).

Experimental

The title compound was crystallized from a mixed solvent composed of dichloromethane and hexane (1:1); colorlessblock-shaped crystals were obtained after several days.