tert-Butyl 6-acetamido-3,4-dihydro-2H-1,4-benzoxazine-4-carboxyl-ate.

The title mol-ecule, C(15)H(20)N(2)O(4), contains a benzene ring fused to an oxazine ring and one tert-but-oxy-carbonyl group bound to the N atom. An intra-molecular C-H⋯O inter-action occurs. In the crystal, mol-ecules are linked through inter-molecular 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 = 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

Δρmax = 0.29 e Å−3

Δρmin = −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.

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

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

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

C15H20N2O4	F(000) = 1248
Mr = 292.33	Dx = 1.321 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8192 reflections
a = 9.675 (2) Å	θ = 3.1–27.5°
b = 13.137 (3) Å	µ = 0.10 mm−1
c = 23.128 (5) Å	T = 103 K
V = 2939.7 (12) Å3	Chunk, colorless
Z = 8	0.43 × 0.40 × 0.18 mm

Rigaku SPIDER diffractometer	3005 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.039
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −12→12
20907 measured reflections	k = −16→17
3367 independent reflections	l = −29→29

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0536P)2 + 1.960P] where P = (Fo2 + 2Fc2)/3
3367 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 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
O1	0.16030 (11)	0.52261 (8)	0.61658 (5)	0.0221 (3)
O2	0.53747 (10)	0.73649 (7)	0.57927 (4)	0.0173 (2)
O3	0.62739 (12)	0.58152 (8)	0.55786 (5)	0.0239 (3)
O4	0.08299 (11)	0.93078 (8)	0.77211 (5)	0.0222 (3)
N1	0.43426 (13)	0.59636 (9)	0.61318 (5)	0.0164 (3)
N2	0.28810 (12)	0.88225 (9)	0.73211 (5)	0.0146 (3)
C1	0.40682 (16)	0.48702 (11)	0.61007 (7)	0.0201 (3)
H1A	0.4110	0.4569	0.6493	0.024*
H1B	0.4775	0.4534	0.5857	0.024*
C2	0.26528 (17)	0.47066 (11)	0.58444 (7)	0.0212 (3)
H2A	0.2647	0.4954	0.5440	0.025*
H2B	0.2445	0.3969	0.5839	0.025*
C3	0.19649 (15)	0.61199 (11)	0.64273 (6)	0.0162 (3)
C4	0.09200 (15)	0.66258 (11)	0.67188 (6)	0.0178 (3)
H4	0.0014	0.6348	0.6718	0.021*
C5	0.11645 (15)	0.75263 (11)	0.70112 (6)	0.0166 (3)
H5	0.0431	0.7872	0.7200	0.020*
C6	0.25037 (15)	0.79196 (10)	0.70245 (6)	0.0140 (3)
C7	0.35627 (14)	0.74149 (10)	0.67329 (6)	0.0145 (3)
H7	0.4475	0.7681	0.6745	0.017*
C8	0.33000 (15)	0.65256 (11)	0.64237 (6)	0.0145 (3)
C9	0.54187 (15)	0.63514 (11)	0.58119 (6)	0.0159 (3)
C10	0.65864 (16)	0.79588 (12)	0.56032 (7)	0.0200 (3)
C11	0.60965 (17)	0.90434 (11)	0.56794 (7)	0.0237 (3)
H11A	0.5321	0.9174	0.5417	0.028*
H11B	0.6855	0.9512	0.5591	0.028*
H11C	0.5796	0.9146	0.6080	0.028*
C12	0.6938 (3)	0.77433 (14)	0.49806 (9)	0.0433 (5)
H12A	0.7274	0.7043	0.4944	0.052*
H12B	0.7658	0.8216	0.4851	0.052*
H12C	0.6111	0.7831	0.4741	0.052*
C13	0.7775 (2)	0.77283 (15)	0.60145 (11)	0.0425 (5)
H13A	0.7467	0.7825	0.6414	0.051*
H13B	0.8548	0.8189	0.5933	0.051*
H13C	0.8077	0.7022	0.5961	0.051*
C14	0.20747 (14)	0.94428 (11)	0.76449 (6)	0.0155 (3)
C15	0.28116 (15)	1.03281 (11)	0.79194 (6)	0.0188 (3)
H15A	0.2406	1.0966	0.7780	0.023*
H15B	0.3793	1.0306	0.7816	0.023*
H15C	0.2715	1.0289	0.8341	0.023*
H2N	0.375 (2)	0.9008 (13)	0.7287 (8)	0.022 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0204 (6)	0.0195 (5)	0.0263 (6)	−0.0049 (4)	0.0015 (4)	−0.0083 (4)
O2	0.0147 (5)	0.0148 (5)	0.0224 (5)	−0.0012 (4)	0.0056 (4)	0.0001 (4)
O3	0.0232 (6)	0.0193 (5)	0.0292 (6)	0.0037 (5)	0.0103 (5)	−0.0013 (5)
O4	0.0124 (5)	0.0268 (6)	0.0275 (6)	−0.0001 (4)	0.0030 (4)	−0.0073 (5)
N1	0.0167 (6)	0.0136 (6)	0.0189 (6)	0.0006 (5)	0.0039 (5)	−0.0008 (5)
N2	0.0107 (6)	0.0153 (6)	0.0179 (6)	−0.0017 (5)	0.0012 (4)	−0.0010 (5)
C1	0.0240 (8)	0.0134 (7)	0.0230 (8)	0.0007 (6)	0.0048 (6)	0.0001 (6)
C2	0.0268 (8)	0.0163 (7)	0.0205 (7)	−0.0020 (6)	0.0038 (6)	−0.0035 (6)
C3	0.0188 (7)	0.0153 (7)	0.0145 (6)	−0.0021 (6)	−0.0023 (5)	0.0000 (5)
C4	0.0128 (7)	0.0205 (7)	0.0202 (7)	−0.0035 (6)	−0.0006 (5)	0.0001 (6)
C5	0.0120 (6)	0.0187 (7)	0.0191 (7)	−0.0006 (5)	0.0022 (5)	−0.0001 (5)
C6	0.0151 (7)	0.0150 (6)	0.0119 (6)	−0.0003 (5)	−0.0001 (5)	0.0016 (5)
C7	0.0125 (7)	0.0164 (7)	0.0146 (6)	−0.0016 (5)	0.0004 (5)	0.0020 (5)
C8	0.0144 (7)	0.0159 (7)	0.0130 (6)	0.0019 (5)	0.0016 (5)	0.0020 (5)
C9	0.0156 (7)	0.0167 (7)	0.0153 (6)	0.0014 (6)	−0.0011 (5)	0.0005 (5)
C10	0.0166 (7)	0.0195 (7)	0.0237 (8)	−0.0036 (6)	0.0076 (6)	0.0011 (6)
C11	0.0250 (8)	0.0182 (7)	0.0280 (8)	−0.0039 (6)	0.0068 (6)	−0.0011 (6)
C12	0.0707 (15)	0.0260 (9)	0.0330 (10)	−0.0041 (10)	0.0303 (10)	−0.0012 (8)
C13	0.0241 (10)	0.0336 (10)	0.0697 (15)	−0.0061 (8)	−0.0121 (9)	0.0070 (10)
C14	0.0146 (7)	0.0170 (7)	0.0148 (7)	0.0012 (5)	−0.0007 (5)	0.0020 (5)
C15	0.0169 (7)	0.0198 (7)	0.0197 (7)	−0.0007 (6)	0.0016 (5)	−0.0034 (6)

O1—C3	1.3664 (17)	C5—C6	1.395 (2)
O1—C2	1.4317 (18)	C5—H5	0.9500
O2—C9	1.3328 (18)	C6—C7	1.394 (2)
O2—C10	1.4749 (17)	C7—C8	1.393 (2)
O3—C9	1.2132 (18)	C7—H7	0.9500
O4—C14	1.2301 (18)	C10—C12	1.506 (2)
N1—C9	1.3752 (19)	C10—C11	1.512 (2)
N1—C8	1.4208 (18)	C10—C13	1.523 (2)
N1—C1	1.4624 (19)	C11—H11A	0.9800
N2—C14	1.3540 (18)	C11—H11B	0.9800
N2—C6	1.4180 (18)	C11—H11C	0.9800
N2—H2N	0.88 (2)	C12—H12A	0.9800
C1—C2	1.508 (2)	C12—H12B	0.9800
C1—H1A	0.9900	C12—H12C	0.9800
C1—H1B	0.9900	C13—H13A	0.9800
C2—H2A	0.9900	C13—H13B	0.9800
C2—H2B	0.9900	C13—H13C	0.9800
C3—C4	1.385 (2)	C14—C15	1.505 (2)
C3—C8	1.398 (2)	C15—H15A	0.9800
C4—C5	1.383 (2)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C3—O1—C2	117.24 (12)	C3—C8—N1	117.45 (13)
C9—O2—C10	120.86 (11)	O3—C9—O2	125.95 (14)
C9—N1—C8	126.92 (12)	O3—C9—N1	122.72 (13)
C9—N1—C1	118.35 (12)	O2—C9—N1	111.33 (12)
C8—N1—C1	113.88 (12)	O2—C10—C12	111.35 (14)
C14—N2—C6	128.51 (12)	O2—C10—C11	102.40 (12)
C14—N2—H2N	115.7 (12)	C12—C10—C11	111.06 (14)
C6—N2—H2N	115.8 (12)	O2—C10—C13	108.04 (13)
N1—C1—C2	108.92 (12)	C12—C10—C13	112.90 (17)
N1—C1—H1A	109.9	C11—C10—C13	110.57 (14)
C2—C1—H1A	109.9	C10—C11—H11A	109.5
N1—C1—H1B	109.9	C10—C11—H11B	109.5
C2—C1—H1B	109.9	H11A—C11—H11B	109.5
H1A—C1—H1B	108.3	C10—C11—H11C	109.5
O1—C2—C1	111.86 (12)	H11A—C11—H11C	109.5
O1—C2—H2A	109.2	H11B—C11—H11C	109.5
C1—C2—H2A	109.2	C10—C12—H12A	109.5
O1—C2—H2B	109.2	C10—C12—H12B	109.5
C1—C2—H2B	109.2	H12A—C12—H12B	109.5
H2A—C2—H2B	107.9	C10—C12—H12C	109.5
O1—C3—C4	116.16 (13)	H12A—C12—H12C	109.5
O1—C3—C8	124.19 (13)	H12B—C12—H12C	109.5
C4—C3—C8	119.64 (13)	C10—C13—H13A	109.5
C5—C4—C3	121.58 (13)	C10—C13—H13B	109.5
C5—C4—H4	119.2	H13A—C13—H13B	109.5
C3—C4—H4	119.2	C10—C13—H13C	109.5
C4—C5—C6	119.10 (13)	H13A—C13—H13C	109.5
C4—C5—H5	120.4	H13B—C13—H13C	109.5
C6—C5—H5	120.4	O4—C14—N2	123.82 (13)
C7—C6—C5	119.71 (13)	O4—C14—C15	121.00 (13)
C7—C6—N2	116.27 (13)	N2—C14—C15	115.18 (12)
C5—C6—N2	124.02 (13)	C14—C15—H15A	109.5
C8—C7—C6	120.86 (13)	C14—C15—H15B	109.5
C8—C7—H7	119.6	H15A—C15—H15B	109.5
C6—C7—H7	119.6	C14—C15—H15C	109.5
C7—C8—C3	119.04 (13)	H15A—C15—H15C	109.5
C7—C8—N1	123.38 (13)	H15B—C15—H15C	109.5
C9—N1—C1—C2	−116.78 (14)	C4—C3—C8—C7	2.4 (2)
C8—N1—C1—C2	53.44 (16)	O1—C3—C8—N1	−0.5 (2)
C3—O1—C2—C1	32.01 (17)	C4—C3—C8—N1	178.35 (12)
N1—C1—C2—O1	−56.42 (16)	C9—N1—C8—C7	−41.1 (2)
C2—O1—C3—C4	177.85 (13)	C1—N1—C8—C7	149.70 (13)
C2—O1—C3—C8	−3.3 (2)	C9—N1—C8—C3	143.12 (14)
O1—C3—C4—C5	178.58 (13)	C1—N1—C8—C3	−26.10 (18)
C8—C3—C4—C5	−0.3 (2)	C10—O2—C9—O3	−15.9 (2)
C3—C4—C5—C6	−1.6 (2)	C10—O2—C9—N1	164.66 (12)
C4—C5—C6—C7	1.5 (2)	C8—N1—C9—O3	179.49 (14)
C4—C5—C6—N2	−178.52 (13)	C1—N1—C9—O3	−11.7 (2)
C14—N2—C6—C7	−178.52 (13)	C8—N1—C9—O2	−1.1 (2)
C14—N2—C6—C5	1.5 (2)	C1—N1—C9—O2	167.70 (12)
C5—C6—C7—C8	0.5 (2)	C9—O2—C10—C12	64.04 (18)
N2—C6—C7—C8	−179.43 (12)	C9—O2—C10—C11	−177.21 (13)
C6—C7—C8—C3	−2.5 (2)	C9—O2—C10—C13	−60.47 (18)
C6—C7—C8—N1	−178.20 (12)	C6—N2—C14—O4	−1.4 (2)
O1—C3—C8—C7	−176.45 (13)	C6—N2—C14—C15	178.02 (13)

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)
C1—H1B···O3	0.99	2.31	2.748 (2)	105
C5—H5···O4	0.95	2.27	2.8771 (19)	121
C7—H7···O2	0.95	2.40	2.7940 (18)	104
C11—H11B···O3ii	0.98	2.49	3.456 (2)	168
C12—H12A···O3	0.98	2.39	2.957 (2)	117
C13—H13C···O3	0.98	2.52	3.073 (2)	116

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

Symmetry codes: (i) ; (ii) .