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

The title mol-ecule, C(13)H(18)N(2)O(3), contains a benzene ring fused to an oxazine ring and one tert-but-oxy-carbonyl group bound to the N atom of the oxazine ring. A weak intra-molecular C-H⋯O inter-action occurs. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds stack the mol-ecules down the b axis. Weak C-H⋯N contacts connect the stacks, generating a three-dimensional network.

Related literature

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

Experimental

Crystal data

C13H18N2O3

M = 250.29

Monoclinic,

a = 9.439 (4) Å

b = 7.941 (3) Å

c = 17.598 (7) Å

β = 97.235 (6)°

V = 1308.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 103 K

0.37 × 0.27 × 0.21 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

13574 measured reflections

3816 independent reflections

3118 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.106

S = 1.00

3816 reflections

174 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053681004777X/sj5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004777X/sj5053Isup2.hkl

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

C13H18N2O3	F(000) = 536
Mr = 250.29	Dx = 1.270 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3844 reflections
a = 9.439 (4) Å	θ = 3.6–30.0°
b = 7.941 (3) Å	µ = 0.09 mm−1
c = 17.598 (7) Å	T = 103 K
β = 97.235 (6)°	Block, colorless
V = 1308.6 (8) Å3	0.37 × 0.27 × 0.21 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	3118 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.035
graphite	θmax = 30.0°, θmin = 2.3°
Detector resolution: 28.5714 pixels mm-1	h = −13→13
φ and ω scans	k = −11→11
13574 measured reflections	l = −22→24
3816 independent reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.506P] where P = (Fo2 + 2Fc2)/3
3816 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.19 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	0.29075 (9)	0.23440 (12)	0.77441 (5)	0.0238 (2)
O2	0.27308 (9)	0.60469 (11)	0.55727 (5)	0.01769 (18)
O3	0.47393 (9)	0.70065 (11)	0.62807 (5)	0.01852 (19)
N1	0.36964 (10)	0.45345 (12)	0.65823 (6)	0.0148 (2)
N2	0.84770 (11)	0.48161 (15)	0.80355 (7)	0.0226 (2)
C1	0.46953 (11)	0.41260 (14)	0.72306 (6)	0.0138 (2)
C2	0.61108 (12)	0.46877 (14)	0.73224 (6)	0.0153 (2)
H2	0.6415	0.5440	0.6956	0.018*
C3	0.70861 (12)	0.41698 (15)	0.79396 (7)	0.0166 (2)
C4	0.66399 (13)	0.30549 (15)	0.84764 (7)	0.0191 (2)
H4	0.7294	0.2684	0.8898	0.023*
C5	0.52391 (13)	0.24943 (15)	0.83905 (7)	0.0200 (2)
H5	0.4941	0.1738	0.8757	0.024*
C6	0.42614 (12)	0.30153 (15)	0.77789 (7)	0.0172 (2)
C7	0.18660 (13)	0.31174 (17)	0.71949 (8)	0.0243 (3)
H7A	0.1574	0.4212	0.7395	0.029*
H7B	0.1010	0.2389	0.7105	0.029*
C8	0.24682 (13)	0.33916 (16)	0.64505 (7)	0.0220 (3)
H8A	0.2771	0.2301	0.6251	0.026*
H8B	0.1728	0.3884	0.6066	0.026*
C9	0.37957 (11)	0.59648 (14)	0.61556 (6)	0.0140 (2)
C10	0.27444 (13)	0.74056 (16)	0.49941 (7)	0.0195 (2)
C11	0.25934 (15)	0.91226 (17)	0.53576 (8)	0.0268 (3)
H11A	0.1790	0.9102	0.5660	0.040*
H11B	0.2419	0.9978	0.4955	0.040*
H11C	0.3474	0.9395	0.5692	0.040*
C12	0.14095 (16)	0.7002 (2)	0.44419 (8)	0.0338 (3)
H12A	0.1490	0.5864	0.4236	0.051*
H12B	0.1314	0.7817	0.4020	0.051*
H12C	0.0567	0.7065	0.4714	0.051*
C13	0.40675 (16)	0.7250 (2)	0.45926 (8)	0.0305 (3)
H13A	0.4910	0.7576	0.4946	0.046*
H13B	0.3977	0.7992	0.4144	0.046*
H13C	0.4171	0.6082	0.4429	0.046*
H2A	0.8731 (17)	0.538 (2)	0.7639 (10)	0.030 (4)*
H2B	0.9124 (19)	0.408 (2)	0.8234 (10)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0165 (4)	0.0260 (5)	0.0295 (5)	−0.0026 (3)	0.0048 (3)	0.0108 (4)
O2	0.0174 (4)	0.0176 (4)	0.0170 (4)	−0.0026 (3)	−0.0021 (3)	0.0026 (3)
O3	0.0171 (4)	0.0165 (4)	0.0210 (4)	−0.0041 (3)	−0.0015 (3)	0.0022 (3)
N1	0.0124 (4)	0.0144 (5)	0.0174 (5)	−0.0023 (3)	0.0006 (3)	0.0006 (4)
N2	0.0170 (5)	0.0221 (6)	0.0268 (6)	−0.0006 (4)	−0.0040 (4)	0.0055 (5)
C1	0.0147 (5)	0.0122 (5)	0.0146 (5)	0.0021 (4)	0.0023 (4)	−0.0006 (4)
C2	0.0159 (5)	0.0137 (5)	0.0164 (5)	0.0012 (4)	0.0029 (4)	0.0006 (4)
C3	0.0164 (5)	0.0145 (5)	0.0184 (5)	0.0022 (4)	0.0007 (4)	−0.0026 (4)
C4	0.0220 (6)	0.0182 (6)	0.0167 (5)	0.0054 (4)	0.0002 (4)	0.0012 (4)
C5	0.0243 (6)	0.0180 (6)	0.0185 (6)	0.0027 (5)	0.0057 (4)	0.0045 (5)
C6	0.0161 (5)	0.0162 (5)	0.0201 (5)	0.0009 (4)	0.0057 (4)	0.0012 (4)
C7	0.0151 (5)	0.0241 (7)	0.0337 (7)	−0.0021 (5)	0.0025 (5)	0.0094 (5)
C8	0.0191 (6)	0.0200 (6)	0.0257 (6)	−0.0085 (5)	−0.0015 (5)	0.0034 (5)
C9	0.0136 (5)	0.0147 (5)	0.0138 (5)	0.0014 (4)	0.0022 (4)	−0.0015 (4)
C10	0.0216 (6)	0.0199 (6)	0.0160 (5)	−0.0003 (5)	−0.0017 (4)	0.0041 (4)
C11	0.0323 (7)	0.0191 (6)	0.0280 (7)	0.0036 (5)	−0.0006 (5)	0.0032 (5)
C12	0.0350 (8)	0.0345 (8)	0.0274 (7)	−0.0065 (6)	−0.0143 (6)	0.0071 (6)
C13	0.0328 (7)	0.0392 (8)	0.0209 (6)	0.0035 (6)	0.0090 (5)	0.0066 (6)

O1—C6	1.3789 (15)	C5—H5	0.9500
O1—C7	1.4278 (15)	C7—C8	1.5081 (19)
O2—C9	1.3443 (13)	C7—H7A	0.9900
O2—C10	1.4848 (15)	C7—H7B	0.9900
O3—C9	1.2152 (14)	C8—H8A	0.9900
N1—C9	1.3713 (15)	C8—H8B	0.9900
N1—C1	1.4230 (14)	C10—C13	1.5154 (19)
N1—C8	1.4675 (15)	C10—C11	1.5204 (19)
N2—C3	1.3999 (16)	C10—C12	1.5253 (17)
N2—H2A	0.887 (17)	C11—H11A	0.9800
N2—H2B	0.884 (19)	C11—H11B	0.9800
C1—C2	1.3985 (16)	C11—H11C	0.9800
C1—C6	1.4058 (16)	C12—H12A	0.9800
C2—C3	1.3945 (16)	C12—H12B	0.9800
C2—H2	0.9500	C12—H12C	0.9800
C3—C4	1.3977 (17)	C13—H13A	0.9800
C4—C5	1.3853 (18)	C13—H13B	0.9800
C4—H4	0.9500	C13—H13C	0.9800
C5—C6	1.3896 (17)
C6—O1—C7	114.78 (10)	N1—C8—H8A	109.8
C9—O2—C10	119.23 (9)	C7—C8—H8A	109.8
C9—N1—C1	122.94 (9)	N1—C8—H8B	109.8
C9—N1—C8	122.19 (10)	C7—C8—H8B	109.8
C1—N1—C8	114.60 (9)	H8A—C8—H8B	108.3
C3—N2—H2A	115.6 (10)	O3—C9—O2	124.46 (10)
C3—N2—H2B	113.3 (12)	O3—C9—N1	124.31 (10)
H2A—N2—H2B	113.7 (16)	O2—C9—N1	111.22 (9)
C2—C1—C6	118.52 (10)	O2—C10—C13	109.84 (10)
C2—C1—N1	123.15 (10)	O2—C10—C11	110.72 (10)
C6—C1—N1	118.19 (10)	C13—C10—C11	113.31 (12)
C3—C2—C1	121.55 (11)	O2—C10—C12	101.90 (10)
C3—C2—H2	119.2	C13—C10—C12	110.43 (12)
C1—C2—H2	119.2	C11—C10—C12	110.06 (11)
C2—C3—C4	119.19 (11)	C10—C11—H11A	109.5
C2—C3—N2	120.19 (11)	C10—C11—H11B	109.5
C4—C3—N2	120.57 (11)	H11A—C11—H11B	109.5
C5—C4—C3	119.64 (11)	C10—C11—H11C	109.5
C5—C4—H4	120.2	H11A—C11—H11C	109.5
C3—C4—H4	120.2	H11B—C11—H11C	109.5
C4—C5—C6	121.37 (11)	C10—C12—H12A	109.5
C4—C5—H5	119.3	C10—C12—H12B	109.5
C6—C5—H5	119.3	H12A—C12—H12B	109.5
O1—C6—C5	116.15 (11)	C10—C12—H12C	109.5
O1—C6—C1	124.09 (10)	H12A—C12—H12C	109.5
C5—C6—C1	119.73 (11)	H12B—C12—H12C	109.5
O1—C7—C8	110.33 (10)	C10—C13—H13A	109.5
O1—C7—H7A	109.6	C10—C13—H13B	109.5
C8—C7—H7A	109.6	H13A—C13—H13B	109.5
O1—C7—H7B	109.6	C10—C13—H13C	109.5
C8—C7—H7B	109.6	H13A—C13—H13C	109.5
H7A—C7—H7B	108.1	H13B—C13—H13C	109.5
N1—C8—C7	109.19 (10)
C9—N1—C1—C2	−26.57 (17)	N1—C1—C6—O1	−2.62 (17)
C8—N1—C1—C2	159.29 (11)	C2—C1—C6—C5	−0.48 (17)
C9—N1—C1—C6	157.74 (11)	N1—C1—C6—C5	175.41 (11)
C8—N1—C1—C6	−16.40 (15)	C6—O1—C7—C8	44.10 (15)
C6—C1—C2—C3	0.09 (17)	C9—N1—C8—C7	−126.86 (12)
N1—C1—C2—C3	−175.59 (10)	C1—N1—C8—C7	47.33 (14)
C1—C2—C3—C4	0.40 (17)	O1—C7—C8—N1	−61.83 (14)
C1—C2—C3—N2	−176.97 (11)	C10—O2—C9—O3	5.54 (17)
C2—C3—C4—C5	−0.49 (17)	C10—O2—C9—N1	−173.22 (9)
N2—C3—C4—C5	176.87 (11)	C1—N1—C9—O3	0.71 (17)
C3—C4—C5—C6	0.10 (18)	C8—N1—C9—O3	174.42 (11)
C7—O1—C6—C5	169.42 (11)	C1—N1—C9—O2	179.48 (10)
C7—O1—C6—C1	−12.48 (17)	C8—N1—C9—O2	−6.81 (15)
C4—C5—C6—O1	178.58 (11)	C9—O2—C10—C13	61.25 (14)
C4—C5—C6—C1	0.40 (18)	C9—O2—C10—C11	−64.64 (14)
C2—C1—C6—O1	−178.52 (11)	C9—O2—C10—C12	178.33 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3i	0.885 (17)	2.088 (17)	2.9581 (19)	167.4 (16)
C2—H2···O3	0.95	2.23	2.7981 (18)	117
C7—H7A···O1ii	0.99	2.55	3.364 (2)	139
C13—H13B···N2iii	0.98	2.61	3.586 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3i	0.885 (17)	2.088 (17)	2.9581 (19)	167.4 (16)
C2—H2⋯O3	0.95	2.23	2.7981 (18)	117
C7—H7A⋯O1ii	0.99	2.55	3.364 (2)	139
C13—H13B⋯N2	0.98	2.61	3.586 (2)	172

Symmetry codes: (i) ; (ii) .