Racemic methyl 3,10-dioxa-2-aza-tri-cyclo-[6.2.1.0]undecane-4-carboxyl-ate.

The structure of the racemic title compound, C(10)H(15)NO(4), consists of a tricyclic skeleton comprising a six-membered piperidine ring and five-membered isoxazolidine and tetra-hydro-furan rings. The piperidine ring adopts a distorted chair conformation, while the isoxazolidine and tetra-hydro-furan rings have envelope conformations.

Related literature

For related piperidine geometry, see: Parkin et al. (2004 ▶). For bicyclic polyhydro­isoxazolopyridines, see: Banerji et al. (2006 ▶); Carmona et al. (2009 ▶). For literature related to cyclo­addition reactions of cyclic nitro­nes, see: Ali & Wazeer (1988 ▶); Ali et al. (1988 ▶); Merino (2004 ▶); Chandrasekhar (2005 ▶); Moosa & Ali (2009 ▶, 2010 ▶). For the natural product SB-219383 and its inhibitory activity against tyrosyl tRNA sythetase, see: Houge-Frydrych et al. (2000 ▶); Stefanska et al. (2000 ▶).

Experimental

Crystal data

C10H15NO4

M = 213.23

Monoclinic,

a = 11.213 (3) Å

b = 7.1075 (18) Å

c = 12.910 (3) Å

β = 91.546 (5)°

V = 1028.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.20 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.995

13498 measured reflections

2563 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.155

S = 1.03

2563 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101484X/om2422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101484X/om2422Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101484X/om2422Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681101484X/om2422Isup4.cml

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

C10H15NO4	F(000) = 456
Mr = 213.23	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13498 reflections
a = 11.213 (3) Å	θ = 1.8–28.4°
b = 7.1075 (18) Å	µ = 0.11 mm−1
c = 12.910 (3) Å	T = 294 K
β = 91.546 (5)°	Block, colourless
V = 1028.4 (4) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	2563 independent reflections
Radiation source: normal-focus sealed tube	1567 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.979, Tmax = 0.995	k = −9→9
13498 measured reflections	l = −17→17

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0701P)2 + 0.2128P] where P = (Fo2 + 2Fc2)/3
2563 reflections	(Δ/σ)max = 0.002
185 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.14231 (14)	0.9997 (2)	0.39231 (12)	0.0433 (4)
O1	0.43183 (15)	0.7626 (3)	0.60910 (14)	0.0821 (6)
O2	0.24093 (17)	0.6880 (3)	0.59172 (15)	0.0838 (6)
O3	0.23751 (14)	0.86158 (19)	0.40074 (11)	0.0559 (4)
O4	0.26276 (13)	1.22561 (19)	0.29897 (11)	0.0516 (4)
C1	0.4428 (3)	0.6375 (5)	0.6972 (2)	0.0950 (11)
H1A	0.3834	0.6687	0.7465	0.142*
H1B	0.5207	0.6507	0.7290	0.142*
H1C	0.4316	0.5099	0.6745	0.142*
C2	0.3263 (2)	0.7726 (3)	0.56322 (17)	0.0514 (5)
C3	0.3243 (2)	0.9186 (3)	0.47749 (16)	0.0484 (5)
C4	0.2854 (2)	1.1087 (3)	0.51816 (18)	0.0508 (5)
C5	0.15285 (19)	1.1108 (3)	0.48841 (15)	0.0458 (5)
C6	0.0935 (2)	1.3043 (3)	0.47755 (17)	0.0515 (5)
C7	0.1024 (2)	1.3900 (3)	0.36965 (17)	0.0535 (6)
C8	0.0548 (2)	1.2468 (3)	0.29092 (19)	0.0542 (6)
C9	0.15798 (18)	1.1088 (3)	0.29848 (15)	0.0441 (5)
C10	0.2287 (2)	1.4113 (3)	0.3337 (2)	0.0565 (6)
H4	0.400 (2)	0.929 (3)	0.4479 (16)	0.056 (6)*
H5	0.3284 (19)	1.202 (3)	0.4850 (17)	0.050 (6)*
H6	0.301 (2)	1.116 (3)	0.590 (2)	0.069 (7)*
H7	0.1119 (18)	1.042 (3)	0.5399 (16)	0.049 (6)*
H8	0.011 (2)	1.290 (3)	0.4920 (18)	0.053 (6)*
H9	0.1310 (19)	1.383 (3)	0.5271 (17)	0.051 (6)*
H10	0.061 (2)	1.508 (4)	0.3653 (17)	0.061 (6)*
H11	−0.020 (2)	1.189 (3)	0.3108 (17)	0.060 (7)*
H12	0.050 (2)	1.304 (4)	0.220 (2)	0.073 (7)*
H13	0.1645 (16)	1.018 (3)	0.2423 (15)	0.041 (5)*
H14	0.235 (2)	1.501 (4)	0.2774 (19)	0.072 (7)*
H15	0.284 (2)	1.451 (3)	0.3903 (18)	0.056 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0489 (10)	0.0403 (9)	0.0410 (9)	−0.0017 (7)	0.0035 (7)	−0.0061 (7)
O1	0.0499 (10)	0.1099 (15)	0.0864 (13)	−0.0060 (9)	−0.0012 (9)	0.0487 (11)
O2	0.0686 (12)	0.0947 (14)	0.0873 (13)	−0.0279 (11)	−0.0100 (10)	0.0354 (11)
O3	0.0732 (11)	0.0427 (8)	0.0513 (9)	0.0081 (7)	−0.0086 (7)	−0.0092 (7)
O4	0.0545 (9)	0.0480 (8)	0.0532 (9)	−0.0020 (7)	0.0173 (7)	−0.0050 (7)
C1	0.0693 (18)	0.124 (3)	0.091 (2)	0.0066 (17)	−0.0051 (15)	0.058 (2)
C2	0.0501 (13)	0.0510 (12)	0.0534 (13)	−0.0031 (10)	0.0046 (10)	0.0037 (10)
C3	0.0473 (12)	0.0519 (12)	0.0462 (12)	−0.0021 (10)	0.0027 (9)	0.0016 (9)
C4	0.0619 (14)	0.0484 (12)	0.0420 (12)	−0.0078 (11)	−0.0028 (10)	−0.0022 (10)
C5	0.0555 (13)	0.0459 (11)	0.0363 (10)	−0.0072 (9)	0.0093 (9)	−0.0032 (9)
C6	0.0563 (14)	0.0519 (12)	0.0470 (12)	0.0013 (11)	0.0122 (10)	−0.0102 (10)
C7	0.0668 (15)	0.0436 (11)	0.0505 (12)	0.0114 (11)	0.0099 (10)	−0.0018 (10)
C8	0.0569 (14)	0.0598 (14)	0.0460 (13)	0.0079 (11)	0.0021 (11)	−0.0017 (10)
C9	0.0495 (12)	0.0448 (11)	0.0382 (11)	0.0015 (9)	0.0059 (9)	−0.0069 (9)
C10	0.0726 (16)	0.0437 (12)	0.0539 (14)	−0.0049 (11)	0.0158 (12)	0.0010 (10)

N1—O3	1.452 (2)	C4—H5	0.93 (2)
N1—C9	1.453 (2)	C4—H6	0.94 (3)
N1—C5	1.473 (2)	C5—C6	1.532 (3)
O1—C2	1.311 (3)	C5—H7	0.95 (2)
O1—C1	1.446 (3)	C6—C7	1.526 (3)
O2—C2	1.197 (3)	C6—H8	0.95 (2)
O3—C3	1.429 (3)	C6—H9	0.94 (2)
O4—C9	1.439 (2)	C7—C10	1.509 (3)
O4—C10	1.449 (3)	C7—C8	1.525 (3)
C1—H1A	0.9600	C7—H10	0.96 (2)
C1—H1B	0.9600	C8—C9	1.518 (3)
C1—H1C	0.9600	C8—H11	0.98 (2)
C2—C3	1.517 (3)	C8—H12	1.01 (3)
C3—C4	1.518 (3)	C9—H13	0.976 (19)
C3—H4	0.95 (2)	C10—H14	0.97 (3)
C4—C5	1.525 (3)	C10—H15	0.99 (2)
O3—N1—C9	108.55 (14)	C6—C5—H7	107.9 (12)
O3—N1—C5	104.91 (14)	C7—C6—C5	113.74 (17)
C9—N1—C5	114.04 (16)	C7—C6—H8	107.9 (14)
C2—O1—C1	116.43 (19)	C5—C6—H8	108.0 (13)
C3—O3—N1	110.24 (14)	C7—C6—H9	110.1 (13)
C9—O4—C10	107.76 (15)	C5—C6—H9	106.8 (13)
O1—C1—H1A	109.5	H8—C6—H9	110.3 (19)
O1—C1—H1B	109.5	C10—C7—C8	100.20 (18)
H1A—C1—H1B	109.5	C10—C7—C6	113.9 (2)
O1—C1—H1C	109.5	C8—C7—C6	108.17 (19)
H1A—C1—H1C	109.5	C10—C7—H10	110.8 (13)
H1B—C1—H1C	109.5	C8—C7—H10	112.4 (14)
O2—C2—O1	123.6 (2)	C6—C7—H10	110.9 (13)
O2—C2—C3	124.9 (2)	C9—C8—C7	97.78 (18)
O1—C2—C3	111.22 (19)	C9—C8—H11	111.8 (14)
O3—C3—C2	107.94 (18)	C7—C8—H11	113.3 (13)
O3—C3—C4	107.17 (17)	C9—C8—H12	110.2 (14)
C2—C3—C4	110.81 (18)	C7—C8—H12	110.5 (15)
O3—C3—H4	110.3 (13)	H11—C8—H12	112 (2)
C2—C3—H4	110.7 (13)	O4—C9—N1	114.92 (16)
C4—C3—H4	109.9 (13)	O4—C9—C8	104.39 (17)
C3—C4—C5	102.07 (17)	N1—C9—C8	106.81 (17)
C3—C4—H5	108.5 (13)	O4—C9—H13	108.0 (11)
C5—C4—H5	113.0 (13)	N1—C9—H13	106.1 (11)
C3—C4—H6	110.0 (15)	C8—C9—H13	117.0 (11)
C5—C4—H6	113.8 (15)	O4—C10—C7	105.13 (18)
H5—C4—H6	109 (2)	O4—C10—H14	110.0 (15)
N1—C5—C4	105.22 (16)	C7—C10—H14	112.6 (15)
N1—C5—C6	112.30 (17)	O4—C10—H15	108.9 (13)
C4—C5—C6	116.70 (19)	C7—C10—H15	112.1 (13)
N1—C5—H7	106.4 (12)	H14—C10—H15	108 (2)
C4—C5—H7	107.7 (13)