tert-Butyl 3-oxo-2-oxa-5-aza-bicyclo-[2.2.1]heptane-5-carboxyl-ate.

The title compound, C(10)H(15)NO(4), also known as N-tert-butyl-oxycarbonyl-allohydr-oxy-l-proline lactone, is quite similar to N-acetyl-allohydr-oxy-l-proline lactone [Lenstra, Petit & Geise (1979 ▶). Cryst. Struct. Commun. 8, 1023-1029], whereby both carbonyl groups point roughly in the same direction because of the trans conformation of the peptide bond.

Related literature

For general background, see: Allen (2002 ▶). For related structures, see: Didier et al. (2004 ▶); Lenstra et al. (1979 ▶); Papaioannou et al. (1989 ▶). For related synthesis, see: Gómez-Vidal & Silverman (2001 ▶). For related literature, see: Flack & Schwarzenbach (1988 ▶).

Experimental

Crystal data

C10H15NO4

M = 213.23

Monoclinic,

a = 6.0710 (7) Å

b = 9.3703 (11) Å

c = 9.3002 (10) Å

β = 100.013 (5)°

V = 521.00 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 (2) K

0.3 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

5951 measured reflections

1143 independent reflections

1054 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.102

S = 1.20

1143 reflections

139 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030651/ww2125sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030651/ww2125Isup2.hkl

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

C10H15NO4	F(000) = 228
Mr = 213.23	Dx = 1.359 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 11845 reflections
a = 6.0710 (7) Å	θ = 0.4–26.4°
b = 9.3703 (11) Å	µ = 0.11 mm−1
c = 9.3002 (10) Å	T = 100 K
β = 100.013 (5)°	Prism, colourless
V = 521.00 (10) Å3	0.3 × 0.2 × 0.2 mm
Z = 2

Nonius KappaCCD area-detector diffractometer	1054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
graphite	θmax = 26.6°, θmin = 3.1°
ω and φ scans	h = −7→7
5951 measured reflections	k = −11→11
1143 independent reflections	l = −11→11

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052	w = 1/[σ2(Fo2) + (0.0035P)2 + 0.6362P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 1.20	Δρmax = 0.23 e Å−3
1143 reflections	Δρmin = −0.22 e Å−3
139 parameters

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.

	x	y	z	Uiso*/Ueq
O1	0.3991 (4)	0.3322 (3)	0.3133 (3)	0.0243 (6)
O2	0.0303 (4)	0.2997 (3)	0.2103 (3)	0.0280 (7)
O3	0.3864 (4)	−0.0967 (3)	0.1079 (3)	0.0262 (7)
O4	0.0299 (5)	−0.1077 (3)	0.1467 (3)	0.0319 (7)
N1	0.3137 (5)	0.1896 (4)	0.1226 (4)	0.0230 (7)
C1	0.3539 (7)	0.4316 (4)	0.4288 (4)	0.0249 (9)
C2	0.2354 (7)	0.5650 (4)	0.3607 (5)	0.0306 (10)
H2A	0.3194	0.6052	0.2893	0.046*
H2B	0.2265	0.6356	0.4372	0.046*
H2C	0.0842	0.54	0.3117	0.046*
C3	0.2204 (8)	0.3563 (5)	0.5297 (5)	0.0315 (10)
H3A	0.075	0.3274	0.4744	0.047*
H3B	0.1977	0.4212	0.6085	0.047*
H3C	0.3024	0.2717	0.5715	0.047*
C4	0.5884 (6)	0.4670 (4)	0.5062 (5)	0.0266 (9)
H4A	0.6574	0.3816	0.5556	0.04*
H4B	0.5813	0.5423	0.5784	0.04*
H4C	0.678	0.5001	0.4347	0.04*
C5	0.2283 (6)	0.2759 (4)	0.2159 (4)	0.0227 (8)
C6	0.5472 (7)	0.1381 (4)	0.1373 (5)	0.0250 (9)
H6A	0.6091	0.1101	0.239	0.03*
H6B	0.646	0.21	0.1032	0.03*
C7	0.5098 (7)	0.0093 (4)	0.0356 (4)	0.0265 (9)
H7	0.648	−0.0281	0.004	0.032*
C8	0.3299 (7)	0.0625 (5)	−0.0887 (4)	0.0259 (9)
H8A	0.3762	0.1478	−0.1388	0.031*
H8B	0.273	−0.0127	−0.1603	0.031*
C9	0.1701 (6)	0.0969 (4)	0.0167 (4)	0.0233 (9)
H9	0.0204	0.1361	−0.0275	0.028*
C10	0.1710 (7)	−0.0459 (4)	0.0960 (4)	0.0256 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0249 (14)	0.0180 (14)	0.0299 (14)	−0.0012 (12)	0.0044 (12)	−0.0053 (12)
O2	0.0234 (14)	0.0253 (16)	0.0352 (16)	0.0018 (13)	0.0050 (12)	−0.0054 (13)
O3	0.0253 (15)	0.0189 (14)	0.0349 (16)	−0.0018 (13)	0.0067 (12)	0.0007 (13)
O4	0.0344 (17)	0.0263 (16)	0.0359 (16)	−0.0089 (14)	0.0091 (13)	0.0022 (14)
N1	0.0215 (17)	0.0192 (17)	0.0275 (18)	0.0024 (14)	0.0017 (14)	−0.0023 (15)
C1	0.027 (2)	0.018 (2)	0.031 (2)	0.0018 (17)	0.0092 (17)	−0.0050 (17)
C2	0.034 (2)	0.018 (2)	0.039 (2)	0.0029 (18)	0.0049 (19)	−0.0017 (19)
C3	0.037 (2)	0.023 (2)	0.035 (2)	−0.0045 (18)	0.0101 (19)	−0.0047 (19)
C4	0.026 (2)	0.020 (2)	0.034 (2)	−0.0009 (17)	0.0064 (17)	−0.0039 (18)
C5	0.023 (2)	0.0157 (19)	0.029 (2)	−0.0012 (16)	0.0028 (16)	0.0015 (16)
C6	0.024 (2)	0.021 (2)	0.030 (2)	−0.0009 (17)	0.0057 (16)	−0.0024 (17)
C7	0.028 (2)	0.022 (2)	0.030 (2)	−0.0006 (18)	0.0099 (19)	−0.0045 (18)
C8	0.031 (2)	0.019 (2)	0.028 (2)	−0.0005 (17)	0.0056 (17)	−0.0007 (18)
C9	0.0238 (19)	0.0187 (19)	0.027 (2)	−0.0022 (17)	0.0049 (17)	−0.0039 (16)
C10	0.031 (2)	0.020 (2)	0.025 (2)	−0.0038 (18)	0.0024 (17)	−0.0047 (17)

O1—C5	1.359 (5)	C3—H3B	0.98
O1—C1	1.484 (5)	C3—H3C	0.98
O2—C5	1.215 (5)	C4—H4A	0.98
O3—C10	1.377 (5)	C4—H4B	0.98
O3—C7	1.475 (5)	C4—H4C	0.98
O4—C10	1.196 (5)	C6—C7	1.526 (6)
N1—C5	1.353 (5)	C6—H6A	0.99
N1—C9	1.478 (5)	C6—H6B	0.99
N1—C6	1.481 (5)	C7—C8	1.529 (6)
C1—C4	1.516 (5)	C7—H7	1
C1—C3	1.516 (6)	C8—C9	1.528 (6)
C1—C2	1.524 (6)	C8—H8A	0.99
C2—H2A	0.98	C8—H8B	0.99
C2—H2B	0.98	C9—C10	1.528 (6)
C2—H2C	0.98	C9—H9	1
C3—H3A	0.98
C5—O1—C1	120.7 (3)	O2—C5—O1	126.3 (4)
C10—O3—C7	106.3 (3)	N1—C5—O1	109.0 (3)
C5—N1—C9	122.1 (3)	N1—C6—C7	99.4 (3)
C5—N1—C6	127.1 (3)	N1—C6—H6A	111.9
C9—N1—C6	108.3 (3)	C7—C6—H6A	111.9
O1—C1—C4	101.8 (3)	N1—C6—H6B	111.9
O1—C1—C3	110.0 (3)	C7—C6—H6B	111.9
C4—C1—C3	111.5 (4)	H6A—C6—H6B	109.6
O1—C1—C2	110.3 (3)	O3—C7—C6	106.4 (3)
C4—C1—C2	110.7 (3)	O3—C7—C8	102.2 (3)
C3—C1—C2	112.0 (3)	C6—C7—C8	102.7 (3)
C1—C2—H2A	109.5	O3—C7—H7	114.7
C1—C2—H2B	109.5	C6—C7—H7	114.7
H2A—C2—H2B	109.5	C8—C7—H7	114.7
C1—C2—H2C	109.5	C9—C8—C7	91.9 (3)
H2A—C2—H2C	109.5	C9—C8—H8A	113.3
H2B—C2—H2C	109.5	C7—C8—H8A	113.3
C1—C3—H3A	109.5	C9—C8—H8B	113.3
C1—C3—H3B	109.5	C7—C8—H8B	113.3
H3A—C3—H3B	109.5	H8A—C8—H8B	110.6
C1—C3—H3C	109.5	N1—C9—C10	103.9 (3)
H3A—C3—H3C	109.5	N1—C9—C8	100.6 (3)
H3B—C3—H3C	109.5	C10—C9—C8	100.1 (3)
C1—C4—H4A	109.5	N1—C9—H9	116.5
C1—C4—H4B	109.5	C10—C9—H9	116.5
H4A—C4—H4B	109.5	C8—C9—H9	116.5
C1—C4—H4C	109.5	O4—C10—O3	122.4 (4)
H4A—C4—H4C	109.5	O4—C10—C9	132.2 (4)
H4B—C4—H4C	109.5	O3—C10—C9	105.4 (3)
O2—C5—N1	124.7 (4)
C5—O1—C1—C4	−178.9 (3)	O3—C7—C8—C9	53.1 (3)
C5—O1—C1—C3	62.7 (5)	C6—C7—C8—C9	−57.1 (3)
C5—O1—C1—C2	−61.3 (4)	C5—N1—C9—C10	−93.9 (4)
C9—N1—C5—O2	−9.6 (6)	C6—N1—C9—C10	69.1 (4)
C6—N1—C5—O2	−169.3 (4)	C5—N1—C9—C8	162.7 (3)
C9—N1—C5—O1	171.3 (3)	C6—N1—C9—C8	−34.2 (4)
C6—N1—C5—O1	11.6 (5)	C7—C8—C9—N1	53.9 (3)
C1—O1—C5—O2	0.9 (6)	C7—C8—C9—C10	−52.5 (3)
C1—O1—C5—N1	179.9 (3)	C7—O3—C10—O4	−178.8 (4)
C5—N1—C6—C7	159.9 (4)	C7—O3—C10—C9	−1.3 (4)
C9—N1—C6—C7	−2.1 (4)	N1—C9—C10—O4	109.5 (5)
C10—O3—C7—C6	73.2 (4)	C8—C9—C10—O4	−146.8 (4)
C10—O3—C7—C8	−34.2 (4)	N1—C9—C10—O3	−67.7 (3)
N1—C6—C7—O3	−69.0 (4)	C8—C9—C10—O3	36.1 (4)
N1—C6—C7—C8	38.0 (4)