tert-Butyl 6-oxo-2,7-diaza-spiro[4.4]nonane-2-carboxyl-ate.

In the title mol-ecule, C(12)H(20)N(2)O(3), both five-membered rings are in envelope conformations. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

Related literature

For applications of substituted pyrrolidines, see: Domagala et al. (1993 ▶); Pedder et al. (1976 ▶); Blanco & Sardina (1994 ▶); Husinec & Savic (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H20N2O3

M = 240.30

Monoclinic,

a = 10.495 (5) Å

b = 6.283 (3) Å

c = 19.247 (10) Å

β = 97.029 (8)°

V = 1259.7 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.21 × 0.15 × 0.06 mm

Data collection

Rigaku Saturn 724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.981, T max = 0.995

3265 measured reflections

1557 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.105

S = 1.09

1557 reflections

157 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681105046X/lh5363sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105046X/lh5363Isup2.hkl

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

C12H20N2O3	F(000) = 520
Mr = 240.30	Dx = 1.267 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2422 reflections
a = 10.495 (5) Å	θ = 1.1–27.5°
b = 6.283 (3) Å	µ = 0.09 mm−1
c = 19.247 (10) Å	T = 173 K
β = 97.029 (8)°	Platelet, colorless
V = 1259.7 (11) Å3	0.21 × 0.15 × 0.06 mm
Z = 4

Rigaku Saturn 724+ diffractometer	1557 independent reflections
Radiation source: rotating anode	1452 reflections with I > 2σ(I)
Confocal	Rint = 0.039
ω scans at fixed χ = 45°	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −13→7
Tmin = 0.981, Tmax = 0.995	k = −8→8
3265 measured reflections	l = −23→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.032P)2 + 0.9713P] where P = (Fo2 + 2Fc2)/3
1557 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.18 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.Absolute configuration is unknown, there being no firm chemical evidence for its assignment to hand and it having not been established by anomalous dispersion effects in diffraction measurements on the crystal. An arbitrary choice of enantiomer has been made.

	x	y	z	Uiso*/Ueq
O1	0.2715 (2)	0.4600 (3)	0.43850 (10)	0.0313 (5)
O2	0.33362 (17)	0.2042 (3)	0.18571 (9)	0.0289 (5)
O3	0.55006 (19)	0.1382 (4)	0.19625 (10)	0.0332 (5)
N1	0.3406 (2)	0.8081 (4)	0.44345 (11)	0.0255 (5)
H1	0.3028	0.8474	0.4798	0.031*
N2	0.4618 (2)	0.3546 (4)	0.27139 (12)	0.0275 (5)
C1	0.3315 (3)	0.6117 (5)	0.41741 (13)	0.0219 (6)
C2	0.4181 (3)	0.9527 (5)	0.40704 (14)	0.0279 (6)
H2B	0.5037	0.9751	0.4339	0.033*
H2A	0.3750	1.0920	0.3984	0.033*
C3	0.4286 (3)	0.8347 (5)	0.33812 (13)	0.0234 (6)
H3B	0.5134	0.8596	0.3220	0.028*
H3A	0.3605	0.8813	0.3011	0.028*
C4	0.4118 (3)	0.5993 (5)	0.35651 (13)	0.0209 (5)
C5	0.5419 (3)	0.4915 (5)	0.38093 (13)	0.0241 (6)
H5B	0.6051	0.5963	0.4027	0.029*
H5A	0.5317	0.3766	0.4150	0.029*
C6	0.5835 (3)	0.4018 (5)	0.31360 (15)	0.0303 (7)
H6B	0.6336	0.5078	0.2902	0.036*
H6A	0.6357	0.2714	0.3230	0.036*
C7	0.3515 (2)	0.4573 (5)	0.29695 (13)	0.0233 (6)
H7B	0.2936	0.3505	0.3143	0.028*
H7A	0.3024	0.5428	0.2596	0.028*
C8	0.4568 (2)	0.2247 (5)	0.21527 (13)	0.0244 (6)
C9	0.3028 (3)	0.0912 (5)	0.11865 (14)	0.0290 (7)
C10	0.3776 (3)	0.1875 (7)	0.06389 (15)	0.0461 (9)
H10A	0.3444	0.1321	0.0176	0.069*
H10C	0.4686	0.1501	0.0745	0.069*
H10B	0.3683	0.3427	0.0641	0.069*
C11	0.3283 (3)	−0.1464 (6)	0.12960 (17)	0.0381 (8)
H11B	0.2717	−0.2031	0.1620	0.057*
H11C	0.4180	−0.1680	0.1492	0.057*
H11A	0.3117	−0.2205	0.0846	0.057*
C12	0.1607 (3)	0.1350 (7)	0.10196 (17)	0.0419 (8)
H12A	0.1281	0.0648	0.0579	0.063*
H12C	0.1466	0.2888	0.0974	0.063*
H12B	0.1154	0.0799	0.1398	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0348 (12)	0.0317 (11)	0.0293 (10)	−0.0073 (10)	0.0115 (8)	0.0027 (10)
O2	0.0228 (10)	0.0378 (11)	0.0253 (9)	0.0021 (10)	0.0002 (7)	−0.0106 (10)
O3	0.0261 (11)	0.0410 (13)	0.0335 (10)	0.0050 (10)	0.0074 (8)	−0.0098 (10)
N1	0.0263 (12)	0.0276 (13)	0.0234 (11)	0.0030 (11)	0.0066 (9)	−0.0023 (11)
N2	0.0190 (11)	0.0345 (13)	0.0284 (11)	0.0033 (11)	0.0004 (9)	−0.0091 (11)
C1	0.0200 (13)	0.0256 (13)	0.0200 (11)	−0.0001 (12)	0.0015 (10)	0.0016 (11)
C2	0.0280 (15)	0.0235 (13)	0.0322 (14)	0.0000 (13)	0.0033 (11)	0.0014 (13)
C3	0.0197 (13)	0.0265 (14)	0.0247 (12)	0.0022 (12)	0.0059 (10)	0.0037 (12)
C4	0.0193 (12)	0.0224 (13)	0.0211 (11)	0.0013 (12)	0.0025 (10)	0.0009 (11)
C5	0.0206 (13)	0.0249 (14)	0.0262 (13)	−0.0010 (12)	0.0001 (10)	−0.0014 (12)
C6	0.0183 (13)	0.0383 (18)	0.0336 (14)	0.0040 (13)	0.0001 (11)	−0.0076 (13)
C7	0.0181 (13)	0.0271 (13)	0.0252 (12)	0.0021 (12)	0.0053 (10)	−0.0021 (12)
C8	0.0219 (13)	0.0270 (14)	0.0248 (13)	0.0016 (12)	0.0048 (10)	−0.0003 (12)
C9	0.0309 (15)	0.0351 (16)	0.0212 (13)	−0.0022 (14)	0.0033 (11)	−0.0045 (13)
C10	0.048 (2)	0.062 (3)	0.0283 (15)	−0.009 (2)	0.0058 (14)	0.0031 (17)
C11	0.0388 (18)	0.0359 (17)	0.0394 (17)	−0.0022 (16)	0.0030 (14)	−0.0081 (15)
C12	0.0337 (18)	0.050 (2)	0.0395 (17)	0.0044 (17)	−0.0073 (14)	−0.0070 (17)

O1—C1	1.238 (3)	C5—C6	1.525 (4)
O2—C8	1.353 (3)	C5—H5B	0.9900
O2—C9	1.474 (3)	C5—H5A	0.9900
O3—C8	1.214 (3)	C6—H6B	0.9900
N1—C1	1.331 (4)	C6—H6A	0.9900
N1—C2	1.454 (4)	C7—H7B	0.9900
N1—H1	0.8800	C7—H7A	0.9900
N2—C8	1.350 (3)	C9—C12	1.511 (4)
N2—C6	1.458 (4)	C9—C10	1.516 (4)
N2—C7	1.462 (3)	C9—C11	1.526 (5)
C1—C4	1.527 (4)	C10—H10A	0.9800
C2—C3	1.535 (4)	C10—H10C	0.9800
C2—H2B	0.9900	C10—H10B	0.9800
C2—H2A	0.9900	C11—H11B	0.9800
C3—C4	1.536 (4)	C11—H11C	0.9800
C3—H3B	0.9900	C11—H11A	0.9800
C3—H3A	0.9900	C12—H12A	0.9800
C4—C7	1.527 (4)	C12—H12C	0.9800
C4—C5	1.545 (4)	C12—H12B	0.9800
C8—O2—C9	120.7 (2)	N2—C6—H6A	111.1
C1—N1—C2	114.6 (2)	C5—C6—H6A	111.1
C1—N1—H1	122.7	H6B—C6—H6A	109.1
C2—N1—H1	122.7	N2—C7—C4	103.8 (2)
C8—N2—C6	121.0 (2)	N2—C7—H7B	111.0
C8—N2—C7	125.5 (2)	C4—C7—H7B	111.0
C6—N2—C7	113.5 (2)	N2—C7—H7A	111.0
O1—C1—N1	127.3 (3)	C4—C7—H7A	111.0
O1—C1—C4	124.3 (3)	H7B—C7—H7A	109.0
N1—C1—C4	108.4 (2)	O3—C8—N2	123.9 (3)
N1—C2—C3	102.6 (2)	O3—C8—O2	126.5 (3)
N1—C2—H2B	111.2	N2—C8—O2	109.6 (2)
C3—C2—H2B	111.2	O2—C9—C12	101.8 (2)
N1—C2—H2A	111.2	O2—C9—C10	109.8 (3)
C3—C2—H2A	111.2	C12—C9—C10	111.2 (3)
H2B—C2—H2A	109.2	O2—C9—C11	109.5 (2)
C2—C3—C4	104.1 (2)	C12—C9—C11	111.1 (3)
C2—C3—H3B	110.9	C10—C9—C11	112.9 (3)
C4—C3—H3B	110.9	C9—C10—H10A	109.5
C2—C3—H3A	110.9	C9—C10—H10C	109.5
C4—C3—H3A	110.9	H10A—C10—H10C	109.5
H3B—C3—H3A	109.0	C9—C10—H10B	109.5
C1—C4—C7	112.9 (2)	H10A—C10—H10B	109.5
C1—C4—C3	102.6 (2)	H10C—C10—H10B	109.5
C7—C4—C3	116.0 (2)	C9—C11—H11B	109.5
C1—C4—C5	109.8 (2)	C9—C11—H11C	109.5
C7—C4—C5	104.0 (2)	H11B—C11—H11C	109.5
C3—C4—C5	111.7 (2)	C9—C11—H11A	109.5
C6—C5—C4	103.8 (2)	H11B—C11—H11A	109.5
C6—C5—H5B	111.0	H11C—C11—H11A	109.5
C4—C5—H5B	111.0	C9—C12—H12A	109.5
C6—C5—H5A	111.0	C9—C12—H12C	109.5
C4—C5—H5A	111.0	H12A—C12—H12C	109.5
H5B—C5—H5A	109.0	C9—C12—H12B	109.5
N2—C6—C5	103.1 (2)	H12A—C12—H12B	109.5
N2—C6—H6B	111.1	H12C—C12—H12B	109.5
C5—C6—H6B	111.1
C2—N1—C1—O1	−179.7 (3)	C7—N2—C6—C5	15.7 (3)
C2—N1—C1—C4	1.7 (3)	C4—C5—C6—N2	−30.5 (3)
C1—N1—C2—C3	15.7 (3)	C8—N2—C7—C4	−175.1 (3)
N1—C2—C3—C4	−25.8 (3)	C6—N2—C7—C4	5.9 (3)
O1—C1—C4—C7	37.5 (4)	C1—C4—C7—N2	−143.8 (2)
N1—C1—C4—C7	−143.8 (2)	C3—C4—C7—N2	98.2 (3)
O1—C1—C4—C3	163.1 (3)	C5—C4—C7—N2	−24.9 (3)
N1—C1—C4—C3	−18.2 (3)	C6—N2—C8—O3	0.5 (4)
O1—C1—C4—C5	−78.0 (3)	C7—N2—C8—O3	−178.4 (3)
N1—C1—C4—C5	100.7 (3)	C6—N2—C8—O2	179.2 (3)
C2—C3—C4—C1	26.7 (3)	C7—N2—C8—O2	0.3 (4)
C2—C3—C4—C7	150.2 (2)	C9—O2—C8—O3	−8.6 (4)
C2—C3—C4—C5	−90.8 (2)	C9—O2—C8—N2	172.7 (2)
C1—C4—C5—C6	155.7 (2)	C8—O2—C9—C12	−172.4 (3)
C7—C4—C5—C6	34.6 (3)	C8—O2—C9—C10	−54.6 (4)
C3—C4—C5—C6	−91.2 (3)	C8—O2—C9—C11	69.9 (3)
C8—N2—C6—C5	−163.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.97	2.848 (3)	175.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.97	2.848 (3)	175

Symmetry code: (i) .