3-(2,6-Dioxopiperidin-3-yl)-3-aza-bicyclo-[3.2.0]heptane-2,4-dione.

The title mol-ecule, C(11)H(12)N(2)O(4), consists of a 3-aza-bicyclo-[3.2.0]heptane group containing a nearly planar cyclo-butane ring (r.m.s. deviation of fitted atoms is 0.0609 Å), fused to a pyrrolidine ring, bonded to a 2,6-dioxopiperidine ring at the 3-position. The angle between the mean planes of the cyclo-butane and fused pyrrolidine ring is 67.6 (6)°. The dihedral angles between the mean planes of the pyrrolidine and cyclo-butane rings and the dioxopiperidine ring are 73.9 (2) and 62.4 (4)°, respectively. The pyrrolidine and dioxopiperidine rings are twisted about the 3-yl group [torsion angles = -55.0 (1) and 115.0 (1)°] in a nearly perpendicular manner. Crystal packing is influenced by extensive inter-molecular C-H⋯O and N-H⋯O inter-actions between all four carbonyl O atoms and H atoms from the cyclo-butane and dioxopiperidine rings, as well as between the N atom and an H atom from the cyclo-butane ring. In addition, weak π-ring interactions also occur between H atoms from the cyclobutane ring and the five-membered pyrrolidine ring. As a result, mol-ecules are linked into infinite chains diagonally along the [101] plane of the unit cell in an alternate inverted pattern.

Related literature

For related structures, see: Muller & Man (2008 ▶); Yamamoto et al. (2008 ▶); Zeldis (2008 ▶). For related literature, see: Carson et al. (2004 ▶); Werbel et al. (1968 ▶); Cremer & Pople (1975 ▶); Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C11H12N2O4

M = 236.23

Monoclinic,

a = 10.7332 (7) Å

b = 9.9358 (5) Å

c = 11.0753 (7) Å

β = 116.201 (8)°

V = 1059.75 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 (2) K

0.57 × 0.34 × 0.19 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.866, T max = 0.975

10798 measured reflections

3496 independent reflections

2193 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 0.99

3496 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlis RED; 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 global, I. DOI: 10.1107/S1600536809002839/cs2103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002839/cs2103Isup2.hkl

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

C11H12N2O4	F(000) = 496
Mr = 236.23	Dx = 1.481 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 4629 reflections
a = 10.7332 (7) Å	θ = 4.9–32.6°
b = 9.9358 (5) Å	µ = 0.11 mm−1
c = 11.0753 (7) Å	T = 200 K
β = 116.201 (8)°	Prism, colorless
V = 1059.75 (13) Å3	0.57 × 0.34 × 0.19 mm
Z = 4

Oxford Diffraction Gemini diffractometer	3496 independent reflections
Radiation source: fine-focus sealed tube	2193 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.5081 pixels mm-1	θmax = 32.5°, θmin = 4.9°
φ and ω scans	h = −14→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −14→13
Tmin = 0.866, Tmax = 0.975	l = −15→15
10798 measured 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
3496 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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.

	x	y	z	Uiso*/Ueq
O1	0.32277 (8)	0.13630 (8)	0.42230 (7)	0.0271 (2)
O2	0.04309 (9)	0.50429 (9)	0.26752 (8)	0.0372 (2)
O3	0.02024 (7)	0.12103 (8)	0.39189 (7)	0.02458 (19)
O4	0.16813 (8)	0.16581 (9)	0.83857 (8)	0.0350 (2)
N1	0.18201 (8)	0.32243 (9)	0.37104 (8)	0.0196 (2)
N2	0.10433 (9)	0.14479 (9)	0.61681 (8)	0.0222 (2)
H2B	0.0683	0.0660	0.6195	0.027*
C1	0.25634 (10)	0.22276 (11)	0.34235 (10)	0.0211 (2)
C2	0.23146 (11)	0.24120 (12)	0.19918 (11)	0.0258 (3)
H2A	0.3154	0.2315	0.1827	0.031*
C3	0.09860 (12)	0.16602 (13)	0.09668 (11)	0.0340 (3)
H3A	0.1154	0.1076	0.0330	0.041*
H3B	0.0487	0.1164	0.1396	0.041*
C4	0.03228 (13)	0.30239 (14)	0.03642 (11)	0.0357 (3)
H4A	−0.0594	0.3172	0.0355	0.043*
H4B	0.0281	0.3205	−0.0532	0.043*
C5	0.15349 (12)	0.37539 (12)	0.15340 (11)	0.0278 (3)
H5A	0.2019	0.4464	0.1259	0.033*
C6	0.11702 (11)	0.41346 (11)	0.26561 (10)	0.0240 (2)
C7	0.15765 (10)	0.31947 (11)	0.49000 (10)	0.0190 (2)
H7A	0.0905	0.3931	0.4805	0.023*
C8	0.08854 (9)	0.18701 (11)	0.49330 (10)	0.0188 (2)
C9	0.17118 (10)	0.21274 (12)	0.73885 (10)	0.0234 (2)
C10	0.24295 (11)	0.34041 (11)	0.73556 (10)	0.0249 (2)
H10A	0.3260	0.3520	0.8228	0.030*
H10B	0.1799	0.4172	0.7239	0.030*
C11	0.28713 (10)	0.34228 (11)	0.62276 (10)	0.0220 (2)
H11A	0.3561	0.2704	0.6369	0.026*
H11B	0.3300	0.4300	0.6209	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0272 (4)	0.0236 (4)	0.0302 (4)	0.0056 (3)	0.0125 (3)	0.0028 (3)
O2	0.0488 (5)	0.0302 (5)	0.0331 (4)	0.0158 (4)	0.0185 (4)	0.0085 (4)
O3	0.0235 (4)	0.0233 (4)	0.0256 (4)	−0.0044 (3)	0.0096 (3)	−0.0028 (3)
O4	0.0448 (5)	0.0383 (5)	0.0276 (4)	−0.0018 (4)	0.0211 (4)	0.0041 (4)
N1	0.0226 (4)	0.0176 (5)	0.0209 (4)	0.0009 (3)	0.0117 (3)	0.0022 (4)
N2	0.0252 (4)	0.0186 (5)	0.0252 (4)	−0.0048 (3)	0.0134 (4)	0.0012 (4)
C1	0.0196 (5)	0.0198 (5)	0.0263 (5)	−0.0028 (4)	0.0124 (4)	−0.0009 (4)
C2	0.0295 (6)	0.0251 (6)	0.0279 (5)	−0.0016 (4)	0.0174 (5)	−0.0016 (5)
C3	0.0441 (7)	0.0330 (7)	0.0254 (6)	−0.0064 (5)	0.0158 (5)	−0.0041 (5)
C4	0.0385 (7)	0.0436 (8)	0.0218 (5)	0.0015 (6)	0.0103 (5)	0.0005 (5)
C5	0.0347 (6)	0.0256 (6)	0.0255 (5)	−0.0027 (5)	0.0155 (5)	0.0034 (5)
C6	0.0265 (5)	0.0203 (6)	0.0238 (5)	−0.0007 (4)	0.0098 (4)	0.0032 (4)
C7	0.0203 (5)	0.0170 (5)	0.0217 (5)	0.0004 (4)	0.0110 (4)	0.0008 (4)
C8	0.0156 (4)	0.0195 (5)	0.0224 (5)	0.0016 (4)	0.0093 (4)	0.0013 (4)
C9	0.0226 (5)	0.0247 (6)	0.0248 (5)	0.0025 (4)	0.0122 (4)	0.0012 (5)
C10	0.0294 (5)	0.0217 (6)	0.0225 (5)	−0.0019 (4)	0.0105 (4)	−0.0023 (4)
C11	0.0215 (5)	0.0193 (5)	0.0248 (5)	−0.0030 (4)	0.0099 (4)	−0.0014 (4)

O1—C1	1.2136 (13)	C3—H3B	0.9900
O2—C6	1.2080 (13)	C4—C5	1.5520 (16)
O3—C8	1.2253 (12)	C4—H4A	0.9900
O4—C9	1.2125 (13)	C4—H4B	0.9900
N1—C1	1.3936 (14)	C5—C6	1.5069 (16)
N1—C6	1.3959 (13)	C5—H5A	1.0000
N1—C7	1.4523 (13)	C7—C8	1.5191 (15)
N2—C8	1.3679 (13)	C7—C11	1.5298 (13)
N2—C9	1.3933 (13)	C7—H7A	1.0000
N2—H2B	0.8800	C9—C10	1.4929 (16)
C1—C2	1.4984 (15)	C10—C11	1.5195 (15)
C2—C5	1.5364 (17)	C10—H10A	0.9900
C2—C3	1.5654 (15)	C10—H10B	0.9900
C2—H2A	1.0000	C11—H11A	0.9900
C3—C4	1.5390 (18)	C11—H11B	0.9900
C3—H3A	0.9900
C1—N1—C6	113.25 (9)	C6—C5—H5A	115.6
C1—N1—C7	122.88 (8)	C2—C5—H5A	115.6
C6—N1—C7	123.25 (9)	C4—C5—H5A	115.6
C8—N2—C9	127.22 (9)	O2—C6—N1	123.98 (10)
C8—N2—H2B	116.4	O2—C6—C5	127.86 (10)
C9—N2—H2B	116.4	N1—C6—C5	108.14 (9)
O1—C1—N1	123.21 (9)	N1—C7—C8	108.95 (8)
O1—C1—C2	129.16 (10)	N1—C7—C11	114.71 (8)
N1—C1—C2	107.57 (9)	C8—C7—C11	110.57 (8)
C1—C2—C5	105.78 (9)	N1—C7—H7A	107.4
C1—C2—C3	112.87 (9)	C8—C7—H7A	107.4
C5—C2—C3	89.18 (8)	C11—C7—H7A	107.4
C1—C2—H2A	115.3	O3—C8—N2	120.82 (10)
C5—C2—H2A	115.3	O3—C8—C7	122.84 (9)
C3—C2—H2A	115.3	N2—C8—C7	116.33 (9)
C4—C3—C2	89.61 (9)	O4—C9—N2	119.20 (10)
C4—C3—H3A	113.7	O4—C9—C10	124.80 (10)
C2—C3—H3A	113.7	N2—C9—C10	116.00 (9)
C4—C3—H3B	113.7	C9—C10—C11	112.47 (9)
C2—C3—H3B	113.7	C9—C10—H10A	109.1
H3A—C3—H3B	111.0	C11—C10—H10A	109.1
C3—C4—C5	89.58 (8)	C9—C10—H10B	109.1
C3—C4—H4A	113.7	C11—C10—H10B	109.1
C5—C4—H4A	113.7	H10A—C10—H10B	107.8
C3—C4—H4B	113.7	C10—C11—C7	107.91 (9)
C5—C4—H4B	113.7	C10—C11—H11A	110.1
H4A—C4—H4B	111.0	C7—C11—H11A	110.1
C6—C5—C2	104.34 (9)	C10—C11—H11B	110.1
C6—C5—C4	112.24 (10)	C7—C11—H11B	110.1
C2—C5—C4	90.21 (9)	H11A—C11—H11B	108.4
C6—N1—C1—O1	178.13 (10)	C2—C5—C6—O2	−171.68 (11)
C7—N1—C1—O1	−10.65 (15)	C4—C5—C6—O2	−75.45 (15)
C6—N1—C1—C2	−4.49 (11)	C2—C5—C6—N1	7.10 (11)
C7—N1—C1—C2	166.72 (9)	C4—C5—C6—N1	103.32 (11)
O1—C1—C2—C5	−174.12 (11)	C1—N1—C7—C8	−55.34 (12)
N1—C1—C2—C5	8.72 (11)	C6—N1—C7—C8	115.01 (10)
O1—C1—C2—C3	89.96 (14)	C1—N1—C7—C11	69.19 (12)
N1—C1—C2—C3	−87.20 (11)	C6—N1—C7—C11	−120.47 (10)
C1—C2—C3—C4	115.83 (10)	C9—N2—C8—O3	−175.72 (9)
C5—C2—C3—C4	9.02 (9)	C9—N2—C8—C7	3.25 (15)
C2—C3—C4—C5	−8.93 (9)	N1—C7—C8—O3	−24.63 (13)
C1—C2—C5—C6	−9.47 (11)	C11—C7—C8—O3	−151.56 (9)
C3—C2—C5—C6	104.11 (9)	N1—C7—C8—N2	156.42 (9)
C1—C2—C5—C4	−122.52 (9)	C11—C7—C8—N2	29.49 (12)
C3—C2—C5—C4	−8.94 (9)	C8—N2—C9—O4	174.97 (10)
C3—C4—C5—C6	−96.51 (11)	C8—N2—C9—C10	−5.28 (15)
C3—C4—C5—C2	9.10 (9)	O4—C9—C10—C11	153.52 (11)
C1—N1—C6—O2	177.01 (10)	N2—C9—C10—C11	−26.21 (13)
C7—N1—C6—O2	5.83 (16)	C9—C10—C11—C7	56.95 (12)
C1—N1—C6—C5	−1.83 (11)	N1—C7—C11—C10	178.27 (9)
C7—N1—C6—C5	−173.01 (9)	C8—C7—C11—C10	−58.05 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3i	0.88	2.06	2.9426 (12)	175
C5—H5A···O4ii	1.00	2.52	3.4424 (15)	153
C10—H10B···O2iii	0.99	2.56	3.4228 (14)	146
C11—H11B···O3ii	0.99	2.53	3.5026 (13)	167
C11—H11B···O1ii	0.99	2.53	3.1072 (14)	117
C3—H3A···O4iv	0.99	2.52	3.2577 (15)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3i	0.88	2.06	2.9426 (12)	175
C5—H5A⋯O4ii	1.00	2.52	3.4424 (15)	153
C10—H10B⋯O2iii	0.99	2.56	3.4228 (14)	146
C11—H11B⋯O3ii	0.99	2.53	3.5026 (13)	167
C11—H11B⋯O1ii	0.99	2.53	3.1072 (14)	117
C3—H3A⋯O4iv	0.99	2.52	3.2577 (15)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .