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The title compound, C8H12N2O4, was prepared from 2-(4-hydr­oxy-2-oxopyrrolidin-1-yl)acetamide and acetic anhydride. In the crystal structure, molecules are linked through N—H...O hydrogen bonds to form an extended network, which contributes to the stability of the structure in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000122/gh6031sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000122/gh6031Isup2.hkl
Contains datablock I

CCDC reference: 298449

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.082
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.71 From the CIF: _reflns_number_total 1157 Count of symmetry unique reflns 1162 Completeness (_total/calc) 99.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-(Carbamoylmethyl)-5-oxopyrrolidin-3-yl acetate top
Crystal data top
C8H12N2O4F(000) = 1696
Mr = 200.20Dx = 1.433 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 1534 reflections
a = 16.838 (9) Åθ = 2.8–21.8°
b = 26.184 (14) ŵ = 0.12 mm1
c = 8.419 (5) ÅT = 294 K
V = 3712 (3) Å3Block, white
Z = 160.56 × 0.34 × 0.22 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1157 independent reflections
Radiation source: fine-focus sealed tube929 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.7°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 2121
Tmin = 0.924, Tmax = 0.975k = 1934
5984 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0537P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
1157 reflectionsΔρmax = 0.12 e Å3
136 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: Friedel Pairs merged
Primary atom site location: structure-invariant direct methods
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.08196 (8)0.39630 (6)0.1799 (2)0.0548 (4)
O20.05504 (10)0.28254 (6)0.4490 (2)0.0521 (4)
O30.05305 (8)0.40066 (6)0.60059 (19)0.0453 (4)
O40.09383 (10)0.47893 (7)0.6730 (3)0.0682 (5)
N10.02518 (9)0.35143 (6)0.2690 (2)0.0352 (4)
N20.05271 (13)0.22155 (8)0.2603 (3)0.0541 (5)
H2C0.0374 (17)0.2130 (11)0.167 (5)0.067 (9)*
H2D0.0880 (19)0.2029 (14)0.321 (6)0.095 (11)*
C10.01983 (11)0.39341 (7)0.2541 (3)0.0377 (4)
C20.02165 (13)0.43620 (8)0.3411 (3)0.0430 (5)
H2A0.01550.45490.40710.052*
H2B0.04610.45970.26680.052*
C30.08403 (12)0.41003 (8)0.4419 (3)0.0420 (5)
H30.13340.42980.44540.050*
C40.09620 (11)0.35903 (8)0.3635 (3)0.0421 (5)
H4A0.14310.35940.29670.051*
H4B0.10180.33220.44210.051*
C50.00571 (12)0.30290 (7)0.1991 (3)0.0408 (5)
H5A0.05410.28630.16360.049*
H5B0.02770.30840.10680.049*
C60.03703 (11)0.26827 (7)0.3154 (2)0.0361 (4)
C70.06030 (12)0.43965 (10)0.7043 (3)0.0466 (5)
C80.02190 (15)0.42761 (11)0.8599 (3)0.0584 (6)
H8A0.05960.43240.94410.088*
H8B0.00400.39280.85950.088*
H8C0.02260.44990.87600.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0506 (9)0.0535 (9)0.0602 (10)0.0079 (7)0.0110 (9)0.0081 (9)
O20.0710 (10)0.0450 (9)0.0402 (9)0.0044 (7)0.0167 (8)0.0004 (7)
O30.0486 (8)0.0515 (9)0.0359 (8)0.0102 (6)0.0049 (7)0.0033 (7)
O40.0751 (11)0.0626 (11)0.0668 (12)0.0191 (9)0.0109 (10)0.0217 (10)
N10.0364 (8)0.0312 (8)0.0380 (9)0.0018 (6)0.0007 (7)0.0013 (7)
N20.0743 (13)0.0445 (10)0.0436 (12)0.0142 (9)0.0019 (11)0.0024 (10)
C10.0411 (10)0.0358 (10)0.0362 (10)0.0019 (8)0.0066 (8)0.0069 (9)
C20.0511 (11)0.0309 (10)0.0469 (12)0.0028 (8)0.0131 (9)0.0022 (9)
C30.0410 (9)0.0446 (10)0.0405 (11)0.0106 (9)0.0091 (9)0.0025 (10)
C40.0349 (9)0.0467 (11)0.0447 (12)0.0045 (8)0.0003 (8)0.0010 (10)
C50.0508 (11)0.0368 (10)0.0348 (10)0.0015 (8)0.0045 (9)0.0035 (9)
C60.0389 (9)0.0338 (9)0.0357 (11)0.0053 (8)0.0029 (8)0.0013 (8)
C70.0408 (10)0.0599 (14)0.0390 (12)0.0056 (10)0.0037 (9)0.0091 (11)
C80.0567 (13)0.0784 (17)0.0401 (12)0.0113 (11)0.0006 (11)0.0057 (13)
Geometric parameters (Å, º) top
O1—C11.221 (3)C2—H2A0.9700
O2—C61.224 (3)C2—H2B0.9700
O3—C71.349 (3)C3—C41.504 (3)
O3—C31.455 (3)C3—H30.9800
O4—C71.203 (3)C4—H4A0.9700
N1—C11.341 (2)C4—H4B0.9700
N1—C51.438 (2)C5—C61.516 (3)
N1—C41.450 (3)C5—H5A0.9700
N2—C61.335 (3)C5—H5B0.9700
N2—H2C0.86 (4)C7—C81.494 (4)
N2—H2D0.92 (4)C8—H8A0.9600
C1—C21.510 (3)C8—H8B0.9600
C2—C31.514 (3)C8—H8C0.9600
C7—O3—C3115.75 (17)N1—C4—H4A110.9
C1—N1—C5123.84 (17)C3—C4—H4A110.9
C1—N1—C4113.91 (16)N1—C4—H4B110.9
C5—N1—C4122.25 (15)C3—C4—H4B110.9
C6—N2—H2C119.9 (19)H4A—C4—H4B108.9
C6—N2—H2D115 (2)N1—C5—C6111.84 (17)
H2C—N2—H2D124 (3)N1—C5—H5A109.2
O1—C1—N1125.69 (19)C6—C5—H5A109.2
O1—C1—C2126.76 (18)N1—C5—H5B109.2
N1—C1—C2107.52 (17)C6—C5—H5B109.2
C1—C2—C3104.90 (17)H5A—C5—H5B107.9
C1—C2—H2A110.8O2—C6—N2123.4 (2)
C3—C2—H2A110.8O2—C6—C5121.92 (19)
C1—C2—H2B110.8N2—C6—C5114.7 (2)
C3—C2—H2B110.8O4—C7—O3123.2 (2)
H2A—C2—H2B108.8O4—C7—C8125.2 (2)
O3—C3—C4107.61 (18)O3—C7—C8111.6 (2)
O3—C3—C2110.02 (17)C7—C8—H8A109.5
C4—C3—C2104.47 (19)C7—C8—H8B109.5
O3—C3—H3111.5H8A—C8—H8B109.5
C4—C3—H3111.5C7—C8—H8C109.5
C2—C3—H3111.5H8A—C8—H8C109.5
N1—C4—C3104.50 (16)H8B—C8—H8C109.5
C5—N1—C1—O10.4 (3)C1—N1—C4—C312.2 (2)
C4—N1—C1—O1179.75 (19)C5—N1—C4—C3167.59 (17)
C5—N1—C1—C2178.81 (18)O3—C3—C4—N196.8 (2)
C4—N1—C1—C21.4 (2)C2—C3—C4—N120.1 (2)
O1—C1—C2—C3167.3 (2)C1—N1—C5—C695.6 (2)
N1—C1—C2—C314.3 (2)C4—N1—C5—C684.2 (2)
C7—O3—C3—C4161.18 (16)N1—C5—C6—O23.4 (3)
C7—O3—C3—C285.6 (2)N1—C5—C6—N2176.38 (17)
C1—C2—C3—O394.21 (19)C3—O3—C7—O43.9 (3)
C1—C2—C3—C421.0 (2)C3—O3—C7—C8176.10 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···O2i0.86 (4)2.41 (4)3.189 (4)152 (3)
N2—H2D···O1ii0.92 (4)2.20 (4)3.113 (3)168 (4)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x1/4, y1/4, z+1/4.
 

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