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The chiral title compound, C8H9NO4, crystallizes in the non-centrosymmetric space group P212121, but in the absence of an atom with significant anomalous dispersion, the absolute configuration could not be determined. The H atoms in both meth­yl groups are eclipsed with respect to the C=O bond. The structure features weak C—H...O inter­actions that link the mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501545X/lh6429sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501545X/lh6429Isup2.hkl
Contains datablock I

CCDC reference: 274587

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.090
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



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 27.38 From the CIF: _reflns_number_total 1140 Count of symmetry unique reflns 1140 Completeness (_total/calc) 100.00% 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 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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

Computing details top

Data collection: locally modified CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

5-Acetoxy-1-acetyl-3-pyrrolin-2-one top
Crystal data top
C8H9NO4F(000) = 384
Mr = 183.16Dx = 1.420 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.946 (2) Åθ = 9.9–12.0°
b = 10.204 (2) ŵ = 0.12 mm1
c = 12.088 (4) ÅT = 150 K
V = 856.8 (4) Å3Block, colourless
Z = 40.30 × 0.25 × 0.25 mm
Data collection top
Enraf–Nonius CAD-4T
diffractometer
Rint = 0.097
Radiation source: rotating anodeθmax = 27.4°, θmin = 2.6°
Graphite monochromatorh = 08
ω/2θ scansk = 1313
4158 measured reflectionsl = 1515
1140 independent reflections3 standard reflections every 60 min
855 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0335P)2]
where P = (Fo2 + 2Fc2)/3
1140 reflections(Δ/σ)max < 0.001
120 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
O10.0224 (3)0.6714 (2)0.66602 (17)0.0284 (5)
O20.1092 (3)0.31308 (19)0.50499 (19)0.0318 (5)
O30.4440 (3)0.64991 (19)0.63081 (16)0.0229 (5)
O40.4015 (3)0.8667 (2)0.60491 (16)0.0277 (5)
N10.1838 (3)0.5245 (2)0.56412 (19)0.0190 (6)
C20.2083 (4)0.4097 (3)0.5003 (3)0.0217 (6)
C30.3775 (5)0.4343 (3)0.4302 (2)0.0240 (7)
H30.43000.37390.37850.029*
C40.4458 (4)0.5531 (3)0.4500 (2)0.0232 (7)
H40.55560.58970.41480.028*
C50.3275 (4)0.6218 (3)0.5348 (2)0.0202 (6)
H50.26700.70310.50430.024*
C60.0268 (4)0.5601 (3)0.6295 (2)0.0222 (6)
C70.1230 (5)0.4598 (3)0.6530 (3)0.0295 (7)
H7A0.22110.49730.70200.044*
H7B0.06350.38390.68910.044*
H7C0.18330.43210.58360.044*
C80.4648 (4)0.7780 (3)0.6591 (2)0.0219 (6)
C90.5793 (5)0.7907 (3)0.7622 (2)0.0313 (8)
H9A0.70500.74880.75200.047*
H9B0.51090.74810.82320.047*
H9C0.59770.88370.77940.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0330 (13)0.0248 (12)0.0273 (11)0.0047 (10)0.0038 (10)0.0010 (10)
O20.0393 (13)0.0206 (11)0.0353 (11)0.0089 (10)0.0003 (12)0.0030 (10)
O30.0240 (12)0.0199 (11)0.0248 (10)0.0009 (9)0.0081 (9)0.0018 (8)
O40.0335 (13)0.0201 (11)0.0295 (11)0.0025 (10)0.0005 (11)0.0023 (9)
N10.0208 (14)0.0174 (13)0.0190 (12)0.0003 (11)0.0010 (10)0.0010 (9)
C20.0299 (16)0.0168 (14)0.0183 (13)0.0002 (12)0.0064 (14)0.0001 (12)
C30.0285 (17)0.0216 (16)0.0219 (14)0.0026 (14)0.0024 (14)0.0005 (12)
C40.0206 (16)0.0253 (16)0.0237 (14)0.0004 (13)0.0003 (13)0.0034 (12)
C50.0199 (16)0.0191 (15)0.0217 (14)0.0000 (12)0.0056 (12)0.0029 (11)
C60.0231 (16)0.0231 (15)0.0204 (14)0.0033 (13)0.0035 (13)0.0024 (12)
C70.0234 (16)0.0292 (17)0.0359 (18)0.0039 (15)0.0053 (15)0.0030 (14)
C80.0149 (14)0.0257 (16)0.0250 (14)0.0020 (13)0.0076 (13)0.0051 (13)
C90.0281 (19)0.037 (2)0.0286 (16)0.0053 (16)0.0015 (14)0.0089 (14)
Geometric parameters (Å, º) top
O1—C61.219 (4)C4—C51.489 (4)
O2—C21.204 (3)C4—H40.9500
O3—C81.359 (3)C5—H51.0000
O3—C51.443 (3)C6—C71.487 (4)
O4—C81.201 (3)C7—H7A0.9800
N1—C61.395 (4)C7—H7B0.9800
N1—C21.413 (4)C7—H7C0.9800
N1—C51.452 (4)C8—C91.484 (4)
C2—C31.470 (4)C9—H9A0.9800
C3—C41.324 (4)C9—H9B0.9800
C3—H30.9500C9—H9C0.9800
C8—O3—C5116.9 (2)O1—C6—N1117.9 (3)
C6—N1—C2128.3 (3)O1—C6—C7123.7 (3)
C6—N1—C5119.8 (2)N1—C6—C7118.4 (3)
C2—N1—C5110.5 (2)C6—C7—H7A109.5
O2—C2—N1125.8 (3)C6—C7—H7B109.5
O2—C2—C3128.6 (3)H7A—C7—H7B109.5
N1—C2—C3105.7 (2)C6—C7—H7C109.5
C4—C3—C2109.8 (3)H7A—C7—H7C109.5
C4—C3—H3125.1H7B—C7—H7C109.5
C2—C3—H3125.1O4—C8—O3123.3 (3)
C3—C4—C5111.0 (3)O4—C8—C9126.0 (3)
C3—C4—H4124.5O3—C8—C9110.7 (3)
C5—C4—H4124.5C8—C9—H9A109.5
O3—C5—N1109.0 (2)C8—C9—H9B109.5
O3—C5—C4109.7 (2)H9A—C9—H9B109.5
N1—C5—C4103.0 (2)C8—C9—H9C109.5
O3—C5—H5111.6H9A—C9—H9C109.5
N1—C5—H5111.6H9B—C9—H9C109.5
C4—C5—H5111.6
C6—N1—C2—O212.3 (5)C6—N1—C5—C4169.9 (2)
C5—N1—C2—O2178.9 (3)C2—N1—C5—C42.0 (3)
C6—N1—C2—C3168.2 (3)C3—C4—C5—O3117.6 (3)
C5—N1—C2—C31.6 (3)C3—C4—C5—N11.6 (3)
O2—C2—C3—C4180.0 (3)C2—N1—C6—O1170.1 (3)
N1—C2—C3—C40.5 (3)C5—N1—C6—O14.6 (4)
C2—C3—C4—C50.7 (4)C2—N1—C6—C711.3 (4)
C8—O3—C5—N1128.3 (2)C5—N1—C6—C7176.8 (3)
C8—O3—C5—C4119.6 (3)C5—O3—C8—O44.6 (4)
C6—N1—C5—O373.6 (3)C5—O3—C8—C9177.1 (2)
C2—N1—C5—O3118.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.952.463.336 (4)154
C5—H5···O41.002.272.688 (4)104
C9—H9A···O1ii0.982.563.508 (4)162
C9—H9B···O2iii0.982.433.384 (4)164
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1, y, z; (iii) x+1/2, y+1, z+1/2.
 

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