The chiral title compound, C
8H
9NO
4, crystallizes in the non-centrosymmetric space group
P2
12
12
1, 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
CCDC reference: 274587
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
C8H9NO4 | F(000) = 384 |
Mr = 183.16 | Dx = 1.420 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.946 (2) Å | θ = 9.9–12.0° |
b = 10.204 (2) Å | µ = 0.12 mm−1 |
c = 12.088 (4) Å | T = 150 K |
V = 856.8 (4) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.25 mm |
Data collection top
Enraf–Nonius CAD-4T diffractometer | Rint = 0.097 |
Radiation source: rotating anode | θmax = 27.4°, θmin = 2.6° |
Graphite monochromator | h = 0→8 |
ω/2θ scans | k = −13→13 |
4158 measured reflections | l = −15→15 |
1140 independent reflections | 3 standard reflections every 60 min |
855 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0224 (3) | 0.6714 (2) | 0.66602 (17) | 0.0284 (5) | |
O2 | 0.1092 (3) | 0.31308 (19) | 0.50499 (19) | 0.0318 (5) | |
O3 | 0.4440 (3) | 0.64991 (19) | 0.63081 (16) | 0.0229 (5) | |
O4 | 0.4015 (3) | 0.8667 (2) | 0.60491 (16) | 0.0277 (5) | |
N1 | 0.1838 (3) | 0.5245 (2) | 0.56412 (19) | 0.0190 (6) | |
C2 | 0.2083 (4) | 0.4097 (3) | 0.5003 (3) | 0.0217 (6) | |
C3 | 0.3775 (5) | 0.4343 (3) | 0.4302 (2) | 0.0240 (7) | |
H3 | 0.4300 | 0.3739 | 0.3785 | 0.029* | |
C4 | 0.4458 (4) | 0.5531 (3) | 0.4500 (2) | 0.0232 (7) | |
H4 | 0.5556 | 0.5897 | 0.4148 | 0.028* | |
C5 | 0.3275 (4) | 0.6218 (3) | 0.5348 (2) | 0.0202 (6) | |
H5 | 0.2670 | 0.7031 | 0.5043 | 0.024* | |
C6 | 0.0268 (4) | 0.5601 (3) | 0.6295 (2) | 0.0222 (6) | |
C7 | −0.1230 (5) | 0.4598 (3) | 0.6530 (3) | 0.0295 (7) | |
H7A | −0.2211 | 0.4973 | 0.7020 | 0.044* | |
H7B | −0.0635 | 0.3839 | 0.6891 | 0.044* | |
H7C | −0.1833 | 0.4321 | 0.5836 | 0.044* | |
C8 | 0.4648 (4) | 0.7780 (3) | 0.6591 (2) | 0.0219 (6) | |
C9 | 0.5793 (5) | 0.7907 (3) | 0.7622 (2) | 0.0313 (8) | |
H9A | 0.7050 | 0.7488 | 0.7520 | 0.047* | |
H9B | 0.5109 | 0.7481 | 0.8232 | 0.047* | |
H9C | 0.5977 | 0.8837 | 0.7794 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0330 (13) | 0.0248 (12) | 0.0273 (11) | 0.0047 (10) | 0.0038 (10) | −0.0010 (10) |
O2 | 0.0393 (13) | 0.0206 (11) | 0.0353 (11) | −0.0089 (10) | 0.0003 (12) | −0.0030 (10) |
O3 | 0.0240 (12) | 0.0199 (11) | 0.0248 (10) | −0.0009 (9) | −0.0081 (9) | −0.0018 (8) |
O4 | 0.0335 (13) | 0.0201 (11) | 0.0295 (11) | −0.0025 (10) | 0.0005 (11) | −0.0023 (9) |
N1 | 0.0208 (14) | 0.0174 (13) | 0.0190 (12) | −0.0003 (11) | −0.0010 (10) | 0.0010 (9) |
C2 | 0.0299 (16) | 0.0168 (14) | 0.0183 (13) | −0.0002 (12) | −0.0064 (14) | −0.0001 (12) |
C3 | 0.0285 (17) | 0.0216 (16) | 0.0219 (14) | 0.0026 (14) | 0.0024 (14) | 0.0005 (12) |
C4 | 0.0206 (16) | 0.0253 (16) | 0.0237 (14) | 0.0004 (13) | −0.0003 (13) | 0.0034 (12) |
C5 | 0.0199 (16) | 0.0191 (15) | 0.0217 (14) | 0.0000 (12) | −0.0056 (12) | 0.0029 (11) |
C6 | 0.0231 (16) | 0.0231 (15) | 0.0204 (14) | 0.0033 (13) | −0.0035 (13) | 0.0024 (12) |
C7 | 0.0234 (16) | 0.0292 (17) | 0.0359 (18) | −0.0039 (15) | 0.0053 (15) | 0.0030 (14) |
C8 | 0.0149 (14) | 0.0257 (16) | 0.0250 (14) | −0.0020 (13) | 0.0076 (13) | −0.0051 (13) |
C9 | 0.0281 (19) | 0.037 (2) | 0.0286 (16) | −0.0053 (16) | −0.0015 (14) | −0.0089 (14) |
Geometric parameters (Å, º) top
O1—C6 | 1.219 (4) | C4—C5 | 1.489 (4) |
O2—C2 | 1.204 (3) | C4—H4 | 0.9500 |
O3—C8 | 1.359 (3) | C5—H5 | 1.0000 |
O3—C5 | 1.443 (3) | C6—C7 | 1.487 (4) |
O4—C8 | 1.201 (3) | C7—H7A | 0.9800 |
N1—C6 | 1.395 (4) | C7—H7B | 0.9800 |
N1—C2 | 1.413 (4) | C7—H7C | 0.9800 |
N1—C5 | 1.452 (4) | C8—C9 | 1.484 (4) |
C2—C3 | 1.470 (4) | C9—H9A | 0.9800 |
C3—C4 | 1.324 (4) | C9—H9B | 0.9800 |
C3—H3 | 0.9500 | C9—H9C | 0.9800 |
| | | |
C8—O3—C5 | 116.9 (2) | O1—C6—N1 | 117.9 (3) |
C6—N1—C2 | 128.3 (3) | O1—C6—C7 | 123.7 (3) |
C6—N1—C5 | 119.8 (2) | N1—C6—C7 | 118.4 (3) |
C2—N1—C5 | 110.5 (2) | C6—C7—H7A | 109.5 |
O2—C2—N1 | 125.8 (3) | C6—C7—H7B | 109.5 |
O2—C2—C3 | 128.6 (3) | H7A—C7—H7B | 109.5 |
N1—C2—C3 | 105.7 (2) | C6—C7—H7C | 109.5 |
C4—C3—C2 | 109.8 (3) | H7A—C7—H7C | 109.5 |
C4—C3—H3 | 125.1 | H7B—C7—H7C | 109.5 |
C2—C3—H3 | 125.1 | O4—C8—O3 | 123.3 (3) |
C3—C4—C5 | 111.0 (3) | O4—C8—C9 | 126.0 (3) |
C3—C4—H4 | 124.5 | O3—C8—C9 | 110.7 (3) |
C5—C4—H4 | 124.5 | C8—C9—H9A | 109.5 |
O3—C5—N1 | 109.0 (2) | C8—C9—H9B | 109.5 |
O3—C5—C4 | 109.7 (2) | H9A—C9—H9B | 109.5 |
N1—C5—C4 | 103.0 (2) | C8—C9—H9C | 109.5 |
O3—C5—H5 | 111.6 | H9A—C9—H9C | 109.5 |
N1—C5—H5 | 111.6 | H9B—C9—H9C | 109.5 |
C4—C5—H5 | 111.6 | | |
| | | |
C6—N1—C2—O2 | −12.3 (5) | C6—N1—C5—C4 | −169.9 (2) |
C5—N1—C2—O2 | −178.9 (3) | C2—N1—C5—C4 | −2.0 (3) |
C6—N1—C2—C3 | 168.2 (3) | C3—C4—C5—O3 | 117.6 (3) |
C5—N1—C2—C3 | 1.6 (3) | C3—C4—C5—N1 | 1.6 (3) |
O2—C2—C3—C4 | 180.0 (3) | C2—N1—C6—O1 | −170.1 (3) |
N1—C2—C3—C4 | −0.5 (3) | C5—N1—C6—O1 | −4.6 (4) |
C2—C3—C4—C5 | −0.7 (4) | C2—N1—C6—C7 | 11.3 (4) |
C8—O3—C5—N1 | −128.3 (2) | C5—N1—C6—C7 | 176.8 (3) |
C8—O3—C5—C4 | 119.6 (3) | C5—O3—C8—O4 | −4.6 (4) |
C6—N1—C5—O3 | 73.6 (3) | C5—O3—C8—C9 | 177.1 (2) |
C2—N1—C5—O3 | −118.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O4i | 0.95 | 2.46 | 3.336 (4) | 154 |
C5—H5···O4 | 1.00 | 2.27 | 2.688 (4) | 104 |
C9—H9A···O1ii | 0.98 | 2.56 | 3.508 (4) | 162 |
C9—H9B···O2iii | 0.98 | 2.43 | 3.384 (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. |