organic compounds
(3R,4R)-2,5-Dioxo-1-m-tolyl-3,4-diyl diacetate
aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and bInstitut for Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
*Correspondence e-mail: javid_zaidi@qau.edu.pk
In the enantiomerically pure title compound, C15H15NO6, the five-membered ring displays a twist conformation with the local axis through the N atom. The acetyl groups are perpendicular to the ring [dihedral angles 80.3 (1) and 89.3 (1)°] and project to opposite sides. The packing is governed by two weak C—H⋯O interactions, forming layers of molecules parallel to the ab plane.
Related literature
For the potential biological activity, pharmaceutical utility and biological effects of cyclic ); Böger & Wakabayashi (1995); Birchfield & Casida (1997); Cechinel Filho, Nunes, Calixto & Yunes (1995); Cechinel Filho, de Campos, Corrêa, Yunes & Nunes (2003); López et al. (2003); Lima et al. (1999); Sami et al. (2000); Wang et al. (2000); Watanabe et al. (1998).
see: Adomat & Böger (2000Experimental
Crystal data
|
Data collection: CrysAlisPro (Oxford Diffraction, 2008); cell CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809020637/at2801sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020637/at2801Isup2.hkl
The title compound was synthesized from 0.005 mole (1.08 g) diacetyl-L-tartaric acid anhydride (2,5-dioxotetrahydrofuran-3,4-diyldiacetate), 3-methylaniline (0.005 mole, 0.53 g) and 10 ml of glacial acetic acid. The mixture was refluxed for 1 h under nitrogen. Glacial acetic acid was removed by extracting the reaction mixture with ethyl acetate and water. The product was purified by
and recrystallized from dry ethanol [yield 68%; m.p. 379–381 K].Methyl H atoms were located in difference syntheses, idealized to C—H 0.98 Å and H—C—H 109.5°, and refined as rigid groups allowed to rotate but not tip. Other H atoms were placed in calculated positions and refined using a riding model with C—H 0.95 Å for aromatic H and 1.00 Å for methine CH. Hydrogen U values were fixed at 1.5 × U(eq) of the parent atom for methyl H and 1.2 × U(eq) of the parent atom for other H. The compound is θ 145°.
and its (R at C8 and C9, crystallographic numbering) was confirmed by the Flack (1983) parameter. Data are 99.7% complete to 2Data collection: CrysAlis PRO (Oxford Diffraction, 2008); cell
CrysAlis PRO (Oxford Diffraction, 2008); data reduction: CrysAlis PRO (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.C15H15NO6 | F(000) = 320 |
Mr = 305.28 | Dx = 1.378 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2yb | Cell parameters from 13866 reflections |
a = 8.2382 (4) Å | θ = 5.5–75.8° |
b = 5.5380 (3) Å | µ = 0.91 mm−1 |
c = 16.6015 (9) Å | T = 100 K |
β = 103.664 (5)° | Tablet, colourless |
V = 735.98 (7) Å3 | 0.20 × 0.15 × 0.08 mm |
Z = 2 |
Oxford Diffraction Nova A diffractometer | 2790 independent reflections |
Radiation source: Nova (Cu) X-ray Source | 2742 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.3543 pixels mm-1 | θmax = 75.9°, θmin = 5.5° |
ω–scan | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008) | k = −6→6 |
Tmin = 0.892, Tmax = 1.000 | l = −20→20 |
15796 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.1139P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2790 reflections | Δρmax = 0.15 e Å−3 |
202 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1097 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (12) |
C15H15NO6 | V = 735.98 (7) Å3 |
Mr = 305.28 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 8.2382 (4) Å | µ = 0.91 mm−1 |
b = 5.5380 (3) Å | T = 100 K |
c = 16.6015 (9) Å | 0.20 × 0.15 × 0.08 mm |
β = 103.664 (5)° |
Oxford Diffraction Nova A diffractometer | 2790 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008) | 2742 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 1.000 | Rint = 0.030 |
15796 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.067 | Δρmax = 0.15 e Å−3 |
S = 1.04 | Δρmin = −0.18 e Å−3 |
2790 reflections | Absolute structure: Flack (1983), 1097 Freidel pairs |
202 parameters | Absolute structure parameter: 0.04 (12) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.83245 (11) | 0.4087 (2) | 0.77707 (5) | 0.0201 (2) | |
O1 | 0.95264 (12) | 0.3617 (2) | 0.66503 (5) | 0.0332 (2) | |
O2 | 0.65363 (10) | 0.53516 (17) | 0.85796 (5) | 0.02392 (19) | |
O3 | 0.45314 (10) | 0.70803 (16) | 0.70307 (5) | 0.02366 (19) | |
O4 | 0.46297 (13) | 1.11400 (18) | 0.71612 (6) | 0.0353 (2) | |
O5 | 0.73911 (11) | 0.75624 (17) | 0.59745 (5) | 0.02408 (19) | |
O6 | 0.63863 (14) | 0.5220 (2) | 0.48590 (6) | 0.0378 (2) | |
C1 | 0.93789 (14) | 0.2475 (2) | 0.83483 (7) | 0.0201 (2) | |
C2 | 0.86415 (14) | 0.0719 (2) | 0.87400 (7) | 0.0211 (2) | |
H2 | 0.7461 | 0.0634 | 0.8653 | 0.025* | |
C3 | 0.96605 (14) | −0.0911 (3) | 0.92619 (7) | 0.0225 (2) | |
H3 | 0.9175 | −0.2128 | 0.9534 | 0.027* | |
C4 | 1.13842 (14) | −0.0773 (3) | 0.93890 (7) | 0.0228 (2) | |
H4 | 1.2066 | −0.1920 | 0.9739 | 0.027* | |
C5 | 1.21311 (14) | 0.1025 (2) | 0.90112 (7) | 0.0222 (2) | |
C6 | 1.11073 (15) | 0.2667 (2) | 0.84868 (7) | 0.0221 (2) | |
H6 | 1.1589 | 0.3912 | 0.8225 | 0.026* | |
C7 | 0.84338 (14) | 0.4369 (3) | 0.69489 (7) | 0.0232 (2) | |
C8 | 0.69155 (14) | 0.5797 (2) | 0.64972 (7) | 0.0215 (2) | |
H8 | 0.6045 | 0.4694 | 0.6169 | 0.026* | |
C9 | 0.62962 (14) | 0.6982 (2) | 0.71900 (7) | 0.0211 (2) | |
H9 | 0.6769 | 0.8647 | 0.7290 | 0.025* | |
C10 | 0.69933 (14) | 0.5396 (2) | 0.79435 (7) | 0.0203 (2) | |
C11 | 0.38285 (15) | 0.9315 (3) | 0.70241 (7) | 0.0259 (3) | |
C12 | 0.19739 (16) | 0.9069 (3) | 0.68349 (9) | 0.0356 (3) | |
H12A | 0.1653 | 0.8170 | 0.7282 | 0.053* | |
H12B | 0.1588 | 0.8199 | 0.6311 | 0.053* | |
H12C | 0.1463 | 1.0676 | 0.6788 | 0.053* | |
C13 | 0.70695 (15) | 0.7034 (3) | 0.51479 (7) | 0.0252 (3) | |
C14 | 0.77036 (16) | 0.9016 (3) | 0.46948 (8) | 0.0314 (3) | |
H14A | 0.8918 | 0.8869 | 0.4779 | 0.047* | |
H14B | 0.7432 | 1.0580 | 0.4906 | 0.047* | |
H14C | 0.7177 | 0.8899 | 0.4102 | 0.047* | |
C15 | 1.40119 (15) | 0.1163 (3) | 0.91705 (8) | 0.0317 (3) | |
H15A | 1.4327 | 0.2568 | 0.8882 | 0.048* | |
H15B | 1.4438 | −0.0310 | 0.8966 | 0.048* | |
H15C | 1.4492 | 0.1322 | 0.9767 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0208 (4) | 0.0202 (5) | 0.0192 (4) | 0.0022 (4) | 0.0047 (3) | 0.0014 (4) |
O1 | 0.0348 (5) | 0.0416 (6) | 0.0264 (4) | 0.0167 (4) | 0.0137 (4) | 0.0088 (4) |
O2 | 0.0247 (4) | 0.0258 (5) | 0.0224 (4) | −0.0010 (3) | 0.0078 (3) | −0.0023 (4) |
O3 | 0.0208 (4) | 0.0199 (5) | 0.0293 (4) | 0.0049 (3) | 0.0040 (3) | −0.0012 (4) |
O4 | 0.0435 (5) | 0.0218 (5) | 0.0354 (5) | 0.0086 (4) | −0.0010 (4) | −0.0048 (4) |
O5 | 0.0279 (4) | 0.0234 (5) | 0.0201 (4) | −0.0003 (4) | 0.0041 (3) | 0.0043 (3) |
O6 | 0.0587 (6) | 0.0312 (5) | 0.0242 (4) | −0.0094 (5) | 0.0113 (4) | −0.0017 (4) |
C1 | 0.0242 (5) | 0.0179 (6) | 0.0175 (5) | 0.0023 (5) | 0.0033 (4) | −0.0004 (5) |
C2 | 0.0218 (5) | 0.0217 (7) | 0.0197 (5) | −0.0014 (5) | 0.0045 (4) | −0.0015 (5) |
C3 | 0.0277 (5) | 0.0204 (6) | 0.0195 (5) | −0.0025 (5) | 0.0058 (4) | 0.0008 (5) |
C4 | 0.0270 (5) | 0.0227 (6) | 0.0180 (5) | 0.0039 (5) | 0.0038 (4) | 0.0016 (5) |
C5 | 0.0221 (5) | 0.0254 (6) | 0.0190 (5) | 0.0000 (5) | 0.0044 (4) | −0.0019 (5) |
C6 | 0.0235 (5) | 0.0225 (6) | 0.0208 (5) | −0.0005 (5) | 0.0066 (4) | 0.0025 (5) |
C7 | 0.0253 (5) | 0.0228 (6) | 0.0219 (5) | 0.0020 (5) | 0.0063 (4) | 0.0028 (5) |
C8 | 0.0243 (5) | 0.0192 (6) | 0.0211 (5) | 0.0019 (5) | 0.0058 (4) | 0.0019 (5) |
C9 | 0.0209 (5) | 0.0191 (6) | 0.0225 (5) | 0.0014 (5) | 0.0040 (4) | −0.0003 (5) |
C10 | 0.0198 (5) | 0.0178 (6) | 0.0225 (5) | −0.0013 (4) | 0.0034 (4) | −0.0017 (5) |
C11 | 0.0337 (6) | 0.0238 (7) | 0.0186 (5) | 0.0096 (6) | 0.0030 (4) | −0.0025 (5) |
C12 | 0.0298 (6) | 0.0397 (9) | 0.0357 (6) | 0.0147 (7) | 0.0046 (5) | −0.0028 (7) |
C13 | 0.0285 (6) | 0.0256 (7) | 0.0219 (5) | 0.0036 (5) | 0.0065 (4) | 0.0043 (5) |
C14 | 0.0374 (6) | 0.0307 (8) | 0.0271 (6) | 0.0003 (6) | 0.0096 (5) | 0.0077 (6) |
C15 | 0.0233 (6) | 0.0380 (9) | 0.0333 (7) | 0.0007 (5) | 0.0056 (5) | 0.0062 (6) |
N1—C7 | 1.3971 (14) | C8—C9 | 1.5136 (16) |
N1—C10 | 1.3996 (15) | C9—C10 | 1.5252 (17) |
N1—C1 | 1.4413 (15) | C11—C12 | 1.4916 (17) |
O1—C7 | 1.2000 (15) | C13—C14 | 1.4931 (18) |
O2—C10 | 1.2023 (14) | C2—H2 | 0.9500 |
O3—C11 | 1.3654 (16) | C3—H3 | 0.9500 |
O3—C9 | 1.4160 (13) | C4—H4 | 0.9500 |
O4—C11 | 1.1990 (18) | C6—H6 | 0.9500 |
O5—C13 | 1.3664 (15) | C8—H8 | 1.0000 |
O5—C8 | 1.4225 (15) | C9—H9 | 1.0000 |
O6—C13 | 1.1952 (18) | C12—H12A | 0.9800 |
C1—C2 | 1.3873 (17) | C12—H12B | 0.9800 |
C1—C6 | 1.3918 (16) | C12—H12C | 0.9800 |
C2—C3 | 1.3881 (17) | C14—H14A | 0.9800 |
C3—C4 | 1.3876 (16) | C14—H14B | 0.9800 |
C4—C5 | 1.3949 (18) | C14—H14C | 0.9800 |
C5—C6 | 1.3962 (17) | C15—H15A | 0.9800 |
C5—C15 | 1.5110 (15) | C15—H15B | 0.9800 |
C7—C8 | 1.5196 (16) | C15—H15C | 0.9800 |
C7—N1—C10 | 112.13 (10) | C1—C2—H2 | 120.6 |
C7—N1—C1 | 123.44 (10) | C3—C2—H2 | 120.6 |
C10—N1—C1 | 124.24 (9) | C4—C3—H3 | 119.8 |
C11—O3—C9 | 116.83 (10) | C2—C3—H3 | 119.8 |
C13—O5—C8 | 116.70 (10) | C3—C4—H4 | 119.5 |
C2—C1—C6 | 121.35 (11) | C5—C4—H4 | 119.5 |
C2—C1—N1 | 118.97 (10) | C1—C6—H6 | 120.1 |
C6—C1—N1 | 119.66 (11) | C5—C6—H6 | 120.1 |
C1—C2—C3 | 118.78 (11) | O5—C8—H8 | 110.6 |
C4—C3—C2 | 120.35 (12) | C9—C8—H8 | 110.6 |
C3—C4—C5 | 121.02 (11) | C7—C8—H8 | 110.6 |
C4—C5—C6 | 118.67 (10) | O3—C9—H9 | 109.8 |
C4—C5—C15 | 120.03 (11) | C8—C9—H9 | 109.8 |
C6—C5—C15 | 121.31 (11) | C10—C9—H9 | 109.8 |
C1—C6—C5 | 119.80 (11) | C11—C12—H12A | 109.5 |
O1—C7—N1 | 126.33 (11) | C11—C12—H12B | 109.5 |
O1—C7—C8 | 125.94 (10) | H12A—C12—H12B | 109.5 |
N1—C7—C8 | 107.73 (9) | C11—C12—H12C | 109.5 |
O5—C8—C9 | 110.88 (10) | H12A—C12—H12C | 109.5 |
O5—C8—C7 | 110.22 (9) | H12B—C12—H12C | 109.5 |
C9—C8—C7 | 103.69 (9) | C13—C14—H14A | 109.5 |
O3—C9—C8 | 112.97 (9) | C13—C14—H14B | 109.5 |
O3—C9—C10 | 110.28 (9) | H14A—C14—H14B | 109.5 |
C8—C9—C10 | 104.14 (10) | C13—C14—H14C | 109.5 |
O2—C10—N1 | 126.34 (11) | H14A—C14—H14C | 109.5 |
O2—C10—C9 | 126.64 (11) | H14B—C14—H14C | 109.5 |
N1—C10—C9 | 106.95 (9) | C5—C15—H15A | 109.5 |
O4—C11—O3 | 123.30 (11) | C5—C15—H15B | 109.5 |
O4—C11—C12 | 127.42 (13) | H15A—C15—H15B | 109.5 |
O3—C11—C12 | 109.28 (12) | C5—C15—H15C | 109.5 |
O6—C13—O5 | 122.99 (12) | H15A—C15—H15C | 109.5 |
O6—C13—C14 | 127.10 (12) | H15B—C15—H15C | 109.5 |
O5—C13—C14 | 109.91 (11) | ||
C7—N1—C1—C2 | −123.73 (13) | N1—C7—C8—O5 | 137.39 (10) |
C10—N1—C1—C2 | 50.86 (16) | O1—C7—C8—C9 | −161.45 (14) |
C7—N1—C1—C6 | 54.68 (16) | N1—C7—C8—C9 | 18.66 (14) |
C10—N1—C1—C6 | −130.73 (12) | C11—O3—C9—C8 | −121.50 (11) |
C6—C1—C2—C3 | −1.77 (18) | C11—O3—C9—C10 | 122.43 (11) |
N1—C1—C2—C3 | 176.61 (10) | O5—C8—C9—O3 | 99.30 (11) |
C1—C2—C3—C4 | 0.19 (18) | C7—C8—C9—O3 | −142.43 (10) |
C2—C3—C4—C5 | 1.31 (18) | O5—C8—C9—C10 | −141.03 (9) |
C3—C4—C5—C6 | −1.23 (17) | C7—C8—C9—C10 | −22.76 (12) |
C3—C4—C5—C15 | 178.99 (12) | C7—N1—C10—O2 | 174.41 (12) |
C2—C1—C6—C5 | 1.85 (18) | C1—N1—C10—O2 | −0.7 (2) |
N1—C1—C6—C5 | −176.52 (11) | C7—N1—C10—C9 | −8.51 (14) |
C4—C5—C6—C1 | −0.33 (17) | C1—N1—C10—C9 | 176.36 (11) |
C15—C5—C6—C1 | 179.45 (12) | O3—C9—C10—O2 | −41.62 (17) |
C10—N1—C7—O1 | 173.58 (14) | C8—C9—C10—O2 | −163.10 (12) |
C1—N1—C7—O1 | −11.3 (2) | O3—C9—C10—N1 | 141.31 (10) |
C10—N1—C7—C8 | −6.52 (15) | C8—C9—C10—N1 | 19.83 (12) |
C1—N1—C7—C8 | 168.64 (11) | C9—O3—C11—O4 | −1.53 (16) |
C13—O5—C8—C9 | −144.04 (10) | C9—O3—C11—C12 | 179.15 (9) |
C13—O5—C8—C7 | 101.73 (12) | C8—O5—C13—O6 | 1.85 (18) |
O1—C7—C8—O5 | −42.72 (18) | C8—O5—C13—C14 | −177.72 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12C···O1i | 0.98 | 2.25 | 3.1957 (17) | 161 |
C15—H15A···O2ii | 0.98 | 2.52 | 3.4104 (17) | 150 |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO6 |
Mr | 305.28 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 8.2382 (4), 5.5380 (3), 16.6015 (9) |
β (°) | 103.664 (5) |
V (Å3) | 735.98 (7) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.20 × 0.15 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Nova A diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2008) |
Tmin, Tmax | 0.892, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15796, 2790, 2742 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.067, 1.04 |
No. of reflections | 2790 |
No. of parameters | 202 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.18 |
Absolute structure | Flack (1983), 1097 Freidel pairs |
Absolute structure parameter | 0.04 (12) |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12C···O1i | 0.98 | 2.25 | 3.1957 (17) | 161.0 |
C15—H15A···O2ii | 0.98 | 2.52 | 3.4104 (17) | 150.3 |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y, z. |
Acknowledgements
The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, and the Institute for Inorganic Chemistry, University of Frankfurt, Germany, for providing laboratory and analytical facilities.
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Synthetic cyclic imides, such as succinimides, maleimides, glutarimides, phthalimides and related compounds, possess structural features that confer potential biological activity and pharmaceutical utility. All these classes of cyclic imides have received attention because of their antibacterial, antifungal, analgesic (Cechinel et al., 2003) and antitumor activities (Sami et al., 2000; Wang et al., 2000). Some of these effects appear to be related to the size and electrophilic characteristics of substituent groups on the imide ring, which can modify its steric properties (Cechinel et al., 1995; Lima et al., 1999; López et al., 2003). Beside these interesting biological effects, some cyclic imides, e.g., chlorophthalim (Adomat & Böger, 2000), N-aryltetrahydrophthalimide (Birchfield & Casida, 1997) and N– (4-chloro-2-fluoro-5-propargyloxy)-phenyl-3,4,5,6-tetrahydrophthalimide (Watanabe et al., 1998) are peroxidizing herbicides, a class of herbicides that inhibit protoporphyrinogen IX oxidase, a key enzyme of heme and chlorophyll biosynthesis (Böger & Wakabayashi, 1995). In the course of our studies of cyclic imides, we have synthesized the title compound (I) and here present its structure (Fig. 1).
In the title molecule (I), the five-membered ring displays a twist conformation with the local twofold axis through N1 and the midpoint of C8—C9. The toluene ring subtends an interplanar angle of 51.3 (1)° with the planar moiety N1/C7/C10/O1/O2. The acetyl groups are perpendicular to the pyrrolidine moiety, whereby the plane C7–C9 subtends an angle of 80.3 (1)° to the plane C8/O5/O6/ C13/C14 and C8–C10 an angle of 89.3 (1)° to C9/O3/O4/C11/C12; the carbonyl O atoms project to opposite sides of the ring. The packing (Fig. 2) consists of broad layers of molecules parallel to the ab plane at z ≈ 1/4, 3/4, the molecules being linked by the weak interactions H15A···O2 [2.52 Å] and H12C···O1 [2.25 Å].