Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050519/bt2534sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050519/bt2534Isup2.hkl |
CCDC reference: 667409
The title compound is synthesized by the Manich condensation of phthalimide (14.71 g, 0.1 mol), 37% aqueous formaldehyde (7.5 ml, 0.1 mol) and pyrrolidone (8.2 ml, 0.1 mol) at 5°C. It was recrystalized from ethanol. The sample melts at 106–107°C.
All the hydrogen atoms were geometrically fixed and allowed to ride on their parent atoms with C—H=0.93 - 0.96 Å, and Uiso=1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for H atoms. The absolute structure was determined using 1957 Friedal pairs.
Substitituted pyrrolidine compounds have been found to have antimicrobial antifungal activity against various pathogens except Basillus substilis (Amal Raj et al., 2003). Pyrrolidine derivatives possess anti-influenza virus (Stylianakis et al., 2003), anticonvulsant (Obniska & Zagorska, 2003; Obniska et al., 2005), and other antiviral (Kolocouris et al., 1994) activities. Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities (Lima et al., 2002; Orzeszka et al., 2000; Bailleux et al., 1993). Phthalimides have also served as starting materials and intermediates for synthesis of alkaloids (Couture et al., 1998) pharmacophores (Couture et al., 1997). Several optically active pyrrolidine compounds have been used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). In view of its importance and to obtain more detailed information of the structure and conformation of the title compound, its crystal structure was determined.
All C—C and C—N bond lengths in the pyrrolidine ring are comparable with values in related pyrrolidine derivatives (Abdul Ajees et al., 2002).
The sum of the angles at N2 of the pyrrolidine ring (340.69°) is in accordance with sp3 hybridization. The pyrrolidine ring adopts an envelope conformation and puckering parameters q2=0.3772 (2) Å and φ2 = 359.7 (4)° (Cremer & Pople,1975). Atom N2 deviates by 0.248 (2) Å from the least squares plane through the remaining four C atoms (C10/C11/C12/C13) of the ring.
The pyrrolidine ring makes a dihedral angle of 78.72 (8)° with the isoindole-1–3-dione ring. The molecular structure is stabilized by C—H···O and C—H···N interactions (Table 2 and Fig 2.).
For related literature, see: Abdul Ajees et al. (2002); Amal Raj et al. (2003); Bailleux et al. (1993); Couture et al. (1997, 1998); Cremer & Pople (1975); Kolocouris et al. (1994); Lima et al. (2002); Obniska & Zagorska (2003); Obniska et al. (2005); Orzeszka et al. (2000); Stylianakis et al. (2003); Suzuki et al. (1994).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C13H14N2O2 | Least Squares Treatment of 25 SET4 setting angles. |
Mr = 230.26 | Dx = 1.287 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3270 reflections |
a = 9.0609 (3) Å | θ = 2.3–26.9° |
b = 10.0777 (3) Å | µ = 0.09 mm−1 |
c = 13.0192 (3) Å | T = 293 K |
V = 1188.82 (6) Å3 | Prism, colorless |
Z = 4 | 0.30 × 0.22 × 0.20 mm |
F(000) = 488 |
Bruker Kappa-APEX2 diffractometer | 2752 independent reflections |
Radiation source: fine focus sealed tube | 1943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and φ scans | θmax = 34.2°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→14 |
Tmin = 0.974, Tmax = 0.983 | k = −13→15 |
10764 measured reflections | l = −20→20 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.134 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2752 reflections | Δρmin = −0.21 e Å−3 |
155 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.017 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1957 Friedel pairs |
Secondary atom site location: difference Fourier map |
C13H14N2O2 | V = 1188.82 (6) Å3 |
Mr = 230.26 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.0609 (3) Å | µ = 0.09 mm−1 |
b = 10.0777 (3) Å | T = 293 K |
c = 13.0192 (3) Å | 0.30 × 0.22 × 0.20 mm |
Bruker Kappa-APEX2 diffractometer | 2752 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1943 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.983 | Rint = 0.023 |
10764 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2752 reflections | Δρmin = −0.21 e Å−3 |
155 parameters | Absolute structure: Flack (1983), 1957 Friedel pairs |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
O1 | 0.18398 (17) | 0.21647 (14) | −0.06749 (9) | 0.0629 (4) | |
O2 | 0.43688 (14) | 0.14885 (13) | 0.23098 (8) | 0.0539 (4) | |
N1 | 0.30783 (15) | 0.21825 (12) | 0.08729 (9) | 0.0410 (3) | |
N2 | 0.22703 (15) | 0.43629 (14) | 0.15153 (11) | 0.0458 (4) | |
C1 | 0.23597 (17) | 0.15773 (17) | 0.00464 (10) | 0.0427 (4) | |
C2 | 0.24128 (18) | 0.01370 (17) | 0.02426 (10) | 0.0420 (4) | |
C3 | 0.1829 (2) | −0.0904 (2) | −0.03067 (13) | 0.0574 (6) | |
C4 | 0.2072 (3) | −0.2164 (2) | 0.00767 (17) | 0.0692 (7) | |
C5 | 0.2855 (3) | −0.2374 (2) | 0.09740 (18) | 0.0687 (7) | |
C6 | 0.3435 (2) | −0.13266 (18) | 0.15237 (15) | 0.0536 (5) | |
C7 | 0.32003 (17) | −0.00686 (15) | 0.11436 (10) | 0.0403 (4) | |
C8 | 0.36506 (15) | 0.12407 (15) | 0.15516 (11) | 0.0396 (4) | |
C9 | 0.33321 (18) | 0.36197 (15) | 0.09495 (12) | 0.0444 (4) | |
C10 | 0.2215 (2) | 0.4163 (2) | 0.26207 (13) | 0.0620 (6) | |
C11 | 0.0869 (3) | 0.4946 (4) | 0.29372 (18) | 0.0900 (10) | |
C12 | −0.0082 (3) | 0.5043 (4) | 0.19898 (18) | 0.0905 (10) | |
C13 | 0.0746 (2) | 0.4311 (2) | 0.11634 (15) | 0.0612 (6) | |
H3A | 0.12962 | −0.07660 | −0.09079 | 0.0689* | |
H4A | 0.16982 | −0.28910 | −0.02784 | 0.0830* | |
H5A | 0.29935 | −0.32358 | 0.12106 | 0.0824* | |
H6A | 0.39631 | −0.14643 | 0.21269 | 0.0642* | |
H9A | 0.42910 | 0.37592 | 0.12627 | 0.0533* | |
H9B | 0.33773 | 0.39790 | 0.02590 | 0.0533* | |
H10A | 0.30976 | 0.45017 | 0.29506 | 0.0744* | |
H10B | 0.21039 | 0.32302 | 0.27884 | 0.0744* | |
H11A | 0.03441 | 0.44943 | 0.34846 | 0.1079* | |
H11B | 0.11495 | 0.58223 | 0.31751 | 0.1079* | |
H12A | −0.10374 | 0.46376 | 0.21084 | 0.1084* | |
H12B | −0.02286 | 0.59635 | 0.17971 | 0.1084* | |
H13A | 0.04060 | 0.34015 | 0.11058 | 0.0734* | |
H13B | 0.06364 | 0.47467 | 0.05035 | 0.0734* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0758 (9) | 0.0638 (8) | 0.0492 (6) | 0.0015 (8) | −0.0174 (6) | 0.0122 (5) |
O2 | 0.0591 (7) | 0.0564 (7) | 0.0462 (5) | −0.0071 (6) | −0.0155 (5) | 0.0043 (5) |
N1 | 0.0463 (7) | 0.0364 (6) | 0.0402 (5) | −0.0019 (5) | −0.0041 (5) | 0.0042 (4) |
N2 | 0.0445 (6) | 0.0416 (7) | 0.0514 (6) | −0.0014 (6) | −0.0012 (6) | 0.0003 (5) |
C1 | 0.0437 (7) | 0.0471 (8) | 0.0373 (6) | −0.0010 (6) | −0.0024 (6) | 0.0030 (5) |
C2 | 0.0434 (7) | 0.0445 (8) | 0.0382 (6) | −0.0015 (6) | 0.0016 (5) | −0.0022 (5) |
C3 | 0.0637 (11) | 0.0584 (10) | 0.0502 (8) | −0.0085 (9) | −0.0011 (8) | −0.0144 (7) |
C4 | 0.0835 (14) | 0.0493 (11) | 0.0747 (12) | −0.0092 (11) | 0.0059 (11) | −0.0199 (9) |
C5 | 0.0834 (14) | 0.0378 (9) | 0.0848 (13) | 0.0019 (10) | 0.0067 (12) | 0.0005 (9) |
C6 | 0.0600 (10) | 0.0418 (8) | 0.0589 (9) | 0.0041 (8) | −0.0001 (8) | 0.0068 (7) |
C7 | 0.0419 (7) | 0.0384 (7) | 0.0407 (6) | −0.0001 (6) | 0.0010 (5) | 0.0027 (5) |
C8 | 0.0380 (6) | 0.0424 (7) | 0.0383 (6) | −0.0014 (6) | −0.0005 (5) | 0.0054 (5) |
C9 | 0.0432 (7) | 0.0384 (7) | 0.0516 (7) | −0.0055 (6) | 0.0033 (6) | 0.0075 (6) |
C10 | 0.0626 (11) | 0.0704 (12) | 0.0531 (9) | 0.0027 (10) | −0.0013 (8) | −0.0048 (8) |
C11 | 0.0835 (16) | 0.115 (2) | 0.0715 (13) | 0.0182 (17) | 0.0118 (12) | −0.0226 (14) |
C12 | 0.0615 (13) | 0.120 (2) | 0.0900 (16) | 0.0255 (16) | 0.0038 (12) | −0.0157 (17) |
C13 | 0.0477 (9) | 0.0724 (12) | 0.0634 (10) | 0.0053 (9) | −0.0076 (8) | −0.0028 (9) |
O1—C1 | 1.2059 (19) | C11—C12 | 1.508 (4) |
O2—C8 | 1.2084 (18) | C12—C13 | 1.505 (4) |
N1—C1 | 1.3978 (19) | C3—H3A | 0.9300 |
N1—C8 | 1.3966 (19) | C4—H4A | 0.9300 |
N1—C9 | 1.4699 (19) | C5—H5A | 0.9300 |
N2—C9 | 1.425 (2) | C6—H6A | 0.9300 |
N2—C10 | 1.454 (2) | C9—H9A | 0.9700 |
N2—C13 | 1.456 (2) | C9—H9B | 0.9700 |
C1—C2 | 1.475 (2) | C10—H10A | 0.9700 |
C2—C3 | 1.375 (2) | C10—H10B | 0.9700 |
C2—C7 | 1.389 (2) | C11—H11A | 0.9700 |
C3—C4 | 1.382 (3) | C11—H11B | 0.9700 |
C4—C5 | 1.383 (3) | C12—H12A | 0.9700 |
C5—C6 | 1.379 (3) | C12—H12B | 0.9700 |
C6—C7 | 1.377 (2) | C13—H13A | 0.9700 |
C7—C8 | 1.480 (2) | C13—H13B | 0.9700 |
C10—C11 | 1.510 (4) | ||
O1···C13 | 3.375 (2) | C13···C2i | 3.575 (2) |
O1···C9i | 3.295 (2) | C13···C1 | 3.441 (3) |
O2···C10 | 3.352 (2) | C1···H13A | 2.9000 |
O2···C6ii | 3.334 (2) | C2···H11Aix | 3.0700 |
O2···C3iii | 3.340 (2) | C2···H13Bv | 3.0800 |
O1···H9Ai | 2.6100 | C6···H12Aix | 2.9700 |
O1···H9B | 2.6000 | C7···H13Bv | 3.0900 |
O2···H9A | 2.6600 | C7···H12Aix | 3.0200 |
O2···H3Aiii | 2.5100 | C8···H10B | 2.9300 |
O2···H10B | 2.7700 | H3A···O2vi | 2.5100 |
O2···H6Aii | 2.6600 | H5A···N2vii | 2.5400 |
N2···C5iv | 3.405 (2) | H6A···O2viii | 2.6600 |
N1···H10B | 2.8500 | H9A···O2 | 2.6600 |
N1···H13A | 2.7300 | H9A···H10A | 2.5600 |
N2···H5Aiv | 2.5400 | H9A···O1v | 2.6100 |
C1···C13 | 3.441 (3) | H9B···O1 | 2.6000 |
C1···C13v | 3.563 (2) | H10A···H9A | 2.5600 |
C2···C13v | 3.575 (2) | H10B···O2 | 2.7700 |
C3···O2vi | 3.340 (2) | H10B···N1 | 2.8500 |
C5···N2vii | 3.405 (2) | H10B···C8 | 2.9300 |
C6···O2viii | 3.334 (2) | H11A···C2x | 3.0700 |
C8···C10 | 3.508 (2) | H12A···C6x | 2.9700 |
C9···O1v | 3.295 (2) | H12A···C7x | 3.0200 |
C10···O2 | 3.352 (2) | H13A···N1 | 2.7300 |
C10···C8 | 3.508 (2) | H13A···C1 | 2.9000 |
C13···C1i | 3.563 (2) | H13B···C2i | 3.0800 |
C13···O1 | 3.375 (2) | H13B···C7i | 3.0900 |
C1—N1—C8 | 111.31 (12) | C5—C4—H4A | 119.00 |
C1—N1—C9 | 123.71 (12) | C4—C5—H5A | 119.00 |
C8—N1—C9 | 124.65 (12) | C6—C5—H5A | 119.00 |
C9—N2—C10 | 117.53 (14) | C5—C6—H6A | 121.00 |
C9—N2—C13 | 117.33 (14) | C7—C6—H6A | 121.00 |
C10—N2—C13 | 105.89 (14) | N1—C9—H9A | 108.00 |
O1—C1—N1 | 124.56 (16) | N1—C9—H9B | 108.00 |
O1—C1—C2 | 129.11 (15) | N2—C9—H9A | 108.00 |
N1—C1—C2 | 106.32 (12) | N2—C9—H9B | 108.00 |
C1—C2—C3 | 130.40 (14) | H9A—C9—H9B | 107.00 |
C1—C2—C7 | 108.06 (13) | N2—C10—H10A | 111.00 |
C3—C2—C7 | 121.54 (16) | N2—C10—H10B | 111.00 |
C2—C3—C4 | 116.85 (17) | C11—C10—H10A | 111.00 |
C3—C4—C5 | 121.83 (19) | C11—C10—H10B | 111.00 |
C4—C5—C6 | 121.11 (19) | H10A—C10—H10B | 109.00 |
C5—C6—C7 | 117.33 (18) | C10—C11—H11A | 111.00 |
C2—C7—C6 | 121.34 (15) | C10—C11—H11B | 111.00 |
C2—C7—C8 | 108.17 (13) | C12—C11—H11A | 111.00 |
C6—C7—C8 | 130.48 (14) | C12—C11—H11B | 111.00 |
O2—C8—N1 | 125.19 (14) | H11A—C11—H11B | 109.00 |
O2—C8—C7 | 128.76 (14) | C11—C12—H12A | 111.00 |
N1—C8—C7 | 106.05 (12) | C11—C12—H12B | 111.00 |
N1—C9—N2 | 116.58 (13) | C13—C12—H12A | 111.00 |
N2—C10—C11 | 103.03 (16) | C13—C12—H12B | 111.00 |
C10—C11—C12 | 105.8 (2) | H12A—C12—H12B | 109.00 |
C11—C12—C13 | 105.6 (2) | N2—C13—H13A | 111.00 |
N2—C13—C12 | 103.32 (17) | N2—C13—H13B | 111.00 |
C2—C3—H3A | 122.00 | C12—C13—H13A | 111.00 |
C4—C3—H3A | 122.00 | C12—C13—H13B | 111.00 |
C3—C4—H4A | 119.00 | H13A—C13—H13B | 109.00 |
C8—N1—C1—O1 | −175.81 (15) | N1—C1—C2—C3 | 177.47 (17) |
C9—N1—C1—O1 | −2.0 (2) | C3—C2—C7—C6 | 0.3 (2) |
C8—N1—C1—C2 | 3.08 (16) | C1—C2—C7—C6 | −179.93 (14) |
C9—N1—C1—C2 | 176.87 (13) | C1—C2—C7—C8 | 0.79 (17) |
C9—N1—C8—C7 | −176.32 (13) | C1—C2—C3—C4 | 179.79 (18) |
C1—N1—C9—N2 | 94.98 (17) | C7—C2—C3—C4 | −0.4 (3) |
C8—N1—C9—N2 | −92.06 (18) | C3—C2—C7—C8 | −179.03 (15) |
C1—N1—C8—C7 | −2.60 (16) | C2—C3—C4—C5 | 0.5 (3) |
C1—N1—C8—O2 | 177.17 (14) | C3—C4—C5—C6 | −0.3 (4) |
C9—N1—C8—O2 | 3.5 (2) | C4—C5—C6—C7 | 0.1 (3) |
C10—N2—C9—N1 | 69.20 (19) | C5—C6—C7—C2 | −0.1 (3) |
C13—N2—C10—C11 | −39.5 (2) | C5—C6—C7—C8 | 179.03 (18) |
C9—N2—C13—C12 | 173.19 (19) | C2—C7—C8—N1 | 1.04 (16) |
C10—N2—C13—C12 | 39.7 (2) | C2—C7—C8—O2 | −178.72 (15) |
C13—N2—C9—N1 | −58.89 (19) | C6—C7—C8—O2 | 2.1 (3) |
C9—N2—C10—C11 | −172.84 (18) | C6—C7—C8—N1 | −178.15 (16) |
O1—C1—C2—C3 | −3.7 (3) | N2—C10—C11—C12 | 23.4 (3) |
N1—C1—C2—C7 | −2.33 (17) | C10—C11—C12—C13 | 0.2 (3) |
O1—C1—C2—C7 | 176.49 (17) | C11—C12—C13—N2 | −23.6 (3) |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1/2, −y, z+1/2; (iv) x, y+1, z; (v) x+1/2, −y+1/2, −z; (vi) −x+1/2, −y, z−1/2; (vii) x, y−1, z; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, y−1/2, −z+1/2; (x) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O2vi | 0.9300 | 2.5100 | 3.340 (2) | 149.00 |
C5—H5A···N2vii | 0.9300 | 2.5400 | 3.405 (2) | 155.00 |
Symmetry codes: (vi) −x+1/2, −y, z−1/2; (vii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C13H14N2O2 |
Mr | 230.26 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 9.0609 (3), 10.0777 (3), 13.0192 (3) |
V (Å3) | 1188.82 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa-APEX2 |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.974, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10764, 2752, 1943 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.791 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.134, 1.03 |
No. of reflections | 2752 |
No. of parameters | 155 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.21 |
Absolute structure | Flack (1983), 1957 Friedel pairs |
Computer programs: APEX2 (Bruker, 2004), APEX2/SAINT (Bruker, 2004), SAINT/XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-32 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O2i | 0.9300 | 2.5100 | 3.340 (2) | 149.00 |
C5—H5A···N2ii | 0.9300 | 2.5400 | 3.405 (2) | 155.00 |
Symmetry codes: (i) −x+1/2, −y, z−1/2; (ii) x, y−1, z. |
Substitituted pyrrolidine compounds have been found to have antimicrobial antifungal activity against various pathogens except Basillus substilis (Amal Raj et al., 2003). Pyrrolidine derivatives possess anti-influenza virus (Stylianakis et al., 2003), anticonvulsant (Obniska & Zagorska, 2003; Obniska et al., 2005), and other antiviral (Kolocouris et al., 1994) activities. Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities (Lima et al., 2002; Orzeszka et al., 2000; Bailleux et al., 1993). Phthalimides have also served as starting materials and intermediates for synthesis of alkaloids (Couture et al., 1998) pharmacophores (Couture et al., 1997). Several optically active pyrrolidine compounds have been used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). In view of its importance and to obtain more detailed information of the structure and conformation of the title compound, its crystal structure was determined.
All C—C and C—N bond lengths in the pyrrolidine ring are comparable with values in related pyrrolidine derivatives (Abdul Ajees et al., 2002).
The sum of the angles at N2 of the pyrrolidine ring (340.69°) is in accordance with sp3 hybridization. The pyrrolidine ring adopts an envelope conformation and puckering parameters q2=0.3772 (2) Å and φ2 = 359.7 (4)° (Cremer & Pople,1975). Atom N2 deviates by 0.248 (2) Å from the least squares plane through the remaining four C atoms (C10/C11/C12/C13) of the ring.
The pyrrolidine ring makes a dihedral angle of 78.72 (8)° with the isoindole-1–3-dione ring. The molecular structure is stabilized by C—H···O and C—H···N interactions (Table 2 and Fig 2.).