organic compounds
The crystal structure of the title compound, C13H13NO3, is stabilized by dipole-dipole and van der Waals forces. The pyrrolidine ring is almost planar, while the central six-membered ring of the indolizine moiety adopts a sofa conformation.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014996/sg6009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014996/sg6009Isup2.hkl |
CCDC reference: 274624
Computing details top
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(10aS)-7-methoxy-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione top
Crystal data top
C13H13NO3 | F(000) = 244 |
Mr = 231.24 | Dx = 1.357 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 864 reflections |
a = 7.423 (1) Å | θ = 3.0–29.9° |
b = 7.034 (1) Å | µ = 0.10 mm−1 |
c = 10.998 (1) Å | T = 296 K |
β = 99.67 (1)° | Block, colorless |
V = 566.08 (12) Å3 | 0.60 × 0.40 × 0.30 mm |
Z = 2 |
Data collection top
Oxford Diffraction Xcalibur CCD diffractometer | 864 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Rotation method data acquisition using ω and φ scans | h = −9→9 |
3959 measured reflections | k = −9→5 |
1380 independent reflections | l = −13→14 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3 |
1380 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.1774 (4) | 0.5473 (6) | 0.0832 (3) | 0.0772 (10) | |
H1A | 0.1110 | 0.4599 | 0.0236 | 0.093* | |
H1B | 0.0900 | 0.6222 | 0.1192 | 0.093* | |
C2 | 0.3005 (5) | 0.6756 (6) | 0.0219 (3) | 0.0807 (10) | |
H2A | 0.2983 | 0.6378 | −0.0632 | 0.097* | |
H2B | 0.2607 | 0.8068 | 0.0233 | 0.097* | |
C3 | 0.4897 (5) | 0.6532 (5) | 0.0951 (3) | 0.0666 (9) | |
N4 | 0.4834 (3) | 0.5212 (4) | 0.1828 (2) | 0.0566 (7) | |
C5 | 0.6373 (3) | 0.4630 (6) | 0.2731 (2) | 0.0599 (7) | |
H5A | 0.7385 | 0.5495 | 0.2709 | 0.072* | |
H5B | 0.6758 | 0.3368 | 0.2529 | 0.072* | |
C6 | 0.7282 (3) | 0.4591 (4) | 0.5027 (2) | 0.0496 (6) | |
H6 | 0.8498 | 0.4587 | 0.4919 | 0.060* | |
C7 | 0.6842 (3) | 0.4571 (5) | 0.6206 (2) | 0.0521 (6) | |
C8 | 0.5028 (4) | 0.4571 (5) | 0.6370 (2) | 0.0585 (7) | |
H8 | 0.4742 | 0.4567 | 0.7162 | 0.070* | |
C9 | 0.3668 (3) | 0.4577 (5) | 0.5371 (3) | 0.0579 (7) | |
H9 | 0.2456 | 0.4574 | 0.5488 | 0.069* | |
C10 | 0.2540 (3) | 0.4516 (5) | 0.3109 (2) | 0.0566 (7) | |
C11 | 0.5891 (3) | 0.4616 (4) | 0.4009 (2) | 0.0442 (6) | |
C12 | 0.4070 (3) | 0.4589 (4) | 0.4165 (2) | 0.0467 (6) | |
C13 | 0.3048 (3) | 0.4383 (5) | 0.1836 (2) | 0.0566 (7) | |
H13 | 0.3074 | 0.3042 | 0.1597 | 0.068* | |
C14 | 0.9993 (4) | 0.4509 (7) | 0.7154 (3) | 0.0850 (11) | |
H14A | 1.0725 | 0.4512 | 0.7961 | 0.128* | |
H14B | 1.0280 | 0.5609 | 0.6705 | 0.128* | |
H14C | 1.0245 | 0.3380 | 0.6721 | 0.128* | |
O15 | 0.6272 (4) | 0.7407 (4) | 0.0806 (2) | 0.0934 (9) | |
O16 | 0.8097 (3) | 0.4548 (4) | 0.72636 (16) | 0.0760 (6) | |
O17 | 0.0945 (2) | 0.4473 (4) | 0.3246 (2) | 0.0870 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0590 (18) | 0.108 (3) | 0.0630 (19) | 0.005 (2) | 0.0056 (15) | −0.007 (2) |
C2 | 0.083 (2) | 0.085 (2) | 0.067 (2) | 0.001 (2) | −0.0077 (19) | 0.001 (2) |
C3 | 0.071 (2) | 0.081 (2) | 0.0474 (17) | −0.008 (2) | 0.0093 (15) | −0.0047 (18) |
N4 | 0.0463 (12) | 0.0768 (18) | 0.0470 (12) | −0.0035 (12) | 0.0085 (10) | 0.0064 (13) |
C5 | 0.0456 (14) | 0.083 (2) | 0.0531 (14) | −0.0005 (18) | 0.0133 (11) | 0.0045 (18) |
C6 | 0.0468 (13) | 0.0509 (15) | 0.0534 (14) | −0.0006 (16) | 0.0148 (11) | 0.0041 (17) |
C7 | 0.0620 (15) | 0.0495 (15) | 0.0469 (14) | 0.0024 (17) | 0.0151 (12) | 0.0033 (16) |
C8 | 0.0706 (17) | 0.0584 (16) | 0.0530 (15) | 0.0066 (19) | 0.0287 (14) | 0.0050 (17) |
C9 | 0.0534 (14) | 0.0588 (16) | 0.0678 (17) | 0.0043 (18) | 0.0285 (13) | 0.0085 (18) |
C10 | 0.0474 (14) | 0.0575 (16) | 0.0669 (18) | 0.0010 (17) | 0.0151 (12) | 0.0073 (18) |
C11 | 0.0455 (13) | 0.0409 (14) | 0.0493 (13) | 0.0010 (15) | 0.0169 (11) | 0.0041 (16) |
C12 | 0.0474 (13) | 0.0412 (14) | 0.0543 (14) | −0.0008 (15) | 0.0167 (11) | 0.0039 (16) |
C13 | 0.0457 (14) | 0.0636 (18) | 0.0609 (16) | −0.0047 (16) | 0.0098 (12) | −0.0047 (17) |
C14 | 0.0652 (18) | 0.128 (3) | 0.0596 (18) | 0.002 (3) | 0.0029 (14) | 0.003 (2) |
O15 | 0.0895 (17) | 0.119 (2) | 0.0703 (14) | −0.0320 (17) | 0.0107 (12) | 0.0209 (14) |
O16 | 0.0701 (12) | 0.1108 (17) | 0.0478 (10) | 0.0047 (16) | 0.0119 (9) | 0.0022 (14) |
O17 | 0.0448 (10) | 0.130 (2) | 0.0899 (14) | −0.0028 (15) | 0.0211 (10) | 0.0148 (17) |
Geometric parameters (Å, º) top
C1—C2 | 1.520 (5) | C6—H6 | 0.9300 |
C1—C13 | 1.533 (4) | C7—O16 | 1.363 (3) |
C1—H1A | 0.9700 | C7—C8 | 1.389 (3) |
C1—H1B | 0.9700 | C8—C9 | 1.361 (4) |
C2—C3 | 1.505 (5) | C8—H8 | 0.9300 |
C2—H2A | 0.9700 | C9—C12 | 1.408 (3) |
C2—H2B | 0.9700 | C9—H9 | 0.9300 |
C3—O15 | 1.225 (4) | C10—O17 | 1.219 (3) |
C3—N4 | 1.345 (4) | C10—C12 | 1.482 (3) |
N4—C5 | 1.441 (3) | C10—C13 | 1.513 (4) |
N4—C13 | 1.450 (3) | C11—C12 | 1.391 (3) |
C5—C11 | 1.508 (3) | C13—H13 | 0.9800 |
C5—H5A | 0.9700 | C14—O16 | 1.433 (3) |
C5—H5B | 0.9700 | C14—H14A | 0.9600 |
C6—C11 | 1.389 (3) | C14—H14B | 0.9600 |
C6—C7 | 1.390 (4) | C14—H14C | 0.9600 |
C2—C1—C13 | 105.8 (2) | C8—C7—C6 | 120.4 (2) |
C2—C1—H1A | 110.6 | C9—C8—C7 | 119.9 (2) |
C13—C1—H1A | 110.6 | C9—C8—H8 | 120.0 |
C2—C1—H1B | 110.6 | C7—C8—H8 | 120.0 |
C13—C1—H1B | 110.6 | C8—C9—C12 | 121.0 (2) |
H1A—C1—H1B | 108.7 | C8—C9—H9 | 119.5 |
C3—C2—C1 | 106.1 (3) | C12—C9—H9 | 119.5 |
C3—C2—H2A | 110.5 | O17—C10—C12 | 122.4 (2) |
C1—C2—H2A | 110.5 | O17—C10—C13 | 120.7 (2) |
C3—C2—H2B | 110.5 | C12—C10—C13 | 116.8 (2) |
C1—C2—H2B | 110.5 | C6—C11—C12 | 120.4 (2) |
H2A—C2—H2B | 108.7 | C6—C11—C5 | 119.4 (2) |
O15—C3—N4 | 124.7 (3) | C12—C11—C5 | 120.1 (2) |
O15—C3—C2 | 126.9 (3) | C11—C12—C9 | 118.7 (2) |
N4—C3—C2 | 108.3 (3) | C11—C12—C10 | 122.4 (2) |
C3—N4—C5 | 124.8 (2) | C9—C12—C10 | 118.9 (2) |
C3—N4—C13 | 115.1 (2) | N4—C13—C10 | 110.5 (2) |
C5—N4—C13 | 120.1 (2) | N4—C13—C1 | 104.4 (3) |
N4—C5—C11 | 111.1 (2) | C10—C13—C1 | 114.6 (2) |
N4—C5—H5A | 109.4 | N4—C13—H13 | 109.0 |
C11—C5—H5A | 109.4 | C10—C13—H13 | 109.0 |
N4—C5—H5B | 109.4 | C1—C13—H13 | 109.0 |
C11—C5—H5B | 109.4 | O16—C14—H14A | 109.5 |
H5A—C5—H5B | 108.0 | O16—C14—H14B | 109.5 |
C11—C6—C7 | 119.5 (2) | H14A—C14—H14B | 109.5 |
C11—C6—H6 | 120.2 | O16—C14—H14C | 109.5 |
C7—C6—H6 | 120.2 | H14A—C14—H14C | 109.5 |
O16—C7—C8 | 115.4 (2) | H14B—C14—H14C | 109.5 |
O16—C7—C6 | 124.2 (2) | C7—O16—C14 | 117.9 (2) |
C13—C1—C2—C3 | −5.6 (4) | C6—C11—C12—C10 | −176.8 (3) |
C1—C2—C3—O15 | −175.4 (3) | C5—C11—C12—C10 | 1.8 (5) |
C1—C2—C3—N4 | 3.5 (4) | C8—C9—C12—C11 | −0.7 (5) |
O15—C3—N4—C5 | 0.1 (5) | C8—C9—C12—C10 | 177.5 (3) |
C2—C3—N4—C5 | −178.8 (3) | O17—C10—C12—C11 | 179.3 (3) |
O15—C3—N4—C13 | 179.1 (3) | C13—C10—C12—C11 | 2.6 (5) |
C2—C3—N4—C13 | 0.2 (4) | O17—C10—C12—C9 | 1.1 (6) |
C3—N4—C5—C11 | 131.8 (3) | C13—C10—C12—C9 | −175.6 (3) |
C13—N4—C5—C11 | −47.2 (4) | C3—N4—C13—C10 | −127.5 (3) |
C11—C6—C7—O16 | −179.9 (3) | C5—N4—C13—C10 | 51.5 (4) |
C11—C6—C7—C8 | 0.2 (5) | C3—N4—C13—C1 | −3.8 (3) |
O16—C7—C8—C9 | −179.5 (3) | C5—N4—C13—C1 | 175.3 (2) |
C6—C7—C8—C9 | 0.5 (5) | O17—C10—C13—N4 | 156.8 (3) |
C7—C8—C9—C12 | −0.2 (6) | C12—C10—C13—N4 | −26.5 (4) |
C7—C6—C11—C12 | −1.1 (5) | O17—C10—C13—C1 | 39.2 (5) |
C7—C6—C11—C5 | −179.8 (3) | C12—C10—C13—C1 | −144.2 (3) |
N4—C5—C11—C6 | −163.0 (3) | C2—C1—C13—N4 | 5.6 (3) |
N4—C5—C11—C12 | 18.3 (4) | C2—C1—C13—C10 | 126.6 (3) |
C6—C11—C12—C9 | 1.4 (5) | C8—C7—O16—C14 | 178.8 (3) |
C5—C11—C12—C9 | −180.0 (3) | C6—C7—O16—C14 | −1.1 (5) |