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In the title compound, C
22H
21NO
5, the pyrrolidine ring and the five-membered ring in the indene group have envelope conformations, while the furan ring adopts a twist conformation. Weak intermolecular C—H
O interactions link the molecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.
Supporting information
CCDC reference: 287539
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.131
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
To a refluxing solution of ninhydrin (1 mmol) and sarcosine (1 mmol) in methanol was added methyl 3-hydroxy-α-methylene-3-phenylpropanate (1 mmol). The completion of the reaction was monitored by thin-layer chromatography and the solvent was evaporated under reduced pressure. The crude products were purified by column chromatography and eluted with a hexane–ethyl acetate (9:1) mixture to afford the title compound. The compound was recrystallized from a hexane–ethyl acetate (1:1) mixture as diffraction quality crystals.
The H atoms were positioned geometrically and treated as riding on their parent C atoms, with C—H = 0.93–0.98 Å, O—H = 0.82 Å and Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C or O) for the other H atoms.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
Methyl 11,2,3,3a-5a-hydroxy-1-methyl-10-oxo-4-phenyl 10
H-indeno[1,2-
b]furo[3,4-
b]pyrrole-3a-carboxylate
top
Crystal data top
C22H21NO5 | Z = 2 |
Mr = 379.40 | F(000) = 400 |
Triclinic, P1 | Dx = 1.324 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6216 (5) Å | Cell parameters from 5288 reflections |
b = 10.3055 (6) Å | θ = 2.5–26.5° |
c = 11.7758 (6) Å | µ = 0.09 mm−1 |
α = 79.462 (1)° | T = 293 K |
β = 79.377 (1)° | Block, colourless |
γ = 68.876 (1)° | 0.24 × 0.22 × 0.19 mm |
V = 951.48 (9) Å3 | |
Data collection top
CCD Area Detector diffractometer | 3820 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −11→11 |
10895 measured reflections | k = −13→13 |
4331 independent reflections | l = −15→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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.1473P] where P = (Fo2 + 2Fc2)/3 |
4331 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C22H21NO5 | γ = 68.876 (1)° |
Mr = 379.40 | V = 951.48 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6216 (5) Å | Mo Kα radiation |
b = 10.3055 (6) Å | µ = 0.09 mm−1 |
c = 11.7758 (6) Å | T = 293 K |
α = 79.462 (1)° | 0.24 × 0.22 × 0.19 mm |
β = 79.377 (1)° | |
Data collection top
CCD Area Detector diffractometer | 3820 reflections with I > 2σ(I) |
10895 measured reflections | Rint = 0.015 |
4331 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
4331 reflections | Δρmin = −0.19 e Å−3 |
255 parameters | |
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 | |
N1 | 0.33283 (14) | 0.84122 (12) | 0.44108 (9) | 0.0475 (3) | |
O1 | −0.01217 (10) | 0.93957 (8) | 0.31743 (7) | 0.0426 (2) | |
O2 | 0.02620 (12) | 0.83333 (10) | 0.50233 (8) | 0.0505 (2) | |
H2 | 0.0818 | 0.8709 | 0.5253 | 0.076* | |
O3 | 0.50446 (12) | 0.58998 (10) | 0.30407 (10) | 0.0593 (3) | |
O4 | 0.53542 (14) | 0.89342 (14) | 0.13066 (11) | 0.0728 (3) | |
O5 | 0.37918 (12) | 0.78388 (10) | 0.08512 (8) | 0.0528 (2) | |
C1 | 0.27034 (14) | 0.80094 (12) | 0.35086 (10) | 0.0378 (2) | |
C2 | 0.26760 (13) | 0.91560 (11) | 0.24361 (9) | 0.0354 (2) | |
C3 | 0.28825 (16) | 1.03305 (13) | 0.29631 (11) | 0.0446 (3) | |
H3A | 0.3437 | 1.0875 | 0.2385 | 0.054* | |
H3B | 0.1803 | 1.0952 | 0.3274 | 0.054* | |
C4 | 0.39500 (19) | 0.95659 (16) | 0.39218 (13) | 0.0559 (3) | |
H4A | 0.5128 | 0.9219 | 0.3613 | 0.067* | |
H4B | 0.3802 | 1.0171 | 0.4503 | 0.067* | |
C5 | 0.4357 (2) | 0.73189 (18) | 0.52009 (13) | 0.0632 (4) | |
H5A | 0.3808 | 0.6646 | 0.5519 | 0.095* | |
H5B | 0.4512 | 0.7730 | 0.5821 | 0.095* | |
H5C | 0.5428 | 0.6861 | 0.4783 | 0.095* | |
C6 | 0.35457 (15) | 0.64900 (12) | 0.32243 (11) | 0.0433 (3) | |
C7 | 0.22171 (16) | 0.59118 (12) | 0.32277 (11) | 0.0448 (3) | |
C8 | 0.2363 (2) | 0.46259 (14) | 0.29157 (13) | 0.0579 (4) | |
H8 | 0.3407 | 0.3993 | 0.2677 | 0.070* | |
C9 | 0.0926 (2) | 0.43207 (16) | 0.29708 (16) | 0.0685 (4) | |
H9 | 0.0996 | 0.3470 | 0.2765 | 0.082* | |
C10 | −0.0630 (2) | 0.52626 (18) | 0.33287 (16) | 0.0679 (4) | |
H10 | −0.1587 | 0.5030 | 0.3366 | 0.081* | |
C11 | −0.07835 (19) | 0.65410 (16) | 0.36308 (13) | 0.0555 (3) | |
H11 | −0.1831 | 0.7175 | 0.3861 | 0.067* | |
C12 | 0.06611 (15) | 0.68548 (12) | 0.35822 (10) | 0.0423 (3) | |
C13 | 0.08061 (14) | 0.81680 (12) | 0.38647 (10) | 0.0392 (3) | |
C14 | 0.09009 (13) | 0.95232 (11) | 0.20878 (10) | 0.0364 (2) | |
H14 | 0.0918 | 0.8826 | 0.1616 | 0.044* | |
C15 | 0.41024 (15) | 0.86508 (13) | 0.14744 (11) | 0.0426 (3) | |
C16 | 0.5120 (2) | 0.7237 (2) | −0.00405 (17) | 0.0811 (5) | |
H16A | 0.4775 | 0.6674 | −0.0439 | 0.122* | |
H16B | 0.6106 | 0.6663 | 0.0311 | 0.122* | |
H16C | 0.5363 | 0.7975 | −0.0587 | 0.122* | |
C17 | 0.02073 (14) | 1.09719 (12) | 0.14414 (10) | 0.0393 (3) | |
C18 | −0.11627 (18) | 1.19970 (14) | 0.19292 (12) | 0.0524 (3) | |
H18 | −0.1690 | 1.1794 | 0.2669 | 0.063* | |
C19 | −0.1755 (2) | 1.33300 (16) | 0.13187 (15) | 0.0648 (4) | |
H19 | −0.2678 | 1.4015 | 0.1650 | 0.078* | |
C20 | −0.0979 (2) | 1.36381 (16) | 0.02252 (15) | 0.0645 (4) | |
H20 | −0.1372 | 1.4532 | −0.0180 | 0.077* | |
C21 | 0.0376 (2) | 1.26252 (17) | −0.02670 (14) | 0.0643 (4) | |
H21 | 0.0901 | 1.2834 | −0.1006 | 0.077* | |
C22 | 0.09664 (18) | 1.12907 (15) | 0.03351 (12) | 0.0531 (3) | |
H22 | 0.1878 | 1.0606 | −0.0007 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0484 (6) | 0.0509 (6) | 0.0427 (5) | −0.0151 (5) | −0.0139 (4) | −0.0001 (4) |
O1 | 0.0324 (4) | 0.0374 (4) | 0.0490 (5) | −0.0078 (3) | 0.0007 (3) | 0.0022 (3) |
O2 | 0.0524 (5) | 0.0540 (5) | 0.0412 (5) | −0.0189 (4) | 0.0075 (4) | −0.0077 (4) |
O3 | 0.0404 (5) | 0.0477 (5) | 0.0735 (7) | −0.0013 (4) | −0.0008 (4) | −0.0022 (5) |
O4 | 0.0491 (6) | 0.0902 (8) | 0.0844 (8) | −0.0360 (6) | 0.0190 (5) | −0.0261 (6) |
O5 | 0.0493 (5) | 0.0563 (6) | 0.0494 (5) | −0.0144 (4) | 0.0053 (4) | −0.0172 (4) |
C1 | 0.0345 (5) | 0.0359 (5) | 0.0385 (5) | −0.0098 (4) | −0.0029 (4) | −0.0001 (4) |
C2 | 0.0329 (5) | 0.0339 (5) | 0.0372 (5) | −0.0110 (4) | −0.0027 (4) | −0.0010 (4) |
C3 | 0.0474 (6) | 0.0411 (6) | 0.0486 (6) | −0.0191 (5) | −0.0073 (5) | −0.0041 (5) |
C4 | 0.0586 (8) | 0.0582 (8) | 0.0599 (8) | −0.0264 (7) | −0.0200 (6) | −0.0038 (6) |
C5 | 0.0577 (8) | 0.0726 (10) | 0.0520 (8) | −0.0145 (7) | −0.0198 (6) | 0.0078 (7) |
C6 | 0.0415 (6) | 0.0366 (6) | 0.0418 (6) | −0.0060 (5) | −0.0020 (5) | 0.0017 (4) |
C7 | 0.0510 (7) | 0.0344 (6) | 0.0437 (6) | −0.0117 (5) | −0.0055 (5) | 0.0021 (5) |
C8 | 0.0692 (9) | 0.0370 (6) | 0.0614 (8) | −0.0111 (6) | −0.0115 (7) | −0.0020 (6) |
C9 | 0.0902 (12) | 0.0430 (7) | 0.0800 (11) | −0.0299 (8) | −0.0222 (9) | −0.0002 (7) |
C10 | 0.0745 (10) | 0.0596 (9) | 0.0819 (11) | −0.0411 (8) | −0.0164 (9) | 0.0054 (8) |
C11 | 0.0511 (7) | 0.0535 (8) | 0.0622 (8) | −0.0248 (6) | −0.0023 (6) | 0.0018 (6) |
C12 | 0.0452 (6) | 0.0376 (6) | 0.0409 (6) | −0.0160 (5) | −0.0026 (5) | 0.0040 (4) |
C13 | 0.0362 (5) | 0.0361 (5) | 0.0399 (6) | −0.0106 (4) | 0.0006 (4) | −0.0004 (4) |
C14 | 0.0329 (5) | 0.0350 (5) | 0.0401 (6) | −0.0112 (4) | −0.0040 (4) | −0.0028 (4) |
C15 | 0.0366 (6) | 0.0426 (6) | 0.0432 (6) | −0.0120 (5) | 0.0005 (5) | −0.0011 (5) |
C16 | 0.0754 (11) | 0.0878 (13) | 0.0702 (11) | −0.0177 (10) | 0.0216 (9) | −0.0375 (10) |
C17 | 0.0386 (6) | 0.0370 (6) | 0.0430 (6) | −0.0121 (4) | −0.0119 (4) | −0.0014 (4) |
C18 | 0.0515 (7) | 0.0455 (7) | 0.0490 (7) | −0.0035 (5) | −0.0094 (6) | −0.0022 (5) |
C19 | 0.0657 (9) | 0.0436 (7) | 0.0721 (10) | 0.0013 (6) | −0.0198 (8) | −0.0052 (7) |
C20 | 0.0737 (10) | 0.0431 (7) | 0.0726 (10) | −0.0148 (7) | −0.0293 (8) | 0.0128 (7) |
C21 | 0.0702 (10) | 0.0620 (9) | 0.0556 (8) | −0.0253 (8) | −0.0133 (7) | 0.0162 (7) |
C22 | 0.0519 (7) | 0.0499 (7) | 0.0493 (7) | −0.0129 (6) | −0.0050 (6) | 0.0033 (6) |
Geometric parameters (Å, º) top
N1—C5 | 1.457 (2) | C7—C8 | 1.3956 (19) |
N1—C1 | 1.458 (2) | C8—C9 | 1.372 (2) |
N1—C4 | 1.459 (2) | C8—H8 | 0.9300 |
O1—C13 | 1.4268 (13) | C9—C10 | 1.386 (3) |
O1—C14 | 1.4275 (13) | C9—H9 | 0.9300 |
O2—C13 | 1.3791 (14) | C10—C11 | 1.381 (2) |
O2—H2 | 0.8200 | C10—H10 | 0.9300 |
O3—C6 | 1.2105 (15) | C11—C12 | 1.3843 (19) |
O4—C15 | 1.1902 (16) | C11—H11 | 0.9300 |
O5—C15 | 1.3300 (16) | C12—C13 | 1.5032 (17) |
O5—C16 | 1.4428 (17) | C14—C17 | 1.5081 (15) |
C1—C6 | 1.5407 (16) | C14—H14 | 0.9800 |
C1—C2 | 1.561 (2) | C16—H16A | 0.9600 |
C1—C13 | 1.5678 (16) | C16—H16B | 0.9600 |
C2—C15 | 1.5188 (16) | C16—H16C | 0.9600 |
C2—C3 | 1.534 (2) | C17—C18 | 1.3833 (18) |
C2—C14 | 1.5528 (15) | C17—C22 | 1.3847 (18) |
C3—C4 | 1.509 (2) | C18—C19 | 1.3904 (19) |
C3—H3A | 0.9700 | C18—H18 | 0.9300 |
C3—H3B | 0.9700 | C19—C20 | 1.376 (2) |
C4—H4A | 0.9700 | C19—H19 | 0.9300 |
C4—H4B | 0.9700 | C20—C21 | 1.372 (3) |
C5—H5A | 0.9600 | C20—H20 | 0.9300 |
C5—H5B | 0.9600 | C21—C22 | 1.3874 (19) |
C5—H5C | 0.9600 | C21—H21 | 0.9300 |
C6—C7 | 1.4685 (19) | C22—H22 | 0.9300 |
C7—C12 | 1.3859 (18) | | |
| | | |
C5—N1—C1 | 119.0 (1) | C11—C10—C9 | 121.10 (15) |
C5—N1—C4 | 115.6 (1) | C11—C10—H10 | 119.4 |
C1—N1—C4 | 109.7 (1) | C9—C10—H10 | 119.4 |
C13—O1—C14 | 107.32 (8) | C10—C11—C12 | 118.33 (14) |
C13—O2—H2 | 109.5 | C10—C11—H11 | 120.8 |
C15—O5—C16 | 115.89 (12) | C12—C11—H11 | 120.8 |
N1—C1—C6 | 117.31 (10) | C11—C12—C7 | 120.58 (12) |
N1—C1—C2 | 106.19 (9) | C11—C12—C13 | 127.85 (12) |
C6—C1—C2 | 114.57 (9) | C7—C12—C13 | 111.56 (11) |
N1—C1—C13 | 110.39 (9) | O2—C13—O1 | 108.43 (9) |
C6—C1—C13 | 104.17 (9) | O2—C13—C12 | 111.36 (9) |
C2—C1—C13 | 103.32 (8) | O1—C13—C12 | 112.38 (10) |
C15—C2—C3 | 110.54 (9) | O2—C13—C1 | 113.02 (10) |
C15—C2—C14 | 114.35 (9) | O1—C13—C1 | 106.56 (8) |
C3—C2—C14 | 113.47 (9) | C12—C13—C1 | 105.03 (9) |
C15—C2—C1 | 112.53 (9) | O1—C14—C17 | 110.06 (9) |
C3—C2—C1 | 102.50 (9) | O1—C14—C2 | 103.86 (8) |
C14—C2—C1 | 102.59 (8) | C17—C14—C2 | 114.81 (9) |
C4—C3—C2 | 104.12 (10) | O1—C14—H14 | 109.3 |
C4—C3—H3A | 110.9 | C17—C14—H14 | 109.3 |
C2—C3—H3A | 110.9 | C2—C14—H14 | 109.3 |
C4—C3—H3B | 110.9 | O4—C15—O5 | 124.09 (12) |
C2—C3—H3B | 110.9 | O4—C15—C2 | 124.12 (12) |
H3A—C3—H3B | 109.0 | O5—C15—C2 | 111.78 (10) |
N1—C4—C3 | 103.37 (10) | O5—C16—H16A | 109.5 |
N1—C4—H4A | 111.1 | O5—C16—H16B | 109.5 |
C3—C4—H4A | 111.1 | H16A—C16—H16B | 109.5 |
N1—C4—H4B | 111.1 | O5—C16—H16C | 109.5 |
C3—C4—H4B | 111.1 | H16A—C16—H16C | 109.5 |
H4A—C4—H4B | 109.1 | H16B—C16—H16C | 109.5 |
N1—C5—H5A | 109.5 | C18—C17—C22 | 119.02 (12) |
N1—C5—H5B | 109.5 | C18—C17—C14 | 121.67 (11) |
H5A—C5—H5B | 109.5 | C22—C17—C14 | 119.31 (11) |
N1—C5—H5C | 109.5 | C17—C18—C19 | 120.30 (14) |
H5A—C5—H5C | 109.5 | C17—C18—H18 | 119.8 |
H5B—C5—H5C | 109.5 | C19—C18—H18 | 119.8 |
O3—C6—C7 | 127.23 (12) | C20—C19—C18 | 120.13 (15) |
O3—C6—C1 | 124.83 (12) | C20—C19—H19 | 119.9 |
C7—C6—C1 | 107.94 (10) | C18—C19—H19 | 119.9 |
C12—C7—C8 | 120.84 (13) | C21—C20—C19 | 119.93 (13) |
C12—C7—C6 | 110.49 (11) | C21—C20—H20 | 120.0 |
C8—C7—C6 | 128.66 (13) | C19—C20—H20 | 120.0 |
C9—C8—C7 | 118.20 (15) | C20—C21—C22 | 120.19 (14) |
C9—C8—H8 | 120.9 | C20—C21—H21 | 119.9 |
C7—C8—H8 | 120.9 | C22—C21—H21 | 119.9 |
C8—C9—C10 | 120.94 (14) | C17—C22—C21 | 120.43 (14) |
C8—C9—H9 | 119.5 | C17—C22—H22 | 119.8 |
C10—C9—H9 | 119.5 | C21—C22—H22 | 119.8 |
| | | |
C5—N1—C1—C6 | −16.33 (16) | C14—O1—C13—C1 | 31.46 (11) |
C4—N1—C1—C6 | 120.05 (12) | C11—C12—C13—O2 | 64.01 (16) |
C5—N1—C1—C2 | −145.93 (11) | C7—C12—C13—O2 | −116.71 (11) |
C4—N1—C1—C2 | −9.54 (13) | C11—C12—C13—O1 | −57.86 (16) |
C5—N1—C1—C13 | 102.74 (13) | C7—C12—C13—O1 | 121.41 (11) |
C4—N1—C1—C13 | −120.88 (11) | C11—C12—C13—C1 | −173.31 (12) |
N1—C1—C2—C15 | 104.64 (11) | C7—C12—C13—C1 | 5.96 (13) |
C6—C1—C2—C15 | −26.52 (14) | N1—C1—C13—O2 | −13.78 (13) |
C13—C1—C2—C15 | −139.16 (10) | C6—C1—C13—O2 | 113.00 (10) |
N1—C1—C2—C3 | −14.12 (11) | C2—C1—C13—O2 | −126.96 (10) |
C6—C1—C2—C3 | −145.27 (10) | N1—C1—C13—O1 | 105.21 (10) |
C13—C1—C2—C3 | 102.08 (10) | C6—C1—C13—O1 | −128.01 (9) |
N1—C1—C2—C14 | −131.99 (9) | C2—C1—C13—O1 | −7.97 (11) |
C6—C1—C2—C14 | 96.85 (11) | N1—C1—C13—C12 | −135.37 (10) |
C13—C1—C2—C14 | −15.79 (11) | C6—C1—C13—C12 | −8.59 (11) |
C15—C2—C3—C4 | −88.43 (12) | C2—C1—C13—C12 | 111.45 (10) |
C14—C2—C3—C4 | 141.57 (11) | C13—O1—C14—C17 | −165.37 (9) |
C1—C2—C3—C4 | 31.71 (12) | C13—O1—C14—C2 | −41.98 (11) |
C5—N1—C4—C3 | 167.76 (12) | C15—C2—C14—O1 | 156.91 (9) |
C1—N1—C4—C3 | 29.75 (14) | C3—C2—C14—O1 | −75.04 (11) |
C2—C3—C4—N1 | −38.00 (13) | C1—C2—C14—O1 | 34.76 (10) |
N1—C1—C6—O3 | −48.73 (17) | C15—C2—C14—C17 | −82.87 (12) |
C2—C1—C6—O3 | 76.80 (15) | C3—C2—C14—C17 | 45.19 (13) |
C13—C1—C6—O3 | −171.07 (12) | C1—C2—C14—C17 | 154.99 (9) |
N1—C1—C6—C7 | 130.88 (11) | C16—O5—C15—O4 | 2.8 (2) |
C2—C1—C6—C7 | −103.59 (11) | C16—O5—C15—C2 | −176.40 (13) |
C13—C1—C6—C7 | 8.55 (12) | C3—C2—C15—O4 | 13.12 (18) |
O3—C6—C7—C12 | 174.30 (13) | C14—C2—C15—O4 | 142.65 (13) |
C1—C6—C7—C12 | −5.30 (14) | C1—C2—C15—O4 | −100.81 (15) |
O3—C6—C7—C8 | −6.8 (2) | C3—C2—C15—O5 | −167.65 (10) |
C1—C6—C7—C8 | 173.60 (13) | C14—C2—C15—O5 | −38.12 (13) |
C12—C7—C8—C9 | −0.1 (2) | C1—C2—C15—O5 | 78.42 (12) |
C6—C7—C8—C9 | −178.86 (13) | O1—C14—C17—C18 | 3.95 (16) |
C7—C8—C9—C10 | −0.1 (2) | C2—C14—C17—C18 | −112.79 (13) |
C8—C9—C10—C11 | 0.6 (3) | O1—C14—C17—C22 | −176.57 (11) |
C9—C10—C11—C12 | −0.8 (2) | C2—C14—C17—C22 | 66.69 (14) |
C10—C11—C12—C7 | 0.6 (2) | C22—C17—C18—C19 | −0.6 (2) |
C10—C11—C12—C13 | 179.86 (13) | C14—C17—C18—C19 | 178.91 (13) |
C8—C7—C12—C11 | −0.2 (2) | C17—C18—C19—C20 | −0.1 (2) |
C6—C7—C12—C11 | 178.80 (11) | C18—C19—C20—C21 | 0.4 (3) |
C8—C7—C12—C13 | −179.53 (12) | C19—C20—C21—C22 | 0.0 (3) |
C6—C7—C12—C13 | −0.54 (14) | C18—C17—C22—C21 | 1.0 (2) |
C14—O1—C13—O2 | 153.40 (9) | C14—C17—C22—C21 | −178.51 (13) |
C14—O1—C13—C12 | −83.06 (11) | C20—C21—C22—C17 | −0.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O2i | 0.97 | 2.45 | 3.317 (2) | 148 |
O2—H2···N1 | 0.82 | 2.15 | 2.636 (2) | 118 |
Symmetry code: (i) −x, −y+2, −z+1. |
Experimental details
Crystal data |
Chemical formula | C22H21NO5 |
Mr | 379.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.6216 (5), 10.3055 (6), 11.7758 (6) |
α, β, γ (°) | 79.462 (1), 79.377 (1), 68.876 (1) |
V (Å3) | 951.48 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.22 × 0.19 |
|
Data collection |
Diffractometer | CCD Area Detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10895, 4331, 3820 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.131, 1.04 |
No. of reflections | 4331 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.19 |
Selected geometric parameters (Å, º) topN1—C5 | 1.457 (2) | C1—C2 | 1.561 (2) |
N1—C1 | 1.458 (2) | C2—C3 | 1.534 (2) |
N1—C4 | 1.459 (2) | C3—C4 | 1.509 (2) |
| | | |
C5—N1—C1 | 119.0 (1) | C1—N1—C4 | 109.7 (1) |
C5—N1—C4 | 115.6 (1) | | |
| | | |
C16—O5—C15—O4 | 2.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O2i | 0.97 | 2.45 | 3.317 (2) | 148 |
O2—H2···N1 | 0.82 | 2.15 | 2.636 (2) | 118 |
Symmetry code: (i) −x, −y+2, −z+1. |
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Highly substituted pyrrolidines have attracted much interest in the past few years, since they constitute the main structural element of many alkaloids and pharmacologically active compounds (Subramaniyan & Raghunathan, 2001). Pyrrolidine derivatives inhibit α-mannosidase activity and growth of human glioblastoma and melanoma cells (Fiaux et al., 2005). These derivatives also exhibit anti-influenza virus activity (Stylianakis et al., 2003). Furan derivatives can promote immune activity, inhibit immune activity and blood platelet aggregation (Li et al., 2005). In view of its medicinal importance, the crystal structure determination of the title compound, (I), was carried out by X-ray diffraction.
A displacement ellipsoid plot of (I) is shown in Fig. 1. It consists of four fused rings, viz. pyrrolidine (A), furan (B), indene (rings C and D) and phenyl (E), and a methoxycarbonyl group. The bond lengths in the pyrrolidine ring are comparable with those observed in related structures (Abdul Ajees et al., 2002; Selvanayagam et al., 2004). The sum of the angles around atom N1 [344.3 (2)°] is in accordance with sp3-hybridization.
The methoxy carbonyl group (C15/O4/O5/C16) is planar, with a maximum deviation of 0.006 (1) Å for atom O5. The C—O bond of the ester group is in a syn orientation. The torsion angle C16—O5—C15—O4 is 2.8 (2)°. The methoxy carbonyl group and phenyl ring E make a dihedral angle of 76.8 (1)°.
Ring A adopts an envelope conformation, with puckering parameters q2 = 0.362 (2) Å and ϕ = −59.6 (2)° (Cremer & Pople, 1975). Atom C3 deviates by −0.521 (1) Å from the least-squares plane N1/C1/C2/C4. Ring B adopts a twist conformation, with puckering parameters q2 = 0.517 (2) Å and ϕ = −121.2 (2)°, and displacement asymmetry parameters ΔS(C13) = 0.086 (1) and Δ2(C14) = 0.032 (1) (Nardelli, 1983).
The five-membered ring of the indene moiety adopts an envelope conformation, with puckering parameters q2 = 0.196 (2) Å and ϕ = 170.0 (3)°. Atom C6 deviates by −0.118 (1) Å from the least-squares plane C1/C7/C12/C14. The dihedral angle between the fused six- and five-membered rings (C and D) of the indene moiety is 4.6 (1)°.
An intramolecular O—H···N hydrogen bond is observed in (I) (Table 2). Weak intermolecular C—H···O interactions (Table 2) link the molecules into centrosymmetric dimers. The crystal packing (Fig. 2) is further stabilized by van der Waals forces.