Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051264/nc2063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051264/nc2063Isup2.hkl |
CCDC reference: 667423
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.160
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT411_ALERT_2_C Short Inter H...H Contact H3 .. H3 .. 2.12 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check
For related literature, see: Fujimori (1990), James et al. (1991), Deshong et al. (1983) and Henrickson et al. (1962).
A mixture of acenapthenequinone (acenaphthylene-1,2-dione) (1 mmol, 0.102 g), sarcosine (2-methylaminoacetic acid)(1 mmol, 0.046 g) and the dipolarophile (3-arylidene-4-chromanone) (1 mmol, 0.2 g) in aqueous methanol (20 ml) was refluxed for 4 h and the reaction was subsequently monitored by TLC for the disappearance of the starting materials. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and petroleum ether-ethyl acetate (9:1) as eluent to give the cycloadduct.
All H atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms using a riding model with C—H = 0.93 - 0.98 Å.
Spiroheterocycles belong to an important class of compounds with highly pronounced biological activities·(James et al. 1991) The central skeleton of many natural products and pharmacologically active compounds contain highly substituted pyrrolidines which are of much prominence (Deshong et al., 1983). Some of the biological active compounds such as rhyncophylline, corynoxeine,nitraphylline,vincatine, horsifiline,etc (Henrickson et al. 1962) contain pyrrolidine and oxindole moiety which forms a separate class of alkaloids (Fujimori 1990). In view of this we have determined the structure of the title compound.
The chromanone moiety consists of a methoxy benzene ring fused with a five membered heterocyclic ring which adopts a sofa conformation. The dihydropyrone ring is in an half chair conformation. The nitrogen atom of the pyrrolidine ring is slightly pyramidal, the sum of the angles amount to 342.04 °.
For related literature, see: Fujimori (1990), James et al. (1991), Deshong et al. (1983) and Henrickson et al. (1962).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. ORTEP representation of the molecule showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability. |
C31H25NO4 | Z = 2 |
Mr = 475.52 | F(000) = 500 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3233 (6) Å | Cell parameters from 6077 reflections |
b = 9.2393 (7) Å | θ = 2.5–27.7° |
c = 15.9107 (12) Å | µ = 0.09 mm−1 |
α = 79.969 (4)° | T = 297 K |
β = 88.820 (4)° | Cubic, colourless |
γ = 86.311 (4)° | 0.25 × 0.22 × 0.20 mm |
V = 1202.30 (16) Å3 |
Bruker APEXII CCD area-detector diffractometer | 5771 independent reflections |
Radiation source: fine-focus sealed tube | 3881 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 28.4°, θmin = 1.3° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→11 |
Tmin = 0.969, Tmax = 0.983 | k = −9→12 |
14955 measured reflections | l = −20→20 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0754P)2 + 0.2718P] where P = (Fo2 + 2Fc2)/3 |
5771 reflections | (Δ/σ)max < 0.001 |
327 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C31H25NO4 | γ = 86.311 (4)° |
Mr = 475.52 | V = 1202.30 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3233 (6) Å | Mo Kα radiation |
b = 9.2393 (7) Å | µ = 0.09 mm−1 |
c = 15.9107 (12) Å | T = 297 K |
α = 79.969 (4)° | 0.25 × 0.22 × 0.20 mm |
β = 88.820 (4)° |
Bruker APEXII CCD area-detector diffractometer | 5771 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3881 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.983 | Rint = 0.038 |
14955 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.28 e Å−3 |
5771 reflections | Δρmin = −0.28 e Å−3 |
327 parameters |
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 | ||
C1 | 0.57850 (18) | 0.03937 (18) | 0.27098 (11) | 0.0360 (4) | |
C2 | 0.40922 (18) | −0.00749 (17) | 0.31375 (10) | 0.0346 (3) | |
C3 | 0.45746 (19) | −0.09347 (19) | 0.40289 (11) | 0.0408 (4) | |
H3 | 0.4611 | −0.0200 | 0.4403 | 0.049* | |
C4 | 0.6312 (2) | −0.1479 (2) | 0.38993 (12) | 0.0462 (4) | |
H4A | 0.6873 | −0.1749 | 0.4438 | 0.055* | |
H4B | 0.6376 | −0.2312 | 0.3601 | 0.055* | |
C5 | 0.61230 (19) | −0.0249 (2) | 0.18623 (12) | 0.0421 (4) | |
C6 | 0.6259 (2) | 0.0998 (2) | 0.11601 (11) | 0.0432 (4) | |
C7 | 0.6504 (2) | 0.1087 (3) | 0.02958 (13) | 0.0577 (5) | |
H7 | 0.6568 | 0.0244 | 0.0048 | 0.069* | |
C8 | 0.6655 (3) | 0.2480 (3) | −0.02011 (14) | 0.0674 (6) | |
H8 | 0.6792 | 0.2555 | −0.0788 | 0.081* | |
C9 | 0.6607 (3) | 0.3738 (3) | 0.01491 (14) | 0.0644 (6) | |
H9 | 0.6743 | 0.4639 | −0.0201 | 0.077* | |
C10 | 0.6304 (2) | 0.4866 (2) | 0.14943 (14) | 0.0565 (5) | |
H10 | 0.6401 | 0.5823 | 0.1205 | 0.068* | |
C11 | 0.6114 (2) | 0.4608 (2) | 0.23585 (15) | 0.0557 (5) | |
H11 | 0.6100 | 0.5400 | 0.2648 | 0.067* | |
C12 | 0.5937 (2) | 0.31861 (19) | 0.28313 (12) | 0.0444 (4) | |
H12 | 0.5827 | 0.3043 | 0.3422 | 0.053* | |
C13 | 0.59326 (18) | 0.20230 (18) | 0.24059 (11) | 0.0364 (4) | |
C14 | 0.61716 (19) | 0.22864 (19) | 0.15170 (11) | 0.0395 (4) | |
C15 | 0.6353 (2) | 0.3685 (2) | 0.10360 (12) | 0.0484 (4) | |
C16 | 0.3152 (2) | −0.10079 (18) | 0.26368 (11) | 0.0407 (4) | |
H16A | 0.3783 | −0.1918 | 0.2606 | 0.049* | |
H16B | 0.2161 | −0.1260 | 0.2942 | 0.049* | |
C17 | 0.30017 (18) | 0.13009 (18) | 0.31895 (11) | 0.0363 (4) | |
C18 | 0.1461 (2) | 0.33730 (19) | 0.22831 (12) | 0.0427 (4) | |
H18 | 0.1476 | 0.3909 | 0.2726 | 0.051* | |
C19 | 0.0768 (2) | 0.3996 (2) | 0.15207 (13) | 0.0484 (4) | |
C20 | 0.0703 (2) | 0.3165 (2) | 0.08699 (13) | 0.0558 (5) | |
H20 | 0.0214 | 0.3583 | 0.0357 | 0.067* | |
C21 | 0.1346 (2) | 0.1749 (2) | 0.09756 (13) | 0.0518 (5) | |
H21 | 0.1281 | 0.1203 | 0.0540 | 0.062* | |
C22 | 0.20975 (19) | 0.11263 (19) | 0.17369 (11) | 0.0396 (4) | |
C23 | 0.21491 (18) | 0.19285 (18) | 0.23951 (11) | 0.0369 (4) | |
C24 | 0.0114 (3) | 0.6291 (3) | 0.19620 (18) | 0.0801 (7) | |
H24A | −0.0518 | 0.5853 | 0.2440 | 0.120* | |
H24B | −0.0346 | 0.7258 | 0.1741 | 0.120* | |
H24C | 0.1196 | 0.6360 | 0.2143 | 0.120* | |
C25 | 0.3443 (2) | −0.2068 (2) | 0.44581 (12) | 0.0490 (5) | |
C26 | 0.3616 (3) | −0.3527 (3) | 0.43840 (17) | 0.0727 (7) | |
H26 | 0.4423 | −0.3846 | 0.4034 | 0.087* | |
C27 | 0.2594 (4) | −0.4537 (3) | 0.4829 (2) | 0.0962 (10) | |
H27 | 0.2717 | −0.5523 | 0.4772 | 0.115* | |
C28 | 0.1417 (4) | −0.4081 (4) | 0.53457 (19) | 0.0990 (11) | |
H28 | 0.0759 | −0.4761 | 0.5658 | 0.119* | |
C29 | 0.1200 (3) | −0.2623 (4) | 0.54074 (17) | 0.0932 (10) | |
H29 | 0.0372 | −0.2309 | 0.5747 | 0.112* | |
C30 | 0.2205 (3) | −0.1618 (3) | 0.49687 (14) | 0.0681 (6) | |
H30 | 0.2051 | −0.0629 | 0.5015 | 0.082* | |
C31 | 0.8618 (2) | −0.0306 (3) | 0.31296 (15) | 0.0604 (6) | |
H31A | 0.9278 | −0.0529 | 0.3629 | 0.091* | |
H31B | 0.8901 | 0.0612 | 0.2795 | 0.091* | |
H31C | 0.8787 | −0.1075 | 0.2797 | 0.091* | |
N1 | 0.69349 (16) | −0.01929 (16) | 0.33844 (10) | 0.0426 (4) | |
O1 | 0.63514 (17) | −0.15490 (15) | 0.18358 (10) | 0.0584 (4) | |
O2 | 0.27733 (15) | −0.02802 (13) | 0.17924 (8) | 0.0454 (3) | |
O3 | 0.28659 (16) | 0.18571 (15) | 0.38289 (8) | 0.0512 (3) | |
O4 | 0.01298 (19) | 0.54128 (16) | 0.13208 (10) | 0.0658 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0284 (7) | 0.0367 (9) | 0.0444 (9) | −0.0016 (6) | 0.0011 (6) | −0.0117 (7) |
C2 | 0.0284 (7) | 0.0340 (8) | 0.0416 (9) | −0.0021 (6) | −0.0004 (6) | −0.0074 (7) |
C3 | 0.0328 (8) | 0.0427 (10) | 0.0457 (10) | −0.0018 (7) | −0.0032 (7) | −0.0041 (7) |
C4 | 0.0353 (9) | 0.0444 (10) | 0.0573 (11) | 0.0005 (7) | −0.0079 (8) | −0.0041 (8) |
C5 | 0.0293 (8) | 0.0431 (10) | 0.0576 (11) | −0.0022 (7) | 0.0030 (7) | −0.0198 (8) |
C6 | 0.0320 (8) | 0.0520 (11) | 0.0485 (10) | −0.0047 (7) | 0.0056 (7) | −0.0173 (8) |
C7 | 0.0466 (11) | 0.0790 (15) | 0.0534 (12) | −0.0086 (10) | 0.0081 (9) | −0.0276 (11) |
C8 | 0.0612 (13) | 0.0972 (19) | 0.0441 (12) | −0.0118 (12) | 0.0066 (9) | −0.0112 (12) |
C9 | 0.0566 (13) | 0.0773 (16) | 0.0537 (13) | −0.0105 (11) | 0.0020 (10) | 0.0064 (11) |
C10 | 0.0549 (12) | 0.0399 (11) | 0.0723 (15) | −0.0078 (8) | −0.0025 (10) | −0.0015 (10) |
C11 | 0.0568 (12) | 0.0395 (11) | 0.0752 (15) | −0.0086 (8) | −0.0005 (10) | −0.0200 (10) |
C12 | 0.0405 (9) | 0.0460 (10) | 0.0507 (11) | −0.0061 (7) | 0.0012 (8) | −0.0184 (8) |
C13 | 0.0285 (8) | 0.0377 (9) | 0.0445 (9) | −0.0022 (6) | 0.0004 (6) | −0.0117 (7) |
C14 | 0.0289 (8) | 0.0445 (10) | 0.0464 (10) | −0.0025 (6) | 0.0010 (7) | −0.0113 (8) |
C15 | 0.0395 (9) | 0.0508 (11) | 0.0526 (11) | −0.0061 (8) | −0.0004 (8) | −0.0019 (9) |
C16 | 0.0323 (8) | 0.0385 (9) | 0.0519 (10) | −0.0024 (6) | −0.0034 (7) | −0.0089 (8) |
C17 | 0.0272 (7) | 0.0407 (9) | 0.0418 (9) | −0.0019 (6) | 0.0031 (6) | −0.0095 (7) |
C18 | 0.0348 (9) | 0.0434 (10) | 0.0498 (10) | 0.0026 (7) | 0.0026 (7) | −0.0102 (8) |
C19 | 0.0381 (9) | 0.0463 (11) | 0.0575 (12) | 0.0059 (7) | 0.0003 (8) | −0.0032 (9) |
C20 | 0.0514 (11) | 0.0614 (13) | 0.0509 (11) | 0.0085 (9) | −0.0113 (9) | −0.0028 (10) |
C21 | 0.0497 (11) | 0.0592 (12) | 0.0479 (11) | 0.0053 (9) | −0.0107 (8) | −0.0147 (9) |
C22 | 0.0301 (8) | 0.0424 (10) | 0.0469 (10) | 0.0002 (7) | −0.0018 (7) | −0.0096 (8) |
C23 | 0.0263 (7) | 0.0419 (9) | 0.0425 (9) | 0.0008 (6) | 0.0009 (6) | −0.0083 (7) |
C24 | 0.0880 (18) | 0.0550 (14) | 0.0968 (19) | 0.0202 (12) | −0.0077 (14) | −0.0201 (13) |
C25 | 0.0379 (9) | 0.0572 (12) | 0.0482 (11) | −0.0075 (8) | −0.0071 (8) | 0.0040 (9) |
C26 | 0.0552 (13) | 0.0555 (14) | 0.1002 (19) | −0.0099 (10) | 0.0027 (12) | 0.0087 (12) |
C27 | 0.0789 (19) | 0.0747 (18) | 0.123 (3) | −0.0311 (14) | −0.0210 (18) | 0.0269 (17) |
C28 | 0.079 (2) | 0.135 (3) | 0.0760 (18) | −0.064 (2) | −0.0102 (15) | 0.0235 (18) |
C29 | 0.0667 (16) | 0.154 (3) | 0.0644 (16) | −0.0524 (18) | 0.0146 (12) | −0.0203 (17) |
C30 | 0.0509 (12) | 0.0996 (18) | 0.0568 (13) | −0.0224 (11) | 0.0060 (10) | −0.0164 (12) |
C31 | 0.0271 (9) | 0.0734 (14) | 0.0803 (15) | −0.0004 (8) | −0.0001 (9) | −0.0134 (11) |
N1 | 0.0266 (7) | 0.0465 (9) | 0.0537 (9) | −0.0015 (6) | −0.0034 (6) | −0.0054 (7) |
O1 | 0.0538 (8) | 0.0449 (8) | 0.0815 (10) | 0.0008 (6) | 0.0071 (7) | −0.0273 (7) |
O2 | 0.0452 (7) | 0.0445 (7) | 0.0488 (7) | 0.0040 (5) | −0.0088 (5) | −0.0155 (6) |
O3 | 0.0511 (8) | 0.0594 (8) | 0.0442 (7) | 0.0100 (6) | 0.0001 (6) | −0.0173 (6) |
O4 | 0.0684 (10) | 0.0510 (9) | 0.0729 (10) | 0.0179 (7) | −0.0084 (7) | −0.0033 (7) |
C1—N1 | 1.461 (2) | C16—H16B | 0.9700 |
C1—C13 | 1.511 (2) | C17—O3 | 1.2173 (19) |
C1—C5 | 1.579 (2) | C17—C23 | 1.472 (2) |
C1—C2 | 1.604 (2) | C18—C19 | 1.371 (3) |
C2—C17 | 1.527 (2) | C18—C23 | 1.401 (2) |
C2—C16 | 1.530 (2) | C18—H18 | 0.9300 |
C2—C3 | 1.547 (2) | C19—O4 | 1.367 (2) |
C3—C25 | 1.517 (2) | C19—C20 | 1.396 (3) |
C3—C4 | 1.522 (2) | C20—C21 | 1.365 (3) |
C3—H3 | 0.9800 | C20—H20 | 0.9300 |
C4—N1 | 1.440 (2) | C21—C22 | 1.390 (2) |
C4—H4A | 0.9700 | C21—H21 | 0.9300 |
C4—H4B | 0.9700 | C22—O2 | 1.371 (2) |
C5—O1 | 1.212 (2) | C22—C23 | 1.387 (2) |
C5—C6 | 1.467 (3) | C24—O4 | 1.409 (3) |
C6—C7 | 1.375 (3) | C24—H24A | 0.9600 |
C6—C14 | 1.403 (2) | C24—H24B | 0.9600 |
C7—C8 | 1.400 (3) | C24—H24C | 0.9600 |
C7—H7 | 0.9300 | C25—C26 | 1.372 (3) |
C8—C9 | 1.372 (3) | C25—C30 | 1.387 (3) |
C8—H8 | 0.9300 | C26—C27 | 1.394 (3) |
C9—C15 | 1.415 (3) | C26—H26 | 0.9300 |
C9—H9 | 0.9300 | C27—C28 | 1.359 (5) |
C10—C11 | 1.362 (3) | C27—H27 | 0.9300 |
C10—C15 | 1.412 (3) | C28—C29 | 1.368 (5) |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—C12 | 1.410 (3) | C29—C30 | 1.378 (3) |
C11—H11 | 0.9300 | C29—H29 | 0.9300 |
C12—C13 | 1.366 (2) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—N1 | 1.453 (2) |
C13—C14 | 1.405 (2) | C31—H31A | 0.9600 |
C14—C15 | 1.398 (3) | C31—H31B | 0.9600 |
C16—O2 | 1.426 (2) | C31—H31C | 0.9600 |
C16—H16A | 0.9700 | ||
N1—C1—C13 | 111.49 (13) | O2—C16—H16B | 109.0 |
N1—C1—C5 | 113.14 (13) | C2—C16—H16B | 109.0 |
C13—C1—C5 | 101.98 (13) | H16A—C16—H16B | 107.8 |
N1—C1—C2 | 102.92 (13) | O3—C17—C23 | 122.31 (15) |
C13—C1—C2 | 116.02 (13) | O3—C17—C2 | 123.07 (15) |
C5—C1—C2 | 111.71 (12) | C23—C17—C2 | 114.61 (14) |
C17—C2—C16 | 105.91 (13) | C19—C18—C23 | 120.01 (17) |
C17—C2—C3 | 112.42 (13) | C19—C18—H18 | 120.0 |
C16—C2—C3 | 111.65 (13) | C23—C18—H18 | 120.0 |
C17—C2—C1 | 109.67 (13) | O4—C19—C18 | 125.42 (18) |
C16—C2—C1 | 114.13 (13) | O4—C19—C20 | 115.01 (17) |
C3—C2—C1 | 103.22 (12) | C18—C19—C20 | 119.56 (17) |
C25—C3—C4 | 116.79 (15) | C21—C20—C19 | 121.00 (18) |
C25—C3—C2 | 117.08 (14) | C21—C20—H20 | 119.5 |
C4—C3—C2 | 103.40 (13) | C19—C20—H20 | 119.5 |
C25—C3—H3 | 106.2 | C20—C21—C22 | 119.74 (18) |
C4—C3—H3 | 106.2 | C20—C21—H21 | 120.1 |
C2—C3—H3 | 106.2 | C22—C21—H21 | 120.1 |
N1—C4—C3 | 100.96 (13) | O2—C22—C23 | 123.02 (15) |
N1—C4—H4A | 111.6 | O2—C22—C21 | 117.01 (16) |
C3—C4—H4A | 111.6 | C23—C22—C21 | 119.97 (16) |
N1—C4—H4B | 111.6 | C22—C23—C18 | 119.67 (15) |
C3—C4—H4B | 111.6 | C22—C23—C17 | 120.31 (15) |
H4A—C4—H4B | 109.4 | C18—C23—C17 | 119.93 (15) |
O1—C5—C6 | 127.80 (17) | O4—C24—H24A | 109.5 |
O1—C5—C1 | 124.22 (17) | O4—C24—H24B | 109.5 |
C6—C5—C1 | 107.73 (14) | H24A—C24—H24B | 109.5 |
C7—C6—C14 | 119.71 (18) | O4—C24—H24C | 109.5 |
C7—C6—C5 | 132.76 (17) | H24A—C24—H24C | 109.5 |
C14—C6—C5 | 107.47 (15) | H24B—C24—H24C | 109.5 |
C6—C7—C8 | 118.2 (2) | C26—C25—C30 | 118.4 (2) |
C6—C7—H7 | 120.9 | C26—C25—C3 | 123.00 (19) |
C8—C7—H7 | 120.9 | C30—C25—C3 | 118.56 (19) |
C9—C8—C7 | 122.2 (2) | C25—C26—C27 | 120.6 (3) |
C9—C8—H8 | 118.9 | C25—C26—H26 | 119.7 |
C7—C8—H8 | 118.9 | C27—C26—H26 | 119.7 |
C8—C9—C15 | 121.0 (2) | C28—C27—C26 | 120.0 (3) |
C8—C9—H9 | 119.5 | C28—C27—H27 | 120.0 |
C15—C9—H9 | 119.5 | C26—C27—H27 | 120.0 |
C11—C10—C15 | 120.14 (18) | C27—C28—C29 | 120.0 (2) |
C11—C10—H10 | 119.9 | C27—C28—H28 | 120.0 |
C15—C10—H10 | 119.9 | C29—C28—H28 | 120.0 |
C10—C11—C12 | 122.58 (18) | C28—C29—C30 | 120.3 (3) |
C10—C11—H11 | 118.7 | C28—C29—H29 | 119.9 |
C12—C11—H11 | 118.7 | C30—C29—H29 | 119.9 |
C13—C12—C11 | 118.85 (18) | C29—C30—C25 | 120.6 (3) |
C13—C12—H12 | 120.6 | C29—C30—H30 | 119.7 |
C11—C12—H12 | 120.6 | C25—C30—H30 | 119.7 |
C12—C13—C14 | 118.45 (16) | N1—C31—H31A | 109.5 |
C12—C13—C1 | 132.26 (16) | N1—C31—H31B | 109.5 |
C14—C13—C1 | 109.23 (14) | H31A—C31—H31B | 109.5 |
C15—C14—C6 | 123.07 (17) | N1—C31—H31C | 109.5 |
C15—C14—C13 | 123.62 (16) | H31A—C31—H31C | 109.5 |
C6—C14—C13 | 113.28 (16) | H31B—C31—H31C | 109.5 |
C14—C15—C10 | 116.31 (17) | C4—N1—C31 | 116.72 (15) |
C14—C15—C9 | 115.80 (19) | C4—N1—C1 | 108.78 (13) |
C10—C15—C9 | 127.87 (19) | C31—N1—C1 | 116.55 (15) |
O2—C16—C2 | 113.12 (14) | C22—O2—C16 | 114.83 (13) |
O2—C16—H16A | 109.0 | C19—O4—C24 | 117.59 (17) |
C2—C16—H16A | 109.0 | ||
N1—C1—C2—C17 | 118.59 (14) | C11—C10—C15—C9 | −177.2 (2) |
C13—C1—C2—C17 | −3.43 (19) | C8—C9—C15—C14 | 0.5 (3) |
C5—C1—C2—C17 | −119.72 (15) | C8—C9—C15—C10 | 178.6 (2) |
N1—C1—C2—C16 | −122.79 (14) | C17—C2—C16—O2 | 60.91 (17) |
C13—C1—C2—C16 | 115.19 (15) | C3—C2—C16—O2 | −176.41 (13) |
C5—C1—C2—C16 | −1.10 (19) | C1—C2—C16—O2 | −59.83 (18) |
N1—C1—C2—C3 | −1.42 (15) | C16—C2—C17—O3 | 139.69 (16) |
C13—C1—C2—C3 | −123.44 (15) | C3—C2—C17—O3 | 17.5 (2) |
C5—C1—C2—C3 | 120.27 (14) | C1—C2—C17—O3 | −96.72 (18) |
C17—C2—C3—C25 | 87.35 (18) | C16—C2—C17—C23 | −41.67 (18) |
C16—C2—C3—C25 | −31.5 (2) | C3—C2—C17—C23 | −163.86 (13) |
C1—C2—C3—C25 | −154.56 (15) | C1—C2—C17—C23 | 81.92 (16) |
C17—C2—C3—C4 | −142.70 (14) | C23—C18—C19—O4 | −176.67 (17) |
C16—C2—C3—C4 | 98.42 (15) | C23—C18—C19—C20 | 2.2 (3) |
C1—C2—C3—C4 | −24.60 (16) | O4—C19—C20—C21 | 177.81 (19) |
C25—C3—C4—N1 | 172.33 (15) | C18—C19—C20—C21 | −1.2 (3) |
C2—C3—C4—N1 | 42.21 (17) | C19—C20—C21—C22 | −0.9 (3) |
N1—C1—C5—O1 | 49.1 (2) | C20—C21—C22—O2 | −177.58 (17) |
C13—C1—C5—O1 | 168.97 (16) | C20—C21—C22—C23 | 1.9 (3) |
C2—C1—C5—O1 | −66.5 (2) | O2—C22—C23—C18 | 178.58 (15) |
N1—C1—C5—C6 | −125.49 (15) | C21—C22—C23—C18 | −0.9 (2) |
C13—C1—C5—C6 | −5.63 (16) | O2—C22—C23—C17 | 2.1 (2) |
C2—C1—C5—C6 | 118.92 (14) | C21—C22—C23—C17 | −177.41 (16) |
O1—C5—C6—C7 | 7.5 (3) | C19—C18—C23—C22 | −1.2 (3) |
C1—C5—C6—C7 | −178.13 (18) | C19—C18—C23—C17 | 175.33 (15) |
O1—C5—C6—C14 | −169.53 (17) | O3—C17—C23—C22 | −168.08 (16) |
C1—C5—C6—C14 | 4.81 (17) | C2—C17—C23—C22 | 13.3 (2) |
C14—C6—C7—C8 | −0.1 (3) | O3—C17—C23—C18 | 15.4 (2) |
C5—C6—C7—C8 | −176.89 (19) | C2—C17—C23—C18 | −163.22 (14) |
C6—C7—C8—C9 | 1.7 (3) | C4—C3—C25—C26 | −30.5 (3) |
C7—C8—C9—C15 | −1.9 (3) | C2—C3—C25—C26 | 92.9 (2) |
C15—C10—C11—C12 | −0.9 (3) | C4—C3—C25—C30 | 147.63 (19) |
C10—C11—C12—C13 | −1.0 (3) | C2—C3—C25—C30 | −89.0 (2) |
C11—C12—C13—C14 | 2.6 (2) | C30—C25—C26—C27 | −1.6 (3) |
C11—C12—C13—C1 | 179.43 (16) | C3—C25—C26—C27 | 176.5 (2) |
N1—C1—C13—C12 | −51.5 (2) | C25—C26—C27—C28 | −0.3 (4) |
C5—C1—C13—C12 | −172.49 (17) | C26—C27—C28—C29 | 2.2 (4) |
C2—C1—C13—C12 | 65.9 (2) | C27—C28—C29—C30 | −2.1 (4) |
N1—C1—C13—C14 | 125.54 (14) | C28—C29—C30—C25 | 0.2 (4) |
C5—C1—C13—C14 | 4.52 (16) | C26—C25—C30—C29 | 1.6 (3) |
C2—C1—C13—C14 | −117.10 (15) | C3—C25—C30—C29 | −176.5 (2) |
C7—C6—C14—C15 | −1.3 (3) | C3—C4—N1—C31 | 179.88 (16) |
C5—C6—C14—C15 | 176.24 (15) | C3—C4—N1—C1 | −45.72 (17) |
C7—C6—C14—C13 | −179.48 (16) | C13—C1—N1—C4 | 154.45 (14) |
C5—C6—C14—C13 | −1.97 (19) | C5—C1—N1—C4 | −91.30 (16) |
C12—C13—C14—C15 | −2.6 (2) | C2—C1—N1—C4 | 29.42 (17) |
C1—C13—C14—C15 | 179.92 (15) | C13—C1—N1—C31 | −71.06 (19) |
C12—C13—C14—C6 | 175.61 (15) | C5—C1—N1—C31 | 43.2 (2) |
C1—C13—C14—C6 | −1.88 (19) | C2—C1—N1—C31 | 163.90 (15) |
C6—C14—C15—C10 | −177.29 (16) | C23—C22—O2—C16 | 16.0 (2) |
C13—C14—C15—C10 | 0.7 (3) | C21—C22—O2—C16 | −164.50 (15) |
C6—C14—C15—C9 | 1.1 (3) | C2—C16—O2—C22 | −49.12 (18) |
C13—C14—C15—C9 | 179.11 (16) | C18—C19—O4—C24 | −3.1 (3) |
C11—C10—C15—C14 | 1.0 (3) | C20—C19—O4—C24 | 178.0 (2) |
Experimental details
Crystal data | |
Chemical formula | C31H25NO4 |
Mr | 475.52 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 297 |
a, b, c (Å) | 8.3233 (6), 9.2393 (7), 15.9107 (12) |
α, β, γ (°) | 79.969 (4), 88.820 (4), 86.311 (4) |
V (Å3) | 1202.30 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.969, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14955, 5771, 3881 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.160, 1.03 |
No. of reflections | 5771 |
No. of parameters | 327 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.28 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
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Spiroheterocycles belong to an important class of compounds with highly pronounced biological activities·(James et al. 1991) The central skeleton of many natural products and pharmacologically active compounds contain highly substituted pyrrolidines which are of much prominence (Deshong et al., 1983). Some of the biological active compounds such as rhyncophylline, corynoxeine,nitraphylline,vincatine, horsifiline,etc (Henrickson et al. 1962) contain pyrrolidine and oxindole moiety which forms a separate class of alkaloids (Fujimori 1990). In view of this we have determined the structure of the title compound.
The chromanone moiety consists of a methoxy benzene ring fused with a five membered heterocyclic ring which adopts a sofa conformation. The dihydropyrone ring is in an half chair conformation. The nitrogen atom of the pyrrolidine ring is slightly pyramidal, the sum of the angles amount to 342.04 °.