6-Methoxy-1′-methyl-4′-phenylchroman-3-spiro-3′-pyrrolidine-2′-spiro-3′′(2′′H)- indole-2′′,4-dione
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038755/bx2097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038755/bx2097Isup2.hkl |
CCDC reference: 660279
A mixture of Isatin (1H-indole-2,3-dione) (1 mmol, 0.082 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 5 h and was subsequently monitored by TLC for the disappearance of starting materials. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and hexane–ethyl acetate (5:1) as eluent to give the cycloadduct.
All the H atoms were geometrically fixed at chemically meaningful positions. The hydrogen atoms of the phenyl ring were allowed to ride at a distance of 0.93 Å from the parent carbons and their thermal parameter were fixed at 1.2 times that of the parent atom.
The secondary CH2 H atoms were fixed at a distance of 0.97 Å from the parent atom and their thermal parameters were fixed at 1.2 times the parent atom.
The CH3 H atoms attached to Nitrogen were fixed at a distance of 0.96 Å from the parent atom and their thermal parameters were fixed at 1.5 times the parent atom. similarly the CH3 H atoms attached to Oxygen were fixed at a distance of 0.96 Å from the parent atom and their thermal parameters were fixed at 1.5 times the parent atom.
Spiroheterocycles represent an important class of naturally occurring substances characterized by their highly pronounced biological activities·(James et al., 1991) Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products and pharmacologically active compounds. (Deshong & Leginus, 1983). Pyrrolidine and oxindole alkaloids (Fujimori, 1990) constitute another class of compounds with significant biological activity which are normally found in rhyncophylline, corynoxeine, nitraphylline, vincatine, horsifiline,etc (Henrickson & Silva, 1962).
In the crystal structure of the title compound, C27H24N2O4, the chromanone moiety consists of a methoxy benzene ring fused with a six membered heterocyclic ring which adopts a sofa conformation (Abdul Ajees et al., 2001). The five membered spiropyrrolidine ring is in an envelope conformation. The oxindole and phenyl rings attached to the five membered rings are nearly perpendicular to each other. The molecules are linked into centrosymmetric R22(14) dimmer by a simple N—H···O interaction (Bernstein et al., 1995)
For related literature, see: Abdul Ajees et al. (2001); Bernstein et al. (1995); Deshong & Leginus (1983); Fujimori (1990); Henrickson & Silva (1962); James et al. (1991).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (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.
Fig. 1. ORTEP representation of the molecule showing the atom numbering scheme. Thermal ellipsoids are drawn with 30% probability. | |
Fig. 2. Packing diagram of title compound projected down the C-axis |
C27H24N2O4 | F(000) = 928 |
Mr = 440.48 | Dx = 1.334 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8137 reflections |
a = 9.2244 (2) Å | θ = 2.4–26.8° |
b = 26.1163 (5) Å | µ = 0.09 mm−1 |
c = 9.3506 (2) Å | T = 295 K |
β = 103.233 (1)° | Rectangular, colourless |
V = 2192.81 (8) Å3 | 0.23 × 0.21 × 0.15 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5379 independent reflections |
Radiation source: fine-focus sealed tube | 3670 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 28.4°, θmin = 1.6° |
Absorption correction: multi-scan (Blessing, 1995) | h = −11→12 |
Tmin = 0.899, Tmax = 0.987 | k = −34→34 |
27791 measured reflections | l = −12→10 |
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) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.486P] where P = (Fo2 + 2Fc2)/3 |
5379 reflections | (Δ/σ)max < 0.001 |
304 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C27H24N2O4 | V = 2192.81 (8) Å3 |
Mr = 440.48 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2244 (2) Å | µ = 0.09 mm−1 |
b = 26.1163 (5) Å | T = 295 K |
c = 9.3506 (2) Å | 0.23 × 0.21 × 0.15 mm |
β = 103.233 (1)° |
Bruker SMART CCD area-detector diffractometer | 5379 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3670 reflections with I > 2σ(I) |
Tmin = 0.899, Tmax = 0.987 | Rint = 0.032 |
27791 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.24 e Å−3 |
5379 reflections | Δρmin = −0.18 e Å−3 |
304 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. The reflections with Bragg angle less than 2.4° could not be collected due to the hinderence of the beam stop. This lead to the absence of 14 low angle reflections from the measured data. As b axis length is quite large (26.116 Å) for the wave length used (0.71073 Å),it became unavoidable. Except for these missing low angle reflections, the data set is complete with in 50° two theta. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.25225 (16) | 0.09504 (5) | 0.02539 (14) | 0.0343 (3) | |
C2 | 0.34793 (15) | 0.14452 (5) | 0.00669 (13) | 0.0312 (3) | |
C3 | 0.23382 (16) | 0.17999 (5) | −0.09708 (14) | 0.0338 (3) | |
H3 | 0.1920 | 0.2025 | −0.0330 | 0.041* | |
C4 | 0.11035 (18) | 0.14375 (6) | −0.16772 (16) | 0.0445 (4) | |
H4A | 0.0178 | 0.1619 | −0.2058 | 0.053* | |
H4B | 0.1367 | 0.1242 | −0.2463 | 0.053* | |
C5 | 0.30377 (17) | 0.04717 (5) | −0.05042 (16) | 0.0401 (3) | |
C6 | 0.31749 (17) | 0.02527 (5) | 0.18915 (16) | 0.0392 (3) | |
C7 | 0.3394 (2) | −0.00243 (6) | 0.31793 (19) | 0.0552 (4) | |
H7 | 0.3771 | −0.0356 | 0.3237 | 0.066* | |
C8 | 0.3033 (2) | 0.02077 (7) | 0.43793 (19) | 0.0640 (5) | |
H8 | 0.3183 | 0.0031 | 0.5264 | 0.077* | |
C9 | 0.2459 (2) | 0.06933 (8) | 0.4293 (2) | 0.0639 (5) | |
H9 | 0.2210 | 0.0840 | 0.5111 | 0.077* | |
C10 | 0.2246 (2) | 0.09686 (7) | 0.29919 (18) | 0.0512 (4) | |
H10 | 0.1848 | 0.1297 | 0.2932 | 0.061* | |
C11 | 0.26312 (16) | 0.07498 (5) | 0.17921 (15) | 0.0366 (3) | |
C12 | 0.40941 (16) | 0.16912 (5) | 0.15696 (14) | 0.0343 (3) | |
C13 | 0.48437 (16) | 0.13335 (5) | −0.05463 (15) | 0.0364 (3) | |
H13A | 0.4520 | 0.1199 | −0.1535 | 0.044* | |
H13B | 0.5375 | 0.1651 | −0.0601 | 0.044* | |
C14 | 0.74957 (18) | 0.08581 (6) | 0.26498 (18) | 0.0462 (4) | |
H14 | 0.8021 | 0.0620 | 0.2227 | 0.055* | |
C15 | 0.79350 (18) | 0.09709 (6) | 0.41191 (19) | 0.0514 (4) | |
H15 | 0.8757 | 0.0805 | 0.4693 | 0.062* | |
C16 | 0.71684 (18) | 0.13301 (6) | 0.47627 (16) | 0.0452 (4) | |
C17 | 0.59566 (17) | 0.15788 (6) | 0.39204 (15) | 0.0403 (3) | |
H17 | 0.5452 | 0.1824 | 0.4342 | 0.048* | |
C18 | 0.54837 (16) | 0.14622 (5) | 0.24221 (15) | 0.0348 (3) | |
C19 | 0.62592 (16) | 0.11033 (5) | 0.18011 (15) | 0.0369 (3) | |
C20 | 0.6949 (2) | 0.17725 (8) | 0.69199 (18) | 0.0620 (5) | |
H20A | 0.7026 | 0.2104 | 0.6497 | 0.093* | |
H20B | 0.7393 | 0.1783 | 0.7954 | 0.093* | |
H20C | 0.5918 | 0.1679 | 0.6772 | 0.093* | |
C21 | 0.29494 (16) | 0.21463 (5) | −0.19882 (15) | 0.0356 (3) | |
C22 | 0.38359 (19) | 0.25574 (6) | −0.14124 (19) | 0.0512 (4) | |
H22 | 0.4076 | 0.2608 | −0.0401 | 0.061* | |
C23 | 0.4371 (2) | 0.28933 (7) | −0.2299 (2) | 0.0655 (5) | |
H23 | 0.4968 | 0.3166 | −0.1882 | 0.079* | |
C24 | 0.4031 (2) | 0.28291 (7) | −0.3794 (2) | 0.0645 (5) | |
H24 | 0.4397 | 0.3056 | −0.4393 | 0.077* | |
C25 | 0.3146 (2) | 0.24280 (8) | −0.4395 (2) | 0.0660 (5) | |
H25 | 0.2905 | 0.2382 | −0.5408 | 0.079* | |
C26 | 0.2605 (2) | 0.20884 (6) | −0.34931 (17) | 0.0523 (4) | |
H26 | 0.2000 | 0.1818 | −0.3914 | 0.063* | |
C27 | −0.0093 (2) | 0.06977 (7) | −0.0786 (2) | 0.0661 (5) | |
H27A | −0.1068 | 0.0841 | −0.1136 | 0.099* | |
H27B | −0.0073 | 0.0499 | 0.0081 | 0.099* | |
H27C | 0.0145 | 0.0482 | −0.1532 | 0.099* | |
N1 | 0.10004 (14) | 0.11104 (5) | −0.04404 (14) | 0.0428 (3) | |
N2 | 0.33944 (15) | 0.00992 (5) | 0.05262 (14) | 0.0447 (3) | |
O1 | 0.30669 (15) | 0.04317 (4) | −0.17904 (12) | 0.0583 (3) | |
O2 | 0.34710 (13) | 0.20420 (4) | 0.20365 (11) | 0.0502 (3) | |
O3 | 0.58380 (11) | 0.09720 (4) | 0.03378 (10) | 0.0406 (2) | |
O4 | 0.76976 (14) | 0.14063 (5) | 0.62380 (12) | 0.0631 (4) | |
H2 | 0.369 (2) | −0.0207 (7) | 0.0335 (18) | 0.056 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0353 (8) | 0.0335 (7) | 0.0331 (7) | 0.0026 (6) | 0.0057 (6) | 0.0026 (5) |
C2 | 0.0316 (7) | 0.0319 (7) | 0.0283 (6) | 0.0027 (5) | 0.0034 (5) | 0.0017 (5) |
C3 | 0.0340 (8) | 0.0341 (7) | 0.0312 (7) | 0.0030 (6) | 0.0031 (6) | 0.0031 (5) |
C4 | 0.0405 (9) | 0.0435 (8) | 0.0434 (8) | −0.0033 (7) | −0.0028 (7) | 0.0106 (6) |
C5 | 0.0416 (9) | 0.0377 (8) | 0.0408 (8) | −0.0044 (6) | 0.0089 (6) | −0.0043 (6) |
C6 | 0.0375 (8) | 0.0360 (7) | 0.0423 (8) | −0.0003 (6) | 0.0052 (6) | 0.0051 (6) |
C7 | 0.0607 (12) | 0.0438 (9) | 0.0566 (10) | 0.0029 (8) | 0.0042 (8) | 0.0178 (8) |
C8 | 0.0752 (14) | 0.0695 (12) | 0.0444 (9) | −0.0103 (10) | 0.0080 (9) | 0.0191 (9) |
C9 | 0.0805 (14) | 0.0718 (13) | 0.0456 (10) | −0.0028 (10) | 0.0274 (9) | 0.0062 (9) |
C10 | 0.0603 (11) | 0.0508 (9) | 0.0486 (9) | 0.0088 (8) | 0.0251 (8) | 0.0042 (7) |
C11 | 0.0359 (8) | 0.0366 (7) | 0.0377 (7) | 0.0028 (6) | 0.0088 (6) | 0.0067 (6) |
C12 | 0.0360 (8) | 0.0350 (7) | 0.0309 (7) | 0.0034 (6) | 0.0059 (6) | 0.0001 (5) |
C13 | 0.0372 (8) | 0.0371 (7) | 0.0342 (7) | 0.0035 (6) | 0.0068 (6) | 0.0017 (6) |
C14 | 0.0381 (9) | 0.0403 (8) | 0.0555 (9) | 0.0088 (7) | 0.0010 (7) | −0.0036 (7) |
C15 | 0.0391 (9) | 0.0468 (9) | 0.0577 (10) | 0.0070 (7) | −0.0110 (7) | 0.0040 (7) |
C16 | 0.0424 (9) | 0.0450 (8) | 0.0400 (8) | −0.0017 (7) | −0.0076 (7) | 0.0000 (6) |
C17 | 0.0397 (9) | 0.0397 (8) | 0.0373 (7) | 0.0019 (6) | 0.0001 (6) | −0.0027 (6) |
C18 | 0.0324 (8) | 0.0347 (7) | 0.0343 (7) | 0.0009 (6) | 0.0017 (6) | 0.0001 (5) |
C19 | 0.0325 (8) | 0.0356 (7) | 0.0395 (7) | −0.0003 (6) | 0.0020 (6) | −0.0011 (6) |
C20 | 0.0552 (12) | 0.0884 (14) | 0.0374 (9) | −0.0034 (10) | 0.0002 (8) | −0.0058 (9) |
C21 | 0.0361 (8) | 0.0329 (7) | 0.0364 (7) | 0.0063 (6) | 0.0056 (6) | 0.0056 (5) |
C22 | 0.0531 (11) | 0.0486 (9) | 0.0514 (9) | −0.0090 (8) | 0.0108 (8) | 0.0020 (7) |
C23 | 0.0593 (12) | 0.0541 (11) | 0.0840 (14) | −0.0137 (9) | 0.0184 (10) | 0.0117 (10) |
C24 | 0.0611 (12) | 0.0623 (12) | 0.0771 (13) | 0.0105 (10) | 0.0303 (10) | 0.0346 (10) |
C25 | 0.0859 (15) | 0.0689 (12) | 0.0454 (10) | 0.0115 (11) | 0.0198 (9) | 0.0215 (9) |
C26 | 0.0691 (12) | 0.0464 (9) | 0.0386 (8) | −0.0006 (8) | 0.0066 (8) | 0.0062 (7) |
C27 | 0.0445 (11) | 0.0580 (11) | 0.0868 (14) | −0.0137 (8) | −0.0037 (9) | 0.0233 (10) |
N1 | 0.0331 (7) | 0.0415 (7) | 0.0501 (7) | −0.0029 (5) | 0.0016 (5) | 0.0129 (5) |
N2 | 0.0542 (9) | 0.0291 (6) | 0.0512 (8) | 0.0048 (6) | 0.0128 (6) | −0.0010 (6) |
O1 | 0.0835 (9) | 0.0523 (7) | 0.0413 (6) | −0.0062 (6) | 0.0193 (6) | −0.0107 (5) |
O2 | 0.0557 (7) | 0.0523 (6) | 0.0382 (6) | 0.0214 (5) | 0.0016 (5) | −0.0078 (5) |
O3 | 0.0389 (6) | 0.0404 (5) | 0.0406 (5) | 0.0098 (4) | 0.0053 (4) | −0.0045 (4) |
O4 | 0.0609 (8) | 0.0731 (8) | 0.0417 (6) | 0.0111 (6) | −0.0166 (6) | −0.0063 (6) |
C1—N1 | 1.4663 (18) | C14—C15 | 1.372 (2) |
C1—C11 | 1.5124 (18) | C14—C19 | 1.388 (2) |
C1—C5 | 1.5638 (19) | C14—H14 | 0.9300 |
C1—C2 | 1.5970 (19) | C15—C16 | 1.392 (2) |
C2—C13 | 1.5258 (19) | C15—H15 | 0.9300 |
C2—C12 | 1.5309 (18) | C16—O4 | 1.3685 (18) |
C2—C3 | 1.5620 (18) | C16—C17 | 1.374 (2) |
C3—C4 | 1.511 (2) | C17—C18 | 1.4022 (19) |
C3—C21 | 1.5123 (19) | C17—H17 | 0.9300 |
C3—H3 | 0.9800 | C18—C19 | 1.3847 (19) |
C4—N1 | 1.4583 (18) | C19—O3 | 1.3774 (16) |
C4—H4A | 0.9700 | C20—O4 | 1.414 (2) |
C4—H4B | 0.9700 | C20—H20A | 0.9600 |
C5—O1 | 1.2136 (17) | C20—H20B | 0.9600 |
C5—N2 | 1.3558 (19) | C20—H20C | 0.9600 |
C6—C7 | 1.379 (2) | C21—C26 | 1.378 (2) |
C6—C11 | 1.387 (2) | C21—C22 | 1.382 (2) |
C6—N2 | 1.3964 (19) | C22—C23 | 1.374 (2) |
C7—C8 | 1.381 (3) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | C23—C24 | 1.371 (3) |
C8—C9 | 1.369 (3) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.367 (3) |
C9—C10 | 1.388 (2) | C24—H24 | 0.9300 |
C9—H9 | 0.9300 | C25—C26 | 1.393 (2) |
C10—C11 | 1.376 (2) | C25—H25 | 0.9300 |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C12—O2 | 1.2147 (16) | C27—N1 | 1.461 (2) |
C12—C18 | 1.4726 (19) | C27—H27A | 0.9600 |
C13—O3 | 1.4384 (16) | C27—H27B | 0.9600 |
C13—H13A | 0.9700 | C27—H27C | 0.9600 |
C13—H13B | 0.9700 | N2—H2 | 0.878 (18) |
N1—C1—C11 | 111.60 (11) | C15—C14—H14 | 120.4 |
N1—C1—C5 | 112.75 (11) | C19—C14—H14 | 120.4 |
C11—C1—C5 | 101.15 (11) | C14—C15—C16 | 120.98 (14) |
N1—C1—C2 | 102.60 (10) | C14—C15—H15 | 119.5 |
C11—C1—C2 | 117.80 (11) | C16—C15—H15 | 119.5 |
C5—C1—C2 | 111.37 (11) | O4—C16—C17 | 124.37 (15) |
C13—C2—C12 | 105.13 (11) | O4—C16—C15 | 115.76 (14) |
C13—C2—C3 | 112.11 (11) | C17—C16—C15 | 119.86 (14) |
C12—C2—C3 | 112.14 (11) | C16—C17—C18 | 119.74 (14) |
C13—C2—C1 | 114.24 (11) | C16—C17—H17 | 120.1 |
C12—C2—C1 | 109.69 (10) | C18—C17—H17 | 120.1 |
C3—C2—C1 | 103.71 (10) | C19—C18—C17 | 119.58 (13) |
C4—C3—C21 | 116.86 (11) | C19—C18—C12 | 121.14 (12) |
C4—C3—C2 | 103.50 (11) | C17—C18—C12 | 119.06 (12) |
C21—C3—C2 | 116.76 (11) | O3—C19—C18 | 121.99 (12) |
C4—C3—H3 | 106.3 | O3—C19—C14 | 117.46 (13) |
C21—C3—H3 | 106.3 | C18—C19—C14 | 120.55 (13) |
C2—C3—H3 | 106.3 | O4—C20—H20A | 109.5 |
N1—C4—C3 | 101.52 (11) | O4—C20—H20B | 109.5 |
N1—C4—H4A | 111.5 | H20A—C20—H20B | 109.5 |
C3—C4—H4A | 111.5 | O4—C20—H20C | 109.5 |
N1—C4—H4B | 111.5 | H20A—C20—H20C | 109.5 |
C3—C4—H4B | 111.5 | H20B—C20—H20C | 109.5 |
H4A—C4—H4B | 109.3 | C26—C21—C22 | 117.43 (14) |
O1—C5—N2 | 125.84 (14) | C26—C21—C3 | 123.00 (13) |
O1—C5—C1 | 126.59 (13) | C22—C21—C3 | 119.50 (13) |
N2—C5—C1 | 107.52 (12) | C23—C22—C21 | 121.54 (17) |
C7—C6—C11 | 121.86 (14) | C23—C22—H22 | 119.2 |
C7—C6—N2 | 128.65 (14) | C21—C22—H22 | 119.2 |
C11—C6—N2 | 109.47 (12) | C24—C23—C22 | 120.48 (18) |
C6—C7—C8 | 117.69 (16) | C24—C23—H23 | 119.8 |
C6—C7—H7 | 121.2 | C22—C23—H23 | 119.8 |
C8—C7—H7 | 121.2 | C25—C24—C23 | 119.24 (16) |
C9—C8—C7 | 121.33 (16) | C25—C24—H24 | 120.4 |
C9—C8—H8 | 119.3 | C23—C24—H24 | 120.4 |
C7—C8—H8 | 119.3 | C24—C25—C26 | 120.14 (17) |
C8—C9—C10 | 120.46 (17) | C24—C25—H25 | 119.9 |
C8—C9—H9 | 119.8 | C26—C25—H25 | 119.9 |
C10—C9—H9 | 119.8 | C21—C26—C25 | 121.17 (16) |
C11—C10—C9 | 119.22 (16) | C21—C26—H26 | 119.4 |
C11—C10—H10 | 120.4 | C25—C26—H26 | 119.4 |
C9—C10—H10 | 120.4 | N1—C27—H27A | 109.5 |
C10—C11—C6 | 119.40 (13) | N1—C27—H27B | 109.5 |
C10—C11—C1 | 131.16 (13) | H27A—C27—H27B | 109.5 |
C6—C11—C1 | 109.40 (12) | N1—C27—H27C | 109.5 |
O2—C12—C18 | 122.46 (12) | H27A—C27—H27C | 109.5 |
O2—C12—C2 | 122.69 (12) | H27B—C27—H27C | 109.5 |
C18—C12—C2 | 114.84 (11) | C4—N1—C27 | 115.06 (13) |
O3—C13—C2 | 112.44 (11) | C4—N1—C1 | 106.76 (11) |
O3—C13—H13A | 109.1 | C27—N1—C1 | 115.48 (12) |
C2—C13—H13A | 109.1 | C5—N2—C6 | 112.41 (12) |
O3—C13—H13B | 109.1 | C5—N2—H2 | 123.1 (11) |
C2—C13—H13B | 109.1 | C6—N2—H2 | 124.4 (11) |
H13A—C13—H13B | 107.8 | C19—O3—C13 | 113.90 (10) |
C15—C14—C19 | 119.28 (14) | C16—O4—C20 | 117.03 (13) |
N1—C1—C2—C13 | −131.28 (11) | C1—C2—C13—O3 | −57.31 (15) |
C11—C1—C2—C13 | 105.74 (13) | C19—C14—C15—C16 | −0.6 (3) |
C5—C1—C2—C13 | −10.42 (15) | C14—C15—C16—O4 | 179.25 (15) |
N1—C1—C2—C12 | 111.00 (12) | C14—C15—C16—C17 | −0.3 (3) |
C11—C1—C2—C12 | −11.98 (16) | O4—C16—C17—C18 | −178.35 (15) |
C5—C1—C2—C12 | −128.14 (12) | C15—C16—C17—C18 | 1.2 (2) |
N1—C1—C2—C3 | −8.95 (13) | C16—C17—C18—C19 | −1.1 (2) |
C11—C1—C2—C3 | −131.93 (12) | C16—C17—C18—C12 | 173.62 (14) |
C5—C1—C2—C3 | 111.90 (12) | O2—C12—C18—C19 | −172.56 (14) |
C13—C2—C3—C4 | 104.93 (13) | C2—C12—C18—C19 | 8.73 (19) |
C12—C2—C3—C4 | −137.07 (12) | O2—C12—C18—C17 | 12.8 (2) |
C1—C2—C3—C4 | −18.80 (13) | C2—C12—C18—C17 | −165.90 (12) |
C13—C2—C3—C21 | −24.98 (16) | C17—C18—C19—O3 | 179.60 (13) |
C12—C2—C3—C21 | 93.02 (14) | C12—C18—C19—O3 | 5.0 (2) |
C1—C2—C3—C21 | −148.71 (11) | C17—C18—C19—C14 | 0.2 (2) |
C21—C3—C4—N1 | 169.87 (12) | C12—C18—C19—C14 | −174.45 (14) |
C2—C3—C4—N1 | 40.03 (14) | C15—C14—C19—O3 | −178.76 (14) |
N1—C1—C5—O1 | 56.5 (2) | C15—C14—C19—C18 | 0.7 (2) |
C11—C1—C5—O1 | 175.82 (15) | C4—C3—C21—C26 | −10.6 (2) |
C2—C1—C5—O1 | −58.19 (19) | C2—C3—C21—C26 | 112.71 (16) |
N1—C1—C5—N2 | −121.14 (13) | C4—C3—C21—C22 | 166.10 (14) |
C11—C1—C5—N2 | −1.84 (15) | C2—C3—C21—C22 | −70.64 (17) |
C2—C1—C5—N2 | 124.15 (12) | C26—C21—C22—C23 | −0.7 (2) |
C11—C6—C7—C8 | 0.8 (3) | C3—C21—C22—C23 | −177.56 (16) |
N2—C6—C7—C8 | −177.26 (16) | C21—C22—C23—C24 | 0.2 (3) |
C6—C7—C8—C9 | 0.9 (3) | C22—C23—C24—C25 | 0.3 (3) |
C7—C8—C9—C10 | −1.0 (3) | C23—C24—C25—C26 | −0.3 (3) |
C8—C9—C10—C11 | −0.6 (3) | C22—C21—C26—C25 | 0.8 (2) |
C9—C10—C11—C6 | 2.2 (2) | C3—C21—C26—C25 | 177.49 (15) |
C9—C10—C11—C1 | 179.56 (16) | C24—C25—C26—C21 | −0.3 (3) |
C7—C6—C11—C10 | −2.4 (2) | C3—C4—N1—C27 | −178.03 (14) |
N2—C6—C11—C10 | 176.04 (14) | C3—C4—N1—C1 | −48.48 (14) |
C7—C6—C11—C1 | 179.73 (14) | C11—C1—N1—C4 | 162.45 (12) |
N2—C6—C11—C1 | −1.85 (17) | C5—C1—N1—C4 | −84.51 (14) |
N1—C1—C11—C10 | −55.2 (2) | C2—C1—N1—C4 | 35.40 (14) |
C5—C1—C11—C10 | −175.36 (16) | C11—C1—N1—C27 | −68.24 (17) |
C2—C1—C11—C10 | 63.1 (2) | C5—C1—N1—C27 | 44.80 (18) |
N1—C1—C11—C6 | 122.33 (13) | C2—C1—N1—C27 | 164.71 (13) |
C5—C1—C11—C6 | 2.20 (15) | O1—C5—N2—C6 | −176.80 (15) |
C2—C1—C11—C6 | −119.38 (13) | C1—C5—N2—C6 | 0.88 (17) |
C13—C2—C12—O2 | 141.65 (14) | C7—C6—N2—C5 | 178.87 (16) |
C3—C2—C12—O2 | 19.57 (19) | C11—C6—N2—C5 | 0.59 (18) |
C1—C2—C12—O2 | −95.10 (16) | C18—C19—O3—C13 | 17.24 (19) |
C13—C2—C12—C18 | −39.64 (15) | C14—C19—O3—C13 | −163.30 (13) |
C3—C2—C12—C18 | −161.72 (12) | C2—C13—O3—C19 | −53.20 (15) |
C1—C2—C12—C18 | 83.61 (14) | C17—C16—O4—C20 | −1.0 (2) |
C12—C2—C13—O3 | 62.99 (13) | C15—C16—O4—C20 | 179.47 (15) |
C3—C2—C13—O3 | −174.93 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.878 (18) | 2.167 (19) | 3.0401 (16) | 172.8 (16) |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C27H24N2O4 |
Mr | 440.48 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 9.2244 (2), 26.1163 (5), 9.3506 (2) |
β (°) | 103.233 (1) |
V (Å3) | 2192.81 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.21 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.899, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27791, 5379, 3670 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 1.02 |
No. of reflections | 5379 |
No. of parameters | 304 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.18 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.878 (18) | 2.167 (19) | 3.0401 (16) | 172.8 (16) |
Symmetry code: (i) −x+1, −y, −z. |
Spiroheterocycles represent an important class of naturally occurring substances characterized by their highly pronounced biological activities·(James et al., 1991) Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products and pharmacologically active compounds. (Deshong & Leginus, 1983). Pyrrolidine and oxindole alkaloids (Fujimori, 1990) constitute another class of compounds with significant biological activity which are normally found in rhyncophylline, corynoxeine, nitraphylline, vincatine, horsifiline,etc (Henrickson & Silva, 1962).
In the crystal structure of the title compound, C27H24N2O4, the chromanone moiety consists of a methoxy benzene ring fused with a six membered heterocyclic ring which adopts a sofa conformation (Abdul Ajees et al., 2001). The five membered spiropyrrolidine ring is in an envelope conformation. The oxindole and phenyl rings attached to the five membered rings are nearly perpendicular to each other. The molecules are linked into centrosymmetric R22(14) dimmer by a simple N—H···O interaction (Bernstein et al., 1995)