organic compounds
Methyl 3′-(2,5-dimethylbenzyl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine]-3′-carboxylate chloroform monosolvate
aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in
In the title solvate, C29H30N2O3·CHCl3, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methylpyrrolidine ring is 88.88 (8)°. The latter ring adopts an with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and dimethylbenzene rings, respectively. The molecular conformation is stabilized by intramolecular C—H⋯O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloroform solvent molecule is linked to the organic molecule by a C—H⋯O hydrogen bond involving the carbonyl O atom of the carboxylate group. In the crystal, molecules are linked via bifurcated N—H⋯(N,O) and C—H⋯O hydrogen bonds, forming chains propagating along [001].
CCDC reference: 988124
Related literature
For the biological activity of et al. (1982); Chande et al. (2005); Glover et al. (1998). For a related see: Karthikeyan et al. (2014). For puckering parameters, see: Cremer & Pople (1975). For graph-set motif notation, see: Bernstein et al. (1995). For bond-length distortions in small rings, see: Allen (1981).
and oxindole derivatives, see: BhattacharyaExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 988124
10.1107/S1600536814004073/su2703sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004073/su2703Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004073/su2703Isup3.cml
A mixture of (E)-methyl 2-(2,5-dimethylbenzyl)-3-phenylacrylate (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) in acetonitrile (8 ml) was refluxed for 12 h. After completion of the reaction, as indicated by TLC, the mixture was concentrated. The resulting crude mass was diluted with water (10 ml) and extracted with ethyl acetate (3 × 10 ml). The combined organic layers were washed with brine (2 × 10 ml) and dried over anhydrous Na2SO4. The organic layer was concentrated and the residue purified by
on silica gel (Acme 100–200 mesh), using ethyl acetate:hexanes (2:8) to afford the title compound as a colourless crystals in 67% yield.The H atoms could all be located in difference electron-density maps. In the final cycles of
they were treated as riding atoms and their distances were geometrically constrained: C—H = 0.93 and 0.96 Å for CH and CH3H atoms, respectively, with Uiso(H) = 1.5 Ueq(C– methyl) and = 1.2Ueq(C) for other H atoms.Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. A partial view along the a axis of the crystal packing of the title compound. The N—H···N, N-H···O and C—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details). |
C29H30N2O3·CHCl3 | F(000) = 1200 |
Mr = 573.92 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8093 reflections |
a = 12.9164 (4) Å | θ = 2.0–30.0° |
b = 17.6167 (5) Å | µ = 0.36 mm−1 |
c = 12.4548 (5) Å | T = 293 K |
β = 98.135 (2)° | Block, colourless |
V = 2805.50 (16) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 4986 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 30.0°, θmin = 2.0° |
ω scans | h = −18→15 |
32563 measured reflections | k = −24→17 |
8093 independent reflections | l = −16→17 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0743P)2 + 0.8771P] where P = (Fo2 + 2Fc2)/3 |
8093 reflections | (Δ/σ)max = 0.029 |
347 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C29H30N2O3·CHCl3 | V = 2805.50 (16) Å3 |
Mr = 573.92 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9164 (4) Å | µ = 0.36 mm−1 |
b = 17.6167 (5) Å | T = 293 K |
c = 12.4548 (5) Å | 0.35 × 0.30 × 0.25 mm |
β = 98.135 (2)° |
Bruker Kappa APEXII CCD diffractometer | 4986 reflections with I > 2σ(I) |
32563 measured reflections | Rint = 0.032 |
8093 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.38 e Å−3 |
8093 reflections | Δρmin = −0.46 e Å−3 |
347 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 | 0.52972 (18) | 0.16392 (14) | 0.1611 (2) | 0.0606 (6) | |
H1 | 0.5616 | 0.1446 | 0.1045 | 0.073* | |
C2 | 0.4214 (2) | 0.16690 (18) | 0.1514 (3) | 0.0870 (10) | |
H2 | 0.3813 | 0.1492 | 0.0884 | 0.104* | |
C3 | 0.3732 (2) | 0.19554 (17) | 0.2334 (3) | 0.0844 (10) | |
H3 | 0.3006 | 0.1969 | 0.2265 | 0.101* | |
C4 | 0.43157 (18) | 0.22214 (14) | 0.3255 (3) | 0.0670 (7) | |
H4 | 0.3987 | 0.2417 | 0.3813 | 0.080* | |
C5 | 0.54030 (15) | 0.22008 (11) | 0.33620 (19) | 0.0473 (5) | |
H5 | 0.5796 | 0.2393 | 0.3986 | 0.057* | |
C6 | 0.59068 (14) | 0.18961 (10) | 0.25467 (16) | 0.0391 (4) | |
C7 | 0.70826 (13) | 0.19113 (9) | 0.25662 (13) | 0.0300 (3) | |
H7 | 0.7220 | 0.1678 | 0.1886 | 0.036* | |
C8 | 0.74566 (13) | 0.27309 (9) | 0.25403 (14) | 0.0319 (3) | |
H8A | 0.7355 | 0.2928 | 0.1805 | 0.038* | |
H8B | 0.7086 | 0.3053 | 0.2991 | 0.038* | |
C9 | 0.86380 (12) | 0.21922 (9) | 0.39155 (12) | 0.0269 (3) | |
C10 | 0.82724 (13) | 0.25825 (9) | 0.49252 (13) | 0.0309 (3) | |
C11 | 0.99571 (13) | 0.21963 (10) | 0.54390 (14) | 0.0347 (4) | |
C12 | 1.09263 (16) | 0.20958 (12) | 0.60490 (17) | 0.0482 (5) | |
H12 | 1.1043 | 0.2224 | 0.6780 | 0.058* | |
C13 | 1.17168 (16) | 0.17983 (13) | 0.5537 (2) | 0.0540 (5) | |
H13 | 1.2374 | 0.1715 | 0.5932 | 0.065* | |
C14 | 1.15450 (15) | 0.16239 (12) | 0.44510 (19) | 0.0497 (5) | |
H14 | 1.2091 | 0.1434 | 0.4117 | 0.060* | |
C15 | 1.05653 (14) | 0.17275 (10) | 0.38447 (16) | 0.0391 (4) | |
H15 | 1.0456 | 0.1616 | 0.3108 | 0.047* | |
C16 | 0.97590 (13) | 0.19984 (9) | 0.43528 (13) | 0.0301 (3) | |
C17 | 0.78538 (12) | 0.15185 (9) | 0.35030 (12) | 0.0272 (3) | |
C18 | 0.73755 (13) | 0.11476 (9) | 0.44370 (14) | 0.0324 (4) | |
H18A | 0.7936 | 0.1058 | 0.5028 | 0.039* | |
H18B | 0.6903 | 0.1511 | 0.4693 | 0.039* | |
C19 | 0.67848 (13) | 0.04089 (9) | 0.42034 (15) | 0.0356 (4) | |
C20 | 0.64281 (14) | 0.01636 (10) | 0.31604 (17) | 0.0418 (4) | |
H20 | 0.6602 | 0.0446 | 0.2581 | 0.050* | |
C21 | 0.58202 (15) | −0.04865 (11) | 0.2939 (2) | 0.0506 (5) | |
C22 | 0.56029 (16) | −0.09077 (12) | 0.3815 (2) | 0.0592 (6) | |
H22 | 0.5208 | −0.1349 | 0.3698 | 0.071* | |
C23 | 0.59634 (16) | −0.06826 (12) | 0.4854 (2) | 0.0573 (6) | |
H23 | 0.5806 | −0.0978 | 0.5429 | 0.069* | |
C24 | 0.65561 (14) | −0.00280 (11) | 0.50774 (18) | 0.0443 (5) | |
C25 | 0.85308 (13) | 0.09330 (9) | 0.30117 (14) | 0.0314 (3) | |
C26 | 0.96441 (19) | −0.01230 (12) | 0.3421 (2) | 0.0563 (6) | |
H26A | 0.9259 | −0.0453 | 0.2896 | 0.084* | |
H26B | 0.9945 | −0.0414 | 0.4039 | 0.084* | |
H26C | 1.0191 | 0.0123 | 0.3103 | 0.084* | |
C27 | 0.90549 (16) | 0.34317 (11) | 0.31638 (17) | 0.0454 (5) | |
H27A | 0.8690 | 0.3715 | 0.3651 | 0.068* | |
H27B | 0.9024 | 0.3701 | 0.2490 | 0.068* | |
H27C | 0.9772 | 0.3368 | 0.3479 | 0.068* | |
C28 | 0.5391 (2) | −0.06896 (15) | 0.1793 (2) | 0.0740 (8) | |
H28A | 0.4752 | −0.0969 | 0.1785 | 0.111* | |
H28B | 0.5891 | −0.0995 | 0.1487 | 0.111* | |
H28C | 0.5256 | −0.0234 | 0.1373 | 0.111* | |
C29 | 0.69211 (19) | 0.01897 (14) | 0.6230 (2) | 0.0604 (6) | |
H29A | 0.6638 | −0.0158 | 0.6706 | 0.091* | |
H29B | 0.6689 | 0.0695 | 0.6358 | 0.091* | |
H29C | 0.7671 | 0.0172 | 0.6366 | 0.091* | |
C30 | 0.8351 (2) | −0.03717 (16) | 0.0148 (2) | 0.0727 (7) | |
H30 | 0.8775 | −0.0035 | 0.0660 | 0.087* | |
N1 | 0.85668 (11) | 0.26899 (7) | 0.29684 (11) | 0.0297 (3) | |
N2 | 0.90658 (11) | 0.25256 (9) | 0.57607 (12) | 0.0391 (4) | |
H2A | 0.9025 | 0.2674 | 0.6411 | 0.047* | |
O1 | 0.74367 (10) | 0.28839 (7) | 0.49619 (10) | 0.0406 (3) | |
O2 | 0.87103 (11) | 0.09300 (8) | 0.20917 (10) | 0.0470 (3) | |
O3 | 0.89518 (10) | 0.04398 (7) | 0.37572 (10) | 0.0376 (3) | |
Cl1 | 0.80296 (6) | −0.11741 (5) | 0.08605 (8) | 0.0992 (3) | |
Cl2 | 0.72435 (8) | 0.01165 (5) | −0.03976 (10) | 0.1107 (3) | |
Cl3 | 0.91063 (9) | −0.06436 (6) | −0.08484 (8) | 0.1116 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0494 (12) | 0.0582 (13) | 0.0670 (15) | −0.0072 (10) | −0.0171 (11) | 0.0041 (11) |
C2 | 0.0539 (16) | 0.086 (2) | 0.108 (3) | −0.0188 (15) | −0.0341 (16) | 0.0200 (18) |
C3 | 0.0336 (12) | 0.0785 (19) | 0.137 (3) | −0.0047 (12) | −0.0028 (16) | 0.0423 (19) |
C4 | 0.0418 (12) | 0.0548 (13) | 0.108 (2) | 0.0071 (10) | 0.0222 (13) | 0.0316 (14) |
C5 | 0.0376 (10) | 0.0399 (10) | 0.0651 (14) | 0.0012 (8) | 0.0102 (9) | 0.0142 (9) |
C6 | 0.0340 (9) | 0.0296 (8) | 0.0517 (11) | −0.0008 (7) | −0.0013 (8) | 0.0098 (8) |
C7 | 0.0339 (8) | 0.0287 (8) | 0.0267 (8) | −0.0002 (6) | 0.0018 (6) | 0.0003 (6) |
C8 | 0.0367 (9) | 0.0299 (8) | 0.0287 (8) | 0.0003 (7) | 0.0039 (7) | 0.0051 (6) |
C9 | 0.0298 (8) | 0.0286 (7) | 0.0228 (7) | −0.0004 (6) | 0.0055 (6) | −0.0013 (6) |
C10 | 0.0341 (9) | 0.0312 (8) | 0.0283 (8) | −0.0014 (7) | 0.0072 (7) | −0.0031 (6) |
C11 | 0.0317 (8) | 0.0382 (9) | 0.0341 (9) | −0.0009 (7) | 0.0044 (7) | −0.0018 (7) |
C12 | 0.0415 (11) | 0.0599 (13) | 0.0399 (11) | 0.0017 (9) | −0.0056 (8) | −0.0038 (9) |
C13 | 0.0344 (10) | 0.0611 (13) | 0.0632 (14) | 0.0037 (9) | −0.0046 (9) | −0.0019 (11) |
C14 | 0.0335 (10) | 0.0517 (12) | 0.0653 (14) | 0.0056 (8) | 0.0119 (9) | −0.0041 (10) |
C15 | 0.0374 (9) | 0.0410 (10) | 0.0402 (10) | 0.0003 (8) | 0.0100 (8) | −0.0042 (8) |
C16 | 0.0306 (8) | 0.0298 (8) | 0.0301 (8) | −0.0030 (6) | 0.0055 (6) | −0.0002 (6) |
C17 | 0.0314 (8) | 0.0250 (7) | 0.0253 (8) | −0.0013 (6) | 0.0046 (6) | 0.0003 (6) |
C18 | 0.0356 (9) | 0.0304 (8) | 0.0324 (9) | −0.0007 (7) | 0.0090 (7) | 0.0043 (6) |
C19 | 0.0292 (8) | 0.0284 (8) | 0.0502 (11) | 0.0026 (6) | 0.0093 (7) | 0.0089 (7) |
C20 | 0.0380 (10) | 0.0307 (9) | 0.0562 (12) | −0.0020 (7) | 0.0049 (8) | 0.0039 (8) |
C21 | 0.0340 (10) | 0.0314 (9) | 0.0848 (16) | 0.0004 (8) | 0.0029 (10) | −0.0025 (10) |
C22 | 0.0367 (10) | 0.0332 (10) | 0.107 (2) | −0.0054 (8) | 0.0098 (12) | 0.0091 (12) |
C23 | 0.0420 (11) | 0.0420 (11) | 0.0911 (19) | 0.0000 (9) | 0.0208 (12) | 0.0279 (11) |
C24 | 0.0349 (9) | 0.0375 (9) | 0.0637 (13) | 0.0059 (8) | 0.0178 (9) | 0.0191 (9) |
C25 | 0.0345 (8) | 0.0276 (8) | 0.0318 (9) | −0.0022 (7) | 0.0036 (7) | −0.0021 (6) |
C26 | 0.0637 (14) | 0.0415 (11) | 0.0639 (14) | 0.0206 (10) | 0.0101 (11) | −0.0004 (10) |
C27 | 0.0527 (11) | 0.0331 (9) | 0.0501 (12) | −0.0124 (8) | 0.0055 (9) | 0.0033 (8) |
C28 | 0.0675 (16) | 0.0518 (14) | 0.097 (2) | −0.0107 (12) | −0.0083 (14) | −0.0168 (13) |
C29 | 0.0594 (14) | 0.0661 (14) | 0.0595 (14) | 0.0025 (11) | 0.0219 (11) | 0.0265 (11) |
C30 | 0.0636 (16) | 0.0764 (17) | 0.0758 (18) | −0.0125 (13) | 0.0022 (13) | −0.0162 (14) |
N1 | 0.0347 (7) | 0.0274 (7) | 0.0272 (7) | −0.0048 (5) | 0.0050 (5) | 0.0023 (5) |
N2 | 0.0374 (8) | 0.0554 (9) | 0.0243 (7) | 0.0019 (7) | 0.0037 (6) | −0.0096 (6) |
O1 | 0.0380 (7) | 0.0472 (7) | 0.0373 (7) | 0.0077 (6) | 0.0084 (5) | −0.0086 (5) |
O2 | 0.0607 (9) | 0.0490 (8) | 0.0330 (7) | 0.0132 (7) | 0.0124 (6) | −0.0031 (6) |
O3 | 0.0426 (7) | 0.0309 (6) | 0.0394 (7) | 0.0085 (5) | 0.0064 (5) | 0.0036 (5) |
Cl1 | 0.0716 (5) | 0.1114 (6) | 0.1077 (7) | −0.0031 (4) | −0.0107 (4) | 0.0367 (5) |
Cl2 | 0.0970 (6) | 0.0791 (5) | 0.1532 (9) | 0.0107 (4) | 0.0078 (6) | 0.0290 (5) |
Cl3 | 0.1246 (8) | 0.1139 (7) | 0.1039 (7) | −0.0108 (6) | 0.0420 (6) | −0.0332 (5) |
C1—C6 | 1.386 (3) | C17—C18 | 1.538 (2) |
C1—C2 | 1.388 (4) | C18—C19 | 1.516 (2) |
C1—H1 | 0.9300 | C18—H18A | 0.9700 |
C2—C3 | 1.366 (5) | C18—H18B | 0.9700 |
C2—H2 | 0.9300 | C19—C20 | 1.385 (3) |
C3—C4 | 1.363 (5) | C19—C24 | 1.398 (3) |
C3—H3 | 0.9300 | C20—C21 | 1.394 (3) |
C4—C5 | 1.392 (3) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.380 (3) |
C5—C6 | 1.389 (3) | C21—C28 | 1.500 (4) |
C5—H5 | 0.9300 | C22—C23 | 1.371 (4) |
C6—C7 | 1.516 (2) | C22—H22 | 0.9300 |
C7—C8 | 1.524 (2) | C23—C24 | 1.390 (3) |
C7—C17 | 1.582 (2) | C23—H23 | 0.9300 |
C7—H7 | 0.9800 | C24—C29 | 1.497 (3) |
C8—N1 | 1.459 (2) | C25—O2 | 1.201 (2) |
C8—H8A | 0.9700 | C25—O3 | 1.330 (2) |
C8—H8B | 0.9700 | C26—O3 | 1.437 (2) |
C9—N1 | 1.462 (2) | C26—H26A | 0.9600 |
C9—C16 | 1.512 (2) | C26—H26B | 0.9600 |
C9—C10 | 1.564 (2) | C26—H26C | 0.9600 |
C9—C17 | 1.597 (2) | C27—N1 | 1.456 (2) |
C10—O1 | 1.210 (2) | C27—H27A | 0.9600 |
C10—N2 | 1.357 (2) | C27—H27B | 0.9600 |
C11—C12 | 1.381 (3) | C27—H27C | 0.9600 |
C11—C16 | 1.385 (2) | C28—H28A | 0.9600 |
C11—N2 | 1.397 (2) | C28—H28B | 0.9600 |
C12—C13 | 1.382 (3) | C28—H28C | 0.9600 |
C12—H12 | 0.9300 | C29—H29A | 0.9600 |
C13—C14 | 1.374 (3) | C29—H29B | 0.9600 |
C13—H13 | 0.9300 | C29—H29C | 0.9600 |
C14—C15 | 1.391 (3) | C30—Cl2 | 1.724 (3) |
C14—H14 | 0.9300 | C30—Cl1 | 1.750 (3) |
C15—C16 | 1.378 (2) | C30—Cl3 | 1.751 (3) |
C15—H15 | 0.9300 | C30—H30 | 0.9800 |
C17—C25 | 1.534 (2) | N2—H2A | 0.8600 |
C6—C1—C2 | 120.4 (3) | C19—C18—H18A | 107.9 |
C6—C1—H1 | 119.8 | C17—C18—H18A | 107.9 |
C2—C1—H1 | 119.8 | C19—C18—H18B | 107.9 |
C3—C2—C1 | 120.6 (3) | C17—C18—H18B | 107.9 |
C3—C2—H2 | 119.7 | H18A—C18—H18B | 107.2 |
C1—C2—H2 | 119.7 | C20—C19—C24 | 118.66 (17) |
C4—C3—C2 | 120.0 (2) | C20—C19—C18 | 122.66 (16) |
C4—C3—H3 | 120.0 | C24—C19—C18 | 118.63 (17) |
C2—C3—H3 | 120.0 | C19—C20—C21 | 123.04 (19) |
C3—C4—C5 | 120.1 (3) | C19—C20—H20 | 118.5 |
C3—C4—H4 | 120.0 | C21—C20—H20 | 118.5 |
C5—C4—H4 | 120.0 | C22—C21—C20 | 117.2 (2) |
C6—C5—C4 | 120.7 (2) | C22—C21—C28 | 122.3 (2) |
C6—C5—H5 | 119.6 | C20—C21—C28 | 120.4 (2) |
C4—C5—H5 | 119.6 | C23—C22—C21 | 120.71 (19) |
C1—C6—C5 | 118.11 (19) | C23—C22—H22 | 119.6 |
C1—C6—C7 | 117.89 (19) | C21—C22—H22 | 119.6 |
C5—C6—C7 | 123.60 (17) | C22—C23—C24 | 122.2 (2) |
C6—C7—C8 | 109.65 (14) | C22—C23—H23 | 118.9 |
C6—C7—C17 | 121.93 (14) | C24—C23—H23 | 118.9 |
C8—C7—C17 | 105.16 (13) | C23—C24—C19 | 118.2 (2) |
C6—C7—H7 | 106.4 | C23—C24—C29 | 119.59 (19) |
C8—C7—H7 | 106.4 | C19—C24—C29 | 122.23 (18) |
C17—C7—H7 | 106.4 | O2—C25—O3 | 123.23 (16) |
N1—C8—C7 | 104.09 (13) | O2—C25—C17 | 125.55 (15) |
N1—C8—H8A | 110.9 | O3—C25—C17 | 111.12 (14) |
C7—C8—H8A | 110.9 | O3—C26—H26A | 109.5 |
N1—C8—H8B | 110.9 | O3—C26—H26B | 109.5 |
C7—C8—H8B | 110.9 | H26A—C26—H26B | 109.5 |
H8A—C8—H8B | 109.0 | O3—C26—H26C | 109.5 |
N1—C9—C16 | 111.94 (13) | H26A—C26—H26C | 109.5 |
N1—C9—C10 | 113.17 (13) | H26B—C26—H26C | 109.5 |
C16—C9—C10 | 101.09 (12) | N1—C27—H27A | 109.5 |
N1—C9—C17 | 102.79 (12) | N1—C27—H27B | 109.5 |
C16—C9—C17 | 118.65 (13) | H27A—C27—H27B | 109.5 |
C10—C9—C17 | 109.60 (12) | N1—C27—H27C | 109.5 |
O1—C10—N2 | 125.77 (16) | H27A—C27—H27C | 109.5 |
O1—C10—C9 | 126.59 (15) | H27B—C27—H27C | 109.5 |
N2—C10—C9 | 107.64 (14) | C21—C28—H28A | 109.5 |
C12—C11—C16 | 122.20 (17) | C21—C28—H28B | 109.5 |
C12—C11—N2 | 127.95 (17) | H28A—C28—H28B | 109.5 |
C16—C11—N2 | 109.79 (15) | C21—C28—H28C | 109.5 |
C11—C12—C13 | 117.80 (19) | H28A—C28—H28C | 109.5 |
C11—C12—H12 | 121.1 | H28B—C28—H28C | 109.5 |
C13—C12—H12 | 121.1 | C24—C29—H29A | 109.5 |
C14—C13—C12 | 120.82 (19) | C24—C29—H29B | 109.5 |
C14—C13—H13 | 119.6 | H29A—C29—H29B | 109.5 |
C12—C13—H13 | 119.6 | C24—C29—H29C | 109.5 |
C13—C14—C15 | 120.86 (19) | H29A—C29—H29C | 109.5 |
C13—C14—H14 | 119.6 | H29B—C29—H29C | 109.5 |
C15—C14—H14 | 119.6 | Cl2—C30—Cl1 | 111.11 (15) |
C16—C15—C14 | 118.99 (18) | Cl2—C30—Cl3 | 111.84 (17) |
C16—C15—H15 | 120.5 | Cl1—C30—Cl3 | 109.54 (16) |
C14—C15—H15 | 120.5 | Cl2—C30—H30 | 108.1 |
C15—C16—C11 | 119.24 (16) | Cl1—C30—H30 | 108.1 |
C15—C16—C9 | 131.30 (15) | Cl3—C30—H30 | 108.1 |
C11—C16—C9 | 109.27 (14) | C27—N1—C8 | 113.35 (14) |
C25—C17—C18 | 109.19 (13) | C27—N1—C9 | 115.28 (14) |
C25—C17—C7 | 109.56 (13) | C8—N1—C9 | 105.71 (12) |
C18—C17—C7 | 117.73 (13) | C10—N2—C11 | 111.97 (14) |
C25—C17—C9 | 104.86 (12) | C10—N2—H2A | 124.0 |
C18—C17—C9 | 112.13 (13) | C11—N2—H2A | 124.0 |
C7—C17—C9 | 102.51 (12) | C25—O3—C26 | 117.19 (15) |
C19—C18—C17 | 117.69 (15) | ||
C6—C1—C2—C3 | 0.4 (4) | C10—C9—C17—C25 | −149.46 (13) |
C1—C2—C3—C4 | 0.6 (4) | N1—C9—C17—C18 | −151.71 (13) |
C2—C3—C4—C5 | −0.1 (4) | C16—C9—C17—C18 | 84.19 (17) |
C3—C4—C5—C6 | −1.4 (3) | C10—C9—C17—C18 | −31.11 (17) |
C2—C1—C6—C5 | −1.8 (3) | N1—C9—C17—C7 | −24.50 (14) |
C2—C1—C6—C7 | −174.9 (2) | C16—C9—C17—C7 | −148.60 (14) |
C4—C5—C6—C1 | 2.3 (3) | C10—C9—C17—C7 | 96.10 (14) |
C4—C5—C6—C7 | 174.93 (18) | C25—C17—C18—C19 | −52.72 (19) |
C1—C6—C7—C8 | 109.52 (19) | C7—C17—C18—C19 | 72.97 (19) |
C5—C6—C7—C8 | −63.2 (2) | C9—C17—C18—C19 | −168.48 (14) |
C1—C6—C7—C17 | −127.14 (19) | C17—C18—C19—C20 | −17.2 (2) |
C5—C6—C7—C17 | 60.2 (2) | C17—C18—C19—C24 | 165.28 (15) |
C6—C7—C8—N1 | 159.17 (14) | C24—C19—C20—C21 | 2.2 (3) |
C17—C7—C8—N1 | 26.43 (16) | C18—C19—C20—C21 | −175.26 (17) |
N1—C9—C10—O1 | 55.2 (2) | C19—C20—C21—C22 | −2.1 (3) |
C16—C9—C10—O1 | 175.02 (17) | C19—C20—C21—C28 | 175.4 (2) |
C17—C9—C10—O1 | −58.9 (2) | C20—C21—C22—C23 | 0.9 (3) |
N1—C9—C10—N2 | −124.66 (15) | C28—C21—C22—C23 | −176.5 (2) |
C16—C9—C10—N2 | −4.79 (17) | C21—C22—C23—C24 | 0.1 (3) |
C17—C9—C10—N2 | 121.26 (15) | C22—C23—C24—C19 | 0.0 (3) |
C16—C11—C12—C13 | 1.1 (3) | C22—C23—C24—C29 | 179.6 (2) |
N2—C11—C12—C13 | −175.89 (19) | C20—C19—C24—C23 | −1.1 (3) |
C11—C12—C13—C14 | 1.3 (3) | C18—C19—C24—C23 | 176.45 (16) |
C12—C13—C14—C15 | −1.3 (3) | C20—C19—C24—C29 | 179.27 (18) |
C13—C14—C15—C16 | −1.0 (3) | C18—C19—C24—C29 | −3.1 (3) |
C14—C15—C16—C11 | 3.2 (3) | C18—C17—C25—O2 | 152.45 (17) |
C14—C15—C16—C9 | 177.68 (17) | C7—C17—C25—O2 | 22.2 (2) |
C12—C11—C16—C15 | −3.3 (3) | C9—C17—C25—O2 | −87.22 (19) |
N2—C11—C16—C15 | 174.10 (16) | C18—C17—C25—O3 | −30.95 (18) |
C12—C11—C16—C9 | −178.93 (17) | C7—C17—C25—O3 | −161.22 (13) |
N2—C11—C16—C9 | −1.49 (19) | C9—C17—C25—O3 | 89.38 (15) |
N1—C9—C16—C15 | −50.4 (2) | C7—C8—N1—C27 | −171.60 (14) |
C10—C9—C16—C15 | −171.15 (18) | C7—C8—N1—C9 | −44.41 (16) |
C17—C9—C16—C15 | 69.1 (2) | C16—C9—N1—C27 | −62.53 (18) |
N1—C9—C16—C11 | 124.47 (15) | C10—C9—N1—C27 | 50.92 (19) |
C10—C9—C16—C11 | 3.73 (16) | C17—C9—N1—C27 | 169.04 (14) |
C17—C9—C16—C11 | −116.06 (15) | C16—C9—N1—C8 | 171.44 (13) |
C6—C7—C17—C25 | 122.61 (16) | C10—C9—N1—C8 | −75.11 (15) |
C8—C7—C17—C25 | −111.99 (14) | C17—C9—N1—C8 | 43.01 (15) |
C6—C7—C17—C18 | −2.9 (2) | O1—C10—N2—C11 | −175.49 (17) |
C8—C7—C17—C18 | 122.51 (15) | C9—C10—N2—C11 | 4.3 (2) |
C6—C7—C17—C9 | −126.44 (15) | C12—C11—N2—C10 | 175.34 (19) |
C8—C7—C17—C9 | −1.03 (16) | C16—C11—N2—C10 | −1.9 (2) |
N1—C9—C17—C25 | 89.93 (14) | O2—C25—O3—C26 | −0.7 (3) |
C16—C9—C17—C25 | −34.17 (17) | C17—C25—O3—C26 | −177.36 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.45 | 3.292 (2) | 151 |
C18—H18B···O1 | 0.97 | 2.52 | 3.127 (2) | 120 |
C30—H30···O2 | 0.98 | 2.47 | 3.319 (3) | 144 |
N2—H2A···O2i | 0.86 | 2.65 | 3.252 (2) | 128 |
N2—H2A···N1i | 0.86 | 2.20 | 2.936 (2) | 143 |
C7—H7···O1ii | 0.98 | 2.57 | 3.359 (2) | 138 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.45 | 3.292 (2) | 151 |
C18—H18B···O1 | 0.97 | 2.52 | 3.127 (2) | 120 |
C30—H30···O2 | 0.98 | 2.47 | 3.319 (3) | 144 |
N2—H2A···O2i | 0.86 | 2.65 | 3.252 (2) | 128 |
N2—H2A···N1i | 0.86 | 2.20 | 2.936 (2) | 143 |
C7—H7···O1ii | 0.98 | 2.57 | 3.359 (2) | 138 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Synthesis of spiro compounds has drawn considerable attention from chemists, in view of their very good antimycobacterial activity (Chande et al., 2005). Oxindole derivatives are known to be potent inhibitors of monoamine oxidase (MAO) in human urine and rat tissues (Glover et al., 1998) and potent antagonists of in vitro receptor binding by atrial natriuretic peptide besides possessing a wide range of central nervous system activities (Bhattacharya et al., 1982).
The molecular structure of the title compound is illustrated in Fig 1. In the molecule, there is C—H···O hydrogen bond, forming an S(6) and S(9) ring motif (Bernstein et al., 1995). The indole ring system is essentially planar with a maximum deviation of 0.0782 (17) Å for the atom C10. The mean plane of the indole ring system forms dihedral angle of 88.88 (8)° with central mean plane of pyrrolidine five membered ring. The latter forms a dihedral angle of 42.08 (10)° with the benzyl ring. Atom O1 significantly deviates from the mean plane of the indole ring system by 0.1965 (12) Å. The molecular dimensions in the title compound are in excellent agreement with the those reported for a related compound (Karthikeyan et al., 2014).
The spiro-pyrrolidine ring adopts an envelope conformation with atom N1 at the flap position. The distance to the flap position from the mean plane of the spiro carbon is 0.2628 (15) Å. The puckering parameters (Cremer & Pople, 1975) of the ring are Q2 = 0.4155 (17) Å and φ2 = 0.5 (2)°. The central spiro-pyrrolidine ring is perpendicular to the phenyl ring (C1—C6) with a dihedral angle of 86.94 (11)°. The carbonyl group and the benzyl ring have an (+)anti-periplanar conformation with the torsion angle (C18—C17—C25—O2) of 152.45 (17)°.
In the benzene ring (C11—C16) of the indole ring system, the expansion of the ipso angles at C11, C13 and C14 [122.20 (17), 120.82 (19) and 120.86 (19)°, respectively] and contraction of the apical angles at C12, C15 and C16 [117.80 (19), 118.99 (18) and 119.24 (16)°, respectively] are caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring and the strain is taken up by the angular distortion rather than by bond-length distortions (Allen, 1981). The carboxyl group and oxindole ring system are (-)syn-clinal to each other with the torsion angle (C9—C17—C25—O2) of -87.22 (9)°.
In the crystal, (Fig. 2 and Table 1), molecules are linked by N2—H2A···N1(i) [x,-y + 1/2,z + 1/2] and N2—H2A···O2(i) [x,-y + 1/2,z + 1/2] bifurcated hydrogen bonds which together generate C21[R21(6)] chains (Bernstein et al., 1995), running parallel to [001]. The intermolecular C7—H7···O1(ii) [x,-y + 1/2,z - 1/2] interaction forms C(6) chains running parallel to the same [001] axis. The CHCl3 solvent molecule is involved in an intramolecular hydrogen bond with the C═ O atom, O2, of the carboxylate group.