organic compounds
5′′-(4-Chlorobenzylidene)-4′-(4-chlorophenyl)-5-fluoro-1′,1′′-dimethylindoline-3-spiro-2′-pyrrolidine-3′-spiro-3′′-piperidine-2,4′′-dione
aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, bDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India, cDepartment of Physics, The Madura College, Madurai 625 011, India, and dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com
The piperidine ring of the title compound, C30H26Cl2FN3O2, adopts a twisted chair conformation. The pyrrolidine ring has a twisted envelope structure with the N atom at the flap [displaced by 0.592 (3) Å]. The fluorooxindole, chlorophenyl and chlorobenzylidene groups are planar with r.m.s. deviations of 0.0348, 0.0048 and 0.0048 Å, respectively. The structure is stabilized by intermolecular N—H⋯O hydrogen bonds.
Related literature
For biological applications of 1,4-dihydropyridine derivatives, see: Jerom & Spencer (1988); Perumal et al. (2001); Hagenbach & Gysin (1952); Mobio et al. (1989); Katritzky & Fan (1990); Ganellin & Spickett (1965); El-Subbagh et al. (2000). For their use as synthetic intermediates in the preparation of various pharmaceuticals, see: Wang & Wuorola (1992). For their ocurrence in natural products such as see: Angle & Breitenbucher (1995).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536811007550/zj2003sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811007550/zj2003Isup2.hkl
A mixture of 1-methyl-3,5-bis[(E)-chlorobenzylidene]tetrahydro-4 (1H)-pyridin-ones (1 mmol), 5-fluoroisatin (1 mmol) and sarcosine in methanol (10 ml) was refluxed for 30 min. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered and washed with water to obtain the pure product. The product was dissolved in methonol and allowed to evoporate at room temperature. Transparent, needle-shaped, colourless crystals of small sizes (8 x 2 x 2 mm3)were obtained in a period of about a week. Yield:94%; M.p:224 °C
H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.97 Å, and Uiso = 1.2Ueq(C) for CH2 and CH groups and Uiso = 1.5Ueq(C) for CH3 group.The N-bound H atom is located in a difference Fourier map and its positional parameters were refined.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. Packing diagram |
C30H26Cl2FN3O2 | F(000) = 1144 |
Mr = 550.44 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 16.694 (3) Å | θ = 2–25° |
b = 8.705 (4) Å | µ = 0.29 mm−1 |
c = 18.474 (3) Å | T = 293 K |
β = 103.27 (4)° | Block, colourless |
V = 2613.3 (14) Å3 | 0.23 × 0.21 × 0.18 mm |
Z = 4 |
Nonius MACH3 diffractometer | 2891 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ω–2θ scans | h = 0→19 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→10 |
Tmin = 0.936, Tmax = 0.950 | l = −21→21 |
5427 measured reflections | 3 standard reflections every 60 min |
4581 independent reflections | intensity decay: none |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0445P)2 + 0.726P] where P = (Fo2 + 2Fc2)/3 |
4581 reflections | (Δ/σ)max = 0.001 |
349 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C30H26Cl2FN3O2 | V = 2613.3 (14) Å3 |
Mr = 550.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.694 (3) Å | µ = 0.29 mm−1 |
b = 8.705 (4) Å | T = 293 K |
c = 18.474 (3) Å | 0.23 × 0.21 × 0.18 mm |
β = 103.27 (4)° |
Nonius MACH3 diffractometer | 2891 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.020 |
Tmin = 0.936, Tmax = 0.950 | 3 standard reflections every 60 min |
5427 measured reflections | intensity decay: none |
4581 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.29 e Å−3 |
4581 reflections | Δρmin = −0.33 e Å−3 |
349 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 | ||
Cl1 | 0.15668 (5) | 0.37573 (8) | 0.72167 (3) | 0.0831 (2) | |
Cl2 | −0.36431 (5) | 0.61752 (10) | 0.00265 (4) | 0.0919 (3) | |
N1 | −0.05322 (10) | 0.13961 (19) | 0.27962 (9) | 0.0464 (4) | |
O1 | 0.07132 (10) | 0.52336 (18) | 0.24553 (8) | 0.0613 (4) | |
C8 | 0.03804 (12) | 0.3538 (2) | 0.33420 (11) | 0.0419 (5) | |
F1 | 0.32228 (9) | 0.21475 (19) | 0.36806 (8) | 0.0808 (5) | |
N3 | 0.05530 (14) | −0.1040 (2) | 0.21711 (12) | 0.0603 (6) | |
C12 | −0.02137 (13) | 0.2314 (2) | 0.34544 (11) | 0.0473 (5) | |
H12A | 0.0060 | 0.1641 | 0.3854 | 0.057* | |
H12B | −0.0671 | 0.2797 | 0.3608 | 0.057* | |
C9 | 0.03991 (12) | 0.4022 (2) | 0.25700 (11) | 0.0435 (5) | |
O2 | −0.05184 (11) | −0.0289 (2) | 0.12232 (10) | 0.0724 (5) | |
N2 | 0.08528 (11) | 0.2056 (2) | 0.11641 (9) | 0.0524 (5) | |
C20 | 0.12500 (14) | −0.0377 (3) | 0.26298 (13) | 0.0511 (6) | |
C15 | 0.12839 (13) | 0.1176 (2) | 0.24568 (11) | 0.0448 (5) | |
C5 | 0.04926 (13) | 0.3405 (3) | 0.50697 (12) | 0.0521 (6) | |
H5 | 0.0001 | 0.3012 | 0.4789 | 0.063* | |
C10 | −0.00213 (12) | 0.2963 (2) | 0.19252 (11) | 0.0420 (5) | |
C11 | −0.07990 (13) | 0.2364 (2) | 0.21440 (11) | 0.0459 (5) | |
H11A | −0.1125 | 0.3216 | 0.2256 | 0.055* | |
H11B | −0.1132 | 0.1776 | 0.1739 | 0.055* | |
C4 | 0.10401 (13) | 0.4086 (2) | 0.47049 (11) | 0.0451 (5) | |
C17 | 0.25566 (14) | 0.1306 (3) | 0.33291 (13) | 0.0570 (6) | |
C25 | −0.10489 (14) | 0.4406 (2) | 0.08703 (11) | 0.0475 (5) | |
C28 | −0.26410 (16) | 0.5504 (3) | 0.03646 (13) | 0.0592 (6) | |
C24 | −0.01808 (13) | 0.3837 (3) | 0.11635 (11) | 0.0487 (5) | |
H24 | 0.0175 | 0.4746 | 0.1241 | 0.058* | |
C14 | 0.05642 (13) | 0.1582 (2) | 0.18243 (11) | 0.0464 (5) | |
C16 | 0.19562 (13) | 0.2034 (3) | 0.28079 (12) | 0.0503 (5) | |
H16 | 0.2002 | 0.3068 | 0.2696 | 0.060* | |
C26 | −0.12471 (17) | 0.5925 (3) | 0.09730 (13) | 0.0588 (6) | |
H26 | −0.0836 | 0.6590 | 0.1214 | 0.071* | |
C1 | 0.13761 (16) | 0.3869 (3) | 0.62522 (12) | 0.0577 (6) | |
C3 | 0.17622 (15) | 0.4682 (3) | 0.51528 (13) | 0.0566 (6) | |
H3 | 0.2138 | 0.5169 | 0.4929 | 0.068* | |
C7 | 0.09049 (13) | 0.4260 (3) | 0.38996 (12) | 0.0468 (5) | |
H7 | 0.1237 | 0.4993 | 0.3747 | 0.056* | |
C21 | 0.01022 (16) | −0.0003 (3) | 0.16971 (14) | 0.0549 (6) | |
C18 | 0.25207 (16) | −0.0208 (3) | 0.35107 (13) | 0.0630 (7) | |
H18 | 0.2942 | −0.0649 | 0.3868 | 0.076* | |
C6 | 0.06523 (15) | 0.3289 (3) | 0.58344 (12) | 0.0562 (6) | |
H6 | 0.0274 | 0.2823 | 0.6064 | 0.067* | |
C23 | 0.01550 (14) | 0.2770 (3) | 0.06552 (12) | 0.0587 (6) | |
H23A | −0.0251 | 0.2010 | 0.0429 | 0.070* | |
H23B | 0.0330 | 0.3337 | 0.0267 | 0.070* | |
C19 | 0.18501 (16) | −0.1081 (3) | 0.31565 (13) | 0.0611 (6) | |
H19 | 0.1809 | −0.2113 | 0.3273 | 0.073* | |
C30 | −0.16798 (15) | 0.3466 (3) | 0.04937 (13) | 0.0584 (6) | |
H30 | −0.1566 | 0.2444 | 0.0410 | 0.070* | |
C29 | −0.24709 (15) | 0.4006 (3) | 0.02398 (14) | 0.0625 (7) | |
H29 | −0.2884 | 0.3358 | −0.0014 | 0.075* | |
C27 | −0.20378 (18) | 0.6475 (3) | 0.07271 (14) | 0.0682 (7) | |
H27 | −0.2159 | 0.7495 | 0.0807 | 0.082* | |
C2 | 0.19346 (16) | 0.4570 (3) | 0.59173 (14) | 0.0636 (7) | |
H2 | 0.2423 | 0.4964 | 0.6203 | 0.076* | |
C13 | −0.11773 (16) | 0.0373 (3) | 0.29201 (14) | 0.0723 (8) | |
H13A | −0.0963 | −0.0271 | 0.3342 | 0.087* | |
H13B | −0.1368 | −0.0255 | 0.2488 | 0.087* | |
H13C | −0.1627 | 0.0970 | 0.3012 | 0.087* | |
C22 | 0.12756 (17) | 0.0882 (3) | 0.08263 (14) | 0.0740 (8) | |
H22A | 0.0902 | 0.0055 | 0.0647 | 0.089* | |
H22B | 0.1737 | 0.0497 | 0.1191 | 0.089* | |
H22C | 0.1465 | 0.1322 | 0.0419 | 0.089* | |
H1N | 0.0456 (17) | −0.198 (3) | 0.2158 (15) | 0.082 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1218 (6) | 0.0714 (4) | 0.0461 (3) | −0.0034 (4) | −0.0010 (4) | −0.0014 (3) |
Cl2 | 0.0795 (5) | 0.1069 (6) | 0.0911 (5) | 0.0369 (5) | 0.0232 (4) | 0.0095 (5) |
N1 | 0.0503 (10) | 0.0402 (10) | 0.0473 (10) | −0.0088 (8) | 0.0085 (8) | 0.0028 (8) |
O1 | 0.0828 (12) | 0.0474 (9) | 0.0543 (10) | −0.0240 (9) | 0.0167 (8) | −0.0025 (8) |
C8 | 0.0432 (11) | 0.0390 (11) | 0.0447 (11) | 0.0002 (10) | 0.0124 (9) | −0.0023 (10) |
F1 | 0.0623 (9) | 0.0975 (12) | 0.0743 (9) | −0.0097 (9) | −0.0015 (7) | 0.0029 (9) |
N3 | 0.0734 (15) | 0.0359 (11) | 0.0717 (14) | −0.0051 (11) | 0.0170 (11) | −0.0048 (11) |
C12 | 0.0506 (12) | 0.0472 (13) | 0.0442 (12) | −0.0026 (11) | 0.0113 (10) | 0.0036 (10) |
C9 | 0.0455 (12) | 0.0373 (12) | 0.0486 (12) | −0.0024 (10) | 0.0127 (10) | −0.0008 (10) |
O2 | 0.0784 (12) | 0.0592 (11) | 0.0723 (11) | −0.0169 (10) | 0.0025 (10) | −0.0181 (9) |
N2 | 0.0589 (11) | 0.0572 (12) | 0.0434 (10) | −0.0002 (10) | 0.0162 (9) | −0.0012 (9) |
C20 | 0.0606 (15) | 0.0426 (12) | 0.0537 (13) | 0.0031 (12) | 0.0205 (12) | −0.0020 (11) |
C15 | 0.0500 (12) | 0.0434 (12) | 0.0432 (11) | −0.0005 (11) | 0.0154 (10) | −0.0017 (10) |
C5 | 0.0487 (13) | 0.0594 (15) | 0.0467 (13) | 0.0006 (11) | 0.0077 (10) | −0.0037 (11) |
C10 | 0.0478 (12) | 0.0371 (11) | 0.0413 (11) | −0.0046 (10) | 0.0104 (9) | −0.0008 (9) |
C11 | 0.0487 (12) | 0.0422 (12) | 0.0459 (12) | −0.0047 (10) | 0.0086 (10) | 0.0018 (10) |
C4 | 0.0475 (12) | 0.0403 (12) | 0.0463 (12) | 0.0032 (10) | 0.0082 (10) | −0.0038 (10) |
C17 | 0.0491 (14) | 0.0706 (17) | 0.0517 (13) | −0.0016 (13) | 0.0125 (11) | −0.0044 (13) |
C25 | 0.0652 (14) | 0.0380 (12) | 0.0396 (11) | −0.0039 (11) | 0.0125 (11) | 0.0057 (9) |
C28 | 0.0681 (16) | 0.0607 (16) | 0.0515 (14) | 0.0134 (14) | 0.0193 (12) | 0.0090 (12) |
C24 | 0.0575 (13) | 0.0437 (12) | 0.0442 (12) | −0.0103 (11) | 0.0101 (10) | 0.0011 (10) |
C14 | 0.0555 (13) | 0.0399 (12) | 0.0442 (12) | −0.0048 (10) | 0.0124 (10) | −0.0037 (10) |
C16 | 0.0539 (13) | 0.0502 (13) | 0.0493 (12) | −0.0017 (12) | 0.0173 (11) | −0.0004 (11) |
C26 | 0.0792 (17) | 0.0440 (13) | 0.0509 (13) | −0.0030 (13) | 0.0103 (12) | −0.0024 (11) |
C1 | 0.0786 (17) | 0.0429 (13) | 0.0457 (12) | 0.0062 (13) | 0.0019 (12) | −0.0018 (11) |
C3 | 0.0594 (15) | 0.0506 (13) | 0.0575 (15) | −0.0081 (12) | 0.0087 (12) | −0.0037 (12) |
C7 | 0.0472 (12) | 0.0440 (12) | 0.0508 (13) | −0.0016 (10) | 0.0142 (10) | −0.0016 (10) |
C21 | 0.0652 (16) | 0.0441 (14) | 0.0570 (14) | −0.0068 (12) | 0.0172 (13) | −0.0107 (12) |
C18 | 0.0652 (16) | 0.0706 (18) | 0.0539 (14) | 0.0174 (14) | 0.0151 (12) | 0.0086 (13) |
C6 | 0.0616 (15) | 0.0574 (15) | 0.0500 (13) | 0.0031 (12) | 0.0137 (12) | 0.0013 (12) |
C23 | 0.0654 (15) | 0.0668 (16) | 0.0437 (12) | −0.0009 (13) | 0.0123 (11) | 0.0007 (12) |
C19 | 0.0769 (17) | 0.0476 (14) | 0.0632 (15) | 0.0096 (14) | 0.0250 (13) | 0.0059 (13) |
C30 | 0.0679 (16) | 0.0395 (13) | 0.0615 (14) | −0.0006 (12) | 0.0015 (12) | 0.0005 (11) |
C29 | 0.0621 (16) | 0.0540 (15) | 0.0657 (15) | −0.0020 (13) | 0.0029 (13) | 0.0061 (13) |
C27 | 0.095 (2) | 0.0495 (15) | 0.0602 (15) | 0.0153 (15) | 0.0188 (15) | −0.0031 (13) |
C2 | 0.0702 (16) | 0.0525 (14) | 0.0582 (15) | −0.0077 (13) | −0.0056 (13) | −0.0046 (12) |
C13 | 0.0798 (18) | 0.0659 (17) | 0.0662 (16) | −0.0311 (15) | 0.0068 (14) | 0.0128 (14) |
C22 | 0.0839 (19) | 0.0835 (19) | 0.0605 (15) | 0.0118 (16) | 0.0286 (14) | −0.0052 (14) |
Cl1—C1 | 1.739 (2) | C17—C16 | 1.375 (3) |
Cl2—C28 | 1.746 (3) | C25—C26 | 1.386 (3) |
N1—C12 | 1.450 (3) | C25—C30 | 1.388 (3) |
N1—C11 | 1.454 (3) | C25—C24 | 1.510 (3) |
N1—C13 | 1.456 (3) | C28—C29 | 1.366 (3) |
O1—C9 | 1.218 (2) | C28—C27 | 1.367 (4) |
C8—C7 | 1.345 (3) | C24—C23 | 1.517 (3) |
C8—C9 | 1.494 (3) | C24—H24 | 0.9800 |
C8—C12 | 1.502 (3) | C14—C21 | 1.572 (3) |
F1—C17 | 1.365 (3) | C16—H16 | 0.9300 |
N3—C21 | 1.358 (3) | C26—C27 | 1.379 (3) |
N3—C20 | 1.397 (3) | C26—H26 | 0.9300 |
N3—H1N | 0.84 (3) | C1—C6 | 1.372 (3) |
C12—H12A | 0.9700 | C1—C2 | 1.374 (4) |
C12—H12B | 0.9700 | C3—C2 | 1.379 (3) |
C9—C10 | 1.542 (3) | C3—H3 | 0.9300 |
O2—C21 | 1.219 (3) | C7—H7 | 0.9300 |
N2—C23 | 1.457 (3) | C18—C19 | 1.387 (3) |
N2—C22 | 1.461 (3) | C18—H18 | 0.9300 |
N2—C14 | 1.469 (3) | C6—H6 | 0.9300 |
C20—C19 | 1.371 (3) | C23—H23A | 0.9700 |
C20—C15 | 1.393 (3) | C23—H23B | 0.9700 |
C15—C16 | 1.380 (3) | C19—H19 | 0.9300 |
C15—C14 | 1.513 (3) | C30—C29 | 1.379 (3) |
C5—C6 | 1.380 (3) | C30—H30 | 0.9300 |
C5—C4 | 1.387 (3) | C29—H29 | 0.9300 |
C5—H5 | 0.9300 | C27—H27 | 0.9300 |
C10—C11 | 1.537 (3) | C2—H2 | 0.9300 |
C10—C24 | 1.568 (3) | C13—H13A | 0.9600 |
C10—C14 | 1.587 (3) | C13—H13B | 0.9600 |
C11—H11A | 0.9700 | C13—H13C | 0.9600 |
C11—H11B | 0.9700 | C22—H22A | 0.9600 |
C4—C3 | 1.396 (3) | C22—H22B | 0.9600 |
C4—C7 | 1.461 (3) | C22—H22C | 0.9600 |
C17—C18 | 1.364 (4) | ||
C12—N1—C11 | 111.05 (16) | C15—C14—C21 | 100.68 (17) |
C12—N1—C13 | 110.34 (18) | N2—C14—C10 | 102.30 (16) |
C11—N1—C13 | 112.83 (17) | C15—C14—C10 | 119.19 (17) |
C7—C8—C9 | 116.53 (19) | C21—C14—C10 | 112.84 (17) |
C7—C8—C12 | 124.05 (19) | C17—C16—C15 | 117.6 (2) |
C9—C8—C12 | 119.41 (17) | C17—C16—H16 | 121.2 |
C21—N3—C20 | 112.2 (2) | C15—C16—H16 | 121.2 |
C21—N3—H1N | 123.9 (19) | C27—C26—C25 | 121.8 (2) |
C20—N3—H1N | 123.5 (19) | C27—C26—H26 | 119.1 |
N1—C12—C8 | 113.68 (17) | C25—C26—H26 | 119.1 |
N1—C12—H12A | 108.8 | C6—C1—C2 | 120.7 (2) |
C8—C12—H12A | 108.8 | C6—C1—Cl1 | 119.1 (2) |
N1—C12—H12B | 108.8 | C2—C1—Cl1 | 120.16 (19) |
C8—C12—H12B | 108.8 | C2—C3—C4 | 122.0 (2) |
H12A—C12—H12B | 107.7 | C2—C3—H3 | 119.0 |
O1—C9—C8 | 120.96 (19) | C4—C3—H3 | 119.0 |
O1—C9—C10 | 121.42 (19) | C8—C7—C4 | 130.8 (2) |
C8—C9—C10 | 117.59 (18) | C8—C7—H7 | 114.6 |
C23—N2—C22 | 114.55 (18) | C4—C7—H7 | 114.6 |
C23—N2—C14 | 106.82 (16) | O2—C21—N3 | 125.6 (2) |
C22—N2—C14 | 116.15 (19) | O2—C21—C14 | 126.4 (2) |
C19—C20—C15 | 122.4 (2) | N3—C21—C14 | 107.9 (2) |
C19—C20—N3 | 128.1 (2) | C17—C18—C19 | 119.3 (2) |
C15—C20—N3 | 109.5 (2) | C17—C18—H18 | 120.3 |
C16—C15—C20 | 119.3 (2) | C19—C18—H18 | 120.3 |
C16—C15—C14 | 130.7 (2) | C1—C6—C5 | 119.1 (2) |
C20—C15—C14 | 109.71 (19) | C1—C6—H6 | 120.4 |
C6—C5—C4 | 122.3 (2) | C5—C6—H6 | 120.4 |
C6—C5—H5 | 118.8 | N2—C23—C24 | 102.47 (17) |
C4—C5—H5 | 118.8 | N2—C23—H23A | 111.3 |
C11—C10—C9 | 105.19 (16) | C24—C23—H23A | 111.3 |
C11—C10—C24 | 114.90 (17) | N2—C23—H23B | 111.3 |
C9—C10—C24 | 110.89 (17) | C24—C23—H23B | 111.3 |
C11—C10—C14 | 110.74 (16) | H23A—C23—H23B | 109.2 |
C9—C10—C14 | 111.11 (16) | C20—C19—C18 | 118.0 (2) |
C24—C10—C14 | 104.14 (16) | C20—C19—H19 | 121.0 |
N1—C11—C10 | 107.35 (16) | C18—C19—H19 | 121.0 |
N1—C11—H11A | 110.2 | C29—C30—C25 | 121.8 (2) |
C10—C11—H11A | 110.2 | C29—C30—H30 | 119.1 |
N1—C11—H11B | 110.2 | C25—C30—H30 | 119.1 |
C10—C11—H11B | 110.2 | C28—C29—C30 | 119.2 (2) |
H11A—C11—H11B | 108.5 | C28—C29—H29 | 120.4 |
C5—C4—C3 | 116.5 (2) | C30—C29—H29 | 120.4 |
C5—C4—C7 | 125.05 (19) | C28—C27—C26 | 119.2 (2) |
C3—C4—C7 | 118.4 (2) | C28—C27—H27 | 120.4 |
C18—C17—F1 | 118.6 (2) | C26—C27—H27 | 120.4 |
C18—C17—C16 | 123.5 (2) | C1—C2—C3 | 119.3 (2) |
F1—C17—C16 | 118.0 (2) | C1—C2—H2 | 120.4 |
C26—C25—C30 | 117.0 (2) | C3—C2—H2 | 120.4 |
C26—C25—C24 | 120.2 (2) | N1—C13—H13A | 109.5 |
C30—C25—C24 | 122.8 (2) | N1—C13—H13B | 109.5 |
C29—C28—C27 | 121.0 (2) | H13A—C13—H13B | 109.5 |
C29—C28—Cl2 | 118.6 (2) | N1—C13—H13C | 109.5 |
C27—C28—Cl2 | 120.4 (2) | H13A—C13—H13C | 109.5 |
C25—C24—C23 | 116.08 (18) | H13B—C13—H13C | 109.5 |
C25—C24—C10 | 115.64 (17) | N2—C22—H22A | 109.5 |
C23—C24—C10 | 104.34 (17) | N2—C22—H22B | 109.5 |
C25—C24—H24 | 106.7 | H22A—C22—H22B | 109.5 |
C23—C24—H24 | 106.7 | N2—C22—H22C | 109.5 |
C10—C24—H24 | 106.7 | H22A—C22—H22C | 109.5 |
N2—C14—C15 | 110.68 (17) | H22B—C22—H22C | 109.5 |
N2—C14—C21 | 111.43 (17) | ||
C11—N1—C12—C8 | −46.9 (2) | C24—C10—C14—N2 | 15.56 (19) |
C13—N1—C12—C8 | −172.82 (19) | C11—C10—C14—C15 | −98.0 (2) |
C7—C8—C12—N1 | −162.6 (2) | C9—C10—C14—C15 | 18.5 (2) |
C9—C8—C12—N1 | 18.2 (3) | C24—C10—C14—C15 | 137.96 (18) |
C7—C8—C9—O1 | −17.5 (3) | C11—C10—C14—C21 | 19.7 (2) |
C12—C8—C9—O1 | 161.9 (2) | C9—C10—C14—C21 | 136.27 (18) |
C7—C8—C9—C10 | 164.77 (18) | C24—C10—C14—C21 | −104.29 (19) |
C12—C8—C9—C10 | −15.9 (3) | C18—C17—C16—C15 | 0.3 (3) |
C21—N3—C20—C19 | −178.2 (2) | F1—C17—C16—C15 | −179.82 (18) |
C21—N3—C20—C15 | −0.7 (3) | C20—C15—C16—C17 | −1.4 (3) |
C19—C20—C15—C16 | 2.2 (3) | C14—C15—C16—C17 | −174.3 (2) |
N3—C20—C15—C16 | −175.45 (19) | C30—C25—C26—C27 | 1.3 (3) |
C19—C20—C15—C14 | 176.5 (2) | C24—C25—C26—C27 | −178.5 (2) |
N3—C20—C15—C14 | −1.1 (2) | C5—C4—C3—C2 | 1.5 (3) |
O1—C9—C10—C11 | −139.5 (2) | C7—C4—C3—C2 | 179.8 (2) |
C8—C9—C10—C11 | 38.2 (2) | C9—C8—C7—C4 | 179.3 (2) |
O1—C9—C10—C24 | −14.7 (3) | C12—C8—C7—C4 | 0.0 (4) |
C8—C9—C10—C24 | 163.01 (17) | C5—C4—C7—C8 | −18.4 (4) |
O1—C9—C10—C14 | 100.6 (2) | C3—C4—C7—C8 | 163.5 (2) |
C8—C9—C10—C14 | −81.7 (2) | C20—N3—C21—O2 | 177.5 (2) |
C12—N1—C11—C10 | 74.2 (2) | C20—N3—C21—C14 | 2.2 (3) |
C13—N1—C11—C10 | −161.35 (19) | N2—C14—C21—O2 | −60.5 (3) |
C9—C10—C11—N1 | −66.3 (2) | C15—C14—C21—O2 | −177.9 (2) |
C24—C10—C11—N1 | 171.46 (16) | C10—C14—C21—O2 | 54.0 (3) |
C14—C10—C11—N1 | 53.8 (2) | N2—C14—C21—N3 | 114.7 (2) |
C6—C5—C4—C3 | −1.2 (3) | C15—C14—C21—N3 | −2.7 (2) |
C6—C5—C4—C7 | −179.3 (2) | C10—C14—C21—N3 | −130.82 (19) |
C26—C25—C24—C23 | −138.5 (2) | F1—C17—C18—C19 | −179.7 (2) |
C30—C25—C24—C23 | 41.7 (3) | C16—C17—C18—C19 | 0.2 (4) |
C26—C25—C24—C10 | 98.8 (2) | C2—C1—C6—C5 | 0.5 (4) |
C30—C25—C24—C10 | −81.1 (3) | Cl1—C1—C6—C5 | 178.68 (18) |
C11—C10—C24—C25 | 18.4 (3) | C4—C5—C6—C1 | 0.2 (4) |
C9—C10—C24—C25 | −100.7 (2) | C22—N2—C23—C24 | 176.68 (19) |
C14—C10—C24—C25 | 139.74 (18) | C14—N2—C23—C24 | 46.6 (2) |
C11—C10—C24—C23 | −110.3 (2) | C25—C24—C23—N2 | −162.38 (18) |
C9—C10—C24—C23 | 130.57 (18) | C10—C24—C23—N2 | −33.9 (2) |
C14—C10—C24—C23 | 11.0 (2) | C15—C20—C19—C18 | −1.7 (3) |
C23—N2—C14—C15 | −166.58 (18) | N3—C20—C19—C18 | 175.5 (2) |
C22—N2—C14—C15 | 64.2 (2) | C17—C18—C19—C20 | 0.5 (3) |
C23—N2—C14—C21 | 82.3 (2) | C26—C25—C30—C29 | −0.8 (3) |
C22—N2—C14—C21 | −46.9 (3) | C24—C25—C30—C29 | 179.1 (2) |
C23—N2—C14—C10 | −38.6 (2) | C27—C28—C29—C30 | 0.9 (4) |
C22—N2—C14—C10 | −167.77 (18) | Cl2—C28—C29—C30 | 179.04 (18) |
C16—C15—C14—N2 | 57.8 (3) | C25—C30—C29—C28 | −0.3 (4) |
C20—C15—C14—N2 | −115.70 (19) | C29—C28—C27—C26 | −0.4 (4) |
C16—C15—C14—C21 | 175.7 (2) | Cl2—C28—C27—C26 | −178.46 (18) |
C20—C15—C14—C21 | 2.3 (2) | C25—C26—C27—C28 | −0.8 (4) |
C16—C15—C14—C10 | −60.4 (3) | C6—C1—C2—C3 | −0.2 (4) |
C20—C15—C14—C10 | 126.16 (19) | Cl1—C1—C2—C3 | −178.34 (19) |
C11—C10—C14—N2 | 139.59 (16) | C4—C3—C2—C1 | −0.9 (4) |
C9—C10—C14—N2 | −103.89 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···O2 | 0.97 | 2.37 | 2.968 (3) | 119 |
C23—H23A···O2 | 0.97 | 2.58 | 3.162 (3) | 119 |
C24—H24···O1 | 0.98 | 2.26 | 2.787 (3) | 113 |
N3—H1N···O1i | 0.84 (3) | 2.50 (3) | 3.288 (3) | 157 (3) |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C30H26Cl2FN3O2 |
Mr | 550.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 16.694 (3), 8.705 (4), 18.474 (3) |
β (°) | 103.27 (4) |
V (Å3) | 2613.3 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.23 × 0.21 × 0.18 |
Data collection | |
Diffractometer | Nonius MACH3 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.936, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5427, 4581, 2891 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.104, 1.02 |
No. of reflections | 4581 |
No. of parameters | 349 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.33 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···O2 | 0.97 | 2.37 | 2.968 (3) | 119 |
C23—H23A···O2 | 0.97 | 2.58 | 3.162 (3) | 119 |
C24—H24···O1 | 0.98 | 2.26 | 2.787 (3) | 113 |
N3—H1N···O1i | 0.84 (3) | 2.50 (3) | 3.288 (3) | 157 (3) |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
JK thanks the UGC for an RFSMS fellowship. SN thanks the CSIR for funding under the Emeritus Scientist Scheme.
References
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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.
In the family of heterocyclic compounds, nitrogen containing heterocycles especially substituted piperidin-4-ones have considerable importance due to their variety of biological properties such as analgesic (Jerom et al., 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), antimicrobial, bactericidal, fungicidal, herbicidal, anticancer, CNS stimulant and depressant activities (Mobio et al., 1989; Katritzky & Fan, 1990; Ganellin & Spickett, 1965) and antiviral, antitumour (El-Subbagh et al., 2000). Also they are important synthetic intermediates in the preparation of various pharmaceuticals (Wang & Wuorola, 1992) and widely prevalent in natural products such as alkaloids (Angle & Breitenbucher, 1995). Hence, the present X-ray crystallographic study of the title compound has been carried out to determine the conformation of the system.
The piperidine ring of the title compound, C30H26N3O2Cl2F, adopts a twisted chair conformation (C8/C9/C10/C11/N1/C12). Pyrrolidine ring has the twisted envelope structure with N atom at the flap (0.592 (3)Å from the mean plane formed by the atoms C10/C14/C23/C24) and this orientation may be influenced by the intramolecular C23—H23A···O2 hydrogen bond (Table 1).
Fluorooxindole, the chlorophenyl and chlorophenylmethylidine groups are planar as confirmed by thevalues of the r.m.s. deviation (0.0348 Å, 0.0048Å and 0.0048 Å), respectively,from the mean planes of the above groups. Flurooxindole is inclined with the plane of chlorophenyl by 33.99 (2)° and 55.56 (2)° with the mean plane of chlorophenylmethilidine. The sum of the bond angles around N1 atom (334.22°) of the piperidine ring in the molecule is in accordance with the sp2 hybridization. Further, the structure is stabilized by intermolecular N—H···O hydrogen bond and intramolecular C—H···O hydrogen bonds.