organic compounds
1-Allyl-3,3-di-p-tolylindolin-2-one
aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and cPost Graduate Research, Department of Chemistry, The New College, Chennai 600 014, India
*Correspondence e-mail: sudharose18@gmail.com
In the title compound, C25H23NO, the indoline system is essentially planar. The molecular structure is stabilized by weak intramolecular C—H⋯N interactions and the crystal packing is determined by intermolecular C—H⋯π interactions.
Related literature
For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Rajeswaran et al. (1999); Stevenson et al. (2000); Sethusankar et al. (2002).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808010088/gw2036sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010088/gw2036Isup2.hkl
To a solution of p-methyl phenyl magnesium bromide in dry THF, at 0°C under N2 atm.,1-N-allyl isatin (0.0125 mol, 2.34 g), in dry THF, was added dropwise. After the complete addition, the mixture was stirred at 0°C for 1 hr and then it was stirred at room temperature for 5 hrs. On completion of the reaction, a
of NH4Cl was added slowly at 0°C. The aqueous layer was extracted with ether, and the combined organic layer was extracted with ether. The crude mass was obtained., which was purified over a column of silica gel using hexane/ethyl acetate as Compound was recrystallized from methanol.H atoms were positioned geometrically and were treated as riding on their parent C atoms, with aromatic C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å and methylene C—H distances of 0.97 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids | |
Fig. 2. The packing of the molecules viewed down b axis. |
C25H23NO | Z = 2 |
Mr = 353.44 | F(000) = 376 |
Triclinic, P1 | Dx = 1.194 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3311 (2) Å | Cell parameters from 9112 reflections |
b = 9.5793 (2) Å | θ = 2.3–30.1° |
c = 11.5736 (2) Å | µ = 0.07 mm−1 |
α = 92.163 (1)° | T = 293 K |
β = 103.192 (1)° | Prism, colourless |
γ = 101.520 (1)° | 0.26 × 0.20 × 0.20 mm |
V = 983.15 (3) Å3 |
Bruker Kappa APEXII diffractometer | 6260 independent reflections |
Radiation source: fine-focus sealed tube | 4310 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and ϕ scan | θmax = 31.0°, θmin = 2.2° |
Absorption correction: multi-scan (Blessing, 1995) | h = −13→13 |
Tmin = 0.982, Tmax = 0.986 | k = −13→13 |
25969 measured reflections | l = −16→16 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1889P] where P = (Fo2 + 2Fc2)/3 |
6260 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C25H23NO | γ = 101.520 (1)° |
Mr = 353.44 | V = 983.15 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3311 (2) Å | Mo Kα radiation |
b = 9.5793 (2) Å | µ = 0.07 mm−1 |
c = 11.5736 (2) Å | T = 293 K |
α = 92.163 (1)° | 0.26 × 0.20 × 0.20 mm |
β = 103.192 (1)° |
Bruker Kappa APEXII diffractometer | 6260 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 4310 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.986 | Rint = 0.023 |
25969 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.25 e Å−3 |
6260 reflections | Δρmin = −0.21 e Å−3 |
244 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 | ||
C2 | 0.21981 (13) | 0.10769 (13) | 0.14416 (10) | 0.0403 (2) | |
C3 | 0.29661 (11) | 0.03653 (12) | 0.25302 (9) | 0.0361 (2) | |
C4 | 0.45434 (12) | 0.05217 (12) | 0.23447 (10) | 0.0391 (2) | |
C5 | 0.57669 (13) | 0.00390 (15) | 0.29710 (12) | 0.0497 (3) | |
H5 | 0.5699 | −0.0478 | 0.3628 | 0.060* | |
C6 | 0.71037 (15) | 0.03411 (17) | 0.26019 (15) | 0.0602 (4) | |
H6 | 0.7938 | 0.0024 | 0.3018 | 0.072* | |
C7 | 0.72086 (16) | 0.10999 (18) | 0.16332 (16) | 0.0629 (4) | |
H7 | 0.8116 | 0.1295 | 0.1405 | 0.075* | |
C8 | 0.59809 (17) | 0.15830 (17) | 0.09859 (14) | 0.0587 (4) | |
H8 | 0.6049 | 0.2096 | 0.0327 | 0.070* | |
C9 | 0.46580 (14) | 0.12724 (13) | 0.13582 (11) | 0.0443 (3) | |
C10 | 0.29599 (19) | 0.24323 (18) | −0.01709 (12) | 0.0614 (4) | |
H10A | 0.1917 | 0.2102 | −0.0604 | 0.074* | |
H10B | 0.3589 | 0.2267 | −0.0701 | 0.074* | |
C11 | 0.32409 (19) | 0.39967 (19) | 0.01642 (16) | 0.0658 (4) | |
H11 | 0.3133 | 0.4583 | −0.0458 | 0.079* | |
C12 | 0.3620 (2) | 0.4623 (2) | 0.12318 (19) | 0.0749 (5) | |
H12A | 0.3742 | 0.4084 | 0.1885 | 0.090* | |
H12B | 0.3770 | 0.5612 | 0.1347 | 0.090* | |
C13 | 0.22090 (12) | −0.12027 (12) | 0.25034 (10) | 0.0391 (2) | |
C14 | 0.24490 (16) | −0.19198 (15) | 0.35239 (13) | 0.0541 (3) | |
H14 | 0.3029 | −0.1423 | 0.4237 | 0.065* | |
C15 | 0.18392 (18) | −0.33608 (16) | 0.34970 (16) | 0.0626 (4) | |
H15 | 0.2020 | −0.3818 | 0.4194 | 0.075* | |
C16 | 0.09700 (17) | −0.41371 (15) | 0.24620 (16) | 0.0592 (4) | |
C17 | 0.07309 (17) | −0.34194 (16) | 0.14492 (15) | 0.0603 (4) | |
H17 | 0.0145 | −0.3920 | 0.0739 | 0.072* | |
C18 | 0.13362 (15) | −0.19778 (14) | 0.14583 (12) | 0.0490 (3) | |
H18 | 0.1156 | −0.1526 | 0.0759 | 0.059* | |
C19 | 0.0294 (3) | −0.57073 (17) | 0.2435 (2) | 0.0907 (6) | |
H19A | −0.0262 | −0.6064 | 0.1639 | 0.136* | |
H19B | −0.0372 | −0.5842 | 0.2963 | 0.136* | |
H19C | 0.1083 | −0.6216 | 0.2686 | 0.136* | |
C20 | 0.28928 (12) | 0.12652 (12) | 0.36267 (10) | 0.0372 (2) | |
C21 | 0.40937 (13) | 0.23204 (14) | 0.42458 (11) | 0.0445 (3) | |
H21 | 0.5003 | 0.2467 | 0.4020 | 0.053* | |
C22 | 0.39541 (16) | 0.31600 (15) | 0.51984 (12) | 0.0530 (3) | |
H22 | 0.4778 | 0.3858 | 0.5605 | 0.064* | |
C23 | 0.26275 (17) | 0.29871 (17) | 0.55575 (12) | 0.0553 (3) | |
C24 | 0.14184 (16) | 0.19372 (17) | 0.49283 (13) | 0.0561 (3) | |
H24 | 0.0506 | 0.1801 | 0.5150 | 0.067* | |
C25 | 0.15471 (14) | 0.10923 (15) | 0.39803 (12) | 0.0483 (3) | |
H25 | 0.0721 | 0.0398 | 0.3573 | 0.058* | |
C26 | 0.2485 (3) | 0.3901 (3) | 0.65992 (18) | 0.0932 (7) | |
H26A | 0.1485 | 0.3626 | 0.6718 | 0.140* | |
H26B | 0.2675 | 0.4889 | 0.6439 | 0.140* | |
H26C | 0.3204 | 0.3771 | 0.7304 | 0.140* | |
N1 | 0.32609 (13) | 0.15965 (12) | 0.08421 (9) | 0.0484 (3) | |
O1 | 0.08971 (10) | 0.11949 (10) | 0.11825 (8) | 0.0515 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0417 (5) | 0.0399 (6) | 0.0385 (5) | 0.0124 (4) | 0.0053 (4) | 0.0024 (4) |
C3 | 0.0306 (5) | 0.0386 (6) | 0.0381 (5) | 0.0075 (4) | 0.0059 (4) | 0.0061 (4) |
C4 | 0.0342 (5) | 0.0399 (6) | 0.0429 (6) | 0.0077 (4) | 0.0094 (4) | 0.0027 (4) |
C5 | 0.0372 (6) | 0.0554 (8) | 0.0569 (7) | 0.0132 (5) | 0.0086 (5) | 0.0103 (6) |
C6 | 0.0364 (6) | 0.0650 (9) | 0.0805 (10) | 0.0145 (6) | 0.0135 (6) | 0.0057 (8) |
C7 | 0.0444 (7) | 0.0637 (9) | 0.0859 (11) | 0.0079 (6) | 0.0305 (7) | 0.0025 (8) |
C8 | 0.0586 (8) | 0.0602 (9) | 0.0656 (9) | 0.0114 (7) | 0.0317 (7) | 0.0128 (7) |
C9 | 0.0444 (6) | 0.0442 (6) | 0.0468 (6) | 0.0109 (5) | 0.0148 (5) | 0.0051 (5) |
C10 | 0.0757 (10) | 0.0732 (10) | 0.0455 (7) | 0.0298 (8) | 0.0202 (7) | 0.0229 (7) |
C11 | 0.0697 (9) | 0.0666 (10) | 0.0719 (10) | 0.0222 (8) | 0.0280 (8) | 0.0323 (8) |
C12 | 0.0729 (11) | 0.0612 (10) | 0.0954 (13) | 0.0132 (8) | 0.0299 (10) | 0.0153 (9) |
C13 | 0.0318 (5) | 0.0389 (6) | 0.0461 (6) | 0.0085 (4) | 0.0074 (4) | 0.0048 (5) |
C14 | 0.0522 (7) | 0.0470 (7) | 0.0556 (7) | 0.0060 (6) | 0.0005 (6) | 0.0122 (6) |
C15 | 0.0626 (9) | 0.0476 (8) | 0.0785 (10) | 0.0132 (6) | 0.0152 (7) | 0.0224 (7) |
C16 | 0.0542 (7) | 0.0368 (7) | 0.0920 (11) | 0.0108 (6) | 0.0280 (7) | 0.0023 (7) |
C17 | 0.0582 (8) | 0.0462 (8) | 0.0716 (9) | 0.0058 (6) | 0.0133 (7) | −0.0137 (7) |
C18 | 0.0499 (7) | 0.0470 (7) | 0.0480 (6) | 0.0096 (5) | 0.0092 (5) | −0.0022 (5) |
C19 | 0.0989 (14) | 0.0380 (8) | 0.1420 (19) | 0.0073 (8) | 0.0500 (14) | 0.0009 (10) |
C20 | 0.0339 (5) | 0.0404 (6) | 0.0373 (5) | 0.0077 (4) | 0.0078 (4) | 0.0079 (4) |
C21 | 0.0372 (5) | 0.0475 (7) | 0.0461 (6) | 0.0038 (5) | 0.0097 (5) | 0.0032 (5) |
C22 | 0.0521 (7) | 0.0519 (8) | 0.0491 (7) | 0.0055 (6) | 0.0063 (6) | −0.0046 (6) |
C23 | 0.0607 (8) | 0.0625 (9) | 0.0456 (7) | 0.0186 (7) | 0.0145 (6) | 0.0007 (6) |
C24 | 0.0486 (7) | 0.0701 (9) | 0.0558 (7) | 0.0148 (6) | 0.0229 (6) | 0.0056 (7) |
C25 | 0.0361 (5) | 0.0550 (7) | 0.0522 (7) | 0.0046 (5) | 0.0121 (5) | 0.0027 (6) |
C26 | 0.0965 (14) | 0.1150 (17) | 0.0707 (11) | 0.0262 (12) | 0.0279 (10) | −0.0268 (11) |
N1 | 0.0520 (6) | 0.0551 (6) | 0.0434 (5) | 0.0188 (5) | 0.0140 (5) | 0.0154 (5) |
O1 | 0.0433 (4) | 0.0595 (6) | 0.0515 (5) | 0.0207 (4) | 0.0023 (4) | 0.0074 (4) |
C2—O1 | 1.2114 (14) | C14—C15 | 1.380 (2) |
C2—N1 | 1.3621 (16) | C14—H14 | 0.9300 |
C2—C3 | 1.5535 (15) | C15—C16 | 1.376 (2) |
C3—C4 | 1.5143 (15) | C15—H15 | 0.9300 |
C3—C13 | 1.5228 (16) | C16—C17 | 1.378 (2) |
C3—C20 | 1.5294 (16) | C16—C19 | 1.507 (2) |
C4—C5 | 1.3788 (16) | C17—C18 | 1.382 (2) |
C4—C9 | 1.3853 (17) | C17—H17 | 0.9300 |
C5—C6 | 1.3895 (19) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.371 (2) | C19—H19B | 0.9600 |
C6—H6 | 0.9300 | C19—H19C | 0.9600 |
C7—C8 | 1.391 (2) | C20—C21 | 1.3847 (16) |
C7—H7 | 0.9300 | C20—C25 | 1.3885 (16) |
C8—C9 | 1.3798 (19) | C21—C22 | 1.3857 (19) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—N1 | 1.4046 (16) | C22—C23 | 1.375 (2) |
C10—N1 | 1.4508 (16) | C22—H22 | 0.9300 |
C10—C11 | 1.489 (2) | C23—C24 | 1.390 (2) |
C10—H10A | 0.9700 | C23—C26 | 1.509 (2) |
C10—H10B | 0.9700 | C24—C25 | 1.380 (2) |
C11—C12 | 1.293 (3) | C24—H24 | 0.9300 |
C11—H11 | 0.9300 | C25—H25 | 0.9300 |
C12—H12A | 0.9300 | C26—H26A | 0.9600 |
C12—H12B | 0.9300 | C26—H26B | 0.9600 |
C13—C18 | 1.3852 (17) | C26—H26C | 0.9600 |
C13—C14 | 1.3853 (17) | ||
O1—C2—N1 | 125.45 (11) | C16—C15—C14 | 121.51 (14) |
O1—C2—C3 | 126.57 (11) | C16—C15—H15 | 119.2 |
N1—C2—C3 | 107.95 (9) | C14—C15—H15 | 119.2 |
C4—C3—C13 | 111.14 (9) | C15—C16—C17 | 117.38 (13) |
C4—C3—C20 | 113.55 (9) | C15—C16—C19 | 121.49 (17) |
C13—C3—C20 | 112.94 (9) | C17—C16—C19 | 121.13 (17) |
C4—C3—C2 | 101.28 (9) | C16—C17—C18 | 121.93 (14) |
C13—C3—C2 | 111.74 (9) | C16—C17—H17 | 119.0 |
C20—C3—C2 | 105.46 (9) | C18—C17—H17 | 119.0 |
C5—C4—C9 | 119.89 (11) | C17—C18—C13 | 120.39 (13) |
C5—C4—C3 | 130.70 (11) | C17—C18—H18 | 119.8 |
C9—C4—C3 | 109.40 (9) | C13—C18—H18 | 119.8 |
C4—C5—C6 | 118.68 (13) | C16—C19—H19A | 109.5 |
C4—C5—H5 | 120.7 | C16—C19—H19B | 109.5 |
C6—C5—H5 | 120.7 | H19A—C19—H19B | 109.5 |
C7—C6—C5 | 120.88 (13) | C16—C19—H19C | 109.5 |
C7—C6—H6 | 119.6 | H19A—C19—H19C | 109.5 |
C5—C6—H6 | 119.6 | H19B—C19—H19C | 109.5 |
C6—C7—C8 | 121.13 (13) | C21—C20—C25 | 117.95 (11) |
C6—C7—H7 | 119.4 | C21—C20—C3 | 122.56 (10) |
C8—C7—H7 | 119.4 | C25—C20—C3 | 119.36 (10) |
C9—C8—C7 | 117.48 (14) | C20—C21—C22 | 120.67 (12) |
C9—C8—H8 | 121.3 | C20—C21—H21 | 119.7 |
C7—C8—H8 | 121.3 | C22—C21—H21 | 119.7 |
C8—C9—C4 | 121.93 (12) | C23—C22—C21 | 121.62 (13) |
C8—C9—N1 | 128.51 (12) | C23—C22—H22 | 119.2 |
C4—C9—N1 | 109.54 (10) | C21—C22—H22 | 119.2 |
N1—C10—C11 | 113.55 (13) | C22—C23—C24 | 117.66 (13) |
N1—C10—H10A | 108.9 | C22—C23—C26 | 121.35 (15) |
C11—C10—H10A | 108.9 | C24—C23—C26 | 120.99 (15) |
N1—C10—H10B | 108.9 | C25—C24—C23 | 121.17 (13) |
C11—C10—H10B | 108.9 | C25—C24—H24 | 119.4 |
H10A—C10—H10B | 107.7 | C23—C24—H24 | 119.4 |
C12—C11—C10 | 126.66 (15) | C24—C25—C20 | 120.91 (12) |
C12—C11—H11 | 116.7 | C24—C25—H25 | 119.5 |
C10—C11—H11 | 116.7 | C20—C25—H25 | 119.5 |
C11—C12—H12A | 120.0 | C23—C26—H26A | 109.5 |
C11—C12—H12B | 120.0 | C23—C26—H26B | 109.5 |
H12A—C12—H12B | 120.0 | H26A—C26—H26B | 109.5 |
C18—C13—C14 | 117.85 (12) | C23—C26—H26C | 109.5 |
C18—C13—C3 | 121.72 (11) | H26A—C26—H26C | 109.5 |
C14—C13—C3 | 120.33 (10) | H26B—C26—H26C | 109.5 |
C15—C14—C13 | 120.95 (13) | C2—N1—C9 | 111.71 (10) |
C15—C14—H14 | 119.5 | C2—N1—C10 | 122.67 (11) |
C13—C14—H14 | 119.5 | C9—N1—C10 | 125.57 (12) |
O1—C2—C3—C4 | 178.68 (12) | C14—C15—C16—C17 | 0.0 (2) |
N1—C2—C3—C4 | −3.41 (12) | C14—C15—C16—C19 | −179.48 (16) |
O1—C2—C3—C13 | 60.29 (16) | C15—C16—C17—C18 | 0.2 (2) |
N1—C2—C3—C13 | −121.80 (11) | C19—C16—C17—C18 | 179.68 (15) |
O1—C2—C3—C20 | −62.78 (15) | C16—C17—C18—C13 | −0.2 (2) |
N1—C2—C3—C20 | 115.14 (10) | C14—C13—C18—C17 | 0.1 (2) |
C13—C3—C4—C5 | −57.30 (16) | C3—C13—C18—C17 | 176.45 (12) |
C20—C3—C4—C5 | 71.33 (16) | C4—C3—C20—C21 | 11.87 (15) |
C2—C3—C4—C5 | −176.12 (13) | C13—C3—C20—C21 | 139.58 (11) |
C13—C3—C4—C9 | 121.92 (11) | C2—C3—C20—C21 | −98.13 (12) |
C20—C3—C4—C9 | −109.45 (11) | C4—C3—C20—C25 | −172.36 (10) |
C2—C3—C4—C9 | 3.10 (12) | C13—C3—C20—C25 | −44.66 (14) |
C9—C4—C5—C6 | 1.0 (2) | C2—C3—C20—C25 | 77.64 (13) |
C3—C4—C5—C6 | −179.88 (12) | C25—C20—C21—C22 | 0.88 (18) |
C4—C5—C6—C7 | −0.2 (2) | C3—C20—C21—C22 | 176.71 (11) |
C5—C6—C7—C8 | −0.4 (2) | C20—C21—C22—C23 | −0.5 (2) |
C6—C7—C8—C9 | 0.2 (2) | C21—C22—C23—C24 | −0.2 (2) |
C7—C8—C9—C4 | 0.7 (2) | C21—C22—C23—C26 | 179.75 (16) |
C7—C8—C9—N1 | −177.86 (14) | C22—C23—C24—C25 | 0.4 (2) |
C5—C4—C9—C8 | −1.2 (2) | C26—C23—C24—C25 | −179.55 (16) |
C3—C4—C9—C8 | 179.45 (12) | C23—C24—C25—C20 | 0.1 (2) |
C5—C4—C9—N1 | 177.52 (12) | C21—C20—C25—C24 | −0.69 (19) |
C3—C4—C9—N1 | −1.79 (14) | C3—C20—C25—C24 | −176.65 (12) |
N1—C10—C11—C12 | −4.5 (3) | O1—C2—N1—C9 | −179.43 (12) |
C4—C3—C13—C18 | −91.47 (13) | C3—C2—N1—C9 | 2.63 (14) |
C20—C3—C13—C18 | 139.57 (11) | O1—C2—N1—C10 | 3.1 (2) |
C2—C3—C13—C18 | 20.86 (15) | C3—C2—N1—C10 | −174.88 (12) |
C4—C3—C13—C14 | 84.82 (14) | C8—C9—N1—C2 | 178.07 (13) |
C20—C3—C13—C14 | −44.14 (14) | C4—C9—N1—C2 | −0.58 (15) |
C2—C3—C13—C14 | −162.84 (11) | C8—C9—N1—C10 | −4.5 (2) |
C18—C13—C14—C15 | 0.1 (2) | C4—C9—N1—C10 | 176.83 (13) |
C3—C13—C14—C15 | −176.30 (13) | C11—C10—N1—C2 | 88.62 (17) |
C13—C14—C15—C16 | −0.2 (2) | C11—C10—N1—C9 | −88.53 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cgi | 0.93 | 2.94 | 3.740 (2) | 145 |
C12—H12A···N1 | 0.93 | 2.54 | 2.858 (2) | 100 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C25H23NO |
Mr | 353.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.3311 (2), 9.5793 (2), 11.5736 (2) |
α, β, γ (°) | 92.163 (1), 103.192 (1), 101.520 (1) |
V (Å3) | 983.15 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.26 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.982, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25969, 6260, 4310 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.725 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.156, 1.00 |
No. of reflections | 6260 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.21 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
C2—O1 | 1.2114 (14) | C9—N1 | 1.4046 (16) |
C2—N1 | 1.3621 (16) | C10—N1 | 1.4508 (16) |
O1—C2—N1 | 125.45 (11) | C4—C9—N1 | 109.54 (10) |
O1—C2—C3 | 126.57 (11) | N1—C10—C11 | 113.55 (13) |
N1—C2—C3 | 107.95 (9) | C2—N1—C9 | 111.71 (10) |
C5—C4—C9 | 119.89 (11) | C2—N1—C10 | 122.67 (11) |
C8—C9—C4 | 121.93 (12) | C9—N1—C10 | 125.57 (12) |
C8—C9—N1 | 128.51 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cgi | 0.93 | 2.94 | 3.740 (2) | 145 |
C12—H12A···N1 | 0.93 | 2.54 | 2.858 (2) | 100 |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management for their support.
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.
Indole compounds can be used as bioactive drugs (Stevenson et al., 2000). Indole derivatives exhibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Indoles have also been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). In view of this biological importance, an X-ray study of the title compound, (I), was carried out.
An ORTEP (Farrugia,1997) plot of the molecular is shown in Fig.1. The indole moiety is planar [maximum deviation of 0.038 (1) from the least square plane defined by all non hydrogen atoms in the molecule] and is nearly orthogonal to methylphenyl rings A and B, and makes a dihedral angle of 72.3 (4)° with the ring A, 76.7 (3)° with the ring B. Both the p-tolyl rings A and B are oriented at an angle of 72.6 (4)° with respect to each other. The sum of angles around N1 [360.0]° is in accordance with sp2 hybridization. The endocyclic angles around C4 is narrowed while those at C9 is widened from 120°. This may be caused by fusion of the smaller pyrrole ring to the six membered benzene ring of oxindole. A similar effect has also been observed by Sethu Sankar et al. (2002). The bond lengths in the oxindole ring systems indicate electron delocalization. The torsion angles C19—C16—C15—C14 [–179.5 (2)°], C19—C16—C17—C18 [179.7 (2)°] and C26—C23—C24—C25 [–179.6 (2)°], C26—C23—C22—C21 [179.8 (2)°] indicates that the methyl groups are coplanar with the plane of the attached benzene rings A and B. The allyl group deviates significantly from the plane of the indole moiety [C12—C11—C10—N1 = – 4.5 (3)°].
Weak intramolecular C—H···N and intermolecular C—H··· Cg interactions, with C5···Cg = 3.740 (2) Å, [Cg denotes centroid of C20—C25 ring] are observed in the molecular structure. In addition the packing is stabilized by van der Waals forces.