organic compounds
1-Allyl-3,3-diphenylindolin-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 cPostgraduate Research, Department of Chemistry, New College, Chennai 600014, India
*Correspondence e-mail: sudharose18@gmail.com
In the title compound, C23H19NO, the oxindole residue is essentially planar and is almost perpendicular to the phenyl rings [dihedral angles = 72.1 (6) and 77.6 (6)°]. The molecular packing is stabilized by C—H⋯O hydrogen bonds and C—H⋯N interactions.
Related literature
For related literature, see: Bandini et al. (2005); Florin et al. (1980); Govind et al. (2003); Rajeswaran et al. (1999); Ramirez & Garcia-Rubio (2003).
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/S1600536808009446/gw2038sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009446/gw2038Isup2.hkl
To a solution of phenyl magnesium bromide in dry THF, at 0°C under N2 atm.,1-N-allyl isatin (0.005 mol, 0.935 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. The progress of the reaction was followed by TLC. On completion of the reaction, a
of NH4Cl was added slowly at 0°C. The aqueous layer was washed with brine (50 ml) and dried. On removal of the solvent under reduced pressure, a crude mass was obtained., which was purified over a column of silica gel (100–200 mesh) using hexane/ethyl acetate as Compound was recrystallized from methanol.H atoms were placed in idealized positions and allowed to ride on their parent atoms with aromatic C—H distances of 0.93 Å, methylene C—H distances of 0.97 Å and with Uiso(H) = 1.2 Ueq(C).In the absence of significant
effects, Friedel pairs have been merged. The parameter is removed from the since the Flack [10.0 (10)] is meaningless.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 a axis. |
C23H19NO | F(000) = 688 |
Mr = 325.39 | Dx = 1.230 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: p 2ac 2ab | Cell parameters from 4984 reflections |
a = 8.8449 (3) Å | θ = 2.5–30.3° |
b = 12.3879 (4) Å | µ = 0.08 mm−1 |
c = 16.0377 (4) Å | T = 293 K |
V = 1757.25 (9) Å3 | Prism, yellow |
Z = 4 | 0.30 × 0.24 × 0.20 mm |
Bruker Kappa APEX2 diffractometer | 3559 independent reflections |
Radiation source: fine-focus sealed tube | 2611 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and ϕ scans | θmax = 32.6°, θmin = 2.5° |
Absorption correction: multi-scan (Blessing, 1995) | h = −13→11 |
Tmin = 0.978, Tmax = 0.985 | k = −18→14 |
14793 measured reflections | l = −20→24 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3 |
3559 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C23H19NO | V = 1757.25 (9) Å3 |
Mr = 325.39 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.8449 (3) Å | µ = 0.08 mm−1 |
b = 12.3879 (4) Å | T = 293 K |
c = 16.0377 (4) Å | 0.30 × 0.24 × 0.20 mm |
Bruker Kappa APEX2 diffractometer | 3559 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 2611 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.985 | Rint = 0.026 |
14793 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.31 e Å−3 |
3559 reflections | Δρmin = −0.21 e Å−3 |
226 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 | 0.7623 (2) | 0.14099 (15) | 0.09508 (12) | 0.0367 (4) | |
C3 | 0.7846 (2) | 0.02597 (14) | 0.13122 (10) | 0.0331 (3) | |
C4 | 0.8751 (2) | −0.02725 (15) | 0.06249 (11) | 0.0349 (4) | |
C5 | 0.9240 (3) | −0.13195 (17) | 0.05340 (13) | 0.0454 (5) | |
H5 | 0.9017 | −0.1836 | 0.0937 | 0.055* | |
C6 | 1.0075 (3) | −0.1595 (2) | −0.01711 (14) | 0.0523 (5) | |
H6 | 1.0420 | −0.2299 | −0.0239 | 0.063* | |
C7 | 1.0390 (3) | −0.0829 (2) | −0.07656 (14) | 0.0570 (6) | |
H7 | 1.0952 | −0.1025 | −0.1231 | 0.068* | |
C8 | 0.9897 (3) | 0.0220 (2) | −0.06920 (13) | 0.0517 (5) | |
H8 | 1.0119 | 0.0733 | −0.1097 | 0.062* | |
C9 | 0.9059 (2) | 0.04807 (16) | 0.00085 (11) | 0.0387 (4) | |
C10 | 0.8516 (3) | 0.24727 (19) | −0.02570 (15) | 0.0543 (6) | |
H10A | 0.9527 | 0.2513 | −0.0490 | 0.065* | |
H10B | 0.8404 | 0.3073 | 0.0126 | 0.065* | |
C11 | 0.7411 (3) | 0.2612 (2) | −0.09456 (17) | 0.0675 (7) | |
H11 | 0.7486 | 0.3252 | −0.1246 | 0.081* | |
C12 | 0.6406 (4) | 0.1988 (3) | −0.1170 (2) | 0.0792 (9) | |
H12A | 0.6272 | 0.1334 | −0.0894 | 0.095* | |
H12B | 0.5781 | 0.2170 | −0.1614 | 0.095* | |
C13 | 0.8731 (2) | 0.03991 (15) | 0.21273 (11) | 0.0363 (4) | |
C14 | 0.8029 (3) | 0.08647 (16) | 0.28170 (13) | 0.0439 (4) | |
H14 | 0.7018 | 0.1067 | 0.2784 | 0.053* | |
C15 | 0.8814 (3) | 0.10282 (19) | 0.35467 (14) | 0.0534 (6) | |
H15 | 0.8327 | 0.1333 | 0.4004 | 0.064* | |
C16 | 1.0312 (3) | 0.0745 (2) | 0.36051 (15) | 0.0643 (7) | |
H16 | 1.0845 | 0.0863 | 0.4097 | 0.077* | |
C17 | 1.1015 (3) | 0.0285 (3) | 0.29290 (17) | 0.0782 (9) | |
H17 | 1.2028 | 0.0090 | 0.2964 | 0.094* | |
C18 | 1.0225 (3) | 0.0110 (3) | 0.21964 (15) | 0.0597 (6) | |
H18 | 1.0713 | −0.0208 | 0.1745 | 0.072* | |
C19 | 0.6328 (2) | −0.03049 (15) | 0.14321 (11) | 0.0347 (4) | |
C20 | 0.5121 (2) | −0.00927 (18) | 0.09117 (14) | 0.0446 (5) | |
H20 | 0.5221 | 0.0426 | 0.0496 | 0.054* | |
C21 | 0.3761 (3) | −0.0640 (2) | 0.09980 (17) | 0.0548 (6) | |
H21 | 0.2957 | −0.0484 | 0.0645 | 0.066* | |
C22 | 0.3604 (3) | −0.1413 (2) | 0.16061 (17) | 0.0572 (6) | |
H22 | 0.2690 | −0.1775 | 0.1669 | 0.069* | |
C23 | 0.4792 (3) | −0.1650 (2) | 0.21185 (15) | 0.0596 (6) | |
H23 | 0.4688 | −0.2178 | 0.2526 | 0.072* | |
C24 | 0.6155 (3) | −0.11038 (18) | 0.20325 (13) | 0.0500 (5) | |
H24 | 0.6961 | −0.1275 | 0.2381 | 0.060* | |
N1 | 0.8393 (2) | 0.14731 (13) | 0.02162 (10) | 0.0414 (4) | |
O1 | 0.69142 (19) | 0.21379 (12) | 0.12636 (10) | 0.0505 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0361 (9) | 0.0371 (9) | 0.0367 (8) | −0.0015 (7) | 0.0006 (7) | 0.0024 (7) |
C3 | 0.0331 (8) | 0.0371 (8) | 0.0290 (7) | 0.0005 (7) | 0.0027 (6) | 0.0012 (7) |
C4 | 0.0326 (8) | 0.0408 (9) | 0.0313 (8) | −0.0012 (7) | 0.0004 (7) | −0.0026 (7) |
C5 | 0.0469 (11) | 0.0442 (10) | 0.0452 (10) | 0.0025 (9) | 0.0027 (9) | −0.0034 (9) |
C6 | 0.0480 (12) | 0.0570 (12) | 0.0518 (12) | 0.0076 (10) | 0.0008 (10) | −0.0170 (10) |
C7 | 0.0455 (12) | 0.0809 (17) | 0.0446 (11) | −0.0002 (11) | 0.0090 (10) | −0.0169 (11) |
C8 | 0.0486 (12) | 0.0700 (14) | 0.0363 (10) | −0.0056 (11) | 0.0102 (9) | 0.0001 (10) |
C9 | 0.0349 (9) | 0.0463 (9) | 0.0351 (8) | −0.0051 (8) | 0.0027 (7) | 0.0006 (8) |
C10 | 0.0559 (13) | 0.0514 (11) | 0.0557 (13) | −0.0076 (10) | 0.0055 (11) | 0.0204 (11) |
C11 | 0.0746 (17) | 0.0706 (17) | 0.0574 (15) | 0.0029 (15) | −0.0022 (14) | 0.0130 (13) |
C12 | 0.088 (2) | 0.084 (2) | 0.0650 (17) | 0.0092 (19) | 0.0007 (16) | −0.0026 (15) |
C13 | 0.0369 (9) | 0.0391 (9) | 0.0329 (8) | −0.0001 (7) | 0.0011 (7) | 0.0000 (7) |
C14 | 0.0458 (11) | 0.0473 (10) | 0.0386 (10) | 0.0052 (9) | 0.0013 (8) | −0.0040 (8) |
C15 | 0.0651 (15) | 0.0582 (13) | 0.0369 (10) | 0.0023 (12) | 0.0004 (10) | −0.0089 (9) |
C16 | 0.0631 (16) | 0.0861 (18) | 0.0437 (12) | −0.0075 (14) | −0.0126 (11) | −0.0102 (12) |
C17 | 0.0463 (13) | 0.126 (3) | 0.0618 (15) | 0.0108 (17) | −0.0163 (12) | −0.0218 (18) |
C18 | 0.0395 (11) | 0.0917 (18) | 0.0479 (11) | 0.0075 (12) | −0.0028 (9) | −0.0165 (12) |
C19 | 0.0354 (9) | 0.0368 (8) | 0.0319 (8) | −0.0017 (7) | 0.0050 (6) | 0.0008 (7) |
C20 | 0.0394 (10) | 0.0457 (10) | 0.0489 (11) | 0.0001 (8) | 0.0001 (8) | 0.0063 (9) |
C21 | 0.0343 (10) | 0.0569 (13) | 0.0730 (15) | −0.0010 (9) | −0.0001 (10) | −0.0082 (12) |
C22 | 0.0471 (12) | 0.0530 (12) | 0.0713 (15) | −0.0151 (10) | 0.0185 (11) | −0.0132 (12) |
C23 | 0.0773 (17) | 0.0548 (13) | 0.0468 (11) | −0.0253 (12) | 0.0135 (12) | 0.0028 (10) |
C24 | 0.0602 (14) | 0.0513 (12) | 0.0387 (10) | −0.0141 (11) | −0.0024 (9) | 0.0105 (9) |
N1 | 0.0439 (9) | 0.0401 (8) | 0.0401 (8) | −0.0042 (7) | 0.0052 (7) | 0.0081 (7) |
O1 | 0.0565 (9) | 0.0411 (7) | 0.0539 (9) | 0.0091 (7) | 0.0066 (7) | 0.0007 (6) |
C2—O1 | 1.207 (2) | C12—H12B | 0.9300 |
C2—N1 | 1.363 (2) | C13—C18 | 1.374 (3) |
C2—C3 | 1.551 (3) | C13—C14 | 1.393 (3) |
C3—C4 | 1.513 (2) | C14—C15 | 1.376 (3) |
C3—C19 | 1.526 (3) | C14—H14 | 0.9300 |
C3—C13 | 1.533 (2) | C15—C16 | 1.374 (4) |
C4—C5 | 1.375 (3) | C15—H15 | 0.9300 |
C4—C9 | 1.387 (3) | C16—C17 | 1.373 (4) |
C5—C6 | 1.393 (3) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.384 (3) |
C6—C7 | 1.374 (3) | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—C8 | 1.375 (4) | C19—C20 | 1.380 (3) |
C7—H7 | 0.9300 | C19—C24 | 1.389 (3) |
C8—C9 | 1.384 (3) | C20—C21 | 1.388 (3) |
C8—H8 | 0.9300 | C20—H20 | 0.9300 |
C9—N1 | 1.404 (3) | C21—C22 | 1.374 (4) |
C10—N1 | 1.456 (3) | C21—H21 | 0.9300 |
C10—C11 | 1.485 (4) | C22—C23 | 1.366 (4) |
C10—H10A | 0.9700 | C22—H22 | 0.9300 |
C10—H10B | 0.9700 | C23—C24 | 1.390 (3) |
C11—C12 | 1.232 (4) | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—H12A | 0.9300 | ||
O1—C2—N1 | 125.14 (18) | C18—C13—C14 | 118.21 (19) |
O1—C2—C3 | 126.65 (17) | C18—C13—C3 | 122.03 (18) |
N1—C2—C3 | 108.20 (15) | C14—C13—C3 | 119.73 (17) |
C4—C3—C19 | 110.95 (15) | C15—C14—C13 | 120.7 (2) |
C4—C3—C13 | 113.58 (15) | C15—C14—H14 | 119.6 |
C19—C3—C13 | 113.16 (14) | C13—C14—H14 | 119.6 |
C4—C3—C2 | 101.25 (14) | C16—C15—C14 | 120.5 (2) |
C19—C3—C2 | 110.88 (15) | C16—C15—H15 | 119.8 |
C13—C3—C2 | 106.26 (14) | C14—C15—H15 | 119.8 |
C5—C4—C9 | 119.81 (17) | C17—C16—C15 | 119.2 (2) |
C5—C4—C3 | 130.89 (17) | C17—C16—H16 | 120.4 |
C9—C4—C3 | 109.29 (16) | C15—C16—H16 | 120.4 |
C4—C5—C6 | 118.9 (2) | C16—C17—C18 | 120.5 (2) |
C4—C5—H5 | 120.5 | C16—C17—H17 | 119.8 |
C6—C5—H5 | 120.5 | C18—C17—H17 | 119.8 |
C7—C6—C5 | 120.1 (2) | C13—C18—C17 | 120.8 (2) |
C7—C6—H6 | 119.9 | C13—C18—H18 | 119.6 |
C5—C6—H6 | 119.9 | C17—C18—H18 | 119.6 |
C6—C7—C8 | 121.9 (2) | C20—C19—C24 | 118.03 (18) |
C6—C7—H7 | 119.0 | C20—C19—C3 | 121.12 (16) |
C8—C7—H7 | 119.0 | C24—C19—C3 | 120.69 (18) |
C7—C8—C9 | 117.4 (2) | C19—C20—C21 | 121.1 (2) |
C7—C8—H8 | 121.3 | C19—C20—H20 | 119.4 |
C9—C8—H8 | 121.3 | C21—C20—H20 | 119.4 |
C8—C9—C4 | 121.79 (19) | C22—C21—C20 | 119.9 (2) |
C8—C9—N1 | 128.49 (18) | C22—C21—H21 | 120.0 |
C4—C9—N1 | 109.72 (16) | C20—C21—H21 | 120.0 |
N1—C10—C11 | 115.9 (2) | C23—C22—C21 | 119.9 (2) |
N1—C10—H10A | 108.3 | C23—C22—H22 | 120.0 |
C11—C10—H10A | 108.3 | C21—C22—H22 | 120.0 |
N1—C10—H10B | 108.3 | C22—C23—C24 | 120.2 (2) |
C11—C10—H10B | 108.3 | C22—C23—H23 | 119.9 |
H10A—C10—H10B | 107.4 | C24—C23—H23 | 119.9 |
C12—C11—C10 | 128.2 (3) | C19—C24—C23 | 120.7 (2) |
C12—C11—H11 | 115.9 | C19—C24—H24 | 119.6 |
C10—C11—H11 | 115.9 | C23—C24—H24 | 119.6 |
C11—C12—H12A | 120.0 | C2—N1—C9 | 111.39 (15) |
C11—C12—H12B | 120.0 | C2—N1—C10 | 122.46 (18) |
H12A—C12—H12B | 120.0 | C9—N1—C10 | 126.12 (17) |
O1—C2—C3—C4 | 177.4 (2) | C3—C13—C14—C15 | −177.99 (18) |
N1—C2—C3—C4 | −3.70 (18) | C13—C14—C15—C16 | 0.7 (4) |
O1—C2—C3—C19 | 59.6 (2) | C14—C15—C16—C17 | −0.7 (4) |
N1—C2—C3—C19 | −121.48 (16) | C15—C16—C17—C18 | 0.1 (5) |
O1—C2—C3—C13 | −63.8 (2) | C14—C13—C18—C17 | −0.6 (4) |
N1—C2—C3—C13 | 115.17 (16) | C3—C13—C18—C17 | 177.3 (3) |
C19—C3—C4—C5 | −57.8 (3) | C16—C17—C18—C13 | 0.6 (5) |
C13—C3—C4—C5 | 71.0 (3) | C4—C3—C19—C20 | −80.4 (2) |
C2—C3—C4—C5 | −175.6 (2) | C13—C3—C19—C20 | 150.58 (17) |
C19—C3—C4—C9 | 120.96 (17) | C2—C3—C19—C20 | 31.3 (2) |
C13—C3—C4—C9 | −110.24 (17) | C4—C3—C19—C24 | 95.0 (2) |
C2—C3—C4—C9 | 3.23 (18) | C13—C3—C19—C24 | −34.0 (2) |
C9—C4—C5—C6 | 1.6 (3) | C2—C3—C19—C24 | −153.30 (18) |
C3—C4—C5—C6 | −179.68 (19) | C24—C19—C20—C21 | 1.6 (3) |
C4—C5—C6—C7 | −0.5 (3) | C3—C19—C20—C21 | 177.17 (19) |
C5—C6—C7—C8 | −0.3 (4) | C19—C20—C21—C22 | −0.5 (4) |
C6—C7—C8—C9 | −0.2 (4) | C20—C21—C22—C23 | −0.7 (4) |
C7—C8—C9—C4 | 1.4 (3) | C21—C22—C23—C24 | 0.6 (4) |
C7—C8—C9—N1 | −177.8 (2) | C20—C19—C24—C23 | −1.7 (3) |
C5—C4—C9—C8 | −2.2 (3) | C3—C19—C24—C23 | −177.3 (2) |
C3—C4—C9—C8 | 178.88 (19) | C22—C23—C24—C19 | 0.6 (4) |
C5—C4—C9—N1 | 177.21 (18) | O1—C2—N1—C9 | −178.1 (2) |
C3—C4—C9—N1 | −1.7 (2) | C3—C2—N1—C9 | 3.0 (2) |
N1—C10—C11—C12 | −0.3 (4) | O1—C2—N1—C10 | 3.8 (3) |
C4—C3—C13—C18 | 3.0 (3) | C3—C2—N1—C10 | −175.20 (18) |
C19—C3—C13—C18 | 130.7 (2) | C8—C9—N1—C2 | 178.5 (2) |
C2—C3—C13—C18 | −107.4 (2) | C4—C9—N1—C2 | −0.8 (2) |
C4—C3—C13—C14 | −179.13 (17) | C8—C9—N1—C10 | −3.4 (4) |
C19—C3—C13—C14 | −51.5 (2) | C4—C9—N1—C10 | 177.25 (19) |
C2—C3—C13—C14 | 70.4 (2) | C11—C10—N1—C2 | −96.5 (3) |
C18—C13—C14—C15 | −0.1 (3) | C11—C10—N1—C9 | 85.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···N1 | 0.93 | 2.59 | 2.905 (4) | 100 |
C10—H10A···O1i | 0.97 | 2.49 | 3.446 (3) | 170 |
C23—H23···O1ii | 0.93 | 2.55 | 3.356 (3) | 146 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H19NO |
Mr | 325.39 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 8.8449 (3), 12.3879 (4), 16.0377 (4) |
V (Å3) | 1757.25 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEX2 diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.978, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14793, 3559, 2611 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.759 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.142, 1.09 |
No. of reflections | 3559 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −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 | 1.207 (2) | C9—N1 | 1.404 (3) |
C2—N1 | 1.363 (2) | C10—N1 | 1.456 (3) |
O1—C2—N1 | 125.14 (18) | C4—C9—N1 | 109.72 (16) |
O1—C2—C3 | 126.65 (17) | N1—C10—C11 | 115.9 (2) |
N1—C2—C3 | 108.20 (15) | C2—N1—C9 | 111.39 (15) |
C5—C4—C9 | 119.81 (17) | C2—N1—C10 | 122.46 (18) |
C8—C9—C4 | 121.79 (19) | C9—N1—C10 | 126.12 (17) |
C8—C9—N1 | 128.49 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···N1 | 0.93 | 2.59 | 2.905 (4) | 100 |
C10—H10A···O1i | 0.97 | 2.49 | 3.446 (3) | 170 |
C23—H23···O1ii | 0.93 | 2.55 | 3.356 (3) | 146 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN also thanks SRM Management, India, 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 and its derivatives form a class of toxic recalcitrant N – heterocyclic compounds that are considered as pollutants (Florin et al., 1980). Derivatives of indole have received much attention because of their widespread applications in materials science, agrichemicals, and pharmaceuticals (Ramirez & Garcia-Rubio, 2003).Their preparation and functionalization continues to be a fascinating subject in organic synthesis due to the frequent appearance of indoles in biologically interesting compounds (Bandini et al., 2005). Compounds containing the indole moiety have been proven to display high activity of aldose reductase inhibition (Rajeswaran et al., 1999). In view of this importance, an X-ray study of the title compound, (I), was carried out.
An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig.1. The indole moiety (N1/C2 – C9) is planar with the maximum deviation of 0.040 (8) for C2 atom. The oxindole ring is nearly orthogonal to phenyl rings A (C13 – C18) and B (C19 – C24), and makes a dihedral angle of 72.1 (6)° with the ring A, 77.6 (6)° with the ring B. Both the phenyl rings A and B are oriented at an angle of 70.4 (7)° with respect to each other. The sum of angles at N1 [360.0]° indicate sp2 hybridization. In the oxindole ring systems, the variation in endocyclic angles are due to fusion of five and six membered rings (Govind et al., 2003). The N1— C2 and C2— O1 bond lengths indicate electron delocalization over atoms N1, C2 and O1. The torsion angle C12—C11—C10—N1 = – 0.3 (4)° indicate that the allyl group deviates significantly from the plane of the attached indole moiety.
Weak intramolecular C—H···N and C—H··· π interactions stabilize the molecule. The crystal packing also involves inter molecular C—H···O interactions and van der Waals forces.