organic compounds
3-(2-Ethyl-2-phenylhydrazin-1-ylidene)indolin-2-one
aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and bH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: uzzmma@hotmail.com, dr.sammer.yousuf@gmail.com
In the title compound, C16H15N3O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The molecular conformation is supported by an intramolecular C—H⋯O interaction, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops.
Related literature
For a related structure, see: Jamal et al. (2011). For background to see: Chaluvaraju & Zaranappa (2011); Khan et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812047988/hb6996sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047988/hb6996Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047988/hb6996Isup3.cml
To a solution of 2,3-Indolinedione (10 mmol, 1.47 g) in 15 ml of ethanol with few drops of glacial acetic acid and 1-ethyl-1-phenylhydrazine (10 mmol,1.36 g) in 15 ml e thanol were added. The mixture was refluxed for 24 h and a solid was obtained upon removal of the solvent by rotary evaporation.The resulting solid was washed with hexane to afford the title compound. Yellow plates were grown from a mixture of ethanol and methanol (1:1) solvents by slow evaporation at room temperature.
H atoms on methyl, methylene, phenyl and nitrogen were positioned geometrically with C—H = 0.96, 0.97, 0.93 and C—H = 0.86 Å respectively, and constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(CH, CH2 and NH) and 1.5Ueq(CH3).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level. | |
Fig. 2. The crystal packing of the title compound. Hydrogen atoms are omitted for clearity. |
C16H15N3O | F(000) = 560 |
Mr = 265.31 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.463 (2) Å | Cell parameters from 1614 reflections |
b = 17.303 (4) Å | θ = 2.7–28.2° |
c = 8.5403 (18) Å | µ = 0.08 mm−1 |
β = 104.427 (5)° | T = 273 K |
V = 1354.3 (5) Å3 | Plate, yellow |
Z = 4 | 0.35 × 0.18 × 0.06 mm |
Bruker SMART APEX CCD diffractometer | 2448 independent reflections |
Radiation source: fine-focus sealed tube | 1783 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scan | θmax = 25.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.971, Tmax = 0.995 | k = −20→20 |
7875 measured reflections | l = −10→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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.2688P] where P = (Fo2 + 2Fc2)/3 |
2448 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C16H15N3O | V = 1354.3 (5) Å3 |
Mr = 265.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.463 (2) Å | µ = 0.08 mm−1 |
b = 17.303 (4) Å | T = 273 K |
c = 8.5403 (18) Å | 0.35 × 0.18 × 0.06 mm |
β = 104.427 (5)° |
Bruker SMART APEX CCD diffractometer | 2448 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1783 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.995 | Rint = 0.032 |
7875 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.18 e Å−3 |
2448 reflections | Δρmin = −0.17 e Å−3 |
181 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 | ||
O1 | 0.65674 (17) | 0.05361 (9) | −0.36767 (16) | 0.0663 (5) | |
N1 | 0.52529 (18) | −0.04875 (9) | −0.31253 (18) | 0.0506 (5) | |
H1A | 0.4712 | −0.0548 | −0.4088 | 0.061* | |
N2 | 0.79812 (16) | 0.02839 (8) | 0.01956 (17) | 0.0389 (4) | |
N3 | 0.89404 (17) | 0.08210 (9) | 0.00675 (17) | 0.0426 (4) | |
C1 | 0.5134 (2) | −0.09387 (10) | −0.1807 (2) | 0.0419 (5) | |
C2 | 0.4213 (2) | −0.15483 (11) | −0.1754 (2) | 0.0508 (5) | |
H2B | 0.3551 | −0.1723 | −0.2682 | 0.061* | |
C3 | 0.4310 (2) | −0.18901 (12) | −0.0267 (3) | 0.0547 (6) | |
H3A | 0.3707 | −0.2306 | −0.0194 | 0.066* | |
C4 | 0.5286 (2) | −0.16256 (11) | 0.1112 (2) | 0.0515 (5) | |
H4A | 0.5317 | −0.1859 | 0.2101 | 0.062* | |
C5 | 0.6221 (2) | −0.10171 (11) | 0.1042 (2) | 0.0446 (5) | |
H5A | 0.6884 | −0.0844 | 0.1971 | 0.053* | |
C6 | 0.6148 (2) | −0.06736 (10) | −0.0437 (2) | 0.0392 (4) | |
C7 | 0.6978 (2) | −0.00462 (10) | −0.0925 (2) | 0.0397 (5) | |
C8 | 0.6314 (2) | 0.00580 (11) | −0.2721 (2) | 0.0473 (5) | |
C9 | 0.9830 (2) | 0.10795 (10) | 0.1577 (2) | 0.0408 (5) | |
C10 | 1.0982 (2) | 0.15798 (12) | 0.1632 (2) | 0.0526 (5) | |
H10A | 1.1160 | 0.1764 | 0.0676 | 0.063* | |
C11 | 1.1871 (2) | 0.18077 (13) | 0.3106 (3) | 0.0639 (6) | |
H11A | 1.2647 | 0.2141 | 0.3128 | 0.077* | |
C12 | 1.1626 (3) | 0.15511 (13) | 0.4522 (3) | 0.0685 (7) | |
H12A | 1.2232 | 0.1703 | 0.5507 | 0.082* | |
C13 | 1.0470 (3) | 0.10645 (13) | 0.4474 (3) | 0.0661 (7) | |
H13A | 1.0295 | 0.0888 | 0.5437 | 0.079* | |
C14 | 0.9564 (2) | 0.08325 (11) | 0.3022 (2) | 0.0524 (5) | |
H14A | 0.8775 | 0.0510 | 0.3012 | 0.063* | |
C15 | 0.9259 (2) | 0.10639 (11) | −0.1461 (2) | 0.0485 (5) | |
H15A | 0.8863 | 0.0684 | −0.2289 | 0.058* | |
H15B | 1.0308 | 0.1079 | −0.1319 | 0.058* | |
C16 | 0.8632 (2) | 0.18441 (12) | −0.2025 (3) | 0.0636 (6) | |
H16A | 0.8869 | 0.1974 | −0.3022 | 0.095* | |
H16B | 0.9037 | 0.2226 | −0.1222 | 0.095* | |
H16C | 0.7592 | 0.1831 | −0.2190 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0818 (11) | 0.0690 (10) | 0.0388 (8) | −0.0259 (9) | −0.0025 (7) | 0.0131 (7) |
N1 | 0.0587 (11) | 0.0518 (10) | 0.0347 (8) | −0.0096 (9) | −0.0008 (7) | −0.0005 (7) |
N2 | 0.0412 (9) | 0.0364 (8) | 0.0376 (8) | 0.0002 (7) | 0.0070 (7) | 0.0019 (7) |
N3 | 0.0475 (10) | 0.0431 (9) | 0.0362 (8) | −0.0058 (8) | 0.0084 (7) | 0.0035 (7) |
C1 | 0.0452 (11) | 0.0397 (10) | 0.0392 (10) | 0.0032 (9) | 0.0075 (8) | −0.0009 (8) |
C2 | 0.0502 (13) | 0.0467 (12) | 0.0536 (12) | −0.0066 (10) | 0.0091 (10) | −0.0082 (10) |
C3 | 0.0551 (13) | 0.0460 (12) | 0.0640 (14) | −0.0083 (10) | 0.0167 (11) | 0.0001 (10) |
C4 | 0.0528 (13) | 0.0500 (12) | 0.0532 (12) | 0.0005 (10) | 0.0158 (10) | 0.0110 (10) |
C5 | 0.0427 (11) | 0.0486 (11) | 0.0405 (11) | 0.0037 (9) | 0.0068 (8) | 0.0036 (9) |
C6 | 0.0381 (10) | 0.0375 (10) | 0.0406 (10) | 0.0039 (8) | 0.0073 (8) | 0.0005 (8) |
C7 | 0.0434 (11) | 0.0384 (10) | 0.0354 (9) | 0.0015 (9) | 0.0063 (8) | 0.0015 (8) |
C8 | 0.0552 (13) | 0.0466 (11) | 0.0362 (10) | −0.0032 (10) | 0.0040 (9) | 0.0017 (9) |
C9 | 0.0418 (11) | 0.0359 (10) | 0.0422 (10) | 0.0025 (9) | 0.0058 (8) | −0.0015 (8) |
C10 | 0.0495 (12) | 0.0522 (12) | 0.0559 (13) | −0.0055 (10) | 0.0124 (10) | −0.0013 (10) |
C11 | 0.0513 (14) | 0.0584 (14) | 0.0742 (16) | −0.0082 (11) | 0.0010 (11) | −0.0089 (12) |
C12 | 0.0771 (17) | 0.0580 (14) | 0.0557 (14) | −0.0023 (13) | −0.0113 (12) | −0.0086 (11) |
C13 | 0.0910 (18) | 0.0603 (14) | 0.0404 (12) | −0.0040 (14) | 0.0042 (11) | −0.0006 (10) |
C14 | 0.0635 (14) | 0.0495 (12) | 0.0422 (11) | −0.0071 (11) | 0.0095 (10) | −0.0004 (9) |
C15 | 0.0481 (12) | 0.0550 (12) | 0.0426 (11) | −0.0001 (10) | 0.0119 (9) | 0.0024 (9) |
C16 | 0.0624 (15) | 0.0605 (14) | 0.0656 (14) | 0.0000 (12) | 0.0113 (11) | 0.0163 (11) |
O1—C8 | 1.227 (2) | C7—C8 | 1.517 (2) |
N1—C8 | 1.359 (2) | C9—C10 | 1.384 (3) |
N1—C1 | 1.398 (2) | C9—C14 | 1.387 (3) |
N1—H1A | 0.8600 | C10—C11 | 1.386 (3) |
N2—C7 | 1.300 (2) | C10—H10A | 0.9300 |
N2—N3 | 1.323 (2) | C11—C12 | 1.361 (3) |
N3—C9 | 1.425 (2) | C11—H11A | 0.9300 |
N3—C15 | 1.472 (2) | C12—C13 | 1.373 (3) |
C1—C2 | 1.376 (3) | C12—H12A | 0.9300 |
C1—C6 | 1.393 (2) | C13—C14 | 1.380 (3) |
C2—C3 | 1.383 (3) | C13—H13A | 0.9300 |
C2—H2B | 0.9300 | C14—H14A | 0.9300 |
C3—C4 | 1.381 (3) | C15—C16 | 1.504 (3) |
C3—H3A | 0.9300 | C15—H15A | 0.9700 |
C4—C5 | 1.386 (3) | C15—H15B | 0.9700 |
C4—H4A | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.382 (2) | C16—H16B | 0.9600 |
C5—H5A | 0.9300 | C16—H16C | 0.9600 |
C6—C7 | 1.460 (3) | ||
C8—N1—C1 | 112.74 (15) | C10—C9—C14 | 118.60 (18) |
C8—N1—H1A | 123.6 | C10—C9—N3 | 120.67 (17) |
C1—N1—H1A | 123.6 | C14—C9—N3 | 120.73 (17) |
C7—N2—N3 | 129.64 (15) | C9—C10—C11 | 120.3 (2) |
N2—N3—C9 | 114.13 (14) | C9—C10—H10A | 119.9 |
N2—N3—C15 | 124.76 (15) | C11—C10—H10A | 119.9 |
C9—N3—C15 | 120.49 (16) | C12—C11—C10 | 121.0 (2) |
C2—C1—C6 | 122.30 (17) | C12—C11—H11A | 119.5 |
C2—C1—N1 | 129.31 (17) | C10—C11—H11A | 119.5 |
C6—C1—N1 | 108.40 (16) | C11—C12—C13 | 119.0 (2) |
C1—C2—C3 | 117.40 (18) | C11—C12—H12A | 120.5 |
C1—C2—H2B | 121.3 | C13—C12—H12A | 120.5 |
C3—C2—H2B | 121.3 | C12—C13—C14 | 121.1 (2) |
C4—C3—C2 | 121.2 (2) | C12—C13—H13A | 119.4 |
C4—C3—H3A | 119.4 | C14—C13—H13A | 119.4 |
C2—C3—H3A | 119.4 | C13—C14—C9 | 120.0 (2) |
C3—C4—C5 | 120.91 (19) | C13—C14—H14A | 120.0 |
C3—C4—H4A | 119.5 | C9—C14—H14A | 120.0 |
C5—C4—H4A | 119.5 | N3—C15—C16 | 112.86 (17) |
C6—C5—C4 | 118.62 (18) | N3—C15—H15A | 109.0 |
C6—C5—H5A | 120.7 | C16—C15—H15A | 109.0 |
C4—C5—H5A | 120.7 | N3—C15—H15B | 109.0 |
C5—C6—C1 | 119.53 (18) | C16—C15—H15B | 109.0 |
C5—C6—C7 | 132.28 (16) | H15A—C15—H15B | 107.8 |
C1—C6—C7 | 108.18 (15) | C15—C16—H16A | 109.5 |
N2—C7—C6 | 117.53 (15) | C15—C16—H16B | 109.5 |
N2—C7—C8 | 137.30 (17) | H16A—C16—H16B | 109.5 |
C6—C7—C8 | 105.09 (15) | C15—C16—H16C | 109.5 |
O1—C8—N1 | 123.66 (17) | H16A—C16—H16C | 109.5 |
O1—C8—C7 | 130.73 (18) | H16B—C16—H16C | 109.5 |
N1—C8—C7 | 105.54 (16) | ||
C7—N2—N3—C9 | 176.71 (17) | C1—N1—C8—O1 | −177.0 (2) |
C7—N2—N3—C15 | −12.3 (3) | C1—N1—C8—C7 | 0.2 (2) |
C8—N1—C1—C2 | −178.8 (2) | N2—C7—C8—O1 | −1.0 (4) |
C8—N1—C1—C6 | 1.2 (2) | C6—C7—C8—O1 | 175.5 (2) |
C6—C1—C2—C3 | 0.9 (3) | N2—C7—C8—N1 | −178.0 (2) |
N1—C1—C2—C3 | −179.08 (19) | C6—C7—C8—N1 | −1.4 (2) |
C1—C2—C3—C4 | 0.5 (3) | N2—N3—C9—C10 | 173.23 (16) |
C2—C3—C4—C5 | −1.3 (3) | C15—N3—C9—C10 | 1.8 (3) |
C3—C4—C5—C6 | 0.6 (3) | N2—N3—C9—C14 | −6.5 (3) |
C4—C5—C6—C1 | 0.7 (3) | C15—N3—C9—C14 | −177.88 (17) |
C4—C5—C6—C7 | −178.50 (19) | C14—C9—C10—C11 | 1.9 (3) |
C2—C1—C6—C5 | −1.6 (3) | N3—C9—C10—C11 | −177.84 (18) |
N1—C1—C6—C5 | 178.46 (17) | C9—C10—C11—C12 | −0.5 (3) |
C2—C1—C6—C7 | 177.86 (17) | C10—C11—C12—C13 | −0.5 (4) |
N1—C1—C6—C7 | −2.1 (2) | C11—C12—C13—C14 | 0.2 (4) |
N3—N2—C7—C6 | 174.94 (17) | C12—C13—C14—C9 | 1.2 (3) |
N3—N2—C7—C8 | −8.8 (4) | C10—C9—C14—C13 | −2.2 (3) |
C5—C6—C7—N2 | −1.2 (3) | N3—C9—C14—C13 | 177.49 (18) |
C1—C6—C7—N2 | 179.53 (16) | N2—N3—C15—C16 | 106.2 (2) |
C5—C6—C7—C8 | −178.5 (2) | C9—N3—C15—C16 | −83.3 (2) |
C1—C6—C7—C8 | 2.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O1 | 0.97 | 2.21 | 2.916 (2) | 128 |
N1—H1A···O1i | 0.86 | 1.99 | 2.844 (2) | 172 |
Symmetry code: (i) −x+1, −y, −z−1. |
Experimental details
Crystal data | |
Chemical formula | C16H15N3O |
Mr | 265.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 9.463 (2), 17.303 (4), 8.5403 (18) |
β (°) | 104.427 (5) |
V (Å3) | 1354.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.18 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.971, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7875, 2448, 1783 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.116, 1.08 |
No. of reflections | 2448 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.17 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O1 | 0.97 | 2.21 | 2.916 (2) | 128 |
N1—H1A···O1i | 0.86 | 1.99 | 2.844 (2) | 172 |
Symmetry code: (i) −x+1, −y, −z−1. |
Acknowledgements
The authors are thankful to the Higher Education Commission (HEC) Pakistan for financial support under the National Research Grants Program for Universities (grant No. 20–1862/R&D/10).
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.
Isatin and its Schiff bases form an important class of organic compounds with a variety of biological activities. Many studies have reported regarding the biological activities of Schiff bases, including their antifungal, antibacterial, anticancer and antiglycation (Khan et al., 2009; Chaluvaraju & Zaranappa. 2011). In order to study the biological activity of title compound, we undertook the synthesis of title compound and report its crystal structure in this paper (Fig. 1). The title compound I was found a potent DPPH radical scavenger.
The title compound, C16H15N3O is an structural analogue of our previously published compound 3-amino-N'-(2-oxoindolin-3-ylidene)- benzohydrazide (Jamal et al., 2011) with the difference that the keto amine phenyl moiety is replaced by phenyl ring (C9–C14) and N3 is substituted with ethyl group (C15–C16). The phenyl and indole rings are each planar with the dihedral angle of 14.49 (9)° between them. The geometry of molecule is stabilized by an intramolecular C15—H15A···O1 hydrogen bond. In the crystal molecules are consolidated by intermolecular N1—H1A···O1 hydrogen bond (Fig. 2. symmetry codes as in Table 2).