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ISSN: 2056-9890

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

(Received 20 November 2012; accepted 21 November 2012; online 28 November 2012)

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[Jamal, R. A., Ashiq, U., Yousuf, S. & Ain, Q. ul (2011). Acta Cryst. E67, o2166.]). For background to Schiff bases, see: Chaluvaraju & Zaranappa (2011[Chaluvaraju, K. C. & Zaranappa (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 541-546.]); Khan et al. (2009[Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O

  • Mr = 265.31

  • Monoclinic, P 21 /c

  • a = 9.463 (2) Å

  • b = 17.303 (4) Å

  • c = 8.5403 (18) Å

  • β = 104.427 (5)°

  • V = 1354.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 273 K

  • 0.35 × 0.18 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.995

  • 7875 measured reflections

  • 2448 independent reflections

  • 1783 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.116

  • S = 1.08

  • 2448 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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).

Related literature top

For a related structure, see: Jamal et al. (2011). For background to Schiff bases, see: Chaluvaraju et al. (2011); Khan et al. (2009).

Experimental top

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.

Refinement top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen atoms are omitted for clearity.
3-(2-Ethyl-2-phenylhydrazin-1-ylidene)indolin-2-one top
Crystal data top
C16H15N3OF(000) = 560
Mr = 265.31Dx = 1.301 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.463 (2) ÅCell parameters from 1614 reflections
b = 17.303 (4) Åθ = 2.7–28.2°
c = 8.5403 (18) ŵ = 0.08 mm1
β = 104.427 (5)°T = 273 K
V = 1354.3 (5) Å3Plate, yellow
Z = 40.35 × 0.18 × 0.06 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
2448 independent reflections
Radiation source: fine-focus sealed tube1783 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scanθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1111
Tmin = 0.971, Tmax = 0.995k = 2020
7875 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-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 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C16H15N3OV = 1354.3 (5) Å3
Mr = 265.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.463 (2) ŵ = 0.08 mm1
b = 17.303 (4) ÅT = 273 K
c = 8.5403 (18) Å0.35 × 0.18 × 0.06 mm
β = 104.427 (5)°
Data collection top
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 = 0.995Rint = 0.032
7875 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.08Δρmax = 0.18 e Å3
2448 reflectionsΔρmin = 0.17 e Å3
181 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.65674 (17)0.05361 (9)0.36767 (16)0.0663 (5)
N10.52529 (18)0.04875 (9)0.31253 (18)0.0506 (5)
H1A0.47120.05480.40880.061*
N20.79812 (16)0.02839 (8)0.01956 (17)0.0389 (4)
N30.89404 (17)0.08210 (9)0.00675 (17)0.0426 (4)
C10.5134 (2)0.09387 (10)0.1807 (2)0.0419 (5)
C20.4213 (2)0.15483 (11)0.1754 (2)0.0508 (5)
H2B0.35510.17230.26820.061*
C30.4310 (2)0.18901 (12)0.0267 (3)0.0547 (6)
H3A0.37070.23060.01940.066*
C40.5286 (2)0.16256 (11)0.1112 (2)0.0515 (5)
H4A0.53170.18590.21010.062*
C50.6221 (2)0.10171 (11)0.1042 (2)0.0446 (5)
H5A0.68840.08440.19710.053*
C60.6148 (2)0.06736 (10)0.0437 (2)0.0392 (4)
C70.6978 (2)0.00462 (10)0.0925 (2)0.0397 (5)
C80.6314 (2)0.00580 (11)0.2721 (2)0.0473 (5)
C90.9830 (2)0.10795 (10)0.1577 (2)0.0408 (5)
C101.0982 (2)0.15798 (12)0.1632 (2)0.0526 (5)
H10A1.11600.17640.06760.063*
C111.1871 (2)0.18077 (13)0.3106 (3)0.0639 (6)
H11A1.26470.21410.31280.077*
C121.1626 (3)0.15511 (13)0.4522 (3)0.0685 (7)
H12A1.22320.17030.55070.082*
C131.0470 (3)0.10645 (13)0.4474 (3)0.0661 (7)
H13A1.02950.08880.54370.079*
C140.9564 (2)0.08325 (11)0.3022 (2)0.0524 (5)
H14A0.87750.05100.30120.063*
C150.9259 (2)0.10639 (11)0.1461 (2)0.0485 (5)
H15A0.88630.06840.22890.058*
H15B1.03080.10790.13190.058*
C160.8632 (2)0.18441 (12)0.2025 (3)0.0636 (6)
H16A0.88690.19740.30220.095*
H16B0.90370.22260.12220.095*
H16C0.75920.18310.21900.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0818 (11)0.0690 (10)0.0388 (8)0.0259 (9)0.0025 (7)0.0131 (7)
N10.0587 (11)0.0518 (10)0.0347 (8)0.0096 (9)0.0008 (7)0.0005 (7)
N20.0412 (9)0.0364 (8)0.0376 (8)0.0002 (7)0.0070 (7)0.0019 (7)
N30.0475 (10)0.0431 (9)0.0362 (8)0.0058 (8)0.0084 (7)0.0035 (7)
C10.0452 (11)0.0397 (10)0.0392 (10)0.0032 (9)0.0075 (8)0.0009 (8)
C20.0502 (13)0.0467 (12)0.0536 (12)0.0066 (10)0.0091 (10)0.0082 (10)
C30.0551 (13)0.0460 (12)0.0640 (14)0.0083 (10)0.0167 (11)0.0001 (10)
C40.0528 (13)0.0500 (12)0.0532 (12)0.0005 (10)0.0158 (10)0.0110 (10)
C50.0427 (11)0.0486 (11)0.0405 (11)0.0037 (9)0.0068 (8)0.0036 (9)
C60.0381 (10)0.0375 (10)0.0406 (10)0.0039 (8)0.0073 (8)0.0005 (8)
C70.0434 (11)0.0384 (10)0.0354 (9)0.0015 (9)0.0063 (8)0.0015 (8)
C80.0552 (13)0.0466 (11)0.0362 (10)0.0032 (10)0.0040 (9)0.0017 (9)
C90.0418 (11)0.0359 (10)0.0422 (10)0.0025 (9)0.0058 (8)0.0015 (8)
C100.0495 (12)0.0522 (12)0.0559 (13)0.0055 (10)0.0124 (10)0.0013 (10)
C110.0513 (14)0.0584 (14)0.0742 (16)0.0082 (11)0.0010 (11)0.0089 (12)
C120.0771 (17)0.0580 (14)0.0557 (14)0.0023 (13)0.0113 (12)0.0086 (11)
C130.0910 (18)0.0603 (14)0.0404 (12)0.0040 (14)0.0042 (11)0.0006 (10)
C140.0635 (14)0.0495 (12)0.0422 (11)0.0071 (11)0.0095 (10)0.0004 (9)
C150.0481 (12)0.0550 (12)0.0426 (11)0.0001 (10)0.0119 (9)0.0024 (9)
C160.0624 (15)0.0605 (14)0.0656 (14)0.0000 (12)0.0113 (11)0.0163 (11)
Geometric parameters (Å, º) top
O1—C81.227 (2)C7—C81.517 (2)
N1—C81.359 (2)C9—C101.384 (3)
N1—C11.398 (2)C9—C141.387 (3)
N1—H1A0.8600C10—C111.386 (3)
N2—C71.300 (2)C10—H10A0.9300
N2—N31.323 (2)C11—C121.361 (3)
N3—C91.425 (2)C11—H11A0.9300
N3—C151.472 (2)C12—C131.373 (3)
C1—C21.376 (3)C12—H12A0.9300
C1—C61.393 (2)C13—C141.380 (3)
C2—C31.383 (3)C13—H13A0.9300
C2—H2B0.9300C14—H14A0.9300
C3—C41.381 (3)C15—C161.504 (3)
C3—H3A0.9300C15—H15A0.9700
C4—C51.386 (3)C15—H15B0.9700
C4—H4A0.9300C16—H16A0.9600
C5—C61.382 (2)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C6—C71.460 (3)
C8—N1—C1112.74 (15)C10—C9—C14118.60 (18)
C8—N1—H1A123.6C10—C9—N3120.67 (17)
C1—N1—H1A123.6C14—C9—N3120.73 (17)
C7—N2—N3129.64 (15)C9—C10—C11120.3 (2)
N2—N3—C9114.13 (14)C9—C10—H10A119.9
N2—N3—C15124.76 (15)C11—C10—H10A119.9
C9—N3—C15120.49 (16)C12—C11—C10121.0 (2)
C2—C1—C6122.30 (17)C12—C11—H11A119.5
C2—C1—N1129.31 (17)C10—C11—H11A119.5
C6—C1—N1108.40 (16)C11—C12—C13119.0 (2)
C1—C2—C3117.40 (18)C11—C12—H12A120.5
C1—C2—H2B121.3C13—C12—H12A120.5
C3—C2—H2B121.3C12—C13—C14121.1 (2)
C4—C3—C2121.2 (2)C12—C13—H13A119.4
C4—C3—H3A119.4C14—C13—H13A119.4
C2—C3—H3A119.4C13—C14—C9120.0 (2)
C3—C4—C5120.91 (19)C13—C14—H14A120.0
C3—C4—H4A119.5C9—C14—H14A120.0
C5—C4—H4A119.5N3—C15—C16112.86 (17)
C6—C5—C4118.62 (18)N3—C15—H15A109.0
C6—C5—H5A120.7C16—C15—H15A109.0
C4—C5—H5A120.7N3—C15—H15B109.0
C5—C6—C1119.53 (18)C16—C15—H15B109.0
C5—C6—C7132.28 (16)H15A—C15—H15B107.8
C1—C6—C7108.18 (15)C15—C16—H16A109.5
N2—C7—C6117.53 (15)C15—C16—H16B109.5
N2—C7—C8137.30 (17)H16A—C16—H16B109.5
C6—C7—C8105.09 (15)C15—C16—H16C109.5
O1—C8—N1123.66 (17)H16A—C16—H16C109.5
O1—C8—C7130.73 (18)H16B—C16—H16C109.5
N1—C8—C7105.54 (16)
C7—N2—N3—C9176.71 (17)C1—N1—C8—O1177.0 (2)
C7—N2—N3—C1512.3 (3)C1—N1—C8—C70.2 (2)
C8—N1—C1—C2178.8 (2)N2—C7—C8—O11.0 (4)
C8—N1—C1—C61.2 (2)C6—C7—C8—O1175.5 (2)
C6—C1—C2—C30.9 (3)N2—C7—C8—N1178.0 (2)
N1—C1—C2—C3179.08 (19)C6—C7—C8—N11.4 (2)
C1—C2—C3—C40.5 (3)N2—N3—C9—C10173.23 (16)
C2—C3—C4—C51.3 (3)C15—N3—C9—C101.8 (3)
C3—C4—C5—C60.6 (3)N2—N3—C9—C146.5 (3)
C4—C5—C6—C10.7 (3)C15—N3—C9—C14177.88 (17)
C4—C5—C6—C7178.50 (19)C14—C9—C10—C111.9 (3)
C2—C1—C6—C51.6 (3)N3—C9—C10—C11177.84 (18)
N1—C1—C6—C5178.46 (17)C9—C10—C11—C120.5 (3)
C2—C1—C6—C7177.86 (17)C10—C11—C12—C130.5 (4)
N1—C1—C6—C72.1 (2)C11—C12—C13—C140.2 (4)
N3—N2—C7—C6174.94 (17)C12—C13—C14—C91.2 (3)
N3—N2—C7—C88.8 (4)C10—C9—C14—C132.2 (3)
C5—C6—C7—N21.2 (3)N3—C9—C14—C13177.49 (18)
C1—C6—C7—N2179.53 (16)N2—N3—C15—C16106.2 (2)
C5—C6—C7—C8178.5 (2)C9—N3—C15—C1683.3 (2)
C1—C6—C7—C82.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O10.972.212.916 (2)128
N1—H1A···O1i0.861.992.844 (2)172
Symmetry code: (i) x+1, y, z1.

Experimental details

Crystal data
Chemical formulaC16H15N3O
Mr265.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)9.463 (2), 17.303 (4), 8.5403 (18)
β (°) 104.427 (5)
V3)1354.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.18 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.971, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
7875, 2448, 1783
Rint0.032
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.116, 1.08
No. of reflections2448
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15A···O10.972.212.916 (2)128
N1—H1A···O1i0.861.992.844 (2)172
Symmetry code: (i) x+1, y, z1.
 

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

First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChaluvaraju, K. C. & Zaranappa (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 541–546.
First citationJamal, R. A., Ashiq, U., Yousuf, S. & Ain, Q. ul (2011). Acta Cryst. E67, o2166.  Web of Science CSD CrossRef IUCr Journals
First citationKhan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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