organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(E)-3-(1-Phenyl­ethyl­­idene)indolin-2-one

aCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
*Correspondence e-mail: yuanms@nwsuaf.edu.cn

(Received 28 September 2011; accepted 7 October 2011; online 12 October 2011)

In the title mol­ecule, C16H13NO, the indoline-2-one ring system is nearly planar [maximum atomic deviation = 0.082 (2) Å] and is oriented at a dihedral angle of 66.60 (12)° with respect to the phenyl ring. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into supra­molecular dimers.

Related literature

For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Stephen et al. (1996[Stephen, C. T., Gary, H. G. & Robert, R. H. (1996). J. Pham. Biomed. Anal. 14, 825-830.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13NO

  • Mr = 235.27

  • Monoclinic, C 2/c

  • a = 22.215 (3) Å

  • b = 8.6259 (13) Å

  • c = 15.062 (2) Å

  • β = 122.097 (2)°

  • V = 2445.1 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • 12693 measured reflections

  • 2168 independent reflections

  • 1599 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.125

  • S = 0.91

  • 2168 reflections

  • 165 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 2.21 2.9002 (19) 137
Symmetry code: (i) [-x+2, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Indoline-2-one and its derivatives have been used as precursors to synthesis pharmaceuticals (Stephen et al., 1996). Rooting from its perfect conformation, indoline-2-one were tried to built electro-optic compounds recently. In the course of synthesis, we obtained the intermediate compound C16H13NO, (I), and the synthesis and structure are reported here.

In the title molecule, the indole system lies approximately in a plane and the maximum displacement from the least-square plane defined by all the 9 atoms of the indole framework is 0.082 (2) Å for C2 atom. The interplanar angle between the benzene plane and that of the indole moiety is 66.60 (12)°.

The title compound has three substituent ring systems, an indoline-2-one ring and two benzene rings which are arranged in a propeller-like fashion around the central atom C9 (Fig. 1). The interplanar dihedral angle between the two benzene rings defined by C10–C15 and C16–C21 is 73.41 (14)°. The interplanar angles between these benzene planes and that of the indoline moiety are 76.61 (12)° and 67.68 (12)°, respectively.

In the crystal structure there is an intermolecular N—H···O hydrogen-bonding interaction (Table 1) linking the molecules into dimers (Fig. 2).

Related literature top

For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Stephen et al. (1996).

Experimental top

Indolin-2-one (0.50 g, 3.76 mmol) was dissolved in THF (20 mL) and KOH (0.80 g, 14.3 mmol) was slowly added. After heating the stirred mixture at reflux temperature for 30 min, a solution of acetophenone (1.00 g, 8.33 mmol) in THF was slowly added and the refluxing continued for 2 h. The mixture was then cooled to 333 K and poured into water (200 mL) and was extracted with chloroform and dried over Na2SO4. After removing the solvent, the crude product was purified by column chromatography on silica gel, affording the title compound (yield: 0.15 g, 17%). The compound was then dissolved in THF, and yellow crystals were formed on slow evaporation at room temperature over one week.

Refinement top

All H atoms were placed in geometrically calculated positions with C—H = 0.93 (aromatic), 0.96 (methyl) and N—H = 0.86 Å, and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of (I) viewed along the c axis, with hydrogen bonds shown as dashed lines.
(E)-3-(1-Phenylethylidene)indolin-2-one top
Crystal data top
C16H13NOF(000) = 992
Mr = 235.27Dx = 1.278 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1702 reflections
a = 22.215 (3) Åθ = 2.8–2.8°
b = 8.6259 (13) ŵ = 0.08 mm1
c = 15.062 (2) ÅT = 296 K
β = 122.097 (2)°Block, colorless
V = 2445.1 (6) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1599 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 25.1°, θmin = 2.2°
ϕ and ω scansh = 2626
12693 measured reflectionsk = 1010
2168 independent reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0724P)2 + 1.3094P]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
2168 reflectionsΔρmax = 0.18 e Å3
165 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (8)
Crystal data top
C16H13NOV = 2445.1 (6) Å3
Mr = 235.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.215 (3) ŵ = 0.08 mm1
b = 8.6259 (13) ÅT = 296 K
c = 15.062 (2) Å0.30 × 0.20 × 0.20 mm
β = 122.097 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1599 reflections with I > 2σ(I)
12693 measured reflectionsRint = 0.043
2168 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 0.91Δρmax = 0.18 e Å3
2168 reflectionsΔρmin = 0.18 e Å3
165 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O11.03263 (7)0.61802 (17)0.39044 (11)0.0561 (4)
N10.91715 (8)0.61084 (19)0.25220 (12)0.0472 (4)
H10.92430.56270.20860.057*
C20.93295 (9)0.7148 (2)0.40348 (14)0.0390 (4)
C30.85779 (9)0.7304 (2)0.31810 (14)0.0403 (4)
C80.85065 (9)0.6645 (2)0.22834 (14)0.0426 (5)
C100.92466 (9)0.8083 (2)0.55170 (13)0.0414 (4)
C10.96899 (10)0.6443 (2)0.35275 (15)0.0429 (4)
C40.79902 (9)0.8025 (3)0.30961 (15)0.0515 (5)
H40.80250.85020.36750.062*
C90.96527 (9)0.7516 (2)0.50547 (14)0.0411 (4)
C110.87633 (10)0.7128 (2)0.55719 (16)0.0510 (5)
H110.86830.61280.53010.061*
C70.78716 (10)0.6622 (3)0.13293 (15)0.0546 (5)
H70.78360.61560.07460.066*
C161.04401 (10)0.7398 (3)0.58193 (16)0.0580 (6)
H16A1.06430.67160.55430.087*
H16B1.05300.69950.64730.087*
H16C1.06510.84070.59310.087*
C50.73531 (10)0.8022 (3)0.21390 (17)0.0608 (6)
H50.69590.85050.20790.073*
C150.93593 (12)0.9552 (3)0.59383 (17)0.0605 (6)
H150.96911.01970.59290.073*
C120.84032 (12)0.7657 (3)0.60250 (17)0.0608 (6)
H120.80850.70070.60660.073*
C130.85102 (13)0.9134 (3)0.64162 (18)0.0689 (7)
H130.82600.94930.67100.083*
C60.72902 (11)0.7317 (3)0.12704 (17)0.0618 (6)
H60.68530.73090.06400.074*
C140.89866 (14)1.0071 (3)0.6371 (2)0.0746 (7)
H140.90601.10740.66360.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0469 (8)0.0770 (10)0.0553 (8)0.0138 (7)0.0345 (7)0.0087 (7)
N10.0536 (10)0.0554 (10)0.0441 (9)0.0045 (7)0.0338 (8)0.0013 (7)
C20.0378 (9)0.0435 (10)0.0429 (10)0.0001 (7)0.0263 (8)0.0033 (8)
C30.0385 (9)0.0476 (11)0.0402 (10)0.0018 (8)0.0245 (8)0.0020 (8)
C80.0464 (10)0.0470 (11)0.0430 (10)0.0040 (8)0.0295 (9)0.0011 (8)
C100.0411 (10)0.0516 (11)0.0322 (9)0.0025 (8)0.0199 (8)0.0014 (8)
C10.0464 (11)0.0473 (11)0.0446 (11)0.0029 (8)0.0306 (9)0.0068 (8)
C40.0421 (11)0.0717 (14)0.0455 (11)0.0022 (9)0.0265 (9)0.0023 (10)
C90.0404 (10)0.0444 (10)0.0420 (10)0.0006 (8)0.0243 (8)0.0037 (8)
C110.0524 (11)0.0547 (12)0.0561 (12)0.0002 (9)0.0358 (10)0.0005 (9)
C70.0544 (12)0.0707 (14)0.0402 (11)0.0096 (10)0.0261 (10)0.0037 (9)
C160.0412 (11)0.0827 (15)0.0466 (12)0.0021 (10)0.0210 (10)0.0004 (10)
C50.0381 (11)0.0907 (17)0.0541 (13)0.0038 (11)0.0248 (10)0.0030 (12)
C150.0648 (14)0.0586 (13)0.0652 (14)0.0076 (11)0.0394 (12)0.0095 (11)
C120.0603 (13)0.0780 (16)0.0607 (14)0.0080 (11)0.0433 (12)0.0105 (11)
C130.0740 (15)0.0903 (18)0.0589 (14)0.0238 (14)0.0464 (13)0.0027 (13)
C60.0432 (11)0.0912 (17)0.0458 (12)0.0070 (11)0.0201 (10)0.0013 (11)
C140.0884 (18)0.0674 (15)0.0819 (18)0.0027 (13)0.0547 (16)0.0203 (13)
Geometric parameters (Å, º) top
O1—C11.233 (2)C15—C141.373 (3)
N1—C11.360 (2)C12—C131.370 (3)
N1—C81.401 (2)C13—C141.362 (3)
C2—C91.343 (3)N1—H10.8600
C2—C31.476 (2)C4—H40.9300
C2—C11.498 (2)C5—H50.9300
C3—C41.389 (2)C6—H60.9300
C3—C81.396 (3)C7—H70.9300
C8—C71.379 (3)C11—H110.9300
C10—C151.379 (3)C12—H120.9300
C10—C111.390 (3)C13—H130.9300
C10—C91.485 (3)C14—H140.9300
C4—C51.383 (3)C15—H150.9300
C9—C161.502 (3)C16—H16A0.9600
C11—C121.376 (3)C16—H16B0.9600
C7—C61.383 (3)C16—H16C0.9600
C5—C61.381 (3)
C1—N1—C8111.66 (15)C13—C14—C15120.7 (2)
C9—C2—C3130.16 (16)C1—N1—H1123.8
C9—C2—C1124.99 (16)C8—N1—H1123.8
C3—C2—C1104.85 (15)C3—C4—H4120.0
C4—C3—C8118.39 (17)C5—C4—H4120.0
C4—C3—C2133.92 (17)C4—C5—H5119.6
C8—C3—C2107.50 (15)C6—C5—H5119.6
C7—C8—C3122.84 (17)C5—C6—H6119.6
C7—C8—N1128.17 (17)C7—C6—H6119.6
C3—C8—N1108.93 (15)C6—C7—H7120.5
C15—C10—C11118.31 (18)C8—C7—H7120.5
C15—C10—C9120.74 (17)C10—C11—H11119.6
C11—C10—C9120.91 (17)C12—C11—H11119.6
O1—C1—N1123.98 (17)C11—C12—H12119.6
O1—C1—C2129.26 (17)C13—C12—H12120.2
N1—C1—C2106.76 (15)C12—C13—H13120.2
C5—C4—C3119.10 (18)C14—C13—H13120.2
C2—C9—C10121.69 (16)C13—C14—H14120.2
C2—C9—C16123.92 (17)C15—C14—H14120.2
C10—C9—C16114.40 (16)C10—C15—H15120.2
C12—C11—C10120.2 (2)C14—C15—H15120.2
C8—C7—C6117.63 (19)C9—C16—H16A109.4
C6—C5—C4121.4 (2)C9—C16—H16B109.4
C14—C15—C10120.7 (2)C9—C16—H16C109.4
C13—C12—C11120.5 (2)H16A—C16—H16B109.0
C14—C13—C12119.5 (2)H16A—C16—H16C109.0
C5—C6—C7120.6 (2)H16B—C16—H16C109.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.212.9002 (19)137
Symmetry code: (i) x+2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H13NO
Mr235.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)22.215 (3), 8.6259 (13), 15.062 (2)
β (°) 122.097 (2)
V3)2445.1 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12693, 2168, 1599
Rint0.043
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.125, 0.91
No. of reflections2168
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.212.9002 (19)137
Symmetry code: (i) x+2, y, z+1/2.
 

Acknowledgements

Financial support from the PhD Programs Foundation of the Ministry of Education of China (No. 20090204120033) is gratefully acknowledged.

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStephen, C. T., Gary, H. G. & Robert, R. H. (1996). J. Pham. Biomed. Anal. 14, 825–830.  Google Scholar

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ISSN: 2056-9890
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