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

Wang, Q.; Zhang, Y.-J.; Yuan, M.-S.; Wang, J.-R.

doi:10.1107/S1600536811041316

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2929

doi:10.1107/S1600536811041316

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

Qi Wang,^a Yue-Jun Zhang,^a Mao-Sen Yuan ^a ^* and Jun-Ru Wang ^a

^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 ).

Experimental

Crystal data

C₁₆H₁₃NO
M_r = 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)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.125
S = 0.91
2168 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041316/xu5343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041316/xu5343Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041316/xu5343Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	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

C₁₆H₁₃NO	F(000) = 992
M_r = 235.27	D_x = 1.278 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1702 reflections
a = 22.215 (3) Å	θ = 2.8–2.8°
b = 8.6259 (13) Å	µ = 0.08 mm⁻¹
c = 15.062 (2) Å	T = 296 K
β = 122.097 (2)°	Block, colorless
V = 2445.1 (6) Å³	0.30 × 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 tube	R_int = 0.043
Graphite monochromator	θ_max = 25.1°, θ_min = 2.2°
ϕ and ω scans	h = −26→26
12693 measured reflections	k = −10→10
2168 independent reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0724P)² + 1.3094P] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
2168 reflections	Δρ_max = 0.18 e Å⁻³
165 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (8)

Crystal data top

C₁₆H₁₃NO	V = 2445.1 (6) Å³
M_r = 235.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.215 (3) Å	µ = 0.08 mm⁻¹
b = 8.6259 (13) Å	T = 296 K
c = 15.062 (2) Å	0.30 × 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 reflections	R_int = 0.043
2168 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 0.91	Δρ_max = 0.18 e Å⁻³
2168 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	1.03263 (7)	0.61802 (17)	0.39044 (11)	0.0561 (4)
N1	0.91715 (8)	0.61084 (19)	0.25220 (12)	0.0472 (4)
H1	0.9243	0.5627	0.2086	0.057*
C2	0.93295 (9)	0.7148 (2)	0.40348 (14)	0.0390 (4)
C3	0.85779 (9)	0.7304 (2)	0.31810 (14)	0.0403 (4)
C8	0.85065 (9)	0.6645 (2)	0.22834 (14)	0.0426 (5)
C10	0.92466 (9)	0.8083 (2)	0.55170 (13)	0.0414 (4)
C1	0.96899 (10)	0.6443 (2)	0.35275 (15)	0.0429 (4)
C4	0.79902 (9)	0.8025 (3)	0.30961 (15)	0.0515 (5)
H4	0.8025	0.8502	0.3675	0.062*
C9	0.96527 (9)	0.7516 (2)	0.50547 (14)	0.0411 (4)
C11	0.87633 (10)	0.7128 (2)	0.55719 (16)	0.0510 (5)
H11	0.8683	0.6128	0.5301	0.061*
C7	0.78716 (10)	0.6622 (3)	0.13293 (15)	0.0546 (5)
H7	0.7836	0.6156	0.0746	0.066*
C16	1.04401 (10)	0.7398 (3)	0.58193 (16)	0.0580 (6)
H16A	1.0643	0.6716	0.5543	0.087*
H16B	1.0530	0.6995	0.6473	0.087*
H16C	1.0651	0.8407	0.5931	0.087*
C5	0.73531 (10)	0.8022 (3)	0.21390 (17)	0.0608 (6)
H5	0.6959	0.8505	0.2079	0.073*
C15	0.93593 (12)	0.9552 (3)	0.59383 (17)	0.0605 (6)
H15	0.9691	1.0197	0.5929	0.073*
C12	0.84032 (12)	0.7657 (3)	0.60250 (17)	0.0608 (6)
H12	0.8085	0.7007	0.6066	0.073*
C13	0.85102 (13)	0.9134 (3)	0.64162 (18)	0.0689 (7)
H13	0.8260	0.9493	0.6710	0.083*
C6	0.72902 (11)	0.7317 (3)	0.12704 (17)	0.0618 (6)
H6	0.6853	0.7309	0.0640	0.074*
C14	0.89866 (14)	1.0071 (3)	0.6371 (2)	0.0746 (7)
H14	0.9060	1.1074	0.6636	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0469 (8)	0.0770 (10)	0.0553 (8)	0.0138 (7)	0.0345 (7)	0.0087 (7)
N1	0.0536 (10)	0.0554 (10)	0.0441 (9)	0.0045 (7)	0.0338 (8)	−0.0013 (7)
C2	0.0378 (9)	0.0435 (10)	0.0429 (10)	0.0001 (7)	0.0263 (8)	0.0033 (8)
C3	0.0385 (9)	0.0476 (11)	0.0402 (10)	−0.0018 (8)	0.0245 (8)	0.0020 (8)
C8	0.0464 (10)	0.0470 (11)	0.0430 (10)	−0.0040 (8)	0.0295 (9)	0.0011 (8)
C10	0.0411 (10)	0.0516 (11)	0.0322 (9)	0.0025 (8)	0.0199 (8)	0.0014 (8)
C1	0.0464 (11)	0.0473 (11)	0.0446 (11)	0.0029 (8)	0.0306 (9)	0.0068 (8)
C4	0.0421 (11)	0.0717 (14)	0.0455 (11)	0.0022 (9)	0.0265 (9)	−0.0023 (10)
C9	0.0404 (10)	0.0444 (10)	0.0420 (10)	−0.0006 (8)	0.0243 (8)	0.0037 (8)
C11	0.0524 (11)	0.0547 (12)	0.0561 (12)	−0.0002 (9)	0.0358 (10)	−0.0005 (9)
C7	0.0544 (12)	0.0707 (14)	0.0402 (11)	−0.0096 (10)	0.0261 (10)	−0.0037 (9)
C16	0.0412 (11)	0.0827 (15)	0.0466 (12)	0.0021 (10)	0.0210 (10)	0.0004 (10)
C5	0.0381 (11)	0.0907 (17)	0.0541 (13)	0.0038 (11)	0.0248 (10)	0.0030 (12)
C15	0.0648 (14)	0.0586 (13)	0.0652 (14)	−0.0076 (11)	0.0394 (12)	−0.0095 (11)
C12	0.0603 (13)	0.0780 (16)	0.0607 (14)	0.0080 (11)	0.0433 (12)	0.0105 (11)
C13	0.0740 (15)	0.0903 (18)	0.0589 (14)	0.0238 (14)	0.0464 (13)	0.0027 (13)
C6	0.0432 (11)	0.0912 (17)	0.0458 (12)	−0.0070 (11)	0.0201 (10)	0.0013 (11)
C14	0.0884 (18)	0.0674 (15)	0.0819 (18)	0.0027 (13)	0.0547 (16)	−0.0203 (13)

Geometric parameters (Å, º) top

O1—C1	1.233 (2)	C15—C14	1.373 (3)
N1—C1	1.360 (2)	C12—C13	1.370 (3)
N1—C8	1.401 (2)	C13—C14	1.362 (3)
C2—C9	1.343 (3)	N1—H1	0.8600
C2—C3	1.476 (2)	C4—H4	0.9300
C2—C1	1.498 (2)	C5—H5	0.9300
C3—C4	1.389 (2)	C6—H6	0.9300
C3—C8	1.396 (3)	C7—H7	0.9300
C8—C7	1.379 (3)	C11—H11	0.9300
C10—C15	1.379 (3)	C12—H12	0.9300
C10—C11	1.390 (3)	C13—H13	0.9300
C10—C9	1.485 (3)	C14—H14	0.9300
C4—C5	1.383 (3)	C15—H15	0.9300
C9—C16	1.502 (3)	C16—H16A	0.9600
C11—C12	1.376 (3)	C16—H16B	0.9600
C7—C6	1.383 (3)	C16—H16C	0.9600
C5—C6	1.381 (3)

C1—N1—C8	111.66 (15)	C13—C14—C15	120.7 (2)
C9—C2—C3	130.16 (16)	C1—N1—H1	123.8
C9—C2—C1	124.99 (16)	C8—N1—H1	123.8
C3—C2—C1	104.85 (15)	C3—C4—H4	120.0
C4—C3—C8	118.39 (17)	C5—C4—H4	120.0
C4—C3—C2	133.92 (17)	C4—C5—H5	119.6
C8—C3—C2	107.50 (15)	C6—C5—H5	119.6
C7—C8—C3	122.84 (17)	C5—C6—H6	119.6
C7—C8—N1	128.17 (17)	C7—C6—H6	119.6
C3—C8—N1	108.93 (15)	C6—C7—H7	120.5
C15—C10—C11	118.31 (18)	C8—C7—H7	120.5
C15—C10—C9	120.74 (17)	C10—C11—H11	119.6
C11—C10—C9	120.91 (17)	C12—C11—H11	119.6
O1—C1—N1	123.98 (17)	C11—C12—H12	119.6
O1—C1—C2	129.26 (17)	C13—C12—H12	120.2
N1—C1—C2	106.76 (15)	C12—C13—H13	120.2
C5—C4—C3	119.10 (18)	C14—C13—H13	120.2
C2—C9—C10	121.69 (16)	C13—C14—H14	120.2
C2—C9—C16	123.92 (17)	C15—C14—H14	120.2
C10—C9—C16	114.40 (16)	C10—C15—H15	120.2
C12—C11—C10	120.2 (2)	C14—C15—H15	120.2
C8—C7—C6	117.63 (19)	C9—C16—H16A	109.4
C6—C5—C4	121.4 (2)	C9—C16—H16B	109.4
C14—C15—C10	120.7 (2)	C9—C16—H16C	109.4
C13—C12—C11	120.5 (2)	H16A—C16—H16B	109.0
C14—C13—C12	119.5 (2)	H16A—C16—H16C	109.0
C5—C6—C7	120.6 (2)	H16B—C16—H16C	109.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.21	2.9002 (19)	137

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO
M_r	235.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	22.215 (3), 8.6259 (13), 15.062 (2)
β (°)	122.097 (2)
V (Å³)	2445.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12693, 2168, 1599
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.125, 0.91
No. of reflections	2168
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.21	2.9002 (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

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