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ISSN: 2056-9890

3-[(E)-Benzyl­­idene]indolin-2-one

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 May 2012; accepted 30 May 2012; online 13 June 2012)

In the title indolin-2-one derivative, C15H11NO, the phenyl ring and the oxoindoline fused-ring system (r.m.s. deviation = 0.011 Å) are aligned at 48.52 (6)°. In the crystal, inversion-related mol­ecules form an N—H⋯O hydrogen-bonded dimer via an eight-membered {⋯HNCO}2 synthon. The dimeric aggregates are linked into a three-dimensional architecture via C—H⋯O and ππ inter­actions between the five- and six-membered rings of the fused ring system, with an inter-centroid distance of 3.4538 (8) Å.

Related literature

For the structure of the Z-isomer of the title compound, see: Milanesio et al. (2000[Milanesio, M., Viterbo, D., Albini, A., Fasani, E., Bianchi, R. & Barzaghi, M. (2000). J. Org. Chem. 65, 3416-3425.]). For background to related thia­zoles, see: Badahdaha et al. (2009[Badahdaha, K. O., Asiri, A. M. & Ng, S. W. (2009). Acta Cryst. E65, o759.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11NO

  • Mr = 221.25

  • Monoclinic, P 21 /n

  • a = 3.9796 (3) Å

  • b = 22.2266 (19) Å

  • c = 12.2484 (10) Å

  • β = 95.027 (1)°

  • V = 1079.24 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • 6831 measured reflections

  • 2460 independent reflections

  • 2153 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.03

  • 2460 reflections

  • 158 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.87 (1) 1.98 (1) 2.846 (1) 172 (2)
C13—H13⋯O1ii 0.95 2.57 3.2535 (15) 129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title compound (I) was isolated as a side-product in the attempted synthesis of thiazole derivatives (Badahdaha et al., 2009) of interest owing to putative biological activity. The indolin-2-onyl fused-ring in (I), Fig. 1, is planar with the r.m.s. deviation being 0.011 Å; the O1 and C9 atoms lie -0.016 (1) and 0.089 (1) Å out of the plane, respectively. The phenyl group is twisted out of this plane, forming a dihedral angle of 48.52 (6)°. The conformation about the C7C9 bond [1.3439 (16) Å] is E; the structure of the Z-isomer is known (Milanesio et al., 2000).

In the crystal packing, inversion related molecules are connected into a dimer via N—H···O hydrogen bonds, Fig. 2 and Table 1. Molecules are linked into undulating layers in the bc plane via C—H···O interactions, Table 1, and are linked along the a axis via ππ interactions occurring between the five- and six-membered rings of the indolin-2-onyl fused ring system [ring centroid(N1,C1, C6–C7)···centroid(C1–C6)i = 3.4538 (8) Å, angle of inclination = 1.15 (6)° for i: -1 + x, y, z], Fig. 3.

Related literature top

For the structure of the Z-isomer of the title compound, see: Milanesio et al. (2000). For background to related thiazoles, see: Badahdaha et al. (2009).

Experimental top

The title compound, an unexpected product, was isolated as a side-product from a reaction between 2-(4-nitrobenzylidene)hydrazinecarbothioamide, triethylamine and N-phenyl-2-oxopropanehydrazonoyl chloride in ethanol solution; m.p. 512 K.

Refinement top

Carbon-bound H atoms were placed in calculated positions [C—H = 0.95 Å, Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The N-bound H atom was located in a difference Fourier map and was refined with a distance restraint of N—H = 0.86 (1) Å; the Uiso value was refined.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

A view of the centrosymmetric dimer in (I) mediated by N—H···O hydrogen bonds shown as blue dashed lines.

A view in projection down the a axis of the unit-cell contents of (I), the direction of the stacking of supramolecular layers. The N—H···O, C—H···O and ππ interactions are shown as blue, orange and purple dashed lines, respectively.
3-[(E)-Benzylidene]indolin-2-one top
Crystal data top
C15H11NOF(000) = 464
Mr = 221.25Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3166 reflections
a = 3.9796 (3) Åθ = 2.5–28.3°
b = 22.2266 (19) ŵ = 0.09 mm1
c = 12.2484 (10) ÅT = 100 K
β = 95.027 (1)°Prism, orange
V = 1079.24 (15) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
2153 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω scansh = 35
6831 measured reflectionsk = 2828
2460 independent reflectionsl = 1515
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2809P]
where P = (Fo2 + 2Fc2)/3
2460 reflections(Δ/σ)max = 0.001
158 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.26 e Å3
Crystal data top
C15H11NOV = 1079.24 (15) Å3
Mr = 221.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.9796 (3) ŵ = 0.09 mm1
b = 22.2266 (19) ÅT = 100 K
c = 12.2484 (10) Å0.30 × 0.20 × 0.10 mm
β = 95.027 (1)°
Data collection top
Bruker SMART APEX
diffractometer
2153 reflections with I > 2σ(I)
6831 measured reflectionsRint = 0.023
2460 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.27 e Å3
2460 reflectionsΔρmin = 0.26 e Å3
158 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5372 (2)0.58258 (4)0.53379 (7)0.0236 (2)
N10.7366 (3)0.52725 (4)0.39388 (8)0.0183 (2)
H1N0.668 (4)0.4920 (5)0.4133 (12)0.032 (4)*
C10.8893 (3)0.53924 (5)0.29780 (9)0.0167 (2)
C20.9905 (3)0.49792 (5)0.22291 (10)0.0194 (3)
H20.95560.45600.23210.023*
C31.1456 (3)0.52014 (6)0.13341 (10)0.0211 (3)
H31.21940.49290.08080.025*
C41.1938 (3)0.58149 (6)0.11990 (10)0.0207 (3)
H41.29870.59560.05800.025*
C51.0897 (3)0.62256 (5)0.19619 (9)0.0184 (2)
H51.12410.66450.18660.022*
C60.9350 (3)0.60162 (5)0.28646 (9)0.0159 (2)
C70.8052 (3)0.62991 (5)0.38267 (9)0.0167 (2)
C80.6761 (3)0.57888 (5)0.44818 (9)0.0180 (3)
C90.7925 (3)0.68631 (5)0.42166 (9)0.0176 (2)
H90.71750.69010.49290.021*
C100.8793 (3)0.74284 (5)0.36866 (9)0.0167 (2)
C110.7759 (3)0.75418 (5)0.25856 (9)0.0179 (2)
H110.65400.72430.21610.021*
C120.8496 (3)0.80862 (5)0.21070 (10)0.0194 (3)
H120.77560.81600.13600.023*
C131.0311 (3)0.85235 (5)0.27155 (10)0.0199 (3)
H131.08620.88920.23820.024*
C141.1317 (3)0.84202 (5)0.38124 (10)0.0203 (3)
H141.25570.87190.42310.024*
C151.0516 (3)0.78813 (5)0.43000 (9)0.0191 (3)
H151.11450.78190.50580.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0347 (5)0.0183 (4)0.0189 (4)0.0028 (4)0.0088 (4)0.0011 (3)
N10.0234 (5)0.0130 (5)0.0186 (5)0.0015 (4)0.0024 (4)0.0020 (4)
C10.0150 (5)0.0178 (6)0.0167 (5)0.0001 (4)0.0015 (4)0.0013 (4)
C20.0178 (5)0.0177 (6)0.0222 (6)0.0018 (4)0.0010 (4)0.0010 (4)
C30.0191 (5)0.0246 (6)0.0193 (6)0.0039 (5)0.0001 (4)0.0044 (5)
C40.0179 (5)0.0265 (6)0.0179 (6)0.0008 (5)0.0019 (4)0.0008 (5)
C50.0164 (5)0.0190 (6)0.0196 (6)0.0018 (4)0.0008 (4)0.0016 (4)
C60.0146 (5)0.0163 (5)0.0163 (5)0.0004 (4)0.0017 (4)0.0002 (4)
C70.0177 (5)0.0170 (6)0.0153 (5)0.0017 (4)0.0004 (4)0.0025 (4)
C80.0209 (6)0.0157 (6)0.0171 (5)0.0015 (4)0.0006 (4)0.0016 (4)
C90.0200 (5)0.0180 (6)0.0148 (5)0.0005 (4)0.0020 (4)0.0006 (4)
C100.0172 (5)0.0146 (5)0.0188 (5)0.0008 (4)0.0046 (4)0.0005 (4)
C110.0183 (5)0.0164 (5)0.0189 (6)0.0009 (4)0.0018 (4)0.0009 (4)
C120.0200 (6)0.0202 (6)0.0181 (5)0.0015 (4)0.0032 (4)0.0022 (4)
C130.0196 (6)0.0151 (5)0.0255 (6)0.0002 (4)0.0058 (4)0.0028 (4)
C140.0214 (6)0.0152 (5)0.0244 (6)0.0020 (4)0.0025 (4)0.0038 (4)
C150.0224 (6)0.0182 (6)0.0167 (5)0.0015 (4)0.0018 (4)0.0013 (4)
Geometric parameters (Å, º) top
O1—C81.2302 (14)C7—C91.3439 (16)
N1—C81.3585 (15)C7—C81.5054 (15)
N1—C11.3968 (14)C9—C101.4693 (15)
N1—H1N0.87 (1)C9—H90.9500
C1—C21.3825 (16)C10—C111.3978 (16)
C1—C61.4068 (16)C10—C151.3993 (16)
C2—C31.3946 (17)C11—C121.3871 (16)
C2—H20.9500C11—H110.9500
C3—C41.3890 (18)C12—C131.3884 (17)
C3—H30.9500C12—H120.9500
C4—C51.3950 (16)C13—C141.3871 (17)
C4—H40.9500C13—H130.9500
C5—C61.3919 (15)C14—C151.3881 (16)
C5—H50.9500C14—H140.9500
C6—C71.4689 (15)C15—H150.9500
C8—N1—C1111.10 (9)O1—C8—N1125.86 (10)
C8—N1—H1N123.7 (11)O1—C8—C7127.13 (10)
C1—N1—H1N124.9 (11)N1—C8—C7106.99 (10)
C2—C1—N1127.28 (11)C7—C9—C10128.54 (10)
C2—C1—C6122.79 (11)C7—C9—H9115.7
N1—C1—C6109.93 (10)C10—C9—H9115.7
C1—C2—C3117.44 (11)C11—C10—C15118.50 (10)
C1—C2—H2121.3C11—C10—C9121.32 (10)
C3—C2—H2121.3C15—C10—C9120.08 (10)
C4—C3—C2121.10 (11)C12—C11—C10120.65 (11)
C4—C3—H3119.4C12—C11—H11119.7
C2—C3—H3119.4C10—C11—H11119.7
C3—C4—C5120.69 (11)C13—C12—C11120.20 (11)
C3—C4—H4119.7C13—C12—H12119.9
C5—C4—H4119.7C11—C12—H12119.9
C4—C5—C6119.42 (11)C14—C13—C12119.78 (11)
C4—C5—H5120.3C14—C13—H13120.1
C6—C5—H5120.3C12—C13—H13120.1
C5—C6—C1118.55 (10)C13—C14—C15120.12 (11)
C5—C6—C7134.85 (11)C13—C14—H14119.9
C1—C6—C7106.56 (10)C15—C14—H14119.9
C9—C7—C6135.33 (11)C14—C15—C10120.67 (11)
C9—C7—C8119.22 (10)C14—C15—H15119.7
C6—C7—C8105.40 (9)C10—C15—H15119.7
C8—N1—C1—C2179.20 (11)C1—N1—C8—C70.80 (13)
C8—N1—C1—C60.09 (13)C9—C7—C8—O14.54 (18)
N1—C1—C2—C3178.59 (11)C6—C7—C8—O1177.79 (11)
C6—C1—C2—C30.41 (16)C9—C7—C8—N1176.49 (10)
C1—C2—C3—C40.48 (17)C6—C7—C8—N11.18 (12)
C2—C3—C4—C50.40 (17)C6—C7—C9—C108.2 (2)
C3—C4—C5—C60.23 (17)C8—C7—C9—C10175.00 (11)
C4—C5—C6—C10.15 (16)C7—C9—C10—C1143.93 (18)
C4—C5—C6—C7177.75 (11)C7—C9—C10—C15139.89 (13)
C2—C1—C6—C50.25 (16)C15—C10—C11—C121.47 (17)
N1—C1—C6—C5178.91 (10)C9—C10—C11—C12177.71 (10)
C2—C1—C6—C7178.47 (10)C10—C11—C12—C130.77 (17)
N1—C1—C6—C70.68 (12)C11—C12—C13—C141.57 (17)
C5—C6—C7—C91.8 (2)C12—C13—C14—C150.09 (18)
C1—C6—C7—C9175.99 (13)C13—C14—C15—C102.20 (18)
C5—C6—C7—C8178.91 (12)C11—C10—C15—C142.95 (17)
C1—C6—C7—C81.11 (11)C9—C10—C15—C14179.24 (10)
C1—N1—C8—O1178.19 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.87 (1)1.98 (1)2.846 (1)172 (2)
C13—H13···O1ii0.952.573.2535 (15)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H11NO
Mr221.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)3.9796 (3), 22.2266 (19), 12.2484 (10)
β (°) 95.027 (1)
V3)1079.24 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6831, 2460, 2153
Rint0.023
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 1.02
No. of reflections2460
No. of parameters158
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.87 (1)1.983 (9)2.846 (1)172.3 (15)
C13—H13···O1ii0.952.573.2535 (15)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+3/2, z1/2.
 

Footnotes

Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

First citationBadahdaha, K. O., Asiri, A. M. & Ng, S. W. (2009). Acta Cryst. E65, o759.  Web of Science CSD CrossRef IUCr Journals
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationMilanesio, M., Viterbo, D., Albini, A., Fasani, E., Bianchi, R. & Barzaghi, M. (2000). J. Org. Chem. 65, 3416–3425.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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