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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2232–o2233.
Published online 2010 August 11. doi:  10.1107/S1600536810030874
PMCID: PMC3007968

(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyrid­yl)ethyl­idene]indolin-2-one

Abstract

The title compound, C23H16N2O3, exists in a Z configuration with respect to the acyclic C=C bond. The pyridine and phenyl rings are oriented at dihedral angles of 72.97 (4) and 45.05 (4)°, respectively, with respect to the almost planar indoline ring system [maximum deviation 0.080 (1) Å]. The pyridine and phenyl rings are oriented almost perpendicular to each other [dihedral angle 88.93 (5)°]. In the crystal, mol­ecules are inter­connected into a three-dimensional framework via inter­molecular C—H(...)O and C—H(...)N hydrogen bonds and weak π–π inter­actions [centroid–centroid distance = 3.681 (1) Å].

Related literature

For general background and applications of indoline compounds, see: Aanandhi et al. (2008 [triangle]); Lawrence et al. (2008 [triangle]); Muthukumar et al. (2008 [triangle]); Wang et al. (2005 [triangle]); Xue et al. (2000 [triangle]); Yu et al. (2010 [triangle]); Zhang & Panek (2009 [triangle]); Zhang et al. (2004a [triangle],b [triangle]). For related indoline structures, see: Fun et al. (2010a [triangle],b [triangle]); Usman et al. (2001 [triangle],2002 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-66-o2232-scheme1.jpg

Experimental

Crystal data

  • C23H16N2O3
  • M r = 368.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2232-efi1.jpg
  • a = 7.9259 (19) Å
  • b = 9.086 (2) Å
  • c = 12.431 (3) Å
  • α = 84.804 (7)°
  • β = 87.064 (7)°
  • γ = 76.843 (6)°
  • V = 867.7 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.23 × 0.19 × 0.16 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.978, T max = 0.985
  • 19600 measured reflections
  • 5017 independent reflections
  • 4237 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.116
  • S = 1.04
  • 5017 reflections
  • 254 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030874/ci5150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030874/ci5150Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the Ministry of Science and Technology of China on the Austria-China Cooperation project (2007DFA41590) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Indole derivatives have a variety of biological activities and are synthetic precursors for many naturally occuring alkaloids (Aanandhi et al., 2008; Muthukumar et al., 2008; Lawrence et al., 2008). The C3 carbonyl group is the common reactive group in isatin (1H-indole-2,3-dione) for further derivation in either thermal reactions or photoreactions (Zhang et al., 2004b; 2009). Photoreactions of N-acetylisatin and alkenes or alkynes have provided a facile way to build various heterocyclic frameworks containing indole moieties (Wang et al., 2005; Zhang et al., 2004a; Xue et al., 2000). Azaaryl substituted acetylenes have been used to react with carbonyl groups which may lead to formation of various heterocyclic polycycles (Yu et al., 2010). In view of the importance of the title compound, (I), as a typical quinone methide product in photoreaction between carbonyl and acetylenes, this paper reports its crystal structure.

The title molecule exists in a cis configuration with respect to the acyclic C8═C9 bond [C8═C9 = 1.3510 (14) Å]. The indoline ring system (C1-C8/N1) is essentially planar, with a maximum deviation of 0.080 (1) Å at atom C7. The phenyl ring (C16-C21) and pyridine ring (C11-C15/N2) are almost perpendicular to each other, as indicated by the interplanar angle of 88.93 (5)° between them. These two rings form dihedral angles of 72.97 (4) and 45.05 (4)° with the indoline ring system, respectively. The bond lengths and angles are consistent to those observed in closely related indole structures (Fun et al., 2010a,b; Usman et al., 2001,2002).

In the crystal packing, intermolecular C12—H12A···O3, C14—H14A···O2 and C20—H20A···N2 hydrogen bonds (Table 1) interconnect adjacent molecules into a three-dimensional framework (Fig. 2). Weak intermolecular π-π interactions involving the pyrrolidine (C1/C6-C8/N1, centroid Cg1) and phenyl (C1-C6, centroid Cg2) rings [Cg1···Cg2* = 3.6812 (11) Å; symmetry code: (*) 2-x, 2-y, -z] further stabilize the crystal packing.

Experimental

The title compound was obtained in the reaction between N-acetylisatin and 3-pyridinyl phenyl acetylene under photo-irradiation with light of wavelength > 400 nm. The compound was purified by flash column chromatography with ethyl acetate-petroleum ether (1:5) as eluents. X-ray quality single crystals of (I) were obtained by slow evaporation of a acetone-petroleum ether (1:2) solution (m.p. 568–571 K).

Refinement

H atoms were placed in their calculated positions, with C—H = 0.93 or 0.96 Å, and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). The rotating group model was applied to the methyl group.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 50 % probability level.
Fig. 2.
The crystal structure of the title compound, viewed along the b axis, showing a three-dimensional framework. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C23H16N2O3Z = 2
Mr = 368.38F(000) = 384
Triclinic, P1Dx = 1.410 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9259 (19) ÅCell parameters from 7658 reflections
b = 9.086 (2) Åθ = 2.3–32.1°
c = 12.431 (3) ŵ = 0.10 mm1
α = 84.804 (7)°T = 100 K
β = 87.064 (7)°Block, yellow
γ = 76.843 (6)°0.23 × 0.19 × 0.16 mm
V = 867.7 (4) Å3

Data collection

Bruker APEXII DUO CCD area-detector diffractometer5017 independent reflections
Radiation source: fine-focus sealed tube4237 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −11→11
Tmin = 0.978, Tmax = 0.985k = −12→12
19600 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0637P)2 + 0.2808P] where P = (Fo2 + 2Fc2)/3
5017 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
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)

xyzUiso*/Ueq
O10.74656 (11)0.64928 (9)0.08150 (6)0.01988 (17)
O20.94194 (10)0.51863 (9)0.29214 (7)0.01842 (17)
O30.61891 (12)0.98853 (10)−0.16758 (7)0.02319 (19)
N10.72823 (12)0.89175 (10)−0.00538 (7)0.01472 (18)
N20.48355 (13)0.38455 (11)0.38814 (8)0.0208 (2)
C10.80969 (13)1.00838 (12)0.13505 (8)0.01429 (19)
C20.86200 (14)1.12405 (12)0.18121 (9)0.0175 (2)
H2A0.89581.11100.25260.021*
C30.86325 (15)1.25906 (13)0.11949 (10)0.0200 (2)
H3A0.89611.33750.15010.024*
C40.81564 (16)1.27772 (13)0.01211 (10)0.0220 (2)
H4A0.81601.3692−0.02790.026*
C50.76744 (15)1.16211 (13)−0.03661 (9)0.0199 (2)
H5A0.73791.1742−0.10880.024*
C60.76495 (13)1.02835 (12)0.02614 (8)0.0149 (2)
C70.75826 (13)0.77964 (12)0.08245 (8)0.01466 (19)
C80.79925 (13)0.85485 (11)0.17647 (8)0.01383 (19)
C90.80773 (13)0.78123 (11)0.27615 (8)0.01317 (19)
C100.80593 (13)0.61403 (11)0.29125 (8)0.01361 (19)
C110.63598 (13)0.57473 (11)0.31789 (8)0.01344 (19)
C120.47958 (14)0.67902 (12)0.29924 (9)0.0165 (2)
H12A0.47840.77760.27110.020*
C130.32642 (14)0.63324 (13)0.32333 (9)0.0187 (2)
H13A0.22010.69960.31040.022*
C140.33486 (14)0.48613 (13)0.36719 (9)0.0192 (2)
H14A0.23120.45590.38310.023*
C150.63067 (14)0.42976 (12)0.36275 (9)0.0170 (2)
H15A0.73520.36060.37570.020*
C160.80906 (13)0.84819 (11)0.38002 (8)0.01300 (19)
C170.90394 (13)0.76491 (12)0.46632 (8)0.0148 (2)
H17A0.97280.66910.45680.018*
C180.89565 (14)0.82461 (12)0.56573 (9)0.0164 (2)
H18A0.95910.76880.62260.020*
C190.79292 (14)0.96743 (12)0.58082 (9)0.0173 (2)
H19A0.78941.00790.64720.021*
C200.69532 (14)1.04977 (12)0.49644 (9)0.0169 (2)
H20A0.62531.14480.50680.020*
C210.70218 (13)0.99052 (12)0.39705 (9)0.0150 (2)
H21A0.63551.04550.34120.018*
C220.66296 (14)0.87655 (13)−0.10556 (9)0.0168 (2)
C230.65025 (17)0.72265 (14)−0.13229 (10)0.0238 (2)
H23D0.60850.7288−0.20410.036*
H23A0.57150.6849−0.08170.036*
H23B0.76260.6552−0.12830.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0294 (4)0.0142 (4)0.0177 (4)−0.0079 (3)−0.0024 (3)−0.0016 (3)
O20.0157 (3)0.0153 (4)0.0234 (4)−0.0011 (3)−0.0024 (3)−0.0019 (3)
O30.0304 (4)0.0212 (4)0.0168 (4)−0.0038 (3)−0.0049 (3)0.0021 (3)
N10.0193 (4)0.0125 (4)0.0125 (4)−0.0037 (3)−0.0008 (3)−0.0007 (3)
N20.0205 (5)0.0161 (4)0.0260 (5)−0.0057 (4)−0.0015 (4)0.0014 (4)
C10.0149 (4)0.0134 (4)0.0147 (5)−0.0037 (4)0.0014 (3)−0.0010 (3)
C20.0196 (5)0.0168 (5)0.0175 (5)−0.0067 (4)0.0016 (4)−0.0029 (4)
C30.0230 (5)0.0148 (5)0.0239 (6)−0.0076 (4)0.0035 (4)−0.0038 (4)
C40.0262 (6)0.0145 (5)0.0250 (6)−0.0062 (4)0.0030 (4)0.0016 (4)
C50.0248 (5)0.0167 (5)0.0176 (5)−0.0048 (4)0.0002 (4)0.0017 (4)
C60.0166 (4)0.0132 (4)0.0147 (5)−0.0035 (4)0.0015 (3)−0.0017 (4)
C70.0167 (4)0.0141 (4)0.0130 (4)−0.0033 (4)−0.0004 (3)−0.0008 (4)
C80.0150 (4)0.0129 (4)0.0141 (5)−0.0038 (3)−0.0006 (3)−0.0017 (3)
C90.0121 (4)0.0126 (4)0.0151 (5)−0.0032 (3)−0.0010 (3)−0.0015 (3)
C100.0157 (4)0.0128 (4)0.0122 (4)−0.0028 (4)−0.0022 (3)−0.0006 (3)
C110.0149 (4)0.0126 (4)0.0131 (4)−0.0035 (4)−0.0015 (3)−0.0009 (3)
C120.0168 (5)0.0135 (4)0.0182 (5)−0.0022 (4)−0.0006 (4)0.0017 (4)
C130.0142 (4)0.0191 (5)0.0213 (5)−0.0015 (4)−0.0010 (4)0.0013 (4)
C140.0177 (5)0.0207 (5)0.0204 (5)−0.0074 (4)−0.0001 (4)−0.0010 (4)
C150.0159 (5)0.0129 (4)0.0213 (5)−0.0020 (4)−0.0024 (4)0.0007 (4)
C160.0136 (4)0.0130 (4)0.0130 (4)−0.0048 (3)−0.0002 (3)−0.0004 (3)
C170.0154 (4)0.0135 (4)0.0154 (5)−0.0031 (4)−0.0007 (4)−0.0003 (4)
C180.0181 (5)0.0175 (5)0.0138 (5)−0.0047 (4)−0.0028 (4)0.0009 (4)
C190.0213 (5)0.0176 (5)0.0139 (5)−0.0059 (4)0.0013 (4)−0.0028 (4)
C200.0194 (5)0.0138 (4)0.0169 (5)−0.0026 (4)0.0025 (4)−0.0024 (4)
C210.0159 (4)0.0139 (4)0.0145 (5)−0.0030 (4)−0.0004 (3)0.0006 (4)
C220.0169 (5)0.0194 (5)0.0136 (5)−0.0023 (4)0.0002 (4)−0.0030 (4)
C230.0328 (6)0.0205 (5)0.0189 (5)−0.0051 (5)−0.0066 (4)−0.0047 (4)

Geometric parameters (Å, °)

O1—C71.2100 (13)C11—C151.3919 (15)
O2—C101.2196 (13)C11—C121.3940 (14)
O3—C221.2146 (14)C12—C131.3807 (15)
N1—C221.4027 (14)C12—H12A0.93
N1—C71.4146 (13)C13—C141.3854 (16)
N1—C61.4293 (14)C13—H13A0.93
N2—C151.3360 (15)C14—H14A0.93
N2—C141.3421 (15)C15—H15A0.93
C1—C21.3920 (15)C16—C171.4020 (14)
C1—C61.4025 (15)C16—C211.4026 (14)
C1—C81.4614 (14)C17—C181.3866 (15)
C2—C31.3884 (16)C17—H17A0.93
C2—H2A0.93C18—C191.3890 (15)
C3—C41.3909 (17)C18—H18A0.93
C3—H3A0.93C19—C201.3914 (15)
C4—C51.3920 (17)C19—H19A0.93
C4—H4A0.93C20—C211.3855 (15)
C5—C61.3868 (15)C20—H20A0.93
C5—H5A0.93C21—H21A0.93
C7—C81.4911 (14)C22—C231.4925 (16)
C8—C91.3510 (14)C23—H23D0.96
C9—C161.4779 (14)C23—H23A0.96
C9—C101.5169 (15)C23—H23B0.96
C10—C111.4844 (15)
C22—N1—C7126.23 (9)C13—C12—H12A120.6
C22—N1—C6124.62 (9)C11—C12—H12A120.6
C7—N1—C6109.05 (8)C12—C13—C14118.45 (10)
C15—N2—C14116.88 (10)C12—C13—H13A120.8
C2—C1—C6119.44 (10)C14—C13—H13A120.8
C2—C1—C8132.38 (10)N2—C14—C13123.95 (10)
C6—C1—C8108.08 (9)N2—C14—H14A118.0
C3—C2—C1119.30 (10)C13—C14—H14A118.0
C3—C2—H2A120.3N2—C15—C11123.54 (10)
C1—C2—H2A120.3N2—C15—H15A118.2
C2—C3—C4120.41 (10)C11—C15—H15A118.2
C2—C3—H3A119.8C17—C16—C21118.84 (10)
C4—C3—H3A119.8C17—C16—C9120.64 (9)
C3—C4—C5121.29 (10)C21—C16—C9120.24 (9)
C3—C4—H4A119.4C18—C17—C16120.34 (10)
C5—C4—H4A119.4C18—C17—H17A119.8
C6—C5—C4117.78 (11)C16—C17—H17A119.8
C6—C5—H5A121.1C17—C18—C19120.29 (10)
C4—C5—H5A121.1C17—C18—H18A119.9
C5—C6—C1121.74 (10)C19—C18—H18A119.9
C5—C6—N1128.68 (10)C18—C19—C20119.87 (10)
C1—C6—N1109.51 (9)C18—C19—H19A120.1
O1—C7—N1126.06 (10)C20—C19—H19A120.1
O1—C7—C8127.05 (10)C21—C20—C19120.17 (10)
N1—C7—C8106.84 (9)C21—C20—H20A119.9
C9—C8—C1133.76 (10)C19—C20—H20A119.9
C9—C8—C7119.91 (10)C20—C21—C16120.45 (10)
C1—C8—C7106.16 (9)C20—C21—H21A119.8
C8—C9—C16126.82 (10)C16—C21—H21A119.8
C8—C9—C10120.64 (9)O3—C22—N1119.12 (10)
C16—C9—C10112.44 (9)O3—C22—C23122.22 (10)
O2—C10—C11122.38 (10)N1—C22—C23118.65 (10)
O2—C10—C9120.09 (9)C22—C23—H23D109.5
C11—C10—C9117.10 (9)C22—C23—H23A109.5
C15—C11—C12118.37 (10)H23D—C23—H23A109.5
C15—C11—C10119.66 (9)C22—C23—H23B109.5
C12—C11—C10121.97 (9)H23D—C23—H23B109.5
C13—C12—C11118.78 (10)H23A—C23—H23B109.5
C6—C1—C2—C32.16 (16)C16—C9—C10—O2−91.54 (12)
C8—C1—C2—C3177.86 (11)C8—C9—C10—C11−95.54 (12)
C1—C2—C3—C4−1.10 (17)C16—C9—C10—C1181.14 (11)
C2—C3—C4—C5−0.66 (18)O2—C10—C11—C1510.99 (16)
C3—C4—C5—C61.30 (17)C9—C10—C11—C15−161.52 (10)
C4—C5—C6—C1−0.20 (17)O2—C10—C11—C12−168.92 (10)
C4—C5—C6—N1−176.92 (10)C9—C10—C11—C1218.58 (15)
C2—C1—C6—C5−1.54 (16)C15—C11—C12—C13−1.65 (16)
C8—C1—C6—C5−178.19 (10)C10—C11—C12—C13178.26 (10)
C2—C1—C6—N1175.75 (9)C11—C12—C13—C141.31 (16)
C8—C1—C6—N1−0.91 (12)C15—N2—C14—C13−1.21 (18)
C22—N1—C6—C5−9.52 (17)C12—C13—C14—N20.14 (18)
C7—N1—C6—C5173.99 (11)C14—N2—C15—C110.83 (17)
C22—N1—C6—C1173.44 (9)C12—C11—C15—N20.58 (17)
C7—N1—C6—C1−3.05 (12)C10—C11—C15—N2−179.33 (10)
C22—N1—C7—O16.86 (17)C8—C9—C16—C17−146.10 (11)
C6—N1—C7—O1−176.72 (10)C10—C9—C16—C1737.46 (13)
C22—N1—C7—C8−170.80 (9)C8—C9—C16—C2140.03 (15)
C6—N1—C7—C85.61 (11)C10—C9—C16—C21−136.40 (10)
C2—C1—C8—C913.1 (2)C21—C16—C17—C18−1.83 (15)
C6—C1—C8—C9−170.79 (11)C9—C16—C17—C18−175.78 (9)
C2—C1—C8—C7−171.80 (11)C16—C17—C18—C190.13 (16)
C6—C1—C8—C74.26 (11)C17—C18—C19—C201.24 (16)
O1—C7—C8—C9−7.79 (17)C18—C19—C20—C21−0.87 (17)
N1—C7—C8—C9169.84 (9)C19—C20—C21—C16−0.86 (16)
O1—C7—C8—C1176.33 (11)C17—C16—C21—C202.19 (15)
N1—C7—C8—C1−6.04 (11)C9—C16—C21—C20176.17 (10)
C1—C8—C9—C168.63 (19)C7—N1—C22—O3168.91 (10)
C7—C8—C9—C16−165.88 (9)C6—N1—C22—O3−6.97 (16)
C1—C8—C9—C10−175.20 (10)C7—N1—C22—C23−11.15 (16)
C7—C8—C9—C1010.28 (15)C6—N1—C22—C23172.96 (10)
C8—C9—C10—O291.78 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C12—H12A···O3i0.932.373.2518 (16)158
C14—H14A···O2ii0.932.533.2381 (16)133
C20—H20A···N2iii0.932.583.3238 (17)137

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z; (iii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5150).

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