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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1686.
Published online 2010 June 16. doi:  10.1107/S1600536810022580
PMCID: PMC3006959

1-Acetyl-3-[2-(2,3,5,6-tetra­fluoro­phen­yl)hydrazin-1-yl­idene]indolin-2-one

Abstract

In the title compound, C16H9F4N3O2, the dihedral angle between the aromatic ring systems is 4.10 (14)° and a bifurcated intra­molecular N—H(...)(O,F) hydrogen bond generates an S(6) ring for the O-atom acceptor and an S(5) ring for the F-atom acceptor. A short C—H(...)O conact also occurs. In the crystal, mol­ecules are linked by C—H(...)O inter­actions.

Related literature

For background on related isatin derivatives, see: Pervez et al. (2007 [triangle], 2008 [triangle], 2010a [triangle]). For related structures, see: Abad et al. (2006 [triangle]); Pervez et al. (2010b [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1686-scheme1.jpg

Experimental

Crystal data

  • C16H9F4N3O2
  • M r = 351.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1686-efi1.jpg
  • a = 9.8993 (19) Å
  • b = 4.7740 (6) Å
  • c = 16.066 (3) Å
  • β = 104.807 (8)°
  • V = 734.0 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 296 K
  • 0.32 × 0.24 × 0.22 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.942, T max = 0.952
  • 6095 measured reflections
  • 1462 independent reflections
  • 749 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.080
  • S = 0.96
  • 1462 reflections
  • 227 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022580/hb5498sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022580/hb5498Isup2.hkl

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

Acknowledgments

MA gratefully acknowledges the Higher Education Commission (HEC), Islamabad, Pakistan, for providing him with a Scholarship under the Indigenous PhD Program and also for partial funding of this research work.

supplementary crystallographic information

Comment

In continuation of our previous work on the synthesis of isatin derivatives having physiological properties (Pervez et al., 2007, 2008, 2010a, 2010b), we report herein the synthesis and crystal structure of the title compound (I), (Fig. 1).

The crystal structure of N-(2-chloropyrid-4-yl)-N'-(2,3,5,6-tetrafluorophenyl)urea (Abad et al., 2006) has been published which contains the same flouro substituted phenyl group as in (I).

In (I), the 2-oxoindolin-3-hydrazono group A (N3/C1–C8/O2/N1/N2) and tetrafluorophenyl B (C11—C16/F1–F4) are planar with r. m. s. deviations of 0.0197 and 0.0121 Å, respectively. The dihedral angle between A/B is 4.10 (14)°. The acetyl moiety (O1/C9/C10) is oriented at 6.21 (83)° with its parent group A. One S(5) ring motif (Bernstein et al., 1995) is formed due to intramolecular H-bonding of N—H···F type, two S(6) ring motifs due to N—H···O and C—H···O interactions (Table 1, Fig. 1) are formed. The molecules are stabilized in the form of one dimensional polymeric chains extending along the a axis (Fig. 2).

Experimental

A solution of 1-acetylisatin (0.95 g, 5.0 mmol) in ethanol (50 ml) was added to the solution of 2,3,5,6-tetrafluorophenyl hydrazine (0.90 g, 5.0 mmol) made in concentrated sulfuric acid (8 ml) and diluted with ethanol (50 ml). The reaction mixture was then refluxed for 30 min. The bright yellow crystalline solid formed during refluxing was collected by suction filtration. Thorough washing with hot ethanol furnished the desired compound (I) in pure form (0.40 g, 23%), m.p. 445 K. Bright yellow prisms of (I) were grown in chloroform by slow evaporation method at room temperature.

Refinement

In the absence of anamolous scattering, the Friedal pairs were merged before refinement. The H-atoms were positioned geometrically (N–H = 0.86 Å, C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. The dotted lines indicate the intra-molecular H-bondings.
Fig. 2.
The partial packing of (I), which shows that molecules form one-dimensional polymeric chains extending along the a axis.

Crystal data

C16H9F4N3O2F(000) = 356
Mr = 351.26Dx = 1.589 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 749 reflections
a = 9.8993 (19) Åθ = 2.6–25.3°
b = 4.7740 (6) ŵ = 0.14 mm1
c = 16.066 (3) ÅT = 296 K
β = 104.807 (8)°Prism, yellow
V = 734.0 (2) Å30.32 × 0.24 × 0.22 mm
Z = 2

Data collection

Bruker Kappa APEXII CCD diffractometer1462 independent reflections
Radiation source: fine-focus sealed tube749 reflections with I > 2σ(I)
graphiteRint = 0.087
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.1°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −5→5
Tmin = 0.942, Tmax = 0.952l = −19→19
6095 measured reflections

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0218P)2] where P = (Fo2 + 2Fc2)/3
1462 reflections(Δ/σ)max < 0.001
227 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = −0.18 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
F10.3005 (3)−0.4142 (6)0.06872 (17)0.0638 (12)
F20.4748 (3)−0.8205 (7)0.0458 (2)0.0791 (16)
F30.7604 (3)−0.6503 (7)0.3236 (2)0.0843 (14)
F40.5877 (3)−0.2576 (8)0.34942 (19)0.0820 (14)
O1−0.1264 (4)0.8071 (9)0.2007 (3)0.0780 (17)
O20.1041 (3)0.1514 (8)0.1326 (2)0.0613 (14)
N10.3432 (4)0.0297 (9)0.2843 (3)0.0520 (17)
N20.3382 (4)−0.1238 (9)0.2140 (3)0.0492 (17)
N30.0446 (4)0.4800 (9)0.2270 (3)0.0472 (17)
C10.2424 (5)0.2126 (11)0.2794 (3)0.045 (2)
C20.2254 (6)0.3936 (11)0.3472 (3)0.048 (2)
C30.3062 (6)0.4269 (12)0.4321 (4)0.067 (3)
C40.2608 (7)0.6204 (15)0.4832 (4)0.085 (3)
C50.1400 (8)0.7727 (13)0.4520 (4)0.082 (3)
C60.0581 (6)0.7417 (12)0.3682 (4)0.064 (3)
C70.1054 (5)0.5532 (10)0.3168 (3)0.046 (2)
C80.1251 (5)0.2667 (11)0.2034 (3)0.047 (2)
C9−0.0694 (6)0.6214 (14)0.1721 (4)0.057 (2)
C10−0.1145 (5)0.5317 (13)0.0791 (3)0.078 (3)
C110.4358 (5)−0.3222 (11)0.2091 (3)0.0415 (19)
C120.4162 (5)−0.4726 (11)0.1331 (3)0.046 (2)
C130.5063 (6)−0.6775 (12)0.1212 (4)0.055 (2)
C140.6244 (6)−0.7476 (12)0.1850 (4)0.058 (3)
C150.6455 (6)−0.5977 (13)0.2589 (4)0.055 (2)
C160.5565 (6)−0.3921 (11)0.2732 (3)0.052 (2)
H20.26986−0.096590.169450.0589*
H30.387100.322860.453290.0808*
H40.312790.648310.539640.1016*
H50.112380.900270.488230.0984*
H6−0.024100.842510.347810.0768*
H10A−0.191070.646430.048920.1164*
H10B−0.143410.339170.075890.1164*
H10C−0.037720.552300.053200.1164*
H140.68534−0.888330.177720.0692*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.059 (2)0.066 (2)0.058 (2)0.0084 (17)−0.0006 (16)0.0018 (17)
F20.096 (3)0.066 (2)0.078 (3)0.010 (2)0.027 (2)−0.013 (2)
F30.062 (2)0.101 (3)0.083 (2)0.018 (2)0.006 (2)0.024 (2)
F40.077 (2)0.098 (3)0.060 (2)0.013 (2)−0.0025 (19)−0.010 (2)
O10.075 (3)0.076 (3)0.083 (3)0.029 (3)0.020 (2)0.002 (2)
O20.061 (2)0.070 (3)0.052 (2)0.010 (2)0.013 (2)−0.010 (2)
N10.062 (3)0.047 (3)0.048 (3)−0.006 (3)0.016 (2)−0.002 (3)
N20.042 (3)0.055 (3)0.048 (3)0.008 (2)0.007 (2)−0.001 (3)
N30.048 (3)0.039 (3)0.055 (3)0.008 (2)0.014 (3)0.006 (2)
C10.048 (4)0.038 (4)0.051 (4)0.003 (3)0.015 (3)0.008 (3)
C20.058 (4)0.043 (4)0.045 (4)−0.004 (3)0.018 (3)0.002 (3)
C30.075 (4)0.069 (5)0.055 (4)0.010 (4)0.011 (4)−0.004 (4)
C40.105 (6)0.083 (6)0.062 (5)0.003 (5)0.014 (4)−0.015 (4)
C50.112 (6)0.068 (5)0.073 (5)0.001 (5)0.035 (4)−0.020 (4)
C60.067 (4)0.056 (4)0.074 (5)0.007 (3)0.027 (4)−0.003 (4)
C70.053 (4)0.037 (4)0.050 (4)−0.004 (3)0.016 (3)−0.001 (3)
C80.049 (4)0.042 (4)0.051 (4)−0.003 (3)0.017 (3)0.006 (3)
C90.051 (4)0.057 (4)0.066 (4)0.005 (3)0.022 (3)0.008 (3)
C100.072 (4)0.095 (5)0.057 (4)0.019 (4)0.000 (3)0.000 (4)
C110.040 (3)0.037 (3)0.051 (4)−0.001 (3)0.018 (3)0.010 (3)
C120.046 (4)0.040 (4)0.052 (4)0.006 (3)0.013 (3)0.006 (3)
C130.068 (4)0.045 (4)0.055 (4)0.001 (3)0.020 (4)−0.002 (3)
C140.057 (4)0.044 (4)0.078 (5)0.008 (3)0.028 (4)0.012 (4)
C150.044 (4)0.057 (4)0.064 (4)0.009 (3)0.012 (3)0.021 (4)
C160.051 (4)0.056 (4)0.048 (4)−0.009 (3)0.013 (3)−0.006 (3)

Geometric parameters (Å, °)

F1—C121.362 (6)C4—C51.380 (10)
F2—C131.356 (7)C5—C61.391 (9)
F3—C151.354 (7)C6—C71.382 (8)
F4—C161.347 (6)C9—C101.508 (8)
O1—C91.203 (8)C11—C161.404 (7)
O2—C81.233 (6)C11—C121.387 (7)
N1—N21.337 (6)C12—C131.370 (8)
N1—C11.313 (7)C13—C141.385 (9)
N2—C111.370 (7)C14—C151.356 (9)
N3—C71.457 (7)C15—C161.377 (8)
N3—C81.404 (7)C3—H30.9300
N3—C91.414 (8)C4—H40.9300
N2—H20.8600C5—H50.9300
C1—C81.477 (7)C6—H60.9300
C1—C21.434 (7)C10—H10A0.9600
C2—C71.391 (8)C10—H10B0.9600
C2—C31.403 (8)C10—H10C0.9600
C3—C41.385 (9)C14—H140.9300
N2—N1—C1116.8 (4)F1—C12—C13119.4 (5)
N1—N2—C11123.6 (4)C11—C12—C13122.9 (5)
C7—N3—C8108.8 (4)F1—C12—C11117.7 (4)
C7—N3—C9124.4 (4)C12—C13—C14121.7 (5)
C8—N3—C9126.6 (5)F2—C13—C12118.4 (5)
N1—N2—H2118.00F2—C13—C14119.9 (5)
C11—N2—H2118.00C13—C14—C15115.6 (6)
N1—C1—C2126.2 (5)F3—C15—C16116.9 (5)
N1—C1—C8126.2 (5)C14—C15—C16124.1 (6)
C2—C1—C8107.6 (4)F3—C15—C14119.1 (5)
C1—C2—C3131.2 (5)C11—C16—C15120.5 (5)
C3—C2—C7120.2 (5)F4—C16—C11120.5 (5)
C1—C2—C7108.6 (4)F4—C16—C15118.9 (5)
C2—C3—C4117.5 (6)C2—C3—H3121.00
C3—C4—C5121.2 (6)C4—C3—H3121.00
C4—C5—C6122.2 (6)C3—C4—H4119.00
C5—C6—C7116.4 (6)C5—C4—H4119.00
C2—C7—C6122.5 (5)C4—C5—H5119.00
N3—C7—C2108.4 (4)C6—C5—H5119.00
N3—C7—C6129.1 (5)C5—C6—H6122.00
N3—C8—C1106.5 (4)C7—C6—H6122.00
O2—C8—N3126.9 (5)C9—C10—H10A110.00
O2—C8—C1126.6 (5)C9—C10—H10B109.00
O1—C9—N3119.4 (6)C9—C10—H10C109.00
O1—C9—C10122.6 (6)H10A—C10—H10B109.00
N3—C9—C10118.0 (5)H10A—C10—H10C109.00
N2—C11—C12117.8 (4)H10B—C10—H10C109.00
C12—C11—C16115.1 (5)C13—C14—H14122.00
N2—C11—C16127.1 (5)C15—C14—H14122.00
C1—N1—N2—C11179.8 (5)C1—C2—C7—C6177.8 (5)
N2—N1—C1—C2178.5 (5)C3—C2—C7—N3178.8 (5)
N2—N1—C1—C8−0.7 (8)C3—C2—C7—C6−2.1 (8)
N1—N2—C11—C12178.2 (5)C2—C3—C4—C50.6 (10)
N1—N2—C11—C16−2.2 (8)C3—C4—C5—C6−0.3 (11)
C8—N3—C7—C22.2 (6)C4—C5—C6—C7−1.2 (10)
C8—N3—C7—C6−176.7 (5)C5—C6—C7—N3−178.8 (5)
C9—N3—C7—C2−172.7 (5)C5—C6—C7—C22.4 (8)
C9—N3—C7—C68.4 (8)N2—C11—C12—F1−0.5 (7)
C7—N3—C8—O2179.4 (5)N2—C11—C12—C13−179.4 (5)
C7—N3—C8—C1−2.2 (5)C16—C11—C12—F1179.8 (4)
C9—N3—C8—O2−5.9 (9)C16—C11—C12—C130.9 (8)
C9—N3—C8—C1172.6 (5)N2—C11—C16—F4−0.6 (8)
C7—N3—C9—O1−3.7 (9)N2—C11—C16—C15180.0 (5)
C7—N3—C9—C10176.2 (5)C12—C11—C16—F4179.1 (5)
C8—N3—C9—O1−177.7 (5)C12—C11—C16—C15−0.4 (8)
C8—N3—C9—C102.3 (8)F1—C12—C13—F2−1.6 (8)
N1—C1—C2—C30.5 (10)F1—C12—C13—C14−179.1 (5)
N1—C1—C2—C7−179.4 (5)C11—C12—C13—F2177.3 (5)
C8—C1—C2—C3179.8 (6)C11—C12—C13—C14−0.2 (9)
C8—C1—C2—C70.0 (6)F2—C13—C14—C15−178.4 (5)
N1—C1—C8—O2−0.8 (9)C12—C13—C14—C15−0.9 (9)
N1—C1—C8—N3−179.3 (5)C13—C14—C15—F3−178.6 (5)
C2—C1—C8—O2179.9 (5)C13—C14—C15—C161.5 (9)
C2—C1—C8—N31.4 (6)F3—C15—C16—F4−0.2 (8)
C1—C2—C3—C4−179.3 (6)F3—C15—C16—C11179.3 (5)
C7—C2—C3—C40.6 (9)C14—C15—C16—F4179.7 (5)
C1—C2—C7—N3−1.3 (6)C14—C15—C16—C11−0.9 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O20.861.992.694 (5)139
N2—H2···F10.862.292.658 (5)106
C6—H6···O10.932.332.857 (8)116
C14—H14···O1i0.932.323.217 (7)163

Symmetry codes: (i) x+1, y−2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5498).

References

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  • Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010a). Lett. Drug Des. Discov.7, 102–108.
  • Pervez, H., Yaqub, M., Ramzan, M., Iqbal, M. S. & Tahir, M. N. (2010b). Acta Cryst. E66, o1018. [PMC free article] [PubMed]
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