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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 6| June 2011| Page o1294
doi:10.1107/S1600536811015285

5-Fluoro-3-(2-phenyl­hydrazinyl­­idene)indolin-2-one

Wen-Bin Wei,a,b Shuo Tian,a,b Hong Shen,a,b Jie Suna,b and Hai-Bo Wanga*

aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 2 March 2011; accepted 22 April 2011; online 7 May 2011)

In the title compound, C14H10FN3O, the six- and five-membered rings of the isatin moiety and the six-membered ring of phenyl­hydrazone are nearly planar with r.m.s. deviations of 0.0003, 0.0004 and 0.007 Å, respectively. The dihedral angle between the phenyl ring and the isatin ring system is 6.09 (9)°. The mol­ecular structure is stabilized by a strong intra­molecular N—H⋯O hydrogen bond, leading to the formation of a pseudo-six-membered ring, generating an S(6) ring. The crystal structure features inter­molecular N—H⋯O inter­actions.

Related literature

For the biological activity of isatin derivatives, see: Samus et al. (2004[Samus, N. M., Tsapkov, V. L. & Culya, A. P. (2004). Russ. J. Gen. Chem. 74, 1428-1432.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the preparation, see: Vine et al. (2007[Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.]).

[Scheme 1]

Experimental

Crystal data

  • C14H10FN3O

  • Mr = 255.25

  • Triclinic, [P \overline 1]

  • a = 6.4840 (13) Å

  • b = 8.7250 (17) Å

  • c = 11.672 (2) Å

  • α = 69.98 (3)°

  • β = 75.43 (3)°

  • γ = 88.33 (3)°

  • V = 599.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.970, Tmax = 0.980

  • 2413 measured reflections

  • 2202 independent reflections

  • 1767 reflections with I > 2σ(I)

  • Rint = 0.014

  • 3 standard reflections every 200 reflections intensity decay: 1%
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.153

  • S = 1.00

  • 2202 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1i 0.86 2.05 2.861 (2) 157
N3—H3A⋯O1 0.86 2.09 2.760 (2) 135
Symmetry code: (i) -x-1, -y+1, -z+2.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015285/aa2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015285/aa2004Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015285/aa2004Isup3.cml

checkCIF report


Comment top

5-fluoro-3-(2-phenylhydrazono)indolin-2-one is one of isatin derivatives which are reported to show a variety of biological activities such as antibacterial, antimicrobial, antifungal and anti-HIV activities (Samus et al., 2004). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). the six- and five-membered rings of the isatin moiety and the six-membered ring of phenylhydrazone are very nearly planar. Rings A (C3—C8) and B(N1/C1/C2/C8/C7) are nearly coplanar, and they are oriented at dihedral angles of A/B = 1.13 (11)°. Rings A (C3—C8) and C(C9—C14) are oriented at dihedral angles of A/C = 6.30 (11)°, and rings B(N1/C1/C2/C8/C7) and C(C9—C14) are oriented at dihedral angles of B/C = 5.90 (11)°.

In the crystal structure, intermolecular N1—H1A···O1 = 2.861 Å interaction may be effective in the stabilization of the structure. The planarity of the molecules was stabilized by a strong intramolecular hydrogen bond N3—H3A···O1 = 2.760 Å leading to the formation of the pseudo six-membered ring(N3/N2/C2/C1/O1/H3A).

Related literature top

For the biological activity of isatin derivatives, see: Samus et al. (2004). For bond-length data, see: Allen et al. (1987). For the preparation, see: Vine et al. (2007).

Experimental top

For the preparation of the title compound, phenylhydrozone was reacted with equimolar amounts of isatin in ethanol, following the standard procedure (Vine et al., 2007). The product precipitated as yellow crystals in 30 min, and was collected by filtration and washed with cold ethanol. Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone:ethyl acetate =2:1 solution (yield: 91%, m.p. 543 K).

Refinement top

H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 Å for aromatic, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: CAD-4 EXPRESS (Enraf–Nonius, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram.
5-Fluoro-3-(2-phenylhydrazinylidene)indolin-2-one top
Crystal data top
C14H10FN3OZ = 2
Mr = 255.25F(000) = 264
Triclinic, P1Dx = 1.415 Mg m−3
Hall symbol: -P 1Melting point: 543 K
a = 6.4840 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.7250 (17) ÅCell parameters from 25 reflections
c = 11.672 (2) Åθ = 10–13°
α = 69.98 (3)°µ = 0.10 mm−1
β = 75.43 (3)°T = 293 K
γ = 88.33 (3)°Block, yellow
V = 599.3 (2) Å30.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		1767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.4°, θmin = 1.9°
ω/2θ scansh = 0→7
Absorption correction: ψ scan
(North et al., 1968)		k = −10→10
Tmin = 0.970, Tmax = 0.980l = −13→14
2413 measured reflections3 standard reflections every 200 reflections
2202 independent reflections intensity decay: 1%
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.1P)2 + 0.108P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2202 reflectionsΔρmax = 0.21 e Å−3
173 parametersΔρmin = −0.20 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.058 (11)
Crystal data top
C14H10FN3Oγ = 88.33 (3)°
Mr = 255.25V = 599.3 (2) Å3
Triclinic, P1Z = 2
a = 6.4840 (13) ÅMo Kα radiation
b = 8.7250 (17) ŵ = 0.10 mm−1
c = 11.672 (2) ÅT = 293 K
α = 69.98 (3)°0.30 × 0.20 × 0.20 mm
β = 75.43 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1767 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.014
Tmin = 0.970, Tmax = 0.9803 standard reflections every 200 reflections
2413 measured reflections intensity decay: 1%
2202 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å−3
2202 reflectionsΔρmin = −0.20 e Å−3
173 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 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) top
xyzUiso*/Ueq
O1−0.3760 (2)0.63511 (17)1.06116 (14)0.0569 (4)
F10.5373 (2)0.7060 (2)0.55092 (14)0.0974 (6)
N1−0.2569 (2)0.5813 (2)0.87432 (15)0.0520 (4)
H1A−0.37240.53530.87430.062*
C1−0.2376 (3)0.6408 (2)0.96456 (18)0.0462 (5)
N20.0754 (2)0.77749 (18)0.98762 (14)0.0453 (4)
C2−0.0150 (3)0.7110 (2)0.92643 (17)0.0438 (4)
N3−0.0413 (2)0.78890 (19)1.09465 (15)0.0494 (4)
H3A−0.17510.75921.11910.059*
C30.2929 (3)0.7207 (2)0.73265 (18)0.0539 (5)
H3B0.39710.77360.75020.065*
C40.3360 (3)0.6740 (3)0.6286 (2)0.0634 (6)
C50.1875 (4)0.5940 (3)0.5986 (2)0.0671 (6)
H5A0.22520.56400.52730.081*
C6−0.0170 (4)0.5592 (3)0.6761 (2)0.0587 (5)
H6A−0.12020.50650.65760.070*
C7−0.0645 (3)0.6043 (2)0.78105 (18)0.0472 (5)
C80.0879 (3)0.6855 (2)0.81030 (17)0.0451 (5)
C90.0503 (3)0.8486 (2)1.16853 (17)0.0451 (5)
C100.2649 (3)0.8988 (2)1.13266 (19)0.0529 (5)
H10A0.35260.89281.05800.063*
C110.3471 (4)0.9576 (3)1.2088 (2)0.0632 (6)
H11A0.49060.99291.18410.076*
C120.2208 (4)0.9652 (3)1.3206 (2)0.0662 (6)
H12A0.27831.00501.37110.079*
C130.0094 (4)0.9132 (3)1.3566 (2)0.0658 (6)
H13A−0.07640.91691.43240.079*
C14−0.0778 (3)0.8555 (2)1.28156 (19)0.0555 (5)
H14A−0.22180.82131.30660.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0418 (7)0.0615 (9)0.0674 (9)−0.0080 (6)−0.0031 (6)−0.0292 (7)
F10.0676 (9)0.1417 (15)0.0798 (10)−0.0157 (9)0.0153 (7)−0.0571 (10)
N10.0429 (9)0.0550 (9)0.0631 (10)−0.0075 (7)−0.0141 (7)−0.0255 (8)
C10.0401 (9)0.0430 (9)0.0556 (11)−0.0028 (7)−0.0109 (8)−0.0176 (8)
N20.0416 (8)0.0456 (9)0.0487 (9)−0.0035 (6)−0.0083 (7)−0.0182 (7)
C20.0390 (9)0.0426 (9)0.0498 (10)−0.0031 (7)−0.0098 (8)−0.0167 (8)
N30.0402 (8)0.0559 (9)0.0520 (9)−0.0075 (7)−0.0044 (7)−0.0230 (7)
C30.0469 (10)0.0590 (12)0.0554 (11)−0.0061 (9)−0.0076 (9)−0.0225 (9)
C40.0560 (12)0.0751 (14)0.0538 (12)−0.0024 (10)0.0003 (9)−0.0254 (10)
C50.0780 (15)0.0738 (14)0.0538 (12)−0.0002 (12)−0.0111 (11)−0.0312 (11)
C60.0658 (13)0.0603 (12)0.0580 (12)−0.0040 (10)−0.0212 (10)−0.0260 (10)
C70.0472 (10)0.0419 (9)0.0524 (11)−0.0011 (8)−0.0155 (8)−0.0141 (8)
C80.0447 (10)0.0409 (9)0.0501 (10)−0.0006 (7)−0.0126 (8)−0.0159 (8)
C90.0465 (10)0.0404 (9)0.0469 (10)−0.0015 (7)−0.0089 (8)−0.0152 (8)
C100.0466 (10)0.0628 (12)0.0512 (11)−0.0037 (9)−0.0053 (8)−0.0268 (9)
C110.0548 (12)0.0778 (15)0.0636 (13)−0.0071 (10)−0.0150 (10)−0.0319 (11)
C120.0752 (15)0.0741 (15)0.0583 (13)−0.0067 (12)−0.0200 (11)−0.0312 (11)
C130.0795 (15)0.0686 (14)0.0480 (11)−0.0029 (11)−0.0046 (11)−0.0264 (10)
C140.0516 (11)0.0555 (11)0.0549 (11)−0.0047 (9)−0.0035 (9)−0.0200 (9)
Geometric parameters (Å, º) top
O1—C11.239 (2)C5—H5A0.9300
F1—C41.363 (2)C6—C71.373 (3)
N1—C11.356 (2)C6—H6A0.9300
N1—C71.401 (2)C7—C81.404 (2)
N1—H1A0.8600C9—C101.386 (3)
C1—C21.483 (2)C9—C141.391 (3)
N2—C21.306 (2)C10—C111.380 (3)
N2—N31.322 (2)C10—H10A0.9300
C2—C81.441 (3)C11—C121.377 (3)
N3—C91.396 (2)C11—H11A0.9300
N3—H3A0.8600C12—C131.370 (3)
C3—C41.371 (3)C12—H12A0.9300
C3—C81.382 (3)C13—C141.382 (3)
C3—H3B0.9300C13—H13A0.9300
C4—C51.382 (3)C14—H14A0.9300
C5—C61.378 (3)
C1—N1—C7111.36 (15)C6—C7—N1129.42 (18)
C1—N1—H1A124.3C6—C7—C8121.89 (19)
C7—N1—H1A124.3N1—C7—C8108.69 (16)
O1—C1—N1127.23 (16)C3—C8—C7119.75 (18)
O1—C1—C2126.46 (17)C3—C8—C2133.33 (17)
N1—C1—C2106.29 (16)C7—C8—C2106.90 (16)
C2—N2—N3118.21 (15)C10—C9—C14119.59 (18)
N2—C2—C8125.87 (16)C10—C9—N3121.66 (17)
N2—C2—C1127.33 (17)C14—C9—N3118.75 (17)
C8—C2—C1106.74 (15)C11—C10—C9119.34 (19)
N2—N3—C9120.78 (15)C11—C10—H10A120.3
N2—N3—H3A119.6C9—C10—H10A120.3
C9—N3—H3A119.6C12—C11—C10121.3 (2)
C4—C3—C8117.08 (19)C12—C11—H11A119.4
C4—C3—H3B121.5C10—C11—H11A119.4
C8—C3—H3B121.5C13—C12—C11119.2 (2)
F1—C4—C3118.3 (2)C13—C12—H12A120.4
F1—C4—C5117.90 (19)C11—C12—H12A120.4
C3—C4—C5123.8 (2)C12—C13—C14120.8 (2)
C6—C5—C4119.1 (2)C12—C13—H13A119.6
C6—C5—H5A120.5C14—C13—H13A119.6
C4—C5—H5A120.5C13—C14—C9119.79 (19)
C7—C6—C5118.42 (19)C13—C14—H14A120.1
C7—C6—H6A120.8C9—C14—H14A120.1
C5—C6—H6A120.8
C7—N1—C1—O1−177.71 (18)C4—C3—C8—C2178.50 (19)
C7—N1—C1—C20.9 (2)C6—C7—C8—C3−0.6 (3)
N3—N2—C2—C8−178.66 (16)N1—C7—C8—C3179.20 (16)
N3—N2—C2—C1−1.7 (3)C6—C7—C8—C2−179.09 (17)
O1—C1—C2—N20.7 (3)N1—C7—C8—C20.7 (2)
N1—C1—C2—N2−177.91 (17)N2—C2—C8—C3−0.9 (3)
O1—C1—C2—C8178.17 (18)C1—C2—C8—C3−178.4 (2)
N1—C1—C2—C8−0.5 (2)N2—C2—C8—C7177.35 (17)
C2—N2—N3—C9175.62 (16)C1—C2—C8—C7−0.1 (2)
C8—C3—C4—F1−179.48 (19)N2—N3—C9—C100.4 (3)
C8—C3—C4—C5−0.5 (3)N2—N3—C9—C14−178.79 (16)
F1—C4—C5—C6179.6 (2)C14—C9—C10—C11−1.2 (3)
C3—C4—C5—C60.6 (4)N3—C9—C10—C11179.65 (17)
C4—C5—C6—C7−0.7 (3)C9—C10—C11—C121.0 (3)
C5—C6—C7—N1−179.05 (19)C10—C11—C12—C13−0.1 (4)
C5—C6—C7—C80.7 (3)C11—C12—C13—C14−0.7 (4)
C1—N1—C7—C6178.71 (19)C12—C13—C14—C90.5 (3)
C1—N1—C7—C8−1.0 (2)C10—C9—C14—C130.4 (3)
C4—C3—C8—C70.4 (3)N3—C9—C14—C13179.65 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.052.861 (2)157
N3—H3A···O10.862.092.760 (2)135
Symmetry code: (i) −x−1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC14H10FN3O
Mr255.25
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.4840 (13), 8.7250 (17), 11.672 (2)
α, β, γ (°)69.98 (3), 75.43 (3), 88.33 (3)
V (Å3)599.3 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.970, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		2413, 2202, 1767
Rint0.014
(sin θ/λ)max (Å−1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.153, 1.00
No. of reflections2202
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.052.861 (2)157
N3—H3A···O10.862.092.760 (2)135
Symmetry code: (i) −x−1, −y+1, −z+2.
 

Acknowledgements

The authors thank the Center of Testing and Analysis of Nanjing University for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationSamus, N. M., Tsapkov, V. L. & Culya, A. P. (2004). Russ. J. Gen. Chem. 74, 1428–1432.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931–938.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 6| June 2011| Page o1294
doi:10.1107/S1600536811015285
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