1-Acetyl-3-[2-(2,3,5,6-tetra-fluoro-phen-yl)hydrazin-1-yl-idene]indolin-2-one.

In the title compound, C(16)H(9)F(4)N(3)O(2), the dihedral angle between the aromatic ring systems is 4.10 (14)° and a bifurcated intra-molecular 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, mol-ecules are linked by C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C16H9F4N3O2

M = 351.26

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

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

C16H9F4N3O2	F(000) = 356
Mr = 351.26	Dx = 1.589 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 749 reflections
a = 9.8993 (19) Å	θ = 2.6–25.3°
b = 4.7740 (6) Å	µ = 0.14 mm−1
c = 16.066 (3) Å	T = 296 K
β = 104.807 (8)°	Prism, yellow
V = 734.0 (2) Å3	0.32 × 0.24 × 0.22 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1462 independent reflections
Radiation source: fine-focus sealed tube	749 reflections with I > 2σ(I)
graphite	Rint = 0.087
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.1°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.942, Tmax = 0.952	l = −19→19
6095 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0218P)2] where P = (Fo2 + 2Fc2)/3
1462 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.3005 (3)	−0.4142 (6)	0.06872 (17)	0.0638 (12)
F2	0.4748 (3)	−0.8205 (7)	0.0458 (2)	0.0791 (16)
F3	0.7604 (3)	−0.6503 (7)	0.3236 (2)	0.0843 (14)
F4	0.5877 (3)	−0.2576 (8)	0.34942 (19)	0.0820 (14)
O1	−0.1264 (4)	0.8071 (9)	0.2007 (3)	0.0780 (17)
O2	0.1041 (3)	0.1514 (8)	0.1326 (2)	0.0613 (14)
N1	0.3432 (4)	0.0297 (9)	0.2843 (3)	0.0520 (17)
N2	0.3382 (4)	−0.1238 (9)	0.2140 (3)	0.0492 (17)
N3	0.0446 (4)	0.4800 (9)	0.2270 (3)	0.0472 (17)
C1	0.2424 (5)	0.2126 (11)	0.2794 (3)	0.045 (2)
C2	0.2254 (6)	0.3936 (11)	0.3472 (3)	0.048 (2)
C3	0.3062 (6)	0.4269 (12)	0.4321 (4)	0.067 (3)
C4	0.2608 (7)	0.6204 (15)	0.4832 (4)	0.085 (3)
C5	0.1400 (8)	0.7727 (13)	0.4520 (4)	0.082 (3)
C6	0.0581 (6)	0.7417 (12)	0.3682 (4)	0.064 (3)
C7	0.1054 (5)	0.5532 (10)	0.3168 (3)	0.046 (2)
C8	0.1251 (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)
C11	0.4358 (5)	−0.3222 (11)	0.2091 (3)	0.0415 (19)
C12	0.4162 (5)	−0.4726 (11)	0.1331 (3)	0.046 (2)
C13	0.5063 (6)	−0.6775 (12)	0.1212 (4)	0.055 (2)
C14	0.6244 (6)	−0.7476 (12)	0.1850 (4)	0.058 (3)
C15	0.6455 (6)	−0.5977 (13)	0.2589 (4)	0.055 (2)
C16	0.5565 (6)	−0.3921 (11)	0.2732 (3)	0.052 (2)
H2	0.26986	−0.09659	0.16945	0.0589*
H3	0.38710	0.32286	0.45329	0.0808*
H4	0.31279	0.64831	0.53964	0.1016*
H5	0.11238	0.90027	0.48823	0.0984*
H6	−0.02410	0.84251	0.34781	0.0768*
H10A	−0.19107	0.64643	0.04892	0.1164*
H10B	−0.14341	0.33917	0.07589	0.1164*
H10C	−0.03772	0.55230	0.05320	0.1164*
H14	0.68534	−0.88833	0.17772	0.0692*

	U11	U22	U33	U12	U13	U23
F1	0.059 (2)	0.066 (2)	0.058 (2)	0.0084 (17)	−0.0006 (16)	0.0018 (17)
F2	0.096 (3)	0.066 (2)	0.078 (3)	0.010 (2)	0.027 (2)	−0.013 (2)
F3	0.062 (2)	0.101 (3)	0.083 (2)	0.018 (2)	0.006 (2)	0.024 (2)
F4	0.077 (2)	0.098 (3)	0.060 (2)	0.013 (2)	−0.0025 (19)	−0.010 (2)
O1	0.075 (3)	0.076 (3)	0.083 (3)	0.029 (3)	0.020 (2)	0.002 (2)
O2	0.061 (2)	0.070 (3)	0.052 (2)	0.010 (2)	0.013 (2)	−0.010 (2)
N1	0.062 (3)	0.047 (3)	0.048 (3)	−0.006 (3)	0.016 (2)	−0.002 (3)
N2	0.042 (3)	0.055 (3)	0.048 (3)	0.008 (2)	0.007 (2)	−0.001 (3)
N3	0.048 (3)	0.039 (3)	0.055 (3)	0.008 (2)	0.014 (3)	0.006 (2)
C1	0.048 (4)	0.038 (4)	0.051 (4)	0.003 (3)	0.015 (3)	0.008 (3)
C2	0.058 (4)	0.043 (4)	0.045 (4)	−0.004 (3)	0.018 (3)	0.002 (3)
C3	0.075 (4)	0.069 (5)	0.055 (4)	0.010 (4)	0.011 (4)	−0.004 (4)
C4	0.105 (6)	0.083 (6)	0.062 (5)	0.003 (5)	0.014 (4)	−0.015 (4)
C5	0.112 (6)	0.068 (5)	0.073 (5)	0.001 (5)	0.035 (4)	−0.020 (4)
C6	0.067 (4)	0.056 (4)	0.074 (5)	0.007 (3)	0.027 (4)	−0.003 (4)
C7	0.053 (4)	0.037 (4)	0.050 (4)	−0.004 (3)	0.016 (3)	−0.001 (3)
C8	0.049 (4)	0.042 (4)	0.051 (4)	−0.003 (3)	0.017 (3)	0.006 (3)
C9	0.051 (4)	0.057 (4)	0.066 (4)	0.005 (3)	0.022 (3)	0.008 (3)
C10	0.072 (4)	0.095 (5)	0.057 (4)	0.019 (4)	0.000 (3)	0.000 (4)
C11	0.040 (3)	0.037 (3)	0.051 (4)	−0.001 (3)	0.018 (3)	0.010 (3)
C12	0.046 (4)	0.040 (4)	0.052 (4)	0.006 (3)	0.013 (3)	0.006 (3)
C13	0.068 (4)	0.045 (4)	0.055 (4)	0.001 (3)	0.020 (4)	−0.002 (3)
C14	0.057 (4)	0.044 (4)	0.078 (5)	0.008 (3)	0.028 (4)	0.012 (4)
C15	0.044 (4)	0.057 (4)	0.064 (4)	0.009 (3)	0.012 (3)	0.021 (4)
C16	0.051 (4)	0.056 (4)	0.048 (4)	−0.009 (3)	0.013 (3)	−0.006 (3)

F1—C12	1.362 (6)	C4—C5	1.380 (10)
F2—C13	1.356 (7)	C5—C6	1.391 (9)
F3—C15	1.354 (7)	C6—C7	1.382 (8)
F4—C16	1.347 (6)	C9—C10	1.508 (8)
O1—C9	1.203 (8)	C11—C16	1.404 (7)
O2—C8	1.233 (6)	C11—C12	1.387 (7)
N1—N2	1.337 (6)	C12—C13	1.370 (8)
N1—C1	1.313 (7)	C13—C14	1.385 (9)
N2—C11	1.370 (7)	C14—C15	1.356 (9)
N3—C7	1.457 (7)	C15—C16	1.377 (8)
N3—C8	1.404 (7)	C3—H3	0.9300
N3—C9	1.414 (8)	C4—H4	0.9300
N2—H2	0.8600	C5—H5	0.9300
C1—C8	1.477 (7)	C6—H6	0.9300
C1—C2	1.434 (7)	C10—H10A	0.9600
C2—C7	1.391 (8)	C10—H10B	0.9600
C2—C3	1.403 (8)	C10—H10C	0.9600
C3—C4	1.385 (9)	C14—H14	0.9300
N2—N1—C1	116.8 (4)	F1—C12—C13	119.4 (5)
N1—N2—C11	123.6 (4)	C11—C12—C13	122.9 (5)
C7—N3—C8	108.8 (4)	F1—C12—C11	117.7 (4)
C7—N3—C9	124.4 (4)	C12—C13—C14	121.7 (5)
C8—N3—C9	126.6 (5)	F2—C13—C12	118.4 (5)
N1—N2—H2	118.00	F2—C13—C14	119.9 (5)
C11—N2—H2	118.00	C13—C14—C15	115.6 (6)
N1—C1—C2	126.2 (5)	F3—C15—C16	116.9 (5)
N1—C1—C8	126.2 (5)	C14—C15—C16	124.1 (6)
C2—C1—C8	107.6 (4)	F3—C15—C14	119.1 (5)
C1—C2—C3	131.2 (5)	C11—C16—C15	120.5 (5)
C3—C2—C7	120.2 (5)	F4—C16—C11	120.5 (5)
C1—C2—C7	108.6 (4)	F4—C16—C15	118.9 (5)
C2—C3—C4	117.5 (6)	C2—C3—H3	121.00
C3—C4—C5	121.2 (6)	C4—C3—H3	121.00
C4—C5—C6	122.2 (6)	C3—C4—H4	119.00
C5—C6—C7	116.4 (6)	C5—C4—H4	119.00
C2—C7—C6	122.5 (5)	C4—C5—H5	119.00
N3—C7—C2	108.4 (4)	C6—C5—H5	119.00
N3—C7—C6	129.1 (5)	C5—C6—H6	122.00
N3—C8—C1	106.5 (4)	C7—C6—H6	122.00
O2—C8—N3	126.9 (5)	C9—C10—H10A	110.00
O2—C8—C1	126.6 (5)	C9—C10—H10B	109.00
O1—C9—N3	119.4 (6)	C9—C10—H10C	109.00
O1—C9—C10	122.6 (6)	H10A—C10—H10B	109.00
N3—C9—C10	118.0 (5)	H10A—C10—H10C	109.00
N2—C11—C12	117.8 (4)	H10B—C10—H10C	109.00
C12—C11—C16	115.1 (5)	C13—C14—H14	122.00
N2—C11—C16	127.1 (5)	C15—C14—H14	122.00
C1—N1—N2—C11	179.8 (5)	C1—C2—C7—C6	177.8 (5)
N2—N1—C1—C2	178.5 (5)	C3—C2—C7—N3	178.8 (5)
N2—N1—C1—C8	−0.7 (8)	C3—C2—C7—C6	−2.1 (8)
N1—N2—C11—C12	178.2 (5)	C2—C3—C4—C5	0.6 (10)
N1—N2—C11—C16	−2.2 (8)	C3—C4—C5—C6	−0.3 (11)
C8—N3—C7—C2	2.2 (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—C2	2.4 (8)
C9—N3—C7—C6	8.4 (8)	N2—C11—C12—F1	−0.5 (7)
C7—N3—C8—O2	179.4 (5)	N2—C11—C12—C13	−179.4 (5)
C7—N3—C8—C1	−2.2 (5)	C16—C11—C12—F1	179.8 (4)
C9—N3—C8—O2	−5.9 (9)	C16—C11—C12—C13	0.9 (8)
C9—N3—C8—C1	172.6 (5)	N2—C11—C16—F4	−0.6 (8)
C7—N3—C9—O1	−3.7 (9)	N2—C11—C16—C15	180.0 (5)
C7—N3—C9—C10	176.2 (5)	C12—C11—C16—F4	179.1 (5)
C8—N3—C9—O1	−177.7 (5)	C12—C11—C16—C15	−0.4 (8)
C8—N3—C9—C10	2.3 (8)	F1—C12—C13—F2	−1.6 (8)
N1—C1—C2—C3	0.5 (10)	F1—C12—C13—C14	−179.1 (5)
N1—C1—C2—C7	−179.4 (5)	C11—C12—C13—F2	177.3 (5)
C8—C1—C2—C3	179.8 (6)	C11—C12—C13—C14	−0.2 (9)
C8—C1—C2—C7	0.0 (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—O2	179.9 (5)	C13—C14—C15—C16	1.5 (9)
C2—C1—C8—N3	1.4 (6)	F3—C15—C16—F4	−0.2 (8)
C1—C2—C3—C4	−179.3 (6)	F3—C15—C16—C11	179.3 (5)
C7—C2—C3—C4	0.6 (9)	C14—C15—C16—F4	179.7 (5)
C1—C2—C7—N3	−1.3 (6)	C14—C15—C16—C11	−0.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.99	2.694 (5)	139
N2—H2···F1	0.86	2.29	2.658 (5)	106
C6—H6···O1	0.93	2.33	2.857 (8)	116
C14—H14···O1i	0.93	2.32	3.217 (7)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.99	2.694 (5)	139
N2—H2⋯F1	0.86	2.29	2.658 (5)	106
C6—H6⋯O1	0.93	2.33	2.857 (8)	116
C14—H14⋯O1i	0.93	2.32	3.217 (7)	163

Symmetry code: (i) .