(Z)-N-Ethyl-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(11)FN(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules form chains through N-H⋯O hydrogen bonds, which are extended by N-H⋯S hydrogen bonds into an infinite three-dimensional network.

Related literature

For related structures, see: Ali et al. (2012a ▶,b ▶); Qasem Ali et al. (2011 ▶; 2012 ▶,c ▶,d ▶). For graph-set analysis, see Bernstein et al. (1995 ▶). For the biological activity of isatin and its derivatives, see: Suryavanshi & Pai (2006 ▶); Pandeya et al. (1999 ▶); Bhandari et al. (2008 ▶).

Experimental

Crystal data

C11H11FN4OS

M = 266.30

Orthorhombic,

a = 4.5151 (1) Å

b = 11.6102 (3) Å

c = 22.3255 (7) Å

V = 1170.33 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.43 × 0.09 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.887, T max = 0.987

8163 measured reflections

3384 independent reflections

2558 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.098

S = 1.09

3384 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 1367 Friedel pairs

Flack parameter: −0.12 (12)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036471/fy2062sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036471/fy2062Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036471/fy2062Isup3.cml

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

C11H11FN4OS	Dx = 1.511 Mg m−3
Mr = 266.30	Melting point = 521.3–522.1 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1888 reflections
a = 4.5151 (1) Å	θ = 3.3–26.6°
b = 11.6102 (3) Å	µ = 0.28 mm−1
c = 22.3255 (7) Å	T = 100 K
V = 1170.33 (5) Å3	Needle, yellow
Z = 4	0.43 × 0.09 × 0.05 mm
F(000) = 552

Bruker APEXII CCD diffractometer	3384 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→3
Tmin = 0.887, Tmax = 0.987	k = −16→16
8163 measured reflections	l = −31→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0233P)2 + 0.3031P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3384 reflections	Δρmax = 0.48 e Å−3
176 parameters	Δρmin = −0.40 e Å−3
0 restraints	Absolute structure: Flack (1983), 1367 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.12 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.

	x	y	z	Uiso*/Ueq
S1	1.24481 (17)	0.73593 (5)	0.74840 (3)	0.01960 (16)
F1	−0.1405 (4)	0.22456 (12)	0.90756 (7)	0.0262 (4)
O1	0.7062 (4)	0.74520 (13)	0.92210 (7)	0.0173 (4)
N1	0.3500 (6)	0.63660 (18)	0.97059 (10)	0.0169 (5)
N2	0.6774 (5)	0.54684 (16)	0.83437 (9)	0.0146 (5)
N3	0.8668 (5)	0.63110 (18)	0.81930 (9)	0.0143 (5)
N4	1.0264 (6)	0.5213 (2)	0.74068 (10)	0.0181 (5)
C1	0.2029 (7)	0.5313 (2)	0.96080 (11)	0.0149 (6)
C2	−0.0082 (7)	0.4801 (2)	0.99618 (11)	0.0173 (6)
H2A	−0.0732	0.5149	1.0324	0.021*
C3	−0.1231 (7)	0.3755 (2)	0.97690 (12)	0.0180 (6)
H3A	−0.2699	0.3370	0.9999	0.022*
C4	−0.0221 (7)	0.3275 (2)	0.92389 (12)	0.0188 (7)
C5	0.1898 (7)	0.3770 (2)	0.88805 (11)	0.0171 (6)
H5A	0.2550	0.3412	0.8521	0.021*
C6	0.3043 (6)	0.48216 (19)	0.90700 (11)	0.0131 (6)
C7	0.5237 (6)	0.5616 (2)	0.88265 (11)	0.0124 (6)
C8	0.5425 (7)	0.6604 (2)	0.92589 (11)	0.0138 (6)
C9	1.0386 (6)	0.6223 (2)	0.76802 (11)	0.0153 (6)
C10	1.1774 (7)	0.4928 (2)	0.68493 (11)	0.0205 (7)
H10A	1.2888	0.4200	0.6901	0.025*
H10B	1.3211	0.5544	0.6751	0.025*
C11	0.9584 (7)	0.4796 (2)	0.63365 (12)	0.0211 (7)
H11A	1.0663	0.4636	0.5965	0.032*
H11B	0.8445	0.5509	0.6291	0.032*
H11C	0.8232	0.4157	0.6423	0.032*
H1N1	0.326 (7)	0.679 (2)	1.0006 (11)	0.026 (9)*
H1N3	0.866 (6)	0.696 (2)	0.8394 (10)	0.009 (7)*
H1N4	0.928 (7)	0.473 (2)	0.7566 (12)	0.018 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0212 (4)	0.0175 (3)	0.0201 (3)	−0.0010 (3)	0.0025 (3)	0.0015 (3)
F1	0.0337 (11)	0.0178 (7)	0.0269 (9)	−0.0080 (8)	0.0005 (8)	0.0005 (7)
O1	0.0213 (12)	0.0156 (8)	0.0150 (9)	−0.0033 (9)	0.0001 (8)	−0.0028 (7)
N1	0.0218 (14)	0.0167 (11)	0.0121 (12)	0.0002 (11)	0.0024 (11)	−0.0060 (10)
N2	0.0146 (14)	0.0166 (10)	0.0124 (11)	0.0004 (10)	−0.0012 (10)	0.0009 (9)
N3	0.0157 (13)	0.0150 (10)	0.0121 (12)	0.0007 (10)	0.0019 (10)	−0.0023 (10)
N4	0.0214 (15)	0.0194 (11)	0.0136 (13)	−0.0022 (11)	0.0043 (11)	−0.0024 (10)
C1	0.0178 (17)	0.0140 (11)	0.0130 (13)	0.0044 (12)	−0.0019 (12)	0.0020 (10)
C2	0.0191 (17)	0.0203 (13)	0.0125 (14)	0.0041 (13)	0.0013 (13)	0.0018 (11)
C3	0.0164 (16)	0.0199 (13)	0.0176 (15)	0.0002 (12)	−0.0001 (12)	0.0089 (12)
C4	0.0226 (18)	0.0130 (12)	0.0209 (15)	0.0001 (13)	−0.0061 (13)	0.0021 (12)
C5	0.0198 (17)	0.0161 (12)	0.0153 (14)	0.0006 (12)	−0.0028 (12)	−0.0008 (11)
C6	0.0149 (16)	0.0140 (11)	0.0105 (13)	0.0030 (11)	0.0004 (11)	0.0020 (10)
C7	0.0148 (16)	0.0138 (12)	0.0085 (13)	0.0030 (11)	−0.0020 (11)	−0.0001 (10)
C8	0.0147 (16)	0.0165 (12)	0.0103 (13)	0.0041 (12)	−0.0033 (11)	−0.0010 (11)
C9	0.0137 (15)	0.0203 (13)	0.0118 (13)	0.0038 (12)	−0.0015 (11)	0.0024 (11)
C10	0.0234 (18)	0.0204 (13)	0.0179 (15)	0.0000 (13)	0.0063 (13)	−0.0042 (11)
C11	0.0266 (19)	0.0200 (13)	0.0166 (15)	−0.0022 (14)	0.0043 (13)	−0.0021 (12)

S1—C9	1.673 (3)	C2—C3	1.390 (4)
F1—C4	1.359 (3)	C2—H2A	0.9500
O1—C8	1.234 (3)	C3—C4	1.385 (4)
N1—C8	1.352 (3)	C3—H3A	0.9500
N1—C1	1.409 (3)	C4—C5	1.373 (4)
N1—H1N1	0.84 (2)	C5—C6	1.392 (3)
N2—C7	1.293 (3)	C5—H5A	0.9500
N2—N3	1.342 (3)	C6—C7	1.459 (4)
N3—C9	1.387 (3)	C7—C8	1.501 (3)
N3—H1N3	0.88 (2)	C10—C11	1.521 (4)
N4—C9	1.323 (3)	C10—H10A	0.9900
N4—C10	1.457 (3)	C10—H10B	0.9900
N4—H1N4	0.80 (3)	C11—H11A	0.9800
C1—C2	1.373 (4)	C11—H11B	0.9800
C1—C6	1.406 (3)	C11—H11C	0.9800
C8—N1—C1	111.5 (2)	C5—C6—C1	119.6 (2)
C8—N1—H1N1	123 (2)	C5—C6—C7	133.9 (2)
C1—N1—H1N1	125 (2)	C1—C6—C7	106.4 (2)
C7—N2—N3	117.0 (2)	N2—C7—C6	126.2 (2)
N2—N3—C9	120.7 (2)	N2—C7—C8	127.4 (2)
N2—N3—H1N3	119.8 (17)	C6—C7—C8	106.4 (2)
C9—N3—H1N3	119.0 (17)	O1—C8—N1	126.8 (2)
C9—N4—C10	125.2 (2)	O1—C8—C7	126.8 (2)
C9—N4—H1N4	116.1 (19)	N1—C8—C7	106.4 (2)
C10—N4—H1N4	118.7 (19)	N4—C9—N3	115.0 (2)
C2—C1—C6	122.8 (2)	N4—C9—S1	126.9 (2)
C2—C1—N1	127.8 (2)	N3—C9—S1	118.02 (19)
C6—C1—N1	109.3 (2)	N4—C10—C11	111.2 (2)
C1—C2—C3	117.3 (2)	N4—C10—H10A	109.4
C1—C2—H2A	121.3	C11—C10—H10A	109.4
C3—C2—H2A	121.3	N4—C10—H10B	109.4
C4—C3—C2	119.6 (3)	C11—C10—H10B	109.4
C4—C3—H3A	120.2	H10A—C10—H10B	108.0
C2—C3—H3A	120.2	C10—C11—H11A	109.5
F1—C4—C5	119.1 (2)	C10—C11—H11B	109.5
F1—C4—C3	116.9 (3)	H11A—C11—H11B	109.5
C5—C4—C3	124.0 (2)	C10—C11—H11C	109.5
C4—C5—C6	116.7 (2)	H11A—C11—H11C	109.5
C4—C5—H5A	121.7	H11B—C11—H11C	109.5
C6—C5—H5A	121.7
C7—N2—N3—C9	−179.6 (2)	N3—N2—C7—C8	−3.2 (4)
C8—N1—C1—C2	−179.4 (3)	C5—C6—C7—N2	−2.3 (5)
C8—N1—C1—C6	0.4 (3)	C1—C6—C7—N2	177.7 (3)
C6—C1—C2—C3	−0.1 (4)	C5—C6—C7—C8	179.8 (3)
N1—C1—C2—C3	179.7 (2)	C1—C6—C7—C8	−0.1 (3)
C1—C2—C3—C4	0.1 (4)	C1—N1—C8—O1	−178.9 (2)
C2—C3—C4—F1	179.4 (2)	C1—N1—C8—C7	−0.4 (3)
C2—C3—C4—C5	0.2 (4)	N2—C7—C8—O1	1.0 (5)
F1—C4—C5—C6	−179.8 (2)	C6—C7—C8—O1	178.8 (2)
C3—C4—C5—C6	−0.6 (4)	N2—C7—C8—N1	−177.5 (3)
C4—C5—C6—C1	0.6 (4)	C6—C7—C8—N1	0.3 (3)
C4—C5—C6—C7	−179.4 (3)	C10—N4—C9—N3	177.4 (2)
C2—C1—C6—C5	−0.3 (4)	C10—N4—C9—S1	−4.7 (4)
N1—C1—C6—C5	179.9 (2)	N2—N3—C9—N4	−7.8 (4)
C2—C1—C6—C7	179.7 (3)	N2—N3—C9—S1	174.10 (18)
N1—C1—C6—C7	−0.2 (3)	C9—N4—C10—C11	−109.6 (3)
N3—N2—C7—C6	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.84 (2)	2.01 (2)	2.836 (3)	168 (3)
N3—H1N3···O1	0.88 (2)	2.06 (2)	2.747 (3)	134 (2)
N4—H1N4···S1ii	0.80 (3)	2.86 (2)	3.541 (2)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.84 (2)	2.01 (2)	2.836 (3)	168 (3)
N3—H1N3⋯O1	0.88 (2)	2.06 (2)	2.747 (3)	134 (2)
N4—H1N4⋯S1ii	0.80 (3)	2.86 (2)	3.541 (2)	144 (2)

Symmetry codes: (i) ; (ii) .