4-(2-Fluoro-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

The title compound, C(15)H(11)FN(4)OS, is almost planar, the dihedral angle between the aromatic ring systems being 5.00 (13)°. The conformation is stabilized by intra-molecular N-H⋯N and N-H⋯O hydrogen bonds, which generate S(5) and S(6) rings, respectively. N-H⋯F and C-H⋯S inter-actions also occur. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, generating R(2) (2)(8) loops.

Related literature

For related structures and medicinal background, see: Pervez et al. (2009 ▶, 2010 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11FN4OS

M = 314.34

Monoclinic,

a = 5.7646 (3) Å

b = 18.4939 (12) Å

c = 13.6772 (8) Å

β = 91.212 (3)°

V = 1457.80 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.971

11407 measured reflections

2626 independent reflections

1437 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 0.96

2626 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.22 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 for Windows (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/S1600536810011682/hb5381sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011682/hb5381Isup2.hkl

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

C15H11FN4OS	F(000) = 648
Mr = 314.34	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2626 reflections
a = 5.7646 (3) Å	θ = 3.5–25.3°
b = 18.4939 (12) Å	µ = 0.24 mm−1
c = 13.6772 (8) Å	T = 296 K
β = 91.212 (3)°	Needle, dark yellow
V = 1457.80 (15) Å3	0.30 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
graphite	Rint = 0.068
Detector resolution: 7.80 pixels mm-1	θmax = 25.3°, θmin = 3.5°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→22
Tmin = 0.963, Tmax = 0.971	l = −16→16
11407 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
2626 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.22 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 esds 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
S1	0.09191 (15)	0.20047 (5)	0.00689 (6)	0.0742 (3)
F1	−0.0601 (3)	0.14317 (12)	0.37578 (11)	0.0911 (9)
O1	0.7157 (3)	0.04818 (11)	0.01234 (13)	0.0575 (8)
N1	0.9081 (4)	−0.02584 (13)	0.12316 (16)	0.0547 (9)
N2	0.4000 (4)	0.06836 (12)	0.18384 (15)	0.0489 (8)
N3	0.3340 (4)	0.10541 (12)	0.10344 (15)	0.0510 (8)
N4	0.0393 (3)	0.15113 (12)	0.19057 (14)	0.0499 (8)
C1	0.5848 (5)	0.02916 (15)	0.17922 (19)	0.0474 (10)
C2	0.7385 (5)	0.01971 (16)	0.0932 (2)	0.0494 (11)
C3	0.8851 (5)	−0.04562 (15)	0.2217 (2)	0.0513 (10)
C4	1.0273 (5)	−0.08819 (17)	0.2785 (2)	0.0696 (12)
C5	0.9689 (6)	−0.09758 (19)	0.3747 (3)	0.0803 (14)
C6	0.7757 (6)	−0.06518 (19)	0.4128 (2)	0.0774 (15)
C7	0.6305 (5)	−0.02238 (17)	0.3550 (2)	0.0658 (11)
C8	0.6871 (4)	−0.01264 (15)	0.25825 (19)	0.0494 (10)
C9	0.1480 (5)	0.15218 (15)	0.10471 (18)	0.0486 (10)
C10	−0.1520 (4)	0.19126 (15)	0.22268 (19)	0.0479 (10)
C11	−0.2029 (5)	0.18597 (18)	0.3198 (2)	0.0626 (11)
C12	−0.3861 (6)	0.2210 (2)	0.3614 (3)	0.0864 (14)
C13	−0.5248 (6)	0.2633 (2)	0.3026 (3)	0.0849 (16)
C14	−0.4818 (5)	0.26920 (18)	0.2062 (3)	0.0743 (14)
C15	−0.2977 (5)	0.23337 (16)	0.1658 (2)	0.0623 (11)
H1	1.01726	−0.04097	0.08643	0.0657*
H3	0.40914	0.09984	0.05030	0.0611*
H4	1.15840	−0.10996	0.25313	0.0834*
H4A	0.09573	0.12107	0.23275	0.0598*
H5	1.06218	−0.12647	0.41499	0.0960*
H6	0.74193	−0.07212	0.47828	0.0929*
H7	0.49911	−0.00091	0.38065	0.0791*
H12	−0.41496	0.21619	0.42776	0.1037*
H13	−0.64912	0.28809	0.32902	0.1015*
H14	−0.57770	0.29779	0.16668	0.0892*
H15	−0.27161	0.23771	0.09919	0.0747*

	U11	U22	U33	U12	U13	U23
S1	0.0779 (6)	0.0878 (7)	0.0577 (5)	0.0167 (5)	0.0193 (4)	0.0148 (5)
F1	0.0833 (14)	0.1408 (19)	0.0495 (10)	0.0171 (13)	0.0103 (9)	−0.0024 (11)
O1	0.0453 (12)	0.0735 (15)	0.0543 (12)	0.0021 (10)	0.0167 (9)	−0.0014 (11)
N1	0.0398 (14)	0.0640 (17)	0.0610 (15)	0.0076 (12)	0.0148 (11)	−0.0042 (13)
N2	0.0410 (14)	0.0541 (15)	0.0519 (14)	0.0019 (12)	0.0100 (11)	−0.0051 (12)
N3	0.0481 (14)	0.0577 (16)	0.0477 (14)	0.0049 (12)	0.0153 (11)	−0.0039 (12)
N4	0.0460 (14)	0.0585 (16)	0.0455 (13)	0.0098 (12)	0.0118 (11)	−0.0016 (11)
C1	0.0397 (16)	0.0486 (18)	0.0544 (17)	−0.0033 (14)	0.0127 (13)	−0.0092 (14)
C2	0.0399 (17)	0.055 (2)	0.0537 (18)	−0.0072 (15)	0.0124 (13)	−0.0104 (15)
C3	0.0417 (17)	0.0550 (19)	0.0574 (18)	0.0009 (15)	0.0072 (14)	−0.0036 (16)
C4	0.054 (2)	0.076 (2)	0.079 (2)	0.0149 (18)	0.0073 (17)	0.0046 (19)
C5	0.075 (2)	0.089 (3)	0.077 (2)	0.017 (2)	0.0008 (19)	0.012 (2)
C6	0.086 (3)	0.090 (3)	0.0564 (19)	0.010 (2)	0.0068 (18)	0.0090 (19)
C7	0.065 (2)	0.077 (2)	0.0558 (19)	0.0075 (19)	0.0142 (16)	−0.0024 (17)
C8	0.0425 (17)	0.0527 (19)	0.0532 (17)	0.0001 (14)	0.0055 (13)	−0.0062 (15)
C9	0.0448 (17)	0.0512 (18)	0.0504 (16)	−0.0002 (15)	0.0124 (13)	−0.0052 (14)
C10	0.0404 (16)	0.0517 (19)	0.0518 (17)	−0.0038 (15)	0.0073 (13)	−0.0137 (14)
C11	0.0508 (19)	0.085 (2)	0.0519 (18)	0.0027 (18)	0.0005 (15)	−0.0134 (17)
C12	0.065 (2)	0.131 (3)	0.064 (2)	0.001 (2)	0.0214 (18)	−0.036 (2)
C13	0.049 (2)	0.106 (3)	0.100 (3)	0.008 (2)	0.010 (2)	−0.044 (2)
C14	0.053 (2)	0.075 (2)	0.095 (3)	0.0098 (18)	0.0041 (18)	−0.016 (2)
C15	0.0504 (18)	0.069 (2)	0.068 (2)	0.0058 (17)	0.0099 (15)	−0.0038 (17)

S1—C9	1.635 (3)	C5—C6	1.377 (5)
F1—C11	1.365 (4)	C6—C7	1.387 (4)
O1—C2	1.229 (3)	C7—C8	1.381 (4)
N1—C2	1.348 (4)	C10—C15	1.375 (4)
N1—C3	1.406 (4)	C10—C11	1.370 (4)
N2—N3	1.344 (3)	C11—C12	1.373 (5)
N2—C1	1.291 (4)	C12—C13	1.368 (5)
N3—C9	1.378 (4)	C13—C14	1.351 (6)
N4—C9	1.343 (3)	C14—C15	1.377 (4)
N4—C10	1.407 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C7—H7	0.9300
C1—C8	1.445 (4)	C12—H12	0.9300
C1—C2	1.498 (4)	C13—H13	0.9300
C3—C8	1.396 (4)	C14—H14	0.9300
C3—C4	1.367 (4)	C15—H15	0.9300
C4—C5	1.376 (5)
S1···C15	3.216 (3)	C9···C2vi	3.403 (4)
S1···C13i	3.661 (4)	C9···C14iii	3.323 (4)
S1···C11ii	3.696 (3)	C9···O1vi	3.372 (3)
S1···C12ii	3.665 (4)	C10···C1vi	3.407 (4)
S1···H15	2.5600	C11···S1vii	3.696 (3)
S1···H13i	2.8900	C12···S1vii	3.665 (4)
F1···N4	2.613 (2)	C13···S1viii	3.661 (4)
F1···H4A	2.2100	C14···C9vi	3.323 (4)
O1···N2	3.022 (3)	C15···N3vi	3.280 (4)
O1···N3	2.762 (3)	C15···S1	3.216 (3)
O1···C9iii	3.372 (3)	C2···H3	2.4700
O1···N3iv	3.262 (3)	C2···H3iv	3.0600
O1···O1iv	3.072 (3)	C2···H1v	2.8800
O1···N1v	2.912 (3)	C5···H14ix	3.0200
O1···C2iv	3.218 (3)	C6···H14ix	2.9800
O1···H3	2.0800	C9···H15	2.8900
O1···H1v	2.0700	C14···H4x	2.9600
N1···O1v	2.912 (3)	H1···O1v	2.0700
N2···O1	3.022 (3)	H1···C2v	2.8800
N2···N4	2.585 (3)	H3···O1	2.0800
N3···O1iv	3.262 (3)	H3···C2	2.4700
N3···O1	2.762 (3)	H3···C2iv	3.0600
N3···C15iii	3.280 (4)	H4···C14xi	2.9600
N4···C2vi	3.254 (4)	H4A···F1	2.2100
N4···F1	2.613 (2)	H4A···N2	2.1300
N4···N2	2.585 (3)	H13···S1viii	2.8900
N2···H4A	2.1300	H14···C5xii	3.0200
C1···C10iii	3.407 (4)	H14···C6xii	2.9800
C2···N4iii	3.254 (4)	H15···S1	2.5600
C2···C9iii	3.403 (4)	H15···C9	2.8900
C2···O1iv	3.218 (3)
C2—N1—C3	111.8 (2)	S1—C9—N4	129.5 (2)
N3—N2—C1	117.8 (2)	C11—C10—C15	116.6 (2)
N2—N3—C9	121.1 (2)	N4—C10—C15	126.6 (2)
C9—N4—C10	130.4 (2)	N4—C10—C11	116.8 (2)
C3—N1—H1	124.00	C10—C11—C12	123.4 (3)
C2—N1—H1	124.00	F1—C11—C10	116.5 (2)
N2—N3—H3	119.00	F1—C11—C12	120.1 (3)
C9—N3—H3	119.00	C11—C12—C13	118.1 (4)
C10—N4—H4A	115.00	C12—C13—C14	120.2 (3)
C9—N4—H4A	115.00	C13—C14—C15	120.8 (3)
N2—C1—C2	127.3 (2)	C10—C15—C14	120.8 (3)
C2—C1—C8	106.6 (2)	C3—C4—H4	121.00
N2—C1—C8	126.0 (2)	C5—C4—H4	121.00
N1—C2—C1	105.8 (2)	C4—C5—H5	119.00
O1—C2—N1	127.2 (3)	C6—C5—H5	119.00
O1—C2—C1	127.1 (3)	C5—C6—H6	119.00
N1—C3—C4	128.9 (3)	C7—C6—H6	119.00
N1—C3—C8	108.9 (2)	C6—C7—H7	121.00
C4—C3—C8	122.2 (3)	C8—C7—H7	121.00
C3—C4—C5	117.4 (3)	C11—C12—H12	121.00
C4—C5—C6	121.6 (3)	C13—C12—H12	121.00
C5—C6—C7	121.1 (3)	C12—C13—H13	120.00
C6—C7—C8	117.9 (3)	C14—C13—H13	120.00
C1—C8—C3	106.9 (2)	C13—C14—H14	120.00
C3—C8—C7	119.8 (2)	C15—C14—H14	120.00
C1—C8—C7	133.3 (2)	C10—C15—H15	120.00
S1—C9—N3	118.23 (19)	C14—C15—H15	120.00
N3—C9—N4	112.3 (2)
C3—N1—C2—O1	177.5 (3)	C8—C3—C4—C5	−0.2 (5)
C3—N1—C2—C1	−1.8 (3)	N1—C3—C8—C1	−0.2 (3)
C2—N1—C3—C4	−177.2 (3)	N1—C3—C8—C7	−178.3 (3)
C2—N1—C3—C8	1.3 (3)	C4—C3—C8—C1	178.5 (3)
C1—N2—N3—C9	−175.5 (3)	C4—C3—C8—C7	0.3 (4)
N3—N2—C1—C2	0.0 (4)	C3—C4—C5—C6	−0.4 (5)
N3—N2—C1—C8	178.0 (2)	C4—C5—C6—C7	0.8 (5)
N2—N3—C9—S1	174.9 (2)	C5—C6—C7—C8	−0.7 (5)
N2—N3—C9—N4	−4.4 (4)	C6—C7—C8—C1	−177.4 (3)
C10—N4—C9—S1	−0.8 (4)	C6—C7—C8—C3	0.1 (4)
C10—N4—C9—N3	178.3 (2)	N4—C10—C11—F1	1.1 (4)
C9—N4—C10—C11	−170.6 (3)	N4—C10—C11—C12	−179.0 (3)
C9—N4—C10—C15	11.8 (4)	C15—C10—C11—F1	179.0 (3)
N2—C1—C2—O1	0.6 (5)	C15—C10—C11—C12	−1.1 (5)
N2—C1—C2—N1	180.0 (3)	N4—C10—C15—C14	179.0 (3)
C8—C1—C2—O1	−177.7 (3)	C11—C10—C15—C14	1.3 (4)
C8—C1—C2—N1	1.7 (3)	F1—C11—C12—C13	−180.0 (3)
N2—C1—C8—C3	−179.2 (3)	C10—C11—C12—C13	0.1 (5)
N2—C1—C8—C7	−1.5 (5)	C11—C12—C13—C14	0.7 (5)
C2—C1—C8—C3	−0.9 (3)	C12—C13—C14—C15	−0.5 (5)
C2—C1—C8—C7	176.9 (3)	C13—C14—C15—C10	−0.6 (5)
N1—C3—C4—C5	178.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1v	0.86	2.07	2.912 (3)	164
N3—H3···O1	0.86	2.08	2.762 (3)	135
N4—H4A···F1	0.86	2.21	2.613 (2)	109
N4—H4A···N2	0.86	2.13	2.585 (3)	113
C15—H15···S1	0.93	2.56	3.216 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.07	2.912 (3)	164
N3—H3⋯O1	0.86	2.08	2.762 (3)	135
N4—H4A⋯F1	0.86	2.21	2.613 (2)	109
N4—H4A⋯N2	0.86	2.13	2.585 (3)	113
C15—H15⋯S1	0.93	2.56	3.216 (3)	128

Symmetry code: (i) .