1-(2-Oxoindolin-3-yl-idene)-4-[2-(tri-fluoro-meth-yl)phen-yl]thio-semicarbazide.

In the title compound, C(16)H(11)F(3)N(4)OS, the dihedral angle between the aromatic ring systems is 69.15 (10)°. Intra-molecular N-H⋯N and N-H⋯O hydrogen bonds generate S(5) and S(6) rings, respectively. A short N-H⋯F contact also occurs. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked by N-H⋯F hydrogen bonds, forming polymeric chains propagating in [100]. π-π inter-actions also exist between the centroids of the benzene rings of the 2-oxoindoline group at a distance of 3.543 (3) Å and a short C=O⋯π contact occurs. Two F atoms of the trifluoro-methyl group are disordered over two sets of sites in a 0.517 (8):0.483 (8) ratio.

Related literature

For the synthetic and biological background see: Pervez et al. (2007 ▶, 2008 ▶, 2010a ▶). For a related structure, see: Pervez et al. (2010b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H11F3N4OS

M = 364.35

Monoclinic,

a = 4.5214 (3) Å

b = 16.6197 (14) Å

c = 21.6111 (18) Å

β = 93.241 (3)°

V = 1621.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.32 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.970

12183 measured reflections

2886 independent reflections

1920 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.167

S = 1.02

2886 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.42 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/S160053681003343X/hb5611sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003343X/hb5611Isup2.hkl

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

C16H11F3N4OS	F(000) = 744
Mr = 364.35	Dx = 1.493 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1920 reflections
a = 4.5214 (3) Å	θ = 2.3–25.1°
b = 16.6197 (14) Å	µ = 0.24 mm−1
c = 21.6111 (18) Å	T = 296 K
β = 93.241 (3)°	Needle, yellow
V = 1621.4 (2) Å3	0.32 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	1920 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 8.3 pixels mm-1	θmax = 25.1°, θmin = 2.3°
ω scans	h = −5→3
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→19
Tmin = 0.962, Tmax = 0.970	l = −25→25
12183 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.076P)2 + 1.5855P] where P = (Fo2 + 2Fc2)/3
2886 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.42 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	Occ. (<1)
S1	0.1580 (3)	0.24551 (7)	0.21357 (6)	0.0553 (4)
F1	−0.0115 (7)	0.0741 (2)	0.08290 (15)	0.0825 (12)
F2A	0.375 (2)	0.0318 (5)	0.0597 (4)	0.0788 (14)	0.517 (8)
F3A	0.0360 (19)	−0.0568 (5)	0.0737 (4)	0.0788 (14)	0.517 (8)
O1	0.4521 (8)	0.42453 (18)	0.06431 (14)	0.0553 (10)
N1	0.7546 (8)	0.4227 (2)	−0.01834 (16)	0.0499 (11)
N2	0.6597 (8)	0.25246 (19)	0.07503 (15)	0.0416 (11)
N3	0.4709 (8)	0.27331 (19)	0.11784 (15)	0.0430 (11)
N4	0.4895 (8)	0.14419 (19)	0.15100 (16)	0.0466 (11)
C1	0.7346 (9)	0.3061 (2)	0.03602 (18)	0.0394 (12)
C2	0.9279 (9)	0.2941 (3)	−0.01449 (18)	0.0427 (12)
C3	1.0847 (11)	0.2284 (3)	−0.0344 (2)	0.0543 (17)
C4	1.2404 (12)	0.2366 (3)	−0.0870 (2)	0.0645 (17)
C5	1.2403 (12)	0.3090 (4)	−0.1191 (2)	0.0662 (19)
C6	1.0873 (11)	0.3748 (3)	−0.0996 (2)	0.0619 (17)
C7	0.9314 (10)	0.3661 (3)	−0.04719 (19)	0.0458 (14)
C8	0.6269 (10)	0.3914 (3)	0.03103 (19)	0.0438 (14)
C9	0.3807 (9)	0.2175 (2)	0.15997 (17)	0.0377 (12)
C10	0.4371 (9)	0.0756 (2)	0.18801 (19)	0.0428 (14)
C11	0.2761 (10)	0.0108 (3)	0.1631 (2)	0.0491 (16)
C12	0.2286 (12)	−0.0553 (3)	0.2002 (3)	0.070 (2)
C13	0.3394 (14)	−0.0571 (3)	0.2602 (3)	0.079 (2)
C14	0.5000 (13)	0.0060 (3)	0.2843 (3)	0.0698 (19)
C15	0.5497 (11)	0.0725 (3)	0.2485 (2)	0.0558 (17)
C16	0.1630 (12)	0.0110 (3)	0.0976 (3)	0.0607 (17)
F2B	0.361 (2)	−0.0028 (6)	0.0569 (4)	0.0788 (14)	0.483 (8)
F3B	−0.057 (2)	−0.0436 (5)	0.0932 (4)	0.0788 (14)	0.483 (8)
H1	0.73080	0.47161	−0.03071	0.0598*
H4	1.34692	0.19316	−0.10120	0.0768*
H3	1.08507	0.18001	−0.01281	0.0654*
H3A	0.40563	0.32185	0.11904	0.0515*
H6	1.08915	0.42337	−0.12097	0.0737*
H12	0.12021	−0.09878	0.18408	0.0849*
H13	0.30519	−0.10167	0.28480	0.0948*
H14	0.57634	0.00410	0.32511	0.0834*
H15	0.65944	0.11541	0.26521	0.0668*
H4A	0.60046	0.13790	0.12033	0.0558*
H5	1.34620	0.31296	−0.15461	0.0794*

	U11	U22	U33	U12	U13	U23
S1	0.0671 (8)	0.0496 (7)	0.0511 (7)	0.0070 (6)	0.0199 (6)	0.0021 (5)
F1	0.086 (2)	0.083 (2)	0.078 (2)	0.0254 (19)	−0.0001 (17)	0.0080 (17)
F2A	0.091 (2)	0.076 (3)	0.070 (2)	0.007 (3)	0.0103 (16)	−0.042 (2)
F3A	0.091 (2)	0.076 (3)	0.070 (2)	0.007 (3)	0.0103 (16)	−0.042 (2)
O1	0.078 (2)	0.0382 (16)	0.0506 (18)	0.0052 (16)	0.0105 (17)	0.0086 (14)
N1	0.063 (2)	0.0381 (19)	0.049 (2)	−0.0037 (17)	0.0070 (18)	0.0155 (16)
N2	0.052 (2)	0.0348 (18)	0.0383 (18)	−0.0034 (16)	0.0060 (16)	0.0034 (15)
N3	0.057 (2)	0.0297 (17)	0.0429 (19)	0.0026 (16)	0.0086 (17)	0.0053 (14)
N4	0.064 (2)	0.0330 (19)	0.045 (2)	−0.0015 (16)	0.0229 (17)	0.0028 (15)
C1	0.049 (2)	0.033 (2)	0.036 (2)	−0.0040 (18)	0.0003 (18)	0.0058 (17)
C2	0.047 (2)	0.042 (2)	0.039 (2)	−0.009 (2)	0.0005 (19)	0.0043 (18)
C3	0.066 (3)	0.048 (3)	0.049 (3)	−0.009 (2)	0.005 (2)	0.003 (2)
C4	0.069 (3)	0.068 (3)	0.058 (3)	−0.008 (3)	0.017 (3)	−0.010 (3)
C5	0.068 (3)	0.085 (4)	0.047 (3)	−0.017 (3)	0.015 (2)	0.003 (3)
C6	0.067 (3)	0.069 (3)	0.050 (3)	−0.015 (3)	0.007 (2)	0.019 (2)
C7	0.045 (2)	0.051 (3)	0.041 (2)	−0.011 (2)	−0.0014 (19)	0.009 (2)
C8	0.055 (3)	0.036 (2)	0.040 (2)	−0.006 (2)	−0.002 (2)	0.0090 (18)
C9	0.047 (2)	0.032 (2)	0.034 (2)	−0.0045 (18)	0.0019 (18)	0.0011 (16)
C10	0.052 (3)	0.031 (2)	0.047 (2)	0.0045 (19)	0.016 (2)	0.0073 (18)
C11	0.057 (3)	0.032 (2)	0.059 (3)	0.005 (2)	0.010 (2)	0.0033 (19)
C12	0.079 (4)	0.033 (3)	0.099 (4)	−0.008 (2)	0.003 (3)	0.013 (3)
C13	0.091 (4)	0.055 (3)	0.093 (4)	0.002 (3)	0.016 (4)	0.038 (3)
C14	0.087 (4)	0.066 (3)	0.057 (3)	0.007 (3)	0.010 (3)	0.023 (3)
C15	0.071 (3)	0.047 (3)	0.050 (3)	−0.003 (2)	0.010 (2)	0.005 (2)
C16	0.066 (3)	0.041 (3)	0.075 (3)	−0.006 (2)	0.004 (3)	−0.007 (2)
F2B	0.091 (2)	0.076 (3)	0.070 (2)	0.007 (3)	0.0103 (16)	−0.042 (2)
F3B	0.091 (2)	0.076 (3)	0.070 (2)	0.007 (3)	0.0103 (16)	−0.042 (2)

S1—C9	1.645 (4)	C2—C7	1.390 (7)
F1—C16	1.340 (6)	C3—C4	1.377 (7)
F2A—C16	1.341 (11)	C4—C5	1.389 (8)
F2B—C16	1.310 (11)	C5—C6	1.373 (8)
F3A—C16	1.354 (10)	C6—C7	1.375 (6)
F3B—C16	1.346 (10)	C10—C15	1.377 (6)
O1—C8	1.229 (6)	C10—C11	1.391 (6)
N1—C8	1.346 (6)	C11—C12	1.384 (7)
N1—C7	1.403 (6)	C11—C16	1.478 (8)
N2—C1	1.286 (5)	C12—C13	1.364 (9)
N2—N3	1.339 (5)	C13—C14	1.362 (8)
N3—C9	1.378 (5)	C14—C15	1.375 (7)
N4—C10	1.420 (5)	C3—H3	0.9300
N4—C9	1.332 (5)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3A	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C12—H12	0.9300
C1—C2	1.450 (6)	C13—H13	0.9300
C1—C8	1.501 (6)	C14—H14	0.9300
C2—C3	1.384 (7)	C15—H15	0.9300
C7—N1—C8	112.0 (4)	C10—C11—C12	119.0 (4)
N3—N2—C1	118.4 (3)	C10—C11—C16	120.9 (4)
N2—N3—C9	120.4 (3)	C11—C12—C13	120.5 (5)
C9—N4—C10	125.3 (3)	C12—C13—C14	120.4 (5)
C8—N1—H1	124.00	C13—C14—C15	120.3 (6)
C7—N1—H1	124.00	C10—C15—C14	120.1 (5)
N2—N3—H3A	120.00	F1—C16—C11	113.3 (5)
C9—N3—H3A	120.00	F1—C16—F2B	113.2 (6)
C10—N4—H4A	117.00	F2B—C16—C11	115.5 (6)
C9—N4—H4A	117.00	F3B—C16—C11	106.3 (6)
N2—C1—C8	127.3 (4)	F2B—C16—F3B	111.4 (7)
N2—C1—C2	126.2 (4)	F1—C16—F3B	95.1 (5)
C2—C1—C8	106.4 (3)	F2A—C16—F3A	106.5 (7)
C1—C2—C7	106.8 (4)	F2A—C16—C11	111.4 (6)
C1—C2—C3	133.1 (4)	F3A—C16—C11	118.7 (6)
C3—C2—C7	120.0 (4)	F1—C16—F2A	94.9 (5)
C2—C3—C4	118.3 (4)	F1—C16—F3A	109.3 (6)
C3—C4—C5	120.8 (5)	C2—C3—H3	121.00
C4—C5—C6	121.5 (4)	C4—C3—H3	121.00
C5—C6—C7	117.4 (5)	C3—C4—H4	120.00
N1—C7—C2	109.2 (4)	C5—C4—H4	120.00
N1—C7—C6	128.8 (4)	C4—C5—H5	119.00
C2—C7—C6	122.0 (4)	C6—C5—H5	119.00
O1—C8—C1	126.7 (4)	C5—C6—H6	121.00
N1—C8—C1	105.7 (4)	C7—C6—H6	121.00
O1—C8—N1	127.6 (4)	C11—C12—H12	120.00
S1—C9—N4	127.4 (3)	C13—C12—H12	120.00
S1—C9—N3	119.4 (3)	C12—C13—H13	120.00
N3—C9—N4	113.2 (3)	C14—C13—H13	120.00
N4—C10—C15	120.0 (4)	C13—C14—H14	120.00
N4—C10—C11	120.3 (4)	C15—C14—H14	120.00
C11—C10—C15	119.7 (4)	C10—C15—H15	120.00
C12—C11—C16	120.0 (5)	C14—C15—H15	120.00
C8—N1—C7—C2	−1.7 (5)	C3—C2—C7—N1	179.4 (4)
C8—N1—C7—C6	177.6 (5)	C3—C2—C7—C6	0.1 (7)
C7—N1—C8—O1	−177.0 (4)	C2—C3—C4—C5	0.1 (7)
C7—N1—C8—C1	1.2 (5)	C3—C4—C5—C6	0.3 (8)
C1—N2—N3—C9	179.0 (4)	C4—C5—C6—C7	−0.6 (7)
N3—N2—C1—C2	−178.0 (4)	C5—C6—C7—N1	−178.8 (5)
N3—N2—C1—C8	−2.0 (6)	C5—C6—C7—C2	0.4 (7)
N2—N3—C9—S1	177.9 (3)	N4—C10—C11—C12	179.9 (4)
N2—N3—C9—N4	−2.7 (5)	N4—C10—C11—C16	1.5 (6)
C10—N4—C9—S1	−1.6 (6)	C15—C10—C11—C12	1.0 (7)
C10—N4—C9—N3	178.9 (4)	C15—C10—C11—C16	−177.5 (4)
C9—N4—C10—C11	113.7 (5)	N4—C10—C15—C14	−179.8 (4)
C9—N4—C10—C15	−67.3 (6)	C11—C10—C15—C14	−0.8 (7)
N2—C1—C2—C3	−1.7 (8)	C10—C11—C12—C13	−0.4 (8)
N2—C1—C2—C7	176.0 (4)	C16—C11—C12—C13	178.1 (5)
C8—C1—C2—C3	−178.3 (5)	C10—C11—C16—F1	−56.9 (6)
C8—C1—C2—C7	−0.7 (5)	C10—C11—C16—F2A	48.7 (7)
N2—C1—C8—O1	1.3 (7)	C10—C11—C16—F3A	172.9 (6)
N2—C1—C8—N1	−176.9 (4)	C12—C11—C16—F1	124.6 (5)
C2—C1—C8—O1	177.9 (4)	C12—C11—C16—F2A	−129.8 (6)
C2—C1—C8—N1	−0.3 (5)	C12—C11—C16—F3A	−5.6 (8)
C1—C2—C3—C4	177.1 (5)	C11—C12—C13—C14	−0.4 (9)
C7—C2—C3—C4	−0.3 (7)	C12—C13—C14—C15	0.6 (9)
C1—C2—C7—N1	1.4 (5)	C13—C14—C15—C10	0.0 (8)
C1—C2—C7—C6	−177.9 (4)

Cg1 is the centroid of the C1/C2/C7/N1/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.03	2.864 (5)	163
N3—H3A···O1	0.86	2.09	2.766 (4)	135
N4—H4A···F1ii	0.86	2.24	2.998 (5)	147
N4—H4A···F2A	0.86	2.39	2.745 (9)	105
N4—H4A···N2	0.86	2.16	2.582 (5)	110
C3—H3···F3Aiii	0.93	2.48	3.017 (10)	117
C8—O1···Cg1iv	1.229 (6)	3.424 (4)	3.835 (5)	100.1 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/C7/N1/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.03	2.864 (5)	163
N3—H3A⋯O1	0.86	2.09	2.766 (4)	135
N4—H4A⋯F1ii	0.86	2.24	2.998 (5)	147
N4—H4A⋯F2A	0.86	2.39	2.745 (9)	105
N4—H4A⋯N2	0.86	2.16	2.582 (5)	110
C3—H3⋯F3Aiii	0.93	2.48	3.017 (10)	117
C8—O1⋯Cg1iv	1.23 (1)	3.42 (1)	3.835 (5)	100 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .