4-(3-Fluoro-phen-yl)-1-(propan-2-yl-idene)thio-semicarbazone.

The title compound, C(10)H(12)FN(3)S, crystallizes in the same space group (P2(1)/c) as two polymorphic forms of 4-phenyl-1-(propan-2-yl-idene)thio-semicarbazone [Jian et al. (2005). Acta Cryst. E61, o653-o654; Venkatraman et al. (2005). Acta Cryst. E61, o3914-o3916]. The arrangement of mol-ecules relative to the twofold screw axes is similar to that in the crystal structure of the lower density polymorph. In the solid state, the mol-ecular conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond. The mol-ecules form centrosymmetric R(2) (2)(8) dimers in the crystal through pairs of N-H⋯S hydrogen bonds.

Related literature

For related structures, see: Basu & Das (2011 ▶); Park & Ahn (1985 ▶); Parsons et al. (2000 ▶); Jian et al. (2005 ▶); Venkatraman et al. (2005 ▶). For description of the Cambridge Structural Database, see: Allen (2002 ▶). For the anti­tumor, anti­viral and anti­fungal activity of thio­semicarbazones, see: Kalinowski et al. (2009 ▶); Smee & Sidwell (2003 ▶); Beraldo & Gambino (2004 ▶). For their metal-chelating properties, see: Paterson & Donnelly (2011 ▶); Casas et al. (2000 ▶).

Experimental

Crystal data

C10H12FN3S

M = 225.29

Monoclinic,

a = 9.038 (2) Å

b = 10.515 (2) Å

c = 11.869 (2) Å

β = 99.77 (3)°

V = 1111.6 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.48 mm−1

T = 296 K

0.55 × 0.30 × 0.10 mm

Data collection

Kuma KM-4 diffractometer

Absorption correction: for a cylinder mounted on the ϕ axis (Dwiggins, 1975 ▶) T min = 0.435, T max = 0.485

3800 measured reflections

1942 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.084

3 standard reflections every 100 reflections intensity decay: 3.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.217

S = 1.04

1942 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.39 e Å−3

Data collection: KM-4 Software (Kuma Diffraction, 1991 ▶); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶), Mercury (Macrae et al., 2006 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042504/fy2024sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811042504/fy2024Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042504/fy2024Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811042504/fy2024Isup4.cml

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

C10H12FN3S	F(000) = 472
Mr = 225.29	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 75 reflections
a = 9.038 (2) Å	θ = 6–20°
b = 10.515 (2) Å	µ = 2.48 mm−1
c = 11.869 (2) Å	T = 296 K
β = 99.77 (3)°	Plate, colourless
V = 1111.6 (4) Å3	0.55 × 0.30 × 0.10 mm
Z = 4

Kuma KM-4 diffractometer	1252 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.084
graphite	θmax = 67.7°, θmin = 5.0°
ω–2θ scans	h = −10→10
Absorption correction: for a cylinder mounted on the φ axis (Dwiggins, 1975)	k = −12→12
Tmin = 0.435, Tmax = 0.485	l = 0→14
3800 measured reflections	3 standard reflections every 100 reflections
1942 independent reflections	intensity decay: 3.3%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1522P)2] where P = (Fo2 + 2Fc2)/3
1942 reflections	(Δ/σ)max = 0.013
138 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. cylinder dimensions used for absorption correction: 0.2 mm radius and a 0.1 mm height

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 > 2σ(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
C1	0.4980 (4)	0.4433 (3)	0.2021 (3)	0.0493 (8)
C1P	0.3908 (4)	0.4006 (4)	0.3776 (3)	0.0506 (9)
C2	0.8673 (4)	0.3455 (4)	0.1991 (3)	0.0557 (9)
C2P	0.3249 (5)	0.5171 (4)	0.3911 (3)	0.0566 (9)
H2P	0.3381	0.5864	0.3451	0.068*
C3	0.9760 (5)	0.2575 (6)	0.2680 (4)	0.0785 (14)
H3A	0.9395	0.2344	0.3366	0.094*
H3B	1.0715	0.2989	0.2876	0.094*
H3C	0.9870	0.1823	0.2242	0.094*
C3P	0.2380 (5)	0.5252 (4)	0.4767 (4)	0.0613 (10)
C4	0.9221 (5)	0.4267 (5)	0.1128 (4)	0.0718 (13)
H4A	0.9086	0.3830	0.0408	0.086*
H4B	1.0268	0.4448	0.1373	0.086*
H5C	0.8665	0.5049	0.1046	0.086*
C4P	0.2123 (5)	0.4283 (5)	0.5460 (4)	0.0675 (11)
H4P	0.1521	0.4384	0.6015	0.081*
C5P	0.2802 (6)	0.3136 (5)	0.5299 (4)	0.0700 (12)
H5P	0.2662	0.2447	0.5761	0.084*
C6P	0.3682 (5)	0.2991 (4)	0.4467 (4)	0.0639 (11)
H6P	0.4124	0.2209	0.4370	0.077*
N1	0.4913 (4)	0.3838 (3)	0.3000 (3)	0.0564 (8)
H1	0.5586	0.3263	0.3189	0.068*
N2	0.6276 (4)	0.4233 (3)	0.1607 (3)	0.0560 (8)
H2	0.6427	0.4587	0.0983	0.067*
N3	0.7337 (4)	0.3444 (4)	0.2220 (3)	0.0567 (8)
S1	0.36293 (11)	0.53442 (10)	0.12753 (8)	0.0578 (4)
F1	0.1751 (4)	0.6403 (3)	0.4920 (3)	0.0941 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0477 (18)	0.0465 (19)	0.0519 (19)	0.0021 (16)	0.0037 (14)	−0.0012 (15)
C1P	0.0412 (17)	0.061 (2)	0.0499 (18)	0.0004 (16)	0.0070 (14)	0.0020 (16)
C2	0.052 (2)	0.057 (2)	0.058 (2)	0.0001 (18)	0.0065 (17)	−0.0026 (18)
C2P	0.063 (2)	0.052 (2)	0.055 (2)	0.0007 (18)	0.0113 (17)	0.0036 (17)
C3	0.062 (3)	0.099 (3)	0.073 (3)	0.027 (3)	0.006 (2)	0.007 (3)
C3P	0.072 (3)	0.061 (2)	0.0521 (19)	0.012 (2)	0.0145 (18)	−0.0026 (18)
C4	0.049 (2)	0.087 (3)	0.078 (3)	−0.008 (2)	0.0078 (19)	0.011 (3)
C4P	0.071 (3)	0.078 (3)	0.058 (2)	0.008 (2)	0.0247 (19)	0.007 (2)
C5P	0.075 (3)	0.071 (3)	0.068 (3)	0.001 (2)	0.026 (2)	0.016 (2)
C6P	0.068 (3)	0.057 (2)	0.067 (2)	0.006 (2)	0.0116 (19)	0.0073 (19)
N1	0.0545 (18)	0.0620 (19)	0.0541 (17)	0.0156 (16)	0.0133 (13)	0.0080 (15)
N2	0.0498 (17)	0.0609 (18)	0.0572 (18)	0.0055 (15)	0.0087 (13)	0.0070 (15)
N3	0.0502 (17)	0.064 (2)	0.0564 (17)	0.0092 (15)	0.0107 (14)	0.0049 (15)
S1	0.0535 (6)	0.0664 (7)	0.0528 (6)	0.0100 (5)	0.0069 (4)	0.0064 (4)
F1	0.139 (3)	0.0729 (18)	0.0802 (18)	0.0358 (19)	0.0475 (18)	0.0055 (15)

C1—N1	1.331 (5)	C3P—C4P	1.354 (6)
C1—N2	1.361 (5)	C3P—F1	1.362 (5)
C1—S1	1.681 (4)	C4—H4A	0.9600
C1P—C6P	1.382 (6)	C4—H4B	0.9600
C1P—C2P	1.383 (6)	C4—H5C	0.9600
C1P—N1	1.409 (5)	C4P—C5P	1.381 (7)
C2—N3	1.282 (5)	C4P—H4P	0.9300
C2—C4	1.482 (6)	C5P—C6P	1.377 (6)
C2—C3	1.489 (6)	C5P—H5P	0.9300
C2P—C3P	1.389 (6)	C6P—H6P	0.9300
C2P—H2P	0.9300	N1—H1	0.8600
C3—H3A	0.9600	N2—N3	1.379 (5)
C3—H3B	0.9600	N2—H2	0.8600
C3—H3C	0.9600
N1—C1—N2	114.4 (3)	C2—C4—H4B	109.5
N1—C1—S1	126.2 (3)	H4A—C4—H4B	109.5
N2—C1—S1	119.4 (3)	C2—C4—H5C	109.5
C6P—C1P—C2P	120.3 (4)	H4A—C4—H5C	109.5
C6P—C1P—N1	117.9 (4)	H4B—C4—H5C	109.5
C2P—C1P—N1	121.6 (4)	C3P—C4P—C5P	116.6 (4)
N3—C2—C4	126.1 (4)	C3P—C4P—H4P	121.7
N3—C2—C3	115.8 (4)	C5P—C4P—H4P	121.7
C4—C2—C3	118.1 (4)	C6P—C5P—C4P	121.3 (4)
C1P—C2P—C3P	116.6 (4)	C6P—C5P—H5P	119.3
C1P—C2P—H2P	121.7	C4P—C5P—H5P	119.3
C3P—C2P—H2P	121.7	C5P—C6P—C1P	120.1 (4)
C2—C3—H3A	109.5	C5P—C6P—H6P	119.9
C2—C3—H3B	109.5	C1P—C6P—H6P	119.9
H3A—C3—H3B	109.5	C1—N1—C1P	129.9 (3)
C2—C3—H3C	109.5	C1—N1—H1	115.0
H3A—C3—H3C	109.5	C1P—N1—H1	115.0
H3B—C3—H3C	109.5	C1—N2—N3	117.8 (3)
C4P—C3P—F1	118.1 (4)	C1—N2—H2	121.1
C4P—C3P—C2P	125.0 (4)	N3—N2—H2	121.1
F1—C3P—C2P	116.9 (4)	C2—N3—N2	118.6 (4)
C2—C4—H4A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.86	2.12	2.553 (5)	111
N2—H2···S1i	0.86	2.67	3.465 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.86	2.12	2.553 (5)	111
N2—H2⋯S1i	0.86	2.67	3.465 (3)	154

Symmetry code: (i) .