1-(4-Fluoro-phen-yl)thio-urea.

In the title compound, C(7)H(7)FN(2)S, the aromatic ring plane and the thio-urea unit are twisted with a torsion angle C-C-N-C7 of 44.6 (2)°. In the crystal, N-H⋯S and N-H⋯F inter-molecular hydrogen bonds link the mol-ecules into infinite sheets that are stacked along the c axis.

Related literature

For the biological activity of fluorinated thio­ureas, see: Sun et al. (2006 ▶); Saeed et al. (2009 ▶); Xu et al. (2003 ▶). For the use of fluorinated thio­ureas in organic synthesis, see: Nosova et al. (2006 ▶, 2007 ▶); Lipunova et al. (2008 ▶); Berkessel et al. (2006 ▶). N′-(2-fluoro­benzo­yl)thio­urea derivatives are suitable substrates for studying intra­molecular hydrogen bonds and Fermi resonance, see: Hritzová & Koščík (2008 ▶).

Experimental

Crystal data

C7n class="CellLine">H7FN2S

M = 170.21

Monoclinic,

a = 9.1384 (8) Å

b = 8.4338 (7) Å

c = 10.5334 (9) Å

β = 109.796 (2)°

V = 763.85 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 120 K

0.43 × 0.39 × 0.29 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.857, T max = 0.900

6816 measured reflections

1814 independent reflections

1645 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.05

1814 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020246/pb2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020246/pb2028Isup2.hkl

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

C7H7FN2S	F(000) = 352
Mr = 170.21	Dx = 1.480 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1384 (8) Å	Cell parameters from 3596 reflections
b = 8.4338 (7) Å	θ = 3.2–28.3°
c = 10.5334 (9) Å	µ = 0.37 mm−1
β = 109.796 (2)°	T = 120 K
V = 763.85 (11) Å3	Block, colourless
Z = 4	0.43 × 0.39 × 0.29 mm

Bruker SMART APEX diffractometer	1814 independent reflections
Radiation source: sealed tube	1645 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.857, Tmax = 0.900	k = −10→11
6816 measured reflections	l = −13→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.3192P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1814 reflections	Δρmax = 0.44 e Å−3
101 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.02935 (4)	0.53586 (4)	0.71645 (4)	0.02753 (15)
F1	0.35073 (11)	0.23014 (12)	0.98827 (10)	0.0374 (3)
N1	0.84161 (13)	0.39046 (13)	0.81980 (12)	0.0224 (3)
H1A	0.8874	0.3066	0.8006	0.027*
N2	0.85423 (14)	0.66261 (14)	0.84570 (13)	0.0257 (3)
H2B	0.7864	0.6574	0.8882	0.031*
H2C	0.8920	0.7550	0.8332	0.031*
C1	0.71613 (14)	0.35888 (15)	0.86719 (13)	0.0195 (3)
C2	0.57627 (15)	0.44244 (16)	0.81997 (14)	0.0214 (3)
H2A	0.5656	0.5286	0.7594	0.026*
C3	0.45251 (16)	0.39984 (17)	0.86130 (14)	0.0247 (3)
H3A	0.3572	0.4568	0.8308	0.030*
C4	0.47151 (16)	0.27309 (18)	0.94755 (14)	0.0254 (3)
C5	0.60776 (17)	0.18705 (17)	0.99488 (14)	0.0261 (3)
H5A	0.6167	0.0995	1.0538	0.031*
C6	0.73102 (16)	0.23144 (17)	0.95434 (14)	0.0233 (3)
H6A	0.8262	0.1745	0.9863	0.028*
C7	0.89954 (15)	0.53115 (15)	0.80043 (14)	0.0206 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0258 (2)	0.0168 (2)	0.0483 (3)	−0.00188 (12)	0.02351 (17)	−0.00191 (14)
F1	0.0391 (5)	0.0376 (5)	0.0475 (6)	−0.0133 (4)	0.0304 (4)	−0.0076 (4)
N1	0.0228 (5)	0.0154 (5)	0.0330 (6)	0.0021 (4)	0.0145 (5)	0.0018 (4)
N2	0.0267 (6)	0.0174 (6)	0.0386 (7)	−0.0017 (4)	0.0184 (5)	−0.0025 (5)
C1	0.0198 (6)	0.0188 (6)	0.0207 (6)	−0.0022 (5)	0.0080 (5)	−0.0014 (5)
C2	0.0233 (6)	0.0190 (6)	0.0222 (6)	0.0008 (5)	0.0080 (5)	0.0007 (5)
C3	0.0218 (6)	0.0250 (7)	0.0284 (7)	−0.0005 (5)	0.0101 (5)	−0.0055 (5)
C4	0.0272 (7)	0.0276 (7)	0.0262 (7)	−0.0106 (5)	0.0154 (5)	−0.0091 (5)
C5	0.0353 (7)	0.0230 (7)	0.0207 (6)	−0.0069 (6)	0.0103 (6)	0.0000 (5)
C6	0.0250 (6)	0.0201 (6)	0.0235 (6)	−0.0010 (5)	0.0066 (5)	0.0013 (5)
C7	0.0164 (6)	0.0189 (6)	0.0261 (7)	0.0003 (4)	0.0066 (5)	0.0014 (5)

S1—C7	1.7035 (14)	C1—C2	1.3954 (18)
F1—C4	1.3616 (15)	C2—C3	1.3897 (19)
N1—C7	1.3427 (17)	C2—H2A	0.9500
N1—C1	1.4222 (15)	C3—C4	1.375 (2)
N1—H1A	0.8800	C3—H3A	0.9500
N2—C7	1.3274 (17)	C4—C5	1.380 (2)
N2—H2B	0.8800	C5—C6	1.3846 (19)
N2—H2C	0.8800	C5—H5A	0.9500
C1—C6	1.3899 (19)	C6—H6A	0.9500
C7—N1—C1	128.69 (11)	C2—C3—H3A	120.9
C7—N1—H1A	115.7	F1—C4—C3	118.71 (13)
C1—N1—H1A	115.7	F1—C4—C5	118.34 (13)
C7—N2—H2B	120.0	C3—C4—C5	122.95 (13)
C7—N2—H2C	120.0	C4—C5—C6	118.37 (13)
H2B—N2—H2C	120.0	C4—C5—H5A	120.8
C6—C1—C2	119.93 (12)	C6—C5—H5A	120.8
C6—C1—N1	117.80 (12)	C5—C6—C1	120.32 (13)
C2—C1—N1	122.03 (12)	C5—C6—H6A	119.8
C3—C2—C1	120.14 (13)	C1—C6—H6A	119.8
C3—C2—H2A	119.9	N2—C7—N1	119.76 (12)
C1—C2—H2A	119.9	N2—C7—S1	121.59 (10)
C4—C3—C2	118.28 (13)	N1—C7—S1	118.64 (10)
C4—C3—H3A	120.9
C7—N1—C1—C6	−141.01 (15)	F1—C4—C5—C6	−179.50 (12)
C7—N1—C1—C2	44.6 (2)	C3—C4—C5—C6	0.5 (2)
C6—C1—C2—C3	0.9 (2)	C4—C5—C6—C1	−0.5 (2)
N1—C1—C2—C3	175.14 (12)	C2—C1—C6—C5	−0.1 (2)
C1—C2—C3—C4	−0.9 (2)	N1—C1—C6—C5	−174.66 (12)
C2—C3—C4—F1	−179.79 (12)	C1—N1—C7—N2	10.3 (2)
C2—C3—C4—C5	0.2 (2)	C1—N1—C7—S1	−169.25 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.88	2.43	3.2841 (12)	163
N2—H2B···F1ii	0.88	2.30	3.0989 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.88	2.43	3.2841 (12)	163
N2—H2B⋯F1ii	0.88	2.30	3.0989 (15)	152

Symmetry codes: (i) ; (ii) .