N-(4-Chloro-benzo-yl)-N'-(3-fluoro-phen-yl)thio-urea.

In the title compound, C(14)H(10)ClFN(2)OS, the mol-ecule adopts a trans-cis geometry of the thio-urea unit. The dihedral angles between the benzene rings is 34.47 (7)°. The crystal packing features inter-molecular N-H⋯S and C-H⋯O hydrogen bonds, forming a chain along the b axis. A short C-H⋯S intramolecular contact is also observed.

Related literature

For the biological and anti corrosion properties of thio­urea derivatives, see: Shen et al. (2006 ▶); Sun et al.(2006 ▶). For the structures of related 4-chloro­benzoyl thio­urea derivatives, see: Khawar Rauf et al. (2009 ▶); Yusof et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10ClFN2OS

M = 308.75

Monoclinic,

a = 8.5778 (1) Å

b = 11.7584 (2) Å

c = 13.4069 (2) Å

β = 92.448 (2)°

V = 1351.00 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.03 mm−1

T = 293 K

0.50 × 0.29 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.238, T max = 0.432

33403 measured reflections

2685 independent reflections

2628 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.06

2685 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030965/dn2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030965/dn2588Isup2.hkl

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

C14H10ClFN2OS	F(000) = 632
Mr = 308.75	Dx = 1.518 Mg m−3
Monoclinic, P21/c	Melting point: 459 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 8.5778 (1) Å	Cell parameters from 24507 reflections
b = 11.7584 (2) Å	θ = 5.0–72.7°
c = 13.4069 (2) Å	µ = 4.03 mm−1
β = 92.448 (2)°	T = 293 K
V = 1351.00 (3) Å3	Block, colourless
Z = 4	0.50 × 0.29 × 0.25 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2685 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2628 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 16.1952 pixels mm-1	θmax = 72.7°, θmin = 5.0°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.238, Tmax = 0.432	l = −16→16
33403 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.5662P] where P = (Fo2 + 2Fc2)/3
2685 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlisPro (Oxford Diffraction, 2010)

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
Cl1	0.68504 (4)	0.20726 (4)	0.98436 (3)	0.03536 (13)
S1	1.21472 (5)	0.03202 (3)	0.43885 (3)	0.03022 (13)
F1	1.42690 (13)	0.17249 (11)	0.12225 (8)	0.0484 (3)
O1	1.06117 (13)	0.36258 (8)	0.58155 (8)	0.0294 (2)
N1	1.06930 (14)	0.17096 (10)	0.55597 (9)	0.0236 (3)
H1A	1.0313	0.1078	0.5764	0.028*
N2	1.20911 (14)	0.26185 (10)	0.43716 (9)	0.0244 (3)
H2A	1.1773	0.3206	0.4686	0.029*
C1	0.94098 (17)	0.14201 (12)	0.75021 (11)	0.0247 (3)
H1B	0.9950	0.0807	0.7247	0.030*
C2	0.86286 (18)	0.12932 (13)	0.83788 (11)	0.0278 (3)
H2B	0.8634	0.0600	0.8712	0.033*
C3	0.78396 (17)	0.22191 (13)	0.87489 (10)	0.0255 (3)
C4	0.78102 (18)	0.32590 (13)	0.82683 (11)	0.0284 (3)
H4A	0.7276	0.3871	0.8530	0.034*
C5	0.85897 (18)	0.33731 (12)	0.73923 (11)	0.0265 (3)
H5A	0.8578	0.4069	0.7062	0.032*
C6	0.93944 (16)	0.24564 (11)	0.69979 (10)	0.0216 (3)
C7	1.02701 (16)	0.26641 (12)	0.60795 (10)	0.0226 (3)
C8	1.16519 (16)	0.16253 (12)	0.47485 (10)	0.0220 (3)
C9	1.29923 (16)	0.28669 (12)	0.35414 (11)	0.0245 (3)
C10	1.35933 (19)	0.39669 (14)	0.34964 (13)	0.0330 (3)
H10A	1.3439	0.4479	0.4012	0.040*
C11	1.4424 (2)	0.42933 (16)	0.26764 (15)	0.0414 (4)
H11A	1.4825	0.5027	0.2651	0.050*
C12	1.46672 (19)	0.35550 (16)	0.19007 (14)	0.0398 (4)
H12A	1.5221	0.3776	0.1352	0.048*
C13	1.40591 (18)	0.24824 (16)	0.19719 (12)	0.0333 (4)
C14	1.32205 (17)	0.21067 (13)	0.27676 (11)	0.0274 (3)
H14A	1.2824	0.1371	0.2784	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.0334 (2)	0.0521 (3)	0.02125 (19)	−0.00362 (16)	0.00978 (15)	−0.00270 (15)
S1	0.0401 (2)	0.01980 (19)	0.0323 (2)	−0.00030 (13)	0.01862 (16)	−0.00299 (13)
F1	0.0517 (6)	0.0658 (7)	0.0294 (5)	0.0014 (5)	0.0214 (4)	0.0013 (5)
O1	0.0390 (6)	0.0187 (5)	0.0315 (6)	−0.0022 (4)	0.0119 (5)	−0.0016 (4)
N1	0.0312 (6)	0.0176 (5)	0.0228 (6)	−0.0027 (5)	0.0098 (5)	−0.0013 (4)
N2	0.0294 (6)	0.0201 (6)	0.0243 (6)	−0.0004 (5)	0.0085 (5)	−0.0008 (4)
C1	0.0313 (7)	0.0213 (6)	0.0219 (7)	0.0031 (5)	0.0034 (5)	−0.0026 (5)
C2	0.0347 (8)	0.0268 (7)	0.0220 (7)	−0.0002 (6)	0.0024 (6)	0.0018 (5)
C3	0.0235 (7)	0.0366 (8)	0.0165 (6)	−0.0032 (6)	0.0030 (5)	−0.0035 (5)
C4	0.0304 (7)	0.0287 (7)	0.0263 (7)	0.0042 (6)	0.0051 (6)	−0.0075 (6)
C5	0.0328 (8)	0.0213 (7)	0.0256 (7)	0.0015 (6)	0.0039 (6)	−0.0029 (5)
C6	0.0237 (6)	0.0216 (6)	0.0194 (6)	−0.0008 (5)	0.0024 (5)	−0.0028 (5)
C7	0.0250 (7)	0.0205 (7)	0.0223 (7)	0.0001 (5)	0.0028 (5)	−0.0025 (5)
C8	0.0242 (6)	0.0217 (6)	0.0202 (6)	−0.0013 (5)	0.0037 (5)	−0.0009 (5)
C9	0.0206 (6)	0.0269 (7)	0.0262 (7)	0.0007 (5)	0.0031 (5)	0.0077 (5)
C10	0.0328 (8)	0.0265 (7)	0.0400 (9)	−0.0007 (6)	0.0041 (6)	0.0072 (6)
C11	0.0337 (8)	0.0351 (9)	0.0558 (11)	−0.0053 (7)	0.0077 (8)	0.0205 (8)
C12	0.0295 (8)	0.0516 (10)	0.0393 (9)	0.0025 (7)	0.0121 (7)	0.0224 (8)
C13	0.0264 (7)	0.0474 (9)	0.0267 (8)	0.0051 (7)	0.0072 (6)	0.0090 (7)
C14	0.0243 (7)	0.0327 (8)	0.0258 (7)	−0.0003 (6)	0.0062 (6)	0.0048 (6)

Cl1—C3	1.7350 (14)	C4—C5	1.383 (2)
S1—C8	1.6691 (14)	C4—H4A	0.9300
F1—C13	1.360 (2)	C5—C6	1.396 (2)
O1—C7	1.2243 (18)	C5—H5A	0.9300
N1—C7	1.3778 (18)	C6—C7	1.4896 (19)
N1—C8	1.3949 (17)	C9—C14	1.390 (2)
N1—H1A	0.8600	C9—C10	1.395 (2)
N2—C8	1.3332 (18)	C10—C11	1.390 (2)
N2—C9	1.4125 (18)	C10—H10A	0.9300
N2—H2A	0.8600	C11—C12	1.377 (3)
C1—C2	1.386 (2)	C11—H11A	0.9300
C1—C6	1.393 (2)	C12—C13	1.370 (3)
C1—H1B	0.9300	C12—H12A	0.9300
C2—C3	1.385 (2)	C13—C14	1.384 (2)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.382 (2)
C7—N1—C8	128.98 (12)	O1—C7—N1	122.32 (13)
C7—N1—H1A	115.5	O1—C7—C6	121.72 (12)
C8—N1—H1A	115.5	N1—C7—C6	115.94 (12)
C8—N2—C9	130.76 (13)	N2—C8—N1	114.77 (12)
C8—N2—H2A	114.6	N2—C8—S1	128.04 (11)
C9—N2—H2A	114.6	N1—C8—S1	117.17 (10)
C2—C1—C6	120.71 (13)	C14—C9—C10	120.01 (14)
C2—C1—H1B	119.6	C14—C9—N2	123.68 (13)
C6—C1—H1B	119.6	C10—C9—N2	116.20 (14)
C3—C2—C1	118.74 (14)	C11—C10—C9	119.56 (16)
C3—C2—H2B	120.6	C11—C10—H10A	120.2
C1—C2—H2B	120.6	C9—C10—H10A	120.2
C2—C3—C4	121.87 (13)	C12—C11—C10	121.50 (16)
C2—C3—Cl1	119.29 (12)	C12—C11—H11A	119.2
C4—C3—Cl1	118.84 (11)	C10—C11—H11A	119.2
C5—C4—C3	118.83 (14)	C13—C12—C11	117.22 (15)
C5—C4—H4A	120.6	C13—C12—H12A	121.4
C3—C4—H4A	120.6	C11—C12—H12A	121.4
C4—C5—C6	120.77 (14)	F1—C13—C12	119.25 (15)
C4—C5—H5A	119.6	F1—C13—C14	116.73 (16)
C6—C5—H5A	119.6	C12—C13—C14	124.02 (17)
C1—C6—C5	119.09 (13)	C13—C14—C9	117.68 (15)
C1—C6—C7	123.35 (12)	C13—C14—H14A	121.2
C5—C6—C7	117.48 (13)	C9—C14—H14A	121.2
C6—C1—C2—C3	−0.4 (2)	C9—N2—C8—N1	−177.20 (13)
C1—C2—C3—C4	0.1 (2)	C9—N2—C8—S1	4.6 (2)
C1—C2—C3—Cl1	179.79 (11)	C7—N1—C8—N2	−7.1 (2)
C2—C3—C4—C5	0.1 (2)	C7—N1—C8—S1	171.32 (12)
Cl1—C3—C4—C5	−179.56 (11)	C8—N2—C9—C14	20.2 (2)
C3—C4—C5—C6	0.0 (2)	C8—N2—C9—C10	−163.45 (15)
C2—C1—C6—C5	0.5 (2)	C14—C9—C10—C11	−0.3 (2)
C2—C1—C6—C7	177.04 (13)	N2—C9—C10—C11	−176.72 (14)
C4—C5—C6—C1	−0.3 (2)	C9—C10—C11—C12	0.2 (3)
C4—C5—C6—C7	−177.01 (13)	C10—C11—C12—C13	−0.2 (3)
C8—N1—C7—O1	6.6 (2)	C11—C12—C13—F1	179.93 (15)
C8—N1—C7—C6	−172.23 (13)	C11—C12—C13—C14	0.3 (3)
C1—C6—C7—O1	−158.63 (14)	F1—C13—C14—C9	180.00 (13)
C5—C6—C7—O1	17.9 (2)	C12—C13—C14—C9	−0.3 (2)
C1—C6—C7—N1	20.2 (2)	C10—C9—C14—C13	0.3 (2)
C5—C6—C7—N1	−163.19 (13)	N2—C9—C14—C13	176.49 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···S1	0.93	2.57	3.1865 (15)	124
N2—H2A···O1	0.86	1.91	2.6402 (16)	141
N1—H1A···S1i	0.86	2.68	3.4134 (13)	145
C2—H2B···O1ii	0.93	2.48	3.3717 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯S1	0.93	2.57	3.1865 (15)	124
N2—H2A⋯O1	0.86	1.91	2.6402 (16)	141
N1—H1A⋯S1i	0.86	2.68	3.4134 (13)	145
C2—H2B⋯O1ii	0.93	2.48	3.3717 (18)	160

Symmetry codes: (i) ; (ii) .