1-(2-Chloro-benzo-yl)-3-(2-trifluoro-methyl-phen-yl)thio-urea.

The dihedral angle between the benzene rings in the title compound, C15H10ClF3N2OS, is 54.02 (4)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, N-H⋯S hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For our previous work on the structural and coordination chemistry of N,N′-disubstituted thio­ureas and a related structure, see: Rauf et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen et al. (2002 ▶).

Experimental

Crystal data

C15H10ClF3N2OS

M = 358.76

Triclinic,

a = 7.705 (3) Å

b = 8.348 (3) Å

c = 12.465 (5) Å

α = 84.92 (1)°

β = 72.913 (9)°

γ = 86.272 (11)°

V = 762.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 123 K

0.45 × 0.36 × 0.28 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

5989 measured reflections

3408 independent reflections

3240 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.075

S = 1.07

3408 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: Yadokari-XG (Wakita, 2001 ▶; Kabuto et al., 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048829/hg5276sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048829/hg5276Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048829/hg5276Isup3.cml

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

C15H10ClF3N2OS	Z = 2
Mr = 358.76	F(000) = 364
Triclinic, P1	Dx = 1.562 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.705 (3) Å	Cell parameters from 2652 reflections
b = 8.348 (3) Å	θ = 3.1–27.5°
c = 12.465 (5) Å	µ = 0.42 mm−1
α = 84.92 (1)°	T = 123 K
β = 72.913 (9)°	Block, colorless
γ = 86.272 (11)°	0.45 × 0.36 × 0.28 mm
V = 762.7 (5) Å3

Rigaku/MSC Mercury CCD diffractometer	3240 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.023
Graphite Monochromator monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 14.62 pixels mm-1	h = −8→10
ω scans	k = −10→10
5989 measured reflections	l = −16→12
3408 independent 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0273P)2 + 0.4772P] where P = (Fo2 + 2Fc2)/3
3408 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	Occ. (<1)
C1	0.88846 (18)	0.27682 (16)	0.40388 (11)	0.0167 (3)
O1	1.00871 (14)	0.25013 (13)	0.31743 (8)	0.0241 (2)
N1	0.72626 (15)	0.35754 (14)	0.40451 (9)	0.0171 (2)
H1	0.6488	0.3712	0.4711	0.020*
C2	0.67122 (17)	0.41979 (16)	0.31202 (11)	0.0157 (2)
S1	0.47107 (4)	0.52082 (4)	0.33205 (3)	0.01981 (10)
N2	0.78777 (15)	0.39383 (14)	0.21154 (9)	0.0181 (2)
H2	0.8874	0.3349	0.2097	0.022*
C3	0.91513 (17)	0.22916 (16)	0.51696 (11)	0.0161 (3)
C4	0.79470 (18)	0.13899 (16)	0.60350 (11)	0.0166 (3)
C5	0.8315 (2)	0.09787 (17)	0.70526 (12)	0.0215 (3)
H5	0.7486	0.0367	0.7637	0.026*
C6	0.9904 (2)	0.14674 (18)	0.72090 (13)	0.0243 (3)
H6	1.0150	0.1206	0.7909	0.029*
C7	1.1135 (2)	0.23331 (19)	0.63536 (13)	0.0255 (3)
H7	1.2228	0.2652	0.6463	0.031*
C8	1.07667 (19)	0.27344 (18)	0.53359 (12)	0.0219 (3)
H8	1.1621	0.3316	0.4746	0.026*
Cl1	0.60119 (5)	0.06558 (4)	0.58431 (3)	0.02446 (10)
C9	0.76060 (17)	0.45602 (16)	0.10645 (10)	0.0157 (3)
C10	0.72840 (17)	0.35187 (16)	0.03331 (11)	0.0168 (3)
C11	0.71224 (18)	0.41280 (17)	−0.07151 (11)	0.0182 (3)
H11	0.6902	0.3424	−0.1215	0.022*
C12	0.72833 (18)	0.57592 (17)	−0.10270 (11)	0.0194 (3)
H12	0.7174	0.6172	−0.1740	0.023*
C13	0.76050 (19)	0.67912 (17)	−0.02973 (12)	0.0211 (3)
H13	0.7715	0.7909	−0.0513	0.025*
C14	0.77660 (19)	0.61922 (17)	0.07490 (12)	0.0199 (3)
H14	0.7985	0.6901	0.1247	0.024*
C15	0.7096 (2)	0.17576 (17)	0.06715 (12)	0.0221 (3)
F1B	0.655 (4)	0.094 (4)	−0.007 (3)	0.031 (2)	0.48 (9)
F2B	0.879 (4)	0.112 (3)	0.082 (2)	0.027 (2)	0.48 (9)
F3B	0.582 (2)	0.1436 (14)	0.1620 (9)	0.040 (4)	0.48 (9)
F1A	0.690 (5)	0.096 (4)	−0.015 (3)	0.035 (3)	0.52 (9)
F2A	0.848 (3)	0.098 (3)	0.086 (2)	0.031 (2)	0.52 (9)
F3A	0.5736 (17)	0.1467 (12)	0.1633 (7)	0.030 (3)	0.52 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0175 (6)	0.0172 (6)	0.0149 (6)	0.0001 (5)	−0.0043 (5)	−0.0007 (5)
O1	0.0208 (5)	0.0306 (6)	0.0164 (5)	0.0078 (4)	−0.0008 (4)	0.0000 (4)
N1	0.0154 (5)	0.0237 (6)	0.0105 (5)	0.0035 (4)	−0.0020 (4)	−0.0019 (4)
C2	0.0169 (6)	0.0172 (6)	0.0130 (6)	−0.0007 (5)	−0.0037 (5)	−0.0028 (5)
S1	0.01603 (16)	0.02989 (19)	0.01299 (16)	0.00589 (13)	−0.00426 (12)	−0.00353 (13)
N2	0.0174 (5)	0.0241 (6)	0.0116 (5)	0.0057 (4)	−0.0037 (4)	−0.0019 (4)
C3	0.0164 (6)	0.0168 (6)	0.0152 (6)	0.0026 (5)	−0.0053 (5)	−0.0019 (5)
C4	0.0178 (6)	0.0153 (6)	0.0173 (6)	0.0000 (5)	−0.0059 (5)	−0.0022 (5)
C5	0.0281 (7)	0.0189 (7)	0.0170 (6)	0.0004 (5)	−0.0069 (5)	0.0015 (5)
C6	0.0318 (8)	0.0236 (7)	0.0220 (7)	0.0063 (6)	−0.0160 (6)	−0.0032 (6)
C7	0.0213 (7)	0.0282 (8)	0.0321 (8)	0.0022 (6)	−0.0151 (6)	−0.0059 (6)
C8	0.0173 (6)	0.0237 (7)	0.0242 (7)	−0.0004 (5)	−0.0056 (5)	−0.0010 (5)
Cl1	0.02307 (17)	0.02779 (19)	0.02433 (18)	−0.00967 (13)	−0.00880 (13)	0.00143 (13)
C9	0.0136 (6)	0.0212 (6)	0.0105 (6)	0.0020 (5)	−0.0012 (4)	−0.0017 (5)
C10	0.0150 (6)	0.0195 (6)	0.0140 (6)	0.0006 (5)	−0.0017 (5)	−0.0015 (5)
C11	0.0170 (6)	0.0239 (7)	0.0134 (6)	−0.0004 (5)	−0.0033 (5)	−0.0032 (5)
C12	0.0156 (6)	0.0273 (7)	0.0136 (6)	0.0001 (5)	−0.0030 (5)	0.0028 (5)
C13	0.0207 (6)	0.0196 (7)	0.0214 (7)	−0.0017 (5)	−0.0044 (5)	0.0028 (5)
C14	0.0208 (6)	0.0209 (7)	0.0182 (6)	−0.0013 (5)	−0.0052 (5)	−0.0037 (5)
C15	0.0263 (7)	0.0209 (7)	0.0181 (7)	0.0001 (5)	−0.0051 (6)	−0.0010 (5)
F1B	0.043 (6)	0.020 (2)	0.034 (6)	−0.010 (4)	−0.015 (5)	−0.005 (3)
F2B	0.021 (5)	0.016 (3)	0.042 (2)	0.003 (3)	−0.011 (3)	0.003 (2)
F3B	0.046 (6)	0.023 (5)	0.042 (6)	−0.003 (3)	0.004 (4)	−0.004 (4)
F1A	0.054 (9)	0.025 (2)	0.029 (3)	−0.010 (5)	−0.014 (6)	−0.0042 (18)
F2A	0.023 (5)	0.024 (3)	0.049 (3)	0.001 (3)	−0.013 (3)	0.000 (2)
F3A	0.032 (4)	0.029 (5)	0.019 (4)	−0.009 (3)	0.002 (3)	0.014 (3)

C1—O1	1.2240 (17)	C8—H8	0.9500
C1—N1	1.3790 (17)	C9—C14	1.387 (2)
C1—C3	1.4992 (18)	C9—C10	1.3964 (19)
N1—C2	1.3898 (17)	C10—C11	1.3968 (19)
N1—H1	0.8800	C10—C15	1.497 (2)
C2—N2	1.3356 (17)	C11—C12	1.386 (2)
C2—S1	1.6714 (14)	C11—H11	0.9500
N2—C9	1.4338 (17)	C12—C13	1.389 (2)
N2—H2	0.8800	C12—H12	0.9500
C3—C4	1.3964 (19)	C13—C14	1.392 (2)
C3—C8	1.3978 (19)	C13—H13	0.9500
C4—C5	1.3889 (19)	C14—H14	0.9500
C4—Cl1	1.7350 (14)	C15—F2A	1.28 (2)
C5—C6	1.386 (2)	C15—F3B	1.317 (13)
C5—H5	0.9500	C15—F1A	1.32 (3)
C6—C7	1.384 (2)	C15—F3A	1.355 (10)
C6—H6	0.9500	C15—F1B	1.37 (3)
C7—C8	1.388 (2)	C15—F2B	1.43 (2)
C7—H7	0.9500
O1—C1—N1	123.21 (12)	C9—C10—C11	119.71 (13)
O1—C1—C3	120.74 (12)	C9—C10—C15	120.33 (12)
N1—C1—C3	115.98 (11)	C11—C10—C15	119.96 (12)
C1—N1—C2	127.40 (11)	C12—C11—C10	120.07 (13)
C1—N1—H1	116.3	C12—C11—H11	120.0
C2—N1—H1	116.3	C10—C11—H11	120.0
N2—C2—N1	115.63 (12)	C11—C12—C13	120.04 (13)
N2—C2—S1	124.81 (10)	C11—C12—H12	120.0
N1—C2—S1	119.55 (10)	C13—C12—H12	120.0
C2—N2—C9	124.05 (11)	C12—C13—C14	120.19 (13)
C2—N2—H2	118.0	C12—C13—H13	119.9
C9—N2—H2	118.0	C14—C13—H13	119.9
C4—C3—C8	118.57 (12)	C9—C14—C13	119.96 (13)
C4—C3—C1	124.71 (12)	C9—C14—H14	120.0
C8—C3—C1	116.66 (12)	C13—C14—H14	120.0
C5—C4—C3	120.93 (13)	F2A—C15—F3B	101.9 (12)
C5—C4—Cl1	118.00 (11)	F2A—C15—F1A	100 (2)
C3—C4—Cl1	120.97 (10)	F3B—C15—F1A	111.6 (15)
C6—C5—C4	119.47 (13)	F2A—C15—F3A	104.1 (12)
C6—C5—H5	120.3	F1A—C15—F3A	111.2 (15)
C4—C5—H5	120.3	F2A—C15—F1B	107.3 (18)
C7—C6—C5	120.53 (13)	F3B—C15—F1B	101.8 (14)
C7—C6—H6	119.7	F3A—C15—F1B	101.3 (13)
C5—C6—H6	119.7	F3B—C15—F2B	107.7 (11)
C6—C7—C8	119.83 (14)	F1A—C15—F2B	104 (2)
C6—C7—H7	120.1	F3A—C15—F2B	109.9 (10)
C8—C7—H7	120.1	F1B—C15—F2B	112.2 (17)
C7—C8—C3	120.63 (13)	F2A—C15—C10	117.1 (11)
C7—C8—H8	119.7	F3B—C15—C10	113.8 (6)
C3—C8—H8	119.7	F1A—C15—C10	111.2 (14)
C14—C9—C10	120.03 (12)	F3A—C15—C10	112.3 (5)
C14—C9—N2	119.62 (12)	F1B—C15—C10	113.3 (14)
C10—C9—N2	120.25 (12)	F2B—C15—C10	107.9 (10)
O1—C1—N1—C2	0.3 (2)	C14—C9—C10—C11	−0.06 (19)
C3—C1—N1—C2	177.38 (12)	N2—C9—C10—C11	−176.44 (11)
C1—N1—C2—N2	2.0 (2)	C14—C9—C10—C15	−179.55 (12)
C1—N1—C2—S1	−177.43 (11)	N2—C9—C10—C15	4.08 (19)
N1—C2—N2—C9	−176.33 (12)	C9—C10—C11—C12	0.07 (19)
S1—C2—N2—C9	3.1 (2)	C15—C10—C11—C12	179.56 (12)
O1—C1—C3—C4	−128.44 (15)	C10—C11—C12—C13	0.0 (2)
N1—C1—C3—C4	54.45 (18)	C11—C12—C13—C14	0.0 (2)
O1—C1—C3—C8	48.70 (19)	C10—C9—C14—C13	0.0 (2)
N1—C1—C3—C8	−128.41 (13)	N2—C9—C14—C13	176.40 (12)
C8—C3—C4—C5	1.8 (2)	C12—C13—C14—C9	0.0 (2)
C1—C3—C4—C5	178.93 (13)	C9—C10—C15—F2A	−62.3 (13)
C8—C3—C4—Cl1	−174.53 (10)	C11—C10—C15—F2A	118.2 (13)
C1—C3—C4—Cl1	2.57 (19)	C9—C10—C15—F3B	56.3 (7)
C3—C4—C5—C6	−0.2 (2)	C11—C10—C15—F3B	−123.2 (7)
Cl1—C4—C5—C6	176.29 (11)	C9—C10—C15—F1A	−176.6 (17)
C4—C5—C6—C7	−1.2 (2)	C11—C10—C15—F1A	3.9 (17)
C5—C6—C7—C8	0.8 (2)	C9—C10—C15—F3A	58.0 (5)
C6—C7—C8—C3	0.9 (2)	C11—C10—C15—F3A	−121.5 (5)
C4—C3—C8—C7	−2.2 (2)	C9—C10—C15—F1B	172.0 (13)
C1—C3—C8—C7	−179.51 (13)	C11—C10—C15—F1B	−7.5 (13)
C2—N2—C9—C14	71.67 (18)	C9—C10—C15—F2B	−63.2 (11)
C2—N2—C9—C10	−111.94 (15)	C11—C10—C15—F2B	117.3 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.58	3.4032 (16)	157
N2—H2···O1	0.88	1.91	2.6179 (16)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.58	3.4032 (16)	157
N2—H2⋯O1	0.88	1.91	2.6179 (16)	136

Symmetry code: (i) .