1-[3,5-Bis(trifluoro-meth-yl)phen-yl]-3-(2-pyrid-yl)thio-urea.

The title compound, C(14)H(9)F(6)N(3)S, exhibits a nearly planar conformation in the solid state, with a dihedral angle between the planes of the benzene and pyridine rings of 14.86 (3)°. The pyridine N atom allows for the formation of a six-membered N-H⋯N(py) hydrogen-bonded ring, thus forcing the two amide H atoms of the thio-urea group to point in opposite directions. The second N-H group forms an inter-molecular N-H⋯S hydrogen bond with the S atom of an adjacent mol-ecule. The F atoms of the two trifluoro-methyl groups display rotational disorder around the C-CF(3) axis, with an occupancy ratio of 0.54 (1):0.46 (1).

Related literature

For related literature, see: Akiyama et al. (2006 ▶); Struga et al. (2007 ▶).

Experimental

Crystal data

C14H9F6N3S

M = 365.30

Orthorhombic,

a = 15.0907 (17) Å

b = 7.7491 (9) Å

c = 26.709 (3) Å

V = 3123.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 293 (2) K

0.41 × 0.31 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.873, T max = 0.962

17235 measured reflections

3406 independent reflections

2585 reflections with I > 2σ(I)

R int = 0.102

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.151

S = 1.06

3406 reflections

280 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus and SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009768/zl2103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009768/zl2103Isup2.hkl

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

C14H9F6N3S	Dx = 1.554 Mg m−3
Mr = 365.30	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 4062 reflections
a = 15.0907 (17) Å	θ = 5.4–45.0º
b = 7.7491 (9) Å	µ = 0.27 mm−1
c = 26.709 (3) Å	T = 293 (2) K
V = 3123.3 (6) Å3	Prismatic, colourless
Z = 8	0.41 × 0.31 × 0.18 mm
F000 = 1472

Bruker SMART CCD area-detector diffractometer	3406 independent reflections
Radiation source: fine-focus sealed tube	2585 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.102
T = 293(2) K	θmax = 27.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.873, Tmax = 0.962	k = −9→9
17235 measured reflections	l = −26→34

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.075P)2 + 0.3374P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.040
3406 reflections	Δρmax = 0.40 e Å−3
280 parameters	Δρmin = −0.30 e Å−3
13 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
S1	0.44883 (4)	1.05153 (11)	0.42753 (2)	0.0699 (3)
N1	0.37456 (12)	0.8647 (3)	0.49769 (7)	0.0499 (5)
N2	0.28358 (12)	0.9220 (3)	0.43161 (6)	0.0468 (5)
N3	0.22735 (11)	0.7940 (2)	0.51757 (6)	0.0480 (5)
C1	0.36381 (13)	0.9414 (3)	0.45239 (8)	0.0456 (5)
C2	0.25117 (14)	0.9797 (3)	0.38500 (7)	0.0406 (5)
C3	0.30288 (14)	1.0050 (3)	0.34296 (7)	0.0435 (5)
H3	0.3640	0.9898	0.3445	0.052*
C4	0.26236 (15)	1.0534 (3)	0.29841 (7)	0.0426 (5)
C5	0.17215 (15)	1.0763 (3)	0.29537 (8)	0.0477 (5)
H5	0.1459	1.1092	0.2653	0.057*
C6	0.12109 (14)	1.0495 (3)	0.33762 (8)	0.0472 (5)
C7	0.15999 (14)	1.0010 (3)	0.38225 (8)	0.0451 (5)
H7	0.1251	0.9825	0.4104	0.054*
C8	0.31247 (13)	0.7912 (3)	0.53057 (7)	0.0431 (5)
C9	0.34218 (16)	0.7222 (3)	0.57550 (8)	0.0538 (6)
H9	0.4023	0.7189	0.5830	0.065*
C10	0.28091 (17)	0.6595 (3)	0.60830 (9)	0.0575 (6)
H10	0.2989	0.6127	0.6387	0.069*
C11	0.19245 (17)	0.6658 (3)	0.59626 (9)	0.0597 (6)
H11	0.1496	0.6260	0.6184	0.072*
C12	0.16964 (15)	0.7320 (3)	0.55103 (9)	0.0565 (6)
H12	0.1098	0.7343	0.5427	0.068*
C13	0.31954 (17)	1.0781 (3)	0.25314 (8)	0.0550 (6)
C14	0.02309 (17)	1.0700 (4)	0.33485 (10)	0.0693 (8)
F1	0.3600 (6)	1.2197 (7)	0.2520 (3)	0.092 (3)	0.540 (15)
F2	0.3770 (6)	0.9559 (14)	0.2476 (4)	0.106 (4)	0.540 (15)
F3	0.2703 (4)	1.0759 (17)	0.21099 (16)	0.105 (3)	0.540 (15)
F4	−0.0158 (11)	0.927 (2)	0.3219 (7)	0.114 (5)	0.540 (15)
F5	−0.0038 (9)	1.1890 (19)	0.3061 (5)	0.111 (6)	0.540 (15)
F6	−0.0122 (7)	1.1014 (17)	0.3796 (3)	0.118 (4)	0.540 (15)
F1'	0.3995 (6)	1.140 (2)	0.2647 (2)	0.112 (5)	0.460 (15)
F2'	0.3344 (11)	0.9413 (13)	0.2292 (4)	0.116 (5)	0.460 (15)
F3'	0.2887 (7)	1.1881 (17)	0.2217 (4)	0.117 (5)	0.460 (15)
F4'	−0.0137 (13)	0.957 (3)	0.3042 (8)	0.115 (7)	0.460 (15)
F5'	0.0011 (10)	1.2244 (16)	0.3174 (6)	0.111 (4)	0.460 (15)
F6'	−0.0171 (6)	1.0587 (17)	0.3773 (3)	0.097 (4)	0.460 (15)
H1	0.4219 (13)	0.877 (3)	0.5105 (9)	0.065 (8)*
H2	0.2456 (16)	0.882 (3)	0.4511 (9)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0397 (3)	0.1245 (7)	0.0456 (4)	−0.0239 (3)	−0.0094 (2)	0.0228 (3)
N1	0.0327 (9)	0.0801 (14)	0.0370 (9)	−0.0038 (9)	−0.0087 (7)	0.0105 (9)
N2	0.0334 (9)	0.0741 (13)	0.0328 (9)	−0.0062 (8)	−0.0037 (7)	0.0073 (8)
N3	0.0371 (9)	0.0676 (12)	0.0394 (9)	−0.0050 (8)	−0.0015 (7)	0.0030 (8)
C1	0.0331 (10)	0.0688 (15)	0.0350 (11)	−0.0001 (9)	−0.0020 (8)	0.0014 (9)
C2	0.0369 (10)	0.0511 (12)	0.0337 (10)	−0.0034 (9)	−0.0056 (8)	−0.0019 (8)
C3	0.0377 (10)	0.0552 (12)	0.0376 (11)	0.0001 (9)	−0.0011 (8)	−0.0029 (9)
C4	0.0482 (12)	0.0452 (12)	0.0345 (10)	−0.0035 (9)	−0.0018 (9)	−0.0024 (8)
C5	0.0523 (13)	0.0542 (13)	0.0368 (11)	−0.0019 (10)	−0.0104 (9)	0.0051 (9)
C6	0.0369 (11)	0.0579 (14)	0.0468 (12)	−0.0021 (9)	−0.0095 (9)	0.0039 (10)
C7	0.0372 (11)	0.0609 (13)	0.0371 (11)	−0.0041 (9)	−0.0025 (8)	0.0031 (9)
C8	0.0405 (11)	0.0522 (12)	0.0367 (10)	−0.0028 (9)	−0.0020 (8)	−0.0010 (9)
C9	0.0520 (13)	0.0655 (15)	0.0440 (12)	−0.0024 (11)	−0.0084 (10)	0.0098 (10)
C10	0.0692 (16)	0.0621 (15)	0.0410 (12)	−0.0048 (12)	−0.0018 (11)	0.0076 (10)
C11	0.0642 (15)	0.0647 (16)	0.0502 (14)	−0.0094 (12)	0.0109 (11)	0.0040 (11)
C12	0.0433 (12)	0.0751 (17)	0.0511 (13)	−0.0084 (11)	0.0034 (10)	0.0018 (11)
C13	0.0656 (16)	0.0613 (16)	0.0380 (12)	−0.0007 (13)	0.0038 (10)	0.0004 (11)
C14	0.0443 (14)	0.103 (2)	0.0601 (17)	−0.0011 (15)	−0.0095 (12)	0.0122 (16)
F1	0.127 (6)	0.066 (3)	0.082 (5)	−0.042 (3)	0.050 (4)	−0.018 (2)
F2	0.124 (6)	0.103 (7)	0.092 (5)	0.055 (6)	0.063 (4)	0.033 (5)
F3	0.103 (3)	0.140 (9)	0.0328 (17)	−0.036 (5)	−0.0070 (17)	0.001 (3)
F4	0.051 (5)	0.135 (7)	0.157 (13)	−0.041 (4)	−0.005 (6)	−0.035 (8)
F5	0.058 (4)	0.147 (15)	0.089 (5)	0.026 (7)	−0.018 (3)	0.067 (7)
F6	0.062 (5)	0.144 (8)	0.097 (6)	0.044 (4)	0.004 (3)	−0.038 (5)
F1'	0.081 (5)	0.151 (15)	0.065 (3)	−0.077 (6)	0.010 (3)	0.009 (6)
F2'	0.148 (12)	0.070 (5)	0.088 (7)	−0.011 (7)	0.077 (7)	−0.023 (5)
F3'	0.113 (9)	0.121 (8)	0.077 (6)	0.054 (7)	0.040 (6)	0.066 (6)
F4'	0.062 (7)	0.147 (14)	0.126 (11)	0.003 (7)	−0.056 (7)	−0.076 (10)
F5'	0.056 (5)	0.098 (5)	0.140 (11)	0.031 (3)	0.005 (5)	0.042 (5)
F6'	0.035 (3)	0.138 (7)	0.088 (6)	−0.008 (4)	−0.002 (3)	0.066 (6)

S1—C1	1.678 (2)	C8—C9	1.388 (3)
N1—C1	1.358 (3)	C9—C10	1.363 (3)
N1—C8	1.405 (3)	C9—H9	0.9300
N1—H1	0.798 (17)	C10—C11	1.374 (3)
N2—C1	1.340 (3)	C10—H10	0.9300
N2—C2	1.410 (3)	C11—C12	1.357 (3)
N2—H2	0.83 (2)	C11—H11	0.9300
N3—C8	1.331 (3)	C12—H12	0.9300
N3—C12	1.337 (3)	C13—F1	1.256 (5)
C2—C3	1.381 (3)	C13—F2'	1.259 (8)
C2—C7	1.388 (3)	C13—F3'	1.285 (5)
C3—C4	1.389 (3)	C13—F2	1.292 (7)
C3—H3	0.9300	C13—F1'	1.335 (6)
C4—C5	1.375 (3)	C13—F3	1.349 (5)
C4—C13	1.498 (3)	C14—F5	1.268 (9)
C5—C6	1.382 (3)	C14—F6'	1.288 (8)
C5—H5	0.9300	C14—F4	1.301 (13)
C6—C7	1.381 (3)	C14—F4'	1.319 (13)
C6—C14	1.489 (3)	C14—F5'	1.326 (10)
C7—H7	0.9300	C14—F6	1.331 (8)
C1—N1—C8	130.91 (18)	N3—C12—C11	124.4 (2)
C1—N1—H1	116 (2)	N3—C12—H12	117.8
C8—N1—H1	112.3 (19)	C11—C12—H12	117.8
C1—N2—C2	130.04 (19)	F1—C13—F2'	129.6 (6)
C1—N2—H2	113.9 (16)	F1—C13—F3'	65.2 (5)
C2—N2—H2	115.5 (16)	F2'—C13—F3'	106.9 (6)
C8—N3—C12	116.63 (19)	F1—C13—F2	108.1 (6)
N2—C1—N1	115.33 (19)	F3'—C13—F2	130.9 (4)
N2—C1—S1	125.73 (17)	F2'—C13—F1'	105.0 (6)
N1—C1—S1	118.94 (15)	F3'—C13—F1'	103.9 (6)
C3—C2—C7	120.02 (18)	F2—C13—F1'	71.5 (7)
C3—C2—N2	124.51 (19)	F1—C13—F3	104.9 (4)
C7—C2—N2	115.35 (18)	F2'—C13—F3	70.3 (6)
C2—C3—C4	119.1 (2)	F2—C13—F3	105.4 (5)
C2—C3—H3	120.5	F1'—C13—F3	134.0 (4)
C4—C3—H3	120.5	F1—C13—C4	114.3 (3)
C5—C4—C3	121.40 (19)	F2'—C13—C4	113.9 (5)
C5—C4—C13	120.41 (19)	F3'—C13—C4	113.8 (3)
C3—C4—C13	118.2 (2)	F2—C13—C4	112.6 (4)
C4—C5—C6	118.98 (19)	F1'—C13—C4	112.4 (3)
C4—C5—H5	120.5	F3—C13—C4	110.8 (3)
C6—C5—H5	120.5	F5—C14—F6'	115.6 (8)
C7—C6—C5	120.6 (2)	F5—C14—F4	108.3 (11)
C7—C6—C14	119.6 (2)	F6'—C14—F4	87.9 (10)
C5—C6—C14	119.8 (2)	F5—C14—F4'	88.3 (12)
C6—C7—C2	119.97 (19)	F6'—C14—F4'	107.6 (11)
C6—C7—H7	120.0	F6'—C14—F5'	104.6 (9)
C2—C7—H7	120.0	F4—C14—F5'	124.2 (11)
N3—C8—C9	122.95 (19)	F4'—C14—F5'	105.9 (12)
N3—C8—N1	118.28 (18)	F5—C14—F6	106.4 (9)
C9—C8—N1	118.76 (19)	F4—C14—F6	102.3 (10)
C10—C9—C8	118.3 (2)	F4'—C14—F6	120.7 (11)
C10—C9—H9	120.9	F5'—C14—F6	92.8 (9)
C8—C9—H9	120.9	F5—C14—C6	115.2 (7)
C9—C10—C11	119.7 (2)	F6'—C14—C6	114.6 (5)
C9—C10—H10	120.1	F4—C14—C6	111.8 (9)
C11—C10—H10	120.1	F4'—C14—C6	112.2 (10)
C12—C11—C10	117.9 (2)	F5'—C14—C6	111.2 (7)
C12—C11—H11	121.0	F6—C14—C6	111.9 (5)
C10—C11—H11	121.0
C2—N2—C1—N1	−178.0 (2)	C8—N3—C12—C11	−0.8 (4)
C2—N2—C1—S1	2.6 (4)	C10—C11—C12—N3	−1.0 (4)
C8—N1—C1—N2	−11.5 (4)	C5—C4—C13—F1	101.7 (6)
C8—N1—C1—S1	167.9 (2)	C3—C4—C13—F1	−79.2 (6)
C1—N2—C2—C3	28.6 (4)	C5—C4—C13—F2'	−93.6 (10)
C1—N2—C2—C7	−155.3 (2)	C3—C4—C13—F2'	85.6 (10)
C7—C2—C3—C4	0.7 (3)	C5—C4—C13—F3'	29.4 (9)
N2—C2—C3—C4	176.6 (2)	C3—C4—C13—F3'	−151.5 (9)
C2—C3—C4—C5	−0.1 (3)	C5—C4—C13—F2	−134.4 (7)
C2—C3—C4—C13	−179.3 (2)	C3—C4—C13—F2	44.7 (7)
C3—C4—C5—C6	−0.3 (3)	C5—C4—C13—F1'	147.1 (10)
C13—C4—C5—C6	178.9 (2)	C3—C4—C13—F1'	−33.7 (10)
C4—C5—C6—C7	0.1 (3)	C5—C4—C13—F3	−16.6 (7)
C4—C5—C6—C14	−178.7 (2)	C3—C4—C13—F3	162.5 (6)
C5—C6—C7—C2	0.4 (3)	C7—C6—C14—F5	145.4 (9)
C14—C6—C7—C2	179.3 (2)	C5—C6—C14—F5	−35.8 (10)
C3—C2—C7—C6	−0.8 (3)	C7—C6—C14—F6'	7.6 (8)
N2—C2—C7—C6	−177.1 (2)	C5—C6—C14—F6'	−173.6 (7)
C12—N3—C8—C9	2.4 (3)	C7—C6—C14—F4	−90.4 (9)
C12—N3—C8—N1	−176.2 (2)	C5—C6—C14—F4	88.4 (9)
C1—N1—C8—N3	−0.6 (4)	C7—C6—C14—F4'	−115.6 (12)
C1—N1—C8—C9	−179.3 (2)	C5—C6—C14—F4'	63.3 (12)
N3—C8—C9—C10	−2.1 (4)	C7—C6—C14—F5'	126.0 (8)
N1—C8—C9—C10	176.5 (2)	C5—C6—C14—F5'	−55.2 (8)
C8—C9—C10—C11	0.1 (4)	C7—C6—C14—F6	23.7 (7)
C9—C10—C11—C12	1.4 (4)	C5—C6—C14—F6	−157.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3	0.83 (2)	1.92 (2)	2.641 (3)	144 (2)
N1—H1···S1i	0.798 (17)	2.617 (18)	3.3931 (19)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3	0.83 (2)	1.92 (2)	2.641 (3)	144 (2)
N1—H1⋯S1i	0.798 (17)	2.617 (18)	3.3931 (19)	165 (3)

Symmetry code: (i) .