2,2-Diphenyl-N-{[2-(tri-fluoro-meth-yl)phen-yl]carbamo-thio-yl}acetamide.

The title mol-ecule, C22H17F3N2OS, adopts a trans-cis conformation with respect to the positions of the carbonyl and tri-fluoro-methyl-benzene groups against the thio-carbonyl group across the C-N bonds. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif. The tri-fluoro-methyl-substituted benzene ring forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings and is twisted from the O=C-N-(C=S)-N carbonyl-thio-urea plane [maximum deviation = 0.0535 (12) Å], making a dihedral angle of 63.59 (8)°. In the crystal, N-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into a layer parallel to the bc plane. A C-H⋯π inter-action is also observed.

Related literature

For the biological activity of thio­urea derivatives, see: Vankatachalam et al. (2001 ▶). For related structures, see: Yusof, Arshad et al. (2012 ▶); Yusof, Embong et al. (2012 ▶); Yusof, Mutalib et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H17F3N2OS

M = 414.44

Orthorhombic,

a = 20.0318 (4) Å

b = 10.2866 (2) Å

c = 9.5351 (2) Å

V = 1964.79 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.56 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.892, T max = 0.987

21265 measured reflections

5618 independent reflections

4608 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.081

S = 1.02

5618 reflections

270 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 2568 Freidel pairs

Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018680/is5283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018680/is5283Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018680/is5283Isup3.cml

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

C22H17F3N2OS	F(000) = 856
Mr = 414.44	Dx = 1.401 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5325 reflections
a = 20.0318 (4) Å	θ = 2.2–27.2°
b = 10.2866 (2) Å	µ = 0.21 mm−1
c = 9.5351 (2) Å	T = 100 K
V = 1964.79 (7) Å3	Plate, colourless
Z = 4	0.56 × 0.18 × 0.06 mm

Bruker SMART APEXII CCD area-detector diffractometer	5618 independent reflections
Radiation source: fine-focus sealed tube	4608 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→28
Tmin = 0.892, Tmax = 0.987	k = −14→14
21265 measured reflections	l = −13→13

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0299P)2 + 0.2655P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5618 reflections	Δρmax = 0.24 e Å−3
270 parameters	Δρmin = −0.25 e Å−3
2 restraints	Absolute structure: Flack (1983), 2568 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1	0.34230 (6)	0.45765 (11)	−0.02227 (17)	0.0418 (4)
F2	0.32081 (5)	0.66244 (10)	−0.02775 (14)	0.0327 (3)
F3	0.29424 (5)	0.54911 (10)	0.15416 (15)	0.0328 (3)
S1	0.35402 (2)	0.73635 (4)	0.50740 (6)	0.02441 (11)
N1	0.36053 (7)	0.78665 (14)	0.2330 (2)	0.0187 (3)
N2	0.28048 (8)	0.90001 (14)	0.3579 (2)	0.0174 (3)
O1	0.27383 (6)	0.95082 (11)	0.12731 (15)	0.0193 (3)
C1	0.14450 (8)	1.10138 (16)	0.0592 (2)	0.0181 (4)
H1A	0.1299	1.0144	0.0731	0.022*
C2	0.12280 (9)	1.16913 (18)	−0.0574 (2)	0.0224 (4)
H2A	0.0944	1.1282	−0.1238	0.027*
C3	0.14277 (9)	1.29838 (18)	−0.0774 (2)	0.0257 (5)
H3A	0.1276	1.3458	−0.1568	0.031*
C4	0.18467 (8)	1.35616 (16)	0.0193 (2)	0.0243 (5)
H4A	0.1982	1.4439	0.0065	0.029*
C5	0.20734 (8)	1.28682 (16)	0.1358 (2)	0.0222 (4)
H5A	0.2365	1.3272	0.2012	0.027*
C6	0.18726 (8)	1.15807 (15)	0.1565 (2)	0.0168 (4)
C7	0.20977 (8)	1.08378 (15)	0.2869 (2)	0.0152 (4)
H7A	0.2368	1.1458	0.3444	0.018*
C8	0.14922 (8)	1.04613 (16)	0.3756 (2)	0.0161 (4)
C9	0.12615 (9)	1.13343 (17)	0.4758 (2)	0.0217 (4)
H9A	0.1498	1.2121	0.4917	0.026*
C10	0.06891 (9)	1.10700 (18)	0.5532 (2)	0.0253 (4)
H10A	0.0533	1.1678	0.6206	0.030*
C11	0.03473 (9)	0.99143 (19)	0.5314 (2)	0.0273 (5)
H11A	−0.0043	0.9727	0.5843	0.033*
C12	0.05759 (9)	0.90365 (18)	0.4329 (2)	0.0240 (5)
H12A	0.0341	0.8246	0.4183	0.029*
C13	0.11465 (9)	0.92994 (16)	0.3548 (2)	0.0201 (4)
H13A	0.1301	0.8689	0.2874	0.024*
C14	0.25639 (8)	0.97102 (14)	0.2475 (2)	0.0148 (3)
C15	0.33231 (8)	0.80792 (16)	0.3580 (2)	0.0176 (4)
C16	0.41583 (8)	0.70043 (16)	0.2104 (2)	0.0185 (4)
C17	0.47773 (9)	0.72797 (17)	0.2680 (2)	0.0216 (4)
H17A	0.4830	0.8010	0.3280	0.026*
C18	0.53209 (9)	0.64879 (18)	0.2380 (2)	0.0260 (5)
H18A	0.5745	0.6681	0.2774	0.031*
C19	0.52477 (9)	0.54208 (18)	0.1511 (3)	0.0295 (5)
H19A	0.5619	0.4874	0.1320	0.035*
C20	0.46349 (9)	0.51515 (18)	0.0922 (3)	0.0269 (5)
H20A	0.4586	0.4424	0.0317	0.032*
C21	0.40852 (9)	0.59409 (16)	0.1208 (2)	0.0213 (4)
C22	0.34224 (9)	0.56611 (17)	0.0566 (3)	0.0261 (5)
H1N2	0.2679 (10)	0.9143 (17)	0.4368 (17)	0.015 (6)*
H1N1	0.3439 (11)	0.823 (2)	0.147 (3)	0.049 (7)*

	U11	U22	U33	U12	U13	U23
F1	0.0392 (7)	0.0294 (6)	0.0567 (11)	−0.0032 (5)	−0.0016 (8)	−0.0226 (7)
F2	0.0323 (6)	0.0328 (6)	0.0330 (8)	−0.0032 (5)	−0.0084 (6)	−0.0004 (6)
F3	0.0265 (5)	0.0316 (6)	0.0403 (9)	−0.0078 (4)	0.0048 (6)	−0.0017 (6)
S1	0.0327 (2)	0.02260 (19)	0.0179 (2)	0.00898 (17)	0.0012 (3)	0.0045 (2)
N1	0.0213 (7)	0.0191 (7)	0.0156 (9)	0.0036 (6)	−0.0009 (8)	−0.0003 (7)
N2	0.0215 (7)	0.0200 (7)	0.0107 (9)	0.0040 (6)	0.0024 (8)	−0.0003 (7)
O1	0.0197 (6)	0.0248 (6)	0.0135 (8)	0.0022 (5)	−0.0008 (6)	0.0012 (6)
C1	0.0161 (7)	0.0196 (8)	0.0187 (10)	−0.0002 (6)	0.0020 (8)	0.0020 (8)
C2	0.0202 (8)	0.0273 (9)	0.0196 (11)	0.0014 (7)	−0.0015 (9)	0.0023 (9)
C3	0.0211 (9)	0.0286 (9)	0.0274 (13)	0.0056 (7)	0.0021 (9)	0.0119 (9)
C4	0.0224 (8)	0.0200 (7)	0.0306 (13)	0.0011 (6)	0.0028 (10)	0.0105 (9)
C5	0.0185 (8)	0.0188 (7)	0.0293 (13)	−0.0021 (6)	0.0018 (10)	0.0033 (9)
C6	0.0150 (7)	0.0169 (7)	0.0186 (11)	0.0018 (6)	0.0020 (8)	0.0023 (8)
C7	0.0163 (7)	0.0154 (7)	0.0138 (10)	−0.0015 (6)	−0.0004 (8)	−0.0005 (7)
C8	0.0165 (7)	0.0195 (8)	0.0124 (10)	0.0018 (6)	−0.0008 (8)	0.0021 (7)
C9	0.0228 (8)	0.0226 (7)	0.0196 (12)	0.0038 (6)	−0.0019 (9)	0.0013 (8)
C10	0.0252 (9)	0.0319 (9)	0.0188 (11)	0.0098 (7)	0.0021 (9)	0.0015 (9)
C11	0.0180 (8)	0.0378 (10)	0.0260 (14)	0.0047 (7)	0.0044 (10)	0.0123 (10)
C12	0.0190 (8)	0.0265 (9)	0.0266 (13)	−0.0021 (7)	−0.0007 (9)	0.0081 (9)
C13	0.0188 (8)	0.0209 (8)	0.0205 (11)	0.0003 (6)	−0.0009 (9)	0.0038 (9)
C14	0.0132 (7)	0.0164 (7)	0.0147 (10)	−0.0030 (6)	−0.0007 (8)	0.0026 (8)
C15	0.0199 (8)	0.0142 (7)	0.0187 (10)	−0.0012 (6)	0.0015 (9)	0.0011 (8)
C16	0.0195 (8)	0.0176 (7)	0.0184 (11)	0.0030 (6)	0.0024 (9)	0.0021 (8)
C17	0.0239 (9)	0.0209 (8)	0.0199 (11)	0.0006 (7)	−0.0005 (9)	0.0008 (8)
C18	0.0201 (8)	0.0277 (9)	0.0303 (13)	0.0017 (7)	0.0004 (10)	0.0047 (10)
C19	0.0255 (9)	0.0252 (9)	0.0378 (15)	0.0072 (7)	0.0066 (11)	0.0030 (10)
C20	0.0301 (9)	0.0196 (8)	0.0309 (14)	0.0026 (7)	0.0053 (10)	−0.0042 (9)
C21	0.0231 (8)	0.0162 (7)	0.0247 (12)	−0.0007 (6)	0.0029 (9)	−0.0006 (8)
C22	0.0275 (9)	0.0197 (8)	0.0313 (13)	−0.0021 (7)	0.0027 (10)	−0.0066 (9)

F1—C22	1.345 (2)	C7—C14	1.536 (2)
F2—C22	1.346 (2)	C7—H7A	1.0000
F3—C22	1.349 (2)	C8—C9	1.391 (3)
S1—C15	1.661 (2)	C8—C13	1.395 (2)
N1—C15	1.337 (3)	C9—C10	1.390 (3)
N1—C16	1.435 (2)	C9—H9A	0.9500
N1—H1N1	0.96 (3)	C10—C11	1.388 (3)
N2—C14	1.369 (3)	C10—H10A	0.9500
N2—C15	1.405 (2)	C11—C12	1.382 (3)
N2—H1N2	0.807 (15)	C11—H11A	0.9500
O1—C14	1.216 (2)	C12—C13	1.391 (3)
C1—C2	1.382 (3)	C12—H12A	0.9500
C1—C6	1.391 (3)	C13—H13A	0.9500
C1—H1A	0.9500	C16—C17	1.386 (2)
C2—C3	1.402 (3)	C16—C21	1.395 (3)
C2—H2A	0.9500	C17—C18	1.390 (2)
C3—C4	1.382 (3)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.383 (3)
C4—C5	1.396 (3)	C18—H18A	0.9500
C4—H4A	0.9500	C19—C20	1.378 (3)
C5—C6	1.398 (2)	C19—H19A	0.9500
C5—H5A	0.9500	C20—C21	1.395 (2)
C6—C7	1.527 (3)	C20—H20A	0.9500
C7—C8	1.529 (2)	C21—C22	1.490 (3)
C15—N1—C16	124.13 (18)	C12—C11—C10	119.86 (18)
C15—N1—H1N1	123.6 (14)	C12—C11—H11A	120.1
C16—N1—H1N1	112.2 (15)	C10—C11—H11A	120.1
C14—N2—C15	128.37 (19)	C11—C12—C13	120.64 (18)
C14—N2—H1N2	120.6 (14)	C11—C12—H12A	119.7
C15—N2—H1N2	110.6 (14)	C13—C12—H12A	119.7
C2—C1—C6	121.25 (16)	C12—C13—C8	119.89 (19)
C2—C1—H1A	119.4	C12—C13—H13A	120.1
C6—C1—H1A	119.4	C8—C13—H13A	120.1
C1—C2—C3	119.90 (18)	O1—C14—N2	122.15 (15)
C1—C2—H2A	120.1	O1—C14—C7	122.26 (17)
C3—C2—H2A	120.1	N2—C14—C7	115.46 (18)
C4—C3—C2	119.35 (19)	N1—C15—N2	114.95 (19)
C4—C3—H3A	120.3	N1—C15—S1	125.53 (14)
C2—C3—H3A	120.3	N2—C15—S1	119.53 (16)
C3—C4—C5	120.61 (16)	C17—C16—C21	119.80 (16)
C3—C4—H4A	119.7	C17—C16—N1	120.32 (16)
C5—C4—H4A	119.7	C21—C16—N1	119.68 (16)
C4—C5—C6	120.18 (18)	C16—C17—C18	119.99 (18)
C4—C5—H5A	119.9	C16—C17—H17A	120.0
C6—C5—H5A	119.9	C18—C17—H17A	120.0
C1—C6—C5	118.69 (17)	C19—C18—C17	120.36 (18)
C1—C6—C7	120.99 (14)	C19—C18—H18A	119.8
C5—C6—C7	120.27 (17)	C17—C18—H18A	119.8
C6—C7—C8	110.06 (13)	C20—C19—C18	119.87 (17)
C6—C7—C14	111.04 (16)	C20—C19—H19A	120.1
C8—C7—C14	115.23 (13)	C18—C19—H19A	120.1
C6—C7—H7A	106.7	C19—C20—C21	120.42 (18)
C8—C7—H7A	106.7	C19—C20—H20A	119.8
C14—C7—H7A	106.7	C21—C20—H20A	119.8
C9—C8—C13	119.07 (17)	C20—C21—C16	119.55 (17)
C9—C8—C7	118.72 (15)	C20—C21—C22	120.68 (17)
C13—C8—C7	122.14 (17)	C16—C21—C22	119.77 (16)
C10—C9—C8	120.82 (17)	F1—C22—F2	106.09 (19)
C10—C9—H9A	119.6	F1—C22—F3	106.16 (14)
C8—C9—H9A	119.6	F2—C22—F3	106.26 (15)
C11—C10—C9	119.71 (18)	F1—C22—C21	112.90 (15)
C11—C10—H10A	120.1	F2—C22—C21	112.79 (15)
C9—C10—H10A	120.1	F3—C22—C21	112.10 (19)
C6—C1—C2—C3	−1.4 (3)	C8—C7—C14—O1	128.74 (18)
C1—C2—C3—C4	0.7 (3)	C6—C7—C14—N2	178.66 (14)
C2—C3—C4—C5	0.3 (3)	C8—C7—C14—N2	−55.4 (2)
C3—C4—C5—C6	−0.6 (3)	C16—N1—C15—N2	177.55 (15)
C2—C1—C6—C5	1.1 (3)	C16—N1—C15—S1	−2.0 (3)
C2—C1—C6—C7	178.57 (16)	C14—N2—C15—N1	−1.1 (3)
C4—C5—C6—C1	−0.1 (3)	C14—N2—C15—S1	178.46 (14)
C4—C5—C6—C7	−177.58 (16)	C15—N1—C16—C17	−65.9 (2)
C1—C6—C7—C8	−60.0 (2)	C15—N1—C16—C21	119.3 (2)
C5—C6—C7—C8	117.41 (17)	C21—C16—C17—C18	−0.8 (3)
C1—C6—C7—C14	68.76 (19)	N1—C16—C17—C18	−175.70 (19)
C5—C6—C7—C14	−113.78 (17)	C16—C17—C18—C19	−0.2 (3)
C6—C7—C8—C9	−88.1 (2)	C17—C18—C19—C20	1.0 (3)
C14—C7—C8—C9	145.37 (17)	C18—C19—C20—C21	−0.7 (3)
C6—C7—C8—C13	88.9 (2)	C19—C20—C21—C16	−0.4 (3)
C14—C7—C8—C13	−37.6 (3)	C19—C20—C21—C22	179.5 (2)
C13—C8—C9—C10	−1.0 (3)	C17—C16—C21—C20	1.1 (3)
C7—C8—C9—C10	176.08 (17)	N1—C16—C21—C20	176.01 (19)
C8—C9—C10—C11	0.8 (3)	C17—C16—C21—C22	−178.75 (18)
C9—C10—C11—C12	−0.3 (3)	N1—C16—C21—C22	−3.9 (3)
C10—C11—C12—C13	0.0 (3)	C20—C21—C22—F1	2.8 (3)
C11—C12—C13—C8	−0.2 (3)	C16—C21—C22—F1	−177.32 (18)
C9—C8—C13—C12	0.7 (3)	C20—C21—C22—F2	−117.5 (2)
C7—C8—C13—C12	−176.30 (18)	C16—C21—C22—F2	62.4 (3)
C15—N2—C14—O1	8.3 (3)	C20—C21—C22—F3	122.6 (2)
C15—N2—C14—C7	−167.60 (16)	C16—C21—C22—F3	−57.5 (2)
C6—C7—C14—O1	2.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2···O1i	0.81 (2)	2.04 (2)	2.838 (2)	174 (2)
C9—H9A···F1ii	0.95	2.53	3.395 (2)	151
C7—H7A···Cg1iii	1.00	2.84	3.7826 (19)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2⋯O1i	0.81 (2)	2.04 (2)	2.838 (2)	174 (2)
C9—H9A⋯F1ii	0.95	2.53	3.395 (2)	151
C7—H7A⋯Cg1iii	1.00	2.84	3.7826 (19)	158

Symmetry codes: (i) ; (ii) ; (iii) .