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The title compound, C16H15F3N2S, is a biologically active anti-implantation agent. The dihedral angle between the phenyl and tri­fluoro­methyl­phenyl rings is 15.9 (2)°. The crystal structure is stabilized by intermolecular N—H...S hydrogen bonds, forming dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024961/sj6015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024961/sj6015Isup2.hkl
Contains datablock I

CCDC reference: 255881

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.089
  • wR factor = 0.186
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.25 Ratio
Author Response: The carbon atoms of the phenyl ring C11-C16 have large thermal parameters compared to the riding hydrogen and hence the ratio Ueq(max)/Ueq(min) has a large value.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.28 Ratio
Author Response: The carbon atoms of the phenyl ring C11-C16 have large thermal parameters compared to the riding hydrogen and hence the ratio Ueq(max)/Ueq(min) has a large value.

Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for C15 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C7 PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 13
Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C11 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08 PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3N ... ?
2 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 2003).

N-phenylethyl-N'-[3-(trifluoromethyl)phenyl]thiourea top
Crystal data top
C16H15F3N2SZ = 2
Mr = 324.37F(000) = 336
Triclinic, P1Dx = 1.361 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.978 (3) ÅCell parameters from 575 reflections
b = 7.298 (3) Åθ = 2.4–24.7°
c = 16.064 (7) ŵ = 0.23 mm1
α = 77.050 (6)°T = 293 K
β = 83.614 (6)°Block, yellow
γ = 86.078 (7)°0.28 × 0.20 × 0.18 mm
V = 791.5 (6) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2987 independent reflections
Radiation source: fine-focus sealed tube1805 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.911, Tmax = 0.959k = 99
6240 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.089Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.1067P)2 + 2.188P]
where P = (Fo2 + 2Fc2)/3
2987 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.73542 (18)0.2913 (2)0.01637 (9)0.0438 (5)
F10.4802 (9)0.0142 (12)0.4066 (3)0.159 (3)
F20.2316 (12)0.1312 (11)0.4477 (4)0.179 (3)
F30.2335 (11)0.1414 (12)0.4576 (3)0.166 (3)
N20.4284 (6)0.2741 (7)0.0966 (3)0.0406 (11)
N30.6168 (6)0.0016 (6)0.1046 (3)0.0392 (11)
C10.2966 (7)0.2102 (7)0.1692 (3)0.0334 (12)
C20.3582 (7)0.1439 (8)0.2494 (3)0.0474 (14)
C30.2250 (8)0.0946 (8)0.3201 (4)0.0512 (15)
C40.0311 (9)0.1109 (9)0.3110 (4)0.0575 (17)
C50.0289 (8)0.1778 (9)0.2311 (4)0.0569 (16)
C60.1013 (7)0.2261 (8)0.1600 (3)0.0421 (13)
C70.2936 (13)0.0300 (16)0.4067 (5)0.093 (3)
C80.5863 (6)0.1806 (7)0.0671 (3)0.0331 (12)
C90.7781 (8)0.1170 (8)0.0784 (4)0.0452 (14)
C100.7525 (8)0.3202 (8)0.1224 (4)0.0499 (15)
C110.7559 (10)0.3612 (8)0.2176 (4)0.0586 (17)
C120.9231 (15)0.3445 (11)0.2524 (6)0.099 (3)
C130.932 (3)0.3853 (17)0.3395 (9)0.169 (7)
C140.768 (4)0.441 (3)0.3916 (10)0.206 (13)
C150.603 (3)0.467 (2)0.3595 (10)0.197 (10)
C160.5950 (16)0.4200 (13)0.2706 (7)0.113 (3)
H2N0.400 (8)0.380 (9)0.067 (4)0.056 (19)*
H3N0.534 (8)0.053 (8)0.143 (4)0.047 (16)*
H20.48950.13220.25600.057*
H40.05850.07710.35860.069*
H50.16030.19070.22480.068*
H60.05820.26930.10600.051*
H9A0.89730.07600.09260.054*
H9B0.78710.10450.01670.054*
H10A0.63040.35790.10950.060*
H10B0.85410.39650.09860.060*
H121.03290.30470.21610.118*
H131.04600.37520.36250.203*
H140.77050.46200.45080.248*
H150.49650.51540.39600.236*
H160.48020.42880.24770.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0337 (7)0.0480 (9)0.0415 (8)0.0064 (6)0.0074 (5)0.0005 (6)
F10.105 (4)0.298 (9)0.055 (3)0.022 (5)0.029 (3)0.004 (4)
F20.245 (8)0.174 (7)0.088 (4)0.058 (6)0.055 (5)0.065 (4)
F30.215 (7)0.233 (8)0.063 (3)0.056 (6)0.037 (4)0.064 (4)
N20.037 (2)0.038 (3)0.040 (3)0.014 (2)0.0048 (18)0.001 (2)
N30.037 (2)0.035 (3)0.040 (2)0.0057 (19)0.0061 (19)0.003 (2)
C10.030 (2)0.032 (3)0.038 (3)0.004 (2)0.001 (2)0.009 (2)
C20.031 (3)0.066 (4)0.042 (3)0.003 (3)0.003 (2)0.008 (3)
C30.053 (4)0.057 (4)0.040 (3)0.001 (3)0.003 (3)0.007 (3)
C40.050 (4)0.067 (4)0.051 (4)0.007 (3)0.018 (3)0.013 (3)
C50.027 (3)0.074 (4)0.070 (4)0.001 (3)0.004 (3)0.019 (3)
C60.037 (3)0.049 (3)0.041 (3)0.002 (2)0.008 (2)0.012 (3)
C70.085 (6)0.145 (9)0.035 (4)0.005 (5)0.003 (4)0.000 (5)
C80.029 (2)0.042 (3)0.028 (3)0.000 (2)0.0035 (19)0.007 (2)
C90.044 (3)0.044 (3)0.045 (3)0.014 (2)0.000 (2)0.012 (3)
C100.052 (3)0.036 (3)0.066 (4)0.007 (3)0.007 (3)0.021 (3)
C110.083 (5)0.033 (3)0.056 (4)0.005 (3)0.005 (3)0.006 (3)
C120.156 (9)0.063 (5)0.081 (6)0.004 (5)0.057 (6)0.003 (4)
C130.32 (2)0.085 (8)0.111 (10)0.003 (11)0.105 (13)0.005 (8)
C140.44 (4)0.109 (12)0.063 (9)0.010 (18)0.022 (15)0.003 (8)
C150.33 (3)0.117 (11)0.108 (13)0.020 (15)0.095 (14)0.006 (10)
C160.137 (8)0.083 (7)0.103 (8)0.009 (6)0.038 (6)0.009 (5)
Geometric parameters (Å, º) top
S1—C81.689 (5)C5—C41.368 (9)
N3—C81.324 (6)C5—H50.9300
N3—C91.456 (6)C4—C31.371 (8)
N3—H3N0.85 (6)C4—H40.9300
C1—C21.376 (7)C3—C71.486 (9)
C1—C61.381 (7)F3—C71.296 (11)
C1—N21.415 (6)C11—C161.364 (10)
N2—C81.353 (6)C11—C121.373 (10)
N2—H2N0.83 (6)F1—C71.299 (9)
C10—C111.493 (9)F2—C71.290 (11)
C10—C91.506 (8)C15—C141.36 (3)
C10—H10A0.9700C15—C161.398 (19)
C10—H10B0.9700C15—H150.9300
C2—C31.383 (7)C12—C131.371 (14)
C2—H20.9300C12—H120.9300
C9—H9A0.9700C14—C131.37 (3)
C9—H9B0.9700C14—H140.9300
C6—C51.374 (7)C16—H160.9300
C6—H60.9300C13—H130.9300
C8—N3—C9123.9 (4)C6—C5—H5119.4
C8—N3—H3N120 (4)C5—C4—C3119.1 (5)
C9—N3—H3N116 (4)C5—C4—H4120.4
C2—C1—C6119.5 (4)C3—C4—H4120.4
C2—C1—N2121.4 (4)C4—C3—C2120.4 (5)
C6—C1—N2119.0 (5)C4—C3—C7120.2 (5)
C8—N2—C1128.0 (4)C2—C3—C7119.4 (6)
C8—N2—H2N117 (4)C16—C11—C12119.4 (8)
C1—N2—H2N115 (4)C16—C11—C10120.5 (8)
N3—C8—N2118.0 (4)C12—C11—C10120.1 (7)
N3—C8—S1122.0 (4)F2—C7—F3103.6 (7)
N2—C8—S1120.0 (4)F2—C7—F1105.6 (9)
C11—C10—C9114.6 (5)F3—C7—F1106.1 (9)
C11—C10—H10A108.6F2—C7—C3113.7 (8)
C9—C10—H10A108.6F3—C7—C3112.5 (8)
C11—C10—H10B108.6F1—C7—C3114.3 (6)
C9—C10—H10B108.6C14—C15—C16118.8 (18)
H10A—C10—H10B107.6C14—C15—H15120.6
C1—C2—C3120.1 (5)C16—C15—H15120.6
C1—C2—H2120.0C13—C12—C11121.3 (12)
C3—C2—H2120.0C13—C12—H12119.3
N3—C9—C10110.9 (4)C11—C12—H12119.3
N3—C9—H9A109.5C15—C14—C13121.8 (17)
C10—C9—H9A109.5C15—C14—H14119.1
N3—C9—H9B109.5C13—C14—H14119.1
C10—C9—H9B109.5C11—C16—C15120.0 (14)
H9A—C9—H9B108.1C11—C16—H16120.0
C5—C6—C1119.6 (5)C15—C16—H16120.0
C5—C6—H6120.2C14—C13—C12118.4 (17)
C1—C6—H6120.2C14—C13—H13120.8
C4—C5—C6121.3 (5)C12—C13—H13120.8
C4—C5—H5119.4
C2—C1—N2—C854.8 (8)C1—C2—C3—C7177.8 (7)
C6—C1—N2—C8129.4 (6)C9—C10—C11—C16114.5 (7)
C9—N3—C8—N2178.5 (5)C9—C10—C11—C1267.2 (8)
C9—N3—C8—S10.4 (7)C4—C3—C7—F256.3 (11)
C1—N2—C8—N36.4 (8)C2—C3—C7—F2125.8 (8)
C1—N2—C8—S1174.6 (4)C4—C3—C7—F361.0 (11)
C6—C1—C2—C30.3 (9)C2—C3—C7—F3116.9 (8)
N2—C1—C2—C3175.5 (5)C4—C3—C7—F1177.8 (8)
C8—N3—C9—C10169.5 (5)C2—C3—C7—F14.3 (13)
C11—C10—C9—N364.8 (7)C16—C11—C12—C130.2 (13)
C2—C1—C6—C50.8 (8)C10—C11—C12—C13178.5 (8)
N2—C1—C6—C5175.1 (5)C16—C15—C14—C135 (3)
C1—C6—C5—C41.1 (9)C12—C11—C16—C151.6 (14)
C6—C5—C4—C30.9 (10)C10—C11—C16—C15176.7 (10)
C5—C4—C3—C20.4 (10)C14—C15—C16—C114 (2)
C5—C4—C3—C7177.5 (7)C15—C14—C13—C124 (3)
C1—C2—C3—C40.1 (9)C11—C12—C13—C140.8 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···S1i0.84 (6)2.51 (6)3.320 (5)164 (6)
Symmetry code: (i) x+1, y+1, z.
 

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