The title compound, C
16H
15F
3N
2S, 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
CCDC reference: 255881
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C16H15F3N2S | Z = 2 |
Mr = 324.37 | F(000) = 336 |
Triclinic, P1 | Dx = 1.361 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.978 (3) Å | Cell parameters from 575 reflections |
b = 7.298 (3) Å | θ = 2.4–24.7° |
c = 16.064 (7) Å | µ = 0.23 mm−1 |
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 tube | 1805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.911, Tmax = 0.959 | k = −9→9 |
6240 measured reflections | l = −19→19 |
Refinement top
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)] = 0.089 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H 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 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.73542 (18) | 0.2913 (2) | −0.01637 (9) | 0.0438 (5) | |
F1 | 0.4802 (9) | 0.0142 (12) | 0.4066 (3) | 0.159 (3) | |
F2 | 0.2316 (12) | −0.1312 (11) | 0.4477 (4) | 0.179 (3) | |
F3 | 0.2335 (11) | 0.1414 (12) | 0.4576 (3) | 0.166 (3) | |
N2 | 0.4284 (6) | 0.2741 (7) | 0.0966 (3) | 0.0406 (11) | |
N3 | 0.6168 (6) | 0.0016 (6) | 0.1046 (3) | 0.0392 (11) | |
C1 | 0.2966 (7) | 0.2102 (7) | 0.1692 (3) | 0.0334 (12) | |
C2 | 0.3582 (7) | 0.1439 (8) | 0.2494 (3) | 0.0474 (14) | |
C3 | 0.2250 (8) | 0.0946 (8) | 0.3201 (4) | 0.0512 (15) | |
C4 | 0.0311 (9) | 0.1109 (9) | 0.3110 (4) | 0.0575 (17) | |
C5 | −0.0289 (8) | 0.1778 (9) | 0.2311 (4) | 0.0569 (16) | |
C6 | 0.1013 (7) | 0.2261 (8) | 0.1600 (3) | 0.0421 (13) | |
C7 | 0.2936 (13) | 0.0300 (16) | 0.4067 (5) | 0.093 (3) | |
C8 | 0.5863 (6) | 0.1806 (7) | 0.0671 (3) | 0.0331 (12) | |
C9 | 0.7781 (8) | −0.1170 (8) | 0.0784 (4) | 0.0452 (14) | |
C10 | 0.7525 (8) | −0.3202 (8) | 0.1224 (4) | 0.0499 (15) | |
C11 | 0.7559 (10) | −0.3612 (8) | 0.2176 (4) | 0.0586 (17) | |
C12 | 0.9231 (15) | −0.3445 (11) | 0.2524 (6) | 0.099 (3) | |
C13 | 0.932 (3) | −0.3853 (17) | 0.3395 (9) | 0.169 (7) | |
C14 | 0.768 (4) | −0.441 (3) | 0.3916 (10) | 0.206 (13) | |
C15 | 0.603 (3) | −0.467 (2) | 0.3595 (10) | 0.197 (10) | |
C16 | 0.5950 (16) | −0.4200 (13) | 0.2706 (7) | 0.113 (3) | |
H2N | 0.400 (8) | 0.380 (9) | 0.067 (4) | 0.056 (19)* | |
H3N | 0.534 (8) | −0.053 (8) | 0.143 (4) | 0.047 (16)* | |
H2 | 0.4895 | 0.1322 | 0.2560 | 0.057* | |
H4 | −0.0585 | 0.0771 | 0.3586 | 0.069* | |
H5 | −0.1603 | 0.1907 | 0.2248 | 0.068* | |
H6 | 0.0582 | 0.2693 | 0.1060 | 0.051* | |
H9A | 0.8973 | −0.0760 | 0.0926 | 0.054* | |
H9B | 0.7871 | −0.1045 | 0.0167 | 0.054* | |
H10A | 0.6304 | −0.3579 | 0.1095 | 0.060* | |
H10B | 0.8541 | −0.3965 | 0.0986 | 0.060* | |
H12 | 1.0329 | −0.3047 | 0.2161 | 0.118* | |
H13 | 1.0460 | −0.3752 | 0.3625 | 0.203* | |
H14 | 0.7705 | −0.4620 | 0.4508 | 0.248* | |
H15 | 0.4965 | −0.5154 | 0.3960 | 0.236* | |
H16 | 0.4802 | −0.4288 | 0.2477 | 0.135* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0337 (7) | 0.0480 (9) | 0.0415 (8) | 0.0064 (6) | 0.0074 (5) | −0.0005 (6) |
F1 | 0.105 (4) | 0.298 (9) | 0.055 (3) | 0.022 (5) | −0.029 (3) | 0.004 (4) |
F2 | 0.245 (8) | 0.174 (7) | 0.088 (4) | −0.058 (6) | −0.055 (5) | 0.065 (4) |
F3 | 0.215 (7) | 0.233 (8) | 0.063 (3) | 0.056 (6) | −0.037 (4) | −0.064 (4) |
N2 | 0.037 (2) | 0.038 (3) | 0.040 (3) | 0.014 (2) | 0.0048 (18) | −0.001 (2) |
N3 | 0.037 (2) | 0.035 (3) | 0.040 (2) | 0.0057 (19) | 0.0061 (19) | −0.003 (2) |
C1 | 0.030 (2) | 0.032 (3) | 0.038 (3) | 0.004 (2) | 0.001 (2) | −0.009 (2) |
C2 | 0.031 (3) | 0.066 (4) | 0.042 (3) | 0.003 (3) | −0.003 (2) | −0.008 (3) |
C3 | 0.053 (4) | 0.057 (4) | 0.040 (3) | 0.001 (3) | 0.003 (3) | −0.007 (3) |
C4 | 0.050 (4) | 0.067 (4) | 0.051 (4) | −0.007 (3) | 0.018 (3) | −0.013 (3) |
C5 | 0.027 (3) | 0.074 (4) | 0.070 (4) | −0.001 (3) | 0.004 (3) | −0.019 (3) |
C6 | 0.037 (3) | 0.049 (3) | 0.041 (3) | 0.002 (2) | −0.008 (2) | −0.012 (3) |
C7 | 0.085 (6) | 0.145 (9) | 0.035 (4) | 0.005 (5) | 0.003 (4) | 0.000 (5) |
C8 | 0.029 (2) | 0.042 (3) | 0.028 (3) | 0.000 (2) | −0.0035 (19) | −0.007 (2) |
C9 | 0.044 (3) | 0.044 (3) | 0.045 (3) | 0.014 (2) | 0.000 (2) | −0.012 (3) |
C10 | 0.052 (3) | 0.036 (3) | 0.066 (4) | 0.007 (3) | −0.007 (3) | −0.021 (3) |
C11 | 0.083 (5) | 0.033 (3) | 0.056 (4) | 0.005 (3) | −0.005 (3) | −0.006 (3) |
C12 | 0.156 (9) | 0.063 (5) | 0.081 (6) | −0.004 (5) | −0.057 (6) | −0.003 (4) |
C13 | 0.32 (2) | 0.085 (8) | 0.111 (10) | −0.003 (11) | −0.105 (13) | −0.005 (8) |
C14 | 0.44 (4) | 0.109 (12) | 0.063 (9) | −0.010 (18) | −0.022 (15) | −0.003 (8) |
C15 | 0.33 (3) | 0.117 (11) | 0.108 (13) | −0.020 (15) | 0.095 (14) | −0.006 (10) |
C16 | 0.137 (8) | 0.083 (7) | 0.103 (8) | −0.009 (6) | 0.038 (6) | −0.009 (5) |
Geometric parameters (Å, º) top
S1—C8 | 1.689 (5) | C5—C4 | 1.368 (9) |
N3—C8 | 1.324 (6) | C5—H5 | 0.9300 |
N3—C9 | 1.456 (6) | C4—C3 | 1.371 (8) |
N3—H3N | 0.85 (6) | C4—H4 | 0.9300 |
C1—C2 | 1.376 (7) | C3—C7 | 1.486 (9) |
C1—C6 | 1.381 (7) | F3—C7 | 1.296 (11) |
C1—N2 | 1.415 (6) | C11—C16 | 1.364 (10) |
N2—C8 | 1.353 (6) | C11—C12 | 1.373 (10) |
N2—H2N | 0.83 (6) | F1—C7 | 1.299 (9) |
C10—C11 | 1.493 (9) | F2—C7 | 1.290 (11) |
C10—C9 | 1.506 (8) | C15—C14 | 1.36 (3) |
C10—H10A | 0.9700 | C15—C16 | 1.398 (19) |
C10—H10B | 0.9700 | C15—H15 | 0.9300 |
C2—C3 | 1.383 (7) | C12—C13 | 1.371 (14) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C9—H9A | 0.9700 | C14—C13 | 1.37 (3) |
C9—H9B | 0.9700 | C14—H14 | 0.9300 |
C6—C5 | 1.374 (7) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| | | |
C8—N3—C9 | 123.9 (4) | C6—C5—H5 | 119.4 |
C8—N3—H3N | 120 (4) | C5—C4—C3 | 119.1 (5) |
C9—N3—H3N | 116 (4) | C5—C4—H4 | 120.4 |
C2—C1—C6 | 119.5 (4) | C3—C4—H4 | 120.4 |
C2—C1—N2 | 121.4 (4) | C4—C3—C2 | 120.4 (5) |
C6—C1—N2 | 119.0 (5) | C4—C3—C7 | 120.2 (5) |
C8—N2—C1 | 128.0 (4) | C2—C3—C7 | 119.4 (6) |
C8—N2—H2N | 117 (4) | C16—C11—C12 | 119.4 (8) |
C1—N2—H2N | 115 (4) | C16—C11—C10 | 120.5 (8) |
N3—C8—N2 | 118.0 (4) | C12—C11—C10 | 120.1 (7) |
N3—C8—S1 | 122.0 (4) | F2—C7—F3 | 103.6 (7) |
N2—C8—S1 | 120.0 (4) | F2—C7—F1 | 105.6 (9) |
C11—C10—C9 | 114.6 (5) | F3—C7—F1 | 106.1 (9) |
C11—C10—H10A | 108.6 | F2—C7—C3 | 113.7 (8) |
C9—C10—H10A | 108.6 | F3—C7—C3 | 112.5 (8) |
C11—C10—H10B | 108.6 | F1—C7—C3 | 114.3 (6) |
C9—C10—H10B | 108.6 | C14—C15—C16 | 118.8 (18) |
H10A—C10—H10B | 107.6 | C14—C15—H15 | 120.6 |
C1—C2—C3 | 120.1 (5) | C16—C15—H15 | 120.6 |
C1—C2—H2 | 120.0 | C13—C12—C11 | 121.3 (12) |
C3—C2—H2 | 120.0 | C13—C12—H12 | 119.3 |
N3—C9—C10 | 110.9 (4) | C11—C12—H12 | 119.3 |
N3—C9—H9A | 109.5 | C15—C14—C13 | 121.8 (17) |
C10—C9—H9A | 109.5 | C15—C14—H14 | 119.1 |
N3—C9—H9B | 109.5 | C13—C14—H14 | 119.1 |
C10—C9—H9B | 109.5 | C11—C16—C15 | 120.0 (14) |
H9A—C9—H9B | 108.1 | C11—C16—H16 | 120.0 |
C5—C6—C1 | 119.6 (5) | C15—C16—H16 | 120.0 |
C5—C6—H6 | 120.2 | C14—C13—C12 | 118.4 (17) |
C1—C6—H6 | 120.2 | C14—C13—H13 | 120.8 |
C4—C5—C6 | 121.3 (5) | C12—C13—H13 | 120.8 |
C4—C5—H5 | 119.4 | | |
| | | |
C2—C1—N2—C8 | 54.8 (8) | C1—C2—C3—C7 | −177.8 (7) |
C6—C1—N2—C8 | −129.4 (6) | C9—C10—C11—C16 | 114.5 (7) |
C9—N3—C8—N2 | 178.5 (5) | C9—C10—C11—C12 | −67.2 (8) |
C9—N3—C8—S1 | −0.4 (7) | C4—C3—C7—F2 | 56.3 (11) |
C1—N2—C8—N3 | 6.4 (8) | C2—C3—C7—F2 | −125.8 (8) |
C1—N2—C8—S1 | −174.6 (4) | C4—C3—C7—F3 | −61.0 (11) |
C6—C1—C2—C3 | −0.3 (9) | C2—C3—C7—F3 | 116.9 (8) |
N2—C1—C2—C3 | 175.5 (5) | C4—C3—C7—F1 | 177.8 (8) |
C8—N3—C9—C10 | −169.5 (5) | C2—C3—C7—F1 | −4.3 (13) |
C11—C10—C9—N3 | −64.8 (7) | C16—C11—C12—C13 | −0.2 (13) |
C2—C1—C6—C5 | 0.8 (8) | C10—C11—C12—C13 | −178.5 (8) |
N2—C1—C6—C5 | −175.1 (5) | C16—C15—C14—C13 | −5 (3) |
C1—C6—C5—C4 | −1.1 (9) | C12—C11—C16—C15 | −1.6 (14) |
C6—C5—C4—C3 | 0.9 (10) | C10—C11—C16—C15 | 176.7 (10) |
C5—C4—C3—C2 | −0.4 (10) | C14—C15—C16—C11 | 4 (2) |
C5—C4—C3—C7 | 177.5 (7) | C15—C14—C13—C12 | 4 (3) |
C1—C2—C3—C4 | 0.1 (9) | C11—C12—C13—C14 | −0.8 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···S1i | 0.84 (6) | 2.51 (6) | 3.320 (5) | 164 (6) |
Symmetry code: (i) −x+1, −y+1, −z. |