In the title molecular structure, C
15H
11F
3N
2OS, the dihedral angle between the two benzene rings is 7.1 (1)°. In the crystal structure, molecules form centrosymmetric dimers
via intermolecular N—H
S and C—H
S hydrogen bonds; the dimers are stacked along [010].
Supporting information
CCDC reference: 610847
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.145
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C7
Alert level C
PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.60 prolat
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1-Benzoyl-3-[3-(trifluoromethyl)phenyl]thiourea
top
Crystal data top
C15H11F3N2OS | F(000) = 664 |
Mr = 324.32 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2506 reflections |
a = 15.8710 (13) Å | θ = 2.6–27.4° |
b = 4.5603 (4) Å | µ = 0.26 mm−1 |
c = 19.6800 (16) Å | T = 120 K |
β = 95.477 (2)° | Needle, colorless |
V = 1417.9 (2) Å3 | 0.37 × 0.09 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 3416 independent reflections |
Radiation source: sealed tube | 2473 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 28.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −20→21 |
Tmin = 0.909, Tmax = 0.981 | k = −6→5 |
13559 measured reflections | l = −26→26 |
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)] = 0.056 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3 |
3416 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.64 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 | 0.61350 (4) | 0.82970 (17) | 0.00752 (3) | 0.0410 (2) | |
F1 | 0.94559 (13) | 0.3625 (4) | 0.06272 (9) | 0.0710 (6) | |
F2 | 0.82368 (13) | 0.2368 (7) | 0.08165 (10) | 0.1156 (11) | |
F3 | 0.90520 (12) | −0.0567 (3) | 0.03606 (8) | 0.0598 (5) | |
O1 | 0.61326 (10) | 1.1841 (4) | −0.20773 (7) | 0.0295 (4) | |
N1 | 0.68252 (11) | 0.8398 (4) | −0.11214 (9) | 0.0222 (4) | |
H1A | 0.6784 | 0.9195 | −0.1530 | 0.027* | |
N2 | 0.56722 (11) | 1.1389 (4) | −0.10209 (8) | 0.0217 (4) | |
H2B | 0.5297 | 1.2061 | −0.0759 | 0.026* | |
C1 | 0.74868 (13) | 0.6343 (5) | −0.10046 (10) | 0.0201 (4) | |
C2 | 0.77704 (13) | 0.5177 (5) | −0.03736 (10) | 0.0229 (5) | |
H2A | 0.7503 | 0.5693 | 0.0021 | 0.028* | |
C3 | 0.84472 (13) | 0.3253 (5) | −0.03260 (11) | 0.0239 (5) | |
C4 | 0.88411 (15) | 0.2424 (5) | −0.08944 (12) | 0.0301 (5) | |
H4A | 0.9299 | 0.1073 | −0.0854 | 0.036* | |
C5 | 0.85560 (15) | 0.3598 (5) | −0.15202 (12) | 0.0314 (6) | |
H5A | 0.8822 | 0.3060 | −0.1914 | 0.038* | |
C6 | 0.78882 (14) | 0.5546 (5) | −0.15791 (11) | 0.0268 (5) | |
H6A | 0.7700 | 0.6351 | −0.2012 | 0.032* | |
C7 | 0.87762 (15) | 0.2152 (6) | 0.03633 (12) | 0.0323 (6) | |
C8 | 0.62462 (13) | 0.9352 (5) | −0.07171 (10) | 0.0217 (5) | |
C9 | 0.56126 (13) | 1.2495 (5) | −0.16766 (10) | 0.0205 (5) | |
C10 | 0.48886 (13) | 1.4457 (5) | −0.18868 (10) | 0.0203 (4) | |
C11 | 0.47039 (14) | 1.4898 (5) | −0.25849 (11) | 0.0269 (5) | |
H11A | 0.5037 | 1.3972 | −0.2899 | 0.032* | |
C12 | 0.40362 (16) | 1.6682 (6) | −0.28210 (12) | 0.0336 (6) | |
H12A | 0.3914 | 1.6988 | −0.3298 | 0.040* | |
C13 | 0.35459 (15) | 1.8023 (5) | −0.23698 (12) | 0.0316 (6) | |
H13A | 0.3084 | 1.9234 | −0.2536 | 0.038* | |
C14 | 0.37274 (15) | 1.7601 (6) | −0.16734 (12) | 0.0308 (5) | |
H14A | 0.3388 | 1.8519 | −0.1362 | 0.037* | |
C15 | 0.44015 (14) | 1.5845 (5) | −0.14307 (11) | 0.0249 (5) | |
H15A | 0.4531 | 1.5588 | −0.0953 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0380 (4) | 0.0655 (5) | 0.0218 (3) | 0.0261 (3) | 0.0144 (3) | 0.0173 (3) |
F1 | 0.0956 (15) | 0.0429 (10) | 0.0634 (12) | −0.0146 (10) | −0.0494 (11) | 0.0087 (9) |
F2 | 0.0689 (13) | 0.235 (3) | 0.0469 (11) | 0.0836 (16) | 0.0265 (10) | 0.0717 (15) |
F3 | 0.0946 (14) | 0.0270 (9) | 0.0510 (10) | 0.0055 (9) | −0.0279 (9) | 0.0062 (7) |
O1 | 0.0291 (9) | 0.0392 (10) | 0.0219 (8) | 0.0096 (7) | 0.0103 (7) | 0.0054 (7) |
N1 | 0.0250 (9) | 0.0263 (10) | 0.0161 (8) | 0.0061 (8) | 0.0056 (7) | 0.0028 (7) |
N2 | 0.0224 (9) | 0.0268 (10) | 0.0169 (8) | 0.0072 (8) | 0.0069 (7) | 0.0027 (7) |
C1 | 0.0187 (10) | 0.0201 (11) | 0.0219 (10) | −0.0005 (9) | 0.0037 (8) | −0.0007 (8) |
C2 | 0.0228 (11) | 0.0248 (12) | 0.0212 (10) | 0.0008 (9) | 0.0025 (8) | −0.0004 (9) |
C3 | 0.0204 (11) | 0.0242 (12) | 0.0266 (11) | −0.0006 (9) | −0.0001 (9) | 0.0014 (9) |
C4 | 0.0229 (12) | 0.0308 (13) | 0.0365 (13) | 0.0079 (10) | 0.0027 (10) | 0.0033 (10) |
C5 | 0.0296 (13) | 0.0371 (14) | 0.0291 (12) | 0.0098 (11) | 0.0106 (10) | −0.0008 (10) |
C6 | 0.0278 (12) | 0.0326 (13) | 0.0206 (11) | 0.0041 (10) | 0.0053 (9) | 0.0029 (9) |
C7 | 0.0280 (13) | 0.0349 (14) | 0.0332 (13) | 0.0068 (11) | −0.0018 (10) | 0.0049 (11) |
C8 | 0.0223 (11) | 0.0245 (12) | 0.0186 (10) | 0.0027 (9) | 0.0040 (8) | −0.0004 (9) |
C9 | 0.0239 (11) | 0.0198 (11) | 0.0178 (10) | −0.0029 (9) | 0.0029 (8) | −0.0004 (8) |
C10 | 0.0208 (10) | 0.0192 (11) | 0.0210 (10) | −0.0032 (9) | 0.0024 (8) | 0.0016 (8) |
C11 | 0.0321 (13) | 0.0280 (12) | 0.0206 (11) | −0.0006 (10) | 0.0024 (9) | −0.0004 (9) |
C12 | 0.0421 (15) | 0.0336 (14) | 0.0231 (11) | 0.0013 (12) | −0.0081 (10) | 0.0026 (10) |
C13 | 0.0275 (13) | 0.0286 (13) | 0.0367 (13) | 0.0051 (10) | −0.0071 (10) | 0.0035 (10) |
C14 | 0.0284 (12) | 0.0315 (13) | 0.0331 (13) | 0.0056 (10) | 0.0068 (10) | 0.0023 (10) |
C15 | 0.0266 (12) | 0.0271 (12) | 0.0213 (10) | 0.0032 (10) | 0.0041 (9) | 0.0044 (9) |
Geometric parameters (Å, º) top
S1—C8 | 1.657 (2) | C4—C5 | 1.379 (3) |
F1—C7 | 1.333 (3) | C4—H4A | 0.9500 |
F2—C7 | 1.298 (3) | C5—C6 | 1.379 (3) |
F3—C7 | 1.315 (3) | C5—H5A | 0.9500 |
O1—C9 | 1.231 (2) | C6—H6A | 0.9500 |
N1—C8 | 1.344 (2) | C9—C10 | 1.484 (3) |
N1—C1 | 1.410 (3) | C10—C15 | 1.392 (3) |
N1—H1A | 0.8800 | C10—C11 | 1.392 (3) |
N2—C9 | 1.380 (3) | C11—C12 | 1.381 (3) |
N2—C8 | 1.395 (3) | C11—H11A | 0.9500 |
N2—H2B | 0.8800 | C12—C13 | 1.378 (3) |
C1—C2 | 1.386 (3) | C12—H12A | 0.9500 |
C1—C6 | 1.398 (3) | C13—C14 | 1.387 (3) |
C2—C3 | 1.383 (3) | C13—H13A | 0.9500 |
C2—H2A | 0.9500 | C14—C15 | 1.384 (3) |
C3—C4 | 1.385 (3) | C14—H14A | 0.9500 |
C3—C7 | 1.493 (3) | C15—H15A | 0.9500 |
| | | |
C8—N1—C1 | 131.25 (18) | F2—C7—C3 | 113.7 (2) |
C8—N1—H1A | 114.4 | F3—C7—C3 | 113.6 (2) |
C1—N1—H1A | 114.4 | F1—C7—C3 | 112.6 (2) |
C9—N2—C8 | 128.87 (17) | N1—C8—N2 | 114.67 (18) |
C9—N2—H2B | 115.6 | N1—C8—S1 | 127.09 (17) |
C8—N2—H2B | 115.6 | N2—C8—S1 | 118.22 (14) |
C2—C1—C6 | 119.4 (2) | O1—C9—N2 | 121.35 (19) |
C2—C1—N1 | 125.05 (18) | O1—C9—C10 | 121.06 (18) |
C6—C1—N1 | 115.51 (18) | N2—C9—C10 | 117.59 (17) |
C3—C2—C1 | 119.20 (19) | C15—C10—C11 | 119.6 (2) |
C3—C2—H2A | 120.4 | C15—C10—C9 | 123.89 (19) |
C1—C2—H2A | 120.4 | C11—C10—C9 | 116.55 (18) |
C2—C3—C4 | 121.7 (2) | C12—C11—C10 | 120.0 (2) |
C2—C3—C7 | 118.5 (2) | C12—C11—H11A | 120.0 |
C4—C3—C7 | 119.7 (2) | C10—C11—H11A | 120.0 |
C5—C4—C3 | 118.7 (2) | C13—C12—C11 | 120.5 (2) |
C5—C4—H4A | 120.6 | C13—C12—H12A | 119.8 |
C3—C4—H4A | 120.6 | C11—C12—H12A | 119.8 |
C4—C5—C6 | 120.6 (2) | C12—C13—C14 | 119.9 (2) |
C4—C5—H5A | 119.7 | C12—C13—H13A | 120.1 |
C6—C5—H5A | 119.7 | C14—C13—H13A | 120.1 |
C5—C6—C1 | 120.3 (2) | C15—C14—C13 | 120.1 (2) |
C5—C6—H6A | 119.8 | C15—C14—H14A | 119.9 |
C1—C6—H6A | 119.8 | C13—C14—H14A | 119.9 |
F2—C7—F3 | 108.4 (2) | C14—C15—C10 | 119.9 (2) |
F2—C7—F1 | 104.8 (2) | C14—C15—H15A | 120.0 |
F3—C7—F1 | 102.67 (19) | C10—C15—H15A | 120.0 |
| | | |
C8—N1—C1—C2 | −11.6 (4) | C1—N1—C8—N2 | −178.73 (19) |
C8—N1—C1—C6 | 170.5 (2) | C1—N1—C8—S1 | −0.7 (4) |
C6—C1—C2—C3 | 0.2 (3) | C9—N2—C8—N1 | 1.3 (3) |
N1—C1—C2—C3 | −177.7 (2) | C9—N2—C8—S1 | −176.93 (18) |
C1—C2—C3—C4 | −1.0 (3) | C8—N2—C9—O1 | −4.1 (3) |
C1—C2—C3—C7 | 176.5 (2) | C8—N2—C9—C10 | 174.69 (19) |
C2—C3—C4—C5 | 1.1 (4) | O1—C9—C10—C15 | −163.9 (2) |
C7—C3—C4—C5 | −176.4 (2) | N2—C9—C10—C15 | 17.3 (3) |
C3—C4—C5—C6 | −0.4 (4) | O1—C9—C10—C11 | 15.9 (3) |
C4—C5—C6—C1 | −0.5 (4) | N2—C9—C10—C11 | −162.94 (19) |
C2—C1—C6—C5 | 0.6 (3) | C15—C10—C11—C12 | −0.6 (3) |
N1—C1—C6—C5 | 178.6 (2) | C9—C10—C11—C12 | 179.6 (2) |
C2—C3—C7—F2 | 20.7 (3) | C10—C11—C12—C13 | −0.4 (4) |
C4—C3—C7—F2 | −161.6 (3) | C11—C12—C13—C14 | 0.6 (4) |
C2—C3—C7—F3 | 145.5 (2) | C12—C13—C14—C15 | 0.2 (4) |
C4—C3—C7—F3 | −36.9 (3) | C13—C14—C15—C10 | −1.2 (4) |
C2—C3—C7—F1 | −98.3 (3) | C11—C10—C15—C14 | 1.4 (3) |
C4—C3—C7—F1 | 79.3 (3) | C9—C10—C15—C14 | −178.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.88 | 1.86 | 2.611 (2) | 142 |
N2—H2B···S1i | 0.88 | 2.75 | 3.5680 (17) | 155 |
C15—H15A···S1i | 0.95 | 2.76 | 3.441 (2) | 130 |
Symmetry code: (i) −x+1, −y+2, −z. |