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In the title mol­ecular structure, C15H11F3N2OS, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018630/lh2079sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018630/lh2079Isup2.hkl
Contains datablock I

CCDC reference: 610847

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.145
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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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

Computing details top

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
C15H11F3N2OSF(000) = 664
Mr = 324.32Dx = 1.519 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2506 reflections
a = 15.8710 (13) Åθ = 2.6–27.4°
b = 4.5603 (4) ŵ = 0.26 mm1
c = 19.6800 (16) ÅT = 120 K
β = 95.477 (2)°Needle, colorless
V = 1417.9 (2) Å30.37 × 0.09 × 0.06 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3416 independent reflections
Radiation source: sealed tube2473 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 28.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2021
Tmin = 0.909, Tmax = 0.981k = 65
13559 measured reflectionsl = 2626
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)] = 0.056Hydrogen site location: difference Fourier map
wR(F2) = 0.145H-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 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.64 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
S10.61350 (4)0.82970 (17)0.00752 (3)0.0410 (2)
F10.94559 (13)0.3625 (4)0.06272 (9)0.0710 (6)
F20.82368 (13)0.2368 (7)0.08165 (10)0.1156 (11)
F30.90520 (12)0.0567 (3)0.03606 (8)0.0598 (5)
O10.61326 (10)1.1841 (4)0.20773 (7)0.0295 (4)
N10.68252 (11)0.8398 (4)0.11214 (9)0.0222 (4)
H1A0.67840.91950.15300.027*
N20.56722 (11)1.1389 (4)0.10209 (8)0.0217 (4)
H2B0.52971.20610.07590.026*
C10.74868 (13)0.6343 (5)0.10046 (10)0.0201 (4)
C20.77704 (13)0.5177 (5)0.03736 (10)0.0229 (5)
H2A0.75030.56930.00210.028*
C30.84472 (13)0.3253 (5)0.03260 (11)0.0239 (5)
C40.88411 (15)0.2424 (5)0.08944 (12)0.0301 (5)
H4A0.92990.10730.08540.036*
C50.85560 (15)0.3598 (5)0.15202 (12)0.0314 (6)
H5A0.88220.30600.19140.038*
C60.78882 (14)0.5546 (5)0.15791 (11)0.0268 (5)
H6A0.77000.63510.20120.032*
C70.87762 (15)0.2152 (6)0.03633 (12)0.0323 (6)
C80.62462 (13)0.9352 (5)0.07171 (10)0.0217 (5)
C90.56126 (13)1.2495 (5)0.16766 (10)0.0205 (5)
C100.48886 (13)1.4457 (5)0.18868 (10)0.0203 (4)
C110.47039 (14)1.4898 (5)0.25849 (11)0.0269 (5)
H11A0.50371.39720.28990.032*
C120.40362 (16)1.6682 (6)0.28210 (12)0.0336 (6)
H12A0.39141.69880.32980.040*
C130.35459 (15)1.8023 (5)0.23698 (12)0.0316 (6)
H13A0.30841.92340.25360.038*
C140.37274 (15)1.7601 (6)0.16734 (12)0.0308 (5)
H14A0.33881.85190.13620.037*
C150.44015 (14)1.5845 (5)0.14307 (11)0.0249 (5)
H15A0.45311.55880.09530.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0380 (4)0.0655 (5)0.0218 (3)0.0261 (3)0.0144 (3)0.0173 (3)
F10.0956 (15)0.0429 (10)0.0634 (12)0.0146 (10)0.0494 (11)0.0087 (9)
F20.0689 (13)0.235 (3)0.0469 (11)0.0836 (16)0.0265 (10)0.0717 (15)
F30.0946 (14)0.0270 (9)0.0510 (10)0.0055 (9)0.0279 (9)0.0062 (7)
O10.0291 (9)0.0392 (10)0.0219 (8)0.0096 (7)0.0103 (7)0.0054 (7)
N10.0250 (9)0.0263 (10)0.0161 (8)0.0061 (8)0.0056 (7)0.0028 (7)
N20.0224 (9)0.0268 (10)0.0169 (8)0.0072 (8)0.0069 (7)0.0027 (7)
C10.0187 (10)0.0201 (11)0.0219 (10)0.0005 (9)0.0037 (8)0.0007 (8)
C20.0228 (11)0.0248 (12)0.0212 (10)0.0008 (9)0.0025 (8)0.0004 (9)
C30.0204 (11)0.0242 (12)0.0266 (11)0.0006 (9)0.0001 (9)0.0014 (9)
C40.0229 (12)0.0308 (13)0.0365 (13)0.0079 (10)0.0027 (10)0.0033 (10)
C50.0296 (13)0.0371 (14)0.0291 (12)0.0098 (11)0.0106 (10)0.0008 (10)
C60.0278 (12)0.0326 (13)0.0206 (11)0.0041 (10)0.0053 (9)0.0029 (9)
C70.0280 (13)0.0349 (14)0.0332 (13)0.0068 (11)0.0018 (10)0.0049 (11)
C80.0223 (11)0.0245 (12)0.0186 (10)0.0027 (9)0.0040 (8)0.0004 (9)
C90.0239 (11)0.0198 (11)0.0178 (10)0.0029 (9)0.0029 (8)0.0004 (8)
C100.0208 (10)0.0192 (11)0.0210 (10)0.0032 (9)0.0024 (8)0.0016 (8)
C110.0321 (13)0.0280 (12)0.0206 (11)0.0006 (10)0.0024 (9)0.0004 (9)
C120.0421 (15)0.0336 (14)0.0231 (11)0.0013 (12)0.0081 (10)0.0026 (10)
C130.0275 (13)0.0286 (13)0.0367 (13)0.0051 (10)0.0071 (10)0.0035 (10)
C140.0284 (12)0.0315 (13)0.0331 (13)0.0056 (10)0.0068 (10)0.0023 (10)
C150.0266 (12)0.0271 (12)0.0213 (10)0.0032 (10)0.0041 (9)0.0044 (9)
Geometric parameters (Å, º) top
S1—C81.657 (2)C4—C51.379 (3)
F1—C71.333 (3)C4—H4A0.9500
F2—C71.298 (3)C5—C61.379 (3)
F3—C71.315 (3)C5—H5A0.9500
O1—C91.231 (2)C6—H6A0.9500
N1—C81.344 (2)C9—C101.484 (3)
N1—C11.410 (3)C10—C151.392 (3)
N1—H1A0.8800C10—C111.392 (3)
N2—C91.380 (3)C11—C121.381 (3)
N2—C81.395 (3)C11—H11A0.9500
N2—H2B0.8800C12—C131.378 (3)
C1—C21.386 (3)C12—H12A0.9500
C1—C61.398 (3)C13—C141.387 (3)
C2—C31.383 (3)C13—H13A0.9500
C2—H2A0.9500C14—C151.384 (3)
C3—C41.385 (3)C14—H14A0.9500
C3—C71.493 (3)C15—H15A0.9500
C8—N1—C1131.25 (18)F2—C7—C3113.7 (2)
C8—N1—H1A114.4F3—C7—C3113.6 (2)
C1—N1—H1A114.4F1—C7—C3112.6 (2)
C9—N2—C8128.87 (17)N1—C8—N2114.67 (18)
C9—N2—H2B115.6N1—C8—S1127.09 (17)
C8—N2—H2B115.6N2—C8—S1118.22 (14)
C2—C1—C6119.4 (2)O1—C9—N2121.35 (19)
C2—C1—N1125.05 (18)O1—C9—C10121.06 (18)
C6—C1—N1115.51 (18)N2—C9—C10117.59 (17)
C3—C2—C1119.20 (19)C15—C10—C11119.6 (2)
C3—C2—H2A120.4C15—C10—C9123.89 (19)
C1—C2—H2A120.4C11—C10—C9116.55 (18)
C2—C3—C4121.7 (2)C12—C11—C10120.0 (2)
C2—C3—C7118.5 (2)C12—C11—H11A120.0
C4—C3—C7119.7 (2)C10—C11—H11A120.0
C5—C4—C3118.7 (2)C13—C12—C11120.5 (2)
C5—C4—H4A120.6C13—C12—H12A119.8
C3—C4—H4A120.6C11—C12—H12A119.8
C4—C5—C6120.6 (2)C12—C13—C14119.9 (2)
C4—C5—H5A119.7C12—C13—H13A120.1
C6—C5—H5A119.7C14—C13—H13A120.1
C5—C6—C1120.3 (2)C15—C14—C13120.1 (2)
C5—C6—H6A119.8C15—C14—H14A119.9
C1—C6—H6A119.8C13—C14—H14A119.9
F2—C7—F3108.4 (2)C14—C15—C10119.9 (2)
F2—C7—F1104.8 (2)C14—C15—H15A120.0
F3—C7—F1102.67 (19)C10—C15—H15A120.0
C8—N1—C1—C211.6 (4)C1—N1—C8—N2178.73 (19)
C8—N1—C1—C6170.5 (2)C1—N1—C8—S10.7 (4)
C6—C1—C2—C30.2 (3)C9—N2—C8—N11.3 (3)
N1—C1—C2—C3177.7 (2)C9—N2—C8—S1176.93 (18)
C1—C2—C3—C41.0 (3)C8—N2—C9—O14.1 (3)
C1—C2—C3—C7176.5 (2)C8—N2—C9—C10174.69 (19)
C2—C3—C4—C51.1 (4)O1—C9—C10—C15163.9 (2)
C7—C3—C4—C5176.4 (2)N2—C9—C10—C1517.3 (3)
C3—C4—C5—C60.4 (4)O1—C9—C10—C1115.9 (3)
C4—C5—C6—C10.5 (4)N2—C9—C10—C11162.94 (19)
C2—C1—C6—C50.6 (3)C15—C10—C11—C120.6 (3)
N1—C1—C6—C5178.6 (2)C9—C10—C11—C12179.6 (2)
C2—C3—C7—F220.7 (3)C10—C11—C12—C130.4 (4)
C4—C3—C7—F2161.6 (3)C11—C12—C13—C140.6 (4)
C2—C3—C7—F3145.5 (2)C12—C13—C14—C150.2 (4)
C4—C3—C7—F336.9 (3)C13—C14—C15—C101.2 (4)
C2—C3—C7—F198.3 (3)C11—C10—C15—C141.4 (3)
C4—C3—C7—F179.3 (3)C9—C10—C15—C14178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.881.862.611 (2)142
N2—H2B···S1i0.882.753.5680 (17)155
C15—H15A···S1i0.952.763.441 (2)130
Symmetry code: (i) x+1, y+2, z.
 

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