In the title compound, C
17H
10F
3NS, the dihedral angle between the fused benzothiophene ring system (r.m.s. deviation = 0.042 Å) and the benzene ring is 29.78 (11)°. The crystal structure features C—H

F and very weak C—H

N hydrogen bonds, which generate (001) sheets.
Supporting information
CCDC reference: 1063141
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(Wav) = 0.000 Å
- R factor = 0.053
- wR factor = 0.141
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5862
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
0 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
To a solution of 2-(2-chlorophenyl)acetonitrile (1.0 mmol), methyl
benzodithioate (1.0 mmol) in DMF (2 ml), K3PO4 (2.0 mmol), pivalic acid
(1.5 mmol), cuprous iodide (0.2 mmol) were added. The mixture was stirred at
80°C and progress was monitored by TLC. When the dithioesters could no longer
be detected, the reaction mixture was extracted with EtOAc (3 × 10 ml).
The organic layer was dried over anhydrous Na2SO4. The solvent was then
removed under reduced pressure and the residue was purified by silica gel
chromatography. White solid single crystals were obtained from slow
evaporation of its solvent.
All H atoms were positioned geometrically and allowed to ride on their parent
atom, with C–H = 0.93–0.97 Å, and with Uiso(H) =
1.2–1.5Ueq(C).
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
2-(
p-Tolyl)-6-(trifluoromethyl)benzo[
b]thiophene-3-carbonitrile
top
Crystal data top
C17H10F3NS | F(000) = 648 |
Mr = 317.33 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 2316 reflections |
a = 13.7576 (5) Å | θ = 6.4–64.7° |
b = 14.5343 (6) Å | µ = 2.29 mm−1 |
c = 7.1353 (3) Å | T = 293 K |
β = 92.817 (3)° | Block, colourless |
V = 1425.03 (10) Å3 | 0.30 × 0.27 × 0.25 mm |
Z = 4 | |
Data collection top
Bruker X8 Proteum diffractometer | 2316 independent reflections |
Radiation source: Rotating Anode | 1860 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.7°, θmin = 6.4° |
ϕ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −15→16 |
Tmin = 0.546, Tmax = 0.598 | l = −8→6 |
7045 measured reflections | |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.2459P] where P = (Fo2 + 2Fc2)/3 |
2316 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Crystal data top
C17H10F3NS | V = 1425.03 (10) Å3 |
Mr = 317.33 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.7576 (5) Å | µ = 2.29 mm−1 |
b = 14.5343 (6) Å | T = 293 K |
c = 7.1353 (3) Å | 0.30 × 0.27 × 0.25 mm |
β = 92.817 (3)° | |
Data collection top
Bruker X8 Proteum diffractometer | 2316 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 1860 reflections with I > 2σ(I) |
Tmin = 0.546, Tmax = 0.598 | Rint = 0.063 |
7045 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.43 e Å−3 |
2316 reflections | Δρmin = −0.40 e Å−3 |
200 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | 0.51842 (5) | 0.17833 (5) | 0.23250 (10) | 0.0214 (2) | |
F13 | 0.10569 (13) | −0.01265 (15) | 0.0632 (4) | 0.0518 (8) | |
F14 | 0.14077 (13) | 0.11887 (16) | −0.0469 (3) | 0.0450 (7) | |
F15 | 0.11752 (13) | 0.10360 (17) | 0.2439 (3) | 0.0484 (8) | |
N11 | 0.64047 (19) | −0.14957 (19) | 0.3600 (4) | 0.0297 (9) | |
C2 | 0.4251 (2) | 0.0996 (2) | 0.1944 (4) | 0.0202 (9) | |
C3 | 0.3272 (2) | 0.1178 (2) | 0.1485 (4) | 0.0212 (9) | |
C4 | 0.2634 (2) | 0.0444 (2) | 0.1373 (4) | 0.0210 (9) | |
C5 | 0.2957 (2) | −0.0459 (2) | 0.1679 (4) | 0.0217 (9) | |
C6 | 0.3920 (2) | −0.0643 (2) | 0.2103 (4) | 0.0203 (8) | |
C7 | 0.4583 (2) | 0.0087 (2) | 0.2249 (4) | 0.0178 (8) | |
C8 | 0.5601 (2) | 0.0069 (2) | 0.2816 (4) | 0.0174 (8) | |
C9 | 0.6018 (2) | 0.0928 (2) | 0.2949 (4) | 0.0183 (8) | |
C10 | 0.6079 (2) | −0.0785 (2) | 0.3267 (4) | 0.0204 (9) | |
C12 | 0.1574 (2) | 0.0636 (2) | 0.0993 (4) | 0.0253 (9) | |
C16 | 0.7014 (2) | 0.1180 (2) | 0.3613 (4) | 0.0182 (8) | |
C17 | 0.7798 (2) | 0.0588 (2) | 0.3430 (4) | 0.0198 (9) | |
C18 | 0.8717 (2) | 0.0826 (2) | 0.4144 (4) | 0.0236 (9) | |
C19 | 0.8890 (2) | 0.1655 (2) | 0.5074 (4) | 0.0235 (9) | |
C20 | 0.8107 (2) | 0.2255 (2) | 0.5220 (4) | 0.0217 (9) | |
C21 | 0.7190 (2) | 0.2025 (2) | 0.4506 (4) | 0.0194 (8) | |
C22 | 0.9878 (2) | 0.1887 (2) | 0.5939 (5) | 0.0306 (10) | |
H3 | 0.30560 | 0.17760 | 0.12600 | 0.0250* | |
H5 | 0.25120 | −0.09410 | 0.15940 | 0.0260* | |
H6 | 0.41310 | −0.12450 | 0.22910 | 0.0240* | |
H17 | 0.77040 | 0.00260 | 0.28230 | 0.0240* | |
H18 | 0.92320 | 0.04210 | 0.39990 | 0.0280* | |
H20 | 0.82050 | 0.28200 | 0.58110 | 0.0260* | |
H21 | 0.66800 | 0.24390 | 0.46190 | 0.0230* | |
H22A | 0.99640 | 0.15870 | 0.71340 | 0.0460* | |
H22B | 0.99300 | 0.25410 | 0.61070 | 0.0460* | |
H22C | 1.03700 | 0.16810 | 0.51280 | 0.0460* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0194 (4) | 0.0164 (4) | 0.0281 (4) | −0.0001 (3) | −0.0009 (3) | 0.0010 (3) |
F13 | 0.0215 (9) | 0.0385 (13) | 0.0941 (17) | −0.0028 (9) | −0.0107 (10) | −0.0047 (12) |
F14 | 0.0293 (10) | 0.0607 (15) | 0.0442 (12) | 0.0123 (10) | −0.0052 (9) | 0.0178 (11) |
F15 | 0.0285 (10) | 0.0782 (17) | 0.0390 (11) | 0.0161 (10) | 0.0059 (9) | −0.0160 (11) |
N11 | 0.0321 (15) | 0.0196 (16) | 0.0369 (16) | 0.0022 (12) | −0.0027 (12) | 0.0019 (13) |
C2 | 0.0237 (15) | 0.0198 (16) | 0.0171 (14) | −0.0014 (12) | 0.0024 (11) | −0.0003 (13) |
C3 | 0.0214 (14) | 0.0211 (17) | 0.0210 (14) | 0.0051 (12) | 0.0011 (12) | −0.0005 (13) |
C4 | 0.0223 (15) | 0.0258 (17) | 0.0149 (13) | −0.0007 (13) | 0.0005 (11) | −0.0005 (13) |
C5 | 0.0244 (15) | 0.0211 (17) | 0.0196 (14) | −0.0038 (12) | −0.0001 (12) | −0.0010 (13) |
C6 | 0.0268 (15) | 0.0145 (15) | 0.0198 (14) | −0.0004 (12) | 0.0026 (12) | 0.0003 (12) |
C7 | 0.0216 (14) | 0.0207 (16) | 0.0111 (13) | 0.0011 (12) | 0.0023 (11) | 0.0016 (12) |
C8 | 0.0203 (14) | 0.0170 (15) | 0.0149 (13) | 0.0012 (12) | 0.0017 (11) | −0.0007 (12) |
C9 | 0.0220 (14) | 0.0191 (16) | 0.0142 (13) | 0.0006 (12) | 0.0041 (11) | −0.0006 (12) |
C10 | 0.0199 (14) | 0.0220 (18) | 0.0191 (15) | −0.0039 (13) | −0.0011 (12) | −0.0006 (13) |
C12 | 0.0240 (15) | 0.0254 (18) | 0.0265 (16) | 0.0002 (13) | 0.0002 (13) | −0.0017 (14) |
C16 | 0.0206 (14) | 0.0174 (16) | 0.0166 (13) | −0.0004 (12) | 0.0005 (11) | 0.0015 (12) |
C17 | 0.0219 (15) | 0.0169 (16) | 0.0209 (14) | −0.0001 (12) | 0.0034 (12) | −0.0013 (13) |
C18 | 0.0229 (15) | 0.0240 (17) | 0.0241 (15) | 0.0042 (13) | 0.0026 (12) | −0.0007 (13) |
C19 | 0.0237 (15) | 0.0293 (18) | 0.0175 (14) | −0.0019 (13) | 0.0003 (12) | 0.0033 (13) |
C20 | 0.0240 (15) | 0.0223 (17) | 0.0187 (14) | −0.0044 (13) | 0.0011 (12) | −0.0009 (13) |
C21 | 0.0204 (14) | 0.0186 (16) | 0.0195 (14) | 0.0003 (12) | 0.0032 (11) | 0.0022 (13) |
C22 | 0.0251 (16) | 0.037 (2) | 0.0295 (16) | 0.0014 (14) | −0.0015 (13) | −0.0015 (16) |
Geometric parameters (Å, º) top
S1—C2 | 1.731 (3) | C16—C17 | 1.391 (4) |
S1—C9 | 1.735 (3) | C16—C21 | 1.399 (4) |
F13—C12 | 1.335 (4) | C17—C18 | 1.384 (4) |
F14—C12 | 1.328 (4) | C18—C19 | 1.390 (4) |
F15—C12 | 1.326 (4) | C19—C20 | 1.394 (4) |
N11—C10 | 1.146 (4) | C19—C22 | 1.503 (4) |
C2—C3 | 1.396 (4) | C20—C21 | 1.378 (4) |
C2—C7 | 1.411 (4) | C3—H3 | 0.9300 |
C3—C4 | 1.381 (4) | C5—H5 | 0.9300 |
C4—C5 | 1.399 (4) | C6—H6 | 0.9300 |
C4—C12 | 1.496 (4) | C17—H17 | 0.9300 |
C5—C6 | 1.371 (4) | C18—H18 | 0.9300 |
C6—C7 | 1.400 (4) | C20—H20 | 0.9300 |
C7—C8 | 1.439 (4) | C21—H21 | 0.9300 |
C8—C9 | 1.375 (4) | C22—H22A | 0.9600 |
C8—C10 | 1.434 (4) | C22—H22B | 0.9600 |
C9—C16 | 1.474 (4) | C22—H22C | 0.9600 |
| | | |
C2—S1—C9 | 92.44 (14) | C17—C16—C21 | 117.9 (3) |
S1—C2—C3 | 127.7 (2) | C16—C17—C18 | 120.6 (3) |
S1—C2—C7 | 111.3 (2) | C17—C18—C19 | 121.6 (3) |
C3—C2—C7 | 121.0 (3) | C18—C19—C20 | 117.6 (3) |
C2—C3—C4 | 118.1 (3) | C18—C19—C22 | 121.4 (3) |
C3—C4—C5 | 121.3 (3) | C20—C19—C22 | 121.0 (3) |
C3—C4—C12 | 118.5 (3) | C19—C20—C21 | 121.2 (3) |
C5—C4—C12 | 120.2 (3) | C16—C21—C20 | 121.1 (3) |
C4—C5—C6 | 120.9 (3) | C2—C3—H3 | 121.00 |
C5—C6—C7 | 119.2 (3) | C4—C3—H3 | 121.00 |
C2—C7—C6 | 119.6 (3) | C4—C5—H5 | 120.00 |
C2—C7—C8 | 111.3 (2) | C6—C5—H5 | 120.00 |
C6—C7—C8 | 129.0 (3) | C5—C6—H6 | 120.00 |
C7—C8—C9 | 113.6 (3) | C7—C6—H6 | 120.00 |
C7—C8—C10 | 120.6 (3) | C16—C17—H17 | 120.00 |
C9—C8—C10 | 125.8 (3) | C18—C17—H17 | 120.00 |
S1—C9—C8 | 111.4 (2) | C17—C18—H18 | 119.00 |
S1—C9—C16 | 119.8 (2) | C19—C18—H18 | 119.00 |
C8—C9—C16 | 128.7 (3) | C19—C20—H20 | 119.00 |
N11—C10—C8 | 175.6 (3) | C21—C20—H20 | 119.00 |
F13—C12—F14 | 106.3 (2) | C16—C21—H21 | 120.00 |
F13—C12—F15 | 106.1 (2) | C20—C21—H21 | 119.00 |
F13—C12—C4 | 112.7 (2) | C19—C22—H22A | 109.00 |
F14—C12—F15 | 106.5 (2) | C19—C22—H22B | 109.00 |
F14—C12—C4 | 112.6 (2) | C19—C22—H22C | 109.00 |
F15—C12—C4 | 112.2 (2) | H22A—C22—H22B | 109.00 |
C9—C16—C17 | 121.9 (3) | H22A—C22—H22C | 110.00 |
C9—C16—C21 | 120.1 (3) | H22B—C22—H22C | 109.00 |
| | | |
C9—S1—C2—C3 | 175.6 (3) | C2—C7—C8—C9 | 0.5 (4) |
C9—S1—C2—C7 | −1.4 (2) | C2—C7—C8—C10 | 177.7 (3) |
C2—S1—C9—C8 | 1.7 (2) | C6—C7—C8—C9 | −175.0 (3) |
C2—S1—C9—C16 | −175.3 (2) | C6—C7—C8—C10 | 2.2 (5) |
S1—C2—C3—C4 | −175.5 (2) | C7—C8—C9—S1 | −1.6 (3) |
C7—C2—C3—C4 | 1.2 (4) | C7—C8—C9—C16 | 175.2 (3) |
S1—C2—C7—C6 | 176.7 (2) | C10—C8—C9—S1 | −178.6 (2) |
S1—C2—C7—C8 | 0.8 (3) | C10—C8—C9—C16 | −1.8 (5) |
C3—C2—C7—C6 | −0.5 (4) | S1—C9—C16—C17 | −154.1 (2) |
C3—C2—C7—C8 | −176.4 (3) | S1—C9—C16—C21 | 27.8 (4) |
C2—C3—C4—C5 | −1.0 (4) | C8—C9—C16—C17 | 29.4 (5) |
C2—C3—C4—C12 | 176.5 (3) | C8—C9—C16—C21 | −148.7 (3) |
C3—C4—C5—C6 | 0.1 (4) | C9—C16—C17—C18 | −177.0 (3) |
C12—C4—C5—C6 | −177.4 (3) | C21—C16—C17—C18 | 1.2 (4) |
C3—C4—C12—F13 | 170.3 (3) | C9—C16—C21—C20 | 176.8 (3) |
C3—C4—C12—F14 | 50.1 (4) | C17—C16—C21—C20 | −1.5 (4) |
C3—C4—C12—F15 | −70.0 (3) | C16—C17—C18—C19 | 0.4 (4) |
C5—C4—C12—F13 | −12.2 (4) | C17—C18—C19—C20 | −1.8 (4) |
C5—C4—C12—F14 | −132.4 (3) | C17—C18—C19—C22 | 176.6 (3) |
C5—C4—C12—F15 | 107.5 (3) | C18—C19—C20—C21 | 1.5 (4) |
C4—C5—C6—C7 | 0.7 (4) | C22—C19—C20—C21 | −176.9 (3) |
C5—C6—C7—C2 | −0.5 (4) | C19—C20—C21—C16 | 0.1 (4) |
C5—C6—C7—C8 | 174.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N11i | 0.93 | 2.62 | 3.411 (4) | 143 |
C22—H22C···F15ii | 0.96 | 2.45 | 3.375 (4) | 162 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N11i | 0.93 | 2.62 | 3.411 (4) | 143 |
C22—H22C···F15ii | 0.96 | 2.45 | 3.375 (4) | 162 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z. |
Benzo[b]thiophene derivatives are important heterocyclic compounds because of their various applications in medicinal chemistry. They represent an important heterocyclic core and are shown to display a range of promising pharmacological properties such as antipsychotic, antidepressive, antithrombolytic, dopamine receptor antagonist and 5-lipoxygenase inhibitor. Number of 2-arylbenzo[b]thiophene derivatives have indeed, these sulfur heterocycles are essential components of clinically important drugs such as Clopidogrel (Bettinetti et al., 2002), Raloxifene (Roberts & Hartley, 2004) and Zileuton.