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In the title compound, C17H10F3NS, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015008671/hb7416sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015008671/hb7416Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015008671/hb7416Isup3.cml
Supplementary material

CCDC reference: 1063141

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For background to benzothiophene derivatives, see: Bettinetti et al. (2002); Roberts & Hartley (2004).

Experimental top

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.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 2 for details).
2-(p-Tolyl)-6-(trifluoromethyl)benzo[b]thiophene-3-carbonitrile top
Crystal data top
C17H10F3NSF(000) = 648
Mr = 317.33Dx = 1.479 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 2316 reflections
a = 13.7576 (5) Åθ = 6.4–64.7°
b = 14.5343 (6) ŵ = 2.29 mm1
c = 7.1353 (3) ÅT = 293 K
β = 92.817 (3)°Block, colourless
V = 1425.03 (10) Å30.30 × 0.27 × 0.25 mm
Z = 4
Data collection top
Bruker X8 Proteum
diffractometer
2316 independent reflections
Radiation source: Rotating Anode1860 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 18.4 pixels mm-1θmax = 64.7°, θmin = 6.4°
ϕ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1516
Tmin = 0.546, Tmax = 0.598l = 86
7045 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C17H10F3NSV = 1425.03 (10) Å3
Mr = 317.33Z = 4
Monoclinic, P21/cCu Kα radiation
a = 13.7576 (5) ŵ = 2.29 mm1
b = 14.5343 (6) ÅT = 293 K
c = 7.1353 (3) Å0.30 × 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 = 0.598Rint = 0.063
7045 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.06Δρmax = 0.43 e Å3
2316 reflectionsΔρmin = 0.40 e Å3
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
xyzUiso*/Ueq
S10.51842 (5)0.17833 (5)0.23250 (10)0.0214 (2)
F130.10569 (13)0.01265 (15)0.0632 (4)0.0518 (8)
F140.14077 (13)0.11887 (16)0.0469 (3)0.0450 (7)
F150.11752 (13)0.10360 (17)0.2439 (3)0.0484 (8)
N110.64047 (19)0.14957 (19)0.3600 (4)0.0297 (9)
C20.4251 (2)0.0996 (2)0.1944 (4)0.0202 (9)
C30.3272 (2)0.1178 (2)0.1485 (4)0.0212 (9)
C40.2634 (2)0.0444 (2)0.1373 (4)0.0210 (9)
C50.2957 (2)0.0459 (2)0.1679 (4)0.0217 (9)
C60.3920 (2)0.0643 (2)0.2103 (4)0.0203 (8)
C70.4583 (2)0.0087 (2)0.2249 (4)0.0178 (8)
C80.5601 (2)0.0069 (2)0.2816 (4)0.0174 (8)
C90.6018 (2)0.0928 (2)0.2949 (4)0.0183 (8)
C100.6079 (2)0.0785 (2)0.3267 (4)0.0204 (9)
C120.1574 (2)0.0636 (2)0.0993 (4)0.0253 (9)
C160.7014 (2)0.1180 (2)0.3613 (4)0.0182 (8)
C170.7798 (2)0.0588 (2)0.3430 (4)0.0198 (9)
C180.8717 (2)0.0826 (2)0.4144 (4)0.0236 (9)
C190.8890 (2)0.1655 (2)0.5074 (4)0.0235 (9)
C200.8107 (2)0.2255 (2)0.5220 (4)0.0217 (9)
C210.7190 (2)0.2025 (2)0.4506 (4)0.0194 (8)
C220.9878 (2)0.1887 (2)0.5939 (5)0.0306 (10)
H30.305600.177600.126000.0250*
H50.251200.094100.159400.0260*
H60.413100.124500.229100.0240*
H170.770400.002600.282300.0240*
H180.923200.042100.399900.0280*
H200.820500.282000.581100.0260*
H210.668000.243900.461900.0230*
H22A0.996400.158700.713400.0460*
H22B0.993000.254100.610700.0460*
H22C1.037000.168100.512800.0460*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0194 (4)0.0164 (4)0.0281 (4)0.0001 (3)0.0009 (3)0.0010 (3)
F130.0215 (9)0.0385 (13)0.0941 (17)0.0028 (9)0.0107 (10)0.0047 (12)
F140.0293 (10)0.0607 (15)0.0442 (12)0.0123 (10)0.0052 (9)0.0178 (11)
F150.0285 (10)0.0782 (17)0.0390 (11)0.0161 (10)0.0059 (9)0.0160 (11)
N110.0321 (15)0.0196 (16)0.0369 (16)0.0022 (12)0.0027 (12)0.0019 (13)
C20.0237 (15)0.0198 (16)0.0171 (14)0.0014 (12)0.0024 (11)0.0003 (13)
C30.0214 (14)0.0211 (17)0.0210 (14)0.0051 (12)0.0011 (12)0.0005 (13)
C40.0223 (15)0.0258 (17)0.0149 (13)0.0007 (13)0.0005 (11)0.0005 (13)
C50.0244 (15)0.0211 (17)0.0196 (14)0.0038 (12)0.0001 (12)0.0010 (13)
C60.0268 (15)0.0145 (15)0.0198 (14)0.0004 (12)0.0026 (12)0.0003 (12)
C70.0216 (14)0.0207 (16)0.0111 (13)0.0011 (12)0.0023 (11)0.0016 (12)
C80.0203 (14)0.0170 (15)0.0149 (13)0.0012 (12)0.0017 (11)0.0007 (12)
C90.0220 (14)0.0191 (16)0.0142 (13)0.0006 (12)0.0041 (11)0.0006 (12)
C100.0199 (14)0.0220 (18)0.0191 (15)0.0039 (13)0.0011 (12)0.0006 (13)
C120.0240 (15)0.0254 (18)0.0265 (16)0.0002 (13)0.0002 (13)0.0017 (14)
C160.0206 (14)0.0174 (16)0.0166 (13)0.0004 (12)0.0005 (11)0.0015 (12)
C170.0219 (15)0.0169 (16)0.0209 (14)0.0001 (12)0.0034 (12)0.0013 (13)
C180.0229 (15)0.0240 (17)0.0241 (15)0.0042 (13)0.0026 (12)0.0007 (13)
C190.0237 (15)0.0293 (18)0.0175 (14)0.0019 (13)0.0003 (12)0.0033 (13)
C200.0240 (15)0.0223 (17)0.0187 (14)0.0044 (13)0.0011 (12)0.0009 (13)
C210.0204 (14)0.0186 (16)0.0195 (14)0.0003 (12)0.0032 (11)0.0022 (13)
C220.0251 (16)0.037 (2)0.0295 (16)0.0014 (14)0.0015 (13)0.0015 (16)
Geometric parameters (Å, º) top
S1—C21.731 (3)C16—C171.391 (4)
S1—C91.735 (3)C16—C211.399 (4)
F13—C121.335 (4)C17—C181.384 (4)
F14—C121.328 (4)C18—C191.390 (4)
F15—C121.326 (4)C19—C201.394 (4)
N11—C101.146 (4)C19—C221.503 (4)
C2—C31.396 (4)C20—C211.378 (4)
C2—C71.411 (4)C3—H30.9300
C3—C41.381 (4)C5—H50.9300
C4—C51.399 (4)C6—H60.9300
C4—C121.496 (4)C17—H170.9300
C5—C61.371 (4)C18—H180.9300
C6—C71.400 (4)C20—H200.9300
C7—C81.439 (4)C21—H210.9300
C8—C91.375 (4)C22—H22A0.9600
C8—C101.434 (4)C22—H22B0.9600
C9—C161.474 (4)C22—H22C0.9600
C2—S1—C992.44 (14)C17—C16—C21117.9 (3)
S1—C2—C3127.7 (2)C16—C17—C18120.6 (3)
S1—C2—C7111.3 (2)C17—C18—C19121.6 (3)
C3—C2—C7121.0 (3)C18—C19—C20117.6 (3)
C2—C3—C4118.1 (3)C18—C19—C22121.4 (3)
C3—C4—C5121.3 (3)C20—C19—C22121.0 (3)
C3—C4—C12118.5 (3)C19—C20—C21121.2 (3)
C5—C4—C12120.2 (3)C16—C21—C20121.1 (3)
C4—C5—C6120.9 (3)C2—C3—H3121.00
C5—C6—C7119.2 (3)C4—C3—H3121.00
C2—C7—C6119.6 (3)C4—C5—H5120.00
C2—C7—C8111.3 (2)C6—C5—H5120.00
C6—C7—C8129.0 (3)C5—C6—H6120.00
C7—C8—C9113.6 (3)C7—C6—H6120.00
C7—C8—C10120.6 (3)C16—C17—H17120.00
C9—C8—C10125.8 (3)C18—C17—H17120.00
S1—C9—C8111.4 (2)C17—C18—H18119.00
S1—C9—C16119.8 (2)C19—C18—H18119.00
C8—C9—C16128.7 (3)C19—C20—H20119.00
N11—C10—C8175.6 (3)C21—C20—H20119.00
F13—C12—F14106.3 (2)C16—C21—H21120.00
F13—C12—F15106.1 (2)C20—C21—H21119.00
F13—C12—C4112.7 (2)C19—C22—H22A109.00
F14—C12—F15106.5 (2)C19—C22—H22B109.00
F14—C12—C4112.6 (2)C19—C22—H22C109.00
F15—C12—C4112.2 (2)H22A—C22—H22B109.00
C9—C16—C17121.9 (3)H22A—C22—H22C110.00
C9—C16—C21120.1 (3)H22B—C22—H22C109.00
C9—S1—C2—C3175.6 (3)C2—C7—C8—C90.5 (4)
C9—S1—C2—C71.4 (2)C2—C7—C8—C10177.7 (3)
C2—S1—C9—C81.7 (2)C6—C7—C8—C9175.0 (3)
C2—S1—C9—C16175.3 (2)C6—C7—C8—C102.2 (5)
S1—C2—C3—C4175.5 (2)C7—C8—C9—S11.6 (3)
C7—C2—C3—C41.2 (4)C7—C8—C9—C16175.2 (3)
S1—C2—C7—C6176.7 (2)C10—C8—C9—S1178.6 (2)
S1—C2—C7—C80.8 (3)C10—C8—C9—C161.8 (5)
C3—C2—C7—C60.5 (4)S1—C9—C16—C17154.1 (2)
C3—C2—C7—C8176.4 (3)S1—C9—C16—C2127.8 (4)
C2—C3—C4—C51.0 (4)C8—C9—C16—C1729.4 (5)
C2—C3—C4—C12176.5 (3)C8—C9—C16—C21148.7 (3)
C3—C4—C5—C60.1 (4)C9—C16—C17—C18177.0 (3)
C12—C4—C5—C6177.4 (3)C21—C16—C17—C181.2 (4)
C3—C4—C12—F13170.3 (3)C9—C16—C21—C20176.8 (3)
C3—C4—C12—F1450.1 (4)C17—C16—C21—C201.5 (4)
C3—C4—C12—F1570.0 (3)C16—C17—C18—C190.4 (4)
C5—C4—C12—F1312.2 (4)C17—C18—C19—C201.8 (4)
C5—C4—C12—F14132.4 (3)C17—C18—C19—C22176.6 (3)
C5—C4—C12—F15107.5 (3)C18—C19—C20—C211.5 (4)
C4—C5—C6—C70.7 (4)C22—C19—C20—C21176.9 (3)
C5—C6—C7—C20.5 (4)C19—C20—C21—C160.1 (4)
C5—C6—C7—C8174.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N11i0.932.623.411 (4)143
C22—H22C···F15ii0.962.453.375 (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···AD—HH···AD···AD—H···A
C3—H3···N11i0.932.623.411 (4)143
C22—H22C···F15ii0.962.453.375 (4)162
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z.
 

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