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The title compound, C18H14F4N2O2S, crystallizes in a conformation where the two benzene rings are parallel. In the crystal structure, mol­ecules form one-dimensional extended chains via O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037147/ww2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037147/ww2047Isup2.hkl
Contains datablock I

CCDC reference: 625035

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.065
  • wR factor = 0.175
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.25 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.35 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C14 - C15 ... 1.35 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C17 ... 1.44 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H111 .. O1 .. 2.62 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-hydroxy- 2-methylpropionamide top
Crystal data top
C18H14F4N2O2SZ = 2
Mr = 398.37F(000) = 408.00
Triclinic, P1Dx = 1.456 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 10.136 (5) ÅCell parameters from 7424 reflections
b = 10.343 (6) Åθ = 3.3–27.5°
c = 10.524 (4) ŵ = 0.23 mm1
α = 106.82 (2)°T = 296 K
β = 116.97 (2)°Block, colorless
γ = 95.19 (2)°0.28 × 0.25 × 0.17 mm
V = 908.9 (8) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
Rint = 0.026
Detector resolution: 10.00 pixels mm-1θmax = 27.5°
ω scansh = 1213
9009 measured reflectionsk = 1313
4135 independent reflectionsl = 1213
2814 reflections with F2 > 2σ(F2)
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065 w = 1/[0.0015Fo2 + 3σ(Fo2) + 0.5]/(4Fo2)
wR(F2) = 0.175(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.31 e Å3
4135 reflectionsΔρmin = 0.35 e Å3
253 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S11.05362 (9)0.66265 (11)0.81085 (8)0.0713 (2)
F10.3255 (2)0.0045 (2)0.7624 (3)0.1071 (9)
F20.5424 (3)0.0978 (2)0.9456 (2)0.1414 (9)
F30.5039 (4)0.0695 (2)0.7535 (4)0.1452 (15)
F410.6412 (12)0.5005 (16)0.1544 (5)0.136 (4)0.40
F420.6827 (11)0.5636 (12)0.1553 (5)0.125 (2)0.60
O10.9926 (2)0.66885 (18)1.07295 (18)0.0498 (4)
O20.6598 (2)0.6361 (2)0.73183 (19)0.0501 (5)
N10.7433 (2)0.4881 (2)0.8566 (2)0.0444 (5)
N20.1879 (3)0.1128 (2)0.3768 (2)0.0750 (8)
C10.9806 (3)0.7893 (2)0.9050 (2)0.0511 (7)
C20.8971 (2)0.7284 (2)0.9706 (2)0.0399 (6)
C30.8414 (3)0.8390 (3)1.0513 (3)0.0563 (8)
C40.7544 (2)0.6118 (2)0.8398 (2)0.0394 (6)
C50.6233 (2)0.3660 (2)0.7574 (2)0.0385 (5)
C60.5300 (2)0.3381 (2)0.6010 (2)0.0407 (6)
C70.4200 (2)0.2130 (2)0.5089 (2)0.0417 (6)
C80.3984 (2)0.1153 (2)0.5687 (2)0.0396 (6)
C90.4899 (2)0.1449 (2)0.7264 (2)0.0397 (6)
C100.6005 (2)0.2696 (2)0.8181 (2)0.0401 (6)
C110.9317 (3)0.6279 (3)0.6132 (2)0.0559 (8)
C120.8210 (3)0.5040 (4)0.5210 (3)0.0717 (10)
C130.7309 (4)0.4758 (5)0.3624 (4)0.0963 (13)
C140.7559 (5)0.5720 (7)0.3070 (3)0.1053 (18)
C150.8668 (6)0.6932 (6)0.3956 (5)0.1030 (18)
C160.9555 (4)0.7216 (4)0.5500 (4)0.0758 (12)
C170.2817 (3)0.0134 (2)0.4641 (2)0.0514 (7)
C180.4695 (3)0.0451 (2)0.7974 (2)0.0990 (13)
H10.91070.82310.83020.061*
H21.06640.86680.98780.061*
H60.54350.40710.55780.049*
H70.35530.19230.39880.050*
H100.66410.29070.92840.048*
H120.80690.43710.56620.086*
H130.65180.38750.29380.115*
H150.88110.75870.34900.124*
H161.03610.80930.61710.091*
H310.79120.79821.09420.067*
H320.92760.91531.13190.067*
H330.77080.87280.97870.067*
H1011.05210.73721.16960.060*
H1110.81710.48340.93750.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0565 (4)0.1081 (7)0.0483 (4)0.0362 (4)0.0218 (3)0.0308 (4)
F10.0872 (15)0.126 (2)0.1361 (19)0.0082 (14)0.0656 (14)0.0755 (17)
F20.191 (2)0.1093 (19)0.0545 (11)0.0607 (18)0.0182 (14)0.0413 (12)
F30.268 (4)0.1039 (19)0.209 (3)0.115 (2)0.186 (3)0.120 (2)
F410.108 (7)0.240 (15)0.037 (3)0.104 (8)0.022 (3)0.029 (4)
F420.114 (4)0.212 (8)0.056 (2)0.064 (4)0.040 (2)0.059 (3)
O10.0529 (10)0.0367 (9)0.0320 (8)0.0082 (8)0.0010 (7)0.0110 (7)
O20.0440 (9)0.0500 (11)0.0439 (9)0.0111 (8)0.0072 (7)0.0264 (8)
N10.0429 (11)0.0373 (11)0.0316 (9)0.0007 (9)0.0016 (7)0.0166 (8)
N20.0672 (17)0.0586 (17)0.0528 (14)0.0070 (14)0.0082 (12)0.0034 (12)
C10.0493 (15)0.0424 (15)0.0453 (13)0.0019 (12)0.0131 (11)0.0159 (11)
C20.0440 (13)0.0337 (13)0.0333 (11)0.0112 (10)0.0110 (9)0.0149 (9)
C30.0659 (18)0.0474 (16)0.0529 (15)0.0220 (14)0.0281 (13)0.0159 (12)
C40.0421 (13)0.0375 (13)0.0326 (11)0.0088 (10)0.0130 (9)0.0154 (9)
C50.0369 (12)0.0370 (13)0.0305 (10)0.0054 (10)0.0083 (8)0.0138 (9)
C60.0402 (12)0.0431 (14)0.0323 (11)0.0096 (11)0.0106 (9)0.0186 (10)
C70.0354 (12)0.0485 (15)0.0285 (10)0.0108 (11)0.0078 (8)0.0115 (10)
C80.0320 (11)0.0390 (13)0.0350 (11)0.0071 (10)0.0096 (9)0.0097 (9)
C90.0370 (12)0.0415 (14)0.0376 (11)0.0084 (10)0.0160 (9)0.0158 (10)
C100.0384 (12)0.0409 (13)0.0292 (10)0.0059 (10)0.0077 (8)0.0144 (9)
C110.0456 (15)0.079 (2)0.0445 (13)0.0195 (15)0.0221 (11)0.0242 (14)
C120.0561 (18)0.085 (2)0.0710 (19)0.0174 (18)0.0369 (15)0.0170 (17)
C130.053 (2)0.123 (3)0.068 (2)0.025 (2)0.0230 (17)0.010 (2)
C140.090 (3)0.185 (5)0.050 (2)0.081 (3)0.035 (2)0.043 (2)
C150.126 (3)0.159 (4)0.071 (2)0.077 (3)0.062 (2)0.072 (2)
C160.080 (2)0.094 (2)0.072 (2)0.031 (2)0.0452 (18)0.041 (2)
C170.0481 (15)0.0477 (16)0.0380 (12)0.0044 (13)0.0101 (11)0.0108 (11)
C180.104 (2)0.099 (2)0.085 (2)0.007 (2)0.042 (2)0.038 (2)
Geometric parameters (Å, º) top
S1—C11.826 (3)C9—C181.488 (4)
S1—C111.772 (2)C11—C121.369 (4)
F1—C181.324 (4)C11—C161.384 (6)
F2—C181.291 (3)C12—C131.411 (5)
F3—C181.283 (4)C13—C141.349 (9)
F41—C141.393 (6)C14—C151.349 (7)
F42—C141.393 (7)C15—C161.373 (5)
O1—C21.422 (3)O1—H1010.921
O2—C41.223 (3)N1—H1110.860
N1—C41.343 (3)C1—H10.970
N1—C51.404 (2)C1—H20.970
N2—C171.135 (3)C3—H310.960
C1—C21.508 (4)C3—H320.960
C2—C31.529 (4)C3—H330.960
C2—C41.536 (2)C6—H60.980
C5—C61.397 (3)C7—H70.980
C5—C101.383 (4)C10—H100.980
C6—C71.375 (3)C12—H120.980
C7—C81.385 (4)C13—H130.980
C8—C91.403 (3)C15—H150.980
C8—C171.439 (3)C16—H160.980
C9—C101.374 (2)
S1···F41i3.582 (14)C5···H101ix3.372
S1···C13i3.580 (5)C6···H6vii3.474
S1···C14i3.526 (6)C7···H1vii3.502
F1···F2ii3.280 (4)C8···H15vii3.566
F1···C3iii3.317 (5)C10···H101ix3.472
F2···F1ii3.280 (4)C11···H7vii3.566
F2···F2ii2.838 (4)C13···H6vii3.471
F2···F3ii3.492 (6)C15···H12i3.582
F2···C18ii3.477 (4)C15···H31viii3.431
F3···F2ii3.492 (6)C16···H7vii3.574
F3···O2iv3.552 (4)C16···H12i3.495
F3···C7v3.191 (5)C17···H32xiii3.506
F41···S1i3.582 (14)C17···H101xiii3.069
F41···F41vi3.208 (12)H1···C7vii3.502
F41···F42vi3.239 (10)H1···H2xv3.150
F41···C5vii3.484 (14)H1···H7vii2.629
F41···C10viii3.466 (9)H1···H32xv2.854
F42···F41vi3.239 (10)H2···C1xv3.554
F42···F42vi3.433 (10)H2···C3xv3.296
F42···N1viii3.359 (9)H2···H1xv3.150
O1···O1ix3.432 (2)H2···H2xv3.171
O1···N1ix3.167 (3)H2···H10ix3.216
O1···N2x2.918 (2)H2···H32xv2.891
O1···C5ix3.577 (3)H2···H33xv2.867
O2···F3xi3.552 (4)H6···O2vii2.662
O2···C6vii3.250 (3)H6···C6vii3.474
O2···C7vii3.188 (3)H6···C13vii3.471
O2···C13vii3.599 (4)H6···H6vii2.577
N1···F42xii3.359 (9)H6···H13vii3.538
N1···O1ix3.167 (3)H7···F3v2.728
N2···O1xiii2.918 (2)H7···O2vii2.516
N2···C3xiii3.478 (3)H7···C1vii3.527
C3···F1iii3.317 (5)H7···C4vii3.530
C3···N2x3.478 (3)H7···C11vii3.566
C5···F41vii3.484 (14)H7···C16vii3.574
C5···O1ix3.577 (3)H7···H1vii2.629
C6···O2vii3.250 (3)H7···H33vii3.400
C6···C13vii3.502 (6)H10···S1ix2.795
C6···C14vii3.566 (6)H10···F41xii2.833
C7···F3v3.191 (5)H10···F42xii3.050
C7···O2vii3.188 (3)H10···O1ix3.474
C8···C15vii3.569 (7)H10···C1ix3.519
C10···F41xii3.466 (9)H10···H2ix3.216
C10···F42vii3.556 (12)H10···H101ix3.477
C11···C12i3.585 (5)H12···N2v3.575
C11···C13i3.597 (6)H12···C15i3.582
C12···C11i3.585 (5)H12···C16i3.495
C12···C16i3.553 (6)H12···H101ix3.575
C13···S1i3.580 (5)H13···F3v3.310
C13···O2vii3.599 (4)H13···O2vii3.026
C13···C6vii3.502 (5)H13···H6vii3.538
C13···C11i3.597 (6)H15···F1vii3.481
C14···S1i3.526 (6)H15···O1viii3.491
C14···C6vii3.566 (6)H15···N2xvi3.118
C15···C8vii3.569 (7)H15···C3viii3.331
C16···C12i3.553 (6)H15···C8vii3.566
C18···F2ii3.477 (4)H15···H31viii2.583
S1···H10ix2.795H15···H32viii3.324
S1···H111ix3.246H15···H101viii3.068
F1···H15vii3.481H16···F1xvi2.845
F1···H16xiv2.845H16···H32xv3.130
F1···H31iii2.849H31···F1iii2.849
F1···H32iii3.309H31···F2iii3.522
F1···H33iii3.259H31···F42xii2.927
F2···H31iii3.522H31···N2x3.572
F2···H33iv3.407H31···C15xii3.431
F3···H7v2.728H31···H15xii2.583
F3···H13v3.310H32···F1iii3.309
F3···H33iv2.930H32···N2x2.845
F41···H10viii2.833H32···C1xv3.294
F41···H111viii3.455H32···C17x3.506
F42···H10viii3.050H32···H1xv2.854
F42···H31viii2.927H32···H2xv2.891
F42···H111viii3.119H32···H15xii3.324
O1···H10ix3.474H32···H16xv3.130
O1···H15xii3.491H33···F1iii3.259
O1···H111ix2.618H33···F2xi3.407
O2···H6vii2.662H33···F3xi2.930
O2···H7vii2.516H33···H2xv2.867
O2···H13vii3.026H33···H7vii3.400
N1···H101ix3.290H101···N1ix3.290
N2···H12v3.575H101···N2x1.997
N2···H15xiv3.118H101···C5ix3.372
N2···H31xiii3.572H101···C10ix3.472
N2···H32xiii2.845H101···C17x3.069
N2···H101xiii1.997H101···H10ix3.477
C1···H2xv3.554H101···H12ix3.575
C1···H7vii3.527H101···H15xii3.068
C1···H10ix3.519H101···H111ix2.941
C1···H32xv3.294H111···S1ix3.246
C3···H2xv3.296H111···F41xii3.455
C3···H15xii3.331H111···F42xii3.119
C4···H7vii3.530H111···O1ix2.618
C1—S1—C11103.32 (15)N2—C17—C8177.1 (3)
C4—N1—C5127.09 (19)F1—C18—F2102.8 (3)
S1—C1—C2112.9 (2)F1—C18—F3104.1 (2)
O1—C2—C1110.5 (2)F1—C18—C9112.6 (2)
O1—C2—C3110.8 (2)F2—C18—F3108.7 (3)
O1—C2—C4108.0 (2)F2—C18—C9113.8 (2)
C1—C2—C3111.0 (2)F3—C18—C9113.9 (3)
C1—C2—C4109.5 (2)C2—O1—H101109.4
C3—C2—C4107.0 (2)C4—N1—H111116.5
O2—C4—N1124.81 (18)C5—N1—H111116.4
O2—C4—C2119.9 (2)S1—C1—H1108.5
N1—C4—C2115.28 (19)S1—C1—H2108.5
N1—C5—C6122.3 (2)C2—C1—H1108.8
N1—C5—C10118.03 (19)C2—C1—H2108.7
C6—C5—C10119.68 (19)H1—C1—H2109.5
C5—C6—C7119.2 (2)C2—C3—H31109.3
C6—C7—C8121.3 (2)C2—C3—H32109.4
C7—C8—C9119.35 (19)C2—C3—H33109.7
C7—C8—C17117.7 (2)H31—C3—H32109.5
C9—C8—C17122.9 (2)H31—C3—H33109.5
C8—C9—C10119.2 (2)H32—C3—H33109.5
C8—C9—C18121.7 (2)C5—C6—H6120.1
C10—C9—C18119.1 (2)C7—C6—H6120.7
C5—C10—C9121.2 (2)C6—C7—H7119.5
S1—C11—C12119.9 (3)C8—C7—H7119.2
S1—C11—C16119.9 (2)C5—C10—H10119.5
C12—C11—C16120.0 (2)C9—C10—H10119.3
C11—C12—C13118.8 (4)C11—C12—H12119.5
C12—C13—C14119.0 (3)C13—C12—H12121.7
F41—C14—C1397.4 (7)C12—C13—H13120.4
F41—C14—C15139.7 (8)C14—C13—H13120.6
F42—C14—C13128.1 (6)C14—C15—H15119.6
F42—C14—C15108.9 (7)C16—C15—H15121.8
C13—C14—C15123.0 (3)C11—C16—H16119.1
C14—C15—C16118.6 (6)C15—C16—H16120.2
C11—C16—C15120.7 (3)
C1—S1—C11—C12105.5 (3)C6—C7—C8—C17179.5 (2)
C1—S1—C11—C1679.1 (3)C7—C8—C9—C100.8 (4)
C11—S1—C1—C2108.02 (19)C7—C8—C9—C18178.7 (2)
F42—F41—C14—C13175.1 (14)C17—C8—C9—C10179.0 (2)
F42—F41—C14—C154 (2)C17—C8—C9—C181.5 (4)
F41—F42—C14—C136.2 (18)C8—C9—C10—C50.2 (4)
F41—F42—C14—C15177.0 (14)C8—C9—C18—F151.7 (4)
C4—N1—C5—C626.2 (4)C8—C9—C18—F2168.1 (3)
C4—N1—C5—C10155.3 (3)C8—C9—C18—F366.6 (3)
C5—N1—C4—O20.9 (5)C10—C9—C18—F1127.8 (2)
C5—N1—C4—C2177.9 (2)C10—C9—C18—F211.4 (4)
S1—C1—C2—O155.44 (19)C10—C9—C18—F3114.0 (3)
S1—C1—C2—C3178.70 (15)C18—C9—C10—C5179.7 (2)
S1—C1—C2—C463.4 (2)S1—C11—C12—C13176.7 (3)
O1—C2—C4—O2175.2 (2)S1—C11—C16—C15176.8 (4)
O1—C2—C4—N15.9 (3)C12—C11—C16—C151.4 (7)
C1—C2—C4—O254.9 (3)C16—C11—C12—C131.2 (6)
C1—C2—C4—N1126.3 (2)C11—C12—C13—C140.4 (7)
C3—C2—C4—O265.5 (3)C12—C13—C14—F41178.3 (7)
C3—C2—C4—N1113.3 (3)C12—C13—C14—F42178.5 (8)
N1—C5—C6—C7176.4 (2)C12—C13—C14—C152.0 (9)
N1—C5—C10—C9176.9 (2)F41—C14—C15—C16178.7 (11)
C6—C5—C10—C91.6 (4)F42—C14—C15—C16178.9 (7)
C10—C5—C6—C72.0 (4)C13—C14—C15—C161.9 (10)
C5—C6—C7—C81.1 (4)C14—C15—C16—C110.1 (6)
C6—C7—C8—C90.3 (4)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z+2; (iii) x+1, y+1, z+2; (iv) x, y1, z; (v) x+1, y, z+1; (vi) x+1, y+1, z; (vii) x+1, y+1, z+1; (viii) x, y, z1; (ix) x+2, y+1, z+2; (x) x+1, y+1, z+1; (xi) x, y+1, z; (xii) x, y, z+1; (xiii) x1, y1, z1; (xiv) x1, y1, z; (xv) x+2, y+2, z+2; (xvi) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···N2x0.922.002.918 (2)178
N1—H111···O1ix0.862.623.167 (3)123
Symmetry codes: (ix) x+2, y+1, z+2; (x) x+1, y+1, z+1.
 

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