organic compounds
N-[2-(3,4-Dimethoxyphenyl)-2-(phenylsulfanyl)ethyl]-2-(2-fluorophenyl)acetamide
aTecnológico Nacional de México/Instituto Tecnológico de Tijuana, Centro de Graduados e Investigación en Química. Apartado Postal 1166, Tijuana, B.C., Mexico
*Correspondence e-mail: gaguirre@tectijuana.mx
The title compound, C24H24FNO3S, is an intermediate in the synthesis of fluorine containing isoquinoline which crystallizes in the triclinic P with one molecule in the The structure presents a of enantiomers. The C—S—C—C torsion angle between the benzene ring system and the sulfonyl benzene ring is −178.5 (1)°. In the crystal, N—H⋯O hydrogen bonds between neighbouring molecules form chains of molecules along the a-axis direction.
CCDC reference: 2052869
Structure description
Sulfur- and fluorine-containing molecules play important roles in medicinal chemistry. Sulfur-containing compounds often show a variety of biological activities and serve important functions in applications in the pharmaceutical industry (Bernardi et al., 1985). A variety of sulfur-containing molecules have been isolated from natural sources and play major roles in drug discovery and development. The role of fluorine in drug design and development is expanding rapidly, as more is learned about the unique properties associated with this unusual element and how to deploy it in the pharmaceutical industry. The introduction of fluorine into a molecule can influence conformation, pKa, intrinsic potency, membrane permeability, metabolic pathways, and pharmacokinetic properties (Gillis et al., 2015). Various sulfur- and fluorine-containing molecules have been studied for their applications in medicinal chemistry, with those containing a sulfone group emerging with promising results. Some examples are the recently reported thiochroman-4-one derivatives (Vargas et al., 2017), in which structure–activity relationships have been studied and it has been found that the vinyl sulfone and fluorine moieties play important roles in the biological activity of the molecules (Fig. 1). The literature also reveals that these types of compounds also serve as neuroprotective agents (Woo et al., 2014), exhibit antituberculosis activity (Tiwari et al., 2015) and inhibit prostate cancer (Goa & Spencer, 1998).
Continuing our interest in developing new sulfur- and fluorine-containing C17 S1 C7 C1biologically active ) as a The torsion angle between the benzene ring system and the sulfonyl benzene ring is −178.5 (1)°. The C11—C10—C9 angle [117.8 (2)°] is slightly widened in comparison to an sp3-hybridized carbon atom; this is probably due to an attractive interaction between the fluorine on the benzene ring and the hydrogen atoms on the benzyl carbon. In the crystal, N—H⋯O hydrogen bonds between neighbouring molecules form chains of molecules along the a-axis direction (Table 1; Fig. 3).
we report here the synthesis and characterization of the title compound (Fig. 2Synthesis and crystallization
The title compound was synthesized by the oxidation of N-(2-(3,4-dimethoxyphenyl)-2-(phenylthio)ethyl)-2-(2-fluorophenyl)acetamide (0.229 g, 0.54 mmol) treated with NaIO4 (0.264, 1.23 mmol) in water (6 ml). The reaction mixture was stirred for 2 h in reflux and then was allowed to cool down at room temperature prior to extractions with DCM (3 × 20 ml). The solvent in the combined organic layer was removed under vacuum and purified by flash on silica gel (DCM/MeOH 95:5) to give a pale-yellow solid in 67% yield (0.163 g, 0.36 mmol).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2052869
https://doi.org/10.1107/S2414314620016636/sj4219sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016636/sj4219Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620016636/sj4219Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR2004 (Burla et al., 2007); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).C24H24FNO5S | Z = 2 |
Mr = 457.50 | F(000) = 480 |
Triclinic, P1 | Dx = 1.364 Mg m−3 |
a = 8.3751 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.7640 (4) Å | Cell parameters from 6250 reflections |
c = 15.3592 (5) Å | θ = 2.9–76.6° |
α = 97.676 (3)° | µ = 1.68 mm−1 |
β = 93.885 (3)° | T = 293 K |
γ = 115.319 (4)° | Irregular, translucent intense colourless |
V = 1114.18 (8) Å3 | 0.21 × 0.12 × 0.07 mm |
Rigaku SuperNova, Dual, Cu at zero, AtlasS2 diffractometer | 4663 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 4030 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.022 |
Detector resolution: 5.1980 pixels mm-1 | θmax = 76.8°, θmin = 2.9° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) | k = −12→12 |
Tmin = 0.816, Tmax = 1.000 | l = −19→17 |
14171 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0751P)2 + 0.4124P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
4663 reflections | Δρmax = 0.37 e Å−3 |
291 parameters | Δρmin = −0.30 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The C-bound H atoms were placed in calculated positions and treated as riding: C—H = 0.95–0.99 A° with Uiso(H) = 1.5Ueq(Cmethyl) and 1.2Ueq(C) for other H atoms. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.39652 (6) | 0.22548 (6) | 0.61360 (4) | 0.04490 (17) | |
F1 | 0.6743 (4) | 0.9600 (3) | 0.84275 (19) | 0.1440 (11) | |
O1 | 0.4440 (2) | 0.1166 (2) | 0.64885 (15) | 0.0685 (5) | |
O2 | 0.4379 (2) | 0.2591 (2) | 0.52804 (11) | 0.0733 (6) | |
O3 | 0.6887 (3) | 0.5399 (3) | 0.93514 (12) | 0.0724 (5) | |
O4 | 1.24722 (18) | 0.61837 (19) | 0.69344 (11) | 0.0505 (4) | |
O5 | 1.09028 (19) | 0.4413 (2) | 0.80129 (10) | 0.0524 (4) | |
N1 | 0.4765 (2) | 0.5359 (2) | 0.83493 (12) | 0.0482 (4) | |
H1 | 0.421805 | 0.586998 | 0.818120 | 0.058* | |
C1 | 0.7007 (2) | 0.4691 (2) | 0.69245 (13) | 0.0387 (4) | |
C2 | 0.7860 (3) | 0.5660 (3) | 0.63531 (15) | 0.0480 (5) | |
H2 | 0.720985 | 0.596306 | 0.597378 | 0.058* | |
C3 | 0.9689 (3) | 0.6187 (3) | 0.63396 (15) | 0.0493 (5) | |
H3 | 1.024558 | 0.683868 | 0.595053 | 0.059* | |
C4 | 1.0682 (2) | 0.5755 (2) | 0.68960 (14) | 0.0416 (4) | |
C5 | 0.9826 (3) | 0.4781 (2) | 0.74848 (13) | 0.0401 (4) | |
C6 | 0.8009 (2) | 0.4252 (2) | 0.74868 (13) | 0.0400 (4) | |
H6 | 0.744532 | 0.359023 | 0.787008 | 0.048* | |
C7 | 0.5010 (2) | 0.4060 (2) | 0.69177 (13) | 0.0395 (4) | |
H7 | 0.464425 | 0.478089 | 0.667997 | 0.047* | |
C8 | 0.4351 (3) | 0.3881 (3) | 0.78194 (14) | 0.0443 (5) | |
H8A | 0.307058 | 0.324890 | 0.773090 | 0.053* | |
H8B | 0.490585 | 0.336217 | 0.813264 | 0.053* | |
C9 | 0.5952 (3) | 0.5977 (3) | 0.90877 (15) | 0.0517 (5) | |
C10 | 0.6108 (4) | 0.7481 (3) | 0.95980 (18) | 0.0684 (7) | |
H10A | 0.599310 | 0.736563 | 1.021142 | 0.082* | |
H10B | 0.730226 | 0.827165 | 0.958892 | 0.082* | |
C11 | 0.4797 (4) | 0.8064 (3) | 0.92863 (16) | 0.0598 (6) | |
C12 | 0.5128 (6) | 0.9088 (4) | 0.8713 (2) | 0.0853 (10) | |
C13 | 0.3893 (8) | 0.9597 (4) | 0.8421 (2) | 0.1011 (14) | |
H13 | 0.416268 | 1.030105 | 0.803685 | 0.121* | |
C14 | 0.2253 (7) | 0.9011 (5) | 0.8724 (3) | 0.1040 (13) | |
H14 | 0.139973 | 0.931991 | 0.853658 | 0.125* | |
C15 | 0.1876 (6) | 0.8014 (5) | 0.9281 (3) | 0.0930 (11) | |
H15 | 0.076739 | 0.762740 | 0.947768 | 0.112* | |
C16 | 0.3134 (4) | 0.7560 (4) | 0.9562 (2) | 0.0728 (8) | |
H16 | 0.285373 | 0.687787 | 0.995874 | 0.087* | |
C17 | 0.1652 (3) | 0.1620 (2) | 0.61424 (14) | 0.0426 (4) | |
C18 | 0.0725 (3) | 0.0374 (3) | 0.65450 (19) | 0.0578 (6) | |
H18 | 0.130805 | −0.013477 | 0.679429 | 0.069* | |
C19 | −0.1083 (4) | −0.0101 (3) | 0.6570 (2) | 0.0741 (8) | |
H19 | −0.171943 | −0.092894 | 0.684308 | 0.089* | |
C20 | −0.1935 (3) | 0.0647 (3) | 0.6194 (2) | 0.0682 (7) | |
H20 | −0.315207 | 0.031227 | 0.620524 | 0.082* | |
C21 | −0.1021 (3) | 0.1872 (4) | 0.58042 (19) | 0.0648 (7) | |
H21 | −0.161059 | 0.238211 | 0.556282 | 0.078* | |
C22 | 0.0794 (3) | 0.2369 (3) | 0.57638 (16) | 0.0552 (6) | |
H22 | 0.141613 | 0.319261 | 0.548562 | 0.066* | |
C23 | 1.0135 (3) | 0.3553 (4) | 0.86799 (19) | 0.0692 (8) | |
H23A | 0.927690 | 0.253193 | 0.840542 | 0.104* | |
H23B | 0.955450 | 0.405134 | 0.902463 | 0.104* | |
H23C | 1.105425 | 0.349513 | 0.905972 | 0.104* | |
C24 | 1.3384 (3) | 0.7113 (3) | 0.6318 (2) | 0.0645 (7) | |
H24A | 1.287198 | 0.656772 | 0.572378 | 0.097* | |
H24B | 1.462304 | 0.733861 | 0.640809 | 0.097* | |
H24C | 1.326957 | 0.805723 | 0.640687 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0308 (2) | 0.0492 (3) | 0.0513 (3) | 0.0168 (2) | 0.00980 (19) | −0.0007 (2) |
F1 | 0.155 (2) | 0.1078 (18) | 0.128 (2) | 0.0098 (17) | 0.0651 (18) | 0.0350 (16) |
O1 | 0.0445 (9) | 0.0507 (9) | 0.1138 (16) | 0.0277 (8) | 0.0078 (9) | 0.0042 (9) |
O2 | 0.0508 (10) | 0.0919 (14) | 0.0495 (10) | 0.0093 (9) | 0.0176 (8) | −0.0057 (9) |
O3 | 0.0679 (12) | 0.0981 (15) | 0.0585 (11) | 0.0487 (11) | −0.0068 (9) | 0.0035 (10) |
O4 | 0.0292 (7) | 0.0595 (9) | 0.0602 (9) | 0.0132 (6) | 0.0144 (6) | 0.0205 (7) |
O5 | 0.0329 (7) | 0.0771 (11) | 0.0533 (9) | 0.0249 (7) | 0.0114 (6) | 0.0270 (8) |
N1 | 0.0403 (9) | 0.0568 (11) | 0.0489 (10) | 0.0267 (8) | 0.0018 (7) | −0.0023 (8) |
C1 | 0.0294 (9) | 0.0432 (10) | 0.0413 (10) | 0.0145 (8) | 0.0053 (7) | 0.0057 (8) |
C2 | 0.0393 (10) | 0.0534 (12) | 0.0534 (12) | 0.0199 (9) | 0.0061 (9) | 0.0189 (10) |
C3 | 0.0398 (11) | 0.0536 (12) | 0.0552 (12) | 0.0164 (9) | 0.0138 (9) | 0.0239 (10) |
C4 | 0.0288 (9) | 0.0451 (10) | 0.0465 (11) | 0.0115 (8) | 0.0105 (8) | 0.0080 (8) |
C5 | 0.0311 (9) | 0.0493 (11) | 0.0390 (10) | 0.0166 (8) | 0.0069 (7) | 0.0088 (8) |
C6 | 0.0316 (9) | 0.0484 (11) | 0.0404 (10) | 0.0161 (8) | 0.0112 (7) | 0.0121 (8) |
C7 | 0.0314 (9) | 0.0442 (10) | 0.0438 (10) | 0.0180 (8) | 0.0066 (7) | 0.0062 (8) |
C8 | 0.0333 (9) | 0.0504 (11) | 0.0499 (11) | 0.0197 (8) | 0.0105 (8) | 0.0045 (9) |
C9 | 0.0410 (11) | 0.0665 (14) | 0.0448 (12) | 0.0226 (10) | 0.0062 (9) | 0.0053 (10) |
C10 | 0.0630 (16) | 0.0700 (17) | 0.0566 (15) | 0.0229 (13) | −0.0015 (12) | −0.0123 (12) |
C11 | 0.0762 (17) | 0.0491 (13) | 0.0452 (12) | 0.0237 (12) | 0.0045 (11) | −0.0052 (10) |
C12 | 0.112 (3) | 0.0577 (16) | 0.0650 (18) | 0.0184 (17) | 0.0204 (17) | 0.0056 (13) |
C13 | 0.174 (5) | 0.0602 (19) | 0.067 (2) | 0.053 (2) | −0.006 (2) | 0.0107 (15) |
C14 | 0.144 (4) | 0.094 (3) | 0.085 (3) | 0.075 (3) | −0.010 (3) | −0.011 (2) |
C15 | 0.099 (3) | 0.106 (3) | 0.087 (2) | 0.063 (2) | 0.0086 (19) | 0.001 (2) |
C16 | 0.082 (2) | 0.0758 (19) | 0.0651 (17) | 0.0404 (16) | 0.0142 (14) | 0.0053 (14) |
C17 | 0.0301 (9) | 0.0480 (11) | 0.0444 (11) | 0.0151 (8) | 0.0050 (8) | −0.0017 (8) |
C18 | 0.0417 (12) | 0.0467 (12) | 0.0840 (17) | 0.0176 (10) | 0.0137 (11) | 0.0130 (12) |
C19 | 0.0440 (13) | 0.0555 (15) | 0.115 (2) | 0.0125 (11) | 0.0274 (14) | 0.0172 (15) |
C20 | 0.0325 (11) | 0.0645 (16) | 0.096 (2) | 0.0165 (11) | 0.0112 (12) | −0.0084 (14) |
C21 | 0.0452 (13) | 0.0781 (18) | 0.0735 (17) | 0.0341 (13) | −0.0057 (11) | 0.0041 (14) |
C22 | 0.0416 (11) | 0.0683 (15) | 0.0540 (13) | 0.0228 (11) | 0.0021 (9) | 0.0127 (11) |
C23 | 0.0491 (13) | 0.102 (2) | 0.0669 (16) | 0.0323 (14) | 0.0147 (12) | 0.0473 (16) |
C24 | 0.0403 (12) | 0.0674 (16) | 0.0872 (19) | 0.0164 (11) | 0.0290 (12) | 0.0344 (14) |
S1—O1 | 1.4378 (19) | C10—H10B | 0.9700 |
S1—O2 | 1.4264 (18) | C10—C11 | 1.515 (4) |
S1—C7 | 1.813 (2) | C11—C12 | 1.372 (4) |
S1—C17 | 1.765 (2) | C11—C16 | 1.382 (4) |
F1—C12 | 1.353 (5) | C12—C13 | 1.398 (6) |
O3—C9 | 1.221 (3) | C13—H13 | 0.9300 |
O4—C4 | 1.367 (2) | C13—C14 | 1.385 (6) |
O4—C24 | 1.428 (3) | C14—H14 | 0.9300 |
O5—C5 | 1.363 (2) | C14—C15 | 1.332 (6) |
O5—C23 | 1.423 (3) | C15—H15 | 0.9300 |
N1—H1 | 0.8600 | C15—C16 | 1.371 (5) |
N1—C8 | 1.443 (3) | C16—H16 | 0.9300 |
N1—C9 | 1.338 (3) | C17—C18 | 1.386 (3) |
C1—C2 | 1.380 (3) | C17—C22 | 1.377 (3) |
C1—C6 | 1.394 (3) | C18—H18 | 0.9300 |
C1—C7 | 1.513 (2) | C18—C19 | 1.387 (3) |
C2—H2 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.394 (3) | C19—C20 | 1.371 (4) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.379 (3) | C20—C21 | 1.358 (4) |
C4—C5 | 1.403 (3) | C21—H21 | 0.9300 |
C5—C6 | 1.383 (3) | C21—C22 | 1.393 (3) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—H7 | 0.9800 | C23—H23A | 0.9600 |
C7—C8 | 1.530 (3) | C23—H23B | 0.9600 |
C8—H8A | 0.9700 | C23—H23C | 0.9600 |
C8—H8B | 0.9700 | C24—H24A | 0.9600 |
C9—C10 | 1.518 (4) | C24—H24B | 0.9600 |
C10—H10A | 0.9700 | C24—H24C | 0.9600 |
O1—S1—C7 | 107.85 (11) | C11—C10—H10B | 107.9 |
O1—S1—C17 | 107.54 (11) | C12—C11—C10 | 124.0 (3) |
O2—S1—O1 | 119.44 (13) | C12—C11—C16 | 115.0 (3) |
O2—S1—C7 | 107.41 (11) | C16—C11—C10 | 121.0 (3) |
O2—S1—C17 | 108.68 (11) | F1—C12—C11 | 116.5 (4) |
C17—S1—C7 | 105.03 (9) | F1—C12—C13 | 120.1 (4) |
C4—O4—C24 | 117.09 (18) | C11—C12—C13 | 123.3 (4) |
C5—O5—C23 | 117.34 (16) | C12—C13—H13 | 121.3 |
C8—N1—H1 | 118.2 | C14—C13—C12 | 117.4 (3) |
C9—N1—H1 | 118.2 | C14—C13—H13 | 121.3 |
C9—N1—C8 | 123.6 (2) | C13—C14—H14 | 119.4 |
C2—C1—C6 | 118.69 (18) | C15—C14—C13 | 121.2 (4) |
C2—C1—C7 | 120.93 (18) | C15—C14—H14 | 119.4 |
C6—C1—C7 | 120.33 (17) | C14—C15—H15 | 120.2 |
C1—C2—H2 | 119.7 | C14—C15—C16 | 119.6 (4) |
C1—C2—C3 | 120.55 (19) | C16—C15—H15 | 120.2 |
C3—C2—H2 | 119.7 | C11—C16—H16 | 118.3 |
C2—C3—H3 | 119.6 | C15—C16—C11 | 123.5 (3) |
C4—C3—C2 | 120.83 (19) | C15—C16—H16 | 118.3 |
C4—C3—H3 | 119.6 | C18—C17—S1 | 118.95 (18) |
O4—C4—C3 | 125.98 (18) | C22—C17—S1 | 120.22 (17) |
O4—C4—C5 | 115.10 (18) | C22—C17—C18 | 120.8 (2) |
C3—C4—C5 | 118.92 (18) | C17—C18—H18 | 120.5 |
O5—C5—C4 | 115.25 (17) | C17—C18—C19 | 119.0 (2) |
O5—C5—C6 | 124.92 (18) | C19—C18—H18 | 120.5 |
C6—C5—C4 | 119.83 (18) | C18—C19—H19 | 120.0 |
C1—C6—H6 | 119.4 | C20—C19—C18 | 120.1 (3) |
C5—C6—C1 | 121.17 (18) | C20—C19—H19 | 120.0 |
C5—C6—H6 | 119.4 | C19—C20—H20 | 119.6 |
S1—C7—H7 | 107.1 | C21—C20—C19 | 120.7 (2) |
C1—C7—S1 | 107.66 (13) | C21—C20—H20 | 119.6 |
C1—C7—H7 | 107.1 | C20—C21—H21 | 119.8 |
C1—C7—C8 | 116.05 (16) | C20—C21—C22 | 120.5 (2) |
C8—C7—S1 | 111.53 (14) | C22—C21—H21 | 119.8 |
C8—C7—H7 | 107.1 | C17—C22—C21 | 118.9 (2) |
N1—C8—C7 | 111.25 (18) | C17—C22—H22 | 120.5 |
N1—C8—H8A | 109.4 | C21—C22—H22 | 120.5 |
N1—C8—H8B | 109.4 | O5—C23—H23A | 109.5 |
C7—C8—H8A | 109.4 | O5—C23—H23B | 109.5 |
C7—C8—H8B | 109.4 | O5—C23—H23C | 109.5 |
H8A—C8—H8B | 108.0 | H23A—C23—H23B | 109.5 |
O3—C9—N1 | 123.5 (2) | H23A—C23—H23C | 109.5 |
O3—C9—C10 | 120.3 (2) | H23B—C23—H23C | 109.5 |
N1—C9—C10 | 116.2 (2) | O4—C24—H24A | 109.5 |
C9—C10—H10A | 107.9 | O4—C24—H24B | 109.5 |
C9—C10—H10B | 107.9 | O4—C24—H24C | 109.5 |
H10A—C10—H10B | 107.2 | H24A—C24—H24B | 109.5 |
C11—C10—C9 | 117.8 (2) | H24A—C24—H24C | 109.5 |
C11—C10—H10A | 107.9 | H24B—C24—H24C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.86 | 2.46 | 3.207 (2) | 145 |
N1—H1···O5i | 0.86 | 2.50 | 2.945 (3) | 113 |
Symmetry code: (i) x−1, y, z. |
Funding information
This work was supported by Consejo Nacional de Ciencia y Tecnología grants (Nos. 6576.18-P, INFR-2011-3-173395, INFRA-2014-224405).
References
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