organic compounds
N-(5-Benzylsulfanyl-1,3,4-thiadiazol-2-yl)-2-(piperidin-1-yl)acetamide
aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
*Correspondence e-mail: raxul@mail.ru
The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzylsulfanyl-5-chloroacetamido-1,3,4-thiadiazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thiadiazole units are twisted by 10.8 (4)°. The thiadiazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S⋯O interaction of 2.628 (4) Å. In the crystal, molecules form centrosymmetric dimers via N—H⋯N hydrogen bonds. These dimers are further connected by C—H⋯O interactions into (100) layers.
CCDC reference: 984204
Related literature
For physiological properties and syntheses of 1,3,4-thiadiazole derivatives, see: Turner et al. (1988); Chapleo et al. (1987); Cleici et al. (2001); Jain & Mishra (2004). For the structures of related 1,3,4-thiadiazole derivatives, see: Leung et al. (1992); Zhang (2009).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 984204
10.1107/S160053681400213X/gk2599sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400213X/gk2599Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400213X/gk2599Isup3.cml
To a solution of 2.99 g (10 mmol) of 2–benzylsulfanyl–5–chloroacetamido–1,3,4–thiadiazole in 15 ml benzene was added dropwise 1.7 g (20 mmol) of piperidine at room temperature. The reaction mixture was refluxed for 8 h. Benzene was distilled off, the residue was washed with water, 2% solution of NaOH, again with water and re-crystallized from hexane [yield 3.02 g (87%); m.p. 376–377 K]. Colourless crystals suitable for X–ray analysis were grown from hexane at room temperature.
The H atoms were placed geometrically with N—H ═ 0.86 Å, C—H =0.93 Å for Car or 0.97 Å for methylene group and included in the in a riding model approximation with Uiso=1.2Ueq(C, N)
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C16H20N4OS2 | F(000) = 736 |
Mr = 348.48 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Melting point < 376(1) K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54184 Å |
a = 17.429 (4) Å | Cell parameters from 124 reflections |
b = 16.748 (3) Å | θ = 5.9–35.8° |
c = 5.8390 (12) Å | µ = 2.92 mm−1 |
β = 95.48 (3)° | T = 290 K |
V = 1696.6 (6) Å3 | Prizmatic, colourless |
Z = 4 | 0.35 × 0.28 × 0.20 mm |
Oxford Diffraction Xcalibur Ruby diffractometer | 2970 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1521 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.117 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 66.6°, θmin = 3.7° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = 0→19 |
Tmin = 0.431, Tmax = 0.558 | l = 0→6 |
7003 measured reflections |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.1068P)2] where P = (Fo2 + 2Fc2)/3 |
2970 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C16H20N4OS2 | V = 1696.6 (6) Å3 |
Mr = 348.48 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 17.429 (4) Å | µ = 2.92 mm−1 |
b = 16.748 (3) Å | T = 290 K |
c = 5.8390 (12) Å | 0.35 × 0.28 × 0.20 mm |
β = 95.48 (3)° |
Oxford Diffraction Xcalibur Ruby diffractometer | 2970 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 1521 reflections with I > 2σ(I) |
Tmin = 0.431, Tmax = 0.558 | Rint = 0.117 |
7003 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.41 e Å−3 |
2970 reflections | Δρmin = −0.39 e Å−3 |
208 parameters |
Experimental. 1H NMR (400 MHz, CDCl3, DMSO): 7.30 (5H, m, H–5,6,7,8,9), 6.36 (1H, s, N–H), 4.39 (2H, s, CH2–11), 3.17 (2H, s CH2–3), 2.47 (4H, t, J═5.0 Hz, CH2–12,16), 1.57 (4H, m, CH2–13,15), 1.42 (2H, t, J═5.1 Hz, CH2–14). |
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. 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.52312 (7) | 0.33111 (9) | 0.9429 (2) | 0.0528 (4) | |
S2 | 0.39119 (9) | 0.32063 (11) | 1.2305 (3) | 0.0642 (5) | |
O1 | 0.6512 (2) | 0.3164 (3) | 0.7429 (8) | 0.0675 (12) | |
N1 | 0.4609 (3) | 0.4532 (3) | 0.7342 (8) | 0.0545 (12) | |
N2 | 0.4113 (3) | 0.4313 (3) | 0.8972 (8) | 0.0536 (12) | |
N3 | 0.5742 (3) | 0.4130 (3) | 0.5819 (8) | 0.0549 (12) | |
H3 | 0.5681 | 0.4490 | 0.4769 | 0.066* | |
N4 | 0.7677 (3) | 0.3620 (3) | 0.4568 (7) | 0.0499 (11) | |
C1 | 0.5195 (3) | 0.4055 (4) | 0.7371 (9) | 0.0496 (14) | |
C2 | 0.4357 (3) | 0.3686 (4) | 1.0141 (9) | 0.0524 (15) | |
C3 | 0.3196 (3) | 0.3937 (4) | 1.3030 (10) | 0.0637 (17) | |
H3B | 0.3186 | 0.3945 | 1.4688 | 0.076* | |
H3C | 0.3357 | 0.4461 | 1.2561 | 0.076* | |
C4 | 0.2399 (3) | 0.3782 (4) | 1.1947 (9) | 0.0526 (14) | |
C5 | 0.2152 (3) | 0.4084 (4) | 0.9797 (10) | 0.0641 (17) | |
H5A | 0.2496 | 0.4359 | 0.8964 | 0.077* | |
C6 | 0.1403 (4) | 0.3980 (5) | 0.8881 (11) | 0.074 (2) | |
H6A | 0.1248 | 0.4181 | 0.7426 | 0.089* | |
C7 | 0.0882 (4) | 0.3586 (4) | 1.0077 (12) | 0.0730 (19) | |
H7A | 0.0371 | 0.3534 | 0.9472 | 0.088* | |
C8 | 0.1127 (4) | 0.3267 (5) | 1.2187 (12) | 0.077 (2) | |
H8A | 0.0782 | 0.2981 | 1.2991 | 0.093* | |
C9 | 0.1871 (3) | 0.3364 (4) | 1.3124 (11) | 0.0677 (18) | |
H9A | 0.2025 | 0.3147 | 1.4562 | 0.081* | |
C10 | 0.6380 (3) | 0.3646 (4) | 0.5903 (10) | 0.0500 (14) | |
C11 | 0.6864 (3) | 0.3734 (4) | 0.3892 (9) | 0.0550 (15) | |
H11A | 0.6694 | 0.3347 | 0.2717 | 0.066* | |
H11B | 0.6784 | 0.4263 | 0.3231 | 0.066* | |
C12 | 0.8104 (3) | 0.3476 (4) | 0.2561 (10) | 0.0606 (16) | |
H12A | 0.8052 | 0.3935 | 0.1545 | 0.073* | |
H12B | 0.7888 | 0.3016 | 0.1719 | 0.073* | |
C13 | 0.8937 (3) | 0.3331 (4) | 0.3287 (11) | 0.0691 (18) | |
H13A | 0.9210 | 0.3260 | 0.1930 | 0.083* | |
H13B | 0.8988 | 0.2841 | 0.4176 | 0.083* | |
C14 | 0.9299 (3) | 0.4006 (5) | 0.4705 (11) | 0.074 (2) | |
H14A | 0.9324 | 0.4477 | 0.3750 | 0.089* | |
H14B | 0.9821 | 0.3862 | 0.5281 | 0.089* | |
C15 | 0.8832 (4) | 0.4190 (5) | 0.6722 (11) | 0.075 (2) | |
H15A | 0.8879 | 0.3751 | 0.7811 | 0.090* | |
H15B | 0.9032 | 0.4667 | 0.7506 | 0.090* | |
C16 | 0.7994 (3) | 0.4313 (4) | 0.5881 (10) | 0.0592 (16) | |
H16A | 0.7701 | 0.4401 | 0.7188 | 0.071* | |
H16B | 0.7944 | 0.4784 | 0.4914 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0408 (7) | 0.0584 (9) | 0.0596 (9) | 0.0043 (7) | 0.0063 (6) | 0.0094 (8) |
S2 | 0.0531 (8) | 0.0744 (11) | 0.0673 (10) | 0.0131 (8) | 0.0177 (7) | 0.0167 (9) |
O1 | 0.053 (2) | 0.074 (3) | 0.077 (3) | 0.014 (2) | 0.017 (2) | 0.030 (3) |
N1 | 0.051 (3) | 0.053 (3) | 0.059 (3) | 0.008 (2) | 0.006 (2) | 0.007 (2) |
N2 | 0.045 (3) | 0.055 (3) | 0.062 (3) | 0.004 (2) | 0.011 (2) | 0.008 (3) |
N3 | 0.045 (2) | 0.064 (3) | 0.055 (3) | 0.001 (2) | 0.005 (2) | 0.014 (3) |
N4 | 0.045 (2) | 0.058 (3) | 0.047 (3) | 0.002 (2) | 0.0067 (19) | −0.003 (2) |
C1 | 0.036 (3) | 0.058 (4) | 0.054 (3) | −0.001 (2) | 0.000 (2) | 0.003 (3) |
C2 | 0.042 (3) | 0.063 (4) | 0.052 (3) | −0.001 (3) | 0.004 (2) | −0.003 (3) |
C3 | 0.053 (3) | 0.085 (5) | 0.054 (4) | 0.005 (3) | 0.008 (3) | −0.007 (3) |
C4 | 0.050 (3) | 0.059 (4) | 0.050 (3) | 0.004 (3) | 0.011 (2) | −0.001 (3) |
C5 | 0.057 (4) | 0.079 (5) | 0.057 (4) | 0.000 (3) | 0.012 (3) | 0.012 (3) |
C6 | 0.065 (4) | 0.092 (6) | 0.063 (4) | 0.006 (4) | −0.001 (3) | 0.009 (4) |
C7 | 0.047 (3) | 0.085 (5) | 0.086 (5) | 0.000 (3) | 0.003 (3) | −0.002 (4) |
C8 | 0.056 (4) | 0.090 (5) | 0.089 (5) | −0.006 (4) | 0.025 (3) | 0.016 (4) |
C9 | 0.059 (4) | 0.088 (5) | 0.058 (4) | 0.007 (3) | 0.015 (3) | 0.018 (4) |
C10 | 0.040 (3) | 0.050 (3) | 0.060 (4) | −0.002 (2) | 0.005 (2) | −0.002 (3) |
C11 | 0.050 (3) | 0.060 (4) | 0.055 (3) | 0.002 (3) | 0.007 (3) | 0.003 (3) |
C12 | 0.061 (4) | 0.070 (4) | 0.052 (3) | −0.002 (3) | 0.012 (3) | −0.012 (3) |
C13 | 0.056 (3) | 0.084 (5) | 0.070 (4) | 0.008 (4) | 0.022 (3) | −0.011 (4) |
C14 | 0.044 (3) | 0.099 (6) | 0.078 (5) | −0.003 (3) | 0.004 (3) | −0.005 (4) |
C15 | 0.054 (4) | 0.102 (6) | 0.071 (4) | −0.006 (4) | 0.007 (3) | −0.027 (4) |
C16 | 0.054 (3) | 0.066 (4) | 0.058 (4) | 0.001 (3) | 0.013 (3) | −0.014 (3) |
S1—C1 | 1.728 (6) | C7—C8 | 1.373 (9) |
S1—C2 | 1.736 (5) | C7—H7A | 0.9300 |
S2—C2 | 1.741 (6) | C8—C9 | 1.368 (9) |
S2—C3 | 1.825 (6) | C8—H8A | 0.9300 |
O1—C10 | 1.208 (7) | C9—H9A | 0.9300 |
N1—C1 | 1.295 (7) | C10—C11 | 1.517 (7) |
N1—N2 | 1.394 (6) | C11—H11A | 0.9700 |
N2—C2 | 1.301 (8) | C11—H11B | 0.9700 |
N3—C10 | 1.372 (7) | C12—C13 | 1.492 (8) |
N3—C1 | 1.383 (7) | C12—H12A | 0.9700 |
N3—H3 | 0.8600 | C12—H12B | 0.9700 |
N4—C11 | 1.448 (7) | C13—C14 | 1.504 (9) |
N4—C12 | 1.467 (7) | C13—H13A | 0.9700 |
N4—C16 | 1.469 (7) | C13—H13B | 0.9700 |
C3—C4 | 1.493 (8) | C14—C15 | 1.527 (8) |
C3—H3B | 0.9700 | C14—H14A | 0.9700 |
C3—H3C | 0.9700 | C14—H14B | 0.9700 |
C4—C5 | 1.383 (8) | C15—C16 | 1.509 (8) |
C4—C9 | 1.390 (8) | C15—H15A | 0.9700 |
C5—C6 | 1.373 (8) | C15—H15B | 0.9700 |
C5—H5A | 0.9300 | C16—H16A | 0.9700 |
C6—C7 | 1.368 (9) | C16—H16B | 0.9700 |
C6—H6A | 0.9300 | ||
C1—S1—C2 | 86.0 (3) | O1—C10—N3 | 121.2 (5) |
C2—S2—C3 | 102.7 (3) | O1—C10—C11 | 123.7 (5) |
C1—N1—N2 | 111.6 (5) | N3—C10—C11 | 115.0 (5) |
C2—N2—N1 | 112.3 (4) | N4—C11—C10 | 112.2 (5) |
C10—N3—C1 | 122.1 (5) | N4—C11—H11A | 109.2 |
C10—N3—H3 | 119.0 | C10—C11—H11A | 109.2 |
C1—N3—H3 | 119.0 | N4—C11—H11B | 109.2 |
C11—N4—C12 | 111.3 (4) | C10—C11—H11B | 109.2 |
C11—N4—C16 | 110.3 (5) | H11A—C11—H11B | 107.9 |
C12—N4—C16 | 110.6 (5) | N4—C12—C13 | 110.7 (5) |
N1—C1—N3 | 121.9 (5) | N4—C12—H12A | 109.5 |
N1—C1—S1 | 115.5 (4) | C13—C12—H12A | 109.5 |
N3—C1—S1 | 122.6 (4) | N4—C12—H12B | 109.5 |
N2—C2—S1 | 114.6 (4) | C13—C12—H12B | 109.5 |
N2—C2—S2 | 127.4 (4) | H12A—C12—H12B | 108.1 |
S1—C2—S2 | 118.0 (4) | C12—C13—C14 | 112.3 (5) |
C4—C3—S2 | 114.5 (5) | C12—C13—H13A | 109.1 |
C4—C3—H3B | 108.6 | C14—C13—H13A | 109.1 |
S2—C3—H3B | 108.6 | C12—C13—H13B | 109.1 |
C4—C3—H3C | 108.6 | C14—C13—H13B | 109.1 |
S2—C3—H3C | 108.6 | H13A—C13—H13B | 107.9 |
H3B—C3—H3C | 107.6 | C13—C14—C15 | 110.4 (5) |
C5—C4—C9 | 118.0 (6) | C13—C14—H14A | 109.6 |
C5—C4—C3 | 121.2 (5) | C15—C14—H14A | 109.6 |
C9—C4—C3 | 120.7 (6) | C13—C14—H14B | 109.6 |
C6—C5—C4 | 120.6 (6) | C15—C14—H14B | 109.6 |
C6—C5—H5A | 119.7 | H14A—C14—H14B | 108.1 |
C4—C5—H5A | 119.7 | C16—C15—C14 | 110.3 (5) |
C7—C6—C5 | 121.0 (7) | C16—C15—H15A | 109.6 |
C7—C6—H6A | 119.5 | C14—C15—H15A | 109.6 |
C5—C6—H6A | 119.5 | C16—C15—H15B | 109.6 |
C6—C7—C8 | 118.7 (6) | C14—C15—H15B | 109.6 |
C6—C7—H7A | 120.6 | H15A—C15—H15B | 108.1 |
C8—C7—H7A | 120.6 | N4—C16—C15 | 111.5 (5) |
C9—C8—C7 | 121.0 (6) | N4—C16—H16A | 109.3 |
C9—C8—H8A | 119.5 | C15—C16—H16A | 109.3 |
C7—C8—H8A | 119.5 | N4—C16—H16B | 109.3 |
C8—C9—C4 | 120.6 (6) | C15—C16—H16B | 109.3 |
C8—C9—H9A | 119.7 | H16A—C16—H16B | 108.0 |
C4—C9—H9A | 119.7 | ||
C1—N1—N2—C2 | 0.3 (7) | C5—C6—C7—C8 | −2.4 (12) |
N2—N1—C1—N3 | 176.5 (5) | C6—C7—C8—C9 | 2.3 (12) |
N2—N1—C1—S1 | −2.1 (7) | C7—C8—C9—C4 | −0.6 (12) |
C10—N3—C1—N1 | 177.3 (5) | C5—C4—C9—C8 | −1.1 (10) |
C10—N3—C1—S1 | −4.2 (8) | C3—C4—C9—C8 | 175.8 (6) |
C2—S1—C1—N1 | 2.5 (5) | C1—N3—C10—O1 | −4.4 (9) |
C2—S1—C1—N3 | −176.1 (5) | C1—N3—C10—C11 | 172.2 (5) |
N1—N2—C2—S1 | 1.7 (7) | C12—N4—C11—C10 | 163.5 (5) |
N1—N2—C2—S2 | −179.1 (4) | C16—N4—C11—C10 | −73.3 (6) |
C1—S1—C2—N2 | −2.3 (5) | O1—C10—C11—N4 | −37.3 (8) |
C1—S1—C2—S2 | 178.4 (4) | N3—C10—C11—N4 | 146.2 (5) |
C3—S2—C2—N2 | −14.8 (6) | C11—N4—C12—C13 | −178.0 (5) |
C3—S2—C2—S1 | 164.4 (3) | C16—N4—C12—C13 | 58.9 (7) |
C2—S2—C3—C4 | 99.2 (5) | N4—C12—C13—C14 | −56.4 (7) |
S2—C3—C4—C5 | −88.5 (7) | C12—C13—C14—C15 | 52.9 (8) |
S2—C3—C4—C9 | 94.7 (6) | C13—C14—C15—C16 | −52.0 (8) |
C9—C4—C5—C6 | 1.0 (10) | C11—N4—C16—C15 | 176.8 (5) |
C3—C4—C5—C6 | −175.9 (6) | C12—N4—C16—C15 | −59.6 (7) |
C4—C5—C6—C7 | 0.7 (12) | C14—C15—C16—N4 | 56.1 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N1i | 0.86 | 2.08 | 2.930 (7) | 169 |
C11—H11A···O1ii | 0.97 | 2.55 | 3.334 (8) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N1i | 0.86 | 2.08 | 2.930 (7) | 169 |
C11—H11A···O1ii | 0.97 | 2.55 | 3.334 (8) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F7–T185).
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1,3,4-Thiadiazoless are a very important class of compounds because of their interesting physiological properties. Derivatives of 1,3,4– thiadiazoles show different biological activities such as antihypertensive (Turner et al., 1988), anticonvulsant (Chapleo et al., 1987), anti-depressant (Cleici et al., 2001), and diuretic (Jain & Mishra, 2004). Acetazolamide, having a 1,3,4-thiadiazole moiety, is known in medicine as narcotic drug.
The title compound was obtained in the reaction of 2-benzylsulfanyl-5-chloroacetamido-1,3,4-thiadiazole and piperidine in a 1:2 ratio in the presence of benzene. The structure of the obtained product was confirmed by single-crystal X-ray analysis and 1H NMR spectroscopy.
Molecular structure of title compound is shown in Figure 1. The acetamido-1,3,4-thiadiazole (S1/C1/N1/N2/C2/N3/C10/O1/C11) unit is essentially planar [r.m.s. deviation 0.082 Å]. The thiadiazole sulfur and the acetamido oxygen atoms are syn oriented due to a hypervalent interaction with the S···O distance of 2.628 (4) Å. In crystal, the molecules form centrosymmetric dimers through N-H···N hydrogen bonds (Table 1, Fig. 2). These dimers are further connected by C11—H···O1 interactions into (100) layers. As well as an intramolecular S···O hypervalent interaction [S1···O1 ═ 2.625 (5) Å] was observed.