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Acta Cryst. (2007). E63, o3668    [ doi:10.1107/S1600536807036136 ]

N-(2,6-Dimethylphenyl)-2-(2-{3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}phenoxy)acetamide

H.-B. Wang, J. Yin and Z.-T. Xing

Abstract top

In the title compound, C25H23N3O5S, a bifurcated intramolecular N-H...O,N hydrogen bond helps to establish the molecular conformation. The dihedral angles between the oxadiazole ring and its adjacent benzene rings are 24.50 (19) and 12.20 (18)°.

Comment top

1,2,4-Oxadiazole derivatives possess biological properties such as intrinsic analgesic (Terashita et al., 2002) and antipicornaviral (Romero, 2001) effects. As part of out studies in this area, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The dihedral angles between the N1/O1/C9/N2/C8 ring and its adjacent bezene rings are 24.50 (19) and 12.20 (18)° for the C2 and C10 rings, respectively.

An intramolecular, bifurcated N—H···(N,O) hydrogen bond (Table 1) helps to establish the molecular conformation of (I). Some short C—H···O and C—H···N contacts are also present.

Related literature top

For related literature, see: Romero (2001); Terashita et al. (2002).

Experimental top

2-Chloro-N-(2,6-dimethylphenyl)acetamide (10 mmol) was dissolved in acetone (100 ml) and potassium carbonate (15 mmol) was added. Then, 5-(2-hydroxyphenyl)-3-(4-methylsulfonyl)-phenyl-1,2,4-oxadiazole (10 mmol) was added to the reaction. The resulting mixture was refluxed for 12 h. After cooling and filtering, the crude title compound was obtained and purified by recrystalization from ethyl acetate. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

All H atoms were placed geometrically (N—H = 0.86 Å, C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl carrier).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Dashed lines indicate the hydrogen bonds.
N-(2,6-Dimethylphenyl)- 2-(2-{3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}phenoxy)acetamide top
Crystal data top
C25H23N3O5SF000 = 2000
Mr = 477.52Dx = 1.340 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 28.848 (6) Åθ = 9–12º
b = 13.648 (3) ŵ = 0.18 mm−1
c = 13.562 (3) ÅT = 293 (2) K
β = 117.58 (3)ºBlock, colourless
V = 4733 (2) Å30.20 × 0.10 × 0.10 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.047
Radiation source: fine-focus sealed tubeθmax = 26.0º
Monochromator: graphiteθmin = 1.6º
T = 293(2) Kh = −35→31
ω/2θ scansk = 0→16
Absorption correction: ψ scan
(North et al., 1968)		l = 0→16
Tmin = 0.979, Tmax = 0.9833 standard reflections
4737 measured reflections every 200 reflections
4643 independent reflections intensity decay: none
3927 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.178  w = 1/[σ2(Fo2) + (0.06P)2 + P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
4643 reflectionsΔρmax = 0.34 e Å−3
283 parametersΔρmin = −0.39 e Å−3
146 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H23N3O5SV = 4733 (2) Å3
Mr = 477.52Z = 8
Monoclinic, C2/cMo Kα
a = 28.848 (6) ŵ = 0.18 mm−1
b = 13.648 (3) ÅT = 293 (2) K
c = 13.562 (3) Å0.20 × 0.10 × 0.10 mm
β = 117.58 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		3927 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.047
Tmin = 0.979, Tmax = 0.9833 standard reflections
4737 measured reflections every 200 reflections
4643 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.075146 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 0.97Δρmax = 0.34 e Å−3
4643 reflectionsΔρmin = −0.39 e Å−3
283 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.14194 (6)0.18555 (9)0.81078 (14)0.0925 (5)
O10.16502 (17)0.1933 (3)0.9251 (4)0.126
O20.11504 (16)0.1004 (3)0.7585 (4)0.125
O3−0.06215 (11)0.6306 (2)0.5510 (2)0.060
O40.06199 (10)0.8113 (2)0.6481 (3)0.0673 (9)
O50.19856 (11)0.8304 (2)0.7637 (3)0.0934 (13)
N1−0.04744 (14)0.5304 (3)0.5690 (3)0.0643 (11)
N20.02244 (12)0.6304 (2)0.6536 (3)0.0453 (9)
N30.14383 (11)0.7053 (2)0.7465 (3)0.0481 (9)
H3A0.11180.68840.72420.058*
C10.1908 (2)0.2025 (4)0.7674 (5)0.108
H1C0.21480.14850.79270.163*
H1D0.20940.26240.79830.163*
H1E0.17470.20590.68770.163*
C20.10088 (18)0.2876 (3)0.7563 (4)0.0582 (12)
C30.04852 (19)0.2760 (3)0.6783 (4)0.0619 (13)
H3B0.03510.21370.65360.074*
C40.01671 (17)0.3567 (3)0.6378 (4)0.0615 (12)
H4A−0.01830.34890.58670.074*
C50.03657 (15)0.4475 (3)0.6726 (3)0.0446 (10)
C60.08838 (15)0.4603 (3)0.7502 (3)0.0514 (11)
H6A0.10150.52310.77310.062*
C70.12050 (17)0.3807 (3)0.7934 (4)0.0640 (13)
H7A0.15510.38910.84690.077*
C80.00352 (17)0.5356 (3)0.6299 (3)0.0468 (10)
C9−0.01894 (15)0.6851 (3)0.6063 (3)0.0463 (10)
C10−0.02598 (14)0.7885 (3)0.5990 (3)0.0460 (10)
C11−0.07551 (15)0.8299 (3)0.5674 (4)0.0607 (12)
H11A−0.10430.78920.54760.073*
C12−0.08211 (19)0.9311 (4)0.5653 (4)0.0719 (14)
H12A−0.11530.95750.54230.086*
C13−0.04122 (19)0.9897 (3)0.5960 (4)0.0657 (13)
H13A−0.04561.05690.59920.079*
C140.00762 (17)0.9529 (3)0.6232 (3)0.0576 (12)
H14A0.03540.99580.64110.069*
C150.01587 (15)0.8543 (3)0.6243 (3)0.0459 (10)
C160.10881 (14)0.8666 (3)0.6885 (4)0.0538 (11)
H16A0.11040.91260.74460.065*
H16B0.10950.90370.62810.065*
C170.15441 (16)0.7993 (3)0.7373 (4)0.0529 (12)
C180.18426 (14)0.6307 (3)0.7926 (3)0.0416 (9)
C190.20946 (14)0.6160 (3)0.9060 (3)0.0478 (10)
C200.24727 (16)0.5436 (3)0.9441 (4)0.0659 (13)
H20A0.26550.53341.02050.079*
C210.25960 (16)0.4870 (3)0.8786 (4)0.0641 (13)
H21A0.28540.43920.90870.077*
C220.23276 (17)0.5023 (3)0.7657 (4)0.0633 (12)
H22A0.23980.46200.71890.076*
C230.19522 (15)0.5760 (3)0.7186 (4)0.0502 (11)
C240.16793 (17)0.5935 (4)0.5952 (4)0.0819 (16)
H24A0.18000.54680.55930.123*
H24B0.17540.65860.57990.123*
H24C0.13090.58620.56760.123*
C250.19565 (17)0.6755 (3)0.9839 (4)0.0660 (13)
H25A0.16860.72160.94130.099*
H25B0.22610.71021.03630.099*
H25C0.18360.63231.02310.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.1070 (12)0.0509 (8)0.0930 (12)0.0056 (8)0.0237 (10)−0.0028 (8)
O10.1260.1260.1260.0000.0590.000
O20.1250.1250.1250.0000.0580.000
O30.0600.0600.0600.0000.0280.000
O40.0303 (15)0.0592 (18)0.104 (3)0.0045 (14)0.0243 (17)0.0019 (18)
O50.0352 (18)0.081 (2)0.139 (3)−0.0110 (16)0.019 (2)0.033 (2)
N10.045 (2)0.066 (3)0.079 (3)−0.0122 (19)0.026 (2)−0.003 (2)
N20.0366 (19)0.051 (2)0.047 (2)0.0039 (17)0.0183 (17)0.0049 (17)
N30.0237 (17)0.054 (2)0.063 (2)0.0083 (15)0.0174 (17)0.0154 (18)
C10.1080.1080.1080.0000.0500.000
C20.071 (3)0.044 (2)0.060 (3)−0.011 (2)0.031 (3)−0.008 (2)
C30.082 (3)0.039 (2)0.064 (3)−0.017 (2)0.033 (3)−0.010 (2)
C40.064 (3)0.064 (3)0.048 (3)−0.016 (2)0.019 (2)−0.006 (2)
C50.045 (2)0.054 (2)0.039 (3)−0.013 (2)0.023 (2)0.001 (2)
C60.049 (2)0.049 (2)0.054 (3)−0.006 (2)0.022 (2)−0.007 (2)
C70.062 (3)0.049 (2)0.068 (3)−0.005 (2)0.019 (2)0.002 (2)
C80.052 (3)0.053 (3)0.044 (3)−0.005 (2)0.029 (2)0.001 (2)
C90.036 (2)0.061 (3)0.047 (3)−0.011 (2)0.024 (2)−0.003 (2)
C100.041 (2)0.063 (3)0.032 (2)0.0101 (19)0.015 (2)0.009 (2)
C110.039 (2)0.072 (3)0.067 (3)0.013 (2)0.021 (2)0.009 (3)
C120.066 (3)0.077 (3)0.070 (4)0.026 (2)0.030 (3)0.010 (3)
C130.065 (3)0.056 (3)0.069 (3)0.022 (2)0.025 (3)0.020 (2)
C140.064 (3)0.059 (3)0.051 (3)0.017 (2)0.028 (2)0.013 (2)
C150.044 (2)0.054 (2)0.034 (2)0.0106 (19)0.013 (2)0.003 (2)
C160.043 (3)0.056 (3)0.054 (3)−0.010 (2)0.016 (2)0.009 (2)
C170.043 (3)0.042 (2)0.056 (3)−0.009 (2)0.007 (2)0.014 (2)
C180.032 (2)0.043 (2)0.046 (3)−0.0009 (17)0.0154 (19)0.003 (2)
C190.039 (2)0.057 (2)0.044 (3)0.0027 (19)0.017 (2)0.008 (2)
C200.049 (3)0.074 (3)0.065 (3)0.008 (2)0.018 (2)0.014 (3)
C210.045 (3)0.061 (3)0.077 (3)0.010 (2)0.020 (3)0.009 (3)
C220.062 (3)0.060 (3)0.075 (3)0.001 (2)0.038 (3)−0.007 (3)
C230.044 (2)0.062 (3)0.049 (3)−0.009 (2)0.026 (2)0.001 (2)
C240.065 (3)0.108 (4)0.060 (4)0.013 (3)0.018 (3)−0.010 (3)
C250.073 (3)0.070 (3)0.069 (3)0.000 (3)0.045 (3)0.002 (3)
Geometric parameters (Å, °) top
S—O11.379 (5)C10—C111.407 (5)
S—O21.395 (4)C10—C151.413 (5)
S—C21.754 (4)C11—C121.392 (6)
S—C11.777 (5)C11—H11A0.9300
O3—C91.343 (4)C12—C131.322 (6)
O3—N11.420 (4)C12—H12A0.9300
O4—C151.349 (4)C13—C141.375 (5)
O4—C161.417 (4)C13—H13A0.9300
O5—C171.228 (4)C14—C151.366 (5)
N1—C81.313 (5)C14—H14A0.9300
N2—C91.298 (4)C16—C171.486 (5)
N2—C81.383 (5)C16—H16A0.9700
N3—C171.337 (4)C16—H16B0.9700
N3—C181.453 (4)C18—C191.378 (5)
N3—H3A0.8600C18—C231.399 (5)
C1—H1C0.9600C19—C201.382 (5)
C1—H1D0.9600C19—C251.524 (5)
C1—H1E0.9600C20—C211.343 (6)
C2—C71.388 (5)C20—H20A0.9300
C2—C31.395 (6)C21—C221.375 (6)
C3—C41.374 (6)C21—H21A0.9300
C3—H3B0.9300C22—C231.398 (5)
C4—C51.356 (5)C22—H22A0.9300
C4—H4A0.9300C23—C241.502 (6)
C5—C61.384 (5)C24—H24A0.9600
C5—C81.476 (5)C24—H24B0.9600
C6—C71.371 (5)C24—H24C0.9600
C6—H6A0.9300C25—H25A0.9600
C7—H7A0.9300C25—H25B0.9600
C9—C101.422 (5)C25—H25C0.9600
O1—S—O2120.0 (3)C13—C12—H12A120.0
O1—S—C2107.0 (2)C11—C12—H12A120.0
O2—S—C2109.8 (2)C12—C13—C14121.2 (4)
O1—S—C1108.6 (3)C12—C13—H13A119.4
O2—S—C1106.3 (3)C14—C13—H13A119.4
C2—S—C1104.0 (2)C15—C14—C13120.9 (4)
C9—O3—N1108.2 (3)C15—C14—H14A119.5
C15—O4—C16121.3 (3)C13—C14—H14A119.5
C8—N1—O3102.4 (3)O4—C15—C14125.3 (4)
C9—N2—C8104.5 (3)O4—C15—C10114.8 (3)
C17—N3—C18122.6 (3)C14—C15—C10119.9 (4)
C17—N3—H3A118.7O4—C16—C17109.4 (3)
C18—N3—H3A118.7O4—C16—H16A109.8
S—C1—H1C109.5C17—C16—H16A109.8
S—C1—H1D109.5O4—C16—H16B109.8
H1C—C1—H1D109.5C17—C16—H16B109.8
S—C1—H1E109.5H16A—C16—H16B108.3
H1C—C1—H1E109.5O5—C17—N3123.7 (4)
H1D—C1—H1E109.5O5—C17—C16120.1 (3)
C7—C2—C3119.7 (4)N3—C17—C16116.2 (3)
C7—C2—S119.5 (3)C19—C18—C23123.0 (4)
C3—C2—S120.8 (3)C19—C18—N3119.1 (4)
C4—C3—C2120.1 (4)C23—C18—N3117.9 (4)
C4—C3—H3B120.0C18—C19—C20116.0 (4)
C2—C3—H3B120.0C18—C19—C25121.6 (4)
C5—C4—C3119.8 (4)C20—C19—C25122.4 (4)
C5—C4—H4A120.1C21—C20—C19124.7 (5)
C3—C4—H4A120.1C21—C20—H20A117.7
C4—C5—C6120.9 (4)C19—C20—H20A117.7
C4—C5—C8121.1 (4)C20—C21—C22117.7 (4)
C6—C5—C8118.0 (4)C20—C21—H21A121.2
C7—C6—C5120.2 (4)C22—C21—H21A121.2
C7—C6—H6A119.9C21—C22—C23122.3 (4)
C5—C6—H6A119.9C21—C22—H22A118.8
C6—C7—C2119.3 (4)C23—C22—H22A118.8
C6—C7—H7A120.3C22—C23—C18116.2 (4)
C2—C7—H7A120.3C22—C23—C24121.2 (4)
N1—C8—N2113.8 (4)C18—C23—C24122.6 (4)
N1—C8—C5122.3 (4)C23—C24—H24A109.5
N2—C8—C5123.8 (4)C23—C24—H24B109.5
N2—C9—O3111.1 (3)H24A—C24—H24B109.5
N2—C9—C10132.4 (4)C23—C24—H24C109.5
O3—C9—C10116.4 (4)H24A—C24—H24C109.5
C11—C10—C15116.8 (4)H24B—C24—H24C109.5
C11—C10—C9120.8 (4)C19—C25—H25A109.5
C15—C10—C9122.3 (3)C19—C25—H25B109.5
C12—C11—C10121.0 (4)H25A—C25—H25B109.5
C12—C11—H11A119.5C19—C25—H25C109.5
C10—C11—H11A119.5H25A—C25—H25C109.5
C13—C12—C11119.9 (4)H25B—C25—H25C109.5
C9—O3—N1—C8−2.3 (4)C9—C10—C11—C12176.9 (4)
O1—S—C2—C750.9 (4)C10—C11—C12—C13−1.7 (7)
O2—S—C2—C7−177.3 (4)C11—C12—C13—C144.4 (8)
C1—S—C2—C7−63.9 (4)C12—C13—C14—C15−3.1 (7)
O1—S—C2—C3−127.6 (4)C16—O4—C15—C148.1 (6)
O2—S—C2—C34.2 (5)C16—O4—C15—C10−172.0 (4)
C1—S—C2—C3117.6 (4)C13—C14—C15—O4178.8 (4)
C7—C2—C3—C40.5 (7)C13—C14—C15—C10−1.0 (6)
S—C2—C3—C4179.0 (4)C11—C10—C15—O4−176.4 (4)
C2—C3—C4—C51.1 (7)C9—C10—C15—O44.5 (6)
C3—C4—C5—C6−1.2 (7)C11—C10—C15—C143.5 (6)
C3—C4—C5—C8179.4 (4)C9—C10—C15—C14−175.6 (4)
C4—C5—C6—C7−0.2 (6)C15—O4—C16—C17163.9 (4)
C8—C5—C6—C7179.2 (4)C18—N3—C17—O52.2 (7)
C5—C6—C7—C21.7 (7)C18—N3—C17—C16−180.0 (4)
C3—C2—C7—C6−1.8 (7)O4—C16—C17—O5170.2 (4)
S—C2—C7—C6179.6 (4)O4—C16—C17—N3−7.7 (5)
O3—N1—C8—N20.9 (4)C17—N3—C18—C1986.6 (5)
O3—N1—C8—C5178.2 (3)C17—N3—C18—C23−94.3 (5)
C9—N2—C8—N10.9 (5)C23—C18—C19—C200.6 (6)
C9—N2—C8—C5−176.4 (4)N3—C18—C19—C20179.7 (3)
C4—C5—C8—N19.5 (6)C23—C18—C19—C25−178.6 (4)
C6—C5—C8—N1−169.9 (4)N3—C18—C19—C250.4 (5)
C4—C5—C8—N2−173.5 (4)C18—C19—C20—C21−1.6 (6)
C6—C5—C8—N27.1 (6)C25—C19—C20—C21177.7 (4)
C8—N2—C9—O3−2.4 (4)C19—C20—C21—C220.1 (7)
C8—N2—C9—C10−179.3 (4)C20—C21—C22—C232.5 (7)
N1—O3—C9—N23.1 (4)C21—C22—C23—C18−3.3 (6)
N1—O3—C9—C10−179.5 (3)C21—C22—C23—C24177.7 (4)
N2—C9—C10—C11−163.6 (4)C19—C18—C23—C221.7 (6)
O3—C9—C10—C1119.6 (6)N3—C18—C23—C22−177.4 (3)
N2—C9—C10—C1515.4 (7)C19—C18—C23—C24−179.3 (4)
O3—C9—C10—C15−161.4 (4)N3—C18—C23—C241.6 (6)
C15—C10—C11—C12−2.2 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.862.142.556 (5)109
N3—H3A···N20.862.433.288 (5)176
C3—H3B···O20.932.592.946 (7)103
C6—H6A···N20.932.562.901 (5)102
C14—H14A···O2i0.932.543.429 (7)160
C16—H16A···O2i0.972.573.310 (6)133
C25—H25A···N30.962.412.883 (6)110
Symmetry codes: (i) x, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.862.142.556 (5)109
N3—H3A···N20.862.433.288 (5)176
C3—H3B···O20.932.592.946 (7)103
C6—H6A···N20.932.562.901 (5)102
C14—H14A···O2i0.932.543.429 (7)160
C16—H16A···O2i0.972.573.310 (6)133
C25—H25A···N30.962.412.883 (6)110
Symmetry codes: (i) x, y+1, z.
references
References top

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Romero, J. R. (2001). Exp. Opin. Investig. Drugs, 10, 369–379.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Siemens (1996). SHELXTL. Version 5.06. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Terashita, Z., Naruo, K. & Morimoto, S. (2002). PCT Int. Appl. WO, 02060439.