Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049501/hk2336sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049501/hk2336Isup2.hkl |
CCDC reference: 667354
For the preparation of the title compound, (I), potassium carbonate (15 mmol) and 5-(2-hydroxyphenyl)-3-(3,5-dimethoxyl)-phenyl-1,2,4-oxadiazole (10 mmol) were added, respectively, to the solution of 2-chloro-N-(2,6-dimethylphenyl)- acetamide (10 mmol) in acetone (100 ml). 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 analysis were obtained by slow evaporation of an ethanol solution (yield; 3.62 g, 78.8%, m.p. 419–420 K).
The highest peak in the final difference electron-density map is located 1.95 Å from the N2 atom. H atoms were positioned geometrically, with N—H = 0.86 (for NH) and C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
1,2,4-Oxadiazole derivatives possess biological properties such as intrinsic analgesic (Terashita et al., 2002) and antipicornaviral (Romero, 2001) effects. As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
Rings A (C3—C8), B (N1/N2/O3/C9/C10), C (C11—C16) and D (C19—C24) are, of course, planar and the dihedral angles between them are A/B = 3.54 (3)°, A/C = 5.65 (2)°, B/C = 5.56 (3)° and C/D = 68.17 (2)°.
The intramolecular N—H···O and C—H···O hydrogen bonds (Table 1) cause to the formation of four five-membered planar rings E (N2/H6A/C6/C7/C9), F (N1/N2/O3/C9/C10), G (O4/N3/H3A/C17/C18) and H (N3/C19/C20/C26/H26A) (Fig. 1), in which they are also nearly co-planar with the adjacent rings, as can be deduced from the dihedral angles of A/E = 2.20 (3)°, B/E = 1.52 (2)°, B/F = 3.03 (3)°, C/F = 2.54 (2)° and D/H = 2.48 (3)°. Hydrogen bonds may be effective in the stabilization of the structure.
For related literature, see: Romero (2001); Terashita et al. (2002). For bond-length data, see: Allen et al. (1987).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: SHELXTL (Siemens, 1996).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C26H25N3O5 | Z = 2 |
Mr = 459.49 | F(000) = 484 |
Triclinic, P1 | Dx = 1.334 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3200 (15) Å | Cell parameters from 25 reflections |
b = 12.630 (3) Å | θ = 9–13° |
c = 13.106 (3) Å | µ = 0.09 mm−1 |
α = 95.37 (3)° | T = 294 K |
β = 101.06 (3)° | Block, colorless |
γ = 103.48 (3)° | 0.30 × 0.10 × 0.10 mm |
V = 1144.2 (5) Å3 |
Enraf–Nonius CAD-4 diffractometer | 2028 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
ω/2θ scans | h = −9→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −15→15 |
Tmin = 0.989, Tmax = 0.991 | l = 0→16 |
4846 measured reflections | 3 standard reflections every 120 min |
4473 independent reflections | intensity decay: none |
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.037P)2 + 0.89P] where P = (Fo2 + 2Fc2)/3 |
4473 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C26H25N3O5 | γ = 103.48 (3)° |
Mr = 459.49 | V = 1144.2 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3200 (15) Å | Mo Kα radiation |
b = 12.630 (3) Å | µ = 0.09 mm−1 |
c = 13.106 (3) Å | T = 294 K |
α = 95.37 (3)° | 0.30 × 0.10 × 0.10 mm |
β = 101.06 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2028 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.047 |
Tmin = 0.989, Tmax = 0.991 | 3 standard reflections every 120 min |
4846 measured reflections | intensity decay: none |
4473 independent reflections |
R[F2 > 2σ(F2)] = 0.083 | 0 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.67 e Å−3 |
4473 reflections | Δρmin = −0.37 e Å−3 |
289 parameters |
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 > 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 | ||
O1 | 0.3738 (5) | −0.2031 (3) | 0.7085 (3) | 0.0770 (11) | |
O2 | 0.6959 (4) | 0.1635 (3) | 0.8227 (2) | 0.0674 (9) | |
O3 | 0.1682 (4) | 0.1486 (2) | 0.3487 (2) | 0.0544 (8) | |
O4 | 0.0182 (4) | 0.1649 (2) | 0.1575 (2) | 0.0618 (9) | |
O5 | 0.1340 (5) | 0.4105 (3) | 0.0536 (2) | 0.073 | |
N1 | 0.2816 (5) | 0.1636 (3) | 0.4531 (2) | 0.0578 (11) | |
N2 | 0.1300 (5) | −0.0156 (3) | 0.3976 (2) | 0.0449 (9) | |
N3 | 0.2857 (5) | 0.3462 (3) | 0.1901 (3) | 0.0601 (11) | |
H3A | 0.2880 | 0.2884 | 0.2197 | 0.072* | |
C1 | 0.2473 (8) | −0.2889 (4) | 0.6317 (5) | 0.102 (2) | |
H1B | 0.2419 | −0.3582 | 0.6571 | 0.153* | |
H1C | 0.2935 | −0.2899 | 0.5680 | 0.153* | |
H1D | 0.1208 | −0.2766 | 0.6182 | 0.153* | |
C2 | 0.7412 (7) | 0.2758 (4) | 0.8085 (4) | 0.0839 (18) | |
H2B | 0.8343 | 0.3184 | 0.8688 | 0.126* | |
H2C | 0.6266 | 0.3016 | 0.8001 | 0.126* | |
H2D | 0.7935 | 0.2834 | 0.7470 | 0.126* | |
C3 | 0.5675 (6) | 0.0903 (4) | 0.7431 (3) | 0.0533 (12) | |
C4 | 0.5289 (6) | −0.0181 (4) | 0.7583 (3) | 0.0601 (13) | |
H4A | 0.5905 | −0.0374 | 0.8200 | 0.072* | |
C5 | 0.4015 (6) | −0.0979 (4) | 0.6841 (3) | 0.0526 (12) | |
C6 | 0.3069 (6) | −0.0714 (4) | 0.5914 (3) | 0.0514 (11) | |
H6A | 0.2181 | −0.1256 | 0.5414 | 0.062* | |
C7 | 0.3476 (6) | 0.0364 (4) | 0.5754 (3) | 0.0448 (10) | |
C8 | 0.4766 (6) | 0.1189 (4) | 0.6499 (3) | 0.0493 (11) | |
H8A | 0.5019 | 0.1918 | 0.6380 | 0.059* | |
C9 | 0.2518 (6) | 0.0642 (3) | 0.4753 (3) | 0.0462 (11) | |
C10 | 0.0835 (6) | 0.0413 (3) | 0.3235 (3) | 0.0436 (10) | |
C11 | −0.0464 (5) | −0.0039 (3) | 0.2205 (3) | 0.0385 (10) | |
C12 | −0.1374 (6) | −0.1151 (3) | 0.2040 (3) | 0.0543 (12) | |
H12A | −0.1090 | −0.1578 | 0.2560 | 0.065* | |
C13 | −0.2688 (7) | −0.1638 (4) | 0.1123 (3) | 0.0579 (13) | |
H13A | −0.3291 | −0.2386 | 0.1018 | 0.070* | |
C14 | −0.3091 (7) | −0.0993 (4) | 0.0366 (3) | 0.0615 (13) | |
H14A | −0.4016 | −0.1307 | −0.0246 | 0.074* | |
C15 | −0.2177 (6) | 0.0085 (3) | 0.0487 (3) | 0.0516 (12) | |
H15A | −0.2460 | 0.0502 | −0.0042 | 0.062* | |
C16 | −0.0824 (6) | 0.0568 (3) | 0.1396 (3) | 0.0426 (10) | |
C17 | −0.0099 (6) | 0.2329 (3) | 0.0789 (3) | 0.0551 (12) | |
H17A | −0.1362 | 0.2469 | 0.0720 | 0.066* | |
H17B | −0.0031 | 0.1962 | 0.0118 | 0.066* | |
C18 | 0.1413 (7) | 0.3383 (4) | 0.1084 (3) | 0.0623 (14) | |
C19 | 0.4371 (7) | 0.4428 (3) | 0.2324 (4) | 0.0619 (14) | |
C20 | 0.4323 (9) | 0.5036 (4) | 0.3245 (4) | 0.0835 (18) | |
C21 | 0.5882 (11) | 0.5932 (4) | 0.3679 (5) | 0.107 (3) | |
H21A | 0.5907 | 0.6348 | 0.4308 | 0.129* | |
C22 | 0.7353 (10) | 0.6200 (4) | 0.3197 (5) | 0.103 (3) | |
H22A | 0.8349 | 0.6820 | 0.3495 | 0.124* | |
C23 | 0.7467 (9) | 0.5593 (5) | 0.2266 (5) | 0.096 | |
H23A | 0.8520 | 0.5785 | 0.1959 | 0.115* | |
C24 | 0.5918 (8) | 0.4688 (4) | 0.1826 (4) | 0.0690 (15) | |
C25 | 0.5993 (8) | 0.4040 (4) | 0.0840 (5) | 0.0942 (19) | |
H25A | 0.7151 | 0.4367 | 0.0623 | 0.141* | |
H25B | 0.4895 | 0.4034 | 0.0302 | 0.141* | |
H25C | 0.5981 | 0.3299 | 0.0955 | 0.141* | |
C26 | 0.2561 (8) | 0.4750 (5) | 0.3734 (5) | 0.097 | |
H26A | 0.1659 | 0.4099 | 0.3333 | 0.146* | |
H26B | 0.1961 | 0.5349 | 0.3733 | 0.146* | |
H26C | 0.2959 | 0.4622 | 0.4444 | 0.146* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.085 (3) | 0.067 (2) | 0.069 (2) | 0.014 (2) | −0.0115 (19) | 0.0325 (19) |
O2 | 0.055 (2) | 0.082 (2) | 0.0471 (18) | 0.0023 (18) | −0.0171 (16) | 0.0205 (17) |
O3 | 0.067 (2) | 0.0465 (18) | 0.0357 (15) | 0.0081 (15) | −0.0181 (14) | 0.0108 (13) |
O4 | 0.072 (2) | 0.0492 (18) | 0.0425 (17) | −0.0050 (16) | −0.0215 (15) | 0.0210 (14) |
O5 | 0.073 | 0.073 | 0.073 | 0.019 | 0.016 | 0.011 |
N1 | 0.069 (3) | 0.061 (2) | 0.0306 (19) | 0.013 (2) | −0.0184 (18) | 0.0103 (17) |
N2 | 0.042 (2) | 0.054 (2) | 0.0353 (18) | 0.0088 (17) | −0.0011 (16) | 0.0151 (16) |
N3 | 0.061 (2) | 0.043 (2) | 0.059 (2) | −0.0001 (19) | −0.018 (2) | 0.0212 (18) |
C1 | 0.101 (5) | 0.079 (4) | 0.112 (5) | 0.015 (4) | −0.014 (4) | 0.042 (4) |
C2 | 0.071 (4) | 0.082 (4) | 0.067 (3) | −0.017 (3) | −0.021 (3) | 0.021 (3) |
C3 | 0.043 (3) | 0.068 (3) | 0.044 (2) | 0.015 (2) | −0.006 (2) | 0.016 (2) |
C4 | 0.054 (3) | 0.081 (4) | 0.042 (2) | 0.021 (3) | −0.010 (2) | 0.029 (2) |
C5 | 0.049 (3) | 0.068 (3) | 0.046 (3) | 0.022 (2) | 0.006 (2) | 0.028 (2) |
C6 | 0.043 (3) | 0.064 (3) | 0.043 (2) | 0.011 (2) | −0.004 (2) | 0.020 (2) |
C7 | 0.041 (2) | 0.064 (3) | 0.032 (2) | 0.019 (2) | 0.0002 (19) | 0.015 (2) |
C8 | 0.047 (3) | 0.060 (3) | 0.039 (2) | 0.013 (2) | −0.001 (2) | 0.019 (2) |
C9 | 0.049 (3) | 0.055 (3) | 0.032 (2) | 0.015 (2) | −0.005 (2) | 0.016 (2) |
C10 | 0.045 (3) | 0.043 (2) | 0.038 (2) | 0.010 (2) | −0.0029 (19) | 0.0126 (19) |
C11 | 0.034 (2) | 0.041 (2) | 0.035 (2) | 0.0071 (19) | −0.0035 (18) | 0.0101 (17) |
C12 | 0.060 (3) | 0.054 (3) | 0.043 (2) | 0.011 (2) | −0.002 (2) | 0.017 (2) |
C13 | 0.070 (3) | 0.047 (3) | 0.043 (3) | −0.004 (2) | 0.002 (2) | 0.011 (2) |
C14 | 0.061 (3) | 0.065 (3) | 0.041 (2) | −0.002 (3) | −0.012 (2) | 0.010 (2) |
C15 | 0.052 (3) | 0.052 (3) | 0.038 (2) | −0.001 (2) | −0.010 (2) | 0.013 (2) |
C16 | 0.045 (3) | 0.038 (2) | 0.036 (2) | 0.002 (2) | −0.0033 (19) | 0.0117 (18) |
C17 | 0.050 (3) | 0.050 (3) | 0.057 (3) | 0.004 (2) | −0.008 (2) | 0.030 (2) |
C18 | 0.062 (3) | 0.054 (3) | 0.062 (3) | 0.006 (2) | −0.013 (2) | 0.040 (2) |
C19 | 0.062 (3) | 0.036 (3) | 0.066 (3) | −0.002 (2) | −0.023 (3) | 0.017 (2) |
C20 | 0.108 (5) | 0.050 (3) | 0.069 (4) | 0.014 (3) | −0.030 (3) | 0.010 (3) |
C21 | 0.177 (7) | 0.047 (3) | 0.062 (4) | 0.010 (4) | −0.036 (4) | 0.007 (3) |
C22 | 0.117 (6) | 0.050 (4) | 0.106 (5) | −0.009 (3) | −0.037 (4) | 0.041 (4) |
C23 | 0.096 | 0.096 | 0.096 | 0.025 | 0.021 | 0.014 |
C24 | 0.064 (3) | 0.034 (3) | 0.084 (4) | −0.007 (2) | −0.023 (3) | 0.013 (3) |
C25 | 0.080 (4) | 0.075 (4) | 0.120 (5) | 0.008 (3) | 0.011 (4) | 0.024 (4) |
C26 | 0.097 | 0.097 | 0.097 | 0.025 | 0.021 | 0.014 |
O1—C5 | 1.374 (5) | C10—C11 | 1.471 (5) |
O1—C1 | 1.419 (6) | C11—C12 | 1.384 (5) |
O2—C3 | 1.365 (5) | C11—C16 | 1.386 (5) |
O2—C2 | 1.418 (5) | C12—C13 | 1.374 (5) |
O3—C10 | 1.332 (4) | C12—H12A | 0.9300 |
O3—N1 | 1.428 (4) | C13—C14 | 1.374 (5) |
O4—C16 | 1.366 (4) | C13—H13A | 0.9300 |
O4—C17 | 1.417 (4) | C14—C15 | 1.350 (5) |
O5—C18 | 1.217 (4) | C14—H14A | 0.9300 |
N1—C9 | 1.294 (5) | C15—C16 | 1.379 (5) |
N2—C10 | 1.302 (4) | C15—H15A | 0.9300 |
N2—C9 | 1.374 (5) | C17—C18 | 1.484 (5) |
N3—C18 | 1.331 (5) | C17—H17A | 0.9700 |
N3—C19 | 1.425 (5) | C17—H17B | 0.9700 |
N3—H3A | 0.8600 | C19—C20 | 1.379 (7) |
C1—H1B | 0.9600 | C19—C24 | 1.402 (7) |
C1—H1C | 0.9600 | C20—C21 | 1.391 (7) |
C1—H1D | 0.9600 | C20—C26 | 1.533 (8) |
C2—H2B | 0.9600 | C21—C22 | 1.343 (9) |
C2—H2C | 0.9600 | C21—H21A | 0.9300 |
C2—H2D | 0.9600 | C22—C23 | 1.406 (8) |
C3—C4 | 1.374 (6) | C22—H22A | 0.9300 |
C3—C8 | 1.395 (5) | C23—C24 | 1.395 (7) |
C4—C5 | 1.364 (6) | C23—H23A | 0.9300 |
C4—H4A | 0.9300 | C24—C25 | 1.481 (7) |
C5—C6 | 1.389 (5) | C25—H25A | 0.9600 |
C6—C7 | 1.370 (5) | C25—H25B | 0.9600 |
C6—H6A | 0.9300 | C25—H25C | 0.9600 |
C7—C8 | 1.388 (5) | C26—H26A | 0.9600 |
C7—C9 | 1.478 (5) | C26—H26B | 0.9600 |
C8—H8A | 0.9300 | C26—H26C | 0.9600 |
C5—O1—C1 | 117.2 (3) | C14—C13—C12 | 118.5 (4) |
C3—O2—C2 | 117.4 (3) | C14—C13—H13A | 120.8 |
C10—O3—N1 | 106.5 (3) | C12—C13—H13A | 120.8 |
C16—O4—C17 | 119.8 (3) | C15—C14—C13 | 121.6 (4) |
C9—N1—O3 | 102.4 (3) | C15—C14—H14A | 119.2 |
C10—N2—C9 | 102.3 (3) | C13—C14—H14A | 119.2 |
C18—N3—C19 | 125.1 (3) | C14—C15—C16 | 119.9 (4) |
C18—N3—H3A | 117.4 | C14—C15—H15A | 120.0 |
C19—N3—H3A | 117.4 | C16—C15—H15A | 120.0 |
O1—C1—H1B | 109.5 | O4—C16—C15 | 123.6 (3) |
O1—C1—H1C | 109.5 | O4—C16—C11 | 116.2 (3) |
H1B—C1—H1C | 109.5 | C15—C16—C11 | 120.1 (4) |
O1—C1—H1D | 109.5 | O4—C17—C18 | 109.1 (3) |
H1B—C1—H1D | 109.5 | O4—C17—H17A | 109.9 |
H1C—C1—H1D | 109.5 | C18—C17—H17A | 109.9 |
O2—C2—H2B | 109.5 | O4—C17—H17B | 109.9 |
O2—C2—H2C | 109.5 | C18—C17—H17B | 109.9 |
H2B—C2—H2C | 109.5 | H17A—C17—H17B | 108.3 |
O2—C2—H2D | 109.5 | O5—C18—N3 | 123.2 (4) |
H2B—C2—H2D | 109.5 | O5—C18—C17 | 118.9 (4) |
H2C—C2—H2D | 109.5 | N3—C18—C17 | 117.8 (3) |
O2—C3—C4 | 116.1 (4) | C20—C19—C24 | 122.2 (5) |
O2—C3—C8 | 124.5 (4) | C20—C19—N3 | 118.8 (5) |
C4—C3—C8 | 119.5 (4) | C24—C19—N3 | 118.8 (5) |
C5—C4—C3 | 120.9 (4) | C19—C20—C21 | 117.7 (6) |
C5—C4—H4A | 119.6 | C19—C20—C26 | 120.3 (5) |
C3—C4—H4A | 119.6 | C21—C20—C26 | 121.9 (6) |
C4—C5—O1 | 115.6 (4) | C22—C21—C20 | 120.5 (6) |
C4—C5—C6 | 120.8 (4) | C22—C21—H21A | 119.8 |
O1—C5—C6 | 123.6 (4) | C20—C21—H21A | 119.8 |
C7—C6—C5 | 118.3 (4) | C21—C22—C23 | 123.5 (6) |
C7—C6—H6A | 120.8 | C21—C22—H22A | 118.3 |
C5—C6—H6A | 120.8 | C23—C22—H22A | 118.3 |
C6—C7—C8 | 121.8 (4) | C24—C23—C22 | 116.6 (6) |
C6—C7—C9 | 118.4 (4) | C24—C23—H23A | 121.7 |
C8—C7—C9 | 119.8 (4) | C22—C23—H23A | 121.7 |
C7—C8—C3 | 118.7 (4) | C23—C24—C19 | 119.5 (5) |
C7—C8—H8A | 120.6 | C23—C24—C25 | 117.7 (6) |
C3—C8—H8A | 120.6 | C19—C24—C25 | 122.8 (4) |
N1—C9—N2 | 115.6 (3) | C24—C25—H25A | 109.5 |
N1—C9—C7 | 122.8 (4) | C24—C25—H25B | 109.5 |
N2—C9—C7 | 121.6 (4) | H25A—C25—H25B | 109.5 |
N2—C10—O3 | 113.2 (3) | C24—C25—H25C | 109.5 |
N2—C10—C11 | 125.5 (4) | H25A—C25—H25C | 109.5 |
O3—C10—C11 | 121.3 (3) | H25B—C25—H25C | 109.5 |
C12—C11—C16 | 118.4 (3) | C20—C26—H26A | 109.5 |
C12—C11—C10 | 117.1 (3) | C20—C26—H26B | 109.5 |
C16—C11—C10 | 124.6 (4) | H26A—C26—H26B | 109.5 |
C13—C12—C11 | 121.3 (4) | C20—C26—H26C | 109.5 |
C13—C12—H12A | 119.3 | H26A—C26—H26C | 109.5 |
C11—C12—H12A | 119.3 | H26B—C26—H26C | 109.5 |
C10—O3—N1—C9 | 0.8 (4) | C10—C11—C12—C13 | 176.6 (4) |
C2—O2—C3—C4 | 178.9 (4) | C11—C12—C13—C14 | −0.2 (7) |
C2—O2—C3—C8 | −1.0 (7) | C12—C13—C14—C15 | 2.6 (8) |
O2—C3—C4—C5 | 179.4 (4) | C13—C14—C15—C16 | −1.0 (8) |
C8—C3—C4—C5 | −0.7 (7) | C17—O4—C16—C15 | −2.0 (6) |
C3—C4—C5—O1 | −179.6 (4) | C17—O4—C16—C11 | 180.0 (4) |
C3—C4—C5—C6 | −0.2 (7) | C14—C15—C16—O4 | 179.1 (4) |
C1—O1—C5—C4 | −177.9 (5) | C14—C15—C16—C11 | −2.9 (7) |
C1—O1—C5—C6 | 2.7 (7) | C12—C11—C16—O4 | −176.7 (4) |
C4—C5—C6—C7 | 1.3 (7) | C10—C11—C16—O4 | 3.0 (6) |
O1—C5—C6—C7 | −179.4 (4) | C12—C11—C16—C15 | 5.2 (6) |
C5—C6—C7—C8 | −1.3 (6) | C10—C11—C16—C15 | −175.1 (4) |
C5—C6—C7—C9 | 178.0 (4) | C16—O4—C17—C18 | −168.9 (4) |
C6—C7—C8—C3 | 0.4 (6) | C19—N3—C18—O5 | 8.0 (8) |
C9—C7—C8—C3 | −178.9 (4) | C19—N3—C18—C17 | −176.6 (5) |
O2—C3—C8—C7 | −179.5 (4) | O4—C17—C18—O5 | −175.4 (4) |
C4—C3—C8—C7 | 0.6 (7) | O4—C17—C18—N3 | 9.0 (6) |
O3—N1—C9—N2 | −0.4 (5) | C18—N3—C19—C20 | 103.5 (6) |
O3—N1—C9—C7 | 177.2 (4) | C18—N3—C19—C24 | −80.6 (6) |
C10—N2—C9—N1 | −0.2 (5) | C24—C19—C20—C21 | −0.1 (7) |
C10—N2—C9—C7 | −177.8 (4) | N3—C19—C20—C21 | 175.6 (4) |
C6—C7—C9—N1 | −179.8 (4) | C24—C19—C20—C26 | 177.4 (4) |
C8—C7—C9—N1 | −0.4 (6) | N3—C19—C20—C26 | −6.9 (7) |
C6—C7—C9—N2 | −2.4 (6) | C19—C20—C21—C22 | 1.4 (8) |
C8—C7—C9—N2 | 177.0 (4) | C26—C20—C21—C22 | −176.0 (5) |
C9—N2—C10—O3 | 0.8 (5) | C20—C21—C22—C23 | −2.4 (9) |
C9—N2—C10—C11 | −180.0 (4) | C21—C22—C23—C24 | 1.9 (9) |
N1—O3—C10—N2 | −1.1 (5) | C22—C23—C24—C19 | −0.4 (7) |
N1—O3—C10—C11 | 179.7 (4) | C22—C23—C24—C25 | 179.5 (5) |
N2—C10—C11—C12 | 5.0 (6) | C20—C19—C24—C23 | −0.4 (7) |
O3—C10—C11—C12 | −175.9 (4) | N3—C19—C24—C23 | −176.1 (4) |
N2—C10—C11—C16 | −174.7 (4) | C20—C19—C24—C25 | 179.7 (4) |
O3—C10—C11—C16 | 4.4 (6) | N3—C19—C24—C25 | 4.0 (7) |
C16—C11—C12—C13 | −3.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4 | 0.86 | 2.17 | 2.582 (5) | 109 |
C6—H6A···N2 | 0.93 | 2.52 | 2.850 (5) | 101 |
C12—H12A···N2 | 0.93 | 2.53 | 2.864 (5) | 102 |
C26—H26A···N3 | 0.96 | 2.37 | 2.846 (7) | 110 |
Experimental details
Crystal data | |
Chemical formula | C26H25N3O5 |
Mr | 459.49 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 7.3200 (15), 12.630 (3), 13.106 (3) |
α, β, γ (°) | 95.37 (3), 101.06 (3), 103.48 (3) |
V (Å3) | 1144.2 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.989, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4846, 4473, 2028 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.083, 0.179, 1.06 |
No. of reflections | 4473 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.37 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4 | 0.8600 | 2.1700 | 2.582 (5) | 109.00 |
C6—H6A···N2 | 0.9300 | 2.5200 | 2.850 (5) | 101.00 |
C12—H12A···N2 | 0.9300 | 2.5300 | 2.864 (5) | 102.00 |
C26—H26A···N3 | 0.9600 | 2.3700 | 2.846 (7) | 110.00 |
1,2,4-Oxadiazole derivatives possess biological properties such as intrinsic analgesic (Terashita et al., 2002) and antipicornaviral (Romero, 2001) effects. As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
Rings A (C3—C8), B (N1/N2/O3/C9/C10), C (C11—C16) and D (C19—C24) are, of course, planar and the dihedral angles between them are A/B = 3.54 (3)°, A/C = 5.65 (2)°, B/C = 5.56 (3)° and C/D = 68.17 (2)°.
The intramolecular N—H···O and C—H···O hydrogen bonds (Table 1) cause to the formation of four five-membered planar rings E (N2/H6A/C6/C7/C9), F (N1/N2/O3/C9/C10), G (O4/N3/H3A/C17/C18) and H (N3/C19/C20/C26/H26A) (Fig. 1), in which they are also nearly co-planar with the adjacent rings, as can be deduced from the dihedral angles of A/E = 2.20 (3)°, B/E = 1.52 (2)°, B/F = 3.03 (3)°, C/F = 2.54 (2)° and D/H = 2.48 (3)°. Hydrogen bonds may be effective in the stabilization of the structure.