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In the title compound, C25H23N3O4, a bifurcated intra­molecular N—H...(O,N) hydrogen bond helps to establish the mol­ecular conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047350/hb2198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047350/hb2198Isup2.hkl
Contains datablock I

CCDC reference: 629887

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.059
  • wR factor = 0.169
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: 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).

N-(2,6-Dimethylphenyl)-2-{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol- 5-yl]phenoxy}acetamide top
Crystal data top
C25H23N3O4Z = 2
Mr = 429.46F(000) = 452
Triclinic, P1Dx = 1.307 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0360 (16) ÅCell parameters from 25 reflections
b = 11.692 (2) Åθ = 9–12°
c = 12.780 (3) ŵ = 0.09 mm1
α = 66.93 (3)°T = 293 K
β = 85.56 (3)°Block, colourless
γ = 81.18 (3)°0.30 × 0.20 × 0.10 mm
V = 1091.5 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω/2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 1214
Tmin = 0.974, Tmax = 0.991l = 015
4271 measured reflections3 standard reflections every 200 reflections
4271 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0809P)2 + 0.1494P]
where P = (Fo2 + 2Fc2)/3
4271 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1472 (3)1.0792 (2)0.35968 (18)0.0837 (7)
O20.2570 (2)1.13202 (15)0.11728 (15)0.0631 (5)
O30.5234 (2)0.79004 (16)0.07785 (15)0.0668 (5)
O40.6533 (2)0.47606 (16)0.09651 (15)0.0673 (5)
N10.1663 (3)1.1272 (2)0.01782 (19)0.0650 (6)
N20.2958 (2)0.93490 (17)0.00285 (16)0.0480 (5)
N30.4544 (3)0.62721 (18)0.11566 (17)0.0538 (5)
H3A0.41420.70540.08650.065*
C10.1885 (5)1.2080 (3)0.2906 (3)0.0943 (11)
H1B0.25891.24900.33340.141*
H1C0.24751.21630.22500.141*
H1D0.08711.24620.26670.141*
C20.0455 (3)1.0053 (3)0.3135 (2)0.0595 (7)
C30.0038 (4)0.8816 (3)0.3856 (3)0.0708 (8)
H3B0.04520.85410.46020.085*
C40.0973 (4)0.7995 (3)0.3488 (2)0.0737 (8)
H4A0.12260.71600.39770.088*
C50.1624 (4)0.8402 (2)0.2386 (2)0.0625 (7)
H5A0.23320.78470.21390.075*
C60.1220 (3)0.9632 (2)0.1661 (2)0.0489 (6)
C70.0161 (3)1.0463 (2)0.2036 (2)0.0527 (6)
H7A0.01251.12930.15440.063*
C80.1937 (3)1.0097 (2)0.0495 (2)0.0472 (6)
C90.3296 (3)1.0141 (2)0.0983 (2)0.0463 (6)
C100.4299 (3)0.9977 (2)0.1926 (2)0.0483 (6)
C110.4302 (4)1.0973 (3)0.2982 (2)0.0647 (7)
H11A0.36601.17380.30760.078*
C120.5234 (4)1.0843 (3)0.3885 (2)0.0747 (9)
H12A0.52111.15150.45850.090*
C130.6194 (4)0.9729 (3)0.3756 (2)0.0671 (8)
H13A0.68350.96500.43680.081*
C140.6225 (3)0.8726 (3)0.2734 (2)0.0603 (7)
H14A0.68780.79690.26560.072*
C150.5283 (3)0.8841 (2)0.1818 (2)0.0505 (6)
C160.6281 (3)0.6747 (2)0.0555 (2)0.0561 (7)
H16A0.74520.68640.05640.067*
H16B0.61400.64290.11340.067*
C170.5797 (3)0.5831 (2)0.0598 (2)0.0525 (6)
C180.1096 (4)0.5862 (3)0.1221 (3)0.0771 (9)
H18A0.17320.63650.05840.116*
H18B0.01340.63800.13670.116*
H18C0.07260.52110.10520.116*
C190.6646 (4)0.5266 (3)0.3139 (2)0.0695 (8)
H19A0.69270.58050.23790.104*
H19B0.74040.44950.33620.104*
H19C0.67400.56730.36500.104*
C200.3855 (3)0.5494 (2)0.2217 (2)0.0497 (6)
C210.4858 (3)0.4989 (2)0.3179 (2)0.0522 (6)
C220.4162 (4)0.4220 (2)0.4186 (2)0.0657 (8)
H22A0.48150.38570.48340.079*
C230.2536 (4)0.3985 (3)0.4250 (3)0.0737 (9)
H23A0.20940.34660.49360.088*
C240.1553 (4)0.4515 (3)0.3298 (3)0.0705 (8)
H24A0.04430.43580.33540.085*
C250.2187 (3)0.5281 (2)0.2255 (2)0.0561 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0891 (15)0.0836 (15)0.0889 (15)0.0107 (12)0.0332 (12)0.0512 (13)
O20.0770 (13)0.0479 (10)0.0569 (11)0.0026 (9)0.0088 (9)0.0161 (8)
O30.0760 (13)0.0536 (10)0.0528 (11)0.0069 (9)0.0213 (9)0.0110 (9)
O40.0779 (13)0.0526 (11)0.0612 (12)0.0113 (9)0.0083 (10)0.0201 (9)
N10.0751 (16)0.0546 (13)0.0633 (14)0.0025 (11)0.0096 (12)0.0249 (11)
N20.0465 (11)0.0470 (11)0.0515 (12)0.0059 (9)0.0042 (9)0.0213 (10)
N30.0576 (13)0.0441 (11)0.0514 (12)0.0015 (9)0.0110 (10)0.0146 (9)
C10.089 (2)0.074 (2)0.133 (3)0.0107 (18)0.034 (2)0.062 (2)
C20.0552 (16)0.0645 (17)0.0684 (18)0.0120 (13)0.0114 (13)0.0369 (15)
C30.0705 (19)0.082 (2)0.0620 (18)0.0169 (16)0.0188 (15)0.0312 (16)
C40.084 (2)0.0618 (18)0.0638 (18)0.0048 (15)0.0126 (16)0.0159 (15)
C50.0664 (18)0.0561 (16)0.0638 (17)0.0010 (13)0.0084 (14)0.0262 (14)
C60.0450 (14)0.0530 (14)0.0548 (14)0.0103 (11)0.0001 (11)0.0262 (12)
C70.0499 (14)0.0510 (14)0.0613 (16)0.0085 (11)0.0019 (12)0.0261 (12)
C80.0444 (13)0.0456 (13)0.0552 (15)0.0052 (10)0.0030 (11)0.0234 (12)
C90.0452 (13)0.0421 (13)0.0513 (14)0.0073 (10)0.0036 (11)0.0166 (11)
C100.0493 (14)0.0521 (14)0.0445 (13)0.0145 (11)0.0011 (11)0.0173 (11)
C110.081 (2)0.0553 (16)0.0520 (16)0.0109 (14)0.0009 (14)0.0146 (13)
C120.097 (2)0.0714 (19)0.0455 (16)0.0190 (18)0.0084 (15)0.0103 (14)
C130.0727 (19)0.083 (2)0.0457 (15)0.0210 (16)0.0137 (13)0.0235 (14)
C140.0577 (16)0.0703 (17)0.0524 (16)0.0088 (13)0.0105 (13)0.0251 (14)
C150.0494 (14)0.0544 (14)0.0448 (14)0.0144 (11)0.0055 (11)0.0146 (11)
C160.0575 (16)0.0510 (14)0.0550 (15)0.0016 (12)0.0109 (12)0.0209 (12)
C170.0529 (15)0.0498 (14)0.0540 (15)0.0007 (12)0.0045 (12)0.0229 (12)
C180.0565 (18)0.093 (2)0.076 (2)0.0055 (16)0.0041 (15)0.0308 (17)
C190.0626 (18)0.0803 (19)0.0718 (19)0.0130 (15)0.0021 (14)0.0355 (16)
C200.0512 (15)0.0422 (12)0.0517 (14)0.0009 (11)0.0075 (12)0.0172 (11)
C210.0569 (15)0.0464 (13)0.0534 (15)0.0034 (11)0.0044 (12)0.0216 (12)
C220.075 (2)0.0588 (16)0.0549 (16)0.0073 (14)0.0017 (14)0.0134 (13)
C230.079 (2)0.0707 (19)0.0593 (18)0.0219 (16)0.0123 (16)0.0097 (15)
C240.0585 (17)0.0694 (18)0.079 (2)0.0181 (15)0.0137 (16)0.0233 (16)
C250.0507 (15)0.0538 (15)0.0615 (16)0.0011 (12)0.0035 (12)0.0237 (13)
Geometric parameters (Å, º) top
O1—C21.367 (3)C10—C151.399 (3)
O1—C11.418 (4)C11—C121.372 (4)
O2—C91.347 (3)C11—H11A0.9300
O2—N11.401 (3)C12—C131.365 (4)
O3—C151.355 (3)C12—H12A0.9300
O3—C161.412 (3)C13—C141.370 (4)
O4—C171.221 (3)C13—H13A0.9300
N1—C81.298 (3)C14—C151.385 (3)
N2—C91.298 (3)C14—H14A0.9300
N2—C81.381 (3)C16—C171.507 (3)
N3—C171.344 (3)C16—H16A0.9700
N3—C201.430 (3)C16—H16B0.9700
N3—H3A0.8600C18—C251.507 (4)
C1—H1B0.9600C18—H18A0.9600
C1—H1C0.9600C18—H18B0.9600
C1—H1D0.9600C18—H18C0.9600
C2—C71.373 (4)C19—C211.513 (4)
C2—C31.381 (4)C19—H19A0.9600
C3—C41.364 (4)C19—H19B0.9600
C3—H3B0.9300C19—H19C0.9600
C4—C51.386 (4)C20—C251.394 (4)
C4—H4A0.9300C20—C211.395 (4)
C5—C61.375 (3)C21—C221.383 (4)
C5—H5A0.9300C22—C231.366 (4)
C6—C71.395 (3)C22—H22A0.9300
C6—C81.475 (3)C23—C241.376 (4)
C7—H7A0.9300C23—H23A0.9300
C9—C101.457 (3)C24—C251.393 (4)
C10—C111.395 (3)C24—H24A0.9300
C2—O1—C1118.0 (2)C12—C13—H13A119.6
C9—O2—N1106.57 (18)C14—C13—H13A119.6
C15—O3—C16120.00 (19)C13—C14—C15119.8 (3)
C8—N1—O2103.75 (19)C13—C14—H14A120.1
C9—N2—C8102.74 (19)C15—C14—H14A120.1
C17—N3—C20122.6 (2)O3—C15—C14123.9 (2)
C17—N3—H3A118.7O3—C15—C10115.5 (2)
C20—N3—H3A118.7C14—C15—C10120.5 (2)
O1—C1—H1B109.5O3—C16—C17108.33 (19)
O1—C1—H1C109.5O3—C16—H16A110.0
H1B—C1—H1C109.5C17—C16—H16A110.0
O1—C1—H1D109.5O3—C16—H16B110.0
H1B—C1—H1D109.5C17—C16—H16B110.0
H1C—C1—H1D109.5H16A—C16—H16B108.4
O1—C2—C7124.6 (3)O4—C17—N3124.3 (2)
O1—C2—C3115.7 (2)O4—C17—C16119.7 (2)
C7—C2—C3119.7 (2)N3—C17—C16116.0 (2)
C4—C3—C2120.7 (3)C25—C18—H18A109.5
C4—C3—H3B119.6C25—C18—H18B109.5
C2—C3—H3B119.6H18A—C18—H18B109.5
C3—C4—C5120.1 (3)C25—C18—H18C109.5
C3—C4—H4A120.0H18A—C18—H18C109.5
C5—C4—H4A120.0H18B—C18—H18C109.5
C6—C5—C4119.7 (2)C21—C19—H19A109.5
C6—C5—H5A120.2C21—C19—H19B109.5
C4—C5—H5A120.2H19A—C19—H19B109.5
C5—C6—C7120.0 (2)C21—C19—H19C109.5
C5—C6—C8120.7 (2)H19A—C19—H19C109.5
C7—C6—C8119.3 (2)H19B—C19—H19C109.5
C2—C7—C6119.8 (2)C25—C20—C21122.3 (2)
C2—C7—H7A120.1C25—C20—N3118.5 (2)
C6—C7—H7A120.1C21—C20—N3119.3 (2)
N1—C8—N2114.3 (2)C22—C21—C20117.8 (2)
N1—C8—C6121.7 (2)C22—C21—C19120.4 (3)
N2—C8—C6124.0 (2)C20—C21—C19121.9 (2)
N2—C9—O2112.7 (2)C23—C22—C21121.4 (3)
N2—C9—C10131.7 (2)C23—C22—H22A119.3
O2—C9—C10115.6 (2)C21—C22—H22A119.3
C11—C10—C15117.7 (2)C22—C23—C24120.0 (3)
C11—C10—C9120.0 (2)C22—C23—H23A120.0
C15—C10—C9122.3 (2)C24—C23—H23A120.0
C12—C11—C10121.2 (3)C23—C24—C25121.4 (3)
C12—C11—H11A119.4C23—C24—H24A119.3
C10—C11—H11A119.4C25—C24—H24A119.3
C13—C12—C11120.0 (3)C24—C25—C20117.1 (3)
C13—C12—H12A120.0C24—C25—C18120.9 (3)
C11—C12—H12A120.0C20—C25—C18122.0 (2)
C12—C13—C14120.7 (3)
C9—O2—N1—C80.3 (3)C11—C12—C13—C140.8 (5)
C1—O1—C2—C71.8 (4)C12—C13—C14—C150.5 (4)
C1—O1—C2—C3177.6 (3)C16—O3—C15—C144.9 (4)
O1—C2—C3—C4179.8 (3)C16—O3—C15—C10175.1 (2)
C7—C2—C3—C40.4 (4)C13—C14—C15—O3179.9 (3)
C2—C3—C4—C51.4 (5)C13—C14—C15—C100.1 (4)
C3—C4—C5—C61.3 (5)C11—C10—C15—O3179.7 (2)
C4—C5—C6—C70.2 (4)C9—C10—C15—O30.4 (3)
C4—C5—C6—C8178.2 (2)C11—C10—C15—C140.2 (4)
O1—C2—C7—C6178.7 (2)C9—C10—C15—C14179.7 (2)
C3—C2—C7—C60.7 (4)C15—O3—C16—C17172.4 (2)
C5—C6—C7—C20.8 (4)C20—N3—C17—O44.8 (4)
C8—C6—C7—C2177.2 (2)C20—N3—C17—C16175.1 (2)
O2—N1—C8—N20.1 (3)O3—C16—C17—O4179.4 (2)
O2—N1—C8—C6179.1 (2)O3—C16—C17—N30.5 (3)
C9—N2—C8—N10.2 (3)C17—N3—C20—C25114.2 (3)
C9—N2—C8—C6179.3 (2)C17—N3—C20—C2166.7 (3)
C5—C6—C8—N1175.3 (2)C25—C20—C21—C222.1 (4)
C7—C6—C8—N12.7 (4)N3—C20—C21—C22178.8 (2)
C5—C6—C8—N23.8 (4)C25—C20—C21—C19177.6 (2)
C7—C6—C8—N2178.2 (2)N3—C20—C21—C191.5 (3)
C8—N2—C9—O20.4 (3)C20—C21—C22—C231.5 (4)
C8—N2—C9—C10179.5 (3)C19—C21—C22—C23178.2 (3)
N1—O2—C9—N20.4 (3)C21—C22—C23—C240.1 (5)
N1—O2—C9—C10179.4 (2)C22—C23—C24—C250.9 (5)
N2—C9—C10—C11172.6 (3)C23—C24—C25—C200.4 (4)
O2—C9—C10—C117.3 (3)C23—C24—C25—C18179.7 (3)
N2—C9—C10—C157.5 (4)C21—C20—C25—C241.2 (4)
O2—C9—C10—C15172.6 (2)N3—C20—C25—C24179.7 (2)
C15—C10—C11—C120.1 (4)C21—C20—C25—C18178.1 (2)
C9—C10—C11—C12180.0 (3)N3—C20—C25—C181.0 (4)
C10—C11—C12—C130.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19A···N30.962.422.893 (4)110
C18—H18A···N30.962.402.873 (4)110
C11—H11A···O20.932.412.741 (3)101
N3—H3A···N20.862.533.385 (3)179
N3—H3A···O30.862.122.543 (3)110
 

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