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The title compound, C23H25N5O4, was synthesized by the reaction of methyl (2-{[3-(3-pyridyl)-1,2,4-oxa­diazol-5-yl]­methoxy}phenyl)­acetate and N,N-di­methyl­form­amide di­methyl acetal. In the crystal structure, there are intramolecular C—H...O and C—H...N and intermolecular C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500766X/cv6467sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500766X/cv6467Isup2.hkl
Contains datablock I

CCDC reference: 270288

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.182
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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

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: SHELXL97.

Methyl 3-dimethylamino-2-(2-{2-dimethylamino-1-[3-(3-pyridyl)-1,2,4-oxadiazol- 5-yl]vinyloxy}phenyl)acrylate top
Crystal data top
C23H25N5O4F(000) = 920
Mr = 435.48Dx = 1.325 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.6250 (17) ÅCell parameters from 25 reflections
b = 9.6390 (19) Åθ = 10–13°
c = 26.273 (5) ŵ = 0.09 mm1
β = 91.28 (3)°T = 293 K
V = 2183.7 (8) Å3Tablet, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2426 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
ω/2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.964, Tmax = 0.982l = 3131
4550 measured reflections3 standard reflections every 200 reflections
4257 independent reflections intensity decay: none
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)] = 0.053H-atom parameters constrained
wR(F2) = 0.182 w = 1/[σ2(Fo2) + (0.1P)2 + 1.2P]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.013
4257 reflectionsΔρmax = 0.29 e Å3
290 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0100 (17)
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
O10.4684 (3)0.6663 (2)0.32844 (8)0.0550 (6)
O20.2363 (2)0.4156 (2)0.39497 (7)0.0399 (5)
O30.2164 (3)0.0530 (3)0.46863 (9)0.0656 (7)
O40.0474 (3)0.2254 (2)0.48021 (8)0.0548 (6)
N10.2789 (4)0.3991 (3)0.13676 (11)0.0626 (8)
N20.4940 (3)0.6675 (3)0.27505 (10)0.0566 (8)
N30.3291 (3)0.4942 (3)0.29525 (9)0.0412 (6)
N40.3353 (3)0.6239 (3)0.47575 (10)0.0564 (8)
N50.1193 (3)0.0355 (3)0.31549 (10)0.0463 (6)
C10.3728 (5)0.4632 (4)0.10467 (14)0.0645 (10)
H1B0.36270.44150.07030.077*
C20.4831 (4)0.5588 (4)0.11896 (13)0.0632 (11)
H2B0.54710.59840.09490.076*
C30.4976 (3)0.5951 (4)0.16947 (12)0.0545 (9)
H3B0.56990.66110.18020.065*
C40.4017 (3)0.5307 (3)0.20415 (11)0.0418 (7)
C50.2969 (4)0.4334 (3)0.18571 (12)0.0506 (8)
H5A0.23460.38880.20910.061*
C60.4101 (3)0.5653 (3)0.25865 (11)0.0403 (7)
C70.3694 (3)0.5606 (3)0.33659 (11)0.0379 (7)
C80.3209 (3)0.5370 (3)0.38798 (11)0.0405 (7)
C90.0789 (3)0.4168 (3)0.38094 (10)0.0327 (6)
C100.0004 (3)0.5362 (3)0.36803 (11)0.0409 (7)
H10A0.05070.62110.36780.049*
C110.1573 (4)0.5289 (3)0.35529 (12)0.0463 (8)
H11A0.21200.60930.34720.056*
C120.2316 (3)0.4032 (4)0.35467 (12)0.0492 (8)
H12A0.33630.39790.34550.059*
C130.1506 (3)0.2847 (3)0.36764 (11)0.0450 (7)
H13A0.20230.20000.36730.054*
C140.0067 (3)0.2878 (3)0.38121 (10)0.0325 (6)
C150.0915 (3)0.1596 (3)0.39666 (10)0.0351 (6)
C160.1278 (3)0.1376 (3)0.45053 (11)0.0426 (7)
C170.0678 (5)0.2074 (4)0.53439 (12)0.0712 (11)
H17A0.00570.27430.55180.107*
H17B0.17500.22050.54380.107*
H17C0.03620.11550.54370.107*
C180.1293 (3)0.0519 (3)0.36618 (11)0.0396 (7)
H18A0.16950.02460.38360.048*
C190.0819 (4)0.1468 (4)0.27997 (12)0.0610 (10)
H19A0.05830.22960.29860.092*
H19B0.00630.12060.25920.092*
H19C0.16900.16360.25870.092*
C200.1558 (5)0.0969 (4)0.29305 (15)0.0715 (11)
H20A0.17890.16290.31950.107*
H20B0.24410.08710.27180.107*
H20C0.06860.12890.27290.107*
C210.3651 (3)0.6239 (3)0.42581 (12)0.0463 (8)
H21A0.42730.69700.41550.056*
C220.2453 (4)0.5195 (4)0.50128 (13)0.0634 (10)
H22A0.21200.45030.47710.095*
H22B0.15620.56200.51600.095*
H22C0.30780.47690.52760.095*
C230.3934 (5)0.7359 (4)0.50808 (15)0.0768 (12)
H23A0.45220.79950.48810.115*
H23B0.45860.69820.53470.115*
H23C0.30770.78390.52280.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0573 (14)0.0649 (15)0.0429 (13)0.0270 (12)0.0058 (10)0.0025 (11)
O20.0312 (10)0.0443 (11)0.0441 (12)0.0071 (9)0.0014 (8)0.0041 (9)
O30.0693 (16)0.0789 (17)0.0483 (14)0.0198 (14)0.0032 (12)0.0132 (12)
O40.0703 (15)0.0612 (14)0.0331 (11)0.0083 (12)0.0029 (10)0.0002 (10)
N10.087 (2)0.0543 (17)0.0461 (17)0.0141 (16)0.0069 (16)0.0050 (14)
N20.0589 (17)0.0697 (19)0.0416 (15)0.0230 (15)0.0080 (13)0.0020 (13)
N30.0387 (13)0.0455 (14)0.0394 (14)0.0060 (11)0.0038 (11)0.0005 (11)
N40.0669 (19)0.0631 (18)0.0394 (15)0.0196 (15)0.0065 (13)0.0091 (13)
N50.0534 (16)0.0421 (14)0.0437 (15)0.0012 (12)0.0043 (12)0.0062 (11)
C10.073 (3)0.078 (3)0.042 (2)0.032 (2)0.0007 (18)0.0042 (18)
C20.0421 (19)0.103 (3)0.045 (2)0.025 (2)0.0125 (15)0.020 (2)
C30.0311 (16)0.081 (2)0.052 (2)0.0084 (16)0.0039 (14)0.0108 (18)
C40.0336 (15)0.0523 (18)0.0394 (16)0.0122 (14)0.0020 (12)0.0055 (13)
C50.062 (2)0.0449 (18)0.0449 (19)0.0061 (16)0.0016 (15)0.0012 (14)
C60.0320 (15)0.0460 (17)0.0429 (17)0.0009 (13)0.0012 (12)0.0038 (14)
C70.0304 (14)0.0426 (16)0.0409 (16)0.0065 (12)0.0022 (12)0.0004 (13)
C80.0331 (15)0.0431 (16)0.0453 (17)0.0083 (13)0.0038 (13)0.0003 (13)
C90.0292 (14)0.0395 (15)0.0296 (14)0.0030 (12)0.0027 (11)0.0017 (12)
C100.0456 (17)0.0354 (16)0.0418 (17)0.0004 (13)0.0039 (13)0.0024 (12)
C110.0426 (17)0.0503 (19)0.0460 (18)0.0117 (15)0.0014 (14)0.0046 (14)
C120.0319 (16)0.062 (2)0.053 (2)0.0015 (15)0.0035 (14)0.0003 (16)
C130.0346 (16)0.0493 (18)0.0510 (19)0.0068 (14)0.0005 (13)0.0007 (15)
C140.0310 (14)0.0377 (15)0.0291 (14)0.0005 (12)0.0040 (11)0.0012 (11)
C150.0333 (15)0.0346 (15)0.0374 (15)0.0051 (12)0.0032 (11)0.0030 (12)
C160.0427 (17)0.0434 (17)0.0418 (17)0.0006 (14)0.0020 (13)0.0024 (14)
C170.097 (3)0.085 (3)0.0323 (18)0.006 (2)0.0059 (18)0.0048 (18)
C180.0372 (16)0.0368 (16)0.0450 (17)0.0029 (13)0.0019 (13)0.0046 (13)
C190.077 (2)0.068 (2)0.0378 (18)0.011 (2)0.0044 (16)0.0016 (16)
C200.087 (3)0.058 (2)0.070 (3)0.004 (2)0.004 (2)0.0255 (19)
C210.0427 (17)0.0515 (19)0.0447 (18)0.0125 (14)0.0049 (13)0.0036 (14)
C220.073 (2)0.077 (2)0.0406 (18)0.015 (2)0.0105 (17)0.0023 (17)
C230.094 (3)0.079 (3)0.058 (2)0.027 (2)0.006 (2)0.022 (2)
Geometric parameters (Å, º) top
O1—C71.350 (3)C9—C141.391 (4)
O1—N21.425 (3)C10—C111.388 (4)
O2—C91.399 (3)C10—H10A0.9300
O2—C81.394 (3)C11—C121.370 (4)
O3—C161.208 (4)C11—H11A0.9300
O4—C161.352 (4)C12—C131.378 (4)
O4—C171.441 (4)C12—H12A0.9300
N1—C51.334 (4)C13—C141.395 (4)
N1—C11.333 (5)C13—H13A0.9300
N2—C61.291 (4)C14—C151.487 (4)
N3—C71.301 (4)C15—C181.355 (4)
N3—C61.383 (4)C15—C161.458 (4)
N4—C211.342 (4)C17—H17A0.9600
N4—C221.445 (4)C17—H17B0.9600
N4—C231.456 (4)C17—H17C0.9600
N5—C181.342 (4)C18—H18A0.9300
N5—C201.444 (4)C19—H19A0.9600
N5—C191.453 (4)C19—H19B0.9600
C1—C21.371 (5)C19—H19C0.9600
C1—H1B0.9300C20—H20A0.9600
C2—C31.375 (5)C20—H20B0.9600
C2—H2B0.9300C20—H20C0.9600
C3—C41.391 (4)C21—H21A0.9300
C3—H3B0.9300C22—H22A0.9600
C4—C51.383 (4)C22—H22B0.9600
C4—C61.470 (4)C22—H22C0.9600
C5—H5A0.9300C23—H23A0.9600
C7—C81.440 (4)C23—H23B0.9600
C8—C211.348 (4)C23—H23C0.9600
C9—C101.378 (4)
C7—O1—N2105.9 (2)C12—C13—C14122.0 (3)
C9—O2—C8117.8 (2)C12—C13—H13A119.0
C16—O4—C17116.2 (3)C14—C13—H13A119.0
C5—N1—C1115.8 (3)C9—C14—C13116.8 (3)
C6—N2—O1103.0 (2)C9—C14—C15121.8 (2)
C7—N3—C6102.0 (2)C13—C14—C15121.4 (2)
C21—N4—C22124.7 (3)C18—C15—C16114.4 (3)
C21—N4—C23120.0 (3)C18—C15—C14126.8 (3)
C22—N4—C23115.3 (3)C16—C15—C14118.6 (2)
C18—N5—C20120.0 (3)O3—C16—O4121.6 (3)
C18—N5—C19124.0 (3)O3—C16—C15126.9 (3)
C20—N5—C19116.0 (3)O4—C16—C15111.5 (3)
N1—C1—C2124.4 (3)O4—C17—H17A109.5
N1—C1—H1B117.8O4—C17—H17B109.5
C2—C1—H1B117.8H17A—C17—H17B109.5
C1—C2—C3118.9 (3)O4—C17—H17C109.5
C1—C2—H2B120.6H17A—C17—H17C109.5
C3—C2—H2B120.6H17B—C17—H17C109.5
C2—C3—C4118.4 (3)N5—C18—C15131.7 (3)
C2—C3—H3B120.8N5—C18—H18A114.1
C4—C3—H3B120.8C15—C18—H18A114.1
C5—C4—C3117.8 (3)N5—C19—H19A109.5
C5—C4—C6120.8 (3)N5—C19—H19B109.5
C3—C4—C6121.3 (3)H19A—C19—H19B109.5
N1—C5—C4124.6 (3)N5—C19—H19C109.5
N1—C5—H5A117.7H19A—C19—H19C109.5
C4—C5—H5A117.7H19B—C19—H19C109.5
N2—C6—N3115.7 (3)N5—C20—H20A109.5
N2—C6—C4120.9 (3)N5—C20—H20B109.5
N3—C6—C4123.4 (3)H20A—C20—H20B109.5
N3—C7—O1113.4 (2)N5—C20—H20C109.5
N3—C7—C8128.8 (3)H20A—C20—H20C109.5
O1—C7—C8117.8 (2)H20B—C20—H20C109.5
C21—C8—O2124.4 (3)N4—C21—C8131.6 (3)
C21—C8—C7120.7 (3)N4—C21—H21A114.2
O2—C8—C7114.8 (2)C8—C21—H21A114.2
C10—C9—C14121.9 (2)N4—C22—H22A109.5
C10—C9—O2123.1 (2)N4—C22—H22B109.5
C14—C9—O2115.0 (2)H22A—C22—H22B109.5
C9—C10—C11119.5 (3)N4—C22—H22C109.5
C9—C10—H10A120.2H22A—C22—H22C109.5
C11—C10—H10A120.2H22B—C22—H22C109.5
C12—C11—C10120.1 (3)N4—C23—H23A109.5
C12—C11—H11A120.0N4—C23—H23B109.5
C10—C11—H11A120.0H23A—C23—H23B109.5
C11—C12—C13119.7 (3)N4—C23—H23C109.5
C11—C12—H12A120.2H23A—C23—H23C109.5
C13—C12—H12A120.2H23B—C23—H23C109.5
C7—O1—N2—C60.2 (3)C14—C9—C10—C110.6 (4)
C5—N1—C1—C20.2 (5)O2—C9—C10—C11179.0 (2)
N1—C1—C2—C31.6 (5)C9—C10—C11—C121.2 (5)
C1—C2—C3—C41.4 (5)C10—C11—C12—C131.2 (5)
C2—C3—C4—C50.1 (4)C11—C12—C13—C140.5 (5)
C2—C3—C4—C6179.5 (3)C10—C9—C14—C130.1 (4)
C1—N1—C5—C41.4 (5)O2—C9—C14—C13179.7 (2)
C3—C4—C5—N11.6 (5)C10—C9—C14—C15178.1 (3)
C6—C4—C5—N1178.0 (3)O2—C9—C14—C151.5 (4)
O1—N2—C6—N30.2 (3)C12—C13—C14—C90.2 (4)
O1—N2—C6—C4179.2 (2)C12—C13—C14—C15178.1 (3)
C7—N3—C6—N20.1 (3)C9—C14—C15—C18111.8 (3)
C7—N3—C6—C4179.1 (3)C13—C14—C15—C1870.0 (4)
C5—C4—C6—N2171.5 (3)C9—C14—C15—C1674.2 (3)
C3—C4—C6—N28.1 (4)C13—C14—C15—C16104.0 (3)
C5—C4—C6—N37.4 (4)C17—O4—C16—O33.0 (4)
C3—C4—C6—N3173.0 (3)C17—O4—C16—C15176.6 (3)
C6—N3—C7—O10.1 (3)C18—C15—C16—O318.4 (4)
C6—N3—C7—C8178.9 (3)C14—C15—C16—O3166.8 (3)
N2—O1—C7—N30.2 (3)C18—C15—C16—O4161.1 (2)
N2—O1—C7—C8178.9 (3)C14—C15—C16—O413.7 (4)
C9—O2—C8—C21104.4 (3)C20—N5—C18—C15174.5 (3)
C9—O2—C8—C779.7 (3)C19—N5—C18—C159.4 (5)
N3—C7—C8—C21174.5 (3)C16—C15—C18—N5177.3 (3)
O1—C7—C8—C214.4 (4)C14—C15—C18—N58.5 (5)
N3—C7—C8—O29.5 (4)C22—N4—C21—C81.8 (6)
O1—C7—C8—O2171.6 (2)C23—N4—C21—C8177.3 (4)
C8—O2—C9—C1010.1 (4)O2—C8—C21—N44.5 (6)
C8—O2—C9—C14170.3 (2)C7—C8—C21—N4179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···N30.932.602.944 (4)103
C18—H18A···O30.932.382.778 (4)105
C21—H21A···O10.932.342.758 (3)107
C22—H22A···O20.962.202.967 (4)136
C22—H22A···O40.962.593.349 (5)136
C13—H13A···Cg1i0.932.583.488 (2)164
Symmetry code: (i) x, y1/2, z+1/2.
 

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