Literature DB >> 21201385

N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl]aniline.

Shu-Wen Wang1, Zheng-Quan Zuo, Wen-Long Yang.   

Abstract

In the mol-ecule of the title compound, C(20)H(19)N(5)O, the pyrazole and oxadiazole rings are not completely conjugated, the dihedral angle between them being 7.97 (6)°. The pyrazole and oxadiazole rings form dihedral angles of 42.74 (6) and 4.35 (5)° with the attached phenyl and benzene rings, respectively.

Entities:  

Year:  2008        PMID： 21201385      PMCID： PMC2960212          DOI： 10.1107/S1600536807067402

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Ashton et al. (1993 ▶); Charles et al. (2004 ▶); Coswami et al. (1984 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C20H19N5O M = 345.40 Monoclinic, a = 17.746 (7) Å b = 6.942 (3) Å c = 14.474 (6) Å β = 99.738 (5)° V = 1757.6 (12) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 (2) K 0.28 × 0.20 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.993 9198 measured reflections 3096 independent reflections 2212 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.108 S = 1.04 3096 reflections 238 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.19 e Å−3 Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067402/rz2184sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067402/rz2184Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H19N5OF000 = 728
Mr = 345.40Dx = 1.305 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2162 reflections
a = 17.746 (7) Åθ = 2.3–23.1º
b = 6.942 (3) ŵ = 0.09 mm−1
c = 14.474 (6) ÅT = 293 (2) K
β = 99.738 (5)ºPlate, colourless
V = 1757.6 (12) Å30.28 × 0.20 × 0.08 mm
Z = 4
Bruker APEXII CCD area-detector diffractometer3096 independent reflections
Radiation source: fine-focus sealed tube2212 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 293(2) Kθmax = 25.0º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −21→20
Tmin = 0.976, Tmax = 0.993k = −7→8
9198 measured reflectionsl = −15→17
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.108  w = 1/[σ2(Fo2) + (0.0598P)2 + 0.1148P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3096 reflectionsΔρmax = 0.19 e Å−3
238 parametersΔρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
O10.23457 (6)0.46275 (15)0.97159 (7)0.0441 (3)
N10.36081 (7)0.98159 (18)0.95277 (9)0.0419 (3)
N20.35181 (8)1.0599 (2)1.03710 (9)0.0519 (4)
N30.22892 (9)0.5614 (2)1.11520 (10)0.0546 (4)
N40.18766 (9)0.3870 (2)1.09869 (10)0.0554 (4)
N50.07036 (9)−0.3315 (2)0.82215 (11)0.0683 (5)
C10.46094 (10)1.2036 (2)0.92564 (13)0.0560 (5)
H10.48141.19980.98920.067*
C20.49418 (11)1.3160 (3)0.86493 (16)0.0666 (6)
H20.53751.38820.88780.080*
C30.46404 (12)1.3224 (3)0.77106 (16)0.0659 (6)
H30.48691.39840.73070.079*
C40.40026 (11)1.2166 (2)0.73698 (13)0.0560 (5)
H40.38021.21990.67330.067*
C50.36550 (9)1.1050 (2)0.79661 (11)0.0465 (4)
H50.32141.03610.77360.056*
C60.39648 (9)1.0964 (2)0.89030 (11)0.0412 (4)
C70.32987 (9)0.8024 (2)0.93957 (10)0.0400 (4)
C80.29830 (9)0.7646 (2)1.01870 (10)0.0420 (4)
C90.31435 (10)0.9277 (2)1.07553 (12)0.0516 (4)
H90.30000.94081.13410.062*
C100.33531 (11)0.6795 (3)0.85662 (12)0.0558 (5)
H10A0.29110.69980.80940.084*
H10B0.33790.54650.87500.084*
H10C0.38050.71300.83190.084*
C110.25474 (9)0.5991 (2)1.03925 (11)0.0428 (4)
C120.19272 (9)0.3352 (2)1.01439 (11)0.0427 (4)
C130.16085 (9)0.1674 (2)0.96261 (11)0.0430 (4)
C140.17535 (9)0.1234 (2)0.87380 (12)0.0471 (4)
H140.20540.20630.84500.057*
C150.14621 (9)−0.0402 (3)0.82743 (12)0.0501 (4)
H150.1573−0.06630.76810.060*
C160.10020 (9)−0.1681 (2)0.86788 (12)0.0484 (4)
C170.08488 (10)−0.1211 (3)0.95697 (12)0.0539 (5)
H170.0540−0.20200.98560.065*
C180.11459 (10)0.0419 (3)1.00279 (12)0.0519 (4)
H180.10360.06911.06200.062*
C190.09588 (13)−0.4001 (3)0.73912 (15)0.0736 (6)
H19A0.0894−0.30050.69240.110*
H19B0.0664−0.51090.71550.110*
H19C0.1489−0.43490.75390.110*
C200.02076 (12)−0.4574 (3)0.86451 (16)0.0731 (6)
H20A0.0480−0.50610.92280.110*
H20B0.0047−0.56310.82300.110*
H20C−0.0233−0.38660.87580.110*
U11U22U33U12U13U23
O10.0498 (6)0.0455 (6)0.0386 (6)−0.0029 (5)0.0125 (5)0.0024 (5)
N10.0463 (8)0.0422 (8)0.0365 (8)−0.0030 (6)0.0049 (6)−0.0006 (6)
N20.0677 (9)0.0506 (8)0.0369 (8)−0.0056 (7)0.0077 (7)−0.0051 (6)
N30.0693 (10)0.0535 (9)0.0438 (9)−0.0081 (8)0.0180 (7)−0.0004 (7)
N40.0689 (10)0.0561 (9)0.0450 (9)−0.0106 (8)0.0205 (7)−0.0011 (7)
N50.0716 (11)0.0739 (11)0.0617 (10)−0.0230 (9)0.0175 (8)−0.0193 (8)
C10.0505 (10)0.0482 (10)0.0648 (12)−0.0017 (8)−0.0034 (9)0.0090 (9)
C20.0499 (11)0.0521 (11)0.0978 (17)−0.0068 (9)0.0128 (11)0.0138 (11)
C30.0708 (14)0.0469 (11)0.0880 (16)0.0084 (10)0.0362 (12)0.0188 (10)
C40.0711 (13)0.0479 (10)0.0527 (11)0.0103 (9)0.0217 (9)0.0107 (8)
C50.0489 (10)0.0443 (9)0.0468 (10)0.0035 (8)0.0094 (8)0.0035 (8)
C60.0415 (9)0.0371 (9)0.0453 (10)0.0027 (7)0.0079 (7)0.0052 (7)
C70.0410 (9)0.0387 (9)0.0395 (9)0.0031 (7)0.0045 (7)0.0005 (7)
C80.0458 (9)0.0429 (9)0.0367 (9)0.0017 (7)0.0054 (7)0.0032 (7)
C90.0653 (11)0.0541 (11)0.0359 (9)−0.0042 (9)0.0102 (8)0.0012 (8)
C100.0702 (12)0.0481 (10)0.0536 (11)−0.0042 (9)0.0239 (9)−0.0066 (8)
C110.0469 (9)0.0444 (9)0.0367 (9)0.0044 (7)0.0060 (7)0.0023 (7)
C120.0431 (9)0.0465 (9)0.0405 (9)0.0017 (7)0.0124 (7)0.0081 (7)
C130.0439 (9)0.0466 (9)0.0396 (9)0.0023 (7)0.0103 (7)0.0043 (7)
C140.0442 (9)0.0541 (10)0.0457 (10)0.0002 (8)0.0148 (7)0.0077 (8)
C150.0495 (10)0.0626 (11)0.0399 (10)0.0008 (9)0.0127 (8)−0.0014 (8)
C160.0435 (9)0.0570 (10)0.0440 (10)−0.0014 (8)0.0052 (7)−0.0016 (8)
C170.0548 (10)0.0601 (11)0.0494 (11)−0.0138 (9)0.0163 (8)0.0006 (9)
C180.0590 (11)0.0586 (11)0.0418 (10)−0.0081 (9)0.0192 (8)−0.0008 (8)
C190.0827 (14)0.0702 (13)0.0685 (14)−0.0006 (11)0.0145 (11)−0.0198 (11)
C200.0697 (13)0.0660 (13)0.0822 (15)−0.0179 (11)0.0089 (11)−0.0085 (11)
O1—C111.3656 (19)C7—C101.489 (2)
O1—C121.3694 (18)C8—C91.400 (2)
N1—C71.360 (2)C8—C111.443 (2)
N1—N21.3701 (18)C9—H90.9300
N1—C61.431 (2)C10—H10A0.9600
N2—C91.311 (2)C10—H10B0.9600
N3—C111.287 (2)C10—H10C0.9600
N3—N41.4140 (19)C12—C131.447 (2)
N4—C121.290 (2)C13—C141.387 (2)
N5—C161.374 (2)C13—C181.390 (2)
N5—C191.435 (2)C14—C151.375 (2)
N5—C201.448 (2)C14—H140.9300
C1—C21.380 (3)C15—C161.400 (2)
C1—C61.388 (2)C15—H150.9300
C1—H10.9300C16—C171.401 (2)
C2—C31.374 (3)C17—C181.371 (2)
C2—H20.9300C17—H170.9300
C3—C41.369 (3)C18—H180.9300
C3—H30.9300C19—H19A0.9600
C4—C51.380 (2)C19—H19B0.9600
C4—H40.9300C19—H19C0.9600
C5—C61.376 (2)C20—H20A0.9600
C5—H50.9300C20—H20B0.9600
C7—C81.383 (2)C20—H20C0.9600
C11—O1—C12102.73 (12)C7—C10—H10C109.5
C7—N1—N2112.53 (13)H10A—C10—H10C109.5
C7—N1—C6129.20 (13)H10B—C10—H10C109.5
N2—N1—C6118.20 (13)N3—C11—O1112.53 (14)
C9—N2—N1104.12 (13)N3—C11—C8128.20 (15)
C11—N3—N4106.20 (14)O1—C11—C8119.24 (13)
C12—N4—N3106.35 (13)N4—C12—O1112.19 (14)
C16—N5—C19121.80 (16)N4—C12—C13129.10 (15)
C16—N5—C20120.45 (16)O1—C12—C13118.71 (14)
C19—N5—C20117.04 (16)C14—C13—C18117.70 (15)
C2—C1—C6118.87 (18)C14—C13—C12122.67 (15)
C2—C1—H1120.6C18—C13—C12119.63 (15)
C6—C1—H1120.6C15—C14—C13121.40 (15)
C3—C2—C1120.74 (19)C15—C14—H14119.3
C3—C2—H2119.6C13—C14—H14119.3
C1—C2—H2119.6C14—C15—C16121.18 (16)
C4—C3—C2119.91 (18)C14—C15—H15119.4
C4—C3—H3120.0C16—C15—H15119.4
C2—C3—H3120.0N5—C16—C15121.80 (16)
C3—C4—C5120.35 (18)N5—C16—C17121.12 (16)
C3—C4—H4119.8C15—C16—C17117.07 (16)
C5—C4—H4119.8C18—C17—C16121.26 (16)
C6—C5—C4119.63 (17)C18—C17—H17119.4
C6—C5—H5120.2C16—C17—H17119.4
C4—C5—H5120.2C17—C18—C13121.39 (16)
C5—C6—C1120.47 (15)C17—C18—H18119.3
C5—C6—N1120.09 (14)C13—C18—H18119.3
C1—C6—N1119.40 (15)N5—C19—H19A109.5
N1—C7—C8105.52 (13)N5—C19—H19B109.5
N1—C7—C10123.88 (14)H19A—C19—H19B109.5
C8—C7—C10130.53 (15)N5—C19—H19C109.5
C7—C8—C9105.22 (14)H19A—C19—H19C109.5
C7—C8—C11128.89 (14)H19B—C19—H19C109.5
C9—C8—C11125.83 (15)N5—C20—H20A109.5
N2—C9—C8112.60 (15)N5—C20—H20B109.5
N2—C9—H9123.7H20A—C20—H20B109.5
C8—C9—H9123.7N5—C20—H20C109.5
C7—C10—H10A109.5H20A—C20—H20C109.5
C7—C10—H10B109.5H20B—C20—H20C109.5
H10A—C10—H10B109.5
C7—N1—N2—C9−0.54 (17)C12—O1—C11—N30.19 (16)
C6—N1—N2—C9176.53 (13)C12—O1—C11—C8−178.00 (13)
C11—N3—N4—C120.29 (18)C7—C8—C11—N3176.18 (16)
C6—C1—C2—C30.1 (3)C9—C8—C11—N3−7.0 (3)
C1—C2—C3—C40.1 (3)C7—C8—C11—O1−5.9 (2)
C2—C3—C4—C50.7 (3)C9—C8—C11—O1170.91 (15)
C3—C4—C5—C6−1.7 (2)N3—N4—C12—O1−0.18 (18)
C4—C5—C6—C12.0 (2)N3—N4—C12—C13−179.99 (15)
C4—C5—C6—N1179.85 (14)C11—O1—C12—N40.01 (16)
C2—C1—C6—C5−1.2 (3)C11—O1—C12—C13179.84 (13)
C2—C1—C6—N1−179.07 (16)N4—C12—C13—C14−175.58 (17)
C7—N1—C6—C541.8 (2)O1—C12—C13—C144.6 (2)
N2—N1—C6—C5−134.74 (15)N4—C12—C13—C183.4 (3)
C7—N1—C6—C1−140.34 (17)O1—C12—C13—C18−176.37 (14)
N2—N1—C6—C143.1 (2)C18—C13—C14—C15−1.1 (2)
N2—N1—C7—C80.98 (17)C12—C13—C14—C15177.95 (15)
C6—N1—C7—C8−175.69 (14)C13—C14—C15—C160.5 (2)
N2—N1—C7—C10−176.36 (14)C19—N5—C16—C1512.1 (3)
C6—N1—C7—C107.0 (2)C20—N5—C16—C15−177.81 (17)
N1—C7—C8—C9−0.98 (16)C19—N5—C16—C17−168.77 (18)
C10—C7—C8—C9176.12 (17)C20—N5—C16—C171.3 (3)
N1—C7—C8—C11176.38 (15)C14—C15—C16—N5179.64 (16)
C10—C7—C8—C11−6.5 (3)C14—C15—C16—C170.5 (2)
N1—N2—C9—C8−0.13 (19)N5—C16—C17—C18180.00 (17)
C7—C8—C9—N20.72 (19)C15—C16—C17—C18−0.8 (3)
C11—C8—C9—N2−176.75 (14)C16—C17—C18—C130.2 (3)
N4—N3—C11—O1−0.30 (18)C14—C13—C18—C170.7 (2)
N4—N3—C11—C8177.69 (15)C12—C13—C18—C17−178.34 (16)
  2 in total

1.  Design and synthesis of 3-(2-pyridyl)pyrazolo[1,5-a]pyrimidines as potent CRF1 receptor antagonists.

Authors:  Charles Q Huang; Keith M Wilcoxen; Dimitri E Grigoriadis; James R McCarthy; Chen Chen
Journal:  Bioorg Med Chem Lett       Date:  2004-08-02       Impact factor: 2.823

2.  Nonpeptide angiotensin II antagonists derived from 1H-pyrazole-5-carboxylates and 4-aryl-1H-imidazole-5-carboxylates.

Authors:  W T Ashton; S M Hutchins; W J Greenlee; G A Doss; R S Chang; V J Lotti; K A Faust; T B Chen; G J Zingaro; S D Kivlighn
Journal:  J Med Chem       Date:  1993-11-12       Impact factor: 7.446
  2 in total

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