Literature DB >> 21754828

6-Amino-3-methyl-4-(3-nitro-phen-yl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile.

Ming-Shu Wu, Du-Lin Kong, Xiang-Zhu Zhang.   

Abstract

The title compound, C(20)H(15)N(5)O(3), was synthesized by the one-pot reaction of a four-component reaction protocol in aqueous medium. The pyrano[2,3-c]pyrazole system is essentially planar, with a maximum deviation of 0.026 (2) Å. The 3-nitro-phenyl and phenyl rings make dihedral angles of 81.11 (5) and 13.36 (1)°, respectively, with the mean plane of the pyrano[2,3-c]pyrazole ring. The crystal structure is stabilized by N-H⋯N hydrogen bonds, which form infinite chain propagating along the c axis and by N-H⋯O hydrogen bonds, which form infinite chains propagating along the a axis. There are also N-O⋯N-C dipole-dipole inter-actions along the a axis with an O⋯N distance of 3.061 (3) Å, which is shorter than that of the N-H⋯O hydrogen bond [3.196 (3) Å].

Entities:  

Year:  2011        PMID： 21754828      PMCID： PMC3120331          DOI： 10.1107/S1600536811017387

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


Related literature

For the anti­microbial, insecticidal and anti-inflammatory activity of pyran­opyrazole derivatives, see: El-Tamany et al. (1999 ▶); Ismail et al. (2003 ▶); Zaki et al. (2006 ▶) and for their applications as pharmaceutical ingredients and biodegradable agrochemicals, see: Junek & Aigner (1973 ▶); Sharanin et al. (1983 ▶); Vasuki & Kumaravel (2008 ▶); Wamhoff et al. (1993 ▶). For the Chk1 kinase inhibitor, see: Foloppe et al. (2006 ▶). For the use of multi-component reaction (MCR) protocols in water in the development of libraries of medicinal scaffolds, see: Chanda & Fokin (2009 ▶); Tejedor & Garcia-Tellado (2007 ▶).

Experimental

Crystal data

C20H15N5O3 M = 373.37 Monoclinic, a = 9.5089 (8) Å b = 13.9137 (11) Å c = 13.3747 (12) Å β = 96.263 (1)° V = 1759.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.50 × 0.48 × 0.47 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.952, T max = 0.955 8659 measured reflections 3087 independent reflections 1961 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.121 S = 1.07 3087 reflections 255 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017387/zk2006sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017387/zk2006Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811017387/zk2006Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H15N5O3F(000) = 776
Mr = 373.37Dx = 1.410 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.5089 (8) ÅCell parameters from 2416 reflections
b = 13.9137 (11) Åθ = 2.6–23.5°
c = 13.3747 (12) ŵ = 0.10 mm−1
β = 96.263 (1)°T = 298 K
V = 1759.0 (3) Å3Plate, colourless
Z = 40.50 × 0.48 × 0.47 mm
Bruker SMART CCD area-detector diffractometer3087 independent reflections
Radiation source: fine-focus sealed tube1961 reflections with I > 2σ(I)
graphiteRint = 0.037
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −11→11
Tmin = 0.952, Tmax = 0.955k = −16→16
8659 measured reflectionsl = −9→15
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.121w = 1/[σ2(Fo2) + (0.0397P)2 + 0.6842P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3087 reflectionsΔρmax = 0.19 e Å−3
255 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0100 (13)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
xyzUiso*/Ueq
N10.71933 (19)0.52908 (13)0.63123 (13)0.0440 (5)
N20.8060 (2)0.46605 (13)0.58687 (15)0.0507 (5)
N30.3851 (2)0.75499 (15)0.52319 (15)0.0565 (6)
H3A0.33390.78790.47850.068*
H3B0.37760.76410.58600.068*
N40.3550 (2)0.74422 (18)0.24916 (17)0.0741 (7)
N51.0378 (2)0.80263 (17)0.3702 (2)0.0674 (7)
O10.54812 (16)0.64832 (11)0.57873 (10)0.0471 (4)
O21.0555 (2)0.79273 (15)0.46155 (19)0.0900 (7)
O31.1104 (2)0.85581 (18)0.3254 (2)0.1121 (9)
C10.6433 (2)0.57976 (15)0.55812 (16)0.0404 (5)
C20.6769 (2)0.55266 (16)0.46700 (16)0.0418 (5)
C30.7801 (2)0.48064 (16)0.48860 (18)0.0466 (6)
C40.8571 (3)0.42635 (18)0.4160 (2)0.0625 (7)
H4A0.91900.46910.38530.094*
H4B0.79030.39870.36510.094*
H4C0.91180.37610.45080.094*
C50.4761 (2)0.68993 (16)0.49508 (17)0.0429 (6)
C60.5006 (2)0.66700 (16)0.40010 (16)0.0429 (6)
C70.6133 (2)0.59767 (16)0.37153 (16)0.0434 (6)
H70.56730.54740.32830.052*
C80.7221 (2)0.64836 (16)0.31459 (16)0.0412 (5)
C90.8293 (2)0.70132 (16)0.36589 (17)0.0445 (6)
H90.83680.70530.43570.053*
C100.9247 (2)0.74805 (16)0.31350 (19)0.0482 (6)
C110.9187 (3)0.74412 (19)0.2108 (2)0.0650 (7)
H110.98480.77620.17670.078*
C120.8126 (3)0.6916 (2)0.1602 (2)0.0722 (8)
H120.80630.68750.09040.087*
C130.7148 (3)0.64464 (19)0.21116 (17)0.0567 (7)
H130.64260.60980.17520.068*
C140.4173 (3)0.71120 (18)0.31880 (18)0.0510 (6)
C150.7217 (3)0.52889 (16)0.73764 (17)0.0466 (6)
C160.6181 (3)0.57274 (18)0.78491 (18)0.0575 (7)
H160.54540.60600.74760.069*
C170.6223 (4)0.5672 (2)0.8885 (2)0.0740 (9)
H170.55210.59670.92080.089*
C180.7290 (4)0.5184 (2)0.9436 (2)0.0851 (10)
H180.73030.51371.01310.102*
C190.8331 (4)0.4768 (2)0.8965 (2)0.0856 (10)
H190.90660.44490.93430.103*
C200.8312 (3)0.4813 (2)0.7935 (2)0.0684 (8)
H200.90280.45270.76190.082*
U11U22U33U12U13U23
N10.0465 (11)0.0447 (11)0.0404 (11)0.0003 (9)0.0034 (9)0.0016 (9)
N20.0507 (12)0.0471 (12)0.0553 (13)0.0015 (10)0.0105 (10)0.0039 (10)
N30.0560 (12)0.0692 (14)0.0443 (12)0.0159 (11)0.0054 (10)0.0013 (10)
N40.0683 (15)0.1012 (19)0.0511 (14)0.0056 (14)−0.0008 (12)0.0171 (14)
N50.0482 (14)0.0591 (14)0.096 (2)−0.0073 (11)0.0149 (14)−0.0085 (15)
O10.0511 (9)0.0555 (10)0.0340 (8)0.0053 (8)0.0018 (7)−0.0017 (7)
O20.0833 (15)0.0804 (14)0.0994 (18)−0.0252 (12)−0.0219 (14)−0.0020 (14)
O30.0880 (16)0.1111 (18)0.147 (2)−0.0534 (15)0.0570 (16)−0.0233 (16)
C10.0384 (12)0.0439 (13)0.0394 (13)−0.0043 (11)0.0059 (10)−0.0012 (11)
C20.0441 (13)0.0418 (12)0.0403 (13)−0.0090 (10)0.0079 (11)0.0008 (10)
C30.0472 (14)0.0436 (13)0.0508 (15)−0.0072 (11)0.0140 (12)0.0025 (11)
C40.0662 (17)0.0579 (16)0.0672 (17)0.0054 (13)0.0251 (14)−0.0015 (14)
C50.0384 (12)0.0509 (14)0.0385 (13)−0.0049 (11)0.0008 (10)0.0035 (11)
C60.0380 (12)0.0541 (14)0.0366 (13)−0.0080 (11)0.0035 (10)0.0033 (11)
C70.0459 (13)0.0486 (13)0.0355 (13)−0.0096 (11)0.0043 (11)−0.0063 (10)
C80.0429 (13)0.0458 (13)0.0351 (12)0.0002 (10)0.0056 (10)−0.0018 (10)
C90.0458 (13)0.0491 (13)0.0390 (13)0.0013 (11)0.0061 (11)−0.0019 (11)
C100.0412 (13)0.0444 (13)0.0606 (16)−0.0014 (11)0.0126 (12)−0.0014 (12)
C110.0699 (18)0.0646 (17)0.0664 (18)−0.0081 (15)0.0342 (15)0.0064 (15)
C120.089 (2)0.090 (2)0.0416 (15)−0.0100 (18)0.0238 (15)0.0038 (15)
C130.0625 (16)0.0697 (17)0.0384 (14)−0.0096 (14)0.0074 (12)−0.0054 (13)
C140.0469 (14)0.0646 (16)0.0416 (14)−0.0040 (12)0.0058 (12)0.0037 (13)
C150.0578 (15)0.0422 (13)0.0382 (13)−0.0122 (12)−0.0012 (12)0.0036 (11)
C160.0750 (18)0.0536 (15)0.0437 (15)−0.0003 (13)0.0049 (13)−0.0018 (12)
C170.109 (2)0.0685 (19)0.0459 (16)−0.0019 (17)0.0144 (17)−0.0063 (14)
C180.142 (3)0.071 (2)0.0397 (16)−0.008 (2)−0.005 (2)0.0044 (15)
C190.113 (3)0.081 (2)0.056 (2)0.008 (2)−0.0179 (19)0.0136 (17)
C200.0764 (19)0.0700 (18)0.0561 (17)0.0042 (15)−0.0050 (15)0.0104 (14)
N1—C11.350 (3)C7—C81.523 (3)
N1—N21.381 (2)C7—H70.9800
N1—C151.421 (3)C8—C91.378 (3)
N2—C31.326 (3)C8—C131.379 (3)
N3—C51.334 (3)C9—C101.369 (3)
N3—H3A0.8600C9—H90.9300
N3—H3B0.8600C10—C111.370 (3)
N4—C141.144 (3)C11—C121.364 (4)
N5—O31.214 (3)C11—H110.9300
N5—O21.222 (3)C12—C131.377 (4)
N5—C101.460 (3)C12—H120.9300
O1—C11.364 (3)C13—H130.9300
O1—C51.374 (2)C15—C161.371 (3)
C1—C21.347 (3)C15—C201.382 (3)
C2—C31.411 (3)C16—C171.384 (3)
C2—C71.490 (3)C16—H160.9300
C3—C41.484 (3)C17—C181.367 (4)
C4—H4A0.9600C17—H170.9300
C4—H4B0.9600C18—C191.360 (4)
C4—H4C0.9600C18—H180.9300
C5—C61.354 (3)C19—C201.377 (4)
C6—C141.414 (3)C19—H190.9300
C6—C71.522 (3)C20—H200.9300
C1—N1—N2108.55 (17)C9—C8—C13118.2 (2)
C1—N1—C15132.5 (2)C9—C8—C7120.29 (19)
N2—N1—C15118.94 (18)C13—C8—C7121.5 (2)
C3—N2—N1105.87 (18)C10—C9—C8119.6 (2)
C5—N3—H3A120.0C10—C9—H9120.2
C5—N3—H3B120.0C8—C9—H9120.2
H3A—N3—H3B120.0C9—C10—C11122.5 (2)
O3—N5—O2122.6 (3)C9—C10—N5118.2 (2)
O3—N5—C10119.1 (3)C11—C10—N5119.3 (2)
O2—N5—C10118.3 (2)C12—C11—C10117.8 (2)
C1—O1—C5114.40 (17)C12—C11—H11121.1
C2—C1—N1110.4 (2)C10—C11—H11121.1
C2—C1—O1127.4 (2)C11—C12—C13120.8 (2)
N1—C1—O1122.27 (19)C11—C12—H12119.6
C1—C2—C3104.0 (2)C13—C12—H12119.6
C1—C2—C7123.0 (2)C12—C13—C8121.1 (2)
C3—C2—C7133.0 (2)C12—C13—H13119.5
N2—C3—C2111.2 (2)C8—C13—H13119.5
N2—C3—C4121.2 (2)N4—C14—C6175.8 (3)
C2—C3—C4127.5 (2)C16—C15—C20120.0 (2)
C3—C4—H4A109.5C16—C15—N1121.8 (2)
C3—C4—H4B109.5C20—C15—N1118.1 (2)
H4A—C4—H4B109.5C15—C16—C17119.5 (3)
C3—C4—H4C109.5C15—C16—H16120.2
H4A—C4—H4C109.5C17—C16—H16120.2
H4B—C4—H4C109.5C18—C17—C16120.4 (3)
N3—C5—C6127.4 (2)C18—C17—H17119.8
N3—C5—O1109.72 (19)C16—C17—H17119.8
C6—C5—O1122.9 (2)C19—C18—C17119.7 (3)
C5—C6—C14118.6 (2)C19—C18—H18120.1
C5—C6—C7125.7 (2)C17—C18—H18120.1
C14—C6—C7115.70 (19)C18—C19—C20120.9 (3)
C2—C7—C6106.39 (18)C18—C19—H19119.5
C2—C7—C8112.92 (18)C20—C19—H19119.5
C6—C7—C8111.56 (18)C19—C20—C15119.3 (3)
C2—C7—H7108.6C19—C20—H20120.3
C6—C7—H7108.6C15—C20—H20120.3
C8—C7—H7108.6
C1—N1—N2—C30.1 (2)C2—C7—C8—C9−40.3 (3)
C15—N1—N2—C3178.88 (19)C6—C7—C8—C979.5 (2)
N2—N1—C1—C2−0.1 (2)C2—C7—C8—C13141.2 (2)
C15—N1—C1—C2−178.6 (2)C6—C7—C8—C13−99.0 (2)
N2—N1—C1—O1−179.75 (18)C13—C8—C9—C10−0.2 (3)
C15—N1—C1—O11.7 (3)C7—C8—C9—C10−178.7 (2)
C5—O1—C1—C23.0 (3)C8—C9—C10—C11−0.3 (4)
C5—O1—C1—N1−177.44 (18)C8—C9—C10—N5−179.3 (2)
N1—C1—C2—C30.1 (2)O3—N5—C10—C9−169.2 (2)
O1—C1—C2—C3179.7 (2)O2—N5—C10—C910.8 (3)
N1—C1—C2—C7−178.24 (19)O3—N5—C10—C1111.8 (4)
O1—C1—C2—C71.4 (3)O2—N5—C10—C11−168.2 (3)
N1—N2—C3—C2−0.1 (2)C9—C10—C11—C120.3 (4)
N1—N2—C3—C4178.7 (2)N5—C10—C11—C12179.3 (2)
C1—C2—C3—N20.0 (3)C10—C11—C12—C130.3 (4)
C7—C2—C3—N2178.1 (2)C11—C12—C13—C8−0.7 (4)
C1—C2—C3—C4−178.7 (2)C9—C8—C13—C120.7 (4)
C7—C2—C3—C4−0.7 (4)C7—C8—C13—C12179.2 (2)
C1—O1—C5—N3179.41 (18)C5—C6—C14—N4175 (4)
C1—O1—C5—C6−2.0 (3)C7—C6—C14—N4−5(4)
N3—C5—C6—C14−4.0 (4)C1—N1—C15—C1613.3 (4)
O1—C5—C6—C14177.69 (19)N2—N1—C15—C16−165.1 (2)
N3—C5—C6—C7175.1 (2)C1—N1—C15—C20−167.8 (2)
O1—C5—C6—C7−3.3 (3)N2—N1—C15—C2013.8 (3)
C1—C2—C7—C6−5.6 (3)C20—C15—C16—C17−1.4 (4)
C3—C2—C7—C6176.6 (2)N1—C15—C16—C17177.4 (2)
C1—C2—C7—C8117.1 (2)C15—C16—C17—C180.1 (4)
C3—C2—C7—C8−60.7 (3)C16—C17—C18—C191.3 (5)
C5—C6—C7—C26.7 (3)C17—C18—C19—C20−1.4 (5)
C14—C6—C7—C2−174.27 (19)C18—C19—C20—C150.0 (5)
C5—C6—C7—C8−116.9 (2)C16—C15—C20—C191.4 (4)
C14—C6—C7—C862.2 (2)N1—C15—C20—C19−177.5 (2)
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.862.633.196 (3)124
N3—H3B···N4ii0.862.223.067 (3)169
C19—H19···O2iii0.932.543.294 (4)139
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3A⋯O2i0.862.633.196 (3)124
N3—H3B⋯N4ii0.862.223.067 (3)169
C19—H19⋯O2iii0.932.543.294 (4)139

Symmetry codes: (i) ; (ii) ; (iii) .

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1.  Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening.

Authors:  Nicolas Foloppe; Lisa M Fisher; Rob Howes; Andrew Potter; Alan G S Robertson; Allan E Surgenor
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2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 3.  Chemo-differentiating ABB' multicomponent reactions. Privileged building blocks.

Authors:  David Tejedor; Fernando García-Tellado
Journal:  Chem Soc Rev       Date:  2006-10-16       Impact factor: 54.564

4.  Pyrazolopyranopyrimidines as a class of anti-inflammatory agents.

Authors:  Magdy E A Zaki; Hanan A Soliman; Ola A Hiekal; Aymn E Rashad
Journal:  Z Naturforsch C J Biosci       Date:  2006 Jan-Feb

Review 5.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622
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