Home Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
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Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5

  • Gao Yan EMAIL logo
Published/Copyright: August 8, 2018

Abstract

C20H21NO5, orthorhombic, Pccn (no. 56), a = 15.114(2) Å, b = 17.574(3) Å, c = 14.123(2) Å, V = 3751.3(10) Å3, Z = 8, Rgt(F) = 0.0626, wRref(F2) = 0.2130, T = 293 K.

CCDC no.: 1851923

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.33 × 0.29 × 0.24 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II CCD, φ and ω
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:17246, 3271, 0.077
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1879
N(param)refined:236
Programs:Olex2 [6], SHELX [7], Bruker [8]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
N10.56606(17)0.11697(14)0.56109(16)0.0684(8)
H1A0.5445110.0732810.5462240.082*
H1B0.5789510.1269220.6190960.082*
O10.52503(16)0.09589(11)0.26536(14)0.0738(7)
O20.51798(18)0.03628(13)0.40470(15)0.0901(8)
O30.61270(13)0.23495(10)0.53707(12)0.0582(6)
O40.66037(15)0.36574(13)0.24665(16)0.0806(7)
O50.70564(13)0.41488(11)0.38271(15)0.0673(6)
C10.4847(3)0.0377(3)0.1210(3)0.143(2)
H1C0.465397−0.0085810.0913500.214*
H1D0.4413380.0767620.1108560.214*
H1E0.5401340.0532390.0939470.214*
C20.4956(3)0.0252(2)0.2207(3)0.0972(13)
H2A0.539013−0.0145140.2313520.117*
H2B0.4399320.0090780.2483090.117*
C30.5339(2)0.09437(17)0.3596(2)0.0624(8)
C40.56393(18)0.16561(15)0.39900(18)0.0527(7)
C50.56934(18)0.23635(15)0.33679(18)0.0532(7)
H50.5956860.2225590.2757550.064*
C60.62827(17)0.29416(15)0.38566(18)0.0498(7)
C70.64356(18)0.29264(15)0.47954(18)0.0508(7)
C80.57951(19)0.16942(15)0.49403(19)0.0543(7)
C90.68814(19)0.35201(16)0.5287(2)0.0598(8)
H90.6978210.3490230.5936290.072*
C100.7156(2)0.41196(17)0.4791(2)0.0637(8)
C110.7577(3)0.48353(18)0.5172(3)0.0897(11)
H11A0.7709150.5173220.4657300.135*
H11B0.7176260.5080280.5602570.135*
H11C0.8113740.4707690.5499370.135*
C120.66338(18)0.35716(16)0.3317(2)0.0582(8)
C130.47794(18)0.27170(15)0.31964(18)0.0527(7)
C140.4245(2)0.29292(19)0.3952(2)0.0715(9)
H140.4439400.2845080.4568270.086*
C150.3429(2)0.32631(19)0.3804(3)0.0790(10)
H150.3084560.3397590.4322990.095*
C160.3112(2)0.34021(18)0.2902(3)0.0755(10)
C170.3636(2)0.31984(19)0.2129(2)0.0740(10)
C180.4468(2)0.28489(17)0.2298(2)0.0634(8)
H180.4813430.2704690.1783380.076*
C190.3354(3)0.3340(3)0.1117(3)0.1219(17)
H19A0.3804680.3159410.0694310.183*
H19B0.2810710.3075060.0993650.183*
H19C0.3267310.3875710.1021360.183*
C200.2202(2)0.3783(2)0.2781(3)0.1111(15)
H20A0.2074110.3841550.2119070.167*
H20B0.1754990.3471810.3069760.167*
H20C0.2208010.4274240.3079130.167*

Source of material

The title compound was synthesized according to a reported procedure [1]. A mixture of 4-hydroxy-6-methylpyran-2-one (10 mmol), 3,4-dimethylbenzaldehyde (10 mmol), ethyl cyanacetate (10 mmol) and 4-(dimethylamino)pyridine (DMAP) (1 mmol) in ethanol (100 mL) was refluxed for 2–3 h and then cooled to room temperature. After filtering the precipitates, they were sequentially washed with ice-cooled water and ethanol and then dried.

Experimental details

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93/0.96 Å and N—H = 0.86 Å with Uiso(H) = 1.2 times Ueq(C) and 1.2 times Ueq(N).

Comment

There is a progress achieved in the synthesis of heterocyclic compounds with biological potential [1]. It is known that many pyran derivatives may have biological activities [1], [2], [3], [4].

In the crystal structure of the title compound, the 4H,5H-pyrano[4,3-b]pyran-5-one unit is almost planar. As expected the best plane of the dimethyl-phenyl group is perpendicular to the plane of the core unit (cf. the figure). Bond lengths and angles are similar to the related phenyl derivative [5].

References

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Liang, L.; Wang, F. Y.; Shi, J. F.; Hu, Q.; Zhang, L.; Ni, H. B.: One-pot synthesis of 4-arylpolyhydroquinoline derivatives and evaluation of their anti-gastric cancer activity. Lat. Am. J. Pharm. 37 (2018) 80–84.Search in Google Scholar

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Song, J.: Crystal structure of 2-amino-7-methyl-5-oxo-4-phenyl-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H12N2O3. Z. Kristallogr. NCS 231 (2016) 747–748.10.1515/ncrs-2015-0255Search in Google Scholar

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Received: 2018-05-14
Accepted: 2018-06-29
Published Online: 2018-08-08
Published in Print: 2018-11-27

©2018 Gao Yan, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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