Jing He

Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C19H18N2O6

De Gruyter | Published online: July 13, 2018

Abstract

C19H18N2O6, monoclinic, P21/c (no. 14), a = 13.052(8) Å, b = 10.091(6) Å, c = 14.454(9) Å, β = 114.446(11)°, V = 1733.0(19) Å3, Z = 4, Rgt(F) = 0.0490, wRref(F2) = 0.1518, T = 296(2) K.

CCDC no.: 1852005

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: Colorless block
Size: 0.26 × 0.21 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω-scans
θmax, completeness: 25°, >99%
N(hkl)measured, N(hkl)unique, Rint: 8487, 3041, 0.046
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2083
N(param)refined: 245
Programs: Bruker programs [1], SHELX [2, 3] , OLEX2 [4]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.07794(13) 0.62356(15) 0.66102(12) 0.0482(5)
O2 0.07846(13) 0.74641(16) 0.50112(11) 0.0511(5)
O3 0.20953(14) 0.95803(17) 0.51976(12) 0.0549(5)
O4 0.29142(12) 0.91682(15) 1.07149(11) 0.0426(4)
O5 0.54182(13) 0.70363(17) 1.04858(13) 0.0536(5)
O6 0.51258(15) 0.7891(2) 0.89905(14) 0.0647(6)
N1 0.1548(2) 1.2354(2) 0.80994(18) 0.0689(7)
N2 0.15421(17) 1.0640(2) 1.02712(15) 0.0528(6)
H2A 0.111785 1.126552 0.990864 0.063*
H2B 0.147108 1.036796 1.080554 0.063*
C1 0.0811(2) 0.5490(3) 0.74526(19) 0.0581(7)
H1A 0.032470 0.473498 0.721429 0.087*
H1B 0.156752 0.519646 0.784835 0.087*
H1C 0.056375 0.603344 0.786571 0.087*
C2 0.14261(18) 0.7354(2) 0.68065(17) 0.0371(6)
C3 0.14185(18) 0.7982(2) 0.59557(16) 0.0389(6)
C4 −0.0175(2) 0.8244(3) 0.4445(2) 0.0626(8)
H4A −0.058673 0.784011 0.379407 0.094*
H4B −0.064701 0.830260 0.480578 0.094*
H4C 0.006005 0.911625 0.435180 0.094*
C5 0.20973(18) 0.9080(2) 0.60686(16) 0.0403(6)
C6 0.2868(2) 1.0616(3) 0.5288(2) 0.0636(8)
H6A 0.278490 1.088305 0.462299 0.095*
H6B 0.271873 1.135721 0.562968 0.095*
H6C 0.362180 1.030683 0.567140 0.095*
C7 0.27312(17) 0.9567(2) 0.70329(16) 0.0395(6)
H7 0.318132 1.031006 0.711375 0.047*
C8 0.27008(17) 0.8959(2) 0.78732(16) 0.0358(5)
C9 0.20601(18) 0.7840(2) 0.77693(17) 0.0389(6)
H9 0.205381 0.741761 0.833860 0.047*
C10 0.48324(19) 0.7879(2) 0.96785(19) 0.0454(6)
C11 0.39532(17) 0.8643(2) 0.97471(16) 0.0370(6)
C12 0.25409(18) 1.0380(2) 0.92081(17) 0.0374(6)
C13 0.1978(2) 1.1457(2) 0.85876(18) 0.0460(6)
C14 0.23108(18) 1.0091(2) 1.00046(17) 0.0393(6)
C15 0.37471(17) 0.8509(2) 1.05793(16) 0.0367(6)
C16 0.43902(18) 0.7670(2) 1.13985(18) 0.0432(6)
H16 0.424258 0.762000 1.197426 0.052*
C17 0.5198(2) 0.6965(2) 1.13289(19) 0.0481(6)
C18 0.5964(2) 0.6030(3) 1.2090(2) 0.0699(9)
H18A 0.647405 0.565111 1.183892 0.105*
H18B 0.638312 0.649445 1.271275 0.105*
H18C 0.553089 0.533740 1.221261 0.105*
C19 0.33355(17) 0.9592(2) 0.89078(16) 0.0370(6)
H19 0.388731 1.020886 0.885187 0.044*

Source of material

The title compound was synthesized according to a reported procedure. A mixture of 4-hydroxy-6-methylpyran-2-one (10 mmol), 3,4,5-trimethoxybenzaldehyde (10 mmol), malononitrile (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 under reduced pressure.

Experimental details

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

Discussion

Pyran derivatives may possess several types of pharmacological properties such as anticancer, anti-HIV, anticoagulant, spasmolytic, and antibacterial activity [5]. A large number of structurally novel pyran derivatives have been reported to show substantial cytotoxic activity in vitro and in vivo [6]. Research focused on the synthesis of the dihydropyran derivatives [7]. Herein, we reported the structure of a new pyran derivative.

In the crystal structure of the title compound (cf. the figure), one methoxy group is connected to 4H,5H-pyrano[4,3-b]pyran-5-one unit at the 7-position. One cyano group and one amino group are linked to the 2 and 4-position of this system, respectively. Three methoxy groups are connected to C13, C15 and C17 atoms respectively. Above mentioned bond lengths fall in their normal ranges compared with those in previously studies [8], [9].

Acknowledgements

This work was supported by the Scientific Research Program Funded by Shaanxi Provincial Education Department (Program No. 16JK1187) and Shaanxi Xueqian Normal University (Program No. 2014YBKJ030).

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Received: 2018-03-11
Accepted: 2018-06-27
Published Online: 2018-07-13
Published in Print: 2018-08-28

©2018 Jing He, published by De Gruyter, Berlin/Boston

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