Crystal Structure of 5,5'-(Furan-2-ylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione)
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TRUCTURE OF ORGANIC COMPOUNDS
Crystal Structure of 5,5'-(Furan-2-ylmethylene)bis(6-amino-1,3dimethylpyrimidine-2,4(1H,3H)-dione) Naresh Sharmaa,* a
Govt. Degree College for Women, Kathua (J & K), India *e-mail: [email protected]
Received April 21, 2020; revised June 9, 2020; accepted June 11, 2020
Abstract—The crystal structure of the title compound is determined by single crystal X-ray structure analysis. The compound C17H20N6O5, crystallizes in the monoclinic crystal system with space group P21/c having unit-cell parameters: a = 11.3123(8), b = 14.8291(10), c = 10.8777(8) Å, β = 102.943(7)°, and Z = 4. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0496 for 2109 observed reflections. The molecules in the crystal are linked into infinite two-dimensional network by C−H⋅⋅⋅O, C−H⋅⋅⋅N, N−H⋅⋅⋅O, N−H⋅⋅⋅N, and C−H⋅⋅⋅π type of hydrogen bonds. Molecules are also reinforced by π⋅⋅⋅π interaction between ring B and ring C, respectively. DOI: 10.1134/S106377452006022X
INTRODUCTION Uracil derivatives represent a “privileged” structural motif in a wide variety of natural and synthetic compounds with a broad spectrum of significant biological activities [1]. 6-Aminouracils are the important starting compounds for the synthesis of medicinally useful xanthines and theophyllines, which are now routinely used as a phosphodiesterase inhibitor for the treatment of asthma [2]. 6-Aminouracils are regarded as the key intermediates for the synthesis of purinesbased drugs, such as penciclovir, caffeine, theophyl-
С23
С22
С
O24
line, and theobromine [3]. In addition, pyrimidine scaffolds are reported to exhibit diverse biological and pharmaceutical activities [4]. Pyrimidine containing organic scaffolds is known to exhibit diverse biological and pharmaceutical activities as well [5]. Heterocycles, particularly bearing a pyrimidine moiety, such as dihydropyrimidines [6], furopyrimidines [7], and pyrazolopyrimidines [8] are regarded as scaffolds of pharmaceutical promise due to their several biological efficacies [9]. Herein we report the crystal structure of a new arylmethylene-bis uracil derivative, namely 5,5'(furan-2-ylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione) synthesized via one-pot pseudo multicomponent reaction at room temperature using Ceric ammonium nitrate (CAN) as inexpensive and eco-friendly catalyst [10] (Fig. 1).
С21
EXPERIMENTAL O4 C13
С20
C4 N18
C19 N3 C2
A
C5 C6
O2
С16
C6'
N1
N1'
C5'
B O4' O2'
C4' N3'
C2'
N15 C14
C17
Fig. 1. ORTEP view of the molecule.
Single crystals of the title compound, C17H20N6O5, suitable for X-ray diffraction analysis, were received from Dr. Goutam Brahmachari. The synthesis of the compound is described in [10]. The crystallographic data contains the CCDC no. 968994. X-ray intensity data of 6278 reflections (of which 3121 unique) were collected on X’calibur CCD area-detector diffractometer equipped
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