2013
DOI: 10.1107/s0108270112050767
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Infinite ladder-like chains organized into a three-dimensional zigzag supramolecular architecture in 9-deazahypoxanthine

Abstract: The asymmetric unit of the title compound, C(6)H(5)N(3)O, consists of discrete molecules of 9-deazahypoxanthine [systematic name: 3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one]. The structure displays N-H···O hydrogen bonding, connecting the molecules into centrosymmetric dimers. These dimers are then connected by N-H···N hydrogen bonds into a ladder-like chain along the c axis. The secondary structure is stabilized by weak noncovalent contacts of the C-H···O and C-H···C types, as well as by π-π stacking interactions, … Show more

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Cited by 3 publications
(3 citation statements)
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“…Reflecting these multiple hydrogen-bonding sites, a remarkable twodimensional hydrogen-bonded network has been constructed in the single crystal. Although some purine bases such as hypoxanthine, 8,9 9-deazahypoxanthine, 10 adenine, 11,12 guanine, 13,14 and 2,6-diaminopurine 15 have already been reported to form a hydrogen-bonded network, the present network based on 1-deazahypoxanthine can be characterized by a strong intermolecular correlation and high dimensionality. Therefore, the geometric and electronic structures of single crystals were discussed in terms of the self-assembling ability of 1deazahypoxanthine.…”
Section: ■ Introductionmentioning
confidence: 80%
“…Reflecting these multiple hydrogen-bonding sites, a remarkable twodimensional hydrogen-bonded network has been constructed in the single crystal. Although some purine bases such as hypoxanthine, 8,9 9-deazahypoxanthine, 10 adenine, 11,12 guanine, 13,14 and 2,6-diaminopurine 15 have already been reported to form a hydrogen-bonded network, the present network based on 1-deazahypoxanthine can be characterized by a strong intermolecular correlation and high dimensionality. Therefore, the geometric and electronic structures of single crystals were discussed in terms of the self-assembling ability of 1deazahypoxanthine.…”
Section: ■ Introductionmentioning
confidence: 80%
“…Firstly, 6-oxo-9-deazapurine (9-deazahypoxanthine, 9dhx) was prepared by utilization of the procedure described in the literature [ 24 ], which represents a modification of the original synthetic pathway published formerly [ 25 ]. The compound was characterized by elemental analysis (C, H, N), FT-IR, 1 H and 13 C NMR spectroscopies.…”
Section: Resultsmentioning
confidence: 99%
“… Pathways for the preparation of 6-oxo-9-deazapurine according to a procedure described in [ 24 ], and complexes 1 and 2 . …”
Section: Resultsmentioning
confidence: 99%