The crystal and molecular structure of a synthetic imidazo-purine

Macintyre, Walter M.; Zahrobsky, Robert F.

doi:10.1524/zkri.1963.119.3-4.226

Cited by 8 publications

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“…Another adenine derivative (5) with a C2 bridge between N(l) and N(6) has also been studied by X-ray diffraction, but was not refined to a stage that merits detailed discussion of the molecular dimensions. 28 As has been pointed out previously,24•29-32 formation of a bond to a third atom by the atom N(l)…”

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Crystal and molecular structure of a derivative of 1,N6-ethenoadenosine hydrochloride. Dimensions and molecular interactions of the fluorescent .epsilon.-adenosine (.epsilon. Ado) system

Wang¹,

Dammann²,

Barrio³

et al. 1974

J. Am. Chem. Soc.

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is much closer to the free rotation model than the fix!d staggered model for a C-N bond length of 1.488 A, suggesting a low barrier to internal rotation in the ion. ratio 0 6 6 / 0 3 5 is bracketed by the free and the eclipsed ratios. A preferentially eclipsed conformer would be indicated rather than staggered. The experimental ratio Abstract: The crystal structure of 7-ethyl-3-P-~-ribofuranosylimidazo[2,1-i]purine hydrochloride monohydrate (3) has been determined both to establish the direction of addition of chloroacetaldehyde to adenine in the preparation of e-adenine derivatives and to probe the molecular interactions of the highly fluoresceat +adenosine derivative. The crystals of 3 are monoclinic, with a = 12.952 (3), b = 6.667 (2), and c = 9.679 (2) A, and = 101 O 34' (1 '). There are two molecules of C14HlsN504+Cl-.H20 in the space group P21. The structure has been refined to an R factor of v.043 in 1373 nonzero reflections. The entire e-adenine moiety is near-planar with a maximum deviation of 0.028 A among the ring atoms. There are some minor differences in bond lengths in the adenine residue in 3 when compared to unbridged adenine rings, but the greatest differences involve the exocyclic angles at C(6). The arrangement about the glycosyl bond is syn (xCN = -109.1 ") and the ribose ring exists in the C(2') endo-C(l ') exo conformation. The C(4')-C(5') exocyclic bond is in the trans-gauche arrangement. The N-H bond in the base, all three 0-H bonds in the sugar, and the water molecules are involved in hydrogen bonding in the monohydrate. The crystal can be divided into successive regions (in the a direction) of polar and nonpolar character. In the nonpolar regions, there are infinite stacks (in the b direction) of +adenine rings, e! ch of which overlap considerably with their neighbors with alternate ring-ring separations of 3.344 and 3.324 A. These overlaps are compared with those found in related molecules.he reaction of chloroacetaldehyde with adenosine (4) N. K. Kochetkov, V. N. Shibaev, and A. A. Kost, Dokl. Akad. These authors did not establish the Nauk. SSSR, 205, 100 (1972). structure of the product. Paul, et al. / Deriuatiws of I,Ne-Ethenoadenosine Hydrochloride a Standard deviations in parentheses. ' The y coordinate of the C1 ion was held constant to define the origin in the b direction.A crystal 0.5 mm in the b direction and 0.2 X 0.06 mm in cross section was used for data collection. The general procedures for data collection were as described previously.6 The a t a n t s of -(6) J. K. Frank and I. C. Paul, J . Amer. Chem. Soc., 95, 2324 (1973).

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“…There was no base-base overlap in the crystal structure of 5. 28 The main interaction in that crystal appeared to be an ion-ion contact between the positively charged heterocyclic base and the iodide ion.…”

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confidence: 97%

Crystal and molecular structure of a derivative of 1,N6-ethenoadenosine hydrochloride. Dimensions and molecular interactions of the fluorescent .epsilon.-adenosine (.epsilon. Ado) system

Wang¹,

Dammann²,

Barrio³

et al. 1974

J. Am. Chem. Soc.

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An open chain product in the reaction of benzil with thiocarbohydrazide

et al. 1994

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An open chain compound was obtained by reaction of benzil with thiocarbohydrazide in acidic condition. Its derivative, namely, benzil bis‐(5‐isopropylidene‐3‐thiocarbohydrazone) has been structurally characterized by X‐ray single crystal diffraction method. Crystallographic data. C22H26N8S2, Mr=466.62, monoclinic, space group C2/c,a=12.215(3), b=11.473(2), c=17.032 (3)Å, β=98.96(2)°, V=2357.7(9)Å3, Z=4, Dc=1.32 g/cm3, F(000)=1040, μ(Mo Kα)=2.43 cm−1. Final R=0.050, Rw=0.061 for 1103 unique and observed reflections with I ≥ 3σ(I). The effect of the structures on the formation of the open‐chain intermediates during the cyclization of (2:2) Schiff base macrocyclic compound has been discussed and a possible mechanism for the ring closure has been suggested.

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1964 - 1965

Schudt¹,

Weitz²

Structure Data of Organic Crystals

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The crystal and molecular structure of a synthetic imidazo-purine

Cited by 8 publications

References 0 publications

Crystal and molecular structure of a derivative of 1,N6-ethenoadenosine hydrochloride. Dimensions and molecular interactions of the fluorescent .epsilon.-adenosine (.epsilon. Ado) system

Crystal and molecular structure of a derivative of 1,N6-ethenoadenosine hydrochloride. Dimensions and molecular interactions of the fluorescent .epsilon.-adenosine (.epsilon. Ado) system

An open chain product in the reaction of benzil with thiocarbohydrazide

1964 - 1965

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