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Crystal and molecular structure of 2-thiouridine

Abstract

The ''minor'' nucleoside 2-thiouridine, C/sub 9/H/sub 12/O/sub 5/N/sub 2/S, crystallizes in a monoclinic cell, space group P2/sub 1/ with a = 5.049 (2), b = 7.526 (2), c = 14.050 (3) A, ..beta.. = 90.17 (2)/sup 0/, and d = 1.619 g cm/sup -3/ (for Z = 2) at 22 +- 2/sup 0/C. The structure was derived from 1334 unique intensities measured with an Oak Ridge computer-controlled diffractometer to a limit of sin theta/lambda = 0.65 A/sup -1/ with Nb-filtered Mo K..cap alpha.. radiation. Atomic parameters were obtained by a combination of Patterson and Fourier techniques and refined by full-matrix least squares to a final R(F) value of 0.023 for all data. The bond lengths and angles in the molecule agree well with those of other thiopyrimidines (C(2) - S = 1.677 A). The conformation of the sugar ring relative to the base is anti with a torsion angle chi(O(1')--C(1') ..-->.. N(1)--C(6)) of 17/sup 0/. The sugar exists in the 3'-endo conformation. The O(5')--C(5') bond is gauche to C(4) - O(1') and trans to C(4')--C(3') (torsion angles of 74 and -169/sup 0/ respectively). The molecules are linked together in the crystal by hydrogen bonds in an intricate network which is  More>>
Authors:
Publication Date:
Jan 01, 1977
Product Type:
Journal Article
Reference Number:
ERA-03-050781; EDB-78-103723
Resource Relation:
Journal Name: Acta Crystallogr., Sect. B; (Denmark); Journal Volume: 33
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; NUCLEOSIDES; STRUCTURAL CHEMICAL ANALYSIS; ORGANIC SULFUR COMPOUNDS; URACILS; BOND ANGLE; BOND LENGTHS; COMPARATIVE EVALUATIONS; FOURIER ANALYSIS; LATTICE PARAMETERS; LEAST SQUARE FIT; MEDIUM TEMPERATURE; MOLECULAR STRUCTURE; MONOCLINIC LATTICES; PATTERSON METHOD; PYRIMIDINES; TEMPERATURE DEPENDENCE; AZINES; CRYSTAL LATTICES; CRYSTAL STRUCTURE; HETEROCYCLIC COMPOUNDS; HYDROXY COMPOUNDS; MAXIMUM-LIKELIHOOD FIT; NUCLEOTIDES; NUMERICAL SOLUTION; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; RIBOSIDES; 400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
OSTI ID:
6855496
Research Organizations:
Oak Ridge National Lab., TN
Country of Origin:
Denmark
Language:
English
Other Identifying Numbers:
Journal ID: CODEN: ACBCA
Submitting Site:
ORNL
Size:
Pages: 80-85
Announcement Date:

Citation Formats

Hawkinson, S W. Crystal and molecular structure of 2-thiouridine. Denmark: N. p., 1977. Web. doi:10.1107/S0567740877002623.
Hawkinson, S W. Crystal and molecular structure of 2-thiouridine. Denmark. doi:10.1107/S0567740877002623.
Hawkinson, S W. 1977. "Crystal and molecular structure of 2-thiouridine." Denmark. doi:10.1107/S0567740877002623. https://www.osti.gov/servlets/purl/10.1107/S0567740877002623.
@misc{etde_6855496,
title = {Crystal and molecular structure of 2-thiouridine}
author = {Hawkinson, S W}
abstractNote = {The ''minor'' nucleoside 2-thiouridine, C/sub 9/H/sub 12/O/sub 5/N/sub 2/S, crystallizes in a monoclinic cell, space group P2/sub 1/ with a = 5.049 (2), b = 7.526 (2), c = 14.050 (3) A, ..beta.. = 90.17 (2)/sup 0/, and d = 1.619 g cm/sup -3/ (for Z = 2) at 22 +- 2/sup 0/C. The structure was derived from 1334 unique intensities measured with an Oak Ridge computer-controlled diffractometer to a limit of sin theta/lambda = 0.65 A/sup -1/ with Nb-filtered Mo K..cap alpha.. radiation. Atomic parameters were obtained by a combination of Patterson and Fourier techniques and refined by full-matrix least squares to a final R(F) value of 0.023 for all data. The bond lengths and angles in the molecule agree well with those of other thiopyrimidines (C(2) - S = 1.677 A). The conformation of the sugar ring relative to the base is anti with a torsion angle chi(O(1')--C(1') ..-->.. N(1)--C(6)) of 17/sup 0/. The sugar exists in the 3'-endo conformation. The O(5')--C(5') bond is gauche to C(4) - O(1') and trans to C(4')--C(3') (torsion angles of 74 and -169/sup 0/ respectively). The molecules are linked together in the crystal by hydrogen bonds in an intricate network which is identical to that inferred by Kojic-Prodic, Liminga, Sljukic and Ruzic-Toros (Acta Cryst. (1974), B30, 1550-1555) for the crystal structure of 5,6-dihydro-2-thiouridine. 2 figures; 6 tables.}
doi = {10.1107/S0567740877002623}
journal = {Acta Crystallogr., Sect. B; (Denmark)}
volume = {33}
journal type = {AC}
place = {Denmark}
year = {1977}
month = {Jan}
}