Intramolecular Michael Additions in Uridine Derivatives: Isolation of the Labile 5′O-C6 Cyclonucleoside
Gissot, Arnaud; Massip, Stéphane; Barthélémy, Philippe; ACS Omega 5 (2020) 24746–24753; doi:10.1021/acsomega.0c03348

data_4518045
_publ_section_title
;
 Intramolecular Michael Additions in Uridine Derivatives: Isolation of the
 Labile 5&#x2032;O-C6 Cyclonucleoside
;
_journal_issue                   38
_journal_name_full               'ACS Omega'
_journal_page_first              24746
_journal_page_last               24753
_journal_paper_doi               10.1021/acsomega.0c03348
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H16 N2 O5 S'
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_space_group_name_Hall           'P 1'
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_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2018-07-11 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
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_cell_length_c                   11.5162(4)
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      4.06
_cell_volume                     660.45(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku PILATUS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.992
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16635
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.885
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_diffrn_reflns_theta_min         4.077
_diffrn_source                   'Rotating Anode'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91588
_exptl_absorpt_correction_type   multi-scan
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_refine_diff_density_max         0.538
_refine_diff_density_min         -0.295
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_refine_ls_abs_structure_details
;
 Flack x determined using 2002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4671
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.2251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                4629
_reflns_number_total             4671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03348_si_004.cif
_cod_data_source_block           ag348
_cod_depositor_comments
;
'Adding full bibliography for 4518045--4518047.cif.

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C24 H32 N4 O10 S2'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     600.65
_cod_database_code               4518045
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.931
_exptl_absorpt_special_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_shelx_res_checksum              20836
_shelx_hkl_checksum              81467