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_4518046
_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            'C13 H17 Cl3 N2 O6'
_chemical_formula_weight         403.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-11 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6577(3)
_cell_length_b                   9.0916(2)
_cell_length_c                   11.5007(2)
_cell_measurement_reflns_used    12802
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      75.6060
_cell_measurement_theta_min      3.9210
_cell_volume                     1701.73(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12488
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         6.485
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    5.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(14)
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0542P)^2^+1.8944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                2824
_reflns_number_total             2865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03348_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4518045--4518047.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4518046
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.575
_shelx_estimated_absorpt_t_max   0.682
_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              4159
_shelx_hkl_checksum              79197