Synthesis of novel C-nucleoside analogues bearing an anomeric cyano and a 1,2,3-triazole nucleobase as potential antiviral agents
Mathe-Allainmat, Monique; LeBreton, Jacques; Sierocki, Pierre; Guillemont, Jerome; Tessier, Arnaud; Arzel, Laurence; Grosse, Sandrine; Gaillard, Krystal; Arellano-Reyes, Ruben Arturo; Lambert, Emilie; Donnard, Chloe; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02451E

data_7158565
_publ_section_title
;
 Synthesis of novel C-nucleoside analogues bearing an anomeric cyano and a
 1,2,3-triazole nucleobase as potential antiviral agents
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02451E
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H11 I N4 O5, H2 O'
_chemical_formula_sum            'C8 H13 I N4 O6'
_chemical_formula_weight         388.12
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-10-16T16:28:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.952(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1449(9)
_cell_length_b                   15.429(3)
_cell_length_c                   11.890(2)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      70.968
_cell_measurement_theta_min      4.653
_cell_volume                     1291.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material
'WinGX publication routines (Farrugia, V2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.497
_diffrn_reflns_theta_min         3.774
_exptl_absorpt_coefficient_mu    19.813
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.51707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1763
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.706
_reflns_number_gt                2910
_reflns_number_total             4304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02451e2.cif
_cod_data_source_block           psi371_n2n6
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H26 I2 N8 O12'
_cod_original_formula_weight         776.25
_cod_original_formula_moiety         '2(C8 H11 I N4 O5), 2(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158565
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              49918