Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
Andreeva, Olga V.; Garifullin, Bulat F.; Sharipova, Radmila R.; Strobykina, Irina Yu.; Sapunova, Anastasiya S.; Voloshina, Alexandra D.; Belenok, Mayya G.; Dobrynin, Alexey B.; Khabibulina, Leysan R.; Kataev, Vladimir E.; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00134

data_1558689
_publ_section_title
;
 Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a
 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00134
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C37 H51 N3 O12'
_chemical_formula_sum            'C37 H51 N3 O12'
_chemical_formula_weight         729.80
_chemical_name_systematic
;
[(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]-methyl 
16-oxo-ent-beyran-19-oat
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.250(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9445(9)
_cell_length_b                   7.3353(6)
_cell_length_c                   23.495(2)
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.42
_cell_volume                     1875.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            33981
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.694
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0750P)^2^+0.7005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                5363
_reflns_number_total             7031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00134_si_003.cif
_cod_data_source_block           53_fin_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558689
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              76477
_shelx_hkl_checksum              73686