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_1558690
_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         'C22 H35 N3 O2'
_chemical_formula_sum            'C22 H35 N3 O2'
_chemical_formula_weight         373.53
_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                 112.133(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5347(19)
_cell_length_b                   8.1076(14)
_cell_length_c                   11.9342(16)
_cell_measurement_reflns_used    1096
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.54
_cell_measurement_theta_min      3.11
_cell_volume                     1033.8(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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_unetI/netI     0.2376
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9430
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.111
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.622
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.2(10)
_refine_ls_extinction_coef       0.027(4)
_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   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.2465
_refine_ls_R_factor_gt           0.0874
_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^)+(0.0255P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                1626
_reflns_number_total             4383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00134_si_002.cif
_cod_data_source_block           20_fin
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558690
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              61274
_shelx_hkl_checksum              45158