Diversity-Oriented Synthesis of Steviol Glycosides.
Qiao, Zhi; Liu, Hui; Sui, Jing-Jing; Liao, Jin-Xi; Tu, Yuan-Hong; Schmidt, Richard R.; Sun, Jian-Song; The Journal of organic chemistry 83 (2018) 11480–11492; doi:10.1021/acs.joc.8b01274

data_4035195
_publ_section_title
;
 Diversity-Oriented Synthesis of Steviol Glycosides.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11480
_journal_page_last               11492
_journal_paper_doi               10.1021/acs.joc.8b01274
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_sum            'C31 H36 O4'
_chemical_formula_weight         472.60
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.236(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5610(5)
_cell_length_b                   6.3397(4)
_cell_length_c                   27.0124(16)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5340
_cell_measurement_theta_min      3.7720
_cell_volume                     1293.84(14)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13646
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52710
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
; 
 Flack x determined using 1516 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_coef       0.063(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.1136
_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^)+(0.1278P)^2^+4.7572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3013
_refine_ls_wR_factor_ref         0.3038
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4467
_reflns_number_total             4746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01274_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035195
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              43966
_shelx_hkl_checksum              71147