Synthesis of Δ<sup>20</sup>-Ginsenosides Rh<sub>4</sub>, (20E)-Rh<sub>3</sub>, Rg<sub>6</sub>, and Rk<sub>1</sub>: A General Approach To Access Dehydrated Ginsenosides.
Shen, Renzeng; Laval, Stephane; Cao, Xin; Yu, Biao; The Journal of organic chemistry 83 (2018) 2601–2610; doi:10.1021/acs.joc.7b02987

data_4034959
_publ_section_title
;
 Synthesis of \D<sup>20</sup>-Ginsenosides Rh<sub>4</sub>,
 (20E)-Rh<sub>3</sub>, Rg<sub>6</sub>, and Rk<sub>1</sub>: A General
 Approach To Access Dehydrated Ginsenosides.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2601
_journal_page_last               2610
_journal_paper_doi               10.1021/acs.joc.7b02987
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C30 H50 O2'
_chemical_formula_weight         442.70
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.613(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3996(13)
_cell_length_b                   7.4707(8)
_cell_length_c                   31.868(4)
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.817
_cell_measurement_theta_min      4.371
_cell_volume                     2713.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15846
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.278
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1946 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         9629
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0769
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                6508
_reflns_number_total             9629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02987_si_002.cif
_cod_data_source_block           cd214543
_cod_original_cell_volume        2713.9(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034959
_shelxl_version_number           2013-4
_shelx_res_checksum              93543
_shelx_hkl_checksum              22151