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_4034960
_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            'C36 H56 O6'
_chemical_formula_weight         584.80
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.984(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.271(6)
_cell_length_b                   7.176(3)
_cell_length_c                   17.155(7)
_cell_measurement_reflns_used    1032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.460
_cell_measurement_theta_min      4.894
_cell_volume                     1704.8(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0513
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10347
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.128
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1040 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0925P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.840
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                3405
_reflns_number_total             6157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02987_si_003.cif
_cod_data_source_block           cd214293
_cod_original_cell_volume        1704.8(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034960
_shelxl_version_number           2013-4
_shelx_res_checksum              66097
_shelx_hkl_checksum              39617