Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone.
Kaplan, Will; Khatri, Hem Raj; Nagorny, Pavel; Journal of the American Chemical Society 138 (2016) 7194–7198; doi:10.1021/jacs.6b04029

data_4125094
_publ_section_title
;
 Concise Enantioselective Total Synthesis of Cardiotonic Steroids
 19-Hydroxysarmentogenin and Trewianin Aglycone.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7194
_journal_page_last               7198
_journal_paper_doi               10.1021/jacs.6b04029
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C28 H34 O8, C H2 Cl2'
_chemical_formula_sum            'C29 H36 Cl2 O8'
_chemical_formula_weight         583.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                91.518(6)
_cell_angle_beta                 110.105(8)
_cell_angle_gamma                113.487(8)
_cell_formula_units_Z            2
_cell_length_a                   10.1108(2)
_cell_length_b                   12.5567(2)
_cell_length_c                   12.7249(9)
_cell_measurement_reflns_used    22291
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.80
_cell_volume                     1366.10(17)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36556
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         3.767
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.612
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4912
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1085P)^2^+2.0549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4386
_reflns_number_total             4912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04029_si_001.cif
_cod_data_source_block           wk1080
_cod_depositor_comments          'Adding full bibliography for 4125094.cif.'
_cod_original_cell_volume        1366.10(14)
_cod_database_code               4125094
_shelx_estimated_absorpt_t_min   0.513
_shelx_estimated_absorpt_t_max   0.861
_shelxl_version_number           2014/6
_shelx_res_checksum              78604
_shelx_hkl_checksum              45063