Synthetic Approach to the Core Structure of Oleandrin and Related Cardiac Glycosides with Highly Functionalized Ring D.
Michalak, Karol; Morawiak, Maja; Wicha, Jerzy; Organic letters 18 (2016) 6148–6151; doi:10.1021/acs.orglett.6b03157

data_1555950
_publ_section_title
;
 Synthetic Approach to the Core Structure of Oleandrin and Related Cardiac
 Glycosides with Highly Functionalized Ring D.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6148
_journal_page_last               6151
_journal_paper_doi               10.1021/acs.orglett.6b03157
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H34 O4'
_chemical_formula_sum            'C24 H34 O4'
_chemical_formula_weight         386.51
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 113.6460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0052(2)
_cell_length_b                   7.56960(10)
_cell_length_c                   12.6467(2)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.35
_cell_measurement_theta_min      3.81
_cell_volume                     1052.77(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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.353
_diffrn_reflns_theta_min         3.815
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.8670
_exptl_absorpt_correction_T_min  0.7470
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.227
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0370P)^2^+0.1569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3189
_reflns_number_total             3734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03157_si_003.cif
_cod_data_source_block           MK9_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555950
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.867
_shelxl_version_number           2014-3
_shelx_res_checksum              53189
_shelx_hkl_checksum              75050