Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C.
Sun, Wang-Bin; Wang, Xuan; Sun, Bing-Feng; Zou, Jian-Ping; Lin, Guo-Qiang; Organic letters 18 (2016) 1219–1221; doi:10.1021/acs.orglett.6b00150

data_1542576
_publ_section_title
;
 Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1219
_journal_page_last               1221
_journal_paper_doi               10.1021/acs.orglett.6b00150
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2935(6)
_cell_length_b                   8.8494(8)
_cell_length_c                   19.3290(17)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.903
_cell_measurement_theta_min      5.063
_cell_volume                     1247.55(19)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7546
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.107
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0655P)^2^+0.0823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2166
_reflns_number_total             2441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00150_si_003.cif
_cod_data_source_block           cd21453
_cod_depositor_comments
'Adding full bibliography for 1542576--1542577.cif.'
_cod_database_code               1542576
_shelxl_version_number           2013-4
_shelx_res_checksum              80633
_shelx_hkl_checksum              5988