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_1542577
_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                   5.5435(6)
_cell_length_b                   7.7426(9)
_cell_length_c                   27.879(3)
_cell_measurement_reflns_used    3510
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.205
_cell_measurement_theta_min      5.461
_cell_volume                     1196.6(2)
_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'
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_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  0.0536
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7110
_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         25.991
_diffrn_reflns_theta_min         1.461
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
; 
 Flack x determined using 858 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.8(7)
_refine_ls_extinction_coef       0.075(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0714P)^2^+0.0848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2217
_reflns_number_total             2355
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00150_si_002.cif
_cod_data_source_block           cd214158
_cod_depositor_comments
'Adding full bibliography for 1542576--1542577.cif.'
_cod_database_code               1542577
_shelxl_version_number           2013-4
_shelx_res_checksum              64320
_shelx_hkl_checksum              30511