Total Synthesis and Structure Revision of (-)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of <i>Illicium simonsii</i>.
Burns, Alexander S.; Rychnovsky, Scott D.; Journal of the American Chemical Society 141 (2019) 13295–13300; doi:10.1021/jacs.9b05065

data_4128921
_publ_section_title
;
 Total Synthesis and Structure Revision of (-)-Illisimonin A, a
 Neuroprotective Sesquiterpenoid from the Fruits of <i>Illicium
 simonsii</i>.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13295
_journal_page_last               13300
_journal_paper_doi               10.1021/jacs.9b05065
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H32 Fe O6'
_chemical_formula_weight         496.36
_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     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.379(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.169(2)
_cell_length_b                   23.029(6)
_cell_length_c                   12.208(3)
_cell_measurement_reflns_used    6799
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.43
_cell_volume                     2296.0(10)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16853
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.350
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.669
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.8014
_exptl_absorpt_correction_T_min  0.6552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.184
_refine_diff_density_max         1.609
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
; 
 Flack x determined using 2982 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         8310
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0710P)^2^+0.9139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                7261
_reflns_number_total             8310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05065_si_002.cif
_cod_data_source_block           sdr34
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2295.9(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128921
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.772
_shelx_estimated_absorpt_t_max   0.882
_exptl_absorpt_special_details
; 
Reflections not merged 
19826 Corrected reflections written to file sdr34s.hkl 
Estimated minimum and maximum transmission:  0.6552  0.8014 
The ratio (0.8176) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.1500 
Lambda/2 correction factor = 0.00150 
  
;
_shelx_res_checksum              32178
_shelx_hkl_checksum              16477