Total Synthesis of (-)-Chromodorolide B By a Computationally-Guided Radical Addition/Cyclization/Fragmentation Cascade.
Tao, Daniel J.; Slutskyy, Yuriy; Muuronen, Mikko; Le, Alexander; Kohler, Philipp; Overman, Larry E.; Journal of the American Chemical Society 140 (2018) 3091–3102; doi:10.1021/jacs.7b13799

data_4132004
_publ_section_title
;
 Total Synthesis of (-)-Chromodorolide B By a Computationally-Guided
 Radical Addition/Cyclization/Fragmentation Cascade.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3091
_journal_page_last               3102
_journal_paper_doi               10.1021/jacs.7b13799
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H22 O6'
_chemical_formula_weight         346.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.2262(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7391(5)
_cell_length_b                   12.8346(14)
_cell_length_c                   14.2014(16)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.89
_cell_volume                     858.70(16)
_computing_cell_refinement       'Bruker SAINT 7.68a, 2009'
_computing_data_collection       'Bruker APEX2 2010.9-0, 2010'
_computing_data_reduction        'Bruker SAINT 7.68a, 2009'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2008/4'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9390
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.633
_diffrn_reflns_theta_min         2.144
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2008/1'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 1711 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0488P)^2^+0.0470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                3792
_reflns_number_total             4014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b13799_si_001.cif
_cod_data_source_block           leo245
_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_sg_symbol_H-M      'P n'
_cod_database_code               4132004
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.987
_exptl_absorpt_special_details
; 
9614 Corrected reflections written to file leo245s.hkl 
Estimated minimum and maximum transmission:  0.6717  1.0000 
The ratio of these values is more reliable than their absolute values 
Lambda/2 correction factor = 0.0015 
;
_shelx_res_checksum              64770
_shelx_hkl_checksum              53815