Total Synthesis of (±)-Brazilin using a [4+1] Palladium-Catalyzed Carbenylative Annulation.
Arredondo, Vanessa; Roa, Daniel E.; Gutman, Eugene S.; Huynh, Nancy O.; Van Vranken, David L.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02343

data_4033669
_publ_section_title
;
 Total Synthesis of (+-)-Brazilin using a [4+1] Palladium-Catalyzed
 Carbenylative Annulation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02343
_journal_year                    2019
_chemical_formula_sum            'C32 H30 O5'
_chemical_formula_weight         494.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.280(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.682(6)
_cell_length_b                   5.2523(17)
_cell_length_c                   25.856(8)
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.24
_cell_volume                     2473.3(13)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4576
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.451
_diffrn_reflns_theta_max         25.451
_diffrn_reflns_theta_min         1.642
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.861965
_exptl_absorpt_correction_T_min  0.734358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker TWINABS 2012/1'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.3511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3322
_reflns_number_total             4576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02343_si_002.cif
_cod_data_source_block           dvv16
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2473.4(14)
_cod_database_code               4033669
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.987
_exptl_absorpt_special_details
; 
HKLF 5 dataset constructed from all observations involving domain 1 
9440 Corrected reflections written to file twin5.hkl 
Reflections merged according to point-group 2/m 
Single reflections that also occur in composites omitted 
Minimum and maximum apparent transmission:  0.734358  0.861965 
Additional spherical absorption correction applied with mu*r =  0.1000 
;
_shelx_res_checksum              30062
_shelx_hkl_checksum              7084