Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and (+)-brazilide A
Xuequan Wang; Hongbin Zhang; Xiaodong Yang; Jingfeng Zhao; Chengxue Pan; Chem.Commun. 49 (2013) 5405–; doi:10.1039/c3cc42385a

data_7109366
_publ_section_title
;
 Enantioselective total synthesis of (+)-brazilin, (-)-brazilein and
 (+)-brazilide A
;
_journal_name_full               Chem.Commun.
_journal_page_first              5405
_journal_paper_doi               10.1039/c3cc42385a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C23 H18 O8'
_chemical_formula_sum            'C23 H18 O8'
_chemical_formula_weight         422.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.231(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.082(4)
_cell_length_b                   8.1761(16)
_cell_length_c                   12.919(3)
_cell_measurement_reflns_used    8380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.20
_cell_volume                     1944.8(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19227
_diffrn_reflns_theta_full        30.45
_diffrn_reflns_theta_max         30.45
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.6194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                4324
_reflns_number_total             5453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42385a.txt
_cod_data_source_block           a
_cod_original_cell_volume        1944.8(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7109366