Boron-Selective Biaryl Coupling Approach to Versatile Dibenzoxaborins and Application to Concise Synthesis of Defucogilvocarcin M.
Sumida, Yuto; Harada, Ryu; Kato-Sumida, Tomoe; Johmoto, Kohei; Uekusa, Hidehiro; Hosoya, Takamitsu; Organic letters 16 (2014) 6240–; doi:10.1021/ol5031734

data_1518690
_publ_section_title
;
 Boron-Selective Biaryl Coupling Approach to Versatile Dibenzoxaborins and
 Application to Concise Synthesis of Defucogilvocarcin M.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6240
_journal_paper_doi               10.1021/ol5031734
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H11 B O2'
_chemical_formula_sum            'C18 H11 B O2'
_chemical_formula_weight         270.08
_chemical_name_common            RH2Y15-1
_chemical_name_systematic        8,9-Dioxa-8a-borabenzo[fg]tetracene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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-2014/5
_cell_angle_alpha                90
_cell_angle_beta                 91.2140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.16120(10)
_cell_length_b                   15.5151(3)
_cell_length_c                   15.9033(3)
_cell_measurement_reflns_used    14557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.98
_cell_volume                     1273.20(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14557
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         3.981
_diffrn_source                   'fine-focus rotating anode x-ray'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'abscor Higashi RIGAKU'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0776P)^2^+0.0873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1736
_reflns_number_total             2293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5031734_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1518690
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2014/5
_shelx_res_checksum              90350
_shelx_hkl_checksum              61455