Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY.
Wang, Sisi; Wang, Zhaoli; Gao, Hu; Jiang, Liang; Liu, Hui; Wu, Fan; Zhao, Yue; Chan, Kin Shing; Shen, Zhen; Chemical communications (Cambridge, England) 57 (2021) 1758–1761; doi:10.1039/d0cc08163a

data_7127768
_publ_section_title
;
 Highly regioselective palladium-catalyzed domino reaction for
 post-functionalization of BODIPY.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1758
_journal_page_last               1761
_journal_paper_doi               10.1039/d0cc08163a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C50 H43 B F2 N2'
_chemical_formula_weight         720.67
_chemical_name_systematic        2d
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-04 deposited with the CCDC.	2021-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.515(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   21.8885(14)
_cell_length_c                   14.3585(8)
_cell_measurement_reflns_used    5469
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.36
_cell_volume                     3860.0(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker 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  0.0421
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15659
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.148
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         6543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0860
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0101P)^2^+15.4354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5067
_reflns_number_total             6543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08163a2.cif
_cod_data_source_block           20180919SZ_WSS_0m_a
_cod_depositor_comments
'Adding full bibliography for 7127767--7127769.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127768
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              98222
_shelx_hkl_checksum              8954