Organotrifluoroborate Salts as Complexation Reagents for Synthesizing BODIPY Dyes Containing Both Fluoride and an Organo Substituent at the Boron Center.
Wang, Zhaoyun; Cheng, Cheng; Kang, Zhengxin; Miao, Wei; Liu, Qingyun; Wang, Hua; Hao, Erhong; The Journal of organic chemistry 84 (2019) 2732–2740; doi:10.1021/acs.joc.8b03145

data_4033726
_publ_section_title
;
 Organotrifluoroborate Salts as Complexation Reagents for Synthesizing
 BODIPY Dyes Containing Both Fluoride and an Organo Substituent at the
 Boron Center.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2732
_journal_page_last               2740
_journal_paper_doi               10.1021/acs.joc.8b03145
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C19 H20 B F N2'
_chemical_formula_weight         306.18
_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_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                 104.1590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0174(9)
_cell_length_b                   17.3665(17)
_cell_length_c                   11.4288(11)
_cell_measurement_reflns_used    6535
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.493
_cell_measurement_theta_min      2.345
_cell_volume                     1735.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD?area?detector
_diffrn_measurement_method       phi?and?omega?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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16743
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.424
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.424
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1562
_reflns_number_gt                2339
_reflns_number_total             3061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b03145_si_003.cif
_cod_data_source_block           test_0m_a
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4033726