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_4033725
_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_moiety         'C28 H30 B F N2'
_chemical_formula_sum            'C28 H30 B F N2'
_chemical_formula_weight         424.35
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   17.46(4)
_cell_length_b                   17.46(4)
_cell_length_c                   48.78(10)
_cell_measurement_reflns_used    9686
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      3.18
_cell_volume                     12878(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            214430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.821
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    0.985
_exptl_crystal_description       block
_exptl_crystal_F_000             4068
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0921P)^2^+12.4345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3466
_reflns_number_total             5038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03145_si_004.cif
_cod_data_source_block           mo_20180624f_0m_a_sq
_cod_original_cell_volume        12878(65)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4033725
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F1, B1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C29(H29), C37(H37), C39(H39), C45(H45), C57(H57), C65(H65),
 C67(H67), C70(H70)
3.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C58(H58A,H58B,H58C), C68(H68A,H68B,H68C), C73(H73A,H73B,
 H73C), C76(H76A,H76B,H76C), C77(H77A,H77B,H77C), C83(H83A,H83B,H83C)
;
_shelx_res_checksum              11971
_shelx_hkl_checksum              9048
_shelx_fab_checksum              70596
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'