Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.
Savoldelli, Andrea; Meng, Qianli; Paolesse, Roberto; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M Graça H; The Journal of organic chemistry 83 (2018) 6498–6507; doi:10.1021/acs.joc.8b00789

data_4035807
_publ_section_title
;
 Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of
 BODIPY Dye Derivatives.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6498
_journal_page_last               6507
_journal_paper_doi               10.1021/acs.joc.8b00789
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H15 B F12 N2'
_chemical_formula_sum            'C29 H15 B F12 N2'
_chemical_formula_weight         630.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 120.683(3)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   32.7756(17)
_cell_length_b                   33.3988(18)
_cell_length_c                   16.7223(9)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    105.0(5)
_cell_measurement_theta_max      69.94
_cell_measurement_theta_min      3.14
_cell_volume                     15742.7(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      105.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            58740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.488
_diffrn_reflns_theta_min         2.051
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            'garnet red'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             7584
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.827
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.555
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1196
_refine_ls_number_reflns         14731
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.556
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.1518
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3601
_refine_ls_wR_factor_ref         0.3944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10527
_reflns_number_total             14731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00789_si_001.cif
_cod_data_source_block           Compound7
_cod_original_cell_volume        15742.6(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035807
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.973