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_4035808
_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 H20 B F6 N2 S2'
_chemical_formula_sum            'C29 H20 B F6 N2 S2'
_chemical_formula_weight         634.87
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.619(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0984(13)
_cell_length_b                   7.4733(4)
_cell_length_c                   30.328(3)
_cell_measurement_reflns_used    1330
_cell_measurement_temperature    110.0(5)
_cell_measurement_theta_max      55.42
_cell_measurement_theta_min      2.99
_cell_volume                     3118.2(5)
_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      110.0(5)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.1094
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16701
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        58.945
_diffrn_reflns_theta_max         58.945
_diffrn_reflns_theta_min         2.986
_exptl_absorpt_coefficient_mu    2.856
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_platon_squeeze_details
;
The 169 electrons per cell removed by SQUEEZE correspond 
approximately to four molecules of disordered dichloromethane
per unit cell, or one per main molecule. This solvent is
included in the formula weight, density, etc., but is not
in the formula nor model.
;
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.1141
_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^)+(0.1944P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2761
_refine_ls_wR_factor_ref         0.3126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             4453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00789_si_001.cif
_cod_data_source_block           compound4d
_cod_original_cell_volume        3118.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035808
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.481
_shelx_estimated_absorpt_t_max   0.945