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_4035809
_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 H21 B F6 N2 S2'
_chemical_formula_sum            'C29 H21 B F6 N2 S2'
_chemical_formula_weight         616.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                112.252(3)
_cell_angle_beta                 94.497(3)
_cell_angle_gamma                95.789(3)
_cell_formula_units_Z            4
_cell_length_a                   12.6276(5)
_cell_length_b                   14.8535(7)
_cell_length_c                   16.4118(8)
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    105.0(5)
_cell_measurement_theta_max      65.74
_cell_measurement_theta_min      2.93
_cell_volume                     2811.7(2)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1318
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            66612
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.746
_diffrn_reflns_theta_max         66.746
_diffrn_reflns_theta_min         2.933
_exptl_absorpt_coefficient_mu    2.936
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2004)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_platon_squeeze_details
;
The 60 electrons removed by SQUEEZE correspond approximately
to 1.5 molecules of disordered dichloromethane per unit cell, 
or 0.37 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         0.674
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         9903
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0739
_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^)+(0.1459P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6323
_reflns_number_total             9903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00789_si_001.cif
_cod_data_source_block           Compound4e
_cod_database_code               4035809
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.620
_shelx_estimated_absorpt_t_max   0.892