Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY.
Roacho, Robinson I.; Metta-Magaña, Alejandro; Peña-Cabrera, Eduardo; Pannell, Keith; Organic & biomolecular chemistry 13 (2015) 995–999; doi:10.1039/c4ob01892c

data_7154217
_publ_section_title
;
 Unprecedented one-pot sequential thiolate substitutions under mild
 conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              995
_journal_page_last               999
_journal_paper_doi               10.1039/c4ob01892c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C21 H15 B F2 N2 S2'
_chemical_formula_weight         408.28
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                83.242(6)
_cell_angle_beta                 75.289(6)
_cell_angle_gamma                68.965(7)
_cell_formula_units_Z            2
_cell_length_a                   9.144(4)
_cell_length_b                   9.856(4)
_cell_length_c                   11.616(4)
_cell_measurement_temperature    296(2)
_cell_volume                     944.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w 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  0.0222
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.813
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.747
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.747
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0410
_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^)+(0.1000P)^2^+0.7034P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             3703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01892c2.cif
_cod_data_source_block           609RR_0mS
_cod_depositor_comments
'Adding full bibliography for 7154216--7154218.cif.'
_cod_original_cell_volume        944.8(6)
_cod_database_code               7154217
_shelxl_version_number           2013-2
_shelx_res_checksum              52514