Phenyliodine(III) bis(trifluoroacetate) (PIFA)-promoted synthesis of Bodipy dimers displaying unusual redox properties.
Rihn, Sandra; Erdem, Mustafa; De Nicola, Antoinette; Retailleau, Pascal; Ziessel, Raymond; Organic letters 13 (2011) 1916–1919; doi:10.1021/ol200189y

data_1502054
_publ_section_title
;
 Phenyliodine(III) bis(trifluoroacetate) (PIFA)-promoted synthesis of
 Bodipy dimers displaying unusual redox properties.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1916
_journal_page_last               1919
_journal_paper_doi               10.1021/ol200189y
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C28 H32 B2 F4 N4'
_chemical_formula_sum            'C28 H32 B2 F4 N4'
_chemical_formula_weight         522.20
_chemical_name_systematic
; 
5,5,5',5'-tetrafluoro-1,1',3,3',7,7',9,9',10,10'
-decamethyl-5H,5'H-[2,2'-bidipyrrolo[1,2-c:2',1'-f]
[1,3,2]diazaborinine]-4,6'-diium-5,5'-diuide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.161(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5280(10)
_cell_length_b                   12.7591(9)
_cell_length_c                   16.6789(13)
_cell_measurement_reflns_used    2399
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      47.1
_cell_measurement_theta_min      6.8
_cell_volume                     2606.2(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details
;
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 720.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: -0.2043
scan:
    Number of images: 25
               Slice: 58.0000 - 108.0000
         Image width: 2.0000
            Exp time: 720.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: -0.2043

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.020372
_diffrn_orient_matrix_UB_12      0.053309
_diffrn_orient_matrix_UB_13      -0.044551
_diffrn_orient_matrix_UB_21      0.076920
_diffrn_orient_matrix_UB_22      0.026286
_diffrn_orient_matrix_UB_23      0.011570
_diffrn_orient_matrix_UB_31      0.018319
_diffrn_orient_matrix_UB_32      -0.051088
_diffrn_orient_matrix_UB_33      -0.040534
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_sigmaI/netI    0.1266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5236
_diffrn_reflns_theta_full        47.20
_diffrn_reflns_theta_max         47.20
_diffrn_reflns_theta_min         6.81
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1096
_exptl_crystal_recrystallization_method 'recrystallized in dichloromethane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0885
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2291
_refine_ls_wR_factor_ref         0.2741
_reflns_number_gt                1291
_reflns_number_total             2173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200189y_si_002.cif
_cod_data_source_block           EM004bis
_cod_original_cell_volume        2606.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502054