Synthesis of Diazo-Bridged BODIPY Dimer and Tetramer by Oxidative Coupling of β-Amino-Substituted BODIPYs.
Yokoi, Hiroki; Hiroto, Satoru; Shinokubo, Hiroshi; Organic letters 16 (2014) 3004–3007; doi:10.1021/ol501131j

data_1516025
_publ_section_title
;
 Synthesis of Diazo-Bridged BODIPY Dimer and Tetramer by Oxidative
 Coupling of \b-Amino-Substituted BODIPYs.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3004
_journal_page_last               3007
_journal_paper_doi               10.1021/ol501131j
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C63 H54 B2 Cl3 F4 N6'
_chemical_formula_weight         1099.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.48(2)
_cell_angle_beta                 79.82(3)
_cell_angle_gamma                80.77(2)
_cell_formula_units_Z            2
_cell_length_a                   12.4210(6)
_cell_length_b                   14.0537(5)
_cell_length_c                   17.9628(6)
_cell_measurement_reflns_used    6492
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.14
_cell_volume                     2815.8(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18373
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1142
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
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_refine_diff_density_max         0.819
_refine_diff_density_min         -0.934
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         9681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0812
_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^)+(0.1451P)^2^+1.2257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2219
_refine_ls_wR_factor_ref         0.2603
_reflns_number_gt                6226
_reflns_number_total             9681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501131j_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1516025.cif.'
_cod_original_cell_volume        2815.71(19)
_cod_database_code               1516025