Oxidative Coupling of 1,7,8-Unsubstituted BODIPYs: Synthesis and Electrochemical and Spectroscopic Properties
Arnaud Poirel; Antoinette De Nicola; Pascal Retailleau; Raymond Ziessel; Journal of Organic Chemistry 77 (2012) 7512–7525; doi:10.1021/jo301300b

data_4027462
_publ_contact_author_address
;Laboratoire de Chimie Mol\'eculaire,
Ecole de Chimie, Polym\`eres, Mat\'eriaux (ECPM),
Universite Louis Pasteur (ULP),
25 rue Becquerel
67087 Strasbourg Cedex 02
France
;
_publ_contact_author_email       ziessel@chimie.u-strasbg.fr
_publ_contact_author_fax         0390242635
_publ_contact_author_name        'ZIESSEL, Raymond'
_publ_contact_author_phone       0390242696
_publ_section_title
;
 Oxidative Coupling of 1,7,8-Unsubstituted BODIPYs: Synthesis and
 Electrochemical and Spectroscopic Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7512
_journal_page_last               7525
_journal_paper_doi               10.1021/jo301300b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C38 H26 B2 Br2 F4 N4 S4, 0.50 (C4 H8 O)'
_chemical_formula_sum            'C40 H30 B2 Br2 F4 N4 O0.5 S4'
_chemical_formula_weight         960.36
_chemical_name_systematic
; 
 7,7'-([2,2'-bithiophene]-5,5'-diyl)bis(3-(5-bromothiophen-2-yl)-
5,5-difluoro-2,8-dimethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]
diazaborinin-6-ium-5-uide) 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.200(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.821(3)
_cell_length_b                   13.0253(12)
_cell_length_c                   11.3123(10)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      67.9
_cell_measurement_theta_min      6.8
_cell_volume                     4174.2(7)
_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      203(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_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  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6269
_diffrn_reflns_theta_full        47.49
_diffrn_reflns_theta_max         47.49
_diffrn_reflns_theta_min         6.80
_exptl_absorpt_coefficient_mu    4.793
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       flint
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0893
_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^)+(0.1904P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2570
_refine_ls_wR_factor_ref         0.3144
_reflns_number_gt                1131
_reflns_number_total             1902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301300b_si_002_3.cif
_cod_data_source_block           compound_13
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C40 H30 B2 Br2 F4 N4 O0.50 S4'
_cod_database_code               4027462