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_4027460
_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         'C19 H15 B F2 N2 S2'
_chemical_formula_sum            'C19 H15 B F2 N2 S2'
_chemical_formula_weight         384.26
_chemical_name_systematic
; 
 5,5-difluoro-2,8-dimethyl-3,7-di(thiophen-2-yl)-5H-dipyrrolo[1,2-c:2',1'-f]
[1,3,2]diazaborinin-6-ium-5-uide 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.100(2)
_cell_length_b                   10.8960(10)
_cell_length_c                   10.7870(10)
_cell_measurement_reflns_used    3704
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.257
_cell_measurement_theta_min      0.407
_cell_volume                     1774.8(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12047
_diffrn_reflns_theta_full        23.19
_diffrn_reflns_theta_max         23.19
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.66(11)
_refine_ls_extinction_coef       0.0136(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0485P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                1944
_reflns_number_total             2391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301300b_si_002_1.cif
_cod_data_source_block           compound_3b
_cod_database_code               4027460