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_4027461
_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         'C13 H15 B F2 N2'
_chemical_formula_sum            'C13 H15 B F2 N2'
_chemical_formula_weight         248.08
_chemical_name_systematic
; 
5,5-difluoro-2,3,7,8-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]
diazaborinin-6-ium-5-uide 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   difmap
_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                   14.048(5)
_cell_length_b                   6.393(6)
_cell_length_c                   14.113(3)
_cell_measurement_reflns_used    96
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.5
_cell_measurement_theta_min      8.2
_cell_volume                     1267.5(13)
_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      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3674
_diffrn_reflns_theta_full        68.17
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_min         6.27
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       'massive block'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.027(2)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0794P)^2^+0.2060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                786
_reflns_number_total             1136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301300b_si_002_2.cif
_cod_data_source_block           compound_3a
_cod_database_code               4027461