Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
Lijuan Jiao; Weidong Pang; Jinyuan Zhou; Yun Wei; Xiaolong Mu; Guifeng Bai; Erhong Hao; Journal of Organic Chemistry 76 (2011) 9988–9996; doi:10.1021/jo201754m

data_4026781
_publ_section_title
;
 Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9988
_journal_page_last               9996
_journal_paper_doi               10.1021/jo201754m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H11 B Br2 F2 N2 O'
_chemical_formula_weight         455.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.743(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.346(4)
_cell_length_b                   10.948(6)
_cell_length_c                   20.674(12)
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.71
_cell_volume                     1662.5(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1463
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13649
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    4.901
_exptl_absorpt_correction_T_max  0.5470
_exptl_absorpt_correction_T_min  0.4259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Semi-empirical from equivalents'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.104
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         13649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0801
_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^)+(0.1032P)^2^+2.7578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2510
_reflns_number_gt                6540
_reflns_number_total             13649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201754m_si_005.cif
_cod_data_source_block           BODIPY3b
_cod_original_cell_volume        1662.6(16)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026781