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_4026783
_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 H8 B Br5 F2 N2 O'
_chemical_formula_weight         692.60
_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                 90.6770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1392(8)
_cell_length_b                   9.0066(6)
_cell_length_c                   19.8041(14)
_cell_measurement_reflns_used    4627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.48
_cell_volume                     1986.7(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16735
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    10.141
_exptl_absorpt_correction_T_max  0.3523
_exptl_absorpt_correction_T_min  0.2362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Semi-empirical from equivalents'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.415
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+3.1836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2914
_reflns_number_total             4578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201754m_si_007.cif
_cod_data_source_block           BODIPY3d
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026783