Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination at Their α-Positions with Aliphatic Amines.
Wang, Dandan; Guo, Xing; Wu, Hao; Wu, Qinghua; Wang, Hua; Zhang, Xiankang; Hao, Erhong; Jiao, Lijuan; The Journal of organic chemistry 85 (2020) 8360–8370; doi:10.1021/acs.joc.0c00620

data_4038512
_publ_section_title
;
 Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination
 at Their \a-Positions with Aliphatic Amines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8360
_journal_page_last               8370
_journal_paper_doi               10.1021/acs.joc.0c00620
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C24 H25 B Br3 F2 N3'
_chemical_formula_weight         644.01
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 104.119(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.489(3)
_cell_length_b                   11.290(2)
_cell_length_c                   18.975(4)
_cell_measurement_reflns_used    8764
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.21
_cell_volume                     2594.7(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28775
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    4.696
_exptl_absorpt_correction_T_max  0.4690
_exptl_absorpt_correction_T_min  0.4248
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.392
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5925
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0703
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+9.8936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                3498
_reflns_number_total             5925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00620_si_002.cif
_cod_data_source_block           test_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038510--4038515.cif.
;
_cod_original_cell_volume        2594.8(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4038512