Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection.
Lv, Fan; Yu, Yang; Hao, Erhong; Yu, Changjiang; Wang, Hua; Boens, Noël; Jiao, Lijuan; Organic & biomolecular chemistry 17 (2019) 5121–5128; doi:10.1039/c9ob00927b

data_7156828
_publ_section_title
;
 Highly regioselective \a-formylation and \a-acylation of BODIPY dyes via
 tandem cross-dehydrogenative coupling with in situ deprotection.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5121
_journal_page_last               5128
_journal_paper_doi               10.1039/c9ob00927b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.08
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-12-18 deposited with the CCDC.    2019-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                101.0320(10)
_cell_angle_beta                 98.3140(10)
_cell_angle_gamma                96.2770(10)
_cell_formula_units_Z            8
_cell_length_a                   10.4898(10)
_cell_length_b                   13.5801(13)
_cell_length_c                   20.312(2)
_cell_measurement_reflns_used    5564
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.31
_cell_volume                     2782.1(5)
_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 0.969
_diffrn_measured_fraction_theta_max 0.969
_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
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_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32025
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.04
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         12508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0686
_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^)+(0.0609P)^2^+0.8467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1683
_reflns_number_gt                6320
_reflns_number_total             12508
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00927b2.cif
_cod_data_source_block           test_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156827--7156830.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156828