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_7156829
_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            'C32 H25 B F2 N2 O2'
_chemical_formula_weight         518.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_audit_update_record
;
2017-12-18 deposited with the CCDC.    2019-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5781(10)
_cell_length_b                   24.622(2)
_cell_length_c                   10.7523(11)
_cell_measurement_reflns_used    5491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.44
_cell_volume                     2725.4(4)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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_sigmaI/netI    0.0396
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_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23176
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.3695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                3796
_reflns_number_total             6177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00927b2.cif
_cod_data_source_block           test_0m_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        2725.4(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7156829