Direct C-H alkoxylation of BODIPY dyes via cation radical accelerated oxidative nucleophilic hydrogen substitution: a new route to building blocks for functionalized BODIPYs.
Li, Heng; Lv, Fan; Guo, Xing; Wu, Qinghua; Wu, Hao; Tang, Bing; Yu, Changjiang; Wang, Hua; Jiao, Lijuan; Hao, Erhong; Chemical communications (Cambridge, England) 57 (2021) 1647–1650; doi:10.1039/d0cc07961h

data_7127785
_publ_section_title
;
 Direct C-H alkoxylation of BODIPY dyes via cation radical accelerated
 oxidative nucleophilic hydrogen substitution: a new route to building
 blocks for functionalized BODIPYs.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1647
_journal_page_last               1650
_journal_paper_doi               10.1039/d0cc07961h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H15 B Cl2 F2 N2 O'
_chemical_formula_sum            'C22 H15 B Cl2 F2 N2 O'
_chemical_formula_weight         443.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-11-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                70.1820(10)
_cell_angle_beta                 78.6320(10)
_cell_angle_gamma                82.1520(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0336(2)
_cell_length_b                   11.3399(4)
_cell_length_c                   14.7341(5)
_cell_measurement_reflns_used    8147
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.98
_cell_volume                     1080.80(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.978
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9278.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0706P)^2^+0.5989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3516
_reflns_number_total             4950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07961h2.cif
_cod_data_source_block           mo_20201015f_0m
_cod_depositor_comments
'Adding full bibliography for 7127784--7127786.cif.'
_cod_database_code               7127785
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.930
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C14, C13
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C9(H9), C10(H10), C2(H2), C6(H6), C19(H19), C21(H21), C1(H1),
 C20(H20), C18(H18), C17(H17), C16(H16), C15(H15)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              28490
_shelx_fab_checksum              94202
_olex2_submission_special_instructions 'No special instructions were received'