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_7127786
_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 O3 S'
_chemical_formula_sum            'C22 H15 B Cl2 F2 N2 O3 S'
_chemical_formula_weight         507.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 112.884(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0000(6)
_cell_length_b                   12.6326(5)
_cell_length_c                   14.1556(5)
_cell_measurement_reflns_used    9353
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.07
_cell_volume                     2306.47(16)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            78020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.901
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9250.
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    1.460
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+2.3064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3131
_reflns_number_total             5325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07961h2.cif
_cod_data_source_block           mo_20201012a_0m
_cod_depositor_comments
'Adding full bibliography for 7127784--7127786.cif.'
_cod_database_code               7127786
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C20(H20), C9(H9), C11(H11), C10(H10), C21(H21), C22(H22),
 C6(H6), C2(H2), C1(H1)
;
_shelx_res_checksum              53791
_olex2_submission_special_instructions 'No special instructions were received'