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_7127784
_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         'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_sum            'C16 H11 B Cl2 F2 N2 O'
_chemical_formula_weight         366.98
_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             2020-09-08
_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                114.913(2)
_cell_angle_beta                 91.931(3)
_cell_angle_gamma                96.868(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5368(3)
_cell_length_b                   10.9882(6)
_cell_length_c                   12.5935(7)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.15
_cell_volume                     810.95(8)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.895
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22138
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         3.153
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.1057
_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^)+(0.0127P)^2^+2.7081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2498
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07961h2.cif
_cod_data_source_block           mo_20200714c_0m
_cod_depositor_comments
'Adding full bibliography for 7127784--7127786.cif.'
_cod_original_cell_volume        810.95(7)
_cod_database_code               7127784
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              83479
_shelx_fab_checksum              47821
_olex2_submission_special_instructions 'No special instructions were received'