Development of BODIPY Dyes with Versatile Functional Groups at 3,5-Positions from Diacyl Peroxides via Cu(II)-Catalyzed Radical Alkylation
Tang, Bing; Lv, Fan; Chen, Kangkang; Jiao, Lijuan; Liu, Qingyun; Wang, Hua; Hao, Erhong; Chemical Communications  (2019) –; doi:10.1039/C9CC01602C

data_7123211
_publ_section_title
;
 Development of BODIPY Dyes with Versatile Functional Groups at
 3,5-Positions from Diacyl Peroxides via Cu(II)-Catalyzed Radical
 Alkylation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01602C
_journal_year                    2019
_chemical_formula_moiety         'C22 H17 B Br Cl2 F2 N3'
_chemical_formula_sum            'C22 H17 B Br Cl2 F2 N3'
_chemical_formula_weight         523.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc21x1yz
_audit_creation_date             2019-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-17 deposited with the CCDC.    2019-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0040(14)
_cell_length_b                   14.206(3)
_cell_length_c                   22.139(5)
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.01
_cell_volume                     2202.8(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.898
_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  0.0632
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            95463
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.634
_diffrn_reflns_theta_min         3.012
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7188.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0578P)^2^+3.2731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3946
_reflns_number_total             5041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01602c2.cif
_cod_data_source_block           5a
_cod_database_code               7123211
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.617
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.99(2)
 0.01(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Riding coordinates:
 N1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C6(H6), C7(H7), C11(H11), C12(H12), C19(H19),
 C20(H20), C21(H21)
;
_shelx_res_checksum              81571
_olex2_submission_special_instructions 'No special instructions were received'