Copper-catalyzed α-benzylation of BODIPYs via radical-triggered oxidative cross-coupling of two C-H bonds.
Lv, Fan; Yu, Yang; Hao, Erhong; Yu, Changjiang; Wang, Hua; Jiao, Lijuan; Boens, Noël; Chemical communications (Cambridge, England) 54 (2018) 9059–9062; doi:10.1039/c8cc04679d

data_7122016
_publ_section_title
;
 Copper-catalyzed \a-benzylation of BODIPYs via radical-triggered
 oxidative cross-coupling of two C-H bonds.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9059
_journal_page_last               9062
_journal_paper_doi               10.1039/c8cc04679d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C20 H21 B F2 N2'
_chemical_formula_weight         338.20
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-11-30 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.8100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5066(11)
_cell_length_b                   11.9871(12)
_cell_length_c                   13.3556(13)
_cell_measurement_reflns_used    6570
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.31
_cell_volume                     1796.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15237
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+0.2749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                2997
_reflns_number_total             4163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc04679d2.cif
_cod_data_source_block           150313b_0m
_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 7122015--7122017.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7122016