Unique regioselectivity of the Pd-catalysed cross-dehydrogenative coupling reaction of simple polyaromatic hydrocarbons with polyfluoroarenes
Sato, Ryota; Iida, Tomoki; Kanbara, Takaki; Kuwabara, Junpei; Chemical Communications  (2022) –; doi:10.1039/D2CC04655E

data_7130751
_publ_section_title
;
 Unique regioselectivity of the Pd-catalysed cross-dehydrogenative
 coupling reaction of simple polyaromatic hydrocarbons with
 polyfluoroarenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04655E
_journal_year                    2022
_chemical_formula_moiety         'C13 H4 F5'
_chemical_formula_sum            'C13 H4 F5'
_chemical_formula_weight         255.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-10-08
_audit_creation_method           'by CrystalStructure 4.3'
_audit_update_record
;
2021-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.248(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   22.572(5)
_cell_length_b                   6.5859(15)
_cell_length_c                   13.304(3)
_cell_measurement_reflns_used    1427
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      3.19
_cell_volume                     1898.7(7)
_computing_cell_refinement       Unknown
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4351
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         1.880
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6090
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            nONE
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nONE
_exptl_crystal_F_000             1016.00
_exptl_crystal_size_max          0.037
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     179
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0460P)^2^+1.2687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1348
_reflns_number_total             1671
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d2cc04655e2.cif
_cod_data_source_block           global
_cod_original_cell_volume        1898.7(8)
_cod_database_code               7130751
_shelx_res_checksum              94629