Catalyst-Controlled Regiodivergent C‒H Arylation Site of Fluorinated 2-Arylpyridine Derivatives: Application to Luminescent Iridium(III) Complexes
Boyaala, Rabab; Touzani, Rachid; Roisnel, Thierry; Dorcet, Vincent; Caytan, Elsa; Jacquemin, Denis; Boixel, Julien; Guerchais, Véronique; Doucet, Henri; Soulé, Jean-François; ACS Catalysis 9 (2018) 1320–; doi:10.1021/acscatal.8b04553

data_4515487
_publ_section_title
;
 Catalyst-Controlled Regiodivergent C--H Arylation Site of Fluorinated
 2-Arylpyridine Derivatives: Application to Luminescent Iridium(III)
 Complexes
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1320
_journal_paper_doi               10.1021/acscatal.8b04553
_journal_volume                  9
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C48 H30 F10 Ir N4, F6 P, C H2 Cl2'
_chemical_formula_sum            'C49 H32 Cl2 F16 Ir N4 P'
_chemical_formula_weight         1274.85
_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
_cell_angle_alpha                81.314(5)
_cell_angle_beta                 80.238(5)
_cell_angle_gamma                73.409(4)
_cell_formula_units_Z            2
_cell_length_a                   11.7565(16)
_cell_length_b                   12.8586(17)
_cell_length_c                   18.657(3)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.23
_cell_measurement_wavelength     0.71073
_cell_volume                     2648.1(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            91491
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.922
_exptl_absorpt_coefficient_mu    2.746
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.080
_refine_diff_density_max         7.492
_refine_diff_density_min         -4.062
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         12070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0852
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+75.0911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10248
_reflns_number_total             12070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs8b04553_si_001.cif
_cod_data_source_block           RB76_2
_cod_original_cell_volume        2648.1(6)
_cod_database_code               4515487
_shelx_res_checksum              41623
_shelx_hkl_checksum              62689
_shelx_fab_checksum              36983