Pd/Cu bimetallic catalysis to access highly fluorinated biaryls from aryl halides and fluorinated arenes
Ponce-de-León, Jaime; Marcos-Ayuso, Guillermo; Casares, Juan A.; Espinet, Pablo; Chemical Communications  (2022) –; doi:10.1039/D2CC00141A

data_7129694
_publ_section_title
;
 Pd/Cu bimetallic catalysis to access highly fluorinated biaryls from aryl
 halides and fluorinated arenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00141A
_journal_year                    2022
_chemical_formula_moiety         'C45 H49 F10 P Pd'
_chemical_formula_sum            'C45 H48.96 F10 P Pd'
_chemical_formula_weight         917.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-05 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.392(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2800(5)
_cell_length_b                   11.8689(3)
_cell_length_c                   17.7116(4)
_cell_measurement_reflns_used    5534
_cell_measurement_temperature    294
_cell_measurement_theta_max      28.4460
_cell_measurement_theta_min      3.8340
_cell_volume                     4129.42(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00  17.00   1.00   17.54    --  -10.48 -77.00-120.00   99
  2  \w     35.00 100.00   1.00   17.54    --   12.36-178.00 120.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064676000
_diffrn_orient_matrix_UB_12      0.0503142000
_diffrn_orient_matrix_UB_13      0.0221956000
_diffrn_orient_matrix_UB_21      0.0249587000
_diffrn_orient_matrix_UB_22      -0.0283987000
_diffrn_orient_matrix_UB_23      0.0289157000
_diffrn_orient_matrix_UB_31      0.0252828000
_diffrn_orient_matrix_UB_32      0.0151490000
_diffrn_orient_matrix_UB_33      -0.0195481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17887
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.630
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             1880
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/n-hexane'
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         9636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+1.8411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6266
_reflns_number_total             9636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00141a2.cif
_cod_data_source_block           7
_cod_database_code               7129694
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C45 H49 F10 P Pd'
_chemical_oxdiff_usercomment     colorless
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 1*[Sof(C44)+Sof(H44A)+Sof(H44B)+Sof(H44C)+Sof(C46)+Sof(H46A)+Sof(H46B)+
 Sof(H46C)]=1 with esd of 1
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=1-FVAR(1)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
 Sof(H43A)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(2)
 Sof(H43)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C19(H19), C13(H13), C40(H40), C37(H37), C43(H43), C43(H43A)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C18(H18A,H18B), C24(H24A,H24B), C14(H14A,H14B), C16(H16A,
 H16B), C23(H23A,H23B), C22(H22A,H22B), C17(H17A,H17B), C21(H21A,H21B),
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C33(H33), C35(H35), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C45A(H45D,H45E,H45F),
 C46(H46A,H46B,H46C)
;
_shelx_res_checksum              96970
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.069
_oxdiff_exptl_absorpt_empirical_full_min 0.927