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_7129693
_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         'C12 H3 F7'
_chemical_formula_sum            'C12 H3 F7'
_chemical_formula_weight         280.14
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-28 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.019(9)
_cell_angle_beta                 79.707(9)
_cell_angle_gamma                78.279(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3590(9)
_cell_length_b                   7.5748(9)
_cell_length_c                   9.8836(10)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    294
_cell_measurement_theta_max      23.5220
_cell_measurement_theta_min      3.6280
_cell_volume                     516.46(11)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_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    -12.00  14.00   1.00    2.13    --  -10.48 -99.00-150.00   26
  2  \w    -84.00  10.00   1.00    2.13    --  -10.48 -57.00 -60.00   94
  3  \w     -4.00  84.00   1.00    2.13    --   12.36  57.00-150.00   88
  4  \w    -64.00  35.00   1.00    2.13    --   12.36 -77.00  90.00   99
;
_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      -0.0434517000
_diffrn_orient_matrix_UB_12      -0.0034847000
_diffrn_orient_matrix_UB_13      0.0705277000
_diffrn_orient_matrix_UB_21      -0.0757967000
_diffrn_orient_matrix_UB_22      0.0676517000
_diffrn_orient_matrix_UB_23      -0.0251548000
_diffrn_orient_matrix_UB_31      -0.0472468000
_diffrn_orient_matrix_UB_32      -0.0712086000
_diffrn_orient_matrix_UB_33      -0.0034862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.448
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.514
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-pentane'
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1181
_reflns_number_total             2392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00141a2.cif
_cod_data_source_block           3bn
_cod_database_code               7129693
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H3 F7'
_chemical_oxdiff_usercomment     'colourless plate'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C11(H11)
;
_shelx_res_checksum              91805
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.737