Selective synthesis of fluorinated biaryls by [MCl<sub>2</sub>(PhPEWO-F)] (M = Ni, Pd) catalysed Negishi cross-coupling.
Ponce-de-León, Jaime; Espinet, Pablo; Chemical communications (Cambridge, England) 57 (2021) 10875–10878; doi:10.1039/d1cc04915a

data_7129006
_publ_section_title
;
 Selective synthesis of fluorinated biaryls by [MCl<sub>2</sub>(PhPEWO-F)]
 (M = Ni, Pd) catalysed Negishi cross-coupling.
;
_journal_issue                   83
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10875
_journal_page_last               10878
_journal_paper_doi               10.1039/d1cc04915a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C54 H34 F8 Ni O2 P2, 0.5(C6 H14)'
_chemical_formula_sum            'C57 H41 F8 Ni O2 P2'
_chemical_formula_weight         1030.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.706(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2684(4)
_cell_length_b                   16.5014(5)
_cell_length_c                   21.5435(6)
_cell_measurement_reflns_used    5843
_cell_measurement_temperature    294
_cell_measurement_theta_max      28.7910
_cell_measurement_theta_min      3.7430
_cell_volume                     5066.7(3)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      294.0
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.816
_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    -57.00  30.00   1.00   38.53    --   12.36 -37.00-180.00   87
  2  \w    -20.00  52.00   1.00   38.53    --   12.36 -99.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21823
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.801
_diffrn_reflns_theta_min         3.294
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.523
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             2116
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene/n-hexane'
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         11837
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+1.6955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8118
_reflns_number_total             11837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04915a2.cif
_cod_data_source_block           ni(phpewof)2_4
_cod_depositor_comments          'Adding full bibliography for 7129006.cif.'
_cod_original_cell_volume        5066.7(2)
_cod_database_code               7129006
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 C0AA-C1AA
 1.55 with sigma of 0.02
 C1AA-C2AA
 1.55 with sigma of 0.02
 C2AA-C3AA
 1.55 with sigma of 0.02
 C3AA-C4AA
 1.55 with sigma of 0.02
 C4AA-C5AA
 1.55 with sigma of 0.02
3. Others
 Fixed Sof: C5AA(0.5) H5AA(0.5) H5AB(0.5) H5AC(0.5) C0AA(0.5) H0AA(0.5)
 H0AB(0.5) H0AC(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5) C2AA(0.5) H2AA(0.5)
 H2AB(0.5) C3AA(0.5) H3AB(0.5) H3AA(0.5) C4AA(0.5) H4AA(0.5) H4AB(0.5)
4.a Ternary CH refined with riding coordinates:
 C34(H34), C8(H8), C35(H35), C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C2AA(H2AA,H2AB), C3AA(H3AB,H3AA), C4AA(H4AA,H4AB)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C48(H48), C26(H26), C44(H44), C11(H11), C52(H52),
 C21(H21), C23(H23), C39(H39), C50(H50), C15(H15), C54(H54), C42(H42), C25(H25),
  C38(H38), C19(H19), C51(H51), C47(H47), C40(H40), C20(H20), C17(H17),
 C46(H46), C53(H53), C45(H45), C13(H13), C14(H14), C18(H18), C41(H41), C12(H12)
4.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              54015
_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
;