General Chemoselective Suzuki‒Miyaura Coupling of Polyhalogenated Aryl Triflates Enabled by an Alkyl-Heteroaryl-Based Phosphine Ligand
So, Chau Ming; Yuen, On Ying; Ng, Shan Shan; Chen, Zicong; ACS Catalysis 11 (2021) 7820–7827; doi:10.1021/acscatal.1c02146

data_4518856
_publ_section_title
;
 General Chemoselective Suzuki--Miyaura Coupling of Polyhalogenated Aryl
 Triflates Enabled by an Alkyl-Heteroaryl-Based Phosphine Ligand
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              7820
_journal_page_last               7827
_journal_paper_doi               10.1021/acscatal.1c02146
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C56 H72 Cl2 F6 N2 O6 P2 Pd2 S2'
_chemical_formula_sum            'C56 H72 Cl2 F6 N2 O6 P2 Pd2 S2'
_chemical_formula_weight         1392.91
_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             2020-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.150(7)
_cell_angle_beta                 89.525(8)
_cell_angle_gamma                79.395(9)
_cell_formula_units_Z            1
_cell_length_a                   10.4985(13)
_cell_length_b                   11.4124(10)
_cell_length_c                   13.4302(12)
_cell_measurement_reflns_used    2914
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6960
_cell_measurement_theta_min      2.0410
_cell_volume                     1552.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.828
_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    -38.00  42.00   1.00   10.00    --  -16.28  19.00   0.00   80
  2  \w    -21.00  22.00   1.00   10.00    --  -16.28 -99.00-150.00   43
  3  \w    -20.00  21.00   1.00   10.00    --  -16.28 -99.00 -60.00   41
  4  \w    -51.00  42.00   1.00   10.00    --   15.34 -77.00  60.00   93
  5  \w    -11.00  81.00   1.00   10.00    --   15.34  77.00-180.00   92
  6  \w     35.00  79.00   1.00   10.00    --   15.34 178.00  30.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0649845000
_diffrn_orient_matrix_UB_12      -0.0092111000
_diffrn_orient_matrix_UB_13      -0.0002951000
_diffrn_orient_matrix_UB_21      -0.0200734000
_diffrn_orient_matrix_UB_22      0.0600768000
_diffrn_orient_matrix_UB_23      -0.0274143000
_diffrn_orient_matrix_UB_31      0.0101208000
_diffrn_orient_matrix_UB_32      -0.0213051000
_diffrn_orient_matrix_UB_33      -0.0462848000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.1184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.373
_diffrn_reflns_theta_min         1.849
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         7088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0662
_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^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4476
_reflns_number_total             7088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02146_si_002.cif
_cod_data_source_block           exp_8201
_cod_database_code               4518856
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.83
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C19(H19), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C27(H27), C26(H26), C24(H24), C6(H6), C5(H5), C23(H23), C4(H4)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C), C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2020-08-26
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.798