Palladium-Catalyzed Homocoupling of Highly Fluorinated Arylboronates: Studies of the Influence of Strongly vs Weakly Coordinating Solvents on the Reductive Elimination Process.
Budiman, Yudha P.; Jayaraman, Arumugam; Friedrich, Alexandra; Kerner, Florian; Radius, Udo; Marder, Todd B.; Journal of the American Chemical Society 142 (2020) 6036–6050; doi:10.1021/jacs.9b11871

data_4134456
_publ_section_title
;
 Palladium-Catalyzed Homocoupling of Highly Fluorinated Arylboronates:
 Studies of the Influence of Strongly vs Weakly Coordinating Solvents on
 the Reductive Elimination Process.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6036
_journal_page_last               6050
_journal_paper_doi               10.1021/jacs.9b11871
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H12 F4 N2 Pd'
_chemical_formula_sum            'C16 H12 F4 N2 Pd'
_chemical_formula_weight         414.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.225(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1923(3)
_cell_length_b                   8.9775(2)
_cell_length_c                   9.5988(3)
_cell_measurement_reflns_used    11092
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.2210
_cell_measurement_theta_min      2.1070
_cell_volume                     792.12(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      1.00  87.00   0.50    3.07    --   13.28  37.00 -60.00  172
  2  \w      1.00  87.00   0.50    3.07    --   13.28  37.00  90.00  172
  3  \w     41.00  87.00   0.50    3.07    --   13.28 178.00  30.00   92
  4  \w     41.00  87.00   0.50    3.07    --   13.28 178.00 120.00   92
  5  \w    -61.00   5.00   0.50    3.07    --   13.28 -19.00 -30.00  132
  6  \w    -23.00  47.00   0.50    3.07    --   13.28 -99.00 -90.00  140
  7  \w     30.00  81.00   0.50    3.07    --   13.28-158.00 -36.00  102
  8  \w      8.00  58.00   0.50    3.07    --   13.28-118.00 117.00  100
  9  \w    -58.00  36.00   0.50    3.07    --   13.28 -77.00   0.00  188
 10  \w    -61.00   5.00   0.50    3.07    --   13.28 -19.00-180.00  132
 11  \w    -61.00   5.00   0.50    3.07    --   13.28 -19.00-120.00  132
 12  \w    -61.00   5.00   0.50    3.07    --   13.28 -19.00   0.00  132
 13  \w    -61.00  -8.00   0.50    3.07    --   13.28 -19.00 120.00  106
 14  \w    -85.00   1.00   0.50    3.07    --  -13.59 -57.00-150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0720446000
_diffrn_orient_matrix_UB_12      0.0214829000
_diffrn_orient_matrix_UB_13      -0.0169093000
_diffrn_orient_matrix_UB_21      -0.0254943000
_diffrn_orient_matrix_UB_22      0.0714514000
_diffrn_orient_matrix_UB_23      -0.0199565000
_diffrn_orient_matrix_UB_31      0.0105659000
_diffrn_orient_matrix_UB_32      0.0259574000
_diffrn_orient_matrix_UB_33      0.0691357000
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24242
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.122
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.211
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.739
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.065
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0246P)^2^+0.5040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0588
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4467
_reflns_number_total             4817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11871_si_007.cif
_cod_data_source_block           cmpd_3e
_cod_depositor_comments
'Adding full bibliography for 4134454--4134458.cif.'
_cod_original_cell_volume        792.13(4)
_cod_database_code               4134456
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H12F4N2Pd
_chemical_oxdiff_usercomment     YPB-424
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.843
_diffrn_oxdiff_digest_frames
;
01bf66b678152e1c7cd7d0dc69267f417a018648e92
;
_diffrn_oxdiff_digest_hkl
;
01e11e893b711a8fc2e92c66c3873f74346a7f
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              33682
_shelx_hkl_checksum              68955
_olex2_date_sample_data_collection 2019-09-11
_olex2_date_sample_submission    2019-09-09
_olex2_exptl_crystal_mounting_method
;
 The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id YPB-424
_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.910