Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights
Madera, Justin; Slattery, Megan; Arman, Hadi D.; Tonzetich, Zachary J.; Inorganica Chimica Acta 504 (2020) 119457–; doi:10.1016/j.ica.2020.119457

data_1565281
_publ_section_title
;
 Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope
 and mechanistic insights
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119457
_journal_paper_doi               10.1016/j.ica.2020.119457
_journal_volume                  504
_journal_year                    2020
_chemical_formula_moiety         'C37 H33 N Ni O P2'
_chemical_formula_sum            'C37 H33 N Ni O P2'
_chemical_formula_weight         628.29
_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
_cell_angle_alpha                80.8730(10)
_cell_angle_beta                 82.6050(10)
_cell_angle_gamma                65.372(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1764(2)
_cell_length_b                   10.2678(2)
_cell_length_c                   17.9622(3)
_cell_measurement_reflns_used    21606
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.4100
_cell_measurement_theta_min      2.5680
_cell_volume                     1515.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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      98(2)
_diffrn_detector                 'CCD plate'
_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    -28.00  94.00   1.00   15.00    --    4.20  72.00-180.00  122
  2  \w    -97.00  25.00   1.00   15.00    --   -7.60 -72.00-150.00  122
  3  \w    -32.00  82.00   1.00   15.00    --   -7.60  38.00 -30.00  114
  4  \w    -97.00  17.00   1.00   15.00    --   -7.60 -38.00  30.00  114
  5  \w    -32.00  82.00   1.00   15.00    --   -7.60  38.00   0.00  114
  6  \w    -37.00  82.00   1.00   15.00    --   -7.60  57.00  60.00  119
  7  \w    -37.00  82.00   1.00   15.00    --   -7.60  57.00-120.00  119
  8  \w    -97.00  22.00   1.00   15.00    --   -7.60 -57.00 -60.00  119
  9  \w    -40.00  82.00   1.00   15.00    --   -7.60  72.00 -60.00  122
 10  \w    -37.00  82.00   1.00   15.00    --   -7.60  57.00 150.00  119
 11  \w    -37.00  21.00   1.00   15.00    --   -7.60  57.00   0.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0677354000
_diffrn_orient_matrix_UB_12      0.0102623000
_diffrn_orient_matrix_UB_13      -0.0190391000
_diffrn_orient_matrix_UB_21      -0.0165964000
_diffrn_orient_matrix_UB_22      -0.0503202000
_diffrn_orient_matrix_UB_23      0.0277616000
_diffrn_orient_matrix_UB_31      -0.0490107000
_diffrn_orient_matrix_UB_32      0.0567177000
_diffrn_orient_matrix_UB_33      0.0217766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53105
_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         25.496
_diffrn_reflns_theta_min         2.302
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0341P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5597
_reflns_number_total             5637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ICA-2020-504-119457.cif
_cod_data_source_block           cd1816
_cod_database_code               1565281
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.800
_reflns_odcompleteness_completeness 99.97
_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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C36(H36), C32(H32), C35(H35), C20(H20), C3(H3), C26(H26), C2(H2),
 C24(H24), C27(H27), C13(H13), C7(H7), C15(H15), C11(H11), C30(H30), C10(H10),
 C23(H23), C8(H8), C22(H22), C17(H17), C9(H9), C14(H14), C21(H21), C29(H29),
 C16(H16), C28(H28)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;