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_1565282
_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         'C36 H68 N2 Ni P2 Si2, 0.5(C7 H16)'
_chemical_formula_sum            'C39.5 H76 N2 Ni P2 Si2'
_chemical_formula_weight         755.85
_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     direct
_cell_angle_alpha                92.469(7)
_cell_angle_beta                 95.953(7)
_cell_angle_gamma                106.944(8)
_cell_formula_units_Z            4
_cell_length_a                   11.294(2)
_cell_length_b                   18.756(3)
_cell_length_c                   22.036(4)
_cell_measurement_reflns_used    15817
_cell_measurement_temperature    98
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.1
_cell_volume                     4428.0(13)
_computing_cell_refinement
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 222
	           Slice: -67.0000 - 44.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 120
	           Slice: -80.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 60
	           Slice: -115.0000 - -85.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 56
	           Slice: -61.0000 - -33.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 35.0000
	          2theta: -35.0000
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.087069
_diffrn_orient_matrix_UB_12      0.030241
_diffrn_orient_matrix_UB_13      -0.004654
_diffrn_orient_matrix_UB_21      0.013144
_diffrn_orient_matrix_UB_22      0.018635
_diffrn_orient_matrix_UB_23      0.044121
_diffrn_orient_matrix_UB_31      0.030706
_diffrn_orient_matrix_UB_32      -0.043167
_diffrn_orient_matrix_UB_33      0.011220
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26868
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.053
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             1654
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     852
_refine_ls_number_reflns         14995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+3.3850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11274
_reflns_number_total             14995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ICA-2020-504-119457.cif
_cod_data_source_block           cd1482a
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C79 H153 N4 Ni2 P4 Si4'
_cod_original_formula_weight         1512.70
_cod_original_formula_moiety
'C36 H68 N2 Ni P2 Si2, C36 H69 N2 Ni P2 Si2, C7 H16'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        4427.8(13)
_cod_database_code               1565282
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.811
_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:
 C61(H61), C42(H42), C6(H6), C48(H48), C19(H19), C25(H25), C55(H55), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C18(H18A,H18B), C5(H5A,H5B), C54(H54A,H54B), C66(H66A,H66B),
 C11(H11A,H11B), C38(H38A,H38B), C7(H7A,H7B), C43(H43A,H43B), C13(H13A,H13B),
 C53(H53A,H53B), C62(H62A,H62B), C44(H44A,H44B), C60(H60A,H60B), C10(H10A,H10B),
  C9(H9A,H9B), C17(H17A,H17B), C49(H49A,H49B), C47(H47A,H47B), C16(H16A,H16B),
 C65(H65A,H65B), C20(H20A,H20B), C51(H51A,H51B), C8(H8A,H8B), C52(H52A,H52B),
 C63(H63A,H63B), C14(H14A,H14B), C57(H57A,H57B), C24(H24A,H24B), C64(H64A,H64B),
  C50(H50A,H50B), C45(H45A,H45B), C59(H59A,H59B), C22(H22A,H22B), C56(H56A,
 H56B), C46(H46A,H46B), C21(H21A,H21B), C75(H75A,H75B), C15(H15A,H15B),
 C78(H78A,H78B), C23(H23A,H23B), C58(H58A,H58B), C30(H30A,H30B), C27(H27A,H27B),
  C76(H76A,H76B), C74(H74A,H74B), C77(H77A,H77B), C26(H26A,H26B), C29(H29A,
 H29B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C39(H39)
2.d Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C67(H67A,H67B,H67C), C31(H31A,H31B,H31C), C68(H68A,H68B,
 H68C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C71(H71A,H71B,H71C), C70(H70A,
 H70B,H70C), C36(H36A,H36B,H36C), C72(H72A,H72B,H72C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C), C79(H79A,H79B,H79C), C73(H73A,H73B,H73C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'