Stepwise synthesis and catalysis in C-S cross-coupling of pyridine-functionalized N-heterocyclic carbene nickel (II) complexes by mechanochemistry
Cui, Xiaoxiao; Hao, Xiujia; Guo, Fang; Dalton Transactions  (2022) –; doi:10.1039/D1DT03651C

data_7709476
_publ_section_title
;
 Stepwise synthesis and catalysis in C-S cross-coupling of
 pyridine-functionalized N-heterocyclic carbene nickel (II) complexes by
 mechanochemistry
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03651C
_journal_year                    2022
_chemical_formula_moiety         'C27 H22 Br N6 Ni, F6 P'
_chemical_formula_sum            'C27 H22 Br F6 N6 Ni P'
_chemical_formula_weight         714.09
_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             2021-08-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-26 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                95.299(2)
_cell_angle_beta                 91.357(2)
_cell_angle_gamma                96.987(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4515(4)
_cell_length_b                   12.4422(6)
_cell_length_c                   12.7049(7)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.288
_cell_measurement_theta_min      2.868
_cell_volume                     1319.57(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      298
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22874
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.868
_exptl_absorpt_coefficient_mu    2.384
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0432P)^2^+1.6483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4878
_reflns_number_total             6447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03651c2.cif
_cod_data_source_block           2021_04_27_gf_cxx_2a_0m
_cod_database_code               7709476
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C6(H6A,H6B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C27(H27), C9(H9), C17(H17), C24(H24), C2(H2), C4(H4), C12(H12),
 C10(H10), C20(H20), C3(H3), C26(H26), C18(H18), C11(H11), C19(H19), C25(H25)
;
_shelx_res_checksum              86968
_olex2_submission_special_instructions 'No special instructions were received'