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_7709477
_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         '2(Br), C27 H22 N6 Ni, C H4 O'
_chemical_formula_sum            'C28 H26 Br2 N6 Ni O'
_chemical_formula_weight         681.08
_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                91.507(4)
_cell_angle_beta                 96.448(4)
_cell_angle_gamma                96.523(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1629(7)
_cell_length_b                   11.9336(10)
_cell_length_c                   12.1402(9)
_cell_measurement_reflns_used    8128
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.410
_cell_measurement_theta_min      2.969
_cell_volume                     1309.52(18)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21435
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.440
_diffrn_reflns_theta_min         2.969
_exptl_absorpt_coefficient_mu    3.827
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_description       needle
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0195P)^2^+2.2054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3965
_reflns_number_total             6004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03651c2.cif
_cod_data_source_block           20210514_gf_hxj_1b_0m
_cod_database_code               7709477
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.956
_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, All O(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:
 C27(H27), C4(H4), C24(H24), C1(H1), C17(H17), C18(H18), C20(H20), C26(H26),
 C12(H12), C9(H9), C2(H2), C19(H19), C25(H25), C10(H10), C3(H3), C11(H11)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              61353
_olex2_submission_special_instructions 'No special instructions were received'