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_7709475
_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, 2(H2 O)'
_chemical_formula_sum            'C27 H26 Br2 N6 Ni O2'
_chemical_formula_weight         685.07
_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   mixed
_audit_creation_date             2021-08-26
_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                91.319(4)
_cell_angle_beta                 95.998(4)
_cell_angle_gamma                102.033(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0554(8)
_cell_length_b                   11.9275(12)
_cell_length_c                   14.1463(13)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.365
_cell_measurement_theta_min      2.833
_cell_volume                     1320.6(2)
_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)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21263
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         2.833
_exptl_absorpt_coefficient_mu    3.798
_exptl_absorpt_correction_T_max  0.738
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0253P)^2^+10.7126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4881
_reflns_number_total             6153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03651c2.cif
_cod_data_source_block           2020_12_18_gf_cxx_1a_0m
_cod_database_code               7709475
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.618
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9902(6)
 0.0098(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2), C24(H24), C3(H3), C9(H9), C26(H26), C27(H27),
 C12(H12), C20(H20), C10(H10), C17(H17), C25(H25), C11(H11), C19(H19), C18(H18)
;
_shelx_res_checksum              7879
_olex2_submission_special_instructions 'No special instructions were received'