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_7709474
_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(C27 H22 N6 Ni), 8(F3 P0.5), C2 H3 N'
_chemical_formula_sum            'C56 H47 F24 N13 Ni2 P4'
_chemical_formula_weight         1599.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 113.261(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.2054(15)
_cell_length_b                   12.4113(6)
_cell_length_c                   17.2760(9)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.332
_cell_measurement_theta_min      2.984
_cell_volume                     6147.1(5)
_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      273
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49237
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    0.842
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       block
_exptl_crystal_F_000             3224
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.414(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     895
_refine_ls_number_reflns         14027
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0566P)^2^+17.7115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                12360
_reflns_number_total             14027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03651c2.cif
_cod_data_source_block           2020_12_18_gf_cxx_2a_0m
_cod_database_code               7709474
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.780
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.586(18)
 0.414(18)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C49(H49A,H49B), C14(H14A,H14B), C41(H41A,H41B), C22(H22A,H22B),
 C33(H33A,H33B)
3.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C44(H44), C54(H54), C12(H12), C18(H18), C29(H29), C46(H46),
 C26(H26), C24(H24), C3(H3), C9(H9), C31(H31), C4(H4), C10(H10), C1(H1),
 C36(H36), C27(H27), C30(H30), C51(H51), C25(H25), C47(H47), C20(H20), C2(H2),
 C53(H53), C11(H11), C38(H38), C19(H19), C45(H45), C52(H52), C39(H39), C37(H37),
  C17(H17)
3.c Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C)
;
_shelx_res_checksum              80374
_olex2_submission_special_instructions 'No special instructions were received'