Synthesis of [CNN] pincer nickel(ii) NHC chlorides and their catalytic effects on the hydrosilylation of aldehydes and ketones under mild conditions
Cao, Shaobo; Xie, Shangqing; Li, Qingshuang; Li, Xiaoyan; Sun, Hongjian; Fuhr, Olaf; Fenske, Dieter; New Journal of Chemistry 47 (2023) 12229–12238; doi:10.1039/D3NJ01375H

data_7062500
_publ_section_title
;
 Synthesis of [CNN] pincer nickel(ii) NHC chlorides and their catalytic
 effects on the hydrosilylation of aldehydes and ketones under mild
 conditions
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12229
_journal_page_last               12238
_journal_paper_doi               10.1039/D3NJ01375H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C23 H27 Br0.106 Cl0.894 N4 Ni'
_chemical_formula_sum            'C23 H27 Br0.11 Cl0.89 N4 Ni'
_chemical_formula_weight         458.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3434(2)
_cell_length_b                   14.2256(4)
_cell_length_c                   17.7157(4)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.7650
_cell_measurement_theta_min      2.7890
_cell_volume                     2102.67(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7023
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.339
_diffrn_reflns_theta_min         3.985
_exptl_absorpt_coefficient_mu    2.735
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.574
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                3202
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01375h2.cif
_cod_data_source_block           complex5a
_cod_depositor_comments
'Adding full bibliography for 7062499--7062501.cif.'
_cod_database_code               7062500
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.791
_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. Shared sites
{Cl1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Br1)
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C4(H4A,H4B), C21(H21A,H21B), C2(H2A,H2B), C3(H3A,H3B),
 C22(H22A,H22B), C23(H23A,H23B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C17(H17), C6(H6), C15(H15), C16(H16), C11(H11), C9(H9),
 C10(H10), C5(H5)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              21717
_olex2_submission_special_instructions 'No special instructions were received'