Synthesis and catalytic performance of nickel phosphinite pincer complexes in deoxygenative hydroboration of amides
Adilkhanova, Aziza; Frolova, Valeriya F.; Yessengazin, Azamat; Öztopçu, Özgür; Gudun, Kristina A.; Segizbayev, Medet; Matsokin, Nikita A.; Dmitrienko, Anton; Pilkington, Melanie; Khalimon, Andrey Y.; Dalton Transactions 52 (2023) 2872–2886; doi:10.1039/D2DT03801C

data_7712446
_publ_section_title
;
 Synthesis and catalytic performance of nickel phosphinite pincer
 complexes in deoxygenative hydroboration of amides
;
_journal_issue                   9
_journal_name_full               'Dalton Transactions'
_journal_page_first              2872
_journal_page_last               2886
_journal_paper_doi               10.1039/D2DT03801C
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C15 H28.36 B0.84 Br0.16 N Ni O P'
_chemical_formula_sum            'C15 H28.36 B0.84 Br0.16 N Ni O P'
_chemical_formula_weight         350.29
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                66.939(4)
_cell_angle_beta                 78.797(4)
_cell_angle_gamma                75.715(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3802(11)
_cell_length_b                   9.4495(11)
_cell_length_c                   10.9044(13)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      28.517
_cell_measurement_theta_min      2.254
_cell_volume                     856.63(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      150.0(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21084
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.557
_diffrn_reflns_theta_min         2.042
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1236 before and 0.0762 after correction. The Ratio of minimum to maximum transmission is 0.6438. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Diethyl ether'
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0297P)^2^+0.5134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4017
_reflns_number_total             4327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03801c2.cif
_cod_data_source_block           az032b_150k_0m
_cod_database_code               7712446
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.651
_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. Restrained distances
 H1D-B1
 1.2 with sigma of 0.02
 H1F-B1
 1.2 with sigma of 0.02
 B1-H1E
 1.2 with sigma of 0.02
 B1-H1G
 1.2 with sigma of 0.02
 H1F-B1 \\sim B1-H1D
 with sigma of 0.02
 H1E-B1 \\sim B1-H1G
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(B1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(H1D)=Sof(H1E)=Sof(H1F)=Sof(H1G)=Sof(B1)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              59360
_olex2_exptl_crystal_mounting_method
'on glass microloop covered with paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'