Ni‒O Cooperation versus Nickel(II) Hydride in Catalytic Hydroboration of N-Heteroarenes
Liu, Jianguo; Chen, Jia-Yi; Jia, Mengjing; Ming, Bangrong; Jia, Jiong; Liao, Rong-Zhen; Tung, Chen-Ho; Wang, Wenguang; ACS Catalysis 9 (2019) 3849–; doi:10.1021/acscatal.8b05136

data_4514712
_publ_section_title
;
 Ni--O Cooperation versus Nickel(II) Hydride in Catalytic Hydroboration of
 N-Heteroarenes
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3849
_journal_paper_doi               10.1021/acscatal.8b05136
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C28 H31 Ni P'
_chemical_formula_sum            'C28 H31 Ni P'
_chemical_formula_weight         457.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                91.217(2)
_cell_angle_beta                 96.831(2)
_cell_angle_gamma                90.693(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8889(3)
_cell_length_b                   15.1597(4)
_cell_length_c                   17.8889(5)
_cell_measurement_reflns_used    12529
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.6110
_cell_measurement_theta_min      3.8570
_cell_volume                     2392.67(12)
_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 (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      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -87.00  -2.00   1.00    0.10    --  -48.45 114.00-167.00   85
  2  \w     28.00  88.00   1.00    0.10    --   48.45-114.00 101.00   60
  3  \w    -39.00 -13.00   1.00    0.17    --  -86.25 114.00-167.00   26
  4  \w   -105.00 -79.00   1.00    0.17    --  -86.25-114.00 101.00   26
  5  \w     99.00 128.00   1.00    0.17    --  107.75 114.00-167.00   29
  6  \w     43.00 110.00   1.00    0.17    --  107.75-114.00 101.00   67
  7  \w    -68.00  22.00   1.00    0.10    --  -48.45  77.00 -30.00   90
  8  \w   -120.00 -71.00   1.00    0.10    --  -48.45-125.00 -90.00   49
  9  \w    -23.00  60.00   1.00    0.10    --   48.45 -57.00-180.00   83
 10  \w   -150.00 -84.00   1.00    0.17    --  -86.25 -99.00 150.00   66
 11  \w   -157.00 -74.00   1.00    0.17    --  -86.25 -37.00 -30.00   83
 12  \w    -83.00 -14.00   1.00    0.17    --  -86.25 125.00  90.00   69
 13  \w     35.00 116.00   1.00    0.17    --  107.75-125.00-150.00   81
 14  \w     41.00  79.00   1.00    0.17    --  107.75 -77.00  30.00   38
 15  \w     95.00 176.00   1.00    0.17    --  107.75  37.00-180.00   81
 16  \w     35.00 123.00   1.00    0.17    --  107.75 -77.00-120.00   88
 17  \w    102.00 177.00   1.00    0.17    --  107.75  57.00  90.00   75
 18  \w     99.00 128.00   1.00    0.17    --  107.75 -77.00  30.00   29
 19  \w    144.00 173.00   1.00    0.17    --  107.75  37.00-120.00   29
 20  \w     95.00 139.00   1.00    0.17    --  107.75  37.00-120.00   44
 21  \w     38.00 117.00   1.00    0.17    --  107.75-125.00  60.00   79
 22  \w     35.00 115.00   1.00    0.17    --  107.75-125.00-120.00   80
 23  \w     35.00 119.00   1.00    0.17    --  107.75 -57.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0968592000
_diffrn_orient_matrix_UB_12      0.0364855000
_diffrn_orient_matrix_UB_13      0.0713487000
_diffrn_orient_matrix_UB_21      0.0666943000
_diffrn_orient_matrix_UB_22      0.0715290000
_diffrn_orient_matrix_UB_23      -0.0469217000
_diffrn_orient_matrix_UB_31      -0.1290172000
_diffrn_orient_matrix_UB_32      0.0623414000
_diffrn_orient_matrix_UB_33      0.0153112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23573
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic intense orange'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0532P)^2^+2.0090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6844
_reflns_number_total             8448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           3H
_cod_depositor_comments
;

2020-05-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H62 Ni2 P2'
_cod_original_formula_weight         914.41
_cod_original_formula_moiety         '2(C28 H31 Ni P)'
_cod_original_formula_units_Z            2
_cod_database_code               4514712
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CPNi
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C46(H46), C42(H42), C18(H18), C28(H28), C40(H40), C12(H12), C56(H56),
 C52(H52), C14(H14), C41(H41), C22(H22), C50(H50), C24(H24), C13(H13), C43(H43),
  C44(H44), C25(H25), C53(H53), C54(H54), C16(H16), C55(H55), C19(H19),
 C47(H47), C49(H49), C20(H20), C15(H15), C26(H26), C48(H48), C21(H21), C27(H27)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C6(H6A,H6B,H6C),
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C7(H7A,H7B,H7C),
  C34(H34A,H34B,H34C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              81804
_shelx_hkl_checksum              58367
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.822
_oxdiff_exptl_absorpt_empirical_full_min 0.492