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_4514713
_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 H30 Br Ni P'
_chemical_formula_sum            'C28 H30 Br Ni P'
_chemical_formula_weight         536.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.75290(10)
_cell_length_b                   10.11990(10)
_cell_length_c                   14.60610(10)
_cell_measurement_reflns_used    24558
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.8480
_cell_measurement_theta_min      3.9700
_cell_volume                     2476.28(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.983
_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   -116.00 -52.00   1.00    0.10    --  -48.45-151.00 103.00   64
  2  \w    -83.00 -39.00   1.00    0.10    --  -48.45 122.00 -13.00   44
  3  \w   -114.00 -75.00   1.00    0.10    --  -48.45-122.00 -95.00   39
  4  \w   -100.00 -73.00   1.00    0.10    --  -48.45 151.00 146.00   27
  5  \w     80.00 121.00   1.00    0.10    --   48.45 151.00 146.00   41
  6  \w     34.00  94.00   1.00    0.10    --   48.45-122.00 -95.00   60
  7  \w     58.00  83.00   1.00    0.10    --   48.45-151.00 103.00   25
  8  \w   -154.00-114.00   1.00    0.30    --  -86.25-151.00 103.00   40
  9  \w   -157.00 -73.00   1.00    0.30    --  -86.25-122.00 -95.00   84
 10  \w    -90.00 -65.00   1.00    0.30    --  -86.25 151.00 146.00   25
 11  \w    -75.00 -50.00   1.00    0.30    --  -86.25 122.00 -13.00   25
 12  \w    100.00 134.00   1.00    0.30    --  107.75-151.00 103.00   34
 13  \w     55.00  97.00   1.00    0.30    --  107.75-151.00 103.00   42
 14  \w     98.00 123.00   1.00    0.30    --  107.75 151.00 146.00   25
 15  \w     36.00 112.00   1.00    0.30    --  107.75-122.00 -95.00   76
 16  \w   -120.00 -70.00   1.00    0.10    --  -48.45-125.00 -30.00   50
 17  \w   -118.00 -27.00   1.00    0.10    --  -48.45 -77.00-120.00   91
 18  \w   -159.00 -91.00   1.00    0.30    --  -86.25 -57.00 -90.00   68
 19  \w   -157.00 -76.00   1.00    0.30    --  -86.25 -37.00 150.00   81
 20  \w     33.00 116.00   1.00    0.30    --  107.75 -19.00  90.00   83
 21  \w    144.00 178.00   1.00    0.30    --  107.75  57.00 120.00   34
 22  \w     85.00 177.00   1.00    0.30    --  107.75  77.00  60.00   92
 23  \w     35.00 109.00   1.00    0.30    --  107.75 -99.00 -60.00   74
 24  \w     44.00 123.00   1.00    0.30    --  107.75 -57.00  60.00   79
 25  \w     35.00 117.00   1.00    0.30    --  107.75-125.00 120.00   82
 26  \w     38.00 101.00   1.00    0.30    --  107.75-125.00  30.00   63
 27  \w     95.00 139.00   1.00    0.30    --  107.75  57.00 120.00   44
 28  \w     36.00 119.00   1.00    0.30    --  107.75 -37.00  30.00   83
 29  \w    153.00 178.00   1.00    0.30    --  107.75 122.00 -13.00   25
;
_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      0.0650304000
_diffrn_orient_matrix_UB_12      -0.0627823000
_diffrn_orient_matrix_UB_13      0.0605616000
_diffrn_orient_matrix_UB_21      0.0393214000
_diffrn_orient_matrix_UB_22      -0.0604421000
_diffrn_orient_matrix_UB_23      -0.0857175000
_diffrn_orient_matrix_UB_31      0.0518052000
_diffrn_orient_matrix_UB_32      0.1247026000
_diffrn_orient_matrix_UB_33      -0.0109492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27330
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.991
_diffrn_reflns_theta_min         5.106
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73053
_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_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.027(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0221
_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^)+(0.0332P)^2^+1.0634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                4957
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           3-Br
_cod_database_code               4514713
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.72
_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. Uiso/Uaniso restraints and constraints
C6 \\sim C1 \\sim C2 \\sim C7 \\sim C3 \\sim C8 \\sim C4 \\sim C9 \\sim C5
\\sim C10: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C21(H21), C14(H14), C27(H27), C28(H28), C20(H20),
 C18(H18), C15(H15), C16(H16), C25(H25), C13(H13), C24(H24), C26(H26), C19(H19)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C),
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              30566
_shelx_hkl_checksum              37608
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.711