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_4514714
_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         'C21 H31 B2 N O4'
_chemical_formula_sum            'C21 H31 B2 N O4'
_chemical_formula_weight         383.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.935(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5880(7)
_cell_length_b                   10.6978(5)
_cell_length_c                   14.1186(7)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.2560
_cell_measurement_theta_min      3.5600
_cell_volume                     2239.97(19)
_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_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.978
_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    -42.00   1.00   1.00    0.10    --  -47.95 107.00  75.00   43
  2  \w     50.00  85.00   1.00    0.10    --   47.95-107.00 -22.00   35
  3  \w    -73.00 -48.00   1.00    0.80    --  -86.25 107.00  75.00   25
  4  \w   -149.00 -95.00   1.00    0.80    --  -86.25-107.00 -22.00   54
  5  \w    102.00 160.00   1.00    0.80    --  107.75 107.00  75.00   58
  6  \w     49.00  74.00   1.00    0.80    --  107.75-107.00 -22.00   25
  7  \w   -118.00 -25.00   1.00    0.10    --  -47.95 -77.00   0.00   93
  8  \w    -43.00  25.00   1.00    0.10    --  -47.95  37.00 -30.00   68
  9  \w   -138.00 -95.00   1.00    0.80    --  -86.25 -99.00  90.00   43
 10  \w     38.00 113.00   1.00    0.80    --  107.75-125.00 -60.00   75
 11  \w     97.00 141.00   1.00    0.80    --  107.75  19.00-120.00   44
 12  \w    146.00 178.00   1.00    0.80    --  107.75  19.00-120.00   32
 13  \w     45.00 127.00   1.00    0.80    --  107.75 -77.00 -30.00   82
 14  \w     35.00 109.00   1.00    0.80    --  107.75 -99.00 150.00   74
 15  \w     38.00 116.00   1.00    0.80    --  107.75 -37.00 -60.00   78
;
_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      0.0507899000
_diffrn_orient_matrix_UB_12      0.1253218000
_diffrn_orient_matrix_UB_13      0.0105941000
_diffrn_orient_matrix_UB_21      -0.0727012000
_diffrn_orient_matrix_UB_22      0.0621884000
_diffrn_orient_matrix_UB_23      0.0373099000
_diffrn_orient_matrix_UB_31      0.0541307000
_diffrn_orient_matrix_UB_32      -0.0338349000
_diffrn_orient_matrix_UB_33      0.1079683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12138
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.098
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39013
_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            colorless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0715P)^2^+1.2139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3630
_reflns_number_total             3961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           7e
_cod_database_code               4514714
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNBO
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C)
;
_shelx_res_checksum              6710
_shelx_hkl_checksum              55089
_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 2.137
_oxdiff_exptl_absorpt_empirical_full_min 0.627