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_4514710
_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         'C34 H42 B Ni O3 P'
_chemical_formula_sum            'C34 H42 B Ni O3 P'
_chemical_formula_weight         599.16
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.271(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1829(13)
_cell_length_b                   9.2102(7)
_cell_length_c                   15.4936(10)
_cell_measurement_reflns_used    4466
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      26.3660
_cell_measurement_theta_min      3.5140
_cell_volume                     3156.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_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 0.968
_diffrn_measured_fraction_theta_max 0.996
_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    -49.00  15.00   2.00   37.32    --    5.65 -63.00  78.00   32
  2  \w    -26.00  24.00   2.00   37.32    --   -4.48 -99.00  60.00   25
  3  \w    -26.00  28.00   2.00   37.32    --   -4.48 -99.00 -90.00   27
  4  \w    -23.00  29.00   2.00   37.32    --    5.65 -99.00-150.00   26
  5  \w    -11.00  31.00   2.00   37.32    --    5.65  63.00-144.00   21
;
_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      -0.0157197000
_diffrn_orient_matrix_UB_12      -0.0472050000
_diffrn_orient_matrix_UB_13      0.0266953000
_diffrn_orient_matrix_UB_21      -0.0278768000
_diffrn_orient_matrix_UB_22      0.0305244000
_diffrn_orient_matrix_UB_23      -0.0164941000
_diffrn_orient_matrix_UB_31      -0.0020642000
_diffrn_orient_matrix_UB_32      -0.0526249000
_diffrn_orient_matrix_UB_33      -0.0335053000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21901
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.579
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0907
_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^)+(0.0734P)^2^+20.5172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2119
_refine_ls_wR_factor_ref         0.2211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4622
_reflns_number_total             5531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           H1(Bpin)
_cod_database_code               4514710
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         NiPOBC
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 C7A, C7, C2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Uiso/Uaniso restraints and constraints
C34 \\sim C33 \\sim C32 \\sim C29 \\sim C31 \\sim C30: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.08
C32 \\sim C33 \\sim C34 \\sim C29 \\sim C31 \\sim C30: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008
C2 \\sim C1 \\sim C5 \\sim C4 \\sim C3: within 1.7A with sigma of 0.004 and
sigma for terminal atoms of 0.008
C7A \\sim C7 \\sim C2: within 1.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008
4. Others
 Fixed Sof: C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C9(0.5) H9A(0.5) H9B(0.5)
 H9C(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5) C7A(0.5) H7AA(0.5) H7AB(0.5)
 H7AC(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C10A(0.5) H10D(0.5) H10E(0.5)
 H10F(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5)
 H8AC(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C27(H27), C16(H16), C18(H18), C22(H22), C24(H24), C15(H15), C26(H26),
 C14(H14), C21(H21), C19(H19), C20(H20), C12(H12), C25(H25), C13(H13)
5.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C33(H33A,H33B,
 H33C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C),
 C6A(H6AA,H6AB,H6AC), C7A(H7AA,H7AB,H7AC), C8(H8A,H8B,H8C), C10A(H10D,H10E,
 H10F), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,H8AC)
;
_shelx_res_checksum              4665
_shelx_hkl_checksum              29991
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.587