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_4514709
_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 H29 Ni P S, C4 H8 O2'
_chemical_formula_sum            'C32 H37 Ni O2 P S'
_chemical_formula_weight         575.35
_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   geom
_audit_creation_date             2018-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.848(10)
_cell_angle_beta                 88.901(9)
_cell_angle_gamma                62.929(13)
_cell_formula_units_Z            2
_cell_length_a                   8.6245(11)
_cell_length_b                   9.0612(12)
_cell_length_c                   20.838(2)
_cell_measurement_reflns_used    3027
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      28.0810
_cell_measurement_theta_min      3.7040
_cell_volume                     1443.8(3)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.781
_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     -2.00  76.00   2.00   60.00    --    5.49  77.00   0.00   39
  2  \w     37.00  77.00   2.00   60.00    --    5.49  77.00  60.00   20
  3  \w      8.00  50.00   2.00   60.00    --    5.49  77.00 150.00   21
  4  \w    -15.00  23.00   2.00   60.00    --    5.49  77.00  60.00   19
  5  \w     24.00  72.00   2.00   60.00    --    5.49  77.00 -90.00   24
  6  \w    -12.00  70.00   2.00   60.00    --    5.49  77.00-150.00   41
;
_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      0.0789705000
_diffrn_orient_matrix_UB_12      -0.0034782000
_diffrn_orient_matrix_UB_13      0.0110548000
_diffrn_orient_matrix_UB_21      -0.0242216000
_diffrn_orient_matrix_UB_22      -0.0081056000
_diffrn_orient_matrix_UB_23      0.0323498000
_diffrn_orient_matrix_UB_31      0.0413828000
_diffrn_orient_matrix_UB_32      -0.0878337000
_diffrn_orient_matrix_UB_33      -0.0002977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.1540
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.781
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15598
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.656
_diffrn_reflns_theta_min         3.262
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82144
_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    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0790
_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^)+(0.0493P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4434
_reflns_number_total             6978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           2
_cod_database_code               4514709
_shelxl_version_number           2013-4
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C33(H33A,H33B), C36(H36A,H36B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C24(H24), C21(H21), C15(H15), C28(H28), C22(H22), C20(H20),
 C13(H13), C14(H14), C27(H27), C26(H26), C19(H19), C25(H25), C12(H12)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C),
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              66830
_shelx_hkl_checksum              52649
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.497