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_4514711
_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         'C36 H44 B Ni O P'
_chemical_formula_sum            'C36 H44 B Ni O P'
_chemical_formula_weight         593.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.230(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8285(6)
_cell_length_b                   20.3843(15)
_cell_length_c                   17.3286(13)
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      29.4090
_cell_measurement_theta_min      3.7410
_cell_volume                     3105.5(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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.967
_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    -13.00  63.00   2.00   22.00    --    5.65  77.00  60.00   38
  2  \w     29.00  77.00   2.00   22.00    --    5.65  77.00-120.00   24
  3  \w      0.00  68.00   2.00   22.00    --    5.65  77.00-180.00   34
;
_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      0.0564860000
_diffrn_orient_matrix_UB_12      -0.0246411000
_diffrn_orient_matrix_UB_13      -0.0009663000
_diffrn_orient_matrix_UB_21      0.0575736000
_diffrn_orient_matrix_UB_22      0.0243526000
_diffrn_orient_matrix_UB_23      0.0042984000
_diffrn_orient_matrix_UB_31      0.0026268000
_diffrn_orient_matrix_UB_32      -0.0031240000
_diffrn_orient_matrix_UB_33      0.0408672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16304
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.308
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86925
_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_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_refine_diff_density_max         1.922
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5448
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0672
_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^)+(0.0590P)^2^+7.2561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3968
_reflns_number_total             5448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05136_si_002.cif
_cod_data_source_block           H1(BBN)
_cod_database_code               4514711
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         NiPOBC
_reflns_odcompleteness_completeness 99.25
_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. Uiso/Uaniso restraints and constraints
C1 \\sim C5 \\sim C4 \\sim C3 \\sim C2: within 1.7A with sigma of 0.004 and
sigma for terminal atoms of 0.008
3. Others
 Fixed Sof: C14A(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5) C15A(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C6(0.5) H6A(0.5) H6B(0.5)
 H6C(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5)
 C11A(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
 C12A(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13A(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
4.a Ternary CH refined with riding coordinates:
 C29(H29), C33(H33)
4.b Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C34(H34A,H34B), C35(H35A,H35B), C30(H30A,H30B), C32(H32A,
 H32B), C31(H31A,H31B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C24(H24), C22(H22), C27(H27), C16(H16), C25(H25), C18(H18),
 C26(H26), C13(H13), C21(H21), C15(H15), C14(H14), C20(H20), C19(H19)
4.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C7(H7A,H7B,H7C), C15A(H15A,H15B,H15C), C6(H6A,H6B,H6C),
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C11A(H11A,H11B,H11C), C10(H10A,H10B,H10C),
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C)
;
_shelx_res_checksum              71767
_shelx_hkl_checksum              27685
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.800