Secondary-Sphere Preorganization Enables Nickel-Catalyzed Nitrile Hydroboration
Afandiyeva, Medina; Wu, Xijue; Brennessel, William W.; Kadam, Abhishek A.; Kennedy, C. Rose; Chemical Communications  (2023) –; doi:10.1039/D3CC04229D

data_7132237
_publ_section_title
;
 Secondary-Sphere Preorganization Enables Nickel-Catalyzed Nitrile
 Hydroboration
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04229D
_journal_year                    2023
_chemical_formula_moiety         'C36 H51 K N4 Ni O7, C6 D6'
_chemical_formula_sum            'C42 H51 D6 K N4 Ni O7'
_chemical_formula_weight         833.76
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-01 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.01330(10)
_cell_length_b                   10.92400(10)
_cell_length_c                   25.6552(2)
_cell_measurement_reflns_used    39343
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.7870
_cell_measurement_theta_min      3.4900
_cell_volume                     4155.63(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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   -122.00 -34.00   0.50    0.42    --  -47.28 -16.00 -86.00  176
  2  \w     -6.00  27.00   0.50    0.42    --  -47.28  16.00  83.00   66
  3  \w    -27.00  26.00   0.50    0.42    --   47.28 -16.00 -86.00  106
  4  \w     34.00 122.00   0.50    0.42    --   47.28  16.00  83.00  176
  5  \w   -166.00 -78.00   0.50    1.67    --  -91.75 -16.00 -86.00  176
  6  \w    100.00 178.00   0.50    1.67    --  113.25  16.00  83.00  156
  7  \w    -31.00  26.00   0.50    0.42    --  -47.28  38.00 120.00  114
  8  \w     -9.00  28.00   0.50    0.42    --  -47.28  19.00-120.00   74
  9  \w     -9.00  28.00   0.50    0.42    --  -47.28  19.00-150.00   74
 10  \w    -27.00  29.00   0.50    0.42    --   47.28 -19.00 150.00  112
 11  \w     34.00  93.00   0.50    0.42    --   47.28-125.00 -30.00  118
 12  \w    -63.00 -19.00   0.50    1.67    --  -91.75  61.00-180.00   88
 13  \w    -63.00 -19.00   0.50    1.67    --  -91.75  61.00  60.00   88
 14  \w     42.00 106.00   0.50    1.67    --  113.25 -94.00 150.00  128
 15  \w     41.00 178.00   0.50    1.67    --  113.25   0.00   0.00  274
 16  \w     42.00  83.00   0.50    1.67    --  113.25 -61.00-150.00   82
 17  \w     42.00 106.00   0.50    1.67    --  113.25 -94.00-150.00  128
 18  \w     41.00 178.00   0.50    1.67    --  113.25   0.00-150.00  274
 19  \w     42.00  75.00   0.50    1.67    --  113.25 -56.00-130.20   66
 20  \w     42.00  83.00   0.50    1.67    --  113.25 -61.00 120.00   82
 21  \w     42.00  83.00   0.50    1.67    --  113.25 -61.00 -90.00   82
 22  \w     41.00 178.00   0.50    1.67    --  113.25   0.00 150.00  274
 23  \w     44.00 108.00   0.50    1.67    --  113.25-106.00 104.31  128
 24  \w     44.00 111.00   0.50    1.67    --  113.25-125.00-150.00  134
 25  \w     42.00  83.00   0.50    1.67    --  113.25 -61.00   0.00   82
 26  \w    101.00 178.00   0.50    1.67    --  113.25  45.00-120.00  154
 27  \w    101.00 178.00   0.50    1.67    --  113.25  30.00-180.00  154
 28  \w     42.00 106.00   0.50    1.67    --  113.25 -94.00-180.00  128
 29  \w    101.00 178.00   0.50    1.67    --  113.25  45.00 -90.00  154
 30  \w     42.00  83.00   0.50    1.67    --  113.25 -61.00  90.00   82
 31  \w     42.00 106.00   0.50    1.67    --  113.25 -94.00  30.00  128
 32  \w     25.00 120.00   0.50    0.42    --   47.28  77.00-120.00  190
 33  \w     32.00 120.00   0.50    0.42    --   47.28  57.00  90.00  176
 34  \w     25.00 120.00   0.50    0.42    --   47.28  77.00 -30.00  190
 35  \w     25.00 120.00   0.50    0.42    --   47.28  77.00-180.00  190
 36  \w     34.00  93.00   0.50    0.42    --   47.28-125.00  30.00  118
 37  \w     25.00 120.00   0.50    0.42    --   47.28  77.00  30.00  190
 38  \w     27.00  67.00   0.50    0.42    --   47.28  72.00 -70.36   80
 39  \w     32.00 120.00   0.50    0.42    --   47.28  57.00 150.00  176
;
_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      0.0426133000
_diffrn_orient_matrix_UB_12      0.0300540000
_diffrn_orient_matrix_UB_13      0.0571522000
_diffrn_orient_matrix_UB_21      -0.0942307000
_diffrn_orient_matrix_UB_22      -0.0012951000
_diffrn_orient_matrix_UB_23      0.0166691000
_diffrn_orient_matrix_UB_31      0.0101329000
_diffrn_orient_matrix_UB_32      -0.1377592000
_diffrn_orient_matrix_UB_33      0.0123346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            72065
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         80.678
_diffrn_reflns_theta_min         3.489
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       plate
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         8958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0362P)^2^+2.5767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8134
_reflns_number_total             8958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04229d2.cif
_cod_data_source_block           kenma12
_cod_original_cell_volume        4155.62(6)
_cod_database_code               7132237
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.768
_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 Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
  C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C14(H14), C15(H15), C16(H16), C37(D37),
 C38(D38), C39(D39), C40(D40), C41(D41), C42(D42)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              35725
_shelx_hkl_checksum              36427
_olex2_submission_original_sample_id kenma12
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.864