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_7132234
_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         'C42 H50 F K N4 Ni O7'
_chemical_formula_sum            'C42 H50 F K N4 Ni O7'
_chemical_formula_weight         839.67
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-05-10
_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                 92.111(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3104(3)
_cell_length_b                   21.2220(6)
_cell_length_c                   15.5022(4)
_cell_measurement_reflns_used    7539
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.4880
_cell_measurement_theta_min      3.5430
_cell_volume                     4047.22(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.926
_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    -82.00  -4.00   0.50   12.00    --  -46.82 113.00 -75.00  156
  2  \w     26.00  85.00   0.50   12.00    --   46.82-113.00-167.00  118
  3  \w     -7.00  21.00   0.50   12.00    --  -46.82  19.00-150.00   56
  4  \w   -110.00 -72.00   0.50   12.00    --  -46.82   0.00-180.00   76
  5  \w     -6.00  29.00   0.50   12.00    --  -46.82  19.00  30.00   70
  6  \w     -5.00  29.00   0.50   12.00    --  -46.82  19.00-180.00   68
  7  \w     -9.00  27.00   0.50   12.00    --  -46.82  19.00 -30.00   72
  8  \w     -1.00  27.00   0.50   12.00    --  -46.82  19.00 -90.00   56
  9  \w     -9.00  27.00   0.50   12.00    --  -46.82  19.00 -60.00   72
 10  \w    -83.00 -23.00   0.50   48.00    --  -91.75 113.00 -75.00  120
 11  \w    -63.00 -26.00   0.50   48.00    --  -91.75  61.00-150.00   74
 12  \w   -162.00-105.00   0.50   48.00    --  -91.75 -68.00 -85.07  114
 13  \w   -158.00 -82.00   0.50   48.00    --  -91.75-113.00-167.00  152
 14  \w   -109.00 -74.00   0.50   48.00    --  -91.75-125.00 -30.00   70
 15  \w    -45.00 -20.00   0.50   48.00    --  -91.75  61.00-120.00   50
 16  \w    -60.00 -34.00   0.50   48.00    --  -91.75  61.00  60.00   52
 17  \w   -158.00-132.00   0.50   48.00    --  -91.75-125.00 -30.00   52
 18  \w     70.00 108.00   0.50   48.00    --  107.80-113.00-167.00   76
 19  \w    103.00 158.00   0.50   48.00    --  107.80 113.00 -75.00  110
 20  \w     36.00 112.00   0.50   48.00    --  107.80 -77.00-180.00  152
 21  \w     87.00 112.00   0.50   48.00    --  107.80-125.00 -30.00   50
 22  \w     44.00  79.00   0.50   48.00    --  107.80-125.00 -30.00   70
 23  \w     35.00  82.00   0.50   48.00    --  107.80 -61.00-150.00   94
 24  \w    116.00 164.00   0.50   48.00    --  107.80   0.00 120.00   96
 25  \w     97.00 178.00   0.50   48.00    --  107.80 125.00  60.00  162
 26  \w    119.00 175.00   0.50   48.00    --  107.80   0.00-150.00  112
;
_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      0.0295506000
_diffrn_orient_matrix_UB_12      -0.0368765000
_diffrn_orient_matrix_UB_13      -0.0816780000
_diffrn_orient_matrix_UB_21      0.0083450000
_diffrn_orient_matrix_UB_22      -0.0610740000
_diffrn_orient_matrix_UB_23      0.0533103000
_diffrn_orient_matrix_UB_31      -0.1213366000
_diffrn_orient_matrix_UB_32      -0.0131568000
_diffrn_orient_matrix_UB_33      -0.0199541000
_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  0.0676
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28405
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.827
_diffrn_reflns_theta_min         3.532
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red-orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.076
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         8003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0747P)^2^+1.8473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5573
_reflns_number_total             8003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04229d2.cif
_cod_data_source_block           kenma11
_cod_database_code               7132234
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.856
_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:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C14(H14), C15(H15), C16(H16), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              36907
_shelx_hkl_checksum              50141
_olex2_submission_original_sample_id kenma11
_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 3.096
_oxdiff_exptl_absorpt_empirical_full_min 0.503