Electrosynthesis of iminophosphoranes and applications in nickel catalysis.
Mdluli, Velabo; Lehnherr, Dan; Lam, Yu-Hong; Chaudhry, Mohammad T.; Newman, Justin A.; DaSilva, Jimmy O.; Regalado, Erik L.; Chemical science 15 (2024) 5980–5992; doi:10.1039/d3sc05357a

data_1571203
_publ_section_title
;
 Electrosynthesis of iminophosphoranes and applications in nickel
 catalysis.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              5980
_journal_page_last               5992
_journal_paper_doi               10.1039/d3sc05357a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C27 H24 N2 O P2'
_chemical_formula_sum            'C27 H24 N2 O P2'
_chemical_formula_weight         454.42
_chemical_name_common            Compound35
_chemical_name_systematic        Compound35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.121(2)
_cell_angle_beta                 72.014(2)
_cell_angle_gamma                84.044(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0468(2)
_cell_length_b                   10.5532(2)
_cell_length_c                   11.2334(2)
_cell_measurement_reflns_used    22036
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3970
_cell_measurement_theta_min      4.1500
_cell_volume                     1117.26(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.938
_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   -116.00 -18.00   0.50    0.05    --  -90.00  88.00-105.00  196
  2  \w    -75.00  22.00   0.50    0.05    --  -49.83  88.00-105.00  194
  3  \w    -45.00 -20.00   0.50    0.05    --  -90.00  38.00 -30.00   50
  4  \w    -44.00 -18.00   0.50    0.05    --  -90.00  38.00  60.00   52
  5  \w    -86.00 -20.00   0.50    0.05    --  -49.83 125.00 120.00  132
  6  \w     -6.00  21.00   0.50    0.05    --   10.00  65.00 110.07   54
  7  \w     16.00  45.00   0.50    0.05    --   26.00  48.00 169.60   58
  8  \w      1.00  29.00   0.50    0.05    --   14.00  58.00  47.49   56
  9  \w     11.00  38.00   0.50    0.05    --   22.00  52.00 -36.39   54
 10  \w     11.00  39.00   0.50    0.05    --   22.00  51.00 -91.91   56
 11  \w     44.00  70.00   0.50    0.05    --  107.23 -88.00 137.00   52
 12  \w     50.00 105.00   0.50    0.05    --  107.23 -99.00 120.00  110
 13  \w     44.00  70.00   0.50    0.05    --  107.23-125.00   0.00   52
 14  \w     78.00 111.00   0.50    0.05    --  107.23-125.00   0.00   66
 15  \w     35.00 107.00   0.50    0.05    --  107.23-125.00 -30.00  144
 16  \w     36.00  84.00   0.50    0.05    --  107.23 -99.00   0.00   96
 17  \w     75.00 102.00   0.50    0.05    --  107.23 -99.00  30.00   54
 18  \w     39.00  99.00   0.50    0.05    --  107.23 -99.00  90.00  120
 19  \w    -21.00  76.00   0.50    0.05    --   49.83 -88.00 137.00  194
 20  \w     38.00  70.00   0.50    0.05    --  107.23 -99.00  30.00   64
 21  \w     35.00 105.00   0.50    0.05    --  107.23 -99.00-150.00  140
 22  \w    -22.00  31.00   0.50    0.05    --   49.83 -19.00-180.00  106
 23  \w     38.00  64.00   0.50    0.05    --  107.23 -57.00-150.00   52
 24  \w     35.00  60.00   0.50    0.05    --  107.23 -57.00 -30.00   50
 25  \w     37.00  62.00   0.50    0.05    --  107.23 -57.00-180.00   50
 26  \w     37.00  62.00   0.50    0.05    --  107.23 -57.00   0.00   50
 27  \w     36.00  64.00   0.50    0.05    --  107.23 -57.00  60.00   56
 28  \w     35.00  60.00   0.50    0.05    --  107.23 -57.00 150.00   50
 29  \w    146.00 176.00   0.50    0.05    --  107.23  38.00 -30.00   60
 30  \w    104.00 145.00   0.50    0.05    --  107.23 125.00-180.00   82
 31  \w    148.00 175.00   0.50    0.05    --  107.23 125.00-180.00   54
 32  \w    101.00 178.00   0.50    0.05    --  107.23  88.00-105.00  154
 33  \w    100.00 134.00   0.50    0.05    --  107.23  38.00 -30.00   68
 34  \w    -48.00 -20.00   0.50    0.05    --  -30.00 -47.00  -0.87   56
 35  \w   -117.00 -37.00   0.50    0.05    --  -46.00 -42.00 -87.16  160
 36  \w   -117.00 -37.00   0.50    0.05    --  -46.00 -42.00 -57.24  160
 37  \w   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00-137.64  160
 38  \w   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00 -10.09  160
 39  \w   -121.00 -42.00   0.50    0.05    --  -50.00 -40.00-110.48  158
 40  \w   -117.00 -37.00   0.50    0.05    --  -46.00 -41.00 -34.82  160
 41  \w   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00  67.40  160
 42  \w   -121.00 -41.00   0.50    0.05    --  -50.00 -42.00 111.11  160
 43  \w    -57.00 -29.00   0.50    0.05    --  -38.00 -44.00 179.83   56
 44  \w   -121.00 -42.00   0.50    0.05    --  -50.00 -40.00 132.65  158
 45  \w   -161.00 -94.00   0.50    0.05    --  -90.00 -44.00 179.20  134
 46  \w   -145.00 -64.00   0.50    0.05    --  -74.00 -42.00 132.32  162
 47  \w   -142.00 -60.00   0.50    0.05    --  -70.00 -42.00  53.28  164
 48  \w   -150.00 -69.00   0.50    0.05    --  -78.00 -41.00 170.86  162
 49  \w   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00  70.30  162
 50  \w   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00  28.92  162
 51  \w   -145.00 -64.00   0.50    0.05    --  -74.00 -42.00  29.21  162
 52  \w   -149.00 -70.00   0.50    0.05    --  -78.00 -40.00 -81.45  158
 53  \w   -142.00 -60.00   0.50    0.05    --  -70.00 -42.00-141.97  164
 54  \w   -142.00 -61.00   0.50    0.05    --  -70.00 -41.00-173.91  162
 55  \w   -145.00 -66.00   0.50    0.05    --  -74.00 -40.00 -54.68  158
 56  \w    -96.00 -70.00   0.50    0.05    --  -78.00 -39.00 -67.25   52
 57  \w   -101.00 -74.00   0.50    0.05    --  -82.00 -40.00 -10.30   54
 58  \w    -96.00 -70.00   0.50    0.05    --  -78.00 -39.00   5.73   52
 59  \w   -149.00 -70.00   0.50    0.05    --  -78.00 -39.00  -3.18  158
 60  \w   -104.00 -78.00   0.50    0.05    --  -86.00 -38.00 -25.23   52
 61  \w   -149.00 -70.00   0.50    0.05    --  -78.00 -38.00  41.40  158
 62  \w   -149.00 -70.00   0.50    0.05    --  -78.00 -38.00 147.99  158
 63  \w   -141.00 -62.00   0.50    0.05    --  -70.00 -40.00 174.17  158
 64  \w   -105.00 -78.00   0.50    0.05    --  -86.00 -40.00  98.19   54
 65  \w   -107.00 -82.00   0.50    0.05    --  -90.00 -38.00  60.00   50
 66  \w   -160.00-114.00   0.50    0.05    --  -90.00 -38.00  60.00   92
 67  \w   -160.00-135.00   0.50    0.05    --  -90.00 -38.00 -30.00   50
 68  \w   -161.00-122.00   0.50    0.05    --  -90.00 -38.00 -60.00   78
 69  \w   -115.00 -88.00   0.50    0.05    --  -90.00 -38.00 -30.00   54
 70  \w   -109.00 -83.00   0.50    0.05    --  -90.00 -38.00 -60.00   52
 71  \w   -145.00 -66.00   0.50    0.05    --  -74.00 -38.00-126.31  158
 72  \w   -116.00 -82.00   0.50    0.05    --  -90.00 -38.00-150.00   68
 73  \w   -110.00 -83.00   0.50    0.05    --  -90.00 -38.00-180.00   54
 74  \w   -116.00 -86.00   0.50    0.05    --  -90.00 -38.00  90.00   60
 75  \w   -133.00 -82.00   0.50    0.05    --  -90.00 -38.00 120.00  102
 76  \w    -96.00 -70.00   0.50    0.05    --  -78.00 -38.00  99.36   52
 77  \w   -126.00 -82.00   0.50    0.05    --  -90.00 -38.00 150.00   88
 78  \w   -161.00-127.00   0.50    0.05    --  -90.00 -38.00 150.00   68
 79  \w   -154.00-120.00   0.50    0.05    --  -90.00 -38.00  90.00   68
 80  \w   -130.00 -82.00   0.50    0.05    --  -90.00 -37.00   6.66   96
 81  \w   -115.00 -74.00   0.50    0.05    --  -82.00 -37.00 -99.66   82
 82  \w   -110.00 -81.00   0.50    0.05    --  -90.00 -36.00-162.05   58
 83  \w   -153.00-126.00   0.50    0.05    --  -90.00 -36.00-162.05   54
 84  \w   -161.00 -82.00   0.50    0.05    --  -90.00 -33.00-112.20  158
 85  \w   -107.00 -82.00   0.50    0.05    --  -90.00 -31.00-141.75   50
 86  \w   -117.00 -82.00   0.50    0.05    --  -90.00 -32.00  31.36   70
 87  \w   -155.00-129.00   0.50    0.05    --  -90.00 -32.00  31.36   52
 88  \w   -157.00-116.00   0.50    0.05    --  -90.00 -99.00  90.00   82
 89  \w   -160.00-113.00   0.50    0.05    --  -90.00 -99.00  30.00   94
 90  \w   -161.00 -79.00   0.50    0.05    --  -90.00 -88.00 137.00  164
;
_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      0.0131634000
_diffrn_orient_matrix_UB_12      0.0299616000
_diffrn_orient_matrix_UB_13      0.1257051000
_diffrn_orient_matrix_UB_21      -0.1534595000
_diffrn_orient_matrix_UB_22      0.0544071000
_diffrn_orient_matrix_UB_23      0.0362878000
_diffrn_orient_matrix_UB_31      -0.0485875000
_diffrn_orient_matrix_UB_32      -0.1343527000
_diffrn_orient_matrix_UB_33      0.0634403000
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.500
_diffrn_reflns_theta_min         4.173
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_recrystallization_method
'cooling from a solution of msd001 in acetonitrile'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0365P)^2^+0.7902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4165
_reflns_number_total             4462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05357a2.cif
_cod_data_source_block           Compound_35
_cod_depositor_comments
'Adding full bibliography for 1571196--1571204.cif.'
_cod_database_code               1571203
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 N O P H'
_chemical_oxdiff_usercomment     Velabo
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.695
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C12(H12), C8(H8), C6(H6), C2(H2), C24(H24), C27(H27), C25(H25),
 C21(H21), C4(H4), C17(H17), C11(H11), C9(H9), C5(H5), C20(H20), C26(H26),
 C10(H10), C3(H3), C18(H18), C19(H19)
;
_shelx_res_checksum              98999
_olex2_date_sample_data_collection 2023-01-09
_olex2_date_sample_submission    2023-01-09
_olex2_exptl_crystal_mounting_method
'mounted using Paratone oil onto a MiTeGen loop'
_olex2_submission_original_sample_id msd001
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.753