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_1571196
_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         'C21 H20 N3 P'
_chemical_formula_sum            'C21 H20 N3 P'
_chemical_formula_weight         345.37
_chemical_name_common            Compound_13
_chemical_name_systematic        Compound_13
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-09
_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                90
_cell_angle_beta                 92.7679(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7059(3)
_cell_length_b                   10.7086(2)
_cell_length_c                   12.8648(2)
_cell_measurement_reflns_used    17240
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.5140
_cell_measurement_theta_min      4.7420
_cell_volume                     1748.37(6)
_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      99.99(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 0.948
_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 -41.00   0.50    0.57    --  -50.08 -45.00 112.00  162
  2  \w    -53.00  22.00   0.50    0.57    --  -50.08  45.00 -97.00  150
  3  \w     41.00 122.00   0.50    0.57    --   50.08  45.00 -97.00  162
  4  \w    -21.00  51.00   0.50    0.57    --   50.08 -45.00 112.00  144
  5  \w    -53.00 -18.00   0.50    2.28    --  -90.00  45.00 -97.00   70
  6  \w   -161.00 -81.00   0.50    2.28    --  -90.00 -45.00 112.00  160
  7  \w     98.00 178.00   0.50    2.28    --  107.23  45.00 -97.00  160
  8  \w   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00   0.00  158
  9  \w   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00 -30.00  158
 10  \w    -46.00  21.00   0.50    0.57    --  -50.08  38.00 120.00  134
 11  \w   -121.00 -42.00   0.50    0.57    --  -50.08 -38.00 -90.00  158
 12  \w     43.00 122.00   0.50    0.57    --   50.08  38.00 -30.00  158
 13  \w     43.00 122.00   0.50    0.57    --   50.08  38.00  90.00  158
 14  \w     34.00  96.00   0.50    0.57    --   50.08-125.00 -60.00  124
 15  \w     43.00 122.00   0.50    0.57    --   50.08  38.00  60.00  158
 16  \w   -161.00 -81.00   0.50    2.28    --  -90.00 -41.00 -29.51  160
 17  \w   -161.00 -85.00   0.50    2.28    --  -90.00 -42.00 -66.76  152
 18  \w   -161.00-111.00   0.50    2.28    --  -90.00 -57.00-150.00  100
 19  \w   -161.00 -82.00   0.50    2.28    --  -90.00 -38.00   0.00  158
 20  \w   -156.00 -82.00   0.50    2.28    --  -90.00 -38.00 -30.00  148
 21  \w   -108.00 -82.00   0.50    2.28    --  -90.00 -35.00 -29.62   52
 22  \w   -121.00 -83.00   0.50    2.28    --  -90.00 -35.00 -59.42   76
 23  \w    -66.00 -18.00   0.50    2.28    --  -90.00  57.00-150.00   96
 24  \w   -136.00 -84.00   0.50    2.28    --  -90.00 -41.00  25.40  104
 25  \w   -139.00-113.00   0.50    2.28    --  -90.00 -36.00  62.00   52
 26  \w    -44.00 -19.00   0.50    2.28    --  -90.00  38.00 -60.00   50
 27  \w    -45.00 -19.00   0.50    2.28    --  -90.00  38.00  90.00   52
 28  \w    -46.00 -21.00   0.50    2.28    --  -90.00  57.00   0.00   50
 29  \w   -120.00 -82.00   0.50    2.28    --  -90.00 -41.00 -59.72   76
 30  \w   -112.00 -85.00   0.50    2.28    --  -90.00 -37.00   4.47   54
 31  \w   -159.00 -95.00   0.50    2.28    --  -90.00 -44.00  54.74  128
 32  \w   -155.00-121.00   0.50    2.28    --  -90.00 -57.00-120.00   68
 33  \w   -156.00-130.00   0.50    2.28    --  -90.00 -33.00 -53.18   52
 34  \w   -112.00 -86.00   0.50    2.28    --  -90.00 -33.00 -53.18   52
 35  \w   -143.00-102.00   0.50    2.28    --  -90.00-125.00  30.00   82
 36  \w    -45.00 -18.00   0.50    2.28    --  -90.00  38.00 120.00   54
 37  \w   -110.00 -82.00   0.50    2.28    --  -90.00 -32.00 -22.03   56
 38  \w    -45.00 -20.00   0.50    2.28    --  -90.00  38.00   0.00   50
 39  \w   -160.00-121.00   0.50    2.28    --  -90.00 -77.00-120.00   78
 40  \w     42.00  98.00   0.50    2.28    --  107.23 -77.00 -60.00  112
 41  \w     75.00 100.00   0.50    2.28    --  107.23-125.00 -30.00   50
 42  \w     37.00  64.00   0.50    2.28    --  107.23 -57.00-150.00   54
 43  \w     36.00  62.00   0.50    2.28    --  107.23-125.00 -30.00   52
 44  \w    118.00 178.00   0.50    2.28    --  107.23  77.00 120.00  120
 45  \w     36.00  62.00   0.50    2.28    --  107.23 -57.00 150.00   52
 46  \w     35.00  64.00   0.50    2.28    --  107.23 -57.00   0.00   58
 47  \w     35.00  95.00   0.50    2.28    --  107.23 -77.00 120.00  120
 48  \w     37.00  63.00   0.50    2.28    --  107.23 -57.00-180.00   52
;
_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      0.0768370000
_diffrn_orient_matrix_UB_12      -0.0800596000
_diffrn_orient_matrix_UB_13      -0.0606496000
_diffrn_orient_matrix_UB_21      0.0736178000
_diffrn_orient_matrix_UB_22      -0.0106189000
_diffrn_orient_matrix_UB_23      0.0982708000
_diffrn_orient_matrix_UB_31      -0.0583330000
_diffrn_orient_matrix_UB_32      -0.1191123000
_diffrn_orient_matrix_UB_33      0.0321997000
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.215
_diffrn_reflns_theta_min         4.778
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method
'grown via slow evaporation from a solution of mds029 in methanol, water, and acetonitrile'
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0502P)^2^+1.0371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3197
_reflns_number_total             3506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05357a2.cif
_cod_data_source_block           Compound_13
_cod_depositor_comments
'Adding full bibliography for 1571196--1571204.cif.'
_cod_original_cell_volume        1748.38(6)
_cod_database_code               1571196
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'P1 C10 N3 H10'
_chemical_oxdiff_usercomment     SWMS-339-47
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C6(H6), C17(H17), C8(H8), C15(H15), C12(H12), C2(H2),
 C5(H5), C10(H10), C11(H11), C9(H9), C4(H4), C3(H3)
1.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              86087
_olex2_date_sample_data_collection 2023-02-08
_olex2_date_sample_submission    2023-02-08
_olex2_exptl_crystal_mounting_method
'mounted onto a MiTiGen loop using paratone oil.'
_olex2_submission_original_sample_id mds029
_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 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.552