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_1571198
_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         'C30 H33 N4 P'
_chemical_formula_sum            'C30 H33 N4 P'
_chemical_formula_weight         480.57
_chemical_name_common            Compound_22
_chemical_name_systematic        Compound_22
_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             2023-02-14
_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                 98.1105(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3525(2)
_cell_length_b                   9.81549(15)
_cell_length_c                   17.3460(2)
_cell_measurement_reflns_used    15608
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3910
_cell_measurement_theta_min      3.5650
_cell_volume                     2587.76(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      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 0.924
_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     35.00 130.00   0.50    0.13    --  107.23 -82.00-155.00  190
  2  \w    -21.00  73.00   0.50    0.05    --   50.08 -82.00-155.00  188
  3  \w    -64.00 -24.00   0.50    0.13    --  -90.00  57.00 -90.00   80
  4  \w    -45.00 -20.00   0.50    0.13    --  -90.00  38.00 -90.00   50
  5  \w    -46.00 -21.00   0.50    0.13    --  -90.00  38.00-180.00   50
  6  \w    -33.00  23.00   0.50    0.05    --  -50.08  19.00 -60.00  112
  7  \w    -45.00 -19.00   0.50    0.13    --  -90.00  38.00  30.00   52
  8  \w    -46.00 -21.00   0.50    0.13    --  -90.00  38.00 120.00   50
  9  \w    -46.00  21.00   0.50    0.05    --  -50.08  38.00  60.00  134
 10  \w   -159.00-125.00   0.50    0.13    --  -90.00 -99.00 150.00   68
 11  \w   -155.00-119.00   0.50    0.13    --  -90.00 -77.00 -30.00   72
 12  \w   -161.00 -79.00   0.50    0.13    --  -90.00 -82.00-155.00  164
 13  \w   -153.00-127.00   0.50    0.13    --  -90.00 -57.00 -90.00   52
 14  \w   -159.00-110.00   0.50    0.13    --  -90.00 -99.00 -90.00   98
 15  \w   -159.00-117.00   0.50    0.13    --  -90.00 -77.00  90.00   84
 16  \w   -161.00-120.00   0.50    0.13    --  -90.00 -57.00 120.00   82
 17  \w   -113.00 -18.00   0.50    0.13    --  -90.00  82.00 -34.00  190
 18  \w    -73.00  22.00   0.50    0.05    --  -50.08  82.00 -34.00  190
 19  \w   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00-150.00  158
 20  \w    -19.00  26.00   0.50    0.05    --   50.08 -19.00-180.00   90
 21  \w     37.00  64.00   0.50    0.13    --  107.23 -57.00-120.00   54
 22  \w     36.00  63.00   0.50    0.13    --  107.23 -57.00 -90.00   54
 23  \w     35.00  60.00   0.50    0.13    --  107.23 -57.00 -30.00   50
 24  \w     35.00  60.00   0.50    0.13    --  107.23 -57.00   0.00   50
 25  \w     37.00  64.00   0.50    0.13    --  107.23 -57.00  30.00   54
 26  \w     38.00  64.00   0.50    0.13    --  107.23 -57.00 120.00   52
 27  \w    101.00 178.00   0.50    0.13    --  107.23  82.00 -34.00  154
;
_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      -0.0614338000
_diffrn_orient_matrix_UB_12      0.0117194000
_diffrn_orient_matrix_UB_13      0.0626533000
_diffrn_orient_matrix_UB_21      0.0436126000
_diffrn_orient_matrix_UB_22      0.1361701000
_diffrn_orient_matrix_UB_23      0.0275050000
_diffrn_orient_matrix_UB_31      -0.0678028000
_diffrn_orient_matrix_UB_32      0.0772075000
_diffrn_orient_matrix_UB_33      -0.0580031000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25482
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.449
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'Grown via slow evaporation of mds042 in acetonitrile/methanol/water'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0386P)^2^+1.1393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4613
_reflns_number_total             5086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05357a2.cif
_cod_data_source_block           Compound_22
_cod_depositor_comments
'Adding full bibliography for 1571196--1571204.cif.'
_cod_original_cell_volume        2587.77(6)
_cod_database_code               1571198
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'P1 C20 N3 H20'
_chemical_oxdiff_usercomment     'MWMS-339-48 other sample from velabo'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.790
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C24(H24), C23(H23), C22(H22),
 C21(H21), C20(H20), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
1.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C8(H8A,H8B,
 H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              86350
_olex2_date_sample_data_collection 2023-02-13
_olex2_date_sample_submission    2023-02-13
_olex2_exptl_crystal_mounting_method
'Mounted onto a MiTiGen loop using paratone oil.'
_olex2_submission_original_sample_id mds042
_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 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.822