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_1571201
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H24 N3 O P'
_chemical_formula_sum            'C25 H24 N3 O P'
_chemical_formula_weight         413.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-27 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.39428(9)
_cell_length_b                   11.00098(13)
_cell_length_c                   20.6966(2)
_cell_measurement_reflns_used    16242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2970
_cell_measurement_theta_min      4.0080
_cell_volume                     2138.92(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(2)
_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 0.947
_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    -80.00  22.00   0.50    0.05    --  -50.08  98.00 101.00  204
  2  \w    -46.00 -18.00   0.50    0.05    --  -90.00  38.00 120.00   56
  3  \w    -46.00 -18.00   0.50    0.05    --  -90.00  38.00  90.00   56
  4  \w    -46.00 -18.00   0.50    0.05    --  -90.00  38.00 -90.00   56
  5  \w    -33.00  23.00   0.50    0.05    --  -50.08  19.00 -30.00  112
  6  \w   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00 -30.00  158
  7  \w   -161.00-115.00   0.50    0.05    --  -90.00 -77.00-120.00   92
  8  \w   -161.00-111.00   0.50    0.05    --  -90.00 -57.00-150.00  100
  9  \w   -161.00-111.00   0.50    0.05    --  -90.00 -57.00-180.00  100
 10  \w   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00-120.00  158
 11  \w   -161.00 -81.00   0.50    0.05    --  -90.00 -45.00  93.00  160
 12  \w   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00 150.00  158
 13  \w   -121.00 -65.00   0.50    0.05    --  -50.08 -38.00  30.00  112
 14  \w   -161.00 -79.00   0.50    0.05    --  -90.00 -87.00-111.00  164
 15  \w   -161.00 -98.00   0.50    0.05    --  -90.00-125.00-180.00  126
 16  \w    -11.00  71.00   0.50    0.05    --   50.08 -77.00   0.00  164
 17  \w     35.00  98.00   0.50    0.05    --  107.23 -77.00 -60.00  126
 18  \w     35.00  64.00   0.50    0.05    --  107.23 -57.00 -90.00   58
 19  \w     35.00  64.00   0.50    0.05    --  107.23 -57.00 -30.00   58
 20  \w     35.00  64.00   0.50    0.05    --  107.23 -57.00  30.00   58
 21  \w     35.00  64.00   0.50    0.05    --  107.23 -57.00  90.00   58
 22  \w    106.00 178.00   0.50    0.05    --  107.23  98.00 101.00  144
;
_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      0.0897681000
_diffrn_orient_matrix_UB_12      0.0888421000
_diffrn_orient_matrix_UB_13      -0.0406258000
_diffrn_orient_matrix_UB_21      -0.0171296000
_diffrn_orient_matrix_UB_22      0.0978559000
_diffrn_orient_matrix_UB_23      0.0526753000
_diffrn_orient_matrix_UB_31      0.1361830000
_diffrn_orient_matrix_UB_32      -0.0463094000
_diffrn_orient_matrix_UB_33      0.0333737000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20050
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.560
_diffrn_reflns_theta_min         4.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.243
_exptl_absorpt_correction_T_min  0.786
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile, acetone'
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0310P)^2^+0.5366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                4100
_reflns_number_total             4197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05357a2.cif
_cod_data_source_block           Compound_R_23
_cod_depositor_comments
'Adding full bibliography for 1571196--1571204.cif.'
_cod_original_cell_volume        2138.91(4)
_cod_database_code               1571201
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H24 N3 O P '
_chemical_oxdiff_usercomment     5057422-0090
_shelx_estimated_absorpt_t_max   0.792
_shelx_estimated_absorpt_t_min   0.677
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
1.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              94039
_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 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.786