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_1571199
_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 P2'
_chemical_formula_sum            'C27 H24 N2 P2'
_chemical_formula_weight         438.42
_chemical_name_common            Compound_36
_chemical_name_systematic        Compound_36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.10450(10)
_cell_length_b                   26.3845(3)
_cell_length_c                   9.35170(10)
_cell_measurement_reflns_used    29506
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5160
_cell_measurement_theta_min      3.3580
_cell_volume                     2241.77(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)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.986
_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  89.00   0.50    0.17    --  107.23 -73.00  31.00  108
  2  \w    -21.00  69.00   0.50    0.05    --   50.08 -73.00  31.00  180
  3  \w    -22.00  31.00   0.50    0.05    --   50.08 -19.00   0.00  106
  4  \w     35.00  64.00   0.50    0.17    --  107.23 -57.00-180.00   58
  5  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00 -90.00  140
  6  \w     35.00 112.00   0.50    0.17    --  107.23-125.00-180.00  154
  7  \w     35.00 112.00   0.50    0.17    --  107.23-125.00-150.00  154
  8  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00 -60.00  140
  9  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00  90.00  140
 10  \w     35.00 112.00   0.50    0.17    --  107.23-125.00 120.00  154
 11  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00 150.00  140
 12  \w     34.00  96.00   0.50    0.05    --   50.08-125.00 150.00  124
 13  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00  30.00  140
 14  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00   0.00  140
 15  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00 -30.00  140
 16  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00-120.00  140
 17  \w     35.00 105.00   0.50    0.17    --  107.23 -99.00-150.00  140
 18  \w     43.00 122.00   0.50    0.05    --   50.08  38.00 -90.00  158
 19  \w    115.00 178.00   0.50    0.17    --  107.23  77.00-180.00  126
 20  \w     42.00  98.00   0.50    0.05    --   50.08  40.00 -26.91  112
 21  \w    100.00 178.00   0.50    0.17    --  107.23  38.00 120.00  156
 22  \w     88.00 178.00   0.50    0.17    --  107.23  73.00 160.00  180
 23  \w     31.00 122.00   0.50    0.05    --   50.08  73.00 160.00  182
 24  \w    -69.00  22.00   0.50    0.05    --  -50.08  73.00 160.00  182
 25  \w    -66.00 -18.00   0.50    0.17    --  -90.00  57.00 150.00   96
 26  \w    -91.00 -18.00   0.50    0.17    --  -90.00  73.00 160.00  146
 27  \w    -33.00  23.00   0.50    0.05    --  -50.08  19.00 150.00  112
 28  \w    -46.00 -18.00   0.50    0.17    --  -90.00  38.00   0.00   56
 29  \w    -66.00 -18.00   0.50    0.17    --  -90.00  57.00   0.00   96
 30  \w    -46.00 -18.00   0.50    0.17    --  -90.00  38.00 -90.00   56
 31  \w   -121.00 -42.00   0.50    0.05    --  -50.08 -38.00  60.00  158
 32  \w   -122.00 -31.00   0.50    0.05    --  -50.08 -73.00  31.00  182
 33  \w   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 -60.00   92
 34  \w   -161.00-111.00   0.50    0.17    --  -90.00 -57.00   0.00  100
 35  \w   -161.00 -71.00   0.50    0.17    --  -90.00 -73.00  31.00  180
 36  \w   -161.00-105.00   0.50    0.17    --  -90.00 -50.00 -50.31  112
 37  \w   -161.00-115.00   0.50    0.17    --  -90.00 -77.00  90.00   92
 38  \w   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 120.00   92
 39  \w   -161.00-115.00   0.50    0.17    --  -90.00 -77.00 150.00   92
;
_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      -0.1305356000
_diffrn_orient_matrix_UB_12      -0.0053009000
_diffrn_orient_matrix_UB_13      0.0958682000
_diffrn_orient_matrix_UB_21      -0.0726978000
_diffrn_orient_matrix_UB_22      0.0470993000
_diffrn_orient_matrix_UB_23      -0.0715045000
_diffrn_orient_matrix_UB_31      -0.0801207000
_diffrn_orient_matrix_UB_32      -0.0341339000
_diffrn_orient_matrix_UB_33      -0.1137346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8774
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.962
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.197
_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    1.299
_exptl_crystal_description       irregular
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Grown via. slow evaporation from a solution of mds066 in MeCN, MeOH, and H2O.'
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 3665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8774
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0512
_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^)+(0.1088P)^2^+1.7790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                8472
_reflns_number_total             8774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05357a2.cif
_cod_data_source_block           Compound_36
_cod_depositor_comments
;
Adding full bibliography for 1571196--1571204.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H48 N4 P4'
_cod_original_formula_weight         876.84
_cod_original_formula_moiety         '2(C27 H24 N2 P2)'
_cod_original_formula_units_Z            2
_cod_database_code               1571199
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'P2 N2 C30 H30'
_chemical_oxdiff_usercomment     SWMS-339-53
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.579
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.00105
 -0.00105
2.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C13(H13A,H13B), C14(H14A,H14B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C29(H29), C17(H17), C45(H45), C43(H43), C26(H26), C44(H44),
 C16(H16), C47(H47), C53(H53), C4(H4), C35(H35), C37(H37), C19(H19), C49(H49),
 C10(H10), C31(H31), C12(H12), C2(H2), C8(H8), C11(H11), C3(H3), C38(H38),
 C6(H6), C46(H46), C18(H18), C30(H30), C33(H33), C36(H36), C22(H22), C39(H39),
 C52(H52), C5(H5), C51(H51), C50(H50), C25(H25), C32(H32), C23(H23), C24(H24)
;
_shelx_res_checksum              93141
_olex2_date_sample_data_collection 2023-02-24
_olex2_date_sample_submission    2023-02-24
_olex2_exptl_crystal_mounting_method
'mounted ontoa nylon loop using paratone oil.'
_olex2_submission_original_sample_id mds066
_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.651