Diastereoselective arylation of bis-lactim ethers catalyzed by <i>N</i>-coordinating ylide-functionalized phosphine (NYPhos).
Sowa Prendes, Daniel; Löffler, Julian; Barreto, Ivan Martins; Sankaran, Nagesh; Remm, Henning; Nascimento de Oliveira, Ronaldo; Gessner, Viktoria H.; Gooßen, Lukas J; Chemical science 16 (2025) 14152–14160; doi:10.1039/d5sc02814k

data_1574993
_publ_section_title
;
 Diastereoselective arylation of bis-lactim ethers catalyzed by
 <i>N</i>-coordinating ylide-functionalized phosphine (NYPhos).
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              14152
_journal_page_last               14160
_journal_paper_doi               10.1039/d5sc02814k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C25 H51 N3 P2'
_chemical_formula_sum            'C25 H51 N3 P2'
_chemical_formula_weight         455.62
_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             2021-09-13
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-03-18 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                66.3050(10)
_cell_angle_beta                 68.1190(10)
_cell_angle_gamma                72.6290(10)
_cell_formula_units_Z            8
_cell_length_a                   17.50500(10)
_cell_length_b                   18.2908(2)
_cell_length_c                   20.1417(2)
_cell_measurement_reflns_used    45484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7490
_cell_measurement_theta_min      2.4640
_cell_volume                     5395.23(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     33.00  58.00   0.50    0.08    --   47.45  76.00 -15.00   50
  2  \w     59.00  87.00   0.50    0.08    --   47.45  76.00 -15.00   56
  3  \w    141.00 176.00   0.50    0.31    --  106.49  30.00 150.00   70
  4  \w     90.00 143.00   0.50    0.31    --  106.49  77.00  30.00  106
  5  \w    107.00 133.00   0.50    0.31    --  106.49  30.00 150.00   52
  6  \w     87.00 178.00   0.50    0.31    --  106.49  76.00 -15.00  182
  7  \w     94.00 164.00   0.50    0.31    --  106.49  45.00 -90.00  140
  8  \w    102.00 177.00   0.50    0.31    --  106.49  30.00 -60.00  150
  9  \w    111.00 140.00   0.50    0.31    --  106.49  15.00 -90.00   58
 10  \w    147.00 176.00   0.50    0.31    --  106.49  15.00-150.00   58
 11  \w     93.00 131.00   0.50    0.31    --  106.49  15.00-150.00   76
 12  \w    -66.00  24.00   0.50    0.08    --  -47.45  76.00 -15.00  180
 13  \w    -48.00 -14.00   0.50    0.31    --  -86.25  45.00 150.00   68
 14  \w    -56.00 -16.00   0.50    0.31    --  -86.25  76.00 -15.00   80
 15  \w    -51.00 -15.00   0.50    0.31    --  -86.25  61.00 -30.00   72
 16  \w    -23.00  28.00   0.50    0.08    --  -47.45  19.00 -90.00  102
 17  \w    -45.00 -19.00   0.50    0.31    --  -86.25  45.00-180.00   52
 18  \w    -96.00 -65.00   0.50    0.08    --  -47.45 -76.00-142.00   62
 19  \w   -120.00 -73.00   0.50    0.08    --  -47.45-125.00 -90.00   94
 20  \w   -140.00-113.00   0.50    0.31    --  -86.25 -94.00 -90.00   54
 21  \w    -97.00 -65.00   0.50    0.31    --  -86.25 -76.00-142.00   64
 22  \w   -119.00 -74.00   0.50    0.08    --  -47.45-125.00   0.00   90
 23  \w   -116.00 -83.00   0.50    0.08    --  -47.45-125.00  30.00   66
 24  \w   -113.00 -87.00   0.50    0.08    --  -47.45-125.00  60.00   52
 25  \w    -26.00  28.00   0.50    0.08    --   47.45 -19.00 -90.00  108
 26  \w    -20.00  67.00   0.50    0.08    --   47.45 -76.00-142.00  174
 27  \w     61.00 100.00   0.50    0.31    --  106.49 -76.00-142.00   78
 28  \w     49.00  84.00   0.50    0.31    --  106.49 -77.00 -90.00   70
 29  \w     38.00  63.00   0.50    0.31    --  106.49 -61.00   0.00   50
 30  \w     41.00  67.00   0.50    0.31    --  106.49 -61.00  60.00   52
 31  \w     39.00  64.00   0.50    0.31    --  106.49 -61.00 120.00   50
 32  \w     35.00  60.00   0.50    0.31    --  106.49 -61.00 150.00   50
 33  \w     44.00  74.00   0.50    0.31    --  106.49 -61.00  90.00   60
 34  \w     99.00 124.00   0.50    0.31    --  106.49-142.00-107.48   50
 35  \w     49.00  75.00   0.50    0.31    --  106.49-142.00-107.48   52
 36  \w     64.00 111.00   0.50    0.31    --  106.49-125.00 -30.00   94
 37  \w     81.00 110.00   0.50    0.31    --  106.49-125.00  30.00   58
 38  \w     81.00 106.00   0.50    0.31    --  106.49-100.00   1.45   50
 39  \w     40.00  65.00   0.50    0.31    --  106.49-125.00  30.00   50
 40  \w     38.00  86.00   0.50    0.31    --  106.49 -94.00 -30.00   96
 41  \w     35.00 105.00   0.50    0.31    --  106.49 -96.00  32.53  140
 42  \w     36.00  77.00   0.50    0.31    --  106.49-125.00 120.00   82
 43  \w     64.00 105.00   0.50    0.31    --  106.49 -94.00 120.00   82
 44  \w     34.00 106.00   0.50    0.31    --  106.49-101.00 114.51  144
 45  \w     45.00 105.00   0.50    0.31    --  106.49 -94.00-120.00  120
 46  \w     45.00 105.00   0.50    0.31    --  106.49 -94.00-180.00  120
;
_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      -0.0336193000
_diffrn_orient_matrix_UB_12      -0.0753261000
_diffrn_orient_matrix_UB_13      0.0139494000
_diffrn_orient_matrix_UB_21      -0.0300050000
_diffrn_orient_matrix_UB_22      0.0446941000
_diffrn_orient_matrix_UB_23      -0.0713863000
_diffrn_orient_matrix_UB_31      0.0851380000
_diffrn_orient_matrix_UB_32      -0.0325018000
_diffrn_orient_matrix_UB_33      -0.0481968000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            69243
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.991
_diffrn_reflns_theta_min         2.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.566
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.056
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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            colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1109
_refine_ls_number_reflns         19572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1163P)^2^+0.1151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16493
_reflns_number_total             19572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02814k6.cif
_cod_data_source_block           JL-NK-21_auto_a
_cod_depositor_comments
'Adding full bibliography for 1574991--1574993.cif.'
_cod_original_cell_volume        5395.24(10)
_cod_database_code               1574993
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.618
_shelx_estimated_absorpt_t_max   0.705
_cell_oxdiff_length_a            17.50498(14)
_cell_oxdiff_length_b            18.29083(16)
_cell_oxdiff_length_c            20.1417(2)
_cell_oxdiff_angle_alpha         66.3048(9)
_cell_oxdiff_angle_beta          68.1186(8)
_cell_oxdiff_angle_gamma         72.6289(7)
_cell_oxdiff_volume              5395.21(8)
_cell_oxdiff_measurement_reflns_used 45484
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_oxdiff_digest_frames
;
01c42697942ed68338886d87bdb55d14390386457c7
;
_diffrn_oxdiff_digest_hkl
;
01af08800aa69b7e70defe315523b82f77ab80
;
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         'C25 H47 P2 N3'
_shelx_res_checksum              83874