Synergistically activating nucleophile strategy enabled organocatalytic asymmetric P-addition of cyclic imines.
Zhang, Hongkui; Tan, Jian-Ping; Ren, Xiaoyu; Wang, Fan; Zheng, Jia-Yan; He, Jiajia; Feng, Yu; Xu, Zhipeng; Su, Zhishan; Wang, Tianli; Chemical science 15 (2024) 12017–12025; doi:10.1039/d4sc02212b

data_1571793
_publ_section_title
;
 Synergistically activating nucleophile strategy enabled organocatalytic
 asymmetric P-addition of cyclic imines.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12017
_journal_page_last               12025
_journal_paper_doi               10.1039/d4sc02212b
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'I, C25 H29 F N2 P S'
_chemical_formula_sum            'C25 H29 F I N2 P S'
_chemical_formula_weight         566.43
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-06-21 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.550(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4752(4)
_cell_length_b                   11.6241(3)
_cell_length_c                   12.9271(6)
_cell_measurement_reflns_used    4293
_cell_measurement_temperature    295.4(6)
_cell_measurement_theta_max      71.5140
_cell_measurement_theta_min      3.6980
_cell_volume                     1324.27(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.4(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -53.00  31.00   1.00    1.32    --  -36.04  57.00-150.00   84
  2  \w   -104.00  -9.00   1.00    1.32    --  -36.04 -77.00 120.00   95
  3  \w   -105.00 -50.00   1.00    1.32    --  -36.04-159.00 159.00   55
  4  \w      1.00  75.00   1.00    1.32    --   36.04 -99.00-120.00   74
  5  \w     23.00  89.00   1.00    1.32    --   36.04-125.00  90.00   66
  6  \w     37.00 109.00   1.00    7.00    --  106.21 -94.00 -30.00   72
  7  \w     36.00 128.00   1.00    7.00    --  106.21 -30.00-120.00   92
  8  \w     85.00 176.00   1.00    7.00    --  106.21  30.00-150.00   91
  9  \w     37.00 109.00   1.00    7.00    --  106.21 -94.00 -60.00   72
 10  \w     36.00 128.00   1.00    7.00    --  106.21 -30.00 -30.00   92
 11  \w     85.00 176.00   1.00    7.00    --  106.21  30.00 -60.00   91
 12  \w    100.00 176.00   1.00    7.00    --  106.21 111.00  30.00   76
 13  \w     36.00 113.00   1.00    7.00    --  106.21-111.00 120.00   77
 14  \w     39.00 133.00   1.00    7.00    --  106.21 -77.00 120.00   94
 15  \w   -104.00 -66.00   1.00    1.32    --  -36.04 -77.00-120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486373000
_diffrn_orient_matrix_UB_12      -0.0159361000
_diffrn_orient_matrix_UB_13      0.1266660000
_diffrn_orient_matrix_UB_21      -0.1637497000
_diffrn_orient_matrix_UB_22      0.0239375000
_diffrn_orient_matrix_UB_23      -0.0085552000
_diffrn_orient_matrix_UB_31      -0.0364175000
_diffrn_orient_matrix_UB_32      -0.1294282000
_diffrn_orient_matrix_UB_33      -0.0172600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6569
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        65.508
_diffrn_reflns_theta_max         65.508
_diffrn_reflns_theta_min         3.676
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.421
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.878
_refine_diff_density_min         -2.256
_refine_diff_density_rms         0.266
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0957
_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^)+(0.1668P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2230
_reflns_Friedel_coverage         0.388
_reflns_Friedel_fraction_full    0.432
_reflns_Friedel_fraction_max     0.432
_reflns_number_gt                3172
_reflns_number_total             3343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02212b2.cif
_cod_data_source_block           wtl-zhk-1
_cod_depositor_comments          'Adding full bibliography for 1571793.cif.'
_cod_original_cell_volume        1324.26(10)
_cod_database_code               1571793
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C12(H12), N13(H13), C16(H16), C18(H18), C19(H19), C20(H20), C22(H22),
 C33(H33), C39(H39), C0AA(H0AA), C11(H11), C9(H9), C1AA(H1AA), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C49(H49A,H49B,H49C), C2AA(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              65866
_shelx_hkl_checksum              77167
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-21
_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 4.343
_oxdiff_exptl_absorpt_empirical_full_min 0.312