The design and preparation of novel imidazolinone-backbone chiral N,P ligands and their highly effective performances in enantioselective allylations.
Cheng, Guo; Lu, Sen; Yu, Jing-Liang; Zhang, Qian-Mao; Wang, Li-Xin; Organic & biomolecular chemistry 23 (2025) 8474–8478; doi:10.1039/d5ob01102g

data_7160675
_publ_section_title
;
 The design and preparation of novel imidazolinone-backbone chiral N,P
 ligands and their highly effective performances in enantioselective
 allylations.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8474
_journal_page_last               8478
_journal_paper_doi               10.1039/d5ob01102g
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H33 N2 O3 P'
_chemical_formula_sum            'C32 H33 N2 O3 P'
_chemical_formula_weight         524.57
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-27 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3934(2)
_cell_length_b                   16.6786(4)
_cell_length_c                   20.8064(7)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7590
_cell_measurement_theta_min      4.2310
_cell_volume                     2912.69(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -102.00 -17.00   1.00    1.50    --  -33.50 -57.00  60.00   85
  2  \w    -28.00  -2.00   1.00    1.50    --  -33.50 -19.00 -90.00   26
  3  \w    -79.00 -42.00   1.00    1.50    --  -33.50 -19.00 -90.00   37
  4  \w     80.00 107.00   1.00    1.50    --   36.47 178.00   0.00   27
  5  \w     23.00  60.00   1.00    1.50    --   36.47  57.00  30.00   37
  6  \w     66.00  94.00   1.00    1.50    --   36.47  57.00  30.00   28
  7  \w     44.00  69.00   1.00    1.50    --   36.47 -99.00 -90.00   25
  8  \w     43.00  70.00   1.00    7.00    --  108.00-111.00 -30.00   27
  9  \w    100.00 174.00   1.00    7.00    --  108.00 111.00 -60.00   74
 10  \w    152.00 178.00   1.00    7.00    --  108.00  45.00  60.00   26
 11  \w     83.00 137.00   1.00    7.00    --  108.00  30.00 -30.00   54
 12  \w     75.00 111.00   1.00    7.00    --  108.00-111.00 -30.00   36
 13  \w     64.00 139.00   1.00    7.00    --  108.00  15.00 -90.00   75
 14  \w    132.00 176.00   1.00    7.00    --  108.00 111.00 150.00   44
 15  \w    -66.00 -32.00   1.00    2.00    --  -33.50 178.00-180.00   34
 16  \w     57.00  93.00   1.00    2.00    --   36.47 178.00 -90.00   36
 17  \w     67.00  97.00   1.00    2.00    --   36.47  57.00  60.00   30
 18  \w     84.00 110.00   1.00    2.00    --   36.47 178.00  60.00   26
 19  \w     63.00  97.00   1.00    2.00    --   36.47 178.00 120.00   34
 20  \w    107.00 134.00   1.00    7.00    --  108.00 111.00-180.00   27
 21  \w     79.00 128.00   1.00    7.00    --  108.00 -61.00 -60.00   49
 22  \w    105.00 134.00   1.00    7.00    --  108.00 178.00-180.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0042644000
_diffrn_orient_matrix_UB_12      -0.0716681000
_diffrn_orient_matrix_UB_13      0.0467115000
_diffrn_orient_matrix_UB_21      -0.0294980000
_diffrn_orient_matrix_UB_22      -0.0572514000
_diffrn_orient_matrix_UB_23      -0.0568687000
_diffrn_orient_matrix_UB_31      0.1810625000
_diffrn_orient_matrix_UB_32      -0.0110098000
_diffrn_orient_matrix_UB_33      -0.0081731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10714
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.895
_diffrn_reflns_theta_min         3.396
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(18)
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0567P)^2^+0.0720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                4612
_reflns_number_total             5310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01102g1.cif
_cod_data_source_block           202112384
_cod_depositor_comments          'Adding full bibliography for 7160675.cif.'
_cod_original_cell_volume        2912.68(15)
_cod_database_code               7160675
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.843
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C26(H26), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_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 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.873