Development of chiral modular bifunctional C2-symmetric bipyridine/phenanthroline-bipyrroloimidazolone ligands and application in noncovalent interaction-assisted enantioselective catalysis
Wang, Xi-Rui; Hu, Pan; Jing, Hui-Xian; Yu, Zhang-Biao; Yao, Zhen; Liu, Xiong-Wei; Zhang, Wen-Jing; Peng, Li-Jun; Liu, Xiong-Li; New Journal of Chemistry 49 (2025) 1138–1144; doi:10.1039/D4NJ05018E

data_7063588
_publ_section_title
;
 Development of chiral modular bifunctional C2-symmetric
 bipyridine/phenanthroline-bipyrroloimidazolone ligands and application in
 noncovalent interaction-assisted enantioselective catalysis
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1138
_journal_page_last               1144
_journal_paper_doi               10.1039/D4NJ05018E
_journal_volume                  49
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H30 Cl2 N6 O2'
_chemical_formula_sum            'C34 H30 Cl2 N6 O2'
_chemical_formula_weight         625.54
_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     dual
_audit_creation_date             2024-08-26
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-08-26 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.657(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2041(3)
_cell_length_b                   8.8612(3)
_cell_length_c                   14.7734(3)
_cell_measurement_reflns_used    12833
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.2370
_cell_measurement_theta_min      2.9410
_cell_volume                     1726.69(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00-150.00  100
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
  3  \w    -96.00  -2.00   1.00    1.00    --  -40.73 125.00 120.00   94
  4  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00   0.00  100
  5  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00  60.00  109
  6  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 -60.00   74
  7  \w     16.00 115.00   1.00    1.00    --   40.73  38.00  30.00   99
  8  \w    -39.00  82.00   1.00    1.00    --   40.73 -19.00-150.00  121
  9  \w     82.00 178.00   1.00    2.67    --  107.58  45.00  60.00   96
 10  \w     34.00 122.00   1.00    2.67    --  107.58-125.00 -30.00   88
 11  \w     75.00 178.00   1.00    2.67    --  107.58  77.00 -90.00  103
 12  \w     78.00 178.00   1.00    2.67    --  107.58  61.00 -30.00  100
 13  \w     26.00 160.00   1.00    2.67    --  107.58 -15.00 -30.00  134
 14  \w     75.00 178.00   1.00    2.67    --  107.58  77.00   0.00  103
 15  \w     75.00 178.00   1.00    2.67    --  107.58  77.00 -60.00  103
 16  \w     31.00 140.00   1.00    2.67    --  107.58 -77.00   0.00  109
 17  \w     75.00 178.00   1.00    2.67    --  107.58  77.00 -30.00  103
 18  \w     78.00 178.00   1.00    2.67    --  107.58  61.00  30.00  100
 19  \w     75.00 178.00   1.00    2.67    --  107.58  77.00  30.00  103
 20  \w     78.00 178.00   1.00    2.67    --  107.58  61.00   0.00  100
 21  \w     82.00 178.00   1.00    2.67    --  107.58  45.00  30.00   96
 22  \w     34.00 122.00   1.00    2.67    --  107.58-125.00 120.00   88
 23  \w     83.00 113.00   1.00    2.67    --  107.58  45.00 -30.00   30
 24  \w    115.00 142.00   1.00    2.67    --  107.58  45.00 -30.00   27
 25  \w     78.00 134.00   1.00    2.67    --  107.58  61.00  60.00   56
 26  \w     78.00 104.00   1.00    2.67    --  107.58  61.00 -60.00   26
 27  \w     82.00 119.00   1.00    2.67    --  107.58  45.00   0.00   37
 28  \w     94.00 175.00   1.00    2.67    --  107.58 125.00 -60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0862847000
_diffrn_orient_matrix_UB_12      0.0684186000
_diffrn_orient_matrix_UB_13      0.0535029000
_diffrn_orient_matrix_UB_21      0.0675130000
_diffrn_orient_matrix_UB_22      -0.0080554000
_diffrn_orient_matrix_UB_23      0.0878094000
_diffrn_orient_matrix_UB_31      0.0404198000
_diffrn_orient_matrix_UB_32      0.1595192000
_diffrn_orient_matrix_UB_33      -0.0184549000
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25280
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.596
_diffrn_reflns_theta_min         2.994
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6690
_refine_ls_number_restraints     451
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1252P)^2^+0.9995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.1991
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                6439
_reflns_number_total             6690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj05018e2.cif
_cod_data_source_block           exp_5570
_cod_depositor_comments          'Adding full bibliography for 7063588.cif.'
_cod_database_code               7063588
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl2-C33 \\sim Cl2A-C33A
 with sigma of 0.02
 C30-C32 \\sim C30A-C32A
 with sigma of 0.04
 C31-C33 \\sim C31A-C33A
 with sigma of 0.04
 N5-C29 \\sim N5-C29A
 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C29-C34 \\sim C29A-C34A
 with sigma of 0.02
 C29-C33 \\sim C29A-C33A
 with sigma of 0.04
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 C30-C34 \\sim C30A-C34A
 with sigma of 0.04
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C32-C34 \\sim C32A-C34A
 with sigma of 0.04
 Cl2-C32 \\sim Cl2A-C32A
 with sigma of 0.04
 Cl2-C34 \\sim Cl2A-C34A
 with sigma of 0.04
 N5-C30 \\sim N5-C30A
 with sigma of 0.04
 N5-C34 \\sim N5-C34A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl2A, O1, O2, N1, N2, N3, N4, N5, N6, C1, C2, C3, C4, C5, C6, C7,
 C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23,
 C24, C25, C26, C27, C28, C29, C29A, C30, C30A, C31, C31A, C32, C32A, C33, C33A,
  C34, C34A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.007
4. Others
 Sof(Cl2A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=
 Sof(H32A)=Sof(C33A)=Sof(C34A)=Sof(H34A)=1-FVAR(1)
 Sof(Cl2)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(C34)=Sof(H34)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C23(H23), C24(H24)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C16(H16), C19(H19),
 C20(H20), C21(H21), C30(H30), C30A(H30A), C31(H31), C31A(H31A), C32(H32),
 C32A(H32A), C34(H34), C34A(H34A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              68078
_shelx_hkl_checksum              68339
_shelx_fab_checksum              25460
_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 2.274
_oxdiff_exptl_absorpt_empirical_full_min 0.510