Supramolecular Chirality Suppresses Molecular Chirality: Selective Chiral Recognition in Hierarchically Coassembled Pyridine-Benzimidazole Conjugates with Precise ee% Detection.
Zhao, Jianjian; Zhang, Peng; Qiao, Hongwei; Hao, Aiyou; Xing, Pengyao; The journal of physical chemistry letters 12 (2021) 2912–2921; doi:10.1021/acs.jpclett.1c00548

data_8000493
_publ_section_title
;
 Supramolecular Chirality Suppresses Molecular Chirality: Selective Chiral
 Recognition in Hierarchically Coassembled Pyridine-Benzimidazole
 Conjugates with Precise ee% Detection.
;
_journal_issue                   11
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              2912
_journal_page_last               2921
_journal_paper_doi               10.1021/acs.jpclett.1c00548
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C19 H13 N5, H2 O'
_chemical_formula_sum            'C19 H15 N5 O'
_chemical_formula_weight         329.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.143(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.93525(14)
_cell_length_b                   29.2968(11)
_cell_length_c                   14.6279(6)
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2930
_cell_measurement_theta_min      2.9880
_cell_volume                     1679.66(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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    102.00 162.00   1.00    1.70    --  106.49 113.00-134.00   60
  2  \w     95.00 175.00   1.00    1.70    --  106.49  19.00  30.00   80
  3  \w    125.00 178.00   1.00    1.70    --  106.49 125.00 150.00   53
  4  \w     95.00 121.00   1.00    1.70    --  106.49 125.00 150.00   26
  5  \w     35.00  65.00   1.00    1.70    --  106.49 -57.00 -60.00   30
  6  \w     42.00 105.00   1.00    1.70    --  106.49 -77.00-180.00   63
  7  \w     35.00  66.00   1.00    1.70    --  106.49-125.00 -30.00   31
  8  \w     62.00  87.00   1.00    1.70    --  106.49-113.00 134.00   25
  9  \w     38.00  70.00   1.00    1.70    --  106.49 -99.00  30.00   32
 10  \w     75.00 110.00   1.00    1.70    --  106.49-125.00 -30.00   35
 11  \w     81.00 106.00   1.00    1.70    --  106.49 -99.00  30.00   25
 12  \w     26.00  59.00   1.00    0.23    --   48.45-113.00 134.00   33
 13  \w    -27.00  26.00   1.00    0.23    --  -48.45  19.00-120.00   53
 14  \w    -41.00 -13.00   1.00    1.70    --  -86.25  38.00-120.00   28
 15  \w    -25.00  27.00   1.00    0.23    --  -48.45  19.00 -30.00   52
 16  \w    -27.00   8.00   1.00    0.23    --  -48.45  19.00 120.00   35
 17  \w    -42.00 -15.00   1.00    1.70    --  -86.25  38.00  90.00   27
 18  \w   -106.00 -81.00   1.00    1.70    --  -86.25-113.00 134.00   25
 19  \w    -80.00 -46.00   1.00    0.23    --  -48.45 113.00-134.00   34
 20  \w    -53.00 -13.00   1.00    1.70    --  -86.25 113.00-134.00   40
;
_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      -0.0754308000
_diffrn_orient_matrix_UB_12      -0.0516046000
_diffrn_orient_matrix_UB_13      -0.0018177000
_diffrn_orient_matrix_UB_21      -0.0066515000
_diffrn_orient_matrix_UB_22      0.0001768000
_diffrn_orient_matrix_UB_23      -0.1054463000
_diffrn_orient_matrix_UB_31      0.3857863000
_diffrn_orient_matrix_UB_32      -0.0100840000
_diffrn_orient_matrix_UB_33      0.0075460000
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8375
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.017
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.530
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0705
_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^)+(0.1053P)^2^+0.5889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2109
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jz1c00548_si_003.cif
_cod_data_source_block           201120b
_cod_original_cell_volume        1679.67(11)
_cod_database_code               8000493
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CN
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 98.58
_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 N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O1(0.5) H1A(0.5) H1B(0.5) O2(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 N9(H9), N17(H17), C13(H13), C11(H11), C7(H7), C6(H6), C4(H4), C22(H22),
 C5(H5), C21(H21), C10(H10), C20(H20), C19(H19)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              36886
_shelx_hkl_checksum              41081
_shelx_fab_checksum              51797
_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 1.747
_oxdiff_exptl_absorpt_empirical_full_min 0.498