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_8000492
_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, C4 H8 O'
_chemical_formula_sum            'C23 H21 N5 O'
_chemical_formula_weight         383.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.872(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9272(3)
_cell_length_b                   22.2895(4)
_cell_length_c                   10.1168(3)
_cell_measurement_reflns_used    4885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3600
_cell_measurement_theta_min      5.1030
_cell_volume                     1960.32(12)
_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  (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    103.00 177.00   1.00    1.50    --  106.49  81.00 168.00   74
  2  \w    132.00 177.00   1.00    1.50    --  106.49  38.00  90.00   45
  3  \w     93.00 121.00   1.00    1.50    --  106.49  38.00  90.00   28
  4  \w     98.00 178.00   1.00    1.50    --  106.49  38.00 -60.00   80
  5  \w     97.00 168.00   1.00    1.50    --  106.49 125.00-150.00   71
  6  \w    -27.00  27.00   1.00    0.45    --  -48.45  19.00-120.00   54
  7  \w    -73.00  22.00   1.00    0.45    --  -48.45  81.00 168.00   95
  8  \w    -63.00 -37.00   1.00    1.50    --  -86.25  81.00 168.00   26
  9  \w    -65.00 -14.00   1.00    1.50    --  -86.25  57.00   0.00   51
 10  \w   -147.00-118.00   1.00    1.50    --  -86.25 -81.00  45.00   29
 11  \w   -120.00 -76.00   1.00    0.45    --  -48.45-125.00-180.00   44
 12  \w     34.00  63.00   1.00    1.50    --  106.49 -57.00 -60.00   29
 13  \w     37.00  65.00   1.00    1.50    --  106.49 -57.00-120.00   28
 14  \w     34.00  64.00   1.00    1.50    --  106.49 -57.00  90.00   30
 15  \w     34.00  62.00   1.00    1.50    --  106.49 -57.00 150.00   28
 16  \w     34.00  66.00   1.00    1.50    --  106.49 -57.00 120.00   32
 17  \w     54.00  83.00   1.00    1.50    --  106.49 -81.00  45.00   29
 18  \w     96.00 131.00   1.00    1.50    --  106.49 -81.00  45.00   35
 19  \w    -18.00  45.00   1.00    0.45    --   48.45 -81.00  45.00   63
;
_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      0.0062720000
_diffrn_orient_matrix_UB_12      -0.0665412000
_diffrn_orient_matrix_UB_13      0.0440120000
_diffrn_orient_matrix_UB_21      0.0044831000
_diffrn_orient_matrix_UB_22      -0.0185958000
_diffrn_orient_matrix_UB_23      -0.1445112000
_diffrn_orient_matrix_UB_31      0.1769697000
_diffrn_orient_matrix_UB_32      0.0028974000
_diffrn_orient_matrix_UB_33      0.0861280000
_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  0.0728
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24037
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         3.967
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82054
_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    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0948P)^2^+0.8534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2978
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jz1c00548_si_002.cif
_cod_data_source_block           201107c
_cod_original_cell_volume        1960.33(11)
_cod_database_code               8000492
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CN
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 90.93
_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 C(H,H,H,H) groups, All N(H) groups
2. Others
 Fixed Sof: H2AA(0.4) H2AB(0.4) H2BC(0.6) H2BD(0.6) H17A(0.4) H17B(0.4)
 H17C(0.6) H17D(0.6) O1(0.4) O2(0.6)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C9(H9A,H9B), C17(H17A,H17B), C17(H17C,H17D),
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 N17(H17), N9(H9), C22(H22), C19(H19), C21(H21), C14(H14), C12(H12), C20(H20),
 C7(H7), C13(H13), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              50511
_shelx_hkl_checksum              15926
_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 2.544
_oxdiff_exptl_absorpt_empirical_full_min 0.631