iso-TEtraQuinoline (i-TEQ): an inherently chiral N4 macrocyclic quinoline tetramer
Yagami, Ryota; Xu, Wei; Kobayashi, Toi; Nagata, Yuuya; Kumagai, Naoya; Chemical Science 16 (2025) 10714–10721; doi:10.1039/D5SC02937F

data_1574690
_publ_section_title
;
 iso-TEtraQuinoline (i-TEQ): an inherently chiral N4 macrocyclic quinoline
 tetramer
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              10714
_journal_page_last               10721
_journal_paper_doi               10.1039/D5SC02937F
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '2(C H2 Cl2), C50 H32 N4 O2'
_chemical_formula_sum            'C52 H36 Cl4 N4 O2'
_chemical_formula_weight         890.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.5543(2)
_cell_length_b                   14.90160(10)
_cell_length_c                   18.95070(10)
_cell_measurement_reflns_used    40434
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.1940
_cell_measurement_theta_min      2.6210
_cell_volume                     9472.82(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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     86.00 174.00   0.50    0.20    --  106.56 105.00-159.00  176
  2  \w    -27.00  16.00   0.50    0.05    --   47.76 -19.00-180.00   86
  3  \w    -27.00  16.00   0.50    0.05    --   47.76 -19.00-150.00   86
  4  \w    -27.00  16.00   0.50    0.05    --   47.76 -19.00 -60.00   86
  5  \w    -24.00  63.00   0.50    0.05    --   47.76 -57.00  90.00  174
  6  \w    -27.00  16.00   0.50    0.05    --   47.76 -19.00 120.00   86
  7  \w      0.00  84.00   0.50    0.05    --   47.76-105.00 100.00  168
  8  \w     34.00 105.00   0.50    0.20    --  106.56 -94.00 150.00  142
  9  \w     36.00 107.00   0.50    0.20    --  106.56-105.00 100.00  142
 10  \w     34.00 105.00   0.50    0.20    --  106.56 -94.00  30.00  142
 11  \w     34.00 105.00   0.50    0.20    --  106.56 -94.00-150.00  142
 12  \w     34.00 105.00   0.50    0.20    --  106.56 -94.00-180.00  142
 13  \w     34.00  72.00   0.50    0.20    --  106.56 -61.00-150.00   76
 14  \w     34.00  72.00   0.50    0.20    --  106.56 -61.00-120.00   76
 15  \w     34.00  72.00   0.50    0.20    --  106.56 -61.00  90.00   76
 16  \w     34.00  72.00   0.50    0.20    --  106.56 -61.00 120.00   76
 17  \w     84.00 174.00   0.50    0.20    --  106.56  77.00   0.00  180
 18  \w     94.00 174.00   0.50    0.20    --  106.56  45.00-180.00  160
 19  \w     33.00  89.00   0.50    0.05    --   47.76  57.00-150.00  112
 20  \w     36.00 121.00   0.50    0.05    --   47.76  38.00-180.00  170
 21  \w     33.00 119.00   0.50    0.05    --   47.76  57.00 -90.00  172
 22  \w     25.00 120.00   0.50    0.05    --   47.76  77.00 -30.00  190
 23  \w     33.00 119.00   0.50    0.05    --   47.76  57.00  90.00  172
 24  \w     90.00 174.00   0.50    0.20    --  106.56  61.00 150.00  168
 25  \w    -42.00  25.00   0.50    0.05    --  -47.76  38.00  60.00  134
 26  \w    -42.00  25.00   0.50    0.05    --  -47.76  38.00 -90.00  134
 27  \w    -75.00 -27.00   0.50    0.20    -- -100.00  61.00  30.00   96
 28  \w    -75.00 -27.00   0.50    0.20    -- -100.00  61.00  60.00   96
 29  \w   -112.00 -30.00   0.50    0.20    -- -100.00 125.00   0.00  164
 30  \w   -112.00 -30.00   0.50    0.20    -- -100.00 125.00  30.00  164
 31  \w   -112.00 -30.00   0.50    0.20    -- -100.00 125.00 150.00  164
 32  \w   -112.00 -30.00   0.50    0.20    -- -100.00 125.00 -60.00  164
 33  \w   -112.00 -30.00   0.50    0.20    -- -100.00 125.00 -90.00  164
 34  \w   -107.00 -29.00   0.50    0.20    -- -100.00 105.00-159.00  156
 35  \w    -83.00  -6.00   0.50    0.05    --  -47.76 105.00-159.00  154
 36  \w   -171.00 -92.00   0.50    0.20    -- -100.00-105.00 100.00  158
 37  \w   -173.00 -81.00   0.50    0.20    -- -100.00 -67.00  39.12  184
 38  \w   -172.00 -85.00   0.50    0.20    -- -100.00 -57.00  15.49  174
 39  \w   -173.00 -87.00   0.50    0.20    -- -100.00 -94.00   0.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0228828000
_diffrn_orient_matrix_UB_12      -0.0865926000
_diffrn_orient_matrix_UB_13      -0.0172872000
_diffrn_orient_matrix_UB_21      0.0398356000
_diffrn_orient_matrix_UB_22      0.0495116000
_diffrn_orient_matrix_UB_23      0.0127494000
_diffrn_orient_matrix_UB_31      -0.0002783000
_diffrn_orient_matrix_UB_32      -0.0271641000
_diffrn_orient_matrix_UB_33      0.0784028000
_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  0.0652
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            87708
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.748
_diffrn_reflns_theta_min         2.634
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.249
_exptl_crystal_description       prism
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.074
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         9779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0928P)^2^+19.3433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8769
_reflns_number_total             9779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02937f2.cif
_cod_data_source_block           exp_1146
_cod_depositor_comments
'Adding full bibliography for 1574686--1574690.cif.'
_cod_database_code               1574690
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     i-TEQ(Ar=p-anisyl)
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.623
_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 Secondary CH2 refined with riding coordinates:
 C01P(H01S,H01T), C01W(H01U,H01V)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00J(H00J), C00N(H00N), C00U(H00U), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017),
 C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D),
 C01E(H01E), C01F(H01F), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K),
 C01L(H01L), C01O(H01O)
2.c Idealised Me refined as rotating group:
 C01N(H01G,H01M,H01N), C01R(H01P,H01Q,H01R)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              31535
_shelx_hkl_checksum              51610
_shelx_fab_checksum              82473
_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 2.199
_oxdiff_exptl_absorpt_empirical_full_min 0.591