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_1574689
_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(C32 H20 N4)'
_chemical_formula_sum            'C64 H40 N8'
_chemical_formula_weight         921.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                97.1790(10)
_cell_angle_beta                 90.8250(10)
_cell_angle_gamma                103.7300(10)
_cell_formula_units_Z            2
_cell_length_a                   11.24280(10)
_cell_length_b                   12.05930(10)
_cell_length_c                   16.9374(2)
_cell_measurement_reflns_used    47847
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.8890
_cell_measurement_theta_min      2.6280
_cell_volume                     2210.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_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     24.00  57.00   0.50    0.05    --   44.00  78.00 139.14   66
  2  \w     33.00  74.00   0.50    0.05    --   56.00  78.00  31.79   82
  3  \w     41.00  66.00   0.50    0.05    --   64.00  78.00  37.60   50
  4  \w     29.00  86.00   0.50    0.05    --   52.00  78.00   0.51  114
  5  \w    102.00 128.00   0.50    0.05    --   68.00  77.00 -11.71   52
  6  \w     33.00  96.00   0.50    0.05    --   56.00  78.00-100.04  126
  7  \w     45.00  70.00   0.50    0.05    --   68.00  77.00-100.41   50
  8  \w     25.00  65.00   0.50    0.05    --   47.69  77.00 -30.00   80
  9  \w     45.00  71.00   0.50    0.05    --   68.00  77.00 -11.71   52
 10  \w     86.00 117.00   0.50    0.22    --  106.75  77.00-120.00   62
 11  \w    139.00 165.00   0.50    0.22    --  106.75  77.00-120.00   52
 12  \w    107.00 132.00   0.50    0.05    --   60.00  76.00-134.14   50
 13  \w     47.00  83.00   0.50    0.05    --   68.00  75.00-163.32   72
 14  \w     38.00  67.00   0.50    0.05    --   60.00  76.00-134.14   58
 15  \w     35.00  61.00   0.50    0.05    --   56.00  75.00 -51.01   52
 16  \w     34.00  68.00   0.50    0.05    --   56.00  75.00 101.64   68
 17  \w     31.00  73.00   0.50    0.05    --   52.00  76.00 155.25   84
 18  \w     38.00  71.00   0.50    0.05    --   60.00  75.00 167.78   66
 19  \w     88.00 114.00   0.50    0.05    --   52.00  76.00 155.25   52
 20  \w    105.00 130.00   0.50    0.05    --   60.00  73.00 123.62   50
 21  \w     39.00  65.00   0.50    0.05    --   60.00  73.00 123.62   52
 22  \w     40.00  65.00   0.50    0.05    --   60.00  72.00  82.23   50
 23  \w     36.00  71.00   0.50    0.05    --   56.00  74.00-174.04   70
 24  \w   -111.00 -36.00   0.50    0.05    --  -47.69 152.00  19.00  150
 25  \w    -73.00 -29.00   0.50    0.22    -- -100.00  61.00-120.00   88
 26  \w    -73.00 -29.00   0.50    0.22    -- -100.00  61.00-180.00   88
 27  \w    -93.00 -21.00   0.50    0.05    --  -47.69 122.00-140.00  144
 28  \w      8.00  33.00   0.50    0.05    --   36.00  88.00-170.04   50
 29  \w     -6.00  25.00   0.50    0.05    --   24.00  93.00 -85.22   62
 30  \w    -21.00   5.00   0.50    0.05    --   12.00 100.00 -22.87   52
 31  \w      7.00  32.00   0.50    0.05    --   36.00  90.00  74.62   50
 32  \w    -25.00   5.00   0.50    0.05    --    8.00 100.00 164.59   60
 33  \w     58.00 119.00   0.50    0.05    --   47.69 152.00  19.00  122
 34  \w     87.00 112.00   0.50    0.22    --  106.75 152.00  19.00   50
 35  \w     78.00 174.00   0.50    0.22    --  106.75 122.00-140.00  192
 36  \w     34.00  66.00   0.50    0.22    --  106.75 -61.00 150.00   64
 37  \w     34.00  73.00   0.50    0.22    --  106.75 -61.00   0.00   78
 38  \w     34.00  71.00   0.50    0.22    --  106.75 -61.00 -30.00   74
 39  \w     39.00  71.00   0.50    0.22    --  106.75 -61.00 -60.00   64
 40  \w     74.00 105.00   0.50    0.22    --  106.75 -94.00   0.00   62
 41  \w     56.00 112.00   0.50    0.22    --  106.75-125.00   0.00  112
 42  \w     34.00 130.00   0.50    0.22    --  106.75-152.00 -23.00  192
 43  \w     50.00 106.00   0.50    0.22    --  106.75 -94.00 -90.00  112
 44  \w     30.00 112.00   0.50    0.05    --   47.69-152.00 -23.00  164
 45  \w     48.00  73.00   0.50    0.22    --  106.75-122.00 137.00   50
 46  \w     39.00 103.00   0.50    0.22    --  106.75 -94.00 120.00  128
 47  \w     16.00  94.00   0.50    0.05    --   47.69-122.00 137.00  156
 48  \w   -106.00 -46.00   0.50    0.22    -- -100.00 101.00-150.79  120
 49  \w    -95.00 -29.00   0.50    0.22    -- -100.00 125.00   0.00  132
 50  \w   -130.00 -36.00   0.50    0.22    -- -100.00 152.00  19.00  188
 51  \w   -110.00 -27.00   0.50    0.22    -- -100.00 122.00-140.00  166
 52  \w   -114.00 -78.00   0.50    0.22    --  -92.00 -52.00-111.70   72
 53  \w    -59.00 -33.00   0.50    0.05    --  -56.00 -78.00 -33.42   52
 54  \w    -50.00 -25.00   0.50    0.05    --  -47.69 -77.00  30.00   50
 55  \w    -67.00 -41.00   0.50    0.05    --  -64.00 -78.00 -55.86   52
 56  \w    -71.00 -45.00   0.50    0.05    --  -68.00 -78.00-115.40   52
 57  \w   -141.00 -69.00   0.50    0.22    --  -92.00 -78.00-123.09  144
 58  \w   -164.00 -77.00   0.50    0.22    -- -100.00 -77.00-150.00  174
 59  \w   -168.00 -73.00   0.50    0.22    --  -96.00 -77.00 -24.24  190
 60  \w   -142.00 -77.00   0.50    0.22    -- -100.00 -77.00  30.00  130
 61  \w    -96.00 -71.00   0.50    0.22    --  -92.00 -76.00  -1.33   50
 62  \w   -165.00-101.00   0.50    0.22    --  -92.00 -76.00  -1.33  128
 63  \w   -168.00 -77.00   0.50    0.22    -- -100.00 -77.00  67.31  182
 64  \w   -173.00 -77.00   0.50    0.22    -- -100.00 -77.00 153.24  192
 65  \w   -168.00 -73.00   0.50    0.22    --  -96.00 -77.00 108.63  190
 66  \w   -140.00 -79.00   0.50    0.22    -- -100.00 -75.00  55.38  122
 67  \w   -161.00 -66.00   0.50    0.22    --  -88.00 -75.00  26.34  190
 68  \w    -83.00 -58.00   0.50    0.22    --  -80.00 -75.00 119.92   50
 69  \w    -84.00 -58.00   0.50    0.22    --  -80.00 -74.00 157.15   52
 70  \w    -87.00 -62.00   0.50    0.22    --  -84.00 -74.00  43.78   50
 71  \w   -170.00 -78.00   0.50    0.22    -- -100.00 -74.00 163.04  184
 72  \w   -148.00-122.00   0.50    0.22    --  -84.00 -74.00  43.78   52
 73  \w   -109.00 -62.00   0.50    0.22    --  -84.00 -75.00  -0.56   94
 74  \w    -92.00 -58.00   0.50    0.22    --  -80.00 -74.00  48.53   68
 75  \w   -102.00 -62.00   0.50    0.22    --  -84.00 -74.00  77.22   80
 76  \w    -88.00 -49.00   0.50    0.05    --  -72.00 -76.00  -6.04   78
 77  \w   -145.00 -78.00   0.50    0.22    -- -100.00 -74.00  -7.04  134
 78  \w   -124.00 -55.00   0.50    0.22    --  -76.00 -73.00-101.14  138
 79  \w    -86.00 -54.00   0.50    0.22    --  -76.00 -74.00-159.72   64
 80  \w    -87.00 -61.00   0.50    0.22    --  -84.00 -76.00-172.19   52
 81  \w    -80.00 -54.00   0.50    0.22    --  -76.00 -74.00 -84.43   52
 82  \w    -92.00 -67.00   0.50    0.22    --  -88.00 -73.00 -67.38   50
 83  \w    -85.00 -59.00   0.50    0.22    --  -80.00 -72.00 -43.70   52
 84  \w    -93.00 -63.00   0.50    0.22    --  -84.00 -73.00  -9.18   60
 85  \w   -170.00 -79.00   0.50    0.22    -- -100.00 -72.00 -69.09  182
 86  \w   -104.00 -59.00   0.50    0.22    --  -80.00 -73.00  84.19   90
 87  \w    -92.00 -59.00   0.50    0.22    --  -80.00 -72.00  32.25   66
 88  \w   -125.00 -99.00   0.50    0.22    --  -88.00 -72.00 109.22   52
 89  \w    -93.00 -67.00   0.50    0.22    --  -88.00 -72.00 109.22   52
 90  \w    -87.00 -61.00   0.50    0.22    --  -80.00 -71.00 168.26   52
 91  \w    -94.00 -68.00   0.50    0.22    --  -88.00 -71.00 169.72   52
 92  \w    -86.00 -50.00   0.50    0.05    --  -68.00 -70.00 112.22   72
 93  \w    -84.00 -48.00   0.50    0.05    --  -68.00 -70.00  33.20   72
 94  \w   -139.00 -79.00   0.50    0.05    --  -68.00 -70.00 -70.37  120
 95  \w    -74.00 -48.00   0.50    0.05    --  -68.00 -70.00 -70.37   52
 96  \w    -79.00 -45.00   0.50    0.05    --  -60.00 -70.00 -92.70   68
 97  \w    -91.00 -61.00   0.50    0.22    --  -80.00 -68.00-126.44   60
 98  \w    -79.00 -52.00   0.50    0.05    --  -72.00 -69.00-157.77   54
 99  \w   -160.00 -70.00   0.50    0.22    --  -88.00 -65.00-165.20  180
100  \w   -109.00 -67.00   0.50    0.22    --  -84.00 -62.00 -66.65   84
101  \w   -102.00 -76.00   0.50    0.22    --  -92.00 -60.00-107.19   52
102  \w   -159.00-101.00   0.50    0.22    --  -88.00 -52.00-130.40  116
103  \w   -161.00-135.00   0.50    0.22    --  -92.00 -60.00-107.19   52
104  \w   -103.00 -53.00   0.50    0.05    --  -72.00 -67.00  83.43  100
105  \w    -93.00 -67.00   0.50    0.22    --  -84.00 -65.00 133.23   52
106  \w   -119.00 -64.00   0.50    0.05    --  -47.69-152.00 -23.00  110
107  \w   -164.00 -64.00   0.50    0.22    -- -100.00-152.00 -23.00  200
108  \w   -173.00 -84.00   0.50    0.22    -- -100.00-122.00 137.00  178
109  \w    -41.00 -16.00   0.50    0.05    --  -44.00 -91.00 -56.78   50
110  \w    -41.00 -16.00   0.50    0.05    --  -44.00 -91.00-137.15   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0085862000
_diffrn_orient_matrix_UB_12      -0.0166915000
_diffrn_orient_matrix_UB_13      -0.0912315000
_diffrn_orient_matrix_UB_21      0.0106472000
_diffrn_orient_matrix_UB_22      -0.1245366000
_diffrn_orient_matrix_UB_23      0.0025859000
_diffrn_orient_matrix_UB_31      -0.1405406000
_diffrn_orient_matrix_UB_32      -0.0425867000
_diffrn_orient_matrix_UB_33      -0.0095920000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            80861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.641
_diffrn_reflns_theta_min         2.632
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0360P)^2^+1.3540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7991
_reflns_number_total             8894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02937f2.cif
_cod_data_source_block           exp_742
_cod_depositor_comments
'Adding full bibliography for 1574686--1574690.cif.'
_cod_database_code               1574689
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     yamagi-2-50
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.829
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C01D(H01A,H01C), C01Q(H01T,H01U), C01S(H01Z,H), C01W(H01D,H01K)
2.b Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00W(H00W), C00Z(H00Z), C011(H011), C013(H013), C014(H014),
 C015(H015), C018(H018), C019(H019), C01A(H01L), C01B(H01B), C01C(H01M),
 C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J),
 C01K(H01O), C01L(H01P), C01M(H01Q), C01N(H01N), C01O(H01R), C01P(H01S),
 C01R(H01W), C01T(H01), C01U(H1), C01V(H01V), C01X(H01X), C01Y(H01Y), C01Z(H2),
 C020(H020)
;
_shelx_res_checksum              19529
_shelx_hkl_checksum              36700
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.760