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_1574686
_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_absolute_configuration rmad
_chemical_formula_moiety         '2(C16 H10 N2 O)'
_chemical_formula_sum            'C32 H20 N4 O2'
_chemical_formula_weight         492.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           81
_space_group_name_Hall           'P -4'
_space_group_name_H-M_alt        'P -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.10340(10)
_cell_length_b                   14.10340(10)
_cell_length_c                   11.60890(10)
_cell_measurement_reflns_used    16291
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.6330
_cell_measurement_theta_min      4.4210
_cell_volume                     2309.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.972
_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   -100.00 -75.00   0.50    1.02    --  -48.46 155.00-148.00   50
  2  \w    -85.00 -52.00   0.50    1.02    --  -48.46 134.00 -43.00   66
  3  \w   -101.00 -76.00   0.50    1.02    --  -48.46  -9.00 102.00   50
  4  \w     -9.00  24.00   0.50    1.02    --  -48.46   9.00 -83.00   66
  5  \w     52.00  77.00   0.50    1.02    --   48.46   9.00 -83.00   50
  6  \w     71.00  96.00   0.50    1.02    --   48.46 134.00 -43.00   50
  7  \w     71.00  96.00   0.50    1.02    --   48.46 135.00 135.00   50
  8  \w   -136.00-111.00   0.50    4.07    -- -100.00-155.00 173.00   50
  9  \w   -101.00 -72.00   0.50    4.07    -- -100.00 134.00 -43.00   58
 10  \w   -167.00-122.00   0.50    4.07    -- -100.00-135.00  70.00   90
 11  \w   -146.00-121.00   0.50    4.07    -- -100.00  -9.00 102.00   50
 12  \w    111.00 136.00   0.50    4.07    --  107.23 134.00 -43.00   50
 13  \w    103.00 128.00   0.50    4.07    --  107.23 120.00  54.00   50
 14  \w    119.00 144.00   0.50    4.07    --  107.23   9.00 -83.00   50
 15  \w     36.00 119.00   0.50    4.07    --  107.23-135.00  70.00  166
 16  \w    -70.00 -33.00   0.50    1.02    --  -48.46 -57.00  30.00   74
 17  \w    -53.00 -27.00   0.50    1.02    --  -48.46 -77.00   0.00   52
 18  \w    -65.00 -36.00   0.50    1.02    --  -48.46 -38.00   0.00   58
 19  \w    -65.00 -29.00   0.50    1.02    --  -48.46 -77.00 -30.00   72
 20  \w     37.00 122.00   0.50    1.02    --   48.46  19.00  30.00  170
 21  \w     26.00  52.00   0.50    1.02    --   48.46  77.00 -30.00   52
 22  \w   -166.00-140.00   0.50    4.07    -- -100.00 -77.00   0.00   52
 23  \w   -173.00 -82.00   0.50    4.07    -- -100.00 -65.00   8.66  182
 24  \w   -106.00 -80.00   0.50    4.07    -- -100.00 -74.00   0.96   52
 25  \w   -109.00 -83.00   0.50    4.07    -- -100.00 -61.00  30.00   52
 26  \w   -117.00 -81.00   0.50    4.07    -- -100.00 -67.00  -5.30   72
 27  \w   -104.00 -78.00   0.50    4.07    -- -100.00 -75.00  52.72   52
 28  \w   -106.00 -81.00   0.50    4.07    -- -100.00 -67.00  -0.08   50
 29  \w   -104.00 -78.00   0.50    4.07    -- -100.00 -75.00  38.42   52
 30  \w   -116.00 -82.00   0.50    4.07    -- -100.00 -65.00  20.65   68
 31  \w   -173.00 -79.00   0.50    4.07    -- -100.00 -75.00 -13.36  188
 32  \w   -172.00 -85.00   0.50    4.07    -- -100.00 -58.00  22.84  174
 33  \w   -108.00 -82.00   0.50    4.07    -- -100.00 -66.00   5.86   52
 34  \w   -106.00 -81.00   0.50    4.07    -- -100.00 -67.00  61.48   50
 35  \w   -102.00 -77.00   0.50    4.07    -- -100.00 -76.00  61.29   50
 36  \w   -103.00 -77.00   0.50    4.07    -- -100.00 -77.00  30.00   52
 37  \w   -106.00 -81.00   0.50    4.07    -- -100.00 -67.00 -19.20   50
 38  \w   -107.00 -81.00   0.50    4.07    -- -100.00 -67.00  30.30   52
 39  \w   -104.00 -78.00   0.50    4.07    -- -100.00 -77.00   0.00   52
 40  \w     35.00  73.00   0.50    4.07    --  107.23 -61.00  30.00   76
 41  \w     35.00  73.00   0.50    4.07    --  107.23 -61.00 -60.00   76
;
_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      -0.1057534000
_diffrn_orient_matrix_UB_12      -0.0240711000
_diffrn_orient_matrix_UB_13      -0.0158137000
_diffrn_orient_matrix_UB_21      -0.0240165000
_diffrn_orient_matrix_UB_22      0.1065870000
_diffrn_orient_matrix_UB_23      -0.0027408000
_diffrn_orient_matrix_UB_31      0.0131820000
_diffrn_orient_matrix_UB_32      0.0006621000
_diffrn_orient_matrix_UB_33      -0.1316692000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24695
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.712
_diffrn_reflns_theta_min         3.133
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0295P)^2^+0.6061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                4284
_reflns_number_total             4617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02937f2.cif
_cod_data_source_block           exp_657_auto
_cod_depositor_comments
'Adding full bibliography for 1574686--1574690.cif.'
_cod_original_cell_volume        2309.08(4)
_cod_database_code               1574686
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     KO20211115-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012)
;
_shelx_res_checksum              34813
_shelx_hkl_checksum              3984
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.689