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_1574687
_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         'C30 H17 Br N2 O3 S'
_chemical_formula_sum            'C30 H17 Br N2 O3 S'
_chemical_formula_weight         565.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-06
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.36400(10)
_cell_length_b                   35.4478(2)
_cell_length_c                   13.14950(10)
_cell_measurement_reflns_used    26371
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.1740
_cell_measurement_theta_min      2.4840
_cell_volume                     5763.12(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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     35.00 120.00   0.50    2.00    --   47.91  48.00 -36.00  170
  2  \w   -171.00 -91.00   0.50   10.00    -- -100.00 -99.00 -45.00  160
  3  \w    -55.00 -27.00   0.50   10.00    -- -100.00  48.00 -36.00   56
  4  \w     93.00 174.00   0.50   10.00    --  106.65  48.00 -36.00  162
  5  \w     82.00 174.00   0.50   10.00    --  106.65  82.00 168.00  184
  6  \w    -93.00 -23.00   0.50    2.00    --  -47.91 125.00-180.00  140
  7  \w    -19.00  28.00   0.50    2.00    --  -47.91  19.00-180.00   94
  8  \w    -42.00  25.00   0.50    2.00    --  -47.91  38.00  60.00  134
  9  \w    -26.00  16.00   0.50    2.00    --   47.91 -19.00  30.00   84
 10  \w    -75.00 -27.00   0.50   10.00    -- -100.00  61.00-180.00   96
 11  \w   -112.00 -30.00   0.50   10.00    -- -100.00 125.00-180.00  164
 12  \w    -75.00 -27.00   0.50   10.00    -- -100.00  61.00   0.00   96
 13  \w     34.00  72.00   0.50   10.00    --  106.65 -61.00   0.00   76
 14  \w     90.00 174.00   0.50   10.00    --  106.65  61.00  60.00  168
 15  \w     90.00 174.00   0.50   10.00    --  106.65  61.00 120.00  168
 16  \w     34.00  72.00   0.50   10.00    --  106.65 -61.00 120.00   76
 17  \w     34.00  72.00   0.50   10.00    --  106.65 -61.00  60.00   76
 18  \w     34.00 105.00   0.50   10.00    --  106.65 -94.00 -90.00  142
 19  \w     34.00  72.00   0.50   10.00    --  106.65 -61.00  30.00   76
 20  \w     34.00  72.00   0.50   10.00    --  106.65 -61.00 -30.00   76
 21  \w     33.00 120.00   0.50    2.00    --   47.91  57.00-180.00  174
 22  \w     25.00 121.00   0.50    2.00    --   47.91  77.00  60.00  192
;
_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      0.0340079000
_diffrn_orient_matrix_UB_12      0.0242094000
_diffrn_orient_matrix_UB_13      -0.0408461000
_diffrn_orient_matrix_UB_21      -0.1030114000
_diffrn_orient_matrix_UB_22      0.0644198000
_diffrn_orient_matrix_UB_23      -0.0051768000
_diffrn_orient_matrix_UB_31      0.0612932000
_diffrn_orient_matrix_UB_32      0.0947941000
_diffrn_orient_matrix_UB_33      0.0139350000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            52540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.633
_diffrn_reflns_theta_min         2.493
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71983
_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    1.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.513
_refine_diff_density_min         -2.438
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0888
_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^)+(0.1169P)^2^+20.8148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2416
_refine_ls_wR_factor_ref         0.2487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5151
_reflns_number_total             5990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02937f2.cif
_cod_data_source_block           exp_1085
_cod_depositor_comments
'Adding full bibliography for 1574686--1574690.cif.'
_cod_database_code               1574687
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Br N O S'
_chemical_oxdiff_usercomment     brosyl-HH-TEQ
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C00Y, C00W, C00Z, C011, C00X, C010, Br00
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Br00 \\sim C00X \\sim C010 \\sim C00Y \\sim C00Z \\sim C011: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
4.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U),
 C00V(H00V), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              67473
_shelx_hkl_checksum              11566
_shelx_fab_checksum              19210
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.786