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_1574688
_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         'C50 H32 N4 O2 Pd, 2(B F4)'
_chemical_formula_sum            'C50 H32 B2 F8 N4 O2 Pd'
_chemical_formula_weight         957.41
_space_group_crystal_system      tetragonal
_space_group_IT_number           130
_space_group_name_Hall           '-P 4a 2ac'
_space_group_name_H-M_alt        'P 4/n c c :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_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                   20.05360(10)
_cell_length_b                   20.05360(10)
_cell_length_c                   24.3689(2)
_cell_measurement_reflns_used    37308
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.3630
_cell_measurement_theta_min      3.1000
_cell_volume                     9799.88(11)
_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 0.998
_diffrn_measured_fraction_theta_max 0.982
_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    -26.00  16.00   0.50    0.16    --   47.88 -19.00  60.00   84
  2  \w    -25.00  39.00   0.50    0.16    --   47.88 -38.00  30.00  128
  3  \w    -24.00  74.00   0.50    0.16    --   47.88 -85.00-158.00  196
  4  \w     34.00  72.00   0.50    1.38    --  106.56 -61.00 -90.00   76
  5  \w     34.00  72.00   0.50    1.38    --  106.56 -61.00  30.00   76
  6  \w     94.00 174.00   0.50    1.38    --  106.56  30.00 120.00  160
  7  \w     93.00 174.00   0.50    1.38    --  106.56  43.00-169.00  162
  8  \w     94.00 174.00   0.50    1.38    --  106.56  45.00-180.00  160
  9  \w     94.00 171.00   0.50    1.38    --  106.56  45.00  60.00  154
 10  \w     94.00 174.00   0.50    1.38    --  106.56  45.00  90.00  160
 11  \w    -19.00  28.00   0.50    0.16    --  -47.88  19.00-150.00   94
 12  \w    -19.00  28.00   0.50    0.16    --  -47.88  19.00 -30.00   94
 13  \w    -75.00 -27.00   0.50    1.38    -- -100.00  61.00-120.00   96
 14  \w    -75.00 -27.00   0.50    1.38    -- -100.00  61.00  30.00   96
 15  \w    -75.00 -27.00   0.50    1.38    -- -100.00  61.00  60.00   96
 16  \w   -123.00 -27.00   0.50    1.38    -- -100.00  77.00  60.00  192
 17  \w   -173.00 -87.00   0.50    1.38    -- -100.00 -30.00   0.00  172
 18  \w   -172.00 -86.00   0.50    1.38    -- -100.00 -43.00  38.00  172
 19  \w   -120.00 -34.00   0.50    0.16    --  -47.88 -43.00  38.00  172
 20  \w   -173.00 -84.00   0.50    1.38    -- -100.00 -85.00-158.00  178
;
_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      -0.0170898000
_diffrn_orient_matrix_UB_12      0.0741751000
_diffrn_orient_matrix_UB_13      -0.0085873000
_diffrn_orient_matrix_UB_21      0.0374828000
_diffrn_orient_matrix_UB_22      -0.0007428000
_diffrn_orient_matrix_UB_23      -0.0551864000
_diffrn_orient_matrix_UB_31      -0.0648680000
_diffrn_orient_matrix_UB_32      -0.0199593000
_diffrn_orient_matrix_UB_33      -0.0295939000
_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  0.1022
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            88311
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.685
_diffrn_reflns_theta_min         3.117
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52978
_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 dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             3868
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0655P)^2^+12.1641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4290
_reflns_number_total             5083
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 14.6790\% 
around [-0.01 -0.02 -1.00] (reciprocal) or [-0.01 -0.03 -1.00] (direct)
;
_cod_data_source_file            d5sc02937f2.cif
_cod_data_source_block           exp_1166_twin1_hklf4
_cod_depositor_comments
;
Adding full bibliography for 1574686--1574690.cif.

2025-07-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C100 H64 B3 F12 N8 O4 Pd2'
_cod_original_formula_weight         1914.82
_cod_original_formula_moiety         '2(C50 H32 N4 O2 Pd), 3(B F4)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        9799.88(13)
_cod_original_sg_symbol_H-M      'P 4/n c c'
_cod_database_code               1574688
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O B F Pd'
_chemical_oxdiff_usercomment     'i-TEQ p-anisyl-Pd 2(BF4)-'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C012(H012)
2.b Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              70291
_shelx_hkl_checksum              9376
_shelx_fab_checksum              80369
_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 2.380
_oxdiff_exptl_absorpt_empirical_full_min 0.704
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2