A 4,4',4''-Nitrilotriphenoxyl Radical Derived from Yang's Biradical
Hong, Qiong-Yan; Huang, Bin; Niu, Yan-Fei; Wang, Cui-Hong; Zhao, Xiao-li; Yang, Hai-Bo; Shi, Xueliang; Chemical Science  (2025) –; doi:10.1039/D5SC06789H

data_1576343
_publ_section_title
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 A 4,4',4''-Nitrilotriphenoxyl Radical Derived from Yang's Biradical
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06789H
_journal_year                    2025
_chemical_formula_moiety         'C42 H60 N O3'
_chemical_formula_sum            'C42 H60 N O3'
_chemical_formula_weight         626.91
_space_group_crystal_system      trigonal
_space_group_IT_number           163
_space_group_name_Hall           '-P 3 2c'
_space_group_name_H-M_alt        'P -3 1 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   15.3640(13)
_cell_length_b                   15.3640(13)
_cell_length_c                   11.5469(12)
_cell_measurement_reflns_used    2741
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      64.3360
_cell_measurement_theta_min      3.2980
_cell_volume                     2360.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -40.00   2.00   1.00    1.00    --    0.00 -37.00 150.00   42
  2  \w    -65.00 -40.00   1.00    1.00    --    0.00 -77.00 -30.00   25
  3  \w     59.00  84.00   1.00    1.00    --    0.00  57.00 -90.00   25
  4  \w    -26.00  88.00   1.00    1.00    --    0.00  37.00  30.00  114
  5  \w    -24.00  25.00   1.00    1.00    --    0.00 -57.00  30.00   49
  6  \w    -54.00 -29.00   1.00    1.00    --    0.00 -57.00  30.00   25
  7  \w     10.00  35.00   1.00    1.00    --    0.00 -19.00-180.00   25
  8  \w    -85.00 -55.00   1.00    1.00    --    0.00 -57.00  30.00   30
  9  \w      3.00  34.00   1.00    3.00    --   92.10 -82.00 -30.00   31
 10  \w      4.00 128.00   1.00    3.00    --   92.10 -82.00 -90.00  124
 11  \w      6.00  88.00   1.00    3.00    --   92.10 -61.00 -90.00   82
 12  \w     75.00 169.00   1.00    3.00    --   92.10  45.00 120.00   94
 13  \w      6.00  32.00   1.00    3.00    --   92.10 -82.00  60.00   26
 14  \w     93.00 126.00   1.00    3.00    --   92.10 -82.00  60.00   33
 15  \w      5.00 127.00   1.00    3.00    --   92.10 -82.00   0.00  122
 16  \w     60.00 122.00   1.00    3.00    --   92.10 -82.00 150.00   62
 17  \w     75.00 101.00   1.00    3.00    --   92.10  30.00  30.00   26
 18  \w     67.00 182.00   1.00    3.00    --   92.10  45.00-120.00  115
 19  \w      3.00 119.00   1.00    3.00    --   92.10 -61.00   0.00  116
 20  \w     66.00 176.00   1.00    3.00    --   92.10  45.00-150.00  110
 21  \w     78.00 103.00   1.00    3.00    --   92.10 -82.00-150.00   25
 22  \w     75.00 100.00   1.00    3.00    --   92.10 -82.00 -30.00   25
 23  \w     54.00  94.00   1.00    3.00    --   92.10 -82.00 120.00   40
 24  \w      3.00 116.00   1.00    3.00    --   92.10 -61.00 120.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1073786000
_diffrn_orient_matrix_UB_12      -0.0170157000
_diffrn_orient_matrix_UB_13      -0.0111552000
_diffrn_orient_matrix_UB_21      0.0359015000
_diffrn_orient_matrix_UB_22      0.1055327000
_diffrn_orient_matrix_UB_23      0.0500659000
_diffrn_orient_matrix_UB_31      0.0243042000
_diffrn_orient_matrix_UB_32      0.0444276000
_diffrn_orient_matrix_UB_33      -0.1231269000
_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  0.1321
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26025
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.998
_diffrn_reflns_theta_max         66.998
_diffrn_reflns_theta_min         3.322
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (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    0.882
_exptl_crystal_description       block
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0955
_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^)+(0.1873P)^2^+0.4560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2938
_refine_ls_wR_factor_ref         0.3109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                993
_reflns_number_total             1410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06789h2.cif
_cod_data_source_block           exp_4119_auto
_cod_original_cell_volume        2360.5(5)
_cod_database_code               1576343
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.900
_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:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49985
_shelx_fab_checksum              32526
_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 3.906
_oxdiff_exptl_absorpt_empirical_full_min 0.318