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_1576341
_publ_section_title
;
 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_absolute_configuration unk
_chemical_formula_moiety         'C42 H63 N O3'
_chemical_formula_sum            'C42 H63 N O3'
_chemical_formula_weight         629.93
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-28
_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            3
_cell_length_a                   15.8786(7)
_cell_length_b                   15.8786(7)
_cell_length_c                   17.1045(9)
_cell_measurement_reflns_used    4175
_cell_measurement_temperature    172(1)
_cell_measurement_theta_max      71.9870
_cell_measurement_theta_min      4.0890
_cell_volume                     3734.8(3)
_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      172(1)
_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    -89.00 -62.00   1.00    1.00    --    0.00 -37.00 120.00   27
  2  \w    -25.00  27.00   1.00    1.00    --    0.00 -37.00  30.00   52
  3  \w    -27.00  10.00   1.00    1.00    --    0.00  37.00   0.00   37
  4  \w     39.00  89.00   1.00    1.00    --    0.00  37.00   0.00   50
  5  \w    -31.00  -1.00   1.00    1.00    --    0.00 -37.00 120.00   30
  6  \w    -82.00 -15.00   1.00    1.00    --    0.00 -37.00   0.00   67
  7  \w     63.00 103.00   1.00    3.00    --   92.10  30.00 -30.00   40
  8  \w     50.00 102.00   1.00    3.00    --   92.10 -82.00-180.00   52
  9  \w     13.00 117.00   1.00    3.00    --   92.10 -45.00 150.00  104
 10  \w      3.00 120.00   1.00    3.00    --   92.10 -61.00  30.00  117
 11  \w     93.00 118.00   1.00    3.00    --   92.10 -82.00-150.00   25
 12  \w     17.00 118.00   1.00    3.00    --   92.10 -61.00 -60.00  101
 13  \w     60.00  86.00   1.00    3.00    --   92.10 -82.00-150.00   26
 14  \w     29.00 118.00   1.00    3.00    --   92.10 -45.00  30.00   89
 15  \w     71.00 101.00   1.00    3.00    --   92.10 -82.00  90.00   30
 16  \w     35.00 122.00   1.00    3.00    --   92.10 -82.00 -60.00   87
 17  \w    124.00 182.00   1.00    3.00    --   92.10  30.00 -30.00   58
 18  \w     12.00  43.00   1.00    3.00    --   92.10 -82.00  30.00   31
 19  \w     67.00 171.00   1.00    3.00    --   92.10  30.00 -90.00  104
 20  \w     87.00 112.00   1.00    3.00    --   92.10 -82.00 -30.00   25
 21  \w      3.00  37.00   1.00    3.00    --   92.10 -82.00 150.00   34
 22  \w     58.00 123.00   1.00    3.00    --   92.10 -82.00 150.00   65
 23  \w     14.00  62.00   1.00    3.00    --   92.10 -30.00 -60.00   48
;
_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      0.0451266000
_diffrn_orient_matrix_UB_12      -0.0607439000
_diffrn_orient_matrix_UB_13      0.0285395000
_diffrn_orient_matrix_UB_21      -0.0375562000
_diffrn_orient_matrix_UB_22      -0.0008378000
_diffrn_orient_matrix_UB_23      0.0832031000
_diffrn_orient_matrix_UB_31      -0.0954359000
_diffrn_orient_matrix_UB_32      -0.0941023000
_diffrn_orient_matrix_UB_33      -0.0192911000
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0336
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12362
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.936
_diffrn_reflns_theta_max         66.936
_diffrn_reflns_theta_min         4.125
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85976
_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 blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    0.840
_exptl_crystal_description       block
_exptl_crystal_F_000             1038
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 842 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1774P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2338
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2082
_reflns_number_total             2901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06789h2.cif
_cod_data_source_block           exp_4250_auto
_cod_original_cell_volume        3734.8(4)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1576341
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2. Restrained distances
 N1-C1 \\sim N1-C15
 with sigma of 0.02
 O2-C4 \\sim O1-C18
 with sigma of 0.02
 O2-C5 \\sim O1-C17
 with sigma of 0.04
 C12-C13 \\sim C27-C28
 with sigma of 0.04
 C14-C13 \\sim C26-C28
 with sigma of 0.04
 O2-C3 \\sim O1-C19
 with sigma of 0.04
 C6-C2 \\sim C16-C20
 with sigma of 0.04
 C14-C12 \\sim C26-C27
 with sigma of 0.04
 C11-C13 \\sim C25-C28
 with sigma of 0.02
 C11-C12 \\sim C25-C27
 with sigma of 0.02
 C5-C13 \\sim C17-C28
 with sigma of 0.04
 C5-C12 \\sim C17-C27
 with sigma of 0.04
 C2-C1 \\sim C20-C15
 with sigma of 0.02
 C6-C5 \\sim C16-C17
 with sigma of 0.02
 C6-C1 \\sim C16-C15
 with sigma of 0.02
 C7-C8 \\sim C21-C23
 with sigma of 0.02
 N1-C6 \\sim N1-C16
 with sigma of 0.04
 C2-C3 \\sim C20-C19
 with sigma of 0.02
 C6-C11 \\sim C16-C25
 with sigma of 0.04
 N1-C2 \\sim N1-C20
 with sigma of 0.04
 C6-C4 \\sim C16-C18
 with sigma of 0.04
 C8-C10 \\sim C23-C22
 with sigma of 0.04
 C7-C2 \\sim C21-C20
 with sigma of 0.04
 C8-C9 \\sim C23-C24
 with sigma of 0.04
 C2-C4 \\sim C20-C18
 with sigma of 0.04
 C14-C11 \\sim C26-C25
 with sigma of 0.02
 C8-C3 \\sim C23-C19
 with sigma of 0.04
 C14-C5 \\sim C26-C17
 with sigma of 0.04
 C7-C10 \\sim C21-C22
 with sigma of 0.02
 C7-C9 \\sim C21-C24
 with sigma of 0.02
 C7-C3 \\sim C21-C19
 with sigma of 0.02
 C11-C5 \\sim C25-C17
 with sigma of 0.02
 C5-C4 \\sim C17-C18
 with sigma of 0.02
 C3-C4 \\sim C19-C18
 with sigma of 0.02
 C7-C4 \\sim C21-C18
 with sigma of 0.04
 C10-C9 \\sim C22-C24
 with sigma of 0.04
 C10-C3 \\sim C22-C19
 with sigma of 0.04
 C11-C4 \\sim C25-C18
 with sigma of 0.04
 C9-C3 \\sim C24-C19
 with sigma of 0.04
 C5-C1 \\sim C17-C15
 with sigma of 0.04
 C5-C3 \\sim C17-C19
 with sigma of 0.04
 C1-C3 \\sim C15-C19
 with sigma of 0.04
3. Rigid bond restraints
 C25, C27, C26, C28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim C15 \\sim C6 \\sim C2 \\sim C16 \\sim C20 \\sim C5 \\sim C3
\\sim C17 \\sim C19 \\sim C11 \\sim C4 \\sim C7 \\sim C25 \\sim C18 \\sim C21
\\sim C14 \\sim C12 \\sim C13 \\sim O2 \\sim C8 \\sim C10 \\sim C9 \\sim C26
\\sim C27 \\sim C28 \\sim O1 \\sim C23 \\sim C22 \\sim C24: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C25 \\sim C27 \\sim C26 \\sim C28: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
5. Others
 Sof(C15)=Sof(C16)=Sof(H16)=Sof(C20)=Sof(H20)=Sof(C17)=Sof(C19)=Sof(C25)=
 Sof(C18)=Sof(C21)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(O1)=Sof(H1)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=1-FVAR(1)
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(H14C)=Sof(O2)=Sof(H2)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C11)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C2)=Sof(H2A)=Sof(C5)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C1)=Sof(C3)=Sof(C4)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=FVAR(1)
 Fixed Z: O2(0.51391)
6.a Riding coordinates:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C23(H23A,H23B,H23C)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2A), C16(H16), C20(H20)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C26(H26A,H26B,H26C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4697
_shelx_fab_checksum              65988
_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 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.604