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_1576344
_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_formula_moiety         'C42 H60 N O3, C16 H36 N'
_chemical_formula_sum            'C58 H96 N2 O3'
_chemical_formula_weight         869.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-28
_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                 97.544(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2641(4)
_cell_length_b                   26.5484(9)
_cell_length_c                   22.5350(9)
_cell_measurement_reflns_used    10000
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      53.4960
_cell_measurement_theta_min      3.3610
_cell_volume                     6087.5(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      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     37.00  88.00   1.00    1.00    --    0.00  57.00 150.00   51
  2  \w    -87.00 -22.00   1.00    1.00    --    0.00 -57.00 -90.00   65
  3  \w    -10.00  27.00   1.00    1.00    --    0.00 -57.00 -90.00   37
  4  \w    -64.00 -19.00   1.00    1.00    --    0.00 -82.00   0.00   45
  5  \w     10.00  35.00   1.00    1.00    --    0.00 -82.00   0.00   25
  6  \w    -43.00  21.00   1.00    1.00    --    0.00 -77.00-150.00   64
  7  \w    -26.00  88.00   1.00    1.00    --    0.00  37.00   0.00  114
  8  \w     82.00 107.00   1.00    3.00    --   92.10 -82.00-180.00   25
  9  \w     77.00 102.00   1.00    3.00    --   92.10 -45.00 150.00   25
 10  \w     41.00 127.00   1.00    3.00    --   92.10 -82.00 120.00   86
 11  \w      3.00  31.00   1.00    3.00    --   92.10 -61.00  30.00   28
 12  \w     35.00  88.00   1.00    3.00    --   92.10 -61.00  30.00   53
 13  \w      4.00 106.00   1.00    3.00    --   92.10 -82.00  30.00  102
 14  \w    127.00 182.00   1.00    3.00    --   92.10 -15.00 120.00   55
 15  \w     18.00  50.00   1.00    3.00    --   92.10 -45.00 150.00   32
 16  \w     82.00 111.00   1.00    3.00    --   92.10 -82.00 -30.00   29
 17  \w     19.00  45.00   1.00    3.00    --   92.10 -82.00 -30.00   26
 18  \w      5.00 111.00   1.00    3.00    --   92.10 -15.00 120.00  106
 19  \w      3.00 118.00   1.00    3.00    --   92.10 -61.00 120.00  115
 20  \w      3.00 110.00   1.00    3.00    --   92.10 -82.00 -90.00  107
 21  \w      6.00 110.00   1.00    3.00    --   92.10 -61.00 -90.00  104
 22  \w     92.00 117.00   1.00    3.00    --   92.10 -45.00 -30.00   25
 23  \w      4.00  38.00   1.00    3.00    --   92.10 -82.00 120.00   34
 24  \w     74.00  99.00   1.00    3.00    --   92.10 -82.00-120.00   25
 25  \w     79.00 104.00   1.00    3.00    --   92.10 -82.00 -60.00   25
 26  \w     37.00 170.00   1.00    3.00    --   92.10  15.00  60.00  133
;
_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      0.0081247000
_diffrn_orient_matrix_UB_12      0.0416038000
_diffrn_orient_matrix_UB_13      -0.0469944000
_diffrn_orient_matrix_UB_21      0.0262562000
_diffrn_orient_matrix_UB_22      0.0393332000
_diffrn_orient_matrix_UB_23      0.0504266000
_diffrn_orient_matrix_UB_31      0.1488719000
_diffrn_orient_matrix_UB_32      -0.0092964000
_diffrn_orient_matrix_UB_33      0.0028130000
_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  0.0821
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68425
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49129
_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 brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    0.949
_exptl_crystal_description       block
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         10828
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1321P)^2^+1.8966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.2691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6789
_reflns_number_total             10828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06789h2.cif
_cod_data_source_block           exp_4406_auto
_cod_database_code               1576344
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C46-C45 = C45-C44 = C44-C43
 1.52 with sigma of 0.01
 C55-C57 = C58-C56
 2.52 with sigma of 0.01
3. Rigid bond restraints
 C55, C56, C57, C58
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C43, C44, C45, C46
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C55 \\sim C56 \\sim C57 \\sim C58: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C46 \\sim C45 \\sim C44 \\sim C43: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
5.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C52(H52A,H52B), C47(H47A,H47B), C55(H55A,H55B), C53(H53A,
 H53B), C43(H43A,H43B), C48(H48A,H48B), C45(H45A,H45B), C56(H56A,H56B),
 C49(H49A,H49B), C44(H44A,H44B), C57(H57A,H57B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C18(H18), C6(H6), C14(H14), C8(H8), C12(H12)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C), C34(H34A,H34B,H34C), C30(H30A,H30B,
 H30C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C33(H33A,
 H33B,H33C), C32(H32A,H32B,H32C), C26(H26A,H26B,H26C), C22(H22A,H22B,H22C),
 C25(H25A,H25B,H25C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C37(H37A,H37B,
 H37C), C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C36(H36A,H36B,H36C), C54(H54A,
 H54B,H54C), C50(H50A,H50B,H50C), C58(H58A,H58B,H58C), C46(H46A,H46B,H46C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              18822
_shelx_fab_checksum              55709
_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 3.255
_oxdiff_exptl_absorpt_empirical_full_min 0.422