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_1576342
_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         'C21 H30.5 N0.5 O1.5, 0.5(C7 H8)'
_chemical_formula_sum            'C24.5 H34.5 N0.5 O1.5'
_chemical_formula_weight         360.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-28
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.22 svn.r631f81ec for OlexSys, GUI svn.r7248)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.430(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4459(11)
_cell_length_b                   17.3442(12)
_cell_length_c                   22.2295(17)
_cell_measurement_reflns_used    1988
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      61.1910
_cell_measurement_theta_min      3.9890
_cell_volume                     4340.1(6)
_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    -27.00  33.00   1.00    4.00    --    0.00  37.00 150.00   60
  2  \w     -7.00  26.00   1.00    4.00    --    0.00 -37.00-120.00   33
  3  \w     46.00  72.00   1.00    4.00    --    0.00  57.00-180.00   26
  4  \w    -88.00  -6.00   1.00    4.00    --    0.00 -37.00 150.00   82
  5  \w     45.00  87.00   1.00    4.00    --    0.00  37.00 150.00   42
  6  \w    -89.00 -39.00   1.00    4.00    --    0.00 -37.00-120.00   50
  7  \w      4.00  53.00   1.00    8.00    --   92.10 -61.00 -60.00   49
  8  \w     58.00 150.00   1.00    8.00    --   92.10  82.00  30.00   92
  9  \w      3.00  53.00   1.00    8.00    --   92.10 -82.00 -60.00   50
 10  \w     66.00 118.00   1.00    8.00    --   92.10  45.00-180.00   52
 11  \w    123.00 182.00   1.00    8.00    --   92.10  45.00-180.00   59
 12  \w      5.00 107.00   1.00    8.00    --   92.10 -82.00  90.00  102
 13  \w     87.00 113.00   1.00    8.00    --   92.10 -77.00   0.00   26
 14  \w      4.00 105.00   1.00    8.00    --   92.10 -61.00  90.00  101
 15  \w      3.00  43.00   1.00    8.00    --   92.10 -77.00   0.00   40
 16  \w     34.00 118.00   1.00    8.00    --   92.10 -61.00-180.00   84
 17  \w     80.00 109.00   1.00    8.00    --   92.10 -61.00 -60.00   29
 18  \w     63.00 125.00   1.00    8.00    --   92.10 -82.00 -60.00   62
 19  \w     92.00 181.00   1.00    8.00    --   92.10  45.00 150.00   89
 20  \w     37.00 128.00   1.00    8.00    --   92.10 -82.00-180.00   91
 21  \w      4.00  34.00   1.00    8.00    --   92.10 -61.00-120.00   30
 22  \w     83.00 118.00   1.00    8.00    --   92.10 -61.00-120.00   35
 23  \w    125.00 150.00   1.00    8.00    --   92.10 -15.00  60.00   25
 24  \w    100.00 126.00   1.00    8.00    --   92.10 -82.00  60.00   26
 25  \w     78.00 103.00   1.00    8.00    --   92.10 -82.00-120.00   25
 26  \w     14.00  66.00   1.00    8.00    --   92.10 -15.00  60.00   52
;
_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      0.0009926000
_diffrn_orient_matrix_UB_12      -0.0420425000
_diffrn_orient_matrix_UB_13      0.0610695000
_diffrn_orient_matrix_UB_21      -0.0692359000
_diffrn_orient_matrix_UB_22      -0.0676329000
_diffrn_orient_matrix_UB_23      -0.0345205000
_diffrn_orient_matrix_UB_31      0.1180700000
_diffrn_orient_matrix_UB_32      -0.0394810000
_diffrn_orient_matrix_UB_33      -0.0059893000
_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  0.1282
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.044
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44061
_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    1.102
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.1398
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3199
_refine_ls_wR_factor_ref         0.3541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2402
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06789h2.cif
_cod_data_source_block           exp_4376_auto
_cod_original_formula_sum        'C24.50 H34.50 N0.50 O1.50'
_cod_database_code               1576342
_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
 C1A-C1B
 1.51 with sigma of 0.02
 C1B-C1C = C1B-C1G = C1D-C1E
 1.39 with sigma of 0.02
 C1C-C1D = C1E-C1F = C1F-C1G
 1.38 with sigma of 0.02
 C1A-C1C = C1A-C1G
 2.52 with sigma of 0.04
 C1B-C1D
 2.42 with sigma of 0.04
 C1B-C1F
 2.41 with sigma of 0.04
 C1C-C1E
 2.39 with sigma of 0.04
 C1D-C1F = C1E-C1G
 2.4 with sigma of 0.04
 C1B-C1C \\sim C1C-C1D \\sim C1D-C1E \\sim C1E-C1F \\sim C1F-C1G \\sim C1G-C1B
 with sigma of 0.02
 C1B-C1F \\sim C1B-C1D \\sim C1G-C1E \\sim C1C-C1G \\sim C1D-C1F \\sim C1C-C1E
 with sigma of 0.04
 C1A-C1G \\sim C1A-C1C
 with sigma of 0.04
3. Restrained planarity
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F \\sim C1G: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H2(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5) C1B(0.5) C1C(0.5)
 H1C(0.5) C1D(0.5) H1D(0.5) C1E(0.5) H1E(0.5) C1F(0.5) H1F(0.5) C1G(0.5)
 H1G(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C1G(H1G)
7.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C22(H22A,H22B,H22C), C1A(H1AA,H1AB,H1AC)
7.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 2.913
_oxdiff_exptl_absorpt_empirical_full_min 0.422