#------------------------------------------------------------------------------
#$Date: 2025-11-28 00:27:35 +0100 (Fri 28 de Nov de 2025) $
#$Revision: 303463 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/63/1576343.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1576343
loop_
_publ_author_name
'Hong, Qiong-Yan'
'Huang, Bin'
'Niu, Yan-Fei'
'Wang, Cui-Hong'
'Zhao, Xiao-li'
'Yang, Hai-Bo'
'Shi, Xueliang'
_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'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00   2.00   1.00    1.00    --    0.00 -37.00 150.00   42
  2  ω    -65.00 -40.00   1.00    1.00    --    0.00 -77.00 -30.00   25
  3  ω     59.00  84.00   1.00    1.00    --    0.00  57.00 -90.00   25
  4  ω    -26.00  88.00   1.00    1.00    --    0.00  37.00  30.00  114
  5  ω    -24.00  25.00   1.00    1.00    --    0.00 -57.00  30.00   49
  6  ω    -54.00 -29.00   1.00    1.00    --    0.00 -57.00  30.00   25
  7  ω     10.00  35.00   1.00    1.00    --    0.00 -19.00-180.00   25
  8  ω    -85.00 -55.00   1.00    1.00    --    0.00 -57.00  30.00   30
  9  ω      3.00  34.00   1.00    3.00    --   92.10 -82.00 -30.00   31
 10  ω      4.00 128.00   1.00    3.00    --   92.10 -82.00 -90.00  124
 11  ω      6.00  88.00   1.00    3.00    --   92.10 -61.00 -90.00   82
 12  ω     75.00 169.00   1.00    3.00    --   92.10  45.00 120.00   94
 13  ω      6.00  32.00   1.00    3.00    --   92.10 -82.00  60.00   26
 14  ω     93.00 126.00   1.00    3.00    --   92.10 -82.00  60.00   33
 15  ω      5.00 127.00   1.00    3.00    --   92.10 -82.00   0.00  122
 16  ω     60.00 122.00   1.00    3.00    --   92.10 -82.00 150.00   62
 17  ω     75.00 101.00   1.00    3.00    --   92.10  30.00  30.00   26
 18  ω     67.00 182.00   1.00    3.00    --   92.10  45.00-120.00  115
 19  ω      3.00 119.00   1.00    3.00    --   92.10 -61.00   0.00  116
 20  ω     66.00 176.00   1.00    3.00    --   92.10  45.00-150.00  110
 21  ω     78.00 103.00   1.00    3.00    --   92.10 -82.00-150.00   25
 22  ω     75.00 100.00   1.00    3.00    --   92.10 -82.00 -30.00   25
 23  ω     54.00  94.00   1.00    3.00    --   92.10 -82.00 120.00   40
 24  ω      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       'ω 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/[σ²(Fo²)+(0.1873P)²+0.4560P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53879(12) 1.0776(2) 0.250000 0.149(2) Uani 1 2 d S T P . .
N1 N 0.333333 0.666667 0.250000 0.0463(11) Uani 1 6 d S T P . .
C1 C 0.38627(12) 0.7725(2) 0.250000 0.0527(9) Uani 1 2 d S T P . .
C2 C 0.47921(19) 0.82467(18) 0.3082(2) 0.0564(8) Uani 1 1 d . . . . .
H2 H 0.504810 0.788016 0.347771 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5329(2) 0.9274(2) 0.3082(3) 0.0750(10) Uani 1 1 d . . . . .
C4 C 0.49110(14) 0.9822(3) 0.250000 0.0859(15) Uani 1 2 d S T P . .
C5 C 0.6361(3) 0.9835(2) 0.3699(3) 0.0929(13) Uani 1 1 d . . . . .
C6 C 0.6330(4) 1.0492(4) 0.4681(5) 0.143(2) Uani 1 1 d . . . . .
H6A H 0.627063 1.104764 0.435119 0.215 Uiso 1 1 calc R U . . .
H6B H 0.694938 1.076222 0.513731 0.215 Uiso 1 1 calc R U . . .
H6C H 0.575057 1.008518 0.518076 0.215 Uiso 1 1 calc R U . . .
C7 C 0.7162(3) 1.0473(3) 0.2808(4) 0.131(2) Uani 1 1 d . . . . .
H7A H 0.716671 1.003954 0.218877 0.196 Uiso 1 1 calc R U . . .
H7B H 0.782227 1.081808 0.318399 0.196 Uiso 1 1 calc R U . . .
H7C H 0.701155 1.097140 0.248006 0.196 Uiso 1 1 calc R U . . .
C8 C 0.6646(2) 0.9118(3) 0.4241(3) 0.0964(14) Uani 1 1 d . . . . .
H8A H 0.613617 0.869665 0.481257 0.145 Uiso 1 1 calc R U . . .
H8B H 0.729993 0.950053 0.462482 0.145 Uiso 1 1 calc R U . . .
H8C H 0.668666 0.869035 0.363865 0.145 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 120.000(1) . 2_665 ?
C1 N1 C1 120.000(1) . 3_565 ?
C1 N1 C1 120.0 2_665 3_565 ?
N1 C1 C2 119.47(15) . 5 ?
N1 C1 C2 119.47(15) . . ?
C2 C1 C2 121.1(3) . 5 ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 C5 120.1(3) . . ?
C4 C3 C5 121.1(3) . . ?
O1 C4 C3 120.10(17) . . ?
O1 C4 C3 120.09(17) . 5 ?
C3 C4 C3 119.8(3) 5 . ?
C6 C5 C3 110.2(3) . . ?
C7 C5 C3 108.7(3) . . ?
C7 C5 C6 110.9(4) . . ?
C8 C5 C3 112.0(3) . . ?
C8 C5 C6 106.8(3) . . ?
C8 C5 C7 108.3(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.269(5) . ?
N1 C1 1.409(3) 3_565 ?
N1 C1 1.409(3) . ?
N1 C1 1.409(3) 2_665 ?
C1 C2 1.410(3) 5 ?
C1 C2 1.410(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(4) . ?
C3 C4 1.454(3) . ?
C3 C5 1.549(4) . ?
C5 C6 1.534(6) . ?
C5 C7 1.525(5) . ?
C5 C8 1.510(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.1(2) . . . . ?
C1 N1 C1 C2 -33.17(12) 3_565 . . . ?
C1 N1 C1 C2 -33.17(12) 2_665 . . 5 ?
C1 N1 C1 C2 146.83(12) 3_565 . . 5 ?
C1 N1 C1 C2 146.83(12) 2_665 . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
C1 C2 C3 C5 -178.5(3) . . . . ?
C2 C1 C2 C3 -0.9(2) 5 . . . ?
C2 C3 C4 O1 179.1(2) . . . . ?
C2 C3 C4 C3 -0.9(2) . . . 5 ?
C2 C3 C5 C6 -118.4(4) . . . . ?
C2 C3 C5 C7 119.9(4) . . . . ?
C2 C3 C5 C8 0.3(5) . . . . ?
C4 C3 C5 C6 61.3(4) . . . . ?
C4 C3 C5 C7 -60.4(5) . . . . ?
C4 C3 C5 C8 -179.9(3) . . . . ?
C5 C3 C4 O1 -0.6(3) . . . . ?
C5 C3 C4 C3 179.4(3) . . . 5 ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.525 395.0 94.3 ?
2 0.333 0.667 0.750 169.7 46.2 ?
3 0.667 0.333 0.250 169.7 46.2 ?
