Photostable triphenylmethyl-based diradicals with a degenerate singlet-triplet ground state and strong photoluminescence.
Arnold, Mona E.; Lebzelter, Anika; Thielert, Philipp; Blinder, Rémi; Schmid, Jonas; Zolg, Julia; Spatola, Emanuele; Jelezko, Fedor; von Delius, Max; Richert, Sabine; Kuehne, Alexander J. C.; Chemical science 16 (2025) 14616–14624; doi:10.1039/d5sc03673a

data_1575066
_publ_section_title
;
 Photostable triphenylmethyl-based diradicals with a degenerate
 singlet-triplet ground state and strong photoluminescence.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              14616
_journal_page_last               14624
_journal_paper_doi               10.1039/d5sc03673a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C56 H22 Cl16 N2, 1.3[C7H8]'
_chemical_formula_sum            'C65.1 H32.4 Cl16 N2'
_chemical_formula_weight         1409.73
_chemical_name_systematic        'Syn 1'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                108.813(11)
_cell_angle_beta                 97.313(12)
_cell_angle_gamma                93.276(11)
_cell_formula_units_Z            2
_cell_length_a                   8.2856(12)
_cell_length_b                   17.898(2)
_cell_length_c                   21.953(3)
_cell_measurement_reflns_used    1217
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      62.2740
_cell_measurement_theta_min      4.2080
_cell_volume                     3039.8(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (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      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_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   -116.00 -28.00   1.00    2.00    --  -42.81 -38.00 150.00   88
  2  \w    -70.00 -10.00   1.00    2.00    --  -42.81 125.00-150.00   60
  3  \w   -117.00 -23.00   1.00    2.00    --  -42.81 -38.00  60.00   94
  4  \w    -71.00 -14.00   1.00    2.00    --  -42.81 125.00 -60.00   57
  5  \w     56.00  93.00   1.00    2.00    --   42.81-125.00-180.00   37
  6  \w     58.00 113.00   1.00    8.00    --  104.63-125.00   0.00   55
  7  \w     28.00 132.00   1.00    8.00    --  104.63 -30.00 -90.00  104
  8  \w     42.00 125.00   1.00    8.00    --  104.63 -45.00-180.00   83
  9  \w    103.00 147.00   1.00    8.00    --  104.63  77.00 -90.00   44
 10  \w     63.00 132.00   1.00    8.00    --  104.63 -61.00 -60.00   69
 11  \w    117.00 162.00   1.00    8.00    --  104.63  77.00 -60.00   45
 12  \w     26.00 106.00   1.00    8.00    --  104.63 -95.00 150.00   80
 13  \w     97.00 124.00   1.00    8.00    --  104.63 -77.00-180.00   27
 14  \w     84.00 113.00   1.00    8.00    --  104.63-125.00  90.00   29
 15  \w     28.00  70.00   1.00    8.00    --  104.63 -77.00-180.00   42
 16  \w     78.00 173.00   1.00    8.00    --  104.63  30.00-120.00   95
 17  \w    108.00 142.00   1.00    8.00    --  104.63  77.00 150.00   34
 18  \w     71.00 113.00   1.00    8.00    --  104.63-125.00 -90.00   42
 19  \w     39.00 120.00   1.00    8.00    --  104.63-135.00 145.46   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0720307000
_diffrn_orient_matrix_UB_12      0.0799093000
_diffrn_orient_matrix_UB_13      0.0243891000
_diffrn_orient_matrix_UB_21      -0.1518268000
_diffrn_orient_matrix_UB_22      -0.0331226000
_diffrn_orient_matrix_UB_23      -0.0526728000
_diffrn_orient_matrix_UB_31      -0.0853767000
_diffrn_orient_matrix_UB_32      -0.0296308000
_diffrn_orient_matrix_UB_33      0.0475477000
_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  0.1930
_diffrn_reflns_av_unetI/netI     0.2999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22156
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.281
_diffrn_reflns_theta_min         3.909
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.978
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       needle
_exptl_crystal_F_000             1418
_exptl_crystal_preparation       'Hexane diffusion in toluene'
_exptl_crystal_recrystallization_method 'Hexane diffusion in toluene'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         11740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.1899
_refine_ls_R_factor_gt           0.0882
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1854
_refine_ls_wR_factor_ref         0.2727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3973
_reflns_number_total             11740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03673a2.cif
_cod_data_source_block           esp24160_auto
_cod_depositor_comments          'Adding full bibliography for 1575066.cif.'
_cod_original_cell_volume        3039.7(7)
_cod_original_formula_sum        'C65.10 H32.40 Cl16 N2'
_cod_database_code               1575066
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C56 H22 Cl16 N2'
_chemical_oxdiff_usercomment     ESSyn1
_shelx_estimated_absorpt_t_max   0.818
_shelx_estimated_absorpt_t_min   0.264
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00M(H00M), C00P(H00P), C00S(H00S), C00T(H00T), C00V(H00V),
 C012(H012), C014(H014), C016(H016), C019(H019), C01A(H01A), C01E(H01E),
 C01G(H01G), C01J(H01J), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O),
 C01V(H01V), C01W(H01W), C01Y(H01Y), C022(H022)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              68268
_shelx_fab_checksum              6992
_olex2_submission_original_sample_id 'Syn 1'
_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 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.508