Synthesis, Structural and Photophysical Studies of Mono-and Dinuclear Alkali Metal 2,6-dibenzhydryl-4-methylphenolates
Bardonov, Daniil; Nasyrova, Darina; Metlin, Mikhail T.; Minyaev, Mikhail E.; Taydakov, Ilya V.; Roitershtein, Dmitrii M.; New Journal of Chemistry  (2026) –; doi:10.1039/D5NJ03734D

data_7064158
_publ_section_title
;
 Synthesis, Structural and Photophysical Studies of Mono-and Dinuclear
 Alkali Metal 2,6-dibenzhydryl-4-methylphenolates
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03734D
_journal_year                    2026
_chemical_formula_moiety         'C76 H64 Li2 N2 O2, 4(C5 H5 N)'
_chemical_formula_sum            'C96 H84 Li2 N6 O2'
_chemical_formula_weight         1367.57
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-12-03
_audit_creation_method
;
Olex2 1.5-ac7-016
(compiled 2025.05.29 svn.r8cd99b3d for Rigaku Oxford Diffraction, GUI svn.r7254)
;
_audit_update_record
;
2025-12-03 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.6426(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.85728(16)
_cell_length_b                   17.91332(8)
_cell_length_c                   15.50682(8)
_cell_measurement_reflns_used    39252
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      79.3690
_cell_measurement_theta_min      2.9410
_cell_volume                     7605.05(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-ac7-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    -26.00  26.00   0.50    1.50    --  -48.68  19.00  22.00  104
  2  \w   -122.00 -39.00   0.50    1.50    --  -48.68 -19.00-145.00  166
  3  \w    -25.00  26.00   0.50    1.50    --   48.68 -19.00-145.00  102
  4  \w     39.00 123.00   0.50    1.50    --   48.68  19.00  22.00  168
  5  \w   -163.00 -79.00   0.50    4.00    --  -90.00 -19.00-145.00  168
  6  \w    102.00 178.00   0.50    4.00    --  111.50  19.00  22.00  152
  7  \w    -26.00  26.00   0.50    1.50    --  -48.68  19.00-180.00  104
  8  \w     34.00  93.00   0.50    1.50    --   48.68-125.00-150.00  118
  9  \w    -25.00  26.00   0.50    1.50    --   48.68 -19.00  90.00  102
 10  \w    -51.00 -18.00   0.50    4.00    --  -90.00  45.00   0.00   66
 11  \w     41.00 107.00   0.50    4.00    --  111.50-105.00-142.60  132
 12  \w    101.00 178.00   0.50    4.00    --  111.50  30.00 -60.00  154
 13  \w     40.00 105.00   0.50    4.00    --  111.50 -77.00 150.00  130
 14  \w     42.00 111.00   0.50    4.00    --  111.50-125.00 150.00  138
 15  \w     40.00  71.00   0.50    4.00    --  111.50 -61.00 120.00   62
 16  \w    111.00 177.00   0.50    4.00    --  111.50  30.00-120.00  132
 17  \w    131.00 157.00   0.50    4.00    --  111.50  15.00 -90.00   52
 18  \w     63.00  89.00   0.50    4.00    --  111.50 -77.00 120.00   52
 19  \w     42.00 109.00   0.50    4.00    --  111.50-125.00 120.00  134
 20  \w    102.00 178.00   0.50    4.00    --  111.50  15.00-180.00  152
 21  \w    118.00 158.00   0.50    4.00    --  111.50  30.00 -30.00   80
 22  \w     46.00  71.00   0.50    4.00    --  111.50 -61.00 -30.00   50
 23  \w    134.00 166.00   0.50    4.00    --  111.50  30.00  90.00   64
 24  \w     42.00 102.00   0.50    4.00    --  111.50 -95.00  30.00  120
 25  \w    127.00 164.00   0.50    4.00    --  111.50 125.00-120.00   74
 26  \w    103.00 175.00   0.50    4.00    --  111.50  45.00-150.00  144
 27  \w    107.00 146.00   0.50    4.00    --  111.50 125.00-180.00   78
 28  \w     40.00  77.00   0.50    4.00    --  111.50 -77.00 -30.00   74
 29  \w    110.00 136.00   0.50    4.00    --  111.50  -2.00  33.40   52
 30  \w     74.00 104.00   0.50    4.00    --  111.50 -95.00 150.00   60
 31  \w     40.00  65.00   0.50    4.00    --  111.50 -61.00  60.00   50
 32  \w     45.00  71.00   0.50    4.00    --  111.50 -61.00  90.00   52
 33  \w     47.00  73.00   0.50    4.00    --  111.50 -83.00 160.62   52
 34  \w     90.00 135.00   0.50    4.00    --  111.50 -83.00 160.62   90
 35  \w     59.00  85.00   0.50    4.00    --  111.50 -77.00  60.00   52
 36  \w     62.00  88.00   0.50    4.00    --  111.50  -2.00  33.40   52
 37  \w    101.00 129.00   0.50    4.00    --  111.50  30.00  90.00   56
 38  \w     74.00 107.00   0.50    4.00    --  111.50-110.00 134.09   66
 39  \w     40.00  65.00   0.50    4.00    --  111.50 -61.00-150.00   50
 40  \w     40.00  66.00   0.50    4.00    --  111.50 -77.00 -60.00   52
 41  \w     61.00  87.00   0.50    4.00    --  111.50 -77.00   0.00   52
 42  \w     76.00 101.00   0.50    4.00    --  111.50 -95.00 120.00   50
 43  \w    101.00 134.00   0.50    4.00    --  111.50  45.00 -90.00   66
 44  \w    120.00 167.00   0.50    4.00    --  111.50  30.00-150.00   94
 45  \w     40.00  71.00   0.50    4.00    --  111.50 -77.00  90.00   62
 46  \w     96.00 122.00   0.50    4.00    --  111.50 -87.00  27.52   52
 47  \w     41.00  68.00   0.50    4.00    --  111.50 -61.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0358078000
_diffrn_orient_matrix_UB_12      -0.0102667000
_diffrn_orient_matrix_UB_13      -0.0638475000
_diffrn_orient_matrix_UB_21      -0.0411595000
_diffrn_orient_matrix_UB_22      0.0189492000
_diffrn_orient_matrix_UB_23      -0.0777321000
_diffrn_orient_matrix_UB_31      0.0137926000
_diffrn_orient_matrix_UB_32      0.0832560000
_diffrn_orient_matrix_UB_33      0.0099483000
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.549
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2896
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.145
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         8178
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+7.3175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7756
_reflns_number_total             8178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03734d2.cif
_cod_data_source_block           LiOArPy
_cod_database_code               7064158
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20O2N2Li
_chemical_oxdiff_usercomment     LiOArPy
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.825
_diffrn_oxdiff_digest_hkl
;
019bda3bc09e1d20e7246f16312f8bdfbaefdd
;
_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. Restrained distances
 Li1-N1A \\sim Li1-N1B
 with sigma of 0.003
 N1A-C34A \\sim N1B-C34B
 with sigma of 0.003
 C34A-C35A \\sim C34B-C35B
 with sigma of 0.003
 C35A-C36A \\sim C35B-C36B
 with sigma of 0.003
 C36A-C37A \\sim C36B-C37B
 with sigma of 0.003
 C37A-C38A \\sim C37B-C38B
 with sigma of 0.003
 C38A-N1A \\sim C38B-N1B
 with sigma of 0.003
 N1A-C35A \\sim N1B-C35B
 with sigma of 0.003
 C34A-C36A \\sim C34B-C36B
 with sigma of 0.003
 C35A-C37A \\sim C35B-C37B
 with sigma of 0.003
 C36A-C38A \\sim C36B-C38B
 with sigma of 0.003
 C37A-N1A \\sim C37B-N1B
 with sigma of 0.003
 C38A-C34A \\sim C38B-C34B
 with sigma of 0.003
 C7-C8A \\sim C7-C8B
 with sigma of 0.003
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.003
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.003
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.003
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.003
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.003
 C8A-C10A \\sim C8B-C10B
 with sigma of 0.003
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.003
 C10A-C12A \\sim C10B-C12B
 with sigma of 0.003
 C11A-C13A \\sim C11B-C13B
 with sigma of 0.003
 C12A-C8A \\sim C12B-C8B
 with sigma of 0.003
 C13A-C9A \\sim C13B-C9B
 with sigma of 0.003
 C7-C14A \\sim C7-C14B
 with sigma of 0.003
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.003
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.003
 C16A-C17A \\sim C16B-C17B
 with sigma of 0.003
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.003
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.003
 C14A-C19A \\sim C14B-C19B
 with sigma of 0.003
 C14A-C16A \\sim C14B-C16B
 with sigma of 0.003
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.003
 C16A-C18A \\sim C16B-C18B
 with sigma of 0.003
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.003
 C18A-C14A \\sim C18B-C14B
 with sigma of 0.003
 C19A-C15A \\sim C19B-C15B
 with sigma of 0.003
 N2A-C40A \\sim N2B-C40B \\sim C44A-N2A \\sim C44B-N2B
 with sigma of 0.02
 C40A-C41A \\sim C40B-C41B \\sim C43A-C44A \\sim C43B-C44B
 with sigma of 0.02
 C41A-C42A \\sim C41B-C42B \\sim C42A-C43A \\sim C42B-C43B
 with sigma of 0.02
3. Restrained planarity
 N2A, C40A, C41A, C42A, C43A, C44A
 with sigma of 0.1
 N2B, C40B, C41B, C42B, C43B, C44B
 with sigma of 0.1
 N1A, C34A, C35A, C36A, C37A, C38A
 with sigma of 0.1
 N1B, C34B, C35B, C36B, C37B, C38B
 with sigma of 0.1
 C8A, C9A, C10A, C11A, C12A, C13A
 with sigma of 0.1
 C8B, C9B, C10B, C11B, C12B, C13B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C11A)
\\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq: with sigma of 0.001
and sigma for terminal atoms of 0.002
Uanis(N1A) = Uanis(N1B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C37A) = Uanis(C37B)
Uanis(C38A) = Uanis(C38B)
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(C14B)
Uanis(C15A) = Uanis(C15B)
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(N2A) = Uanis(N2B)
Uanis(C40A) = Uanis(C40B)
Uanis(C41A) = Uanis(C41B)
Uanis(C42A) = Uanis(C42B)
Uanis(C43A) = Uanis(C43B)
Uanis(C44A) = Uanis(C44B)
5. Others
 Sof(N1B)=Sof(C34B)=Sof(H34B)=Sof(C35B)=Sof(H35B)=Sof(C36B)=Sof(H36B)=
 Sof(C37B)=Sof(H37B)=Sof(C38B)=Sof(H38B)=1-FVAR(1)
 Sof(N1A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=FVAR(1)
 Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(2)
 Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(2)
 Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=1-FVAR(3)
 Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=FVAR(3)
 Sof(N2B)=Sof(C40B)=Sof(H40B)=Sof(C41B)=Sof(H41B)=Sof(C42B)=Sof(H42B)=
 Sof(C43B)=Sof(H43B)=Sof(C44B)=Sof(H44B)=1-FVAR(4)
 Sof(N2A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(H42A)=
 Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C21(H21)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C15B(H15B), C16B(H16B),
 C17B(H17B), C18B(H18B), C19B(H19B), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C34A(H34A),
 C35A(H35A), C36A(H36A), C37A(H37A), C38A(H38A), C34B(H34B), C35B(H35B),
 C36B(H36B), C37B(H37B), C38B(H38B), C40A(H40A), C41A(H41A), C42A(H42A),
 C43A(H43A), C44A(H44A), C40B(H40B), C41B(H41B), C42B(H42B), C43B(H43B),
 C44B(H44B)
6.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              25341
_shelx_fab_checksum              66893
_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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.566