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_7064161
_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         'C74 H70 Li2 O4, 2(C7 H8)'
_chemical_formula_sum            'C88 H86 Li2 O4'
_chemical_formula_weight         1221.45
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2025-09-05 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.4110(10)
_cell_angle_beta                 94.4380(10)
_cell_angle_gamma                111.613(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8054(3)
_cell_length_b                   14.1131(3)
_cell_length_c                   24.2657(2)
_cell_measurement_reflns_used    28669
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.2170
_cell_measurement_theta_min      3.6550
_cell_volume                     3427.44(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_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 0.980
_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     25.00  85.00   0.50    2.00    --   48.70-112.00-146.00  120
  2  \w    -83.00 -18.00   0.50    9.50    --  -86.25 112.00 -53.00  130
  3  \w   -154.00 -81.00   0.50    9.50    --  -86.25-112.00-146.00  146
  4  \w     40.00 109.00   0.50    9.50    --  107.75-112.00-146.00  138
  5  \w    103.00 176.00   0.50    9.50    --  107.75 112.00 -53.00  146
  6  \w   -121.00 -39.00   0.50    2.00    --  -48.70 -38.00-180.00  164
  7  \w    -82.00  -3.00   0.50    2.00    --  -48.70 112.00 -53.00  158
  8  \w    -26.00  26.00   0.50    2.00    --  -48.70  19.00-150.00  104
  9  \w    -63.00  24.00   0.50    2.00    --  -48.70  57.00 -60.00  174
 10  \w   -118.00 -73.00   0.50    2.00    --  -48.70-125.00  30.00   90
 11  \w    -25.00  26.00   0.50    2.00    --   48.70 -19.00 120.00  102
 12  \w    -25.00  26.00   0.50    2.00    --   48.70 -19.00  60.00  102
 13  \w   -159.00 -75.00   0.50    9.50    --  -86.25 -30.00-150.00  168
 14  \w   -158.00 -75.00   0.50    9.50    --  -86.25 -45.00 -90.00  166
 15  \w     36.00 105.00   0.50    9.50    --  107.75 -95.00-120.00  138
 16  \w     36.00 166.00   0.50    9.50    --  107.75   0.00  60.00  260
 17  \w     93.00 178.00   0.50    9.50    --  107.75  61.00   0.00  170
 18  \w     38.00 106.00   0.50    9.50    --  107.75-101.00 128.29  136
 19  \w     36.00 166.00   0.50    9.50    --  107.75   0.00  60.00  260
 20  \w     36.00  71.00   0.50    9.50    --  107.75 -61.00 -60.00   70
 21  \w     86.00 178.00   0.50    9.50    --  107.75  77.00 120.00  184
 22  \w     39.00 111.00   0.50    9.50    --  107.75-125.00 -60.00  144
 23  \w     47.00 128.00   0.50    9.50    --  107.75-148.00-136.24  162
 24  \w     39.00 111.00   0.50    9.50    --  107.75-125.00-150.00  144
 25  \w     39.00 111.00   0.50    9.50    --  107.75-125.00 -90.00  144
 26  \w     44.00 125.00   0.50    9.50    --  107.75-143.00  36.57  162
 27  \w     39.00 108.00   0.50    9.50    --  107.75-109.00  51.73  138
 28  \w     97.00 178.00   0.50    9.50    --  107.75  45.00 120.00  162
 29  \w     36.00 105.00   0.50    9.50    --  107.75 -95.00-150.00  138
 30  \w     36.00 105.00   0.50    9.50    --  107.75 -77.00-120.00  138
 31  \w     97.00 178.00   0.50    9.50    --  107.75  30.00  90.00  162
 32  \w     97.00 178.00   0.50    9.50    --  107.75  30.00  60.00  162
 33  \w     36.00 105.00   0.50    9.50    --  107.75 -95.00  60.00  138
 34  \w     36.00 105.00   0.50    9.50    --  107.75 -77.00 120.00  138
 35  \w     39.00  71.00   0.50    9.50    --  107.75 -61.00  30.00   64
 36  \w     39.00 104.00   0.50    9.50    --  107.75-125.00 150.00  130
 37  \w    137.00 163.00   0.50    9.50    --  107.75 125.00-150.00   52
 38  \w     40.00  69.00   0.50    9.50    --  107.75 -61.00 150.00   58
 39  \w    102.00 146.00   0.50    9.50    --  107.75  45.00 -30.00   88
 40  \w     43.00  93.00   0.50    9.50    --  107.75 -77.00 -30.00  100
 41  \w     99.00 125.00   0.50    9.50    --  107.75  61.00-120.00   52
 42  \w     54.00  82.00   0.50    9.50    --  107.75-136.00 124.91   56
 43  \w     86.00 120.00   0.50    9.50    --  107.75-136.00 124.91   68
 44  \w     97.00 134.00   0.50    9.50    --  107.75  15.00 120.00   74
 45  \w     97.00 134.00   0.50    9.50    --  107.75 125.00  60.00   74
 46  \w     36.00  69.00   0.50    9.50    --  107.75 -95.00 -30.00   66
 47  \w    128.00 160.00   0.50    9.50    --  107.75 125.00 120.00   64
 48  \w     95.00 146.00   0.50    9.50    --  107.75  61.00 -90.00  102
 49  \w     89.00 116.00   0.50    9.50    --  107.75  72.00  41.87   54
 50  \w    140.00 172.00   0.50    9.50    --  107.75  72.00  41.87   64
 51  \w     93.00 119.00   0.50    9.50    --  107.75 -87.00 -15.09   52
 52  \w    101.00 142.00   0.50    9.50    --  107.75  30.00-120.00   82
 53  \w     75.00 113.00   0.50    9.50    --  107.75 -83.00-122.41   76
 54  \w     71.00 103.00   0.50    9.50    --  107.75-101.00 -55.09   64
 55  \w     57.00  88.00   0.50    9.50    --  107.75 -77.00  30.00   62
 56  \w     39.00  64.00   0.50    9.50    --  107.75 -77.00  90.00   50
 57  \w     80.00 105.00   0.50    9.50    --  107.75 -77.00  90.00   50
 58  \w     39.00  93.00   0.50    9.50    --  107.75-125.00-120.00  108
 59  \w     83.00 109.00   0.50    9.50    --  107.75-125.00  30.00   52
 60  \w     40.00  66.00   0.50    9.50    --  107.75-125.00 120.00   52
 61  \w     66.00 111.00   0.50    9.50    --  107.75-125.00  60.00   90
 62  \w     55.00 101.00   0.50    9.50    --  107.75 -77.00 -90.00   92
 63  \w    149.00 175.00   0.50    9.50    --  107.75  15.00 120.00   52
 64  \w     38.00  71.00   0.50    9.50    --  107.75 -61.00 120.00   66
 65  \w    119.00 145.00   0.50    9.50    --  107.75 142.00 106.11   52
 66  \w     47.00  72.00   0.50    9.50    --  107.75 -83.00-151.44   50
 67  \w    105.00 130.00   0.50    9.50    --  107.75 -83.00-151.44   50
;
_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      0.1219222000
_diffrn_orient_matrix_UB_12      -0.0210605000
_diffrn_orient_matrix_UB_13      -0.0173366000
_diffrn_orient_matrix_UB_21      -0.0689318000
_diffrn_orient_matrix_UB_22      -0.1133577000
_diffrn_orient_matrix_UB_23      0.0126635000
_diffrn_orient_matrix_UB_31      -0.0638503000
_diffrn_orient_matrix_UB_32      -0.0226437000
_diffrn_orient_matrix_UB_33      -0.0600000000
_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  0.0707
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            83883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.967
_diffrn_reflns_theta_min         3.371
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     912
_refine_ls_number_reflns         14365
_refine_ls_number_restraints     94
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0890
_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^)+(0.1612P)^2^+2.9633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2730
_refine_ls_wR_factor_ref         0.2842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11605
_reflns_number_total             14365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03734d2.cif
_cod_data_source_block           lioartol
_cod_database_code               7064161
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20Li
_chemical_oxdiff_usercomment     LiOArTol
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.810
_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
 C82A-C83A \\sim C82B-C83B \\sim C83A-C84A \\sim C83B-C84B \\sim C84A-C85A
\\sim C84B-C85B \\sim C85A-
 C86A \\sim C85B-C86B \\sim C86A-C87A \\sim C86B-C87B \\sim C87A-C82A \\sim
C87B-C82B
 with sigma of 0.003
 C88A-C85A \\sim C88B-C85B
 with sigma of 0.003
 C88A-C84A \\sim C88B-C84B
 with sigma of 0.003
 C88A-C86A \\sim C88B-C86B
 with sigma of 0.003
 Li1A-O1 \\sim Li1B-O1
 with sigma of 0.003
 O2A-Li1A \\sim O2B-Li1B
 with sigma of 0.003
 O2A-C34A \\sim O2B-C34B
 with sigma of 0.003
 O2A-C37A \\sim O2B-C37B
 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
 Li2A-O3 \\sim Li2B-O3
 with sigma of 0.003
 O4A-Li2A \\sim O4B-Li2B
 with sigma of 0.003
 O4A-C71A \\sim O4B-C71B
 with sigma of 0.003
 O4A-C74A \\sim O4B-C74B
 with sigma of 0.003
 C71A-C72A \\sim C71B-C72B
 with sigma of 0.003
 C72A-C73A \\sim C72B-C73B
 with sigma of 0.003
 C73A-C74A \\sim C73B-C74B
 with sigma of 0.003
 C71A-C74A \\sim C71B-C74B
 with sigma of 0.003
 C72A-C74A \\sim C72B-C74B
 with sigma of 0.003
 C71A-C73A \\sim C71B-C73B
 with sigma of 0.003
3. Restrained planarity
 C82A, C83A, C84A, C85A, C86A, C87A, C88A
 with sigma of 0.1
 C82B, C83B, C84B, C85B, C86B, C87B, C88B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C82A) = Uanis(C82B)
Uanis(C83A) = Uanis(C83B)
Uanis(C84A) = Uanis(C84B)
Uanis(C85A) = Uanis(C85B)
Uanis(C86A) = Uanis(C86B)
Uanis(C87A) = Uanis(C87B)
Uanis(C88A) = Uanis(C88B)
Uanis(Li1A) = Uanis(Li1B)
Uanis(O2A) = Uanis(O2B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C37A) = Uanis(C37B)
Uanis(Li2A) = Uanis(Li2B)
Uanis(O4A) = Uanis(O4B)
Uanis(C71A) = Uanis(C71B)
Uanis(C72A) = Uanis(C72B)
Uanis(C73A) = Uanis(C73B)
Uanis(C74A) = Uanis(C74B)
5. Others
 Sof(C82B)=Sof(H82B)=Sof(C83B)=Sof(H83B)=Sof(C84B)=Sof(H84B)=Sof(C85B)=
 Sof(C86B)=Sof(H86B)=Sof(C87B)=Sof(H87B)=Sof(C88B)=Sof(H88D)=Sof(H88E)=
 Sof(H88F)=1-FVAR(1)
 Sof(C82A)=Sof(H82A)=Sof(C83A)=Sof(H83A)=Sof(C84A)=Sof(H84A)=Sof(C85A)=
 Sof(C86A)=Sof(H86A)=Sof(C87A)=Sof(H87A)=Sof(C88A)=Sof(H88A)=Sof(H88B)=
 Sof(H88C)=FVAR(1)
 Sof(Li1B)=Sof(O2B)=Sof(C34B)=Sof(H34C)=Sof(H34D)=Sof(C35B)=Sof(H35C)=
 Sof(H35D)=Sof(C36B)=Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37C)=Sof(H37D)=1-FVAR(2)
 Sof(Li1A)=Sof(O2A)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(C35A)=Sof(H35A)=
 Sof(H35B)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=Sof(H37B)=FVAR(2)
 Sof(Li2B)=Sof(O4B)=Sof(C74B)=Sof(H74C)=Sof(H74D)=Sof(C73B)=Sof(H73C)=
 Sof(H73D)=Sof(C72B)=Sof(H72C)=Sof(H72D)=Sof(C71B)=Sof(H71C)=Sof(H71D)=1-FVAR(3)
 Sof(Li2A)=Sof(O4A)=Sof(C74A)=Sof(H74A)=Sof(H74B)=Sof(C73A)=Sof(H73A)=
 Sof(H73B)=Sof(C72A)=Sof(H72A)=Sof(H72B)=Sof(C71A)=Sof(H71A)=Sof(H71B)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C21(H21), C44(H44), C58(H58)
6.b Secondary CH2 refined with riding coordinates:
 C74A(H74A,H74B), C73A(H73A,H73B), C72A(H72A,H72B), C71A(H71A,H71B), C74B(H74C,
 H74D), C73B(H73C,H73D), C72B(H72C,H72D), C71B(H71C,H71D), C34A(H34A,H34B),
 C35A(H35A,H35B), C36A(H36A,H36B), C37A(H37A,H37B), C34B(H34C,H34D), C35B(H35C,
 H35D), C36B(H36C,H36D), C37B(H37C,H37D)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C40(H40),
 C42(H42), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53),
  C54(H54), C55(H55), C56(H56), C60(H60), C61(H61), C62(H62), C63(H63),
 C64(H64), C66(H66), C67(H67), C68(H68), C69(H69), C70(H70), C76(H76), C77(H77),
  C78(H78), C79(H79), C80(H80), C82A(H82A), C83A(H83A), C84A(H84A), C86A(H86A),
 C87A(H87A), C82B(H82B), C83B(H83B), C84B(H84B), C86B(H86B), C87B(H87B)
6.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C57(H57A,H57B,H57C), C81(H81A,H81B,H81C), C88A(H88A,H88B,
 H88C), C88B(H88D,H88E,H88F)
;
_shelx_res_checksum              89431
_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 4.261
_oxdiff_exptl_absorpt_empirical_full_min 0.320