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_7064162
_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         'C33 H27 O, C16 H32 Na O8'
_chemical_formula_sum            'C49 H59 Na O9'
_chemical_formula_weight         814.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-10-08
_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
_cell_angle_beta                 106.1050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.18710(10)
_cell_length_b                   19.16610(10)
_cell_length_c                   17.48590(10)
_cell_measurement_reflns_used    44500
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.5590
_cell_measurement_theta_min      2.3080
_cell_volume                     4246.04(5)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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   -122.00 -39.00   0.50    0.30    --  -48.70 -28.00 122.00  166
  2  \w    -27.00  -1.00   0.50    0.30    --  -48.70  28.00 -75.00   52
  3  \w    -20.00   5.00   0.50    0.30    --   48.70 -28.00 122.00   50
  4  \w   -142.00-117.00   0.50    1.20    --  -86.25 -28.00 122.00   50
  5  \w    150.00 176.00   0.50    1.20    --  107.75  28.00 -75.00   52
  6  \w    115.00 142.00   0.50    1.20    --  107.75  28.00 -75.00   54
  7  \w     -8.00  23.00   0.50    0.30    --  -48.70  19.00  60.00   62
  8  \w   -118.00 -73.00   0.50    0.30    --  -48.70-125.00 -90.00   90
  9  \w    -23.00  18.00   0.50    0.30    --   48.70 -19.00 -30.00   82
 10  \w     38.00  93.00   0.50    0.30    --   48.70  28.00 -75.00  110
 11  \w    -25.00  25.00   0.50    0.30    --   48.70 -19.00   0.00  100
 12  \w    -47.00 -15.00   0.50    1.20    --  -86.25  45.00  90.00   64
 13  \w    -50.00 -14.00   0.50    1.20    --  -86.25  45.00   0.00   72
 14  \w    113.00 145.00   0.50    1.20    --  107.75  61.00 120.00   64
 15  \w     66.00  92.00   0.50    1.20    --  107.75 -95.00  30.00   52
 16  \w     37.00  69.00   0.50    1.20    --  107.75 -61.00  30.00   64
 17  \w     36.00  61.00   0.50    1.20    --  107.75 -61.00  60.00   50
 18  \w    105.00 165.00   0.50    1.20    --  107.75  15.00  60.00  120
 19  \w     93.00 138.00   0.50    1.20    --  107.75  61.00 150.00   90
 20  \w     36.00  76.00   0.50    1.20    --  107.75 -77.00  30.00   80
 21  \w     46.00 101.00   0.50    1.20    --  107.75-112.00  27.72  110
 22  \w    138.00 178.00   0.50    1.20    --  107.75  15.00 -90.00   80
 23  \w     41.00  70.00   0.50    1.20    --  107.75 -60.00-163.92   58
 24  \w    110.00 135.00   0.50    1.20    --  107.75  15.00 -90.00   50
 25  \w    105.00 131.00   0.50    1.20    --  107.75 -80.00  84.16   52
 26  \w     60.00 105.00   0.50    1.20    --  107.75 -77.00   0.00   90
 27  \w     44.00  69.00   0.50    1.20    --  107.75-110.00 135.65   50
 28  \w     36.00  91.00   0.50    1.20    --  107.75 -77.00-150.00  110
 29  \w     45.00 103.00   0.50    1.20    --  107.75 -77.00 -60.00  116
 30  \w    120.00 176.00   0.50    1.20    --  107.75 125.00 -60.00  112
 31  \w     36.00  67.00   0.50    1.20    --  107.75 -61.00-120.00   62
 32  \w     97.00 178.00   0.50    1.20    --  107.75  15.00 120.00  162
 33  \w     48.00 105.00   0.50    1.20    --  107.75 -77.00-180.00  114
 34  \w     36.00  66.00   0.50    1.20    --  107.75 -61.00-180.00   60
 35  \w     38.00  77.00   0.50    1.20    --  107.75 -77.00 -30.00   78
 36  \w     37.00  70.00   0.50    1.20    --  107.75 -61.00   0.00   66
 37  \w     68.00  93.00   0.50    1.20    --  107.75 -77.00-120.00   50
 38  \w    116.00 171.00   0.50    1.20    --  107.75  61.00 -30.00  110
 39  \w     79.00 105.00   0.50    1.20    --  107.75 -95.00 -30.00   52
 40  \w     36.00  62.00   0.50    1.20    --  107.75 -95.00 -30.00   52
 41  \w     39.00  70.00   0.50    1.20    --  107.75 -61.00-150.00   62
 42  \w    127.00 167.00   0.50    1.20    --  107.75 125.00  60.00   80
 43  \w     39.00  75.00   0.50    1.20    --  107.75 -95.00  92.01   72
 44  \w     44.00  70.00   0.50    1.20    --  107.75 -80.00  84.16   52
 45  \w     95.00 121.00   0.50    1.20    --  107.75 -82.00-119.47   52
 46  \w     58.00  84.00   0.50    1.20    --  107.75 -88.00-110.86   52
 47  \w     86.00 112.00   0.50    1.20    --  107.75 -88.00-110.86   52
 48  \w     39.00  71.00   0.50    1.20    --  107.75-106.00 -16.82   64
 49  \w     36.00  81.00   0.50    1.20    --  107.75 -95.00-180.00   90
 50  \w     78.00 104.00   0.50    1.20    --  107.75-110.00 135.65   52
 51  \w     55.00  81.00   0.50    1.20    --  107.75-100.00-148.23   52
 52  \w     57.00  83.00   0.50    1.20    --  107.75-125.00-180.00   52
 53  \w    100.00 126.00   0.50    1.20    --  107.75  45.00  60.00   52
 54  \w     95.00 126.00   0.50    1.20    --  107.75 125.00 -90.00   62
 55  \w    139.00 165.00   0.50    1.20    --  107.75 125.00 150.00   52
 56  \w     38.00  71.00   0.50    1.20    --  107.75 -61.00 -30.00   66
;
_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      0.0871347000
_diffrn_orient_matrix_UB_12      -0.0267613000
_diffrn_orient_matrix_UB_13      0.0722469000
_diffrn_orient_matrix_UB_21      -0.0829305000
_diffrn_orient_matrix_UB_22      -0.0117113000
_diffrn_orient_matrix_UB_23      0.0458200000
_diffrn_orient_matrix_UB_31      -0.0180760000
_diffrn_orient_matrix_UB_32      -0.0748419000
_diffrn_orient_matrix_UB_33      -0.0330301000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            60706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.875
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.784
_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            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         8992
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0391P)^2^+1.7741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8553
_reflns_number_total             8992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03734d2.cif
_cod_data_source_block           naoar_crown_3
_cod_original_cell_volume        4246.03(5)
_cod_database_code               7064162
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10O5Na
_chemical_oxdiff_usercomment     NaOAr_Crown_3
_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
 O2A-C40A \\sim O2B-C40B
 with sigma of 0.003
 C40A-C41A \\sim C40B-C41B
 with sigma of 0.003
 C41A-O3A \\sim C41B-O3B
 with sigma of 0.003
 O3A-C34A \\sim O3B-C34B
 with sigma of 0.003
 C34A-C35A \\sim C34B-C35B
 with sigma of 0.003
 C35A-O4A \\sim C35B-O4B
 with sigma of 0.003
 O4A-C36A \\sim O4B-C36B
 with sigma of 0.003
 C36A-C37A \\sim C36B-C37B
 with sigma of 0.003
 O5A-C37A \\sim O5B-C37B
 with sigma of 0.003
 O5A-C38A \\sim O5B-C38B
 with sigma of 0.003
 C39A-C38A \\sim C39B-C38B
 with sigma of 0.003
 C39A-O2A \\sim C39B-O2B
 with sigma of 0.003
 O2A-Na1 \\sim O2B-Na1
 with sigma of 0.003
 O3A-Na1 \\sim O3B-Na1
 with sigma of 0.003
 O4A-Na1 \\sim O4B-Na1
 with sigma of 0.003
 O5A-Na1 \\sim O5B-Na1
 with sigma of 0.003
 C39A-C40A \\sim C39B-C40B
 with sigma of 0.003
 C34A-C41A \\sim C34B-C41B
 with sigma of 0.003
 C35A-C36A \\sim C35B-C36B
 with sigma of 0.003
 C37A-C38A \\sim C37B-C38B
 with sigma of 0.003
 C21-C28A \\sim C21-C28B
 with sigma of 0.003
 C28A-C29A \\sim C28B-C29B
 with sigma of 0.003
 C29A-C30A \\sim C29B-C30B
 with sigma of 0.003
 C30A-C31A \\sim C30B-C31B
 with sigma of 0.003
 C31A-C32A \\sim C31B-C32B
 with sigma of 0.003
 C32A-C33A \\sim C32B-C33B
 with sigma of 0.003
 C33A-C28A \\sim C33B-C28B
 with sigma of 0.003
 C28A-C30A \\sim C28B-C30B
 with sigma of 0.003
 C29A-C31A \\sim C29B-C31B
 with sigma of 0.003
 C30A-C32A \\sim C30B-C32B
 with sigma of 0.003
 C31A-C33A \\sim C31B-C33B
 with sigma of 0.003
 C32A-C28A \\sim C32B-C28B
 with sigma of 0.003
 C33A-C29A \\sim C33B-C29B
 with sigma of 0.003
 C21-C22A \\sim C21-C22B
 with sigma of 0.003
 C22A-C23A \\sim C22B-C23B
 with sigma of 0.003
 C23A-C24A \\sim C23B-C24B
 with sigma of 0.003
 C24A-C25A \\sim C24B-C25B
 with sigma of 0.003
 C25A-C26A \\sim C25B-C26B
 with sigma of 0.003
 C26A-C27A \\sim C26B-C27B
 with sigma of 0.003
 C27A-C22A \\sim C27B-C22B
 with sigma of 0.003
 C22A-C24A \\sim C22B-C24B
 with sigma of 0.003
 C23A-C25A \\sim C23B-C25B
 with sigma of 0.003
 C24A-C26A \\sim C24B-C26B
 with sigma of 0.003
 C25A-C27A \\sim C25B-C27B
 with sigma of 0.003
 C26A-C22A \\sim C26B-C22B
 with sigma of 0.003
 C27A-C23A \\sim C27B-C23B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) = Uanis(O2B)
Uanis(O3A) = Uanis(O3B)
Uanis(O4A) = Uanis(O4B)
Uanis(O5A) = Uanis(O5B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C37A) = Uanis(C37B)
Uanis(C38A) = Uanis(C38B)
Uanis(C39A) = Uanis(C39B)
Uanis(C40A) = Uanis(C40B)
Uanis(C41A) = Uanis(C41B)
Uanis(C28A) = Uanis(C28B)
Uanis(C29A) = Uanis(C29B)
Uanis(C30A) = Uanis(C30B)
Uanis(C31A) = Uanis(C31B)
Uanis(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C24A) = Uanis(C24B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
Uanis(C27A) = Uanis(C27B)
4. Others
 Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(O5B)=Sof(C34B)=Sof(H34C)=Sof(H34D)=Sof(C35B)=
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37C)=
 Sof(H37D)=Sof(C38B)=Sof(H38C)=Sof(H38D)=Sof(C39B)=Sof(H39C)=Sof(H39D)=
 Sof(C40B)=Sof(H40C)=Sof(H40D)=Sof(C41B)=Sof(H41C)=Sof(H41D)=1-FVAR(1)
 Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(O5A)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(C35A)=
 Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=
 Sof(H37B)=Sof(C38A)=Sof(H38A)=Sof(H38B)=Sof(C39A)=Sof(H39A)=Sof(H39B)=
 Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(C41A)=Sof(H41A)=Sof(H41B)=FVAR(1)
 Sof(C28B)=Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=
 Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(H33B)=1-FVAR(2)
 Sof(C28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=
 Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=FVAR(2)
 Sof(H21A)=Sof(C22B)=Sof(C23B)=Sof(H23B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=
 Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=1-FVAR(3)
 Sof(H21)=Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C21(H21), C21(H21A)
5.b Secondary CH2 refined with riding coordinates:
 C34A(H34A,H34B), C35A(H35A,H35B), C36A(H36A,H36B), C37A(H37A,H37B), C38A(H38A,
 H38B), C39A(H39A,H39B), C40A(H40A,H40B), C41A(H41A,H41B), C34B(H34C,H34D),
 C35B(H35C,H35D), C36B(H36C,H36D), C37B(H37C,H37D), C38B(H38C,H38D), C39B(H39C,
 H39D), C40B(H40C,H40D), C41B(H41C,H41D), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B),
  C49(H49A,H49B)
5.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), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A), C27A(H27A), C23B(H23B), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A),
 C29B(H29B), C30B(H30B), C31B(H31B), C32B(H32B), C33B(H33B)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              42712
_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.771