Unlocking iminodioxocines and amine-bis(phenols) <i>via</i> sterically guided ammonia condensation: a shortcut to tunable ONO pincer ligands.
Strunin, Daniil; Pak, Alexandra; Khakina, Ekaterina; Solov'eva, Svetlana; Nelyubina, Yulia; Nikovskiy, Igor; Organic & biomolecular chemistry 23 (2025) 8332–8340; doi:10.1039/d5ob01127b

data_7160704
_publ_section_title
;
 Unlocking iminodioxocines and amine-bis(phenols) <i>via</i> sterically
 guided ammonia condensation: a shortcut to tunable ONO pincer ligands.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8332
_journal_page_last               8340
_journal_paper_doi               10.1039/d5ob01127b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C42 H53 N O2'
_chemical_formula_sum            'C42 H53 N O2'
_chemical_formula_weight         603.85
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_audit_update_record
;
2025-06-19 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                106.343(4)
_cell_angle_beta                 94.889(4)
_cell_angle_gamma                97.001(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5731(16)
_cell_length_b                   13.252(2)
_cell_length_c                   15.012(3)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.43
_cell_volume                     1799.5(5)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.1237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8421.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         8704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0573P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4451
_reflns_number_total             8704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01127b2.cif
_cod_data_source_block           5bOx
_cod_depositor_comments
'Adding full bibliography for 7160703--7160705.cif.'
_cod_database_code               7160704
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O1(H1A), O2(H2)
2.b Ternary CH refined with riding coordinates:
 C1(H1)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C20(H20), C22(H22), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              6979
_olex2_submission_special_instructions 'No special instructions were received'