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_7160705
_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         'C38 H63 N O2'
_chemical_formula_sum            'C38 H63 N O2'
_chemical_formula_weight         565.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 95.845(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6175(10)
_cell_length_b                   18.7821(17)
_cell_length_c                   18.3618(17)
_cell_measurement_reflns_used    6118
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.17
_cell_volume                     3642.7(6)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.928
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8554.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_description       cube
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         8792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0526P)^2^+1.5656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5697
_reflns_number_total             8792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01127b2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7160703--7160705.cif.'
_cod_database_code               7160705
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C13')=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14')=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=Sof(C15')=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
 Sof(C28')=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29')=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=Sof(C30)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(2)
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 Sof(C30')=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(2)
 Sof(H7)=Sof(O1)=Sof(H1B)=1-FVAR(3)
 Sof(H3)=Sof(O1')=Sof(H1')=FVAR(3)
3.a Riding coordinates:
 N1(H1A), O2(H2), O1(H1B), O1'(H1')
3.b Ternary CH refined with riding coordinates:
 C1(H1), C16(H16)
3.c Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,
 H36B), C37(H37A,H37B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C20(H20), C22(H22)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C38(H38A,
 H38B,H38C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30'(H30A,H30B,H30C), C13'(H13D,H13E,
 H13F), C14'(H14D,H14E,H14F), C15'(H15D,H15E,H15F), C28'(H28D,H28E,H28F),
 C29'(H29D,H29E,H29F), C30(H30D,H30E,H30F)
;
_shelx_res_checksum              81677
_olex2_submission_special_instructions 'No special instructions were received'