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_7160703
_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         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.44
_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
_audit_creation_date             2024-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-19 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.357(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.629(5)
_cell_length_b                   9.551(5)
_cell_length_c                   19.910(11)
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    200
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.37
_cell_volume                     1830.5(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII Quazar CCD '
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14641
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.365
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1646 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.7810.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0137(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0345P)^2^+0.6602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01127b2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7160703--7160705.cif.'
_cod_database_code               7160703
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C11 \\sim C9-C11'
 with sigma of 0.02
 N1-H1B \\sim N1-H1A
 with sigma of 0.02
 C11-C9 \\sim C11'-C9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C11') = Uanis(C11)
4. Others
 Sof(C11')=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
 Sof(H1B)=1-FVAR(2)
 Sof(H1A)=FVAR(2)
5.a Riding coordinates:
 N1(H1A,H1B)
5.b Ternary CH refined with riding coordinates:
 C20(H20), C12(H12), C1(H1), C9(H9)
5.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C5(H5), C6(H6)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C), C11(H11A,H11B,H11C), C11'(H11D,H11E,H11F)
;
_shelx_res_checksum              2679
_olex2_submission_special_instructions 'No special instructions were received'