Morpholine-Derived Hydrophilic 1,10-phenanthroline-2,9-dicarboxamide for Americium–Lanthanide Separation in Phosphine Oxide Extraction Systems
Evsiunina, Mariia V.; Domnikov, Kirill S.; Matveev, Petr I.; Kalle, Paulina; Matazova, Ekaterina; Gerasimov, Mikhail A.; Lemport, Pavel S.; Sonin, Igor; Petrov, Vladimir G.; Kostikova, Galina V.; Ustynyuk, Yuri; Nenajdenko, Valentine; Dalton Transactions  (2025) –; doi:10.1039/D5DT02131F

data_7719889
_publ_section_title
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 Morpholine-Derived Hydrophilic 1,10-phenanthroline-2,9-dicarboxamide for
 Americium--Lanthanide Separation in Phosphine Oxide Extraction Systems
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D5DT02131F
_journal_year                    2025
_chemical_formula_moiety         'C26 H35 Eu N9 O14, H2 O, N O3'
_chemical_formula_sum            'C26 H37 Eu N10 O18'
_chemical_formula_weight         929.61
_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             2025-08-18
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-08-18 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                98.190(2)
_cell_angle_beta                 92.689(2)
_cell_angle_gamma                110.491(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2372(6)
_cell_length_b                   9.2714(5)
_cell_length_c                   21.8651(12)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.339
_cell_measurement_theta_min      2.366
_cell_volume                     1726.71(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART Photon II'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25475
_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         26.998
_diffrn_reflns_theta_min         1.892
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'fine-focus sealed X-ray tube'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.7452.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         4.096
_refine_diff_density_min         -3.716
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7524
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0265P)^2^+23.8229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7194
_reflns_number_total             7524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt02131f2.cif
_cod_data_source_block           2341
_cod_database_code               7719889
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.737
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9319(10)
 0.0681(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 N6-H6
 0.85 with sigma of 0.02
 O18-N11 \\sim O20-N11 \\sim O19-N11
 with sigma of 0.02
 O16-N10 \\sim O17-N10 \\sim O15-N10
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O18, O19, O20, N11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O15, O16, O17, N10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O8, O9, O10, N8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N6, C23, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O15(0.5) O16(0.5) O17(0.5) N10(0.5) O18(0.5) O19(0.5) O20(0.5)
 N11(0.5)
6.a Free rotating group:
 O21(H21C,H21D)
6.b Rotating group:
 O14(H14A,H14B)
6.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
6.d Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C3(H3A), C4(H4A), C10(H10), C9(H9), C11(H11), C12(H12)
6.e Fitted hexagon refined as free rotating group:
 C8(C7,C6,C5,C10,C9)
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_shelx_res_checksum              75583
_olex2_submission_special_instructions 'No special instructions were received'