Effect of Alkyl Substituent on the Amide of Bis-lactam-1,10-phenanthroline Ligands for Lanthanide Extraction
Gao, Fengxin; Fang, Dong; Xiao, Chengliang; Dalton Transactions  (2026) –; doi:10.1039/D5DT03012A

data_7720715
_publ_section_title
;
 Effect of alkyl substituent on the amide of
 bis-lactam-1,10-phenanthroline ligands for lanthanide extraction.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5679
_journal_page_last               5688
_journal_paper_doi               10.1039/d5dt03012a
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C84 H92 Eu N8 O4, 3(Cl O4), 2[H2O], 4[H2O]'
_chemical_formula_sum            'C88 H116 Cl3 Eu N8 O24'
_chemical_formula_weight         1928.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2026-03-15
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-03-15 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.476(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.562(3)
_cell_length_b                   18.3118(19)
_cell_length_c                   20.898(2)
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      50.408
_cell_measurement_theta_min      2.220
_cell_volume                     9583.1(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      240(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            69688
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.850
_diffrn_reflns_theta_min         4.880
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    6.068
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             4024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.313
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.00092(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         8518
_refine_ls_number_restraints     423
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1400P)^2^+5.3757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7111
_reflns_number_total             8518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt03012a2.cif
_cod_data_source_block           z_amended
_cod_depositor_comments
'Adding full bibliography for 7720715--7720716.cif.'
_cod_database_code               7720715
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.408
_shelx_estimated_absorpt_t_min   0.336
_olex2_refinement_description
;
1. Shared sites
{C8, C126}
{C15, C129}
{C26, C51}
2. Restrained distances
 C48-C51 = C62-C26 = C51-C34 = C26-C34 = C51-C28 = C26-C31 = C51-C40 = C26-C22
 = C51-C28 = C51-C40
 1.54 with sigma of 0.01
 C130-C15 = C37-C15 = C35-C15 = C15-C74 = C129-C74 = C32-C129 = C19-C129 = C16-
 C129 = C130-C129 = C37-C129 = C32-C15
 1.54 with sigma of 0.01
 Cl47-O44 = Cl47-O67 = Cl47-O43 = Cl47-O64 = Cl56-O68 = Cl56-O45 = Cl56-O60 =
 Cl56-O17
 1.44 with sigma of 0.01
 C19-C32
 2.51 with sigma of 0.02
 C94-C126 = C8-C12 = C12-C115 = C94-C156 = C151-C115 = C156-C146
 1.54 with sigma of 0.01
 Cl5-O10 = Cl5-O14 = Cl5-O4 = Cl5-O7
 1.43 with sigma of 0.01
 C146-C156
 1.5 with sigma of 0.02
 C113-C1 = C114-C113 = C96A-C1 = C96-C114
 1.54 with sigma of 0.01
 C32-C74 = C130-C74 = C19-C74 = C35-C74 = C16-C74 = C37-C74 = C35-C130 = C130-
 C37 = C37-C35 = C32-C16 = C16-C19
 2.51 with sigma of 0.03
 C48-C28 \\sim C62-C31 \\sim C48-C40 \\sim C62-C22 \\sim C28-C40 \\sim C31-C22
 with sigma of 0.04
 O44-O43 \\sim O67-O64 \\sim O44-O64 \\sim O67-O43 \\sim O44-O67 \\sim O43-O64
\\sim O68-O45 \\sim O68-O60
 \\sim O68-O17 \\sim O45-O60 \\sim O45-O17 \\sim O60-O17
 with sigma of 0.04
 O10-O4 \\sim O14-O7 \\sim O10-O7 \\sim O14-O4 \\sim O10-O14 \\sim O4-O7
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C19 \\sim C130 \\sim C32 \\sim C37 \\sim C35 \\sim C16: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C48 \\sim C28 \\sim C40 \\sim C62 \\sim C22 \\sim C31: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Cl47 \\sim O44 \\sim O67 \\sim O43 \\sim O64 \\sim Cl56 \\sim O68 \\sim O45
\\sim O17 \\sim O60: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
C94 \\sim C115 \\sim C12 \\sim C156 \\sim C146 \\sim C151: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
O14 \\sim O10 \\sim Cl5 \\sim O4 \\sim O7: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(C15) = Uanis(C129)
Uanis(C26) = Uanis(C51)
Uanis(Cl47) = Uanis(Cl56)
Uanis(O44) = Uanis(O68)
Uanis(C94) = Uanis(C12)
Uanis(C8) = Uanis(C126)
Uanis(C114) = Uanis(C1)
Uanis(C96) = Uanis(C96A)
4. Others
 1*[Sof(Cl47)+Sof(O44)+Sof(O67)+Sof(O43)+Sof(O64)]+1*[Sof(Cl56)+Sof(O68)+
 Sof(O45)+Sof(O17)+Sof(O60)]=1 with esd of 0
 Sof(Cl47)=Sof(O44)=Sof(O67)=Sof(O43)=Sof(O64)=FVAR(1)
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C26)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=1-FVAR(2)
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C51)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(2)
 Sof(C115)=Sof(H11G)=Sof(H11H)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C12)=Sof(H12C)=
 Sof(H12D)=Sof(C151)=Sof(H15C)=Sof(H15D)=Sof(H15E)=1-FVAR(3)
 Sof(C126)=Sof(H12A)=Sof(H12B)=Sof(C94)=Sof(H94A)=Sof(H94B)=Sof(C156)=
 Sof(H15A)=Sof(H15B)=Sof(C146)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(3)
 Sof(Cl56)=Sof(O68)=Sof(O45)=Sof(O17)=Sof(O60)=FVAR(4)
 Sof(H11C)=Sof(H11D)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C96A)=Sof(H96D)=Sof(H96E)=
 Sof(H96F)=1-FVAR(5)
 Sof(C96)=Sof(H96A)=Sof(H96B)=Sof(H96C)=Sof(H11A)=Sof(H11B)=Sof(C114)=
 Sof(H11E)=Sof(H11F)=FVAR(5)
 Fixed Sof: C129(0.5) C130(0.5) H13A(0.5) H13B(0.5) H13C(0.5) C35(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5) C37(0.5) H37A(0.5) H37B(0.5) H37C(0.5) C15(0.5)
 C19(0.5) H19A(0.5) H19B(0.5) H19C(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C32(0.5) H32A(0.5) H32B(0.5) H32C(0.5) Cl5(0.5) O10(0.5) O14(0.5) O4(0.5)
 O7(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C126(H12A,H12B), C94(H94A,H94B), C113(H11A,H11B), C113(H11C,
 H11D), C114(H11E,H11F), C115(H11G,H11H), C8(H8A,H8B), C12(H12C,H12D),
 C156(H15A,H15B), C1(H1A,H1B)
5.b Me refined with riding coordinates:
 C130(H13A,H13B,H13C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C19(H19A,H19B,
 H19C), C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C48(H48A,H48B,H48C), C28(H28A,
 H28B,H28C), C40(H40A,H40B,H40C), C62(H62A,H62B,H62C), C22(H22A,H22B,H22C),
 C31(H31A,H31B,H31C)
5.c Aromatic/amide H refined with riding coordinates:
 C117(H117), C124(H124), C106(H106), C91(H91), C111(H111), C110(H110),
 C84(H84), C75(H75), C81(H81), C112(H112)
5.d Idealised Me refined as rotating group:
 C96(H96A,H96B,H96C), C146(H14A,H14B,H14C), C151(H15C,H15D,H15E), C96A(H96D,
 H96E,H96F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              62844
_shelx_hkl_checksum              82570
_shelx_fab_checksum              75815
_olex2_submission_special_instructions 'No special instructions were received'