First 4,7-oxygenated 1,10-phenanthroline-2,9-diamides: synthesis, tautomerism and complexation with REE nitrates.
Avagyan, Nane A.; Lemport, Pavel S.; Roznyatovsky, Vitaly A.; Averin, Alexei D.; Yakushev, Alexei A.; Lyssenko, Konstantin A.; Perfilyev, Pavel D.; Isakovskaya, Ksenia L.; Aksenova, Svetlana A.; Nelyubina, Yulia V.; Vokuev, Mikhail F.; Rodin, Igor A.; Gloriozov, Igor P.; Ustynyuk, Yuri A.; Nenajdenko, Valentine G.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 3052–3064; doi:10.1039/d3dt03643j

data_7714953
_publ_section_title
;
 First 4,7-oxygenated 1,10-phenanthroline-2,9-diamides: synthesis,
 tautomerism and complexation with REE nitrates.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3052
_journal_page_last               3064
_journal_paper_doi               10.1039/d3dt03643j
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C30 H42 N4 O4'
_chemical_formula_sum            'C30 H42 N4 O4'
_chemical_formula_weight         522.67
_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             2023-09-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                94.930(2)
_cell_angle_beta                 103.562(2)
_cell_angle_gamma                109.844(2)
_cell_formula_units_Z            4
_cell_length_a                   14.0169(5)
_cell_length_b                   16.3104(6)
_cell_length_c                   16.3280(6)
_cell_measurement_reflns_used    8831
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.25
_cell_volume                     3357.0(2)
_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      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49422
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.764
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.7465.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.034
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         13183
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1034P)^2^+1.7003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.2256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7159
_reflns_number_total             13183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03643j2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7714953--7714954.cif.'
_cod_database_code               7714953
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C37-C36 \\sim C29A-C28A
 with sigma of 0.02
 C36-C27A \\sim C28A-C27A
 with sigma of 0.02
 C38-C37 \\sim C30A-C29A
 with sigma of 0.02
 C24A-C23A \\sim C39-C34
 with sigma of 0.02
 C20A-C21A \\sim C33-C31
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C26A) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C21A) \\sim Ueq, Uanis(C33) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19A) = Uanis(C32)
Uanis(C26A) = Uanis(C40)
Uanis(C21A) = Uanis(C33)
Uanis(C31) = Uanis(C20A)
Uanis(C20') = Uanis(C20)
Uanis(C21') = Uanis(C21)
Uanis(C23A) = Uanis(C39)
Uanis(C24A) = Uanis(C34)
Uanis(C25A) = Uanis(C35)
Uanis(C36) = Uanis(C28A)
Uanis(C38) = Uanis(C30A)
Uanis(C37) = Uanis(C29A)
4. Others
 Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=1-FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
 Sof(H19C)=Sof(H19D)=Sof(C20)=Sof(H20C)=Sof(H20D)=Sof(C21)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=1-FVAR(2)
 Sof(H19E)=Sof(H19F)=Sof(C20')=Sof(H20E)=Sof(H20F)=Sof(C21')=Sof(H21G)=
 Sof(H21H)=Sof(H21I)=FVAR(2)
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(C25A)=Sof(H25A)=Sof(H25B)=1-FVAR(3)
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C39)=Sof(H39A)=
 Sof(H39B)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(3)
 Sof(H27C)=Sof(H27D)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=1-FVAR(4)
 Sof(H27A)=Sof(H27B)=Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(C29A)=Sof(H29A)=
 Sof(H29B)=Sof(C30A)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(4)
5.a Riding coordinates:
 N1(H1), O2A(H2A), N1A(H1A)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14C,H14D), C15(H15C,H15D), C16(H16C,H16D), C18(H18E,H18F), C19(H19E,
 H19F), C19(H19C,H19D), C23(H23C,H23D), C24(H24C,H24D), C25(H25C,H25D),
 C27(H27E,H27F), C28(H28C,H28D), C29(H29C,H29D), C20(H20C,H20D), C20'(H20E,
 H20F), C14A(H14A,H14B), C15A(H15A,H15B), C16A(H16A,H16B), C18A(H18A,H18B),
 C18A(H18C,H18D), C27A(H27A,H27B), C27A(H27C,H27D), C23A(H23A,H23B), C19A(H19A,
 H19B), C20A(H20A,H20B), C24A(H24A,H24B), C25A(H25A,H25B), C28A(H28A,H28B),
 C29A(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C39(H39A,H39B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2B), C5(H5), C6(H6), C9(H9), C2A(H2AA), C5A(H5A), C6A(H6A), C9A(H9A)
5.d Idealised Me refined as rotating group:
 C17(H17D,H17E,H17F), C26(H26D,H26E,H26F), C30(H30D,H30E,H30F), C21(H21D,H21E,
 H21F), C21'(H21G,H21H,H21I), C17A(H17A,H17B,H17C), C26A(H26A,H26B,H26C),
 C21A(H21A,H21B,H21C), C30A(H30A,H30B,H30C), C33(H33A,H33B,H33C), C38(H38A,H38B,
 H38C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              89980
_shelx_fab_checksum              74043
_olex2_submission_special_instructions 'No special instructions were received'