Di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines and their Ru(II)-Pd(II) dinuclear complexes: synthesis, characterization and application in Cu-free Sonogashira reaction.
Ionova, Violetta A.; Dmitrieva, Alena V.; Abel, Anton S.; Sergeev, Aleksandr D.; Evko, Grigory S.; Yakushev, Alexei A.; Gontcharenko, Victoria E.; Nefedov, Sergei E.; Roznyatovsky, Vitaly A.; Cheprakov, Andrey V.; Averin, Alexei D.; Magdesieva, Tatiana V.; Beletskaya, Irina P.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 17021–17035; doi:10.1039/d4dt02067g

data_1572686
_publ_section_title
;
 Di(pyridin-2-yl)amino-substituted 1,10-phenanthrolines and their
 Ru(II)-Pd(II) dinuclear complexes: synthesis, characterization and
 application in Cu-free Sonogashira reaction.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17021
_journal_page_last               17035
_journal_paper_doi               10.1039/d4dt02067g
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C42 H31 Cl2 N9 Pd Ru, 2(F6 P)'
_chemical_formula_sum            'C42 H31 Cl2 F12 N9 P2 Pd Ru'
_chemical_formula_weight         1230.07
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                84.687(11)
_cell_angle_beta                 88.882(11)
_cell_angle_gamma                83.021(11)
_cell_formula_units_Z            2
_cell_length_a                   12.689(8)
_cell_length_b                   14.266(9)
_cell_length_c                   14.621(9)
_cell_measurement_reflns_used    2448
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      19.369
_cell_measurement_theta_min      2.294
_cell_volume                     2616(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'omega and phi shutterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1205
_diffrn_reflns_av_unetI/netI     0.2014
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.6465
_exptl_absorpt_correction_T_min  0.4516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1272 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.6985.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         9206
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0732
_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^)+(0.0008P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.2142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3821
_reflns_number_total             9206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02067g2.cif
_cod_data_source_block           q_CCDC2
_cod_depositor_comments
'Adding full bibliography for 1572684--1572687.cif.'
_cod_database_code               1572686
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Ru1-N6 \\sim Ru1-N6A
 with sigma of 0.02
 Ru1-N7 \\sim Ru1-N7A
 with sigma of 0.02
 N6-C27 \\sim N6A-C27A
 with sigma of 0.02
 N6-C23 \\sim N6A-C23A
 with sigma of 0.02
 C27-C26 \\sim C27A-C26A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C26-C28 \\sim C26A-C28A
 with sigma of 0.04
 C26-C25 \\sim C26A-C25A
 with sigma of 0.02
 C32-C30 \\sim C32A-C30A
 with sigma of 0.04
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C24-C23 \\sim C24A-C23A
 with sigma of 0.02
 C28-C32 \\sim C28A-C32A
 with sigma of 0.04
 N7-C29 \\sim N7A-C29A
 with sigma of 0.04
 C28-N7 \\sim C28A-N7A
 with sigma of 0.02
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 N7-C32 \\sim N7A-C32A
 with sigma of 0.02
 C26-C24 \\sim C26A-C24A
 with sigma of 0.04
 C32-C31 \\sim C32A-C31A
 with sigma of 0.02
 C25-C23 \\sim C25A-C23A
 with sigma of 0.04
 C31-C30 \\sim C31A-C30A
 with sigma of 0.02
 C30-C29 \\sim C30A-C29A
 with sigma of 0.02
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 Ru1-C27 \\sim Ru1-C27A
 with sigma of 0.04
 Ru1-C23 \\sim Ru1-C23A
 with sigma of 0.04
 N7-C31 \\sim N7A-C31A
 with sigma of 0.04
 Ru1-C28 \\sim Ru1-C28A
 with sigma of 0.04
 Ru1-C32 \\sim Ru1-C32A
 with sigma of 0.04
 N6-C26 \\sim N6A-C26A
 with sigma of 0.04
 N6-C24 \\sim N6A-C24A
 with sigma of 0.04
 N6-C28 \\sim N6A-C28A
 with sigma of 0.04
 C31-C29 \\sim C31A-C29A
 with sigma of 0.04
 C27-C25 \\sim C27A-C25A
 with sigma of 0.04
 C27-C23 \\sim C27A-C23A
 with sigma of 0.04
 C27-N7 \\sim C27A-N7A
 with sigma of 0.04
 C27-C29 \\sim C27A-C29A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C27) \\sim Ueq,
Uanis(N6) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C23A) \\sim Ueq, Uanis(N6A) \\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C25A)
\\sim Ueq, Uanis(C26A) \\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C23A) = Uanis(C23)
Uanis(C24A) = Uanis(C24)
Uanis(N6A) = Uanis(N6)
Uanis(N7A) = Uanis(N7)
Uanis(C32A) = Uanis(C32)
4. Others
 Fixed Sof: Pd1(0.7) Cl1(0.7) Cl2(0.7) N6(0.6) C27(0.6) C26(0.6) H26(0.6)
 C25(0.6) H25(0.6) C24(0.6) H24(0.6) C23(0.6) H23(0.6) C28(0.6) N7(0.6)
 C32(0.6) H32(0.6) C31(0.6) H31(0.6) C30(0.6) H30(0.6) C29(0.6) H29(0.6)
 Cl2A(0.3) Pd1A(0.3) Cl1A(0.3) N6A(0.4) C27A(0.4) C26A(0.4) H26A(0.4) C25A(0.4)
 H25A(0.4) C24A(0.4) H24A(0.4) C23A(0.4) H23A(0.4) C28A(0.4) N7A(0.4) C32A(0.4)
 H32A(0.4) C31A(0.4) H31A(0.4) C30A(0.4) H30A(0.4) C29A(0.4) H29A(0.4)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C26(H26), C25(H25), C24(H24), C23(H23), C4(H4), C3(H3),
 C6(H6), C9(H9), C42(H42), C7(H7), C39(H39), C33(H33), C15(H15), C41(H41),
 C16(H16), C40(H40), C1(H1), C2(H2), C36(H36), C32(H32), C31(H31), C30(H30),
 C29(H29), C35(H35), C8(H8), C20(H20), C34(H34), C19(H19), C18(H18), C26A(H26A),
  C25A(H25A), C24A(H24A), C23A(H23A), C32A(H32A), C31A(H31A), C30A(H30A),
 C29A(H29A)
5.b Fitted hexagon refined as free rotating group:
 N6(C27,C26,C25,C24,C23), C28(N7,C32,C31,C30,C29), N6A(C27A,C26A,C25A,C24A,
 C23A), C28A(N7A,C32A,C31A,C30A,C29A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              8531
_shelx_hkl_checksum              37696
_shelx_fab_checksum              15892
_olex2_submission_special_instructions 'No special instructions were received'