Ruthenium complexes with triazenide ligands bearing an N-heterocyclic moiety, and their catalytic properties in the reduction of nitroarenes
Romero-Soto, Christian A.; Iglesias, Ana L.; Velázquez-Ham, Amor F.; Camarena-Díaz, Juan P.; Correa-Ayala, Erick; Gomez-Lopez, Jessica L.; Chávez, Daniel; Ochoa-Terán, Adrián; Aguirre, Gerardo; Rheingold, Arnold L.; Grotjahn, Douglas B.; Parra-Hake, Miguel; Miranda-Soto, Valentín; RSC Advances 14 (2024) 24019–24030; doi:10.1039/D4RA04813J

data_7249162
_publ_section_title
;
 Ruthenium complexes with triazenide ligands bearing an N-heterocyclic
 moiety, and their catalytic properties in the reduction of nitroarenes
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              24019
_journal_page_last               24030
_journal_paper_doi               10.1039/D4RA04813J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C25 H24 Cl2 N4 Ru'
_chemical_formula_sum            'C25 H24 Cl2 N4 Ru'
_chemical_formula_weight         552.45
_chemical_name_common            RuCl-triazenide-Quinoline
_chemical_name_systematic
'[RuCl(1-ClPh-3-quinolinetriazenide)(p-cymene)]'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-21
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-06-01 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.96150(10)
_cell_length_b                   11.85520(10)
_cell_length_c                   25.7291(2)
_cell_measurement_reflns_used    9310
_cell_measurement_temperature    293.4(3)
_cell_measurement_theta_max      70.7000
_cell_measurement_theta_min      1.7150
_cell_volume                     2428.45(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1970
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -42.00  92.00   1.00    1.00    --    0.00  57.00 -90.00  134
  2  \w     85.00 149.00   1.00    1.00    --   54.67 148.00  59.00   64
  3  \w     97.00 146.00   1.00    1.00    --   54.67 125.00  30.00   49
  4  \w    -39.00 149.00   1.00    1.00    --   54.67  19.00 -30.00  188
  5  \w     61.00 146.00   1.00    1.00    --  109.35 178.00   0.00   85
  6  \w     18.00 109.00   1.00    1.00    --  109.35-111.00-180.00   91
  7  \w     63.00 178.00   1.00    1.00    --  109.35  38.00-180.00  115
  8  \w    103.00 178.00   1.00    1.00    --  109.35  77.00 -90.00   75
  9  \w    104.00 178.00   1.00    1.00    --  109.35 111.00 150.00   74
 10  \w    -99.00 -37.00   1.00    1.00    --    0.00 178.00   0.00   62
 11  \w     97.00 146.00   1.00    1.00    --   54.67 125.00-150.00   49
 12  \w      8.00 145.00   1.00    1.00    --   54.67  38.00 120.00  137
 13  \w     65.00 165.00   1.00    1.00    --  109.35  64.00  90.00  100
 14  \w     68.00 178.00   1.00    1.00    --  109.35  50.00   0.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016842000
_diffrn_orient_matrix_UB_12      -0.1050049000
_diffrn_orient_matrix_UB_13      -0.0352662000
_diffrn_orient_matrix_UB_21      0.0297828000
_diffrn_orient_matrix_UB_22      -0.0758028000
_diffrn_orient_matrix_UB_23      0.0477567000
_diffrn_orient_matrix_UB_31      -0.1911779000
_diffrn_orient_matrix_UB_32      -0.0108686000
_diffrn_orient_matrix_UB_33      0.0077666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12917
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.808
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense red'
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone-d6'
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0490P)^2^+0.2080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4357
_reflns_number_total             4509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04813j2.cif
_cod_data_source_block           vm1285-165-1
_cod_database_code               7249162
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNClRu
_diffrn_oxdiff_digest_frames
;
01d92df16dda85d01b6f0379dc97f7ab5100038fb3e
;
_diffrn_oxdiff_digest_hkl
;
01a8c8aaf50dfcc49b41bde9334e1f277ce5b0
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              96828
_olex2_date_sample_data_collection 2021-05-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.737