Para-substituted benzoic acid ruthenium(ii) complexes: structural features modulating cytotoxicity
Dutra, Jocely L.; Marcon, Pedro H. S.; Moselli, Gustavo; Niquini, Fabiano M.; da Costa, João Victor F.; Moraes, Carlos André F.; Braga, Ataualpa A. C.; Ellena, Javier; Batista, Alzir A.; de Araujo-Neto, João Honorato; RSC Advances 16 (2026) 19763–19778; doi:10.1039/D5RA07271A

data_7251886
_publ_section_title
;
 Para-substituted benzoic acid ruthenium(ii) complexes: structural
 features modulating cytotoxicity
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              19763
_journal_page_last               19778
_journal_paper_doi               10.1039/D5RA07271A
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C45 H40 N3 O4 P2 Ru, F6 P'
_chemical_formula_sum            'C45 H40 F6 N3 O4 P3 Ru'
_chemical_formula_weight         994.814
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-05 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                65.493(2)
_cell_angle_beta                 66.109(2)
_cell_angle_gamma                73.468(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8102(2)
_cell_length_b                   13.9899(2)
_cell_length_c                   14.5412(3)
_cell_measurement_reflns_used    26742
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      79.1440
_cell_measurement_theta_min      3.8000
_cell_volume                     2146.65(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 44.125a 64-bit (release 17-10-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9961
_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    -37.00   4.00   0.50    0.40    --  -48.80  34.00 -72.00   82
  2  \w   -108.00 -52.00   0.50    0.40    --  -48.80 -34.00 129.00  112
  3  \w    -15.00  37.00   0.50    0.40    --   48.80 -34.00 129.00  104
  4  \w     42.00 122.00   0.50    0.40    --   48.80  34.00 -72.00  160
  5  \w   -108.00 -80.00   0.50    1.00    --  -90.00 -34.00 129.00   56
  6  \w    122.00 168.00   0.50    1.00    --  111.50  34.00 -72.00   92
  7  \w    -69.00  16.00   0.50    0.40    --  -48.80  77.00 -60.00  170
  8  \w    -22.00  26.00   0.50    0.40    --  -48.80  19.00  60.00   96
  9  \w    -26.00  11.00   0.50    0.40    --  -48.80  19.00-150.00   74
 10  \w    -68.00 -35.00   0.50    0.40    --  -48.80 125.00  90.00   66
 11  \w     48.00  74.00   0.50    0.40    --   48.80-125.00-150.00   52
 12  \w   -159.00 -97.00   0.50    1.00    --  -90.00-125.00 -90.00  124
 13  \w    -48.00 -22.00   0.50    1.00    --  -90.00  45.00  90.00   52
 14  \w     60.00 105.00   0.50    1.00    --  111.50 -95.00  30.00   90
 15  \w     40.00  65.00   0.50    1.00    --  111.50 -77.00 120.00   50
 16  \w     40.00  66.00   0.50    1.00    --  111.50 -61.00 -60.00   52
 17  \w     62.00  88.00   0.50    1.00    --  111.50 -77.00 150.00   52
 18  \w     47.00  73.00   0.50    1.00    --  111.50 -95.00 120.00   52
 19  \w     78.00 104.00   0.50    1.00    --  111.50 -95.00 120.00   52
 20  \w     41.00  73.00   0.50    1.00    --  111.50-125.00-120.00   64
 21  \w     40.00  65.00   0.50    1.00    --  111.50 -95.00-150.00   50
 22  \w     75.00 109.00   0.50    1.00    --  111.50-125.00   0.00   68
 23  \w     42.00  68.00   0.50    1.00    --  111.50 -61.00 -30.00   52
 24  \w    135.00 165.00   0.50    1.00    --  111.50  30.00   0.00   60
 25  \w    116.00 160.00   0.50    1.00    --  111.50  30.00  60.00   88
 26  \w     57.00 104.00   0.50    1.00    --  111.50 -95.00   0.00   94
 27  \w     41.00  70.00   0.50    1.00    --  111.50 -79.00 172.71   58
 28  \w    105.00 178.00   0.50    1.00    --  111.50  15.00 150.00  146
 29  \w     49.00 103.00   0.50    1.00    --  111.50 -95.00  60.00  108
 30  \w     75.00 122.00   0.50    1.00    --  111.50 -80.00 -89.08   94
 31  \w    103.00 165.00   0.50    1.00    --  111.50 125.00   0.00  124
 32  \w     41.00  71.00   0.50    1.00    --  111.50 -95.00 150.00   60
 33  \w     80.00 105.00   0.50    1.00    --  111.50 -95.00 150.00   50
 34  \w     44.00  69.00   0.50    1.00    --  111.50 -61.00   0.00   50
 35  \w     81.00 111.00   0.50    1.00    --  111.50-125.00-120.00   60
 36  \w     98.00 123.00   0.50    1.00    --  111.50 125.00 120.00   50
 37  \w    102.00 127.00   0.50    1.00    --  111.50  30.00   0.00   50
 38  \w     41.00  70.00   0.50    1.00    --  111.50-125.00   0.00   58
 39  \w     63.00  89.00   0.50    1.00    --  111.50-125.00 -90.00   52
 40  \w    119.00 145.00   0.50    1.00    --  111.50  77.00  60.00   52
 41  \w     41.00  67.00   0.50    1.00    --  111.50-125.00 150.00   52
 42  \w     71.00  97.00   0.50    1.00    --  111.50-125.00 150.00   52
 43  \w     95.00 127.00   0.50    1.00    --  111.50 125.00-180.00   64
 44  \w    135.00 165.00   0.50    1.00    --  111.50 125.00-180.00   60
 45  \w     96.00 168.00   0.50    1.00    --  111.50 125.00 150.00  144
 46  \w    109.00 150.00   0.50    1.00    --  111.50  61.00 -60.00   82
 47  \w     46.00  72.00   0.50    1.00    --  111.50 -95.00 -60.00   52
 48  \w     79.00 105.00   0.50    1.00    --  111.50 -95.00 -60.00   52
 49  \w     70.00 101.00   0.50    1.00    --  111.50 -95.00 -90.00   62
 50  \w    103.00 134.00   0.50    1.00    --  111.50 -79.00 172.71   62
 51  \w     95.00 159.00   0.50    1.00    --  111.50 125.00-150.00  128
 52  \w    112.00 178.00   0.50    1.00    --  111.50  77.00 -90.00  132
 53  \w     79.00 105.00   0.50    1.00    --  111.50 -95.00-180.00   52
 54  \w    143.00 171.00   0.50    1.00    --  111.50  77.00 -30.00   56
 55  \w    121.00 164.00   0.50    1.00    --  111.50  77.00  30.00   86
 56  \w    106.00 177.00   0.50    1.00    --  111.50  61.00  60.00  142
 57  \w     45.00  70.00   0.50    1.00    --  111.50 -77.00  60.00   50
 58  \w     41.00  70.00   0.50    1.00    --  111.50 -61.00-120.00   58
 59  \w     44.00  70.00   0.50    1.00    --  111.50 -77.00 -60.00   52
 60  \w     48.00  74.00   0.50    1.00    --  111.50 -82.00  40.08   52
 61  \w     83.00 109.00   0.50    1.00    --  111.50 -82.00  40.08   52
 62  \w    139.00 178.00   0.50    1.00    --  111.50  77.00-120.00   78
 63  \w    115.00 141.00   0.50    1.00    --  111.50  77.00 -60.00   52
 64  \w     71.00  97.00   0.50    1.00    --  111.50-125.00-180.00   52
 65  \w     41.00  67.00   0.50    1.00    --  111.50 -77.00   0.00   52
 66  \w    130.00 156.00   0.50    1.00    --  111.50 125.00 120.00   52
 67  \w     64.00 103.00   0.50    1.00    --  111.50 -77.00-180.00   78
 68  \w     62.00  88.00   0.50    1.00    --  111.50 -77.00 -90.00   52
 69  \w     42.00  68.00   0.50    1.00    --  111.50 -95.00 -90.00   52
 70  \w     41.00  69.00   0.50    1.00    --  111.50 -61.00-150.00   56
 71  \w     41.00  71.00   0.50    1.00    --  111.50 -97.00  92.55   60
 72  \w     78.00 106.00   0.50    1.00    --  111.50 -97.00  92.55   56
 73  \w    134.00 160.00   0.50    1.00    --  111.50  45.00-150.00   52
 74  \w     48.00 109.00   0.50    1.00    --  111.50-125.00-150.00  122
 75  \w     79.00 106.00   0.50    1.00    --  111.50-125.00 120.00   54
 76  \w    146.00 178.00   0.50    1.00    --  111.50  61.00 -30.00   64
 77  \w    115.00 177.00   0.50    1.00    --  111.50  61.00   0.00  124
 78  \w    150.00 172.50   0.50    1.00    --  111.50  45.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1022106000
_diffrn_orient_matrix_UB_12      -0.0465550000
_diffrn_orient_matrix_UB_13      0.0980029000
_diffrn_orient_matrix_UB_21      -0.0422612000
_diffrn_orient_matrix_UB_22      -0.0253320000
_diffrn_orient_matrix_UB_23      -0.0715708000
_diffrn_orient_matrix_UB_31      0.0735769000
_diffrn_orient_matrix_UB_32      -0.1101388000
_diffrn_orient_matrix_UB_33      0.0217989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.9970
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43388
_diffrn_reflns_point_group_measured_fraction_full 0.9970
_diffrn_reflns_point_group_measured_fraction_max 0.9961
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         4.81
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.658
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       plate
_exptl_crystal_F_000             1017.500
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.4881
_refine_diff_density_min         -0.4637
_refine_diff_density_rms         0.0941
_refine_ls_d_res_high            0.8200
_refine_ls_d_res_low             9.2006
_refine_ls_goodness_of_fit_ref   1.0472
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    76
_refine_ls_number_parameters     584
_refine_ls_number_reflns         8114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0472
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+2.0186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -13
_reflns_limit_k_max              17
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                7429
_reflns_number_total             8114
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ra07271a2.cif
_cod_data_source_block           RuNO2
_cod_database_code               7251886
_chemical_oxdiff_formula         'Ru C H N O P F '
_cell_oxdiff_angle_alpha         65.4933(19)
_cell_oxdiff_angle_beta          66.1087(19)
_cell_oxdiff_angle_gamma         73.4682(15)
_cell_oxdiff_length_a            12.8102(2)
_cell_oxdiff_length_b            13.9899(2)
_cell_oxdiff_length_c            14.5412(3)
_cell_oxdiff_measurement_reflns_used 26742
_cell_oxdiff_volume              2146.66(6)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C230(H23a,H23b), C130(H13a,H13b), C131(H13c,H13d), C231(H23c,H23d)
2.b Aromatic/amide H refined with riding coordinates:
 C221(H221), C225(H225), C211(H211), C111(H111), C213(H213), C7(H7), C8(H8),
 C125(H125), C122(H122), C115(H115), C212(H212), C14(H14), C113(H113), C17(H17),
  C224(H224), C214(H214), C3(H3), C121(H121), C222(H222), C114(H114), C6(H6),
 C124(H124), C9(H9), C215(H215), C15(H15), C112(H112), C11(H11), C223(H223),
 C4(H4), C123(H123), C16(H16), C10(H10)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.497
_oxdiff_exptl_absorpt_empirical_full_min 0.787