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_7251885
_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         'C46 H42 Br N2 O2 P2 Ru, F6 P, 0.3[H2O]'
_chemical_formula_sum            'C46 H42.6 Br F6 N2 O2.3 P3 Ru'
_chemical_formula_weight         1048.143
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-10 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.520(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7262(1)
_cell_length_b                   14.8624(1)
_cell_length_c                   19.3587(1)
_cell_measurement_reflns_used    42982
_cell_measurement_temperature    100.1(3)
_cell_measurement_theta_max      79.0820
_cell_measurement_theta_min      2.8350
_cell_volume                     4462.38(5)
_computing_cell_refinement       'CrysAlisPro 1.171.44.118a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.118a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.118a (Rigaku OD, 2025)'
_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      100.1(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_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    -81.00   0.00   0.50    0.31    --  -48.85 108.00  91.00  162
  2  \w     26.00  75.00   0.50    0.31    --   48.85-108.00  -6.00   98
  3  \w    -74.00 -49.00   0.50    1.22    --  -90.00 108.00  91.00   50
  4  \w   -146.00-121.00   0.50    1.22    --  -90.00-108.00  -6.00   50
  5  \w     73.00 104.00   0.50    1.22    --  111.50-108.00  -6.00   62
  6  \w    112.00 154.00   0.50    1.22    --  111.50 108.00  91.00   84
  7  \w   -119.00 -94.00   0.50    0.31    --  -48.85-125.00  60.00   50
  8  \w    -26.00  15.00   0.50    0.31    --  -48.85  19.00-150.00   82
  9  \w    -24.00   2.00   0.50    0.31    --  -48.85  19.00 -60.00   52
 10  \w    -42.00  23.00   0.50    0.31    --  -48.85  38.00-120.00  130
 11  \w   -120.00 -94.00   0.50    0.31    --  -48.85-125.00 150.00   52
 12  \w    -22.00  19.00   0.50    0.31    --   48.85 -19.00 -90.00   82
 13  \w     45.00  70.00   0.50    1.22    --  111.50 -61.00   0.00   50
 14  \w     54.00 101.00   0.50    1.22    --  111.50 -78.00-139.24   94
 15  \w     43.00  69.00   0.50    1.22    --  111.50 -61.00  60.00   52
 16  \w     64.00  91.00   0.50    1.22    --  111.50 -82.00 120.23   54
 17  \w    101.00 132.00   0.50    1.22    --  111.50  45.00-150.00   62
 18  \w     85.00 111.00   0.50    1.22    --  111.50-125.00-120.00   52
 19  \w    110.00 146.00   0.50    1.22    --  111.50  77.00 -90.00   72
 20  \w    110.00 137.00   0.50    1.22    --  111.50  61.00  30.00   54
 21  \w    106.00 155.00   0.50    1.22    --  111.50  61.00   0.00   98
 22  \w     52.00 102.00   0.50    1.22    --  111.50 -77.00  60.00  100
 23  \w     65.00 105.00   0.50    1.22    --  111.50 -94.00   0.00   80
 24  \w    133.00 159.00   0.50    1.22    --  111.50  77.00 150.00   52
 25  \w     41.00  67.00   0.50    1.22    --  111.50 -94.00  60.00   52
 26  \w     79.00 105.00   0.50    1.22    --  111.50 -94.00  60.00   52
 27  \w     40.00  74.00   0.50    1.22    --  111.50 -77.00 -60.00   68
 28  \w    130.00 156.00   0.50    1.22    --  111.50  30.00   0.00   52
 29  \w    138.00 173.00   0.50    1.22    --  111.50  45.00-150.00   70
 30  \w     43.00  78.00   0.50    1.22    --  111.50-125.00-120.00   70
 31  \w     51.00  77.00   0.50    1.22    --  111.50 -83.00  31.72   52
 32  \w     41.00  66.00   0.50    1.22    --  111.50 -77.00  90.00   50
 33  \w     72.00 102.00   0.50    1.22    --  111.50 -77.00  90.00   60
 34  \w     40.00  66.00   0.50    1.22    --  111.50 -94.00  30.00   52
 35  \w     80.00 105.00   0.50    1.22    --  111.50 -94.00  30.00   50
 36  \w     73.00  98.00   0.50    1.22    --  111.50-125.00   0.00   50
 37  \w     43.00  69.00   0.50    1.22    --  111.50 -61.00  90.00   52
 38  \w    116.00 142.00   0.50    1.22    --  111.50 125.00-120.00   52
 39  \w     74.00 100.00   0.50    1.22    --  111.50 -77.00  30.00   52
 40  \w     44.00  91.00   0.50    1.22    --  111.50-125.00-150.00   94
 41  \w     42.00  72.00   0.50    1.22    --  111.50 -77.00  30.00   60
 42  \w     40.00  70.00   0.50    1.22    --  111.50 -61.00 -60.00   60
 43  \w     44.00  78.00   0.50    1.22    --  111.50 -82.00-118.94   68
 44  \w     40.00  89.00   0.50    1.22    --  111.50 -94.00  90.00   98
 45  \w    151.00 176.00   0.50    1.22    --  111.50  77.00-150.00   50
 46  \w     73.00  98.00   0.50    1.22    --  111.50-125.00  60.00   50
 47  \w    111.00 155.00   0.50    1.22    --  111.50  30.00 -90.00   88
 48  \w    125.00 176.00   0.50    1.22    --  111.50  15.00   0.00  102
 49  \w    103.00 177.00   0.50    1.22    --  111.50  15.00 150.00  148
 50  \w    152.00 177.00   0.50    1.22    --  111.50  61.00  30.00   50
 51  \w    146.00 177.00   0.50    1.22    --  111.50  77.00-180.00   62
 52  \w    121.00 147.00   0.50    1.22    --  111.50  61.00  90.00   52
 53  \w     82.00 108.00   0.50    1.22    --  111.50 -83.00 -12.14   52
 54  \w    101.00 157.00   0.50    1.22    --  111.50  30.00-180.00  112
 55  \w    145.00 171.00   0.50    1.22    --  111.50  45.00  30.00   52
 56  \w    106.00 132.00   0.50    1.22    --  111.50 125.00  90.00   52
 57  \w     40.00  96.00   0.50    1.22    --  111.50 -77.00   0.00  112
 58  \w    113.00 138.00   0.50    1.22    --  111.50 -88.00-138.10   50
 59  \w     41.00  70.00   0.50    1.22    --  111.50 -61.00 120.00   58
;
_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      0.0581140000
_diffrn_orient_matrix_UB_12      0.0742750000
_diffrn_orient_matrix_UB_13      0.0380501000
_diffrn_orient_matrix_UB_21      -0.0745885000
_diffrn_orient_matrix_UB_22      0.0679817000
_diffrn_orient_matrix_UB_23      -0.0164419000
_diffrn_orient_matrix_UB_31      -0.0305385000
_diffrn_orient_matrix_UB_32      -0.0246664000
_diffrn_orient_matrix_UB_33      0.0691859000
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            63786
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9993
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.49
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.486
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.118a (Rigaku Oxford Diffraction, 2025)
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            'clear intense red'
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             2123.997
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.2027
_refine_diff_density_min         -3.5945
_refine_diff_density_rms         0.1139
_refine_ls_d_res_high            0.8200
_refine_ls_d_res_low             9.8482
_refine_ls_goodness_of_fit_ref   1.0542
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    129
_refine_ls_number_parameters     799
_refine_ls_number_reflns         8467
_refine_ls_number_restraints     373
_refine_ls_restrained_S_all      1.0295
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+15.3706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                8071
_reflns_number_total             8467
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ra07271a2.cif
_cod_data_source_block           RuCBr
_cod_original_formula_sum        'C46 H42.6 Br1 F6 N2 O2.3 P3 Ru1'
_cod_database_code               7251885
_chemical_oxdiff_formula         'C45 H40 Br N2 O2 P2 Ru'
_chemical_oxdiff_usercomment     'Amostra cristalina Ru-Br da Jocely-Alzir'
_diffrn_oxdiff_digest_hkl
;
433c41d898a95393266d0accf58215ce69da2b
;
_diffrn_oxdiff_digest_od_ed
;

;
_diffrn_oxdiff_measurement_exp_name 20250908_Ru-Br.par
_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
2. Restrained distances
 O2A-C1A = O2-C1 = O1-C1 = O1A-C1A
 1.27 with sigma of 0.00002
3. Uiso/Uaniso restraints and constraints
C1 \\sim O1 \\sim O2 \\sim C2 \\sim C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3
\\sim C8 \\sim Br1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
O1A \\sim C1A \\sim O2A \\sim C2A \\sim C7A \\sim C6A \\sim C5A \\sim Br1A
\\sim C4A \\sim C3A \\sim C8A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C40 \\sim C41 \\sim C42 \\sim C37 \\sim C38 \\sim C39: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C39A \\sim C40A \\sim C41A \\sim C42A \\sim C37A \\sim C38A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Br1A \\sim C8A \\sim C5A \\sim C6A \\sim C4A \\sim C3A \\sim C2A \\sim C7A
\\sim C1A \\sim O1A \\sim O2A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C38A \\sim C39A \\sim C40A \\sim C41A \\sim C42A \\sim C37A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(Br1A) = Uanis(Br1)
Uanis(O2A) = Uanis(O1A)
Uanis(C1) = Uanis(C1A)
Uanis(C37A) = Uanis(C38A) = Uanis(C42A) = Uanis(C41A) = Uanis(C40A) =
Uanis(C39A)
Uanis(O1A) = Uanis(O1) = Uanis(O2) = Uanis(O2A)
Uanis(O1A) = Uanis(O1) = Uanis(O2A) = Uanis(O2)
Uanis(O2A) = Uanis(O2)
Uanis(O1A) = Uanis(O1)
4. Rigid body (RIGU) restrains
 O1, C1, O2, C2, C7, C5, C6, C4, C3, C8, Br1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1A, C1A, O2A, C2A, C7A, C6A, C5A, C4A, C3A, Br1A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C40, C41, C42, C37, C38, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C39A, C40A, C41A, C42A, C37A, C38A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Br1A, C8A, C5A, C4A, C3A, C2A, C7A, C6A, C1A, O1A, O2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C37A, C38A, C39A, C40A, C41A, C42A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Br1(0.76) O2(0.76) O1(0.76) C1(0.76) C37(0.6) C38(0.6) H38(0.6)
 C39(0.6) H39(0.6) C40(0.6) H40(0.6) C41(0.6) H41(0.6) C42(0.6) H42(0.6)
 C8(0.76) H8a(0.76) H8b(0.76) C43(0.5) C48(0.5) H48(0.5) C47(0.5) H47(0.5)
 C46(0.5) H46(0.5) C45(0.5) H45(0.5) C44(0.5) H44(0.5) C2(0.76) C3(0.76)
 H3(0.76) C4(0.76) H4(0.76) C5(0.76) C6(0.76) H6(0.76) C7(0.76) H7(0.76)
 O2A(0.24) O1A(0.24) C1A(0.24) C8A(0.24) H8Aa(0.24) H8Ab(0.24) C2A(0.24)
 C3A(0.24) H3A(0.24) C4A(0.24) H4A(0.24) C5A(0.24) C6A(0.24) H6A(0.24)
 C7A(0.24) H7A(0.24) Br1A(0.24) H32a(0.58) H32b(0.58) H32c(0.42) H32d(0.42)
 C34(0.58) H34a(0.58) H34b(0.58) C33(0.58) H33a(0.58) H33b(0.58) C36(0.42)
 H36a(0.42) H36b(0.42) C35(0.42) H35a(0.42) H35b(0.42) C37A(0.4) C38A(0.4)
 H38A(0.4) C39A(0.4) H39A(0.4) C40A(0.4) H40A(0.4) C41A(0.4) H41A(0.4)
 C42A(0.4) H42A(0.4) C43A(0.5) C48A(0.5) H48A(0.5) C47A(0.5) H47A(0.5)
 C46A(0.5) H46A(0.5) C45A(0.5) H45A(0.5) C44A(0.5) H44A(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C8A(H8Aa,H8Ab), C31(H31a,H31b), C32(H32a,H32b), C32(H32c,H32d),
 C34(H34a,H34b), C33(H33a,H33b), C36(H36a,H36b), C35(H35a,H35b)
6.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C38(H38), C39(H39), C40(H40), C41(H41),
  C42(H42), C15(H15), C9(H9), C12(H12), C17(H17), C10(H10), C16(H16), C11(H11),
 C48(H48), C47(H47), C46(H46), C45(H45), C44(H44), C3(H3), C4(H4), C6(H6),
 C7(H7), C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C38A(H38A), C39A(H39A),
 C40A(H40A), C41A(H41A), C42A(H42A), C48A(H48A), C47A(H47A), C46A(H46A),
 C45A(H45A), C44A(H44A)
6.c Fitted hexagon refined as free rotating group:
 C25(C26,C27,C28,C29,C30), C19(C20,C21,C22,C23,C24), C37(C38,C39,C40,C41,C42),
 C43(C48,C47,C46,C45,C44), C37A(C38A,C39A,C40A,C41A,C42A), C43A(C48A,C47A,C46A,
 C45A,C44A)
;
_smtbx_masks_void_probe_radius   1.0
_smtbx_masks_void_truncation_radius 1.0
_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 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.904