The effect of halogenation of salicylaldehyde on antiproliferative activities of {∆/Λ-[Ru(bpy)2(X,Y-sal)]BF4} complexes
Taghizadeh Shool, Maryam; Amiri Rudbari, Hadi; Gil-Antón, Tania Gil-Antón; Cuevas-Vicario, José Vicente; Garcia, Begona; Busto, Natalia; Moini, Nakisa; Blacque, Olivier; Dalton Transactions  (2022) –; doi:10.1039/D2DT00401A

data_7710088
_publ_section_title
;
 The effect of halogenation of salicylaldehyde on antiproliferative
 activities of {&#x2206;/\L-[Ru(bpy)2(X,Y-sal)]BF4} complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00401A
_journal_year                    2022
_chemical_formula_moiety
'2(C27 H19 Br Cl N4 O2 Ru), 2(B F4), H2 O, 2(C2 H6 O)'
_chemical_formula_sum            'C58 H52 B2 Br2 Cl2 F8 N8 O7 Ru2'
_chemical_formula_weight         1579.55
_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             2021-09-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-10 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                63.333(6)
_cell_angle_beta                 70.416(6)
_cell_angle_gamma                76.745(5)
_cell_formula_units_Z            1
_cell_length_a                   11.7796(7)
_cell_length_b                   12.0345(7)
_cell_length_c                   12.9612(8)
_cell_measurement_reflns_used    6157
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.3530
_cell_measurement_theta_min      3.9460
_cell_volume                     1540.17(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_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    -80.00  25.00   0.50    4.80    --  -51.54  95.00 119.00  210
  2  \w    -10.00  83.00   0.50    4.80    --   51.54 -95.00   9.00  186
  3  \w    -80.00  -9.00   0.50   19.20    --  -86.25  95.00 119.00  142
  4  \w   -163.00 -83.00   0.50   19.20    --  -86.25 -95.00   9.00  160
  5  \w    104.00 178.00   0.50   19.20    --  107.75  95.00 119.00  148
  6  \w     31.00 106.00   0.50   19.20    --  107.75 -95.00   9.00  150
  7  \w    -87.00 -12.00   0.50    4.80    --  -51.54 125.00 -90.00  150
  8  \w   -125.00 -29.00   0.50    4.80    --  -51.54 -77.00 120.00  192
  9  \w   -124.00 -37.00   0.50    4.80    --  -51.54 -57.00-180.00  174
 10  \w    -64.00  28.00   0.50    4.80    --  -51.54  19.00 -60.00  184
 11  \w     37.00 124.00   0.50    4.80    --   51.54  57.00 -30.00  174
 12  \w   -166.00-103.00   0.50   19.20    --  -86.25 -15.00-150.00  126
 13  \w   -157.00 -68.00   0.50   19.20    --  -86.25 -69.00 142.74  178
 14  \w     85.00 143.00   0.50   19.20    --  107.75  77.00 -90.00  116
 15  \w     75.00 109.00   0.50   19.20    --  107.75-111.00-120.00   68
 16  \w     98.00 127.00   0.50   19.20    --  107.75 -77.00  90.00   58
 17  \w    108.00 167.00   0.50   19.20    --  107.75  45.00-120.00  118
 18  \w     68.00 106.00   0.50   19.20    --  107.75 -94.00-120.00   76
 19  \w     72.00 109.00   0.50   19.20    --  107.75-111.00-180.00   74
 20  \w     55.00 119.00   0.50   19.20    --  107.75 -15.00 -30.00  128
 21  \w     38.00  69.00   0.50   19.20    --  107.75-111.00-120.00   62
 22  \w     38.00  78.00   0.50   19.20    --  107.75 -45.00  60.00   80
 23  \w     47.00 106.00   0.50   19.20    --  107.75 -94.00  60.00  118
 24  \w     36.00  65.00   0.50   19.20    --  107.75 -77.00  90.00   58
 25  \w     95.00 120.00   0.50   19.20    --  107.75 -45.00  60.00   50
 26  \w     31.00 105.00   0.50   19.20    --  107.75 -94.00  30.00  148
 27  \w     75.00 106.00   0.50   19.20    --  107.75 -94.00 -90.00   62
 28  \w    104.00 133.00   0.50   19.20    --  107.75 111.00 -60.00   58
 29  \w    136.00 177.00   0.50   19.20    --  107.75 111.00 -60.00   82
 30  \w     31.00  72.00   0.50   19.20    --  107.75 -94.00 -90.00   82
 31  \w     50.00  83.00   0.50   19.20    --  107.75-111.00  90.00   66
 32  \w     32.00 108.00   0.50   19.20    --  107.75-111.00   0.00  152
 33  \w     31.00  70.00   0.50   19.20    --  107.75-111.00-180.00   78
 34  \w    104.00 175.00   0.50   19.20    --  107.75 111.00-120.00  142
 35  \w     97.00 145.00   0.50   19.20    --  107.75  61.00 -60.00   96
 36  \w     95.00 178.00   0.50   19.20    --  107.75  30.00  30.00  166
 37  \w     94.00 154.00   0.50   19.20    --  107.75  61.00-180.00  120
 38  \w     93.00 138.00   0.50   19.20    --  107.75 178.00  30.00   90
 39  \w     65.00 114.00   0.50   19.20    --  107.75 -45.00 150.00   98
 40  \w     55.00  82.00   0.50   19.20    --  107.75 -94.00 -60.00   54
 41  \w     60.00 106.00   0.50   19.20    --  107.75 -94.00  90.00   92
 42  \w     33.00  34.00   0.50   19.20    --  107.75 -45.00 150.00    2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1077176000
_diffrn_orient_matrix_UB_12      -0.0481240000
_diffrn_orient_matrix_UB_13      0.0559119000
_diffrn_orient_matrix_UB_21      -0.0796923000
_diffrn_orient_matrix_UB_22      -0.0903641000
_diffrn_orient_matrix_UB_23      0.1157011000
_diffrn_orient_matrix_UB_31      0.0385416000
_diffrn_orient_matrix_UB_32      -0.1010952000
_diffrn_orient_matrix_UB_33      -0.0503642000
_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  0.0855
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.504
_diffrn_reflns_theta_min         3.960
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.006
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       plate
_exptl_crystal_F_000             786
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6270
_refine_ls_number_restraints     195
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0851P)^2^+0.7578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4042
_reflns_number_total             6270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00401a2.cif
_cod_data_source_block           hadi0809
_cod_original_cell_volume        1540.17(19)
_cod_database_code               7710088
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.767
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 F1B-F2B
 2.41 with sigma of 0.01
 F1B-F3B
 2.41 with sigma of 0.01
 F4B-F3B
 2.41 with sigma of 0.01
 F1B-F4B
 2.41 with sigma of 0.01
 F3B-F2B
 2.41 with sigma of 0.01
 F4B-F2B
 2.41 with sigma of 0.01
 F3A-F1A
 2.41 with sigma of 0.01
 F2A-F4A
 2.41 with sigma of 0.01
 F1A-F2A
 2.41 with sigma of 0.01
 F3A-F2A
 2.41 with sigma of 0.01
 F4A-F1A
 2.41 with sigma of 0.01
 F3A-F4A
 2.41 with sigma of 0.01
 F3B-B1 \\sim F4A-B1 \\sim F4B-B1 \\sim F2A-B1 \\sim F2B-B1 \\sim F3A-B1 \\sim
F1B-B1
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
F1A \\sim F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B \\sim F4A: within 3A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 3A
F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B \\sim F4A \\sim F4B: within 3A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 3A
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=FVAR(1)
 Fixed Sof: O3(0.5) H3A(0.5) H3B(0.5)
 Fixed X: H3A(-0.1644) H3B(-0.202391)
 Fixed Y: H3A(-0.024571) H3B(0.100261)
 Fixed Z: H3A(0.935489) H3B(0.9058)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23),
  C25(H25), C27(H27)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              54792
_shelx_hkl_checksum              98553
_shelx_fab_checksum              89430