Clinically used antifungal azoles as ligands for gold(iii) complexes: the influence of the Au(iii) ion on the antimicrobial activity of the complex
Stevanović, Nevena Lj.; Kljun, Jakob; Aleksic, Ivana; Bogojevic, Sanja Skaro; Milivojevic, Dusan; Veselinovic, Aleksandar; Turel, Iztok; Djuran, Miloš I.; Nikodinovic-Runic, Jasmina; Glišić, Biljana Đ.; Dalton Transactions  (2022) –; doi:10.1039/D2DT00411A

data_7709765
_publ_section_title
;
 Clinically used antifungal azoles as ligands for gold(iii) complexes: the
 influence of the Au(iii) ion on the antimicrobial activity of the complex
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00411A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 Au Cl3 F3 N5 O'
_chemical_formula_sum            'C16 H14 Au Cl3 F3 N5 O'
_chemical_formula_weight         652.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.004(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1732(6)
_cell_length_b                   5.8139(2)
_cell_length_c                   15.0734(7)
_cell_measurement_reflns_used    7220
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      2.7300
_cell_volume                     1050.58(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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    -14.00  82.00   1.00    6.28    --   10.78  37.00 -30.00   96
  2  \w    -13.00  85.00   1.00    6.28    --   10.78  37.00 120.00   98
  3  \w    -16.00  83.00   1.00    6.28    --   10.78  57.00-150.00   99
  4  \w    -58.00  35.00   1.00    6.28    --   10.78 -37.00 150.00   93
  5  \w    -14.00  52.00   1.00    6.28    --   10.78 -99.00 -60.00   66
  6  \w     -7.00  23.00   1.00    6.28    --  -11.01 -99.00 -60.00   30
  7  \w    -44.00  21.00   1.00    6.28    --  -11.01  77.00 -30.00   65
  8  \w    -44.00  21.00   1.00    6.28    --  -11.01  77.00  60.00   65
  9  \w    -63.00 -37.00   1.00    6.28    --  -11.01 118.00 123.35   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0135950000
_diffrn_orient_matrix_UB_12      0.1182263000
_diffrn_orient_matrix_UB_13      0.0022672000
_diffrn_orient_matrix_UB_21      0.0511189000
_diffrn_orient_matrix_UB_22      0.0196319000
_diffrn_orient_matrix_UB_23      0.0296471000
_diffrn_orient_matrix_UB_31      0.0265543000
_diffrn_orient_matrix_UB_32      0.0227499000
_diffrn_orient_matrix_UB_33      -0.0373940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17737
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.744
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_description       needle
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.358
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Flack x determined using 1817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0268P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0578
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4391
_reflns_number_total             4754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00411a2.cif
_cod_data_source_block           moc471
_cod_original_cell_volume        1050.57(8)
_cod_database_code               7709765
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Au1 Cl3 C16 H14 F3 N5 O1'
_shelx_estimated_absorpt_t_max   0.524
_shelx_estimated_absorpt_t_min   0.214
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C15(H15), C23(H23), C13(H13), C22(H22), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              12469
_shelx_hkl_checksum              45959
_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 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.632