Synthesis of novel heteroleptic delocalised cationic pyrazole gold complexes as potent HepG2 cytotoxic agents.
Afolabi, Fatai; Souissi, Wided; Rivière, Guillaume; Lemaitre, Clément; Roe, S. Mark; Crickmore, Neil; Viseux, Eddy M. E.; Dalton transactions (Cambridge, England : 2003) 47 (2018) 15338–15343; doi:10.1039/c8dt02832j

data_7047652
_publ_section_title
;
 Synthesis of novel heteroleptic delocalised cationic pyrazole gold
 complexes as potent HepG2 cytotoxic agents.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15338
_journal_page_last               15343
_journal_paper_doi               10.1039/c8dt02832j
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C22 H21 Au Br N3 P, Cl O4, C H2 Cl2'
_chemical_formula_sum            'C23 H23 Au Br Cl3 N3 O4 P'
_chemical_formula_weight         819.64
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-07-06 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.268(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8129(4)
_cell_length_b                   6.9184(2)
_cell_length_c                   29.6985(9)
_cell_measurement_reflns_used    8392
_cell_measurement_temperature    173
_cell_measurement_theta_max      70.8280
_cell_measurement_theta_min      4.9890
_cell_volume                     2762.33(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -106.00 -79.00   1.00   10.00    --  -36.75-178.00 -60.00   27
  2  \w    -84.00 -28.00   1.00   10.00    --  -36.75 114.00 -85.00   56
  3  \w    -84.00 -58.00   1.00   10.00    --  -36.75-178.00  30.00   26
  4  \w    -17.00  40.00   1.00   10.00    --   36.75 -57.00-150.00   57
  5  \w    -31.00   1.00   1.00   10.00    --   36.75 -38.00 -90.00   32
  6  \w     13.00  39.00   1.00   10.00    --   36.75  77.00-150.00   26
  7  \w     33.00  73.00   1.00   10.00    --   36.75-178.00 -90.00   40
  8  \w     26.00 106.00   1.00   10.00    --   36.75  38.00  90.00   80
  9  \w     28.00  76.00   1.00   10.00    --   36.75 -99.00 120.00   48
 10  \w    -30.00  22.00   1.00   10.00    --   36.75 -19.00 -90.00   52
 11  \w     23.00  54.00   1.00   10.00    --   36.75 -38.00 -90.00   31
 12  \w     32.00  66.00   1.00   10.00    --   36.75 -19.00 -90.00   34
 13  \w     38.00 123.00   1.00   60.00    --  107.00 -30.00-120.00   85
 14  \w     52.00  78.00   1.00   60.00    --  107.00-111.00  90.00   26
 15  \w    128.00 175.00   1.00   60.00    --  107.00  45.00  60.00   47
 16  \w     39.00  65.00   1.00   60.00    --  107.00 -95.00 120.00   26
 17  \w     52.00 141.00   1.00   60.00    --  107.00 -91.00 139.29   89
 18  \w     48.00  73.00   1.00   60.00    --  107.00 -93.00  -8.08   25
 19  \w    149.00 174.00   1.00   60.00    --  107.00  77.00 -90.00   25
 20  \w     44.00  77.00   1.00   60.00    --  107.00 -95.00  30.00   33
 21  \w    136.00 174.00   1.00   60.00    --  107.00  45.00 -90.00   38
 22  \w     78.00 137.00   1.00   60.00    --  107.00 -93.00-116.53   59
 23  \w     40.00 122.00   1.00   60.00    --  107.00 -45.00 120.00   82
 24  \w     90.00 119.00   1.00   60.00    --  107.00  45.00 -90.00   29
 25  \w     37.00 128.00   1.00   60.00    --  107.00 -30.00 -30.00   91
 26  \w     38.00  79.00   1.00   60.00    --  107.00 -95.00 -60.00   41
 27  \w     69.00 178.00   1.00   60.00    --  107.00  15.00-150.00  109
 28  \w     81.00 131.00   1.00   60.00    --  107.00 -93.00  -8.08   50
 29  \w     94.00 120.00   1.00   60.00    --  107.00 -93.00-146.13   26
 30  \w     85.00 110.00   1.00   60.00    --  107.00 -93.00  98.85   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0926990000
_diffrn_orient_matrix_UB_12      -0.0753377000
_diffrn_orient_matrix_UB_13      0.0348403000
_diffrn_orient_matrix_UB_21      -0.0327070000
_diffrn_orient_matrix_UB_22      0.1089761000
_diffrn_orient_matrix_UB_23      0.0392894000
_diffrn_orient_matrix_UB_31      -0.0588108000
_diffrn_orient_matrix_UB_32      -0.1788454000
_diffrn_orient_matrix_UB_33      0.0093066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16828
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         3.943
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_description       needle
_exptl_crystal_F_000             1576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, hexane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         3.262
_refine_diff_density_min         -1.289
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0575P)^2^+32.1063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4473
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt02832j2.cif
_cod_data_source_block           v04af77d
_cod_depositor_comments
'Adding full bibliography for 7047652--7047655.cif.'
_cod_database_code               7047652
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O Cl Br Au P'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 Cl1, Cl1, Cl1, Cl1, Cl1, O1, O1, O2, O2, O3, O3, O4, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2, Cl2, Cl3, Cl3, C27, C27, C27, C27, C27, H27A, H27A, H27B, H27B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Rotating group:
 N6(H6A,H6B)
3.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2017-12-14
_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.722