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_7047654
_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         'C24 H23 Au N4 O P, Cl O4'
_chemical_formula_sum            'C24 H23 Au Cl N4 O5 P'
_chemical_formula_weight         710.85
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_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                66.312(8)
_cell_angle_beta                 74.845(7)
_cell_angle_gamma                66.970(8)
_cell_formula_units_Z            4
_cell_length_a                   13.2511(11)
_cell_length_b                   14.8189(13)
_cell_length_c                   15.7353(12)
_cell_measurement_reflns_used    8023
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.1710
_cell_measurement_theta_min      3.7600
_cell_volume                     2584.0(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -100.00 -69.00   1.00    5.00    --  -36.88-178.00-180.00   31
  2  \w    -87.00 -28.00   1.00    5.00    --  -36.88 119.00 -43.00   59
  3  \w   -108.00 -60.00   1.00    5.00    --  -36.88-178.00   0.00   48
  4  \w   -108.00 -39.00   1.00    5.00    --  -36.88 158.00 110.00   69
  5  \w     20.00 104.00   1.00    5.00    --   36.88  57.00  30.00   84
  6  \w    -27.00  14.00   1.00    5.00    --   36.88 -57.00 150.00   41
  7  \w     36.00  65.00   1.00    5.00    --   36.88 178.00 -60.00   29
  8  \w     51.00 101.00   1.00    5.00    --   36.88 178.00-180.00   50
  9  \w      8.00 108.00   1.00    5.00    --   36.88  19.00 -30.00  100
 10  \w    114.00 174.00   1.00   30.00    --  107.00  45.00 120.00   60
 11  \w     69.00 176.00   1.00   30.00    --  107.00  15.00  60.00  107
 12  \w     89.00 116.00   1.00   30.00    --  107.00 -92.00  22.03   27
 13  \w    126.00 172.00   1.00   30.00    --  107.00  30.00  90.00   46
 14  \w     39.00 114.00   1.00   30.00    --  107.00 -45.00 -90.00   75
 15  \w     42.00 124.00   1.00   30.00    --  107.00 -45.00-180.00   82
 16  \w     41.00 113.00   1.00   30.00    --  107.00 -45.00  60.00   72
 17  \w     41.00  66.00   1.00   30.00    --  107.00-111.00 -60.00   25
 18  \w     54.00 119.00   1.00   30.00    --  107.00 -30.00  90.00   65
 19  \w     61.00 124.00   1.00   30.00    --  107.00 -45.00 -30.00   63
 20  \w     51.00 143.00   1.00   30.00    --  107.00 -93.00  80.85   92
 21  \w     71.00 121.00   1.00   30.00    --  107.00 -91.00-171.33   50
 22  \w     59.00 133.00   1.00   30.00    --  107.00 -92.00 -64.15   74
;
_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      -0.0705084000
_diffrn_orient_matrix_UB_12      -0.0649097000
_diffrn_orient_matrix_UB_13      0.0070740000
_diffrn_orient_matrix_UB_21      -0.0036689000
_diffrn_orient_matrix_UB_22      0.0490501000
_diffrn_orient_matrix_UB_23      -0.1064568000
_diffrn_orient_matrix_UB_31      0.1059335000
_diffrn_orient_matrix_UB_32      -0.0881918000
_diffrn_orient_matrix_UB_33      -0.0149953000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_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            15895
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         3.442
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41190
_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    1.827
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, hexane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.252
_refine_diff_density_min         -1.828
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         9215
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8225
_reflns_number_total             9215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt02832j2.cif
_cod_data_source_block           v04af71d
_cod_depositor_comments
'Adding full bibliography for 7047652--7047655.cif.'
_cod_database_code               7047654
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C80 H120 Au4 Cl2 N26 O20 P6 '
_reflns_odcompleteness_completeness 99.73
_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 C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C6A-C1AA
 1.5 with sigma of 0.02
3. Rigid bond restraints
 O1A, C6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1A \\sim C6A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
5. Others
 Sof(O1A)=Sof(H1A)=Sof(H1AC)=Sof(H1AD)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(H1AA)=Sof(H1AB)=Sof(C6)=Sof(H6C)=Sof(H6D)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C1AA(H1AC,H1AD), C6(H6C,H6D), C6A(H6AA,H6AB), C127(H12A,
 H12B), C128(H12C,H12D)
6.b 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),
  C105(H105), C112(H112), C113(H113), C114(H114), C115(H115), C116(H116),
 C117(H117), C118(H118), C119(H119), C120(H120), C121(H121), C122(H122),
 C123(H123), C124(H124), C125(H125), C126(H126)
6.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N106(H10A,H10B)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A), O129(H129)
;
_olex2_date_sample_data_collection 2017-11-14
_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 4.334
_oxdiff_exptl_absorpt_empirical_full_min 0.676