A simple synthetic entryway into new families of NHC-gold-amido complexes and their in vitro antitumor activity
Nolan, Steven P.; Martynova, Ekaterina A.; Van Hecke, Kristof; Rizzolio, Flavio; Peng, Min; Cavarzenari, Enrico; Scattolin, Thomas; Dalton Transactions  (2022) –; doi:10.1039/D2DT00239F

data_7709429
_publ_section_title
;
 A simple synthetic entryway into new families of NHC-gold-amido complexes
 and their in vitro antitumor activity
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00239F
_journal_year                    2022
_chemical_formula_moiety         'C78 H65 Au N4'
_chemical_formula_sum            'C78 H65 Au N4'
_chemical_formula_weight         1255.31
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-04
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-05 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                88.846(2)
_cell_angle_beta                 83.837(2)
_cell_angle_gamma                86.417(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0142(2)
_cell_length_b                   13.9263(3)
_cell_length_c                   21.1975(5)
_cell_measurement_reflns_used    16931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8500
_cell_measurement_theta_min      3.1570
_cell_volume                     3226.02(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_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      100(2)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -66.00  33.00   1.00    3.80    --  -41.68  38.00 -60.00   99
  2  \w   -116.00 -17.00   1.00    3.80    --  -41.68 -38.00 120.00   99
  3  \w    -74.00  34.00   1.00    3.80    --  -41.68  77.00  30.00  108
  4  \w      7.00  34.00   1.00    3.80    --   41.68  83.00-103.60   27
  5  \w      7.00  33.00   1.00    3.80    --   41.68  84.00  98.55   26
  6  \w      7.00  33.00   1.00    3.80    --   41.68  84.00 137.20   26
  7  \w     78.00 178.00   1.00   24.00    --  106.01  30.00-120.00  100
  8  \w     23.00 107.00   1.00   24.00    --  106.01 -94.00  30.00   84
  9  \w     33.00 132.00   1.00   24.00    --  106.01 -45.00-180.00   99
 10  \w     23.00 107.00   1.00   24.00    --  106.01 -94.00-180.00   84
 11  \w     78.00 178.00   1.00   24.00    --  106.01  30.00 150.00  100
 12  \w     33.00 112.00   1.00   24.00    --  106.01-125.00   0.00   79
 13  \w    103.00 178.00   1.00   24.00    --  106.01  77.00 -90.00   75
 14  \w    103.00 178.00   1.00   24.00    --  106.01  77.00   0.00   75
 15  \w    103.00 178.00   1.00   24.00    --  106.01  77.00 -60.00   75
 16  \w     33.00 132.00   1.00   24.00    --  106.01 -45.00 -60.00   99
 17  \w     34.00 120.00   1.00   24.00    --  106.01-135.00 -44.00   86
 18  \w     25.00 107.00   1.00   24.00    --  106.01 -99.00 120.00   82
 19  \w   -116.00 -17.00   1.00    3.80    --  -41.68 -38.00 -60.00   99
 20  \w    -87.00  -6.00   1.00    3.80    --  -41.68 125.00  90.00   81
 21  \w      8.00  42.00   1.00    3.80    --   41.68  82.00 -57.29   34
 22  \w      8.00  42.00   1.00    3.80    --   41.68  82.00  44.79   34
 23  \w      9.00  42.00   1.00    3.80    --   41.68  76.00-148.85   33
 24  \w     80.00 178.00   1.00   24.00    --  106.01  45.00 -60.00   98
 25  \w     77.00 178.00   1.00   24.00    --  106.01  59.00  47.62  101
 26  \w     53.00 178.00   1.00   24.00    --  106.01  15.00  60.00  125
 27  \w     77.00 178.00   1.00   24.00    --  106.01  59.00 -29.33  101
 28  \w     76.00 178.00   1.00   24.00    --  106.01  64.00-104.61  102
 29  \w     76.00 178.00   1.00   24.00    --  106.01  65.00 167.29  102
 30  \w     76.00 178.00   1.00   24.00    --  106.01  65.00   9.35  102
 31  \w     75.00 178.00   1.00   24.00    --  106.01  69.00 127.57  103
 32  \w     75.00 178.00   1.00   24.00    --  106.01  71.00-139.56  103
 33  \w     78.00 178.00   1.00   24.00    --  106.01  54.00  87.57  100
 34  \w   -116.00 -17.00   1.00    3.80    --  -41.68 -38.00-120.00   99
 35  \w   -116.00 -17.00   1.00    3.80    --  -41.68 -38.00   0.00   99
 36  \w      7.00  34.00   1.00    3.80    --   41.68  83.00 169.79   27
 37  \w      8.00  42.00   1.00    3.80    --   41.68  81.00 -86.34   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            60247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.847
_diffrn_reflns_theta_min         3.180
_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.371
_refine_diff_density_min         -1.525
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         12847
_refine_ls_number_restraints     532
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0682P)^2^+1.6265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10523
_reflns_number_total             12847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00239f2.cif
_cod_data_source_block           em_120_3
_cod_database_code               7709429
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.913
_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
2. Restrained distances
 C18A-C19A = C19A-C20A = C20A-C21A = C21A-C22A = C22A-C23A = C23A-C18A
 1.39 with sigma of 0.01
 C18B-C19B = C19B-C20B = C20B-C21B = C21B-C22B = C22B-C23B = C23B-C18B
 1.39 with sigma of 0.01
 C45-C46 = C46-C47 = C47-C48 = C48-C49 = C49-C50 = C50-C45
 1.39 with sigma of 0.01
 C31A-C32A = C32A-C33A = C33A-C34A = C34A-C35A = C35A-C36A = C36A-C31A
 1.39 with sigma of 0.01
 C31B-C32B = C32B-C33B = C33B-C34B = C34B-C35B = C35B-C36B = C36B-C31B
 1.39 with sigma of 0.01
 C11-C18A = C11-C18B
 1.526 with sigma of 0.01
 C24A-C25A = C24A-C31A
 1.526 with sigma of 0.01
 C25A-C26A = C26A-C27A = C27A-C28A = C28A-C29A = C29A-C30A = C30A-C25A
 1.39 with sigma of 0.01
 C25B-C26B = C26B-C27B = C27B-C28B = C28B-C29B = C29B-C30B = C30B-C25B
 1.39 with sigma of 0.01
 C24B-C25B = C24B-C31B
 1.526 with sigma of 0.01
 C58-C59 = C59-C60 = C60-C61 = C61-C62 = C62-C63 = C63-C58
 1.39 with sigma of 0.01
 C64A-C65A = C65A-C66A = C66A-C67A = C67A-C68A = C68A-C69A = C69A-C64A
 1.39 with sigma of 0.01
 C64B-C65B = C65B-C66B = C66B-C67B = C67B-C68B = C68B-C69B = C69B-C64B
 1.39 with sigma of 0.01
 C57-C64A = C57-C64B
 1.526 with sigma of 0.01
 C31A-C33A = C32A-C34A = C33A-C35A = C34A-C36A = C35A-C31A
 2.4 with sigma of 0.02
 C31B-C33B = C32B-C34B = C33B-C35B = C34B-C36B = C35B-C31B
 2.4 with sigma of 0.02
 C25A-C27A = C26A-C28A = C27A-C29A = C28A-C30A = C29A-C25A
 2.4 with sigma of 0.02
 C25B-C27B = C26B-C28B = C27B-C29B = C28B-C30B = C29B-C25B
 2.4 with sigma of 0.02
 C64A-C66A = C65A-C67A = C66A-C68A = C67A-C69A = C68A-C64A
 2.4 with sigma of 0.02
 C64B-C66B = C65B-C67B = C66B-C68B = C67B-C69B = C68B-C64B
 2.4 with sigma of 0.02
3. Restrained planarity
 C24A, C31A, C32A, C33A, C34A, C35A, C36A
 with sigma of 0.001
 C24A, C31B, C32B, C33B, C34B, C35B, C36B
 with sigma of 0.001
 C25A, C26A, C27A, C28A, C29A, C30A
 with sigma of 0.001
 C25B, C26B, C27B, C28B, C29B, C30B
 with sigma of 0.001
 C64A, C65A, C66A, C67A, C68A, C69A
 with sigma of 0.001
 C64B, C65B, C66B, C67B, C68B, C69B
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C23A: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C18B \\sim C19B \\sim C20B \\sim C21B \\sim C22B \\sim C23B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C31B \\sim C32B \\sim C33B \\sim C34B \\sim C35B \\sim C36B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C24A \\sim C25A \\sim C26A \\sim C27A \\sim C28A \\sim C29A \\sim C30A: within
2A with sigma of 0.005 and sigma for terminal atoms of 0.01
C24B \\sim C25B \\sim C26B \\sim C27B \\sim C28B \\sim C29B \\sim C30B: within
2A with sigma of 0.005 and sigma for terminal atoms of 0.01
C58 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
C64A \\sim C65A \\sim C66A \\sim C67A \\sim C68A \\sim C69A: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
C64B \\sim C65B \\sim C66B \\sim C67B \\sim C68B \\sim C69B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(C20A) = Uanis(C20B)
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C31A) = Uanis(C31B)
Uanis(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
Uanis(C27A) = Uanis(C27B)
Uanis(C28A) = Uanis(C28B)
Uanis(C29A) = Uanis(C29B)
Uanis(C30A) = Uanis(C30B)
Uanis(C64A) = Uanis(C64B)
Uanis(C65A) = Uanis(C65B)
Uanis(C66A) = Uanis(C66B)
Uanis(C67A) = Uanis(C67B)
Uanis(C68A) = Uanis(C68B)
Uanis(C69A) = Uanis(C69B)
Uanis(C24A) = Uanis(C24B)
5. Others
 Sof(H11A)=Sof(C18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=
 Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23B)=1-FVAR(1)
 Sof(H11)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=FVAR(1)
 Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=
 Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=
 Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(H33B)=Sof(C34B)=Sof(H34B)=Sof(C35B)=
 Sof(H35B)=Sof(C36B)=Sof(H36B)=1-FVAR(2)
 Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=
 Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=
 Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=
 Sof(H35A)=Sof(C36A)=Sof(H36A)=FVAR(2)
 Sof(H57A)=Sof(C64B)=Sof(C65B)=Sof(H65B)=Sof(C66B)=Sof(H66B)=Sof(C67B)=
 Sof(H67B)=Sof(C68B)=Sof(H68B)=Sof(C69B)=Sof(H69B)=1-FVAR(3)
 Sof(H57)=Sof(C64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=Sof(C67A)=
 Sof(H67A)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69A)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C11(H11A), C44(H44), C57(H57), C57(H57A), C24A(H24A), C24B(H24B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C39(H39), C41(H41), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
  C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63), C70(H70), C72(H72), C75(H75), C19A(H19A),
 C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C26A(H26A), C27A(H27A),
 C28A(H28A), C29A(H29A), C30A(H30A), C32A(H32A), C33A(H33A), C34A(H34A),
 C35A(H35A), C36A(H36A), C65A(H65A), C66A(H66A), C67A(H67A), C68A(H68A),
 C69A(H69A), C19B(H19B), C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B),
 C26B(H26B), C27B(H27B), C28B(H28B), C29B(H29B), C30B(H30B), C32B(H32B),
 C33B(H33B), C34B(H34B), C35B(H35B), C36B(H36B), C65B(H65B), C66B(H66B),
 C67B(H67B), C68B(H68B), C69B(H69B)
6.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C43(H43A,H43B,H43C), C77(H77A,H77B,H77C), C78(H78A,H78B,
 H78C)
;
_shelx_res_checksum              56434
_shelx_fab_checksum              41606
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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
;