A new generation of N-heterocyclic carbene (NHC) gold-selenolato complexes as potent anticancer agents: distinct synthetic routes and evaluation in 2D and 3D cancer models.
Arnaut, Pierre; Pozsoni, Nestor Bracho; Bondar, Denys; Lippmann, Petra; Boschuk, Susanne; Semenyuta, Ivan; Bhandary, Subhrajyoti; Van Hecke, Kristof; Karpichev, Yevgen; Cavarzerani, Enrico; Canzonieri, Vincenzo; Rizzolio, Flavio; Scattolin, Thomas; Vougioukalakis, Georgios C.; Ott, Ingo; Tzouras, Nikolaos V.; Nolan, Steven P.; Chemical science 16 (2025) 17221–17231; doi:10.1039/d5sc04490a

data_1575506
_publ_section_title
;
 A new generation of N-heterocyclic carbene (NHC) gold-selenolato
 complexes as potent anticancer agents: distinct synthetic routes and
 evaluation in 2D and 3D cancer models.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              17221
_journal_page_last               17231
_journal_paper_doi               10.1039/d5sc04490a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C41 H57 Au N2 Se'
_chemical_formula_sum            'C41 H57 Au N2 Se'
_chemical_formula_weight         853.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.21590(10)
_cell_length_b                   12.08800(10)
_cell_length_c                   19.21060(10)
_cell_measurement_reflns_used    25233
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5700
_cell_measurement_theta_min      2.7630
_cell_volume                     3699.64(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.61a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.72a (release 07-10-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.61a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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   -129.00  47.00   1.00    1.00    --  -41.28   0.00-180.00  176
  2  \w     72.00 119.00   1.00    1.00    --   41.28 164.00 -36.00   47
  3  \w    103.00 178.00   1.00    1.80    --  105.65  77.00 -90.00   75
  4  \w    103.00 178.00   1.00    1.80    --  105.65  77.00 150.00   75
  5  \w    103.00 178.00   1.00    1.80    --  105.65  77.00  60.00   75
  6  \w     77.00 178.00   1.00    1.80    --  105.65  30.00-120.00  101
  7  \w     33.00 135.00   1.00    1.80    --  105.65 -61.00 150.00  102
  8  \w     34.00 109.00   1.00    1.80    --  105.65-116.00  87.00   75
  9  \w     13.00 114.00   1.00    1.00    --   41.28  57.00  60.00  101
 10  \w     13.00 114.00   1.00    1.00    --   41.28  57.00 150.00  101
 11  \w     80.00 178.00   1.00    1.80    --  105.65  45.00   0.00   98
 12  \w     34.00 113.00   1.00    1.80    --  105.65-125.00   0.00   79
 13  \w     80.00 178.00   1.00    1.80    --  105.65  45.00  60.00   98
 14  \w     77.00 178.00   1.00    1.80    --  105.65  61.00 120.00  101
 15  \w     27.00  95.00   1.00    1.00    --   41.28-125.00  60.00   68
 16  \w     13.00 114.00   1.00    1.00    --   41.28  57.00 -30.00  101
 17  \w     77.00 178.00   1.00    1.80    --  105.65  61.00 -60.00  101
 18  \w     23.00  56.00   1.00    1.80    --  105.65 -94.00 120.00   33
;
_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      -0.0550442000
_diffrn_orient_matrix_UB_12      0.0773832000
_diffrn_orient_matrix_UB_13      -0.0531304000
_diffrn_orient_matrix_UB_21      -0.0080504000
_diffrn_orient_matrix_UB_22      0.0800763000
_diffrn_orient_matrix_UB_23      0.0607490000
_diffrn_orient_matrix_UB_31      0.0790861000
_diffrn_orient_matrix_UB_32      0.0619905000
_diffrn_orient_matrix_UB_33      -0.0122118000
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.518
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.61a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0204
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.9084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7008
_reflns_number_total             7352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04490a2.cif
_cod_data_source_block           db022-ben-pent
_cod_depositor_comments
'Adding full bibliography for 1575505--1575508.cif.'
_cod_database_code               1575506
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 AU Se'
_shelx_estimated_absorpt_t_max   0.413
_shelx_estimated_absorpt_t_min   0.278
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C28(H28), C17(H17), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C32(H32A,H32B), C11(H11A,H11B), C13(H13A,H13B), C18(H18A,
 H18B), C29(H29A,H29B), C34(H34A,H34B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C22(H22), C41(H41), C6(H6), C24(H24), C8(H8), C23(H23),
 C37(H37), C38(H38), C7(H7), C40(H40), C39(H39)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C35(H35A,H35B,H35C), C26(H26A,H26B,H26C), C12(H12A,H12B,
 H12C), C14(H14A,H14B,H14C), C31(H31A,H31B,H31C), C15(H15A,H15B,H15C), C30(H30A,
 H30B,H30C)
;
_shelx_res_checksum              97255
_olex2_date_sample_data_collection 2023-08-11
_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 2.461
_oxdiff_exptl_absorpt_empirical_full_min 0.435