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_1575505
_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         'C34 H40 Au F3 N2 Se'
_chemical_formula_sum            'C34 H40 Au F3 N2 Se'
_chemical_formula_weight         809.60
_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             2021-12-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.959(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3647(2)
_cell_length_b                   14.9049(2)
_cell_length_c                   16.6539(2)
_cell_measurement_reflns_used    15108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.3210
_cell_measurement_theta_min      3.3930
_cell_volume                     3232.68(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_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      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 0.985
_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    --  -41.16   0.00   0.00  176
  2  \w    -87.00  -6.00   1.00    1.00    --  -41.16 125.00-150.00   81
  3  \w     27.00  97.00   1.00    1.00    --   41.16-125.00  90.00   70
  4  \w    103.00 178.00   1.00    2.50    --  106.28  77.00 -90.00   75
  5  \w     33.00 112.00   1.00    2.50    --  106.28-125.00 -30.00   79
  6  \w     80.00 178.00   1.00    2.50    --  106.28  45.00  60.00   98
  7  \w     24.00 106.00   1.00    2.50    --  106.28 -94.00 -30.00   82
  8  \w     33.00 112.00   1.00    2.50    --  106.28-125.00 150.00   79
  9  \w     33.00 132.00   1.00    2.50    --  106.28 -45.00 -90.00   99
 10  \w    103.00 178.00   1.00    2.50    --  106.28  77.00-180.00   75
 11  \w     24.00 106.00   1.00    2.50    --  106.28 -94.00-180.00   82
 12  \w   -114.00 -13.00   1.00    1.00    --  -41.16 -57.00 -30.00  101
 13  \w     13.00 114.00   1.00    1.00    --   41.16  57.00 -90.00  101
 14  \w     13.00 114.00   1.00    1.00    --   41.16  57.00-180.00  101
 15  \w     78.00 178.00   1.00    2.50    --  106.28  30.00 -90.00  100
 16  \w     78.00 178.00   1.00    2.50    --  106.28  30.00 150.00  100
 17  \w     77.00 109.00   1.00    2.50    --  106.28  61.00 -60.00   32
 18  \w     80.00 178.00   1.00    2.50    --  106.28  45.00   0.00   98
;
_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      0.0648244000
_diffrn_orient_matrix_UB_12      -0.0864353000
_diffrn_orient_matrix_UB_13      0.0264962000
_diffrn_orient_matrix_UB_21      -0.0979160000
_diffrn_orient_matrix_UB_22      -0.0566231000
_diffrn_orient_matrix_UB_23      -0.0472213000
_diffrn_orient_matrix_UB_31      0.0144729000
_diffrn_orient_matrix_UB_32      0.0043636000
_diffrn_orient_matrix_UB_33      -0.0863863000
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.701
_diffrn_reflns_theta_min         3.421
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
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    1.663
_exptl_crystal_description       plate
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.091
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6437
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0329P)^2^+3.6880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5602
_reflns_number_total             6437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04490a2.cif
_cod_data_source_block           nb071-cdcl3-hex-100k
_cod_depositor_comments
'Adding full bibliography for 1575505--1575508.cif.'
_cod_original_cell_volume        3232.67(9)
_cod_database_code               1575505
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.686
_shelx_estimated_absorpt_t_min   0.293
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C34A-C31 \\sim C34-C31
 with sigma of 0.01
 F2-C34 \\sim F1-C34 \\sim F2A-C34A \\sim F1A-C34A \\sim F3A-C34A \\sim F3-C34
 with sigma of 0.01
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F3 \\sim C34 \\sim F2 \\sim F1 \\sim C34A \\sim F3A \\sim F2A \\sim F1A: within
2A with sigma of 0.008 and sigma for terminal atoms of 0.016 within 2A
C25 \\sim C27 \\sim C26: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(C34A)=Sof(F3A)=Sof(F2A)=Sof(F1A)=1-FVAR(1)
 Sof(F3)=Sof(C34)=Sof(F2)=Sof(F1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10), C22(H22), C25(H25)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C32(H32), C6(H6), C33(H33), C29(H29), C20(H20), C7(H7),
 C30(H30), C8(H8), C18(H18), C19(H19)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C24(H24A,H24B,
 H24C), C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C26(H26A,
 H26B,H26C)
;
_shelx_res_checksum              7413
_olex2_date_sample_data_collection 2021-11-23
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.688