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_1575508
_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_absolute_configuration syn
_chemical_formula_moiety         'C33 H43 Au N2 Se'
_chemical_formula_sum            'C33 H43 Au N2 Se'
_chemical_formula_weight         743.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-08-27 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7867(2)
_cell_length_b                   12.45932(18)
_cell_length_c                   14.6750(3)
_cell_measurement_reflns_used    10858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9500
_cell_measurement_theta_min      4.3930
_cell_volume                     3069.29(9)
_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  (Sheldrick, 2015)'
_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 0.990
_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   -116.00 -17.00   1.00    1.00    --  -41.28 -38.00-120.00   99
  2  \w    -87.00  -6.00   1.00    1.00    --  -41.28 125.00  60.00   81
  3  \w   -116.00 -17.00   1.00    1.00    --  -41.28 -38.00 -30.00   99
  4  \w     54.00 178.00   1.00    1.00    --  106.28  15.00-180.00  124
  5  \w    103.00 178.00   1.00    1.00    --  106.28  77.00-150.00   75
  6  \w     33.00 132.00   1.00    1.00    --  106.28 -45.00 -90.00   99
  7  \w     77.00 178.00   1.00    1.00    --  106.28  61.00 -90.00  101
  8  \w     24.00 106.00   1.00    1.00    --  106.28 -94.00 -30.00   82
  9  \w     24.00 106.00   1.00    1.00    --  106.28 -94.00  60.00   82
 10  \w   -114.00 -13.00   1.00    1.00    --  -41.28 -57.00-180.00  101
 11  \w    -87.00  -6.00   1.00    1.00    --  -41.28 125.00-150.00   81
 12  \w   -114.00 -13.00   1.00    1.00    --  -41.28 -57.00  90.00  101
 13  \w     78.00 178.00   1.00    1.00    --  106.28  30.00   0.00  100
 14  \w     77.00 178.00   1.00    1.00    --  106.28  61.00  60.00  101
 15  \w     24.00 106.00   1.00    1.00    --  106.28 -94.00-180.00   82
 16  \w     77.00 167.00   1.00    1.00    --  106.28  61.00-150.00   90
 17  \w     30.00 135.00   1.00    1.00    --  106.28 -30.00 120.00  105
;
_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      0.0407806000
_diffrn_orient_matrix_UB_12      0.1049662000
_diffrn_orient_matrix_UB_13      -0.0300484000
_diffrn_orient_matrix_UB_21      0.0788001000
_diffrn_orient_matrix_UB_22      -0.0384538000
_diffrn_orient_matrix_UB_23      0.0428895000
_diffrn_orient_matrix_UB_31      0.0236530000
_diffrn_orient_matrix_UB_32      -0.0528313000
_diffrn_orient_matrix_UB_33      -0.0909176000
_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  0.1198
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28558
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.057
_diffrn_reflns_theta_min         4.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.522
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.488
_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    1.609
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.097
_refine_diff_density_max         1.356
_refine_diff_density_min         -1.588
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 1937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5927
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+6.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                4993
_reflns_number_total             5927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04490a2.cif
_cod_data_source_block           db008-cdcl3-hex
_cod_depositor_comments
'Adding full bibliography for 1575505--1575508.cif.'
_cod_database_code               1575508
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C75 N2 Au1 Se1'
_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. Uiso/Uaniso restraints and constraints
C1 \\sim N3 \\sim C2 \\sim C3 \\sim N2: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C22(H22), C10(H10), C25(H25), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C7(H7), C33(H33), C30(H30), C19(H19), C31(H31), C6(H6), C8(H8),
 C18(H18), C20(H20), C32(H32)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C23(H23A,H23B,H23C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C12(H12A,
 H12B,H12C)
;
_shelx_res_checksum              78832
_olex2_date_sample_data_collection 2023-04-12
_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 3.457
_oxdiff_exptl_absorpt_empirical_full_min 0.355