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_7709433
_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         'C48 H53 Au N4'
_chemical_formula_sum            'C48 H53 Au N4'
_chemical_formula_weight         882.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-01-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-11-05 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.73610(10)
_cell_length_b                   18.81190(10)
_cell_length_c                   25.19810(10)
_cell_measurement_reflns_used    75690
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8480
_cell_measurement_theta_min      3.0090
_cell_volume                     8407.34(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_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 0.993
_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   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00-150.00  101
  2  \w      6.00  83.00   1.00    5.00    --   41.68 -99.00 150.00   77
  3  \w     27.00  98.00   1.00    5.00    --   41.68-125.00-120.00   71
  4  \w    103.00 178.00   1.00   18.00    --  106.01  77.00 -30.00   75
  5  \w    103.00 178.00   1.00   18.00    --  106.01  77.00   0.00   75
  6  \w     30.00 139.00   1.00   18.00    --  106.01 -77.00  90.00  109
  7  \w     30.00 134.00   1.00   18.00    --  106.01 -30.00 120.00  104
  8  \w     33.00 112.00   1.00   18.00    --  106.01-125.00  90.00   79
  9  \w    103.00 178.00   1.00   18.00    --  106.01 114.00 121.00   75
 10  \w    103.00 178.00   1.00   18.00    --  106.01  77.00-150.00   75
 11  \w   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00 -30.00  101
 12  \w   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00  90.00  101
 13  \w    -21.00  74.00   1.00    5.00    --   41.68 -77.00 -30.00   95
 14  \w     33.00 112.00   1.00   18.00    --  106.01-125.00 -30.00   79
 15  \w     78.00 178.00   1.00   18.00    --  106.01  30.00 120.00  100
 16  \w     80.00 178.00   1.00   18.00    --  106.01  45.00-180.00   98
 17  \w     77.00 178.00   1.00   18.00    --  106.01  61.00 -30.00  101
 18  \w     77.00 178.00   1.00   18.00    --  106.01  61.00  30.00  101
 19  \w     78.00 178.00   1.00   18.00    --  106.01  30.00 -60.00  100
 20  \w   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00 150.00  101
 21  \w   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00  30.00  101
 22  \w   -115.00 -14.00   1.00    5.00    --  -41.68 -57.00 -90.00  101
 23  \w     77.00 178.00   1.00   18.00    --  106.01  61.00  60.00  101
 24  \w     77.00 178.00   1.00   18.00    --  106.01  61.00 120.00  101
 25  \w     80.00 178.00   1.00   18.00    --  106.01  45.00-150.00   98
 26  \w     77.00 178.00   1.00   18.00    --  106.01  61.00 -60.00  101
 27  \w     77.00 178.00   1.00   18.00    --  106.01  61.00   0.00  101
 28  \w     80.00 178.00   1.00   18.00    --  106.01  45.00-120.00   98
 29  \w    -87.00  -6.00   1.00    5.00    --  -41.68 125.00  30.00   81
 30  \w    -87.00  -6.00   1.00    5.00    --  -41.68 125.00-180.00   81
 31  \w      1.00 122.00   1.00    5.00    --   41.68  19.00  30.00  121
 32  \w     77.00 102.00   1.00   18.00    --  106.01  61.00  90.00   25
 33  \w     77.00 178.00   1.00   18.00    --  106.01  61.00 -90.00  101
;
_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      0.0242578000
_diffrn_orient_matrix_UB_12      0.0762437000
_diffrn_orient_matrix_UB_13      0.0143671000
_diffrn_orient_matrix_UB_21      0.0083574000
_diffrn_orient_matrix_UB_22      -0.0221720000
_diffrn_orient_matrix_UB_23      0.0585604000
_diffrn_orient_matrix_UB_31      0.0829703000
_diffrn_orient_matrix_UB_32      -0.0200889000
_diffrn_orient_matrix_UB_33      -0.0101127000
_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  0.0589
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            159999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.066
_diffrn_reflns_theta_min         2.931
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             3584
_exptl_crystal_preparation       synthesis
_exptl_crystal_recrystallization_method 'DCM/pentane slow diffusion'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.291(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         16900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0220
_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^)+(0.0291P)^2^+2.7549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0529
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                16209
_reflns_number_total             16900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00239f2.cif
_cod_data_source_block           em_109_2
_cod_database_code               7709433
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.709(5)
 0.291(5)
2. 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
3.a Ternary CH refined with riding coordinates:
 C31(H31), C34(H34), C43(H43), C46(H46), C53(H53), C61(H61), C70(H70), C74(H74)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C49(H49A,H49B), C50(H50A,H50B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C27(H27),
  C28(H28), C29(H29), C39(H39), C40(H40), C41(H41), C58(H58), C59(H59),
 C60(H60), C66(H66), C67(H67), C68(H68), C78(H78), C79(H79), C80(H80), C81(H81),
  C82(H82), C86(H86), C87(H87), C88(H88), C89(H89), C90(H90), C92(H92),
 C93(H93), C94(H94), C95(H95), C96(H96)
3.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C62(H62A,H62B,H62C),
 C63(H63A,H63B,H63C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C73(H73A,H73B,
 H73C), C75(H75A,H75B,H75C)
;
_shelx_res_checksum              16222
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.821
_oxdiff_exptl_absorpt_empirical_full_min 0.724