Straightforward synthetic route to gold(i)-thiolato glycoconjugate complexes bearing NHC ligands (NHC = N-heterocyclic carbene) and their promising anticancer activity
Safir Filho, Mauro; Scattolin, Thomas; Dao, Pascal; Tzouras, Nikolaos V.; Benhida, Rachid; Saab, Marina; Van Hecke, Kristof; Lippmann, Petra; Martin, Anthony R.; Ott, Ingo; Nolan, Steven P.; New Journal of Chemistry 45 (2021) 9995–10001; doi:10.1039/D1NJ02117F

data_7060659
_publ_section_title
;
 Straightforward synthetic route to gold(i)-thiolato glycoconjugate
 complexes bearing NHC ligands (NHC = N-heterocyclic carbene) and their
 promising anticancer activity
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9995
_journal_page_last               10001
_journal_paper_doi               10.1039/D1NJ02117F
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H51 Au N2 O9 S, C4 H8 O'
_chemical_formula_sum            'C41 H59 Au N2 O10 S'
_chemical_formula_weight         968.93
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-23 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                100.4360(10)
_cell_angle_beta                 104.2830(10)
_cell_angle_gamma                99.455(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0155(2)
_cell_length_b                   10.9223(2)
_cell_length_c                   20.2357(3)
_cell_measurement_reflns_used    29387
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      29.3350
_cell_measurement_theta_min      2.8150
_cell_volume                     2058.38(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.958
_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    -44.00  21.00   1.00   15.00    --  -11.19  77.00-120.00   65
  2  \w    -36.00  63.00   1.00   15.00    --  -11.19  38.00 120.00   99
  3  \w    -15.00  30.00   1.00   15.00    --  -11.19 -99.00 120.00   45
  4  \w    -15.00  30.00   1.00   15.00    --  -11.19 -99.00 -30.00   45
  5  \w    -39.00  62.00   1.00   15.00    --  -11.19  57.00   0.00  101
  6  \w    -15.00  84.00   1.00   15.00    --   10.01  38.00 150.00   99
  7  \w    -15.00  84.00   1.00   15.00    --   10.01  38.00  60.00   99
  8  \w    -42.00  21.00   1.00   15.00    --  -11.19 -77.00-180.00   63
  9  \w    -44.00  21.00   1.00   15.00    --  -11.19  77.00  60.00   65
 10  \w    -42.00  -6.00   1.00   15.00    --  -11.19 -77.00-120.00   36
 11  \w    -44.00  21.00   1.00   15.00    --  -11.19  77.00 150.00   65
;
_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      -0.0735884000
_diffrn_orient_matrix_UB_12      -0.0263390000
_diffrn_orient_matrix_UB_13      -0.0096270000
_diffrn_orient_matrix_UB_21      -0.0131599000
_diffrn_orient_matrix_UB_22      0.0623288000
_diffrn_orient_matrix_UB_23      0.0060878000
_diffrn_orient_matrix_UB_31      -0.0046723000
_diffrn_orient_matrix_UB_32      0.0013976000
_diffrn_orient_matrix_UB_33      -0.0353957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45550
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.495
_diffrn_reflns_theta_min         2.425
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.474
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       irregular
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 7792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1051
_refine_ls_number_reflns         18920
_refine_ls_number_restraints     266
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0256P)^2^+0.7948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                17674
_reflns_number_total             18920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02117f2.cif
_cod_data_source_block           man-au-iad
_cod_depositor_comments          'Adding full bibliography for 7060659.cif.'
_cod_database_code               7060659
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C37 H51 Au N2 O9 S'
_shelx_estimated_absorpt_t_max   0.733
_shelx_estimated_absorpt_t_min   0.415
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C10-H10A
 0.922 with sigma of 0.01
 C81A-C82A \\sim C81B-C82B
 with sigma of 0.02
 C81A-C80A \\sim C81B-C80B
 with sigma of 0.02
 C83A-C82A \\sim C83B-C82B
 with sigma of 0.02
 C83A-C80A \\sim C83B-C80B
 with sigma of 0.04
 C82A-C80A \\sim C82B-C80B
 with sigma of 0.04
 C83A-O79A \\sim C83B-O79B
 with sigma of 0.02
 C80A-O79A \\sim C80B-O79B
 with sigma of 0.02
 C82A-O79A \\sim C82B-O79B
 with sigma of 0.04
 C81A-C83A \\sim C81B-C83B
 with sigma of 0.04
 C81A-O79A \\sim C81B-O79B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O19 \\sim C75 \\sim C77 \\sim C76 \\sim C78 \\sim O79A \\sim C82A \\sim C80A
\\sim C83A \\sim C81A \\sim O79B \\sim C83B \\sim C81B \\sim C80B \\sim C82B:
within 2A with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(O3) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of
0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 O79A, C82A, C80A, C83A, C81A, O79B, C83B, C81B, C80B, C82B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O79B)=Sof(C83B)=Sof(H83C)=Sof(H83D)=Sof(C81B)=Sof(H81C)=Sof(H81D)=
 Sof(C80B)=Sof(H80C)=Sof(H80D)=Sof(C82B)=Sof(H82C)=Sof(H82D)=1-FVAR(1)
 Sof(O79A)=Sof(C82A)=Sof(H82A)=Sof(H82B)=Sof(C80A)=Sof(H80A)=Sof(H80B)=
 Sof(C83A)=Sof(H83A)=Sof(H83B)=Sof(C81A)=Sof(H81A)=Sof(H81B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C11(H11), C18(H18), C20(H20), C24(H24), C26(H26), C27(H27),
 C28(H28), C25(H25), C6(H6), C8(H8), C62(H62), C48(H48), C58(H58), C64(H64),
 C43(H43), C45(H45), C53(H53), C55(H55), C61(H61), C63(H63), C65(H65)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B), C12(H12A,H12B), C13(H13A,H13B), C22(H22A,
 H22B), C23(H23A,H23B), C21(H21A,H21B), C33(H33A,H33B), C5(H5A,H5B), C7(H7A,
 H7B), C9(H9A,H9B), C17(H17A,H17B), C46(H46A,H46B), C42(H42A,H42B), C44(H44A,
 H44B), C50(H50A,H50B), C54(H54A,H54B), C56(H56A,H56B), C52(H52A,H52B),
 C60(H60A,H60B), C72(H72A,H72B), C47(H47A,H47B), C49(H49A,H49B), C57(H57A,H57B),
  C59(H59A,H59B), C75(H75A,H75B), C77(H77A,H77B), C76(H76A,H76B), C78(H78A,
 H78B), C82A(H82A,H82B), C80A(H80A,H80B), C83A(H83A,H83B), C81A(H81A,H81B),
 C83B(H83C,H83D), C81B(H81C,H81D), C80B(H80C,H80D), C82B(H82C,H82D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C40(H40), C39(H39)
6.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C30(H30A,H30B,
 H30C), C74(H74A,H74B,H74C), C67(H67A,H67B,H67C), C69(H69A,H69B,H69C), C71(H71A,
 H71B,H71C)
;
_shelx_res_checksum              68852
_olex2_date_sample_data_collection 2021-02-01
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.842