Free-Catalysed Synthesis of Thiazolidine-Thiourea Ligands for Metal Coordination (Au and Ag) and Preliminary Cytotoxic Studies
Salvador, Daniel; Herrera, Raquel; Gimeno, Maria Concepcion; Dalton Transactions  (2023) –; doi:10.1039/D3DT00079F

data_7712396
_publ_section_title
;
 Free-Catalysed Synthesis of Thiazolidine-Thiourea Ligands for Metal
 Coordination (Au and Ag) and Preliminary Cytotoxic Studies
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00079F
_journal_year                    2023
_chemical_formula_moiety         'C35 H29 Au F2 N3 P S2, C F3 O3 S'
_chemical_formula_sum            'C36 H29 Au F5 N3 O3 P S3'
_chemical_formula_weight         970.74
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-31
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_audit_update_record
;
2023-02-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.8662(2)
_cell_length_b                   13.8662(2)
_cell_length_c                   32.5715(5)
_cell_measurement_reflns_used    14146
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3010
_cell_measurement_theta_min      3.4890
_cell_volume                     5423.55(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w rotations'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            27642
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.193
_exptl_absorpt_coefficient_mu    4.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_description       prism
_exptl_crystal_F_000             2862
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 2529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     1501
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+12.5958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6297
_reflns_number_total             6726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00079f2.cif
_cod_data_source_block           c567
_cod_original_cell_volume        5423.57(19)
_cod_database_code               7712396
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.695
_shelx_estimated_absorpt_t_min   0.492
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-F3 = C1A-F4 = C1A-F5
 1.33 with sigma of 0.02
 C1A-S6
 1.82 with sigma of 0.02
 S6-O7 = S6-O8 = S6-O9
 1.44 with sigma of 0.02
 C1A-O7
 2.58 with sigma of 0.04
 C1A-O8
 2.56 with sigma of 0.04
 C1A-O9
 2.57 with sigma of 0.04
 N3-C5 \\sim N3A-C5
 with sigma of 0.02
 N3-C6 \\sim N3A-C6A
 with sigma of 0.02
 F1-C10 \\sim F1A-C10A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C6-C11 \\sim C6A-C11A
 with sigma of 0.02
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 N3-C7 \\sim N3A-C7A
 with sigma of 0.04
 N3-C11 \\sim N3A-C11A
 with sigma of 0.04
 F1-C9 \\sim F1A-C9A
 with sigma of 0.04
 F1-C11 \\sim F1A-C11A
 with sigma of 0.04
 C5-C6 \\sim C5-C6A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C6-C10 \\sim C6A-C10A
 with sigma of 0.04
 C7-C9 \\sim C7A-C9A
 with sigma of 0.04
 C7-C11 \\sim C7A-C11A
 with sigma of 0.04
 C8-C10 \\sim C8A-C10A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 N2-C1 \\sim N2A-C1
 with sigma of 0.02
 N2-C12 \\sim N2A-C12A
 with sigma of 0.02
 F2-C16 \\sim F2A-C16A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C12-C17 \\sim C12A-C17A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 N2-C13 \\sim N2A-C13A
 with sigma of 0.04
 N2-C17 \\sim N2A-C17A
 with sigma of 0.04
 F2-C15 \\sim F2A-C15A
 with sigma of 0.04
 F2-C17 \\sim F2A-C17A
 with sigma of 0.04
 C1-C12 \\sim C1-C12A
 with sigma of 0.04
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 C12-C16 \\sim C12A-C16A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C13-C17 \\sim C13A-C17A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C17-F2 \\sim F2-C15
 with sigma of 0.001
 C17A-F2A \\sim F2A-C15A
 with sigma of 0.001
 C1A-F3 \\sim C1A-F4 \\sim C1A-F5
 with sigma of 0.02
 F3-F4 \\sim F4-F5 \\sim F5-F3
 with sigma of 0.04
 S6-F3 \\sim S6-F4 \\sim S6-F5
 with sigma of 0.04
 S6-O7 \\sim S6-O8 \\sim S6-O9
 with sigma of 0.02
 O7-O8 \\sim O8-O9 \\sim O7-O9
 with sigma of 0.04
 C1A-O7 \\sim C1A-O8 \\sim C1A-O9
 with sigma of 0.04
 C1A-F3 \\sim C1B-F3A
 with sigma of 0.02
 C1A-F4 \\sim C1B-F4A
 with sigma of 0.02
 C1A-F5 \\sim C1B-F5A
 with sigma of 0.02
 C1A-S6 \\sim C1B-S6A
 with sigma of 0.02
 S6-O7 \\sim S6A-O7A
 with sigma of 0.02
 S6-O8 \\sim S6A-O8A
 with sigma of 0.02
 S6-O9 \\sim S6A-O9A
 with sigma of 0.02
 C1A-O7 \\sim C1B-O7A
 with sigma of 0.04
 C1A-O8 \\sim C1B-O8A
 with sigma of 0.04
 C1A-O9 \\sim C1B-O9A
 with sigma of 0.04
 F3-F4 \\sim F3A-F4A
 with sigma of 0.04
 F3-F5 \\sim F3A-F5A
 with sigma of 0.04
 F3-S6 \\sim F3A-S6A
 with sigma of 0.04
 F4-F5 \\sim F4A-F5A
 with sigma of 0.04
 F4-S6 \\sim F4A-S6A
 with sigma of 0.04
 F5-S6 \\sim F5A-S6A
 with sigma of 0.04
 O7-O8 \\sim O7A-O8A
 with sigma of 0.04
 O7-O9 \\sim O7A-O9A
 with sigma of 0.04
 O8-O9 \\sim O8A-O9A
 with sigma of 0.04
3. Restrained planarity
 F2, C16, C15, C14, C13, C12, C17
 with sigma of 0.001
 N2, F2, C16, C15, C14, C13, C12, C17
 with sigma of 0.001
4. Rigid bond restraints
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C16, C15, C14, C13, C12, C17,
 C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33,
  C34, C35, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A,
 C1A, C1B, N1, N2, N3, N3A, N2A, F1, F2, F1A, F2A, F3, F4, F5, F4A, F3A, F5A,
 O7, O8, O9, O7A, O8A, O9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(N2) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
6. Rigid body (RIGU) restrains
 F2A, C12A, C13A, C14A, C15A, C16A, C17A, N2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, C6A, C7A, C8A, C9A, C10A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, F2, C16, C15, C14, C13, C12, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, F3, F4, F5, S6, O7, O8, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S6, C1A, F3, F4, F5, O7, O8, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5A, F4A, C1B, F3A, S6A, O7A, O8A, O9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(F1A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(N3A)=1-FVAR(1)
 Sof(N3)=Sof(F1)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(C11)=Sof(H11)=FVAR(1)
 Sof(F2A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(N2A)=Sof(H2AA)=1-FVAR(2)
 Sof(N2)=Sof(H2)=Sof(F2)=Sof(C16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C13)=
 Sof(H13)=Sof(C12)=Sof(C17)=Sof(H17)=FVAR(2)
 Sof(F4A)=Sof(C1B)=Sof(F3A)=Sof(F5A)=Sof(S6A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=1-
 FVAR(3)
 Sof(C1A)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(S6)=Sof(O7)=Sof(O8)=Sof(O9)=FVAR(3)
8.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
8.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C14(H14), C13(H13),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C13A(H13A), C14A(H14A),
 C15A(H15A), C17A(H17A), N2A(H2AA)
8.c Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C16(C15,C14,C13,C12,C17), C18(C19,C20,C21,C22,C23),
 C24(C25,C26,C27,C28,C29), C30(C31,C32,C33,C34,C35), C12A(C13A,C14A,C15A,C16A,
 C17A)
8.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              30051
_shelx_hkl_checksum              42495
_olex2_submission_special_instructions 'No special instructions were received'