Thiophenyl and benzothiophenyl gold isocyanide complexes: synthesis, structures, and aurophilic and gold-involving chalcogen bonding interactions
Pavlov, Kirill G.; Grudova, Mariya R.; Kubasov, Alexey S.; Khrustalev, Victor N.; Kritchenkov, Ilia S.; Gomila, Rosa M.; Frontera, Antonio; Tskhovrebov, Alexander G.; CrystEngComm 27 (2025) 7021–7031; doi:10.1039/D5CE00724K

data_7250889
_publ_section_title
;
 Thiophenyl and benzothiophenyl gold isocyanide complexes: synthesis,
 structures, and aurophilic and gold-involving chalcogen bonding
 interactions
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              7021
_journal_page_last               7031
_journal_paper_doi               10.1039/D5CE00724K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '0.111(C117 H108 Au9 N9 S9)'
_chemical_formula_sum            'C13 H12 Au N S'
_chemical_formula_weight         411.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                113.9380(10)
_cell_angle_beta                 100.457(2)
_cell_angle_gamma                90.668(2)
_cell_formula_units_Z            18
_cell_length_a                   11.6478(5)
_cell_length_b                   21.7736(8)
_cell_length_c                   25.2892(10)
_cell_measurement_reflns_used    9599
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.64
_cell_measurement_theta_min      2.20
_cell_volume                     5738.7(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            42954
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.623
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.671
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.2541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.3407.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.865
_refine_diff_density_min         -2.642
_refine_diff_density_rms         0.269
_refine_ls_extinction_coef       0.00022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1142
_refine_ls_number_reflns         20097
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0306P)^2^+101.1594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17227
_reflns_number_total             20097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00724k2.cif
_cod_data_source_block           mg6_4_a
_cod_depositor_comments
'Adding full bibliography for 7250880--7250889.cif.'
_cod_database_code               7250889
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.388
_shelx_estimated_absorpt_t_min   0.089
_olex2_refinement_description
;
1. Restrained distances
 C15-C105
 1.455 with sigma of 0.02
 S9-C15
 1.712 with sigma of 0.02
 C107-S9
 1.712 with sigma of 0.02
 C105-C106
 1.471 with sigma of 0.02
 C106-C107
 1.455 with sigma of 0.02
 S7A-C79
 1.712 with sigma of 0.02
 C79-S7B
 1.712 with sigma of 0.02
 C80B-C79
 1.455 with sigma of 0.02
 S7B-C79
 1.712 with sigma of 0.02
 S7A-C82
 1.712 with sigma of 0.02
 C80A-C79
 1.455 with sigma of 0.02
 C79-S7A
 1.712 with sigma of 0.02
 C82-C81
 1.455 with sigma of 0.02
 C81-S7B
 1.712 with sigma of 0.02
 C66-C67B
 1.455 with sigma of 0.02
 S6B-C66
 1.712 with sigma of 0.02
 C67A-C68
 1.455 with sigma of 0.02
 S6A-C69
 1.712 with sigma of 0.02
 C69-C68
 1.471 with sigma of 0.02
 C66-S6A
 1.712 with sigma of 0.02
 S6B-C68
 1.712 with sigma of 0.02
 C16-C17
 1.455 with sigma of 0.02
 C17-S2A
 1.712 with sigma of 0.02
 C14-S2A
 1.712 with sigma of 0.02
 C15A-C14
 1.455 with sigma of 0.02
 C15A-C16
 1.455 with sigma of 0.02
 S2B-C14
 1.712 with sigma of 0.02
 S2B-C16
 1.712 with sigma of 0.02
 C15B-C14
 1.455 with sigma of 0.02
 C17-C15B
 1.471 with sigma of 0.02
 C29-C30
 1.455 with sigma of 0.02
 S3A-C30
 1.712 with sigma of 0.02
 S3A-C27
 1.712 with sigma of 0.02
 C29-S3B
 1.712 with sigma of 0.02
 C28A-C29
 1.471 with sigma of 0.02
 S3B-C27
 1.712 with sigma of 0.02
 C28A-C27
 1.455 with sigma of 0.02
 C28B-C27
 1.455 with sigma of 0.02
 C28B-C30
 1.471 with sigma of 0.02
2. Restrained planarity
 S6B, C66, C67B, C68, C69
 with sigma of 0.1
 S6A, C66, C67A, C68, C69
 with sigma of 0.1
 S2A, C14, C15A, C16, C17
 with sigma of 0.1
 S2B, C14, C15B, C16, C17
 with sigma of 0.1
 S3B, C27, C28B, C29, C30
 with sigma of 0.1
 C15, C105, C106, C107
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(C80A) = Uanis(C80B)
Uanis(C80A) = Uanis(C81)
Uanis(S7A) = Uanis(S7B)
Uanis(C67B) = Uanis(C67A)
Uanis(S6A) = Uanis(S6B)
Uanis(S2B) = Uanis(S2A)
Uanis(C15A) = Uanis(C15B)
Uanis(C28B) = Uanis(C28A)
Uanis(S3B) = Uanis(S3A)
Uanis(C28A) = Uanis(C29)
Uanis(C67A) = Uanis(C68)
Uanis(C15A) = Uanis(C16)
Uanis(C15A) = Uanis(C14)
Uanis(C72) = Uanis(C60)
Uanis(C74) = Uanis(C61)
Uanis(C57) = Uanis(C70)
Uanis(C77) = Uanis(C64)
Uanis(N5) = Uanis(N6)
Uanis(C73) = Uanis(C60)
Uanis(C71) = Uanis(C58)
Uanis(C65) = Uanis(C78)
Uanis(C63) = Uanis(C76)
Uanis(C75) = Uanis(C62)
Uanis(C105) = Uanis(C15)
Uanis(C106) = Uanis(C42)
Uanis(C13) = Uanis(C12)
Uanis(C85) = Uanis(C86)
Uanis(C110) = Uanis(C114)
Uanis(C89) = Uanis(C88)
Uanis(C53) = Uanis(C54)
Uanis(N2) = Uanis(N1)
Uanis(C30) = Uanis(C29)
Uanis(C27) = Uanis(C1)
Uanis(C4) = Uanis(C2)
Uanis(C2) = Uanis(C1)
Uanis(C3) = Uanis(C4)
Uanis(C108) = Uanis(C44)
Uanis(C19) = Uanis(C32)
Uanis(C16) = Uanis(C17)
4. Others
 Fixed Sof: S2A(0.75) S2B(0.25) S3A(0.75) S3B(0.25) S6A(0.5) S6B(0.5) S7A(0.5)
 S7B(0.5) C15A(0.75) H15A(0.75) C15B(0.25) H15B(0.25) H16(0.75) H16A(0.25)
 H17(0.75) H17A(0.25) C28A(0.75) H28A(0.75) C28B(0.25) H28B(0.25) H29A(0.25)
 H29(0.75) H30(0.75) H30A(0.25) C67A(0.5) H67A(0.5) C67B(0.5) H67B(0.5)
 H68A(0.5) H68(0.5) H69(0.5) H69A(0.5) C80A(0.5) H80A(0.5) C80B(0.5) H80B(0.5)
 H81A(0.5) H81(0.5) H82(0.5) H82A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C15A(H15A), C15B(H15B),
 C16(H16), C16(H16A), C17(H17), C17(H17A), C21(H21), C22(H22), C23(H23),
 C28A(H28A), C28B(H28B), C29(H29A), C29(H29), C30(H30), C30(H30A), C34(H34),
 C35(H35), C36(H36), C41(H41), C42(H42), C43(H43), C47(H47), C48(H48), C49(H49),
  C54(H54), C55(H55), C56(H56), C61(H61), C60(H60), C62(H62), C67A(H67A),
 C67B(H67B), C68(H68A), C68(H68), C69(H69), C69(H69A), C73(H73), C74(H74),
 C75(H75), C80A(H80A), C80B(H80B), C81(H81A), C81(H81), C82(H82), C82(H82A),
 C86(H86), C87(H87), C88(H88), C93(H93), C94(H94), C95(H95), C99(H99),
 C100(H100), C101(H101), C105(H105), C106(H106), C107(H107), C111(H111),
 C112(H112), C113(H113)
5.b Fitted hexagon refined as free rotating group:
 C61(C60,C59,C58,C63,C62)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C51(H51A,H51B,H51C), C52(H52A,
 H52B,H52C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C77(H77A,H77B,H77C),
 C78(H78A,H78B,H78C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C103(H10A,H10B,
 H10C), C104(H10D,H10E,H10F), C115(H11A,H11B,H11C), C116(H11D,H11E,H11F)
;
_shelx_res_checksum              94634
_olex2_submission_special_instructions 'No special instructions were received'