Synthesis of N-heterocyclic carbene (NHC)-Au/Ag/Cu benzotriazolyl complexes and their catalytic activity in propargylamide cycloisomerization and carbonyl hydrosilylation reactions.
Kaplanai, Entzy; Tzouras, Nikolaos V.; Tsoureas, Nikolaos; Bracho Pozsoni, Nestor; Bhandary, Subhrajyoti; Van Hecke, Kristof; Nolan, Steven P.; Vougioukalakis, Georgios C.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 11001–11008; doi:10.1039/d4dt01414f

data_7716337
_publ_section_title
;
 Synthesis of N-heterocyclic carbene (NHC)-Au/Ag/Cu benzotriazolyl
 complexes and their catalytic activity in propargylamide
 cycloisomerization and carbonyl hydrosilylation reactions.
;
_journal_issue                   26
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11001
_journal_page_last               11008
_journal_paper_doi               10.1039/d4dt01414f
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C33 H40 Ag N5, C H1 Cl3'
_chemical_formula_sum            'C34 H41 Ag Cl3 N5'
_chemical_formula_weight         733.94
_chemical_name_systematic        5a
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.405(2)
_cell_length_b                   14.1492(12)
_cell_length_c                   23.243(2)
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.468
_cell_measurement_theta_min      2.879
_cell_volume                     7039.5(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS Inc, 2016)'
_computing_data_collection       'APEX4 (Bruker AXS Inc, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8-Venture with Photon-III'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            916707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         1.935
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       rod
_exptl_crystal_F_000             3024
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, n-pentane'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         10766
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+5.0931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9609
_reflns_number_total             10766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01414f2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7716334--7716337.cif.'
_cod_original_cell_volume        7039.3(11)
_cod_database_code               7716337
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.856
_olex2_refinement_description
;
1. Restrained distances
 C34-Cl8
 1.78 with sigma of 0.02
 C34-Cl9
 1.78 with sigma of 0.02
 C34-Cl7
 1.78 with sigma of 0.02
 Cl3-Cl2 \\sim Cl8-Cl7
 with sigma of 0.02
 Cl3-Cl1 \\sim Cl8-Cl9
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl9-Cl7
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(Cl3) = Uanis(Cl6)
Uanis(Cl3) = Uanis(Cl8)
Uanis(Cl1) = Uanis(Cl4)
Uanis(Cl2) = Uanis(Cl7)
3. Others
 1*[Sof(H34)+Sof(Cl3)+Sof(Cl1)+Sof(Cl2)]+1*[Sof(H34A)+Sof(Cl5)+Sof(Cl4)+
 Sof(Cl6)]+1*[Sof(H34B)+Sof(Cl7)+Sof(Cl9)+Sof(Cl8)]=1 with esd of 0.0001
 Sof(H34)=Sof(Cl3)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(H34A)=Sof(Cl5)=Sof(Cl4)=Sof(Cl6)=FVAR(2)
 Sof(H34B)=Sof(Cl7)=Sof(Cl9)=Sof(Cl8)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10), C22(H22), C34(H34), C34(H34A), C34(H34B), C26(H26)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C7(H7), C31(H31), C20(H20), C19(H19),
 C28(H28), C18(H18), C29(H29), C30(H30)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C23(H23A,H23B,
 H23C), C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C24(H24A,
 H24B,H24C)
;
_shelx_res_checksum              14747
_shelx_hkl_checksum              26426
_olex2_submission_special_instructions 'No special instructions were received'