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_7716336
_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 H42 Cu N5'
_chemical_formula_sum            'C33 H42 Cu N5'
_chemical_formula_weight         572.25
_chemical_name_systematic        6b
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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            4
_cell_length_a                   16.4504(11)
_cell_length_b                   12.4536(8)
_cell_length_c                   15.0423(10)
_cell_measurement_reflns_used    9719
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.106
_cell_measurement_theta_min      2.458
_cell_volume                     3081.7(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            89547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         2.051
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0905 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.9453.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, n-pentane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         8294
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0304P)^2^+0.7107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7753
_reflns_number_total             8294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01414f2.cif
_cod_data_source_block           6b
_cod_depositor_comments
'Adding full bibliography for 7716334--7716337.cif.'
_cod_database_code               7716336
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.98885
 0.01115
2.a Ternary CH refined with riding coordinates:
 C25(H25), C13(H13), C10(H10), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C6(H6), C34(H34), C7(H7), C31(H31), C33(H33),
 C8(H8), C32(H32)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C12(H12A,H12B,
 H12C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C18(H18A,
 H18B,H18C)
;
_shelx_res_checksum              22962
_shelx_hkl_checksum              18857
_olex2_submission_special_instructions 'No special instructions were received'