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_7716335
_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 Cu N5'
_chemical_formula_sum            'C33 H40 Cu N5'
_chemical_formula_weight         570.24
_chemical_name_systematic        6a
_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             2024-02-19
_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                68.805(2)
_cell_angle_beta                 75.145(2)
_cell_angle_gamma                82.058(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7992(4)
_cell_length_b                   12.5935(5)
_cell_length_c                   12.9797(5)
_cell_measurement_reflns_used    6161
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      72.099
_cell_measurement_theta_min      6.263
_cell_volume                     1588.79(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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8-Venture with Photon-III'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6191
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.222
_diffrn_reflns_theta_min         4.994
_exptl_absorpt_coefficient_mu    1.174
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1423 before and 0.0611 after correction.
 
For component 2:
 wR2(int) was 0.1877 before and 0.0651 after correction.
 The Ratio of minimum to maximum transmission is 0.88.

Final HKLF 4 output contains 214307 reflections, Rint = 0.0449
 (155306 with I > 3sig(I), Rint = 0.0434)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, n-pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6191
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0816P)^2^+0.1589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5908
_reflns_number_total             6191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01414f2.cif
_cod_data_source_block           6a
_cod_depositor_comments
'Adding full bibliography for 7716334--7716337.cif.'
_cod_database_code               7716335
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.782
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.889(3)
 0.111(3)
2. 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
3. Restrained distances
 C23-C22 \\sim C24-C23
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C22A) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
5. Others
 Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=
 Sof(H9A)=1-FVAR(1)
 Sof(C5)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(1)
 Sof(H23A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C24A)=Sof(H24D)=
 Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(H23)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C23(H23), C23(H23A), C17(H17), C19(H19), C31(H31)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C12(H12), C27(H27),
 C14(H14), C29(H29), C9(H9), C28(H28), C13(H13), C8(H8), C6(H6), C7(H7)
6.c Fitted hexagon refined as free rotating group:
 C4(C5A,C6A,C7A,C8A,C9A)
6.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C32(H32A,H32B,
 H32C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C22A(H22D,H22E,H22F),
 C24A(H24D,H24E,H24F), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              76439
_shelx_hkl_checksum              18842
_olex2_submission_special_instructions 'No special instructions were received'