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_7716334
_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 Au N5, H2 O'
_chemical_formula_sum            'C33 H42 Au N5 O'
_chemical_formula_weight         721.68
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-18 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                86.470(2)
_cell_angle_beta                 79.752(2)
_cell_angle_gamma                77.217(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1790(2)
_cell_length_b                   9.1789(2)
_cell_length_c                   21.4433(4)
_cell_measurement_reflns_used    19586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.6520
_cell_measurement_theta_min      4.1740
_cell_volume                     1544.48(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -86.00  -6.00   1.00    1.00    --  -41.41 125.00-150.00   80
  2  \w    -70.00  32.00   1.00    1.00    --  -41.41  57.00 150.00  102
  3  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00   0.00  101
  4  \w    -33.00  66.00   1.00    1.00    --   41.41 -38.00-150.00   99
  5  \w     30.00 135.00   1.00    2.00    --  106.28 -30.00-120.00  105
  6  \w     33.00 132.00   1.00    2.00    --  106.28 -45.00   0.00   99
  7  \w     24.00 106.00   1.00    2.00    --  106.28 -94.00 150.00   82
  8  \w     24.00 106.00   1.00    2.00    --  106.28 -94.00-150.00   82
  9  \w    103.00 178.00   1.00    2.00    --  106.28  77.00 -60.00   75
 10  \w     34.00 135.00   1.00    2.00    --  106.28 -61.00-150.00  101
 11  \w     33.00 112.00   1.00    2.00    --  106.28-125.00 120.00   79
 12  \w     33.00 112.00   1.00    2.00    --  106.28-125.00  60.00   79
 13  \w     31.00 109.00   1.00    2.00    --  106.28-115.00  -8.00   78
 14  \w     25.00 159.00   1.00    2.00    --  106.28 -15.00 120.00  134
 15  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00 -90.00  101
 16  \w    -66.00  33.00   1.00    1.00    --  -41.41  38.00  60.00   99
 17  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00-180.00  101
 18  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00  90.00  101
 19  \w     77.00 178.00   1.00    2.00    --  106.28  61.00  90.00  101
 20  \w     54.00 178.00   1.00    2.00    --  106.28  15.00   0.00  124
 21  \w     80.00 178.00   1.00    2.00    --  106.28  45.00 150.00   98
 22  \w     77.00 178.00   1.00    2.00    --  106.28  61.00-180.00  101
 23  \w     78.00 178.00   1.00    2.00    --  106.28  30.00-120.00  100
 24  \w     80.00 178.00   1.00    2.00    --  106.28  45.00 -90.00   98
 25  \w     77.00 178.00   1.00    2.00    --  106.28  61.00   0.00  101
 26  \w     77.00 178.00   1.00    2.00    --  106.28  61.00  60.00  101
 27  \w     13.00 114.00   1.00    1.00    --   41.41  57.00-120.00  101
 28  \w     13.00 114.00   1.00    1.00    --   41.41  57.00  60.00  101
 29  \w     13.00 114.00   1.00    1.00    --   41.41  57.00 120.00  101
 30  \w     27.00  97.00   1.00    1.00    --   41.41-125.00 -30.00   70
 31  \w     77.00 178.00   1.00    2.00    --  106.28  61.00 -30.00  101
 32  \w     77.00 178.00   1.00    2.00    --  106.28  61.00 -60.00  101
 33  \w     77.00 178.00   1.00    2.00    --  106.28  61.00  30.00  101
 34  \w     80.00 178.00   1.00    2.00    --  106.28  45.00-120.00   98
 35  \w     77.00 178.00   1.00    2.00    --  106.28  61.00 150.00  101
 36  \w     77.00 178.00   1.00    2.00    --  106.28  61.00 -90.00  101
 37  \w     77.00 178.00   1.00    2.00    --  106.28  61.00 120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004451000
_diffrn_orient_matrix_UB_12      0.1066960000
_diffrn_orient_matrix_UB_13      -0.0583399000
_diffrn_orient_matrix_UB_21      -0.0020964000
_diffrn_orient_matrix_UB_22      -0.1296406000
_diffrn_orient_matrix_UB_23      -0.0419867000
_diffrn_orient_matrix_UB_31      -0.1959422000
_diffrn_orient_matrix_UB_32      0.0380076000
_diffrn_orient_matrix_UB_33      0.0129083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.877
_diffrn_reflns_theta_min         4.191
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.202
_exptl_absorpt_correction_T_max  0.08531
_exptl_absorpt_correction_T_min  0.01552
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         3.592
_refine_diff_density_min         -1.174
_refine_diff_density_rms         0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6169
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0586
_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^)+(0.1039P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5541
_reflns_number_total             6169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01414f2.cif
_cod_data_source_block           nb072-100k
_cod_depositor_comments
'Adding full bibliography for 7716334--7716337.cif.'
_cod_database_code               7716334
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H40 N5 Au'
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.288
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.01
 H1A-H1B
 1.34 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C25(H25), C10(H10), C22(H22), C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C31(H31), C28(H28), C18(H18), C8(H8), C6(H6), C7(H7),
 C30(H30), C20(H20), C19(H19), C29(H29)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C26(H26A,H26B,H26C), C23(H23A,H23B,
 H23C), C12(H12A,H12B,H12C), C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C11(H11A,
 H11B,H11C)
;
_shelx_res_checksum              63264
_shelx_hkl_checksum              84543
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.360
_oxdiff_exptl_absorpt_empirical_full_min 0.480