Improved synthetic routes to N-heterocyclic carbene-metal-diketonato complexes of gold and copper
Ibni Hashim, Ishfaq; Tzouras, Nikolaos V.; Ma, Xinyuan; Bourda, Laurens; Van Hecke, Kristof; Nolan, Steven P.; Cazin, Catherine S. J.; Dalton Transactions  (2022) –; doi:10.1039/D2DT02276A

data_7711019
_publ_section_title
;
 Improved synthetic routes to N-heterocyclic carbene-metal-diketonato
 complexes of gold and copper
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02276A
_journal_year                    2022
_chemical_formula_moiety         'C42 H49 Cu N2 O2'
_chemical_formula_sum            'C42 H49 Cu N2 O2'
_chemical_formula_weight         677.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.24530(10)
_cell_length_b                   16.59370(10)
_cell_length_c                   16.23040(10)
_cell_measurement_reflns_used    43895
_cell_measurement_temperature    293.15(1)
_cell_measurement_theta_max      73.7440
_cell_measurement_theta_min      3.7820
_cell_volume                     3836.27(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 -60.00   99
  2  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00-180.00   81
  3  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  90.00   81
  4  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-120.00   99
  5  \w   -122.00  -1.00   1.00    1.00    --  -41.68 -19.00  30.00  121
  6  \w     77.00 178.00   1.00    6.00    --  106.01  61.00-120.00  101
  7  \w     53.00 178.00   1.00    6.00    --  106.01  15.00-150.00  125
  8  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 -90.00  101
  9  \w    103.00 178.00   1.00    6.00    --  106.01  77.00  60.00   75
 10  \w     97.00 178.00   1.00    6.00    --  106.01 125.00  90.00   81
 11  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 -60.00  101
 12  \w     80.00 178.00   1.00    6.00    --  106.01  45.00 -30.00   98
 13  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 -30.00  101
 14  \w     33.00 132.00   1.00    6.00    --  106.01 -45.00 -90.00   99
 15  \w     23.00 107.00   1.00    6.00    --  106.01 -94.00  90.00   84
 16  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 150.00   99
 17  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
 18  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 19  \w     14.00 115.00   1.00    1.00    --   41.68  57.00  60.00  101
 20  \w      6.00  83.00   1.00    1.00    --   41.68 -99.00  30.00   77
 21  \w     33.00 112.00   1.00    6.00    --  106.01-125.00 -90.00   79
 22  \w     30.00 139.00   1.00    6.00    --  106.01 -77.00 150.00  109
 23  \w     77.00 178.00   1.00    6.00    --  106.01  61.00  30.00  101
 24  \w     77.00 178.00   1.00    6.00    --  106.01  61.00   0.00  101
 25  \w     77.00 178.00   1.00    6.00    --  106.01  61.00-150.00  101
 26  \w     33.00 112.00   1.00    6.00    --  106.01-125.00  60.00   79
 27  \w     77.00 178.00   1.00    6.00    --  106.01  61.00  60.00  101
 28  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 120.00  101
 29  \w     77.00 178.00   1.00    6.00    --  106.01  61.00-180.00  101
 30  \w     77.00 178.00   1.00    6.00    --  106.01  61.00  90.00  101
 31  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-150.00  101
 32  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
 33  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
 34  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00   0.00  101
 35  \w    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -90.00   81
 36  \w     79.00 178.00   1.00    6.00    --  106.01  49.00-172.00   99
 37  \w     80.00 178.00   1.00    6.00    --  106.01  45.00   0.00   98
 38  \w     77.00 178.00   1.00    6.00    --  106.01  61.00 150.00  101
 39  \w     33.00 112.00   1.00    6.00    --  106.01-125.00   0.00   79
 40  \w     80.00 178.00   1.00    6.00    --  106.01  45.00-120.00   98
 41  \w     80.00 178.00   1.00    6.00    --  106.01  45.00 -60.00   98
 42  \w     80.00 178.00   1.00    6.00    --  106.01  45.00  30.00   98
 43  \w     80.00 178.00   1.00    6.00    --  106.01  45.00  90.00   98
 44  \w     80.00 178.00   1.00    6.00    --  106.01  45.00  60.00   98
 45  \w     80.00 178.00   1.00    6.00    --  106.01  45.00 -90.00   98
 46  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -60.00  101
 47  \w     14.00 115.00   1.00    1.00    --   41.68  57.00-180.00  101
 48  \w     14.00 115.00   1.00    1.00    --   41.68  57.00  30.00  101
 49  \w     14.00 115.00   1.00    1.00    --   41.68  57.00 -90.00  101
 50  \w      1.00 122.00   1.00    1.00    --   41.68  19.00 -90.00  121
 51  \w     80.00 178.00   1.00    6.00    --  106.01  45.00-150.00   98
 52  \w     33.00 112.00   1.00    6.00    --  106.01-125.00-120.00   79
 53  \w     80.00 178.00   1.00    6.00    --  106.01  45.00 120.00   98
 54  \w     78.00 178.00   1.00    6.00    --  106.01  30.00-180.00  100
 55  \w     80.00 178.00   1.00    6.00    --  106.01  45.00-180.00   98
 56  \w     34.00 135.00   1.00    6.00    --  106.01 -61.00   0.00  101
 57  \w     78.00 178.00   1.00    6.00    --  106.01  30.00-120.00  100
 58  \w     78.00 178.00   1.00    6.00    --  106.01  30.00 -60.00  100
 59  \w     78.00 178.00   1.00    6.00    --  106.01  30.00   0.00  100
 60  \w     80.00 178.00   1.00    6.00    --  106.01  45.00 150.00   98
 61  \w     17.00 116.00   1.00    1.00    --   41.68  38.00-180.00   99
;
_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      -0.0443535000
_diffrn_orient_matrix_UB_12      -0.0232601000
_diffrn_orient_matrix_UB_13      -0.0837447000
_diffrn_orient_matrix_UB_21      0.0736406000
_diffrn_orient_matrix_UB_22      0.0515762000
_diffrn_orient_matrix_UB_23      -0.0444626000
_diffrn_orient_matrix_UB_31      0.0656047000
_diffrn_orient_matrix_UB_32      -0.0736155000
_diffrn_orient_matrix_UB_33      -0.0047130000
_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  0.0651
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            142078
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.948
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         7764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.6886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6387
_reflns_number_total             7764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02276a2.cif
_cod_data_source_block           nt457_4
_cod_database_code               7711019
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C42H50CuN2O2
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.628
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41),
  C42(H42)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_res_checksum              21143
_olex2_date_sample_data_collection 2022-08-01
_olex2_exptl_crystal_mounting_method 'Mounted on a LythoLoop'
_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.620