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_7711017
_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         'C84 H67 Cu N2 O2, 1[CHCl3], 0.5[CHCl3]'
_chemical_formula_sum            'C85.5 H68.5 Cl4.5 Cu N2 O2'
_chemical_formula_weight         1378.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-01
_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                 105.635(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3647(2)
_cell_length_b                   24.9607(4)
_cell_length_c                   21.2880(4)
_cell_measurement_reflns_used    26117
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8930
_cell_measurement_theta_min      2.7590
_cell_volume                     6838.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (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_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -66.00  33.00   1.00    2.00    --  -41.68  38.00 120.00   99
  2  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -30.00  101
  3  \w    -21.00  74.00   1.00    2.00    --   41.68 -77.00-150.00   95
  4  \w     33.00 112.00   1.00    9.00    --  106.01-125.00   0.00   79
  5  \w    103.00 178.00   1.00    9.00    --  106.01  77.00  30.00   75
  6  \w     30.00 139.00   1.00    9.00    --  106.01 -77.00   0.00  109
  7  \w    103.00 178.00   1.00    9.00    --  106.01  77.00 120.00   75
  8  \w    103.00 178.00   1.00    9.00    --  106.01  77.00-120.00   75
  9  \w     78.00 178.00   1.00    9.00    --  106.01  30.00-180.00  100
 10  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 120.00  101
 11  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-150.00  101
 12  \w     80.00 178.00   1.00    9.00    --  106.01  45.00 -30.00   98
 13  \w     33.00 112.00   1.00    9.00    --  106.01-125.00-120.00   79
 14  \w     77.00 178.00   1.00    9.00    --  106.01  61.00-150.00  101
 15  \w     53.00 178.00   1.00    9.00    --  106.01  15.00  90.00  125
 16  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00  60.00  101
 17  \w      6.00  68.00   1.00    2.00    --   41.68 -99.00 -30.00   62
;
_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      0.0024271000
_diffrn_orient_matrix_UB_12      0.0187638000
_diffrn_orient_matrix_UB_13      0.0693563000
_diffrn_orient_matrix_UB_21      0.1142269000
_diffrn_orient_matrix_UB_22      -0.0178917000
_diffrn_orient_matrix_UB_23      0.0245562000
_diffrn_orient_matrix_UB_31      0.0357053000
_diffrn_orient_matrix_UB_32      0.0559874000
_diffrn_orient_matrix_UB_33      -0.0154003000
_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     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            64513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.887
_diffrn_reflns_theta_min         2.789
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             2868
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.057
_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     804
_refine_ls_number_reflns         13633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0480
_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^)+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11262
_reflns_number_total             13633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02276a2.cif
_cod_data_source_block           121_01_auto
_cod_original_formula_sum        'C85.50 H68.50 Cl4.50 Cu N2 O2'
_cod_database_code               7711017
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.638
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C24(H24), C43(H43), C57(H57)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C39(H39), C41(H41), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49),
  C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69),
  C70(H70), C71(H71), C72(H72), C73(H73), C74(H74), C77(H77), C80(H80),
 C81(H81), C82(H82), C83(H83), C84(H84)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C56(H56A,H56B,H56C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 340 electrons were 
found in a volume of 898\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
1[CHCl3], 0.5[CHCl3] per Formula Unit 
which account for 348 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              36158
_shelx_fab_checksum              44540
_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 1.915
_oxdiff_exptl_absorpt_empirical_full_min 0.722