The carbene transfer to strong Lewis acids: copper is better than silver.
Mikhaylov, Vladimir N.; Kazakov, Igor V.; Parfeniuk, Tatiana N.; Khoroshilova, Olesya V.; Scheer, Manfred; Timoshkin, Alexey Y.; Balova, Irina A.; Dalton transactions (Cambridge, England : 2003) 50 (2021) 2872–2879; doi:10.1039/d1dt00235j

data_7706543
_publ_section_title
;
 The carbene transfer to strong Lewis acids: copper is better than silver.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2872
_journal_page_last               2879
_journal_paper_doi               10.1039/d1dt00235j
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C54 H72 Ag N4, Cl4 In'
_chemical_formula_sum            'C54 H72 Ag Cl4 In N4'
_chemical_formula_weight         1141.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-16 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9667(2)
_cell_length_b                   18.3327(2)
_cell_length_c                   18.2364(3)
_cell_measurement_reflns_used    20487
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2560
_cell_measurement_theta_min      3.5460
_cell_volume                     5577.31(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 10.0000
_diffrn_detector_type            HyPix3000
_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    -84.00 -26.00   0.50    0.51    --  -38.95 117.00 154.00  116
  2  \w   -101.00 -54.00   0.50    0.51    --  -38.95-162.00 -83.00   94
  3  \w    -92.00 -67.00   0.50    0.51    --  -38.95 162.00 -55.00   50
  4  \w     53.00  78.00   0.50    0.51    --   38.95 162.00 -55.00   50
  5  \w     44.00  69.00   0.50    0.51    --   38.95-162.00 -83.00   50
  6  \w     41.00  67.00   0.50    0.51    --   38.95-117.00  66.00   52
  7  \w     72.00 110.00   0.50    2.04    --  100.00-117.00  66.00   76
  8  \w    115.00 157.00   0.50    2.04    --  100.00 117.00 154.00   84
  9  \w     66.00  96.00   0.50    2.04    --  100.00 162.00 -55.00   60
 10  \w     87.00 112.00   0.50    2.04    --  100.00-162.00 -83.00   50
 11  \w    -18.00  30.00   0.50    0.51    --  -38.95  32.00 -60.00   96
 12  \w     -2.00  25.00   0.50    0.51    --  -38.95  32.00 150.00   54
 13  \w    -52.00  -8.00   0.50    0.51    --  -38.95  32.00 150.00   88
 14  \w    -52.00 -26.00   0.50    0.51    --  -38.95  32.00 -60.00   52
 15  \w    -55.00  24.00   0.50    0.51    --  -38.95  65.00-180.00  158
 16  \w   -104.00 -27.00   0.50    0.51    --  -38.95 -43.00  30.00  154
 17  \w     34.00  85.00   0.50    0.51    --   38.95  32.00 -90.00  102
 18  \w     36.00  62.00   0.50    0.51    --   38.95  43.00 150.00   52
 19  \w     27.00 108.00   0.50    0.51    --   38.95  32.00   0.00  162
 20  \w     22.00  94.00   0.50    0.51    --   38.95-138.00  60.00  144
 21  \w    112.00 152.00   0.50    2.04    --  100.00 111.00   0.00   80
 22  \w     68.00  96.00   0.50    2.04    --  100.00 -86.00   0.00   56
 23  \w     86.00 136.00   0.50    2.04    --  100.00  30.00   0.00  100
 24  \w     66.00 109.00   0.50    2.04    --  100.00-111.00  90.00   86
 25  \w     86.00 155.00   0.50    2.04    --  100.00  15.00-150.00  138
 26  \w     33.00  80.00   0.50    2.04    --  100.00 -93.00-180.00   94
 27  \w     26.00 108.00   0.50    2.04    --  100.00 -93.00-120.00  164
 28  \w     87.00 157.00   0.50    2.04    --  100.00  45.00 -60.00  140
 29  \w     80.00 130.00   0.50    2.04    --  100.00 -86.00  60.00  100
 30  \w     37.00 124.00   0.50    2.04    --  100.00 -69.00-120.00  174
 31  \w     35.00  74.00   0.50    2.04    --  100.00 -30.00   0.00   78
 32  \w     79.00 113.00   0.50    2.04    --  100.00 -30.00   0.00   68
 33  \w     37.00  82.00   0.50    2.04    --  100.00-133.00 150.00   90
 34  \w     35.00  77.00   0.50    2.04    --  100.00 -86.00  60.00   84
 35  \w     73.00 154.00   0.50    2.04    --  100.00  77.00-180.00  162
 36  \w     98.00 144.00   0.50    2.04    --  100.00  30.00 -30.00   92
 37  \w     76.00 117.00   0.50    2.04    --  100.00-133.00-120.00   82
 38  \w     27.00  68.00   0.50    2.04    --  100.00 -15.00-150.00   82
 39  \w     91.00 116.00   0.50    2.04    --  100.00 -22.00   0.00   50
 40  \w     44.00  83.00   0.50    2.04    --  100.00 -22.00   0.00   78
 41  \w     74.00 100.00   0.50    2.04    --  100.00-162.00 -83.00   52
 42  \w    -42.00 -16.00   0.50    0.51    --  -38.95  54.00 150.00   52
 43  \w    -59.00 -31.00   0.50    0.51    --  -38.95  21.00 -60.00   56
 44  \w      8.00  33.00   0.50    0.51    --  -38.95  21.00 -60.00   50
 45  \w     -9.00  49.00   0.50    0.51    --   38.95 -43.00-150.00  116
 46  \w     19.00  48.00   0.50    0.51    --   38.95-104.00 -60.00   58
 47  \w     80.00 105.00   0.50    0.51    --   38.95  32.00 120.00   50
 48  \w     47.00  73.00   0.50    0.51    --   38.95-138.00-180.00   52
 49  \w    -13.00  13.00   0.50    0.51    --   38.95-104.00 -60.00   52
 50  \w     35.00  61.00   0.50    2.04    --  100.00 -77.00 -60.00   52
 51  \w     36.00  69.00   0.50    2.04    --  100.00 -45.00 -30.00   66
 52  \w     77.00 124.00   0.50    2.04    --  100.00 -69.00  30.00   94
 53  \w     93.00 118.00   0.50    2.04    --  100.00 -45.00 -30.00   50
 54  \w    102.00 127.00   0.50    2.04    --  100.00 -77.00 -60.00   50
 55  \w    113.00 151.00   0.50    2.04    --  100.00  30.00  30.00   76
 56  \w     28.00  71.00   0.50    2.04    --  100.00 -22.00  90.00   86
 57  \w     84.00 120.00   0.50    2.04    --  100.00-133.00  30.00   72
 58  \w     84.00 137.00   0.50    2.04    --  100.00  45.00-120.00  106
 59  \w     85.00 132.00   0.50    2.04    --  100.00  53.00 120.00   94
 60  \w     72.00 117.00   0.50    2.04    --  100.00 -53.00  90.00   90
 61  \w     80.00 157.00   0.50    2.04    --  100.00  53.00  90.00  154
 62  \w    111.00 137.00   0.50    2.04    --  100.00  45.00  30.00   52
 63  \w     98.00 123.00   0.50    2.04    --  100.00-133.00-150.00   50
 64  \w     91.00 138.00   0.50    2.04    --  100.00 111.00  30.00   94
 65  \w     91.00 132.00   0.50    2.04    --  100.00 111.00 120.00   82
 66  \w     70.00  96.00   0.50    2.04    --  100.00  15.00 -60.00   52
 67  \w    119.00 145.00   0.50    2.04    --  100.00  15.00 -60.00   52
 68  \w     48.00  73.00   0.50    2.04    --  100.00 -22.00-120.00   50
 69  \w     99.00 125.00   0.50    2.04    --  100.00  22.00-120.00   52
 70  \w     59.00  85.00   0.50    2.04    --  100.00-111.00  60.00   52
 71  \w     84.00 110.00   0.50    2.04    --  100.00-111.00-180.00   52
 72  \w     67.00 109.00   0.50    2.04    --  100.00-111.00-120.00   84
 73  \w     67.00 110.00   0.50    2.04    --  100.00-133.00  60.00   86
 74  \w     41.00 116.00   0.50    2.04    --  100.00 -45.00  60.00  150
 75  \w     98.00 123.00   0.50    2.04    --  100.00-133.00  90.00   50
 76  \w    104.00 130.00   0.50    2.04    --  100.00 -86.00  90.00   52
 77  \w     85.00 115.00   0.50    2.04    --  100.00 -37.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520422000
_diffrn_orient_matrix_UB_12      -0.0288620000
_diffrn_orient_matrix_UB_13      -0.0723051000
_diffrn_orient_matrix_UB_21      -0.0069906000
_diffrn_orient_matrix_UB_22      0.0779140000
_diffrn_orient_matrix_UB_23      -0.0322194000
_diffrn_orient_matrix_UB_31      0.0759246000
_diffrn_orient_matrix_UB_32      -0.0126250000
_diffrn_orient_matrix_UB_33      -0.0334645000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30987
_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         70.344
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
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    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0371P)^2^+10.9757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5110
_reflns_number_total             5329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt00235j2.cif
_cod_data_source_block           iprincl3
_cod_depositor_comments
'Adding full bibliography for 7706540--7706543.cif.'
_cod_database_code               7706543
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C27 H36 N2 In Cl3'
_shelx_estimated_absorpt_t_max   0.441
_shelx_estimated_absorpt_t_min   0.174
_reflns_odcompleteness_completeness 96.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C22(H22), C25(H25), C16(H16), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C13(H13), C12(H12), C14(H14), C6(H6), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C)
;
_shelx_res_checksum              54387
_shelx_hkl_checksum              29706
_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 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.721