Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes.
Babula, Dawid J.; Charman, Rex S. C.; Hobson, Josie A.; Mahon, Mary F.; Liptrot, David J.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 3990–3993; doi:10.1039/d4dt00334a

data_7715140
_publ_section_title
;
 Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper
 complexes.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3990
_journal_page_last               3993
_journal_paper_doi               10.1039/d4dt00334a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C34 H45 Cu N2, 0.25[C5H12]'
_chemical_formula_sum            'C35.25 H48 Cu N2'
_chemical_formula_weight         563.29
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-17 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   27.8759(4)
_cell_length_b                   27.8759(4)
_cell_length_c                   22.0267(4)
_cell_measurement_reflns_used    13784
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6040
_cell_measurement_theta_min      4.4040
_cell_volume                     14823.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_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  0.0864
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.001
_diffrn_reflns_theta_min         4.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             5445
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+6.1182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2635
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00334a2.cif
_cod_data_source_block           s23djl17
_cod_depositor_comments
'Adding full bibliography for 7715138--7715141.cif.'
_cod_original_cell_volume        14823.1(5)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               7715140
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.844
_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. Restrained distances
 C2-H2B = C2-H2D = C2-H2A = C2-H2C
 0.98 with sigma of 0.005
 C5-C10 \\sim C5-C10A
 with sigma of 0.005
 C10-C11 \\sim C10A-C11A \\sim C10-C12 \\sim C10A-C12A
 with sigma of 0.005
 H2C-H2D \\sim H2A-H2B \\sim H3B-H3A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C10A \\sim C11A \\sim C12A: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) H2D(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C10(0.55) H10(0.55) C11(0.55) H11A(0.55) H11B(0.55) H11C(0.55) C12(0.55)
 H12A(0.55) H12B(0.55) H12C(0.55) C10A(0.45) H10A(0.45) C11A(0.45) H11D(0.45)
 H11E(0.45) H11F(0.45) C12A(0.45) H12D(0.45) H12E(0.45) H12F(0.45)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10), C10A(H10A)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              42112
_shelx_fab_checksum              91092