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_7715139
_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         'C32 H49 Cu N2'
_chemical_formula_sum            'C32 H49 Cu N2'
_chemical_formula_weight         525.27
_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             2023-11-16
_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                 100.920(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9361(6)
_cell_length_b                   15.2910(6)
_cell_length_c                   18.7521(8)
_cell_measurement_reflns_used    9663
_cell_measurement_temperature    149.9(6)
_cell_measurement_theta_max      29.4080
_cell_measurement_theta_min      3.3060
_cell_volume                     3079.0(2)
_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      149.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1468
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27835
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.647
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96284
_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    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         8130
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0510P)^2^+1.3182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5881
_reflns_number_total             8130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00334a2.cif
_cod_data_source_block           e23djl04
_cod_depositor_comments
'Adding full bibliography for 7715138--7715141.cif.'
_cod_database_code               7715139
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3 \\sim C4-C3A \\sim C2-C3 \\sim C2-C3A
 with sigma of 0.005
 C29-C30 \\sim C29-C30A \\sim C29-C31 \\sim C29-C31A \\sim C29-C32 \\sim
C29-C32A
 with sigma of 0.005
 C30-C31 \\sim C31-C32 \\sim C32-C30 \\sim C30A-C31A \\sim C31A-C32A \\sim
C32A-C30A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C3 \\sim C3A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01
within 2A
C30 \\sim C31 \\sim C32 \\sim C30A \\sim C31A \\sim C32A: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Fixed Sof: H2AA(0.55) H2AB(0.55) H2BC(0.45) H2BD(0.45) H4AA(0.55) H4AB(0.55)
 H4BC(0.45) H4BD(0.45) C3(0.55) H3A(0.55) H3B(0.55) C30(0.7) H30A(0.7)
 H30B(0.7) H30C(0.7) C31(0.7) H31A(0.7) H31B(0.7) H31C(0.7) C32(0.7) H32A(0.7)
 H32B(0.7) H32C(0.7) C3A(0.45) H3AA(0.45) H3AB(0.45) C30A(0.3) H30D(0.3)
 H30E(0.3) H30F(0.3) C31A(0.3) H31D(0.3) H31E(0.3) H31F(0.3) C32A(0.3)
 H32D(0.3) H32E(0.3) H32F(0.3)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C23(H23), C26(H26)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2AA,H2AB), C2(H2BC,H2BD), C4(H4AA,H4AB), C4(H4BC,H4BD), C3(H3A,H3B),
 C3A(H3AA,H3AB)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F)
;
_shelx_res_checksum              91015