Selective hydroboration of electron-rich isocyanates by an NHC-copper(I) alkoxide.
English, Laura E.; Horsley Downie, Thomas M.; Lyall, Catherine L.; Mahon, Mary F.; McMullin, Claire L.; Neale, Samuel E.; Saunders, Carla M.; Liptrot, David J.; Chemical communications (Cambridge, England) 59 (2023) 1074–1077; doi:10.1039/d2cc04742j

data_7131147
_publ_section_title
;
 Selective hydroboration of electron-rich isocyanates by an NHC-copper(I)
 alkoxide.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1074
_journal_page_last               1077
_journal_paper_doi               10.1039/d2cc04742j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C32 H48 Cu N3 O, C6 H6'
_chemical_formula_sum            'C38 H54 Cu N3 O'
_chemical_formula_weight         632.38
_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             2020-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-06 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.54930(10)
_cell_length_b                   16.05570(10)
_cell_length_c                   19.4851(2)
_cell_measurement_reflns_used    14996
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.9220
_cell_measurement_theta_min      3.5630
_cell_volume                     3602.27(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.072
_diffrn_reflns_theta_min         3.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0407P)^2^+1.4525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6672
_reflns_number_total             7138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04742j2.cif
_cod_data_source_block           s20djl11
_cod_depositor_comments
'Adding full bibliography for 7131146--7131147.cif.'
_cod_database_code               7131147
_shelxl_version_number           2014-3
_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. Others
 Fixed Sof: C33A(0.4) H33A(0.4) C34A(0.4) H34A(0.4) C35A(0.4) H35A(0.4)
 C36A(0.4) H36A(0.4) C37A(0.4) H37A(0.4) C38A(0.4) H38A(0.4) C33(0.6) H33(0.6)
 C34(0.6) H34(0.6) C35(0.6) H35(0.6) C36(0.6) H36(0.6) C37(0.6) H37(0.6)
 C38(0.6) H38(0.6)
3.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C23(H23), C26(H26), C29(H29)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C32(H32), C33A(H33A),
 C34A(H34A), C35A(H35A), C36A(H36A), C37A(H37A), C38A(H38A), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38)
3.d Fitted hexagon refined as free rotating group:
 C33A(C34A,C35A,C36A,C37A,C38A), C33(C34,C35,C36,C37,C38)
3.e 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)
;