Chiral oxazolidines acting as transient hydroxyalkyl-functionalized N-heterocyclic carbenes: an efficient route to air stable copper and gold complexes for asymmetric catalysis
Pichon-Barré, Delphine; Zhang, Ziyun; Cador, Aël; Vives, Thomas; Roisnel, Thierry; Baslé, Olivier; Jarrige, Lucie; Cavallo, Luigi; Falivene, Laura; Mauduit, Marc; Chemical Science  (2022) –; doi:10.1039/D2SC02908A

data_1567340
_publ_section_title
;
 Chiral oxazolidines acting as transient hydroxyalkyl-functionalized
 N-heterocyclic carbenes: an efficient route to air stable copper and gold
 complexes for asymmetric catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02908A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H28 Au Cl N2 O'
_chemical_formula_sum            'C18 H28 Au Cl N2 O'
_chemical_formula_weight         520.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.115(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.311(3)
_cell_length_b                   9.3672(9)
_cell_length_c                   15.1782(16)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5163
_cell_measurement_theta_min      2.2953
_cell_measurement_wavelength     0.710730
_cell_volume                     3935.5(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0287471
_diffrn_orient_matrix_UB_12      0.0489914
_diffrn_orient_matrix_UB_13      0.0147841
_diffrn_orient_matrix_UB_21      0.0214785
_diffrn_orient_matrix_UB_22      0.0499220
_diffrn_orient_matrix_UB_23      0.0515025
_diffrn_orient_matrix_UB_31      0.0041675
_diffrn_orient_matrix_UB_32      0.0806492
_diffrn_orient_matrix_UB_33      -0.0408609
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21092
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.213
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    7.617
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.035
_refine_diff_density_max         1.727
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.013(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         8916
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0057P)^2^+1.3139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                8163
_reflns_number_total             8916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc02908a2.cif
_cod_data_source_block           DPI494_3
_cod_original_cell_volume        3935.6(7)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1567340
_shelx_res_checksum              55150