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_1567341
_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         'C21 H34 Au Cl N2 O'
_chemical_formula_sum            'C21 H34 Au Cl N2 O'
_chemical_formula_weight         562.92
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7764(12)
_cell_length_b                   14.6129(18)
_cell_length_c                   16.587(2)
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4800
_cell_measurement_theta_min      2.4182
_cell_measurement_wavelength     0.71073
_cell_volume                     2369.6(5)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_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  0.0789
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13335
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.418
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    6.332
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.530
_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    1.578
_exptl_crystal_description       board
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.499
_refine_diff_density_min         -1.761
_refine_diff_density_rms         0.226
_refine_ls_abs_structure_details
;
Flack x determined using 1590 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+39.6003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                4340
_reflns_number_total             5320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2sc02908a2.cif
_cod_data_source_block           DPI280
_cod_original_cell_volume        2369.7(5)
_cod_database_code               1567341
_shelx_res_checksum              76734