Enantioselective Synthesis of α-Amidoboronates Catalyzed by Planar-Chiral NHC-Cu(I) Complexes.
Schwamb, C. Benjamin; Fitzpatrick, Keegan P.; Brueckner, Alexander C.; Richardson, H. Camille; Cheong, Paul H.-Y.; Scheidt, Karl A.; Journal of the American Chemical Society 140 (2018) 10644–10648; doi:10.1021/jacs.8b05045

data_4132598
_publ_section_title
;
 Enantioselective Synthesis of \a-Amidoboronates Catalyzed by
 Planar-Chiral NHC-Cu(I) Complexes.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10644
_journal_page_last               10648
_journal_paper_doi               10.1021/jacs.8b05045
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C29 H32 Cl Cu Fe N2 O2'
_chemical_formula_sum            'C29 H32 Cl Cu Fe N2 O2'
_chemical_formula_weight         595.40
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4799(10)
_cell_length_b                   15.0428(13)
_cell_length_c                   15.3127(13)
_cell_measurement_reflns_used    9666
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      68.03
_cell_measurement_theta_min      4.12
_cell_volume                     2644.3(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45535
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_min         4.120
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.549
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.8039.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Precipitated with n-pentane from a saturated solution in CHCl3.'
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0049(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0211
_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^)+(0.0304P)^2^+1.4805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0558
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4795
_reflns_number_total             4798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05045_si_003.cif
_cod_data_source_block           omecpstcucl-pl
_cod_database_code               4132598
_shelx_estimated_absorpt_t_max   0.581
_shelx_estimated_absorpt_t_min   0.413
_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.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C17(H17), C18(H18), C4(H4), C3(H3), C2(H2), C16(H16)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C26(H26a,H26b,H26c), C10(H10a,H10b,H10c), C24(H24a,H24b,
 H24c), C9(H9a,H9b,H9c), C28(H28a,H28b,H28c), C27(H27a,H27b,H27c), C29(H29a,
 H29b,H29c)
;
_shelx_res_checksum              51455
_shelx_hkl_checksum              6678
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id OMeCpstCuCl
_olex2_submission_special_instructions 'No special instructions were received'