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_4132599
_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 ad
_chemical_formula_moiety         'C17 H26 B N O3, C18 H20 N2 O2'
_chemical_formula_sum            'C35 H46 B N3 O5'
_chemical_formula_weight         599.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.805(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9592(17)
_cell_length_b                   9.3307(12)
_cell_length_c                   16.2386(19)
_cell_measurement_reflns_used    1677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.620
_cell_measurement_theta_min      4.036
_cell_volume                     1659.7(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1119
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12226
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        65.080
_diffrn_reflns_theta_max         65.080
_diffrn_reflns_theta_min         2.722
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0913 before and 0.0546 after correction. The Ratio of minimum to maximum transmission is 0.8190. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5335
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0566P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                3632
_reflns_number_total             5335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05045_si_005.cif
_cod_data_source_block           cx1055
_cod_database_code               4132599
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.867
_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 Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C25(H25), C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C)
;
_shelx_res_checksum              45192
_shelx_hkl_checksum              58687
_olex2_date_sample_data_collection 2017-08-24
_olex2_date_sample_submission    2017-08-19
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1055
_olex2_submission_special_instructions 'No special instructions were received'