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_4132596
_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         'C54 H42 Cl Cu Fe N2 O2, 3(C H2 Cl2)'
_chemical_formula_sum            'C57 H48 Cl7 Cu Fe N2 O2'
_chemical_formula_weight         1160.51
_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             2016-04-26
_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                   15.6465(4)
_cell_length_b                   16.9240(4)
_cell_length_c                   19.6011(5)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.040
_cell_measurement_theta_min      2.401
_cell_volume                     5190.4(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.04
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'QuazarTM optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            198690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.216
_diffrn_reflns_theta_min         1.590
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.9346.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.483
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Flack x determined using 7200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.016(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         19753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0720P)^2^+4.8575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                17365
_reflns_number_total             19753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05045_si_004.cif
_cod_data_source_block           cx0743
_cod_database_code               4132596
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H7(0.02) H8(0.024) H9(0.025) H10(0.022) H11(0.018) H13(0.021)
 H14(0.028) H15(0.031) H16(0.029) H17(0.021) H19(0.023) H20(0.03) H21(0.033)
 H22(0.03) H23(0.023) H25(0.022) H26(0.032) H27(0.034) H28(0.028) H29(0.02)
 H31(0.019) H32(0.023) H33(0.023) H34(0.025) H35(0.021) H37(0.017) H38(0.019)
 H39(0.017) H42(0.02) H44(0.02) H46A(0.028) H46B(0.028) H46C(0.028) H49(0.03)
 H50(0.031) H51(0.03) H53A(0.046) H53B(0.046) H53C(0.046) H54A(0.063)
 H54B(0.063) H54C(0.063) H56A(0.043) H56B(0.043) H55A(0.057) H55B(0.057)
 H57A(0.046) H57B(0.046)
 Fixed X: H7(0.6738) H8(0.7595) H9(0.8604) H10(0.8727) H11(0.7864) H13(0.5871)
 H14(0.6153) H15(0.6896) H16(0.7345) H17(0.7021) H19(0.4968) H20(0.4285)
 H21(0.4376) H22(0.522) H23(0.5922) H25(0.709) H26(0.6785) H27(0.5403)
 H28(0.4288) H29(0.4578) H31(0.8126) H32(0.8749) H33(0.7897) H34(0.6416)
 H35(0.5788) H37(0.3783) H38(0.4461) H39(0.5153) H42(0.3804) H44(0.4755)
 H46A(0.3508) H46B(0.3081) H46C(0.2716) H49(0.7496) H50(0.7115) H51(0.5899)
 H53A(0.7493) H53B(0.7921) H53C(0.741) H54A(0.3959) H54B(0.4414) H54C(0.491)
 H56A(0.3706) H56B(0.3873) H55A(0.8227) H55B(0.7751) H57A(1.0217) H57B(0.9533)
 Fixed Y: H7(0.3353) H8(0.372) H9(0.4742) H10(0.538) H11(0.5014) H13(0.5542)
 H14(0.6897) H15(0.7402) H16(0.6558) H17(0.5208) H19(0.5128) H20(0.553)
 H21(0.4769) H22(0.3627) H23(0.3223) H25(0.1927) H26(0.0799) H27(0.0546)
 H28(0.1398) H29(0.2498) H31(0.2758) H32(0.1653) H33(0.0613) H34(0.0665)
 H35(0.1759) H37(0.3384) H38(0.2311) H39(0.2967) H42(0.6085) H44(0.6463)
 H46A(0.4886) H46B(0.5631) H46C(0.4761) H49(0.6708) H50(0.6316) H51(0.5563)
 H53A(0.6844) H53B(0.6478) H53C(0.7295) H54A(0.459) H54B(0.538) H54C(0.4554)
 H56A(0.3279) H56B(0.4144) H55A(0.1712) H55B(0.2201) H57A(0.7193) H57B(0.7103)
 Fixed Z: H7(0.6997) H8(0.7905) H9(0.7779) H10(0.6726) H11(0.5811) H13(0.6047)
 H14(0.5977) H15(0.5035) H16(0.4171) H17(0.4215) H19(0.4439) H20(0.3442)
 H21(0.246) H22(0.245) H23(0.3448) H25(0.4462) H26(0.3808) H27(0.3445)
 H28(0.375) H29(0.4442) H31(0.5837) H32(0.6355) H33(0.6734) H34(0.6571)
 H35(0.6048) H37(0.5118) H38(0.5843) H39(0.6882) H42(0.6092) H44(0.7316)
 H46A(0.4723) H46B(0.5093) H46C(0.5228) H49(0.8664) H50(0.9757) H51(0.9952)
 H53A(0.688) H53B(0.7551) H53C(0.7594) H54A(0.9633) H54B(0.9898) H54C(0.9931)
 H56A(0.7971) H56B(0.8274) H55A(0.7733) H55B(0.8319) H57A(0.5373) H57B(0.4771)
;
_shelx_res_checksum              64718
_shelx_hkl_checksum              34204
_olex2_date_sample_data_collection 2016-04-25
_olex2_date_sample_submission    2016-04-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre in Paratone oil'
_olex2_submission_original_sample_id cx0743
_olex2_submission_special_instructions 'No special instructions were received'