Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters.
Chen, Lili; Zou, Xiaoliang; Zhao, Haonan; Xu, Senmiao; Organic letters 19 (2017) 3676–3679; doi:10.1021/acs.orglett.7b01740

data_1547102
_publ_section_title
;
 Copper-Catalyzed Asymmetric Protoboration of \b-Amidoacrylonitriles and
 \b-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral
 \a-Amino Boronate Esters.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3676
_journal_page_last               3679
_journal_paper_doi               10.1021/acs.orglett.7b01740
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H27 B I N O5'
_chemical_formula_sum            'C19 H27 B I N O5'
_chemical_formula_weight         487.12
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8874(10)
_cell_length_b                   11.4556(12)
_cell_length_c                   37.795(4)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.32
_cell_volume                     4280.9(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            27830
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.097
_diffrn_reflns_theta_max         25.097
_diffrn_reflns_theta_min         1.858
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.524
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1212 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.5945.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.456
_refine_diff_density_min         -2.229
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 3005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         7567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+15.8631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7245
_reflns_number_total             7567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01740_si_003.cif
_cod_data_source_block           10
_cod_depositor_comments
;

2019-03-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H27 B I N O5)'
_cod_original_formula_sum        'C38 H54 B2 I2 N2 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     974.25
_cod_database_code               1547102
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C27(H27), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C37(H37A,H37B), C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25), C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C), C38(H38A,H38B,H38C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              73472
_shelx_hkl_checksum              51319
_olex2_submission_special_instructions 'No special instructions were received'