Enantioselective synthesis of cyclic α-aminoboronates via copper-catalyzed dearomative borylation of 4-quinolinols
Xu, Ming; Ouyang, Yizhao; Wang, Linghua; Zhang, Shuai; Li, Pengfei; Chemical Communications  (2022) –; doi:10.1039/D2CC00027J

data_7129724
_publ_section_title
;
 Enantioselective synthesis of cyclic \a-aminoboronates via
 copper-catalyzed dearomative borylation of 4-quinolinols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00027J
_journal_year                    2022
_chemical_absolute_configuration S
_chemical_formula_moiety         'C21 H30 B N O5 S, H2 O'
_chemical_formula_sum            'C21 H32 B N O6 S'
_chemical_formula_weight         437.34
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-10-18 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2610(2)
_cell_length_b                   16.8304(6)
_cell_length_c                   18.6890(6)
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.42
_cell_measurement_theta_min      2.63
_cell_volume                     2283.90(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30751
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.449
_diffrn_reflns_theta_min         3.534
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1465 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.029(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0325P)^2^+0.3657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4544
_reflns_number_total             4594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00027j2.cif
_cod_data_source_block           cu_xm1012_0m
_cod_database_code               7129724
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.687
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.971(13)
 0.029(13)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C17(H17)
3.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C23(H23)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,
 H29B,H29C)
;
_shelx_res_checksum              23441
_olex2_submission_special_instructions 'No special instructions were received'