Concise synthesis of α-amino cyclic boronates via multicomponent coupling of salicylaldehydes, amines, and B2(OH)4
Ming, Wenbo; Liu, Xiaocui; Friedrich, Alexandra; Krebs, Johannes; Budiman, Yudha P.; Huang, Mingming; Marder, Todd B.; Green Chemistry 22 (2020) 2184–2190; doi:10.1039/D0GC00346H

data_7240065
_publ_section_title
;
 Concise synthesis of \a-amino cyclic boronates via multicomponent
 coupling of salicylaldehydes, amines, and B2(OH)4
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2184
_journal_page_last               2190
_journal_paper_doi               10.1039/D0GC00346H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C11 H16 B3 N O7'
_chemical_formula_sum            'C11 H16 B3 N O7'
_chemical_formula_weight         306.68
_chemical_name_systematic
4',6'-dihydroxy-3-(morpholino-4-ium)-3H-spiro[benzo[d][1,2]oxaborole-2,2'-[1,3,5,2,4,6]trioxatriborinan]-2-uide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-11
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-07 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   9.073(7)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.42
_cell_volume                     1312.2(17)
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
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_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10207
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.057
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    0.123
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_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone/toluene'
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0554P)^2^+0.8515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1992
_reflns_number_total             2587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00346h2.cif
_cod_data_source_block           cmpd_4a
_cod_depositor_comments
;Adding full bibliography for 7240065--7240067.cif.

 Adding full bibliography for 7240065--7240067.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240065
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              46261