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_7240067
_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         'C19 H32 B3 N O7'
_chemical_formula_sum            'C19 H32 B3 N O7'
_chemical_formula_weight         418.88
_chemical_name_systematic
5,7-di-tert-butyl-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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2019-11-07 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                72.586(9)
_cell_angle_beta                 79.494(13)
_cell_angle_gamma                72.755(19)
_cell_formula_units_Z            4
_cell_length_a                   11.314(7)
_cell_length_b                   11.980(8)
_cell_length_c                   17.961(10)
_cell_measurement_reflns_used    3088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.24
_cell_volume                     2207(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40586
_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         26.420
_diffrn_reflns_theta_min         1.895
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.1 x 1 mm fine focus'
_diffrn_source_type              'Nonius FR-591'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0749 before and 0.0626 after correction. The Ratio of 
minimum to maximum transmission is 0.8078. The \l/2 correction factor 
is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         9038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0718
_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^)+(0.0438P)^2^+2.3934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4916
_reflns_number_total             9038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00346h2.cif
_cod_data_source_block           cmpd_4p
_cod_depositor_comments
;Adding full bibliography for 7240065--7240067.cif.

 Adding full bibliography for 7240065--7240067.cif.
;
_cod_database_code               7240067
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H5O_1-H5O_$1
 2.2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), N1(H1N), C1(H1), N1(H1N)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C16(H16A,H16B), C19(H19A,
 H19B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5(H5), C7(H7)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C9(H9A,H9B,
 H9C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C14(H14A,
 H14B,H14C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C),
 C9(H9A,H9B,H9C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5O), O4(H4), O5(H5O)
;
_shelx_res_checksum              67954
_olex2_submission_original_sample_id WM-D088-D1
_olex2_submission_special_instructions 'No special instructions were received'