Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) <i>via</i> trifluoroborate-iminiums (TIMs).
Shiro, Tomoya; Schuhmacher, Anne; Jackl, Moritz K.; Bode, Jeffrey W.; Chemical science 9 (2018) 5191–5196; doi:10.1039/c8sc01486h

data_1549415
_publ_section_title
;
 Facile synthesis of \a-aminoboronic acids from amines and potassium
 acyltrifluoroborates (KATs) <i>via</i> trifluoroborate-iminiums (TIMs).
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              5191
_journal_page_last               5196
_journal_paper_doi               10.1039/c8sc01486h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C8 H8 B F4 N'
_chemical_formula_sum            'C8 H8 B F4 N'
_chemical_formula_weight         204.96
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.529(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.1042(2)
_cell_length_b                   37.0556(10)
_cell_length_c                   7.9394(2)
_cell_measurement_reflns_used    13847
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.6570
_cell_measurement_theta_min      4.7500
_cell_volume                     1792.45(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00  24.36   0.38    1.50    --  -50.21  19.00 -30.00  222
  2  \w   -121.00 -35.88   0.38    1.50    --  -50.21 -57.00 -30.00  224
  3  \w   -120.00 -39.06   0.38    1.50    --  -50.21-178.00-120.00  213
  4  \w    -76.00   3.80   0.38    9.00    --  -70.00  19.00  90.00  210
  5  \w   -140.00 -70.84   0.38    9.00    --  -70.00-125.00  60.00  182
  6  \w     33.00  74.80   0.38    9.00    --  107.75 -19.00  60.00  110
  7  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00 -30.00   94
  8  \w     33.00  74.80   0.38    9.00    --  107.75 -19.00 -90.00  110
  9  \w     39.00 110.06   0.38    9.00    --  107.75 -99.00-120.00  187
 10  \w     33.00  74.80   0.38    9.00    --  107.75 -19.00   0.00  110
 11  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00  60.00   94
 12  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00 -60.00   94
 13  \w     39.00 110.06   0.38    9.00    --  107.75 -99.00-180.00  187
 14  \w     37.00 105.02   0.38    9.00    --  107.75 -57.00 120.00  179
 15  \w     33.00  74.80   0.38    9.00    --  107.75 -19.00 150.00  110
 16  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00 150.00   94
 17  \w     37.00 105.02   0.38    9.00    --  107.75 -57.00 -90.00  179
 18  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00  90.00   94
 19  \w     37.00 105.02   0.38    9.00    --  107.75 -57.00-150.00  179
 20  \w     33.00  68.72   0.38    9.00    --  107.75 -38.00-180.00   94
 21  \w   -121.00 -35.88   0.38    1.50    --  -50.21 -57.00  30.00  224
 22  \w   -115.00 -29.12   0.38    1.50    --  -50.21 -77.00 120.00  226
 23  \w   -115.00 -29.12   0.38    1.50    --  -50.21 -77.00 -90.00  226
 24  \w   -135.00 -47.98   0.38    9.00    --  -70.00 -77.00-150.00  229
 25  \w   -135.00 -47.98   0.38    9.00    --  -70.00 -77.00 -60.00  229
 26  \w     97.00 177.18   0.38    9.00    --  107.75  19.00 120.00  211
 27  \w     98.00 168.68   0.38    9.00    --  107.75  38.00 -30.00  186
 28  \w     97.00 177.18   0.38    9.00    --  107.75  19.00  60.00  211
 29  \w     39.00 110.06   0.38    9.00    --  107.75 -99.00  60.00  187
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0604759000
_diffrn_orient_matrix_UB_12      0.0266207000
_diffrn_orient_matrix_UB_13      0.1445977000
_diffrn_orient_matrix_UB_21      -0.0111635000
_diffrn_orient_matrix_UB_22      0.0315078000
_diffrn_orient_matrix_UB_23      -0.1265839000
_diffrn_orient_matrix_UB_31      -0.2453189000
_diffrn_orient_matrix_UB_32      0.0051166000
_diffrn_orient_matrix_UB_33      0.0291041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6644
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_min         4.774
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6644
_refine_ls_number_restraints     89
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1057P)^2^+0.9150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6029
_reflns_number_total             6644
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9876\% 
 around [1.00 -0.00 -0.00] (reciprocal) or [1.00 0.00 0.05] (direct)
;
_cod_data_source_file            c8sc01486h1.cif
_cod_data_source_block           jb211116_1_1
_cod_depositor_comments
'Adding full bibliography for 1549414--1549418.cif.'
_cod_database_code               1549415
_chemical_oxdiff_formula         'C8 H8 B1 F4 N1'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6815(17) 0.3185(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1A-H1A = N1B-H1B
 0.93 with sigma of 0.02
 F1C-B1B \\sim F1B-B1B \\sim F3C-B1B \\sim F3B-B1B \\sim F2C-B1B \\sim F2B-B1B
 with sigma of 0.02
 F1B-F2B \\sim F2B-F3B \\sim F3B-F1B \\sim F1C-F2C \\sim F2C-F3C \\sim F3C-F1C
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 F1B, F2B, F3B, B1B, F2C, F1C, F3C, C2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F2C)=Sof(F1C)=Sof(F3C)=1-FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B)
6.b Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              13296
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-22
_olex2_date_sample_submission    2016-11-21
_olex2_submission_original_sample_id jb211116_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.312
_oxdiff_exptl_absorpt_empirical_full_min 0.619
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2