A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones
Kassin, Victor-Emmanuel H.; Morodo, Romain; Toupy, Thomas; Jacquemin, Isaline; Van Hecke, Kristof; Robiette, Raphaël; Monbaliu, Jean-Christophe M.; Green Chemistry 23 (2021) 2336–2351; doi:10.1039/D0GC04395H

data_7242224
_publ_section_title
;
 A modular, low footprint and scalable flow platform for the expedient
 \a-aminohydroxylation of enolizable ketones
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2336
_journal_page_last               2351
_journal_paper_doi               10.1039/D0GC04395H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H12 O6'
_chemical_formula_sum            'C7 H12 O6'
_chemical_formula_weight         192.17
_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     direct
_audit_creation_date             2019-05-24
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                81.705(2)
_cell_angle_beta                 88.677(2)
_cell_angle_gamma                73.562(3)
_cell_formula_units_Z            4
_cell_length_a                   7.6334(2)
_cell_length_b                   8.7609(3)
_cell_length_c                   14.2366(3)
_cell_measurement_reflns_used    14607
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.0890
_cell_measurement_theta_min      5.2870
_cell_volume                     903.45(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-150.00  100
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00  60.00   99
  3  \w   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 -30.00   99
  4  \w    -66.00  32.00   1.00    1.00    --  -41.80  38.00 150.00   98
  5  \w     23.00  98.00   1.00    1.00    --   41.80-125.00 -60.00   75
  6  \w    -30.00  70.00   1.00    1.00    --   41.80 -57.00   0.00  100
  7  \w     12.00  45.00   1.00    1.00    --   46.00  81.00  76.01   33
  8  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 157.99   27
  9  \w     17.00  45.00   1.00    1.00    --   50.00  79.00-122.30   28
 10  \w     16.00  45.00   1.00    1.00    --   50.00  82.00 -42.95   29
 11  \w     17.00  45.00   1.00    1.00    --   50.00  79.00-101.05   28
 12  \w     25.00 134.00   1.00    1.00    --   58.00  77.00 148.34  109
 13  \w     30.00 138.00   1.00    1.00    --   62.00  76.00  31.62  108
 14  \w     30.00 137.00   1.00    1.00    --   62.00  73.00  -2.60  107
 15  \w     31.00 136.00   1.00    1.00    --   62.00  71.00 -44.30  105
 16  \w     31.00 136.00   1.00    1.00    --   62.00  71.00 179.34  105
 17  \w     36.00 139.00   1.00    1.00    --   66.00  68.00 -19.48  103
 18  \w     34.00 141.00   1.00    1.00    --   66.00  75.00  73.90  107
 19  \w     39.00 144.00   1.00    1.00    --   70.00  70.00  28.03  105
 20  \w     39.00 144.00   1.00    1.00    --   70.00  70.00 122.33  105
 21  \w     37.00 146.00   1.00    1.00    --   70.00  77.00-119.99  109
 22  \w     41.00 150.00   1.00    1.00    --   74.00  77.00-154.52  109
 23  \w     47.00 151.00   1.00    4.00    --   78.00  69.00 -95.74  104
 24  \w     47.00 151.00   1.00    4.00    --   78.00  69.00  42.82  104
 25  \w     60.00 163.00   1.00    4.00    --   90.00  64.00  36.40  103
 26  \w     59.00 163.00   1.00    4.00    --   90.00  69.00 -85.23  104
 27  \w     63.00 168.00   1.00    4.00    --   94.00  71.00 -57.62  105
 28  \w     62.00 169.00   1.00    4.00    --   94.00  75.00 174.78  107
 29  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 30  \w     33.00 142.00   1.00    4.00    --  109.13 -77.00  60.00  109
 31  \w     36.00 117.00   1.00    4.00    --  109.13-125.00 -60.00   81
 32  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 120.00   98
 33  \w     83.00 178.00   1.00    4.00    --  109.13  45.00 120.00   95
 34  \w     77.00 178.00   1.00    4.00    --  109.13  77.00  60.00  101
 35  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 36  \w     80.00 178.00   1.00    4.00    --  109.13  61.00  60.00   98
 37  \w     80.00 178.00   1.00    4.00    --  109.13  61.00  30.00   98
 38  \w     26.00 110.00   1.00    4.00    --  109.13 -94.00  30.00   84
 39  \w     36.00 135.00   1.00    4.00    --  109.13 -45.00 120.00   99
 40  \w     80.00 178.00   1.00    4.00    --  109.13  61.00-120.00   98
 41  \w     26.00 110.00   1.00    4.00    --  109.13 -94.00 150.00   84
 42  \w     79.00 178.00   1.00    4.00    --  109.13  68.00 -14.05   99
 43  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -30.00   98
 44  \w     36.00 117.00   1.00    4.00    --  109.13-125.00   0.00   81
 45  \w     77.00 178.00   1.00    4.00    --  109.13  77.00-180.00  101
 46  \w     78.00 178.00   1.00    4.00    --  109.13  70.00-142.96  100
 47  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 120.00  101
 48  \w     17.00 116.00   1.00    1.00    --   41.80  38.00 -60.00   99
 49  \w     13.00  45.00   1.00    1.00    --   46.00  78.00-102.01   32
 50  \w     13.00  45.00   1.00    1.00    --   46.00  79.00 -64.92   32
 51  \w     12.00  45.00   1.00    1.00    --   46.00  82.00   9.61   33
 52  \w     22.00 129.00   1.00    1.00    --   54.00  75.00-154.43  107
 53  \w     25.00 134.00   1.00    1.00    --   58.00  77.00  86.82  109
 54  \w     26.00 111.00   1.00    1.00    --   58.00  76.00  35.18   85
 55  \w     30.00 137.00   1.00    1.00    --   62.00  75.00 110.96  107
 56  \w     34.00 141.00   1.00    1.00    --   66.00  73.00  49.09  107
 57  \w     42.00 142.00   1.00    1.00    --   70.00  54.00  39.28  100
 58  \w     37.00 146.00   1.00    1.00    --   70.00  77.00-103.14  109
 59  \w     39.00 143.00   1.00    1.00    --   70.00  69.00-166.49  104
 60  \w     42.00 150.00   1.00    1.00    --   74.00  76.00-145.42  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1887452000
_diffrn_orient_matrix_UB_12      -0.0413972000
_diffrn_orient_matrix_UB_13      0.0490855000
_diffrn_orient_matrix_UB_21      -0.0922787000
_diffrn_orient_matrix_UB_22      0.0107137000
_diffrn_orient_matrix_UB_23      0.0971594000
_diffrn_orient_matrix_UB_31      0.0123118000
_diffrn_orient_matrix_UB_32      -0.1802579000
_diffrn_orient_matrix_UB_33      0.0106484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         3.138
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0657P)^2^+0.3443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm008
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242224
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H12 O6'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C10(H10A,H10B), C13(H13A,H13B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C4(H4A,H4B,H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8), O1(H1), O2(H2)
;
_shelx_res_checksum              11350
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.770
_oxdiff_exptl_absorpt_empirical_full_min 0.575