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_7242221
_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         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7022(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9356(3)
_cell_length_b                   3.81317(10)
_cell_length_c                   21.6720(5)
_cell_measurement_reflns_used    14698
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.6410
_cell_measurement_theta_min      4.1480
_cell_volume                     1532.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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 -57.00-180.00  100
  2  \w    -74.00  34.00   1.00    1.00    --  -41.80  77.00  90.00  108
  3  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
  4  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -30.00  100
  5  \w    -34.00  74.00   1.00    1.00    --   41.80 -77.00-180.00  108
  6  \w     23.00  98.00   1.00    1.00    --   41.80-125.00  60.00   75
  7  \w      5.00  32.00   1.00    1.00    --   42.00  90.00  98.07   27
  8  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 176.00   27
  9  \w     12.00  40.00   1.00    1.00    --   46.00  83.00 -75.64   28
 10  \w     17.00  45.00   1.00    1.00    --   50.00  80.00-149.23   28
 11  \w     16.00  45.00   1.00    1.00    --   50.00  81.00 112.39   29
 12  \w     16.00  45.00   1.00    1.00    --   50.00  81.00   2.03   29
 13  \w     33.00 142.00   1.00    1.00    --   66.00  77.00  39.37  109
 14  \w     34.00 141.00   1.00    1.00    --   66.00  75.00 169.00  107
 15  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 -85.20  108
 16  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 -55.27  108
 17  \w     37.00 146.00   1.00    1.00    --   70.00  77.00-123.20  109
 18  \w     38.00 146.00   1.00    1.00    --   70.00  76.00  68.89  108
 19  \w     37.00 146.00   1.00    1.00    --   70.00  77.00 131.98  109
 20  \w     42.00 150.00   1.00    1.00    --   74.00  76.00-179.27  108
 21  \w     42.00 149.00   1.00    1.00    --   74.00  75.00 -57.94  107
 22  \w     41.00 150.00   1.00    1.00    --   74.00  77.00 -29.52  109
 23  \w     41.00 150.00   1.00    1.00    --   74.00  77.00   0.21  109
 24  \w     41.00 150.00   1.00    1.00    --   74.00  77.00-152.61  109
 25  \w     47.00 152.00   1.00    1.00    --   78.00  71.00  95.87  105
 26  \w     51.00 156.00   1.00    1.00    --   82.00  71.00  73.73  105
 27  \w     54.00 162.00   1.00    1.00    --   86.00  76.00-107.65  108
 28  \w     59.00 164.00   1.00    1.00    --   90.00  71.00 113.00  105
 29  \w     59.00 164.00   1.00    1.00    --   90.00  72.00   1.09  105
 30  \w     60.00 163.00   1.00    1.00    --   90.00  65.00-142.90  103
 31  \w     65.00 166.00   1.00    1.00    --   94.00  61.00 -17.07  101
 32  \w     67.00 172.00   1.00    1.00    --   98.00  70.00 168.73  105
 33  \w     36.00 117.00   1.00    1.00    --  109.13-125.00-120.00   81
 34  \w     77.00 178.00   1.00    1.00    --  109.13  77.00 120.00  101
 35  \w     80.00 178.00   1.00    1.00    --  109.13  61.00  90.00   98
 36  \w     26.00 110.00   1.00    1.00    --  109.13 -94.00 -30.00   84
 37  \w     33.00 142.00   1.00    1.00    --  109.13 -77.00  60.00  109
 38  \w     77.00 178.00   1.00    1.00    --  109.13  77.00  60.00  101
 39  \w     36.00 117.00   1.00    1.00    --  109.13-125.00 -60.00   81
 40  \w     77.00 178.00   1.00    1.00    --  109.13  77.00  30.00  101
 41  \w     80.00 178.00   1.00    1.00    --  109.13  61.00 -90.00   98
 42  \w     77.00 178.00   1.00    1.00    --  109.13  77.00-180.00  101
 43  \w     83.00 178.00   1.00    1.00    --  109.13  45.00 -30.00   95
 44  \w     77.00 178.00   1.00    1.00    --  109.13  77.00 -90.00  101
 45  \w     77.00 178.00   1.00    1.00    --  109.13  77.00-150.00  101
 46  \w     77.00 178.00   1.00    1.00    --  109.13  77.00   0.00  101
 47  \w     26.00 110.00   1.00    1.00    --  109.13 -94.00  30.00   84
 48  \w     82.00 178.00   1.00    1.00    --  110.00  55.00-107.29   96
 49  \w     17.00 116.00   1.00    1.00    --   41.80  38.00 120.00   99
 50  \w     16.00 115.00   1.00    1.00    --   41.80  43.00  25.80   99
 51  \w      1.00 122.00   1.00    1.00    --   41.80  19.00   0.00  121
 52  \w      7.00  36.00   1.00    1.00    --   42.00  85.00 -86.03   29
 53  \w     11.00  38.00   1.00    1.00    --   46.00  84.00-131.82   27
 54  \w     11.00  38.00   1.00    1.00    --   46.00  84.00  95.57   27
 55  \w     30.00 138.00   1.00    1.00    --   62.00  76.00  87.47  108
 56  \w     30.00 137.00   1.00    1.00    --   62.00  75.00  -3.45  107
 57  \w     29.00 138.00   1.00    1.00    --   62.00  77.00-162.14  109
 58  \w     35.00 140.00   1.00    1.00    --   66.00  72.00  29.25  105
 59  \w     34.00 141.00   1.00    1.00    --   66.00  75.00 107.96  107
 60  \w     38.00 146.00   1.00    1.00    --   70.00  76.00 -46.99  108
 61  \w     38.00 146.00   1.00    1.00    --   70.00  76.00-159.25  108
 62  \w     38.00 145.00   1.00    1.00    --   70.00  75.00 124.67  107
 63  \w     43.00 147.00   1.00    1.00    --   74.00  69.00 -74.31  104
 64  \w     51.00 150.00   1.00    1.00    --   78.00  52.00  69.38   99
 65  \w     48.00 151.00   1.00    1.00    --   78.00  67.00-141.95  103
 66  \w     52.00 155.00   1.00    1.00    --   82.00  65.00  72.36  103
 67  \w     21.00 178.00   1.00    1.00    --  109.13   0.00-150.00  157
 68  \w     21.00 178.00   1.00    1.00    --  109.13   0.00-180.00  157
 69  \w     80.00 178.00   1.00    1.00    --  109.13  61.00-150.00   98
 70  \w     36.00 117.00   1.00    1.00    --  109.13-125.00 -30.00   81
 71  \w     77.00 178.00   1.00    1.00    --  109.13  77.00  90.00  101
 72  \w     77.00 178.00   1.00    1.00    --  109.13  77.00-120.00  101
 73  \w     80.00 178.00   1.00    1.00    --  109.13  61.00  60.00   98
 74  \w     80.00 178.00   1.00    1.00    --  109.13  61.00 -30.00   98
 75  \w     83.00 178.00   1.00    1.00    --  109.13  45.00  30.00   95
 76  \w     36.00 117.00   1.00    1.00    --  109.13-125.00-150.00   81
 77  \w     21.00  94.00   1.00    1.00    --  109.13   0.00   0.00   73
 78  \w     80.00 178.00   1.00    1.00    --  109.13  61.00 150.00   98
 79  \w     21.00 178.00   1.00    1.00    --  109.13   0.00 -30.00  157
 80  \w     21.00 178.00   1.00    1.00    --  109.13   0.00 -60.00  157
 81  \w     80.00 178.00   1.00    1.00    --  109.13  61.00 120.00   98
 82  \w     21.00 178.00   1.00    1.00    --  109.13   0.00 -90.00  157
 83  \w     21.00 178.00   1.00    1.00    --  109.13   0.00-120.00  157
 84  \w     80.00 178.00   1.00    1.00    --  109.13  61.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214467000
_diffrn_orient_matrix_UB_12      0.2582056000
_diffrn_orient_matrix_UB_13      0.0553363000
_diffrn_orient_matrix_UB_21      0.0792303000
_diffrn_orient_matrix_UB_22      -0.1165705000
_diffrn_orient_matrix_UB_23      0.0079177000
_diffrn_orient_matrix_UB_31      0.0127838000
_diffrn_orient_matrix_UB_32      0.2881895000
_diffrn_orient_matrix_UB_33      -0.0463009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38369
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         4.166
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0578P)^2^+1.2741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1386
_reflns_number_total             1577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm003
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_original_cell_volume        1532.30(6)
_cod_database_code               7242221
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C8 H8 N2 O2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              48147
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.667