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_7242220
_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         'C10 H13 N O2'
_chemical_formula_sum            'C10 H13 N O2'
_chemical_formula_weight         179.21
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-06
_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                90
_cell_angle_beta                 96.167(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7769(3)
_cell_length_b                   7.6286(5)
_cell_length_c                   21.5338(10)
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      74.9950
_cell_measurement_theta_min      4.1050
_cell_volume                     943.50(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.954
_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   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00  90.00   99
  2  \w   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00-120.00  101
  3  \w    -92.00  -2.00   1.00    6.00    --  -41.68 125.00  30.00   90
  4  \w   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00   0.00   99
  5  \w    -34.00  74.00   1.00    6.00    --   41.68 -77.00 -60.00  108
  6  \w     27.00  87.00   1.00   30.00    --  109.13 -96.00 -12.00   60
  7  \w     94.00 178.00   1.00   30.00    --  109.13 125.00-120.00   84
  8  \w     36.00 117.00   1.00   30.00    --  109.13-125.00-150.00   81
  9  \w     87.00 178.00   1.00   30.00    --  109.13  45.00 150.00   91
 10  \w     36.00  81.00   1.00   30.00    --  109.13-125.00 120.00   45
 11  \w     81.00 178.00   1.00   30.00    --  109.13  30.00  30.00   97
 12  \w     33.00 137.00   1.00   30.00    --  109.13 -30.00  60.00  104
 13  \w     36.00  66.00   1.00   30.00    --  109.13-125.00 -30.00   30
 14  \w     81.00 178.00   1.00   30.00    --  109.13  30.00-150.00   97
 15  \w     33.00  53.00   1.00   30.00    --  109.13 -30.00-150.00   20
 16  \w     36.00  61.00   1.00   30.00    --  109.13 -45.00 -30.00   25
 17  \w   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00 -30.00  101
 18  \w     68.00 118.00   1.00    6.00    --   41.68  77.00-180.00   50
 19  \w     98.00 118.00   1.00    6.00    --   41.68  77.00  90.00   20
 20  \w      1.00  71.00   1.00    6.00    --   41.68 -99.00-150.00   70
 21  \w     83.00 178.00   1.00   30.00    --  109.13  45.00  90.00   95
 22  \w    111.00 178.00   1.00   30.00    --  109.13  77.00  90.00   67
 23  \w     81.00 178.00   1.00   30.00    --  109.13  30.00 -60.00   97
 24  \w    111.00 178.00   1.00   30.00    --  109.13  77.00  30.00   67
 25  \w    107.00 178.00   1.00   30.00    --  109.13  45.00-120.00   71
 26  \w    129.00 178.00   1.00   30.00    --  109.13  61.00 -30.00   49
 27  \w    144.00 178.00   1.00   30.00    --  109.13  61.00 -60.00   34
 28  \w    126.00 178.00   1.00   30.00    --  109.13  77.00-180.00   52
 29  \w    129.00 178.00   1.00   30.00    --  109.13  61.00-120.00   49
 30  \w     36.00  81.00   1.00   30.00    --  109.13-125.00 -90.00   45
 31  \w     38.00  69.00   1.00    6.00    --   41.68  77.00   0.00   31
;
_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      -0.0097755000
_diffrn_orient_matrix_UB_12      0.1409510000
_diffrn_orient_matrix_UB_13      -0.0515029000
_diffrn_orient_matrix_UB_21      0.1407785000
_diffrn_orient_matrix_UB_22      0.1257671000
_diffrn_orient_matrix_UB_23      0.0455849000
_diffrn_orient_matrix_UB_31      0.2279319000
_diffrn_orient_matrix_UB_32      -0.0715472000
_diffrn_orient_matrix_UB_33      -0.0212359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9351
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.308
_diffrn_reflns_theta_min         4.130
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.262
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0640P)^2^+0.1570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1435
_reflns_number_total             1859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm012
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242220
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H13 N O2'
_reflns_odcompleteness_completeness 98.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O2-H2
 0.84 with sigma of 0.01
 N1-H1
 0.88 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              38889
_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 2.254
_oxdiff_exptl_absorpt_empirical_full_min 0.210