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_7242223
_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         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_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     direct
_audit_creation_date             2019-06-14
_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                 99.123(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0379(3)
_cell_length_b                   10.0440(3)
_cell_length_c                   11.0835(3)
_cell_measurement_reflns_used    4897
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      75.0820
_cell_measurement_theta_min      4.9080
_cell_volume                     993.40(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
_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 0.988
_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    -66.00  32.00   1.00    2.00    --  -41.80  38.00   0.00   98
  2  \w    -66.00  32.00   1.00    2.00    --  -41.80  38.00 -90.00   98
  3  \w     23.00  98.00   1.00    2.00    --   41.80-125.00  90.00   75
  4  \w     14.00 115.00   1.00    2.00    --   41.80  57.00 -90.00  101
  5  \w      1.00  83.00   1.00    2.00    --   41.80 -99.00 -90.00   82
  6  \w    -30.00  70.00   1.00    2.00    --   41.80 -57.00  30.00  100
  7  \w     33.00 137.00   1.00    6.00    --  109.13 -30.00 120.00  104
  8  \w     36.00 117.00   1.00    6.00    --  109.13-125.00 120.00   81
  9  \w     36.00 135.00   1.00    6.00    --  109.13 -45.00-150.00   99
 10  \w     83.00 178.00   1.00    6.00    --  109.13  45.00  60.00   95
 11  \w     94.00 178.00   1.00    6.00    --  109.13 125.00 -90.00   84
 12  \w     36.00 135.00   1.00    6.00    --  109.13 -45.00  30.00   99
 13  \w     33.00 142.00   1.00    6.00    --  109.13 -77.00-120.00  109
 14  \w     33.00 142.00   1.00    6.00    --  109.13 -77.00   0.00  109
 15  \w     37.00 123.00   1.00    6.00    --  109.13-133.00-113.00   86
 16  \w     28.00 162.00   1.00    6.00    --  109.13 -15.00 -60.00  134
 17  \w     14.00 115.00   1.00    2.00    --   41.80  57.00 150.00  101
 18  \w     14.00 115.00   1.00    2.00    --   41.80  57.00-150.00  101
 19  \w     14.00 115.00   1.00    2.00    --   41.80  57.00  30.00  101
 20  \w      9.00 118.00   1.00    2.00    --   41.80  77.00 -60.00  109
 21  \w     77.00 178.00   1.00    6.00    --  109.13  77.00 150.00  101
 22  \w     56.00 178.00   1.00    6.00    --  109.13  15.00 -60.00  122
 23  \w     81.00 178.00   1.00    6.00    --  109.13  30.00   0.00   97
 24  \w     79.00 178.00   1.00    6.00    --  109.13  68.00  77.00   99
 25  \w     56.00 178.00   1.00    6.00    --  109.13  15.00-180.00  122
 26  \w     83.00 178.00   1.00    6.00    --  109.13  45.00 -60.00   95
 27  \w     83.00 178.00   1.00    6.00    --  109.13  45.00  30.00   95
 28  \w     77.00 178.00   1.00    6.00    --  109.13  77.00-180.00  101
 29  \w      1.00  83.00   1.00    2.00    --   41.80 -99.00-180.00   82
 30  \w      9.00 118.00   1.00    2.00    --   41.80  77.00-180.00  109
 31  \w      9.00 118.00   1.00    2.00    --   41.80  77.00  60.00  109
;
_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      0.0823683000
_diffrn_orient_matrix_UB_12      -0.0345238000
_diffrn_orient_matrix_UB_13      -0.1074844000
_diffrn_orient_matrix_UB_21      0.0190360000
_diffrn_orient_matrix_UB_22      0.1494519000
_diffrn_orient_matrix_UB_23      -0.0247110000
_diffrn_orient_matrix_UB_31      0.1504254000
_diffrn_orient_matrix_UB_32      -0.0000449000
_diffrn_orient_matrix_UB_33      0.0875947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.607
_diffrn_reflns_theta_min         4.956
_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  0.857
_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    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0554P)^2^+0.2815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1589
_reflns_number_total             2033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm010
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242223
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H13 N O2'
_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, H9 of C9, H11 of C11, H8 of C8, H10 of C10, H7 of C7,
  All C(H,H,H) groups
 At 1.5 times of:
  H1 of C3
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.01
 N1-H1A
 0.88 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              88775
_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 2.148
_oxdiff_exptl_absorpt_empirical_full_min 0.471