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_7242218
_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 H11 F3 N O2, Cl'
_chemical_formula_sum            'C10 H11 Cl F3 N O2'
_chemical_formula_weight         269.65
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-27
_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                95.374(3)
_cell_angle_beta                 95.693(4)
_cell_angle_gamma                96.475(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6416(2)
_cell_length_b                   5.8788(2)
_cell_length_c                   18.0049(8)
_cell_measurement_reflns_used    6177
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5310
_cell_measurement_theta_min      4.9380
_cell_volume                     587.08(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.932
_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    2.00    --  -41.68 -38.00  60.00   99
  2  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00 150.00   99
  3  \w     52.00 124.00   1.00    2.00    --   41.68-169.00  -0.00   72
  4  \w      7.00  33.00   1.00    2.00    --   41.68  84.00  32.23   26
  5  \w    -33.00  66.00   1.00    2.00    --   41.68 -38.00  30.00   99
  6  \w     14.00  42.00   1.00    2.00    --   46.00  76.00-119.46   28
  7  \w     16.00  42.00   1.00    2.00    --   50.00  81.00 -76.80   26
  8  \w     16.00  42.00   1.00    2.00    --   50.00  82.00 127.20   26
  9  \w     24.00 127.00   1.00    2.00    --   54.00  66.00 153.14  103
 10  \w     27.00 132.00   1.00    2.00    --   58.00  72.00 -61.61  105
 11  \w     30.00 137.00   1.00    2.00    --   62.00  73.00  73.57  107
 12  \w     31.00 136.00   1.00    2.00    --   62.00  72.00  -5.63  105
 13  \w     32.00 135.00   1.00    2.00    --   62.00  64.00-142.77  103
 14  \w     34.00 141.00   1.00    2.00    --   66.00  73.00  26.19  107
 15  \w     87.00 145.00   1.00    2.00    --   70.00  73.00-117.97   58
 16  \w     39.00 144.00   1.00    2.00    --   70.00  72.00 -36.07  105
 17  \w     42.00 142.00   1.00    2.00    --   70.00  55.00 173.30  100
 18  \w     54.00 154.00   1.00   12.00    --   82.00  55.00  21.42  100
 19  \w     50.00 157.00   1.00   12.00    --   82.00  74.00-162.36  107
 20  \w     63.00 168.00   1.00   12.00    --   94.00  71.00 140.39  105
 21  \w     87.00 167.00   1.00   12.00    --   94.00  69.00-110.46   80
 22  \w    103.00 167.00   1.00   12.00    --   94.00  66.00-154.40   64
 23  \w     23.00  83.00   1.00   12.00    --  106.01 -94.00   0.00   60
 24  \w     33.00  93.00   1.00   12.00    --  106.01-125.00 -60.00   60
 25  \w     77.00 178.00   1.00   12.00    --  106.01  61.00  90.00  101
 26  \w     30.00 100.00   1.00   12.00    --  106.01 -77.00  90.00   70
 27  \w     77.00 178.00   1.00   12.00    --  106.01  61.00 -90.00  101
 28  \w     33.00  93.00   1.00   12.00    --  106.01-125.00 -30.00   60
 29  \w     77.00 178.00   1.00   12.00    --  106.01  61.00 -30.00  101
 30  \w     77.00 178.00   1.00   12.00    --  106.01  61.00   0.00  101
 31  \w     33.00 112.00   1.00   12.00    --  106.01-125.00  90.00   79
 32  \w     77.00 178.00   1.00   12.00    --  106.01  61.00 120.00  101
 33  \w     77.00 178.00   1.00   12.00    --  106.01  61.00  30.00  101
 34  \w     77.00 178.00   1.00   12.00    --  106.01  61.00  60.00  101
 35  \w     77.00 178.00   1.00   12.00    --  106.01  61.00 -60.00  101
 36  \w     77.00 178.00   1.00   12.00    --  106.01  61.00-180.00  101
 37  \w     79.00 178.00   1.00   12.00    --  106.01  52.00-122.81   99
 38  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00-150.00  176
 39  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00 -60.00  176
 40  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00 -90.00  176
 41  \w     27.00  98.00   1.00    2.00    --   41.68-125.00-180.00   71
 42  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00 -30.00  176
 43  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00-120.00  176
 44  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00-180.00  176
 45  \w     61.00 160.00   1.00   12.00    --   86.00  40.00 178.35   99
 46  \w     80.00 178.00   1.00   12.00    --  106.01  45.00 120.00   98
 47  \w     18.00 153.00   1.00   12.00    --  106.01   0.00-180.00  135
 48  \w     77.00 178.00   1.00   12.00    --  106.01  61.00-150.00  101
 49  \w     34.00  84.00   1.00   12.00    --  106.01 -61.00-150.00   50
;
_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      0.0184863000
_diffrn_orient_matrix_UB_12      0.0077966000
_diffrn_orient_matrix_UB_13      -0.0845396000
_diffrn_orient_matrix_UB_21      -0.0350475000
_diffrn_orient_matrix_UB_22      -0.2651110000
_diffrn_orient_matrix_UB_23      -0.0117361000
_diffrn_orient_matrix_UB_31      -0.2736768000
_diffrn_orient_matrix_UB_32      0.0014593000
_diffrn_orient_matrix_UB_33      -0.0139017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17106
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.328
_diffrn_reflns_theta_min         4.965
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.209
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (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    1.525
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0724
_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^)+(0.0378P)^2^+4.2400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1905
_reflns_number_total             2262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm016
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242218
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H11 Cl F3 N O2'
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.541
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9938(10)
 0.0062(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
3. Restrained distances
 O2-H2
 0.84 with sigma of 0.02
 N1-H1A = N1-H1B
 0.88 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              62767
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.484