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_7242222
_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         'C12 H14 Cl N O2'
_chemical_formula_sum            'C12 H14 Cl N O2'
_chemical_formula_weight         239.69
_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     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                110.243(5)
_cell_angle_beta                 102.912(5)
_cell_angle_gamma                100.879(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7548(3)
_cell_length_b                   10.5744(5)
_cell_length_c                   10.5916(6)
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.0080
_cell_measurement_theta_min      4.6240
_cell_volume                     563.94(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -66.00  32.00   1.00    1.00    --  -41.80  38.00 -30.00   98
  3  \w      1.00  83.00   1.00    1.00    --   41.80 -99.00 -30.00   82
  4  \w    -34.00  74.00   1.00    1.00    --   41.80 -77.00  60.00  108
  5  \w     36.00 117.00   1.00    4.00    --  109.13-125.00 150.00   81
  6  \w     94.00 178.00   1.00    4.00    --  109.13 125.00  30.00   84
  7  \w     94.00 178.00   1.00    4.00    --  109.13 125.00  90.00   84
  8  \w     98.00 178.00   1.00    4.00    --  109.13  86.00-114.00   80
  9  \w     81.00 178.00   1.00    4.00    --  109.13  30.00 150.00   97
 10  \w     36.00 117.00   1.00    4.00    --  109.13-125.00 -30.00   81
 11  \w     83.00 178.00   1.00    4.00    --  109.13  45.00-150.00   95
 12  \w     37.00 138.00   1.00    4.00    --  109.13 -61.00 120.00  101
 13  \w     36.00 117.00   1.00    4.00    --  109.13-125.00  60.00   81
 14  \w     36.00 135.00   1.00    4.00    --  109.13 -45.00 -30.00   99
 15  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
 16  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00   0.00  100
 17  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -90.00  100
 18  \w    -32.00  66.00   1.00    1.00    --   41.80 -38.00 120.00   98
 19  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 20  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 21  \w     83.00 178.00   1.00    4.00    --  109.13  45.00  60.00   95
 22  \w     83.00 178.00   1.00    4.00    --  109.13  45.00-120.00   95
 23  \w     81.00 178.00   1.00    4.00    --  109.13  30.00   0.00   97
 24  \w     77.00 178.00   1.00    4.00    --  109.13  77.00   0.00  101
 25  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -60.00   98
 26  \w     83.00 178.00   1.00    4.00    --  109.13  45.00  90.00   95
 27  \w   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00-120.00  109
 28  \w   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00  60.00  109
 29  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -60.00  100
 30  \w     23.00  98.00   1.00    1.00    --   41.80-125.00-180.00   75
 31  \w     80.00 178.00   1.00    4.00    --  109.13  61.00-180.00   98
 32  \w     80.00 158.00   1.00    4.00    --  109.13  61.00-120.00   78
 33  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 -30.00  101
;
_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      -0.0520011000
_diffrn_orient_matrix_UB_12      0.1437265000
_diffrn_orient_matrix_UB_13      0.0325973000
_diffrn_orient_matrix_UB_21      0.0135280000
_diffrn_orient_matrix_UB_22      0.0152090000
_diffrn_orient_matrix_UB_23      0.1516758000
_diffrn_orient_matrix_UB_31      0.2819856000
_diffrn_orient_matrix_UB_32      0.0738384000
_diffrn_orient_matrix_UB_33      0.0508150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10603
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.488
_diffrn_reflns_theta_min         4.658
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.751
_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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.1413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2051
_reflns_number_total             2285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm009
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242222
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H14 Cl 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) groups, All C(H,H) groups, All C(H,H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
3. Others
 Sof(H9BC)=Sof(H9BD)=Sof(H12C)=Sof(H12D)=Sof(C10B)=Sof(H10C)=Sof(H10D)=
 Sof(C11B)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(H12A)=Sof(H12B)=Sof(C10A)=Sof(H10A)=Sof(H10B)=
 Sof(C11A)=Sof(H11A)=Sof(H11B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C12(H12A,H12B), C12(H12C,H12D), C10A(H10A,H10B),
  C11A(H11A,H11B), C10B(H10C,H10D), C11B(H11C,H11D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              35729
_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 3.218
_oxdiff_exptl_absorpt_empirical_full_min 0.449