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_7242219
_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 H16 N O2, Cl'
_chemical_formula_sum            'C12 H16 Cl N O2'
_chemical_formula_weight         241.71
_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             2020-08-28
_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                 94.075(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.09900(10)
_cell_length_b                   7.70410(10)
_cell_length_c                   25.2722(4)
_cell_measurement_reflns_used    12930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5470
_cell_measurement_theta_min      3.2110
_cell_volume                     1184.47(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.948
_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    -15.00  51.00   1.00   15.00    --   10.17 -99.00   0.00   66
  2  \w    -78.00  98.00   1.00   15.00    --   10.17   0.00  30.00  176
  3  \w    -31.00  90.00   1.00   15.00    --   10.17  19.00-150.00  121
  4  \w    -14.00  84.00   1.00   15.00    --   10.17  38.00  90.00   98
  5  \w    -44.00  21.00   1.00   15.00    --  -11.34  77.00 120.00   65
  6  \w    -15.00  30.00   1.00   15.00    --  -11.34 -99.00   0.00   45
  7  \w    -44.00  21.00   1.00   15.00    --  -11.34  77.00  30.00   65
  8  \w    -15.00  30.00   1.00   15.00    --  -11.34 -99.00-120.00   45
  9  \w    -44.00  21.00   1.00   15.00    --  -11.34  77.00-120.00   65
 10  \w    -15.00  17.00   1.00   15.00    --   10.17 -99.00-120.00   32
;
_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      -0.0398580000
_diffrn_orient_matrix_UB_12      -0.0582628000
_diffrn_orient_matrix_UB_13      0.0188106000
_diffrn_orient_matrix_UB_21      0.0683952000
_diffrn_orient_matrix_UB_22      0.0400091000
_diffrn_orient_matrix_UB_23      0.0203663000
_diffrn_orient_matrix_UB_31      -0.0856403000
_diffrn_orient_matrix_UB_32      0.0590038000
_diffrn_orient_matrix_UB_33      0.0047676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.648
_diffrn_reflns_theta_min         2.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.250
_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    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0366P)^2^+0.5606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm017
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_database_code               7242219
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H16 N O2, Cl'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H2A of C2, H5 of C5, H6 of C6, H3 of C3, All C(H,H,H)
  groups, All C(H,H,H,H) groups
 At 1.5 times of:
  H2 of C4
2. Restrained distances
 O2-H2
 0.84 with sigma of 0.02
 N1-H1A = N1-H1B
 0.88 with sigma of 0.02
3. Others
 Sof(H10C)=Sof(H10D)=Sof(H12D)=Sof(H12C)=Sof(C11B)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H12B)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(H11B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10C,H10D), C10(H10A,H10B), C12(H12D,H12C), C12(H12B,H12A),
 C11A(H11A,H11B), C11B(H11C,H11D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              41643
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.801