#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:05:21 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242221.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242221
loop_
_publ_author_name
'Kassin, Victor-Emmanuel H.'
'Morodo, Romain'
'Toupy, Thomas'
'Jacquemin, Isaline'
'Van Hecke, Kristof'
'Robiette, Raphaël'
'Monbaliu, Jean-Christophe M.'
_publ_section_title
;
 A modular, low footprint and scalable flow platform for the expedient
 α-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         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7022(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9356(3)
_cell_length_b                   3.81317(10)
_cell_length_c                   21.6720(5)
_cell_measurement_reflns_used    14698
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.6410
_cell_measurement_theta_min      4.1480
_cell_volume                     1532.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-180.00  100
  2  ω    -74.00  34.00   1.00    1.00    --  -41.80  77.00  90.00  108
  3  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
  4  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -30.00  100
  5  ω    -34.00  74.00   1.00    1.00    --   41.80 -77.00-180.00  108
  6  ω     23.00  98.00   1.00    1.00    --   41.80-125.00  60.00   75
  7  ω      5.00  32.00   1.00    1.00    --   42.00  90.00  98.07   27
  8  ω     11.00  38.00   1.00    1.00    --   46.00  84.00 176.00   27
  9  ω     12.00  40.00   1.00    1.00    --   46.00  83.00 -75.64   28
 10  ω     17.00  45.00   1.00    1.00    --   50.00  80.00-149.23   28
 11  ω     16.00  45.00   1.00    1.00    --   50.00  81.00 112.39   29
 12  ω     16.00  45.00   1.00    1.00    --   50.00  81.00   2.03   29
 13  ω     33.00 142.00   1.00    1.00    --   66.00  77.00  39.37  109
 14  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 169.00  107
 15  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -85.20  108
 16  ω     34.00 142.00   1.00    1.00    --   66.00  76.00 -55.27  108
 17  ω     37.00 146.00   1.00    1.00    --   70.00  77.00-123.20  109
 18  ω     38.00 146.00   1.00    1.00    --   70.00  76.00  68.89  108
 19  ω     37.00 146.00   1.00    1.00    --   70.00  77.00 131.98  109
 20  ω     42.00 150.00   1.00    1.00    --   74.00  76.00-179.27  108
 21  ω     42.00 149.00   1.00    1.00    --   74.00  75.00 -57.94  107
 22  ω     41.00 150.00   1.00    1.00    --   74.00  77.00 -29.52  109
 23  ω     41.00 150.00   1.00    1.00    --   74.00  77.00   0.21  109
 24  ω     41.00 150.00   1.00    1.00    --   74.00  77.00-152.61  109
 25  ω     47.00 152.00   1.00    1.00    --   78.00  71.00  95.87  105
 26  ω     51.00 156.00   1.00    1.00    --   82.00  71.00  73.73  105
 27  ω     54.00 162.00   1.00    1.00    --   86.00  76.00-107.65  108
 28  ω     59.00 164.00   1.00    1.00    --   90.00  71.00 113.00  105
 29  ω     59.00 164.00   1.00    1.00    --   90.00  72.00   1.09  105
 30  ω     60.00 163.00   1.00    1.00    --   90.00  65.00-142.90  103
 31  ω     65.00 166.00   1.00    1.00    --   94.00  61.00 -17.07  101
 32  ω     67.00 172.00   1.00    1.00    --   98.00  70.00 168.73  105
 33  ω     36.00 117.00   1.00    1.00    --  109.13-125.00-120.00   81
 34  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 120.00  101
 35  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  90.00   98
 36  ω     26.00 110.00   1.00    1.00    --  109.13 -94.00 -30.00   84
 37  ω     33.00 142.00   1.00    1.00    --  109.13 -77.00  60.00  109
 38  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  60.00  101
 39  ω     36.00 117.00   1.00    1.00    --  109.13-125.00 -60.00   81
 40  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  30.00  101
 41  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -90.00   98
 42  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-180.00  101
 43  ω     83.00 178.00   1.00    1.00    --  109.13  45.00 -30.00   95
 44  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 -90.00  101
 45  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-150.00  101
 46  ω     77.00 178.00   1.00    1.00    --  109.13  77.00   0.00  101
 47  ω     26.00 110.00   1.00    1.00    --  109.13 -94.00  30.00   84
 48  ω     82.00 178.00   1.00    1.00    --  110.00  55.00-107.29   96
 49  ω     17.00 116.00   1.00    1.00    --   41.80  38.00 120.00   99
 50  ω     16.00 115.00   1.00    1.00    --   41.80  43.00  25.80   99
 51  ω      1.00 122.00   1.00    1.00    --   41.80  19.00   0.00  121
 52  ω      7.00  36.00   1.00    1.00    --   42.00  85.00 -86.03   29
 53  ω     11.00  38.00   1.00    1.00    --   46.00  84.00-131.82   27
 54  ω     11.00  38.00   1.00    1.00    --   46.00  84.00  95.57   27
 55  ω     30.00 138.00   1.00    1.00    --   62.00  76.00  87.47  108
 56  ω     30.00 137.00   1.00    1.00    --   62.00  75.00  -3.45  107
 57  ω     29.00 138.00   1.00    1.00    --   62.00  77.00-162.14  109
 58  ω     35.00 140.00   1.00    1.00    --   66.00  72.00  29.25  105
 59  ω     34.00 141.00   1.00    1.00    --   66.00  75.00 107.96  107
 60  ω     38.00 146.00   1.00    1.00    --   70.00  76.00 -46.99  108
 61  ω     38.00 146.00   1.00    1.00    --   70.00  76.00-159.25  108
 62  ω     38.00 145.00   1.00    1.00    --   70.00  75.00 124.67  107
 63  ω     43.00 147.00   1.00    1.00    --   74.00  69.00 -74.31  104
 64  ω     51.00 150.00   1.00    1.00    --   78.00  52.00  69.38   99
 65  ω     48.00 151.00   1.00    1.00    --   78.00  67.00-141.95  103
 66  ω     52.00 155.00   1.00    1.00    --   82.00  65.00  72.36  103
 67  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-150.00  157
 68  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-180.00  157
 69  ω     80.00 178.00   1.00    1.00    --  109.13  61.00-150.00   98
 70  ω     36.00 117.00   1.00    1.00    --  109.13-125.00 -30.00   81
 71  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  90.00  101
 72  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-120.00  101
 73  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  60.00   98
 74  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -30.00   98
 75  ω     83.00 178.00   1.00    1.00    --  109.13  45.00  30.00   95
 76  ω     36.00 117.00   1.00    1.00    --  109.13-125.00-150.00   81
 77  ω     21.00  94.00   1.00    1.00    --  109.13   0.00   0.00   73
 78  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 150.00   98
 79  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -30.00  157
 80  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -60.00  157
 81  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 120.00   98
 82  ω     21.00 178.00   1.00    1.00    --  109.13   0.00 -90.00  157
 83  ω     21.00 178.00   1.00    1.00    --  109.13   0.00-120.00  157
 84  ω     80.00 178.00   1.00    1.00    --  109.13  61.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214467000
_diffrn_orient_matrix_UB_12      0.2582056000
_diffrn_orient_matrix_UB_13      0.0553363000
_diffrn_orient_matrix_UB_21      0.0792303000
_diffrn_orient_matrix_UB_22      -0.1165705000
_diffrn_orient_matrix_UB_23      0.0079177000
_diffrn_orient_matrix_UB_31      0.0127838000
_diffrn_orient_matrix_UB_32      0.2881895000
_diffrn_orient_matrix_UB_33      -0.0463009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38369
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_min         4.166
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_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/[σ²(Fo²)+(0.0578P)²+1.2741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1386
_reflns_number_total             1577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc04395h2.cif
_cod_data_source_block           jcm003
_cod_depositor_comments
'Adding full bibliography for 7242218--7242224.cif.'
_cod_original_cell_volume        1532.30(6)
_cod_database_code               7242221
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C8 H8 N2 O2'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.94
_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,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.667
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56583(4) 0.0283(3) 0.46114(4) 0.0272(3) Uani 1 1 d . . . . .
H1 H 0.5661 -0.0490 0.4975 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.42177(5) 0.3972(3) 0.27929(4) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.49435(5) 0.1148(3) 0.43139(5) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.55296(6) 0.2971(4) 0.35094(6) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.49430(7) 0.2429(4) 0.37610(6) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.42287(7) 0.3303(4) 0.33458(6) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.35531(7) 0.3236(4) 0.35955(6) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.35172(7) 0.4496(4) 0.41914(6) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.3937 0.5386 0.4462 0.028 Uiso 1 1 calc R . . . .
C5 C 0.28664(7) 0.4443(4) 0.43879(6) 0.0265(3) Uani 1 1 d . . . . .
H5 H 0.2840 0.5311 0.4794 0.032 Uiso 1 1 calc R . . . .
C6 C 0.22506(7) 0.3131(4) 0.39961(7) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.1808 0.3061 0.4138 0.035 Uiso 1 1 calc R . . . .
H2A H 0.5468(9) 0.343(5) 0.3104(9) 0.035 Uiso 1 1 d R . . . .
H2B H 0.5933(9) 0.201(5) 0.3722(8) 0.035 Uiso 1 1 d R . . . .
C7 C 0.22813(7) 0.1920(4) 0.33980(7) 0.0282(3) Uani 1 1 d . . . . .
H7 H 0.1859 0.1040 0.3129 0.034 Uiso 1 1 calc R . . . .
C8 C 0.29297(7) 0.1999(4) 0.31956(6) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.2951 0.1209 0.2784 0.029 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -2 0.0745
7 -1 -13 0.1392
1 -2 1 0.1044
-7 1 12 0.0279
-10 1 -4 0.0565
-12 0 -1 0.0553
11 0 2 0.0180
10 -1 4 0.0339
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 109.33(10) . . ?
N1 C1 N2 125.89(12) . . ?
N1 C1 C2 118.04(11) . . ?
N2 C1 C2 116.04(11) . . ?
O2 C2 C1 117.92(11) . . ?
O2 C2 C3 121.07(11) . . ?
C3 C2 C1 120.98(11) . . ?
C4 C3 C2 122.62(12) . . ?
C4 C3 C8 119.85(12) . . ?
C8 C3 C2 117.46(11) . . ?
C5 C4 C3 119.65(12) . . ?
C4 C5 C6 120.45(12) . . ?
C7 C6 C5 120.12(12) . . ?
C8 C7 C6 119.73(12) . . ?
C7 C8 C3 120.17(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4151(13) . ?
O2 C2 1.2211(16) . ?
N1 C1 1.2937(17) . ?
N2 C1 1.3490(16) . ?
C1 C2 1.5021(17) . ?
C2 C3 1.4870(17) . ?
C3 C4 1.3923(18) . ?
C3 C8 1.3971(18) . ?
C4 C5 1.3831(18) . ?
C5 C6 1.389(2) . ?
C6 C7 1.388(2) . ?
C7 C8 1.3854(18) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0031 1.9998 -2.0010 0.3841 -0.3284 0.6561
7.0002 -1.0003 -12.9952 -0.8272 0.5683 0.4029
1.0028 -1.9998 1.0014 -0.4395 0.3205 -0.6099
-7.0005 1.0002 11.9955 0.7719 -0.5763 -0.3566
-10.0073 0.9994 -3.9986 -0.1778 -0.9410 0.3452
-12.0064 -0.0005 -0.9986 -0.3129 -0.9591 -0.1074
11.0062 0.0005 1.9983 0.3468 0.8878 0.0483
10.0073 -0.9994 3.9986 0.1778 0.9410 -0.3452
