#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:05:21 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/22/7242222.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_7242222
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         '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  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    -66.00  32.00   1.00    1.00    --  -41.80  38.00 -30.00   98
  3  ω      1.00  83.00   1.00    1.00    --   41.80 -99.00 -30.00   82
  4  ω    -34.00  74.00   1.00    1.00    --   41.80 -77.00  60.00  108
  5  ω     36.00 117.00   1.00    4.00    --  109.13-125.00 150.00   81
  6  ω     94.00 178.00   1.00    4.00    --  109.13 125.00  30.00   84
  7  ω     94.00 178.00   1.00    4.00    --  109.13 125.00  90.00   84
  8  ω     98.00 178.00   1.00    4.00    --  109.13  86.00-114.00   80
  9  ω     81.00 178.00   1.00    4.00    --  109.13  30.00 150.00   97
 10  ω     36.00 117.00   1.00    4.00    --  109.13-125.00 -30.00   81
 11  ω     83.00 178.00   1.00    4.00    --  109.13  45.00-150.00   95
 12  ω     37.00 138.00   1.00    4.00    --  109.13 -61.00 120.00  101
 13  ω     36.00 117.00   1.00    4.00    --  109.13-125.00  60.00   81
 14  ω     36.00 135.00   1.00    4.00    --  109.13 -45.00 -30.00   99
 15  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  90.00  100
 16  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00   0.00  100
 17  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -90.00  100
 18  ω    -32.00  66.00   1.00    1.00    --   41.80 -38.00 120.00   98
 19  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 20  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 21  ω     83.00 178.00   1.00    4.00    --  109.13  45.00  60.00   95
 22  ω     83.00 178.00   1.00    4.00    --  109.13  45.00-120.00   95
 23  ω     81.00 178.00   1.00    4.00    --  109.13  30.00   0.00   97
 24  ω     77.00 178.00   1.00    4.00    --  109.13  77.00   0.00  101
 25  ω     80.00 178.00   1.00    4.00    --  109.13  61.00 -60.00   98
 26  ω     83.00 178.00   1.00    4.00    --  109.13  45.00  90.00   95
 27  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00-120.00  109
 28  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00  60.00  109
 29  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -60.00  100
 30  ω     23.00  98.00   1.00    1.00    --   41.80-125.00-180.00   75
 31  ω     80.00 178.00   1.00    4.00    --  109.13  61.00-180.00   98
 32  ω     80.00 158.00   1.00    4.00    --  109.13  61.00-120.00   78
 33  ω     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       'ω 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/[σ²(Fo²)+(0.0568P)²+0.1413P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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 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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 1.03025(8) 0.06878(4) 0.20181(4) 0.02295(14) Uani 1 1 d . . . . .
O1 O 1.1702(2) 0.33049(13) 0.48801(12) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.6095(3) 0.02563(12) 0.38117(12) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.562(5) -0.044(3) 0.408(3) 0.037 Uiso 1 1 d R . . . .
N1 N 0.5771(3) 0.14533(13) 0.48808(14) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.8280(3) 0.16978(16) 0.18759(16) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.6995(3) 0.15527(18) 0.05380(17) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.727786 0.094377 -0.027598 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5293(3) 0.23029(19) 0.03951(17) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.443219 0.222334 -0.051843 0.029 Uiso 1 1 calc R . . . .
C4 C 0.4842(3) 0.31708(18) 0.15836(18) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.365480 0.367213 0.148116 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6132(3) 0.33048(16) 0.29259(17) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.581306 0.389442 0.373638 0.023 Uiso 1 1 calc R . . . .
C6 C 0.7883(3) 0.25819(16) 0.30879(15) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.9453(3) 0.28258(15) 0.45419(15) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.8205(3) 0.25409(16) 0.55910(15) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.7748(3) 0.39048(16) 0.65554(16) 0.0177(3) Uani 1 1 d . . . . .
H9AA H 0.851359 0.472118 0.637798 0.021 Uiso 0.792(7) 1 calc R . P A 1
H9AB H 0.593967 0.379148 0.635943 0.021 Uiso 0.792(7) 1 calc R . P A 1
H9BC H 0.606384 0.396636 0.616124 0.021 Uiso 0.208(7) 1 calc R . P A 2
H9BD H 0.901500 0.476437 0.670651 0.021 Uiso 0.208(7) 1 calc R . P A 2
C12 C 0.9906(3) 0.21188(18) 0.66230(17) 0.0223(4) Uani 1 1 d . . . . .
H12A H 1.168617 0.255022 0.677966 0.027 Uiso 0.792(7) 1 calc R . P A 1
H12B H 0.956058 0.108260 0.626141 0.027 Uiso 0.792(7) 1 calc R . P A 1
H12C H 0.914420 0.113107 0.645772 0.027 Uiso 0.208(7) 1 calc R . P A 2
H12D H 1.154150 0.218726 0.645545 0.027 Uiso 0.208(7) 1 calc R . P A 2
C10A C 0.8946(7) 0.4132(4) 0.8088(3) 0.0290(7) Uani 0.792(7) 1 d . . P A 1
H10A H 1.059238 0.485222 0.850616 0.035 Uiso 0.792(7) 1 calc R . P A 1
H10B H 0.787013 0.444038 0.867222 0.035 Uiso 0.792(7) 1 calc R . P A 1
C11A C 0.9220(7) 0.2704(3) 0.8000(2) 0.0231(6) Uani 0.792(7) 1 d . . P A 1
H11A H 0.764037 0.208392 0.793929 0.028 Uiso 0.792(7) 1 calc R . P A 1
H11B H 1.055590 0.280572 0.883277 0.028 Uiso 0.792(7) 1 calc R . P A 1
C10B C 0.802(3) 0.3657(14) 0.7949(12) 0.0290(7) Uani 0.208(7) 1 d . . P A 2
H10C H 0.836965 0.455323 0.877481 0.035 Uiso 0.208(7) 1 calc R . P A 2
H10D H 0.649540 0.298318 0.787232 0.035 Uiso 0.208(7) 1 calc R . P A 2
C11B C 1.025(3) 0.3047(13) 0.8078(11) 0.0231(6) Uani 0.208(7) 1 d . . P A 2
H11C H 1.185252 0.380366 0.848057 0.028 Uiso 0.208(7) 1 calc R . P A 2
H11D H 1.021917 0.251418 0.868382 0.028 Uiso 0.208(7) 1 calc R . P A 2
H1 H 0.466(4) 0.174(2) 0.437(2) 0.028 Uiso 1 1 d 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'
Cl Cl 0.3639 0.7018 '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
0 -7 1 0.0803
0 7 -1 0.0653
-3 4 -1 0.0209
3 -4 1 0.1024
0 -1 6 0.0378
0 1 -6 0.0148
2 2 -7 0.0689
3 0 1 0.0990
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
O2 N1 C8 107.65(12) . . ?
C2 C1 Cl1 118.48(12) . . ?
C2 C1 C6 121.24(15) . . ?
C6 C1 Cl1 120.21(12) . . ?
C1 C2 C3 119.49(15) . . ?
C2 C3 C4 120.23(14) . . ?
C3 C4 C5 119.91(15) . . ?
C6 C5 C4 120.49(14) . . ?
C1 C6 C7 120.54(14) . . ?
C5 C6 C1 118.62(14) . . ?
C5 C6 C7 120.69(13) . . ?
O1 C7 C6 118.79(14) . . ?
O1 C7 C8 121.10(13) . . ?
C6 C7 C8 120.04(13) . . ?
N1 C8 C7 112.70(12) . . ?
N1 C8 C9 107.12(13) . . ?
N1 C8 C12 109.54(13) . . ?
C7 C8 C9 110.84(12) . . ?
C7 C8 C12 111.33(13) . . ?
C12 C8 C9 104.93(12) . . ?
C8 C9 C10B 100.4(5) . . ?
C10A C9 C8 106.85(14) . . ?
C8 C12 C11A 103.40(15) . . ?
C11B C12 C8 109.8(4) . . ?
C11A C10A C9 104.9(2) . . ?
C10A C11A C12 103.3(2) . . ?
C11B C10B C9 103.7(9) . . ?
C12 C11B C10B 103.6(9) . . ?
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
Cl1 C1 1.7381(16) . ?
O1 C7 1.216(2) . ?
O2 N1 1.4527(16) . ?
N1 C8 1.474(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.398(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.507(2) . ?
C7 C8 1.532(2) . ?
C8 C9 1.5608(19) . ?
C8 C12 1.542(2) . ?
C9 C10A 1.528(3) . ?
C9 C10B 1.565(12) . ?
C12 C11A 1.547(3) . ?
C12 C11B 1.456(11) . ?
C10A C11A 1.521(4) . ?
C10B C11B 1.542(19) . ?
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
0.0032 -6.5028 1.4981 -0.8860 0.1284 -0.4031
-0.0032 6.5028 -1.4981 0.8860 -0.1284 0.4031
-3.0006 4.0021 -0.9970 0.6987 -0.1309 -0.6013
3.0006 -4.0021 0.9970 -0.6987 0.1309 0.6013
-0.0031 -0.5064 6.4995 0.1393 0.9781 0.2920
0.0031 0.5064 -6.4995 -0.1393 -0.9781 -0.2920
2.0016 1.5064 -6.5004 -0.0995 -0.9360 0.3453
2.9975 0.4983 1.4983 -0.0354 0.2754 0.9582
