# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jb190920_1_1
_database_code_depnum_ccdc_archive 'CCDC 2169258'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H25 Cl N2 O'
_chemical_formula_sum            'C18 H25 Cl N2 O'
_chemical_formula_weight         320.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H25ClN2O
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.01210(10)
_cell_length_b                   24.36780(10)
_cell_length_c                   11.42100(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.6950(10)
_cell_angle_gamma                90
_cell_volume                     1667.58(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    32882
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.5890
_cell_measurement_theta_min      3.6180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.045
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.1171
2 -1 0 0.0912
-2 1 0 0.1124
0 14 4 0.0186
0 -14 -4 0.0598
4 3 1 0.0899
-4 -3 -1 0.1234
4 -2 -1 0.0885
-1 6 7 0.0739
-2 6 6 0.0708
-2 9 -4 0.1262
-1 -10 5 0.0949
-1 -15 2 0.0663
-3 8 0 0.1038
0 -16 0 0.0553
0 -8 -6 0.0607
-1 3 -7 0.1056
0 15 -2 0.0870

_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.088
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
-0.0001 1.0012 -0.9996 0.0589 -0.1369 -0.0095
2.0001 -0.9985 0.0005 -0.0234 0.0249 0.5169
-2.0001 0.9985 -0.0005 0.0234 -0.0249 -0.5169
-0.4291 13.6572 3.7051 0.8676 0.4717 -0.1576
-0.0299 -13.6742 -3.7089 -0.8777 -0.4775 0.0401
3.7486 3.1581 0.8499 0.2767 0.1524 0.9488
-3.7330 -3.3499 -0.9020 -0.2887 -0.1589 -0.9441
3.8837 -1.5585 -0.7008 -0.0243 -0.0473 0.9986
-0.9611 6.4793 6.6395 0.4169 0.8751 -0.2456
-1.7564 6.2418 6.1923 0.3844 0.8059 -0.4503
-2.2074 9.0067 -4.0644 0.5070 -0.5910 -0.6275
-1.1182 -10.0862 5.4558 -0.6350 0.7427 -0.2124
-0.5185 -14.9333 2.3078 -0.9417 0.3326 -0.0505
-3.4149 7.6485 0.3258 0.4158 -0.0088 -0.9094
-0.1343 -15.8076 -0.0102 -0.9988 0.0252 0.0410
-0.0630 -7.8368 -6.4070 -0.5217 -0.8531 -0.0090
-0.5206 3.4797 -7.0582 0.1796 -0.9665 -0.1833
-0.1274 15.0504 -2.2390 0.9366 -0.3310 -0.1151

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45091
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.091
_diffrn_reflns_theta_min         3.628
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -39.00   0.50    0.10    --  -48.87 -38.00   0.00   94
  2  ω    -64.00 -33.00   0.50    0.10    --  -48.87 -57.00   0.00   62
  3  ω    -91.00 -57.00   0.50    0.10    --  -48.87 -77.00 -60.00   68
  4  ω    -50.00 -25.00   0.50    0.10    --  -48.87 -77.00 -60.00   50
  5  ω    -62.00  22.00   0.50    0.10    --  -48.87  57.00  90.00  168
  6  ω    -99.00 -37.00   0.50    0.10    --  -48.87 -38.00  60.00  124
  7  ω    -87.00 -33.00   0.50    0.10    --  -48.87 -57.00 150.00  108
  8  ω     25.00  60.00   0.50    0.10    --   48.87  77.00-150.00   70
  9  ω     83.00 108.00   0.50    0.10    --   48.87  77.00-150.00   50
 10  ω     33.00  63.00   0.50    0.10    --   48.87  57.00-150.00   60
 11  ω     39.00  85.00   0.50    0.10    --   48.87  38.00-180.00   92
 12  ω     25.00  56.00   0.50    0.10    --   48.87  77.00-180.00   62
 13  ω     25.00  51.00   0.50    0.10    --   48.87  77.00  90.00   52
 14  ω     90.00 116.00   0.50    0.10    --   48.87  19.00 150.00   52
 15  ω     25.00  55.00   0.50    0.10    --   48.87  77.00 -30.00   60
 16  ω     63.00 119.00   0.50    0.10    --   48.87 178.00 -90.00  112
 17  ω     70.00 118.00   0.50    0.10    --   48.87-178.00 120.00   96
 18  ω     38.00  88.00   0.50    0.10    --   48.87  19.00 150.00  100
 19  ω     34.00  59.00   0.50    0.10    --   58.00  79.00 -50.07   50
 20  ω     33.00  64.00   0.50    0.10    --   58.00  80.00   4.48   62
 21  ω     33.00  59.00   0.50    0.10    --   58.00  80.00 -85.64   52
 22  ω     98.00 123.00   0.50    0.10    --   62.00  79.00-144.07   50
 23  ω     38.00  63.00   0.50    0.10    --   62.00  78.00 108.53   50
 24  ω     38.00  64.00   0.50    0.10    --   62.00  79.00-144.07   52
 25  ω    -75.00 -46.00   0.50    0.14    --  -70.00 -77.00  48.48   58
 26  ω    -85.00 -19.00   0.50    0.14    --  -70.00 125.00-120.00  132
 27  ω     45.00  75.00   0.50    0.10    --   70.00  80.00-152.93   60
 28  ω    110.00 136.00   0.50    0.10    --   70.00  80.00-152.93   52
 29  ω    -83.00 -48.00   0.50    0.14    --  -70.00 -77.00 -60.00   70
 30  ω     91.00 117.00   0.50    0.10    --   70.00  80.00 162.99   52
 31  ω    -72.00 -47.00   0.50    0.14    --  -70.00 -76.00-137.39   50
 32  ω     45.00  70.00   0.50    0.10    --   70.00  80.00 162.99   50
 33  ω    -99.00 -46.00   0.50    0.14    --  -70.00 -78.00  98.50  106
 34  ω    -73.00 -46.00   0.50    0.14    --  -70.00 -78.00-170.79   54
 35  ω    -72.00 -46.00   0.50    0.14    --  -70.00 -79.00 142.71   52
 36  ω     48.00  79.00   0.50    0.10    --   70.00  76.00  35.06   62
 37  ω     48.00  77.00   0.50    0.10    --   70.00  73.00  18.83   58
 38  ω    -73.00 -47.00   0.50    0.14    --  -70.00 -75.00-117.79   52
 39  ω    -74.00 -46.00   0.50    0.14    --  -70.00 -77.00 -30.00   56
 40  ω   -135.00-108.00   0.50    0.14    --  -70.00 -78.00  98.50   54
 41  ω    -73.00 -46.00   0.50    0.14    --  -70.00 -77.00  31.90   54
 42  ω    -71.00 -46.00   0.50    0.14    --  -70.00 -78.00  65.71   50
 43  ω   -135.00 -98.00   0.50    0.14    --  -70.00 -77.00  31.90   74
 44  ω    -81.00 -46.00   0.50    0.14    --  -70.00 -78.00 118.56   70
 45  ω     54.00  91.00   0.50    0.10    --   74.00  72.00 142.31   74
 46  ω     89.00 131.00   0.50    0.10    --   74.00  75.00 -85.10   84
 47  ω     53.00  85.00   0.50    0.10    --   74.00  75.00 -85.10   64
 48  ω    115.00 140.00   0.50    0.10    --   74.00  72.00 142.31   50
 49  ω    118.00 159.00   0.50    0.14    --   90.00  51.00 118.61   82
 50  ω     76.00 105.00   0.50    0.14    --   90.00  51.00 118.61   58
 51  ω    128.00 167.00   0.50    0.14    --   94.00  53.00  28.51   78
 52  ω     81.00 112.00   0.50    0.14    --   94.00  53.00  28.51   62
 53  ω     39.00 113.00   0.50    0.14    --  110.00-125.00-150.00  148
 54  ω     90.00 116.00   0.50    0.14    --  110.00 -77.00 -30.00   52
 55  ω     47.00  80.00   0.50    0.14    --  110.00 -77.00 -30.00   66
 56  ω     86.00 113.00   0.50    0.14    --  110.00  77.00 -60.00   54
 57  ω     96.00 178.00   0.50    0.14    --  110.00  57.00   0.00  164
 58  ω    116.00 155.00   0.50    0.14    --  110.00  38.00-120.00   78
 59  ω     41.00  92.00   0.50    0.14    --  110.00 -99.00 -90.00  102
 60  ω    101.00 150.00   0.50    0.14    --  110.00  38.00  90.00   98
 61  ω     96.00 132.00   0.50    0.14    --  110.00  57.00-150.00   72
 62  ω     58.00 110.00   0.50    0.14    --  110.00-113.00  63.67  104
 63  ω    139.00 168.00   0.50    0.14    --  110.00  77.00 120.00   58
 64  ω     86.00 126.00   0.50    0.14    --  110.00  77.00 120.00   80
 65  ω    147.00 173.00   0.50    0.14    --  110.00  77.00  30.00   52
 66  ω     87.00 112.00   0.50    0.14    --  110.00  77.00  30.00   50
 67  ω     99.00 127.00   0.50    0.14    --  110.00  38.00-180.00   56
 68  ω     50.00  76.00   0.50    0.14    --  110.00-125.00-120.00   52
 69  ω     81.00 106.00   0.50    0.14    --  110.00 -99.00 -30.00   50
 70  ω     40.00  75.00   0.50    0.14    --  110.00 -99.00 -30.00   70
 71  ω     88.00 113.00   0.50    0.14    --  110.00-125.00 -90.00   50
 72  ω     57.00  82.00   0.50    0.14    --  110.00-125.00 -90.00   50
 73  ω     88.00 114.00   0.50    0.14    --  110.00  77.00  90.00   52
 74  ω     96.00 153.00   0.50    0.14    --  110.00  57.00 -30.00  114
 75  ω     86.00 176.00   0.50    0.14    --  110.00  77.00-150.00  180
 76  ω    123.00 176.00   0.50    0.14    --  110.00  77.00 150.00  106
 77  ω     86.00 112.00   0.50    0.14    --  110.00  77.00 150.00   52
 78  ω     61.00 112.00   0.50    0.14    --  110.00-125.00 150.00  102
 79  ω    142.00 170.00   0.50    0.14    --  110.00  77.00 -30.00   56
 80  ω     86.00 112.00   0.50    0.14    --  110.00  77.00 -30.00   52
 81  ω     90.00 176.00   0.50    0.14    --  110.00  77.00-120.00  172
 82  ω     96.00 122.00   0.50    0.14    --  110.00  57.00 120.00   52
 83  ω     88.00 113.00   0.50    0.14    --  110.00-125.00   0.00   50
 84  ω    130.00 168.00   0.50    0.14    --  110.00  77.00  90.00   76
 85  ω     99.00 125.00   0.50    0.14    --  110.00  38.00-150.00   52
 86  ω     98.00 158.00   0.50    0.14    --  110.00  57.00 -60.00  120
 87  ω    131.00 175.00   0.50    0.14    --  110.00  77.00 -90.00   88
 88  ω     98.00 128.00   0.50    0.14    --  110.00  38.00 -60.00   60
 89  ω     86.00 112.00   0.50    0.14    --  110.00  77.00 -90.00   52
 90  ω     88.00 113.00   0.50    0.14    --  110.00-125.00-120.00   50
 91  ω     96.00 125.00   0.50    0.14    --  110.00  57.00  30.00   58
 92  ω     86.00 167.00   0.50    0.14    --  110.00  77.00-180.00  162
 93  ω    149.00 178.00   0.50    0.14    --  110.00  57.00  60.00   58
 94  ω    101.00 141.00   0.50    0.14    --  110.00  57.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197729000
_diffrn_orient_matrix_UB_12      0.0630168000
_diffrn_orient_matrix_UB_13      0.0041581000
_diffrn_orient_matrix_UB_21      0.0115053000
_diffrn_orient_matrix_UB_22      -0.0017783000
_diffrn_orient_matrix_UB_23      0.1352072000
_diffrn_orient_matrix_UB_31      0.2560603000
_diffrn_orient_matrix_UB_32      -0.0047746000
_diffrn_orient_matrix_UB_33      0.0047302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3450
_reflns_number_total             3611
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.074
_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)+(0.0399P)²+0.5885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.93 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.58597(5) 0.68675(2) 0.21831(2) 0.02746(9) Uani 1 1 d . . . . .
O1 O 0.33478(12) 0.63097(3) 0.55957(6) 0.01914(17) Uani 1 1 d . . . . .
N1 N 0.79890(15) 0.61516(4) 0.57203(8) 0.01727(19) Uani 1 1 d D . . . .
H1 H 0.943(2) 0.6259(6) 0.5718(12) 0.021 Uiso 1 1 d D U . . .
N2 N 0.22704(16) 0.66214(4) 0.96239(8) 0.0202(2) Uani 1 1 d D . . . .
H2 H 0.255(2) 0.6497(6) 1.0367(11) 0.024 Uiso 1 1 d D U . . .
C1 C 0.75454(19) 0.62874(5) 0.24404(10) 0.0209(2) Uani 1 1 d . . . . .
C2 C 0.8519(2) 0.60598(5) 0.14884(10) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.828307 0.622083 0.073085 0.031 Uiso 1 1 calc R U . . .
C3 C 0.9834(2) 0.55959(5) 0.16589(11) 0.0270(3) Uani 1 1 d . . . . .
H3 H 1.051028 0.543752 0.101587 0.032 Uiso 1 1 calc R U . . .
C4 C 1.01666(19) 0.53618(5) 0.27663(10) 0.0243(2) Uani 1 1 d . . . . .
H4 H 1.105366 0.504063 0.288083 0.029 Uiso 1 1 calc R U . . .
C5 C 0.91959(18) 0.55991(4) 0.37094(10) 0.0203(2) Uani 1 1 d . . . . .
H5 H 0.944131 0.543742 0.446579 0.024 Uiso 1 1 calc R U . . .
C6 C 0.78736(17) 0.60678(4) 0.35716(9) 0.0176(2) Uani 1 1 d . . . . .
C7 C 0.67989(17) 0.63139(4) 0.46025(9) 0.0169(2) Uani 1 1 d . . . . .
H7 H 0.679011 0.672311 0.453501 0.020 Uiso 1 1 calc R U . . .
C8 C 0.44033(18) 0.61037(5) 0.46086(9) 0.0193(2) Uani 1 1 d . . . . .
H8A H 0.353758 0.621898 0.387516 0.023 Uiso 1 1 calc R U . . .
H8B H 0.441357 0.569763 0.463273 0.023 Uiso 1 1 calc R U . . .
C9 C 0.45443(17) 0.61883(4) 0.67225(9) 0.0167(2) Uani 1 1 d . . . . .
C10 C 0.69235(17) 0.64072(4) 0.66940(9) 0.0176(2) Uani 1 1 d . . . . .
H10A H 0.688849 0.681063 0.659100 0.021 Uiso 1 1 calc R U . . .
H10B H 0.779327 0.632337 0.744637 0.021 Uiso 1 1 calc R U . . .
C11 C 0.32306(17) 0.65012(4) 0.75980(9) 0.0176(2) Uani 1 1 d . . . . .
H11A H 0.345955 0.689937 0.748498 0.021 Uiso 1 1 calc R U . . .
H11B H 0.162172 0.642454 0.741820 0.021 Uiso 1 1 calc R U . . .
C12 C 0.38612(18) 0.63608(4) 0.88858(9) 0.0186(2) Uani 1 1 d . . . . .
H12 H 0.540059 0.649851 0.911956 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3779(2) 0.57423(5) 0.90795(10) 0.0238(2) Uani 1 1 d . . . . .
H13A H 0.221255 0.561549 0.895601 0.029 Uiso 1 1 calc R U . . .
H13B H 0.432399 0.565831 0.990135 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5196(2) 0.54326(5) 0.82469(10) 0.0256(3) Uani 1 1 d . . . . .
H14A H 0.504166 0.503280 0.837131 0.031 Uiso 1 1 calc R U . . .
H14B H 0.678623 0.553104 0.842219 0.031 Uiso 1 1 calc R U . . .
C15 C 0.44749(19) 0.55719(5) 0.69665(10) 0.0216(2) Uani 1 1 d . . . . .
H15A H 0.546943 0.538064 0.645028 0.026 Uiso 1 1 calc R U . . .
H15B H 0.293774 0.543576 0.677150 0.026 Uiso 1 1 calc R U . . .
C16 C 0.23635(19) 0.72120(5) 0.96575(10) 0.0218(2) Uani 1 1 d . . . . .
H16 H 0.387655 0.738138 0.979940 0.026 Uiso 1 1 calc R U . . .
C17 C 0.0670(2) 0.75260(5) 0.88884(11) 0.0280(3) Uani 1 1 d . . . . .
H17A H -0.041730 0.731375 0.837152 0.034 Uiso 1 1 calc R U . . .
H17B H 0.113893 0.787914 0.855754 0.034 Uiso 1 1 calc R U . . .
C18 C 0.0483(2) 0.74964(5) 1.01931(11) 0.0289(3) Uani 1 1 d . . . . .
H18A H 0.083786 0.783135 1.066235 0.035 Uiso 1 1 calc R U . . .
H18B H -0.071831 0.726597 1.047634 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.7501(12) . ?
O1 C8 1.4291(12) . ?
O1 C9 1.4524(12) . ?
N1 H1 0.906(12) . ?
N1 C7 1.4658(13) . ?
N1 C10 1.4669(13) . ?
N2 H2 0.904(12) . ?
N2 C12 1.4698(13) . ?
N2 C16 1.4407(14) . ?
C1 C2 1.3915(16) . ?
C1 C6 1.3974(15) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3842(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3870(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3922(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3931(16) . ?
C6 C7 1.5126(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5292(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5294(14) . ?
C9 C11 1.5278(14) . ?
C9 C15 1.5289(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5273(14) . ?
C12 H12 1.0000 . ?
C12 C13 1.5247(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5273(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5290(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
C16 C17 1.4992(16) . ?
C16 C18 1.4985(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5052(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C8 O1 C9 114.06(8) . . ?
C7 N1 H1 108.6(9) . . ?
C7 N1 C10 109.47(8) . . ?
C10 N1 H1 110.9(9) . . ?
C12 N2 H2 108.4(9) . . ?
C16 N2 H2 107.9(9) . . ?
C16 N2 C12 114.90(9) . . ?
C2 C1 Cl1 117.74(9) . . ?
C2 C1 C6 122.22(11) . . ?
C6 C1 Cl1 120.04(9) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 C1 119.18(11) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.15(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.76(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.65(11) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 122.06(10) . . ?
C5 C6 C1 117.03(10) . . ?
C5 C6 C7 120.88(10) . . ?
N1 C7 C6 111.21(9) . . ?
N1 C7 H7 109.6 . . ?
N1 C7 C8 107.36(8) . . ?
C6 C7 H7 109.6 . . ?
C6 C7 C8 109.47(8) . . ?
C8 C7 H7 109.6 . . ?
O1 C8 C7 111.42(8) . . ?
O1 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O1 C9 C10 107.84(8) . . ?
O1 C9 C11 103.49(8) . . ?
O1 C9 C15 110.04(9) . . ?
C11 C9 C10 111.99(9) . . ?
C11 C9 C15 110.34(9) . . ?
C15 C9 C10 112.71(9) . . ?
N1 C10 C9 109.59(8) . . ?
N1 C10 H10A 109.8 . . ?
N1 C10 H10B 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C9 C11 H11A 108.6 . . ?
C9 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C9 114.69(9) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
N2 C12 C11 109.49(9) . . ?
N2 C12 H12 109.5 . . ?
N2 C12 C13 108.26(9) . . ?
C11 C12 H12 109.5 . . ?
C13 C12 C11 110.65(9) . . ?
C13 C12 H12 109.5 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.82(9) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.90(10) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C9 C15 C14 112.50(9) . . ?
C9 C15 H15A 109.1 . . ?
C9 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
N2 C16 H16 116.7 . . ?
N2 C16 C17 118.12(10) . . ?
N2 C16 C18 116.35(10) . . ?
C17 C16 H16 116.7 . . ?
C18 C16 H16 116.7 . . ?
C18 C16 C17 60.28(8) . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
C16 C17 C18 59.84(8) . . ?
H17A C17 H17B 114.9 . . ?
C18 C17 H17A 117.8 . . ?
C18 C17 H17B 117.8 . . ?
C16 C18 C17 59.88(8) . . ?
C16 C18 H18A 117.8 . . ?
C16 C18 H18B 117.8 . . ?
C17 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
H18A C18 H18B 114.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.03(9) . . . . ?
Cl1 C1 C6 C5 178.67(8) . . . . ?
Cl1 C1 C6 C7 0.37(15) . . . . ?
O1 C9 C10 N1 -58.20(11) . . . . ?
O1 C9 C11 C12 169.01(8) . . . . ?
O1 C9 C15 C14 -166.12(9) . . . . ?
N1 C7 C8 O1 56.95(11) . . . . ?
N2 C12 C13 C14 173.82(9) . . . . ?
N2 C16 C17 C18 105.93(12) . . . . ?
N2 C16 C18 C17 -108.84(11) . . . . ?
C1 C2 C3 C4 0.18(18) . . . . ?
C1 C6 C7 N1 -159.17(10) . . . . ?
C1 C6 C7 C8 82.37(12) . . . . ?
C2 C1 C6 C5 -1.23(16) . . . . ?
C2 C1 C6 C7 -179.53(10) . . . . ?
C2 C3 C4 C5 -0.82(18) . . . . ?
C3 C4 C5 C6 0.43(17) . . . . ?
C4 C5 C6 C1 0.57(16) . . . . ?
C4 C5 C6 C7 178.89(10) . . . . ?
C5 C6 C7 N1 22.59(13) . . . . ?
C5 C6 C7 C8 -95.87(12) . . . . ?
C6 C1 C2 C3 0.87(18) . . . . ?
C6 C7 C8 O1 177.78(8) . . . . ?
C7 N1 C10 C9 63.97(11) . . . . ?
C8 O1 C9 C10 55.23(11) . . . . ?
C8 O1 C9 C11 174.03(8) . . . . ?
C8 O1 C9 C15 -68.07(11) . . . . ?
C9 O1 C8 C7 -56.03(12) . . . . ?
C9 C11 C12 N2 -171.47(9) . . . . ?
C9 C11 C12 C13 -52.23(12) . . . . ?
C10 N1 C7 C6 178.87(8) . . . . ?
C10 N1 C7 C8 -61.41(11) . . . . ?
C10 C9 C11 C12 -75.10(11) . . . . ?
C10 C9 C15 C14 73.47(12) . . . . ?
C11 C9 C10 N1 -171.42(8) . . . . ?
C11 C9 C15 C14 -52.54(12) . . . . ?
C11 C12 C13 C14 53.83(13) . . . . ?
C12 N2 C16 C17 99.25(12) . . . . ?
C12 N2 C16 C18 168.00(10) . . . . ?
C12 C13 C14 C15 -56.34(13) . . . . ?
C13 C14 C15 C9 55.93(13) . . . . ?
C15 C9 C10 N1 63.46(11) . . . . ?
C15 C9 C11 C12 51.32(12) . . . . ?
C16 N2 C12 C11 -67.11(12) . . . . ?
C16 N2 C12 C13 172.18(9) . . . . ?

_olex2_submission_original_sample_id jb190920_1_1
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.745
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jb180920_1_1
_database_code_depnum_ccdc_archive 'CCDC 2169554'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 F3 N O2, H2 O'
_chemical_formula_sum            'C13 H14 F3 N O3'
_chemical_formula_weight         289.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H12F3NO2
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'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.36257(3)
_cell_length_b                   8.48172(5)
_cell_length_c                   27.61854(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.197(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25134
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.7950
_cell_measurement_theta_min      5.4480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0359
-3 2 -4 0.0986
-3 2 2 0.0991
-2 3 -11 0.0832
-2 4 5 0.0841
1 -3 13 0.0887
0 3 -15 0.0471
-1 5 -5 0.0497
0 0 -18 0.0598
0 5 7 0.0401
0 4 -11 0.0434
1 5 4 0.0679
1 4 -10 0.0675
-1 -4 -11 0.0776
-2 -4 -8 0.0981
2 3 11 0.1061
0 3 15 0.0614
3 1 7 0.1174
3 0 -6 0.0877
0 1 17 0.0701
0 -1 -17 0.0636
-3 0 1 0.1105
-2 4 -5 0.0847

_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.084
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
-0.0002 -1.0013 1.0042 -0.0065 0.1900 0.0081
-3.2134 1.7475 -3.8824 0.9409 -0.3324 -0.0653
-3.1930 2.1301 1.6738 0.9129 -0.3219 0.2509
-1.8862 3.1772 -10.9529 0.5934 -0.6948 -0.4064
-2.0088 4.2436 4.8413 0.5656 -0.6595 0.4951
1.2115 -3.3195 12.8688 -0.4084 0.7528 0.5163
-0.2536 3.1896 -14.5530 0.1406 -0.7622 -0.6318
-0.5157 5.1796 -5.4669 0.1828 -0.9821 -0.0462
0.1137 -0.1064 -17.9150 0.0415 -0.2336 -0.9714
0.0147 5.1226 6.5759 -0.0192 -0.8079 0.5890
0.2743 4.4331 -10.5358 -0.0243 -0.9292 -0.3689
1.0464 5.1303 3.6537 -0.3026 -0.8596 0.4117
1.2656 4.1958 -9.6032 -0.3127 -0.8834 -0.3492
-0.6446 -4.3433 -10.5094 0.2178 0.6215 -0.7525
-1.6418 -4.2150 -7.8483 0.4928 0.6454 -0.5837
2.1416 2.7828 10.8482 -0.6518 -0.3562 0.6695
0.0779 3.0604 14.8999 -0.0768 -0.3294 0.9411
3.1620 0.8223 7.0009 -0.9329 -0.0749 0.3522
3.2519 -0.2670 -6.3304 -0.9060 -0.0713 -0.4172
0.0202 1.4257 17.3170 -0.0742 -0.0078 0.9972
0.0069 -1.4237 -17.3190 0.0664 0.0072 -0.9978
-3.4672 -0.1474 1.4946 0.9868 0.0783 0.1421
-2.1644 4.0492 -4.8248 0.6498 -0.7595 -0.0310

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            29963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.089
_diffrn_reflns_theta_min         3.200
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  51.00   0.50    0.10    --   48.87  77.00 -30.00   52
  2  ω     29.00  66.00   0.50    0.10    --   50.00  77.00 -92.58   74
  3  ω     25.00  51.00   0.50    0.10    --   48.87  77.00-180.00   52
  4  ω     37.00  64.00   0.50    0.10    --   48.87  57.00-150.00   54
  5  ω     37.00  92.00   0.50    0.10    --   48.87  38.00-180.00  110
  6  ω     76.00 102.00   0.50    0.10    --   48.87  57.00-150.00   52
  7  ω     57.00  84.00   0.50    0.10    --   48.87  38.00  60.00   54
  8  ω     29.00  67.00   0.50    0.10    --   54.00  80.00  32.65   76
  9  ω     49.00  75.00   0.50    0.10    --   74.00  80.00 -17.48   52
 10  ω     49.00 113.00   0.50    0.10    --   74.00  80.00  -3.61  128
 11  ω     39.00  73.00   0.50    0.10    --   62.00  79.00  76.13   68
 12  ω     29.00  56.00   0.50    0.10    --   54.00  80.00 147.84   54
 13  ω     45.00  75.00   0.50    0.10    --   70.00  80.00 157.05   60
 14  ω     34.00  59.00   0.50    0.10    --   54.00  79.00  79.49   50
 15  ω     46.00  71.00   0.50    0.10    --   70.00  78.00 -52.15   50
 16  ω    114.00 144.00   0.50    0.10    --   78.00  79.00-136.49   60
 17  ω     86.00 133.00   0.50    0.10    --  110.00  77.00 -60.00   94
 18  ω     52.00  78.00   0.50    0.10    --   74.00  77.00 -32.93   52
 19  ω     34.00  62.00   0.50    0.10    --   58.00  78.00-165.86   56
 20  ω     50.00  75.00   0.50    0.10    --   74.00  79.00-127.61   50
 21  ω     54.00 102.00   0.50    0.10    --   78.00  79.00-136.49   96
 22  ω     87.00 124.00   0.50    0.10    --  110.00  77.00-150.00   74
 23  ω    132.00 171.00   0.50    0.10    --  110.00  77.00-150.00   78
 24  ω     87.00 175.00   0.50    0.10    --  110.00  77.00 -30.00  176
 25  ω     89.00 114.00   0.50    0.10    --  110.00  77.00-120.00   50
 26  ω    131.00 175.00   0.50    0.10    --  110.00  77.00-120.00   88
 27  ω    145.00 175.00   0.50    0.10    --  110.00  77.00 -60.00   60
 28  ω    123.00 161.00   0.50    0.10    --  110.00  77.00  30.00   76
 29  ω     87.00 112.00   0.50    0.10    --  110.00  77.00  30.00   50
 30  ω     87.00 155.00   0.50    0.10    --  110.00  77.00  60.00  136
 31  ω    137.00 173.00   0.50    0.10    --  110.00  77.00 120.00   72
 32  ω     86.00 176.00   0.50    0.10    --  110.00  77.00 150.00  180
 33  ω     87.00 123.00   0.50    0.10    --  110.00  77.00 120.00   72
 34  ω     97.00 131.00   0.50    0.10    --   74.00  75.00 122.18   68
 35  ω     51.00  91.00   0.50    0.10    --   74.00  75.00 122.18   80
 36  ω     86.00 166.00   0.50    0.10    --  110.00  77.00  90.00  160
 37  ω     89.00 176.00   0.50    0.10    --  110.00  77.00   0.00  174
 38  ω     59.00  86.00   0.50    0.10    --   82.00  75.00 -64.67   54
 39  ω     61.00  86.00   0.50    0.10    --   82.00  70.00 -94.01   50
 40  ω     79.00 112.00   0.50    0.10    --   90.00  71.00 -67.80   66
 41  ω     88.00 174.00   0.50    0.10    --  110.00  77.00-180.00  172
 42  ω    134.00 178.00   0.50    0.10    --  110.00  57.00 -90.00   88
 43  ω    101.00 126.00   0.50    0.10    --  110.00  57.00 -90.00   50
 44  ω    119.00 146.00   0.50    0.10    --   82.00  75.00 -64.67   54
 45  ω     98.00 126.00   0.50    0.10    --  110.00  38.00-180.00   56
 46  ω     97.00 134.00   0.50    0.10    --  110.00  57.00  60.00   74
 47  ω     98.00 123.00   0.50    0.10    --  110.00  38.00  60.00   50
 48  ω    111.00 137.00   0.50    0.10    --   78.00  57.00  37.96   52
 49  ω     65.00 110.00   0.50    0.10    --   78.00  57.00  37.96   90
 50  ω    -78.00 -49.00   0.50    0.10    --  -70.00 -70.00  48.79   58
 51  ω    -70.00 -45.00   0.50    0.10    --  -70.00 -79.00   9.64   50
 52  ω    -71.00 -46.00   0.50    0.10    --  -70.00 -77.00  30.00   50
 53  ω    -64.00 -37.00   0.50    0.10    --  -62.00 -79.00 -57.17   54
 54  ω    -63.00 -37.00   0.50    0.10    --  -62.00 -79.00-134.54   52
 55  ω    -83.00 -50.00   0.50    0.10    --  -70.00 -72.00-175.40   66
 56  ω    -72.00 -47.00   0.50    0.10    --  -70.00 -76.00-104.48   50
 57  ω   -127.00 -82.00   0.50    0.10    --  -62.00 -79.00 -57.17   90
 58  ω    -90.00 -47.00   0.50    0.10    --  -70.00 -76.00 165.71   86
 59  ω    -81.00 -49.00   0.50    0.10    --  -70.00 -72.00  88.94   64
 60  ω    -67.00 -35.00   0.50    0.10    --  -48.87 -38.00 -60.00   64
 61  ω    -64.00 -33.00   0.50    0.10    --  -48.87 -57.00  90.00   62
 62  ω    -77.00 -34.00   0.50    0.10    --  -48.87 -57.00 150.00   86
 63  ω    -58.00 -33.00   0.50    0.10    --  -48.87 -57.00-180.00   50
 64  ω   -109.00 -82.00   0.50    0.10    --  -48.87 -57.00-180.00   54
 65  ω    -65.00 -33.00   0.50    0.10    --  -48.87 -57.00   0.00   64
 66  ω    -93.00  -4.00   0.50    0.10    --  -70.00  77.00  30.00  178
 67  ω    -89.00 -26.00   0.50    0.10    --  -26.00 150.00 133.31  126
 68  ω     38.00  66.00   0.50    0.10    --  110.00 -57.00 120.00   56
 69  ω     82.00 134.00   0.50    0.10    --  110.00 -77.00 150.00  104
 70  ω     72.00 134.00   0.50    0.10    --  110.00 -77.00 -30.00  124
 71  ω     74.00 117.00   0.50    0.10    --   48.87 178.00-150.00   86
 72  ω     53.00 106.00   0.50    0.10    --  110.00 -99.00 150.00  106
 73  ω     69.00 110.00   0.50    0.10    --  110.00-125.00 120.00   82
 74  ω     61.00 113.00   0.50    0.10    --  110.00-125.00  30.00  104
 75  ω     54.00 127.00   0.50    0.10    --  110.00-144.00   1.12  146
 76  ω     68.00 113.00   0.50    0.10    --  110.00-125.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2864858000
_diffrn_orient_matrix_UB_12      0.0023967000
_diffrn_orient_matrix_UB_13      -0.0041460000
_diffrn_orient_matrix_UB_21      -0.0090585000
_diffrn_orient_matrix_UB_22      -0.1756985000
_diffrn_orient_matrix_UB_23      0.0140263000
_diffrn_orient_matrix_UB_31      -0.0197286000
_diffrn_orient_matrix_UB_32      0.0459333000
_diffrn_orient_matrix_UB_33      0.0538273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2680
_reflns_number_total             2708
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1074 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.069
_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)+(0.0357P)²+0.3964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O3-H3B = O3-H3A
 0.93 with sigma of 0.02
 N007-H007
 0.93 with sigma of 0.02
 H3A-H3B
 1.44 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F 0.2353(2) -0.13568(13) 0.32654(4) 0.0235(3) Uani 1 1 d . . . . .
F2 F 0.5984(2) -0.19802(12) 0.26065(4) 0.0234(2) Uani 1 1 d . . . . .
F3 F 0.9740(2) 0.00845(13) 0.24772(4) 0.0240(2) Uani 1 1 d . . . . .
O1 O 1.1931(3) 0.86649(16) 0.46928(5) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.5736(2) 0.64111(14) 0.36563(4) 0.0165(3) Uani 1 1 d . . . . .
N007 N 0.8971(3) 0.38439(17) 0.39374(5) 0.0147(3) Uani 1 1 d D . . . .
H007 H 0.931(4) 0.303(2) 0.4146(7) 0.018 Uiso 1 1 d D U . . .
C1 C 0.6388(3) 0.20266(19) 0.34495(6) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.4404(3) 0.0981(2) 0.35063(6) 0.0161(3) Uani 1 1 d . . . . .
H2 H 0.317368 0.117824 0.373589 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4277(3) -0.0351(2) 0.32190(6) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.6093(4) -0.0671(2) 0.28795(6) 0.0168(3) Uani 1 1 d . . . . .
C5 C 0.8030(3) 0.0386(2) 0.28228(6) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.8222(3) 0.1729(2) 0.31023(6) 0.0150(3) Uani 1 1 d . . . . .
H6 H 0.954683 0.242313 0.306030 0.018 Uiso 1 1 calc R U . . .
C7 C 0.6456(3) 0.35404(19) 0.37410(6) 0.0145(3) Uani 1 1 d . . . . .
H7 H 0.527462 0.345400 0.401049 0.017 Uiso 1 1 calc R U . . .
C8 C 0.5659(3) 0.49187(19) 0.34128(6) 0.0157(3) Uani 1 1 d . . . . .
H8A H 0.675106 0.495680 0.313316 0.019 Uiso 1 1 calc R U . . .
H8B H 0.397610 0.473036 0.329756 0.019 Uiso 1 1 calc R U . . .
C9 C 0.8823(3) 0.53354(19) 0.42011(6) 0.0142(3) Uani 1 1 d . . . . .
H9 H 0.749676 0.525852 0.444404 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8167(3) 0.66363(19) 0.38458(6) 0.0152(3) Uani 1 1 d . . . . .
H10 H 0.937894 0.664154 0.358020 0.018 Uiso 1 1 calc R U . . .
C11 C 0.8464(3) 0.8133(2) 0.41455(6) 0.0182(3) Uani 1 1 d . . . . .
H11A H 0.881363 0.903806 0.394188 0.022 Uiso 1 1 calc R U . . .
H11B H 0.698639 0.834275 0.433756 0.022 Uiso 1 1 calc R U . . .
C12 C 1.0685(4) 0.7725(2) 0.44645(6) 0.0180(4) Uani 1 1 d . . . . .
C13 C 1.1172(3) 0.5961(2) 0.44434(6) 0.0177(4) Uani 1 1 d . . . . .
H13A H 1.137688 0.552211 0.476522 0.021 Uiso 1 1 calc R U . . .
H13B H 1.264375 0.572723 0.425220 0.021 Uiso 1 1 calc R U . . .
O3 O 0.6136(3) 0.30374(17) 0.51707(6) 0.0319(3) Uani 1 1 d D . . . .
H3A H 0.635(5) 0.412(2) 0.5212(10) 0.048 Uiso 1 1 d D U . . .
H3B H 0.778(4) 0.273(3) 0.5113(10) 0.048 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
F1 C3 1.345(2) . ?
F2 C4 1.3437(19) . ?
F3 C5 1.348(2) . ?
O1 C12 1.217(2) . ?
O2 C8 1.4339(19) . ?
O2 C10 1.418(2) . ?
N007 H007 0.916(17) . ?
N007 C7 1.476(2) . ?
N007 C9 1.462(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.516(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C3 C4 1.379(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.540(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.518(2) . ?
C9 C13 1.522(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.524(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.521(3) . ?
C12 C13 1.519(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O3 H3A 0.93(2) . ?
O3 H3B 0.93(2) . ?

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
C10 O2 C8 108.59(13) . . ?
C7 N007 H007 106.2(15) . . ?
C9 N007 H007 110.5(13) . . ?
C9 N007 C7 106.52(13) . . ?
C2 C1 C6 120.00(16) . . ?
C2 C1 C7 119.83(15) . . ?
C6 C1 C7 120.04(15) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.52(16) . . ?
C3 C2 H2 120.2 . . ?
F1 C3 C2 120.09(16) . . ?
F1 C3 C4 118.78(16) . . ?
C4 C3 C2 121.12(16) . . ?
F2 C4 C3 120.92(17) . . ?
F2 C4 C5 120.37(16) . . ?
C3 C4 C5 118.71(16) . . ?
F3 C5 C4 117.97(15) . . ?
F3 C5 C6 120.12(16) . . ?
C6 C5 C4 121.91(16) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.73(16) . . ?
C5 C6 H6 120.6 . . ?
N007 C7 C1 111.40(13) . . ?
N007 C7 H7 108.9 . . ?
N007 C7 C8 109.73(14) . . ?
C1 C7 H7 108.9 . . ?
C1 C7 C8 108.89(13) . . ?
C8 C7 H7 108.9 . . ?
O2 C8 C7 112.71(13) . . ?
O2 C8 H8A 109.0 . . ?
O2 C8 H8B 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N007 C9 H9 108.8 . . ?
N007 C9 C10 108.64(13) . . ?
N007 C9 C13 118.43(14) . . ?
C10 C9 H9 108.8 . . ?
C10 C9 C13 102.85(13) . . ?
C13 C9 H9 108.8 . . ?
O2 C10 C9 110.72(14) . . ?
O2 C10 H10 109.5 . . ?
O2 C10 C11 114.13(14) . . ?
C9 C10 H10 109.5 . . ?
C9 C10 C11 103.32(13) . . ?
C11 C10 H10 109.5 . . ?
C10 C11 H11A 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 C10 101.93(14) . . ?
C12 C11 H11A 111.4 . . ?
C12 C11 H11B 111.4 . . ?
O1 C12 C11 125.53(16) . . ?
O1 C12 C13 124.78(17) . . ?
C13 C12 C11 109.67(15) . . ?
C9 C13 H13A 111.3 . . ?
C9 C13 H13B 111.3 . . ?
C12 C13 C9 102.58(14) . . ?
C12 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
H3A O3 H3B 100(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C3 C4 F2 -1.5(2) . . . . ?
F1 C3 C4 C5 178.19(15) . . . . ?
F2 C4 C5 F3 2.1(2) . . . . ?
F2 C4 C5 C6 -178.92(15) . . . . ?
F3 C5 C6 C1 178.51(15) . . . . ?
O1 C12 C13 C9 169.03(17) . . . . ?
O2 C10 C11 C12 156.45(14) . . . . ?
N007 C7 C8 O2 -56.19(18) . . . . ?
N007 C9 C10 O2 65.76(17) . . . . ?
N007 C9 C10 C11 -171.64(14) . . . . ?
N007 C9 C13 C12 154.79(14) . . . . ?
C1 C2 C3 F1 -179.01(15) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C7 C8 O2 -178.35(14) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C7 N007 136.45(15) . . . . ?
C2 C1 C7 C8 -102.41(17) . . . . ?
C2 C3 C4 F2 178.89(15) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 F3 -177.64(15) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C7 N007 -47.7(2) . . . . ?
C6 C1 C7 C8 73.43(19) . . . . ?
C7 N007 C9 C10 -62.94(16) . . . . ?
C7 N007 C9 C13 -179.65(14) . . . . ?
C7 C1 C2 C3 176.20(15) . . . . ?
C7 C1 C6 C5 -176.23(15) . . . . ?
C8 O2 C10 C9 -59.89(16) . . . . ?
C8 O2 C10 C11 -175.95(13) . . . . ?
C9 N007 C7 C1 178.91(13) . . . . ?
C9 N007 C7 C8 58.25(16) . . . . ?
C9 C10 C11 C12 36.15(16) . . . . ?
C10 O2 C8 C7 55.63(17) . . . . ?
C10 C9 C13 C12 35.04(16) . . . . ?
C10 C11 C12 O1 163.83(18) . . . . ?
C10 C11 C12 C13 -14.38(18) . . . . ?
C11 C12 C13 C9 -12.74(19) . . . . ?
C13 C9 C10 O2 -167.92(13) . . . . ?
C13 C9 C10 C11 -45.33(16) . . . . ?

_olex2_date_sample_submission    2020-09-16
_olex2_submission_original_sample_id jb180920_1_1
_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 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.889
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jb051020_1_1
_database_code_depnum_ccdc_archive 'CCDC 2169260'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 Cl N2 O, 2(C2 F3 O2)'
_chemical_formula_sum            'C22 H27 Cl F6 N2 O5'
_chemical_formula_weight         548.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H26ClF3N2O3
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'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.12500(10)
_cell_length_b                   10.2780(2)
_cell_length_c                   13.8974(3)
_cell_angle_alpha                77.831(2)
_cell_angle_beta                 85.1830(10)
_cell_angle_gamma                67.565(2)
_cell_volume                     1177.66(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18071
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.6140
_cell_measurement_theta_min      3.2370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.560
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0395
0 0 1 0.0477
0 -2 1 0.0618
0 2 -1 0.0480
1 0 0 0.1161
-1 0 0 0.1074
-5 -4 1 0.1202
5 5 -2 0.1176
-5 -5 -1 0.1161
-5 -1 -5 0.1030
1 -4 6 0.0631
5 5 1 0.1227
-4 -2 -7 0.0861
-5 -6 -1 0.1123
1 -2 8 0.0576
-3 -2 -8 0.0700
-1 -3 -9 0.0469
-4 -6 -2 0.1021
0 -1 -9 0.0391
1 2 9 0.0445
0 -4 -8 0.0362
1 -2 -9 0.0518
-1 2 9 0.0600
0 -5 -6 0.0390
-1 6 4 0.0617
0 -6 -4 0.0485
3 -3 -6 0.0803
-3 2 6 0.0928
0 6 1 0.0534
4 2 6 0.0904
2 1 9 0.0399

_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.087
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
-0.0003 0.0000 -0.9995 -0.0104 -0.1028 -0.0466
0.0003 -0.0000 0.9995 0.0104 0.1028 0.0466
-0.0029 -2.0015 1.0002 0.2230 0.0409 0.2922
0.0029 2.0015 -1.0002 -0.2230 -0.0409 -0.2922
0.9990 -0.0024 -0.0006 0.1735 0.0074 -0.0564
-0.9990 0.0024 0.0006 -0.1735 -0.0074 0.0564
-5.2298 -4.4410 1.4139 -0.4196 -0.0312 0.9071
4.6055 5.1423 -1.7250 0.2335 0.0162 -0.9722
-5.0691 -5.3112 -0.6709 -0.3207 -0.2714 0.9075
-4.8449 -1.4183 -5.4149 -0.7454 -0.6371 0.1962
0.6290 -3.6524 5.7098 0.5571 0.4789 0.6784
5.0485 5.3299 0.6154 0.3145 0.2661 -0.9112
-3.7762 -1.9974 -7.3615 -0.5185 -0.8472 0.1157
-4.7309 -5.7414 -1.4497 -0.2243 -0.3622 0.9047
1.2656 -1.5042 7.6837 0.4592 0.7532 0.4710
-2.8492 -2.3199 -8.2450 -0.3325 -0.9411 0.0615
-1.2667 -2.6832 -8.8201 -0.0252 -0.9996 -0.0106
-3.8226 -6.3316 -2.4670 -0.0144 -0.4783 0.8781
-0.3517 -1.2253 -9.0165 -0.0238 -0.9678 -0.2504
0.8775 2.0679 8.9696 0.0248 0.9930 0.1151
-0.3499 -3.9953 -8.0071 0.2819 -0.9497 0.1362
1.1448 -1.5468 -8.5763 0.2746 -0.9213 -0.2754
-1.0597 1.7029 8.5835 -0.2763 0.9275 0.2517
-0.1838 -5.1445 -6.4782 0.4489 -0.8268 0.3390
-0.5381 5.6051 4.3142 -0.6455 0.6131 -0.4554
0.0158 -5.9884 -3.7586 0.6015 -0.5717 0.5580
2.7190 -2.9536 -5.9783 0.7243 -0.6858 -0.0710
-3.4410 1.5066 6.1742 -0.6934 0.6558 0.2985
-0.3753 5.9490 0.6307 -0.6920 0.2461 -0.6786
4.4747 2.3837 6.4426 0.5890 0.7699 -0.2456
1.6541 1.3877 8.8149 0.2303 0.9619 0.1472

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28389
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.776
_diffrn_reflns_theta_min         3.253
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  51.00   0.50    0.10    --   48.62  77.00   0.00   52
  2  ω     26.00  52.00   0.50    0.10    --   48.62  77.00  90.00   52
  3  ω     33.00  67.00   0.50    0.10    --   48.62  57.00  90.00   68
  4  ω     33.00  98.00   0.50    0.10    --   48.62  57.00   0.00  130
  5  ω     35.00  92.00   0.50    0.10    --   48.62  57.00-120.00  114
  6  ω     76.00 119.00   0.50    0.10    --   58.00  79.00 110.04   86
  7  ω     36.00  69.00   0.50    0.10    --   58.00  79.00 110.04   66
  8  ω     46.00  77.00   0.50    0.10    --   70.00  79.00  88.37   62
  9  ω     46.00  74.00   0.50    0.10    --   70.00  79.00 153.71   56
 10  ω     46.00  71.00   0.50    0.10    --   70.00  79.00  29.94   50
 11  ω     80.00 107.00   0.50    0.10    --   70.00  79.00 153.71   54
 12  ω    107.00 139.00   0.50    0.10    --   74.00  79.00 -17.49   64
 13  ω     51.00  83.00   0.50    0.10    --   74.00  79.00 -17.49   64
 14  ω     50.00  84.00   0.50    0.10    --   74.00  79.00 -39.54   68
 15  ω     93.00 134.00   0.50    0.10    --   74.00  78.00 179.92   82
 16  ω     51.00  84.00   0.50    0.10    --   74.00  78.00 179.92   66
 17  ω     42.00  67.00   0.50    0.10    --   66.00  78.00  22.22   50
 18  ω     43.00  80.00   0.50    0.10    --   66.00  78.00-133.48   74
 19  ω     34.00  80.00   0.50    0.10    --   58.00  78.00-152.00   92
 20  ω     46.00  83.00   0.50    0.10    --   70.00  77.00 128.14   74
 21  ω     46.00  71.00   0.50    0.10    --   70.00  77.00 -41.14   50
 22  ω     86.00 115.00   0.50    0.13    --  110.00  77.00 -30.00   58
 23  ω    128.00 154.00   0.50    0.13    --  110.00  77.00  60.00   52
 24  ω     86.00 123.00   0.50    0.13    --  110.00  77.00  60.00   74
 25  ω     87.00 175.00   0.50    0.13    --  110.00  77.00-120.00  176
 26  ω     86.00 175.00   0.50    0.13    --  110.00  77.00 120.00  178
 27  ω     86.00 170.00   0.50    0.13    --  110.00  77.00-150.00  168
 28  ω     86.00 176.00   0.50    0.13    --  110.00  77.00 -60.00  180
 29  ω     86.00 173.00   0.50    0.13    --  110.00  77.00  90.00  174
 30  ω     89.00 176.00   0.50    0.13    --  110.00  77.00 -90.00  174
 31  ω    128.00 176.00   0.50    0.13    --  110.00  77.00 150.00   96
 32  ω     89.00 125.00   0.50    0.13    --  110.00  77.00 150.00   72
 33  ω    119.00 171.00   0.50    0.13    --  110.00  77.00 -30.00  104
 34  ω     36.00  61.00   0.50    0.10    --   58.00  76.00 162.49   50
 35  ω     53.00  85.00   0.50    0.10    --   74.00  74.00  58.66   64
 36  ω     53.00  94.00   0.50    0.10    --   74.00  73.00-135.00   82
 37  ω     53.00  79.00   0.50    0.10    --   74.00  71.00 -80.38   52
 38  ω     85.00 113.00   0.50    0.10    --   74.00  71.00 -80.38   56
 39  ω    153.00 178.00   0.50    0.13    --  110.00  57.00 -90.00   50
 40  ω     96.00 127.00   0.50    0.13    --  110.00  57.00 -90.00   62
 41  ω     95.00 121.00   0.50    0.13    --  110.00  57.00 150.00   52
 42  ω     95.00 139.00   0.50    0.13    --  110.00  57.00  60.00   88
 43  ω    150.00 178.00   0.50    0.13    --  110.00  57.00   0.00   56
 44  ω     94.00 163.00   0.50    0.13    --  110.00  57.00  90.00  138
 45  ω    142.00 177.00   0.50    0.13    --  110.00  57.00  30.00   70
 46  ω     95.00 125.00   0.50    0.13    --  110.00  57.00   0.00   60
 47  ω     94.00 177.00   0.50    0.13    --  110.00  57.00-180.00  166
 48  ω     97.00 139.00   0.50    0.13    --  110.00  57.00  30.00   84
 49  ω    108.00 140.00   0.50    0.13    --  110.00  38.00  30.00   64
 50  ω     82.00 108.00   0.50    0.13    --  110.00-125.00  60.00   52
 51  ω     71.00 113.00   0.50    0.13    --  110.00-125.00 120.00   84
 52  ω     42.00  68.00   0.50    0.13    --  110.00 -99.00-120.00   52
 53  ω     48.00 100.00   0.50    0.13    --  110.00 -99.00-180.00  104
 54  ω     73.00 103.00   0.50    0.13    --  110.00 -99.00-120.00   60
 55  ω     77.00 103.00   0.50    0.13    --  110.00 -99.00 -90.00   52
 56  ω     70.00  96.00   0.50    0.13    --  110.00 -99.00 -60.00   52
 57  ω     40.00  66.00   0.50    0.13    --  110.00 -99.00 -60.00   52
 58  ω     41.00  67.00   0.50    0.13    --  110.00 -99.00 -90.00   52
 59  ω     47.00  90.00   0.50    0.13    --  110.00 -99.00 120.00   86
 60  ω     62.00 118.00   0.50    0.10    --   48.62 178.00-180.00  112
 61  ω     68.00 120.00   0.50    0.10    --   48.62 178.00  60.00  104
 62  ω     46.00 121.00   0.50    0.13    --  110.00 -77.00 -60.00  150
 63  ω     40.00  68.00   0.50    0.13    --  110.00 -57.00  30.00   56
 64  ω    -19.00   6.00   0.50    0.10    --   48.62 -19.00-150.00   50
 65  ω    -84.00 -27.00   0.50    0.10    --  -26.00 150.00  58.39  114
 66  ω    -85.00 -18.00   0.50    0.13    --  -70.00 125.00-120.00  134
 67  ω     -1.00  26.00   0.50    0.10    --  -48.62  19.00 -30.00   54
 68  ω    -50.00 -25.00   0.50    0.10    --  -48.62 -77.00-120.00   50
 69  ω    -50.00 -25.00   0.50    0.10    --  -48.62 -77.00   0.00   50
 70  ω    -79.00 -38.00   0.50    0.10    --  -48.62 -38.00-120.00   82
 71  ω   -119.00 -92.00   0.50    0.10    --  -48.62 -38.00 -30.00   54
 72  ω    -88.00 -35.00   0.50    0.10    --  -48.62 -38.00-150.00  106
 73  ω    -90.00 -36.00   0.50    0.10    --  -48.62 -38.00 -30.00  108
 74  ω   -124.00 -55.00   0.50    0.10    --  -48.62 -19.00   0.00  138
 75  ω    -71.00 -46.00   0.50    0.13    --  -70.00 -77.00 -90.00   50
 76  ω    -72.00 -47.00   0.50    0.13    --  -70.00 -76.00  67.97   50
 77  ω    -78.00 -47.00   0.50    0.13    --  -70.00 -75.00 -54.37   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1734566000
_diffrn_orient_matrix_UB_12      -0.1064776000
_diffrn_orient_matrix_UB_13      0.0103435000
_diffrn_orient_matrix_UB_21      0.0075025000
_diffrn_orient_matrix_UB_22      0.0309402000
_diffrn_orient_matrix_UB_23      0.1028451000
_diffrn_orient_matrix_UB_31      -0.0567375000
_diffrn_orient_matrix_UB_32      -0.1226022000
_diffrn_orient_matrix_UB_33      0.0466457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4577
_reflns_number_total             4976
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.072
_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)+(0.0394P)²+0.5108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N2-H2A = N2-H2B
 0.93 with sigma of 0.02
 H2A-H2B
 1.44 with sigma of 0.02
 H1A-H1B
 1.44 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74224(4) 0.87287(3) 0.43243(2) 0.02528(9) Uani 1 1 d . . . . .
O1 O 0.42181(11) 0.84299(10) 0.75464(7) 0.01785(19) Uani 1 1 d . . . . .
N1 N 0.52104(13) 0.65636(11) 0.61757(8) 0.0150(2) Uani 1 1 d D . . . .
H1A H 0.5222(19) 0.6463(17) 0.5541(9) 0.018 Uiso 1 1 d D U . . .
H1B H 0.5660(18) 0.5648(15) 0.6516(10) 0.018 Uiso 1 1 d D U . . .
N2 N 0.32011(13) 0.42801(12) 0.93818(8) 0.0166(2) Uani 1 1 d D . . . .
H2A H 0.4282(15) 0.3884(17) 0.9392(12) 0.020 Uiso 1 1 d D U . . .
H2B H 0.2935(18) 0.4700(17) 0.9924(11) 0.020 Uiso 1 1 d D U . . .
C1 C 0.85555(16) 0.73136(14) 0.52205(10) 0.0195(3) Uani 1 1 d . . . . .
C2 C 1.01739(17) 0.67074(16) 0.50452(11) 0.0243(3) Uani 1 1 d . . . . .
H2 H 1.062571 0.710090 0.449342 0.029 Uiso 1 1 calc R U . . .
C3 C 1.11093(17) 0.55146(17) 0.56965(12) 0.0262(3) Uani 1 1 d . . . . .
H3 H 1.219354 0.510566 0.558281 0.031 Uiso 1 1 calc R U . . .
C4 C 1.04363(17) 0.49281(16) 0.65169(11) 0.0242(3) Uani 1 1 d . . . . .
H4 H 1.106408 0.411399 0.694591 0.029 Uiso 1 1 calc R U . . .
C5 C 0.88245(16) 0.55551(15) 0.66991(10) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.838280 0.516143 0.725581 0.024 Uiso 1 1 calc R U . . .
C6 C 0.78516(15) 0.67727(14) 0.60571(10) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.61156(15) 0.74733(13) 0.62945(9) 0.0158(2) Uani 1 1 d . . . . .
H7 H 0.567850 0.839303 0.583538 0.019 Uiso 1 1 calc R U . . .
C8 C 0.58604(15) 0.77635(14) 0.73409(10) 0.0171(3) Uani 1 1 d . . . . .
H8A H 0.630868 0.686602 0.780586 0.021 Uiso 1 1 calc R U . . .
H8B H 0.640490 0.838107 0.741972 0.021 Uiso 1 1 calc R U . . .
C9 C 0.33135(15) 0.75661(14) 0.74978(9) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.35060(15) 0.72125(14) 0.64659(9) 0.0165(3) Uani 1 1 d . . . . .
H10A H 0.299127 0.654877 0.644688 0.020 Uiso 1 1 calc R U . . .
H10B H 0.298187 0.808402 0.599281 0.020 Uiso 1 1 calc R U . . .
C11 C 0.38157(15) 0.62304(14) 0.83271(9) 0.0161(2) Uani 1 1 d . . . . .
H11A H 0.486647 0.558225 0.818131 0.019 Uiso 1 1 calc R U . . .
H11B H 0.387692 0.651998 0.893845 0.019 Uiso 1 1 calc R U . . .
C12 C 0.26818(15) 0.54301(14) 0.84670(9) 0.0162(3) Uani 1 1 d . . . . .
H12 H 0.278195 0.497186 0.790095 0.019 Uiso 1 1 calc R U . . .
C13 C 0.09503(15) 0.64043(14) 0.85697(10) 0.0183(3) Uani 1 1 d . . . . .
H13A H 0.079840 0.670784 0.919817 0.022 Uiso 1 1 calc R U . . .
H13B H 0.027637 0.587139 0.855826 0.022 Uiso 1 1 calc R U . . .
C14 C 0.04654(15) 0.77274(14) 0.77389(10) 0.0195(3) Uani 1 1 d . . . . .
H14A H 0.046552 0.743399 0.711967 0.023 Uiso 1 1 calc R U . . .
H14B H -0.060235 0.836895 0.785951 0.023 Uiso 1 1 calc R U . . .
C15 C 0.15983(15) 0.85212(14) 0.76647(10) 0.0191(3) Uani 1 1 d . . . . .
H15A H 0.127052 0.934135 0.712524 0.023 Uiso 1 1 calc R U . . .
H15B H 0.153329 0.887688 0.826661 0.023 Uiso 1 1 calc R U . . .
C16 C 0.25694(16) 0.31362(15) 0.94701(10) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.141379 0.343993 0.944889 0.024 Uiso 1 1 calc R U . . .
C17 C 0.35198(18) 0.18747(16) 0.90159(12) 0.0280(3) Uani 1 1 d . . . . .
H17A H 0.450334 0.186715 0.868779 0.034 Uiso 1 1 calc R U . . .
H17B H 0.294957 0.143347 0.871963 0.034 Uiso 1 1 calc R U . . .
C18 C 0.34461(19) 0.17240(16) 1.01161(12) 0.0278(3) Uani 1 1 d . . . . .
H18A H 0.283053 0.119306 1.048211 0.033 Uiso 1 1 calc R U . . .
H18B H 0.438456 0.162681 1.045026 0.033 Uiso 1 1 calc R U . . .
F1A F 1.01376(10) 0.14065(9) 0.95223(7) 0.02759(19) Uani 1 1 d . . . . .
F2A F 0.86697(10) 0.08234(9) 0.86951(7) 0.02770(19) Uani 1 1 d . . . . .
F3A F 0.97393(10) 0.23111(9) 0.79758(6) 0.0293(2) Uani 1 1 d . . . . .
O1A O 0.64346(11) 0.28852(11) 0.94310(7) 0.0230(2) Uani 1 1 d . . . . .
O2A O 0.78383(12) 0.43144(10) 0.90238(7) 0.0229(2) Uani 1 1 d . . . . .
C1A C 0.90310(16) 0.19174(15) 0.88054(10) 0.0199(3) Uani 1 1 d . . . . .
C2A C 0.76011(15) 0.31770(14) 0.91005(9) 0.0179(3) Uani 1 1 d . . . . .
F1B F 0.36529(12) 0.90352(9) 0.41532(7) 0.0332(2) Uani 1 1 d . . . . .
F2B F 0.16810(10) 0.89176(9) 0.34901(7) 0.0322(2) Uani 1 1 d . . . . .
F3B F 0.36054(11) 0.91913(9) 0.25889(6) 0.0285(2) Uani 1 1 d . . . . .
O1B O 0.50784(12) 0.62567(10) 0.42492(7) 0.0236(2) Uani 1 1 d . . . . .
O2B O 0.36892(13) 0.63311(10) 0.29697(8) 0.0265(2) Uani 1 1 d . . . . .
C1B C 0.32563(16) 0.85124(14) 0.34535(10) 0.0191(3) Uani 1 1 d . . . . .
C2B C 0.40975(15) 0.68632(14) 0.35730(9) 0.0172(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.7437(14) . ?
O1 C8 1.4226(15) . ?
O1 C9 1.4381(16) . ?
N1 H1A 0.908(12) . ?
N1 H1B 0.909(13) . ?
N1 C7 1.5038(16) . ?
N1 C10 1.4975(16) . ?
N2 H2A 0.913(13) . ?
N2 H2B 0.916(13) . ?
N2 C12 1.5093(16) . ?
N2 C16 1.4745(17) . ?
C1 C2 1.3892(19) . ?
C1 C6 1.3957(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3876(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.4016(19) . ?
C6 C7 1.5094(17) . ?
C7 H7 0.9800 . ?
C7 C8 1.5267(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5325(18) . ?
C9 C11 1.5376(17) . ?
C9 C15 1.5262(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5276(18) . ?
C12 H12 0.9800 . ?
C12 C13 1.5278(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5306(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5282(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9800 . ?
C16 C17 1.4921(19) . ?
C16 C18 1.496(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.502(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
F1A C1A 1.3534(16) . ?
F2A C1A 1.3268(16) . ?
F3A C1A 1.3374(16) . ?
O1A C2A 1.2399(17) . ?
O2A C2A 1.2496(17) . ?
C1A C2A 1.5464(18) . ?
F1B C1B 1.3390(16) . ?
F2B C1B 1.3349(16) . ?
F3B C1B 1.3357(16) . ?
O1B C2B 1.2415(16) . ?
O2B C2B 1.2418(16) . ?
C1B C2B 1.5490(18) . ?

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
C8 O1 C9 113.85(9) . . ?
H1A N1 H1B 104.1(13) . . ?
C7 N1 H1A 111.5(10) . . ?
C7 N1 H1B 112.1(10) . . ?
C10 N1 H1A 106.9(10) . . ?
C10 N1 H1B 110.3(10) . . ?
C10 N1 C7 111.63(10) . . ?
H2A N2 H2B 104.2(13) . . ?
C12 N2 H2A 108.7(11) . . ?
C12 N2 H2B 109.1(10) . . ?
C16 N2 H2A 109.3(11) . . ?
C16 N2 H2B 110.6(11) . . ?
C16 N2 C12 114.35(10) . . ?
C2 C1 Cl1 117.23(11) . . ?
C2 C1 C6 121.49(13) . . ?
C6 C1 Cl1 121.21(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.58(14) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.20(13) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.97(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.03(13) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.68(12) . . ?
C1 C6 C7 122.30(12) . . ?
C5 C6 C7 120.01(12) . . ?
N1 C7 C6 111.39(10) . . ?
N1 C7 H7 108.3 . . ?
N1 C7 C8 108.60(10) . . ?
C6 C7 H7 108.3 . . ?
C6 C7 C8 111.93(11) . . ?
C8 C7 H7 108.3 . . ?
O1 C8 C7 110.95(10) . . ?
O1 C8 H8A 109.4 . . ?
O1 C8 H8B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O1 C9 C10 108.56(10) . . ?
O1 C9 C11 110.14(10) . . ?
O1 C9 C15 104.82(10) . . ?
C10 C9 C11 113.52(10) . . ?
C15 C9 C10 110.11(10) . . ?
C15 C9 C11 109.34(11) . . ?
N1 C10 C9 112.36(10) . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C9 C11 H11A 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C9 113.29(10) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N2 C12 C11 107.04(10) . . ?
N2 C12 H12 108.9 . . ?
N2 C12 C13 109.96(10) . . ?
C11 C12 H12 108.9 . . ?
C11 C12 C13 113.15(11) . . ?
C13 C12 H12 108.9 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.37(11) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.18(11) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C9 C15 C14 112.40(11) . . ?
C9 C15 H15A 109.1 . . ?
C9 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 H16 116.6 . . ?
N2 C16 C17 117.20(12) . . ?
N2 C16 C18 117.56(12) . . ?
C17 C16 H16 116.6 . . ?
C17 C16 C18 60.37(10) . . ?
C18 C16 H16 116.6 . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
C16 C17 C18 59.94(9) . . ?
H17A C17 H17B 114.9 . . ?
C18 C17 H17A 117.8 . . ?
C18 C17 H17B 117.8 . . ?
C16 C18 C17 59.69(10) . . ?
C16 C18 H18A 117.8 . . ?
C16 C18 H18B 117.8 . . ?
C17 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
H18A C18 H18B 114.9 . . ?
F1A C1A C2A 108.85(11) . . ?
F2A C1A F1A 106.90(11) . . ?
F2A C1A F3A 107.57(11) . . ?
F2A C1A C2A 113.71(11) . . ?
F3A C1A F1A 106.47(11) . . ?
F3A C1A C2A 112.93(11) . . ?
O1A C2A O2A 129.80(13) . . ?
O1A C2A C1A 115.48(12) . . ?
O2A C2A C1A 114.56(12) . . ?
F1B C1B C2B 112.96(11) . . ?
F2B C1B F1B 106.54(11) . . ?
F2B C1B F3B 106.69(11) . . ?
F2B C1B C2B 111.84(11) . . ?
F3B C1B F1B 106.90(11) . . ?
F3B C1B C2B 111.51(11) . . ?
O1B C2B O2B 128.95(12) . . ?
O1B C2B C1B 116.35(11) . . ?
O2B C2B C1B 114.70(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -175.25(10) . . . . ?
Cl1 C1 C6 C5 174.53(10) . . . . ?
Cl1 C1 C6 C7 -6.99(18) . . . . ?
O1 C9 C10 N1 52.94(13) . . . . ?
O1 C9 C11 C12 167.51(10) . . . . ?
O1 C9 C15 C14 -174.38(10) . . . . ?
N1 C7 C8 O1 -56.90(13) . . . . ?
N2 C12 C13 C14 170.28(11) . . . . ?
N2 C16 C17 C18 107.83(14) . . . . ?
N2 C16 C18 C17 -107.23(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C6 C7 N1 110.27(14) . . . . ?
C1 C6 C7 C8 -127.93(13) . . . . ?
C2 C1 C6 C5 -2.52(19) . . . . ?
C2 C1 C6 C7 175.96(12) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 1.19(19) . . . . ?
C4 C5 C6 C7 -177.32(12) . . . . ?
C5 C6 C7 N1 -71.29(15) . . . . ?
C5 C6 C7 C8 50.51(16) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C6 C7 C8 O1 179.70(10) . . . . ?
C7 N1 C10 C9 -52.76(14) . . . . ?
C8 O1 C9 C10 -58.31(13) . . . . ?
C8 O1 C9 C11 66.54(13) . . . . ?
C8 O1 C9 C15 -175.95(10) . . . . ?
C9 O1 C8 C7 62.05(13) . . . . ?
C9 C11 C12 N2 -172.54(10) . . . . ?
C9 C11 C12 C13 -51.24(14) . . . . ?
C10 N1 C7 C6 176.72(10) . . . . ?
C10 N1 C7 C8 53.01(13) . . . . ?
C10 C9 C11 C12 -70.53(14) . . . . ?
C10 C9 C15 C14 69.04(14) . . . . ?
C11 C9 C10 N1 -69.89(14) . . . . ?
C11 C9 C15 C14 -56.33(14) . . . . ?
C11 C12 C13 C14 50.65(15) . . . . ?
C12 N2 C16 C17 89.01(15) . . . . ?
C12 N2 C16 C18 157.98(12) . . . . ?
C12 C13 C14 C15 -53.47(15) . . . . ?
C13 C14 C15 C9 57.77(15) . . . . ?
C15 C9 C10 N1 167.16(10) . . . . ?
C15 C9 C11 C12 52.84(14) . . . . ?
C16 N2 C12 C11 -162.48(10) . . . . ?
C16 N2 C12 C13 74.23(13) . . . . ?
F1A C1A C2A O1A -101.78(13) . . . . ?
F1A C1A C2A O2A 74.09(14) . . . . ?
F2A C1A C2A O1A 17.27(16) . . . . ?
F2A C1A C2A O2A -166.87(11) . . . . ?
F3A C1A C2A O1A 140.21(12) . . . . ?
F3A C1A C2A O2A -43.92(16) . . . . ?
F1B C1B C2B O1B -3.98(17) . . . . ?
F1B C1B C2B O2B 176.10(12) . . . . ?
F2B C1B C2B O1B -124.17(13) . . . . ?
F2B C1B C2B O2B 55.90(16) . . . . ?
F3B C1B C2B O1B 116.45(13) . . . . ?
F3B C1B C2B O2B -63.48(16) . . . . ?

_olex2_date_sample_data_collection 2020-10-05
_olex2_date_sample_submission    2020-10-02
_olex2_submission_original_sample_id jb051020_1_1
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.800
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jb250920_1_1
_database_code_depnum_ccdc_archive 'CCDC 2169267'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H26 Cl N2 O, C2 F3 O2'
_chemical_formula_sum            'C20 H26 Cl F3 N2 O3'
_chemical_formula_weight         434.88
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H25ClN2O
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'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.51880(10)
_cell_length_b                   8.84740(10)
_cell_length_c                   11.0858(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.4560(10)
_cell_angle_gamma                90
_cell_volume                     1027.02(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18046
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.6190
_cell_measurement_theta_min      4.0040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (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_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1336
0 0 -1 0.0451
1 0 0 0.0215
-1 0 0 0.0215
4 -1 5 0.0466
-7 0 1 0.0249
0 -2 7 0.0552
-4 0 -6 0.0357
-5 -3 4 0.0771
-6 -2 -3 0.0540
5 4 0 0.0874
2 3 6 0.0951
-1 2 7 0.0879
-2 5 -1 0.1272
1 -4 4 0.1033
2 -4 -5 0.1138
4 -4 3 0.0866
5 -3 -3 0.0778
2 0 -7 0.0444
-3 1 6 0.0612
-5 4 0 0.0894
5 -2 4 0.0547
7 -1 -1 0.0405
6 0 -5 0.0350
-6 0 4 0.0432
-7 2 0 0.0444
-5 0 -4 0.0282
-7 -1 -1 0.0374
-5 -2 5 0.0516

_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.043
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
-0.0003 1.0003 0.0001 -0.0170 0.1653 -0.0522
0.0014 0.0012 -1.0009 0.0138 -0.0404 -0.1330
0.9991 0.0007 -0.0004 0.1436 0.0220 0.0225
-0.9991 -0.0007 0.0004 -0.1436 -0.0220 -0.0225
3.7917 -1.2563 5.3702 0.4933 0.0935 0.8648
-6.8092 -0.4006 0.7932 -0.9827 -0.1831 -0.0277
0.2867 -1.7771 6.7775 -0.0207 -0.0122 0.9997
-3.8221 -0.1066 -5.5541 -0.4721 -0.3268 -0.8187
-4.6122 -3.1348 4.0098 -0.6643 -0.4562 0.5922
-5.7450 -1.7723 -2.6039 -0.7604 -0.5244 -0.3833
5.2320 3.6392 0.2328 0.6872 0.7253 -0.0408
1.5591 2.8665 5.8333 0.0963 0.7446 0.6605
-0.9440 2.3519 6.5545 -0.2646 0.6341 0.7266
-1.8067 5.4341 -1.1555 -0.3361 0.8114 -0.4782
1.3650 -4.3410 4.3309 0.2109 -0.5116 0.8330
1.5722 -4.3520 -4.5308 0.3613 -0.8686 -0.3391
4.2234 -3.6173 2.9444 0.6284 -0.3857 0.6756
5.1692 -2.9538 -3.3996 0.8393 -0.5129 -0.1805
2.0912 -0.0055 -7.0282 0.3961 -0.2405 -0.8861
-3.4176 1.0804 6.3941 -0.5964 0.3633 0.7158
-5.1342 3.7202 -0.3611 -0.7961 0.4876 -0.3584
4.8264 -2.1266 3.8363 0.6777 -0.0899 0.7299
6.6072 -1.3154 -1.4035 0.9911 -0.1296 0.0316
5.5328 -0.2475 -4.7364 0.8638 -0.1120 -0.4912
-5.8856 0.4720 4.1680 -0.9106 0.1183 0.3960
-6.5123 1.6352 -0.0294 -0.9634 0.1264 -0.2366
-5.3863 -0.1372 -3.8619 -0.7194 -0.2974 -0.6277
-6.5349 -1.2336 -0.7365 -0.9084 -0.3768 -0.1812
-4.9107 -1.8858 4.8747 -0.7401 -0.2212 0.6351

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.158
_diffrn_reflns_theta_min         4.006
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -35.00   0.50    0.40    --  -48.62 -38.00   0.00   58
  2  ω     -2.00  26.00   0.50    0.40    --  -48.62  19.00  60.00   56
  3  ω    -67.00 -37.00   0.50    0.40    --  -48.62 -19.00  90.00   60
  4  ω    -73.00 -47.00   0.50    1.41    --  -70.00 -74.00  96.32   52
  5  ω    -72.00 -46.00   0.50    1.41    --  -70.00 -77.00  60.00   52
  6  ω    -76.00 -49.00   0.50    1.41    --  -70.00 -73.00 -21.83   54
  7  ω    -73.00 -45.00   0.50    1.41    --  -70.00 -80.00 -43.76   56
  8  ω    -73.00 -46.00   0.50    1.41    --  -70.00 -77.00-105.16   54
  9  ω    -79.00 -48.00   0.50    1.41    --  -70.00 -77.00   0.00   62
 10  ω    -78.00 -52.00   0.50    1.41    --  -70.00 -78.00  26.23   52
 11  ω    -84.00 -47.00   0.50    1.41    --  -70.00 -77.00  35.77   74
 12  ω    -92.00 -41.00   0.50    0.40    --  -48.62 -38.00 150.00  102
 13  ω    -73.00 -47.00   0.50    1.41    --  -70.00 -74.00 175.78   52
 14  ω   -123.00 -86.00   0.50    0.40    --  -48.62 -19.00  90.00   74
 15  ω   -124.00 -74.00   0.50    0.40    --  -48.62 -38.00   0.00  100
 16  ω   -119.00 -92.00   0.50    1.41    --  -70.00 -80.00 -43.76   54
 17  ω   -136.00-103.00   0.50    1.41    --  -70.00 -74.00  96.32   66
 18  ω    -25.00   8.00   0.50    0.40    --   48.62 -19.00  90.00   66
 19  ω     34.00  91.00   0.50    0.40    --   48.62  57.00   0.00  114
 20  ω     67.00  93.00   0.50    1.41    --   82.00  54.00 -39.34   52
 21  ω     71.00 119.00   0.50    1.41    --   90.00  65.00 -12.39   96
 22  ω    126.00 159.00   0.50    1.41    --   90.00  65.00 -12.39   66
 23  ω    134.00 166.00   0.50    1.41    --  110.00  77.00   0.00   64
 24  ω    127.00 162.00   0.50    1.41    --  110.00  77.00 -60.00   70
 25  ω    128.00 177.00   0.50    1.41    --  110.00 125.00 -90.00   98
 26  ω    152.00 177.00   0.50    1.41    --  110.00  57.00-180.00   50
 27  ω    126.00 157.00   0.50    1.41    --  110.00  77.00-120.00   62
 28  ω    114.00 146.00   0.50    1.41    --   82.00  74.00-143.66   64
 29  ω    105.00 141.00   0.50    1.41    --  110.00  38.00-120.00   72
 30  ω    101.00 144.00   0.50    1.41    --  110.00  57.00-180.00   86
 31  ω    106.00 135.00   0.50    1.41    --  110.00  19.00-120.00   58
 32  ω     99.00 177.00   0.50    1.41    --  110.00  38.00 -30.00  156
 33  ω    131.00 175.00   0.50    1.41    --  110.00  77.00  60.00   88
 34  ω    128.00 163.00   0.50    1.41    --  110.00  77.00  90.00   70
 35  ω    119.00 176.00   0.50    1.41    --  110.00  77.00  30.00  114
 36  ω    123.00 174.00   0.50    1.41    --  110.00  77.00 120.00  102
 37  ω    117.00 143.00   0.50    0.40    --   74.00  68.00 163.15   52
 38  ω    109.00 151.00   0.50    1.41    --   86.00  75.00 175.91   84
 39  ω     98.00 124.00   0.50    0.40    --   74.00  79.00 103.49   52
 40  ω     99.00 159.00   0.50    1.41    --  110.00  38.00 150.00  120
 41  ω     98.00 132.00   0.50    1.41    --  110.00  38.00  30.00   68
 42  ω     89.00 115.00   0.50    1.41    --  110.00  77.00   0.00   52
 43  ω     86.00 112.00   0.50    1.41    --  110.00  77.00 -60.00   52
 44  ω     87.00 123.00   0.50    1.41    --  110.00  77.00-120.00   72
 45  ω     96.00 160.00   0.50    1.41    --  110.00 125.00-150.00  128
 46  ω     87.00 161.00   0.50    1.41    --  110.00  77.00 -90.00  148
 47  ω     98.00 128.00   0.50    1.41    --  110.00  38.00  60.00   60
 48  ω     98.00 145.00   0.50    1.41    --  110.00  38.00  90.00   94
 49  ω     90.00 115.00   0.50    1.41    --  110.00  77.00 120.00   50
 50  ω     87.00 112.00   0.50    1.41    --  110.00  77.00  60.00   50
 51  ω     87.00 112.00   0.50    1.41    --  110.00  77.00  30.00   50
 52  ω     87.00 121.00   0.50    1.41    --  110.00  77.00  90.00   68
 53  ω     54.00  84.00   0.50    0.40    --   74.00  68.00 163.15   60
 54  ω     64.00 112.00   0.50    0.40    --   78.00  58.00 146.62   96
 55  ω     63.00 105.00   0.50    1.41    --   86.00  75.00 175.91   84
 56  ω     50.00  89.00   0.50    0.40    --   74.00  79.00 103.49   78
 57  ω     45.00  71.00   0.50    0.40    --   70.00  80.00 164.42   52
 58  ω     34.00  60.00   0.50    0.40    --   48.62  57.00  90.00   52
 59  ω     34.00  59.00   0.50    0.40    --   58.00  80.00 115.88   50
 60  ω     39.00  66.00   0.50    0.40    --   58.00  78.00 143.86   54
 61  ω     26.00  59.00   0.50    0.40    --   48.62  77.00 120.00   66
 62  ω     26.00  60.00   0.50    0.40    --   50.00  77.00  58.93   68
 63  ω     28.00  54.00   0.50    0.40    --   48.62  77.00   0.00   52
 64  ω     34.00  78.00   0.50    0.40    --   58.00  78.00 -80.11   88
 65  ω     62.00  97.00   0.50    1.41    --   82.00  74.00-143.66   70
 66  ω     66.00  97.00   0.50    0.40    --   48.62  19.00-120.00   62
 67  ω     60.00  96.00   0.50    1.41    --   82.00  74.00 -96.52   72
 68  ω     40.00  65.00   0.50    0.40    --   48.62  19.00-120.00   50
 69  ω     34.00  75.00   0.50    0.40    --   48.62  57.00-120.00   82
 70  ω     50.00  77.00   0.50    0.40    --   74.00  78.00-134.63   54
 71  ω     35.00  63.00   0.50    0.40    --   58.00  77.00-110.97   56
 72  ω     26.00  51.00   0.50    0.40    --   48.62  77.00-120.00   50
 73  ω     33.00  76.00   0.50    0.40    --   48.62  57.00-180.00   86
 74  ω     39.00  68.00   0.50    1.41    --  110.00 -57.00-180.00   58
 75  ω     56.00 105.00   0.50    1.41    --  110.00 -99.00-180.00   98
 76  ω     60.00 121.00   0.50    0.40    --   48.62-178.00-120.00  122
 77  ω     78.00 113.00   0.50    1.41    --  110.00-125.00 -60.00   70
 78  ω     45.00 107.00   0.50    1.41    --  110.00 -98.00 -20.31  124
 79  ω     85.00 112.00   0.50    1.41    --  110.00-125.00  60.00   54
 80  ω     69.00 105.00   0.50    1.41    --  110.00 -99.00  90.00   72
 81  ω     39.00  66.00   0.50    1.41    --  110.00 -57.00 150.00   54
 82  ω     39.00  66.00   0.50    1.41    --  110.00 -57.00  90.00   54
 83  ω     40.00  65.00   0.50    1.41    --  110.00 -57.00  30.00   50
 84  ω     38.00  64.00   0.50    1.41    --  110.00 -57.00   0.00   52
 85  ω     40.00  95.00   0.50    1.41    --  110.00 -99.00 -90.00  110
 86  ω     42.00  81.00   0.50    1.41    --  110.00-125.00  60.00   78
 87  ω    -82.00 -14.00   0.50    1.41    --  -70.00 125.00 -90.00  136
 88  ω     70.00 106.00   0.50    0.40    --   48.62 178.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1437360000
_diffrn_orient_matrix_UB_12      -0.0169495000
_diffrn_orient_matrix_UB_13      -0.0135849000
_diffrn_orient_matrix_UB_21      0.0218984000
_diffrn_orient_matrix_UB_22      0.1652335000
_diffrn_orient_matrix_UB_23      0.0406007000
_diffrn_orient_matrix_UB_31      0.0226102000
_diffrn_orient_matrix_UB_32      -0.0522286000
_diffrn_orient_matrix_UB_33      0.1328524000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4178
_reflns_number_total             4341
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.316(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.067
_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)+(0.0390P)²+0.2427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          
'Refined as inversion twin (sample crystallized from racemic mixture). Disorder of the CF3 group in the anion.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.684(15)
 0.316(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
3. Restrained distances
 H2B-H2A
 1.44 with sigma of 0.02
 N2-H2A = N2-H2B
 0.93 with sigma of 0.02
 N1-H1
 0.93 with sigma of 0.02
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F1B-F2B \\sim F2B-F3B \\sim F3B-F1B
 with sigma of 0.02
 F1A-C1A \\sim F3B-C1B \\sim F2B-C1B \\sim F2A-C1A \\sim F1B-C1B \\sim F3A-C1A
 with sigma of 0.02
 C2A-C1B \\sim C2A-C1A
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 C2A, F1A, C1A, F2A, F3A, O1A, O2A, C1B, F2B, F3B, F1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1B)=Sof(F2B)=Sof(F3B)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C1A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12), C16(H16)
6.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.21159(5) 0.77797(6) -0.21060(5) 0.03113(14) Uani 1 1 d . . . . .
F1A F 0.9178(9) 0.3525(12) 0.5012(6) 0.0535(18) Uani 0.66(2) 1 d D . P A 1
F2A F 0.9233(3) 0.1395(4) 0.5939(9) 0.0525(18) Uani 0.66(2) 1 d D . P A 1
F3A F 0.8801(6) 0.3405(6) 0.6873(5) 0.0473(12) Uani 0.66(2) 1 d D . P A 1
O1 O 0.53209(14) 0.84647(16) 0.16085(14) 0.0209(3) Uani 1 1 d . . . . .
O1A O 0.65903(18) 0.3728(2) 0.52507(19) 0.0373(4) Uani 1 1 d . . . . .
O2A O 0.67326(16) 0.12218(19) 0.53691(17) 0.0305(4) Uani 1 1 d . . . . .
N1 N 0.45686(19) 0.5645(2) 0.05948(18) 0.0234(4) Uani 1 1 d D . . . .
H1 H 0.445(3) 0.500(3) -0.003(2) 0.028 Uiso 1 1 d D U . . .
N2 N 0.58753(18) 0.6703(2) 0.51957(17) 0.0195(4) Uani 1 1 d D . . . .
H2A H 0.5042(19) 0.656(3) 0.511(3) 0.023 Uiso 1 1 d D U . . .
H2B H 0.629(2) 0.581(3) 0.524(3) 0.023 Uiso 1 1 d D U . . .
C1 C 0.1575(2) 0.6764(3) -0.0900(2) 0.0273(5) Uani 1 1 d . . . . .
C1A C 0.8627(7) 0.2701(11) 0.5801(9) 0.0307(16) Uani 0.66(2) 1 d D . P A 1
C2 C 0.0329(2) 0.6217(3) -0.1058(3) 0.0360(6) Uani 1 1 d . . . . .
H2 H -0.018185 0.638470 -0.179998 0.043 Uiso 1 1 calc R U . . .
C2A C 0.7173(2) 0.2521(2) 0.5403(2) 0.0240(5) Uani 1 1 d D . . . .
C3 C -0.0159(3) 0.5431(3) -0.0132(3) 0.0412(7) Uani 1 1 d . . . . .
H3 H -0.100927 0.505658 -0.023305 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0591(3) 0.5189(3) 0.0947(3) 0.0382(6) Uani 1 1 d . . . . .
H4 H 0.024990 0.466920 0.159276 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1839(3) 0.5704(3) 0.1083(3) 0.0304(5) Uani 1 1 d . . . . .
H5 H 0.234936 0.551452 0.182095 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2368(2) 0.6498(2) 0.0159(2) 0.0239(5) Uani 1 1 d . . . . .
C7 C 0.3751(2) 0.6983(2) 0.0340(2) 0.0218(4) Uani 1 1 d . . . . .
H7 H 0.398891 0.748622 -0.041378 0.026 Uiso 1 1 calc R U . . .
C8 C 0.3998(2) 0.8067(2) 0.1406(2) 0.0214(4) Uani 1 1 d . . . . .
H8A H 0.348341 0.899431 0.124385 0.026 Uiso 1 1 calc R U . . .
H8B H 0.372363 0.758745 0.214576 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6165(2) 0.7170(2) 0.1810(2) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.5914(2) 0.6100(3) 0.0735(2) 0.0233(4) Uani 1 1 d . . . . .
H10A H 0.613289 0.660911 -0.001273 0.028 Uiso 1 1 calc R U . . .
H10B H 0.646128 0.519301 0.086401 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5943(2) 0.6388(2) 0.3003(2) 0.0203(4) Uani 1 1 d . . . . .
H11A H 0.504108 0.606086 0.298003 0.024 Uiso 1 1 calc R U . . .
H11B H 0.649070 0.547886 0.310907 0.024 Uiso 1 1 calc R U . . .
C12 C 0.6252(2) 0.7462(2) 0.40710(19) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.571629 0.838933 0.392635 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7645(2) 0.7933(3) 0.4162(2) 0.0233(4) Uani 1 1 d . . . . .
H13A H 0.820380 0.703290 0.426278 0.028 Uiso 1 1 calc R U . . .
H13B H 0.784130 0.860487 0.487000 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7870(2) 0.8764(3) 0.2996(2) 0.0248(5) Uani 1 1 d . . . . .
H14A H 0.877897 0.906391 0.302485 0.030 Uiso 1 1 calc R U . . .
H14B H 0.734741 0.969687 0.293619 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7527(2) 0.7789(3) 0.18714(19) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.762208 0.840158 0.113779 0.029 Uiso 1 1 calc R U . . .
H15B H 0.813394 0.693355 0.187442 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6133(2) 0.7607(3) 0.63032(19) 0.0239(4) Uani 1 1 d . . . . .
H16 H 0.613055 0.872880 0.619313 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5643(3) 0.7041(3) 0.7433(2) 0.0316(5) Uani 1 1 d . . . . .
H17A H 0.517368 0.606945 0.739362 0.038 Uiso 1 1 calc R U . . .
H17B H 0.533411 0.779522 0.799747 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7051(3) 0.7001(3) 0.7292(2) 0.0317(5) Uani 1 1 d . . . . .
H18A H 0.760719 0.773185 0.776909 0.038 Uiso 1 1 calc R U . . .
H18B H 0.744674 0.600574 0.716513 0.038 Uiso 1 1 calc R U . . .
C1B C 0.8628(15) 0.263(2) 0.5543(19) 0.040(4) Uani 0.34(2) 1 d D . P A 2
F2B F 0.9236(7) 0.1463(10) 0.512(3) 0.082(7) Uani 0.34(2) 1 d D . P A 2
F3B F 0.9008(16) 0.272(4) 0.6717(14) 0.094(7) Uani 0.34(2) 1 d D . P A 2
F1B F 0.910(2) 0.3835(18) 0.5025(16) 0.069(5) Uani 0.34(2) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.750(3) . ?
F1A C1A 1.315(9) . ?
F2A C1A 1.321(9) . ?
F3A C1A 1.338(9) . ?
O1 C8 1.432(3) . ?
O1 C9 1.454(3) . ?
O1A C2A 1.235(3) . ?
O2A C2A 1.239(3) . ?
N1 H1 0.90(2) . ?
N1 C7 1.474(3) . ?
N1 C10 1.465(3) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.90(2) . ?
N2 C12 1.502(3) . ?
N2 C16 1.469(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.395(3) . ?
C1A C2A 1.559(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(5) . ?
C2A C1B 1.526(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.511(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.525(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(3) . ?
C9 C11 1.530(3) . ?
C9 C15 1.529(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.531(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
C16 C17 1.486(3) . ?
C16 C18 1.491(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.505(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C1B F2B 1.323(16) . ?
C1B F3B 1.327(15) . ?
C1B F1B 1.331(16) . ?

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
C8 O1 C9 113.62(15) . . ?
C7 N1 H1 108.9(18) . . ?
C10 N1 H1 108.7(18) . . ?
C10 N1 C7 109.86(17) . . ?
H2A N2 H2B 111(2) . . ?
C12 N2 H2A 107.9(19) . . ?
C12 N2 H2B 105.6(18) . . ?
C16 N2 H2A 105.9(19) . . ?
C16 N2 H2B 112.7(18) . . ?
C16 N2 C12 114.11(16) . . ?
C2 C1 Cl1 116.9(2) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 Cl1 121.18(19) . . ?
F1A C1A F2A 108.9(7) . . ?
F1A C1A F3A 107.5(7) . . ?
F1A C1A C2A 110.5(7) . . ?
F2A C1A F3A 106.3(6) . . ?
F2A C1A C2A 113.2(6) . . ?
F3A C1A C2A 110.3(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
O1A C2A O2A 128.2(2) . . ?
O1A C2A C1A 114.3(4) . . ?
O1A C2A C1B 116.2(7) . . ?
O2A C2A C1A 117.2(4) . . ?
O2A C2A C1B 115.3(7) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.9(2) . . ?
C1 C6 C7 123.7(2) . . ?
C5 C6 C7 119.3(2) . . ?
N1 C7 C6 109.52(18) . . ?
N1 C7 H7 109.3 . . ?
N1 C7 C8 107.66(17) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C8 111.85(18) . . ?
C8 C7 H7 109.3 . . ?
O1 C8 C7 111.55(17) . . ?
O1 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O1 C9 C10 108.12(17) . . ?
O1 C9 C11 110.33(17) . . ?
O1 C9 C15 106.28(18) . . ?
C10 C9 C11 111.45(18) . . ?
C10 C9 C15 110.46(18) . . ?
C15 C9 C11 110.06(18) . . ?
N1 C10 C9 110.34(18) . . ?
N1 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C9 C11 H11A 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C9 110.50(18) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
N2 C12 C11 108.17(16) . . ?
N2 C12 H12 108.1 . . ?
N2 C12 C13 113.38(18) . . ?
C11 C12 H12 108.1 . . ?
C13 C12 C11 110.82(18) . . ?
C13 C12 H12 108.1 . . ?
C12 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C12 C13 C14 107.61(17) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C13 C14 C15 112.05(19) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C9 C15 C14 112.66(17) . . ?
C9 C15 H15A 109.1 . . ?
C9 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
N2 C16 H16 116.1 . . ?
N2 C16 C17 118.0(2) . . ?
N2 C16 C18 118.3(2) . . ?
C17 C16 H16 116.1 . . ?
C17 C16 C18 60.75(17) . . ?
C18 C16 H16 116.1 . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
C16 C17 C18 59.77(16) . . ?
H17A C17 H17B 114.9 . . ?
C18 C17 H17A 117.8 . . ?
C18 C17 H17B 117.8 . . ?
C16 C18 C17 59.48(16) . . ?
C16 C18 H18A 117.8 . . ?
C16 C18 H18B 117.8 . . ?
C17 C18 H18A 117.8 . . ?
C17 C18 H18B 117.8 . . ?
H18A C18 H18B 115.0 . . ?
F2B C1B C2A 115.5(12) . . ?
F2B C1B F3B 106.8(14) . . ?
F2B C1B F1B 105.1(14) . . ?
F3B C1B C2A 108.0(12) . . ?
F3B C1B F1B 106.5(14) . . ?
F1B C1B C2A 114.4(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -178.9(2) . . . . ?
Cl1 C1 C6 C5 178.60(18) . . . . ?
Cl1 C1 C6 C7 -2.9(3) . . . . ?
F1A C1A C2A O1A -56.6(8) . . . . ?
F1A C1A C2A O2A 128.8(7) . . . . ?
F2A C1A C2A O1A -179.0(6) . . . . ?
F2A C1A C2A O2A 6.4(8) . . . . ?
F3A C1A C2A O1A 62.1(8) . . . . ?
F3A C1A C2A O2A -112.6(6) . . . . ?
O1 C9 C10 N1 -57.6(2) . . . . ?
O1 C9 C11 C12 -62.1(2) . . . . ?
O1 C9 C15 C14 67.9(2) . . . . ?
O1A C2A C1B F2B -147.7(15) . . . . ?
O1A C2A C1B F3B 92.9(17) . . . . ?
O1A C2A C1B F1B -25(2) . . . . ?
O2A C2A C1B F2B 27.3(17) . . . . ?
O2A C2A C1B F3B -92.2(14) . . . . ?
O2A C2A C1B F1B 149.5(14) . . . . ?
N1 C7 C8 O1 56.9(2) . . . . ?
N2 C12 C13 C14 -176.70(17) . . . . ?
N2 C16 C17 C18 108.5(2) . . . . ?
N2 C16 C18 C17 -108.1(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C7 N1 -120.9(2) . . . . ?
C1 C6 C7 C8 119.8(2) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C1 C6 C7 176.0(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 N1 57.5(3) . . . . ?
C5 C6 C7 C8 -61.7(3) . . . . ?
C6 C1 C2 C3 2.2(4) . . . . ?
C6 C7 C8 O1 177.22(17) . . . . ?
C7 N1 C10 C9 62.1(2) . . . . ?
C8 O1 C9 C10 55.5(2) . . . . ?
C8 O1 C9 C11 -66.6(2) . . . . ?
C8 O1 C9 C15 174.09(16) . . . . ?
C9 O1 C8 C7 -56.7(2) . . . . ?
C9 C11 C12 N2 173.58(16) . . . . ?
C9 C11 C12 C13 -61.6(2) . . . . ?
C10 N1 C7 C6 178.31(18) . . . . ?
C10 N1 C7 C8 -59.9(2) . . . . ?
C10 C9 C11 C12 177.74(17) . . . . ?
C10 C9 C15 C14 -175.10(19) . . . . ?
C11 C9 C10 N1 63.8(2) . . . . ?
C11 C9 C15 C14 -51.6(2) . . . . ?
C11 C12 C13 C14 61.4(2) . . . . ?
C12 N2 C16 C17 172.3(2) . . . . ?
C12 N2 C16 C18 -117.7(2) . . . . ?
C12 C13 C14 C15 -57.6(2) . . . . ?
C13 C14 C15 C9 54.3(3) . . . . ?
C15 C9 C10 N1 -173.49(18) . . . . ?
C15 C9 C11 C12 54.8(2) . . . . ?
C16 N2 C12 C11 179.41(17) . . . . ?
C16 N2 C12 C13 56.1(2) . . . . ?

_olex2_date_sample_data_collection 2020-09-25
_olex2_date_sample_submission    2020-09-23
_olex2_submission_original_sample_id jb250920_1_1
_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.791
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.684(15)
2 0.316(15)

