# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shl-20211012
_database_code_depnum_ccdc_archive 'CCDC 2169815'
loop_
_audit_author_name
_audit_author_address
'Bo Zhu'
;Bo zhu
China
;
_audit_update_record             
;
2022-05-02 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H16 Cl F3 N2 O3'
_chemical_formula_sum            'C19 H16 Cl F3 N2 O3'
_chemical_formula_weight         412.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl1 F1 N1 C1 H1 O1'
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                   7.9325(3)
_cell_length_b                   10.1011(2)
_cell_length_c                   12.3118(3)
_cell_angle_alpha                98.974(2)
_cell_angle_beta                 91.487(2)
_cell_angle_gamma                97.911(2)
_cell_volume                     964.02(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19521
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4200
_cell_measurement_theta_min      4.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clearless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.315
_diffrn_reflns_theta_min         3.639
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00   9.00   1.00    1.00    --  -35.62 112.00  81.00   91
  2  ω     13.00  82.00   1.00    1.00    --   35.62-112.00 -11.00   69
  3  ω    101.00 177.00   1.00    1.00    --  107.12 112.00  81.00   76
  4  ω     37.00 112.00   1.00    1.00    --  107.12-112.00 -11.00   75
  5  ω    -44.00  -5.00   1.00    1.00    --   12.00 129.00 115.19   39
  6  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00 -30.00   88
  7  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-180.00   84
  8  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-180.00   73
  9  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00  60.00   88
 10  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
 11  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 120.00   51
 12  ω      0.00  27.00   1.00    1.00    --   36.00  93.00 -91.63   27
 13  ω      7.00  33.00   1.00    1.00    --   40.00  88.00 118.30   26
 14  ω      6.00  32.00   1.00    1.00    --   40.00  90.00-179.81   26
 15  ω      8.00  34.00   1.00    1.00    --   40.00  87.00  61.18   26
 16  ω     14.00  45.00   1.00    1.00    --   44.00  82.00-130.23   31
 17  ω     14.00  40.00   1.00    1.00    --   44.00  83.00  -2.18   26
 18  ω     18.00  45.00   1.00    1.00    --   48.00  82.00 -71.35   27
 19  ω     26.00 119.00   1.00    1.00    --   52.00  75.00 111.02   93
 20  ω     29.00 124.00   1.00    1.00    --   56.00  77.00-174.79   95
 21  ω     30.00 123.00   1.00    1.00    --   56.00  75.00  14.04   93
 22  ω     29.00 124.00   1.00    1.00    --   56.00  77.00 138.04   95
 23  ω     30.00 123.00   1.00    1.00    --   56.00  75.00 -97.63   93
 24  ω     29.00 124.00   1.00    1.00    --   56.00  77.00 -72.96   95
 25  ω     30.00 123.00   1.00    1.00    --   56.00  75.00-154.05   93
 26  ω     31.00 123.00   1.00    1.00    --   56.00  74.00  79.47   92
 27  ω     43.00 128.00   1.00    1.00    --   60.00  53.00 162.80   85
 28  ω     43.00 131.00   1.00    1.00    --   64.00  67.00 -25.74   88
 29  ω     47.00 132.00   1.00    1.00    --   64.00  50.00 -39.98   85
 30  ω     39.00 131.00   1.00    1.00    --   64.00  73.00  46.70   92
 31  ω     63.00 155.00   1.00    1.00    --   88.00  74.00-127.64   92
 32  ω     70.00 155.00   1.00    1.00    --   88.00  60.00  22.35   85
 33  ω     75.00 160.00   1.00    1.00    --   92.00  47.00-132.77   85
 34  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00   0.00   72
 35  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  30.00   95
 36  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -30.00   95
 37  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  90.00   95
 38  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 150.00   85
 39  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  90.00   85
 40  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 -90.00   85
 41  ω     80.00 175.00   1.00    1.00    --  107.12  77.00   0.00   95
 42  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -90.00   95
 43  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -60.00   95
 44  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 150.00   95
 45  ω     40.00 125.00   1.00    1.00    --  107.12 -61.00   0.00   85
 46  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-120.00   95
 47  ω     40.00 125.00   1.00    1.00    --  107.12 -61.00 150.00   85
 48  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 -60.00   85
 49  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  60.00   95
 50  ω     89.00 174.00   1.00    1.00    --  107.12  61.00-180.00   85
 51  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 -30.00   85
 52  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00-180.00   72
 53  ω     57.00 150.00   1.00    1.00    --  107.12 178.00   0.00   93
 54  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 120.00   95
 55  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  60.00   85
 56  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-150.00   95
 57  ω     37.00 113.00   1.00    1.00    --  107.12-111.00 150.00   76
 58  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00 -90.00  139
 59  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00 -60.00  139
 60  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00-180.00  139
 61  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00 -30.00  139
 62  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00  30.00  139
 63  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00   0.00  139
 64  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00-150.00  139
 65  ω   -105.00  34.00   1.00    1.00    --  -35.62   0.00-120.00  139
 66  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00 -90.00  139
 67  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00-120.00  139
 68  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00-150.00  139
 69  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00  60.00  139
 70  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00-180.00  139
 71  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-180.00   51
 72  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00 -60.00  139
 73  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00 150.00  139
 74  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00  30.00  139
 75  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00 120.00  139
 76  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00 -30.00  139
 77  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00  90.00  139
 78  ω    -34.00 105.00   1.00    1.00    --   35.62   0.00   0.00  139
 79  ω     17.00 105.00   1.00    1.00    --   35.62  38.00-180.00   88
 80  ω      7.00  33.00   1.00    1.00    --   40.00  89.00 129.13   26
 81  ω     14.00  40.00   1.00    1.00    --   44.00  83.00 -23.11   26
 82  ω     19.00  45.00   1.00    1.00    --   48.00  81.00 -34.95   26
 83  ω     22.00 115.00   1.00    1.00    --   48.00  76.00-120.00   93
 84  ω     26.00 119.00   1.00    1.00    --   52.00  76.00   3.94   93
 85  ω     27.00 119.00   1.00    1.00    --   52.00  73.00-108.94   92
 86  ω     30.00 123.00   1.00    1.00    --   56.00  76.00 -33.41   93
 87  ω     47.00 132.00   1.00    1.00    --   64.00  49.00  37.18   85
 88  ω     55.00 140.00   1.00    1.00    --   72.00  51.00 -84.65   85
 89  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  30.00   85
 90  ω     38.00 172.00   1.00    1.00    --  107.12   0.00 -60.00  134
 91  ω     38.00 176.00   1.00    1.00    --  107.12   0.00 -90.00  138
 92  ω     38.00 176.00   1.00    1.00    --  107.12   0.00-120.00  138
 93  ω     38.00 176.00   1.00    1.00    --  107.12   0.00-180.00  138
 94  ω     86.00 177.00   1.00    1.00    --  107.12  30.00 150.00   91
 95  ω     86.00 177.00   1.00    1.00    --  107.12  30.00-150.00   91
 96  ω     90.00 176.00   1.00    1.00    --  107.12  45.00 150.00   86
 97  ω     90.00 176.00   1.00    1.00    --  107.12  45.00  90.00   86
 98  ω     90.00 176.00   1.00    1.00    --  107.12  45.00 -60.00   86
 99  ω     38.00 176.00   1.00    1.00    --  107.12   0.00-150.00  138
100  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00 -90.00   72
101  ω     89.00 174.00   1.00    1.00    --  107.12  61.00   0.00   85
102  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-180.00   95
103  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0112645000
_diffrn_orient_matrix_UB_12      0.0731166000
_diffrn_orient_matrix_UB_13      -0.1009848000
_diffrn_orient_matrix_UB_21      -0.0911009000
_diffrn_orient_matrix_UB_22      -0.1294293000
_diffrn_orient_matrix_UB_23      -0.0726674000
_diffrn_orient_matrix_UB_31      -0.1735210000
_diffrn_orient_matrix_UB_32      0.0473709000
_diffrn_orient_matrix_UB_33      0.0246406000
_diffrn_oxdiff_digest_frames     
;
0195345328d198e5f1f9756d69357b12250003692e6
;
_diffrn_oxdiff_digest_hkl        
;
011cf6737e7a45ef6db61a6bc77583e8764192
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2996
_reflns_number_total             3815
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0861
_refine_ls_restrained_S_all      1.075
_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)+(0.0697P)²+1.3709P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2152
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00M(H00D,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_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
Cl01 Cl -0.24700(18) 0.39193(14) 0.18751(13) 0.1094(6) Uani 1 1 d . . . . .
F002 F 0.4530(3) 0.8437(3) 0.0906(2) 0.0844(8) Uani 1 1 d . . . . .
O003 O -0.0875(3) 0.8311(3) 0.2757(3) 0.0714(9) Uani 1 1 d . . . . .
F004 F 0.3215(3) 1.0136(3) 0.1261(2) 0.0893(9) Uani 1 1 d . . . . .
F005 F 0.5794(3) 1.0265(3) 0.1863(3) 0.0929(9) Uani 1 1 d . . . . .
O006 O 0.1006(3) 1.0163(3) 0.3318(3) 0.0673(8) Uani 1 1 d . . . . .
N007 N 0.1931(3) 0.6943(3) 0.2065(2) 0.0486(7) Uani 1 1 d . . . . .
N008 N 0.1972(3) 0.8271(3) 0.2574(3) 0.0488(7) Uani 1 1 d . . . . .
O009 O 0.3599(4) 0.8629(4) 0.4900(3) 0.0951(11) Uani 1 1 d . . . . .
C00A C 0.0562(4) 0.8864(3) 0.2876(3) 0.0484(8) Uani 1 1 d . . . . .
C00B C 0.3709(4) 0.9006(3) 0.2754(3) 0.0489(8) Uani 1 1 d . . . . .
H00B H 0.3672 0.9825 0.3291 0.059 Uiso 1 1 calc R . . . .
C00C C 0.4943(4) 0.8188(4) 0.3217(3) 0.0515(9) Uani 1 1 d . . . . .
H00A H 0.4814 0.7289 0.2782 0.062 Uiso 1 1 calc R . . . .
H00C H 0.6100 0.8618 0.3155 0.062 Uiso 1 1 calc R . . . .
C00D C 0.0728(5) 0.4747(4) 0.1268(3) 0.0527(8) Uani 1 1 d . . . . .
C00E C 0.0571(4) 0.6120(3) 0.1826(3) 0.0507(8) Uani 1 1 d . . . . .
H00E H -0.0487 0.6374 0.1996 0.061 Uiso 1 1 calc R . . . .
C00F C 0.5717(4) 0.7221(4) 0.4943(3) 0.0545(9) Uani 1 1 d . . . . .
C00G C 0.4658(4) 0.8065(4) 0.4407(3) 0.0561(9) Uani 1 1 d . . . . .
C00H C 0.4304(4) 0.9446(4) 0.1686(4) 0.0611(10) Uani 1 1 d . . . . .
C00I C 0.6856(5) 0.6490(4) 0.4388(4) 0.0648(10) Uani 1 1 d . . . . .
H00I H 0.7003 0.6530 0.3647 0.078 Uiso 1 1 calc R . . . .
C00J C 0.2188(6) 0.4473(5) 0.0743(4) 0.0691(11) Uani 1 1 d . . . . .
H00J H 0.3092 0.5166 0.0745 0.083 Uiso 1 1 calc R . . . .
C00K C -0.0594(6) 0.3670(4) 0.1235(3) 0.0671(11) Uani 1 1 d . . . . .
C00L C 0.5534(6) 0.7169(5) 0.6063(4) 0.0751(12) Uani 1 1 d . . . . .
H00L H 0.4764 0.7649 0.6454 0.090 Uiso 1 1 calc R . . . .
C00M C -0.0364(5) 1.0887(5) 0.3691(5) 0.0852(16) Uani 1 1 d . . . . .
H00D H -0.1075 1.0971 0.3070 0.128 Uiso 1 1 calc GR . . . .
H00F H 0.0096 1.1771 0.4071 0.128 Uiso 1 1 calc GR . . . .
H00G H -0.1028 1.0400 0.4182 0.128 Uiso 1 1 calc GR . . . .
C00N C 0.7792(6) 0.5692(5) 0.4918(5) 0.0845(14) Uani 1 1 d . . . . .
H00N H 0.8539 0.5185 0.4530 0.101 Uiso 1 1 calc R . . . .
C00O C -0.0449(8) 0.2385(5) 0.0701(4) 0.0878(15) Uani 1 1 d . . . . .
H00O H -0.1346 0.1685 0.0689 0.105 Uiso 1 1 calc R . . . .
C00P C 0.2323(8) 0.3179(6) 0.0212(4) 0.0935(17) Uani 1 1 d . . . . .
H00P H 0.3317 0.3010 -0.0135 0.112 Uiso 1 1 calc R . . . .
C00Q C 0.6504(7) 0.6402(6) 0.6582(5) 0.0948(16) Uani 1 1 d . . . . .
H00Q H 0.6406 0.6389 0.7332 0.114 Uiso 1 1 calc R . . . .
C00R C 0.1001(9) 0.2146(5) 0.0196(5) 0.0978(18) Uani 1 1 d . . . . .
H00R H 0.1099 0.1281 -0.0163 0.117 Uiso 1 1 calc R . . . .
C00S C 0.7605(7) 0.5659(6) 0.6017(5) 0.0918(16) Uani 1 1 d . . . . .
H00S H 0.8230 0.5129 0.6377 0.110 Uiso 1 1 calc R . . . .


_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
Cl01 C00K 1.732(5) . ?
F002 C00H 1.322(5) . ?
O003 C00A 1.193(4) . ?
F004 C00H 1.327(4) . ?
F005 C00H 1.338(4) . ?
O006 C00A 1.335(4) . ?
O006 C00M 1.438(4) . ?
N007 N008 1.385(4) . ?
N007 C00E 1.266(4) . ?
N008 C00A 1.373(4) . ?
N008 C00B 1.466(4) . ?
O009 C00G 1.204(4) . ?
C00B H00B 0.9800 . ?
C00B C00C 1.519(5) . ?
C00B C00H 1.518(5) . ?
C00C H00A 0.9700 . ?
C00C H00C 0.9700 . ?
C00C C00G 1.511(5) . ?
C00D C00E 1.472(5) . ?
C00D C00J 1.381(5) . ?
C00D C00K 1.398(5) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.487(5) . ?
C00F C00I 1.373(5) . ?
C00F C00L 1.399(6) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.389(6) . ?
C00J H00J 0.9300 . ?
C00J C00P 1.387(6) . ?
C00K C00O 1.381(6) . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.376(7) . ?
C00M H00D 0.9600 . ?
C00M H00F 0.9600 . ?
C00M H00G 0.9600 . ?
C00N H00N 0.9300 . ?
C00N C00S 1.369(7) . ?
C00O H00O 0.9300 . ?
C00O C00R 1.355(8) . ?
C00P H00P 0.9300 . ?
C00P C00R 1.371(8) . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.364(8) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?

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
C00A O006 C00M 116.0(3) . . ?
C00E N007 N008 123.6(3) . . ?
N007 N008 C00B 112.6(2) . . ?
C00A N008 N007 124.8(3) . . ?
C00A N008 C00B 122.6(3) . . ?
O003 C00A O006 123.8(3) . . ?
O003 C00A N008 125.3(3) . . ?
O006 C00A N008 110.9(3) . . ?
N008 C00B H00B 107.8 . . ?
N008 C00B C00C 112.6(3) . . ?
N008 C00B C00H 109.4(3) . . ?
C00C C00B H00B 107.8 . . ?
C00H C00B H00B 107.8 . . ?
C00H C00B C00C 111.4(3) . . ?
C00B C00C H00A 109.1 . . ?
C00B C00C H00C 109.1 . . ?
H00A C00C H00C 107.9 . . ?
C00G C00C C00B 112.4(3) . . ?
C00G C00C H00A 109.1 . . ?
C00G C00C H00C 109.1 . . ?
C00J C00D C00E 121.1(4) . . ?
C00J C00D C00K 117.2(4) . . ?
C00K C00D C00E 121.7(3) . . ?
N007 C00E C00D 117.4(3) . . ?
N007 C00E H00E 121.3 . . ?
C00D C00E H00E 121.3 . . ?
C00I C00F C00G 123.1(4) . . ?
C00I C00F C00L 118.7(4) . . ?
C00L C00F C00G 118.2(4) . . ?
O009 C00G C00C 120.7(4) . . ?
O009 C00G C00F 121.4(4) . . ?
C00F C00G C00C 117.9(3) . . ?
F002 C00H F004 106.5(4) . . ?
F002 C00H F005 106.7(3) . . ?
F002 C00H C00B 114.3(3) . . ?
F004 C00H F005 106.7(3) . . ?
F004 C00H C00B 111.9(3) . . ?
F005 C00H C00B 110.3(3) . . ?
C00F C00I H00I 119.5 . . ?
C00F C00I C00N 121.0(4) . . ?
C00N C00I H00I 119.5 . . ?
C00D C00J H00J 119.6 . . ?
C00D C00J C00P 120.8(5) . . ?
C00P C00J H00J 119.6 . . ?
C00D C00K Cl01 120.3(3) . . ?
C00O C00K Cl01 118.1(4) . . ?
C00O C00K C00D 121.5(4) . . ?
C00F C00L H00L 120.3 . . ?
C00Q C00L C00F 119.5(5) . . ?
C00Q C00L H00L 120.3 . . ?
O006 C00M H00D 109.5 . . ?
O006 C00M H00F 109.5 . . ?
O006 C00M H00G 109.5 . . ?
H00D C00M H00F 109.5 . . ?
H00D C00M H00G 109.5 . . ?
H00F C00M H00G 109.5 . . ?
C00I C00N H00N 120.3 . . ?
C00S C00N C00I 119.5(5) . . ?
C00S C00N H00N 120.3 . . ?
C00K C00O H00O 120.0 . . ?
C00R C00O C00K 120.0(5) . . ?
C00R C00O H00O 120.0 . . ?
C00J C00P H00P 119.8 . . ?
C00R C00P C00J 120.4(5) . . ?
C00R C00P H00P 119.8 . . ?
C00L C00Q H00Q 119.4 . . ?
C00S C00Q C00L 121.1(5) . . ?
C00S C00Q H00Q 119.4 . . ?
C00O C00R C00P 120.1(5) . . ?
C00O C00R H00R 120.0 . . ?
C00P C00R H00R 120.0 . . ?
C00N C00S H00S 120.0 . . ?
C00Q C00S C00N 120.1(5) . . ?
C00Q C00S H00S 120.0 . . ?

_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 4.747
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_fhh-20210519
_database_code_depnum_ccdc_archive 'CCDC 2169816'
loop_
_audit_author_name
_audit_author_address
'Bo Zhu'
;Bo zhu
China
;
_audit_update_record             
;
2022-05-02 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-06-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H17 F3 N2 O3'
_chemical_formula_sum            'C19 H17 F3 N2 O3'
_chemical_formula_weight         378.34
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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      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                   12.6089(2)
_cell_length_b                   5.61820(10)
_cell_length_c                   13.0437(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.762(2)
_cell_angle_gamma                90
_cell_volume                     893.51(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3790
_cell_measurement_theta_min      5.6410
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23354
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         84.532
_diffrn_reflns_theta_min         3.504
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  36.00   1.00    1.00    --  -35.62  24.00 -24.00   97
  2  ω   -107.00 -10.00   1.00    1.00    --  -35.62 -24.00 170.00   97
  3  ω    -36.00  61.00   1.00    1.00    --   35.62 -24.00 170.00   97
  4  ω     10.00 107.00   1.00    1.00    --   35.62  24.00 -24.00   97
  5  ω     36.00 133.00   1.00    1.70    --  107.12 -24.00 170.00   97
  6  ω     81.00 178.00   1.00    1.70    --  107.12  24.00 -24.00   97
  7  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 120.00   84
  8  ω    -52.00  32.00   1.00    1.00    --  -35.62  57.00  30.00   84
  9  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-180.00   94
 10  ω     19.00 103.00   1.00    1.00    --   35.62  57.00 120.00   84
 11  ω     19.00 103.00   1.00    1.00    --   35.62  57.00  60.00   84
 12  ω      9.00 103.00   1.00    1.00    --   35.62  77.00   0.00   94
 13  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-150.00   84
 14  ω     55.00 108.00   1.00    1.00    --   35.62-178.00 120.00   53
 15  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-180.00   84
 16  ω      9.00 103.00   1.00    1.00    --   35.62  77.00  60.00   94
 17  ω     55.00 108.00   1.00    1.00    --   35.62-178.00-180.00   53
 18  ω      2.00  32.00   1.00    1.00    --   35.62  90.00 170.05   30
 19  ω     80.00 175.00   1.00    1.70    --  107.12  77.00 120.00   95
 20  ω     84.00 174.00   1.00    1.70    --  107.12  71.00  16.00   90
 21  ω     80.00 175.00   1.00    1.70    --  107.12  77.00  60.00   95
 22  ω     86.00 177.00   1.00    1.70    --  107.12  30.00 150.00   91
 23  ω     80.00 175.00   1.00    1.70    --  107.12  77.00 -30.00   95
 24  ω     40.00 134.00   1.00    1.70    --  107.12 -77.00-150.00   94
 25  ω     90.00 175.00   1.00    1.70    --  107.12  48.00   7.35   85
 26  ω     86.00 177.00   1.00    1.70    --  107.12  30.00 120.00   91
 27  ω     37.00 113.00   1.00    1.70    --  107.12-111.00   0.00   76
 28  ω     38.00 110.00   1.00    1.70    --  107.12 -95.00-180.00   72
 29  ω     90.00 176.00   1.00    1.70    --  107.12  45.00  90.00   86
 30  ω     86.00 177.00   1.00    1.70    --  107.12  30.00  90.00   91
 31  ω     89.00 174.00   1.00    1.70    --  107.12  61.00  90.00   85
 32  ω     86.00 177.00   1.00    1.70    --  107.12  30.00  30.00   91
 33  ω     80.00 175.00   1.00    1.70    --  107.12  77.00   0.00   95
 34  ω     80.00 175.00   1.00    1.70    --  107.12  77.00  30.00   95
 35  ω     89.00 174.00   1.00    1.70    --  107.12  61.00 120.00   85
 36  ω     89.00 174.00   1.00    1.70    --  107.12  61.00   0.00   85
 37  ω     89.00 174.00   1.00    1.70    --  107.12  61.00  60.00   85
 38  ω     80.00 175.00   1.00    1.70    --  107.12  77.00  90.00   95
 39  ω     88.00 174.00   1.00    1.70    --  107.12  64.00   0.13   86
 40  ω     86.00 177.00   1.00    1.70    --  107.12  30.00  60.00   91
 41  ω     86.00 177.00   1.00    1.70    --  107.12  32.00  67.63   91
 42  ω     85.00 177.00   1.00    1.70    --  107.12  29.00 167.71   92
 43  ω     37.00 113.00   1.00    1.70    --  107.12-111.00-180.00   76
 44  ω   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00  60.00   94
 45  ω     -1.00  26.00   1.00    1.00    --   35.62  94.00   4.02   27
 46  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -90.00   94
 47  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00   0.00   74
 48  ω     19.00 103.00   1.00    1.00    --   35.62  57.00 -30.00   84
 49  ω    -36.00  65.00   1.00    1.00    --   35.62 -19.00  60.00  101
 50  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
 51  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-150.00   94
 52  ω    -32.00  52.00   1.00    1.00    --   35.62 -57.00-180.00   84
 53  ω      6.00 107.00   1.00    1.00    --   35.62  19.00-120.00  101
 54  ω     55.00 108.00   1.00    1.00    --   35.62-178.00   0.00   53
 55  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
 56  ω     55.00 108.00   1.00    1.00    --   35.62-178.00-120.00   53
 57  ω     17.00 105.00   1.00    1.00    --   35.62  38.00 -30.00   88
 58  ω     89.00 174.00   1.00    1.70    --  107.12  61.00-120.00   85
 59  ω     80.00 175.00   1.00    1.70    --  107.12  77.00 -90.00   95
 60  ω     80.00 175.00   1.00    1.70    --  107.12  77.00 150.00   95
 61  ω     89.00 174.00   1.00    1.70    --  107.12  61.00-180.00   85
 62  ω     80.00 175.00   1.00    1.70    --  107.12  77.00 -60.00   95
 63  ω     80.00 175.00   1.00    1.70    --  107.12  77.00-150.00   95
 64  ω     90.00 176.00   1.00    1.70    --  107.12  45.00-180.00   86
 65  ω     80.00 175.00   1.00    1.70    --  107.12  77.00-120.00   95
 66  ω     40.00 134.00   1.00    1.70    --  107.12 -77.00   0.00   94
 67  ω     90.00 176.00   1.00    1.70    --  107.12  45.00-150.00   86
 68  ω     89.00 174.00   1.00    1.70    --  107.12  61.00 -90.00   85
 69  ω    100.00 177.00   1.00    1.70    --  107.12 111.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180027000
_diffrn_orient_matrix_UB_12      0.0274118000
_diffrn_orient_matrix_UB_13      0.1207301000
_diffrn_orient_matrix_UB_21      0.1184088000
_diffrn_orient_matrix_UB_22      0.0839111000
_diffrn_orient_matrix_UB_23      0.0094301000
_diffrn_orient_matrix_UB_31      -0.0401574000
_diffrn_orient_matrix_UB_32      0.2596786000
_diffrn_orient_matrix_UB_33      -0.0158049000
_diffrn_oxdiff_digest_frames     
;
01f437061bf3629f41c706cf7a8e0b9e320003661e2
;
_diffrn_oxdiff_digest_hkl        
;
010a00cf5c1ffcefa1ea9ee44f9256e72131c9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.726
_reflns_number_gt                3054
_reflns_number_total             3255
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.139
_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)+(0.0528P)²+0.1321P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N006(H006)
2.b Ternary CH refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00F(H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.d Idealised Me refined as rotating group:
 C00R(H00A,H00C,H00H)
;
_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
O001 O 0.28276(18) 0.1598(4) 0.35336(16) 0.0516(5) Uani 1 1 d . . . . .
F002 F 0.60156(14) 0.5353(7) 0.29281(19) 0.0940(9) Uani 1 1 d . . . . .
F003 F 0.51430(18) 0.8414(5) 0.3242(2) 0.0862(8) Uani 1 1 d . . . . .
N004 N 0.37928(17) 0.5504(5) 0.16701(17) 0.0463(6) Uani 1 1 d . . . . .
F005 F 0.54736(16) 0.5523(7) 0.43542(16) 0.0942(9) Uani 1 1 d . . . . .
N006 N 0.29284(18) 0.7181(5) 0.14738(18) 0.0468(6) Uani 1 1 d . . . . .
H006 H 0.3123 0.8635 0.1427 0.056 Uiso 1 1 d R . . . .
O007 O 0.3406(2) 0.4633(6) -0.00540(18) 0.0786(9) Uani 1 1 d . . . . .
O008 O 0.4386(2) 0.2035(7) 0.1134(2) 0.0853(9) Uani 1 1 d . . . . .
C009 C 0.2742(2) 0.3635(5) 0.3798(2) 0.0379(6) Uani 1 1 d . . . . .
C00A C 0.13074(19) 0.5198(5) 0.18648(19) 0.0370(6) Uani 1 1 d . . . . .
C00B C 0.23131(19) 0.6730(5) 0.22738(19) 0.0380(6) Uani 1 1 d . . . . .
H00B H 0.2072 0.8267 0.2488 0.046 Uiso 1 1 calc R . . . .
C00C C 0.2183(2) 0.4187(5) 0.4647(2) 0.0395(6) Uani 1 1 d . . . . .
C00D C 0.1302(2) 0.3134(5) 0.1283(2) 0.0451(7) Uani 1 1 d . . . . .
H00D H 0.1945 0.2636 0.1122 0.054 Uiso 1 1 calc R . . . .
C00E C 0.31887(19) 0.5658(5) 0.32533(19) 0.0374(6) Uani 1 1 d . . . . .
H00E H 0.3457 0.6927 0.3770 0.045 Uiso 1 1 calc R . . . .
C00F C 0.4125(2) 0.4836(6) 0.2786(2) 0.0441(7) Uani 1 1 d . . . . .
H00F H 0.4212 0.3106 0.2855 0.053 Uiso 1 1 calc R . . . .
C00G C 0.2392(3) 0.6235(6) 0.5257(3) 0.0573(8) Uani 1 1 d . . . . .
H00G H 0.2854 0.7399 0.5105 0.069 Uiso 1 1 calc R . . . .
C00H C 0.5194(2) 0.6064(8) 0.3322(3) 0.0636(11) Uani 1 1 d . . . . .
C00I C 0.0341(2) 0.5877(7) 0.2096(2) 0.0517(8) Uani 1 1 d . . . . .
H00I H 0.0329 0.7249 0.2491 0.062 Uiso 1 1 calc R . . . .
C00J C 0.3888(3) 0.3869(8) 0.0915(3) 0.0612(9) Uani 1 1 d . . . . .
C00K C 0.1462(3) 0.2522(7) 0.4868(3) 0.0578(8) Uani 1 1 d . . . . .
H00K H 0.1306 0.1148 0.4460 0.069 Uiso 1 1 calc R . . . .
C00L C 0.1209(3) 0.4879(8) 0.6305(3) 0.0651(10) Uani 1 1 d . . . . .
H00L H 0.0892 0.5100 0.6868 0.078 Uiso 1 1 calc R . . . .
C00M C 0.0360(3) 0.1808(7) 0.0939(2) 0.0553(8) Uani 1 1 d . . . . .
H00M H 0.0370 0.0425 0.0550 0.066 Uiso 1 1 calc R . . . .
C00N C -0.0600(3) 0.2522(8) 0.1170(3) 0.0646(10) Uani 1 1 d . . . . .
H00N H -0.1237 0.1631 0.0933 0.078 Uiso 1 1 calc R . . . .
C00O C 0.1914(3) 0.6551(8) 0.6092(3) 0.0713(11) Uani 1 1 d . . . . .
H00O H 0.2073 0.7908 0.6511 0.086 Uiso 1 1 calc R . . . .
C00P C -0.0608(3) 0.4552(9) 0.1750(3) 0.0684(11) Uani 1 1 d . . . . .
H00P H -0.1252 0.5040 0.1910 0.082 Uiso 1 1 calc R . . . .
C00Q C 0.0972(3) 0.2879(8) 0.5687(3) 0.0677(10) Uani 1 1 d . . . . .
H00Q H 0.0480 0.1762 0.5821 0.081 Uiso 1 1 calc R . . . .
C00R C 0.3583(4) 0.3157(14) -0.0902(4) 0.112(2) Uani 1 1 d . . . . .
H00A H 0.3159 0.3760 -0.1570 0.169 Uiso 1 1 calc GR . . . .
H00C H 0.3360 0.1554 -0.0808 0.169 Uiso 1 1 calc GR . . . .
H00H H 0.4347 0.3175 -0.0892 0.169 Uiso 1 1 calc GR . . . .


_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
O001 C009 1.208(4) . ?
F002 C00H 1.329(4) . ?
F003 C00H 1.324(5) . ?
N004 N006 1.414(3) . ?
N004 C00F 1.458(3) . ?
N004 C00J 1.374(5) . ?
F005 C00H 1.336(4) . ?
N006 H006 0.8599 . ?
N006 C00B 1.472(3) . ?
O007 C00J 1.327(4) . ?
O007 C00R 1.445(5) . ?
O008 C00J 1.203(5) . ?
C009 C00C 1.489(4) . ?
C009 C00E 1.523(4) . ?
C00A C00B 1.513(4) . ?
C00A C00D 1.385(4) . ?
C00A C00I 1.381(4) . ?
C00B H00B 0.9800 . ?
C00B C00E 1.580(3) . ?
C00C C00G 1.386(4) . ?
C00C C00K 1.385(4) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.378(4) . ?
C00E H00E 0.9800 . ?
C00E C00F 1.531(3) . ?
C00F H00F 0.9800 . ?
C00F C00H 1.517(4) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.384(4) . ?
C00I H00I 0.9300 . ?
C00I C00P 1.384(5) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.378(5) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.369(5) . ?
C00L C00Q 1.370(6) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.378(5) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.370(6) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00A 0.9600 . ?
C00R H00C 0.9600 . ?
C00R H00H 0.9600 . ?

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
N006 N004 C00F 111.4(2) . . ?
C00J N004 N006 121.3(2) . . ?
C00J N004 C00F 119.2(3) . . ?
N004 N006 H006 115.2 . . ?
N004 N006 C00B 106.1(2) . . ?
C00B N006 H006 115.2 . . ?
C00J O007 C00R 114.9(4) . . ?
O001 C009 C00C 120.2(3) . . ?
O001 C009 C00E 120.2(2) . . ?
C00C C009 C00E 119.5(2) . . ?
C00D C00A C00B 123.8(2) . . ?
C00I C00A C00B 118.2(3) . . ?
C00I C00A C00D 118.0(3) . . ?
N006 C00B C00A 113.2(2) . . ?
N006 C00B H00B 108.0 . . ?
N006 C00B C00E 104.65(19) . . ?
C00A C00B H00B 108.0 . . ?
C00A C00B C00E 114.8(2) . . ?
C00E C00B H00B 108.0 . . ?
C00G C00C C009 122.9(2) . . ?
C00K C00C C009 118.3(3) . . ?
C00K C00C C00G 118.7(3) . . ?
C00A C00D H00D 119.5 . . ?
C00M C00D C00A 121.0(3) . . ?
C00M C00D H00D 119.5 . . ?
C009 C00E C00B 113.4(2) . . ?
C009 C00E H00E 109.1 . . ?
C009 C00E C00F 112.0(2) . . ?
C00B C00E H00E 109.1 . . ?
C00F C00E C00B 104.13(19) . . ?
C00F C00E H00E 109.1 . . ?
N004 C00F C00E 105.4(2) . . ?
N004 C00F H00F 110.1 . . ?
N004 C00F C00H 109.8(2) . . ?
C00E C00F H00F 110.1 . . ?
C00H C00F C00E 111.4(3) . . ?
C00H C00F H00F 110.1 . . ?
C00C C00G H00G 120.0 . . ?
C00O C00G C00C 120.0(3) . . ?
C00O C00G H00G 120.0 . . ?
F002 C00H F005 106.9(3) . . ?
F002 C00H C00F 111.9(3) . . ?
F003 C00H F002 107.2(3) . . ?
F003 C00H F005 107.5(4) . . ?
F003 C00H C00F 113.4(3) . . ?
F005 C00H C00F 109.6(3) . . ?
C00A C00I H00I 119.4 . . ?
C00A C00I C00P 121.2(3) . . ?
C00P C00I H00I 119.4 . . ?
O007 C00J N004 111.4(4) . . ?
O008 C00J N004 122.6(3) . . ?
O008 C00J O007 126.0(4) . . ?
C00C C00K H00K 119.6 . . ?
C00Q C00K C00C 120.7(3) . . ?
C00Q C00K H00K 119.6 . . ?
C00O C00L H00L 120.0 . . ?
C00O C00L C00Q 119.9(3) . . ?
C00Q C00L H00L 120.0 . . ?
C00D C00M H00M 119.9 . . ?
C00D C00M C00N 120.3(3) . . ?
C00N C00M H00M 119.9 . . ?
C00M C00N H00N 120.2 . . ?
C00P C00N C00M 119.5(3) . . ?
C00P C00N H00N 120.2 . . ?
C00G C00O H00O 119.8 . . ?
C00L C00O C00G 120.5(4) . . ?
C00L C00O H00O 119.8 . . ?
C00I C00P H00P 120.0 . . ?
C00N C00P C00I 120.0(3) . . ?
C00N C00P H00P 120.0 . . ?
C00K C00Q H00Q 120.0 . . ?
C00L C00Q C00K 120.1(3) . . ?
C00L C00Q H00Q 120.0 . . ?
O007 C00R H00A 109.5 . . ?
O007 C00R H00C 109.5 . . ?
O007 C00R H00H 109.5 . . ?
H00A C00R H00C 109.5 . . ?
H00A C00R H00H 109.5 . . ?
H00C C00R H00H 109.5 . . ?

_olex2_date_sample_data_collection 2021-05-20
_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 2.743
_oxdiff_exptl_absorpt_empirical_full_min 0.644
