# 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_zq-5-120
_database_code_depnum_ccdc_archive 'CCDC 2108432'
loop_
_audit_author_name
_audit_author_address
'Yajun Li'
;Fujian Institute of Research on the Structure of Matter(FJIRSM)
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2020-09-04
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H17 F3 O3'
_chemical_formula_sum            'C22 H17 F3 O3'
_chemical_formula_weight         386.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0147 0.0070 '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 0.0599 0.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   11.6118(11)
_cell_length_b                   9.7486(8)
_cell_length_c                   17.4474(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.403(9)
_cell_angle_gamma                90
_cell_volume                     1928.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13440
_cell_measurement_temperature    290.00(14)
_cell_measurement_theta_max      60.5890
_cell_measurement_theta_min      4.5290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.591
_diffrn_reflns_theta_min         4.512
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_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  87.00   0.50    0.20    --   72.03  57.00   0.00   52
  2  ω     96.00 139.00   0.50    0.20    --   72.03  57.00   0.00   86
  3  ω     81.00 143.00   0.50    0.20    --   72.03 125.00  90.00  124
  4  ω     91.00 121.00   0.50    0.20    --   72.03  93.00  75.00   60
  5  ω     49.00 103.00   0.50    0.20    --   72.03 -93.00 -36.00  108
  6  ω     21.00 106.00   0.50    0.20    --   72.03-125.00 -60.00  170
  7  ω     27.00  53.00   0.50    0.20    --   72.03-125.00-180.00   52
  8  ω     56.00  86.00   0.50    0.20    --   72.03-125.00-180.00   60
  9  ω     21.00  47.00   0.50    0.20    --   72.03 -93.00 -36.00   52
 10  ω     30.00  94.00   0.50    0.20    --   72.03 -77.00  30.00  128
 11  ω      0.00  43.00   0.50    0.20    --   72.03 -38.00 120.00   86
 12  ω     -3.00  22.00   0.50    0.20    --   72.03 -19.00 120.00   50
 13  ω     -3.00  26.00   0.50    0.20    --   72.03 -19.00  30.00   58
 14  ω     -3.00  25.00   0.50    0.20    --   72.03 -19.00   0.00   56
 15  ω     -2.00  26.00   0.50    0.20    --   72.03 -19.00 -30.00   56
 16  ω     -3.00  26.00   0.50    0.20    --   72.03 -19.00-120.00   58
 17  ω    -11.00  15.00   0.50    0.05    --   -1.72 -57.00-150.00   52
 18  ω    -29.00  11.00   0.50    0.05    --   -1.72 -93.00 -36.00   80
 19  ω    -69.00 -43.00   0.50    0.05    --   -1.72 -57.00-150.00   52
 20  ω   -112.00 -85.00   0.50    0.20    --  -75.46 -93.00 -36.00   54
 21  ω    -26.00  -1.00   0.50    0.20    --  -75.46  19.00 -90.00   50
 22  ω    -66.00 -16.00   0.50    0.20    --  -75.46  57.00-180.00  100
 23  ω    -98.00 -30.00   0.50    0.20    --  -75.46  77.00-150.00  136
 24  ω    -30.00  -5.00   0.50    0.20    --  -75.46  38.00 -90.00   50
 25  ω    -52.00  -7.00   0.50    0.20    --  -75.46  57.00 -60.00   90
 26  ω    -62.00  -7.00   0.50    0.20    --  -75.46  57.00   0.00  110
 27  ω    -42.00  -6.00   0.50    0.20    --  -75.46  38.00  60.00   72
 28  ω    -43.00  -5.00   0.50    0.20    --  -75.46  38.00 120.00   76
 29  ω     40.00  71.00   0.50    0.05    --   -1.72  57.00 -30.00   62
 30  ω    -12.00  22.00   0.50    0.05    --   -1.72  57.00 -30.00   68
 31  ω    -25.00   0.00   0.50    0.20    --  -75.46  19.00-150.00   50
 32  ω    -26.00  -1.00   0.50    0.20    --  -75.46  19.00-180.00   50
 33  ω   -106.00 -23.00   0.50    0.20    --  -75.46 125.00-180.00  166
 34  ω   -109.00 -23.00   0.50    0.20    --  -75.46 125.00   0.00  172
 35  ω    -42.00 -15.00   0.50    0.20    --  -75.46  93.00  75.00   54
 36  ω    -72.00 -46.00   0.50    0.20    --  -75.46  93.00  75.00   52
 37  ω    -32.00  30.00   0.50    0.05    --   -1.72  93.00  75.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328709000
_diffrn_orient_matrix_UB_12      -0.0664310000
_diffrn_orient_matrix_UB_13      0.0683808000
_diffrn_orient_matrix_UB_21      -0.0915393000
_diffrn_orient_matrix_UB_22      0.0545625000
_diffrn_orient_matrix_UB_23      0.0245799000
_diffrn_orient_matrix_UB_31      -0.0670013000
_diffrn_orient_matrix_UB_32      -0.1071946000
_diffrn_orient_matrix_UB_33      -0.0298906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3265
_reflns_number_total             4396
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.129
_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)+(0.0759P)²+0.4678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1733
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C8(H8), C25(H25), C7(H7), C23(H23), C26(H26), C27(H27),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O21 O 0.44317(15) 0.22979(13) 0.66641(8) 0.0676(4) Uani 1 1 d . . . . .
O22 O 0.51339(13) 0.38400(14) 0.84557(7) 0.0628(4) Uani 1 1 d . . . . .
O19 O 0.41467(15) 0.30211(14) 0.54301(7) 0.0709(4) Uani 1 1 d . . . . .
F18 F 0.28923(16) 0.5358(3) 0.85802(10) 0.1269(7) Uani 1 1 d . . . . .
C1 C 0.51565(16) 0.43276(16) 0.78187(10) 0.0481(4) Uani 1 1 d . . . . .
C3 C 0.40940(16) 0.47031(17) 0.63989(10) 0.0482(4) Uani 1 1 d . . . . .
F16 F 0.17075(17) 0.5925(2) 0.75385(12) 0.1264(7) Uani 1 1 d . . . . .
C10 C 0.62865(16) 0.45122(17) 0.75670(10) 0.0510(4) Uani 1 1 d . . . . .
C11 C 0.42333(16) 0.31995(17) 0.61906(10) 0.0494(4) Uani 1 1 d . . . . .
C12 C 0.30365(18) 0.53236(19) 0.59067(11) 0.0574(5) Uani 1 1 d . . . . .
C13 C 0.2192(2) 0.5935(2) 0.55665(12) 0.0630(5) Uani 1 1 d . . . . .
C2 C 0.40226(15) 0.48009(18) 0.72728(9) 0.0480(4) Uani 1 1 d . . . . .
H2 H 0.393240 0.577572 0.738395 0.058 Uiso 1 1 calc R U . . .
F17 F 0.14124(16) 0.4120(2) 0.81183(13) 0.1377(8) Uani 1 1 d . . . . .
C4 C 0.51911(18) 0.55096(19) 0.62837(11) 0.0564(5) Uani 1 1 d . . . . .
H4A H 0.527809 0.539321 0.574690 0.068 Uiso 1 1 calc R U . . .
H4B H 0.506958 0.647824 0.636600 0.068 Uiso 1 1 calc R U . . .
C5 C 0.63040(17) 0.50572(18) 0.68300(11) 0.0553(4) Uani 1 1 d . . . . .
C24 C 0.11633(19) 0.6676(2) 0.51828(12) 0.0633(5) Uani 1 1 d . . . . .
C9 C 0.73320(18) 0.4112(2) 0.80700(13) 0.0664(5) Uani 1 1 d . . . . .
H9 H 0.731138 0.373416 0.855625 0.080 Uiso 1 1 calc R U . . .
C14 C 0.29387(17) 0.4066(2) 0.74506(12) 0.0611(5) Uani 1 1 d . . . . .
H14A H 0.241661 0.382256 0.695715 0.073 Uiso 1 1 calc R U . . .
H14B H 0.319700 0.321985 0.772719 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7391(2) 0.5195(3) 0.66200(15) 0.0792(7) Uani 1 1 d . . . . .
H6 H 0.742483 0.554612 0.612962 0.095 Uiso 1 1 calc R U . . .
C15 C 0.2263(2) 0.4866(3) 0.79210(14) 0.0783(7) Uani 1 1 d . . . . .
C8 C 0.8392(2) 0.4271(3) 0.78539(18) 0.0857(7) Uani 1 1 d . . . . .
H8 H 0.908955 0.401168 0.819376 0.103 Uiso 1 1 calc R U . . .
C25 C 0.0160(2) 0.6687(3) 0.54873(16) 0.0878(7) Uani 1 1 d . . . . .
H25 H 0.015280 0.620346 0.594595 0.105 Uiso 1 1 calc R U . . .
C20 C 0.4340(3) 0.1635(2) 0.51828(14) 0.0901(8) Uani 1 1 d . . . . .
H20A H 0.425268 0.161375 0.462317 0.135 Uiso 1 1 calc R U . . .
H20B H 0.377376 0.102969 0.533183 0.135 Uiso 1 1 calc R U . . .
H20C H 0.512154 0.134420 0.542979 0.135 Uiso 1 1 calc R U . . .
C7 C 0.8416(2) 0.4815(3) 0.71331(19) 0.0968(9) Uani 1 1 d . . . . .
H7 H 0.913575 0.492975 0.698829 0.116 Uiso 1 1 calc R U . . .
C23 C 0.1132(3) 0.7369(3) 0.44925(18) 0.1039(10) Uani 1 1 d . . . . .
H23 H 0.179271 0.737646 0.427134 0.125 Uiso 1 1 calc R U . . .
C26 C -0.0828(2) 0.7397(3) 0.51252(18) 0.0973(9) Uani 1 1 d . . . . .
H26 H -0.148852 0.740677 0.534642 0.117 Uiso 1 1 calc R U . . .
C27 C -0.0847(3) 0.8083(3) 0.4449(2) 0.1041(10) Uani 1 1 d . . . . .
H27 H -0.151540 0.857008 0.420655 0.125 Uiso 1 1 calc R U . . .
C28 C 0.0119(3) 0.8054(4) 0.4126(2) 0.1308(14) Uani 1 1 d . . . . .
H28 H 0.009943 0.850089 0.365197 0.157 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
O21 C11 1.194(2) . ?
O22 C1 1.214(2) . ?
O19 C11 1.321(2) . ?
O19 C20 1.450(2) . ?
F18 C15 1.314(3) . ?
C1 C10 1.481(2) . ?
C1 C2 1.521(2) . ?
C3 C11 1.527(2) . ?
C3 C12 1.469(3) . ?
C3 C2 1.548(2) . ?
C3 C4 1.547(2) . ?
F16 C15 1.320(3) . ?
C10 C5 1.395(3) . ?
C10 C9 1.392(3) . ?
C12 C13 1.191(3) . ?
C13 C24 1.433(3) . ?
C2 H2 0.9800 . ?
C2 C14 1.537(2) . ?
F17 C15 1.330(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.498(3) . ?
C5 C6 1.395(3) . ?
C24 C25 1.381(3) . ?
C24 C23 1.374(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.372(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.474(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.371(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7 H7 0.9300 . ?
C23 H23 0.9300 . ?
C23 C28 1.384(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.353(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.360(5) . ?
C28 H28 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
C11 O19 C20 116.00(15) . . ?
O22 C1 C10 120.90(17) . . ?
O22 C1 C2 120.39(16) . . ?
C10 C1 C2 118.69(14) . . ?
C11 C3 C2 108.93(13) . . ?
C11 C3 C4 108.95(14) . . ?
C12 C3 C11 111.97(15) . . ?
C12 C3 C2 109.62(14) . . ?
C12 C3 C4 108.85(14) . . ?
C4 C3 C2 108.46(14) . . ?
C5 C10 C1 120.57(16) . . ?
C9 C10 C1 119.15(17) . . ?
C9 C10 C5 120.27(18) . . ?
O21 C11 O19 124.05(16) . . ?
O21 C11 C3 123.81(15) . . ?
O19 C11 C3 112.11(14) . . ?
C13 C12 C3 173.0(2) . . ?
C12 C13 C24 178.0(2) . . ?
C1 C2 C3 112.08(13) . . ?
C1 C2 H2 106.6 . . ?
C1 C2 C14 111.62(14) . . ?
C3 C2 H2 106.6 . . ?
C14 C2 C3 112.93(15) . . ?
C14 C2 H2 106.6 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.94(14) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C10 C5 C4 121.14(16) . . ?
C6 C5 C10 118.2(2) . . ?
C6 C5 C4 120.69(18) . . ?
C25 C24 C13 120.8(2) . . ?
C23 C24 C13 121.3(2) . . ?
C23 C24 C25 117.9(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C2 C14 H14A 108.5 . . ?
C2 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C2 114.98(19) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
F18 C15 F16 106.1(3) . . ?
F18 C15 F17 106.1(2) . . ?
F18 C15 C14 114.73(19) . . ?
F16 C15 F17 104.4(2) . . ?
F16 C15 C14 113.2(2) . . ?
F17 C15 C14 111.6(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C28 120.2(3) . . ?
C28 C23 H23 119.9 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.6 . . ?

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
O22 C1 C10 C5 179.19(16) . . . . ?
O22 C1 C10 C9 0.3(3) . . . . ?
O22 C1 C2 C3 -151.70(16) . . . . ?
O22 C1 C2 C14 -23.9(2) . . . . ?
C1 C10 C5 C4 1.9(3) . . . . ?
C1 C10 C5 C6 -179.33(18) . . . . ?
C1 C10 C9 C8 -179.9(2) . . . . ?
C1 C2 C14 C15 100.2(2) . . . . ?
C3 C2 C14 C15 -132.49(18) . . . . ?
C3 C4 C5 C10 -28.9(2) . . . . ?
C3 C4 C5 C6 152.38(19) . . . . ?
C10 C1 C2 C3 30.1(2) . . . . ?
C10 C1 C2 C14 157.91(15) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C10 C9 C8 C7 -0.7(4) . . . . ?
C11 C3 C2 C1 63.89(18) . . . . ?
C11 C3 C2 C14 -63.21(19) . . . . ?
C11 C3 C4 C5 -64.22(19) . . . . ?
C12 C3 C11 O21 -131.6(2) . . . . ?
C12 C3 C11 O19 50.4(2) . . . . ?
C12 C3 C2 C1 -173.28(14) . . . . ?
C12 C3 C2 C14 59.61(19) . . . . ?
C12 C3 C4 C5 173.42(15) . . . . ?
C13 C24 C25 C26 179.8(3) . . . . ?
C13 C24 C23 C28 178.7(3) . . . . ?
C2 C1 C10 C5 -2.6(2) . . . . ?
C2 C1 C10 C9 178.50(16) . . . . ?
C2 C3 C11 O21 -10.2(2) . . . . ?
C2 C3 C11 O19 171.80(15) . . . . ?
C2 C3 C4 C5 54.21(19) . . . . ?
C2 C14 C15 F18 -53.0(3) . . . . ?
C2 C14 C15 F16 68.9(3) . . . . ?
C2 C14 C15 F17 -173.70(19) . . . . ?
C4 C3 C11 O21 107.9(2) . . . . ?
C4 C3 C11 O19 -70.06(19) . . . . ?
C4 C3 C2 C1 -54.55(18) . . . . ?
C4 C3 C2 C14 178.34(14) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C10 C9 C8 1.2(3) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C24 C25 C26 C27 1.4(5) . . . . ?
C24 C23 C28 C27 1.6(6) . . . . ?
C9 C10 C5 C4 -179.26(17) . . . . ?
C9 C10 C5 C6 -0.5(3) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C25 C24 C23 C28 0.3(5) . . . . ?
C25 C26 C27 C28 0.5(6) . . . . ?
C20 O19 C11 O21 -1.6(3) . . . . ?
C20 O19 C11 C3 176.35(19) . . . . ?
C23 C24 C25 C26 -1.8(4) . . . . ?
C26 C27 C28 C23 -2.0(7) . . . . ?

_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 1.932
_oxdiff_exptl_absorpt_empirical_full_min 0.645
####################################################################### 
# 
# 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_zq-6-55-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2108433'
loop_
_audit_author_name
_audit_author_address
'Yajun Li'
;Fujian Institute of Research on the Structure of Matter(FJIRSM)
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cl F3 O4'
_chemical_formula_sum            'C23 H18 Cl F3 O4'
_chemical_formula_weight         450.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOFCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9925(11)
_cell_length_b                   15.5533(14)
_cell_length_c                   16.006(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.451(14)
_cell_angle_gamma                90
_cell_volume                     2157.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.0620
_cell_measurement_theta_min      3.4950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.026
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18027
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.694
_diffrn_reflns_theta_min         3.508
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  -2.00   0.50    0.09    --  -74.78  75.00  67.00  186
  2  ω    -17.00  60.00   0.50    0.05    --   -0.62  75.00  67.00  154
  3  ω     99.00 143.00   0.50    0.09    --   73.53  75.00  67.00   88
  4  ω     64.00  90.00   0.50    0.09    --   73.53 -75.00 -60.00   52
  5  ω    -14.00  14.00   0.50    0.05    --   -0.62  38.00-180.00   56
  6  ω     18.00  64.00   0.50    0.05    --   -0.62  38.00-180.00   92
  7  ω    -70.00  -1.00   0.50    0.09    --  -74.78  38.00  30.00  138
  8  ω    -26.00   9.00   0.50    0.05    --   -0.62 -75.00 -60.00   70
  9  ω   -132.00 -52.00   0.50    0.09    --  -74.78 -75.00 -60.00  160
 10  ω   -149.00 -74.00   0.50    0.09    --  -74.78 -19.00   0.00  150
 11  ω   -142.00 -62.00   0.50    0.09    --  -74.78 -57.00   0.00  160
 12  ω   -148.00-122.00   0.50    0.09    --  -74.78 -99.00  60.00   52
 13  ω   -147.00 -89.00   0.50    0.09    --  -74.78-125.00   0.00  116
 14  ω   -138.00 -92.00   0.50    0.09    --  -74.78 -99.00   0.00   92
 15  ω   -144.00 -83.00   0.50    0.09    --  -74.78-125.00  90.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0085762000
_diffrn_orient_matrix_UB_12      0.0703726000
_diffrn_orient_matrix_UB_13      0.0492083000
_diffrn_orient_matrix_UB_21      -0.1545483000
_diffrn_orient_matrix_UB_22      0.0050595000
_diffrn_orient_matrix_UB_23      -0.0220751000
_diffrn_orient_matrix_UB_31      -0.0039102000
_diffrn_orient_matrix_UB_32      -0.0492105000
_diffrn_orient_matrix_UB_33      0.0679434000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3352
_reflns_number_total             4880
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.141
_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)+(0.1444P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2622
_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:
 C00L(H00A,H00C), C00M(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00F,H00G,H00I), C00V(H00K,H00L,H00M)
;
_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 0.87446(12) 0.91634(5) 0.43869(7) 0.0954(4) Uani 1 1 d . . . . .
O002 O 0.8224(2) 0.42271(14) 0.79974(13) 0.0729(6) Uani 1 1 d . . . . .
O003 O 0.9455(2) 0.39131(16) 0.69916(14) 0.0787(6) Uani 1 1 d . . . . .
O004 O 0.4486(3) 0.38767(16) 0.79364(16) 0.0853(7) Uani 1 1 d . . . . .
F005 F 0.2733(3) 0.5534(2) 0.6954(2) 0.1294(10) Uani 1 1 d . . . . .
O006 O 0.6806(3) 0.19010(14) 0.53724(16) 0.0892(7) Uani 1 1 d . . . . .
F007 F 0.3942(4) 0.61978(18) 0.61627(16) 0.1326(10) Uani 1 1 d . . . . .
C008 C 0.8235(3) 0.41532(15) 0.72461(17) 0.0558(6) Uani 1 1 d . . . . .
F009 F 0.4109(4) 0.66313(16) 0.7438(2) 0.1433(12) Uani 1 1 d . . . . .
C00A C 0.6833(3) 0.43371(15) 0.64842(16) 0.0557(6) Uani 1 1 d . . . . .
C00B C 0.5396(3) 0.45316(16) 0.68021(18) 0.0603(6) Uani 1 1 d . . . . .
H00B H 0.452872 0.458195 0.628231 0.072 Uiso 1 1 calc R U . . .
C00C C 0.7226(3) 0.50859(16) 0.60106(17) 0.0616(6) Uani 1 1 d . . . . .
C00D C 0.7854(3) 0.65525(16) 0.53624(17) 0.0609(6) Uani 1 1 d . . . . .
C00E C 0.7529(3) 0.57297(17) 0.56919(18) 0.0638(6) Uani 1 1 d . . . . .
C00F C 0.5964(3) 0.27914(16) 0.63332(18) 0.0623(6) Uani 1 1 d . . . . .
C00G C 0.5026(3) 0.37683(19) 0.73203(19) 0.0652(7) Uani 1 1 d . . . . .
C00H C 0.7271(4) 0.72896(18) 0.5650(2) 0.0699(7) Uani 1 1 d . . . . .
H00H H 0.668179 0.724409 0.604485 0.084 Uiso 1 1 calc R U . . .
C00I C 0.5297(3) 0.28965(17) 0.70126(19) 0.0645(7) Uani 1 1 d . . . . .
C00J C 0.7559(4) 0.80881(18) 0.5353(2) 0.0689(7) Uani 1 1 d . . . . .
H00J H 0.717141 0.857997 0.555041 0.083 Uiso 1 1 calc R U . . .
C00K C 0.8410(4) 0.81522(17) 0.4774(2) 0.0681(7) Uani 1 1 d . . . . .
C00L C 0.6476(3) 0.35465(16) 0.58822(17) 0.0604(6) Uani 1 1 d . . . . .
H00A H 0.566893 0.369065 0.536565 0.072 Uiso 1 1 calc R U . . .
H00C H 0.739044 0.338880 0.570521 0.072 Uiso 1 1 calc R U . . .
C00M C 0.5445(4) 0.53766(19) 0.7307(2) 0.0722(7) Uani 1 1 d . . . . .
H00D H 0.552087 0.524374 0.790934 0.087 Uiso 1 1 calc R U . . .
H00E H 0.636271 0.569484 0.728793 0.087 Uiso 1 1 calc R U . . .
C00N C 0.8721(4) 0.66335(19) 0.4776(2) 0.0799(9) Uani 1 1 d . . . . .
H00N H 0.911092 0.614254 0.457923 0.096 Uiso 1 1 calc R U . . .
C00O C 0.6151(4) 0.19530(18) 0.6050(2) 0.0724(8) Uani 1 1 d . . . . .
C00P C 0.4822(4) 0.2186(2) 0.7424(2) 0.0805(9) Uani 1 1 d . . . . .
H00P H 0.437895 0.226554 0.788151 0.097 Uiso 1 1 calc R U . . .
C00Q C 0.9026(5) 0.7434(2) 0.4473(3) 0.0855(10) Uani 1 1 d . . . . .
H00Q H 0.962220 0.748734 0.408223 0.103 Uiso 1 1 calc R U . . .
C00R C 0.4066(5) 0.5929(2) 0.6960(2) 0.0907(11) Uani 1 1 d . . . . .
C00S C 0.5026(4) 0.1379(2) 0.7137(3) 0.0904(11) Uani 1 1 d . . . . .
H00S H 0.471652 0.090467 0.740259 0.108 Uiso 1 1 calc R U . . .
C00T C 0.5683(4) 0.12536(19) 0.6459(3) 0.0875(10) Uani 1 1 d . . . . .
H00T H 0.581441 0.069846 0.627483 0.105 Uiso 1 1 calc R U . . .
C00U C 1.0857(4) 0.3750(3) 0.7662(3) 0.0944(11) Uani 1 1 d . . . . .
H00F H 1.163531 0.353739 0.740520 0.142 Uiso 1 1 calc R U . . .
H00G H 1.066048 0.332933 0.805912 0.142 Uiso 1 1 calc R U . . .
H00I H 1.120789 0.427352 0.796895 0.142 Uiso 1 1 calc R U . . .
C00V C 0.7055(6) 0.1070(3) 0.5057(3) 0.1098(14) Uani 1 1 d . . . . .
H00K H 0.766428 0.112309 0.464981 0.165 Uiso 1 1 calc R U . . .
H00L H 0.607957 0.081253 0.477566 0.165 Uiso 1 1 calc R U . . .
H00M H 0.758883 0.071414 0.553276 0.165 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
Cl01 C00K 1.745(3) . ?
O002 C008 1.211(3) . ?
O003 C008 1.322(3) . ?
O003 C00U 1.444(4) . ?
O004 C00G 1.222(4) . ?
F005 C00R 1.344(5) . ?
O006 C00O 1.367(4) . ?
O006 C00V 1.427(4) . ?
F007 C00R 1.320(4) . ?
C008 C00A 1.529(4) . ?
F009 C00R 1.328(4) . ?
C00A C00B 1.540(4) . ?
C00A C00C 1.483(3) . ?
C00A C00L 1.542(3) . ?
C00B H00B 0.9800 . ?
C00B C00G 1.534(4) . ?
C00B C00M 1.538(4) . ?
C00C C00E 1.188(4) . ?
C00D C00E 1.443(4) . ?
C00D C00H 1.389(4) . ?
C00D C00N 1.376(4) . ?
C00F C00I 1.385(4) . ?
C00F C00L 1.513(4) . ?
C00F C00O 1.406(4) . ?
C00G C00I 1.484(4) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.378(4) . ?
C00I C00P 1.409(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.355(4) . ?
C00K C00Q 1.388(4) . ?
C00L H00A 0.9700 . ?
C00L H00C 0.9700 . ?
C00M H00D 0.9700 . ?
C00M H00E 0.9700 . ?
C00M C00R 1.489(5) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.391(4) . ?
C00O C00T 1.391(5) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.367(5) . ?
C00Q H00Q 0.9300 . ?
C00S H00S 0.9300 . ?
C00S C00T 1.380(6) . ?
C00T H00T 0.9300 . ?
C00U H00F 0.9600 . ?
C00U H00G 0.9600 . ?
C00U H00I 0.9600 . ?
C00V H00K 0.9600 . ?
C00V H00L 0.9600 . ?
C00V H00M 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
C008 O003 C00U 116.9(3) . . ?
C00O O006 C00V 118.4(3) . . ?
O002 C008 O003 124.1(3) . . ?
O002 C008 C00A 123.5(2) . . ?
O003 C008 C00A 112.5(2) . . ?
C008 C00A C00B 111.1(2) . . ?
C008 C00A C00L 109.8(2) . . ?
C00B C00A C00L 108.0(2) . . ?
C00C C00A C008 107.3(2) . . ?
C00C C00A C00B 110.5(2) . . ?
C00C C00A C00L 110.2(2) . . ?
C00A C00B H00B 106.4 . . ?
C00G C00B C00A 110.4(2) . . ?
C00G C00B H00B 106.4 . . ?
C00G C00B C00M 110.9(2) . . ?
C00M C00B C00A 115.6(2) . . ?
C00M C00B H00B 106.4 . . ?
C00E C00C C00A 174.1(3) . . ?
C00H C00D C00E 118.7(3) . . ?
C00N C00D C00E 122.5(3) . . ?
C00N C00D C00H 118.8(3) . . ?
C00C C00E C00D 175.0(3) . . ?
C00I C00F C00L 122.3(2) . . ?
C00I C00F C00O 118.5(3) . . ?
C00O C00F C00L 119.2(3) . . ?
O004 C00G C00B 121.3(3) . . ?
O004 C00G C00I 122.0(3) . . ?
C00I C00G C00B 116.7(2) . . ?
C00D C00H H00H 119.7 . . ?
C00J C00H C00D 120.5(3) . . ?
C00J C00H H00H 119.7 . . ?
C00F C00I C00G 120.8(2) . . ?
C00F C00I C00P 121.6(3) . . ?
C00P C00I C00G 117.7(3) . . ?
C00H C00J H00J 120.2 . . ?
C00K C00J C00H 119.6(3) . . ?
C00K C00J H00J 120.2 . . ?
C00J C00K Cl01 119.4(2) . . ?
C00J C00K C00Q 121.9(3) . . ?
C00Q C00K Cl01 118.7(2) . . ?
C00A C00L H00A 109.4 . . ?
C00A C00L H00C 109.4 . . ?
C00F C00L C00A 111.1(2) . . ?
C00F C00L H00A 109.4 . . ?
C00F C00L H00C 109.4 . . ?
H00A C00L H00C 108.0 . . ?
C00B C00M H00D 109.0 . . ?
C00B C00M H00E 109.0 . . ?
H00D C00M H00E 107.8 . . ?
C00R C00M C00B 113.1(3) . . ?
C00R C00M H00D 109.0 . . ?
C00R C00M H00E 109.0 . . ?
C00D C00N H00N 119.3 . . ?
C00D C00N C00Q 121.3(3) . . ?
C00Q C00N H00N 119.3 . . ?
O006 C00O C00F 115.1(3) . . ?
O006 C00O C00T 125.1(3) . . ?
C00T C00O C00F 119.7(3) . . ?
C00I C00P H00P 120.7 . . ?
C00S C00P C00I 118.6(4) . . ?
C00S C00P H00P 120.7 . . ?
C00K C00Q C00N 117.8(3) . . ?
C00K C00Q H00Q 121.1 . . ?
C00N C00Q H00Q 121.1 . . ?
F005 C00R C00M 113.1(3) . . ?
F007 C00R F005 107.0(4) . . ?
F007 C00R F009 106.1(3) . . ?
F007 C00R C00M 113.0(3) . . ?
F009 C00R F005 105.6(3) . . ?
F009 C00R C00M 111.5(3) . . ?
C00P C00S H00S 119.4 . . ?
C00P C00S C00T 121.2(3) . . ?
C00T C00S H00S 119.4 . . ?
C00O C00T H00T 119.8 . . ?
C00S C00T C00O 120.4(3) . . ?
C00S C00T H00T 119.8 . . ?
O003 C00U H00F 109.5 . . ?
O003 C00U H00G 109.5 . . ?
O003 C00U H00I 109.5 . . ?
H00F C00U H00G 109.5 . . ?
H00F C00U H00I 109.5 . . ?
H00G C00U H00I 109.5 . . ?
O006 C00V H00K 109.5 . . ?
O006 C00V H00L 109.5 . . ?
O006 C00V H00M 109.5 . . ?
H00K C00V H00L 109.5 . . ?
H00K C00V H00M 109.5 . . ?
H00L C00V H00M 109.5 . . ?

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
Cl01 C00K C00Q C00N -178.8(3) . . . . ?
O002 C008 C00A C00B -5.9(3) . . . . ?
O002 C008 C00A C00C 114.9(3) . . . . ?
O002 C008 C00A C00L -125.3(3) . . . . ?
O003 C008 C00A C00B 174.7(2) . . . . ?
O003 C008 C00A C00C -64.5(3) . . . . ?
O003 C008 C00A C00L 55.2(3) . . . . ?
O004 C00G C00I C00F -177.6(3) . . . . ?
O004 C00G C00I C00P 3.7(4) . . . . ?
O006 C00O C00T C00S -179.7(3) . . . . ?
C008 C00A C00B C00G -59.1(3) . . . . ?
C008 C00A C00B C00M 67.9(3) . . . . ?
C008 C00A C00L C00F 66.0(3) . . . . ?
C00A C00B C00G O004 145.8(3) . . . . ?
C00A C00B C00G C00I -36.7(3) . . . . ?
C00A C00B C00M C00R 127.9(3) . . . . ?
C00B C00A C00L C00F -55.3(3) . . . . ?
C00B C00G C00I C00F 4.9(4) . . . . ?
C00B C00G C00I C00P -173.8(2) . . . . ?
C00B C00M C00R F005 58.0(4) . . . . ?
C00B C00M C00R F007 -63.7(4) . . . . ?
C00B C00M C00R F009 176.8(3) . . . . ?
C00C C00A C00B C00G -177.9(2) . . . . ?
C00C C00A C00B C00M -51.0(3) . . . . ?
C00C C00A C00L C00F -176.1(2) . . . . ?
C00D C00H C00J C00K 0.4(5) . . . . ?
C00D C00N C00Q C00K -0.7(6) . . . . ?
C00E C00D C00H C00J 179.8(3) . . . . ?
C00E C00D C00N C00Q -179.6(3) . . . . ?
C00F C00I C00P C00S -0.3(4) . . . . ?
C00F C00O C00T C00S 0.5(5) . . . . ?
C00G C00B C00M C00R -105.5(3) . . . . ?
C00G C00I C00P C00S 178.4(3) . . . . ?
C00H C00D C00N C00Q 0.3(5) . . . . ?
C00H C00J C00K Cl01 178.9(2) . . . . ?
C00H C00J C00K C00Q -0.9(5) . . . . ?
C00I C00F C00L C00A 25.0(3) . . . . ?
C00I C00F C00O O006 179.5(2) . . . . ?
C00I C00F C00O C00T -0.7(4) . . . . ?
C00I C00P C00S C00T 0.1(5) . . . . ?
C00J C00K C00Q C00N 1.0(6) . . . . ?
C00L C00A C00B C00G 61.5(3) . . . . ?
C00L C00A C00B C00M -171.6(2) . . . . ?
C00L C00F C00I C00G 1.1(4) . . . . ?
C00L C00F C00I C00P 179.8(2) . . . . ?
C00L C00F C00O O006 0.3(4) . . . . ?
C00L C00F C00O C00T -179.9(3) . . . . ?
C00M C00B C00G O004 16.3(4) . . . . ?
C00M C00B C00G C00I -166.2(2) . . . . ?
C00N C00D C00H C00J -0.1(4) . . . . ?
C00O C00F C00I C00G -178.1(2) . . . . ?
C00O C00F C00I C00P 0.6(4) . . . . ?
C00O C00F C00L C00A -155.8(2) . . . . ?
C00P C00S C00T C00O -0.2(5) . . . . ?
C00U O003 C008 O002 -1.3(4) . . . . ?
C00U O003 C008 C00A 178.1(3) . . . . ?
C00V O006 C00O C00F 179.1(3) . . . . ?
C00V O006 C00O C00T -0.7(5) . . . . ?

_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 2.047
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_zq-6-58-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2108434'
loop_
_audit_author_name
_audit_author_address
'Yajun Li'
;Fujian Institute of Research on the Structure of Matter(FJIRSM)
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cl F3 O3'
_chemical_formula_sum            'C23 H18 Cl F3 O3'
_chemical_formula_weight         434.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOClF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   12.5234(6)
_cell_length_b                   9.7432(5)
_cell_length_c                   17.5168(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.018(5)
_cell_angle_gamma                90
_cell_volume                     2121.35(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.5840
_cell_measurement_theta_min      4.5020
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    1.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15318
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.778
_diffrn_reflns_theta_min         4.523
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_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     78.00 103.00   0.50    0.05    --   73.53  58.00  61.00   50
  2  ω     21.00  47.00   0.50    0.05    --   73.53 -58.00 -79.00   52
  3  ω     32.00  70.00   0.50    0.05    --   73.53 -38.00-180.00   76
  4  ω    -14.00  21.00   0.50    0.05    --   -0.62  38.00-180.00   70
  5  ω     26.00  60.00   0.50    0.05    --   -0.62  38.00-180.00   68
  6  ω    -17.00  70.00   0.50    0.05    --   -0.62  58.00  61.00  174
  7  ω    -89.00  -5.00   0.50    0.05    --  -74.78  58.00  61.00  168
  8  ω    -67.00 -15.00   0.50    0.05    --  -74.78  38.00  30.00  104
  9  ω    -56.00 -28.00   0.50    0.05    --   -0.62 -58.00 -79.00   56
 10  ω   -142.00 -91.00   0.50    0.05    --  -74.78 -99.00  60.00  102
 11  ω   -146.00 -80.00   0.50    0.05    --  -74.78-125.00  60.00  132
 12  ω   -146.00 -87.00   0.50    0.05    --  -74.78-125.00   0.00  118
 13  ω   -144.00-110.00   0.50    0.05    --  -74.78 -99.00  30.00   68
 14  ω   -148.00 -80.00   0.50    0.05    --  -74.78 -58.00 -79.00  136
 15  ω   -147.00 -96.00   0.50    0.05    --  -74.78 -99.00-180.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0572864000
_diffrn_orient_matrix_UB_12      0.0933904000
_diffrn_orient_matrix_UB_13      -0.0436252000
_diffrn_orient_matrix_UB_21      0.0668518000
_diffrn_orient_matrix_UB_22      -0.0131294000
_diffrn_orient_matrix_UB_23      -0.0536671000
_diffrn_orient_matrix_UB_31      -0.0620427000
_diffrn_orient_matrix_UB_32      -0.1001881000
_diffrn_orient_matrix_UB_33      -0.0338151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3479
_reflns_number_total             4752
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.123
_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)+(0.1014P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1974
_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(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00J(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00K(H00K), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00U(H00U)
2.d Idealised Me refined as rotating group:
 C00L(H00F,H00G,H00I), C00T(H00J,H00L,H00M)
;
_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 1.15820(7) 0.14142(12) 0.58270(8) 0.1394(5) Uani 1 1 d . . . . .
O002 O 0.55686(14) 0.77188(14) 0.32946(8) 0.0632(4) Uani 1 1 d . . . . .
O003 O 0.58313(14) 0.69698(15) 0.45090(8) 0.0651(4) Uani 1 1 d . . . . .
O004 O 0.47157(12) 0.61201(16) 0.15822(8) 0.0607(4) Uani 1 1 d . . . . .
F005 F 0.81394(14) 0.5893(2) 0.15054(12) 0.1165(7) Uani 1 1 d . . . . .
F006 F 0.68272(16) 0.4512(3) 0.12586(11) 0.1196(7) Uani 1 1 d . . . . .
F007 F 0.80000(16) 0.4161(2) 0.22130(13) 0.1244(8) Uani 1 1 d . . . . .
C008 C 0.57674(15) 0.6808(2) 0.37532(11) 0.0474(4) Uani 1 1 d . . . . .
C009 C 0.49874(16) 0.4443(2) 0.37734(11) 0.0513(4) Uani 1 1 d . . . . .
H00A H 0.510375 0.348397 0.365936 0.062 Uiso 1 1 calc R U . . .
H00B H 0.498206 0.452877 0.432456 0.062 Uiso 1 1 calc R U . . .
C00A C 0.59207(14) 0.53068(19) 0.35262(10) 0.0458(4) Uani 1 1 d . . . . .
C00B C 0.58789(15) 0.5207(2) 0.26394(10) 0.0466(4) Uani 1 1 d . . . . .
H00C H 0.596487 0.423454 0.251765 0.056 Uiso 1 1 calc R U . . .
C00C C 0.69330(16) 0.4738(2) 0.39148(12) 0.0534(5) Uani 1 1 d . . . . .
C00D C 0.39174(16) 0.4888(2) 0.33701(11) 0.0518(5) Uani 1 1 d . . . . .
C00E C 0.38214(15) 0.5442(2) 0.26325(11) 0.0493(4) Uani 1 1 d . . . . .
C00F C 0.47901(16) 0.56505(19) 0.22301(10) 0.0476(4) Uani 1 1 d . . . . .
C00G C 0.77124(17) 0.4143(2) 0.42162(12) 0.0566(5) Uani 1 1 d . . . . .
C00H C 0.28165(17) 0.5850(2) 0.22673(13) 0.0607(5) Uani 1 1 d . . . . .
H00H H 0.276564 0.623349 0.177792 0.073 Uiso 1 1 calc R U . . .
C00I C 0.86403(16) 0.3443(2) 0.45895(12) 0.0562(5) Uani 1 1 d . . . . .
C00J C 0.68040(17) 0.5981(2) 0.23230(13) 0.0590(5) Uani 1 1 d . . . . .
H00D H 0.650628 0.676325 0.202712 0.071 Uiso 1 1 calc R U . . .
H00E H 0.728930 0.633105 0.275292 0.071 Uiso 1 1 calc R U . . .
C00K C 0.29960(19) 0.4745(3) 0.37298(15) 0.0744(7) Uani 1 1 d . . . . .
H00K H 0.304282 0.438566 0.422467 0.089 Uiso 1 1 calc R U . . .
C00L C 0.5628(3) 0.8341(3) 0.47787(15) 0.0828(8) Uani 1 1 d . . . . .
H00F H 0.493326 0.864439 0.454912 0.124 Uiso 1 1 calc R U . . .
H00G H 0.617037 0.895563 0.463739 0.124 Uiso 1 1 calc R U . . .
H00I H 0.564745 0.833074 0.532822 0.124 Uiso 1 1 calc R U . . .
C00M C 0.7431(2) 0.5140(3) 0.18309(15) 0.0736(7) Uani 1 1 d . . . . .
C00N C 0.18965(19) 0.5693(3) 0.26232(16) 0.0750(7) Uani 1 1 d . . . . .
C00O C 1.0441(2) 0.2160(3) 0.53309(18) 0.0821(8) Uani 1 1 d . . . . .
C00P C 0.9647(2) 0.3682(3) 0.43857(18) 0.0903(9) Uani 1 1 d . . . . .
H00P H 0.972492 0.429813 0.399061 0.108 Uiso 1 1 calc R U . . .
C00Q C 1.0549(2) 0.3034(4) 0.4751(2) 0.0957(10) Uani 1 1 d . . . . .
H00Q H 1.122279 0.319958 0.459858 0.115 Uiso 1 1 calc R U . . .
C00R C 0.8559(2) 0.2516(4) 0.5160(2) 0.1018(11) Uani 1 1 d . . . . .
H00R H 0.788414 0.231148 0.530089 0.122 Uiso 1 1 calc R U . . .
C00S C 0.2013(2) 0.5135(3) 0.33547(17) 0.0869(8) Uani 1 1 d . . . . .
H00S H 0.140360 0.501888 0.360259 0.104 Uiso 1 1 calc R U . . .
C00T C 0.0811(2) 0.6138(4) 0.2238(2) 0.1071(11) Uani 1 1 d . . . . .
H00J H 0.049804 0.677828 0.256304 0.161 Uiso 1 1 calc R U . . .
H00L H 0.035128 0.535112 0.215027 0.161 Uiso 1 1 calc R U . . .
H00M H 0.089239 0.656797 0.175549 0.161 Uiso 1 1 calc R U . . .
C00U C 0.9451(2) 0.1874(4) 0.5533(2) 0.1222(15) Uani 1 1 d . . . . .
H00U H 0.937785 0.124619 0.592323 0.147 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
Cl01 C00O 1.738(3) . ?
O002 C008 1.202(2) . ?
O003 C008 1.326(2) . ?
O003 C00L 1.450(3) . ?
O004 C00F 1.217(2) . ?
F005 C00M 1.332(3) . ?
F006 C00M 1.329(3) . ?
F007 C00M 1.323(3) . ?
C008 C00A 1.534(3) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00A 1.545(3) . ?
C009 C00D 1.500(3) . ?
C00A C00B 1.551(2) . ?
C00A C00C 1.472(3) . ?
C00B H00C 0.9800 . ?
C00B C00F 1.524(3) . ?
C00B C00J 1.541(3) . ?
C00C C00G 1.201(3) . ?
C00D C00E 1.392(3) . ?
C00D C00K 1.388(3) . ?
C00E C00F 1.490(3) . ?
C00E C00H 1.398(3) . ?
C00G C00I 1.434(3) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.384(3) . ?
C00I C00P 1.372(3) . ?
C00I C00R 1.361(3) . ?
C00J H00D 0.9700 . ?
C00J H00E 0.9700 . ?
C00J C00M 1.482(3) . ?
C00K H00K 0.9300 . ?
C00K C00S 1.376(4) . ?
C00L H00F 0.9600 . ?
C00L H00G 0.9600 . ?
C00L H00I 0.9600 . ?
C00N C00S 1.383(4) . ?
C00N C00T 1.505(4) . ?
C00O C00Q 1.344(4) . ?
C00O C00U 1.359(4) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.381(4) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00U 1.374(4) . ?
C00S H00S 0.9300 . ?
C00T H00J 0.9600 . ?
C00T H00L 0.9600 . ?
C00T H00M 0.9600 . ?
C00U H00U 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
C008 O003 C00L 116.31(17) . . ?
O002 C008 O003 124.18(18) . . ?
O002 C008 C00A 123.56(17) . . ?
O003 C008 C00A 112.19(16) . . ?
H00A C009 H00B 107.9 . . ?
C00A C009 H00A 109.2 . . ?
C00A C009 H00B 109.2 . . ?
C00D C009 H00A 109.2 . . ?
C00D C009 H00B 109.2 . . ?
C00D C009 C00A 111.93(15) . . ?
C008 C00A C009 108.91(15) . . ?
C008 C00A C00B 109.23(15) . . ?
C009 C00A C00B 108.20(15) . . ?
C00C C00A C008 111.55(16) . . ?
C00C C00A C009 107.67(15) . . ?
C00C C00A C00B 111.18(15) . . ?
C00A C00B H00C 106.7 . . ?
C00F C00B C00A 111.86(14) . . ?
C00F C00B H00C 106.7 . . ?
C00F C00B C00J 111.15(16) . . ?
C00J C00B C00A 113.25(16) . . ?
C00J C00B H00C 106.7 . . ?
C00G C00C C00A 173.3(2) . . ?
C00E C00D C009 121.33(17) . . ?
C00K C00D C009 120.11(19) . . ?
C00K C00D C00E 118.6(2) . . ?
C00D C00E C00F 120.61(17) . . ?
C00D C00E C00H 120.40(18) . . ?
C00H C00E C00F 118.97(18) . . ?
O004 C00F C00B 120.52(17) . . ?
O004 C00F C00E 121.25(18) . . ?
C00E C00F C00B 118.19(16) . . ?
C00C C00G C00I 178.9(2) . . ?
C00E C00H H00H 119.5 . . ?
C00N C00H C00E 121.0(2) . . ?
C00N C00H H00H 119.5 . . ?
C00P C00I C00G 121.3(2) . . ?
C00R C00I C00G 121.4(2) . . ?
C00R C00I C00P 117.3(2) . . ?
C00B C00J H00D 108.7 . . ?
C00B C00J H00E 108.7 . . ?
H00D C00J H00E 107.6 . . ?
C00M C00J C00B 114.4(2) . . ?
C00M C00J H00D 108.7 . . ?
C00M C00J H00E 108.7 . . ?
C00D C00K H00K 120.0 . . ?
C00S C00K C00D 120.0(2) . . ?
C00S C00K H00K 120.0 . . ?
O003 C00L H00F 109.5 . . ?
O003 C00L H00G 109.5 . . ?
O003 C00L H00I 109.5 . . ?
H00F C00L H00G 109.5 . . ?
H00F C00L H00I 109.5 . . ?
H00G C00L H00I 109.5 . . ?
F005 C00M C00J 111.9(2) . . ?
F006 C00M F005 106.1(2) . . ?
F006 C00M C00J 113.6(2) . . ?
F007 C00M F005 105.5(2) . . ?
F007 C00M F006 105.7(3) . . ?
F007 C00M C00J 113.3(2) . . ?
C00H C00N C00T 121.5(3) . . ?
C00S C00N C00H 117.5(2) . . ?
C00S C00N C00T 121.0(2) . . ?
C00Q C00O Cl01 119.3(2) . . ?
C00Q C00O C00U 120.4(2) . . ?
C00U C00O Cl01 120.3(2) . . ?
C00I C00P H00P 119.1 . . ?
C00I C00P C00Q 121.8(2) . . ?
C00Q C00P H00P 119.1 . . ?
C00O C00Q C00P 119.2(2) . . ?
C00O C00Q H00Q 120.4 . . ?
C00P C00Q H00Q 120.4 . . ?
C00I C00R H00R 119.3 . . ?
C00I C00R C00U 121.4(2) . . ?
C00U C00R H00R 119.3 . . ?
C00K C00S C00N 122.5(2) . . ?
C00K C00S H00S 118.7 . . ?
C00N C00S H00S 118.7 . . ?
C00N C00T H00J 109.5 . . ?
C00N C00T H00L 109.5 . . ?
C00N C00T H00M 109.5 . . ?
H00J C00T H00L 109.5 . . ?
H00J C00T H00M 109.5 . . ?
H00L C00T H00M 109.5 . . ?
C00O C00U C00R 119.8(3) . . ?
C00O C00U H00U 120.1 . . ?
C00R C00U H00U 120.1 . . ?

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
Cl01 C00O C00Q C00P -176.5(3) . . . . ?
Cl01 C00O C00U C00R 177.1(3) . . . . ?
O002 C008 C00A C009 -113.0(2) . . . . ?
O002 C008 C00A C00B 5.0(3) . . . . ?
O002 C008 C00A C00C 128.3(2) . . . . ?
O003 C008 C00A C009 64.1(2) . . . . ?
O003 C008 C00A C00B -177.88(15) . . . . ?
O003 C008 C00A C00C -54.6(2) . . . . ?
C008 C00A C00B C00F -62.53(19) . . . . ?
C008 C00A C00B C00J 64.0(2) . . . . ?
C009 C00A C00B C00F 55.9(2) . . . . ?
C009 C00A C00B C00J -177.56(16) . . . . ?
C009 C00D C00E C00F -1.9(3) . . . . ?
C009 C00D C00E C00H -179.98(19) . . . . ?
C009 C00D C00K C00S -179.1(3) . . . . ?
C00A C009 C00D C00E 30.4(3) . . . . ?
C00A C009 C00D C00K -149.9(2) . . . . ?
C00A C00B C00F O004 152.79(18) . . . . ?
C00A C00B C00F C00E -29.6(2) . . . . ?
C00A C00B C00J C00M 126.6(2) . . . . ?
C00B C00J C00M F005 173.1(2) . . . . ?
C00B C00J C00M F006 52.9(3) . . . . ?
C00B C00J C00M F007 -67.8(3) . . . . ?
C00C C00A C00B C00F 173.95(16) . . . . ?
C00C C00A C00B C00J -59.5(2) . . . . ?
C00D C009 C00A C008 62.3(2) . . . . ?
C00D C009 C00A C00B -56.3(2) . . . . ?
C00D C009 C00A C00C -176.56(16) . . . . ?
C00D C00E C00F O004 179.18(18) . . . . ?
C00D C00E C00F C00B 1.5(3) . . . . ?
C00D C00E C00H C00N -1.1(3) . . . . ?
C00D C00K C00S C00N -0.9(5) . . . . ?
C00E C00D C00K C00S 0.7(4) . . . . ?
C00E C00H C00N C00S 0.8(4) . . . . ?
C00E C00H C00N C00T 179.6(3) . . . . ?
C00F C00B C00J C00M -106.5(2) . . . . ?
C00F C00E C00H C00N -179.2(2) . . . . ?
C00G C00I C00P C00Q 178.7(3) . . . . ?
C00G C00I C00R C00U -178.1(4) . . . . ?
C00H C00E C00F O004 -2.7(3) . . . . ?
C00H C00E C00F C00B 179.63(18) . . . . ?
C00H C00N C00S C00K 0.2(5) . . . . ?
C00I C00P C00Q C00O -1.0(6) . . . . ?
C00I C00R C00U C00O -0.3(7) . . . . ?
C00J C00B C00F O004 25.1(3) . . . . ?
C00J C00B C00F C00E -157.23(16) . . . . ?
C00K C00D C00E C00F 178.4(2) . . . . ?
C00K C00D C00E C00H 0.3(3) . . . . ?
C00L O003 C008 O002 0.9(3) . . . . ?
C00L O003 C008 C00A -176.2(2) . . . . ?
C00P C00I C00R C00U 1.9(5) . . . . ?
C00Q C00O C00U C00R -2.1(7) . . . . ?
C00R C00I C00P C00Q -1.2(5) . . . . ?
C00T C00N C00S C00K -178.6(3) . . . . ?
C00U C00O C00Q C00P 2.7(6) . . . . ?

_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 1.828
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_zq-ys_auto
_database_code_depnum_ccdc_archive 'CCDC 2108435'
loop_
_audit_author_name
_audit_author_address
'Yajun Li'
;Fujian Institute of Research on the Structure of Matter(FJIRSM)
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F3 O3'
_chemical_formula_sum            'C22 H19 F3 O3'
_chemical_formula_weight         388.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   15.1282(19)
_cell_length_b                   11.8989(10)
_cell_length_c                   11.6230(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.112(15)
_cell_angle_gamma                90
_cell_volume                     1951.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.4320
_cell_measurement_theta_min      4.2090
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13341
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.697
_diffrn_reflns_theta_min         4.225
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  97.00   0.50    0.80    --   72.28  57.00 150.00   68
  2  ω    119.00 144.00   0.50    0.80    --   72.28  57.00 150.00   50
  3  ω     77.00 102.00   0.50    0.80    --   72.28  45.00  21.00   50
  4  ω     83.00 108.00   0.50    0.80    --   72.28 125.00 -90.00   50
  5  ω     90.00 144.00   0.50    0.80    --   72.28 125.00-150.00  108
  6  ω    -31.00  -2.00   0.50    0.80    --  -74.78  38.00-150.00   58
  7  ω    -70.00  -3.00   0.50    0.80    --  -74.78  45.00  21.00  134
  8  ω    -15.00  54.00   0.50    0.20    --   -1.25  45.00  21.00  138
  9  ω     35.00  70.00   0.50    0.80    --   72.28 -45.00-128.00   70
 10  ω    -14.00  70.00   0.50    0.20    --   -1.25  57.00-180.00  168
 11  ω    -71.00 -35.00   0.50    0.80    --  -74.78  38.00-150.00   72
 12  ω   -147.00 -60.00   0.50    0.80    --  -74.78 -45.00-128.00  174
 13  ω    -72.00 -21.00   0.50    0.20    --   -1.25 -45.00-128.00  102
 14  ω    -81.00 -54.00   0.50    0.80    --  -74.78 -77.00 150.00   54
 15  ω   -148.00 -91.00   0.50    0.80    --  -74.78 -77.00 150.00  114
 16  ω   -148.00-100.00   0.50    0.80    --  -74.78-125.00 -30.00   96
 17  ω   -147.00-105.00   0.50    0.80    --  -74.78-125.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0873691000
_diffrn_orient_matrix_UB_12      0.0382456000
_diffrn_orient_matrix_UB_13      -0.0190737000
_diffrn_orient_matrix_UB_21      -0.0320994000
_diffrn_orient_matrix_UB_22      -0.0511666000
_diffrn_orient_matrix_UB_23      -0.1099759000
_diffrn_orient_matrix_UB_31      -0.0182307000
_diffrn_orient_matrix_UB_32      -0.0927611000
_diffrn_orient_matrix_UB_33      0.0529258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2744
_reflns_number_total             4310
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.055
_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)+(0.1044P)²+0.3682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1926
_refine_ls_wR_factor_ref         0.2132
_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:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00G(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00M(H00G,H00H,H00M)
;
_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
O001 O 0.68688(14) 0.34750(13) 0.56171(15) 0.0713(5) Uani 1 1 d . . . . .
O002 O 0.63102(14) 0.06860(14) 0.48980(16) 0.0751(5) Uani 1 1 d . . . . .
O003 O 0.64809(14) 0.49212(14) 0.43000(16) 0.0767(5) Uani 1 1 d . . . . .
C004 C 0.61830(17) 0.14593(17) 0.4169(2) 0.0567(5) Uani 1 1 d . . . . .
C005 C 0.52256(17) 0.19177(17) 0.34983(19) 0.0559(5) Uani 1 1 d . . . . .
C006 C 0.67523(17) 0.38703(18) 0.4617(2) 0.0588(6) Uani 1 1 d . . . . .
C007 C 0.50898(18) 0.28020(18) 0.2663(2) 0.0610(6) Uani 1 1 d . . . . .
C008 C 0.70025(17) 0.19553(19) 0.3882(2) 0.0591(6) Uani 1 1 d . . . . .
H008 H 0.699895 0.157377 0.313285 0.071 Uiso 1 1 calc R U . . .
C009 C 0.68520(18) 0.32201(19) 0.3545(2) 0.0614(6) Uani 1 1 d . . . . .
F00A F 0.92747(17) 0.0501(2) 0.5459(3) 0.1608(11) Uani 1 1 d . . . . .
F00B F 0.8016(2) -0.0134(2) 0.4131(3) 0.1779(13) Uani 1 1 d . . . . .
C00C C 0.44483(19) 0.1446(2) 0.3702(2) 0.0669(6) Uani 1 1 d . . . . .
H00C H 0.454205 0.086606 0.427036 0.080 Uiso 1 1 calc R U . . .
C00D C 0.5917(2) 0.3317(2) 0.2425(2) 0.0688(7) Uani 1 1 d . . . . .
H00A H 0.578453 0.410386 0.221709 0.083 Uiso 1 1 calc R U . . .
H00B H 0.599270 0.294605 0.172254 0.083 Uiso 1 1 calc R U . . .
F00E F 0.8776(2) 0.1102(3) 0.3622(3) 0.1669(11) Uani 1 1 d . . . . .
C00F C 0.4171(2) 0.3185(2) 0.2051(2) 0.0781(7) Uani 1 1 d . . . . .
H00F H 0.406443 0.377859 0.149681 0.094 Uiso 1 1 calc R U . . .
C00G C 0.79604(19) 0.1671(2) 0.4882(3) 0.0741(7) Uani 1 1 d . . . . .
H00D H 0.835428 0.233849 0.505318 0.089 Uiso 1 1 calc R U . . .
H00E H 0.785419 0.147492 0.563219 0.089 Uiso 1 1 calc R U . . .
C00H C 0.86282(19) 0.5215(2) 0.4510(3) 0.0759(7) Uani 1 1 d . . . . .
C00I C 0.7644(2) 0.3625(2) 0.3136(3) 0.0817(8) Uani 1 1 d . . . . .
H00I H 0.765665 0.323066 0.245057 0.098 Uiso 1 1 calc R U . . .
C00J C 0.8316(2) 0.4386(3) 0.3498(3) 0.0873(9) Uani 1 1 d . . . . .
H00J H 0.868033 0.440810 0.300148 0.105 Uiso 1 1 calc R U . . .
C00K C 0.3559(2) 0.1828(2) 0.3080(3) 0.0828(8) Uani 1 1 d . . . . .
H00K H 0.304464 0.150154 0.321076 0.099 Uiso 1 1 calc R U . . .
C00L C 0.3419(2) 0.2696(3) 0.2255(3) 0.0881(9) Uani 1 1 d . . . . .
H00L H 0.280818 0.295595 0.182967 0.106 Uiso 1 1 calc R U . . .
C00M C 0.6364(3) 0.5633(3) 0.5243(3) 0.1031(11) Uani 1 1 d . . . . .
H00G H 0.611927 0.635026 0.489366 0.155 Uiso 1 1 calc R U . . .
H00H H 0.696554 0.573543 0.589632 0.155 Uiso 1 1 calc R U . . .
H00M H 0.592902 0.528691 0.556655 0.155 Uiso 1 1 calc R U . . .
C00N C 0.8861(2) 0.6278(3) 0.4246(3) 0.0963(10) Uani 1 1 d . . . . .
H00N H 0.880327 0.644981 0.344187 0.116 Uiso 1 1 calc R U . . .
C00O C 0.8761(3) 0.4980(3) 0.5729(3) 0.0997(10) Uani 1 1 d . . . . .
H00O H 0.863007 0.426315 0.594405 0.120 Uiso 1 1 calc R U . . .
C00P C 0.8482(3) 0.0750(3) 0.4575(4) 0.1088(11) Uani 1 1 d . . . . .
C00Q C 0.9086(3) 0.5800(4) 0.6632(4) 0.1226(14) Uani 1 1 d . . . . .
H00Q H 0.917261 0.562521 0.744508 0.147 Uiso 1 1 calc R U . . .
C00R C 0.9177(3) 0.7098(3) 0.5145(5) 0.1228(14) Uani 1 1 d . . . . .
H00R H 0.932140 0.781399 0.494328 0.147 Uiso 1 1 calc R U . . .
C00S C 0.9278(3) 0.6844(4) 0.6347(5) 0.1285(15) Uani 1 1 d . . . . .
H00S H 0.947825 0.739317 0.695614 0.154 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
O001 C006 1.206(3) . ?
O002 C004 1.218(2) . ?
O003 C006 1.326(3) . ?
O003 C00M 1.446(3) . ?
C004 C005 1.480(3) . ?
C004 C008 1.515(3) . ?
C005 C007 1.396(3) . ?
C005 C00C 1.398(3) . ?
C006 C009 1.520(3) . ?
C007 C00D 1.506(3) . ?
C007 C00F 1.391(4) . ?
C008 H008 0.9800 . ?
C008 C009 1.551(3) . ?
C008 C00G 1.534(4) . ?
C009 C00D 1.543(4) . ?
C009 C00I 1.519(3) . ?
F00A C00P 1.302(4) . ?
F00B C00P 1.267(4) . ?
C00C H00C 0.9300 . ?
C00C C00K 1.356(4) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
F00E C00P 1.398(5) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.371(4) . ?
C00G H00D 0.9700 . ?
C00G H00E 0.9700 . ?
C00G C00P 1.467(4) . ?
C00H C00J 1.477(4) . ?
C00H C00N 1.378(4) . ?
C00H C00O 1.386(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.312(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00L 1.373(4) . ?
C00L H00L 0.9300 . ?
C00M H00G 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00M 0.9600 . ?
C00N H00N 0.9300 . ?
C00N C00R 1.383(6) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.387(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.344(6) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.383(6) . ?
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
C006 O003 C00M 116.8(2) . . ?
O002 C004 C005 121.6(2) . . ?
O002 C004 C008 120.7(2) . . ?
C005 C004 C008 117.60(19) . . ?
C007 C005 C004 121.0(2) . . ?
C007 C005 C00C 119.9(2) . . ?
C00C C005 C004 119.1(2) . . ?
O001 C006 O003 124.0(2) . . ?
O001 C006 C009 124.6(2) . . ?
O003 C006 C009 111.35(18) . . ?
C005 C007 C00D 120.7(2) . . ?
C00F C007 C005 118.2(2) . . ?
C00F C007 C00D 121.1(2) . . ?
C004 C008 H008 105.8 . . ?
C004 C008 C009 112.09(19) . . ?
C004 C008 C00G 111.8(2) . . ?
C009 C008 H008 105.8 . . ?
C00G C008 H008 105.8 . . ?
C00G C008 C009 114.7(2) . . ?
C006 C009 C008 109.65(17) . . ?
C006 C009 C00D 108.8(2) . . ?
C00D C009 C008 106.96(19) . . ?
C00I C009 C006 114.7(2) . . ?
C00I C009 C008 109.0(2) . . ?
C00I C009 C00D 107.36(19) . . ?
C005 C00C H00C 119.7 . . ?
C00K C00C C005 120.6(3) . . ?
C00K C00C H00C 119.7 . . ?
C007 C00D C009 112.59(18) . . ?
C007 C00D H00A 109.1 . . ?
C007 C00D H00B 109.1 . . ?
C009 C00D H00A 109.1 . . ?
C009 C00D H00B 109.1 . . ?
H00A C00D H00B 107.8 . . ?
C007 C00F H00F 119.6 . . ?
C00L C00F C007 120.7(3) . . ?
C00L C00F H00F 119.6 . . ?
C008 C00G H00D 108.5 . . ?
C008 C00G H00E 108.5 . . ?
H00D C00G H00E 107.5 . . ?
C00P C00G C008 115.1(2) . . ?
C00P C00G H00D 108.5 . . ?
C00P C00G H00E 108.5 . . ?
C00N C00H C00J 118.1(3) . . ?
C00N C00H C00O 117.3(3) . . ?
C00O C00H C00J 124.6(3) . . ?
C009 C00I H00I 111.7 . . ?
C00J C00I C009 136.6(2) . . ?
C00J C00I H00I 111.7 . . ?
C00H C00J H00J 112.6 . . ?
C00I C00J C00H 134.8(2) . . ?
C00I C00J H00J 112.6 . . ?
C00C C00K H00K 120.1 . . ?
C00C C00K C00L 119.9(3) . . ?
C00L C00K H00K 120.1 . . ?
C00F C00L C00K 120.7(3) . . ?
C00F C00L H00L 119.6 . . ?
C00K C00L H00L 119.6 . . ?
O003 C00M H00G 109.5 . . ?
O003 C00M H00H 109.5 . . ?
O003 C00M H00M 109.5 . . ?
H00G C00M H00H 109.5 . . ?
H00G C00M H00M 109.5 . . ?
H00H C00M H00M 109.5 . . ?
C00H C00N H00N 119.1 . . ?
C00H C00N C00R 121.8(4) . . ?
C00R C00N H00N 119.1 . . ?
C00H C00O H00O 119.6 . . ?
C00H C00O C00Q 120.9(3) . . ?
C00Q C00O H00O 119.6 . . ?
F00A C00P F00E 103.2(3) . . ?
F00A C00P C00G 113.6(3) . . ?
F00B C00P F00A 110.6(4) . . ?
F00B C00P F00E 102.4(4) . . ?
F00B C00P C00G 116.8(3) . . ?
F00E C00P C00G 108.7(3) . . ?
C00O C00Q H00Q 119.6 . . ?
C00S C00Q C00O 120.9(4) . . ?
C00S C00Q H00Q 119.6 . . ?
C00N C00R H00R 120.3 . . ?
C00N C00R C00S 119.4(4) . . ?
C00S C00R H00R 120.3 . . ?
C00Q C00S C00R 119.7(4) . . ?
C00Q C00S H00S 120.1 . . ?
C00R C00S H00S 120.1 . . ?

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
O001 C006 C009 C008 6.8(3) . . . . ?
O001 C006 C009 C00D 123.5(3) . . . . ?
O001 C006 C009 C00I -116.2(3) . . . . ?
O002 C004 C005 C007 -179.8(2) . . . . ?
O002 C004 C005 C00C -0.3(3) . . . . ?
O002 C004 C008 C009 -149.8(2) . . . . ?
O002 C004 C008 C00G -19.4(3) . . . . ?
O003 C006 C009 C008 -170.5(2) . . . . ?
O003 C006 C009 C00D -53.8(2) . . . . ?
O003 C006 C009 C00I 66.4(3) . . . . ?
C004 C005 C007 C00D -0.2(3) . . . . ?
C004 C005 C007 C00F 179.2(2) . . . . ?
C004 C005 C00C C00K -178.3(2) . . . . ?
C004 C008 C009 C006 59.7(3) . . . . ?
C004 C008 C009 C00D -58.1(2) . . . . ?
C004 C008 C009 C00I -173.91(19) . . . . ?
C004 C008 C00G C00P 100.9(3) . . . . ?
C005 C004 C008 C009 32.6(3) . . . . ?
C005 C004 C008 C00G 163.03(18) . . . . ?
C005 C007 C00D C009 -28.2(3) . . . . ?
C005 C007 C00F C00L -0.7(4) . . . . ?
C005 C00C C00K C00L -1.0(4) . . . . ?
C006 C009 C00D C007 -62.6(2) . . . . ?
C006 C009 C00I C00J 3.3(5) . . . . ?
C007 C005 C00C C00K 1.1(3) . . . . ?
C007 C00F C00L C00K 0.8(4) . . . . ?
C008 C004 C005 C007 -2.2(3) . . . . ?
C008 C004 C005 C00C 177.27(19) . . . . ?
C008 C009 C00D C007 55.8(2) . . . . ?
C008 C009 C00I C00J -120.1(4) . . . . ?
C008 C00G C00P F00A -177.6(3) . . . . ?
C008 C00G C00P F00B -47.0(5) . . . . ?
C008 C00G C00P F00E 68.1(4) . . . . ?
C009 C008 C00G C00P -130.0(3) . . . . ?
C009 C00I C00J C00H 1.0(7) . . . . ?
C00C C005 C007 C00D -179.7(2) . . . . ?
C00C C005 C007 C00F -0.2(3) . . . . ?
C00C C00K C00L C00F 0.1(4) . . . . ?
C00D C007 C00F C00L 178.7(2) . . . . ?
C00D C009 C00I C00J 124.4(4) . . . . ?
C00F C007 C00D C009 152.4(2) . . . . ?
C00G C008 C009 C006 -69.2(2) . . . . ?
C00G C008 C009 C00D 172.97(18) . . . . ?
C00G C008 C009 C00I 57.2(3) . . . . ?
C00H C00N C00R C00S 1.0(6) . . . . ?
C00H C00O C00Q C00S 0.2(6) . . . . ?
C00I C009 C00D C007 172.7(2) . . . . ?
C00J C00H C00N C00R -178.7(3) . . . . ?
C00J C00H C00O C00Q 177.8(3) . . . . ?
C00M O003 C006 O001 2.9(4) . . . . ?
C00M O003 C006 C009 -179.7(2) . . . . ?
C00N C00H C00J C00I -137.5(4) . . . . ?
C00N C00H C00O C00Q 2.0(5) . . . . ?
C00N C00R C00S C00Q 1.3(7) . . . . ?
C00O C00H C00J C00I 46.7(6) . . . . ?
C00O C00H C00N C00R -2.6(5) . . . . ?
C00O C00Q C00S C00R -1.9(7) . . . . ?

_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 8.094
_oxdiff_exptl_absorpt_empirical_full_min 0.560
