# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_CTBB_113K_Form_I
_database_code_depnum_ccdc_archive 'CCDC 2286243'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.5603(2)
_cell_length_b                   10.25450(10)
_cell_length_c                   7.79550(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.4500(10)
_cell_angle_gamma                90
_cell_volume                     1479.22(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6966
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      78.3570
_cell_measurement_theta_min      4.7980
_shelx_estimated_absorpt_T_max   0.641
_shelx_estimated_absorpt_T_min   0.550
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10857
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.033
_diffrn_reflns_theta_min         4.780
_diffrn_ambient_temperature      113.15
_diffrn_detector                 PILATUS
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -27.00   1.00    1.00    --  -49.00 -72.00   0.00   56
  2  ω    -77.00  17.00   1.00    1.00    --  -49.00  57.00-150.00   94
  3  ω   -133.00-107.00   1.00    1.00    --  -49.00 -72.00 -30.00   26
  4  ω   -136.00 -99.00   1.00    1.00    --  -49.00 -72.00   0.00   37
  5  ω    -98.00 -17.00   1.00    1.00    --  -49.00 -72.00 -30.00   81
  6  ω   -199.00-138.00   1.00    1.00    -- -110.00 -57.00 -60.00   61
  7  ω   -128.00-101.00   1.00    1.00    -- -110.00 -72.00 150.00   27
  8  ω   -143.00 -32.00   1.00    1.00    -- -110.00  38.00  90.00  111
  9  ω   -104.00 -46.00   1.00    1.00    -- -110.00  72.00 -60.00   58
 10  ω   -129.00 -77.00   1.00    1.00    -- -110.00 -38.00  60.00   52
 11  ω   -141.00 -25.00   1.00    1.00    -- -110.00  72.00-150.00  116
 12  ω   -197.00-134.00   1.00    1.00    -- -110.00 -72.00 150.00   63
 13  ω   -173.00-132.00   1.00    1.00    -- -110.00 -38.00  60.00   41
 14  ω   -124.00 -73.00   1.00    1.00    -- -110.00  72.00-180.00   51
 15  ω   -122.00 -81.00   1.00    1.00    -- -110.00 -57.00 -60.00   41
 16  ω    -53.00 -28.00   1.00    1.00    -- -110.00  57.00 -90.00   25
 17  ω   -139.00 -86.00   1.00    1.00    -- -110.00  72.00 -90.00   53
 18  ω    -93.00 -67.00   1.00    1.00    -- -110.00  57.00-180.00   26
 19  ω   -131.00 -86.00   1.00    1.00    -- -110.00  72.00 -30.00   45
 20  ω   -118.00 -92.00   1.00    1.00    -- -110.00  57.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224867000
_diffrn_orient_matrix_UB_12      0.1417504000
_diffrn_orient_matrix_UB_13      0.0265255000
_diffrn_orient_matrix_UB_21      -0.0151745000
_diffrn_orient_matrix_UB_22      0.0480404000
_diffrn_orient_matrix_UB_23      -0.0788313000
_diffrn_orient_matrix_UB_31      -0.1964797000
_diffrn_orient_matrix_UB_32      0.0125222000
_diffrn_orient_matrix_UB_33      0.0026862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2841
_reflns_number_total             3087
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0024(4)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.205
_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)+(0.0513P)²+0.7653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.02
 C15-F1 \\sim C15-F2 \\sim C15-F3 \\sim C15-F3A \\sim C15-F2A \\sim C15-F1A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim
Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14)
;
_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
Cl1 Cl 0.76520(2) 0.14646(5) 0.43967(6) 0.03756(16) Uani 1 1 d . . . . .
O1 O 0.44975(6) 0.10202(10) 0.79872(14) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.03177(6) 0.49725(14) 0.71149(18) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.42209(6) 0.26438(12) 0.60496(16) 0.0215(3) Uani 1 1 d . . . . .
H1 H 0.436672 0.311691 0.520060 0.026 Uiso 1 1 calc R U . . .
N2 N 0.35312(6) 0.28104(12) 0.65683(17) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.67853(8) 0.15594(16) 0.5092(2) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.64473(8) 0.27614(16) 0.5118(2) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.668637 0.352191 0.475888 0.031 Uiso 1 1 calc R U . . .
C3 C 0.57567(8) 0.28460(15) 0.5672(2) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.551843 0.366546 0.568617 0.029 Uiso 1 1 calc R U . . .
C4 C 0.54130(8) 0.17251(15) 0.62076(18) 0.0201(3) Uani 1 1 d . . . . .
C5 C 0.57684(8) 0.05302(15) 0.6211(2) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.553925 -0.022748 0.661117 0.027 Uiso 1 1 calc R U . . .
C6 C 0.64555(8) 0.04379(16) 0.5633(2) 0.0258(3) Uani 1 1 d . . . . .
H6 H 0.669484 -0.038007 0.560981 0.031 Uiso 1 1 calc R U . . .
C7 C 0.46732(8) 0.17560(14) 0.68418(19) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.31352(8) 0.35775(15) 0.5601(2) 0.0222(3) Uani 1 1 d . . . . .
H8 H 0.332288 0.393820 0.460541 0.027 Uiso 1 1 calc R U . . .
C9 C 0.23992(8) 0.39095(15) 0.5999(2) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.20028(8) 0.47935(16) 0.4941(2) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.220770 0.514506 0.396179 0.033 Uiso 1 1 calc R U . . .
C11 C 0.13109(9) 0.51640(18) 0.5309(2) 0.0315(4) Uani 1 1 d . . . . .
H11 H 0.103952 0.576265 0.458767 0.038 Uiso 1 1 calc R U . . .
C12 C 0.10277(8) 0.46461(16) 0.6737(2) 0.0276(4) Uani 1 1 d . . . . .
C13 C 0.13992(9) 0.37496(16) 0.7792(2) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.118767 0.339241 0.875925 0.034 Uiso 1 1 calc R U . . .
C14 C 0.20854(8) 0.33841(16) 0.7410(2) 0.0268(3) Uani 1 1 d . . . . .
H14 H 0.234675 0.276545 0.812016 0.032 Uiso 1 1 calc R U . . .
C15 C 0.02332(11) 0.6087(2) 0.7935(3) 0.0464(5) Uani 1 1 d D . . . .
F1 F -0.0439(3) 0.6333(12) 0.8216(15) 0.0581(19) Uani 0.579(12) 1 d D U P A 1
F2 F 0.0597(2) 0.5962(5) 0.9520(4) 0.0450(9) Uani 0.579(12) 1 d D U P A 1
F3 F 0.0549(4) 0.7186(3) 0.7381(8) 0.0703(15) Uani 0.579(12) 1 d D U P A 1
F1A F -0.0443(4) 0.6039(15) 0.840(2) 0.050(2) Uani 0.421(12) 1 d D U P A 2
F2A F 0.0668(4) 0.6415(11) 0.9183(13) 0.095(3) Uani 0.421(12) 1 d D U P A 2
F3A F 0.0179(5) 0.6935(7) 0.6599(12) 0.083(3) Uani 0.421(12) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7396(16) . ?
O1 C7 1.2321(19) . ?
O2 C12 1.4126(18) . ?
O2 C15 1.325(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.3827(16) . ?
N1 C7 1.3544(19) . ?
N2 C8 1.281(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.384(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 C5 1.391(2) . ?
C4 C7 1.495(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.464(2) . ?
C9 C10 1.396(2) . ?
C9 C14 1.393(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(3) . ?
C12 C13 1.382(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(2) . ?
C14 H14 0.9500 . ?
C15 F1 1.308(5) . ?
C15 F2 1.367(4) . ?
C15 F3 1.357(4) . ?
C15 F1A 1.333(5) . ?
C15 F2A 1.260(6) . ?
C15 F3A 1.354(5) . ?

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
C15 O2 C12 116.89(14) . . ?
N2 N1 H1 119.8 . . ?
C7 N1 H1 119.8 . . ?
C7 N1 N2 120.32(12) . . ?
C8 N2 N1 113.93(13) . . ?
C2 C1 Cl1 119.04(13) . . ?
C2 C1 C6 121.60(14) . . ?
C6 C1 Cl1 119.35(12) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.42(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.81(14) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C7 122.33(13) . . ?
C5 C4 C3 119.91(14) . . ?
C5 C4 C7 117.73(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.45(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.78(14) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 N1 123.54(14) . . ?
O1 C7 C4 121.87(13) . . ?
N1 C7 C4 114.58(13) . . ?
N2 C8 H8 119.3 . . ?
N2 C8 C9 121.34(14) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 118.91(14) . . ?
C14 C9 C8 122.12(14) . . ?
C14 C9 C10 118.97(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.58(15) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.61(15) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 O2 119.93(15) . . ?
C11 C12 C13 122.33(15) . . ?
C13 C12 O2 117.65(15) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.54(15) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.95(15) . . ?
C13 C14 H14 119.5 . . ?
O2 C15 F2 106.7(2) . . ?
O2 C15 F3 119.5(2) . . ?
O2 C15 F1A 104.3(8) . . ?
O2 C15 F3A 100.8(4) . . ?
F1 C15 O2 113.4(6) . . ?
F1 C15 F2 106.1(5) . . ?
F1 C15 F3 109.6(5) . . ?
F3 C15 F2 99.8(3) . . ?
F1A C15 F3A 102.5(6) . . ?
F2A C15 O2 120.7(4) . . ?
F2A C15 F1A 111.1(8) . . ?
F2A C15 F3A 115.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.93(12) . . . . ?
Cl1 C1 C6 C5 178.98(11) . . . . ?
O2 C12 C13 C14 177.84(15) . . . . ?
N1 N2 C8 C9 -177.39(13) . . . . ?
N2 N1 C7 O1 3.3(2) . . . . ?
N2 N1 C7 C4 -177.16(12) . . . . ?
N2 C8 C9 C10 177.30(15) . . . . ?
N2 C8 C9 C14 -1.9(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C2 C3 C4 C7 179.12(13) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C3 C4 C7 O1 -145.67(15) . . . . ?
C3 C4 C7 N1 34.7(2) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C5 C4 C7 O1 32.5(2) . . . . ?
C5 C4 C7 N1 -147.14(14) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C7 N1 N2 C8 -173.04(13) . . . . ?
C7 C4 C5 C6 179.82(13) . . . . ?
C8 C9 C10 C11 -177.97(15) . . . . ?
C8 C9 C14 C13 177.65(15) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C9 C14 C13 -1.5(2) . . . . ?
C10 C11 C12 O2 -178.05(15) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 O2 C15 F1 179.0(5) . . . . ?
C12 O2 C15 F2 -64.5(3) . . . . ?
C12 O2 C15 F3 47.4(5) . . . . ?
C12 O2 C15 F1A -169.1(6) . . . . ?
C12 O2 C15 F2A -43.3(7) . . . . ?
C12 O2 C15 F3A 84.9(5) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C14 C9 C10 C11 1.2(2) . . . . ?
C15 O2 C12 C11 -82.5(2) . . . . ?
C15 O2 C12 C13 100.9(2) . . . . ?

_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 1.619
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# 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_CTBB_365K_Form_I
_database_code_depnum_ccdc_archive 'CCDC 2286249'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   18.847(6)
_cell_length_b                   10.089(3)
_cell_length_c                   8.313(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.989(10)
_cell_angle_gamma                90
_cell_volume                     1580.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    365.00
_cell_measurement_theta_max      21.47
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.8521.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14647
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.161
_diffrn_ambient_temperature      365.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1587
_reflns_number_total             3610
_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       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.047
_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)+(0.0684P)²+0.4931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1986
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 O1-C15 \\sim O1-C15A
 with sigma of 0.02
 F2-F1 \\sim F2-F3 \\sim F3-F1
 with sigma of 0.02
 F3-C15 \\sim F2-C15 \\sim F1-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim C15 \\sim F1A \\sim F2A \\sim F3A \\sim C15A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{F1A, F2A, F3A, C15A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{F1, F2, F3, C15}
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C15A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C15)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14)
;
_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
Cl1 Cl 0.23669(6) 0.12935(14) 0.57882(16) 0.1492(6) Uani 1 1 d . . . . .
O1 O 0.96263(15) 0.4955(4) 0.2817(4) 0.1446(12) Uani 1 1 d D . . . .
O2 O 0.54957(12) 0.1141(2) 0.2113(3) 0.0895(7) Uani 1 1 d . . . . .
N1 N 0.57603(13) 0.2643(2) 0.4063(3) 0.0777(7) Uani 1 1 d . . . . .
H1 H 0.561734 0.305866 0.490064 0.093 Uiso 1 1 calc R U . . .
N2 N 0.64421(14) 0.2838(3) 0.3533(3) 0.0775(7) Uani 1 1 d . . . . .
C1 C 0.32205(19) 0.1451(4) 0.5077(4) 0.0925(11) Uani 1 1 d . . . . .
C2 C 0.35639(19) 0.2648(4) 0.5204(5) 0.1028(12) Uani 1 1 d . . . . .
H2 H 0.333879 0.336714 0.567488 0.123 Uiso 1 1 calc R U . . .
C3 C 0.42455(17) 0.2784(3) 0.4631(4) 0.0901(10) Uani 1 1 d . . . . .
H3 H 0.447531 0.359692 0.471660 0.108 Uiso 1 1 calc R U . . .
C4 C 0.45881(16) 0.1724(3) 0.3935(3) 0.0690(8) Uani 1 1 d . . . . .
C5 C 0.42263(18) 0.0529(3) 0.3801(4) 0.0820(9) Uani 1 1 d . . . . .
H5 H 0.444489 -0.019167 0.331742 0.098 Uiso 1 1 calc R U . . .
C6 C 0.3549(2) 0.0394(4) 0.4373(4) 0.0964(11) Uani 1 1 d . . . . .
H6 H 0.331399 -0.041403 0.428190 0.116 Uiso 1 1 calc R U . . .
C7 C 0.53159(17) 0.1805(3) 0.3279(4) 0.0735(8) Uani 1 1 d . . . . .
C8 C 0.68371(18) 0.3544(3) 0.4444(4) 0.0807(9) Uani 1 1 d . . . . .
H8 H 0.665681 0.385318 0.540814 0.097 Uiso 1 1 calc R U . . .
C9 C 0.75654(17) 0.3886(3) 0.4029(4) 0.0779(9) Uani 1 1 d . . . . .
C10 C 0.7949(2) 0.4749(4) 0.4979(5) 0.1086(12) Uani 1 1 d . . . . .
H10 H 0.774938 0.508265 0.591040 0.130 Uiso 1 1 calc R U . . .
C11 C 0.8630(2) 0.5130(4) 0.4574(6) 0.1202(14) Uani 1 1 d . . . . .
H11 H 0.888476 0.571703 0.522466 0.144 Uiso 1 1 calc R U . . .
C12 C 0.89164(19) 0.4639(4) 0.3226(5) 0.1026(12) Uani 1 1 d . . . . .
C13 C 0.8562(2) 0.3763(4) 0.2277(5) 0.1045(12) Uani 1 1 d . . . . .
H13 H 0.877054 0.342251 0.136013 0.125 Uiso 1 1 calc R U . . .
C14 C 0.78889(19) 0.3384(3) 0.2688(4) 0.0942(11) Uani 1 1 d . . . . .
H14 H 0.764616 0.277486 0.204443 0.113 Uiso 1 1 calc R U . . .
F1 F 0.9925(5) 0.6774(9) 0.3670(12) 0.183(3) Uani 0.483(9) 1 d D U P A 1
F2 F 1.0397(6) 0.5940(15) 0.1590(19) 0.191(4) Uani 0.483(9) 1 d D U P A 1
F3 F 0.9331(6) 0.6710(13) 0.1490(17) 0.204(4) Uani 0.483(9) 1 d D U P A 1
C15 C 0.9807(7) 0.6107(13) 0.2354(17) 0.169(3) Uani 0.483(9) 1 d D U P A 1
F1A F 1.0395(6) 0.6431(14) 0.184(2) 0.200(4) Uani 0.517(9) 1 d D U P A 2
F2A F 0.9416(5) 0.5949(11) 0.0678(10) 0.183(3) Uani 0.517(9) 1 d D U P A 2
F3A F 0.9437(7) 0.7193(8) 0.2701(16) 0.195(4) Uani 0.517(9) 1 d D U P A 2
C15A C 0.9735(7) 0.6093(12) 0.2135(17) 0.168(3) Uani 0.517(9) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.731(4) . ?
O1 C12 1.423(4) . ?
O1 C15 1.272(12) . ?
O1 C15A 1.298(11) . ?
O2 C7 1.231(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.380(3) . ?
N1 C7 1.350(4) . ?
N2 C8 1.271(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.369(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.487(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.462(4) . ?
C9 C10 1.374(4) . ?
C9 C14 1.376(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.347(5) . ?
C12 C13 1.353(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(5) . ?
C14 H14 0.9300 . ?
F1 C15 1.300(12) . ?
F2 C15 1.301(11) . ?
F3 C15 1.292(11) . ?
F1A C15A 1.317(11) . ?
F2A C15A 1.351(12) . ?
F3A C15A 1.333(11) . ?

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
C15 O1 C12 122.4(7) . . ?
C15A O1 C12 117.3(7) . . ?
N2 N1 H1 119.7 . . ?
C7 N1 H1 119.7 . . ?
C7 N1 N2 120.6(3) . . ?
C8 N2 N1 115.4(3) . . ?
C2 C1 Cl1 119.6(3) . . ?
C6 C1 Cl1 120.2(3) . . ?
C6 C1 C2 120.2(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 C7 123.5(3) . . ?
C5 C4 C7 118.3(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O2 C7 N1 123.0(3) . . ?
O2 C7 C4 121.8(3) . . ?
N1 C7 C4 115.2(3) . . ?
N2 C8 H8 118.9 . . ?
N2 C8 C9 122.3(3) . . ?
C9 C8 H8 118.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 C14 117.6(3) . . ?
C14 C9 C8 122.4(3) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 O1 120.6(4) . . ?
C11 C12 C13 121.6(4) . . ?
C13 C12 O1 117.7(4) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.1(4) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
O1 C15 F1 105.1(10) . . ?
O1 C15 F2 105.4(12) . . ?
O1 C15 F3 114.3(12) . . ?
F1 C15 F2 110.1(11) . . ?
F3 C15 F1 109.3(11) . . ?
F3 C15 F2 112.4(11) . . ?
O1 C15A F1A 117.8(13) . . ?
O1 C15A F2A 103.0(10) . . ?
O1 C15A F3A 120.8(11) . . ?
F1A C15A F2A 105.5(11) . . ?
F1A C15A F3A 104.8(10) . . ?
F3A C15A F2A 102.9(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.7(3) . . . . ?
Cl1 C1 C6 C5 179.6(3) . . . . ?
O1 C12 C13 C14 176.6(3) . . . . ?
N1 N2 C8 C9 -177.7(3) . . . . ?
N2 N1 C7 O2 3.0(4) . . . . ?
N2 N1 C7 C4 -177.7(2) . . . . ?
N2 C8 C9 C10 174.1(3) . . . . ?
N2 C8 C9 C14 -5.1(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C2 C3 C4 C7 179.3(3) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C3 C4 C7 O2 -147.5(3) . . . . ?
C3 C4 C7 N1 33.2(4) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C5 C4 C7 O2 30.7(4) . . . . ?
C5 C4 C7 N1 -148.6(3) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C7 N1 N2 C8 -173.4(3) . . . . ?
C7 C4 C5 C6 -179.5(3) . . . . ?
C8 C9 C10 C11 -177.3(4) . . . . ?
C8 C9 C14 C13 177.0(3) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C9 C14 C13 -2.2(5) . . . . ?
C10 C11 C12 O1 -176.8(4) . . . . ?
C10 C11 C12 C13 -1.4(7) . . . . ?
C11 C12 C13 C14 1.1(6) . . . . ?
C12 O1 C15 F1 84.6(12) . . . . ?
C12 O1 C15 F2 -159.1(8) . . . . ?
C12 O1 C15 F3 -35.3(15) . . . . ?
C12 O1 C15A F1A 176.0(10) . . . . ?
C12 O1 C15A F2A -68.4(11) . . . . ?
C12 O1 C15A F3A 45.4(15) . . . . ?
C12 C13 C14 C9 0.7(6) . . . . ?
C14 C9 C10 C11 1.9(6) . . . . ?
C15 O1 C12 C11 -70.5(9) . . . . ?
C15 O1 C12 C13 114.0(9) . . . . ?
C15A O1 C12 C11 -80.4(9) . . . . ?
C15A O1 C12 C13 104.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_CTBB_113K_Form_III
_database_code_depnum_ccdc_archive 'CCDC 2286530'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2022-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.8875(3)
_cell_length_b                   8.26765(14)
_cell_length_c                   19.4727(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.5615(14)
_cell_angle_gamma                90
_cell_volume                     3020.84(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13815
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      78.6700
_cell_measurement_theta_min      4.5940
_shelx_estimated_absorpt_T_max   0.632
_shelx_estimated_absorpt_T_min   0.556
_exptl_absorpt_coefficient_mu    2.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22817
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.985
_diffrn_reflns_theta_min         4.571
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  17.00   0.50    0.50    --    5.00  57.00-180.00   52
  2  ω     42.00  68.00   0.50    0.50    --    5.00  57.00-180.00   52
  3  ω    -95.00 -14.00   0.50    0.50    --  -48.80 -72.00  90.00  162
  4  ω   -135.00 -99.00   0.50    0.50    --  -48.80 -72.00  90.00   72
  5  ω    -67.00   6.00   0.50    0.50    --  -48.80  57.00 -30.00  146
  6  ω   -131.00 -20.00   0.50    0.50    --  -48.80 -57.00-180.00  222
  7  ω    -78.00 -25.00   0.50    1.50    -- -110.00  19.00  30.00  106
  8  ω   -123.00 -47.00   0.50    1.50    -- -110.00  72.00 -30.00  152
  9  ω   -191.00-117.50   0.50    1.50    -- -110.00 -72.00 -90.00  147
 10  ω   -192.00-152.00   0.50    1.50    -- -110.00 -72.00  90.00   80
 11  ω   -190.00 -90.00   0.50    1.50    -- -110.00 -72.00 -30.00  200
 12  ω   -155.00-102.00   0.50    1.50    -- -110.00  19.00  30.00  106
 13  ω    -69.00 -24.00   0.50    1.50    -- -110.00  72.00  60.00   90
 14  ω   -140.00 -63.00   0.50    1.50    -- -110.00  72.00  30.00  154
 15  ω   -139.00 -39.00   0.50    1.50    -- -110.00  72.00  90.00  200
 16  ω   -111.00 -86.00   0.50    1.50    -- -110.00  72.00 -60.00   50
 17  ω   -132.00 -89.00   0.50    1.50    -- -110.00  72.00  60.00   86
 18  ω   -109.00 -84.00   0.50    1.50    -- -110.00  72.00   0.00   50
 19  ω   -185.00 -94.00   0.50    1.50    -- -110.00 -72.00  30.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016714000
_diffrn_orient_matrix_UB_12      -0.1487277000
_diffrn_orient_matrix_UB_13      0.0474484000
_diffrn_orient_matrix_UB_21      0.0064541000
_diffrn_orient_matrix_UB_22      0.1116901000
_diffrn_orient_matrix_UB_23      0.0638183000
_diffrn_orient_matrix_UB_31      -0.0817612000
_diffrn_orient_matrix_UB_32      0.0119931000
_diffrn_orient_matrix_UB_33      -0.0050982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5850
_reflns_number_total             6291
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.00079(10)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.100
_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)+(0.0517P)²+7.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1767
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), N3(H3A), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C25(H25),
 C26(H26), C28(H28), C29(H29)
;
_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
Cl1 Cl 0.23727(4) 0.79717(12) 0.24524(5) 0.0502(3) Uani 1 1 d . . . . .
F1 F 0.98955(14) 0.9193(4) 0.1707(2) 0.1037(13) Uani 1 1 d . . . . .
F2 F 1.00302(15) 0.6666(4) 0.1769(2) 0.0928(11) Uani 1 1 d . . . . .
F3 F 1.07812(12) 0.8200(5) 0.23130(18) 0.0889(10) Uani 1 1 d . . . . .
O1 O 0.54428(10) 0.8870(3) 0.12354(10) 0.0305(5) Uani 1 1 d . . . . .
O2 O 0.98059(13) 0.7960(5) 0.27177(17) 0.0681(9) Uani 1 1 d . . . . .
N1 N 0.58104(12) 0.8122(3) 0.23717(13) 0.0257(5) Uani 1 1 d . . . . .
H1 H 0.568970 0.792186 0.278663 0.031 Uiso 1 1 calc R U . . .
N2 N 0.64985(12) 0.8105(3) 0.22431(13) 0.0272(5) Uani 1 1 d . . . . .
C1 C 0.32288(15) 0.8105(4) 0.22844(17) 0.0319(6) Uani 1 1 d . . . . .
C2 C 0.34032(15) 0.9164(4) 0.17656(17) 0.0321(6) Uani 1 1 d . . . . .
H2 H 0.304457 0.980013 0.151235 0.039 Uiso 1 1 calc R U . . .
C3 C 0.40852(15) 0.9266(4) 0.16321(16) 0.0285(6) Uani 1 1 d . . . . .
H3 H 0.421619 0.996903 0.128212 0.034 Uiso 1 1 calc R U . . .
C4 C 0.45926(14) 0.8322(3) 0.20159(14) 0.0227(5) Uani 1 1 d . . . . .
C5 C 0.44034(14) 0.7276(3) 0.25343(16) 0.0271(6) Uani 1 1 d . . . . .
H5 H 0.476142 0.664562 0.279161 0.032 Uiso 1 1 calc R U . . .
C6 C 0.37221(15) 0.7153(4) 0.26720(17) 0.0315(6) Uani 1 1 d . . . . .
H6 H 0.358890 0.644484 0.301929 0.038 Uiso 1 1 calc R U . . .
C7 C 0.53183(14) 0.8459(3) 0.18347(15) 0.0243(6) Uani 1 1 d . . . . .
C8 C 0.69314(15) 0.8218(4) 0.28049(16) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.675643 0.836368 0.323911 0.036 Uiso 1 1 calc R U . . .
C9 C 0.76743(15) 0.8120(4) 0.27576(16) 0.0298(6) Uani 1 1 d . . . . .
C10 C 0.79341(17) 0.7456(5) 0.21684(19) 0.0415(8) Uani 1 1 d . . . . .
H10 H 0.761039 0.705900 0.179747 0.050 Uiso 1 1 calc R U . . .
C11 C 0.86412(18) 0.7384(6) 0.2131(2) 0.0514(10) Uani 1 1 d . . . . .
H11 H 0.882958 0.692278 0.174395 0.062 Uiso 1 1 calc R U . . .
C12 C 0.90829(17) 0.8019(5) 0.2688(2) 0.0457(9) Uani 1 1 d . . . . .
C13 C 0.88423(17) 0.8679(5) 0.3273(2) 0.0437(8) Uani 1 1 d . . . . .
H13 H 0.916887 0.908635 0.363912 0.052 Uiso 1 1 calc R U . . .
C14 C 0.81338(17) 0.8730(5) 0.33104(18) 0.0381(7) Uani 1 1 d . . . . .
H14 H 0.795106 0.917127 0.370467 0.046 Uiso 1 1 calc R U . . .
C15 C 1.01111(18) 0.8031(6) 0.2128(3) 0.0548(10) Uani 1 1 d . . . . .
Cl2 Cl 0.24636(4) 0.98664(11) 0.46323(5) 0.0451(2) Uani 1 1 d . . . . .
F4 F 0.91717(13) 0.1776(4) 0.45479(15) 0.0756(9) Uani 1 1 d . . . . .
F5 F 1.01984(12) 0.1891(3) 0.50867(15) 0.0679(8) Uani 1 1 d . . . . .
F6 F 0.93557(15) 0.1142(3) 0.56414(17) 0.0766(8) Uani 1 1 d . . . . .
O3 O 0.56445(11) 0.8394(3) 0.37994(11) 0.0350(5) Uani 1 1 d . . . . .
O4 O 0.94764(11) 0.3704(3) 0.53355(15) 0.0454(6) Uani 1 1 d . . . . .
N3 N 0.57534(12) 0.7101(3) 0.48626(13) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.555267 0.683225 0.523260 0.032 Uiso 1 1 calc R U . . .
N4 N 0.64306(12) 0.6672(3) 0.47890(13) 0.0278(5) Uani 1 1 d . . . . .
C16 C 0.33150(15) 0.9296(4) 0.45569(18) 0.0332(7) Uani 1 1 d . . . . .
C17 C 0.36668(17) 1.0037(4) 0.40560(17) 0.0327(7) Uani 1 1 d . . . . .
H17 H 0.343871 1.084158 0.376066 0.039 Uiso 1 1 calc R U . . .
C18 C 0.43451(16) 0.9580(4) 0.40003(16) 0.0311(6) Uani 1 1 d . . . . .
H18 H 0.460325 1.006536 0.366338 0.037 Uiso 1 1 calc R U . . .
C19 C 0.46631(14) 0.8391(3) 0.44407(15) 0.0248(6) Uani 1 1 d . . . . .
C20 C 0.42952(15) 0.7651(4) 0.49422(17) 0.0333(7) Uani 1 1 d . . . . .
H20 H 0.451963 0.684078 0.523735 0.040 Uiso 1 1 calc R U . . .
C21 C 0.36165(16) 0.8105(4) 0.49999(19) 0.0376(7) Uani 1 1 d . . . . .
H21 H 0.335382 0.762199 0.533400 0.045 Uiso 1 1 calc R U . . .
C22 C 0.53946(15) 0.7969(4) 0.43381(15) 0.0266(6) Uani 1 1 d . . . . .
C23 C 0.67588(15) 0.6022(4) 0.53423(16) 0.0289(6) Uani 1 1 d . . . . .
H23 H 0.652500 0.591575 0.574668 0.035 Uiso 1 1 calc R U . . .
C24 C 0.74722(15) 0.5470(4) 0.53390(16) 0.0292(6) Uani 1 1 d . . . . .
C25 C 0.78540(16) 0.5825(4) 0.47725(17) 0.0329(7) Uani 1 1 d . . . . .
H25 H 0.764794 0.647295 0.439905 0.039 Uiso 1 1 calc R U . . .
C26 C 0.85176(16) 0.5220(4) 0.47763(18) 0.0374(7) Uani 1 1 d . . . . .
H26 H 0.879133 0.542800 0.440584 0.045 Uiso 1 1 calc R U . . .
C27 C 0.87910(15) 0.4277(4) 0.53424(18) 0.0355(7) Uani 1 1 d . . . . .
C28 C 0.84396(17) 0.3957(4) 0.59150(19) 0.0398(8) Uani 1 1 d . . . . .
H28 H 0.865662 0.334912 0.629648 0.048 Uiso 1 1 calc R U . . .
C29 C 0.77685(17) 0.4558(4) 0.59016(18) 0.0376(7) Uani 1 1 d . . . . .
H29 H 0.750047 0.435476 0.627671 0.045 Uiso 1 1 calc R U . . .
C30 C 0.95373(19) 0.2163(5) 0.5149(2) 0.0498(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.690(3) . ?
F1 C15 1.298(5) . ?
F2 C15 1.326(5) . ?
F3 C15 1.283(4) . ?
O1 C7 1.263(4) . ?
O2 C12 1.361(4) . ?
O2 C15 1.343(5) . ?
N1 H1 0.8800 . ?
N1 N2 1.351(3) . ?
N1 C7 1.347(4) . ?
N2 C8 1.292(4) . ?
C1 C2 1.404(5) . ?
C1 C6 1.377(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.345(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 C5 1.406(4) . ?
C4 C7 1.458(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.348(4) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.419(4) . ?
C9 C10 1.409(5) . ?
C9 C14 1.397(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.347(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(5) . ?
C12 C13 1.385(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.349(4) . ?
C14 H14 0.9500 . ?
Cl2 C16 1.698(3) . ?
F4 C30 1.329(5) . ?
F5 C30 1.288(4) . ?
F6 C30 1.350(5) . ?
O3 C22 1.249(4) . ?
O4 C27 1.380(3) . ?
O4 C30 1.333(5) . ?
N3 H3A 0.8800 . ?
N3 N4 1.351(3) . ?
N3 C22 1.363(4) . ?
N4 C23 1.296(4) . ?
C16 C17 1.384(5) . ?
C16 C21 1.388(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.352(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(4) . ?
C19 C20 1.402(4) . ?
C19 C22 1.461(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.353(4) . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.423(4) . ?
C24 C25 1.416(4) . ?
C24 C29 1.394(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.349(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.400(5) . ?
C27 C28 1.387(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.359(4) . ?
C29 H29 0.9500 . ?

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
C15 O2 C12 119.3(3) . . ?
N2 N1 H1 121.6 . . ?
C7 N1 H1 121.6 . . ?
C7 N1 N2 116.8(2) . . ?
C8 N2 N1 111.8(2) . . ?
C2 C1 Cl1 119.2(2) . . ?
C6 C1 Cl1 117.3(2) . . ?
C6 C1 C2 123.4(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 C7 115.9(3) . . ?
C5 C4 C7 123.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 121.6 . . ?
C5 C6 C1 116.7(3) . . ?
C5 C6 H6 121.6 . . ?
O1 C7 N1 126.0(2) . . ?
O1 C7 C4 121.6(3) . . ?
N1 C7 C4 112.4(2) . . ?
N2 C8 H8 120.8 . . ?
N2 C8 C9 118.4(3) . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.9(3) . . ?
C14 C9 C8 117.5(3) . . ?
C14 C9 C10 121.6(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(4) . . ?
C12 C11 H11 121.6 . . ?
O2 C12 C11 121.9(4) . . ?
O2 C12 C13 113.7(3) . . ?
C13 C12 C11 124.4(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 H14 120.7 . . ?
C13 C14 C9 118.6(3) . . ?
C13 C14 H14 120.7 . . ?
F1 C15 F2 106.8(4) . . ?
F1 C15 O2 115.9(4) . . ?
F2 C15 O2 112.2(4) . . ?
F3 C15 F1 108.9(4) . . ?
F3 C15 F2 106.9(3) . . ?
F3 C15 O2 105.7(4) . . ?
C30 O4 C27 116.2(3) . . ?
N4 N3 H3A 121.5 . . ?
N4 N3 C22 117.0(2) . . ?
C22 N3 H3A 121.5 . . ?
C23 N4 N3 112.9(2) . . ?
C17 C16 Cl2 118.3(2) . . ?
C17 C16 C21 123.8(3) . . ?
C21 C16 Cl2 118.0(3) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 117.9(3) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 121.5(3) . . ?
C18 C19 C22 115.6(3) . . ?
C20 C19 C22 122.8(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 H21 121.0 . . ?
C20 C21 C16 118.1(3) . . ?
C20 C21 H21 121.0 . . ?
O3 C22 N3 125.0(3) . . ?
O3 C22 C19 120.1(3) . . ?
N3 C22 C19 114.9(2) . . ?
N4 C23 H23 120.3 . . ?
N4 C23 C24 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.2(3) . . ?
C29 C24 C23 117.7(3) . . ?
C29 C24 C25 122.0(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.3(3) . . ?
C26 C25 H25 120.8 . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 118.0(3) . . ?
C27 C26 H26 121.0 . . ?
O4 C27 C26 116.5(3) . . ?
O4 C27 C28 118.5(3) . . ?
C28 C27 C26 124.9(3) . . ?
C27 C28 H28 121.8 . . ?
C29 C28 C27 116.5(3) . . ?
C29 C28 H28 121.8 . . ?
C24 C29 H29 119.9 . . ?
C28 C29 C24 120.2(3) . . ?
C28 C29 H29 119.9 . . ?
F4 C30 F6 109.0(4) . . ?
F4 C30 O4 114.7(3) . . ?
F5 C30 F4 106.6(3) . . ?
F5 C30 F6 106.6(3) . . ?
F5 C30 O4 107.9(3) . . ?
O4 C30 F6 111.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.9(2) . . . . ?
Cl1 C1 C6 C5 -179.7(2) . . . . ?
O2 C12 C13 C14 -177.1(4) . . . . ?
N1 N2 C8 C9 176.3(3) . . . . ?
N2 N1 C7 O1 -5.3(4) . . . . ?
N2 N1 C7 C4 175.5(2) . . . . ?
N2 C8 C9 C10 -18.3(5) . . . . ?
N2 C8 C9 C14 160.6(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C7 178.6(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C7 O1 -26.1(4) . . . . ?
C3 C4 C7 N1 153.2(3) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C5 C4 C7 O1 152.4(3) . . . . ?
C5 C4 C7 N1 -28.3(4) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C7 N1 N2 C8 162.2(3) . . . . ?
C7 C4 C5 C6 -178.1(3) . . . . ?
C8 C9 C10 C11 179.5(4) . . . . ?
C8 C9 C14 C13 -178.8(3) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C9 C14 C13 0.2(5) . . . . ?
C10 C11 C12 O2 177.6(4) . . . . ?
C10 C11 C12 C13 1.3(7) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 O2 C15 F1 49.7(6) . . . . ?
C12 O2 C15 F2 -73.4(5) . . . . ?
C12 O2 C15 F3 170.4(4) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C14 C9 C10 C11 0.6(6) . . . . ?
C15 O2 C12 C11 31.8(6) . . . . ?
C15 O2 C12 C13 -151.5(4) . . . . ?
Cl2 C16 C17 C18 179.8(2) . . . . ?
Cl2 C16 C21 C20 -179.8(3) . . . . ?
O4 C27 C28 C29 179.4(3) . . . . ?
N3 N4 C23 C24 178.4(3) . . . . ?
N4 N3 C22 O3 -0.1(4) . . . . ?
N4 N3 C22 C19 179.6(2) . . . . ?
N4 C23 C24 C25 8.7(5) . . . . ?
N4 C23 C24 C29 -170.2(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C16 C21 C20 0.5(5) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C17 C18 C19 C22 179.5(3) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C18 C19 C22 O3 -14.8(4) . . . . ?
C18 C19 C22 N3 165.5(3) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C20 C19 C22 O3 164.6(3) . . . . ?
C20 C19 C22 N3 -15.1(4) . . . . ?
C21 C16 C17 C18 -0.5(5) . . . . ?
C22 N3 N4 C23 172.3(3) . . . . ?
C22 C19 C20 C21 -179.5(3) . . . . ?
C23 C24 C25 C26 -177.2(3) . . . . ?
C23 C24 C29 C28 177.9(3) . . . . ?
C24 C25 C26 C27 -0.1(5) . . . . ?
C25 C24 C29 C28 -0.9(5) . . . . ?
C25 C26 C27 O4 -178.8(3) . . . . ?
C25 C26 C27 C28 -2.2(5) . . . . ?
C26 C27 C28 C29 2.9(5) . . . . ?
C27 O4 C30 F4 53.4(5) . . . . ?
C27 O4 C30 F5 172.0(3) . . . . ?
C27 O4 C30 F6 -71.2(4) . . . . ?
C27 C28 C29 C24 -1.2(5) . . . . ?
C29 C24 C25 C26 1.7(5) . . . . ?
C30 O4 C27 C26 -101.3(4) . . . . ?
C30 O4 C27 C28 81.9(4) . . . . ?

_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 2.538
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_CTBB_380K_Form_II
_database_code_depnum_ccdc_archive 'CCDC 2286528'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   19.031(16)
_cell_length_b                   9.539(8)
_cell_length_c                   8.813(7)
_cell_angle_alpha                90
_cell_angle_beta                 86.26(3)
_cell_angle_gamma                90
_cell_volume                     1596(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    380.00
_cell_measurement_theta_max      19.69
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4410
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1754 before and 0.1126 after correction.
The Ratio of minimum to maximum transmission is 0.5915.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1302
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12382
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.803
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_temperature      380.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1115
_reflns_number_total             3669
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.053
_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     245
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     176
_refine_ls_R_factor_all          0.3019
_refine_ls_R_factor_gt           0.1317
_refine_ls_restrained_S_all      1.068
_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)+(0.1419P)²+1.1224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3205
_refine_ls_wR_factor_ref         0.4244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 O2-C15A = O2-C15
 1.3 with sigma of 0.01
 F3A-C15A \\sim F2A-C15A \\sim F1A-C15A \\sim F2-C15 \\sim F3-C15 \\sim F1-C15
 with sigma of 0.02
 F2A-F1A \\sim F3A-F2A \\sim F3A-F1A \\sim F3-F2 \\sim F2-F1 \\sim F3-F1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O2 \\sim C15 \\sim F3A \\sim F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim
C15A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=Sof(C15A)=1-FVAR(1)
 Sof(C15)=Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), N1(H1)
;
_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
C1 C 0.6848(4) -0.1237(11) -0.5248(10) 0.126(3) Uani 1 1 d . . . . .
C2 C 0.6510(5) -0.0280(9) -0.4315(11) 0.135(3) Uani 1 1 d . . . . .
H2 H 0.674122 0.052807 -0.403010 0.162 Uiso 1 1 calc R U . . .
C3 C 0.5821(4) -0.0520(8) -0.3796(8) 0.111(2) Uani 1 1 d . . . . .
H3 H 0.559279 0.013880 -0.316091 0.133 Uiso 1 1 calc R U . . .
C4 C 0.5458(4) -0.1708(7) -0.4191(7) 0.0956(19) Uani 1 1 d . . . . .
C5 C 0.5814(4) -0.2674(9) -0.5108(10) 0.132(3) Uani 1 1 d . . . . .
H5 H 0.558840 -0.349544 -0.536830 0.158 Uiso 1 1 calc R U . . .
C6 C 0.6500(4) -0.2444(11) -0.5647(10) 0.135(3) Uani 1 1 d . . . . .
H6 H 0.672968 -0.310181 -0.628067 0.162 Uiso 1 1 calc R U . . .
C7 C 0.4732(4) -0.1853(8) -0.3496(10) 0.104(2) Uani 1 1 d . . . . .
C8 C 0.3242(5) -0.3572(9) -0.4576(10) 0.123(3) Uani 1 1 d . . . . .
H8 H 0.343362 -0.388471 -0.551314 0.148 Uiso 1 1 calc R U . . .
C9 C 0.2503(4) -0.3886(9) -0.4113(9) 0.114(2) Uani 1 1 d . . . . .
C10 C 0.2163(4) -0.3343(9) -0.2842(10) 0.128(3) Uani 1 1 d . . . . .
H10 H 0.239551 -0.271259 -0.224503 0.154 Uiso 1 1 calc R U . . .
C11 C 0.1479(5) -0.3716(10) -0.2428(13) 0.150(3) Uani 1 1 d . . . . .
H11 H 0.124884 -0.334715 -0.155382 0.180 Uiso 1 1 calc R U . . .
C12 C 0.1152(5) -0.4609(12) -0.3295(16) 0.155(4) Uani 1 1 d . . . . .
C13 C 0.1451(7) -0.5168(12) -0.4566(16) 0.175(4) Uani 1 1 d . . . . .
H13 H 0.120436 -0.578983 -0.514506 0.210 Uiso 1 1 calc R U . . .
C14 C 0.2133(6) -0.4803(11) -0.4998(11) 0.153(3) Uani 1 1 d . . . . .
H14 H 0.234939 -0.517076 -0.588805 0.183 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77138(13) -0.1010(3) -0.5907(3) 0.1864(15) Uani 1 1 d . . . . .
N1 N 0.4307(3) -0.2667(6) -0.4260(7) 0.1084(18) Uani 1 1 d . . . . .
H1 H 0.446495 -0.305667 -0.509410 0.130 Uiso 1 1 calc R U . . .
N2 N 0.3614(4) -0.2893(6) -0.3728(7) 0.1117(19) Uani 1 1 d . . . . .
O1 O 0.4545(3) -0.1307(6) -0.2291(6) 0.1275(19) Uani 1 1 d . . . . .
O2 O 0.0424(4) -0.4882(11) -0.2847(12) 0.220(3) Uani 1 1 d D U . . .
C15 C 0.0217(9) -0.6104(16) -0.234(2) 0.232(4) Uani 0.515(10) 1 d D U P A 1
F3A F -0.0441(8) -0.599(3) -0.218(2) 0.241(6) Uani 0.485(10) 1 d D U P A 2
F1 F 0.0041(9) -0.655(2) -0.3711(16) 0.240(5) Uani 0.515(10) 1 d D U P A 1
F2 F 0.0699(7) -0.696(2) -0.184(2) 0.227(5) Uani 0.515(10) 1 d D U P A 1
F3 F -0.0346(9) -0.621(2) -0.1401(18) 0.238(5) Uani 0.515(10) 1 d D U P A 1
F1A F 0.0477(10) -0.7201(19) -0.300(3) 0.240(6) Uani 0.485(10) 1 d D U P A 2
F2A F 0.0525(8) -0.588(2) -0.1004(19) 0.239(5) Uani 0.485(10) 1 d D U P A 2
C15A C 0.0241(10) -0.6082(15) -0.226(2) 0.232(4) Uani 0.485(10) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.362(11) . ?
C1 C6 1.386(11) . ?
C1 Cl1 1.724(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(9) . ?
C4 C5 1.375(9) . ?
C4 C7 1.481(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(10) . ?
C6 H6 0.9300 . ?
C7 N1 1.335(9) . ?
C7 O1 1.215(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.469(11) . ?
C8 N2 1.245(9) . ?
C9 C10 1.359(10) . ?
C9 C14 1.394(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.326(13) . ?
C12 C13 1.335(14) . ?
C12 O2 1.438(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(13) . ?
C14 H14 0.9300 . ?
N1 H1 0.8600 . ?
N1 N2 1.389(7) . ?
O2 C15 1.300(10) . ?
O2 C15A 1.293(10) . ?
C15 F1 1.344(15) . ?
C15 F2 1.323(13) . ?
C15 F3 1.314(13) . ?
F3A C15A 1.298(14) . ?
F1A C15A 1.312(13) . ?
F2A C15A 1.281(14) . ?

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
C2 C1 C6 119.7(7) . . ?
C2 C1 Cl1 121.6(8) . . ?
C6 C1 Cl1 118.7(8) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(8) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(7) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C7 116.2(7) . . ?
C5 C4 C3 117.5(7) . . ?
C5 C4 C7 126.3(8) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(8) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(8) . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C4 115.2(7) . . ?
O1 C7 C4 122.3(8) . . ?
O1 C7 N1 122.5(7) . . ?
C9 C8 H8 119.7 . . ?
N2 C8 H8 119.7 . . ?
N2 C8 C9 120.7(8) . . ?
C10 C9 C8 123.2(9) . . ?
C10 C9 C14 118.0(8) . . ?
C14 C9 C8 118.8(9) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(9) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(9) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 123.3(10) . . ?
C11 C12 O2 115.9(11) . . ?
C13 C12 O2 120.6(13) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.5(11) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(9) . . ?
C13 C14 H14 119.8 . . ?
C7 N1 H1 119.6 . . ?
C7 N1 N2 120.9(6) . . ?
N2 N1 H1 119.6 . . ?
C8 N2 N1 116.3(7) . . ?
C15 O2 C12 121.4(11) . . ?
C15A O2 C12 120.0(12) . . ?
O2 C15 F1 93.7(13) . . ?
O2 C15 F2 117.8(16) . . ?
O2 C15 F3 120.0(17) . . ?
F2 C15 F1 108.6(14) . . ?
F3 C15 F1 107.5(14) . . ?
F3 C15 F2 107.4(12) . . ?
O2 C15A F3A 101.9(17) . . ?
O2 C15A F1A 116.7(18) . . ?
F3A C15A F1A 113.1(13) . . ?
F2A C15A O2 95.4(14) . . ?
F2A C15A F3A 114.7(14) . . ?
F2A C15A F1A 113.4(14) . . ?

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
C1 C2 C3 C4 0.1(13) . . . . ?
C2 C1 C6 C5 0.3(14) . . . . ?
C2 C3 C4 C5 1.2(11) . . . . ?
C2 C3 C4 C7 177.5(7) . . . . ?
C3 C4 C5 C6 -1.8(12) . . . . ?
C3 C4 C7 N1 156.4(6) . . . . ?
C3 C4 C7 O1 -25.9(10) . . . . ?
C4 C5 C6 C1 1.1(14) . . . . ?
C4 C7 N1 N2 179.8(5) . . . . ?
C5 C4 C7 N1 -27.7(11) . . . . ?
C5 C4 C7 O1 150.0(8) . . . . ?
C6 C1 C2 C3 -0.9(13) . . . . ?
C7 C4 C5 C6 -177.6(7) . . . . ?
C7 N1 N2 C8 174.4(7) . . . . ?
C8 C9 C10 C11 -177.4(8) . . . . ?
C8 C9 C14 C13 177.2(9) . . . . ?
C9 C8 N2 N1 179.2(6) . . . . ?
C9 C10 C11 C12 -0.4(15) . . . . ?
C10 C9 C14 C13 -1.7(14) . . . . ?
C10 C11 C12 C13 -0.4(18) . . . . ?
C10 C11 C12 O2 -176.2(9) . . . . ?
C11 C12 C13 C14 0.1(19) . . . . ?
C11 C12 O2 C15 -112.5(15) . . . . ?
C11 C12 O2 C15A -108.5(15) . . . . ?
C12 C13 C14 C9 0.9(17) . . . . ?
C12 O2 C15 F1 -94.7(16) . . . . ?
C12 O2 C15 F2 19(2) . . . . ?
C12 O2 C15 F3 152.7(15) . . . . ?
C12 O2 C15A F3A -172.9(14) . . . . ?
C12 O2 C15A F1A -49(2) . . . . ?
C12 O2 C15A F2A 70.4(17) . . . . ?
C13 C12 O2 C15 71.6(18) . . . . ?
C13 C12 O2 C15A 75.6(18) . . . . ?
C14 C9 C10 C11 1.4(13) . . . . ?
Cl1 C1 C2 C3 -178.9(6) . . . . ?
Cl1 C1 C6 C5 178.3(7) . . . . ?
N2 C8 C9 C10 7.3(13) . . . . ?
N2 C8 C9 C14 -171.6(8) . . . . ?
O1 C7 N1 N2 2.1(11) . . . . ?
O2 C12 C13 C14 175.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CTBB_298K_Form_I
_database_code_depnum_ccdc_archive 'CCDC 2286247'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   18.6718(16)
_cell_length_b                   10.1775(10)
_cell_length_c                   8.0982(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.583(3)
_cell_angle_gamma                90
_cell_volume                     1537.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4217
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8223.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14054
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      298.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2365
_reflns_number_total             3511
_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       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.059
_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)+(0.0430P)²+0.6787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 F3-C15 \\sim F1-C15 \\sim F2-C15
 with sigma of 0.02
 O2-C15 \\sim O2-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A \\sim C15 \\sim C15A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{F1A, F2A, F3A, C15A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{F1, F2, F3, C15}
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C15A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C15)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14)
;
_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
Cl1 Cl 0.23688(4) 0.13805(9) 0.57288(11) 0.1053(3) Uani 1 1 d . . . . .
F1 F 1.0408(6) 0.5961(15) 0.1590(19) 0.136(3) Uani 0.434(9) 1 d D U P A 1
F2 F 0.9320(5) 0.6700(12) 0.1415(17) 0.159(3) Uani 0.434(9) 1 d D U P A 1
F3 F 0.9915(4) 0.6800(8) 0.3674(11) 0.132(3) Uani 0.434(9) 1 d D U P A 1
C15 C 0.9804(7) 0.6119(11) 0.2313(16) 0.116(3) Uani 0.434(9) 1 d D U P A 1
F1A F 1.0413(5) 0.6372(12) 0.1812(16) 0.146(3) Uani 0.566(9) 1 d D U P A 2
F2A F 0.9396(3) 0.5994(7) 0.0593(7) 0.128(2) Uani 0.566(9) 1 d D U P A 2
F3A F 0.9467(5) 0.7170(5) 0.2698(12) 0.154(3) Uani 0.566(9) 1 d D U P A 2
C15A C 0.9737(6) 0.6086(9) 0.2073(13) 0.110(2) Uani 0.566(9) 1 d D U P A 2
O1 O 0.55000(8) 0.10933(15) 0.20599(18) 0.0601(4) Uani 1 1 d . . . . .
O2 O 0.96470(9) 0.4960(2) 0.2828(3) 0.0989(7) Uani 1 1 d D . . . .
N1 N 0.57695(8) 0.26400(17) 0.4006(2) 0.0529(4) Uani 1 1 d . . . . .
H1 H 0.562668 0.307310 0.484116 0.063 Uiso 1 1 calc R U . . .
N2 N 0.64567(8) 0.28238(17) 0.3479(2) 0.0531(4) Uani 1 1 d . . . . .
C1 C 0.32253(11) 0.1507(3) 0.5009(3) 0.0633(6) Uani 1 1 d . . . . .
C2 C 0.35539(12) 0.0421(3) 0.4380(3) 0.0665(6) Uani 1 1 d . . . . .
H2 H 0.331961 -0.038563 0.434628 0.080 Uiso 1 1 calc R U . . .
C3 C 0.42314(11) 0.0535(2) 0.3801(3) 0.0573(5) Uani 1 1 d . . . . .
H3 H 0.445294 -0.019575 0.336085 0.069 Uiso 1 1 calc R U . . .
C4 C 0.45882(10) 0.1731(2) 0.3865(2) 0.0480(5) Uani 1 1 d . . . . .
C5 C 0.42478(11) 0.2815(2) 0.4482(3) 0.0604(6) Uani 1 1 d . . . . .
H5 H 0.447931 0.362396 0.451169 0.072 Uiso 1 1 calc R U . . .
C6 C 0.35642(11) 0.2706(3) 0.5056(3) 0.0682(6) Uani 1 1 d . . . . .
H6 H 0.333527 0.343912 0.547002 0.082 Uiso 1 1 calc R U . . .
C7 C 0.53229(10) 0.1785(2) 0.3214(3) 0.0491(5) Uani 1 1 d . . . . .
C8 C 0.68498(11) 0.3554(2) 0.4420(3) 0.0553(5) Uani 1 1 d . . . . .
H8 H 0.666742 0.387975 0.538823 0.066 Uiso 1 1 calc R U . . .
C9 C 0.75804(10) 0.3892(2) 0.4010(3) 0.0528(5) Uani 1 1 d . . . . .
C10 C 0.78993(12) 0.3386(2) 0.2637(3) 0.0649(6) Uani 1 1 d . . . . .
H10 H 0.765021 0.278088 0.197050 0.078 Uiso 1 1 calc R U . . .
C11 C 0.85760(12) 0.3762(3) 0.2241(3) 0.0716(7) Uani 1 1 d . . . . .
H11 H 0.878304 0.342233 0.130861 0.086 Uiso 1 1 calc R U . . .
C12 C 0.89393(11) 0.4636(3) 0.3230(3) 0.0689(7) Uani 1 1 d . . . . .
C13 C 0.86567(13) 0.5130(3) 0.4619(4) 0.0810(8) Uani 1 1 d . . . . .
H13 H 0.891844 0.570980 0.529793 0.097 Uiso 1 1 calc R U . . .
C14 C 0.79705(13) 0.4752(3) 0.5002(3) 0.0722(7) Uani 1 1 d . . . . .
H14 H 0.777074 0.508524 0.594623 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.731(2) . ?
F1 C15 1.304(11) . ?
F2 C15 1.279(11) . ?
F3 C15 1.311(12) . ?
C15 O2 1.289(11) . ?
F1A C15A 1.322(9) . ?
F2A C15A 1.335(10) . ?
F3A C15A 1.323(9) . ?
C15A O2 1.313(9) . ?
O1 C7 1.227(2) . ?
O2 C12 1.414(2) . ?
N1 H1 0.8600 . ?
N1 N2 1.383(2) . ?
N1 C7 1.348(3) . ?
N2 C8 1.273(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.374(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 C5 1.378(3) . ?
C4 C7 1.493(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.459(3) . ?
C9 C10 1.384(3) . ?
C9 C14 1.374(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.358(3) . ?
C12 C13 1.360(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 H14 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
F1 C15 F3 109.6(10) . . ?
F2 C15 F1 113.9(11) . . ?
F2 C15 F3 108.4(10) . . ?
F2 C15 O2 116.3(11) . . ?
O2 C15 F1 104.2(11) . . ?
O2 C15 F3 104.0(9) . . ?
F1A C15A F2A 107.0(8) . . ?
F1A C15A F3A 105.1(8) . . ?
F3A C15A F2A 103.1(8) . . ?
O2 C15A F1A 114.2(9) . . ?
O2 C15A F2A 106.9(8) . . ?
O2 C15A F3A 119.4(8) . . ?
C15 O2 C12 121.0(6) . . ?
C15A O2 C12 116.8(5) . . ?
N2 N1 H1 119.9 . . ?
C7 N1 H1 119.9 . . ?
C7 N1 N2 120.23(17) . . ?
C8 N2 N1 114.35(17) . . ?
C2 C1 Cl1 119.99(19) . . ?
C2 C1 C6 120.8(2) . . ?
C6 C1 Cl1 119.21(19) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C7 117.80(18) . . ?
C5 C4 C3 119.17(19) . . ?
C5 C4 C7 123.01(18) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O1 C7 N1 123.40(18) . . ?
O1 C7 C4 122.11(19) . . ?
N1 C7 C4 114.48(17) . . ?
N2 C8 H8 119.3 . . ?
N2 C8 C9 121.40(19) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 122.4(2) . . ?
C14 C9 C8 119.6(2) . . ?
C14 C9 C10 118.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 O2 117.7(2) . . ?
C11 C12 C13 121.9(2) . . ?
C13 C12 O2 120.4(2) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C13 121.1(2) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 179.49(18) . . . . ?
Cl1 C1 C6 C5 -179.94(18) . . . . ?
F1 C15 O2 C12 -160.7(8) . . . . ?
F2 C15 O2 C12 -34.5(14) . . . . ?
F3 C15 O2 C12 84.5(10) . . . . ?
C15 O2 C12 C11 112.0(7) . . . . ?
C15 O2 C12 C13 -72.0(8) . . . . ?
F1A C15A O2 C12 176.3(7) . . . . ?
F2A C15A O2 C12 -65.5(8) . . . . ?
F3A C15A O2 C12 50.9(11) . . . . ?
C15A O2 C12 C11 101.6(6) . . . . ?
C15A O2 C12 C13 -82.3(6) . . . . ?
O2 C12 C13 C14 -177.7(2) . . . . ?
N1 N2 C8 C9 -177.50(18) . . . . ?
N2 N1 C7 O1 3.2(3) . . . . ?
N2 N1 C7 C4 -177.32(17) . . . . ?
N2 C8 C9 C10 -3.6(3) . . . . ?
N2 C8 C9 C14 175.8(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 C7 -180.0(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C7 O1 32.2(3) . . . . ?
C3 C4 C7 N1 -147.27(19) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C5 C4 C7 O1 -146.1(2) . . . . ?
C5 C4 C7 N1 34.4(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C7 N1 N2 C8 -173.35(19) . . . . ?
C7 C4 C5 C6 179.5(2) . . . . ?
C8 C9 C10 C11 177.2(2) . . . . ?
C8 C9 C14 C13 -177.7(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C10 C11 C12 O2 177.3(2) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 -2.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_CTBB_374K_Form_II
_database_code_depnum_ccdc_archive 'CCDC 2341752'
loop_
_audit_author_name
_audit_author_address
'Wenbo Wu'
;Tianjin university
China
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2024-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl F3 N2 O2'
_chemical_formula_sum            'C15 H10 Cl F3 N2 O2'
_chemical_formula_weight         342.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   19.0164(19)
_cell_length_b                   9.4918(12)
_cell_length_c                   8.9166(11)
_cell_angle_alpha                90
_cell_angle_beta                 85.985(10)
_cell_angle_gamma                90
_cell_volume                     1605.5(3)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    374.4
_cell_measurement_theta_max      62.3770
_cell_measurement_theta_min      4.9850
_shelx_estimated_absorpt_T_max   0.641
_shelx_estimated_absorpt_T_min   0.550
_exptl_absorpt_coefficient_mu    2.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7062
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.385
_diffrn_reflns_theta_min         2.329
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      374.4
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    150.00 175.00   0.50    0.34    --  108.45  77.00  90.00   50
  2  ω    107.00 139.00   0.50    0.34    --  108.45  77.00  90.00   64
  3  ω     73.00  98.00   0.50    0.34    --  108.45  77.00  90.00   50
  4  ω     78.00 115.00   0.50    0.34    --  108.45  61.00  60.00   74
  5  ω    119.00 175.00   0.50    0.34    --  108.45  61.00  60.00  112
  6  ω    136.00 175.00   0.50    0.34    --  108.45  45.00   0.00   78
  7  ω     80.00 114.00   0.50    0.34    --  108.45  45.00   0.00   68
  8  ω     82.00 108.00   0.50    0.34    --  108.45  61.00 -60.00   52
  9  ω    126.00 174.00   0.50    0.34    --  108.45  61.00 -60.00   96
 10  ω      2.00 114.00   0.50    0.08    --   36.37  77.00  60.00  224
 11  ω     -9.00  32.00   0.50    0.08    --  -36.37  57.00  30.00   82
 12  ω    -62.00 -15.00   0.50    0.08    --  -36.37  57.00  30.00   94
 13  ω    -33.00  39.00   0.50    0.08    --  -36.37  57.00 -90.00  144
 14  ω     -3.00  23.00   0.50    0.08    --  -36.37  57.00-180.00   52
 15  ω    -51.00 -22.00   0.50    0.34    -- -100.00  45.00  60.00   58
 16  ω   -137.00 -29.00   0.50    0.34    -- -100.00  80.00 105.85  216
 17  ω   -138.00 -70.00   0.50    0.34    -- -100.00  80.00  59.53  136
 18  ω    -46.00 -21.00   0.50    0.34    -- -100.00  45.00 150.00   50
 19  ω    -70.00 -25.00   0.50    0.34    -- -100.00  61.00  60.00   90
 20  ω    -49.00 -23.00   0.50    0.34    -- -100.00  45.00  30.00   52
 21  ω    -52.00 -27.00   0.50    0.34    -- -100.00  45.00 -90.00   50
 22  ω    -52.00 -19.00   0.50    0.34    -- -100.00  45.00-120.00   66
 23  ω    -49.00 -19.00   0.50    0.34    -- -100.00  45.00-180.00   60
 24  ω   -103.00 -77.00   0.50    0.34    -- -100.00  77.00-180.00   52
;
_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      -0.0271209000
_diffrn_orient_matrix_UB_12      0.1521850000
_diffrn_orient_matrix_UB_13      -0.0224729000
_diffrn_orient_matrix_UB_21      0.0765493000
_diffrn_orient_matrix_UB_22      0.0527596000
_diffrn_orient_matrix_UB_23      -0.0011974000
_diffrn_orient_matrix_UB_31      -0.0026188000
_diffrn_orient_matrix_UB_32      -0.0193413000
_diffrn_orient_matrix_UB_33      -0.1717121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1866
_reflns_number_total             2942
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.210
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2936
_refine_ls_wR_factor_ref         0.3238
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C009(H009), C00A(H00A), C00D(H00D), C00E(H00E),
 C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L)
;
_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
Cl00 Cl -0.22848(7) -0.10064(19) 0.40944(18) 0.1941(8) Uani 1 1 d . . . . .
O002 O -0.54594(14) -0.1299(3) 0.7699(3) 0.1384(9) Uani 1 1 d . . . . .
N003 N -0.56946(14) -0.2673(3) 0.5719(3) 0.1181(8) Uani 1 1 d . . . . .
H003 H -0.554047 -0.304165 0.487881 0.142 Uiso 1 1 calc R U . . .
N004 N -0.63778(14) -0.2898(3) 0.6267(3) 0.1203(8) Uani 1 1 d . . . . .
C005 C -0.52682(17) -0.1873(3) 0.6503(3) 0.1156(9) Uani 1 1 d . . . . .
C006 C -0.45338(16) -0.1694(3) 0.5831(3) 0.1109(8) Uani 1 1 d . . . . .
C007 C -0.4170(2) -0.0505(3) 0.6222(4) 0.1252(10) Uani 1 1 d . . . . .
H007 H -0.439460 0.015979 0.685474 0.150 Uiso 1 1 calc R U . . .
C008 C -0.7490(2) -0.3878(4) 0.5866(4) 0.1300(10) Uani 1 1 d . . . . .
C009 C -0.3489(2) -0.0287(4) 0.5698(4) 0.1359(11) Uani 1 1 d . . . . .
H009 H -0.324918 0.051081 0.598837 0.163 Uiso 1 1 calc R U . . .
C00A C -0.6762(2) -0.3550(4) 0.5414(4) 0.1289(10) Uani 1 1 d . . . . .
H00A H -0.657478 -0.382862 0.446910 0.155 Uiso 1 1 calc R U . . .
O00B O -0.9574(2) -0.4876(5) 0.7160(8) 0.228(2) Uani 1 1 d . . . . .
C00C C -0.3157(2) -0.1243(4) 0.4744(4) 0.1355(11) Uani 1 1 d . . . . .
C00D C -0.7837(2) -0.3309(5) 0.7139(5) 0.1419(12) Uani 1 1 d . . . . .
H00D H -0.761016 -0.263850 0.769239 0.170 Uiso 1 1 calc R U . . .
C00E C -0.41958(19) -0.2673(4) 0.4867(5) 0.1396(11) Uani 1 1 d . . . . .
H00E H -0.443452 -0.347765 0.459178 0.167 Uiso 1 1 calc R U . . .
C00F C -0.8863(2) -0.4596(6) 0.6738(7) 0.1667(16) Uani 1 1 d . . . . .
C00G C -0.8513(2) -0.3716(5) 0.7603(7) 0.1626(15) Uani 1 1 d . . . . .
H00G H -0.872489 -0.338467 0.850658 0.195 Uiso 1 1 calc R U . . .
C00H C -0.8559(3) -0.5129(7) 0.5449(8) 0.1819(19) Uani 1 1 d . . . . .
H00H H -0.881117 -0.572609 0.485779 0.218 Uiso 1 1 calc R U . . .
C00I C -0.7866(3) -0.4779(5) 0.5010(6) 0.1660(15) Uani 1 1 d . . . . .
H00I H -0.765239 -0.515700 0.412991 0.199 Uiso 1 1 calc R U . . .
C00L C -0.3511(2) -0.2455(5) 0.4322(5) 0.1559(14) Uani 1 1 d . . . . .
H00L H -0.328502 -0.310853 0.367715 0.187 Uiso 1 1 calc R U . . .
F1 F -1.0402(3) -0.6096(8) 0.8229(8) 0.316(3) Uani 1 1 d . . . . .
F2 F -0.9702(7) -0.6975(10) 0.6716(16) 0.444(9) Uani 1 1 d . . . . .
C3 C -0.9779(5) -0.6000(15) 0.7656(15) 0.262(5) Uani 1 1 d . . . . .
F4 F -0.9405(5) -0.6400(16) 0.8634(16) 0.455(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl00 C00C 1.733(4) . ?
O002 C005 1.230(4) . ?
N003 H003 0.8600 . ?
N003 N004 1.372(4) . ?
N003 C005 1.342(4) . ?
N004 C00A 1.253(5) . ?
C005 C006 1.490(4) . ?
C006 C007 1.381(5) . ?
C006 C00E 1.393(5) . ?
C007 H007 0.9300 . ?
C007 C009 1.362(5) . ?
C008 C00A 1.449(5) . ?
C008 C00D 1.383(6) . ?
C008 C00I 1.378(6) . ?
C009 H009 0.9300 . ?
C009 C00C 1.367(6) . ?
C00A H00A 0.9300 . ?
O00B C00F 1.403(6) . ?
O00B C3 1.210(12) . ?
C00C C00L 1.398(6) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.377(6) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.373(5) . ?
C00F C00G 1.345(8) . ?
C00F C00H 1.349(8) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00I 1.389(7) . ?
C00I H00I 0.9300 . ?
C00L H00L 0.9300 . ?
F1 C3 1.261(10) . ?
F2 C3 1.250(13) . ?
C3 F4 1.223(14) . ?

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
N004 N003 H003 120.2 . . ?
C005 N003 H003 120.2 . . ?
C005 N003 N004 119.7(3) . . ?
C00A N004 N003 116.0(3) . . ?
O002 C005 N003 123.3(3) . . ?
O002 C005 C006 120.6(3) . . ?
N003 C005 C006 116.0(3) . . ?
C007 C006 C005 117.6(3) . . ?
C007 C006 C00E 118.9(3) . . ?
C00E C006 C005 123.4(3) . . ?
C006 C007 H007 119.4 . . ?
C009 C007 C006 121.2(3) . . ?
C009 C007 H007 119.4 . . ?
C00D C008 C00A 122.4(4) . . ?
C00I C008 C00A 120.1(4) . . ?
C00I C008 C00D 117.4(4) . . ?
C007 C009 H009 120.0 . . ?
C007 C009 C00C 120.0(4) . . ?
C00C C009 H009 120.0 . . ?
N004 C00A C008 121.6(3) . . ?
N004 C00A H00A 119.2 . . ?
C008 C00A H00A 119.2 . . ?
C3 O00B C00F 123.0(7) . . ?
C009 C00C Cl00 120.7(3) . . ?
C009 C00C C00L 120.2(4) . . ?
C00L C00C Cl00 119.0(3) . . ?
C008 C00D H00D 119.4 . . ?
C00G C00D C008 121.3(5) . . ?
C00G C00D H00D 119.4 . . ?
C006 C00E H00E 119.9 . . ?
C00L C00E C006 120.2(3) . . ?
C00L C00E H00E 119.9 . . ?
C00G C00F O00B 118.1(6) . . ?
C00G C00F C00H 121.5(4) . . ?
C00H C00F O00B 120.4(6) . . ?
C00D C00G H00G 120.3 . . ?
C00F C00G C00D 119.4(5) . . ?
C00F C00G H00G 120.3 . . ?
C00F C00H H00H 120.3 . . ?
C00F C00H C00I 119.5(5) . . ?
C00I C00H H00H 120.3 . . ?
C008 C00I C00H 120.7(5) . . ?
C008 C00I H00I 119.6 . . ?
C00H C00I H00I 119.6 . . ?
C00C C00L H00L 120.3 . . ?
C00E C00L C00C 119.4(4) . . ?
C00E C00L H00L 120.3 . . ?
O00B C3 F1 118.8(14) . . ?
O00B C3 F2 112.8(11) . . ?
O00B C3 F4 110.3(10) . . ?
F2 C3 F1 106.4(9) . . ?
F4 C3 F1 105.4(12) . . ?
F4 C3 F2 101.7(17) . . ?

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
Cl00 C00C C00L C00E 178.0(3) . . . . ?
O002 C005 C006 C007 -24.3(4) . . . . ?
O002 C005 C006 C00E 154.2(3) . . . . ?
N003 N004 C00A C008 178.9(3) . . . . ?
N003 C005 C006 C007 155.0(3) . . . . ?
N003 C005 C006 C00E -26.5(4) . . . . ?
N004 N003 C005 O002 -1.2(4) . . . . ?
N004 N003 C005 C006 179.5(2) . . . . ?
C005 N003 N004 C00A 173.9(3) . . . . ?
C005 C006 C007 C009 177.7(3) . . . . ?
C005 C006 C00E C00L -178.3(3) . . . . ?
C006 C007 C009 C00C 1.3(6) . . . . ?
C006 C00E C00L C00C 0.0(7) . . . . ?
C007 C006 C00E C00L 0.2(6) . . . . ?
C007 C009 C00C Cl00 -178.6(3) . . . . ?
C007 C009 C00C C00L -1.0(6) . . . . ?
C008 C00D C00G C00F -5.5(7) . . . . ?
C009 C00C C00L C00E 0.4(7) . . . . ?
C00A C008 C00D C00G -175.2(4) . . . . ?
C00A C008 C00I C00H 178.5(5) . . . . ?
O00B C00F C00G C00D -173.5(5) . . . . ?
O00B C00F C00H C00I 176.5(5) . . . . ?
C00D C008 C00A N004 10.7(6) . . . . ?
C00D C008 C00I C00H -2.0(7) . . . . ?
C00E C006 C007 C009 -0.9(5) . . . . ?
C00F O00B C3 F1 168.8(9) . . . . ?
C00F O00B C3 F2 -65.8(17) . . . . ?
C00F O00B C3 F4 47.1(18) . . . . ?
C00F C00H C00I C008 -1.0(9) . . . . ?
C00G C00F C00H C00I 0.9(10) . . . . ?
C00H C00F C00G C00D 2.3(9) . . . . ?
C00I C008 C00A N004 -169.8(4) . . . . ?
C00I C008 C00D C00G 5.3(6) . . . . ?
C3 O00B C00F C00G -109.1(10) . . . . ?
C3 O00B C00F C00H 75.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.817
_oxdiff_exptl_absorpt_empirical_full_min 0.394
