# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

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

data_PTZ-OCH3
_database_code_depnum_ccdc_archive 'CCDC 2132708'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2020-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H12 F3 N O3 S, C H2 Cl2'
_chemical_formula_sum            'C20 H14 Cl2 F3 N O3 S'
_chemical_formula_weight         476.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H12 S1 N1 F3 O3'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.89904(16)
_cell_length_b                   19.4573(3)
_cell_length_c                   9.08595(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.1856(15)
_cell_angle_gamma                90.00
_cell_volume                     2056.21(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3782
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0810
_cell_measurement_theta_min      4.4030
_exptl_absorpt_coefficient_mu    4.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7665
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.80
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -42.00   1.00    1.49    --  -41.12 -77.00 -90.00   30
  2  ω   -111.00 -19.00   1.00    1.49    --  -41.12 -57.00 -30.00   92
  3  ω    -64.00  28.00   1.00    1.49    --  -41.12  57.00 120.00   92
  4  ω     93.00 119.00   1.00    5.95    --  105.32 -45.00-150.00   26
  5  ω     96.00 121.00   1.00    5.95    --  105.32 125.00-120.00   25
  6  ω     83.00 175.00   1.00    5.95    --  105.32  61.00   0.00   92
  7  ω     58.00 131.00   1.00    5.95    --  105.32 -77.00  30.00   73
  8  ω     40.00 126.00   1.00    5.95    --  105.32 -77.00 -90.00   86
  9  ω     36.00 133.00   1.00    5.95    --  105.32 -30.00  30.00   97
 10  ω     33.00  64.00   1.00    5.95    --  105.32 -45.00-150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1112579000
_diffrn_orient_matrix_UB_12      -0.0092098000
_diffrn_orient_matrix_UB_13      -0.1207044000
_diffrn_orient_matrix_UB_21      -0.0134257000
_diffrn_orient_matrix_UB_22      -0.0732964000
_diffrn_orient_matrix_UB_23      0.0581658000
_diffrn_orient_matrix_UB_31      -0.0706799000
_diffrn_orient_matrix_UB_32      0.0284729000
_diffrn_orient_matrix_UB_33      0.1101425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3198
_reflns_number_total             3678
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0895P)²+0.8611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1618
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C30(H30B,H30A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C17(H17), C19(H19), C20(H20), C22(H22),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.07251(5) 0.14387(3) 0.07851(7) 0.0495(2) Uani 1 d . . .
O3 O 0.06208(17) -0.10385(9) 0.4367(2) 0.0603(5) Uani 1 d . . .
N2 N -0.14743(16) 0.07822(11) 0.1373(2) 0.0481(5) Uani 1 d . . .
O1 O 0.09449(18) 0.19809(10) 0.1887(2) 0.0665(5) Uani 1 d . . .
C4 C -0.04418(18) 0.04440(11) 0.1971(2) 0.0413(5) Uani 1 d . . .
C5 C -0.0445(2) -0.01352(12) 0.2887(3) 0.0452(5) Uani 1 d . . .
H5 H -0.1133 -0.0291 0.3099 0.054 Uiso 1 calc . . R
C6 C -0.1601(2) 0.12498(12) 0.0173(3) 0.0456(5) Uani 1 d . . .
C7 C 0.0567(2) -0.04767(12) 0.3478(3) 0.0481(5) Uani 1 d . . .
O2 O 0.15341(18) 0.13729(11) -0.0178(3) 0.0704(6) Uani 1 d . . .
C9 C 0.06079(19) 0.06651(12) 0.1680(3) 0.0449(5) Uani 1 d . . .
C11 C -0.24980(19) 0.05849(13) 0.1876(3) 0.0488(5) Uani 1 d . . .
C12 C 0.1613(2) -0.02543(14) 0.3176(3) 0.0565(6) Uani 1 d . . .
H12 H 0.2291 -0.0487 0.3574 0.068 Uiso 1 calc . . R
C13 C 0.1622(2) 0.03086(14) 0.2291(3) 0.0539(6) Uani 1 d . . .
H13 H 0.2315 0.0460 0.2087 0.065 Uiso 1 calc . . R
C14 C -0.2697(2) 0.14328(14) -0.0640(3) 0.0578(6) Uani 1 d . . .
H14 H -0.3345 0.1257 -0.0353 0.069 Uiso 1 calc . . R
F3 F -0.4701(2) -0.07105(15) 0.1240(3) 0.1203(10) Uani 1 d . . .
C16 C -0.0656(2) 0.15435(12) -0.0287(3) 0.0482(5) Uani 1 d . . .
C17 C -0.3098(2) 0.00001(15) 0.1293(3) 0.0603(7) Uani 1 d . . .
H17 H -0.2842 -0.0277 0.0596 0.072 Uiso 1 calc . . R
F2 F -0.54517(18) 0.00856(19) 0.3242(3) 0.1369(12) Uani 1 d . . .
C19 C -0.2825(3) 0.18697(16) -0.1858(3) 0.0680(8) Uani 1 d . . .
H19 H -0.3560 0.1987 -0.2375 0.082 Uiso 1 calc . . R
C20 C -0.0801(3) 0.19758(13) -0.1533(3) 0.0597(7) Uani 1 d . . .
H20 H -0.0161 0.2157 -0.1832 0.072 Uiso 1 calc . . R
C21 C -0.0434(3) -0.13289(15) 0.4584(4) 0.0658(7) Uani 1 d . . .
H21A H -0.0897 -0.1460 0.3628 0.099 Uiso 1 calc . . GR
H21B H -0.0841 -0.0995 0.5052 0.099 Uiso 1 calc . . GR
H21C H -0.0274 -0.1727 0.5219 0.099 Uiso 1 calc . . GR
C22 C -0.1887(3) 0.21361(15) -0.2324(3) 0.0712(8) Uani 1 d . . .
H22 H -0.1986 0.2421 -0.3164 0.085 Uiso 1 calc . . R
C23 C -0.2858(2) 0.09923(17) 0.2922(3) 0.0632(7) Uani 1 d . . .
H23 H -0.2438 0.1378 0.3314 0.076 Uiso 1 calc . . R
C24 C -0.4090(3) -0.01545(19) 0.1785(4) 0.0763(10) Uani 1 d . . .
F1 F -0.4219(2) 0.1202(2) 0.4402(3) 0.1365(11) Uani 1 d . . .
C27 C -0.4476(2) 0.0243(2) 0.2807(4) 0.0856(12) Uani 1 d . . .
C28 C -0.3851(3) 0.0818(2) 0.3379(4) 0.0826(11) Uani 1 d . . .
Cl1 Cl 0.34196(17) 0.15842(11) 0.5649(3) 0.1933(10) Uani 1 d . . .
Cl2 Cl 0.44974(19) 0.28865(12) 0.5779(3) 0.2168(13) Uani 1 d . . .
C30 C 0.3382(5) 0.2365(3) 0.4926(8) 0.151(3) Uani 1 d . . .
H30B H 0.2662 0.2581 0.5002 0.182 Uiso 1 calc . . R
H30A H 0.3394 0.2327 0.3864 0.182 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.440(2) . ?
S1 O2 1.437(2) . ?
S1 C9 1.730(2) . ?
S1 C16 1.736(3) . ?
O3 C7 1.353(3) . ?
O3 C21 1.428(4) . ?
N2 C4 1.399(3) . ?
N2 C6 1.403(3) . ?
N2 C11 1.441(3) . ?
C4 C5 1.402(3) . ?
C4 C9 1.398(3) . ?
C5 C7 1.381(3) . ?
C6 C14 1.402(4) . ?
C6 C16 1.402(3) . ?
C7 C12 1.398(4) . ?
C9 C13 1.401(4) . ?
C11 C17 1.388(4) . ?
C11 C23 1.374(4) . ?
C12 C13 1.360(4) . ?
C14 C19 1.378(4) . ?
F3 C24 1.339(4) . ?
C16 C20 1.392(4) . ?
C17 C24 1.381(4) . ?
F2 C27 1.338(4) . ?
C19 C22 1.376(5) . ?
C20 C22 1.375(5) . ?
C23 C28 1.375(4) . ?
C24 C27 1.360(6) . ?
F1 C28 1.336(4) . ?
C27 C28 1.383(6) . ?
Cl1 C30 1.651(7) . ?
Cl2 C30 1.721(7) . ?

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
O1 S1 C9 109.36(12) . . ?
O1 S1 C16 108.39(12) . . ?
O2 S1 O1 116.23(13) . . ?
O2 S1 C9 109.84(12) . . ?
O2 S1 C16 110.20(13) . . ?
C9 S1 C16 101.84(11) . . ?
C7 O3 C21 118.0(2) . . ?
C4 N2 C6 123.30(19) . . ?
C4 N2 C11 118.89(19) . . ?
C6 N2 C11 117.37(19) . . ?
N2 C4 C5 119.8(2) . . ?
C9 C4 N2 121.9(2) . . ?
C9 C4 C5 118.3(2) . . ?
C7 C5 C4 120.4(2) . . ?
C14 C6 N2 120.6(2) . . ?
C14 C6 C16 117.1(2) . . ?
C16 C6 N2 122.3(2) . . ?
O3 C7 C5 123.2(2) . . ?
O3 C7 C12 115.8(2) . . ?
C5 C7 C12 121.0(2) . . ?
C4 C9 S1 121.37(18) . . ?
C4 C9 C13 120.1(2) . . ?
C13 C9 S1 117.96(18) . . ?
C17 C11 N2 119.9(2) . . ?
C23 C11 N2 118.3(2) . . ?
C23 C11 C17 121.8(3) . . ?
C13 C12 C7 118.9(2) . . ?
C12 C13 C9 121.3(2) . . ?
C19 C14 C6 120.8(3) . . ?
C6 C16 S1 120.60(19) . . ?
C20 C16 S1 117.9(2) . . ?
C20 C16 C6 121.3(2) . . ?
C24 C17 C11 117.5(3) . . ?
C22 C19 C14 121.3(3) . . ?
C22 C20 C16 120.3(3) . . ?
C20 C22 C19 119.2(3) . . ?
C11 C23 C28 118.6(3) . . ?
F3 C24 C17 119.4(4) . . ?
F3 C24 C27 118.4(3) . . ?
C27 C24 C17 122.2(3) . . ?
F2 C27 C24 120.7(4) . . ?
F2 C27 C28 120.3(4) . . ?
C24 C27 C28 118.9(3) . . ?
C23 C28 C27 121.0(3) . . ?
F1 C28 C23 120.1(4) . . ?
F1 C28 C27 118.9(3) . . ?
Cl1 C30 Cl2 114.2(3) . . ?

_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.816
####################################################################### 
# 
# 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_PTZ-Cl-RTP-inactive
_database_code_depnum_ccdc_archive 'CCDC 2132717'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H9 Cl F3 N O2 S'
_chemical_formula_sum            'C18 H9 Cl F3 N O2 S'
_chemical_formula_weight         395.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H9 S1 N1 F3 O2 Cl1'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2251(3)
_cell_length_b                   17.7371(4)
_cell_length_c                   7.86265(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.328(2)
_cell_angle_gamma                90.00
_cell_volume                     1703.50(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8890
_cell_measurement_theta_min      6.1460
_exptl_absorpt_coefficient_mu    3.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5959
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.62
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -17.00   1.00    2.19    --  -41.12 -37.00-150.00   93
  2  ω     15.00  97.00   1.00    2.19    --   41.12  57.00   0.00   82
  3  ω     20.00  47.00   1.00    2.19    --   41.12 -99.00 -90.00   27
  4  ω     34.00  81.00   1.00    2.19    --   41.12 -99.00-120.00   47
  5  ω     51.00 114.00   1.00    8.76    --  105.32-125.00 120.00   63
  6  ω     35.00  92.00   1.00    8.76    --  105.32 -45.00-150.00   57
  7  ω     86.00 175.00   1.00    8.76    --  105.32  45.00 -60.00   89
  8  ω     90.00 166.00   1.00    8.76    --  105.32  30.00  30.00   76
  9  ω     29.00 122.00   1.00    8.76    --  105.32 -77.00 120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1256408000
_diffrn_orient_matrix_UB_12      -0.0044083000
_diffrn_orient_matrix_UB_13      -0.0215986000
_diffrn_orient_matrix_UB_21      0.0099187000
_diffrn_orient_matrix_UB_22      -0.0149753000
_diffrn_orient_matrix_UB_23      -0.1917740000
_diffrn_orient_matrix_UB_31      0.0048509000
_diffrn_orient_matrix_UB_32      -0.0854298000
_diffrn_orient_matrix_UB_33      0.0348451000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2575
_reflns_number_total             3045
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1186P)²+1.4144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2125
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: Cl2(0.5) Cl1(0.5)
 Fixed Uiso: H9(0.061) H13(0.052) H14(0.056) H15(0.066) H18(0.058) H19(0.071)
 H21(0.065) H24(0.081)
 Fixed X: H9(0.1457) H13(0.4028) H14(0.3366) H15(0.3978) H18(0.1266)
 H19(0.4147) H21(0.3892) H24(0.2012)
 Fixed Y: H9(-0.0673) H13(-0.125) H14(-0.0811) H15(-0.0233) H18(-0.1008)
 H19(0.1066) H21(0.177) H24(0.1898)
 Fixed Z: H9(-0.0362) H13(0.0825) H14(0.5055) H15(0.7534) H18(0.3384)
 H19(0.7679) H21(0.5253) H24(-0.0784)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.34649(9) 0.14305(5) 0.18361(12) 0.0554(3) Uani 1 d . . .
N1 N 0.2813(2) -0.02081(14) 0.2088(3) 0.0423(6) Uani 1 d . . .
C2 C 0.2669(3) -0.10136(17) 0.2108(4) 0.0407(7) Uani 1 d . . .
C3 C 0.2294(3) 0.01981(19) 0.0756(4) 0.0431(7) Uani 1 d . . .
F4 F 0.0835(2) -0.24119(15) 0.3711(4) 0.0819(8) Uani 1 d . . .
F5 F 0.4030(2) -0.26992(13) 0.0746(4) 0.0748(8) Uani 1 d . . .
C6 C 0.3242(3) 0.01304(17) 0.3594(4) 0.0397(7) Uani 1 d . . .
C7 C 0.3310(3) -0.22354(19) 0.1451(5) 0.0492(8) Uani 1 d . . .
F8 F 0.2342(3) -0.33006(12) 0.2306(4) 0.0792(8) Uani 1 d . . .
C9 C 0.1576(3) -0.0157(2) -0.0432(4) 0.0508(8) Uani 1 d A . .
H9 H 0.1457 -0.0673 -0.0362 0.061 Uiso 1 calc . . R
C10 C 0.2439(3) -0.25491(19) 0.2232(5) 0.0532(9) Uani 1 d . . .
C11 C 0.2455(3) 0.0974(2) 0.0586(5) 0.0503(8) Uani 1 d A . .
C12 C 0.3450(3) 0.09021(18) 0.3693(4) 0.0431(7) Uani 1 d . . .
C13 C 0.3439(3) -0.14617(18) 0.1366(4) 0.0430(7) Uani 1 d . . .
H13 H 0.4028 -0.1250 0.0825 0.052 Uiso 1 calc . . R
C14 C 0.3462(3) -0.0291(2) 0.5076(4) 0.0467(8) Uani 1 d . . .
H14 H 0.3366 -0.0811 0.5055 0.056 Uiso 1 calc . . R
C15 C 0.3820(3) 0.0058(2) 0.6570(5) 0.0548(9) Uani 1 d . . .
H15 H 0.3978 -0.0233 0.7534 0.066 Uiso 1 calc . . R
O16 O 0.4494(3) 0.1314(2) 0.1069(4) 0.0751(9) Uani 1 d . . .
O17 O 0.3155(4) 0.21922(16) 0.2154(5) 0.0901(12) Uani 1 d . . .
C18 C 0.1782(3) -0.13167(19) 0.2897(5) 0.0484(8) Uani 1 d . . .
H18 H 0.1266 -0.1008 0.3384 0.058 Uiso 1 calc . . R
C19 C 0.3949(3) 0.0834(3) 0.6652(5) 0.0590(10) Uani 1 d . . .
H19 H 0.4147 0.1066 0.7679 0.071 Uiso 1 calc . . R
C20 C 0.1048(3) 0.0258(3) -0.1704(5) 0.0631(11) Uani 1 d . . .
C21 C 0.3783(3) 0.1251(2) 0.5219(5) 0.0541(9) Uani 1 d . . .
H21 H 0.3892 0.1770 0.5253 0.065 Uiso 1 calc . . R
C23 C 0.1683(3) -0.2092(2) 0.2944(5) 0.0529(9) Uani 1 d . . .
C24 C 0.1902(4) 0.1380(3) -0.0705(6) 0.0671(12) Uani 1 d . . .
H24 H 0.2012 0.1898 -0.0784 0.081 Uiso 1 calc A . R
C25 C 0.1218(4) 0.1040(3) -0.1827(7) 0.0762(14) Uani 1 d A . .
Cl2 Cl 0.0175(8) -0.0508(6) -0.2992(8) 0.177(5) Uani 0.50 d A 2 .
Cl1 Cl 0.0281(7) -0.0072(5) -0.2962(9) 0.147(3) Uani 0.50 d A . .
H25 H 0.082(5) 0.122(3) -0.284(7) 0.091(17) Uiso 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
S1 C11 1.746(4) . ?
S1 C12 1.736(3) . ?
S1 O16 1.433(3) . ?
S1 O17 1.428(3) . ?
N1 C2 1.440(4) . ?
N1 C3 1.401(4) . ?
N1 C6 1.409(4) . ?
C2 C13 1.380(5) . ?
C2 C18 1.379(5) . ?
C3 C9 1.405(5) . ?
C3 C11 1.397(5) . ?
F4 C23 1.346(4) . ?
F5 C7 1.341(4) . ?
C6 C12 1.394(4) . ?
C6 C14 1.401(5) . ?
C7 C10 1.369(6) . ?
C7 C13 1.383(5) . ?
F8 C10 1.340(4) . ?
C9 C20 1.381(5) . ?
C10 C23 1.367(6) . ?
C11 C24 1.397(5) . ?
C12 C21 1.396(5) . ?
C14 C15 1.383(5) . ?
C15 C19 1.387(6) . ?
C18 C23 1.381(5) . ?
C19 C21 1.356(6) . ?
C20 C25 1.406(7) . ?
C20 Cl2 1.980(10) . ?
C20 Cl1 1.457(10) . ?
C24 C25 1.335(8) . ?
Cl2 Cl1 0.784(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
C12 S1 C11 101.08(16) . . ?
O16 S1 C11 107.98(18) . . ?
O16 S1 C12 108.38(18) . . ?
O17 S1 C11 110.6(2) . . ?
O17 S1 C12 110.60(19) . . ?
O17 S1 O16 117.0(2) . . ?
C3 N1 C2 117.8(3) . . ?
C3 N1 C6 123.4(3) . . ?
C6 N1 C2 117.1(2) . . ?
C13 C2 N1 118.7(3) . . ?
C18 C2 N1 119.4(3) . . ?
C18 C2 C13 121.9(3) . . ?
N1 C3 C9 121.2(3) . . ?
C11 C3 N1 121.1(3) . . ?
C11 C3 C9 117.7(3) . . ?
C12 C6 N1 121.8(3) . . ?
C12 C6 C14 116.6(3) . . ?
C14 C6 N1 121.6(3) . . ?
F5 C7 C10 118.1(3) . . ?
F5 C7 C13 120.7(3) . . ?
C10 C7 C13 121.2(3) . . ?
C20 C9 C3 120.3(4) . . ?
F8 C10 C7 119.7(4) . . ?
F8 C10 C23 120.7(4) . . ?
C23 C10 C7 119.6(3) . . ?
C3 C11 S1 120.1(3) . . ?
C24 C11 S1 118.7(3) . . ?
C24 C11 C3 120.8(4) . . ?
C6 C12 S1 119.4(2) . . ?
C6 C12 C21 122.0(3) . . ?
C21 C12 S1 118.1(3) . . ?
C2 C13 C7 118.0(3) . . ?
C15 C14 C6 120.8(3) . . ?
C14 C15 C19 121.0(3) . . ?
C2 C18 C23 118.2(3) . . ?
C21 C19 C15 119.4(3) . . ?
C9 C20 C25 120.6(4) . . ?
C9 C20 Cl2 103.4(4) . . ?
C9 C20 Cl1 123.1(5) . . ?
C25 C20 Cl2 136.0(4) . . ?
C25 C20 Cl1 116.3(5) . . ?
Cl1 C20 Cl2 19.8(5) . . ?
C19 C21 C12 120.0(3) . . ?
F4 C23 C10 118.6(3) . . ?
F4 C23 C18 120.2(4) . . ?
C10 C23 C18 121.2(3) . . ?
C25 C24 C11 121.2(4) . . ?
C24 C25 C20 119.4(4) . . ?
Cl1 Cl2 C20 39.0(10) . . ?
Cl2 Cl1 C20 121.2(13) . . ?

_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 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_PTZ-Cl
_database_code_depnum_ccdc_archive 'CCDC 2132714'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2020-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H9 Cl F3 N O2 S'
_chemical_formula_sum            'C18 H9 Cl F3 N O2 S'
_chemical_formula_weight         395.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H9 S1 N1 F3 O2 Cl1'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.2364(2)
_cell_length_b                   15.4778(3)
_cell_length_c                   21.0591(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3336.54(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9950
_cell_measurement_theta_min      5.5650
_exptl_absorpt_coefficient_mu    3.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8041
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.20
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  32.00   1.00    3.31    --  -41.12  57.00  60.00   85
  2  ω    -31.00  27.00   1.00    3.31    --   41.12 -37.00-120.00   58
  3  ω     54.00  80.00   1.00    3.31    --   41.12-125.00-180.00   26
  4  ω    112.00 162.00   1.00   13.23    --  105.32  61.00  60.00   50
  5  ω     94.00 175.00   1.00   13.23    --  105.32 125.00-180.00   81
  6  ω     41.00 117.00   1.00   13.23    --  105.32-125.00 -60.00   76
  7  ω    100.00 178.00   1.00   13.23    --  105.32 125.00 120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1430439000
_diffrn_orient_matrix_UB_12      -0.0164068000
_diffrn_orient_matrix_UB_13      0.0192933000
_diffrn_orient_matrix_UB_21      -0.0203746000
_diffrn_orient_matrix_UB_22      0.0978304000
_diffrn_orient_matrix_UB_23      0.0091475000
_diffrn_orient_matrix_UB_31      -0.0420658000
_diffrn_orient_matrix_UB_32      0.0082888000
_diffrn_orient_matrix_UB_33      -0.0699682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2383
_reflns_number_total             2978
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0603P)²+1.3733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C14(H14), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.20299(7) 0.37385(4) 0.47407(4) 0.0585(2) Uani 1 d . . .
Cl2 Cl -0.10068(12) 0.42012(9) 0.72560(4) 0.1091(4) Uani 1 d . . .
N2 N 0.2376(2) 0.52485(14) 0.56630(11) 0.0546(5) Uani 1 d . . .
O2 O 0.3090(2) 0.31862(14) 0.49263(13) 0.0817(7) Uani 1 d . . .
C4 C 0.1092(3) 0.39555(16) 0.54101(14) 0.0547(6) Uani 1 d . . .
C5 C 0.2861(3) 0.53606(17) 0.50484(14) 0.0540(6) Uani 1 d . . .
O1 O 0.1204(3) 0.34410(16) 0.42363(12) 0.0840(7) Uani 1 d . . .
F1 F 0.1548(3) 0.80027(16) 0.66170(12) 0.1203(10) Uani 1 d . . .
C8 C 0.2647(3) 0.47519(17) 0.45642(14) 0.0551(6) Uani 1 d . . .
C9 C 0.1427(3) 0.46370(16) 0.58193(13) 0.0522(6) Uani 1 d . . .
C10 C 0.1927(3) 0.66510(19) 0.61490(14) 0.0611(7) Uani 1 d . . .
H10 H 0.1231 0.6731 0.5871 0.073 Uiso 1 calc . . R
F2 F 0.3510(3) 0.77601(16) 0.74423(12) 0.1128(9) Uani 1 d . . .
C12 C 0.0098(3) 0.33808(18) 0.55606(16) 0.0648(8) Uani 1 d . . .
H12 H -0.0126 0.2948 0.5274 0.078 Uiso 1 calc . . R
C13 C 0.3045(3) 0.4914(2) 0.39431(15) 0.0690(8) Uani 1 d . . .
H13 H 0.2865 0.4512 0.3627 0.083 Uiso 1 calc . . R
C14 C 0.0757(3) 0.46950(19) 0.63942(14) 0.0627(7) Uani 1 d . . .
H14 H 0.0960 0.5132 0.6681 0.075 Uiso 1 calc . . R
C15 C 0.2669(3) 0.59087(17) 0.61265(13) 0.0534(6) Uani 1 d . . .
C16 C 0.3239(4) 0.7156(2) 0.70109(16) 0.0744(9) Uani 1 d . . .
C17 C -0.0205(3) 0.4108(2) 0.65374(15) 0.0717(9) Uani 1 d . . .
C18 C -0.0554(3) 0.3442(2) 0.61236(17) 0.0732(9) Uani 1 d . . .
H18 H -0.1211 0.3053 0.6229 0.088 Uiso 1 calc . . R
F3 F 0.4989(3) 0.6327(2) 0.73690(17) 0.1539(15) Uani 1 d . . .
C20 C 0.2238(4) 0.7267(2) 0.65896(15) 0.0700(8) Uani 1 d . . .
C21 C 0.3571(3) 0.60970(19) 0.48834(17) 0.0712(9) Uani 1 d . . .
H21 H 0.3765 0.6503 0.5195 0.085 Uiso 1 calc . . R
C22 C 0.3988(4) 0.6237(2) 0.42745(19) 0.0837(11) Uani 1 d . . .
H22 H 0.4475 0.6729 0.4182 0.100 Uiso 1 calc . . R
C23 C 0.3695(4) 0.5656(2) 0.37937(18) 0.0806(10) Uani 1 d . . .
H23 H 0.3938 0.5770 0.3377 0.097 Uiso 1 calc . . R
C24 C 0.3698(3) 0.5793(2) 0.65323(18) 0.0764(9) Uani 1 d . . .
H24 H 0.4203 0.5294 0.6513 0.092 Uiso 1 calc . . R
C25 C 0.3971(4) 0.6427(3) 0.69681(19) 0.0852(11) Uani 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
S1 O2 1.436(2) . ?
S1 C4 1.738(3) . ?
S1 O1 1.433(2) . ?
S1 C8 1.731(3) . ?
Cl2 C17 1.728(3) . ?
N2 C5 1.397(4) . ?
N2 C9 1.395(3) . ?
N2 C15 1.444(3) . ?
C4 C9 1.405(4) . ?
C4 C12 1.388(4) . ?
C5 C8 1.405(4) . ?
C5 C21 1.396(4) . ?
F1 C20 1.341(4) . ?
C8 C13 1.393(4) . ?
C9 C14 1.395(4) . ?
C10 C15 1.378(4) . ?
C10 C20 1.368(4) . ?
F2 C16 1.333(4) . ?
C12 C18 1.364(5) . ?
C13 C23 1.364(5) . ?
C14 C17 1.373(4) . ?
C15 C24 1.369(4) . ?
C16 C20 1.366(5) . ?
C16 C25 1.357(5) . ?
C17 C18 1.396(5) . ?
F3 C25 1.350(4) . ?
C21 C22 1.369(5) . ?
C22 C23 1.388(5) . ?
C24 C25 1.372(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
O2 S1 C4 108.18(15) . . ?
O2 S1 C8 108.78(14) . . ?
O1 S1 O2 117.13(15) . . ?
O1 S1 C4 109.71(15) . . ?
O1 S1 C8 110.31(15) . . ?
C8 S1 C4 101.57(13) . . ?
C5 N2 C15 117.7(2) . . ?
C9 N2 C5 123.4(2) . . ?
C9 N2 C15 117.7(2) . . ?
C9 C4 S1 120.5(2) . . ?
C12 C4 S1 117.8(2) . . ?
C12 C4 C9 121.4(3) . . ?
N2 C5 C8 122.2(2) . . ?
C21 C5 N2 121.1(3) . . ?
C21 C5 C8 116.6(3) . . ?
C5 C8 S1 120.6(2) . . ?
C13 C8 S1 118.1(2) . . ?
C13 C8 C5 121.0(3) . . ?
N2 C9 C4 122.3(3) . . ?
C14 C9 N2 120.2(2) . . ?
C14 C9 C4 117.4(3) . . ?
C20 C10 C15 118.4(3) . . ?
C18 C12 C4 120.8(3) . . ?
C23 C13 C8 120.7(3) . . ?
C17 C14 C9 120.1(3) . . ?
C10 C15 N2 119.9(2) . . ?
C24 C15 N2 119.3(3) . . ?
C24 C15 C10 120.8(3) . . ?
F2 C16 C20 120.6(3) . . ?
F2 C16 C25 120.9(3) . . ?
C25 C16 C20 118.4(3) . . ?
C14 C17 Cl2 118.5(3) . . ?
C14 C17 C18 122.3(3) . . ?
C18 C17 Cl2 119.1(3) . . ?
C12 C18 C17 118.0(3) . . ?
F1 C20 C10 119.9(3) . . ?
F1 C20 C16 118.3(3) . . ?
C16 C20 C10 121.8(3) . . ?
C22 C21 C5 121.7(3) . . ?
C21 C22 C23 120.9(3) . . ?
C13 C23 C22 118.9(3) . . ?
C15 C24 C25 118.7(3) . . ?
C16 C25 C24 121.8(3) . . ?
F3 C25 C16 118.7(3) . . ?
F3 C25 C24 119.6(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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.898
####################################################################### 
# 
# 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_PTZ-H
_database_code_depnum_ccdc_archive 'CCDC 2132713'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2020-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.143(C18 H10 F3 N O2 S)'
_chemical_formula_sum            'C20.57 H11.43 F3.43 N1.14 O2.29 S1.14'
_chemical_formula_weight         412.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H10 S1 NS O2 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6605(2)
_cell_length_b                   15.5563(2)
_cell_length_c                   18.6230(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3088.40(9)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.0450
_cell_measurement_theta_min      4.7380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.749
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.57    --  -41.12 -37.00 120.00   99
  2  ω     27.00 121.00   1.00    2.57    --   41.12  19.00  30.00   94
  3  ω     84.00 177.00   1.00   10.28    --  105.32  45.00 150.00   93
  4  ω    101.00 178.00   1.00   10.28    --  105.32  77.00 -30.00   77
  5  ω     43.00 124.00   1.00   10.28    --  105.32 -45.00 -30.00   81
  6  ω     25.00  68.00   1.00   10.28    --  105.32 -94.00-120.00   43
  7  ω     90.00 178.00   1.00   10.28    --  105.32  45.00-120.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1031552000
_diffrn_orient_matrix_UB_12      -0.0656132000
_diffrn_orient_matrix_UB_13      -0.0188401000
_diffrn_orient_matrix_UB_21      -0.0227862000
_diffrn_orient_matrix_UB_22      -0.0162486000
_diffrn_orient_matrix_UB_23      0.0806485000
_diffrn_orient_matrix_UB_31      -0.0984592000
_diffrn_orient_matrix_UB_32      0.0723018000
_diffrn_orient_matrix_UB_33      0.0010123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             2766
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.043
_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)+(0.0476P)²+0.8998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P)
;
_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
S001 S 0.70831(4) 0.63702(3) 0.52924(2) 0.04630(15) Uani 1 1 d . . . . .
F002 F 0.63668(14) 0.20401(8) 0.32309(8) 0.0800(4) Uani 1 1 d . . . . .
F003 F 0.84415(15) 0.21982(8) 0.24350(7) 0.0796(4) Uani 1 1 d . . . . .
N004 N 0.71876(13) 0.47628(8) 0.43591(7) 0.0413(3) Uani 1 1 d . . . . .
O005 O 0.81250(14) 0.68459(9) 0.50098(9) 0.0692(4) Uani 1 1 d . . . . .
O006 O 0.63878(16) 0.67631(10) 0.58673(8) 0.0723(4) Uani 1 1 d . . . . .
F007 F 0.99199(15) 0.35927(11) 0.25807(9) 0.1007(5) Uani 1 1 d . . . . .
C008 C 0.77109(15) 0.46971(10) 0.50486(8) 0.0379(3) Uani 1 1 d . . . . .
C009 C 0.62979(15) 0.53861(10) 0.41659(8) 0.0393(3) Uani 1 1 d . . . . .
C00A C 0.76070(15) 0.53634(10) 0.55526(9) 0.0403(4) Uani 1 1 d . . . . .
C00B C 0.60857(16) 0.61163(11) 0.45879(9) 0.0423(4) Uani 1 1 d . . . . .
C00C C 0.74837(15) 0.40926(10) 0.38524(8) 0.0390(3) Uani 1 1 d . . . . .
C00D C 0.67337(16) 0.33743(11) 0.37908(9) 0.0448(4) Uani 1 1 d . . . . .
H00D H 0.601388 0.331641 0.406876 0.054 Uiso 1 1 calc R U . . .
C00E C 0.81312(19) 0.28192(12) 0.28985(9) 0.0517(4) Uani 1 1 d . . . . .
C00F C 0.70724(18) 0.27459(11) 0.33102(10) 0.0484(4) Uani 1 1 d . . . . .
C00G C 0.51520(17) 0.67106(11) 0.44098(11) 0.0517(4) Uani 1 1 d . . . . .
H00G H 0.500769 0.718176 0.470584 0.062 Uiso 1 1 calc R U . . .
C00H C 0.80407(18) 0.52654(12) 0.62519(10) 0.0511(4) Uani 1 1 d . . . . .
H00H H 0.793595 0.570816 0.658206 0.061 Uiso 1 1 calc R U . . .
C00I C 0.83291(18) 0.39498(11) 0.52692(10) 0.0495(4) Uani 1 1 d . . . . .
H00I H 0.843422 0.350020 0.494554 0.059 Uiso 1 1 calc R U . . .
C00J C 0.85531(17) 0.41814(12) 0.34438(10) 0.0512(4) Uani 1 1 d . . . . .
H00J H 0.905361 0.466852 0.348527 0.061 Uiso 1 1 calc R U . . .
C00K C 0.87834(19) 0.38685(12) 0.59557(11) 0.0560(5) Uani 1 1 d . . . . .
H00K H 0.920590 0.336952 0.608653 0.067 Uiso 1 1 calc R U . . .
C00L C 0.55774(17) 0.52958(12) 0.35441(10) 0.0498(4) Uani 1 1 d . . . . .
H00L H 0.570584 0.482451 0.324574 0.060 Uiso 1 1 calc R U . . .
C00M C 0.8864(2) 0.35355(13) 0.29740(11) 0.0577(5) Uani 1 1 d . . . . .
C00N C 0.44485(18) 0.66012(13) 0.38004(11) 0.0581(5) Uani 1 1 d . . . . .
H00N H 0.382654 0.699491 0.368027 0.070 Uiso 1 1 calc R U . . .
C00O C 0.86229(19) 0.45176(13) 0.64567(10) 0.0562(5) Uani 1 1 d . . . . .
H00O H 0.890575 0.444758 0.692544 0.067 Uiso 1 1 calc R U . . .
C00P C 0.46774(18) 0.58968(13) 0.33669(10) 0.0569(5) Uani 1 1 d . . . . .
H00P H 0.421532 0.582672 0.294735 0.068 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
S001 O005 1.4346(15) . ?
S001 O006 1.4385(15) . ?
S001 C00A 1.7320(16) . ?
S001 C00B 1.7343(18) . ?
F002 C00F 1.339(2) . ?
F003 C00E 1.337(2) . ?
N004 C008 1.404(2) . ?
N004 C009 1.403(2) . ?
N004 C00C 1.441(2) . ?
F007 C00M 1.346(2) . ?
C008 C00A 1.403(2) . ?
C008 C00I 1.398(2) . ?
C009 C00B 1.400(2) . ?
C009 C00L 1.397(2) . ?
C00A C00H 1.390(3) . ?
C00B C00G 1.398(2) . ?
C00C C00D 1.379(2) . ?
C00C C00J 1.378(2) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.374(2) . ?
C00E C00F 1.369(3) . ?
C00E C00M 1.368(3) . ?
C00G H00G 0.9300 . ?
C00G C00N 1.371(3) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.373(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.373(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.373(3) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.385(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.380(3) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.383(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 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
O005 S001 O006 116.93(10) . . ?
O005 S001 C00A 108.62(9) . . ?
O005 S001 C00B 108.34(9) . . ?
O006 S001 C00A 110.01(9) . . ?
O006 S001 C00B 110.11(9) . . ?
C00A S001 C00B 101.74(8) . . ?
C008 N004 C00C 117.34(13) . . ?
C009 N004 C008 123.61(13) . . ?
C009 N004 C00C 118.68(13) . . ?
C00A C008 N004 121.79(14) . . ?
C00I C008 N004 121.11(14) . . ?
C00I C008 C00A 117.07(15) . . ?
C00B C009 N004 121.73(15) . . ?
C00L C009 N004 120.99(15) . . ?
C00L C009 C00B 117.28(15) . . ?
C008 C00A S001 120.43(13) . . ?
C00H C00A S001 117.93(13) . . ?
C00H C00A C008 121.30(16) . . ?
C009 C00B S001 120.70(13) . . ?
C00G C00B S001 117.73(14) . . ?
C00G C00B C009 121.22(17) . . ?
C00D C00C N004 120.91(15) . . ?
C00J C00C N004 118.06(15) . . ?
C00J C00C C00D 121.01(15) . . ?
C00C C00D H00D 120.7 . . ?
C00F C00D C00C 118.59(16) . . ?
C00F C00D H00D 120.7 . . ?
F003 C00E C00F 120.35(18) . . ?
F003 C00E C00M 120.89(18) . . ?
C00M C00E C00F 118.76(16) . . ?
F002 C00F C00D 120.50(17) . . ?
F002 C00F C00E 118.01(17) . . ?
C00E C00F C00D 121.48(17) . . ?
C00B C00G H00G 119.9 . . ?
C00N C00G C00B 120.25(18) . . ?
C00N C00G H00G 119.9 . . ?
C00A C00H H00H 119.9 . . ?
C00O C00H C00A 120.24(17) . . ?
C00O C00H H00H 119.9 . . ?
C008 C00I H00I 119.5 . . ?
C00K C00I C008 121.09(17) . . ?
C00K C00I H00I 119.5 . . ?
C00C C00J H00J 120.7 . . ?
C00M C00J C00C 118.59(17) . . ?
C00M C00J H00J 120.7 . . ?
C00I C00K H00K 119.5 . . ?
C00I C00K C00O 121.10(18) . . ?
C00O C00K H00K 119.5 . . ?
C009 C00L H00L 119.6 . . ?
C00P C00L C009 120.84(17) . . ?
C00P C00L H00L 119.6 . . ?
F007 C00M C00E 118.40(18) . . ?
F007 C00M C00J 120.04(19) . . ?
C00E C00M C00J 121.56(17) . . ?
C00G C00N H00N 120.5 . . ?
C00G C00N C00P 119.03(17) . . ?
C00P C00N H00N 120.5 . . ?
C00H C00O C00K 119.11(17) . . ?
C00H C00O H00O 120.4 . . ?
C00K C00O H00O 120.4 . . ?
C00L C00P C00N 121.33(18) . . ?
C00L C00P H00P 119.3 . . ?
C00N C00P H00P 119.3 . . ?

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
S001 C00A C00H C00O -171.09(15) . . . . ?
S001 C00B C00G C00N 171.13(14) . . . . ?
F003 C00E C00F F002 -0.2(3) . . . . ?
F003 C00E C00F C00D 179.93(17) . . . . ?
F003 C00E C00M F007 -1.3(3) . . . . ?
F003 C00E C00M C00J 179.51(19) . . . . ?
N004 C008 C00A S001 -12.0(2) . . . . ?
N004 C008 C00A C00H 174.80(16) . . . . ?
N004 C008 C00I C00K -176.56(17) . . . . ?
N004 C009 C00B S001 10.3(2) . . . . ?
N004 C009 C00B C00G -176.66(15) . . . . ?
N004 C009 C00L C00P 178.05(16) . . . . ?
N004 C00C C00D C00F -178.64(15) . . . . ?
N004 C00C C00J C00M 178.15(17) . . . . ?
O005 S001 C00A C008 -83.87(16) . . . . ?
O005 S001 C00A C00H 89.53(16) . . . . ?
O005 S001 C00B C009 84.86(15) . . . . ?
O005 S001 C00B C00G -88.41(15) . . . . ?
O006 S001 C00A C008 146.98(14) . . . . ?
O006 S001 C00A C00H -39.61(17) . . . . ?
O006 S001 C00B C009 -146.13(14) . . . . ?
O006 S001 C00B C00G 40.60(16) . . . . ?
C008 N004 C009 C00B 15.8(2) . . . . ?
C008 N004 C009 C00L -163.53(15) . . . . ?
C008 N004 C00C C00D 90.87(19) . . . . ?
C008 N004 C00C C00J -87.63(19) . . . . ?
C008 C00A C00H C00O 2.3(3) . . . . ?
C008 C00I C00K C00O 1.3(3) . . . . ?
C009 N004 C008 C00A -14.9(2) . . . . ?
C009 N004 C008 C00I 163.17(16) . . . . ?
C009 N004 C00C C00D -82.4(2) . . . . ?
C009 N004 C00C C00J 99.12(19) . . . . ?
C009 C00B C00G C00N -2.1(3) . . . . ?
C009 C00L C00P C00N -0.7(3) . . . . ?
C00A S001 C00B C009 -29.50(15) . . . . ?
C00A S001 C00B C00G 157.23(14) . . . . ?
C00A C008 C00I C00K 1.6(3) . . . . ?
C00A C00H C00O C00K 0.7(3) . . . . ?
C00B S001 C00A C008 30.28(15) . . . . ?
C00B S001 C00A C00H -156.32(14) . . . . ?
C00B C009 C00L C00P -1.3(3) . . . . ?
C00B C00G C00N C00P 0.0(3) . . . . ?
C00C N004 C008 C00A 172.19(15) . . . . ?
C00C N004 C008 C00I -9.7(2) . . . . ?
C00C N004 C009 C00B -171.36(15) . . . . ?
C00C N004 C009 C00L 9.3(2) . . . . ?
C00C C00D C00F F002 -179.65(16) . . . . ?
C00C C00D C00F C00E 0.2(3) . . . . ?
C00C C00J C00M F007 -178.30(19) . . . . ?
C00C C00J C00M C00E 0.9(3) . . . . ?
C00D C00C C00J C00M -0.3(3) . . . . ?
C00F C00E C00M F007 178.35(19) . . . . ?
C00F C00E C00M C00J -0.8(3) . . . . ?
C00G C00N C00P C00L 1.4(3) . . . . ?
C00I C008 C00A S001 169.82(13) . . . . ?
C00I C008 C00A C00H -3.4(3) . . . . ?
C00I C00K C00O C00H -2.5(3) . . . . ?
C00J C00C C00D C00F -0.2(3) . . . . ?
C00L C009 C00B S001 -170.30(13) . . . . ?
C00L C009 C00B C00G 2.7(2) . . . . ?
C00M C00E C00F F002 -179.85(18) . . . . ?
C00M C00E C00F C00D 0.3(3) . . . . ?

_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 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.744
####################################################################### 
# 
# 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_PTZ-F
_database_code_depnum_ccdc_archive 'CCDC 2132715'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2021-12-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H9 F4 N O2 S'
_chemical_formula_sum            'C18 H9 F4 N O2 S'
_chemical_formula_weight         379.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.5098(6)
_cell_length_b                   15.5106(7)
_cell_length_c                   19.2985(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3145.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      28.7960
_cell_measurement_theta_min      2.1480
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59197
_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    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.568
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0436270000
_diffrn_orient_matrix_UB_12      -0.0303713000
_diffrn_orient_matrix_UB_13      0.0137834000
_diffrn_orient_matrix_UB_21      0.0412203000
_diffrn_orient_matrix_UB_22      0.0071570000
_diffrn_orient_matrix_UB_23      -0.0285250000
_diffrn_orient_matrix_UB_31      0.0308043000
_diffrn_orient_matrix_UB_32      0.0334323000
_diffrn_orient_matrix_UB_33      0.0186587000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2303
_reflns_number_total             3085
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0043(6)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.035
_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)+(0.0548P)²+1.4771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C14(H14), C18(H18)
;
_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
S1 S 0.70192(6) 0.63339(4) 0.53016(4) 0.0482(2) Uani 1 1 d . . . . .
F1 F 1.0004(2) 0.36650(14) 0.25644(13) 0.1175(9) Uani 1 1 d . . . . .
F2 F 0.8570(2) 0.22321(12) 0.24523(9) 0.0901(7) Uani 1 1 d . . . . .
F3 F 0.6544(2) 0.20178(12) 0.32843(11) 0.0946(7) Uani 1 1 d . . . . .
F4 F 0.41657(19) 0.57691(13) 0.27744(9) 0.0806(6) Uani 1 1 d . . . . .
O1 O 0.8078(2) 0.68482(12) 0.50757(12) 0.0708(6) Uani 1 1 d . . . . .
O2 O 0.6243(2) 0.66864(13) 0.58472(11) 0.0732(6) Uani 1 1 d . . . . .
N1 N 0.73043(19) 0.47668(11) 0.43518(10) 0.0416(5) Uani 1 1 d . . . . .
C1 C 0.7585(2) 0.53220(14) 0.55338(12) 0.0417(6) Uani 1 1 d . . . . .
C2 C 0.7961(3) 0.51982(17) 0.62204(14) 0.0536(7) Uani 1 1 d . . . . .
H2 H 0.779106 0.561974 0.655032 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8580(3) 0.44586(18) 0.64094(15) 0.0617(8) Uani 1 1 d . . . . .
H3 H 0.881988 0.436905 0.686773 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8845(3) 0.38448(17) 0.59079(16) 0.0620(8) Uani 1 1 d . . . . .
H4 H 0.929753 0.335250 0.602989 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8454(3) 0.39486(16) 0.52370(15) 0.0546(7) Uani 1 1 d . . . . .
H5 H 0.863697 0.352286 0.491269 0.065 Uiso 1 1 calc R U . . .
C6 C 0.7782(2) 0.46840(14) 0.50300(13) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.6087(2) 0.60867(14) 0.45909(12) 0.0423(6) Uani 1 1 d . . . . .
C8 C 0.5115(2) 0.66626(15) 0.44039(14) 0.0509(6) Uani 1 1 d . . . . .
H8 H 0.491501 0.711802 0.469796 0.061 Uiso 1 1 calc R U . . .
C9 C 0.4458(3) 0.65667(17) 0.37996(15) 0.0578(7) Uani 1 1 d . . . . .
H9 H 0.381353 0.694749 0.367488 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4788(3) 0.58802(17) 0.33801(13) 0.0523(7) Uani 1 1 d . . . . .
C11 C 0.5711(3) 0.52916(16) 0.35433(13) 0.0492(6) Uani 1 1 d . . . . .
H11 H 0.588690 0.483692 0.324417 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6385(2) 0.53796(14) 0.41627(12) 0.0405(5) Uani 1 1 d . . . . .
C13 C 0.7618(2) 0.41000(14) 0.38570(12) 0.0404(5) Uani 1 1 d . . . . .
C14 C 0.8664(3) 0.42163(17) 0.34383(15) 0.0560(7) Uani 1 1 d . . . . .
H14 H 0.915284 0.471457 0.346952 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8968(3) 0.35798(19) 0.29737(15) 0.0627(8) Uani 1 1 d . . . . .
C16 C 0.8258(3) 0.28480(17) 0.29141(13) 0.0567(7) Uani 1 1 d . . . . .
C17 C 0.7228(3) 0.27458(16) 0.33412(14) 0.0533(7) Uani 1 1 d . . . . .
C18 C 0.6889(2) 0.33635(16) 0.38155(13) 0.0470(6) Uani 1 1 d . . . . .
H18 H 0.618605 0.328718 0.410138 0.056 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
S1 O1 1.437(2) . ?
S1 O2 1.440(2) . ?
S1 C1 1.737(2) . ?
S1 C7 1.728(3) . ?
F1 C15 1.352(3) . ?
F2 C16 1.347(3) . ?
F3 C17 1.343(3) . ?
F4 C10 1.351(3) . ?
N1 C6 1.408(3) . ?
N1 C12 1.404(3) . ?
N1 C13 1.446(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C7 C8 1.405(3) . ?
C7 C12 1.408(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 C11 1.368(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(3) . ?
C13 C14 1.376(3) . ?
C13 C18 1.378(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(4) . ?
C15 C16 1.363(4) . ?
C16 C17 1.369(4) . ?
C17 C18 1.372(3) . ?
C18 H18 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
O1 S1 O2 116.72(13) . . ?
O1 S1 C1 108.35(12) . . ?
O1 S1 C7 108.73(12) . . ?
O2 S1 C1 110.39(12) . . ?
O2 S1 C7 110.10(12) . . ?
C7 S1 C1 101.43(11) . . ?
C6 N1 C13 117.86(18) . . ?
C12 N1 C6 123.31(19) . . ?
C12 N1 C13 118.02(19) . . ?
C2 C1 S1 117.77(18) . . ?
C2 C1 C6 121.3(2) . . ?
C6 C1 S1 120.61(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 N1 121.8(2) . . ?
C5 C6 N1 121.3(2) . . ?
C5 C6 C1 116.9(2) . . ?
C8 C7 S1 118.36(19) . . ?
C8 C7 C12 120.4(2) . . ?
C12 C7 S1 120.85(18) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.2(2) . . ?
C10 C9 H9 121.4 . . ?
F4 C10 C9 118.9(2) . . ?
F4 C10 C11 117.2(2) . . ?
C11 C10 C9 123.9(3) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
N1 C12 C7 121.8(2) . . ?
C11 C12 N1 120.4(2) . . ?
C11 C12 C7 117.8(2) . . ?
C14 C13 N1 118.5(2) . . ?
C14 C13 C18 121.2(2) . . ?
C18 C13 N1 120.3(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.4(2) . . ?
C15 C14 H14 120.8 . . ?
F1 C15 C14 120.0(3) . . ?
F1 C15 C16 118.2(3) . . ?
C16 C15 C14 121.8(3) . . ?
F2 C16 C15 120.8(3) . . ?
F2 C16 C17 120.6(3) . . ?
C15 C16 C17 118.6(2) . . ?
F3 C17 C16 118.1(2) . . ?
F3 C17 C18 120.2(3) . . ?
C16 C17 C18 121.7(2) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 C13 118.3(2) . . ?
C17 C18 H18 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -170.7(2) . . . . ?
S1 C1 C6 N1 -12.9(3) . . . . ?
S1 C1 C6 C5 168.58(19) . . . . ?
S1 C7 C8 C9 171.2(2) . . . . ?
S1 C7 C12 N1 10.8(3) . . . . ?
S1 C7 C12 C11 -170.70(18) . . . . ?
F1 C15 C16 F2 -0.9(4) . . . . ?
F1 C15 C16 C17 178.1(3) . . . . ?
F2 C16 C17 F3 -0.1(4) . . . . ?
F2 C16 C17 C18 -180.0(2) . . . . ?
F3 C17 C18 C13 179.9(2) . . . . ?
F4 C10 C11 C12 179.8(2) . . . . ?
O1 S1 C1 C2 89.9(2) . . . . ?
O1 S1 C1 C6 -83.4(2) . . . . ?
O1 S1 C7 C8 -88.6(2) . . . . ?
O1 S1 C7 C12 84.2(2) . . . . ?
O2 S1 C1 C2 -39.1(2) . . . . ?
O2 S1 C1 C6 147.6(2) . . . . ?
O2 S1 C7 C8 40.4(2) . . . . ?
O2 S1 C7 C12 -146.8(2) . . . . ?
N1 C13 C14 C15 179.4(2) . . . . ?
N1 C13 C18 C17 -179.6(2) . . . . ?
C1 S1 C7 C8 157.32(19) . . . . ?
C1 S1 C7 C12 -29.9(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C1 C6 N1 174.0(2) . . . . ?
C2 C1 C6 C5 -4.5(4) . . . . ?
C2 C3 C4 C5 -2.8(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 N1 -175.7(3) . . . . ?
C4 C5 C6 C1 2.9(4) . . . . ?
C6 N1 C12 C7 15.3(3) . . . . ?
C6 N1 C12 C11 -163.3(2) . . . . ?
C6 N1 C13 C14 -93.7(3) . . . . ?
C6 N1 C13 C18 85.6(3) . . . . ?
C6 C1 C2 C3 2.6(4) . . . . ?
C7 S1 C1 C2 -155.8(2) . . . . ?
C7 S1 C1 C6 30.9(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C7 C12 N1 -176.6(2) . . . . ?
C8 C7 C12 C11 2.0(3) . . . . ?
C8 C9 C10 F4 -179.4(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 N1 177.8(2) . . . . ?
C10 C11 C12 C7 -0.8(4) . . . . ?
C12 N1 C6 C1 -14.1(3) . . . . ?
C12 N1 C6 C5 164.4(2) . . . . ?
C12 N1 C13 C14 96.3(3) . . . . ?
C12 N1 C13 C18 -84.5(3) . . . . ?
C12 C7 C8 C9 -1.6(4) . . . . ?
C13 N1 C6 C1 176.5(2) . . . . ?
C13 N1 C6 C5 -5.1(3) . . . . ?
C13 N1 C12 C7 -175.3(2) . . . . ?
C13 N1 C12 C11 6.2(3) . . . . ?
C13 C14 C15 F1 -178.6(3) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
C14 C15 C16 F2 179.7(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 F3 -179.2(3) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 0.1(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.708
####################################################################### 
# 
# 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_PTZ-Br
_database_code_depnum_ccdc_archive 'CCDC 2132716'
loop_
_audit_author_name
_audit_author_address
'Jia Ren'
;Tianjin University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2021-10-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H9 Br F3 N O2 S'
_chemical_formula_sum            'C18 H9 Br F3 N O2 S'
_chemical_formula_weight         440.242
_chemical_oxdiff_formula         'C18 H9 S1 N1 F3 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 x+1/3,y+2/3,z+2/3
8 -y+1/3,x-y+2/3,z+2/3
9 -x+y+1/3,-x+2/3,z+2/3
10 -x+1/3,-y+2/3,-z+2/3
11 y+1/3,-x+y+2/3,-z+2/3
12 x-y+1/3,x+2/3,-z+2/3
13 x+2/3,y+1/3,z+1/3
14 -y+2/3,x-y+1/3,z+1/3
15 -x+y+2/3,-x+1/3,z+1/3
16 -x+2/3,-y+1/3,-z+1/3
17 y+2/3,-x+y+1/3,-z+1/3
18 x-y+2/3,x+1/3,-z+1/3

_symmetry_Int_Tables_number      148
_cell_length_a                   23.3444(4)
_cell_length_b                   23.3444(4)
_cell_length_c                   16.0383(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7569.3(2)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    4192
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.1090
_cell_measurement_theta_min      3.7770
_exptl_absorpt_coefficient_mu    4.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       block
_exptl_crystal_F_000             3930.762
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.9921
_diffrn_reflns_Laue_measured_fraction_max 0.9921
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5981
_diffrn_reflns_point_group_measured_fraction_full 0.9921
_diffrn_reflns_point_group_measured_fraction_max 0.9921
_diffrn_reflns_theta_full        67.0737
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  10.00   1.00    6.73    --  -41.12  57.00  60.00   79
  2  ω     44.00  93.00   1.00    6.73    --   41.12-125.00-180.00   49
  3  ω     80.00 106.00   1.00   26.93    --  105.32-125.00  60.00   26
  4  ω     35.00 115.00   1.00   26.93    --  105.32-125.00   0.00   80
  5  ω     84.00 177.00   1.00   26.93    --  105.32  45.00 -90.00   93
  6  ω    142.00 168.00   1.00   26.93    --  105.32 105.00 -90.00   26
  7  ω    110.00 149.00   1.00   26.93    --  105.32 123.00-141.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0717391000
_diffrn_orient_matrix_UB_12      -0.0143764000
_diffrn_orient_matrix_UB_13      0.0086274000
_diffrn_orient_matrix_UB_21      0.0256821000
_diffrn_orient_matrix_UB_22      0.0720829000
_diffrn_orient_matrix_UB_23      0.0272767000
_diffrn_orient_matrix_UB_31      0.0008917000
_diffrn_orient_matrix_UB_32      0.0200906000
_diffrn_orient_matrix_UB_33      -0.0916683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2775
_reflns_number_total             2995
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.1558
_refine_diff_density_min         -1.1282
_refine_diff_density_rms         0.1384
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             12.5647
_refine_ls_goodness_of_fit_ref   1.0413
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      1.0413
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1231P)²+20.1717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1894
_refine_ls_wR_factor_ref         0.1923
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C00P(H00P), C00G(H00G), C00D(H00D), C00B(H00B), C00M(H00M),
 C00N(H00N), C00L(H00L), C00E(H00E)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br01 Br 0.58877(3) 0.20276(4) 0.43223(5) 0.1057(3) Uani 1.000000 .
S002 S 0.45688(6) 0.29027(5) 0.71409(6) 0.0645(3) Uani 1.000000 .
F003 F 0.42630(16) 0.36321(15) 0.27428(17) 0.0860(8) Uani 1.000000 .
F004 F 0.34191(17) 0.24807(18) 0.20294(14) 0.0876(9) Uani 1.000000 .
F005 F 0.29070(18) 0.13520(15) 0.29098(17) 0.0883(9) Uani 1.000000 .
N006 N 0.40749(17) 0.25570(17) 0.53525(17) 0.0553(7) Uani 1.000000 .
O007 O 0.4538(2) 0.2616(2) 0.79447(19) 0.0922(11) Uani 1.000000 .
O008 O 0.49615(19) 0.36102(16) 0.7069(2) 0.0886(10) Uani 1.000000 .
C009 C 0.46159(19) 0.24870(18) 0.5566(2) 0.0527(8) Uani 1.000000 .
C00A C 0.39041(19) 0.25264(19) 0.4480(2) 0.0497(8) Uani 1.000000 .
C00B C 0.3476(2) 0.19339(19) 0.4118(2) 0.0568(9) Uani 1.000000 .
C00C C 0.36207(19) 0.25450(17) 0.5941(2) 0.0507(8) Uani 1.000000 .
C00D C 0.4182(2) 0.3114(2) 0.4034(2) 0.0550(8) Uani 1.000000 .
C00E C 0.2995(2) 0.2418(2) 0.5692(2) 0.0567(9) Uani 1.000000 .
C00F C 0.3583(2) 0.2497(2) 0.2831(2) 0.0584(9) Uani 1.000000 .
C00G C 0.4940(2) 0.2325(2) 0.4953(3) 0.0610(9) Uani 1.000000 .
C00H C 0.4006(2) 0.3079(2) 0.3210(2) 0.0574(9) Uani 1.000000 .
C00I C 0.4851(2) 0.25637(19) 0.6387(2) 0.0595(9) Uani 1.000000 .
C00J C 0.3774(2) 0.26470(18) 0.6788(2) 0.0555(9) Uani 1.000000 .
C00K C 0.3321(2) 0.1923(2) 0.3292(2) 0.0589(9) Uani 1.000000 .
C00L C 0.2545(2) 0.2397(2) 0.6266(2) 0.0610(9) Uani 1.000000 .
C00M C 0.3310(2) 0.26183(19) 0.7372(2) 0.0622(10) Uani 1.000000 .
C00N C 0.2706(2) 0.2499(2) 0.7113(2) 0.0667(11) Uani 1.000000 .
C00O C 0.5458(2) 0.2229(2) 0.5182(3) 0.0728(11) Uani 1.000000 .
C00P C 0.5352(2) 0.2439(3) 0.6595(3) 0.0774(12) Uani 1.000000 .
C00Q C 0.5661(2) 0.2273(3) 0.5993(4) 0.0867(15) Uani 1.000000 .
H00Q H 0.6001(2) 0.2192(3) 0.6132(4) 0.1041(18) Uiso 1.000000 R
H00P H 0.5482(2) 0.2469(3) 0.7149(3) 0.0928(15) Uiso 1.000000 R
H00G H 0.4809(2) 0.2284(2) 0.4398(3) 0.0733(11) Uiso 1.000000 R
H00D H 0.4476(2) 0.3516(2) 0.4282(2) 0.0660(10) Uiso 1.000000 R
H00B H 0.3293(2) 0.15448(19) 0.4427(2) 0.0682(11) Uiso 1.000000 R
H00M H 0.3417(2) 0.26810(19) 0.7935(2) 0.0747(12) Uiso 1.000000 R
H00N H 0.2402(2) 0.2486(2) 0.7498(2) 0.0801(13) Uiso 1.000000 R
H00L H 0.2131(2) 0.2315(2) 0.6088(2) 0.0732(11) Uiso 1.000000 R
H00E H 0.2879(2) 0.2346(2) 0.5131(2) 0.0681(11) Uiso 1.000000 R


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
Br01 C00O 1.897(5) . ?
S002 O007 1.438(3) . ?
S002 O008 1.438(4) . ?
S002 C00I 1.744(5) . ?
S002 C00J 1.735(4) . ?
F003 C00H 1.347(4) . ?
F004 C00F 1.338(4) . ?
F005 C00K 1.342(5) . ?
N006 C009 1.395(5) . ?
N006 C00A 1.447(4) . ?
N006 C00C 1.409(5) . ?
C009 C00G 1.403(6) . ?
C009 C00I 1.403(5) . ?
C00A C00B 1.366(6) . ?
C00A C00D 1.388(5) . ?
C00B C00K 1.372(6) . ?
C00C C00E 1.396(6) . ?
C00C C00J 1.396(5) . ?
C00D C00H 1.374(6) . ?
C00E C00L 1.379(6) . ?
C00F C00H 1.359(6) . ?
C00F C00K 1.375(6) . ?
C00G C00O 1.384(6) . ?
C00I C00P 1.381(7) . ?
C00J C00M 1.408(6) . ?
C00L C00N 1.398(6) . ?
C00M C00N 1.357(7) . ?
C00O C00Q 1.371(8) . ?
C00P C00Q 1.372(8) . ?

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
O008 S002 O007 117.5(2) . . ?
C00I S002 O007 110.6(2) . . ?
C00I S002 O008 107.3(2) . . ?
C00J S002 O007 109.7(2) . . ?
C00J S002 O008 109.1(2) . . ?
C00J S002 C00I 101.49(18) . . ?
C00A N006 C009 118.3(3) . . ?
C00C N006 C009 123.4(3) . . ?
C00C N006 C00A 117.4(3) . . ?
C00G C009 N006 120.1(3) . . ?
C00I C009 N006 122.3(3) . . ?
C00I C009 C00G 117.6(4) . . ?
C00B C00A N006 120.3(3) . . ?
C00D C00A N006 117.9(4) . . ?
C00D C00A C00B 121.8(3) . . ?
C00K C00B C00A 118.8(3) . . ?
C00E C00C N006 120.7(3) . . ?
C00J C00C N006 121.5(4) . . ?
C00J C00C C00E 117.8(3) . . ?
C00H C00D C00A 117.3(4) . . ?
C00L C00E C00C 121.0(3) . . ?
C00H C00F F004 120.8(4) . . ?
C00K C00F F004 120.5(4) . . ?
C00K C00F C00H 118.7(3) . . ?
C00O C00G C009 119.4(4) . . ?
C00D C00H F003 120.0(4) . . ?
C00F C00H F003 117.6(4) . . ?
C00F C00H C00D 122.4(3) . . ?
C009 C00I S002 119.8(3) . . ?
C00P C00I S002 118.7(3) . . ?
C00P C00I C009 121.2(4) . . ?
C00C C00J S002 121.0(3) . . ?
C00M C00J S002 117.7(3) . . ?
C00M C00J C00C 120.9(4) . . ?
C00B C00K F005 120.8(4) . . ?
C00F C00K F005 118.1(4) . . ?
C00F C00K C00B 121.1(4) . . ?
C00N C00L C00E 120.4(4) . . ?
C00N C00M C00J 120.2(3) . . ?
C00M C00N C00L 119.7(4) . . ?
C00G C00O Br01 117.4(4) . . ?
C00Q C00O Br01 120.1(4) . . ?
C00Q C00O C00G 122.5(5) . . ?
C00Q C00P C00I 120.7(5) . . ?
C00P C00Q C00O 118.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C00O C00G C009 -178.9(3) . . . . ?
Br01 C00O C00Q C00P 178.0(4) . . . . ?
S002 C00I C009 N006 -12.1(4) . . . . ?
S002 C00I C009 C00G 168.8(3) . . . . ?
S002 C00I C00P C00Q -169.6(4) . . . . ?
S002 C00J C00C N006 8.7(3) . . . . ?
S002 C00J C00C C00E -172.4(3) . . . . ?
S002 C00J C00M C00N 172.1(3) . . . . ?
F003 C00H C00D C00A -179.5(3) . . . . ?
F003 C00H C00F F004 -1.7(4) . . . . ?
F003 C00H C00F C00K 179.0(3) . . . . ?
F004 C00F C00H C00D 179.6(4) . . . . ?
F004 C00F C00K F005 0.9(4) . . . . ?
F004 C00F C00K C00B -178.8(4) . . . . ?
F005 C00K C00B C00A 179.5(4) . . . . ?
F005 C00K C00F C00H -179.8(4) . . . . ?
N006 C009 C00G C00O -177.1(4) . . . . ?
N006 C009 C00I C00P 174.7(4) . . . . ?
N006 C00A C00B C00K 179.5(4) . . . . ?
N006 C00A C00D C00H -178.8(3) . . . . ?
N006 C00C C00E C00L 179.2(4) . . . . ?
N006 C00C C00J C00M -178.5(3) . . . . ?
C009 C00G C00O C00Q 1.3(5) . . . . ?
C009 C00I C00P C00Q 3.7(5) . . . . ?
C00A C00B C00K C00F -0.8(4) . . . . ?
C00A C00D C00H C00F -0.8(4) . . . . ?
C00B C00K C00F C00H 0.5(5) . . . . ?
C00C C00E C00L C00N -0.5(5) . . . . ?
C00C C00J C00M C00N -0.9(4) . . . . ?
C00D C00H C00F C00K 0.3(4) . . . . ?
C00E C00L C00N C00M -0.1(5) . . . . ?
C00G C00O C00Q C00P -2.1(6) . . . . ?
C00I C00P C00Q C00O -0.4(6) . . . . ?
C00J C00M C00N C00L 0.8(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 1.842
_oxdiff_exptl_absorpt_empirical_full_min 0.631
