# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_2secf33h
_database_code_depnum_ccdc_archive 'CCDC 2125421'
loop_
_audit_author_name
_audit_author_address
'hui wang'
;Westlake University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        P21/c
_chemical_formula_moiety         'C16 H12 F3 N O2 S Se'
_chemical_formula_sum            'C16 H12 F3 N O2 S Se'
_chemical_formula_weight         418.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.620(4)
_cell_length_b                   8.759(3)
_cell_length_c                   19.797(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.899(13)
_cell_angle_gamma                90
_cell_volume                     1648.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.942
_cell_measurement_theta_min      2.748
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5086
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1186 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.6825.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.032
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2076
_reflns_number_total             2914
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.6883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C2(H2), C11(H11), C10(H10), C4(H4), C7(H7), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.75963(5) 0.29546(4) 0.41056(3) 0.0635(2) Uani 1 1 d . . . . .
S1 S 0.79275(10) 0.67304(11) 0.35905(5) 0.0489(3) Uani 1 1 d . . . . .
O1 O 0.8524(3) 0.5558(3) 0.32272(14) 0.0635(8) Uani 1 1 d . . . . .
O2 O 0.8466(3) 0.8248(3) 0.35883(15) 0.0651(8) Uani 1 1 d . . . . .
N005 N 0.8147(3) 0.6204(3) 0.44153(16) 0.0458(7) Uani 1 1 d . . . . .
F2 F 0.4969(3) 0.3889(4) 0.4299(2) 0.1330(14) Uani 1 1 d . . . . .
C9 C 0.6093(4) 0.6776(4) 0.33372(19) 0.0448(9) Uani 1 1 d . . . . .
C8 C 0.8351(3) 0.7193(4) 0.4988(2) 0.0463(9) Uani 1 1 d . . . . .
C14 C 0.5310(4) 0.7865(4) 0.3624(2) 0.0544(10) Uani 1 1 d . . . . .
H14 H 0.575131 0.854586 0.394829 0.065 Uiso 1 1 calc R U . . .
F3 F 0.5043(4) 0.1685(5) 0.3901(2) 0.1492(17) Uani 1 1 d . . . . .
C12 C 0.3181(4) 0.6933(5) 0.2944(2) 0.0555(11) Uani 1 1 d . . . . .
C1 C 0.8043(4) 0.4700(4) 0.4664(2) 0.0482(9) Uani 1 1 d . . . . .
C13 C 0.3876(4) 0.7926(5) 0.3423(2) 0.0609(11) Uani 1 1 d . . . . .
H13 H 0.335964 0.865971 0.361586 0.073 Uiso 1 1 calc R U . . .
C3 C 0.8414(4) 0.6280(4) 0.5574(2) 0.0503(10) Uani 1 1 d . . . . .
C2 C 0.8232(4) 0.4724(4) 0.5348(2) 0.0548(10) Uani 1 1 d . . . . .
H2 H 0.824423 0.387445 0.563028 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3981(5) 0.5875(5) 0.2672(2) 0.0678(12) Uani 1 1 d . . . . .
H11 H 0.353702 0.519366 0.234738 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5434(4) 0.5778(5) 0.2861(2) 0.0637(11) Uani 1 1 d . . . . .
H10 H 0.594817 0.504475 0.266596 0.076 Uiso 1 1 calc R U . . .
C4 C 0.8617(5) 0.6960(5) 0.6222(2) 0.0663(12) Uani 1 1 d . . . . .
H4 H 0.867324 0.636907 0.661559 0.080 Uiso 1 1 calc R U . . .
C7 C 0.8487(4) 0.8771(4) 0.5033(2) 0.0566(11) Uani 1 1 d . . . . .
H7 H 0.844964 0.937771 0.464501 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8729(4) 0.8515(6) 0.6262(3) 0.0700(13) Uani 1 1 d . . . . .
H5 H 0.884037 0.898650 0.668840 0.084 Uiso 1 1 calc R U . . .
C6 C 0.8679(4) 0.9395(5) 0.5682(3) 0.0658(12) Uani 1 1 d . . . . .
H6 H 0.877893 1.044752 0.572838 0.079 Uiso 1 1 calc R U . . .
F1 F 0.5686(5) 0.2108(6) 0.4922(2) 0.171(2) Uani 1 1 d . . . . .
C16 C 0.5720(5) 0.2666(6) 0.4317(3) 0.0722(13) Uani 1 1 d . . . . .
C15 C 0.1615(5) 0.7038(6) 0.2723(3) 0.0826(16) Uani 1 1 d . . . . .
H15A H 0.115639 0.712505 0.311944 0.124 Uiso 1 1 calc R U . . .
H15B H 0.128746 0.613633 0.247222 0.124 Uiso 1 1 calc R U . . .
H15C H 0.140138 0.791912 0.243799 0.124 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
Se1 C1 1.897(4) . ?
Se1 C16 1.931(5) . ?
S1 O1 1.424(3) . ?
S1 O2 1.427(3) . ?
S1 N005 1.678(3) . ?
S1 C9 1.759(4) . ?
N005 C8 1.416(5) . ?
N005 C1 1.416(4) . ?
F2 C16 1.289(6) . ?
C9 C14 1.389(5) . ?
C9 C10 1.368(5) . ?
C8 C3 1.404(5) . ?
C8 C7 1.390(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.376(6) . ?
F3 C16 1.294(5) . ?
C12 C13 1.381(6) . ?
C12 C11 1.368(6) . ?
C12 C15 1.505(6) . ?
C1 C2 1.337(5) . ?
C13 H13 0.9300 . ?
C3 C2 1.436(5) . ?
C3 C4 1.400(6) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.392(6) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.368(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(6) . ?
C6 H6 0.9300 . ?
F1 C16 1.299(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C16 96.54(18) . . ?
O1 S1 O2 119.68(18) . . ?
O1 S1 N005 107.05(16) . . ?
O1 S1 C9 109.70(18) . . ?
O2 S1 N005 105.55(17) . . ?
O2 S1 C9 109.06(17) . . ?
N005 S1 C9 104.69(16) . . ?
C8 N005 S1 126.2(2) . . ?
C8 N005 C1 107.4(3) . . ?
C1 N005 S1 126.1(3) . . ?
C14 C9 S1 118.9(3) . . ?
C10 C9 S1 121.3(3) . . ?
C10 C9 C14 119.8(4) . . ?
C3 C8 N005 107.2(3) . . ?
C7 C8 N005 131.3(4) . . ?
C7 C8 C3 121.4(4) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C13 C12 C15 121.2(4) . . ?
C11 C12 C13 117.1(4) . . ?
C11 C12 C15 121.7(4) . . ?
N005 C1 Se1 124.6(3) . . ?
C2 C1 Se1 125.9(3) . . ?
C2 C1 N005 109.4(3) . . ?
C14 C13 C12 122.1(4) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C8 C3 C2 107.1(3) . . ?
C4 C3 C8 119.8(4) . . ?
C4 C3 C2 133.0(4) . . ?
C1 C2 C3 108.8(3) . . ?
C1 C2 H2 125.6 . . ?
C3 C2 H2 125.6 . . ?
C12 C11 H11 118.7 . . ?
C12 C11 C10 122.5(4) . . ?
C10 C11 H11 118.7 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C8 C7 H7 121.6 . . ?
C6 C7 C8 116.8(4) . . ?
C6 C7 H7 121.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C7 C6 H6 118.8 . . ?
C5 C6 C7 122.4(4) . . ?
C5 C6 H6 118.8 . . ?
F2 C16 Se1 115.1(3) . . ?
F2 C16 F3 108.0(5) . . ?
F2 C16 F1 104.1(5) . . ?
F3 C16 Se1 110.2(3) . . ?
F3 C16 F1 104.7(5) . . ?
F1 C16 Se1 114.0(4) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C1 C2 C3 -174.3(3) . . . . ?
S1 N005 C8 C3 177.0(2) . . . . ?
S1 N005 C8 C7 -3.3(5) . . . . ?
S1 N005 C1 Se1 -1.0(4) . . . . ?
S1 N005 C1 C2 -177.8(3) . . . . ?
S1 C9 C14 C13 179.1(3) . . . . ?
S1 C9 C10 C11 -179.2(3) . . . . ?
O1 S1 N005 C8 148.2(3) . . . . ?
O1 S1 N005 C1 -37.6(3) . . . . ?
O1 S1 C9 C14 -178.8(3) . . . . ?
O1 S1 C9 C10 0.4(4) . . . . ?
O2 S1 N005 C8 19.7(3) . . . . ?
O2 S1 N005 C1 -166.1(3) . . . . ?
O2 S1 C9 C14 -45.9(4) . . . . ?
O2 S1 C9 C10 133.3(3) . . . . ?
N005 S1 C9 C14 66.6(3) . . . . ?
N005 S1 C9 C10 -114.2(3) . . . . ?
N005 C8 C3 C2 -0.6(4) . . . . ?
N005 C8 C3 C4 179.8(3) . . . . ?
N005 C8 C7 C6 -179.9(4) . . . . ?
N005 C1 C2 C3 2.4(4) . . . . ?
C9 S1 N005 C8 -95.4(3) . . . . ?
C9 S1 N005 C1 78.8(3) . . . . ?
C9 C14 C13 C12 0.2(6) . . . . ?
C8 N005 C1 Se1 174.0(2) . . . . ?
C8 N005 C1 C2 -2.7(4) . . . . ?
C8 C3 C2 C1 -1.1(4) . . . . ?
C8 C3 C4 C5 0.9(6) . . . . ?
C8 C7 C6 C5 -0.4(6) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C12 C11 C10 C9 0.0(7) . . . . ?
C1 N005 C8 C3 1.9(4) . . . . ?
C1 N005 C8 C7 -178.4(4) . . . . ?
C13 C12 C11 C10 0.1(6) . . . . ?
C3 C8 C7 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 -1.6(6) . . . . ?
C2 C3 C4 C5 -178.7(4) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C10 C9 C14 C13 -0.1(6) . . . . ?
C4 C3 C2 C1 178.5(4) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
C7 C8 C3 C2 179.7(3) . . . . ?
C7 C8 C3 C4 0.1(5) . . . . ?
C16 Se1 C1 N005 -107.9(3) . . . . ?
C16 Se1 C1 C2 68.3(4) . . . . ?
C15 C12 C13 C14 -179.0(4) . . . . ?
C15 C12 C11 C10 178.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2secf33bz
_database_code_depnum_ccdc_archive 'CCDC 2129692'
loop_
_audit_author_name
_audit_author_address
'hui wang'
;Westlake University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        P-1
_chemical_formula_moiety         'C23 H16 F3 N O3 S Se'
_chemical_formula_sum            'C23 H16 F3 N O3 S Se'
_chemical_formula_weight         522.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6028(9)
_cell_length_b                   9.6813(8)
_cell_length_c                   12.1098(12)
_cell_angle_alpha                95.599(3)
_cell_angle_beta                 107.070(3)
_cell_angle_gamma                98.588(3)
_cell_volume                     1052.18(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.002
_cell_measurement_theta_min      2.259
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
wR2(int) was 0.2782 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8324.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.083
_diffrn_reflns_theta_max         25.083
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             3730
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.037
_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)+(0.0260P)²+0.8941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C22(H22), C4(H4), C18(H18), C21(H21), C19(H19), C5(H5), C6(H6),
 C11(H11), C15(H15), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
Se1 Se 0.18930(2) 0.52186(2) 0.23355(2) 0.03085(8) Uani 1 1 d . . . . .
S1 S 0.79564(5) 0.74984(5) 0.34246(4) 0.02236(12) Uani 1 1 d . . . . .
O1 O 0.90430(16) 0.66754(15) 0.33444(13) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.74978(16) 0.84342(15) 0.26059(13) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.44980(18) 0.88363(15) 0.29462(13) 0.0330(4) Uani 1 1 d . . . . .
F1 F 0.20812(19) 0.26906(16) 0.11774(14) 0.0564(4) Uani 1 1 d . . . . .
F2 F 0.00151(17) 0.3371(2) 0.05304(16) 0.0703(5) Uani 1 1 d . . . . .
F3 F 0.1921(2) 0.42943(19) 0.01042(14) 0.0687(5) Uani 1 1 d . . . . .
N1 N 0.63934(18) 0.63356(17) 0.32658(14) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.4942(2) 0.6524(2) 0.27357(16) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.4824(2) 0.4449(2) 0.34673(16) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.3980(2) 0.5390(2) 0.28282(17) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.8441(2) 0.8384(2) 0.48532(17) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.6329(2) 0.5058(2) 0.37344(17) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.9171(2) 0.9777(2) 0.71226(19) 0.0268(5) Uani 1 1 d . . . . .
C7 C 0.7458(2) 0.4418(2) 0.43516(18) 0.0253(4) Uani 1 1 d . . . . .
H7 H 0.845155 0.482550 0.452100 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9442(2) 0.7923(2) 0.57558(19) 0.0265(5) Uani 1 1 d . . . . .
H22 H 0.987175 0.715564 0.560523 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4439(2) 0.3158(2) 0.38306(18) 0.0242(4) Uani 1 1 d . . . . .
H4 H 0.344891 0.273612 0.365801 0.029 Uiso 1 1 calc R U . . .
C18 C 0.7793(2) 0.9529(2) 0.50675(19) 0.0260(4) Uani 1 1 d . . . . .
H18 H 0.712219 0.983323 0.445916 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4189(2) 0.7881(2) 0.09953(18) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.4552(2) 0.7862(2) 0.22622(18) 0.0231(4) Uani 1 1 d . . . . .
C21 C 0.9790(2) 0.8617(2) 0.68798(19) 0.0290(5) Uani 1 1 d . . . . .
H21 H 1.045199 0.830345 0.748797 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8162(2) 1.0208(2) 0.61980(19) 0.0293(5) Uani 1 1 d . . . . .
H19 H 0.772673 1.097154 0.634698 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5550(2) 0.2526(2) 0.44472(18) 0.0273(5) Uani 1 1 d . . . . .
H5 H 0.530810 0.167086 0.469854 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7037(2) 0.3149(2) 0.47011(19) 0.0278(5) Uani 1 1 d . . . . .
H6 H 0.776590 0.269577 0.511829 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3578(2) 0.8993(2) 0.0521(2) 0.0328(5) Uani 1 1 d . . . . .
H11 H 0.337471 0.969794 0.099709 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9591(3) 1.0555(3) 0.8340(2) 0.0378(5) Uani 1 1 d . . . . .
H23A H 0.962361 0.988882 0.888010 0.057 Uiso 1 1 calc R U . . .
H23B H 0.886919 1.112608 0.838978 0.057 Uiso 1 1 calc R U . . .
H23C H 1.054837 1.114946 0.852928 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1473(3) 0.3818(3) 0.0956(2) 0.0402(6) Uani 1 1 d . . . . .
C15 C 0.4492(3) 0.6848(3) 0.0274(2) 0.0413(6) Uani 1 1 d . . . . .
H15 H 0.489703 0.610214 0.058381 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3277(3) 0.9039(3) -0.0665(2) 0.0430(7) Uani 1 1 d . . . . .
H12 H 0.286119 0.977515 -0.098536 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3583(3) 0.8016(3) -0.1366(2) 0.0519(7) Uani 1 1 d . . . . .
H13 H 0.337626 0.806116 -0.216025 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4195(4) 0.6920(3) -0.0910(2) 0.0548(7) Uani 1 1 d . . . . .
H14 H 0.440955 0.622911 -0.139158 0.066 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
Se1 C2 1.8915(19) . ?
Se1 C16 1.947(3) . ?
S1 O1 1.4233(15) . ?
S1 O2 1.4267(15) . ?
S1 N1 1.6854(16) . ?
S1 C17 1.750(2) . ?
O3 C9 1.211(3) . ?
F1 C16 1.327(3) . ?
F2 C16 1.329(3) . ?
F3 C16 1.324(3) . ?
N1 C1 1.400(2) . ?
N1 C8 1.411(2) . ?
C1 C2 1.362(3) . ?
C1 C9 1.520(3) . ?
C3 C2 1.441(3) . ?
C3 C8 1.405(3) . ?
C3 C4 1.399(3) . ?
C17 C22 1.387(3) . ?
C17 C18 1.388(3) . ?
C8 C7 1.391(3) . ?
C20 C21 1.392(3) . ?
C20 C19 1.393(3) . ?
C20 C23 1.499(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.380(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C10 C9 1.473(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.383(3) . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.386(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 C16 97.09(9) . . ?
O1 S1 O2 121.33(9) . . ?
O1 S1 N1 106.05(8) . . ?
O1 S1 C17 109.17(9) . . ?
O2 S1 N1 104.27(8) . . ?
O2 S1 C17 110.16(9) . . ?
N1 S1 C17 104.37(9) . . ?
C1 N1 S1 126.00(13) . . ?
C1 N1 C8 108.49(15) . . ?
C8 N1 S1 125.32(13) . . ?
N1 C1 C9 124.08(17) . . ?
C2 C1 N1 108.77(16) . . ?
C2 C1 C9 126.85(17) . . ?
C8 C3 C2 106.90(16) . . ?
C4 C3 C2 133.71(18) . . ?
C4 C3 C8 119.39(18) . . ?
C1 C2 Se1 124.49(15) . . ?
C1 C2 C3 108.45(17) . . ?
C3 C2 Se1 126.74(14) . . ?
C22 C17 S1 119.88(16) . . ?
C22 C17 C18 120.95(19) . . ?
C18 C17 S1 119.17(16) . . ?
C3 C8 N1 107.37(16) . . ?
C7 C8 N1 130.54(18) . . ?
C7 C8 C3 122.08(18) . . ?
C21 C20 C19 118.1(2) . . ?
C21 C20 C23 121.1(2) . . ?
C19 C20 C23 120.8(2) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 C8 116.94(19) . . ?
C6 C7 H7 121.5 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.12(19) . . ?
C21 C22 H22 120.4 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.76(19) . . ?
C5 C4 H4 120.6 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.85(19) . . ?
C19 C18 H18 120.6 . . ?
C11 C10 C9 119.2(2) . . ?
C15 C10 C9 121.39(19) . . ?
C15 C10 C11 119.4(2) . . ?
O3 C9 C1 117.84(18) . . ?
O3 C9 C10 123.52(19) . . ?
C10 C9 C1 118.56(17) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.4(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C19 H19 119.2 . . ?
C18 C19 C20 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.88(19) . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.95(19) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F1 C16 Se1 113.36(16) . . ?
F1 C16 F2 107.1(2) . . ?
F2 C16 Se1 108.40(18) . . ?
F3 C16 Se1 114.45(17) . . ?
F3 C16 F1 105.8(2) . . ?
F3 C16 F2 107.4(2) . . ?
C10 C15 H15 119.8 . . ?
C10 C15 C14 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -176.87(14) . . . . ?
S1 N1 C1 C9 -2.9(3) . . . . ?
S1 N1 C8 C3 176.30(13) . . . . ?
S1 N1 C8 C7 -4.0(3) . . . . ?
S1 C17 C22 C21 -178.78(15) . . . . ?
S1 C17 C18 C19 178.95(15) . . . . ?
O1 S1 N1 C1 -146.95(16) . . . . ?
O1 S1 N1 C8 38.73(18) . . . . ?
O1 S1 C17 C22 -18.61(19) . . . . ?
O1 S1 C17 C18 162.52(15) . . . . ?
O2 S1 N1 C1 -17.79(18) . . . . ?
O2 S1 N1 C8 167.89(16) . . . . ?
O2 S1 C17 C22 -154.17(16) . . . . ?
O2 S1 C17 C18 26.96(18) . . . . ?
N1 S1 C17 C22 94.42(17) . . . . ?
N1 S1 C17 C18 -84.45(17) . . . . ?
N1 C1 C2 Se1 175.56(13) . . . . ?
N1 C1 C2 C3 1.7(2) . . . . ?
N1 C1 C9 O3 -82.6(2) . . . . ?
N1 C1 C9 C10 100.4(2) . . . . ?
N1 C8 C7 C6 179.9(2) . . . . ?
C1 N1 C8 C3 1.1(2) . . . . ?
C1 N1 C8 C7 -179.1(2) . . . . ?
C3 C8 C7 C6 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C2 C1 C9 O3 90.3(3) . . . . ?
C2 C1 C9 C10 -86.7(2) . . . . ?
C2 C3 C8 N1 -0.1(2) . . . . ?
C2 C3 C8 C7 -179.91(18) . . . . ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C17 S1 N1 C1 97.82(17) . . . . ?
C17 S1 N1 C8 -76.51(17) . . . . ?
C17 C22 C21 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C8 N1 C1 C2 -1.8(2) . . . . ?
C8 N1 C1 C9 172.26(17) . . . . ?
C8 C3 C2 Se1 -174.67(14) . . . . ?
C8 C3 C2 C1 -0.9(2) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C8 C7 C6 C5 0.3(3) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C4 C3 C2 Se1 5.4(3) . . . . ?
C4 C3 C2 C1 179.1(2) . . . . ?
C4 C3 C8 N1 179.82(17) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C18 C17 C22 C21 0.1(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C10 C15 C14 C13 -0.7(4) . . . . ?
C9 C1 C2 Se1 1.8(3) . . . . ?
C9 C1 C2 C3 -172.15(18) . . . . ?
C9 C10 C11 C12 178.03(19) . . . . ?
C9 C10 C15 C14 -177.4(2) . . . . ?
C21 C20 C19 C18 -1.0(3) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C11 C10 C9 O3 -8.1(3) . . . . ?
C11 C10 C9 C1 168.72(18) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C23 C20 C21 C22 -178.01(19) . . . . ?
C23 C20 C19 C18 178.2(2) . . . . ?
C16 Se1 C2 C1 106.90(18) . . . . ?
C16 Se1 C2 C3 -80.32(18) . . . . ?
C15 C10 C9 O3 169.5(2) . . . . ?
C15 C10 C9 C1 -13.7(3) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2secf33br
_database_code_depnum_ccdc_archive 'CCDC 2125422'
loop_
_audit_author_name
_audit_author_address
'hui wang'
;FuZhou University
China
;
_audit_update_record             
;
2021-12-01 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2021-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        P-1
_chemical_formula_moiety         'C16 H11 Br F3 N O2 S Se'
_chemical_formula_sum            'C16 H11 Br F3 N O2 S Se'
_chemical_formula_weight         497.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5456(9)
_cell_length_b                   9.8957(11)
_cell_length_c                   10.3385(12)
_cell_angle_alpha                93.546(4)
_cell_angle_beta                 93.810(4)
_cell_angle_gamma                103.595(4)
_cell_volume                     845.19(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.035
_cell_measurement_theta_min      2.461
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    4.750
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3433
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.4607.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21073
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.114
_diffrn_reflns_theta_max         25.114
_diffrn_reflns_theta_min         2.124
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2800
_reflns_number_total             3002
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.126
_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     227
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0299
_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)+(0.0371P)²+0.9801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C7(H7), C10(H10), C5(H5), C11(H11), C6(H6)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
Se1 Se 0.35763(4) 0.62537(3) 0.46960(3) 0.02479(11) Uani 1 1 d . . . . .
Br1 Br -0.03997(4) 0.67217(3) 0.40916(3) 0.03142(11) Uani 1 1 d . . . . .
S1 S 0.47614(8) 0.79177(8) 0.79437(7) 0.02185(17) Uani 1 1 d . . . . .
F1 F 0.5921(2) 0.8742(2) 0.47311(18) 0.0377(5) Uani 1 1 d . . . . .
F3 F 0.3979(2) 0.8575(2) 0.32904(18) 0.0360(4) Uani 1 1 d . . . . .
F2 F 0.5708(3) 0.7342(2) 0.3011(2) 0.0468(5) Uani 1 1 d . . . . .
O2 O 0.5437(3) 0.9210(2) 0.8673(2) 0.0299(5) Uani 1 1 d . . . . .
O1 O 0.5743(2) 0.7253(2) 0.7188(2) 0.0306(5) Uani 1 1 d . . . . .
N1 N 0.3302(3) 0.8230(2) 0.6894(2) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.0759(3) 0.8543(3) 0.6471(3) 0.0204(6) Uani 1 1 d . . . . .
C2 C 0.1069(3) 0.7554(3) 0.5510(3) 0.0207(6) Uani 1 1 d . . . . .
C1 C 0.2569(3) 0.7349(3) 0.5767(3) 0.0191(6) Uani 1 1 d . . . . .
C9 C 0.3711(3) 0.6726(3) 0.8961(3) 0.0203(6) Uani 1 1 d . . . . .
C4 C -0.0577(4) 0.9101(3) 0.6663(3) 0.0298(7) Uani 1 1 d . . . . .
H4 H -0.149751 0.885187 0.608454 0.036 Uiso 1 1 calc R . . . .
C16 C 0.4888(4) 0.7855(3) 0.3900(3) 0.0267(7) Uani 1 1 d . . . . .
C8 C 0.2147(3) 0.8940(3) 0.7334(3) 0.0204(6) Uani 1 1 d . . . . .
C13 C 0.2348(4) 0.6249(3) 1.0888(3) 0.0257(6) Uani 1 1 d . . . . .
H13 H 0.199539 0.656359 1.165696 0.031 Uiso 1 1 calc R . . . .
C12 C 0.1990(3) 0.4824(3) 1.0533(3) 0.0251(6) Uani 1 1 d . . . . .
C14 C 0.3219(4) 0.7212(3) 1.0124(3) 0.0245(6) Uani 1 1 d . . . . .
H14 H 0.346875 0.816060 1.038101 0.029 Uiso 1 1 calc R . . . .
C7 C 0.2244(4) 0.9885(3) 0.8413(3) 0.0270(7) Uani 1 1 d . . . . .
H7 H 0.316617 1.015432 0.898850 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3376(4) 0.5315(3) 0.8587(3) 0.0275(7) Uani 1 1 d . . . . .
H10 H 0.371973 0.500069 0.781444 0.033 Uiso 1 1 calc R . . . .
C15 C 0.1078(4) 0.3805(3) 1.1398(3) 0.0321(7) Uani 1 1 d . . . . .
H15A H 0.182374 0.342106 1.190670 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.032942 0.306689 1.087297 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.049684 0.427535 1.196561 0.048 Uiso 1 1 calc GR . . . .
C5 C -0.0491(4) 1.0023(3) 0.7724(4) 0.0359(8) Uani 1 1 d . . . . .
H5 H -0.136751 1.040133 0.787381 0.043 Uiso 1 1 calc R . . . .
C11 C 0.2523(4) 0.4375(3) 0.9376(3) 0.0312(7) Uani 1 1 d . . . . .
H11 H 0.230083 0.342507 0.912787 0.037 Uiso 1 1 calc R . . . .
C6 C 0.0889(4) 1.0397(3) 0.8579(3) 0.0330(8) Uani 1 1 d . . . . .
H6 H 0.090611 1.101997 0.929402 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.887(3) . ?
Se1 C16 1.973(3) . ?
Br1 C2 1.877(3) . ?
S1 O2 1.419(2) . ?
S1 O1 1.425(2) . ?
S1 N1 1.695(2) . ?
S1 C9 1.756(3) . ?
F1 C16 1.315(4) . ?
F3 C16 1.327(4) . ?
F2 C16 1.337(3) . ?
N1 C1 1.426(4) . ?
N1 C8 1.421(4) . ?
C3 C2 1.433(4) . ?
C3 C4 1.400(4) . ?
C3 C8 1.398(4) . ?
C2 C1 1.356(4) . ?
C9 C14 1.394(4) . ?
C9 C10 1.383(4) . ?
C4 C5 1.370(5) . ?
C8 C7 1.396(4) . ?
C13 C12 1.391(4) . ?
C13 C14 1.387(4) . ?
C12 C15 1.503(4) . ?
C12 C11 1.392(4) . ?
C7 C6 1.385(5) . ?
C10 C11 1.384(5) . ?
C5 C6 1.388(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
C1 Se1 C16 94.72(12) . . ?
O2 S1 O1 120.58(14) . . ?
O2 S1 N1 105.31(13) . . ?
O2 S1 C9 109.36(13) . . ?
O1 S1 N1 106.58(12) . . ?
O1 S1 C9 109.27(14) . . ?
N1 S1 C9 104.47(12) . . ?
C1 N1 S1 125.09(19) . . ?
C8 N1 S1 120.93(19) . . ?
C8 N1 C1 107.4(2) . . ?
C4 C3 C2 133.0(3) . . ?
C8 C3 C2 106.5(2) . . ?
C8 C3 C4 120.5(3) . . ?
C3 C2 Br1 123.8(2) . . ?
C1 C2 Br1 126.1(2) . . ?
C1 C2 C3 110.0(2) . . ?
N1 C1 Se1 126.4(2) . . ?
C2 C1 Se1 125.4(2) . . ?
C2 C1 N1 107.9(2) . . ?
C14 C9 S1 119.8(2) . . ?
C10 C9 S1 119.1(2) . . ?
C10 C9 C14 121.0(3) . . ?
C5 C4 C3 118.2(3) . . ?
F1 C16 Se1 114.1(2) . . ?
F1 C16 F3 107.0(3) . . ?
F1 C16 F2 108.8(3) . . ?
F3 C16 Se1 112.0(2) . . ?
F3 C16 F2 107.5(2) . . ?
F2 C16 Se1 107.2(2) . . ?
C3 C8 N1 108.2(2) . . ?
C7 C8 N1 130.2(3) . . ?
C7 C8 C3 121.6(3) . . ?
C14 C13 C12 121.6(3) . . ?
C13 C12 C15 120.3(3) . . ?
C13 C12 C11 118.3(3) . . ?
C11 C12 C15 121.4(3) . . ?
C13 C14 C9 118.5(3) . . ?
C6 C7 C8 116.2(3) . . ?
C9 C10 C11 119.3(3) . . ?
C4 C5 C6 120.7(3) . . ?
C10 C11 C12 121.2(3) . . ?
C7 C6 C5 122.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpsecf3d
_database_code_depnum_ccdc_archive 'CCDC 2179724'
loop_
_audit_author_name
_audit_author_address
ZZP
;Fuzhou University
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 D F3 N O2 S Se'
_chemical_formula_sum            'C16 H11 D F3 N O2 S Se'
_chemical_formula_weight         419.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2225(6)
_cell_length_b                   14.7903(7)
_cell_length_c                   9.8263(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.732(2)
_cell_angle_gamma                90
_cell_volume                     1672.04(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5164
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1145 before and 0.0496 after correction.
The Ratio of minimum to maximum transmission is 0.6930.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.078
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2475
_reflns_number_total             2969
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.020
_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)+(0.0339P)²+0.4948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(D00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C)
;
_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
Se01 Se 0.60513(2) 0.70846(2) 0.68119(3) 0.05526(11) Uani 1 1 d . . . . .
S002 S 0.26995(5) 0.66030(4) 0.13919(6) 0.04881(16) Uani 1 1 d . . . . .
N003 N 0.39551(15) 0.64749(12) 0.2730(2) 0.0436(4) Uani 1 1 d . . . . .
O004 O 0.29045(15) 0.63449(12) 0.01038(17) 0.0620(5) Uani 1 1 d . . . . .
F005 F 0.77687(17) 0.74684(15) 0.5690(2) 0.1008(6) Uani 1 1 d . . . . .
O006 O 0.23156(16) 0.74909(12) 0.1560(2) 0.0687(5) Uani 1 1 d . . . . .
F007 F 0.6673(2) 0.85706(13) 0.5559(2) 0.1087(7) Uani 1 1 d . . . . .
C008 C 0.47938(19) 0.57904(14) 0.2867(2) 0.0415(5) Uani 1 1 d . . . . .
F009 F 0.7877(2) 0.81906(17) 0.7600(2) 0.1226(8) Uani 1 1 d . . . . .
C00A C 0.56427(19) 0.58981(14) 0.4230(2) 0.0413(5) Uani 1 1 d . . . . .
C00B C 0.4289(2) 0.69775(14) 0.4006(2) 0.0443(5) Uani 1 1 d . . . . .
D00B D 0.387526 0.746006 0.419789 0.053 Uiso 1 1 calc R U . . .
C00C C 0.5298(2) 0.66584(14) 0.4914(2) 0.0422(5) Uani 1 1 d . . . . .
C00D C 0.4861(2) 0.51179(16) 0.1920(3) 0.0510(6) Uani 1 1 d . . . . .
H00D H 0.429727 0.505664 0.101114 0.061 Uiso 1 1 calc R U . . .
C00E C 0.17617(19) 0.58126(16) 0.1744(2) 0.0463(5) Uani 1 1 d . . . . .
C00F C 0.6590(2) 0.53118(15) 0.4668(3) 0.0520(6) Uani 1 1 d . . . . .
H00F H 0.716448 0.537572 0.556808 0.062 Uiso 1 1 calc R U . . .
C00G C 0.1673(2) 0.49550(17) 0.1172(3) 0.0549(6) Uani 1 1 d . . . . .
H00G H 0.208273 0.479754 0.056395 0.066 Uiso 1 1 calc R U . . .
C00H C 0.5802(2) 0.45430(16) 0.2384(3) 0.0590(7) Uani 1 1 d . . . . .
H00H H 0.587129 0.408034 0.177734 0.071 Uiso 1 1 calc R U . . .
C00I C 0.6652(2) 0.46377(17) 0.3739(3) 0.0598(7) Uani 1 1 d . . . . .
H00I H 0.727348 0.423617 0.401893 0.072 Uiso 1 1 calc R U . . .
C00J C 0.1140(2) 0.6055(2) 0.2631(3) 0.0649(7) Uani 1 1 d . . . . .
H00J H 0.119878 0.663488 0.301581 0.078 Uiso 1 1 calc R U . . .
C00K C 0.7146(3) 0.78716(19) 0.6378(3) 0.0647(7) Uani 1 1 d . . . . .
C00L C 0.0963(2) 0.43299(19) 0.1516(3) 0.0660(8) Uani 1 1 d . . . . .
H00L H 0.090537 0.374910 0.113523 0.079 Uiso 1 1 calc R U . . .
C00M C 0.0423(2) 0.5411(3) 0.2934(3) 0.0773(9) Uani 1 1 d . . . . .
H00M H -0.001308 0.557005 0.351080 0.093 Uiso 1 1 calc R U . . .
C00N C 0.0345(2) 0.4544(2) 0.2399(3) 0.0727(9) Uani 1 1 d . . . . .
C00O C -0.0401(3) 0.3854(3) 0.2803(4) 0.1159(15) Uani 1 1 d . . . . .
H00A H -0.056247 0.336102 0.212825 0.174 Uiso 1 1 calc R U . . .
H00B H -0.111839 0.413036 0.277834 0.174 Uiso 1 1 calc R U . . .
H00C H 0.000189 0.363128 0.375923 0.174 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
Se01 C00C 1.888(2) . ?
Se01 C00K 1.927(3) . ?
S002 N003 1.6606(19) . ?
S002 O004 1.4229(18) . ?
S002 O006 1.4228(19) . ?
S002 C00E 1.751(2) . ?
N003 C008 1.414(3) . ?
N003 C00B 1.395(3) . ?
F005 C00K 1.319(3) . ?
F007 C00K 1.318(3) . ?
C008 C00A 1.399(3) . ?
C008 C00D 1.384(3) . ?
F009 C00K 1.319(3) . ?
C00A C00C 1.444(3) . ?
C00A C00F 1.393(3) . ?
C00B D00B 0.9300 . ?
C00B C00C 1.340(3) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.379(4) . ?
C00E C00G 1.377(3) . ?
C00E C00J 1.384(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.372(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.385(4) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.391(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.393(4) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.366(4) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.377(4) . ?
C00N C00O 1.509(4) . ?
C00O H00A 0.9600 . ?
C00O H00B 0.9600 . ?
C00O H00C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C Se01 C00K 97.27(10) . . ?
N003 S002 C00E 105.01(10) . . ?
O004 S002 N003 106.30(10) . . ?
O004 S002 C00E 108.66(11) . . ?
O006 S002 N003 105.44(10) . . ?
O006 S002 O004 120.99(12) . . ?
O006 S002 C00E 109.26(12) . . ?
C008 N003 S002 127.11(15) . . ?
C00B N003 S002 124.25(15) . . ?
C00B N003 C008 108.24(18) . . ?
C00A C008 N003 106.81(18) . . ?
C00D C008 N003 131.0(2) . . ?
C00D C008 C00A 122.2(2) . . ?
C008 C00A C00C 107.20(19) . . ?
C00F C00A C008 119.7(2) . . ?
C00F C00A C00C 133.1(2) . . ?
N003 C00B D00B 125.2 . . ?
C00C C00B N003 109.57(19) . . ?
C00C C00B D00B 125.2 . . ?
C00A C00C Se01 126.76(17) . . ?
C00B C00C Se01 124.91(17) . . ?
C00B C00C C00A 108.16(19) . . ?
C008 C00D H00D 121.5 . . ?
C00H C00D C008 117.0(2) . . ?
C00H C00D H00D 121.5 . . ?
C00G C00E S002 120.10(19) . . ?
C00G C00E C00J 120.8(2) . . ?
C00J C00E S002 119.1(2) . . ?
C00A C00F H00F 120.9 . . ?
C00I C00F C00A 118.3(2) . . ?
C00I C00F H00F 120.9 . . ?
C00E C00G H00G 120.5 . . ?
C00E C00G C00L 119.0(3) . . ?
C00L C00G H00G 120.5 . . ?
C00D C00H H00H 119.2 . . ?
C00D C00H C00I 121.6(2) . . ?
C00I C00H H00H 119.2 . . ?
C00F C00I C00H 121.3(2) . . ?
C00F C00I H00I 119.4 . . ?
C00H C00I H00I 119.4 . . ?
C00E C00J H00J 120.8 . . ?
C00E C00J C00M 118.4(3) . . ?
C00M C00J H00J 120.8 . . ?
F005 C00K Se01 113.85(19) . . ?
F005 C00K F009 107.3(3) . . ?
F007 C00K Se01 114.5(2) . . ?
F007 C00K F005 104.6(2) . . ?
F007 C00K F009 107.3(2) . . ?
F009 C00K Se01 108.8(2) . . ?
C00G C00L H00L 119.1 . . ?
C00N C00L C00G 121.7(3) . . ?
C00N C00L H00L 119.1 . . ?
C00J C00M H00M 119.2 . . ?
C00N C00M C00J 121.5(3) . . ?
C00N C00M H00M 119.2 . . ?
C00L C00N C00M 118.5(3) . . ?
C00L C00N C00O 121.5(3) . . ?
C00M C00N C00O 120.0(3) . . ?
C00N C00O H00A 109.5 . . ?
C00N C00O H00B 109.5 . . ?
C00N C00O H00C 109.5 . . ?
H00A C00O H00B 109.5 . . ?
H00A C00O H00C 109.5 . . ?
H00B C00O H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S002 N003 C008 C00A -173.90(15) . . . . ?
S002 N003 C008 C00D 6.6(4) . . . . ?
S002 N003 C00B C00C 174.57(16) . . . . ?
S002 C00E C00G C00L 177.26(19) . . . . ?
S002 C00E C00J C00M -178.2(2) . . . . ?
N003 S002 C00E C00G -90.9(2) . . . . ?
N003 S002 C00E C00J 87.4(2) . . . . ?
N003 C008 C00A C00C 0.2(2) . . . . ?
N003 C008 C00A C00F -179.98(19) . . . . ?
N003 C008 C00D C00H -179.7(2) . . . . ?
N003 C00B C00C Se01 -176.68(15) . . . . ?
N003 C00B C00C C00A -1.2(2) . . . . ?
O004 S002 N003 C008 -36.4(2) . . . . ?
O004 S002 N003 C00B 151.71(18) . . . . ?
O004 S002 C00E C00G 22.5(2) . . . . ?
O004 S002 C00E C00J -159.17(19) . . . . ?
O006 S002 N003 C008 -165.96(18) . . . . ?
O006 S002 N003 C00B 22.1(2) . . . . ?
O006 S002 C00E C00G 156.44(19) . . . . ?
O006 S002 C00E C00J -25.3(2) . . . . ?
C008 N003 C00B C00C 1.4(2) . . . . ?
C008 C00A C00C Se01 175.97(16) . . . . ?
C008 C00A C00C C00B 0.6(2) . . . . ?
C008 C00A C00F C00I -0.4(3) . . . . ?
C008 C00D C00H C00I -0.5(4) . . . . ?
C00A C008 C00D C00H 0.8(3) . . . . ?
C00A C00F C00I C00H 0.7(4) . . . . ?
C00B N003 C008 C00A -0.9(2) . . . . ?
C00B N003 C008 C00D 179.5(2) . . . . ?
C00C C00A C00F C00I 179.4(2) . . . . ?
C00D C008 C00A C00C 179.8(2) . . . . ?
C00D C008 C00A C00F -0.4(3) . . . . ?
C00D C00H C00I C00F -0.3(4) . . . . ?
C00E S002 N003 C008 78.7(2) . . . . ?
C00E S002 N003 C00B -93.23(19) . . . . ?
C00E C00G C00L C00N 0.4(4) . . . . ?
C00E C00J C00M C00N 1.5(4) . . . . ?
C00F C00A C00C Se01 -3.8(4) . . . . ?
C00F C00A C00C C00B -179.2(2) . . . . ?
C00G C00E C00J C00M 0.1(4) . . . . ?
C00G C00L C00N C00M 1.1(4) . . . . ?
C00G C00L C00N C00O -178.3(3) . . . . ?
C00J C00E C00G C00L -1.0(4) . . . . ?
C00J C00M C00N C00L -2.1(4) . . . . ?
C00J C00M C00N C00O 177.4(3) . . . . ?
C00K Se01 C00C C00A 87.0(2) . . . . ?
C00K Se01 C00C C00B -98.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zzp20230304cpcd3_auto
_database_code_depnum_ccdc_archive 'CCDC 2246259'
loop_
_audit_author_name
_audit_author_address
'Zhang Zipeng'
;Fuzhou University
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 D3 F3 N O2 S Se'
_chemical_formula_sum            'C17 H11 D3 F3 N O2 S Se'
_chemical_formula_weight         435.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFSSeD
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'
D D 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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5480(2)
_cell_length_b                   21.1621(5)
_cell_length_c                   8.8566(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.580(2)
_cell_angle_gamma                90
_cell_volume                     1769.50(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0030
_cell_measurement_theta_min      4.1720
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8638
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.157
_diffrn_reflns_theta_min         4.178
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  76.00   0.50    0.50    --   42.30  34.00  15.00   52
  2  ω    -46.00  30.00   0.50    0.50    --   42.30 -34.00-142.00  152
  3  ω     69.00 153.00   0.50    1.13    --   93.70  34.00  15.00  168
  4  ω     11.00  59.00   0.50    1.13    --   93.70 -34.00-142.00   96
  5  ω    -47.00  64.00   0.50    0.50    --   42.30 -77.00 -30.00  222
  6  ω     68.00  94.00   0.50    0.50    --   42.30  65.00-180.00   52
  7  ω    -37.00  71.00   0.50    0.50    --   42.30 -43.00  30.00  216
  8  ω     22.00  61.00   0.50    0.50    --   42.30  65.00-180.00   78
  9  ω     89.00 131.00   0.50    0.50    --   42.30  32.00 150.00   84
 10  ω     19.00  44.00   0.50    0.50    --   42.30  32.00 150.00   50
 11  ω     35.00  61.00   0.50    0.50    --   42.30  77.00  60.00   52
 12  ω     83.00 132.00   0.50    0.50    --   42.30  77.00  60.00   98
 13  ω    141.00 170.00   0.50    1.13    --   93.70  68.00 -60.00   58
 14  ω     98.00 175.00   0.50    1.13    --   93.70  33.00 -30.00  154
 15  ω     43.00 118.00   0.50    1.13    --   93.70 -77.00  30.00  150
 16  ω     69.00 120.00   0.50    1.13    --   93.70  68.00 -60.00  102
 17  ω     88.00 114.00   0.50    1.13    --   93.70 -82.00   0.00   52
 18  ω      6.00 106.00   0.50    1.13    --   93.70 -33.00  30.00  200
 19  ω      4.00 118.00   0.50    1.13    --   93.70 -77.00-120.00  228
 20  ω      5.00 123.00   0.50    1.13    --   93.70 -50.00  30.00  236
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067196000
_diffrn_orient_matrix_UB_12      -0.0142526000
_diffrn_orient_matrix_UB_13      0.1693165000
_diffrn_orient_matrix_UB_21      0.1486099000
_diffrn_orient_matrix_UB_22      0.0288699000
_diffrn_orient_matrix_UB_23      0.0441544000
_diffrn_orient_matrix_UB_31      -0.0670002000
_diffrn_orient_matrix_UB_32      0.0653223000
_diffrn_orient_matrix_UB_33      0.0174469000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2577
_reflns_number_total             3214
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.119
_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)+(0.1209P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00J(D00A,D00B,D00C), C00P(H00A,H00B,H00C)
;
_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
SeE0 Se 0.31043(5) 0.59852(2) 0.71581(6) 0.0751(3) Uani 1 1 d . . . . .
S S 0.72430(13) 0.59194(5) 0.32625(11) 0.0653(3) Uani 1 1 d . . . . .
N N 0.6357(3) 0.57325(15) 0.4701(3) 0.0566(7) Uani 1 1 d . . . . .
O1 O 0.8316(4) 0.54515(15) 0.3303(3) 0.0818(9) Uani 1 1 d . . . . .
F F 0.3949(4) 0.72145(15) 0.6908(4) 0.1220(12) Uani 1 1 d . . . . .
F1 F 0.4727(4) 0.6828(2) 0.9032(4) 0.1272(13) Uani 1 1 d . . . . .
O O 0.6230(4) 0.59915(17) 0.1937(3) 0.0892(11) Uani 1 1 d . . . . .
F2 F 0.2544(4) 0.7076(2) 0.8503(5) 0.1399(15) Uani 1 1 d . . . . .
C009 C 0.6036(4) 0.55365(18) 0.7137(4) 0.0556(8) Uani 1 1 d . . . . .
C00A C 0.4795(4) 0.58326(18) 0.6337(4) 0.0575(8) Uani 1 1 d . . . . .
C00B C 0.4991(4) 0.59605(18) 0.4877(4) 0.0577(9) Uani 1 1 d . . . . .
C00C C 0.7012(4) 0.54783(17) 0.6118(4) 0.0532(8) Uani 1 1 d . . . . .
C00D C 0.8028(4) 0.66492(19) 0.3772(4) 0.0622(9) Uani 1 1 d . . . . .
C00E C 0.6391(4) 0.5319(2) 0.8633(4) 0.0692(11) Uani 1 1 d . . . . .
H00E H 0.576240 0.535963 0.933417 0.083 Uiso 1 1 calc R U . . .
C00F C 0.8330(4) 0.5204(2) 0.6528(4) 0.0647(9) Uani 1 1 d . . . . .
H00F H 0.897236 0.516335 0.584066 0.078 Uiso 1 1 calc R U . . .
C00G C 0.3632(5) 0.6823(3) 0.7967(6) 0.0843(14) Uani 1 1 d . . . . .
C00H C 0.8639(5) 0.4992(2) 0.8032(5) 0.0788(13) Uani 1 1 d . . . . .
H00H H 0.951736 0.480800 0.835745 0.095 Uiso 1 1 calc R U . . .
C00I C 0.7697(5) 0.5045(2) 0.9039(5) 0.0786(13) Uani 1 1 d . . . . .
H00I H 0.794420 0.489080 1.002695 0.094 Uiso 1 1 calc R U . . .
C00J C 0.3995(5) 0.6261(2) 0.3628(5) 0.0789(12) Uani 1 1 d . . . . .
D00A D 0.435002 0.666942 0.340221 0.118 Uiso 1 1 calc R U . . .
D00B D 0.308232 0.630747 0.394596 0.118 Uiso 1 1 calc R U . . .
D00C D 0.391138 0.600037 0.273260 0.118 Uiso 1 1 calc R U . . .
C00K C 0.9229(6) 0.7822(2) 0.4626(8) 0.0972(17) Uani 1 1 d . . . . .
C00L C 0.9290(5) 0.6685(3) 0.4716(6) 0.0876(13) Uani 1 1 d . . . . .
H00L H 0.976228 0.631919 0.508452 0.105 Uiso 1 1 calc R U . . .
C00M C 0.7377(6) 0.7202(3) 0.3189(7) 0.0979(16) Uani 1 1 d . . . . .
H00M H 0.653525 0.718605 0.251013 0.117 Uiso 1 1 calc R U . . .
C00N C 0.9854(7) 0.7270(3) 0.5116(7) 0.1059(19) Uani 1 1 d . . . . .
H00N H 1.071614 0.728729 0.576144 0.127 Uiso 1 1 calc R U . . .
C00O C 0.7990(7) 0.7775(3) 0.3626(10) 0.116(2) Uani 1 1 d . . . . .
H00O H 0.754827 0.814324 0.322895 0.139 Uiso 1 1 calc R U . . .
C00P C 0.9881(8) 0.8453(3) 0.5137(11) 0.141(3) Uani 1 1 d . . . . .
H00A H 1.070400 0.838560 0.588587 0.211 Uiso 1 1 calc R U . . .
H00B H 0.920383 0.870184 0.557568 0.211 Uiso 1 1 calc R U . . .
H00C H 1.014923 0.867136 0.427442 0.211 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
SeE0 C00A 1.895(4) . ?
SeE0 C00G 1.951(5) . ?
S N 1.678(3) . ?
S O1 1.421(3) . ?
S O 1.414(3) . ?
S C00D 1.746(4) . ?
N C00B 1.421(5) . ?
N C00C 1.421(4) . ?
F C00G 1.320(6) . ?
F1 C00G 1.300(6) . ?
F2 C00G 1.319(5) . ?
C009 C00A 1.431(5) . ?
C009 C00C 1.397(5) . ?
C009 C00E 1.395(5) . ?
C00A C00B 1.361(5) . ?
C00B C00J 1.489(6) . ?
C00C C00F 1.385(5) . ?
C00D C00L 1.363(6) . ?
C00D C00M 1.388(6) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.374(6) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.395(6) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.363(7) . ?
C00I H00I 0.9300 . ?
C00J D00A 0.9600 . ?
C00J D00B 0.9600 . ?
C00J D00C 0.9600 . ?
C00K C00N 1.353(8) . ?
C00K C00O 1.372(9) . ?
C00K C00P 1.514(8) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.376(8) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.376(9) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00A 0.9600 . ?
C00P H00B 0.9600 . ?
C00P H00C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A SeE0 C00G 96.18(17) . . ?
N S C00D 104.93(16) . . ?
O1 S N 105.05(17) . . ?
O1 S C00D 109.3(2) . . ?
O S N 107.3(2) . . ?
O S O1 119.8(2) . . ?
O S C00D 109.4(2) . . ?
C00B N S 125.3(3) . . ?
C00B N C00C 108.8(3) . . ?
C00C N S 123.7(2) . . ?
C00C C009 C00A 107.5(3) . . ?
C00E C009 C00A 132.9(3) . . ?
C00E C009 C00C 119.6(3) . . ?
C009 C00A SeE0 125.1(3) . . ?
C00B C00A SeE0 125.2(3) . . ?
C00B C00A C009 109.7(3) . . ?
N C00B C00J 124.0(3) . . ?
C00A C00B N 107.2(3) . . ?
C00A C00B C00J 128.8(4) . . ?
C009 C00C N 106.8(3) . . ?
C00F C00C N 130.8(3) . . ?
C00F C00C C009 122.4(3) . . ?
C00L C00D S 120.9(3) . . ?
C00L C00D C00M 119.2(5) . . ?
C00M C00D S 119.9(4) . . ?
C009 C00E H00E 121.0 . . ?
C00I C00E C009 118.1(4) . . ?
C00I C00E H00E 121.0 . . ?
C00C C00F H00F 121.9 . . ?
C00C C00F C00H 116.1(4) . . ?
C00H C00F H00F 121.9 . . ?
F C00G SeE0 112.5(3) . . ?
F1 C00G SeE0 114.2(4) . . ?
F1 C00G F 105.4(4) . . ?
F1 C00G F2 109.1(4) . . ?
F2 C00G SeE0 109.1(4) . . ?
F2 C00G F 106.1(5) . . ?
C00F C00H H00H 118.9 . . ?
C00I C00H C00F 122.2(4) . . ?
C00I C00H H00H 118.9 . . ?
C00E C00I H00I 119.2 . . ?
C00H C00I C00E 121.6(4) . . ?
C00H C00I H00I 119.2 . . ?
C00B C00J D00A 109.5 . . ?
C00B C00J D00B 109.5 . . ?
C00B C00J D00C 109.5 . . ?
D00A C00J D00B 109.5 . . ?
D00A C00J D00C 109.5 . . ?
D00B C00J D00C 109.5 . . ?
C00N C00K C00O 116.2(5) . . ?
C00N C00K C00P 121.6(7) . . ?
C00O C00K C00P 122.3(6) . . ?
C00D C00L H00L 120.5 . . ?
C00D C00L C00N 119.0(5) . . ?
C00N C00L H00L 120.5 . . ?
C00D C00M H00M 120.3 . . ?
C00O C00M C00D 119.4(6) . . ?
C00O C00M H00M 120.3 . . ?
C00K C00N C00L 123.9(6) . . ?
C00K C00N H00N 118.1 . . ?
C00L C00N H00N 118.1 . . ?
C00K C00O C00M 122.4(5) . . ?
C00K C00O H00O 118.8 . . ?
C00M C00O H00O 118.8 . . ?
C00K C00P H00A 109.5 . . ?
C00K C00P H00B 109.5 . . ?
C00K C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
SeE0 C00A C00B N -175.7(3) . . . . ?
SeE0 C00A C00B C00J 2.5(6) . . . . ?
S N C00B C00A -165.2(3) . . . . ?
S N C00B C00J 16.5(5) . . . . ?
S N C00C C009 165.2(3) . . . . ?
S N C00C C00F -16.1(6) . . . . ?
S C00D C00L C00N -178.5(4) . . . . ?
S C00D C00M C00O 178.6(5) . . . . ?
N S C00D C00L 84.1(4) . . . . ?
N S C00D C00M -97.1(4) . . . . ?
N C00C C00F C00H -179.1(4) . . . . ?
O1 S N C00B -163.0(3) . . . . ?
O1 S N C00C 36.0(3) . . . . ?
O1 S C00D C00L -28.1(4) . . . . ?
O1 S C00D C00M 150.6(4) . . . . ?
O S N C00B -34.5(3) . . . . ?
O S N C00C 164.5(3) . . . . ?
O S C00D C00L -161.1(4) . . . . ?
O S C00D C00M 17.7(4) . . . . ?
C009 C00A C00B N 1.5(4) . . . . ?
C009 C00A C00B C00J 179.6(4) . . . . ?
C009 C00C C00F C00H -0.5(6) . . . . ?
C009 C00E C00I C00H 1.1(7) . . . . ?
C00A C009 C00C N -0.6(4) . . . . ?
C00A C009 C00C C00F -179.4(4) . . . . ?
C00A C009 C00E C00I 179.2(4) . . . . ?
C00B N C00C C009 1.5(4) . . . . ?
C00B N C00C C00F -179.8(4) . . . . ?
C00C N C00B C00A -1.8(4) . . . . ?
C00C N C00B C00J 179.9(4) . . . . ?
C00C C009 C00A SeE0 176.6(3) . . . . ?
C00C C009 C00A C00B -0.6(4) . . . . ?
C00C C009 C00E C00I -1.0(6) . . . . ?
C00C C00F C00H C00I 0.6(7) . . . . ?
C00D S N C00B 81.8(3) . . . . ?
C00D S N C00C -79.2(3) . . . . ?
C00D C00L C00N C00K 0.0(9) . . . . ?
C00D C00M C00O C00K -0.1(10) . . . . ?
C00E C009 C00A SeE0 -3.6(6) . . . . ?
C00E C009 C00A C00B 179.2(4) . . . . ?
C00E C009 C00C N 179.6(3) . . . . ?
C00E C009 C00C C00F 0.8(6) . . . . ?
C00F C00H C00I C00E -0.9(8) . . . . ?
C00G SeE0 C00A C009 90.4(4) . . . . ?
C00G SeE0 C00A C00B -92.9(4) . . . . ?
C00L C00D C00M C00O -2.6(8) . . . . ?
C00M C00D C00L C00N 2.7(8) . . . . ?
C00N C00K C00O C00M 2.7(9) . . . . ?
C00O C00K C00N C00L -2.6(9) . . . . ?
C00P C00K C00N C00L 178.4(6) . . . . ?
C00P C00K C00O C00M -178.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.630
_oxdiff_exptl_absorpt_empirical_full_min 0.436
####################################################################### 
# 
# 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_zzp20220707zn_auto
_database_code_depnum_ccdc_archive 'CCDC 2184810'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H20 Br2 F6 N2 O4 S2 Se2 Zn'
_chemical_formula_sum            'C32 H20 Br2 F6 N2 O4 S2 Se2 Zn'
_chemical_formula_weight         1057.73
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   9.9255(3)
_cell_length_b                   9.9255(3)
_cell_length_c                   37.9613(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3739.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6640
_cell_measurement_theta_min      2.3370
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    7.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            12192
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.451
_diffrn_reflns_theta_min         4.455
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -20.00   0.50    2.14    --   42.40 -19.00 148.00   52
  2  ω     81.00 107.00   0.50    2.14    --   42.40 -19.00 148.00   52
  3  ω     10.00  58.00   0.50    2.14    --   42.40 -19.00 148.00   96
  4  ω     35.00  61.00   0.50    8.55    --   93.70 -19.00 148.00   52
  5  ω      8.00  64.00   0.50    2.14    --   42.40  32.00  30.00  112
  6  ω     98.00 123.00   0.50    2.14    --   42.40  19.00 -43.00   50
  7  ω     48.00  74.00   0.50    2.14    --   42.40  65.00-180.00   52
  8  ω     72.00 119.00   0.50    2.14    --   42.40  32.00  30.00   94
  9  ω     26.00 129.00   0.50    2.14    --   42.40  65.00 150.00  206
 10  ω     70.00 158.00   0.50    8.55    --   93.70  77.00 -60.00  176
 11  ω     64.00  90.00   0.50    8.55    --   93.70 -68.00 -90.00   52
 12  ω     69.00  94.00   0.50    8.55    --   93.70  19.00 -43.00   50
 13  ω     24.00  50.00   0.50    8.55    --   93.70 -68.00 -90.00   52
 14  ω      4.00 119.00   0.50    8.55    --   93.70 -50.00 120.00  230
 15  ω     30.00 122.00   0.50    8.55    --   93.70 -50.00   0.00  184
 16  ω    113.00 139.00   0.50    8.55    --   93.70  19.00 -43.00   52
 17  ω     79.00 104.00   0.50    8.55    --   93.70  68.00 -30.00   50
 18  ω     69.00  94.00   0.50    8.55    --   93.70 -19.00 148.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_full    0.651
_reflns_Friedel_fraction_max     0.643
_reflns_number_gt                4224
_reflns_number_total             5610
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         5610
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+27.2296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.1683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00O(H00O), C00P(H00P), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C010(H010), C012(H012), C016(H016),
 C017(H017), C019(H019)
2.b Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01F(H01D,H01E,H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Se01 Se 0.4266(3) 0.5243(3) 0.55734(7) 0.0778(7) Uani 1 1 d . . . . .
Zn02 Zn 0.5134(3) 0.2194(3) 0.50087(7) 0.0620(7) Uani 1 1 d . . . . .
Se03 Se 0.1926(3) 0.1083(3) 0.44955(8) 0.0925(9) Uani 1 1 d . . . . .
Br2 Br 0.6147(3) 0.2028(3) 0.28688(6) 0.1012(10) Uani 1 1 d . . . . .
Br1 Br 0.5402(4) 0.0681(3) 0.71319(6) 0.0982(10) Uani 1 1 d . . . . .
S006 S 0.7116(5) 0.3126(5) 0.43944(11) 0.0503(11) Uani 1 1 d . . . . .
S007 S 0.6215(5) 0.0004(5) 0.55728(13) 0.0572(12) Uani 1 1 d . . . . .
O008 O 0.8133(13) 0.2616(13) 0.4168(3) 0.060(3) Uani 1 1 d . . . . .
O009 O 0.7178(13) 0.2849(14) 0.4770(3) 0.059(3) Uani 1 1 d . . . . .
N00A N 0.5687(15) 0.2462(16) 0.4270(4) 0.050(4) Uani 1 1 d . . . . .
O00B O 0.5899(16) 0.0082(14) 0.5202(3) 0.070(4) Uani 1 1 d . . . . .
O00C O 0.5723(15) -0.1067(14) 0.5781(4) 0.068(4) Uani 1 1 d . . . . .
N00D N 0.5578(15) 0.1410(15) 0.5729(4) 0.051(4) Uani 1 1 d . . . . .
F00E F 0.1831(18) 0.399(2) 0.5454(5) 0.130(6) Uani 1 1 d . . . . .
C00F C 0.521(2) 0.2534(17) 0.5513(5) 0.049(5) Uani 1 1 d . . . . .
C00G C 0.871(2) 0.070(2) 0.5365(6) 0.073(6) Uani 1 1 d . . . . .
H00G H 0.832002 0.104625 0.516191 0.087 Uiso 1 1 calc R U . . .
C00H C 0.477(2) 0.297(2) 0.6720(6) 0.062(6) Uani 1 1 d . . . . .
H00H H 0.455614 0.335496 0.693571 0.075 Uiso 1 1 calc R U . . .
C00I C 0.793(2) 0.0103(19) 0.5620(6) 0.062(6) Uani 1 1 d . . . . .
F00J F 0.1988(17) 0.475(2) 0.5963(5) 0.141(8) Uani 1 1 d . . . . .
C00K C 0.4622(19) 0.2097(18) 0.4513(5) 0.052(5) Uani 1 1 d . . . . .
C00L C 0.697(2) 0.4875(19) 0.4336(5) 0.051(5) Uani 1 1 d . . . . .
C00M C 0.5400(19) 0.181(2) 0.6090(5) 0.052(5) Uani 1 1 d . . . . .
C00N C 0.524(2) 0.2229(19) 0.3921(5) 0.052(5) Uani 1 1 d . . . . .
C00O C 0.733(2) 0.685(2) 0.4004(6) 0.067(6) Uani 1 1 d . . . . .
H00O H 0.764874 0.725906 0.379977 0.081 Uiso 1 1 calc R U . . .
C00P C 0.592(2) 0.236(2) 0.3605(5) 0.059(5) Uani 1 1 d . . . . .
H00P H 0.678268 0.272311 0.359445 0.071 Uiso 1 1 calc R U . . .
C00Q C 0.526(2) 0.194(2) 0.3309(5) 0.063(6) Uani 1 1 d . . . . .
C00R C 0.855(2) -0.040(2) 0.5928(6) 0.072(6) Uani 1 1 d . . . . .
H00R H 0.803255 -0.080123 0.610377 0.086 Uiso 1 1 calc R U . . .
C00S C 0.4922(19) 0.3097(17) 0.6098(5) 0.050(5) Uani 1 1 d . . . . .
C00T C 0.623(2) 0.699(2) 0.4555(6) 0.066(6) Uani 1 1 d . . . . .
H00T H 0.580854 0.748439 0.473062 0.079 Uiso 1 1 calc R U . . .
C00U C 0.401(3) 0.145(2) 0.3317(6) 0.075(6) Uani 1 1 d . . . . .
H00U H 0.360258 0.118211 0.310676 0.090 Uiso 1 1 calc R U . . .
C00V C 0.747(2) 0.549(2) 0.4037(6) 0.065(6) Uani 1 1 d . . . . .
H00V H 0.790229 0.498486 0.386343 0.078 Uiso 1 1 calc R U . . .
C00W C 0.634(2) 0.564(2) 0.4594(5) 0.057(5) Uani 1 1 d . . . . .
H00W H 0.599296 0.522083 0.479370 0.068 Uiso 1 1 calc R U . . .
C00X C 0.525(2) 0.168(2) 0.6705(5) 0.059(5) Uani 1 1 d . . . . .
C00Y C 0.395(2) 0.1683(19) 0.3947(6) 0.061(5) Uani 1 1 d . . . . .
F00Z F 0.168(2) 0.606(2) 0.5530(7) 0.178(10) Uani 1 1 d . . . . .
C010 C 0.561(2) 0.102(2) 0.6396(5) 0.056(5) Uani 1 1 d . . . . .
H010 H 0.594986 0.014859 0.638965 0.068 Uiso 1 1 calc R U . . .
C011 C 0.4819(19) 0.354(2) 0.5728(5) 0.055(5) Uani 1 1 d . . . . .
C012 C 0.329(2) 0.132(2) 0.3632(6) 0.070(6) Uani 1 1 d . . . . .
H012 H 0.240228 0.101261 0.363425 0.084 Uiso 1 1 calc R U . . .
C013 C 0.236(4) 0.501(3) 0.5637(8) 0.109(10) Uani 1 1 d . . . . .
C014 C 0.673(2) 0.765(2) 0.4259(6) 0.073(6) Uani 1 1 d . . . . .
C015 C 0.359(2) 0.164(2) 0.4309(6) 0.057(5) Uani 1 1 d . . . . .
C016 C 0.460(2) 0.367(2) 0.6417(6) 0.066(6) Uani 1 1 d . . . . .
H016 H 0.426917 0.454998 0.642486 0.079 Uiso 1 1 calc R U . . .
C017 C 1.008(3) 0.078(3) 0.5413(7) 0.098(9) Uani 1 1 d . . . . .
H017 H 1.059103 0.121137 0.524164 0.118 Uiso 1 1 calc R U . . .
C018 C 1.072(2) 0.026(3) 0.5705(8) 0.090(8) Uani 1 1 d . . . . .
C019 C 0.990(3) -0.029(3) 0.5964(7) 0.092(8) Uani 1 1 d . . . . .
H019 H 1.029247 -0.060578 0.617084 0.111 Uiso 1 1 calc R U . . .
C01A C 0.664(3) 0.914(2) 0.4221(8) 0.110(10) Uani 1 1 d . . . . .
H01A H 0.736698 0.956113 0.434427 0.165 Uiso 1 1 calc R U . . .
H01B H 0.579517 0.944597 0.431711 0.165 Uiso 1 1 calc R U . . .
H01C H 0.668014 0.937690 0.397553 0.165 Uiso 1 1 calc R U . . .
F01B F 0.260(4) -0.133(2) 0.4203(9) 0.235(17) Uani 1 1 d . . . . .
F01C F 0.114(3) -0.145(2) 0.4598(10) 0.255(18) Uani 1 1 d . . . . .
F01D F 0.318(3) -0.123(3) 0.4704(10) 0.227(15) Uani 1 1 d . . . . .
C01E C 0.220(4) -0.084(4) 0.4502(14) 0.136(14) Uani 1 1 d . . . . .
C01F C 1.221(3) 0.037(4) 0.5763(11) 0.152(16) Uani 1 1 d . . . . .
H01D H 1.266757 0.029410 0.554160 0.228 Uiso 1 1 calc R U . . .
H01E H 1.249817 -0.033438 0.591787 0.228 Uiso 1 1 calc R U . . .
H01F H 1.241185 0.123080 0.586731 0.228 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
Se01 C011 1.87(2) . ?
Se01 C013 1.92(4) . ?
Zn02 O009 2.314(13) . ?
Zn02 O00B 2.347(14) . ?
Zn02 C00F 1.944(18) . ?
Zn02 C00K 1.95(2) . ?
Se03 C015 1.88(2) . ?
Se03 C01E 1.92(4) . ?
Br2 C00Q 1.89(2) . ?
Br1 C00X 1.90(2) . ?
S006 O008 1.420(13) . ?
S006 O009 1.455(12) . ?
S006 N00A 1.634(16) . ?
S006 C00L 1.756(19) . ?
S007 O00B 1.445(13) . ?
S007 O00C 1.412(14) . ?
S007 N00D 1.642(15) . ?
S007 C00I 1.72(2) . ?
N00A C00K 1.45(2) . ?
N00A C00N 1.41(2) . ?
N00D C00F 1.43(2) . ?
N00D C00M 1.44(2) . ?
F00E C013 1.33(3) . ?
C00F C011 1.35(3) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.38(3) . ?
C00G C017 1.37(3) . ?
C00H H00H 0.9300 . ?
C00H C00X 1.36(3) . ?
C00H C016 1.36(3) . ?
C00I C00R 1.41(3) . ?
F00J C013 1.32(3) . ?
C00K C015 1.36(3) . ?
C00L C00V 1.38(3) . ?
C00L C00W 1.38(3) . ?
C00M C00S 1.36(3) . ?
C00M C010 1.42(3) . ?
C00N C00P 1.38(3) . ?
C00N C00Y 1.40(3) . ?
C00O H00O 0.9300 . ?
C00O C00V 1.37(3) . ?
C00O C014 1.39(3) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.36(3) . ?
C00Q C00U 1.34(3) . ?
C00R H00R 0.9300 . ?
C00R C019 1.35(3) . ?
C00S C011 1.47(3) . ?
C00S C016 1.38(3) . ?
C00T H00T 0.9300 . ?
C00T C00W 1.35(3) . ?
C00T C014 1.40(3) . ?
C00U H00U 0.9300 . ?
C00U C012 1.40(3) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X C010 1.39(3) . ?
C00Y C012 1.41(3) . ?
C00Y C015 1.42(3) . ?
F00Z C013 1.31(3) . ?
C010 H010 0.9300 . ?
C012 H012 0.9300 . ?
C014 C01A 1.49(3) . ?
C016 H016 0.9300 . ?
C017 H017 0.9300 . ?
C017 C018 1.38(4) . ?
C018 C019 1.39(3) . ?
C018 C01F 1.50(4) . ?
C019 H019 0.9300 . ?
C01A H01A 0.9600 . ?
C01A H01B 0.9600 . ?
C01A H01C 0.9600 . ?
F01B C01E 1.30(5) . ?
F01C C01E 1.27(4) . ?
F01D C01E 1.29(5) . ?
C01F H01D 0.9600 . ?
C01F H01E 0.9600 . ?
C01F H01F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C011 Se01 C013 98.1(12) . . ?
O009 Zn02 O00B 95.1(5) . . ?
C00F Zn02 O009 107.7(6) . . ?
C00F Zn02 O00B 80.5(6) . . ?
C00F Zn02 C00K 165.2(8) . . ?
C00K Zn02 O009 82.3(6) . . ?
C00K Zn02 O00B 110.0(6) . . ?
C015 Se03 C01E 99.9(14) . . ?
O008 S006 O009 119.8(8) . . ?
O008 S006 N00A 107.3(8) . . ?
O008 S006 C00L 109.6(9) . . ?
O009 S006 N00A 104.2(8) . . ?
O009 S006 C00L 108.3(9) . . ?
N00A S006 C00L 106.9(9) . . ?
O00B S007 N00D 102.9(8) . . ?
O00B S007 C00I 108.4(10) . . ?
O00C S007 O00B 120.6(9) . . ?
O00C S007 N00D 107.8(8) . . ?
O00C S007 C00I 109.2(10) . . ?
N00D S007 C00I 107.2(9) . . ?
S006 O009 Zn02 113.5(7) . . ?
C00K N00A S006 123.2(13) . . ?
C00N N00A S006 127.5(13) . . ?
C00N N00A C00K 109.2(15) . . ?
S007 O00B Zn02 115.0(8) . . ?
C00F N00D S007 123.6(12) . . ?
C00F N00D C00M 107.4(14) . . ?
C00M N00D S007 128.8(13) . . ?
N00D C00F Zn02 116.0(12) . . ?
C011 C00F Zn02 135.7(15) . . ?
C011 C00F N00D 107.6(16) . . ?
C00I C00G H00G 120.3 . . ?
C017 C00G H00G 120.3 . . ?
C017 C00G C00I 119(2) . . ?
C00X C00H H00H 120.2 . . ?
C016 C00H H00H 120.2 . . ?
C016 C00H C00X 120(2) . . ?
C00G C00I S007 120.7(19) . . ?
C00G C00I C00R 119(2) . . ?
C00R C00I S007 119.8(17) . . ?
N00A C00K Zn02 114.4(13) . . ?
C015 C00K Zn02 139.6(16) . . ?
C015 C00K N00A 105.5(17) . . ?
C00V C00L S006 120.5(16) . . ?
C00V C00L C00W 120.2(19) . . ?
C00W C00L S006 119.3(15) . . ?
C00S C00M N00D 108.8(16) . . ?
C00S C00M C010 123.7(18) . . ?
C010 C00M N00D 127.5(18) . . ?
C00P C00N N00A 130.3(19) . . ?
C00P C00N C00Y 122.9(19) . . ?
C00Y C00N N00A 106.6(17) . . ?
C00V C00O H00O 118.4 . . ?
C00V C00O C014 123(2) . . ?
C014 C00O H00O 118.4 . . ?
C00N C00P H00P 121.5 . . ?
C00Q C00P C00N 117(2) . . ?
C00Q C00P H00P 121.5 . . ?
C00P C00Q Br2 119.4(17) . . ?
C00U C00Q Br2 117.8(18) . . ?
C00U C00Q C00P 123(2) . . ?
C00I C00R H00R 120.4 . . ?
C019 C00R C00I 119(2) . . ?
C019 C00R H00R 120.4 . . ?
C00M C00S C011 106.5(16) . . ?
C00M C00S C016 119.2(19) . . ?
C016 C00S C011 134.2(18) . . ?
C00W C00T H00T 119.1 . . ?
C00W C00T C014 122(2) . . ?
C014 C00T H00T 119.1 . . ?
C00Q C00U H00U 119.2 . . ?
C00Q C00U C012 122(2) . . ?
C012 C00U H00U 119.2 . . ?
C00L C00V H00V 120.9 . . ?
C00O C00V C00L 118(2) . . ?
C00O C00V H00V 120.9 . . ?
C00L C00W H00W 120.0 . . ?
C00T C00W C00L 120.0(19) . . ?
C00T C00W H00W 120.0 . . ?
C00H C00X Br1 118.7(16) . . ?
C00H C00X C010 124(2) . . ?
C010 C00X Br1 117.0(16) . . ?
C00N C00Y C012 118(2) . . ?
C00N C00Y C015 107.8(18) . . ?
C012 C00Y C015 134(2) . . ?
C00M C010 H010 123.4 . . ?
C00X C010 C00M 113.2(18) . . ?
C00X C010 H010 123.4 . . ?
C00F C011 Se01 124.3(15) . . ?
C00F C011 C00S 109.7(17) . . ?
C00S C011 Se01 126.0(14) . . ?
C00U C012 C00Y 118(2) . . ?
C00U C012 H012 121.2 . . ?
C00Y C012 H012 121.2 . . ?
F00E C013 Se01 115(2) . . ?
F00J C013 Se01 115(2) . . ?
F00J C013 F00E 103(3) . . ?
F00Z C013 Se01 112(3) . . ?
F00Z C013 F00E 104(3) . . ?
F00Z C013 F00J 108(3) . . ?
C00O C014 C00T 116(2) . . ?
C00O C014 C01A 122(2) . . ?
C00T C014 C01A 122(2) . . ?
C00K C015 Se03 123.0(17) . . ?
C00K C015 C00Y 110.8(19) . . ?
C00Y C015 Se03 126.1(16) . . ?
C00H C016 C00S 120(2) . . ?
C00H C016 H016 120.0 . . ?
C00S C016 H016 120.0 . . ?
C00G C017 H017 118.6 . . ?
C00G C017 C018 123(2) . . ?
C018 C017 H017 118.6 . . ?
C017 C018 C019 117(2) . . ?
C017 C018 C01F 123(3) . . ?
C019 C018 C01F 120(3) . . ?
C00R C019 C018 123(3) . . ?
C00R C019 H019 118.7 . . ?
C018 C019 H019 118.7 . . ?
C014 C01A H01A 109.5 . . ?
C014 C01A H01B 109.5 . . ?
C014 C01A H01C 109.5 . . ?
H01A C01A H01B 109.5 . . ?
H01A C01A H01C 109.5 . . ?
H01B C01A H01C 109.5 . . ?
F01B C01E Se03 114(3) . . ?
F01C C01E Se03 111(3) . . ?
F01C C01E F01B 109(4) . . ?
F01C C01E F01D 108(5) . . ?
F01D C01E Se03 114(3) . . ?
F01D C01E F01B 100(4) . . ?
C018 C01F H01D 109.5 . . ?
C018 C01F H01E 109.5 . . ?
C018 C01F H01F 109.5 . . ?
H01D C01F H01E 109.5 . . ?
H01D C01F H01F 109.5 . . ?
H01E C01F H01F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn02 C00F C011 Se01 -12(3) . . . . ?
Zn02 C00F C011 C00S 169.4(16) . . . . ?
Zn02 C00K C015 Se03 11(3) . . . . ?
Zn02 C00K C015 C00Y -170.0(17) . . . . ?
Br2 C00Q C00U C012 178.7(18) . . . . ?
Br1 C00X C010 C00M 177.0(14) . . . . ?
S006 N00A C00K Zn02 -9(2) . . . . ?
S006 N00A C00K C015 177.3(13) . . . . ?
S006 N00A C00N C00P 7(3) . . . . ?
S006 N00A C00N C00Y -178.3(14) . . . . ?
S006 C00L C00V C00O 179.8(17) . . . . ?
S006 C00L C00W C00T 179.3(16) . . . . ?
S007 N00D C00F Zn02 13(2) . . . . ?
S007 N00D C00F C011 -175.5(14) . . . . ?
S007 N00D C00M C00S 175.8(14) . . . . ?
S007 N00D C00M C010 -7(3) . . . . ?
S007 C00I C00R C019 -178.8(19) . . . . ?
O008 S006 O009 Zn02 -134.9(8) . . . . ?
O008 S006 N00A C00K 144.8(15) . . . . ?
O008 S006 N00A C00N -39.5(18) . . . . ?
O008 S006 C00L C00V 18(2) . . . . ?
O008 S006 C00L C00W -161.5(15) . . . . ?
O009 S006 N00A C00K 16.8(17) . . . . ?
O009 S006 N00A C00N -167.5(15) . . . . ?
O009 S006 C00L C00V 150.8(17) . . . . ?
O009 S006 C00L C00W -29.1(19) . . . . ?
N00A S006 O009 Zn02 -15.0(10) . . . . ?
N00A S006 C00L C00V -97.5(18) . . . . ?
N00A S006 C00L C00W 82.6(17) . . . . ?
N00A C00K C015 Se03 -178.1(13) . . . . ?
N00A C00K C015 C00Y 1(2) . . . . ?
N00A C00N C00P C00Q 174(2) . . . . ?
N00A C00N C00Y C012 -178.4(18) . . . . ?
N00A C00N C00Y C015 2(2) . . . . ?
O00B S007 N00D C00F -16.4(17) . . . . ?
O00B S007 N00D C00M 169.8(16) . . . . ?
O00B S007 C00I C00G 24(2) . . . . ?
O00B S007 C00I C00R -158.1(17) . . . . ?
O00C S007 O00B Zn02 131.9(9) . . . . ?
O00C S007 N00D C00F -144.8(15) . . . . ?
O00C S007 N00D C00M 41.3(18) . . . . ?
O00C S007 C00I C00G 156.8(17) . . . . ?
O00C S007 C00I C00R -25(2) . . . . ?
N00D S007 O00B Zn02 11.9(11) . . . . ?
N00D S007 C00I C00G -86.7(19) . . . . ?
N00D S007 C00I C00R 91.6(18) . . . . ?
N00D C00F C011 Se01 178.8(13) . . . . ?
N00D C00F C011 C00S 0(2) . . . . ?
N00D C00M C00S C011 -1(2) . . . . ?
N00D C00M C00S C016 176.4(17) . . . . ?
N00D C00M C010 C00X -175.5(19) . . . . ?
C00F N00D C00M C00S 1(2) . . . . ?
C00F N00D C00M C010 178.2(19) . . . . ?
C00G C00I C00R C019 -1(3) . . . . ?
C00G C017 C018 C019 -4(4) . . . . ?
C00G C017 C018 C01F -179(3) . . . . ?
C00H C00X C010 C00M -1(3) . . . . ?
C00I S007 O00B Zn02 -101.4(10) . . . . ?
C00I S007 N00D C00F 97.8(16) . . . . ?
C00I S007 N00D C00M -76.1(17) . . . . ?
C00I C00G C017 C018 2(4) . . . . ?
C00I C00R C019 C018 -2(4) . . . . ?
C00K N00A C00N C00P -177(2) . . . . ?
C00K N00A C00N C00Y -2(2) . . . . ?
C00L S006 O009 Zn02 98.5(9) . . . . ?
C00L S006 N00A C00K -97.7(16) . . . . ?
C00L S006 N00A C00N 78.0(17) . . . . ?
C00M N00D C00F Zn02 -172.5(12) . . . . ?
C00M N00D C00F C011 -1(2) . . . . ?
C00M C00S C011 Se01 -178.1(15) . . . . ?
C00M C00S C011 C00F 1(2) . . . . ?
C00M C00S C016 C00H 0(3) . . . . ?
C00N N00A C00K Zn02 174.3(12) . . . . ?
C00N N00A C00K C015 1(2) . . . . ?
C00N C00P C00Q Br2 -177.6(15) . . . . ?
C00N C00P C00Q C00U 2(3) . . . . ?
C00N C00Y C012 C00U 4(3) . . . . ?
C00N C00Y C015 Se03 176.7(14) . . . . ?
C00N C00Y C015 C00K -2(2) . . . . ?
C00P C00N C00Y C012 -3(3) . . . . ?
C00P C00N C00Y C015 177.4(19) . . . . ?
C00P C00Q C00U C012 0(4) . . . . ?
C00Q C00U C012 C00Y -3(3) . . . . ?
C00S C00M C010 C00X 1(3) . . . . ?
C00V C00L C00W C00T -1(3) . . . . ?
C00V C00O C014 C00T -2(4) . . . . ?
C00V C00O C014 C01A 178(2) . . . . ?
C00W C00L C00V C00O 0(3) . . . . ?
C00W C00T C014 C00O 1(3) . . . . ?
C00W C00T C014 C01A -179(2) . . . . ?
C00X C00H C016 C00S 0(3) . . . . ?
C00Y C00N C00P C00Q 0(3) . . . . ?
C010 C00M C00S C011 -178.4(18) . . . . ?
C010 C00M C00S C016 -1(3) . . . . ?
C011 C00S C016 C00H 177(2) . . . . ?
C012 C00Y C015 Se03 -2(4) . . . . ?
C012 C00Y C015 C00K 179(2) . . . . ?
C013 Se01 C011 C00F 103(2) . . . . ?
C013 Se01 C011 C00S -77.8(19) . . . . ?
C014 C00O C00V C00L 2(4) . . . . ?
C014 C00T C00W C00L 0(3) . . . . ?
C015 C00Y C012 C00U -177(2) . . . . ?
C016 C00H C00X Br1 -177.3(17) . . . . ?
C016 C00H C00X C010 1(3) . . . . ?
C016 C00S C011 Se01 5(3) . . . . ?
C016 C00S C011 C00F -176(2) . . . . ?
C017 C00G C00I S007 178.9(19) . . . . ?
C017 C00G C00I C00R 1(3) . . . . ?
C017 C018 C019 C00R 4(4) . . . . ?
C01E Se03 C015 C00K -98(2) . . . . ?
C01E Se03 C015 C00Y 83(2) . . . . ?
C01F C018 C019 C00R 179(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
;
####################################################################### 
# 
# 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_cp2h3secf3
_database_code_depnum_ccdc_archive 'CCDC 2160370'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F3 N O2 S Se'
_chemical_formula_sum            'C16 H12 F3 N O2 S Se'
_chemical_formula_weight         418.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2370(14)
_cell_length_b                   14.7897(15)
_cell_length_c                   9.8404(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.903(4)
_cell_angle_gamma                90
_cell_volume                     1674.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.029
_cell_measurement_theta_min      2.243
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    2.406
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.7789.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29147
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.043
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1860
_reflns_number_total             2948
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.015
_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)+(0.0592P)²+0.2750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1176
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00C,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Se01 Se 0.60479(4) 0.70833(3) 0.68039(5) 0.0607(2) Uani 1 1 d . . . . .
S002 S 0.26967(10) 0.66034(7) 0.13861(14) 0.0546(3) Uani 1 1 d . . . . .
O003 O 0.2897(3) 0.6340(2) 0.0098(3) 0.0660(9) Uani 1 1 d . . . . .
N004 N 0.3952(3) 0.6475(2) 0.2722(4) 0.0471(9) Uani 1 1 d . . . . .
O005 O 0.2310(3) 0.7489(2) 0.1548(4) 0.0732(10) Uani 1 1 d . . . . .
F006 F 0.6669(3) 0.8566(2) 0.5561(4) 0.1128(12) Uani 1 1 d . . . . .
F007 F 0.7765(3) 0.7468(2) 0.5698(4) 0.1063(11) Uani 1 1 d . . . . .
F008 F 0.7867(4) 0.8196(3) 0.7590(4) 0.1281(14) Uani 1 1 d . . . . .
C009 C 0.4795(4) 0.5791(2) 0.2877(5) 0.0448(11) Uani 1 1 d . . . . .
C00A C 0.5639(4) 0.5898(2) 0.4234(5) 0.0441(10) Uani 1 1 d . . . . .
C00B C 0.4289(4) 0.6983(3) 0.4006(5) 0.0491(11) Uani 1 1 d . . . . .
H00B H 0.387990 0.746798 0.419670 0.059 Uiso 1 1 calc R U . . .
C00C C 0.5289(4) 0.6657(3) 0.4905(5) 0.0465(11) Uani 1 1 d . . . . .
C00D C 0.4857(4) 0.5121(3) 0.1916(5) 0.0541(12) Uani 1 1 d . . . . .
H00D H 0.429300 0.506375 0.100578 0.065 Uiso 1 1 calc R U . . .
C00E C 0.1760(4) 0.5819(3) 0.1741(5) 0.0495(11) Uani 1 1 d . . . . .
C00F C 0.6585(4) 0.5313(3) 0.4670(5) 0.0554(12) Uani 1 1 d . . . . .
H00F H 0.716377 0.537425 0.556832 0.066 Uiso 1 1 calc R U . . .
C00G C 0.1670(4) 0.4957(3) 0.1183(5) 0.0594(12) Uani 1 1 d . . . . .
H00G H 0.208037 0.479397 0.058013 0.071 Uiso 1 1 calc R U . . .
C00H C 0.6637(4) 0.4638(3) 0.3723(6) 0.0632(14) Uani 1 1 d . . . . .
H00H H 0.725660 0.423388 0.400169 0.076 Uiso 1 1 calc R U . . .
C00I C 0.1153(4) 0.6059(3) 0.2636(6) 0.0714(14) Uani 1 1 d . . . . .
H00I H 0.122491 0.663480 0.303575 0.086 Uiso 1 1 calc R U . . .
C00J C 0.5800(4) 0.4546(3) 0.2383(6) 0.0635(13) Uani 1 1 d . . . . .
H00J H 0.587092 0.408461 0.177547 0.076 Uiso 1 1 calc R U . . .
C00K C 0.7137(5) 0.7871(3) 0.6375(6) 0.0680(14) Uani 1 1 d . . . . .
C00L C 0.0355(4) 0.4551(4) 0.2406(7) 0.0810(17) Uani 1 1 d . . . . .
C00M C 0.0963(4) 0.4342(3) 0.1529(6) 0.0735(16) Uani 1 1 d . . . . .
H00M H 0.090203 0.376100 0.114794 0.088 Uiso 1 1 calc R U . . .
C00N C 0.0429(4) 0.5417(5) 0.2927(6) 0.0841(17) Uani 1 1 d . . . . .
H00N H -0.001563 0.558057 0.348976 0.101 Uiso 1 1 calc R U . . .
C00O C -0.0406(5) 0.3867(5) 0.2814(8) 0.123(3) Uani 1 1 d . . . . .
H00A H -0.055100 0.336191 0.216472 0.185 Uiso 1 1 calc R U . . .
H00C H -0.113094 0.414541 0.275075 0.185 Uiso 1 1 calc R U . . .
H00E H -0.001789 0.366243 0.378518 0.185 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
Se01 C00C 1.889(4) . ?
Se01 C00K 1.922(5) . ?
S002 O003 1.424(3) . ?
S002 N004 1.658(4) . ?
S002 O005 1.420(3) . ?
S002 C00E 1.748(4) . ?
N004 C009 1.415(5) . ?
N004 C00B 1.406(5) . ?
F006 C00K 1.310(6) . ?
F007 C00K 1.318(5) . ?
F008 C00K 1.315(6) . ?
C009 C00A 1.392(6) . ?
C009 C00D 1.389(6) . ?
C00A C00C 1.439(5) . ?
C00A C00F 1.392(6) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.333(6) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.381(6) . ?
C00E C00G 1.377(6) . ?
C00E C00I 1.378(6) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.382(6) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.376(6) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.374(7) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.393(7) . ?
C00J H00J 0.9300 . ?
C00L C00M 1.354(7) . ?
C00L C00N 1.371(8) . ?
C00L C00O 1.519(7) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00A 0.9600 . ?
C00O H00C 0.9600 . ?
C00O H00E 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C Se01 C00K 97.4(2) . . ?
O003 S002 N004 106.30(18) . . ?
O003 S002 C00E 108.6(2) . . ?
N004 S002 C00E 105.01(19) . . ?
O005 S002 O003 121.1(2) . . ?
O005 S002 N004 105.75(19) . . ?
O005 S002 C00E 108.9(2) . . ?
C009 N004 S002 127.7(3) . . ?
C00B N004 S002 124.1(3) . . ?
C00B N004 C009 107.7(4) . . ?
C00A C009 N004 107.3(3) . . ?
C00D C009 N004 130.0(4) . . ?
C00D C009 C00A 122.7(4) . . ?
C009 C00A C00C 106.9(4) . . ?
C009 C00A C00F 119.5(4) . . ?
C00F C00A C00C 133.6(4) . . ?
N004 C00B H00B 125.5 . . ?
C00C C00B N004 109.0(3) . . ?
C00C C00B H00B 125.5 . . ?
C00A C00C Se01 126.2(3) . . ?
C00B C00C Se01 124.6(3) . . ?
C00B C00C C00A 109.1(4) . . ?
C009 C00D H00D 121.7 . . ?
C00J C00D C009 116.5(5) . . ?
C00J C00D H00D 121.7 . . ?
C00G C00E S002 120.2(3) . . ?
C00G C00E C00I 120.4(4) . . ?
C00I C00E S002 119.3(4) . . ?
C00A C00F H00F 121.1 . . ?
C00H C00F C00A 117.8(4) . . ?
C00H C00F H00F 121.1 . . ?
C00E C00G H00G 120.5 . . ?
C00M C00G C00E 119.0(5) . . ?
C00M C00G H00G 120.5 . . ?
C00F C00H H00H 119.0 . . ?
C00J C00H C00F 121.9(4) . . ?
C00J C00H H00H 119.0 . . ?
C00E C00I H00I 120.8 . . ?
C00E C00I C00N 118.4(5) . . ?
C00N C00I H00I 120.8 . . ?
C00D C00J H00J 119.2 . . ?
C00H C00J C00D 121.6(4) . . ?
C00H C00J H00J 119.2 . . ?
F006 C00K Se01 114.8(4) . . ?
F006 C00K F007 104.7(4) . . ?
F006 C00K F008 106.8(4) . . ?
F007 C00K Se01 113.8(3) . . ?
F008 C00K Se01 109.2(4) . . ?
F008 C00K F007 107.0(5) . . ?
C00M C00L C00N 118.2(5) . . ?
C00M C00L C00O 122.4(7) . . ?
C00N C00L C00O 119.4(6) . . ?
C00G C00M H00M 118.8 . . ?
C00L C00M C00G 122.3(5) . . ?
C00L C00M H00M 118.8 . . ?
C00I C00N H00N 119.2 . . ?
C00L C00N C00I 121.6(5) . . ?
C00L C00N H00N 119.2 . . ?
C00L C00O H00A 109.5 . . ?
C00L C00O H00C 109.5 . . ?
C00L C00O H00E 109.5 . . ?
H00A C00O H00C 109.5 . . ?
H00A C00O H00E 109.5 . . ?
H00C C00O H00E 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S002 N004 C009 C00A -173.6(3) . . . . ?
S002 N004 C009 C00D 7.5(6) . . . . ?
S002 N004 C00B C00C 174.2(3) . . . . ?
S002 C00E C00G C00M 177.3(4) . . . . ?
S002 C00E C00I C00N -178.7(4) . . . . ?
O003 S002 N004 C009 -36.4(4) . . . . ?
O003 S002 N004 C00B 152.0(3) . . . . ?
O003 S002 C00E C00G 22.9(4) . . . . ?
O003 S002 C00E C00I -159.9(4) . . . . ?
N004 S002 C00E C00G -90.4(4) . . . . ?
N004 S002 C00E C00I 86.7(4) . . . . ?
N004 C009 C00A C00C 0.4(4) . . . . ?
N004 C009 C00A C00F -179.6(3) . . . . ?
N004 C009 C00D C00J 179.9(4) . . . . ?
N004 C00B C00C Se01 -176.8(3) . . . . ?
N004 C00B C00C C00A -1.0(4) . . . . ?
O005 S002 N004 C009 -166.3(3) . . . . ?
O005 S002 N004 C00B 22.1(4) . . . . ?
O005 S002 C00E C00G 156.7(4) . . . . ?
O005 S002 C00E C00I -26.2(4) . . . . ?
C009 N004 C00B C00C 1.2(4) . . . . ?
C009 C00A C00C Se01 176.1(3) . . . . ?
C009 C00A C00C C00B 0.4(4) . . . . ?
C009 C00A C00F C00H -0.5(6) . . . . ?
C009 C00D C00J C00H -0.6(6) . . . . ?
C00A C009 C00D C00J 1.1(6) . . . . ?
C00A C00F C00H C00J 1.0(6) . . . . ?
C00B N004 C009 C00A -0.9(4) . . . . ?
C00B N004 C009 C00D -179.8(4) . . . . ?
C00C C00A C00F C00H 179.6(4) . . . . ?
C00D C009 C00A C00C 179.4(4) . . . . ?
C00D C009 C00A C00F -0.5(6) . . . . ?
C00E S002 N004 C009 78.6(4) . . . . ?
C00E S002 N004 C00B -93.0(3) . . . . ?
C00E C00G C00M C00L -0.2(7) . . . . ?
C00E C00I C00N C00L 3.2(8) . . . . ?
C00F C00A C00C Se01 -4.0(6) . . . . ?
C00F C00A C00C C00B -179.7(4) . . . . ?
C00F C00H C00J C00D -0.5(7) . . . . ?
C00G C00E C00I C00N -1.6(7) . . . . ?
C00I C00E C00G C00M 0.1(7) . . . . ?
C00K Se01 C00C C00A 87.1(4) . . . . ?
C00K Se01 C00C C00B -97.8(4) . . . . ?
C00M C00L C00N C00I -3.3(9) . . . . ?
C00N C00L C00M C00G 1.8(8) . . . . ?
C00O C00L C00M C00G -178.7(5) . . . . ?
C00O C00L C00N C00I 177.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cp2br3secf3
_database_code_depnum_ccdc_archive 'CCDC 2160368'
loop_
_audit_author_name
_audit_author_address
'hui wang'
;FuZhou University
China
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Br F3 N O2 S Se'
_chemical_formula_sum            'C16 H11 Br F3 N O2 S Se'
_chemical_formula_weight         497.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0017(8)
_cell_length_b                   9.8234(6)
_cell_length_c                   15.0873(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.072(2)
_cell_angle_gamma                90
_cell_volume                     1778.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7618
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.770
_cell_measurement_theta_min      2.188
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    4.515
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.6952.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36323
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.277
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             3201
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.011
_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)+(0.0286P)²+2.1730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00D,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Se01 Se 0.37750(4) 0.32618(4) 0.68395(3) 0.06090(15) Uani 1 1 d . . . . .
Br02 Br 0.56966(4) 0.53686(5) 0.80110(3) 0.06359(16) Uani 1 1 d . . . . .
S003 S 0.60194(8) 0.83164(9) 0.67253(6) 0.0439(2) Uani 1 1 d . . . . .
O004 O 0.5550(2) 0.9466(2) 0.62914(18) 0.0560(7) Uani 1 1 d . . . . .
O005 O 0.6154(2) 0.8305(3) 0.76626(17) 0.0585(7) Uani 1 1 d . . . . .
N006 N 0.5177(2) 0.7001(3) 0.64636(18) 0.0371(7) Uani 1 1 d . . . . .
C007 C 0.4262(3) 0.5003(3) 0.6493(2) 0.0394(8) Uani 1 1 d . . . . .
C008 C 0.4537(3) 0.6908(3) 0.5659(2) 0.0342(8) Uani 1 1 d . . . . .
C009 C 0.3960(3) 0.5680(3) 0.5681(2) 0.0353(8) Uani 1 1 d . . . . .
C00A C 0.4995(3) 0.5796(3) 0.6940(2) 0.0398(8) Uani 1 1 d . . . . .
C00B C 0.4425(3) 0.7800(4) 0.4954(2) 0.0444(9) Uani 1 1 d . . . . .
H00B H 0.481214 0.861923 0.494267 0.053 Uiso 1 1 calc R . . . .
C00C C 0.3243(3) 0.5331(4) 0.4984(2) 0.0464(9) Uani 1 1 d . . . . .
H00C H 0.284787 0.451631 0.499184 0.056 Uiso 1 1 calc R . . . .
C00D C 0.7287(3) 0.7909(4) 0.6240(2) 0.0438(9) Uani 1 1 d . . . . .
C00E C 0.3717(3) 0.7425(4) 0.4271(3) 0.0522(10) Uani 1 1 d . . . . .
H00E H 0.363060 0.800255 0.378604 0.063 Uiso 1 1 calc R . . . .
C00F C 0.7999(3) 0.6997(4) 0.6656(3) 0.0519(10) Uani 1 1 d . . . . .
H00F H 0.780121 0.658925 0.718692 0.062 Uiso 1 1 calc R . . . .
C00G C 0.3130(3) 0.6214(4) 0.4283(3) 0.0526(10) Uani 1 1 d . . . . .
H00G H 0.265361 0.599553 0.381046 0.063 Uiso 1 1 calc R . . . .
C00H C 0.9007(4) 0.6697(4) 0.6276(3) 0.0618(11) Uani 1 1 d . . . . .
H00H H 0.948220 0.607162 0.654953 0.074 Uiso 1 1 calc R . . . .
C00I C 0.7580(4) 0.8519(4) 0.5457(3) 0.0584(11) Uani 1 1 d . . . . .
H00I H 0.709902 0.913147 0.517703 0.070 Uiso 1 1 calc R . . . .
C00J C 0.9322(4) 0.7311(5) 0.5493(3) 0.0655(12) Uani 1 1 d . . . . .
C00K C 0.8599(4) 0.8212(5) 0.5091(3) 0.0711(13) Uani 1 1 d . . . . .
H00K H 0.879826 0.862491 0.456194 0.085 Uiso 1 1 calc R . . . .
F00L F 0.2669(4) 0.4690(6) 0.8110(3) 0.179(2) Uani 1 1 d . . . . .
F00M F 0.1781(3) 0.4579(6) 0.6954(4) 0.181(2) Uani 1 1 d . . . . .
F00N F 0.1927(4) 0.2854(5) 0.7733(4) 0.220(3) Uani 1 1 d . . . . .
C00O C 0.2466(6) 0.3859(7) 0.7449(5) 0.1000(19) Uani 1 1 d . . . . .
C00P C 1.0456(4) 0.7003(6) 0.5103(4) 0.106(2) Uani 1 1 d . . . . .
H00A H 1.090177 0.781480 0.510815 0.159 Uiso 1 1 calc GR . . . .
H00D H 1.035849 0.668906 0.450366 0.159 Uiso 1 1 calc GR . . . .
H00J H 1.082334 0.631146 0.545001 0.159 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C007 1.885(3) . ?
Se01 C00O 1.926(7) . ?
Br02 C00A 1.857(3) . ?
S003 O004 1.416(3) . ?
S003 O005 1.420(3) . ?
S003 N006 1.683(3) . ?
S003 C00D 1.747(4) . ?
N006 C008 1.428(4) . ?
N006 C00A 1.404(4) . ?
C007 C009 1.434(5) . ?
C007 C00A 1.346(5) . ?
C008 C009 1.392(4) . ?
C008 C00B 1.382(5) . ?
C009 C00C 1.390(5) . ?
C00B C00E 1.373(5) . ?
C00C C00G 1.373(5) . ?
C00D C00F 1.381(5) . ?
C00D C00I 1.376(5) . ?
C00E C00G 1.383(5) . ?
C00F C00H 1.381(6) . ?
C00H C00J 1.385(6) . ?
C00I C00K 1.385(6) . ?
C00J C00K 1.373(6) . ?
C00J C00P 1.523(7) . ?
F00L C00O 1.308(8) . ?
F00M C00O 1.308(8) . ?
F00N C00O 1.260(6) . ?

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
C007 Se01 C00O 96.7(2) . . ?
O004 S003 O005 120.20(17) . . ?
O004 S003 N006 105.76(15) . . ?
O004 S003 C00D 109.30(18) . . ?
O005 S003 N006 106.52(16) . . ?
O005 S003 C00D 109.37(17) . . ?
N006 S003 C00D 104.49(15) . . ?
C008 N006 S003 124.0(2) . . ?
C00A N006 S003 128.7(2) . . ?
C00A N006 C008 107.2(3) . . ?
C009 C007 Se01 125.6(3) . . ?
C00A C007 Se01 126.1(3) . . ?
C00A C007 C009 108.2(3) . . ?
C009 C008 N006 107.1(3) . . ?
C00B C008 N006 131.1(3) . . ?
C00B C008 C009 121.8(3) . . ?
C008 C009 C007 107.7(3) . . ?
C00C C009 C007 132.5(3) . . ?
C00C C009 C008 119.8(3) . . ?
N006 C00A Br02 124.3(2) . . ?
C007 C00A Br02 125.9(3) . . ?
C007 C00A N006 109.7(3) . . ?
C00E C00B C008 117.2(3) . . ?
C00G C00C C009 118.6(3) . . ?
C00F C00D S003 119.6(3) . . ?
C00I C00D S003 119.9(3) . . ?
C00I C00D C00F 120.5(4) . . ?
C00B C00E C00G 121.9(4) . . ?
C00D C00F C00H 119.3(4) . . ?
C00C C00G C00E 120.7(3) . . ?
C00F C00H C00J 121.2(4) . . ?
C00D C00I C00K 119.3(4) . . ?
C00H C00J C00P 120.3(5) . . ?
C00K C00J C00H 118.5(4) . . ?
C00K C00J C00P 121.2(5) . . ?
C00J C00K C00I 121.3(4) . . ?
F00L C00O Se01 114.4(5) . . ?
F00L C00O F00M 101.7(6) . . ?
F00M C00O Se01 113.6(5) . . ?
F00N C00O Se01 110.6(5) . . ?
F00N C00O F00L 108.7(7) . . ?
F00N C00O F00M 107.2(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zzp20240429-mdseph_auto
_database_code_depnum_ccdc_archive 'CCDC 2353238'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Br N O2 S Se'
_chemical_formula_sum            'C21 H16 Br N O2 S Se'
_chemical_formula_weight         505.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONSSe
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'
Br Br -0.6763 1.2805 '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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8150(3)
_cell_length_b                   10.9504(5)
_cell_length_c                   12.0931(5)
_cell_angle_alpha                84.186(3)
_cell_angle_beta                 72.079(3)
_cell_angle_gamma                84.207(3)
_cell_volume                     976.96(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5501
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      67.9620
_cell_measurement_theta_min      3.8400
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.749
_exptl_absorpt_coefficient_mu    6.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7924
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.098
_diffrn_reflns_theta_min         3.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  10.00   0.50    0.50    --   42.30 -82.00-120.00  106
  2  ω     42.00  70.00   0.50    0.50    --   42.30 -82.00 120.00   56
  3  ω     68.00 120.00   0.50    0.50    --   42.30  65.00 -90.00  104
  4  ω     30.00  56.00   0.50    0.50    --   42.30 -82.00-120.00   52
  5  ω    -37.00  -1.00   0.50    0.50    --   42.30 -43.00-120.00   72
  6  ω    -36.00 -10.00   0.50    0.50    --   42.30 -77.00-120.00   52
  7  ω     27.00  68.00   0.50    0.50    --   42.30 -82.00  60.00   82
  8  ω     83.00 131.00   0.50    0.50    --   42.30  82.00-180.00   96
  9  ω     34.00  67.00   0.50    0.50    --   42.30 -82.00   0.00   66
 10  ω     92.00 119.00   0.50    0.50    --   42.30  82.00 120.00   54
 11  ω     13.00  39.00   0.50    0.50    --   42.30 -43.00-120.00   52
 12  ω    -46.00 -17.00   0.50    0.50    --   42.30 -77.00  30.00   58
 13  ω     -1.00  28.00   0.50    0.50    --   42.30 -77.00-120.00   58
 14  ω     -1.00  33.00   0.50    0.50    --   42.30 -77.00  30.00   68
 15  ω     32.00  63.00   0.50    0.50    --   42.30 -77.00-120.00   62
 16  ω     29.00  66.00   0.50    0.50    --   42.30  82.00-180.00   74
 17  ω     17.00  68.00   0.50    0.50    --   42.30 -82.00 -60.00  102
 18  ω      9.00  61.00   0.50    0.50    --   42.30 -77.00  90.00  104
 19  ω     18.00  87.00   0.50    0.50    --   42.30  82.00 120.00  138
 20  ω     38.00  63.00   0.50    0.50    --   42.30  65.00 -90.00   50
 21  ω    -32.00  -5.00   0.50    0.50    --   42.30 -82.00 120.00   54
 22  ω    110.00 183.00   0.50    0.55    --   93.70  68.00-150.00  146
 23  ω     48.00  89.00   0.50    0.55    --   93.70 -50.00 -60.00   82
 24  ω     50.00  85.00   0.50    0.55    --   93.70 -82.00  90.00   70
 25  ω     66.00 129.00   0.50    0.55    --   93.70  82.00 120.00  126
 26  ω      7.00 106.00   0.50    0.55    --   93.70 -82.00 150.00  198
 27  ω      4.00  65.00   0.50    0.55    --   93.70 -82.00-180.00  122
 28  ω     18.00 116.00   0.50    0.55    --   93.70 -82.00-120.00  196
 29  ω     84.00 110.00   0.50    0.55    --   93.70 -82.00 120.00   52
 30  ω      7.00 100.00   0.50    0.55    --   93.70 -82.00-150.00  186
 31  ω      5.00 109.00   0.50    0.55    --   93.70 -82.00 -60.00  208
 32  ω      4.00 100.00   0.50    0.55    --   93.70 -82.00  60.00  192
 33  ω    102.00 180.00   0.50    0.55    --   93.70  77.00  90.00  156
 34  ω     60.00 135.00   0.50    0.55    --   93.70  33.00  30.00  150
 35  ω    124.00 177.00   0.50    0.55    --   93.70  17.00 -30.00  106
 36  ω      9.00  86.00   0.50    0.55    --   93.70  17.00 -30.00  154
 37  ω     76.00 103.00   0.50    0.55    --   93.70 -82.00 -30.00   54
 38  ω     25.00  67.00   0.50    0.55    --   93.70 -59.00-120.00   84
 39  ω    123.00 180.00   0.50    0.55    --   93.70  59.00-120.00  114
 40  ω     23.00 116.00   0.50    0.55    --   93.70 -82.00  38.89  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1249529000
_diffrn_orient_matrix_UB_12      -0.0009471000
_diffrn_orient_matrix_UB_13      0.1264977000
_diffrn_orient_matrix_UB_21      -0.0805725000
_diffrn_orient_matrix_UB_22      -0.1166804000
_diffrn_orient_matrix_UB_23      -0.0175268000
_diffrn_orient_matrix_UB_31      0.1450976000
_diffrn_orient_matrix_UB_32      -0.0805704000
_diffrn_orient_matrix_UB_33      0.0414279000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2907
_reflns_number_total             3443
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.052
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.052
_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)+(0.1470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N006(H006), C009(H009), C00D(H00D), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00Q(H00a,H00b,H00c)
;
_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
Se01 Se 0.61698(8) 0.31223(5) 0.06580(5) 0.0432(3) Uani 1 1 d . . . . .
Br02 Br 0.02502(8) 0.61183(5) 0.77164(5) 0.0489(3) Uani 1 1 d . . . . .
S003 S 0.14357(18) 0.78684(10) 0.28987(12) 0.0381(4) Uani 1 1 d . . . . .
O004 O -0.0269(5) 0.8148(3) 0.3746(4) 0.0488(10) Uani 1 1 d . . . . .
O005 O 0.1562(6) 0.7990(3) 0.1685(4) 0.0514(10) Uani 1 1 d . . . . .
N006 N 0.2145(6) 0.6441(3) 0.3117(4) 0.0382(10) Uani 1 1 d . . . . .
H006 H 0.252172 0.601215 0.249813 0.046 Uiso 1 1 calc R U . . .
C007 C 0.2229(6) 0.5807(4) 0.4175(4) 0.0325(10) Uani 1 1 d . . . . .
C008 C 0.2990(6) 0.8780(4) 0.3146(4) 0.0319(10) Uani 1 1 d . . . . .
C009 C 0.1378(7) 0.6246(4) 0.5246(5) 0.0364(11) Uani 1 1 d . . . . .
H009 H 0.071502 0.702554 0.530611 0.044 Uiso 1 1 calc R U . . .
C00A C 0.4115(7) 0.2549(4) 0.0345(4) 0.0370(11) Uani 1 1 d . . . . .
C00B C 0.1500(7) 0.5531(4) 0.6243(4) 0.0345(11) Uani 1 1 d . . . . .
C00C C 0.5515(7) 1.0283(4) 0.3371(5) 0.0403(12) Uani 1 1 d . . . . .
C00D C 0.2491(7) 0.4396(4) 0.6185(5) 0.0391(12) Uani 1 1 d . . . . .
H00D H 0.256817 0.392374 0.687353 0.047 Uiso 1 1 calc R U . . .
C00E C 0.4170(7) 0.4200(4) 0.2967(5) 0.0366(12) Uani 1 1 d . . . . .
C00F C 0.3268(6) 0.4653(4) 0.4092(4) 0.0315(11) Uani 1 1 d . . . . .
C00G C 0.3355(7) 0.3977(4) 0.5104(5) 0.0378(11) Uani 1 1 d . . . . .
H00G H 0.403069 0.320222 0.505258 0.045 Uiso 1 1 calc R U . . .
C00H C 0.2418(7) 0.9880(4) 0.3635(5) 0.0414(12) Uani 1 1 d . . . . .
H00H H 0.116774 1.012923 0.389201 0.050 Uiso 1 1 calc R U . . .
C00I C 0.4921(7) 0.3797(4) 0.2049(5) 0.0386(12) Uani 1 1 d . . . . .
C00J C 0.3057(8) 0.3330(4) -0.0189(5) 0.0436(13) Uani 1 1 d . . . . .
H00J H 0.333814 0.415965 -0.041588 0.052 Uiso 1 1 calc R U . . .
C00K C 0.1181(8) 0.1680(5) -0.0062(5) 0.0488(13) Uani 1 1 d . . . . .
H00K H 0.018103 0.137575 -0.020751 0.059 Uiso 1 1 calc R U . . .
C00L C 0.3722(8) 0.1333(4) 0.0662(5) 0.0440(13) Uani 1 1 d . . . . .
H00L H 0.446818 0.078530 0.100690 0.053 Uiso 1 1 calc R U . . .
C00M C 0.4812(7) 0.8421(5) 0.2755(5) 0.0425(12) Uani 1 1 d . . . . .
H00M H 0.521230 0.766293 0.240670 0.051 Uiso 1 1 calc R U . . .
C00N C 0.6043(7) 0.9179(5) 0.2878(5) 0.0449(13) Uani 1 1 d . . . . .
H00N H 0.729203 0.892783 0.261239 0.054 Uiso 1 1 calc R U . . .
C00O C 0.3662(8) 1.0626(5) 0.3754(5) 0.0480(13) Uani 1 1 d . . . . .
H00O H 0.325658 1.138474 0.410208 0.058 Uiso 1 1 calc R U . . .
C00P C 0.2229(8) 0.0933(5) 0.0468(5) 0.0520(15) Uani 1 1 d . . . . .
H00P H 0.192721 0.010961 0.071280 0.062 Uiso 1 1 calc R U . . .
C00Q C 0.6867(8) 1.1102(5) 0.3485(6) 0.0559(16) Uani 1 1 d . . . . .
H00A H 0.807848 1.068745 0.322420 0.084 Uiso 1 1 calc R U . . .
H00B H 0.658958 1.128215 0.430141 0.084 Uiso 1 1 calc R U . . .
H00C H 0.681735 1.187264 0.300293 0.084 Uiso 1 1 calc R U . . .
C00R C 0.1582(8) 0.2898(5) -0.0392(5) 0.0441(13) Uani 1 1 d . . . . .
H00R H 0.084595 0.343203 -0.075532 0.053 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
Se01 C00A 1.934(6) . ?
Se01 C00I 1.851(5) . ?
Br02 C00B 1.892(5) . ?
S003 O004 1.435(4) . ?
S003 O005 1.434(4) . ?
S003 N006 1.629(4) . ?
S003 C008 1.758(5) . ?
N006 H006 0.8800 . ?
N006 C007 1.409(6) . ?
C007 C009 1.371(7) . ?
C007 C00F 1.427(6) . ?
C008 C00H 1.369(7) . ?
C008 C00M 1.384(7) . ?
C009 H009 0.9500 . ?
C009 C00B 1.393(7) . ?
C00A C00J 1.380(8) . ?
C00A C00L 1.385(7) . ?
C00B C00D 1.393(7) . ?
C00C C00N 1.371(8) . ?
C00C C00O 1.402(8) . ?
C00C C00Q 1.499(7) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.374(8) . ?
C00E C00F 1.438(7) . ?
C00E C00I 1.191(8) . ?
C00F C00G 1.382(7) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00O 1.380(8) . ?
C00J H00J 0.9500 . ?
C00J C00R 1.386(9) . ?
C00K H00K 0.9500 . ?
C00K C00P 1.353(8) . ?
C00K C00R 1.391(8) . ?
C00L H00L 0.9500 . ?
C00L C00P 1.379(8) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.381(8) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q H00A 0.9800 . ?
C00Q H00B 0.9800 . ?
C00Q H00C 0.9800 . ?
C00R H00R 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I Se01 C00A 97.1(2) . . ?
O004 S003 N006 110.2(2) . . ?
O004 S003 C008 106.8(2) . . ?
O005 S003 O004 119.4(3) . . ?
O005 S003 N006 103.7(2) . . ?
O005 S003 C008 109.6(2) . . ?
N006 S003 C008 106.5(2) . . ?
S003 N006 H006 116.0 . . ?
C007 N006 S003 128.0(4) . . ?
C007 N006 H006 116.0 . . ?
N006 C007 C00F 116.5(4) . . ?
C009 C007 N006 123.4(4) . . ?
C009 C007 C00F 120.1(4) . . ?
C00H C008 S003 120.3(4) . . ?
C00H C008 C00M 120.3(5) . . ?
C00M C008 S003 119.2(4) . . ?
C007 C009 H009 120.5 . . ?
C007 C009 C00B 119.0(4) . . ?
C00B C009 H009 120.5 . . ?
C00J C00A Se01 120.9(4) . . ?
C00J C00A C00L 120.2(5) . . ?
C00L C00A Se01 118.8(4) . . ?
C009 C00B Br02 118.7(4) . . ?
C009 C00B C00D 122.0(5) . . ?
C00D C00B Br02 119.3(4) . . ?
C00N C00C C00O 117.6(5) . . ?
C00N C00C C00Q 121.3(5) . . ?
C00O C00C C00Q 121.0(5) . . ?
C00B C00D H00D 120.9 . . ?
C00G C00D C00B 118.3(5) . . ?
C00G C00D H00D 120.9 . . ?
C00I C00E C00F 178.3(5) . . ?
C007 C00F C00E 119.9(4) . . ?
C00G C00F C007 118.9(5) . . ?
C00G C00F C00E 121.2(4) . . ?
C00D C00G C00F 121.8(4) . . ?
C00D C00G H00G 119.1 . . ?
C00F C00G H00G 119.1 . . ?
C008 C00H H00H 120.1 . . ?
C008 C00H C00O 119.9(5) . . ?
C00O C00H H00H 120.1 . . ?
C00E C00I Se01 177.1(5) . . ?
C00A C00J H00J 120.1 . . ?
C00A C00J C00R 119.7(4) . . ?
C00R C00J H00J 120.1 . . ?
C00P C00K H00K 120.3 . . ?
C00P C00K C00R 119.4(6) . . ?
C00R C00K H00K 120.3 . . ?
C00A C00L H00L 120.6 . . ?
C00P C00L C00A 118.8(5) . . ?
C00P C00L H00L 120.6 . . ?
C008 C00M H00M 120.4 . . ?
C00N C00M C008 119.2(5) . . ?
C00N C00M H00M 120.4 . . ?
C00C C00N C00M 122.0(5) . . ?
C00C C00N H00N 119.0 . . ?
C00M C00N H00N 119.0 . . ?
C00C C00O H00O 119.5 . . ?
C00H C00O C00C 121.0(5) . . ?
C00H C00O H00O 119.5 . . ?
C00K C00P C00L 121.9(5) . . ?
C00K C00P H00P 119.1 . . ?
C00L C00P H00P 119.1 . . ?
C00C C00Q H00A 109.5 . . ?
C00C C00Q H00B 109.5 . . ?
C00C C00Q H00C 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
C00J C00R C00K 119.9(5) . . ?
C00J C00R H00R 120.1 . . ?
C00K C00R H00R 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C00A C00J C00R -179.3(4) . . . . ?
Se01 C00A C00L C00P 178.2(4) . . . . ?
Br02 C00B C00D C00G 178.6(4) . . . . ?
S003 N006 C007 C009 13.5(7) . . . . ?
S003 N006 C007 C00F -166.5(4) . . . . ?
S003 C008 C00H C00O -175.7(4) . . . . ?
S003 C008 C00M C00N 175.6(4) . . . . ?
O004 S003 N006 C007 -48.1(5) . . . . ?
O004 S003 C008 C00H -27.4(5) . . . . ?
O004 S003 C008 C00M 157.8(4) . . . . ?
O005 S003 N006 C007 -177.0(4) . . . . ?
O005 S003 C008 C00H 103.2(4) . . . . ?
O005 S003 C008 C00M -71.6(4) . . . . ?
N006 S003 C008 C00H -145.1(4) . . . . ?
N006 S003 C008 C00M 40.1(5) . . . . ?
N006 C007 C009 C00B 178.0(4) . . . . ?
N006 C007 C00F C00E 0.4(7) . . . . ?
N006 C007 C00F C00G -178.2(4) . . . . ?
C007 C009 C00B Br02 -177.8(4) . . . . ?
C007 C009 C00B C00D 1.4(7) . . . . ?
C007 C00F C00G C00D -1.0(7) . . . . ?
C008 S003 N006 C007 67.4(5) . . . . ?
C008 C00H C00O C00C 0.7(9) . . . . ?
C008 C00M C00N C00C -0.4(8) . . . . ?
C009 C007 C00F C00E -179.5(4) . . . . ?
C009 C007 C00F C00G 1.8(7) . . . . ?
C009 C00B C00D C00G -0.5(8) . . . . ?
C00A C00J C00R C00K -0.3(8) . . . . ?
C00A C00L C00P C00K 2.5(9) . . . . ?
C00B C00D C00G C00F 0.4(8) . . . . ?
C00E C00F C00G C00D -179.6(5) . . . . ?
C00F C007 C009 C00B -2.0(7) . . . . ?
C00H C008 C00M C00N 0.8(8) . . . . ?
C00J C00A C00L C00P -2.0(8) . . . . ?
C00L C00A C00J C00R 0.9(8) . . . . ?
C00M C008 C00H C00O -0.9(8) . . . . ?
C00N C00C C00O C00H -0.2(8) . . . . ?
C00O C00C C00N C00M 0.1(8) . . . . ?
C00P C00K C00R C00J 0.8(9) . . . . ?
C00Q C00C C00N C00M -179.3(5) . . . . ?
C00Q C00C C00O C00H 179.1(6) . . . . ?
C00R C00K C00P C00L -1.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.913
_oxdiff_exptl_absorpt_empirical_full_min 0.254
####################################################################### 
# 
# 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_zzp20240501-cpcn_auto
_database_code_depnum_ccdc_archive 'CCDC 2353239'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Br F3 N2 O2 S Se'
_chemical_formula_sum            'C17 H10 Br F3 N2 O2 S Se'
_chemical_formula_weight         522.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFSSeBr
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'
Br Br -0.6763 1.2805 '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'
Se Se -0.7943 1.1372 '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                   12.3271(2)
_cell_length_b                   16.2838(2)
_cell_length_c                   18.4587(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3705.25(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8906
_cell_measurement_temperature    200.0(2)
_cell_measurement_theta_max      67.9520
_cell_measurement_theta_min      2.4010
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    6.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13411
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         4.791
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -21.00   0.50    1.00    --   42.40 -22.00 154.00   50
  2  ω    158.00 183.00   0.50    2.54    --   93.70 -22.00 154.00   50
  3  ω     93.00 128.00   0.50    2.54    --   93.70  22.00 -40.00   70
  4  ω     75.00 101.00   0.50    2.54    --   93.70 -22.00 154.00   52
  5  ω      1.00  65.00   0.50    1.00    --   42.40 -65.00 -30.00  128
  6  ω    -47.00  11.00   0.50    1.00    --   42.40 -43.00 -30.00  116
  7  ω     18.00  43.00   0.50    1.00    --   42.40  22.00 -40.00   50
  8  ω     84.00 110.00   0.50    1.00    --   42.40  65.00-180.00   52
  9  ω    -34.00  -9.00   0.50    1.00    --   42.40 -65.00 -30.00   50
 10  ω    -46.00  17.00   0.50    1.00    --   42.40 -82.00 -30.00  126
 11  ω     33.00  72.00   0.50    1.00    --   42.40 -43.00 -30.00   78
 12  ω    -44.00   8.00   0.50    1.00    --   42.40 -54.00-120.00  104
 13  ω     12.00  42.00   0.50    1.00    --   42.40 -54.00-120.00   60
 14  ω     28.00  53.00   0.50    1.00    --   42.40 -82.00 -30.00   50
 15  ω     76.00 102.00   0.50    2.54    --   93.70 -82.00   0.00   52
 16  ω     76.00 112.00   0.50    2.54    --   93.70 -59.00  60.00   72
 17  ω     26.00 121.00   0.50    2.54    --   93.70 -82.00 -30.00  190
 18  ω     27.00  52.00   0.50    2.54    --   93.70 -59.00  60.00   50
 19  ω     70.00 183.00   0.50    2.54    --   93.70  59.00  60.00  226
 20  ω     73.00 180.00   0.50    2.54    --   93.70  68.00 -60.00  214
 21  ω     15.00  82.00   0.50    2.54    --   93.70 -82.00  60.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0195469000
_diffrn_orient_matrix_UB_12      -0.0903133000
_diffrn_orient_matrix_UB_13      -0.0213262000
_diffrn_orient_matrix_UB_21      0.0300181000
_diffrn_orient_matrix_UB_22      0.0271709000
_diffrn_orient_matrix_UB_23      -0.0774641000
_diffrn_orient_matrix_UB_31      0.1196315000
_diffrn_orient_matrix_UB_32      0.0079110000
_diffrn_orient_matrix_UB_33      0.0226998000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2974
_reflns_number_total             3360
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.134
_refine_diff_density_min         -1.105
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1071P)²+11.0007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00J(H00J), C00L(H00L), C00M(H00M),
 C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00Q(H00a,H00b,H00f)
;
_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
Se01 Se 0.63854(6) 0.26784(4) 0.62490(4) 0.0376(3) Uani 1 1 d . . . . .
Br02 Br 0.37800(5) 0.35384(4) 0.58977(4) 0.0428(3) Uani 1 1 d . . . . .
S003 S 0.81927(12) 0.44433(9) 0.62019(8) 0.0330(4) Uani 1 1 d . . . . .
O004 O 0.8540(3) 0.5178(3) 0.6552(3) 0.0422(10) Uani 1 1 d . . . . .
O005 O 0.8517(4) 0.3665(3) 0.6464(3) 0.0433(11) Uani 1 1 d . . . . .
N006 N 0.6809(4) 0.4474(3) 0.6257(3) 0.0302(10) Uani 1 1 d . . . . .
C007 C 0.5154(5) 0.5005(3) 0.5995(3) 0.0265(11) Uani 1 1 d . . . . .
C008 C 0.5088(5) 0.4115(3) 0.6013(3) 0.0288(11) Uani 1 1 d . . . . .
C009 C 0.4717(5) 0.6419(3) 0.5891(3) 0.0316(13) Uani 1 1 d . . . . .
C00A C 0.6074(5) 0.3816(3) 0.6157(3) 0.0292(12) Uani 1 1 d . . . . .
C00B C 0.8452(5) 0.4516(3) 0.5272(3) 0.0319(12) Uani 1 1 d . . . . .
C00C C 0.4378(5) 0.5607(3) 0.5860(3) 0.0314(12) Uani 1 1 d . . . . .
H00C H 0.364786 0.546747 0.575181 0.038 Uiso 1 1 calc R U . . .
C00D C 0.8518(5) 0.3787(4) 0.4868(3) 0.0358(13) Uani 1 1 d . . . . .
H00D H 0.845158 0.326699 0.509657 0.043 Uiso 1 1 calc R U . . .
C00E C 0.8573(5) 0.5276(4) 0.4950(4) 0.0384(14) Uani 1 1 d . . . . .
H00E H 0.854531 0.576252 0.523376 0.046 Uiso 1 1 calc R U . . .
N00F N 0.3412(5) 0.7592(4) 0.5561(4) 0.0533(15) Uani 1 1 d . . . . .
C00G C 0.6227(5) 0.5204(3) 0.6150(3) 0.0285(12) Uani 1 1 d . . . . .
F00H F 0.6502(7) 0.1876(3) 0.7516(3) 0.120(3) Uani 1 1 d . . . . .
C00I C 0.3967(5) 0.7073(3) 0.5713(4) 0.0363(13) Uani 1 1 d . . . . .
C00J C 0.5792(5) 0.6626(3) 0.6065(3) 0.0353(13) Uani 1 1 d . . . . .
H00J H 0.599251 0.718797 0.609394 0.042 Uiso 1 1 calc R U . . .
F00K F 0.6913(8) 0.3154(4) 0.7640(3) 0.122(3) Uani 1 1 d . . . . .
C00L C 0.8738(5) 0.5320(4) 0.4203(4) 0.0377(14) Uani 1 1 d . . . . .
H00L H 0.882032 0.584031 0.397631 0.045 Uiso 1 1 calc R U . . .
C00M C 0.6562(5) 0.6030(4) 0.6195(3) 0.0369(14) Uani 1 1 d . . . . .
H00M H 0.729005 0.617026 0.631078 0.044 Uiso 1 1 calc R U . . .
C00N C 0.8783(5) 0.4607(4) 0.3785(3) 0.0380(14) Uani 1 1 d . . . . .
C00O C 0.8684(6) 0.3844(4) 0.4130(4) 0.0427(16) Uani 1 1 d . . . . .
H00O H 0.873056 0.335626 0.385006 0.051 Uiso 1 1 calc R U . . .
F00P F 0.5361(7) 0.2809(5) 0.7564(4) 0.129(3) Uani 1 1 d . . . . .
C00Q C 0.8899(6) 0.4659(5) 0.2971(4) 0.0528(18) Uani 1 1 d . . . . .
H00A H 0.819386 0.479116 0.275509 0.079 Uiso 1 1 calc R U . . .
H00B H 0.915511 0.413135 0.278262 0.079 Uiso 1 1 calc R U . . .
H00F H 0.942270 0.509016 0.284797 0.079 Uiso 1 1 calc R U . . .
C00R C 0.6289(8) 0.2644(5) 0.7303(5) 0.059(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C00A 1.899(6) . ?
Se01 C00R 1.951(8) . ?
Br02 C008 1.878(6) . ?
S003 O004 1.426(5) . ?
S003 O005 1.414(5) . ?
S003 N006 1.709(5) . ?
S003 C00B 1.751(6) . ?
N006 C00A 1.416(7) . ?
N006 C00G 1.402(7) . ?
C007 C008 1.452(7) . ?
C007 C00C 1.391(8) . ?
C007 C00G 1.392(8) . ?
C008 C00A 1.337(8) . ?
C009 C00C 1.388(8) . ?
C009 C00I 1.447(8) . ?
C009 C00J 1.405(9) . ?
C00B C00D 1.405(8) . ?
C00B C00E 1.380(9) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00O 1.380(9) . ?
C00E H00E 0.9500 . ?
C00E C00L 1.397(10) . ?
N00F C00I 1.124(9) . ?
C00G C00M 1.409(8) . ?
F00H C00R 1.337(9) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.379(9) . ?
F00K C00R 1.290(11) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.395(10) . ?
C00M H00M 0.9500 . ?
C00N C00O 1.400(10) . ?
C00N C00Q 1.512(9) . ?
C00O H00O 0.9500 . ?
F00P C00R 1.270(11) . ?
C00Q H00A 0.9800 . ?
C00Q H00B 0.9800 . ?
C00Q H00F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A Se01 C00R 96.0(3) . . ?
O004 S003 N006 104.3(2) . . ?
O004 S003 C00B 109.5(3) . . ?
O005 S003 O004 120.8(3) . . ?
O005 S003 N006 106.7(3) . . ?
O005 S003 C00B 110.2(3) . . ?
N006 S003 C00B 103.8(3) . . ?
C00A N006 S003 127.5(4) . . ?
C00G N006 S003 121.8(4) . . ?
C00G N006 C00A 107.2(5) . . ?
C00C C007 C008 132.0(5) . . ?
C00C C007 C00G 121.7(5) . . ?
C00G C007 C008 106.3(5) . . ?
C007 C008 Br02 123.0(4) . . ?
C00A C008 Br02 128.4(4) . . ?
C00A C008 C007 108.5(5) . . ?
C00C C009 C00I 120.0(6) . . ?
C00C C009 C00J 121.4(5) . . ?
C00J C009 C00I 118.5(5) . . ?
N006 C00A Se01 126.7(4) . . ?
C008 C00A Se01 123.8(4) . . ?
C008 C00A N006 109.4(5) . . ?
C00D C00B S003 118.3(4) . . ?
C00E C00B S003 120.2(5) . . ?
C00E C00B C00D 121.5(6) . . ?
C007 C00C H00C 121.4 . . ?
C009 C00C C007 117.2(5) . . ?
C009 C00C H00C 121.4 . . ?
C00B C00D H00D 120.8 . . ?
C00O C00D C00B 118.4(6) . . ?
C00O C00D H00D 120.8 . . ?
C00B C00E H00E 120.4 . . ?
C00B C00E C00L 119.1(6) . . ?
C00L C00E H00E 120.4 . . ?
N006 C00G C00M 130.6(5) . . ?
C007 C00G N006 108.6(5) . . ?
C007 C00G C00M 120.8(5) . . ?
N00F C00I C009 177.6(8) . . ?
C009 C00J H00J 119.3 . . ?
C00M C00J C009 121.4(5) . . ?
C00M C00J H00J 119.3 . . ?
C00E C00L H00L 119.7 . . ?
C00N C00L C00E 120.6(6) . . ?
C00N C00L H00L 119.7 . . ?
C00G C00M H00M 121.3 . . ?
C00J C00M C00G 117.4(6) . . ?
C00J C00M H00M 121.3 . . ?
C00L C00N C00O 118.9(6) . . ?
C00L C00N C00Q 120.3(6) . . ?
C00O C00N C00Q 120.7(6) . . ?
C00D C00O C00N 121.4(6) . . ?
C00D C00O H00O 119.3 . . ?
C00N C00O H00O 119.3 . . ?
C00N C00Q H00A 109.5 . . ?
C00N C00Q H00B 109.5 . . ?
C00N C00Q H00F 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00F 109.5 . . ?
H00B C00Q H00F 109.5 . . ?
F00H C00R Se01 107.9(6) . . ?
F00K C00R Se01 115.2(6) . . ?
F00K C00R F00H 110.1(8) . . ?
F00P C00R Se01 115.3(7) . . ?
F00P C00R F00H 105.2(8) . . ?
F00P C00R F00K 102.6(8) . . ?

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
Br02 C008 C00A Se01 2.4(8) . . . . ?
Br02 C008 C00A N006 -175.2(4) . . . . ?
S003 N006 C00A Se01 22.3(7) . . . . ?
S003 N006 C00A C008 -160.2(4) . . . . ?
S003 N006 C00G C007 160.9(4) . . . . ?
S003 N006 C00G C00M -20.8(9) . . . . ?
S003 C00B C00D C00O 177.7(5) . . . . ?
S003 C00B C00E C00L -177.6(5) . . . . ?
O004 S003 N006 C00A -163.2(5) . . . . ?
O004 S003 N006 C00G 40.7(5) . . . . ?
O004 S003 C00B C00D 158.9(5) . . . . ?
O004 S003 C00B C00E -21.8(6) . . . . ?
O005 S003 N006 C00A -34.3(5) . . . . ?
O005 S003 N006 C00G 169.6(4) . . . . ?
O005 S003 C00B C00D 23.8(5) . . . . ?
O005 S003 C00B C00E -156.9(5) . . . . ?
N006 S003 C00B C00D -90.1(5) . . . . ?
N006 S003 C00B C00E 89.2(5) . . . . ?
N006 C00G C00M C00J -179.4(6) . . . . ?
C007 C008 C00A Se01 179.1(4) . . . . ?
C007 C008 C00A N006 1.5(6) . . . . ?
C007 C00G C00M C00J -1.3(9) . . . . ?
C008 C007 C00C C009 179.6(6) . . . . ?
C008 C007 C00G N006 0.3(6) . . . . ?
C008 C007 C00G C00M -178.3(5) . . . . ?
C009 C00J C00M C00G -0.3(9) . . . . ?
C00A N006 C00G C007 0.6(6) . . . . ?
C00A N006 C00G C00M 178.9(6) . . . . ?
C00B S003 N006 C00A 82.2(5) . . . . ?
C00B S003 N006 C00G -73.9(5) . . . . ?
C00B C00D C00O C00N 0.0(10) . . . . ?
C00B C00E C00L C00N -0.2(9) . . . . ?
C00C C007 C008 Br02 -4.1(9) . . . . ?
C00C C007 C008 C00A 179.0(6) . . . . ?
C00C C007 C00G N006 -179.8(5) . . . . ?
C00C C007 C00G C00M 1.7(9) . . . . ?
C00C C009 C00J C00M 1.7(9) . . . . ?
C00D C00B C00E C00L 1.7(9) . . . . ?
C00E C00B C00D C00O -1.6(9) . . . . ?
C00E C00L C00N C00O -1.3(9) . . . . ?
C00E C00L C00N C00Q 176.6(6) . . . . ?
C00G N006 C00A Se01 -178.8(4) . . . . ?
C00G N006 C00A C008 -1.3(6) . . . . ?
C00G C007 C008 Br02 175.8(4) . . . . ?
C00G C007 C008 C00A -1.1(6) . . . . ?
C00G C007 C00C C009 -0.3(8) . . . . ?
C00I C009 C00C C007 176.3(5) . . . . ?
C00I C009 C00J C00M -176.0(6) . . . . ?
C00J C009 C00C C007 -1.3(8) . . . . ?
C00L C00N C00O C00D 1.4(10) . . . . ?
C00Q C00N C00O C00D -176.4(6) . . . . ?
C00R Se01 C00A N006 80.5(5) . . . . ?
C00R Se01 C00A C008 -96.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 24.573
_oxdiff_exptl_absorpt_empirical_full_min 0.376
####################################################################### 
# 
# 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_cpsecf3ts09
_database_code_depnum_ccdc_archive 'CCDC 2179735'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Br0.994 F4 N O2 S Se'
_chemical_formula_sum            'C16 H10 Br F4 N O2 S Se'
_chemical_formula_weight         515.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5730(5)
_cell_length_b                   9.7379(5)
_cell_length_c                   10.6701(6)
_cell_angle_alpha                73.547(2)
_cell_angle_beta                 67.327(2)
_cell_angle_gamma                84.288(2)
_cell_volume                     880.17(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    4.572
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.5604.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29483
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.079
_diffrn_reflns_theta_max         25.079
_diffrn_reflns_theta_min         2.146
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3138
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0070(9)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²+0.7898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00a,H00b,H00c)
;
_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
Se01 Se 0.05037(4) 0.26045(3) 0.50742(4) 0.05326(14) Uani 1 1 d . . . . .
Br02 Br 0.32831(4) 0.42745(3) 0.17269(3) 0.05584(16) Uani 0.9937(17) 1 d . . .
. .
S003 S 0.49959(8) 0.69663(7) 0.22049(7) 0.03935(18) Uani 1 1 d . . . . .
O004 O 0.5793(2) 0.6279(2) 0.1128(2) 0.0487(5) Uani 1 1 d . . . . .
O005 O 0.5774(2) 0.7496(2) 0.2867(2) 0.0520(5) Uani 1 1 d . . . . .
F006 F 0.3166(2) 0.1153(2) 0.4839(3) 0.0835(7) Uani 1 1 d . . . . .
F007 F 0.1186(3) -0.01742(19) 0.5782(3) 0.0744(6) Uani 1 1 d . . . . .
N008 N 0.3746(3) 0.5744(2) 0.3536(2) 0.0387(5) Uani 1 1 d . . . . .
F009 F 0.2934(3) 0.7275(3) 0.7729(2) 0.0909(7) Uani 1 1 d . . . . .
F00A F 0.1718(3) 0.0972(2) 0.6970(2) 0.0849(7) Uani 1 1 d . . . . .
C00B C 0.3104(3) 0.5812(3) 0.4960(3) 0.0390(6) Uani 1 1 d . . . . .
C00C C 0.3846(3) 0.8306(3) 0.1639(3) 0.0384(6) Uani 1 1 d . . . . .
C00D C 0.1849(3) 0.4102(3) 0.4688(3) 0.0418(6) Uani 1 1 d . . . . .
C00E C 0.2911(3) 0.4702(3) 0.3420(3) 0.0389(6) Uani 1 1 d . . . . .
C00F C 0.1920(3) 0.4795(3) 0.5682(3) 0.0418(6) Uani 1 1 d . . . . .
C00G C 0.3517(4) 0.8324(3) 0.0483(3) 0.0484(7) Uani 1 1 d . . . . .
H00G H 0.389941 0.762738 -0.000139 0.058 Uiso 1 1 calc R U . . .
C00H C 0.2016(3) 1.0437(3) 0.0782(3) 0.0480(7) Uani 1 1 d . . . . .
C00I C 0.3479(4) 0.6665(3) 0.5628(3) 0.0498(7) Uani 1 1 d . . . . .
H00I H 0.426920 0.732984 0.515658 0.060 Uiso 1 1 calc R U . . .
C00J C 0.3298(4) 0.9346(3) 0.2351(3) 0.0488(7) Uani 1 1 d . . . . .
H00J H 0.354834 0.934022 0.311283 0.059 Uiso 1 1 calc R U . . .
C00K C 0.1085(4) 0.4639(3) 0.7104(3) 0.0540(8) Uani 1 1 d . . . . .
H00K H 0.030034 0.396954 0.759619 0.065 Uiso 1 1 calc R U . . .
C00L C 0.1735(4) 0.1063(3) 0.5704(4) 0.0517(8) Uani 1 1 d . . . . .
C00M C 0.2605(4) 0.9400(4) 0.0058(3) 0.0543(8) Uani 1 1 d . . . . .
H00M H 0.238448 0.942871 -0.072442 0.065 Uiso 1 1 calc R U . . .
C00N C 0.2380(4) 1.0390(3) 0.1925(4) 0.0533(8) Uani 1 1 d . . . . .
H00N H 0.199469 1.108093 0.241656 0.064 Uiso 1 1 calc R U . . .
C00O C 0.2608(5) 0.6462(4) 0.7028(4) 0.0596(9) Uani 1 1 d . . . . .
C00P C 0.1435(5) 0.5485(4) 0.7771(3) 0.0645(10) Uani 1 1 d . . . . .
H00P H 0.088207 0.540108 0.872269 0.077 Uiso 1 1 calc R U . . .
C00Q C 0.1004(4) 1.1597(4) 0.0329(4) 0.0660(10) Uani 1 1 d . . . . .
H00A H 0.108396 1.163032 -0.060371 0.099 Uiso 1 1 calc R U . . .
H00B H 0.131033 1.250396 0.033391 0.099 Uiso 1 1 calc R U . . .
H00C H -0.002611 1.139310 0.097074 0.099 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
Se01 C00D 1.892(3) . ?
Se01 C00L 1.944(3) . ?
Br02 C00E 1.861(3) . ?
S003 O004 1.417(2) . ?
S003 O005 1.418(2) . ?
S003 N008 1.697(2) . ?
S003 C00C 1.749(3) . ?
F006 C00L 1.319(4) . ?
F007 C00L 1.330(3) . ?
N008 C00B 1.421(3) . ?
N008 C00E 1.413(3) . ?
F009 C00O 1.359(4) . ?
F00A C00L 1.323(4) . ?
C00B C00F 1.406(4) . ?
C00B C00I 1.385(4) . ?
C00C C00G 1.382(4) . ?
C00C C00J 1.379(4) . ?
C00D C00E 1.347(4) . ?
C00D C00F 1.433(4) . ?
C00F C00K 1.386(4) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.385(4) . ?
C00H C00M 1.388(5) . ?
C00H C00N 1.380(5) . ?
C00H C00Q 1.510(4) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.368(5) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.371(4) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.366(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00P 1.377(5) . ?
C00P H00P 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D Se01 C00L 95.78(12) . . ?
O004 S003 O005 120.61(13) . . ?
O004 S003 N008 106.76(12) . . ?
O004 S003 C00C 110.01(13) . . ?
O005 S003 N008 104.43(12) . . ?
O005 S003 C00C 109.66(13) . . ?
N008 S003 C00C 103.91(12) . . ?
C00B N008 S003 124.26(19) . . ?
C00E N008 S003 127.43(19) . . ?
C00E N008 C00B 106.9(2) . . ?
C00F C00B N008 107.4(2) . . ?
C00I C00B N008 130.6(3) . . ?
C00I C00B C00F 122.0(3) . . ?
C00G C00C S003 120.0(2) . . ?
C00J C00C S003 119.0(2) . . ?
C00J C00C C00G 121.0(3) . . ?
C00E C00D Se01 125.5(2) . . ?
C00E C00D C00F 108.2(2) . . ?
C00F C00D Se01 126.3(2) . . ?
N008 C00E Br02 123.01(19) . . ?
C00D C00E Br02 127.0(2) . . ?
C00D C00E N008 110.0(2) . . ?
C00B C00F C00D 107.4(2) . . ?
C00K C00F C00B 119.6(3) . . ?
C00K C00F C00D 133.0(3) . . ?
C00C C00G H00G 120.6 . . ?
C00C C00G C00M 118.7(3) . . ?
C00M C00G H00G 120.6 . . ?
C00M C00H C00Q 121.0(3) . . ?
C00N C00H C00M 118.5(3) . . ?
C00N C00H C00Q 120.5(3) . . ?
C00B C00I H00I 122.3 . . ?
C00O C00I C00B 115.5(3) . . ?
C00O C00I H00I 122.3 . . ?
C00C C00J H00J 120.3 . . ?
C00N C00J C00C 119.3(3) . . ?
C00N C00J H00J 120.3 . . ?
C00F C00K H00K 120.5 . . ?
C00P C00K C00F 118.9(3) . . ?
C00P C00K H00K 120.5 . . ?
F006 C00L Se01 113.3(2) . . ?
F006 C00L F007 107.4(3) . . ?
F006 C00L F00A 107.1(3) . . ?
F007 C00L Se01 108.5(2) . . ?
F00A C00L Se01 113.7(2) . . ?
F00A C00L F007 106.6(3) . . ?
C00G C00M C00H 121.1(3) . . ?
C00G C00M H00M 119.4 . . ?
C00H C00M H00M 119.4 . . ?
C00H C00N H00N 119.3 . . ?
C00J C00N C00H 121.4(3) . . ?
C00J C00N H00N 119.3 . . ?
F009 C00O C00I 117.6(4) . . ?
F009 C00O C00P 118.1(3) . . ?
C00I C00O C00P 124.3(3) . . ?
C00K C00P C00O 119.7(3) . . ?
C00K C00P H00P 120.2 . . ?
C00O C00P H00P 120.2 . . ?
C00H C00Q H00A 109.5 . . ?
C00H C00Q H00B 109.5 . . ?
C00H C00Q H00C 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C00D C00E Br02 2.5(4) . . . . ?
Se01 C00D C00E N008 -177.58(19) . . . . ?
Se01 C00D C00F C00B 178.4(2) . . . . ?
Se01 C00D C00F C00K -1.8(5) . . . . ?
S003 N008 C00B C00F 168.67(19) . . . . ?
S003 N008 C00B C00I -11.6(4) . . . . ?
S003 N008 C00E Br02 10.7(3) . . . . ?
S003 N008 C00E C00D -169.2(2) . . . . ?
S003 C00C C00G C00M -179.9(2) . . . . ?
S003 C00C C00J C00N -179.2(2) . . . . ?
O004 S003 N008 C00B 157.8(2) . . . . ?
O004 S003 N008 C00E -37.3(3) . . . . ?
O004 S003 C00C C00G 16.4(3) . . . . ?
O004 S003 C00C C00J -162.7(2) . . . . ?
O005 S003 N008 C00B 29.1(2) . . . . ?
O005 S003 N008 C00E -166.1(2) . . . . ?
O005 S003 C00C C00G 151.3(2) . . . . ?
O005 S003 C00C C00J -27.8(3) . . . . ?
N008 S003 C00C C00G -97.6(2) . . . . ?
N008 S003 C00C C00J 83.4(2) . . . . ?
N008 C00B C00F C00D 0.2(3) . . . . ?
N008 C00B C00F C00K -179.6(2) . . . . ?
N008 C00B C00I C00O 179.4(3) . . . . ?
F009 C00O C00P C00K -179.3(3) . . . . ?
C00B N008 C00E Br02 177.66(19) . . . . ?
C00B N008 C00E C00D -2.3(3) . . . . ?
C00B C00F C00K C00P 0.1(4) . . . . ?
C00B C00I C00O F009 180.0(3) . . . . ?
C00B C00I C00O C00P 0.5(5) . . . . ?
C00C S003 N008 C00B -85.9(2) . . . . ?
C00C S003 N008 C00E 79.0(3) . . . . ?
C00C C00G C00M C00H -0.6(5) . . . . ?
C00C C00J C00N C00H -1.2(5) . . . . ?
C00D C00F C00K C00P -179.7(3) . . . . ?
C00E N008 C00B C00F 1.2(3) . . . . ?
C00E N008 C00B C00I -179.0(3) . . . . ?
C00E C00D C00F C00B -1.6(3) . . . . ?
C00E C00D C00F C00K 178.2(3) . . . . ?
C00F C00B C00I C00O -0.8(4) . . . . ?
C00F C00D C00E Br02 -177.5(2) . . . . ?
C00F C00D C00E N008 2.4(3) . . . . ?
C00F C00K C00P C00O -0.5(5) . . . . ?
C00G C00C C00J C00N 1.8(4) . . . . ?
C00I C00B C00F C00D -179.6(3) . . . . ?
C00I C00B C00F C00K 0.6(4) . . . . ?
C00I C00O C00P C00K 0.2(6) . . . . ?
C00J C00C C00G C00M -0.8(4) . . . . ?
C00L Se01 C00D C00E 95.0(3) . . . . ?
C00L Se01 C00D C00F -85.1(3) . . . . ?
C00M C00H C00N C00J -0.2(5) . . . . ?
C00N C00H C00M C00G 1.2(5) . . . . ?
C00Q C00H C00M C00G -179.1(3) . . . . ?
C00Q C00H C00N C00J -180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cpsecf304
_database_code_depnum_ccdc_archive 'CCDC 2179736'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Br F3 N O2 S Se'
_chemical_formula_sum            'C20 H19 Br F3 N O2 S Se'
_chemical_formula_weight         553.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.206(3)
_cell_length_b                   9.369(2)
_cell_length_c                   25.462(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.527(11)
_cell_angle_gamma                90
_cell_volume                     2189.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8405
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.710
_shelx_estimated_absorpt_T_min   0.527
_exptl_absorpt_coefficient_mu    3.677
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.4848.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27190
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.155
_diffrn_reflns_theta_max         25.155
_diffrn_reflns_theta_min         2.300
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2895
_reflns_number_total             3897
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.024
_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)+(0.0422P)²+2.2900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00Q(H00a,H00b,H00c), C00R(H00d,H00e,H00g), C00S(H00k,H00n,H00p), C00T(H00q,
 H00r,H00s)
;
_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
Se01 Se 0.52266(5) 0.58418(5) 0.40492(2) 0.06635(18) Uani 1 1 d . . . . .
Br02 Br 0.19609(6) 0.53048(5) 0.46933(2) 0.06986(19) Uani 1 1 d . . . . .
S003 S 0.03625(11) 0.22635(11) 0.41412(4) 0.0505(3) Uani 1 1 d . . . . .
O004 O -0.0253(3) 0.1405(3) 0.37253(11) 0.0616(8) Uani 1 1 d . . . . .
O005 O -0.0502(3) 0.3265(3) 0.43949(12) 0.0657(8) Uani 1 1 d . . . . .
N006 N 0.1696(3) 0.3193(3) 0.38716(12) 0.0482(8) Uani 1 1 d . . . . .
F007 F 0.4600(4) 0.6768(4) 0.30383(12) 0.1047(10) Uani 1 1 d . . . . .
F008 F 0.3239(4) 0.7662(4) 0.35620(15) 0.1178(12) Uani 1 1 d . . . . .
C009 C 0.2498(4) 0.2649(4) 0.34579(14) 0.0436(9) Uani 1 1 d . . . . .
F00A F 0.5423(5) 0.8358(4) 0.35646(16) 0.1401(16) Uani 1 1 d . . . . .
C00B C 0.3763(4) 0.3453(4) 0.34470(14) 0.0441(9) Uani 1 1 d . . . . .
C00C C 0.1336(4) 0.1207(4) 0.46103(15) 0.0460(9) Uani 1 1 d . . . . .
C00D C 0.3757(4) 0.4489(4) 0.38677(16) 0.0505(10) Uani 1 1 d . . . . .
C00E C 0.4509(4) 0.2042(4) 0.27246(15) 0.0478(9) Uani 1 1 d . . . . .
C00F C 0.1345(5) 0.1533(4) 0.51426(16) 0.0558(10) Uani 1 1 d . . . . .
H00F H 0.082222 0.230932 0.525533 0.067 Uiso 1 1 calc R U . . .
C00G C 0.2541(5) 0.4288(4) 0.41152(15) 0.0498(9) Uani 1 1 d . . . . .
C00H C 0.4743(4) 0.3156(4) 0.30721(15) 0.0502(9) Uani 1 1 d . . . . .
H00H H 0.556844 0.372166 0.305649 0.060 Uiso 1 1 calc R U . . .
C00I C 0.2208(5) 0.1545(4) 0.31065(15) 0.0550(10) Uani 1 1 d . . . . .
H00I H 0.135825 0.100945 0.311160 0.066 Uiso 1 1 calc R U . . .
C00J C 0.3217(5) 0.1259(4) 0.27472(16) 0.0543(10) Uani 1 1 d . . . . .
H00J H 0.303139 0.051418 0.250970 0.065 Uiso 1 1 calc R U . . .
C00K C 0.2950(4) -0.0458(4) 0.53427(17) 0.0567(11) Uani 1 1 d . . . . .
C00L C 0.2109(5) 0.0059(4) 0.44428(17) 0.0588(11) Uani 1 1 d . . . . .
H00L H 0.208545 -0.016897 0.408678 0.071 Uiso 1 1 calc R U . . .
C00M C 0.2146(5) 0.0681(5) 0.55016(17) 0.0618(11) Uani 1 1 d . . . . .
H00M H 0.214243 0.088125 0.585920 0.074 Uiso 1 1 calc R U . . .
C00N C 0.5601(5) 0.1695(4) 0.23203(17) 0.0588(11) Uani 1 1 d . . . . .
C00O C 0.2920(5) -0.0748(5) 0.48121(19) 0.0660(12) Uani 1 1 d . . . . .
H00O H 0.346311 -0.151014 0.469923 0.079 Uiso 1 1 calc R U . . .
C00P C 0.4588(6) 0.7226(5) 0.3526(2) 0.0708(13) Uani 1 1 d . . . . .
C00Q C 0.3817(6) -0.1378(5) 0.5735(2) 0.0848(15) Uani 1 1 d . . . . .
H00A H 0.481075 -0.105889 0.576879 0.127 Uiso 1 1 calc R U . . .
H00B H 0.377974 -0.235118 0.561735 0.127 Uiso 1 1 calc R U . . .
H00C H 0.341391 -0.131140 0.607094 0.127 Uiso 1 1 calc R U . . .
C00R C 0.5648(8) 0.2920(7) 0.1934(2) 0.117(2) Uani 1 1 d . . . . .
H00D H 0.473000 0.298509 0.172847 0.176 Uiso 1 1 calc R U . . .
H00E H 0.641064 0.275681 0.170508 0.176 Uiso 1 1 calc R U . . .
H00G H 0.583180 0.379525 0.212394 0.176 Uiso 1 1 calc R U . . .
C00S C 0.7105(6) 0.1538(8) 0.2607(2) 0.112(2) Uani 1 1 d . . . . .
H00K H 0.737948 0.241824 0.277990 0.168 Uiso 1 1 calc R U . . .
H00N H 0.779921 0.130658 0.235727 0.168 Uiso 1 1 calc R U . . .
H00P H 0.708769 0.078848 0.286324 0.168 Uiso 1 1 calc R U . . .
C00T C 0.5266(8) 0.0330(7) 0.2034(3) 0.135(3) Uani 1 1 d . . . . .
H00Q H 0.529662 -0.044410 0.228192 0.203 Uiso 1 1 calc R U . . .
H00R H 0.597299 0.017128 0.178316 0.203 Uiso 1 1 calc R U . . .
H00S H 0.431108 0.038588 0.185425 0.203 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
Se01 C00D 1.884(4) . ?
Se01 C00P 1.917(5) . ?
Br02 C00G 1.866(4) . ?
S003 O004 1.412(3) . ?
S003 O005 1.419(3) . ?
S003 N006 1.694(3) . ?
S003 C00C 1.744(4) . ?
N006 C009 1.427(4) . ?
N006 C00G 1.403(5) . ?
F007 C00P 1.315(5) . ?
F008 C00P 1.318(6) . ?
C009 C00B 1.390(5) . ?
C009 C00I 1.380(5) . ?
F00A C00P 1.309(5) . ?
C00B C00D 1.446(5) . ?
C00B C00H 1.392(5) . ?
C00C C00F 1.389(5) . ?
C00C C00L 1.376(5) . ?
C00D C00G 1.341(5) . ?
C00E C00H 1.375(5) . ?
C00E C00J 1.403(5) . ?
C00E C00N 1.529(5) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.382(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.380(5) . ?
C00J H00J 0.9300 . ?
C00K C00M 1.377(6) . ?
C00K C00O 1.376(6) . ?
C00K C00Q 1.501(6) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.379(6) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.514(7) . ?
C00N C00S 1.521(7) . ?
C00N C00T 1.491(7) . ?
C00O H00O 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?
C00R H00D 0.9600 . ?
C00R H00E 0.9600 . ?
C00R H00G 0.9600 . ?
C00S H00K 0.9600 . ?
C00S H00N 0.9600 . ?
C00S H00P 0.9600 . ?
C00T H00Q 0.9600 . ?
C00T H00R 0.9600 . ?
C00T H00S 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D Se01 C00P 96.30(19) . . ?
O004 S003 O005 120.76(19) . . ?
O004 S003 N006 104.46(16) . . ?
O004 S003 C00C 110.16(19) . . ?
O005 S003 N006 107.19(18) . . ?
O005 S003 C00C 109.88(18) . . ?
N006 S003 C00C 102.68(17) . . ?
C009 N006 S003 123.3(2) . . ?
C00G N006 S003 126.2(3) . . ?
C00G N006 C009 106.7(3) . . ?
C00B C009 N006 107.7(3) . . ?
C00I C009 N006 131.4(3) . . ?
C00I C009 C00B 120.9(3) . . ?
C009 C00B C00D 107.3(3) . . ?
C009 C00B C00H 119.7(3) . . ?
C00H C00B C00D 133.0(3) . . ?
C00F C00C S003 120.5(3) . . ?
C00L C00C S003 118.8(3) . . ?
C00L C00C C00F 120.7(4) . . ?
C00B C00D Se01 126.1(3) . . ?
C00G C00D Se01 126.1(3) . . ?
C00G C00D C00B 107.8(3) . . ?
C00H C00E C00J 117.4(4) . . ?
C00H C00E C00N 121.1(4) . . ?
C00J C00E C00N 121.4(3) . . ?
C00C C00F H00F 120.7 . . ?
C00M C00F C00C 118.7(4) . . ?
C00M C00F H00F 120.7 . . ?
N006 C00G Br02 122.6(3) . . ?
C00D C00G Br02 126.9(3) . . ?
C00D C00G N006 110.5(3) . . ?
C00B C00H H00H 119.5 . . ?
C00E C00H C00B 121.1(4) . . ?
C00E C00H H00H 119.5 . . ?
C009 C00I H00I 121.0 . . ?
C009 C00I C00J 118.0(4) . . ?
C00J C00I H00I 121.0 . . ?
C00E C00J H00J 118.6 . . ?
C00I C00J C00E 122.9(4) . . ?
C00I C00J H00J 118.6 . . ?
C00M C00K C00Q 121.3(4) . . ?
C00O C00K C00M 118.2(4) . . ?
C00O C00K C00Q 120.6(4) . . ?
C00C C00L H00L 120.6 . . ?
C00C C00L C00O 118.9(4) . . ?
C00O C00L H00L 120.6 . . ?
C00F C00M H00M 119.2 . . ?
C00K C00M C00F 121.6(4) . . ?
C00K C00M H00M 119.2 . . ?
C00R C00N C00E 109.3(4) . . ?
C00R C00N C00S 108.3(5) . . ?
C00S C00N C00E 108.7(4) . . ?
C00T C00N C00E 112.9(4) . . ?
C00T C00N C00R 110.4(5) . . ?
C00T C00N C00S 107.2(5) . . ?
C00K C00O C00L 121.9(4) . . ?
C00K C00O H00O 119.0 . . ?
C00L C00O H00O 119.0 . . ?
F007 C00P Se01 114.2(4) . . ?
F007 C00P F008 104.1(4) . . ?
F008 C00P Se01 113.6(3) . . ?
F00A C00P Se01 110.5(4) . . ?
F00A C00P F007 106.6(4) . . ?
F00A C00P F008 107.2(5) . . ?
C00K C00Q H00A 109.5 . . ?
C00K C00Q H00B 109.5 . . ?
C00K C00Q H00C 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
C00N C00R H00D 109.5 . . ?
C00N C00R H00E 109.5 . . ?
C00N C00R H00G 109.5 . . ?
H00D C00R H00E 109.5 . . ?
H00D C00R H00G 109.5 . . ?
H00E C00R H00G 109.5 . . ?
C00N C00S H00K 109.5 . . ?
C00N C00S H00N 109.5 . . ?
C00N C00S H00P 109.5 . . ?
H00K C00S H00N 109.5 . . ?
H00K C00S H00P 109.5 . . ?
H00N C00S H00P 109.5 . . ?
C00N C00T H00Q 109.5 . . ?
C00N C00T H00R 109.5 . . ?
C00N C00T H00S 109.5 . . ?
H00Q C00T H00R 109.5 . . ?
H00Q C00T H00S 109.5 . . ?
H00R C00T H00S 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C00D C00G Br02 1.2(6) . . . . ?
Se01 C00D C00G N006 179.9(3) . . . . ?
S003 N006 C009 C00B -161.6(3) . . . . ?
S003 N006 C009 C00I 18.3(6) . . . . ?
S003 N006 C00G Br02 -20.2(5) . . . . ?
S003 N006 C00G C00D 161.1(3) . . . . ?
S003 C00C C00F C00M -179.1(3) . . . . ?
S003 C00C C00L C00O 177.8(3) . . . . ?
O004 S003 N006 C009 -31.0(3) . . . . ?
O004 S003 N006 C00G 173.9(3) . . . . ?
O004 S003 C00C C00F -143.8(3) . . . . ?
O004 S003 C00C C00L 37.0(4) . . . . ?
O005 S003 N006 C009 -160.3(3) . . . . ?
O005 S003 N006 C00G 44.6(4) . . . . ?
O005 S003 C00C C00F -8.4(4) . . . . ?
O005 S003 C00C C00L 172.4(3) . . . . ?
N006 S003 C00C C00F 105.4(3) . . . . ?
N006 S003 C00C C00L -73.8(3) . . . . ?
N006 C009 C00B C00D 1.2(4) . . . . ?
N006 C009 C00B C00H -179.1(3) . . . . ?
N006 C009 C00I C00J -179.4(4) . . . . ?
C009 N006 C00G Br02 -178.6(3) . . . . ?
C009 N006 C00G C00D 2.7(4) . . . . ?
C009 C00B C00D Se01 178.6(3) . . . . ?
C009 C00B C00D C00G 0.4(4) . . . . ?
C009 C00B C00H C00E -2.6(6) . . . . ?
C009 C00I C00J C00E -0.2(6) . . . . ?
C00B C009 C00I C00J 0.4(6) . . . . ?
C00B C00D C00G Br02 179.4(3) . . . . ?
C00B C00D C00G N006 -1.9(4) . . . . ?
C00C S003 N006 C009 84.0(3) . . . . ?
C00C S003 N006 C00G -71.1(3) . . . . ?
C00C C00F C00M C00K 1.2(6) . . . . ?
C00C C00L C00O C00K 1.6(7) . . . . ?
C00D C00B C00H C00E 176.9(4) . . . . ?
C00F C00C C00L C00O -1.3(6) . . . . ?
C00G N006 C009 C00B -2.3(4) . . . . ?
C00G N006 C009 C00I 177.6(4) . . . . ?
C00H C00B C00D Se01 -1.0(6) . . . . ?
C00H C00B C00D C00G -179.2(4) . . . . ?
C00H C00E C00J C00I -1.4(6) . . . . ?
C00H C00E C00N C00R -65.2(6) . . . . ?
C00H C00E C00N C00S 52.8(6) . . . . ?
C00H C00E C00N C00T 171.6(5) . . . . ?
C00I C009 C00B C00D -178.7(3) . . . . ?
C00I C009 C00B C00H 0.9(6) . . . . ?
C00J C00E C00H C00B 2.8(6) . . . . ?
C00J C00E C00N C00R 113.3(5) . . . . ?
C00J C00E C00N C00S -128.8(5) . . . . ?
C00J C00E C00N C00T -9.9(7) . . . . ?
C00L C00C C00F C00M 0.0(6) . . . . ?
C00M C00K C00O C00L -0.4(7) . . . . ?
C00N C00E C00H C00B -178.7(4) . . . . ?
C00N C00E C00J C00I -179.9(4) . . . . ?
C00O C00K C00M C00F -1.0(6) . . . . ?
C00P Se01 C00D C00B 82.4(4) . . . . ?
C00P Se01 C00D C00G -99.7(4) . . . . ?
C00Q C00K C00M C00F -180.0(4) . . . . ?
C00Q C00K C00O C00L 178.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zzp20240521cppybr_auto
_database_code_depnum_ccdc_archive 'CCDC 2278531'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br F3 N2 O2 S Se'
_chemical_formula_sum            'C15 H10 Br F3 N2 O2 S Se'
_chemical_formula_weight         498.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFSSeBr
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'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3611(5)
_cell_length_b                   9.7326(5)
_cell_length_c                   11.2063(6)
_cell_angle_alpha                97.441(4)
_cell_angle_beta                 91.205(5)
_cell_angle_gamma                112.146(5)
_cell_volume                     835.10(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5186
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.7680
_cell_measurement_theta_min      1.8350
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.730
_exptl_absorpt_coefficient_mu    4.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.153
_diffrn_reflns_theta_min         1.838
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  10.00   0.50    1.18    --    9.30 -16.00 -30.00   96
  2  ω    -15.00  10.00   0.50    1.18    --    9.30  16.00 139.00   50
  3  ω    -40.00  14.00   0.50    1.18    --   -9.70  16.00 139.00  108
  4  ω    -34.00  -9.00   0.50    1.18    --   -9.70 -16.00 -30.00   50
  5  ω      5.00  99.00   0.50    1.18    --    9.30  77.00-120.00  188
  6  ω    -17.00  43.00   0.50    1.18    --    9.30  82.00 120.00  120
  7  ω     28.00  94.00   0.50    1.18    --    9.30  82.00 -90.00  132
  8  ω    -14.00  11.00   0.50    1.18    --    9.30  82.00 -90.00   50
  9  ω     22.00  99.00   0.50    1.18    --    9.30  57.00  30.00  154
 10  ω    -18.00  93.00   0.50    1.18    --    9.30  82.00-180.00  222
 11  ω     50.00  76.00   0.50    1.18    --    9.30  82.00 120.00   52
 12  ω     -7.00  18.00   0.50    1.18    --   -9.70 -82.00-150.00   50
 13  ω    -31.00   6.00   0.50    1.18    --   -9.70 -82.00  90.00   74
 14  ω    -10.00  79.00   0.50    1.18    --   -9.70  77.00 120.00  178
 15  ω    -60.00  17.00   0.50    1.18    --   -9.70 -82.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0503548000
_diffrn_orient_matrix_UB_12      -0.0781423000
_diffrn_orient_matrix_UB_13      -0.0078576000
_diffrn_orient_matrix_UB_21      0.0754616000
_diffrn_orient_matrix_UB_22      -0.0149692000
_diffrn_orient_matrix_UB_23      -0.0112522000
_diffrn_orient_matrix_UB_31      0.0144047000
_diffrn_orient_matrix_UB_32      -0.0004235000
_diffrn_orient_matrix_UB_33      0.0625293000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             3478
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      0.982
_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)+(0.0563P)²+0.8374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00N(H00N),
 C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_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
Se01 Se 0.64486(5) 0.38884(4) 0.53260(3) 0.02488(13) Uani 1 1 d . . . . .
Br02 Br 1.01356(5) 0.29932(5) 0.58447(4) 0.03139(14) Uani 1 1 d . . . . .
S003 S 0.49103(12) 0.22021(11) 0.21880(8) 0.0205(2) Uani 1 1 d . . . . .
F004 F 0.5506(3) 0.1271(3) 0.6344(2) 0.0376(6) Uani 1 1 d . . . . .
F005 F 0.3551(3) 0.1224(3) 0.5065(2) 0.0414(6) Uani 1 1 d . . . . .
F006 F 0.3997(4) 0.2591(3) 0.6803(2) 0.0460(7) Uani 1 1 d . . . . .
O007 O 0.4218(3) 0.3080(3) 0.2974(2) 0.0280(6) Uani 1 1 d . . . . .
O008 O 0.3827(3) 0.0732(3) 0.1630(2) 0.0250(6) Uani 1 1 d . . . . .
N009 N 0.6498(4) 0.2000(3) 0.3038(3) 0.0175(6) Uani 1 1 d . . . . .
N00A N 0.7188(4) 0.0434(3) 0.1451(3) 0.0198(7) Uani 1 1 d . . . . .
C00B C 0.8680(5) 0.2397(4) 0.4415(3) 0.0202(8) Uani 1 1 d . . . . .
C00C C 0.7276(5) 0.2740(4) 0.4207(3) 0.0184(8) Uani 1 1 d . . . . .
C00D C 1.0028(5) 0.0766(4) 0.3078(4) 0.0231(8) Uani 1 1 d . . . . .
H00D H 1.097596 0.087350 0.361519 0.028 Uiso 1 1 calc R U . . .
C00E C 0.7492(5) 0.1216(4) 0.2546(3) 0.0187(8) Uani 1 1 d . . . . .
C00F C 0.7193(5) 0.3440(4) -0.0829(4) 0.0235(8) Uani 1 1 d . . . . .
H00F H 0.733898 0.296872 -0.159216 0.028 Uiso 1 1 calc R U . . .
C00G C 0.6235(5) 0.2560(4) -0.0013(3) 0.0196(8) Uani 1 1 d . . . . .
H00G H 0.572375 0.149899 -0.021561 0.024 Uiso 1 1 calc R U . . .
C00H C 0.9718(5) -0.0073(4) 0.1945(4) 0.0238(9) Uani 1 1 d . . . . .
H00H H 1.046591 -0.056563 0.168698 0.029 Uiso 1 1 calc R U . . .
C00I C 0.6039(5) 0.3254(4) 0.1097(3) 0.0206(8) Uani 1 1 d . . . . .
C00J C 0.8326(5) -0.0205(4) 0.1176(3) 0.0221(8) Uani 1 1 d . . . . .
H00J H 0.817053 -0.078789 0.040206 0.027 Uiso 1 1 calc R U . . .
C00K C 0.8865(4) 0.1444(4) 0.3383(3) 0.0176(8) Uani 1 1 d . . . . .
C00L C 0.4765(5) 0.2124(5) 0.5905(4) 0.0287(9) Uani 1 1 d . . . . .
C00M C 0.7941(5) 0.4990(5) -0.0555(4) 0.0265(9) Uani 1 1 d . . . . .
C00N C 0.7716(6) 0.5660(4) 0.0573(4) 0.0321(10) Uani 1 1 d . . . . .
H00N H 0.821648 0.672099 0.077485 0.039 Uiso 1 1 calc R U . . .
C00O C 0.6780(5) 0.4807(4) 0.1398(4) 0.0286(9) Uani 1 1 d . . . . .
H00O H 0.664138 0.527455 0.216546 0.034 Uiso 1 1 calc R U . . .
C00P C 0.8994(6) 0.5949(5) -0.1434(4) 0.0343(10) Uani 1 1 d . . . . .
H00A H 0.923471 0.531084 -0.209678 0.051 Uiso 1 1 calc R U . . .
H00B H 1.008810 0.667195 -0.101829 0.051 Uiso 1 1 calc R U . . .
H00C H 0.834309 0.648975 -0.175671 0.051 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
Se01 C00C 1.886(4) . ?
Se01 C00L 1.964(4) . ?
Br02 C00B 1.878(4) . ?
S003 O007 1.429(3) . ?
S003 O008 1.424(3) . ?
S003 N009 1.703(3) . ?
S003 C00I 1.754(4) . ?
F004 C00L 1.340(5) . ?
F005 C00L 1.327(5) . ?
F006 C00L 1.327(5) . ?
N009 C00C 1.423(4) . ?
N009 C00E 1.402(4) . ?
N00A C00E 1.322(5) . ?
N00A C00J 1.341(5) . ?
C00B C00C 1.360(5) . ?
C00B C00K 1.435(5) . ?
C00D H00D 0.9500 . ?
C00D C00H 1.380(5) . ?
C00D C00K 1.393(5) . ?
C00E C00K 1.399(5) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.388(5) . ?
C00F C00M 1.386(6) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.381(5) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.389(5) . ?
C00I C00O 1.391(5) . ?
C00J H00J 0.9500 . ?
C00M C00N 1.396(6) . ?
C00M C00P 1.507(5) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.377(6) . ?
C00O H00O 0.9500 . ?
C00P H00A 0.9800 . ?
C00P H00B 0.9800 . ?
C00P H00C 0.9800 . ?

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
C00C Se01 C00L 93.78(16) . . ?
O007 S003 N009 105.85(15) . . ?
O007 S003 C00I 109.62(17) . . ?
O008 S003 O007 120.40(16) . . ?
O008 S003 N009 106.06(15) . . ?
O008 S003 C00I 109.93(17) . . ?
N009 S003 C00I 103.52(16) . . ?
C00C N009 S003 129.9(2) . . ?
C00E N009 S003 121.5(3) . . ?
C00E N009 C00C 107.6(3) . . ?
C00E N00A C00J 113.8(3) . . ?
C00C C00B Br02 126.3(3) . . ?
C00C C00B C00K 109.7(3) . . ?
C00K C00B Br02 124.0(3) . . ?
N009 C00C Se01 126.8(3) . . ?
C00B C00C Se01 125.3(3) . . ?
C00B C00C N009 107.8(3) . . ?
C00H C00D H00D 122.1 . . ?
C00H C00D C00K 115.8(3) . . ?
C00K C00D H00D 122.1 . . ?
N00A C00E N009 124.7(3) . . ?
N00A C00E C00K 126.5(3) . . ?
C00K C00E N009 108.8(3) . . ?
C00G C00F H00F 119.2 . . ?
C00M C00F H00F 119.2 . . ?
C00M C00F C00G 121.6(4) . . ?
C00F C00G H00G 120.6 . . ?
C00F C00G C00I 118.8(3) . . ?
C00I C00G H00G 120.6 . . ?
C00D C00H H00H 119.6 . . ?
C00D C00H C00J 120.8(4) . . ?
C00J C00H H00H 119.6 . . ?
C00G C00I S003 121.0(3) . . ?
C00G C00I C00O 120.9(4) . . ?
C00O C00I S003 118.1(3) . . ?
N00A C00J C00H 124.5(4) . . ?
N00A C00J H00J 117.8 . . ?
C00H C00J H00J 117.8 . . ?
C00D C00K C00B 135.3(3) . . ?
C00D C00K C00E 118.6(3) . . ?
C00E C00K C00B 106.1(3) . . ?
F004 C00L Se01 112.8(3) . . ?
F005 C00L Se01 113.8(3) . . ?
F005 C00L F004 106.4(3) . . ?
F006 C00L Se01 108.5(3) . . ?
F006 C00L F004 106.9(3) . . ?
F006 C00L F005 108.3(3) . . ?
C00F C00M C00N 118.3(4) . . ?
C00F C00M C00P 121.8(4) . . ?
C00N C00M C00P 119.9(4) . . ?
C00M C00N H00N 119.5 . . ?
C00O C00N C00M 121.0(4) . . ?
C00O C00N H00N 119.5 . . ?
C00I C00O H00O 120.3 . . ?
C00N C00O C00I 119.4(4) . . ?
C00N C00O H00O 120.3 . . ?
C00M C00P H00A 109.5 . . ?
C00M C00P H00B 109.5 . . ?
C00M C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br02 C00B C00C Se01 -0.7(5) . . . . ?
Br02 C00B C00C N009 -177.0(3) . . . . ?
Br02 C00B C00K C00D -2.8(6) . . . . ?
Br02 C00B C00K C00E 177.2(3) . . . . ?
S003 N009 C00C Se01 14.4(5) . . . . ?
S003 N009 C00C C00B -169.4(3) . . . . ?
S003 N009 C00E N00A -7.9(5) . . . . ?
S003 N009 C00E C00K 170.2(2) . . . . ?
S003 C00I C00O C00N 178.1(3) . . . . ?
O007 S003 N009 C00C -11.3(4) . . . . ?
O007 S003 N009 C00E -178.6(3) . . . . ?
O007 S003 C00I C00G -154.0(3) . . . . ?
O007 S003 C00I C00O 28.1(4) . . . . ?
O008 S003 N009 C00C -140.3(3) . . . . ?
O008 S003 N009 C00E 52.4(3) . . . . ?
O008 S003 C00I C00G -19.5(4) . . . . ?
O008 S003 C00I C00O 162.6(3) . . . . ?
N009 S003 C00I C00G 93.5(3) . . . . ?
N009 S003 C00I C00O -84.5(3) . . . . ?
N009 C00E C00K C00B 0.1(4) . . . . ?
N009 C00E C00K C00D -179.8(3) . . . . ?
N00A C00E C00K C00B 178.2(3) . . . . ?
N00A C00E C00K C00D -1.8(6) . . . . ?
C00C N009 C00E N00A -177.7(3) . . . . ?
C00C N009 C00E C00K 0.3(4) . . . . ?
C00C C00B C00K C00D 179.4(4) . . . . ?
C00C C00B C00K C00E -0.6(4) . . . . ?
C00D C00H C00J N00A -0.5(6) . . . . ?
C00E N009 C00C Se01 -176.9(3) . . . . ?
C00E N009 C00C C00B -0.7(4) . . . . ?
C00E N00A C00J C00H -0.4(5) . . . . ?
C00F C00G C00I S003 -177.7(3) . . . . ?
C00F C00G C00I C00O 0.2(5) . . . . ?
C00F C00M C00N C00O 0.2(6) . . . . ?
C00G C00F C00M C00N 0.2(6) . . . . ?
C00G C00F C00M C00P 179.5(3) . . . . ?
C00G C00I C00O C00N 0.2(6) . . . . ?
C00H C00D C00K C00B -179.2(4) . . . . ?
C00H C00D C00K C00E 0.7(5) . . . . ?
C00I S003 N009 C00C 104.0(3) . . . . ?
C00I S003 N009 C00E -63.3(3) . . . . ?
C00J N00A C00E N009 179.3(3) . . . . ?
C00J N00A C00E C00K 1.6(5) . . . . ?
C00K C00B C00C Se01 177.0(3) . . . . ?
C00K C00B C00C N009 0.8(4) . . . . ?
C00K C00D C00H C00J 0.3(5) . . . . ?
C00L Se01 C00C N009 81.0(3) . . . . ?
C00L Se01 C00C C00B -94.6(3) . . . . ?
C00M C00F C00G C00I -0.4(6) . . . . ?
C00M C00N C00O C00I -0.4(6) . . . . ?
C00P C00M C00N C00O -179.1(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_zzp20240430-cpseph_auto
_database_code_depnum_ccdc_archive 'CCDC 2353241'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Br N O2 S Se'
_chemical_formula_sum            'C21 H16 Br N O2 S Se'
_chemical_formula_weight         505.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONSSeBr
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'
Br Br -0.6763 1.2805 '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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.1799(2)
_cell_length_b                   10.0887(2)
_cell_length_c                   14.8295(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.326(2)
_cell_angle_gamma                90
_cell_volume                     1966.23(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7315
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      68.0190
_cell_measurement_theta_min      4.3280
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.581
_exptl_absorpt_coefficient_mu    6.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10111
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.126
_diffrn_reflns_theta_min         4.329
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  66.00   0.50    2.00    --   42.40 -66.00  90.00  136
  2  ω     22.00  62.00   0.50    2.00    --   42.40  66.00-134.00   80
  3  ω     69.00 161.00   0.50    4.00    --   93.70  66.00-134.00  184
  4  ω     46.00 117.00   0.50    4.00    --   93.70 -66.00  90.00  142
  5  ω     86.00 129.00   0.50    2.00    --   42.40  43.00 -90.00   86
  6  ω    102.00 132.00   0.50    2.00    --   42.40  43.00-180.00   60
  7  ω     96.00 124.00   0.50    2.00    --   42.40  77.00 -30.00   56
  8  ω     85.00 127.00   0.50    2.00    --   42.40  66.00-134.00   84
  9  ω     15.00  68.00   0.50    2.00    --   42.40  43.00 -90.00  106
 10  ω     18.00 132.00   0.50    2.00    --   42.40  77.00 -60.00  228
 11  ω     87.00 112.00   0.50    2.00    --   42.40  54.00  30.00   50
 12  ω     13.00  62.00   0.50    2.00    --   42.40  54.00  30.00   98
 13  ω     45.00  70.00   0.50    2.00    --   42.40  77.00 -30.00   50
 14  ω     36.00  64.00   0.50    2.00    --   42.40  43.00-180.00   56
 15  ω     97.00 175.00   0.50    4.00    --   93.70  77.00  90.00  156
 16  ω     64.00 150.00   0.50    4.00    --   93.70  50.00 150.00  172
 17  ω    101.00 183.00   0.50    4.00    --   93.70  68.00 120.00  164
 18  ω     77.00 102.00   0.50    4.00    --   93.70  68.00 -30.00   50
 19  ω     25.00  50.00   0.50    4.00    --   93.70 -68.00-180.00   50
 20  ω    128.00 178.00   0.50    4.00    --   93.70  77.00-180.00  100
 21  ω    118.00 144.00   0.50    4.00    --   93.70  77.00 -30.00   52
 22  ω     68.00  93.00   0.50    4.00    --   93.70  77.00 -30.00   50
 23  ω     77.00 161.00   0.50    4.00    --   93.70  82.00-120.00  168
 24  ω     76.00 109.00   0.50    4.00    --   93.70 -68.00-180.00   66
 25  ω     70.00 121.00   0.50    4.00    --   93.70  77.00-180.00  102
 26  ω     69.00 178.00   0.50    4.00    --   93.70  77.00 150.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0641375000
_diffrn_orient_matrix_UB_12      -0.1078988000
_diffrn_orient_matrix_UB_13      -0.0509220000
_diffrn_orient_matrix_UB_21      0.0420525000
_diffrn_orient_matrix_UB_22      0.0437738000
_diffrn_orient_matrix_UB_23      -0.0894621000
_diffrn_orient_matrix_UB_31      0.0887024000
_diffrn_orient_matrix_UB_32      -0.0987286000
_diffrn_orient_matrix_UB_33      0.0159983000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3092
_reflns_number_total             3555
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.624
_refine_diff_density_min         -1.670
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.036
_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)+(0.1546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1940
_refine_ls_wR_factor_ref         0.1984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00M(H00a,H00e,H00f)
;
_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
Br01 Br 0.35590(4) 0.05775(5) -0.01313(3) 0.0452(3) Uani 1 1 d . . . . .
Se02 Se 0.60087(4) 0.64461(5) 0.23171(3) 0.0421(3) Uani 1 1 d . . . . .
S003 S 0.61051(9) 0.11436(12) 0.33834(7) 0.0402(3) Uani 1 1 d . . . . .
O004 O 0.6059(3) -0.0041(3) 0.2857(2) 0.0470(9) Uani 1 1 d . . . . .
O005 O 0.6978(3) 0.1447(4) 0.3973(2) 0.0522(10) Uani 1 1 d . . . . .
N006 N 0.6025(3) 0.2405(4) 0.2644(2) 0.0369(8) Uani 1 1 d . . . . .
C007 C 0.5182(4) 0.3845(5) 0.1676(3) 0.0336(10) Uani 1 1 d . . . . .
C008 C 0.5308(4) 0.2476(5) 0.1887(3) 0.0337(9) Uani 1 1 d . . . . .
C009 C 0.4206(4) 0.1894(5) 0.0630(3) 0.0356(10) Uani 1 1 d . . . . .
C00A C 0.5009(4) 0.1293(5) 0.3976(3) 0.0372(10) Uani 1 1 d . . . . .
C00B C 0.4067(4) 0.3222(5) 0.0396(3) 0.0352(9) Uani 1 1 d . . . . .
H00B H 0.364014 0.345440 -0.012437 0.042 Uiso 1 1 calc R U . . .
C00C C 0.4546(4) 0.4197(5) 0.0917(3) 0.0362(10) Uani 1 1 d . . . . .
H00C H 0.444520 0.510394 0.076281 0.043 Uiso 1 1 calc R U . . .
C00D C 0.6300(4) 0.3701(5) 0.2898(3) 0.0403(11) Uani 1 1 d . . . . .
H00D H 0.675910 0.393084 0.339809 0.048 Uiso 1 1 calc R U . . .
C00E C 0.4611(4) 0.6933(4) 0.2428(3) 0.0386(10) Uani 1 1 d . . . . .
C00F C 0.5813(4) 0.4581(5) 0.2325(3) 0.0371(10) Uani 1 1 d . . . . .
C00G C 0.3329(5) 0.0615(5) 0.4259(4) 0.0485(13) Uani 1 1 d . . . . .
H00G H 0.276963 0.003261 0.413699 0.058 Uiso 1 1 calc R U . . .
C00H C 0.4822(4) 0.1484(4) 0.1377(3) 0.0358(10) Uani 1 1 d . . . . .
H00H H 0.490641 0.057413 0.152896 0.043 Uiso 1 1 calc R U . . .
C00I C 0.4163(4) 0.7849(5) 0.1826(3) 0.0457(12) Uani 1 1 d . . . . .
H00I H 0.453301 0.819954 0.135430 0.055 Uiso 1 1 calc R U . . .
C00J C 0.3268(4) 0.1589(5) 0.4904(3) 0.0415(11) Uani 1 1 d . . . . .
C00K C 0.4059(4) 0.6411(5) 0.3108(4) 0.0485(13) Uani 1 1 d . . . . .
H00K H 0.436162 0.577295 0.351563 0.058 Uiso 1 1 calc R U . . .
C00L C 0.4192(4) 0.0464(5) 0.3784(3) 0.0443(12) Uani 1 1 d . . . . .
H00L H 0.421738 -0.020115 0.333284 0.053 Uiso 1 1 calc R U . . .
C00M C 0.2327(4) 0.1749(6) 0.5412(4) 0.0506(13) Uani 1 1 d . . . . .
H00A H 0.181399 0.225097 0.504014 0.076 Uiso 1 1 calc R U . . .
H00E H 0.250023 0.222782 0.597747 0.076 Uiso 1 1 calc R U . . .
H00F H 0.205495 0.087374 0.554732 0.076 Uiso 1 1 calc R U . . .
C00N C 0.3156(5) 0.8256(5) 0.1919(4) 0.0529(13) Uani 1 1 d . . . . .
H00N H 0.284181 0.888118 0.150867 0.063 Uiso 1 1 calc R U . . .
C00O C 0.3075(5) 0.6820(6) 0.3190(4) 0.0599(15) Uani 1 1 d . . . . .
H00O H 0.269965 0.646095 0.365482 0.072 Uiso 1 1 calc R U . . .
C00P C 0.4975(4) 0.2266(6) 0.4635(4) 0.0566(15) Uani 1 1 d . . . . .
H00P H 0.553951 0.283799 0.476548 0.068 Uiso 1 1 calc R U . . .
C00Q C 0.4111(5) 0.2393(7) 0.5100(4) 0.0587(15) Uani 1 1 d . . . . .
H00Q H 0.409326 0.304302 0.556213 0.070 Uiso 1 1 calc R U . . .
C00R C 0.2629(4) 0.7749(6) 0.2603(4) 0.0549(14) Uani 1 1 d . . . . .
H00R H 0.195340 0.803811 0.267285 0.066 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
Br01 C009 1.903(4) . ?
Se02 C00E 1.925(5) . ?
Se02 C00F 1.900(5) . ?
S003 O004 1.426(4) . ?
S003 O005 1.425(4) . ?
S003 N006 1.678(4) . ?
S003 C00A 1.753(5) . ?
N006 C008 1.415(6) . ?
N006 C00D 1.401(6) . ?
C007 C008 1.423(6) . ?
C007 C00C 1.398(6) . ?
C007 C00F 1.430(7) . ?
C008 C00H 1.382(7) . ?
C009 C00B 1.392(6) . ?
C009 C00H 1.386(6) . ?
C00A C00L 1.376(7) . ?
C00A C00P 1.389(7) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.375(7) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00F 1.356(7) . ?
C00E C00I 1.386(7) . ?
C00E C00K 1.391(7) . ?
C00G H00G 0.9500 . ?
C00G C00J 1.377(7) . ?
C00G C00L 1.391(8) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00N 1.405(8) . ?
C00J C00M 1.508(7) . ?
C00J C00Q 1.389(8) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.375(9) . ?
C00L H00L 0.9500 . ?
C00M H00A 0.9800 . ?
C00M H00E 0.9800 . ?
C00M H00F 0.9800 . ?
C00N H00N 0.9500 . ?
C00N C00R 1.371(8) . ?
C00O H00O 0.9500 . ?
C00O C00R 1.380(9) . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.380(8) . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00F Se02 C00E 96.9(2) . . ?
O004 S003 N006 106.3(2) . . ?
O004 S003 C00A 110.1(2) . . ?
O005 S003 O004 121.0(2) . . ?
O005 S003 N006 104.2(2) . . ?
O005 S003 C00A 109.4(2) . . ?
N006 S003 C00A 104.4(2) . . ?
C008 N006 S003 124.2(3) . . ?
C00D N006 S003 122.0(3) . . ?
C00D N006 C008 108.0(4) . . ?
C008 C007 C00F 107.7(4) . . ?
C00C C007 C008 118.4(4) . . ?
C00C C007 C00F 133.8(4) . . ?
N006 C008 C007 106.4(4) . . ?
C00H C008 N006 130.7(4) . . ?
C00H C008 C007 122.8(4) . . ?
C00B C009 Br01 118.6(3) . . ?
C00H C009 Br01 118.4(3) . . ?
C00H C009 C00B 123.0(4) . . ?
C00L C00A S003 120.3(4) . . ?
C00L C00A C00P 120.6(5) . . ?
C00P C00A S003 119.1(4) . . ?
C009 C00B H00B 119.9 . . ?
C00C C00B C009 120.1(4) . . ?
C00C C00B H00B 119.9 . . ?
C007 C00C H00C 120.2 . . ?
C00B C00C C007 119.5(4) . . ?
C00B C00C H00C 120.2 . . ?
N006 C00D H00D 125.0 . . ?
C00F C00D N006 110.0(4) . . ?
C00F C00D H00D 125.0 . . ?
C00I C00E Se02 118.6(4) . . ?
C00I C00E C00K 119.9(5) . . ?
C00K C00E Se02 121.4(4) . . ?
C007 C00F Se02 125.6(3) . . ?
C00D C00F Se02 126.4(4) . . ?
C00D C00F C007 107.8(4) . . ?
C00J C00G H00G 119.2 . . ?
C00J C00G C00L 121.5(5) . . ?
C00L C00G H00G 119.2 . . ?
C008 C00H C009 116.1(4) . . ?
C008 C00H H00H 121.9 . . ?
C009 C00H H00H 121.9 . . ?
C00E C00I H00I 120.3 . . ?
C00E C00I C00N 119.4(5) . . ?
C00N C00I H00I 120.3 . . ?
C00G C00J C00M 121.1(5) . . ?
C00G C00J C00Q 118.3(5) . . ?
C00Q C00J C00M 120.5(5) . . ?
C00E C00K H00K 120.0 . . ?
C00O C00K C00E 119.9(5) . . ?
C00O C00K H00K 120.0 . . ?
C00A C00L C00G 119.0(5) . . ?
C00A C00L H00L 120.5 . . ?
C00G C00L H00L 120.5 . . ?
C00J C00M H00A 109.5 . . ?
C00J C00M H00E 109.5 . . ?
C00J C00M H00F 109.5 . . ?
H00A C00M H00E 109.5 . . ?
H00A C00M H00F 109.5 . . ?
H00E C00M H00F 109.5 . . ?
C00I C00N H00N 120.0 . . ?
C00R C00N C00I 120.0(5) . . ?
C00R C00N H00N 120.0 . . ?
C00K C00O H00O 119.7 . . ?
C00K C00O C00R 120.5(5) . . ?
C00R C00O H00O 119.7 . . ?
C00A C00P H00P 120.4 . . ?
C00Q C00P C00A 119.3(5) . . ?
C00Q C00P H00P 120.4 . . ?
C00J C00Q H00Q 119.4 . . ?
C00P C00Q C00J 121.2(5) . . ?
C00P C00Q H00Q 119.4 . . ?
C00N C00R C00O 120.3(6) . . ?
C00N C00R H00R 119.9 . . ?
C00O C00R H00R 119.9 . . ?

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
Br01 C009 C00B C00C -178.2(4) . . . . ?
Br01 C009 C00H C008 177.4(3) . . . . ?
Se02 C00E C00I C00N -177.4(4) . . . . ?
Se02 C00E C00K C00O 177.4(4) . . . . ?
S003 N006 C008 C007 155.4(3) . . . . ?
S003 N006 C008 C00H -27.8(7) . . . . ?
S003 N006 C00D C00F -156.0(4) . . . . ?
S003 C00A C00L C00G -179.4(4) . . . . ?
S003 C00A C00P C00Q 179.6(5) . . . . ?
O004 S003 N006 C008 46.3(4) . . . . ?
O004 S003 N006 C00D -163.5(4) . . . . ?
O004 S003 C00A C00L -10.5(5) . . . . ?
O004 S003 C00A C00P 170.0(4) . . . . ?
O005 S003 N006 C008 175.2(4) . . . . ?
O005 S003 N006 C00D -34.7(4) . . . . ?
O005 S003 C00A C00L -145.7(4) . . . . ?
O005 S003 C00A C00P 34.8(5) . . . . ?
N006 S003 C00A C00L 103.2(4) . . . . ?
N006 S003 C00A C00P -76.3(5) . . . . ?
N006 C008 C00H C009 -175.7(4) . . . . ?
N006 C00D C00F Se02 -174.4(3) . . . . ?
N006 C00D C00F C007 0.8(6) . . . . ?
C007 C008 C00H C009 0.8(7) . . . . ?
C008 N006 C00D C00F -1.6(5) . . . . ?
C008 C007 C00C C00B -0.4(7) . . . . ?
C008 C007 C00F Se02 175.6(3) . . . . ?
C008 C007 C00F C00D 0.3(6) . . . . ?
C009 C00B C00C C007 0.8(7) . . . . ?
C00A S003 N006 C008 -70.1(4) . . . . ?
C00A S003 N006 C00D 80.1(4) . . . . ?
C00A C00P C00Q C00J -1.6(10) . . . . ?
C00B C009 C00H C008 -0.3(7) . . . . ?
C00C C007 C008 N006 176.7(4) . . . . ?
C00C C007 C008 C00H -0.4(7) . . . . ?
C00C C007 C00F Se02 -2.0(8) . . . . ?
C00C C007 C00F C00D -177.3(5) . . . . ?
C00D N006 C008 C007 1.7(5) . . . . ?
C00D N006 C008 C00H 178.6(5) . . . . ?
C00E Se02 C00F C007 61.0(4) . . . . ?
C00E Se02 C00F C00D -124.5(5) . . . . ?
C00E C00I C00N C00R 0.2(8) . . . . ?
C00E C00K C00O C00R -0.1(9) . . . . ?
C00F C007 C008 N006 -1.3(5) . . . . ?
C00F C007 C008 C00H -178.4(4) . . . . ?
C00F C007 C00C C00B 177.0(5) . . . . ?
C00G C00J C00Q C00P 2.9(9) . . . . ?
C00H C009 C00B C00C -0.4(8) . . . . ?
C00I C00E C00K C00O -0.9(8) . . . . ?
C00I C00N C00R C00O -1.3(9) . . . . ?
C00J C00G C00L C00A 1.3(8) . . . . ?
C00K C00E C00I C00N 0.9(7) . . . . ?
C00K C00O C00R C00N 1.3(9) . . . . ?
C00L C00A C00P C00Q 0.1(9) . . . . ?
C00L C00G C00J C00M 179.6(5) . . . . ?
C00L C00G C00J C00Q -2.7(8) . . . . ?
C00M C00J C00Q C00P -179.4(6) . . . . ?
C00P C00A C00L C00G 0.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.983
_oxdiff_exptl_absorpt_empirical_full_min 0.335
####################################################################### 
# 
# 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_zzp20240501-cpnhph-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2353240'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 F3 N Se'
_chemical_formula_sum            'C15 H10 F3 N Se'
_chemical_formula_weight         340.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNFSe
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'
Se Se -0.7943 1.1372 '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                   18.3963(3)
_cell_length_b                   7.89020(10)
_cell_length_c                   18.5690(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2695.30(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5935
_cell_measurement_temperature    200.0(3)
_cell_measurement_theta_max      68.0080
_cell_measurement_theta_min      2.3560
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    4.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9264
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.104
_diffrn_reflns_theta_min         4.763
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  67.00   0.50    1.00    --   42.30 -82.00 -67.00   92
  2  ω    -34.00  -8.00   0.50    1.00    --   42.30 -82.00 -67.00   52
  3  ω      0.00  26.00   0.50    1.00    --   42.30 -41.00 114.00   52
  4  ω     74.00 120.00   0.50    1.00    --   42.30  82.00  54.00   92
  5  ω     79.00 105.00   0.50    1.00    --   93.70 -82.00 -67.00   52
  6  ω     36.00  62.00   0.50    1.00    --   93.70 -41.00 114.00   52
  7  ω     19.00  75.00   0.50    1.00    --   93.70 -82.00 -67.00  112
  8  ω     79.00 129.00   0.50    1.00    --   93.70  41.00 -92.00  100
  9  ω     92.00 132.00   0.50    1.00    --   42.30  65.00-180.00   80
 10  ω     98.00 132.00   0.50    1.00    --   42.30  65.00 120.00   68
 11  ω     48.00  73.00   0.50    1.00    --   42.30  41.00 -92.00   50
 12  ω    -45.00  33.00   0.50    1.00    --   42.30 -54.00 -60.00  156
 13  ω     82.00 132.00   0.50    1.00    --   42.30  82.00 -30.00  100
 14  ω     29.00  54.00   0.50    1.00    --   42.30  82.00 -30.00   50
 15  ω     26.00  86.00   0.50    1.00    --   42.30  65.00 120.00  120
 16  ω     68.00 182.00   0.50    1.00    --   93.70  77.00 150.00  228
 17  ω     37.00  62.00   0.50    1.00    --   93.70 -77.00  60.00   50
 18  ω    158.00 183.00   0.50    1.00    --   93.70  82.00 120.00   50
 19  ω     66.00 146.00   0.50    1.00    --   93.70  82.00 120.00  160
 20  ω     93.00 183.00   0.50    1.00    --   93.70  68.00  30.00  180
 21  ω     97.00 122.00   0.50    1.00    --   93.70  68.00-150.00   50
 22  ω    158.00 183.00   0.50    1.00    --   93.70  68.00-150.00   50
 23  ω    100.00 125.00   0.50    1.00    --   93.70  82.00  54.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0721612000
_diffrn_orient_matrix_UB_12      -0.0987411000
_diffrn_orient_matrix_UB_13      0.0028234000
_diffrn_orient_matrix_UB_21      -0.0083184000
_diffrn_orient_matrix_UB_22      -0.0200607000
_diffrn_orient_matrix_UB_23      0.0821273000
_diffrn_orient_matrix_UB_31      -0.0416096000
_diffrn_orient_matrix_UB_32      -0.1672972000
_diffrn_orient_matrix_UB_33      -0.0114817000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2015
_reflns_number_total             2437
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.620
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       0.0008(2)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1591P)²+0.3273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2176
_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:
 C007(H007), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J)
;
_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
Se01 Se 0.29638(3) 0.49167(6) 0.61175(2) 0.0379(4) Uani 1 1 d . . . . .
N002 N 0.36894(16) 0.3436(4) 0.73575(15) 0.0287(7) Uani 1 1 d . . . . .
F003 F 0.35399(18) 0.7559(5) 0.54146(18) 0.0842(11) Uani 1 1 d . . . . .
C004 C 0.3593(2) 0.3268(4) 0.80911(19) 0.0273(8) Uani 1 1 d . . . . .
F005 F 0.43521(17) 0.6001(6) 0.5851(3) 0.1061(15) Uani 1 1 d . . . . .
C006 C 0.43085(19) 0.2824(5) 0.69652(18) 0.0281(8) Uani 1 1 d . . . . .
C007 C 0.2668(3) 0.4881(4) 0.7648(2) 0.0356(10) Uani 1 1 d . . . . .
H007 H 0.223999 0.554942 0.761035 0.043 Uiso 1 1 calc R U . . .
C008 C 0.2959(2) 0.4150(5) 0.8293(2) 0.0337(9) Uani 1 1 d . . . . .
C009 C 0.4023(2) 0.2397(4) 0.85929(19) 0.0321(9) Uani 1 1 d . . . . .
H009 H 0.445003 0.180813 0.845076 0.039 Uiso 1 1 calc R U . . .
C00A C 0.4995(2) 0.3397(5) 0.7156(2) 0.0349(9) Uani 1 1 d . . . . .
H00A H 0.505430 0.417666 0.754163 0.042 Uiso 1 1 calc R U . . .
C00B C 0.2750(3) 0.4161(6) 0.9012(2) 0.0431(10) Uani 1 1 d . . . . .
H00B H 0.232231 0.474206 0.915707 0.052 Uiso 1 1 calc R U . . .
C00C C 0.4214(2) 0.1696(5) 0.6407(2) 0.0364(9) Uani 1 1 d . . . . .
H00C H 0.374120 0.129570 0.628917 0.044 Uiso 1 1 calc R U . . .
C00D C 0.3118(2) 0.4439(5) 0.7100(2) 0.0327(8) Uani 1 1 d . . . . .
C00E C 0.5594(2) 0.2807(6) 0.6774(2) 0.0436(10) Uani 1 1 d . . . . .
H00E H 0.606891 0.315753 0.690825 0.052 Uiso 1 1 calc R U . . .
C00F C 0.4813(3) 0.1148(6) 0.6019(2) 0.0445(11) Uani 1 1 d . . . . .
H00F H 0.475179 0.038324 0.562843 0.053 Uiso 1 1 calc R U . . .
C00G C 0.3800(2) 0.2434(5) 0.9302(2) 0.0385(10) Uani 1 1 d . . . . .
H00G H 0.407709 0.184987 0.965507 0.046 Uiso 1 1 calc R U . . .
C00H C 0.3172(2) 0.3314(5) 0.9514(2) 0.0429(10) Uani 1 1 d . . . . .
H00H H 0.303587 0.332980 1.000745 0.051 Uiso 1 1 calc R U . . .
F00I F 0.3777(3) 0.7659(5) 0.6518(2) 0.126(2) Uani 1 1 d . . . . .
C00J C 0.5502(3) 0.1716(6) 0.6200(2) 0.0446(11) Uani 1 1 d . . . . .
H00J H 0.591184 0.135318 0.592908 0.054 Uiso 1 1 calc R U . . .
C00K C 0.3709(3) 0.6629(6) 0.5974(2) 0.0515(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C00D 1.885(4) . ?
Se01 C00K 1.944(5) . ?
N002 C004 1.380(4) . ?
N002 C006 1.435(4) . ?
N002 C00D 1.400(5) . ?
F003 C00K 1.310(5) . ?
C004 C008 1.409(5) . ?
C004 C009 1.402(5) . ?
F005 C00K 1.303(6) . ?
C006 C00A 1.387(5) . ?
C006 C00C 1.377(5) . ?
C007 H007 0.9500 . ?
C007 C008 1.433(6) . ?
C007 C00D 1.357(6) . ?
C008 C00B 1.389(5) . ?
C009 H009 0.9500 . ?
C009 C00G 1.380(5) . ?
C00A H00A 0.9500 . ?
C00A C00E 1.392(5) . ?
C00B H00B 0.9500 . ?
C00B C00H 1.386(6) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.387(6) . ?
C00E H00E 0.9500 . ?
C00E C00J 1.380(7) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.386(7) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.403(6) . ?
C00H H00H 0.9500 . ?
F00I C00K 1.303(6) . ?
C00J H00J 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D Se01 C00K 99.51(18) . . ?
C004 N002 C006 124.8(3) . . ?
C004 N002 C00D 107.1(3) . . ?
C00D N002 C006 127.8(3) . . ?
N002 C004 C008 108.7(3) . . ?
N002 C004 C009 129.1(3) . . ?
C009 C004 C008 122.2(3) . . ?
C00A C006 N002 118.9(3) . . ?
C00C C006 N002 119.9(3) . . ?
C00C C006 C00A 121.2(3) . . ?
C008 C007 H007 126.4 . . ?
C00D C007 H007 126.4 . . ?
C00D C007 C008 107.1(4) . . ?
C004 C008 C007 106.6(3) . . ?
C00B C008 C004 119.2(4) . . ?
C00B C008 C007 134.2(4) . . ?
C004 C009 H009 121.4 . . ?
C00G C009 C004 117.1(4) . . ?
C00G C009 H009 121.4 . . ?
C006 C00A H00A 120.6 . . ?
C006 C00A C00E 118.8(4) . . ?
C00E C00A H00A 120.6 . . ?
C008 C00B H00B 120.4 . . ?
C00H C00B C008 119.3(4) . . ?
C00H C00B H00B 120.4 . . ?
C006 C00C H00C 120.3 . . ?
C006 C00C C00F 119.4(4) . . ?
C00F C00C H00C 120.3 . . ?
N002 C00D Se01 123.8(3) . . ?
C007 C00D Se01 125.6(3) . . ?
C007 C00D N002 110.4(3) . . ?
C00A C00E H00E 119.8 . . ?
C00J C00E C00A 120.4(4) . . ?
C00J C00E H00E 119.8 . . ?
C00C C00F H00F 120.0 . . ?
C00J C00F C00C 120.1(4) . . ?
C00J C00F H00F 120.0 . . ?
C009 C00G H00G 119.2 . . ?
C009 C00G C00H 121.5(4) . . ?
C00H C00G H00G 119.2 . . ?
C00B C00H C00G 120.7(4) . . ?
C00B C00H H00H 119.6 . . ?
C00G C00H H00H 119.6 . . ?
C00E C00J C00F 120.1(4) . . ?
C00E C00J H00J 120.0 . . ?
C00F C00J H00J 120.0 . . ?
F003 C00K Se01 109.3(3) . . ?
F005 C00K Se01 113.6(4) . . ?
F005 C00K F003 106.8(4) . . ?
F005 C00K F00I 106.7(5) . . ?
F00I C00K Se01 113.3(4) . . ?
F00I C00K F003 106.8(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
N002 C004 C008 C007 -0.3(4) . . . . ?
N002 C004 C008 C00B -180.0(4) . . . . ?
N002 C004 C009 C00G 180.0(4) . . . . ?
N002 C006 C00A C00E -179.8(3) . . . . ?
N002 C006 C00C C00F 178.3(3) . . . . ?
C004 N002 C006 C00A -58.1(5) . . . . ?
C004 N002 C006 C00C 122.2(4) . . . . ?
C004 N002 C00D Se01 -175.5(3) . . . . ?
C004 N002 C00D C007 -0.7(4) . . . . ?
C004 C008 C00B C00H 0.4(6) . . . . ?
C004 C009 C00G C00H -0.5(6) . . . . ?
C006 N002 C004 C008 174.7(3) . . . . ?
C006 N002 C004 C009 -5.2(6) . . . . ?
C006 N002 C00D Se01 10.6(5) . . . . ?
C006 N002 C00D C007 -174.6(4) . . . . ?
C006 C00A C00E C00J 2.1(6) . . . . ?
C006 C00C C00F C00J 1.0(6) . . . . ?
C007 C008 C00B C00H -179.2(4) . . . . ?
C008 C004 C009 C00G 0.1(5) . . . . ?
C008 C007 C00D Se01 175.2(3) . . . . ?
C008 C007 C00D N002 0.5(5) . . . . ?
C008 C00B C00H C00G -0.8(7) . . . . ?
C009 C004 C008 C007 179.7(3) . . . . ?
C009 C004 C008 C00B -0.1(6) . . . . ?
C009 C00G C00H C00B 0.9(6) . . . . ?
C00A C006 C00C C00F -1.4(6) . . . . ?
C00A C00E C00J C00F -2.5(6) . . . . ?
C00C C006 C00A C00E -0.1(6) . . . . ?
C00C C00F C00J C00E 1.0(6) . . . . ?
C00D N002 C004 C008 0.6(4) . . . . ?
C00D N002 C004 C009 -179.3(4) . . . . ?
C00D N002 C006 C00A 114.8(4) . . . . ?
C00D N002 C006 C00C -64.8(5) . . . . ?
C00D C007 C008 C004 -0.2(4) . . . . ?
C00D C007 C008 C00B 179.5(5) . . . . ?
C00K Se01 C00D N002 -77.2(4) . . . . ?
C00K Se01 C00D C007 108.8(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 11.926
_oxdiff_exptl_absorpt_empirical_full_min 0.202
####################################################################### 
# 
# 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_zzp20220908cp06-i_auto
_database_code_depnum_ccdc_archive 'CCDC 2267080'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-07 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 F3 I N O2 Se'
_chemical_formula_sum            'C11 H7 F3 I N O2 Se'
_chemical_formula_weight         448.04
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFSeI
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'
I I -0.3257 6.8362 '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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.8228(2)
_cell_length_b                   10.4090(4)
_cell_length_c                   27.0551(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1358.18(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9370
_cell_measurement_theta_min      3.2520
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.218
_exptl_absorpt_coefficient_mu    21.932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            3977
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.992
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  42.00   0.50    1.00    --   42.40  12.00 -81.00   54
  2  ω    -32.00  -6.00   0.50    1.00    --   42.40  12.00 -81.00   52
  3  ω     45.00 127.00   0.50    1.00    --   42.40  54.00-180.00  164
  4  ω     -5.00  23.00   0.50    1.00    --   42.40 -65.00 -30.00   56
  5  ω     18.00  79.00   0.50    1.00    --   42.40  65.00 120.00  122
  6  ω     26.00  70.00   0.50    1.00    --   42.40 -82.00 -60.00   88
  7  ω    -31.00  -6.00   0.50    1.00    --   42.40 -82.00 -60.00   50
  8  ω     43.00  68.00   0.50    1.00    --   42.40 -77.00 -60.00   50
  9  ω     52.00  98.00   0.50    1.41    --   93.70 -82.00 -90.00   92
 10  ω     75.00 126.00   0.50    1.41    --   93.70  68.00  30.00  102
 11  ω      4.00  72.00   0.50    1.41    --   93.70 -42.00   0.00  136
 12  ω     52.00 120.00   0.50    1.41    --   93.70 -82.00 -60.00  136
 13  ω     16.00  41.00   0.50    1.41    --   93.70 -82.00 -60.00   50
 14  ω    151.00 183.00   0.50    1.41    --   93.70  68.00  30.00   64
 15  ω     94.00 119.00   0.50    1.41    --   93.70 -42.00   0.00   50
 16  ω    130.00 181.00   0.50    1.41    --   93.70 -12.00 106.00  102
 17  ω      8.00  91.00   0.50    1.41    --   93.70 -12.00 106.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0502934000
_diffrn_orient_matrix_UB_12      0.1243165000
_diffrn_orient_matrix_UB_13      0.0295779000
_diffrn_orient_matrix_UB_21      -0.0119884000
_diffrn_orient_matrix_UB_22      0.0769233000
_diffrn_orient_matrix_UB_23      -0.0486075000
_diffrn_orient_matrix_UB_31      -0.3151644000
_diffrn_orient_matrix_UB_32      -0.0227426000
_diffrn_orient_matrix_UB_33      -0.0028818000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_full    0.676
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                1701
_reflns_number_total             2119
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.473
_refine_diff_density_min         -1.692
_refine_diff_density_rms         0.246
_refine_ls_abs_structure_details 
;
 Flack x determined using 384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0935
_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     
'w=1/[σ²(Fo²)+(0.1176P)²+38.2441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2610
_refine_ls_wR_factor_ref         0.2848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C008(H008), C00E(H00E), C00F(H00F)
3.b Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C)
;
_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
I01 I 0.6813(6) 0.8388(2) 0.44409(7) 0.0748(9) Uani 1 1 d . . . . .
Se02 Se 0.9778(7) 0.5144(4) 0.40850(13) 0.0630(10) Uani 1 1 d . . . . .
N003 N 0.383(6) 0.752(2) 0.3534(8) 0.052(6) Uani 1 1 d . . . . .
H003 H 0.279672 0.818978 0.354619 0.063 Uiso 1 1 calc R U . . .
O004 O -0.074(6) 0.639(2) 0.1884(8) 0.071(6) Uani 1 1 d . . . . .
F005 F 0.927(5) 0.342(3) 0.4804(10) 0.117(9) Uani 1 1 d . . . . .
F006 F 0.601(6) 0.325(3) 0.4281(9) 0.114(8) Uani 1 1 d . . . . .
C007 C 0.547(7) 0.557(3) 0.3305(10) 0.051(6) Uani 1 1 d . . . . .
C008 C 0.562(7) 0.449(3) 0.3007(10) 0.052(6) Uani 1 1 d . . . . .
H008 H 0.682682 0.382368 0.308347 0.062 Uiso 1 1 calc R U . . .
F009 F 0.591(6) 0.473(3) 0.4805(9) 0.110(8) Uani 1 1 d . . . . .
O00A O 0.019(6) 0.4314(19) 0.1790(8) 0.069(6) Uani 1 1 d . . . . .
C00B C 0.372(7) 0.655(2) 0.3178(8) 0.048(5) Uani 1 1 d . . . . .
C00C C 0.592(7) 0.718(3) 0.3869(9) 0.055(6) Uani 1 1 d . . . . .
C00D C 0.225(6) 0.541(2) 0.2476(9) 0.045(5) Uani 1 1 d . . . . .
C00E C 0.393(7) 0.442(3) 0.2592(11) 0.057(7) Uani 1 1 d . . . . .
H00E H 0.396573 0.369092 0.239405 0.068 Uiso 1 1 calc R U . . .
C00F C 0.192(8) 0.654(2) 0.2758(9) 0.055(7) Uani 1 1 d . . . . .
H00F H 0.068742 0.719157 0.267986 0.066 Uiso 1 1 calc R U . . .
C00G C 0.044(6) 0.530(3) 0.2014(10) 0.048(5) Uani 1 1 d . . . . .
C00H C 0.674(7) 0.598(3) 0.3747(10) 0.054(5) Uani 1 1 d . . . . .
C00I C -0.254(10) 0.637(4) 0.1450(13) 0.092(14) Uani 1 1 d . . . . .
H00A H -0.143737 0.625263 0.115807 0.138 Uiso 1 1 calc R U . . .
H00B H -0.354471 0.715948 0.142807 0.138 Uiso 1 1 calc R U . . .
H00C H -0.382642 0.566503 0.147943 0.138 Uiso 1 1 calc R U . . .
C00J C 0.762(8) 0.407(3) 0.4525(12) 0.069(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I01 C00C 2.04(3) . ?
Se02 C00H 1.94(3) . ?
Se02 C00J 1.94(4) . ?
N003 H003 0.8600 . ?
N003 C00B 1.40(3) . ?
N003 C00C 1.40(4) . ?
O004 C00G 1.32(3) . ?
O004 C00I 1.46(4) . ?
F005 C00J 1.29(4) . ?
F006 C00J 1.33(4) . ?
C007 C008 1.39(4) . ?
C007 C00B 1.37(4) . ?
C007 C00H 1.41(4) . ?
C008 H008 0.9300 . ?
C008 C00E 1.39(4) . ?
F009 C00J 1.31(4) . ?
O00A C00G 1.20(3) . ?
C00B C00F 1.43(4) . ?
C00C C00H 1.35(4) . ?
C00D C00E 1.35(4) . ?
C00D C00F 1.41(4) . ?
C00D C00G 1.53(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00I H00A 0.9600 . ?
C00I H00B 0.9600 . ?
C00I H00C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00H Se02 C00J 98.2(13) . . ?
C00B N003 H003 126.4 . . ?
C00B N003 C00C 107(2) . . ?
C00C N003 H003 126.4 . . ?
C00G O004 C00I 117(2) . . ?
C008 C007 C00H 136(3) . . ?
C00B C007 C008 119(3) . . ?
C00B C007 C00H 105(3) . . ?
C007 C008 H008 120.6 . . ?
C007 C008 C00E 119(3) . . ?
C00E C008 H008 120.6 . . ?
N003 C00B C00F 125(3) . . ?
C007 C00B N003 110(2) . . ?
C007 C00B C00F 125(2) . . ?
N003 C00C I01 119(2) . . ?
C00H C00C I01 134(3) . . ?
C00H C00C N003 106(3) . . ?
C00E C00D C00F 125(3) . . ?
C00E C00D C00G 119(2) . . ?
C00F C00D C00G 116(2) . . ?
C008 C00E H00E 119.9 . . ?
C00D C00E C008 120(3) . . ?
C00D C00E H00E 119.9 . . ?
C00B C00F H00F 124.2 . . ?
C00D C00F C00B 112(3) . . ?
C00D C00F H00F 124.2 . . ?
O004 C00G C00D 114(2) . . ?
O00A C00G O004 124(3) . . ?
O00A C00G C00D 122(3) . . ?
C007 C00H Se02 126(2) . . ?
C00C C00H Se02 121(2) . . ?
C00C C00H C007 111(3) . . ?
O004 C00I H00A 109.5 . . ?
O004 C00I H00B 109.5 . . ?
O004 C00I H00C 109.5 . . ?
H00A C00I H00B 109.5 . . ?
H00A C00I H00C 109.5 . . ?
H00B C00I H00C 109.5 . . ?
F005 C00J Se02 109(3) . . ?
F005 C00J F006 108(3) . . ?
F005 C00J F009 109(3) . . ?
F006 C00J Se02 112(2) . . ?
F009 C00J Se02 113(2) . . ?
F009 C00J F006 105(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
I01 C00C C00H Se02 -11(4) . . . . ?
I01 C00C C00H C007 180(2) . . . . ?
N003 C00B C00F C00D -178(3) . . . . ?
N003 C00C C00H Se02 176.3(18) . . . . ?
N003 C00C C00H C007 7(3) . . . . ?
C007 C008 C00E C00D 2(5) . . . . ?
C007 C00B C00F C00D -2(4) . . . . ?
C008 C007 C00B N003 178(3) . . . . ?
C008 C007 C00B C00F 2(5) . . . . ?
C008 C007 C00H Se02 9(5) . . . . ?
C008 C007 C00H C00C 177(3) . . . . ?
C00B N003 C00C I01 178.4(18) . . . . ?
C00B N003 C00C C00H -8(3) . . . . ?
C00B C007 C008 C00E -1(4) . . . . ?
C00B C007 C00H Se02 -172(2) . . . . ?
C00B C007 C00H C00C -4(3) . . . . ?
C00C N003 C00B C007 6(3) . . . . ?
C00C N003 C00B C00F -178(3) . . . . ?
C00E C00D C00F C00B 3(4) . . . . ?
C00E C00D C00G O004 -168(3) . . . . ?
C00E C00D C00G O00A 10(5) . . . . ?
C00F C00D C00E C008 -3(5) . . . . ?
C00F C00D C00G O004 14(4) . . . . ?
C00F C00D C00G O00A -167(3) . . . . ?
C00G C00D C00E C008 179(3) . . . . ?
C00G C00D C00F C00B -179(2) . . . . ?
C00H C007 C008 C00E 178(3) . . . . ?
C00H C007 C00B N003 -2(3) . . . . ?
C00H C007 C00B C00F -178(3) . . . . ?
C00I O004 C00G O00A 2(5) . . . . ?
C00I O004 C00G C00D -179(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 4.580
_oxdiff_exptl_absorpt_empirical_full_min 0.320
####################################################################### 
# 
# 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_zzp20240521mdscf3_auto
_database_code_depnum_ccdc_archive 'CCDC 2267469'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F3 N O2 S2'
_chemical_formula_sum            'C16 H12 F3 N O2 S2'
_chemical_formula_weight         371.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFS
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9478(4)
_cell_length_b                   9.8016(5)
_cell_length_c                   10.5477(5)
_cell_angle_alpha                93.502(4)
_cell_angle_beta                 113.364(5)
_cell_angle_gamma                104.943(4)
_cell_volume                     806.46(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6769
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.0760
_cell_measurement_theta_min      2.1230
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10785
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.177
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  99.00   0.50    2.00    --    9.30  38.00 -60.00  106
  2  ω    -14.00  18.00   0.50    2.00    --    9.30  38.00 -60.00   64
  3  ω     59.00  85.00   0.50    2.00    --    9.30  82.00 150.00   52
  4  ω    -18.00  37.00   0.50    2.00    --    9.30  82.00 150.00  110
  5  ω    -55.00  16.00   0.50    2.00    --   -9.70 -57.00   0.00  142
  6  ω    -97.00  18.00   0.50    2.00    --   -9.70 -82.00-180.00  230
  7  ω    -96.00  12.00   0.50    2.00    --   -9.70 -82.00 -30.00  216
  8  ω    -28.00   3.00   0.50    2.00    --   -9.70 -82.00 120.00   62
  9  ω    -85.00 -59.00   0.50    2.00    --   -9.70 -57.00   0.00   52
 10  ω    -15.00  13.00   0.50    2.00    --   -9.70 -82.00 -90.00   56
 11  ω    -99.00   1.00   0.50    2.00    --   -9.70 -77.00-120.00  200
 12  ω    -48.00  30.00   0.50    2.00    --   -9.70  19.00 150.00  156
 13  ω    -92.00 -67.00   0.50    2.00    --   -9.70  19.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0803766000
_diffrn_orient_matrix_UB_12      -0.0446440000
_diffrn_orient_matrix_UB_13      -0.0516061000
_diffrn_orient_matrix_UB_21      0.0054024000
_diffrn_orient_matrix_UB_22      0.0462839000
_diffrn_orient_matrix_UB_23      -0.0482120000
_diffrn_orient_matrix_UB_31      0.0418064000
_diffrn_orient_matrix_UB_32      -0.0408837000
_diffrn_orient_matrix_UB_33      -0.0238092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2943
_reflns_number_total             3387
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.5761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N008(H008), C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00E)
;
_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 0.18008(6) 0.07526(5) 0.72911(5) 0.01958(14) Uani 1 1 d . . . . .
S002 S 0.21755(8) 0.20472(6) 0.19053(6) 0.03630(17) Uani 1 1 d . . . . .
O003 O 0.25569(18) 0.04936(15) 0.86914(14) 0.0259(3) Uani 1 1 d . . . . .
O004 O 0.00320(17) -0.00055(15) 0.64127(15) 0.0261(3) Uani 1 1 d . . . . .
F005 F 0.1197(2) 0.41582(18) 0.10033(16) 0.0561(4) Uani 1 1 d . . . . .
F006 F 0.1619(3) 0.4141(2) 0.31318(18) 0.0675(5) Uani 1 1 d . . . . .
F007 F 0.3730(2) 0.48125(17) 0.2632(2) 0.0714(6) Uani 1 1 d . . . . .
N008 N 0.28388(19) 0.03426(16) 0.64198(16) 0.0194(3) Uani 1 1 d . . . . .
H008 H 0.226476 -0.025591 0.560891 0.023 Uiso 1 1 calc R U . . .
C009 C 0.4649(2) 0.09340(19) 0.6947(2) 0.0195(4) Uani 1 1 d . . . . .
C00A C 0.5350(2) 0.1610(2) 0.6080(2) 0.0214(4) Uani 1 1 d . . . . .
C00B C 0.2121(2) 0.2612(2) 0.7392(2) 0.0204(4) Uani 1 1 d . . . . .
C00C C 0.7486(3) 0.1368(2) 0.8773(2) 0.0278(5) Uani 1 1 d . . . . .
H00C H 0.821346 0.130087 0.969542 0.033 Uiso 1 1 calc R U . . .
C00D C 0.5726(2) 0.0806(2) 0.8283(2) 0.0238(4) Uani 1 1 d . . . . .
H00D H 0.525414 0.033289 0.886065 0.029 Uiso 1 1 calc R U . . .
C00E C 0.3408(3) 0.1934(2) 0.3560(2) 0.0269(4) Uani 1 1 d . . . . .
C00F C 0.8190(3) 0.2026(2) 0.7928(2) 0.0320(5) Uani 1 1 d . . . . .
H00F H 0.939681 0.240578 0.826837 0.038 Uiso 1 1 calc R U . . .
C00G C 0.4277(3) 0.1770(2) 0.4704(2) 0.0235(4) Uani 1 1 d . . . . .
C00H C 0.2797(3) 0.3496(2) 0.8692(2) 0.0257(4) Uani 1 1 d . . . . .
H00H H 0.313655 0.311006 0.952904 0.031 Uiso 1 1 calc R U . . .
C00I C 0.2540(3) 0.5535(2) 0.7551(2) 0.0298(5) Uani 1 1 d . . . . .
C00J C 0.2974(3) 0.4951(2) 0.8756(2) 0.0306(5) Uani 1 1 d . . . . .
H00J H 0.339946 0.555377 0.964203 0.037 Uiso 1 1 calc R U . . .
C00K C 0.7135(3) 0.2132(2) 0.6586(2) 0.0281(5) Uani 1 1 d . . . . .
H00K H 0.762447 0.256296 0.600042 0.034 Uiso 1 1 calc R U . . .
C00L C 0.1893(3) 0.4635(2) 0.6258(2) 0.0350(5) Uani 1 1 d . . . . .
H00L H 0.160253 0.502816 0.542375 0.042 Uiso 1 1 calc R U . . .
C00M C 0.1667(3) 0.3173(2) 0.6169(2) 0.0303(5) Uani 1 1 d . . . . .
H00M H 0.120670 0.256439 0.528089 0.036 Uiso 1 1 calc R U . . .
C00N C 0.2206(3) 0.3889(3) 0.2211(2) 0.0343(5) Uani 1 1 d . . . . .
C00O C 0.2783(4) 0.7125(2) 0.7628(3) 0.0457(6) Uani 1 1 d . . . . .
H00A H 0.330223 0.760084 0.861403 0.069 Uiso 1 1 calc R U . . .
H00B H 0.167064 0.727888 0.713473 0.069 Uiso 1 1 calc R U . . .
H00E H 0.353452 0.752861 0.718563 0.069 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 O003 1.4302(14) . ?
S001 O004 1.4359(14) . ?
S001 N008 1.6411(16) . ?
S001 C00B 1.7599(19) . ?
S002 C00E 1.683(2) . ?
S002 C00N 1.805(2) . ?
F005 C00N 1.327(3) . ?
F006 C00N 1.313(3) . ?
F007 C00N 1.307(3) . ?
N008 H008 0.8800 . ?
N008 C009 1.425(2) . ?
C009 C00A 1.408(3) . ?
C009 C00D 1.392(3) . ?
C00A C00G 1.433(3) . ?
C00A C00K 1.402(3) . ?
C00B C00H 1.386(3) . ?
C00B C00M 1.385(3) . ?
C00C H00C 0.9500 . ?
C00C C00D 1.387(3) . ?
C00C C00F 1.383(3) . ?
C00D H00D 0.9500 . ?
C00E C00G 1.197(3) . ?
C00F H00F 0.9500 . ?
C00F C00K 1.383(3) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.388(3) . ?
C00I C00J 1.380(3) . ?
C00I C00L 1.392(3) . ?
C00I C00O 1.510(3) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00M 1.386(3) . ?
C00M H00M 0.9500 . ?
C00O H00A 0.9800 . ?
C00O H00B 0.9800 . ?
C00O H00E 0.9800 . ?

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
O003 S001 O004 119.02(9) . . ?
O003 S001 N008 109.19(8) . . ?
O003 S001 C00B 107.80(9) . . ?
O004 S001 N008 104.90(8) . . ?
O004 S001 C00B 109.11(9) . . ?
N008 S001 C00B 106.11(9) . . ?
C00E S002 C00N 98.89(10) . . ?
S001 N008 H008 119.3 . . ?
C009 N008 S001 121.47(13) . . ?
C009 N008 H008 119.3 . . ?
C00A C009 N008 119.23(17) . . ?
C00D C009 N008 120.85(17) . . ?
C00D C009 C00A 119.87(18) . . ?
C009 C00A C00G 121.28(17) . . ?
C00K C00A C009 118.79(18) . . ?
C00K C00A C00G 119.93(18) . . ?
C00H C00B S001 119.74(15) . . ?
C00M C00B S001 119.56(15) . . ?
C00M C00B C00H 120.68(19) . . ?
C00D C00C H00C 119.8 . . ?
C00F C00C H00C 119.8 . . ?
C00F C00C C00D 120.45(19) . . ?
C009 C00D H00D 119.9 . . ?
C00C C00D C009 120.18(19) . . ?
C00C C00D H00D 119.9 . . ?
C00G C00E S002 175.99(19) . . ?
C00C C00F H00F 120.0 . . ?
C00C C00F C00K 119.95(19) . . ?
C00K C00F H00F 120.0 . . ?
C00E C00G C00A 178.5(2) . . ?
C00B C00H H00H 120.4 . . ?
C00B C00H C00J 119.26(19) . . ?
C00J C00H H00H 120.4 . . ?
C00J C00I C00L 118.8(2) . . ?
C00J C00I C00O 120.9(2) . . ?
C00L C00I C00O 120.3(2) . . ?
C00H C00J H00J 119.5 . . ?
C00I C00J C00H 121.0(2) . . ?
C00I C00J H00J 119.5 . . ?
C00A C00K H00K 119.6 . . ?
C00F C00K C00A 120.7(2) . . ?
C00F C00K H00K 119.6 . . ?
C00I C00L H00L 119.5 . . ?
C00M C00L C00I 121.0(2) . . ?
C00M C00L H00L 119.5 . . ?
C00B C00M C00L 119.1(2) . . ?
C00B C00M H00M 120.4 . . ?
C00L C00M H00M 120.4 . . ?
F005 C00N S002 107.60(16) . . ?
F006 C00N S002 113.20(17) . . ?
F006 C00N F005 107.28(19) . . ?
F007 C00N S002 113.16(17) . . ?
F007 C00N F005 107.8(2) . . ?
F007 C00N F006 107.6(2) . . ?
C00I C00O H00A 109.5 . . ?
C00I C00O H00B 109.5 . . ?
C00I C00O H00E 109.5 . . ?
H00A C00O H00B 109.5 . . ?
H00A C00O H00E 109.5 . . ?
H00B C00O H00E 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 N008 C009 C00A -127.81(16) . . . . ?
S001 N008 C009 C00D 54.5(2) . . . . ?
S001 C00B C00H C00J -177.17(15) . . . . ?
S001 C00B C00M C00L 178.77(17) . . . . ?
O003 S001 N008 C009 -53.21(16) . . . . ?
O003 S001 C00B C00H -7.76(19) . . . . ?
O003 S001 C00B C00M 173.28(16) . . . . ?
O004 S001 N008 C009 178.16(14) . . . . ?
O004 S001 C00B C00H 122.82(16) . . . . ?
O004 S001 C00B C00M -56.14(19) . . . . ?
N008 S001 C00B C00H -124.64(16) . . . . ?
N008 S001 C00B C00M 56.39(18) . . . . ?
N008 C009 C00A C00G 2.9(3) . . . . ?
N008 C009 C00A C00K -177.23(17) . . . . ?
N008 C009 C00D C00C 179.01(18) . . . . ?
C009 C00A C00K C00F -2.0(3) . . . . ?
C00A C009 C00D C00C 1.3(3) . . . . ?
C00B S001 N008 C009 62.73(16) . . . . ?
C00B C00H C00J C00I -2.2(3) . . . . ?
C00C C00F C00K C00A 1.6(3) . . . . ?
C00D C009 C00A C00G -179.41(17) . . . . ?
C00D C009 C00A C00K 0.5(3) . . . . ?
C00D C00C C00F C00K 0.3(3) . . . . ?
C00E S002 C00N F005 -176.61(16) . . . . ?
C00E S002 C00N F006 -58.25(19) . . . . ?
C00E S002 C00N F007 64.47(19) . . . . ?
C00F C00C C00D C009 -1.7(3) . . . . ?
C00G C00A C00K C00F 177.95(19) . . . . ?
C00H C00B C00M C00L -0.2(3) . . . . ?
C00I C00L C00M C00B -1.1(4) . . . . ?
C00J C00I C00L C00M 0.7(3) . . . . ?
C00L C00I C00J C00H 1.0(3) . . . . ?
C00M C00B C00H C00J 1.8(3) . . . . ?
C00O C00I C00J C00H -178.2(2) . . . . ?
C00O C00I C00L C00M 179.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.697
_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_zzp20240521cpscf3_auto
_database_code_depnum_ccdc_archive 'CCDC 2267084'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Br F3 N O2 S2'
_chemical_formula_sum            'C16 H11 Br F3 N O2 S2'
_chemical_formula_weight         450.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONFSBr
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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2036(5)
_cell_length_b                   9.8316(4)
_cell_length_c                   14.5213(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.303(4)
_cell_angle_gamma                90
_cell_volume                     1740.87(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11026
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.9070
_cell_measurement_theta_min      2.1290
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    2.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23185
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.269
_diffrn_reflns_theta_min         2.138
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  79.00   0.50    4.73    --    9.30  82.00 150.00  194
  2  ω      4.00  41.00   0.50    4.73    --    9.30 -38.00-120.00   74
  3  ω     -6.00  19.00   0.50    4.73    --    9.30  82.00  30.00   50
  4  ω     62.00  99.00   0.50    4.73    --    9.30  57.00   0.00   74
  5  ω    -11.00  42.00   0.50    4.73    --    9.30  57.00  90.00  106
  6  ω    -18.00  99.00   0.50    4.73    --    9.30  82.00-120.00  234
  7  ω     73.00  99.00   0.50    4.73    --    9.30  82.00   0.00   52
  8  ω     65.00  91.00   0.50    4.73    --    9.30  77.00 150.00   52
  9  ω    -10.00  17.00   0.50    4.73    --    9.30  82.00 -30.00   54
 10  ω     54.00  81.00   0.50    4.73    --    9.30  82.00 -30.00   54
 11  ω     -2.00  44.00   0.50    4.73    --    9.30  82.00-180.00   92
 12  ω    -70.00 -38.00   0.50    4.73    --    9.30 -38.00-120.00   64
 13  ω    -99.00  18.00   0.50    4.73    --   -9.70 -82.00 -30.00  234
 14  ω    -84.00 -32.00   0.50    4.73    --   -9.70 -57.00  90.00  104
 15  ω     51.00  79.00   0.50    4.73    --   -9.70  82.00-150.00   56
 16  ω    -29.00  13.00   0.50    4.73    --   -9.70  82.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0274072000
_diffrn_orient_matrix_UB_12      -0.0421712000
_diffrn_orient_matrix_UB_13      0.0313555000
_diffrn_orient_matrix_UB_21      -0.0444223000
_diffrn_orient_matrix_UB_22      -0.0074075000
_diffrn_orient_matrix_UB_23      -0.0326434000
_diffrn_orient_matrix_UB_31      0.0255400000
_diffrn_orient_matrix_UB_32      -0.0580399000
_diffrn_orient_matrix_UB_33      -0.0186349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3195
_reflns_number_total             3715
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+2.5475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00I(H00I), C00J(H00J),
 C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00E,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.72980(3) 0.27697(3) 0.51203(2) 0.03436(12) Uani 1 1 d . . . . .
S002 S 0.39288(5) 0.24539(7) 0.24257(5) 0.01771(15) Uani 1 1 d . . . . .
S003 S 0.59147(6) 0.05683(7) 0.36144(5) 0.02593(18) Uani 1 1 d . . . . .
O004 O 0.41977(16) 0.1123(2) 0.21269(14) 0.0246(4) Uani 1 1 d . . . . .
O005 O 0.35987(16) 0.3467(2) 0.17670(13) 0.0236(4) Uani 1 1 d . . . . .
N006 N 0.50626(17) 0.3079(2) 0.29734(15) 0.0165(5) Uani 1 1 d . . . . .
F007 F 0.7246(2) -0.0896(2) 0.2754(2) 0.0813(9) Uani 1 1 d . . . . .
C008 C 0.5138(2) 0.4466(3) 0.32407(18) 0.0167(5) Uani 1 1 d . . . . .
F009 F 0.7867(2) 0.1051(3) 0.3020(2) 0.0833(9) Uani 1 1 d . . . . .
F00A F 0.6691(2) 0.0829(4) 0.19669(18) 0.0897(11) Uani 1 1 d . . . . .
C00B C 0.4646(2) 0.5631(3) 0.2865(2) 0.0226(6) Uani 1 1 d . . . . .
H00B H 0.414975 0.558317 0.234539 0.027 Uiso 1 1 calc R U . . .
C00C C 0.2200(2) 0.3402(3) 0.33538(19) 0.0208(6) Uani 1 1 d . . . . .
H00C H 0.222950 0.418116 0.296872 0.025 Uiso 1 1 calc R U . . .
C00D C 0.2918(2) 0.1204(3) 0.38368(19) 0.0206(6) Uani 1 1 d . . . . .
H00D H 0.343047 0.048642 0.377323 0.025 Uiso 1 1 calc R U . . .
C00E C 0.2948(2) 0.2347(3) 0.32712(18) 0.0167(5) Uani 1 1 d . . . . .
C00F C 0.2128(2) 0.1133(3) 0.4492(2) 0.0239(6) Uani 1 1 d . . . . .
H00F H 0.210620 0.036199 0.488589 0.029 Uiso 1 1 calc R U . . .
C00G C 0.5895(2) 0.4557(3) 0.39942(18) 0.0185(5) Uani 1 1 d . . . . .
C00H C 0.1365(2) 0.2173(3) 0.4585(2) 0.0246(6) Uani 1 1 d . . . . .
C00I C 0.1412(2) 0.3293(3) 0.4008(2) 0.0261(6) Uani 1 1 d . . . . .
H00I H 0.089147 0.400321 0.406427 0.031 Uiso 1 1 calc R U . . .
C00J C 0.4909(3) 0.6855(3) 0.3280(2) 0.0281(7) Uani 1 1 d . . . . .
H00J H 0.457445 0.766181 0.304434 0.034 Uiso 1 1 calc R U . . .
C00K C 0.5751(2) 0.2323(3) 0.36061(19) 0.0187(6) Uani 1 1 d . . . . .
C00L C 0.6259(2) 0.3213(3) 0.41972(18) 0.0211(6) Uani 1 1 d . . . . .
C00M C 0.6153(2) 0.5815(3) 0.4394(2) 0.0249(6) Uani 1 1 d . . . . .
H00M H 0.666574 0.587861 0.490179 0.030 Uiso 1 1 calc R U . . .
C00N C 0.5651(3) 0.6951(3) 0.4036(2) 0.0276(7) Uani 1 1 d . . . . .
H00N H 0.580838 0.781490 0.430295 0.033 Uiso 1 1 calc R U . . .
C00O C 0.6959(3) 0.0372(4) 0.2776(3) 0.0405(8) Uani 1 1 d . . . . .
C00P C 0.0495(3) 0.2055(4) 0.5294(2) 0.0409(8) Uani 1 1 d . . . . .
H00A H -0.018658 0.171516 0.499769 0.061 Uiso 1 1 calc R U . . .
H00E H 0.036437 0.295125 0.556413 0.061 Uiso 1 1 calc R U . . .
H00G H 0.074412 0.142239 0.578044 0.061 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
Br01 C00L 1.859(3) . ?
S002 O004 1.421(2) . ?
S002 O005 1.428(2) . ?
S002 N006 1.684(2) . ?
S002 C00E 1.752(3) . ?
S003 C00K 1.737(3) . ?
S003 C00O 1.807(3) . ?
N006 C008 1.420(3) . ?
N006 C00K 1.428(3) . ?
F007 C00O 1.297(4) . ?
C008 C00B 1.395(4) . ?
C008 C00G 1.406(4) . ?
F009 C00O 1.329(5) . ?
F00A C00O 1.288(4) . ?
C00B H00B 0.9500 . ?
C00B C00J 1.378(4) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.389(4) . ?
C00C C00I 1.383(4) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.393(4) . ?
C00D C00F 1.383(4) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.394(4) . ?
C00G C00L 1.421(4) . ?
C00G C00M 1.396(4) . ?
C00H C00I 1.386(4) . ?
C00H C00P 1.513(4) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00N 1.397(4) . ?
C00K C00L 1.358(4) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.367(4) . ?
C00N H00N 0.9500 . ?
C00P H00A 0.9800 . ?
C00P H00E 0.9800 . ?
C00P H00G 0.9800 . ?

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
O004 S002 O005 120.00(12) . . ?
O004 S002 N006 106.54(12) . . ?
O004 S002 C00E 109.37(12) . . ?
O005 S002 N006 105.44(11) . . ?
O005 S002 C00E 109.20(12) . . ?
N006 S002 C00E 105.22(12) . . ?
C00K S003 C00O 100.67(15) . . ?
C008 N006 S002 121.52(18) . . ?
C008 N006 C00K 107.1(2) . . ?
C00K N006 S002 124.40(18) . . ?
C00B C008 N006 131.3(2) . . ?
C00B C008 C00G 120.7(2) . . ?
C00G C008 N006 107.9(2) . . ?
C008 C00B H00B 121.4 . . ?
C00J C00B C008 117.2(3) . . ?
C00J C00B H00B 121.4 . . ?
C00E C00C H00C 120.7 . . ?
C00I C00C H00C 120.7 . . ?
C00I C00C C00E 118.6(3) . . ?
C00E C00D H00D 120.6 . . ?
C00F C00D H00D 120.6 . . ?
C00F C00D C00E 118.8(3) . . ?
C00C C00E S002 119.0(2) . . ?
C00C C00E C00D 121.2(2) . . ?
C00D C00E S002 119.7(2) . . ?
C00D C00F H00F 119.5 . . ?
C00D C00F C00H 121.1(3) . . ?
C00H C00F H00F 119.5 . . ?
C008 C00G C00L 107.0(2) . . ?
C00M C00G C008 120.7(3) . . ?
C00M C00G C00L 132.3(3) . . ?
C00F C00H C00P 120.0(3) . . ?
C00I C00H C00F 118.7(3) . . ?
C00I C00H C00P 121.3(3) . . ?
C00C C00I C00H 121.6(3) . . ?
C00C C00I H00I 119.2 . . ?
C00H C00I H00I 119.2 . . ?
C00B C00J H00J 118.8 . . ?
C00B C00J C00N 122.3(3) . . ?
C00N C00J H00J 118.8 . . ?
N006 C00K S003 125.8(2) . . ?
C00L C00K S003 125.9(2) . . ?
C00L C00K N006 108.3(2) . . ?
C00G C00L Br01 124.5(2) . . ?
C00K C00L Br01 125.8(2) . . ?
C00K C00L C00G 109.7(2) . . ?
C00G C00M H00M 120.8 . . ?
C00N C00M C00G 118.4(3) . . ?
C00N C00M H00M 120.8 . . ?
C00J C00N H00N 119.7 . . ?
C00M C00N C00J 120.6(3) . . ?
C00M C00N H00N 119.7 . . ?
F007 C00O S003 108.5(3) . . ?
F007 C00O F009 105.4(3) . . ?
F009 C00O S003 111.8(3) . . ?
F00A C00O S003 114.7(3) . . ?
F00A C00O F007 111.8(4) . . ?
F00A C00O F009 104.2(3) . . ?
C00H C00P H00A 109.5 . . ?
C00H C00P H00E 109.5 . . ?
C00H C00P H00G 109.5 . . ?
H00A C00P H00E 109.5 . . ?
H00A C00P H00G 109.5 . . ?
H00E C00P H00G 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S002 N006 C008 C00B -28.5(4) . . . . ?
S002 N006 C008 C00G 154.39(19) . . . . ?
S002 N006 C00K S003 26.6(3) . . . . ?
S002 N006 C00K C00L -153.7(2) . . . . ?
S003 C00K C00L Br01 3.0(4) . . . . ?
S003 C00K C00L C00G -178.2(2) . . . . ?
O004 S002 N006 C008 170.4(2) . . . . ?
O004 S002 N006 C00K -42.8(2) . . . . ?
O004 S002 C00E C00C -149.8(2) . . . . ?
O004 S002 C00E C00D 29.2(3) . . . . ?
O005 S002 N006 C008 41.8(2) . . . . ?
O005 S002 N006 C00K -171.3(2) . . . . ?
O005 S002 C00E C00C -16.7(2) . . . . ?
O005 S002 C00E C00D 162.3(2) . . . . ?
N006 S002 C00E C00C 96.1(2) . . . . ?
N006 S002 C00E C00D -84.9(2) . . . . ?
N006 C008 C00B C00J -178.6(3) . . . . ?
N006 C008 C00G C00L -1.4(3) . . . . ?
N006 C008 C00G C00M 178.7(2) . . . . ?
N006 C00K C00L Br01 -176.73(19) . . . . ?
N006 C00K C00L C00G 2.0(3) . . . . ?
C008 N006 C00K S003 177.4(2) . . . . ?
C008 N006 C00K C00L -2.8(3) . . . . ?
C008 C00B C00J C00N 1.1(5) . . . . ?
C008 C00G C00L Br01 178.35(19) . . . . ?
C008 C00G C00L C00K -0.4(3) . . . . ?
C008 C00G C00M C00N 0.2(4) . . . . ?
C00B C008 C00G C00L -178.8(3) . . . . ?
C00B C008 C00G C00M 1.2(4) . . . . ?
C00B C00J C00N C00M 0.2(5) . . . . ?
C00D C00F C00H C00I -0.3(4) . . . . ?
C00D C00F C00H C00P 178.7(3) . . . . ?
C00E S002 N006 C008 -73.6(2) . . . . ?
C00E S002 N006 C00K 73.3(2) . . . . ?
C00E C00C C00I C00H 0.9(4) . . . . ?
C00E C00D C00F C00H 0.7(4) . . . . ?
C00F C00D C00E S002 -179.2(2) . . . . ?
C00F C00D C00E C00C -0.3(4) . . . . ?
C00F C00H C00I C00C -0.5(4) . . . . ?
C00G C008 C00B C00J -1.8(4) . . . . ?
C00G C00M C00N C00J -0.9(5) . . . . ?
C00I C00C C00E S002 178.5(2) . . . . ?
C00I C00C C00E C00D -0.5(4) . . . . ?
C00K S003 C00O F007 174.8(3) . . . . ?
C00K S003 C00O F009 58.9(3) . . . . ?
C00K S003 C00O F00A -59.4(3) . . . . ?
C00K N006 C008 C00B 179.7(3) . . . . ?
C00K N006 C008 C00G 2.6(3) . . . . ?
C00L C00G C00M C00N -179.8(3) . . . . ?
C00M C00G C00L Br01 -1.7(5) . . . . ?
C00M C00G C00L C00K 179.5(3) . . . . ?
C00O S003 C00K N006 84.7(3) . . . . ?
C00O S003 C00K C00L -95.0(3) . . . . ?
C00P C00H C00I C00C -179.5(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 1.912
_oxdiff_exptl_absorpt_empirical_full_min 0.843
####################################################################### 
# 
# 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_cpsecf3-i
_database_code_depnum_ccdc_archive 'CCDC 2165430'
loop_
_audit_author_name
_audit_author_address
'Zipeng Zhang'
;Fuzhou University
China
;
_audit_update_record             
;
2024-05-08 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F3 I N O2 S Se'
_chemical_formula_sum            'C16 H11 F3 I N O2 S Se'
_chemical_formula_weight         544.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8830(4)
_cell_length_b                   14.6781(7)
_cell_length_c                   12.5748(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.1570(10)
_cell_angle_gamma                90
_cell_volume                     1800.90(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    3.954
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8402.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.068
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2690
_reflns_number_total             3188
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+2.7770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00N(H00N), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_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
I01 I 0.55525(3) 0.16192(2) 0.61978(3) 0.06874(12) Uani 1 1 d . . . . .
Se02 Se 0.29150(4) 0.31929(3) 0.48433(3) 0.04815(12) Uani 1 1 d . . . . .
S003 S 0.86375(9) 0.29041(7) 0.58303(8) 0.0466(2) Uani 1 1 d . . . . .
O004 O 0.8651(3) 0.20011(18) 0.6230(2) 0.0593(7) Uani 1 1 d . . . . .
O005 O 0.9624(3) 0.3188(2) 0.5194(2) 0.0619(8) Uani 1 1 d . . . . .
N006 N 0.7103(3) 0.3047(2) 0.5024(2) 0.0414(7) Uani 1 1 d . . . . .
F007 F 0.2751(4) 0.2820(3) 0.2700(2) 0.1106(11) Uani 1 1 d . . . . .
F008 F 0.3139(4) 0.1665(2) 0.3652(3) 0.1143(12) Uani 1 1 d . . . . .
C009 C 0.5414(3) 0.3971(2) 0.4177(3) 0.0368(8) Uani 1 1 d . . . . .
C00A C 0.5816(3) 0.2757(2) 0.5282(3) 0.0399(8) Uani 1 1 d . . . . .
C00B C 0.6829(3) 0.3820(2) 0.4343(3) 0.0386(8) Uani 1 1 d . . . . .
F00C F 0.1173(3) 0.2251(3) 0.3423(3) 0.1344(15) Uani 1 1 d . . . . .
C00D C 0.4810(3) 0.3291(2) 0.4768(3) 0.0388(8) Uani 1 1 d . . . . .
C00E C 0.8587(3) 0.3679(3) 0.6879(3) 0.0423(8) Uani 1 1 d . . . . .
C00F C 0.4861(4) 0.4681(3) 0.3509(3) 0.0474(9) Uani 1 1 d . . . . .
H00F H 0.392188 0.478890 0.339056 0.057 Uiso 1 1 calc R U . . .
C00G C 0.5730(4) 0.5218(3) 0.3031(3) 0.0537(10) Uani 1 1 d . . . . .
H00G H 0.537821 0.569746 0.258734 0.064 Uiso 1 1 calc R U . . .
C00H C 0.9118(4) 0.4541(3) 0.6806(3) 0.0544(10) Uani 1 1 d . . . . .
H00H H 0.949844 0.470780 0.620430 0.065 Uiso 1 1 calc R U . . .
C00I C 0.7703(4) 0.4352(3) 0.3847(3) 0.0518(10) Uani 1 1 d . . . . .
H00I H 0.864096 0.424123 0.394705 0.062 Uiso 1 1 calc R U . . .
C00J C 0.7131(4) 0.5050(3) 0.3204(3) 0.0568(10) Uani 1 1 d . . . . .
H00J H 0.769919 0.542312 0.287234 0.068 Uiso 1 1 calc R U . . .
C00K C 0.2466(4) 0.2448(3) 0.3573(4) 0.0610(11) Uani 1 1 d . . . . .
C00L C 0.8025(4) 0.3425(3) 0.7770(3) 0.0578(10) Uani 1 1 d . . . . .
H00L H 0.768152 0.284006 0.782465 0.069 Uiso 1 1 calc R U . . .
C00M C 0.8500(4) 0.4923(3) 0.8521(3) 0.0560(10) Uani 1 1 d . . . . .
C00N C 0.9081(4) 0.5152(3) 0.7629(4) 0.0618(11) Uani 1 1 d . . . . .
H00N H 0.945483 0.572966 0.758444 0.074 Uiso 1 1 calc R U . . .
C00O C 0.7982(4) 0.4054(3) 0.8578(3) 0.0637(11) Uani 1 1 d . . . . .
H00O H 0.759499 0.388900 0.917731 0.076 Uiso 1 1 calc R U . . .
C00P C 0.8442(5) 0.5596(3) 0.9416(4) 0.0797(15) Uani 1 1 d . . . . .
H00A H 0.932196 0.588095 0.960855 0.120 Uiso 1 1 calc R U . . .
H00B H 0.820350 0.528482 1.003156 0.120 Uiso 1 1 calc R U . . .
H00C H 0.776512 0.605263 0.917971 0.120 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
I01 C00A 2.069(3) . ?
Se02 C00D 1.896(3) . ?
Se02 C00K 1.928(4) . ?
S003 O004 1.417(3) . ?
S003 O005 1.418(3) . ?
S003 N006 1.698(3) . ?
S003 C00E 1.748(4) . ?
N006 C00A 1.426(4) . ?
N006 C00B 1.421(4) . ?
F007 C00K 1.298(5) . ?
F008 C00K 1.323(5) . ?
C009 C00B 1.398(5) . ?
C009 C00D 1.430(5) . ?
C009 C00F 1.394(5) . ?
C00A C00D 1.348(5) . ?
C00B C00I 1.384(5) . ?
F00C C00K 1.293(5) . ?
C00E C00H 1.378(5) . ?
C00E C00L 1.378(5) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.373(5) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.389(6) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.374(6) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.370(5) . ?
C00J H00J 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00O 1.379(6) . ?
C00M C00N 1.381(6) . ?
C00M C00O 1.380(6) . ?
C00M C00P 1.505(6) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00A 0.9600 . ?
C00P H00B 0.9600 . ?
C00P H00C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D Se02 C00K 95.79(16) . . ?
O004 S003 O005 120.42(18) . . ?
O004 S003 N006 106.52(16) . . ?
O004 S003 C00E 109.95(18) . . ?
O005 S003 N006 104.82(16) . . ?
O005 S003 C00E 109.78(18) . . ?
N006 S003 C00E 103.90(15) . . ?
C00A N006 S003 124.9(2) . . ?
C00B N006 S003 121.7(2) . . ?
C00B N006 C00A 106.5(3) . . ?
C00B C009 C00D 107.6(3) . . ?
C00F C009 C00B 119.7(3) . . ?
C00F C009 C00D 132.7(3) . . ?
N006 C00A I01 124.3(2) . . ?
C00D C00A I01 126.0(2) . . ?
C00D C00A N006 109.5(3) . . ?
C009 C00B N006 107.8(3) . . ?
C00I C00B N006 130.5(3) . . ?
C00I C00B C009 121.6(3) . . ?
C009 C00D Se02 125.2(3) . . ?
C00A C00D Se02 126.2(3) . . ?
C00A C00D C009 108.5(3) . . ?
C00H C00E S003 119.4(3) . . ?
C00H C00E C00L 120.6(4) . . ?
C00L C00E S003 120.0(3) . . ?
C009 C00F H00F 120.6 . . ?
C00G C00F C009 118.7(4) . . ?
C00G C00F H00F 120.6 . . ?
C00F C00G H00G 119.8 . . ?
C00F C00G C00J 120.4(4) . . ?
C00J C00G H00G 119.8 . . ?
C00E C00H H00H 120.2 . . ?
C00N C00H C00E 119.6(4) . . ?
C00N C00H H00H 120.2 . . ?
C00B C00I H00I 121.3 . . ?
C00J C00I C00B 117.3(4) . . ?
C00J C00I H00I 121.3 . . ?
C00G C00J H00J 118.9 . . ?
C00I C00J C00G 122.2(4) . . ?
C00I C00J H00J 118.9 . . ?
F007 C00K Se02 114.1(3) . . ?
F007 C00K F008 104.7(4) . . ?
F008 C00K Se02 112.6(3) . . ?
F00C C00K Se02 109.8(3) . . ?
F00C C00K F007 108.2(4) . . ?
F00C C00K F008 106.9(4) . . ?
C00E C00L H00L 120.6 . . ?
C00E C00L C00O 118.8(4) . . ?
C00O C00L H00L 120.6 . . ?
C00N C00M C00P 121.2(4) . . ?
C00O C00M C00N 118.2(4) . . ?
C00O C00M C00P 120.6(4) . . ?
C00H C00N C00M 121.2(4) . . ?
C00H C00N H00N 119.4 . . ?
C00M C00N H00N 119.4 . . ?
C00L C00O C00M 121.7(4) . . ?
C00L C00O H00O 119.1 . . ?
C00M C00O H00O 119.1 . . ?
C00M C00P H00A 109.5 . . ?
C00M C00P H00B 109.5 . . ?
C00M C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I01 C00A C00D Se02 5.2(5) . . . . ?
I01 C00A C00D C009 -176.7(2) . . . . ?
S003 N006 C00A I01 -32.1(4) . . . . ?
S003 N006 C00A C00D 152.8(3) . . . . ?
S003 N006 C00B C009 -153.4(2) . . . . ?
S003 N006 C00B C00I 29.3(5) . . . . ?
S003 C00E C00H C00N -180.0(3) . . . . ?
S003 C00E C00L C00O -179.1(3) . . . . ?
O004 S003 N006 C00A 44.3(3) . . . . ?
O004 S003 N006 C00B -169.0(3) . . . . ?
O004 S003 C00E C00H 153.4(3) . . . . ?
O004 S003 C00E C00L -26.3(4) . . . . ?
O005 S003 N006 C00A 172.9(3) . . . . ?
O005 S003 N006 C00B -40.4(3) . . . . ?
O005 S003 C00E C00H 18.8(3) . . . . ?
O005 S003 C00E C00L -161.0(3) . . . . ?
N006 S003 C00E C00H -92.9(3) . . . . ?
N006 S003 C00E C00L 87.3(3) . . . . ?
N006 C00A C00D Se02 -179.8(2) . . . . ?
N006 C00A C00D C009 -1.7(4) . . . . ?
N006 C00B C00I C00J 178.3(4) . . . . ?
C009 C00B C00I C00J 1.4(6) . . . . ?
C009 C00F C00G C00J 0.5(6) . . . . ?
C00A N006 C00B C009 -1.5(4) . . . . ?
C00A N006 C00B C00I -178.7(4) . . . . ?
C00B N006 C00A I01 177.0(2) . . . . ?
C00B N006 C00A C00D 2.0(4) . . . . ?
C00B C009 C00D Se02 178.9(2) . . . . ?
C00B C009 C00D C00A 0.8(4) . . . . ?
C00B C009 C00F C00G -0.1(5) . . . . ?
C00B C00I C00J C00G -1.1(6) . . . . ?
C00D C009 C00B N006 0.5(4) . . . . ?
C00D C009 C00B C00I 178.0(3) . . . . ?
C00D C009 C00F C00G -178.7(4) . . . . ?
C00E S003 N006 C00A -71.8(3) . . . . ?
C00E S003 N006 C00B 74.9(3) . . . . ?
C00E C00H C00N C00M -1.1(6) . . . . ?
C00E C00L C00O C00M -0.7(6) . . . . ?
C00F C009 C00B N006 -178.4(3) . . . . ?
C00F C009 C00B C00I -0.8(5) . . . . ?
C00F C009 C00D Se02 -2.4(6) . . . . ?
C00F C009 C00D C00A 179.4(4) . . . . ?
C00F C00G C00J C00I 0.1(6) . . . . ?
C00H C00E C00L C00O 1.1(6) . . . . ?
C00K Se02 C00D C009 87.7(3) . . . . ?
C00K Se02 C00D C00A -94.5(3) . . . . ?
C00L C00E C00H C00N -0.2(6) . . . . ?
C00N C00M C00O C00L -0.6(6) . . . . ?
C00O C00M C00N C00H 1.5(6) . . . . ?
C00P C00M C00N C00H -179.2(4) . . . . ?
C00P C00M C00O C00L -179.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
