# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2363156'
loop_
_audit_author_name
_audit_author_address
'congcong zhang'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2024-06-17 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H5 F9 O2 Se3'
_chemical_formula_weight         565.02

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.5035(7)
_cell_length_b                   14.3112(18)
_cell_length_c                   10.2822(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.415(2)
_cell_angle_gamma                90
_cell_volume                     806.23(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1627
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      24.80

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.327
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    6.940
_shelx_estimated_absorpt_T_min   0.287
_shelx_estimated_absorpt_T_max   0.324
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4078
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1479
_reflns_number_gt                1118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1479
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Se2 Se 0.63751(15) 0.7500 0.38680(9) 0.0647(3) Uani 1 2 d S T P . .
Se1 Se 0.01442(11) 0.54697(4) 0.69665(7) 0.0734(3) Uani 1 1 d . . . . .
O1 O 0.3996(8) 0.5853(3) 0.5126(4) 0.0708(11) Uani 1 1 d . . . . .
H1 H 0.5462 0.5818 0.5353 0.106 Uiso 1 1 calc R U . . .
F1 F 0.2013(10) 0.4454(3) 0.8997(5) 0.1245(18) Uani 1 1 d . . . . .
F5 F 0.5172(17) 0.7500 0.1274(6) 0.127(3) Uani 1 2 d S T P . .
C6 C 0.3992(12) 0.7500 0.5096(7) 0.0494(16) Uani 1 2 d S T P . .
C5 C 0.3114(9) 0.6663(3) 0.5561(5) 0.0511(12) Uani 1 1 d . . . . .
F4 F 0.2548(10) 0.6757(4) 0.2259(5) 0.1286(18) Uani 1 1 d . . . . .
F3 F 0.4738(7) 0.5212(5) 0.8163(5) 0.143(2) Uani 1 1 d . . . . .
F2 F 0.2458(12) 0.5889(4) 0.9355(5) 0.138(2) Uani 1 1 d . . . . .
C3 C 0.0467(13) 0.7500 0.6946(7) 0.0570(19) Uani 1 2 d S T P . .
C2 C 0.1354(9) 0.6670(3) 0.6481(5) 0.0533(12) Uani 1 1 d . . . . .
C1 C 0.2494(13) 0.5242(5) 0.8439(7) 0.0799(18) Uani 1 1 d . . . . .
C4 C -0.1406(14) 0.7500 0.7941(9) 0.076(2) Uani 1 2 d S T P . .
H4A H -0.0768 0.7835 0.8707 0.114 Uiso 0.5 1 calc R U P A -1
H4B H -0.1758 0.6868 0.8174 0.114 Uiso 0.5 1 calc R U P A -1
H4C H -0.2876 0.7797 0.7571 0.114 Uiso 0.5 1 calc R U P A -1
C7 C 0.396(2) 0.7500 0.2309(10) 0.085(3) Uani 1 2 d S T P . .


_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
Se2 C6 1.905(7) . ?
Se2 C7 1.984(12) . ?
Se1 C2 1.926(5) . ?
Se1 C1 1.924(7) . ?
O1 C5 1.349(6) . ?
O1 H1 0.8200 . ?
F1 C1 1.304(8) . ?
F5 C7 1.309(12) . ?
C6 C5 1.393(6) 4_575 ?
C6 C5 1.393(6) . ?
C5 C2 1.416(7) . ?
F4 C7 1.314(8) . ?
F3 C1 1.294(8) . ?
F2 C1 1.322(9) . ?
C3 C2 1.386(6) 4_575 ?
C3 C2 1.386(6) . ?
C3 C4 1.519(11) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C7 F4 1.314(8) 4_575 ?

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
C6 Se2 C7 94.8(4) . . ?
C2 Se1 C1 97.6(3) . . ?
C5 O1 H1 109.5 . . ?
C5 C6 C5 118.6(6) 4_575 . ?
C5 C6 Se2 120.7(3) 4_575 . ?
C5 C6 Se2 120.7(3) . . ?
O1 C5 C6 118.5(5) . . ?
O1 C5 C2 121.2(4) . . ?
C6 C5 C2 120.2(5) . . ?
C2 C3 C2 117.9(7) 4_575 . ?
C2 C3 C4 121.1(3) 4_575 . ?
C2 C3 C4 121.1(3) . . ?
C3 C2 C5 121.5(5) . . ?
C3 C2 Se1 122.2(4) . . ?
C5 C2 Se1 116.2(4) . . ?
F3 C1 F1 107.7(7) . . ?
F3 C1 F2 104.9(7) . . ?
F1 C1 F2 106.0(6) . . ?
F3 C1 Se1 114.7(5) . . ?
F1 C1 Se1 110.1(5) . . ?
F2 C1 Se1 112.8(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
F5 C7 F4 108.2(6) . 4_575 ?
F5 C7 F4 108.2(6) . . ?
F4 C7 F4 108.0(10) 4_575 . ?
F5 C7 Se2 107.6(8) . . ?
F4 C7 Se2 112.3(5) 4_575 . ?
F4 C7 Se2 112.3(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
C5 C6 C5 O1 -178.9(4) 4_575 . . . ?
Se2 C6 C5 O1 0.3(8) . . . . ?
C5 C6 C5 C2 0.4(10) 4_575 . . . ?
Se2 C6 C5 C2 179.6(4) . . . . ?
C2 C3 C2 C5 0.2(10) 4_575 . . . ?
C4 C3 C2 C5 -179.5(6) . . . . ?
C2 C3 C2 Se1 -176.3(3) 4_575 . . . ?
C4 C3 C2 Se1 4.0(9) . . . . ?
O1 C5 C2 C3 179.0(5) . . . . ?
C6 C5 C2 C3 -0.3(9) . . . . ?
O1 C5 C2 Se1 -4.3(7) . . . . ?
C6 C5 C2 Se1 176.4(4) . . . . ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2363182'
loop_
_audit_author_name
_audit_author_address
'congcong zhang'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2024-06-17 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F6 N Se2'
_chemical_formula_weight         461.13

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.120(3)
_cell_length_b                   15.873(4)
_cell_length_c                   7.9225(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.703(3)
_cell_angle_gamma                90
_cell_volume                     1510.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1943
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.38

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.955
_shelx_estimated_absorpt_T_min   0.383
_shelx_estimated_absorpt_T_max   0.437
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3795
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1335
_reflns_number_gt                1127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.4839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1335
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.17887(2) 0.35065(2) 0.79843(4) 0.06171(17) Uani 1 1 d . . . . .
F3 F 0.03478(16) 0.40247(13) 0.4561(3) 0.0828(6) Uani 1 1 d . . . . .
F1 F 0.01229(18) 0.27553(13) 0.5221(3) 0.0874(7) Uani 1 1 d . . . . .
F2 F 0.14433(18) 0.30976(15) 0.4411(3) 0.0886(6) Uani 1 1 d . . . . .
N1 N 0.5000 0.61040(19) 0.7500 0.0466(7) Uani 1 2 d S T P . .
H1 H 0.5000 0.6646 0.7500 0.056 Uiso 1 2 calc R U P . .
C6 C 0.44626(19) 0.47542(14) 0.7550(3) 0.0360(5) Uani 1 1 d . . . . .
C7 C 0.3751(2) 0.41237(16) 0.7640(3) 0.0418(6) Uani 1 1 d . . . . .
H7 H 0.3940 0.3559 0.7645 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4157(2) 0.56103(15) 0.7565(3) 0.0407(6) Uani 1 1 d . . . . .
C2 C 0.2756(2) 0.43534(17) 0.7722(3) 0.0453(6) Uani 1 1 d . . . . .
C4 C 0.3151(2) 0.58358(18) 0.7641(4) 0.0499(7) Uani 1 1 d . . . . .
H4 H 0.2955 0.6399 0.7637 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2457(2) 0.52047(18) 0.7722(4) 0.0513(7) Uani 1 1 d . . . . .
H3 H 0.1781 0.5341 0.7778 0.062 Uiso 1 1 calc R U . . .
C1 C 0.0882(3) 0.33462(18) 0.5397(4) 0.0538(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
Se1 C2 1.916(3) . ?
Se1 C1 1.929(3) . ?
F3 C1 1.310(3) . ?
F1 C1 1.334(3) . ?
F2 C1 1.330(3) . ?
N1 C5 1.373(3) 2_656 ?
N1 C5 1.373(3) . ?
N1 H1 0.8600 . ?
C6 C7 1.390(3) . ?
C6 C5 1.418(3) . ?
C6 C6 1.444(5) 2_656 ?
C7 C2 1.382(4) . ?
C7 H7 0.9300 . ?
C5 C4 1.392(4) . ?
C2 C3 1.407(4) . ?
C4 C3 1.373(4) . ?
C4 H4 0.9300 . ?
C3 H3 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 C1 97.44(11) . . ?
C5 N1 C5 110.4(3) 2_656 . ?
C5 N1 H1 124.8 2_656 . ?
C5 N1 H1 124.8 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 C6 133.94(14) . 2_656 ?
C5 C6 C6 106.60(14) . 2_656 ?
C2 C7 C6 118.6(2) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C5 C4 130.3(2) . . ?
N1 C5 C6 108.2(2) . . ?
C4 C5 C6 121.5(2) . . ?
C7 C2 C3 121.5(3) . . ?
C7 C2 Se1 119.9(2) . . ?
C3 C2 Se1 118.5(2) . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
F3 C1 F1 107.4(3) . . ?
F3 C1 F2 104.9(3) . . ?
F1 C1 F2 107.3(2) . . ?
F3 C1 Se1 113.9(2) . . ?
F1 C1 Se1 108.6(2) . . ?
F2 C1 Se1 114.4(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
C5 C6 C7 C2 0.7(3) . . . . ?
C6 C6 C7 C2 -179.9(3) 2_656 . . . ?
C5 N1 C5 C4 -180.0(3) 2_656 . . . ?
C5 N1 C5 C6 0.28(11) 2_656 . . . ?
C7 C6 C5 N1 178.87(18) . . . . ?
C6 C6 C5 N1 -0.7(3) 2_656 . . . ?
C7 C6 C5 C4 -0.9(3) . . . . ?
C6 C6 C5 C4 179.5(2) 2_656 . . . ?
C6 C7 C2 C3 -0.2(4) . . . . ?
C6 C7 C2 Se1 -176.57(17) . . . . ?
N1 C5 C4 C3 -179.1(2) . . . . ?
C6 C5 C4 C3 0.7(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C7 C2 C3 C4 0.0(4) . . . . ?
Se1 C2 C3 C4 176.4(2) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2363183'
loop_
_audit_author_name
_audit_author_address
'congcong zhang'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2024-06-17 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 Cl2 F3 O8 Se'
_chemical_formula_weight         646.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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'

_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. 
;

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                   11.7699(17)
_cell_length_b                   13.869(2)
_cell_length_c                   16.099(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2627.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3088
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      20.03

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.700
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13444
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4601
_reflns_number_gt                3562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.001(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.87462(5) 0.60169(4) 0.55105(4) 0.0482(2) Uani 1 1 d . . . . .
Cl2 Cl 0.4669(2) 0.0549(2) 0.75908(16) 0.1016(8) Uani 1 1 d . . . . .
Cl1 Cl 0.6775(3) -0.0504(2) 0.7173(2) 0.1306(12) Uani 1 1 d . . . . .
O2 O 0.2875(3) 0.5403(3) 0.5464(3) 0.0580(11) Uani 1 1 d . . . . .
O4 O 0.9024(3) 0.2835(3) 0.4043(3) 0.0528(11) Uani 1 1 d . . . . .
O1 O 0.2113(3) 0.4186(3) 0.4652(3) 0.0541(12) Uani 1 1 d . . . . .
O7 O 0.8367(4) 0.3966(4) 0.8206(2) 0.0625(13) Uani 1 1 d . . . . .
O3 O 0.5380(4) 0.1928(3) 0.3826(3) 0.0549(12) Uani 1 1 d . . . . .
H3 H 0.5229 0.1764 0.4303 0.082 Uiso 1 1 calc R U . . .
O8 O 0.9189(4) 0.5464(3) 0.7293(3) 0.0572(12) Uani 1 1 d . . . . .
O5 O 0.9471(3) 0.4186(4) 0.4692(3) 0.0592(13) Uani 1 1 d . . . . .
O6 O 0.6713(5) 0.2728(3) 0.7494(3) 0.0653(14) Uani 1 1 d . . . . .
C9 C 0.7053(5) 0.2865(4) 0.4202(3) 0.0348(13) Uani 1 1 d . . . . .
H9 H 0.7018 0.2593 0.4763 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5875(5) 0.2860(4) 0.3834(4) 0.0369(13) Uani 1 1 d . . . . .
H8 H 0.5940 0.3075 0.3256 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7506(4) 0.3883(4) 0.4255(3) 0.0338(13) Uani 1 1 d . . . . .
H12 H 0.7410 0.4173 0.3705 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7170(6) 0.3487(4) 0.7055(4) 0.0431(15) Uani 1 1 d . . . . .
C18 C 0.8435(5) 0.4841(4) 0.6940(4) 0.0412(15) Uani 1 1 d . . . . .
C13 C 0.6861(4) 0.4518(4) 0.4869(3) 0.0318(12) Uani 1 1 d . . . . .
H13 H 0.7010 0.5191 0.4719 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5586(4) 0.4342(4) 0.4764(3) 0.0310(13) Uani 1 1 d . . . . .
C7 C 0.3281(5) 0.4151(4) 0.4618(4) 0.0407(14) Uani 1 1 d . . . . .
C14 C 0.7244(4) 0.4378(4) 0.5765(3) 0.0305(12) Uani 1 1 d . . . . .
C11 C 0.8763(6) 0.3697(4) 0.4367(4) 0.0440(14) Uani 1 1 d . . . . .
C3 C 0.4879(5) 0.4996(4) 0.5169(4) 0.0386(14) Uani 1 1 d . . . . .
H3A H 0.5180 0.5496 0.5485 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5132(5) 0.3593(4) 0.4292(3) 0.0308(13) Uani 1 1 d . . . . .
C17 C 0.7996(5) 0.4072(5) 0.7400(3) 0.0431(14) Uani 1 1 d . . . . .
C2 C 0.3734(5) 0.4884(4) 0.5089(3) 0.0395(13) Uani 1 1 d . . . . .
F1 F 0.8213(6) 0.7868(3) 0.5616(4) 0.128(2) Uani 1 1 d . . . . .
F3 F 0.6787(5) 0.7010(4) 0.5786(5) 0.137(2) Uani 1 1 d . . . . .
C15 C 0.6815(5) 0.3647(4) 0.6243(3) 0.0374(14) Uani 1 1 d . . . . .
H15 H 0.6265 0.3243 0.6016 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7994(5) 0.2371(5) 0.3729(4) 0.0466(15) Uani 1 1 d . . . . .
H10A H 0.8002 0.1684 0.3842 0.056 Uiso 1 1 calc R U . . .
H10B H 0.7913 0.2471 0.3136 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3950(5) 0.3504(4) 0.4218(4) 0.0397(15) Uani 1 1 d . . . . .
H6 H 0.3632 0.3013 0.3901 0.048 Uiso 1 1 calc R U . . .
F2 F 0.7938(8) 0.7201(4) 0.6737(4) 0.150(3) Uani 1 1 d . . . . .
C19 C 0.8052(5) 0.5010(4) 0.6127(3) 0.0360(13) Uani 1 1 d . . . . .
C23 C 0.7879(7) 0.7077(6) 0.5962(5) 0.066(2) Uani 1 1 d . . . . .
C1 C 0.1857(5) 0.5033(5) 0.5111(5) 0.0606(19) Uani 1 1 d . . . . .
H1A H 0.1519 0.5511 0.4747 0.073 Uiso 1 1 calc R U . . .
H1B H 0.1317 0.4884 0.5547 0.073 Uiso 1 1 calc R U . . .
C22 C 1.0299(6) 0.5096(6) 0.7435(5) 0.077(2) Uani 1 1 d . . . . .
H22A H 1.0491 0.4646 0.7004 0.116 Uiso 1 1 calc R U . . .
H22B H 1.0322 0.4777 0.7963 0.116 Uiso 1 1 calc R U . . .
H22C H 1.0835 0.5618 0.7433 0.116 Uiso 1 1 calc R U . . .
C21 C 0.8946(9) 0.3089(6) 0.8385(5) 0.098(3) Uani 1 1 d . . . . .
H21A H 0.9496 0.2963 0.7959 0.147 Uiso 1 1 calc R U . . .
H21B H 0.8408 0.2569 0.8406 0.147 Uiso 1 1 calc R U . . .
H21C H 0.9323 0.3143 0.8912 0.147 Uiso 1 1 calc R U . . .
C011 C 0.6040(10) 0.0572(7) 0.7173(8) 0.121(4) Uani 1 1 d . . . . .
H01A H 0.5989 0.0799 0.6604 0.145 Uiso 1 1 calc R U . . .
H01B H 0.6483 0.1042 0.7480 0.145 Uiso 1 1 calc R U . . .
C20 C 0.6004(10) 0.2980(7) 0.8159(6) 0.117(4) Uani 1 1 d . . . . .
H20A H 0.5256 0.3118 0.7954 0.175 Uiso 1 1 calc R U . . .
H20B H 0.6304 0.3540 0.8432 0.175 Uiso 1 1 calc R U . . .
H20C H 0.5968 0.2454 0.8546 0.175 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 C19 1.898(6) . ?
Se1 C23 1.932(8) . ?
Cl2 C011 1.749(11) . ?
Cl1 C011 1.725(11) . ?
O2 C2 1.381(7) . ?
O2 C1 1.421(8) . ?
O4 C11 1.340(7) . ?
O4 C10 1.462(8) . ?
O1 C7 1.377(7) . ?
O1 C1 1.420(8) . ?
O7 C17 1.378(6) . ?
O7 C21 1.424(9) . ?
O3 C8 1.418(7) . ?
O3 H3 0.8200 . ?
O8 C18 1.363(7) . ?
O8 C22 1.421(8) . ?
O5 C11 1.196(7) . ?
O6 C16 1.377(7) . ?
O6 C20 1.403(10) . ?
C9 C8 1.508(8) . ?
C9 C10 1.508(8) . ?
C9 C12 1.512(8) . ?
C9 H9 0.9800 . ?
C8 C5 1.530(8) . ?
C8 H8 0.9800 . ?
C12 C11 1.512(8) . ?
C12 C13 1.525(8) . ?
C12 H12 0.9800 . ?
C16 C17 1.383(9) . ?
C16 C15 1.390(8) . ?
C18 C17 1.397(9) . ?
C18 C19 1.404(8) . ?
C13 C4 1.529(7) . ?
C13 C14 1.524(7) . ?
C13 H13 0.9800 . ?
C4 C3 1.393(7) . ?
C4 C5 1.394(7) . ?
C7 C6 1.357(8) . ?
C7 C2 1.375(8) . ?
C14 C15 1.370(7) . ?
C14 C19 1.418(7) . ?
C3 C2 1.363(8) . ?
C3 H3A 0.9300 . ?
C5 C6 1.402(8) . ?
F1 C23 1.291(9) . ?
F3 C23 1.318(10) . ?
C15 H15 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 H6 0.9300 . ?
F2 C23 1.262(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C19 Se1 C23 97.8(3) . . ?
C2 O2 C1 104.7(5) . . ?
C11 O4 C10 109.7(4) . . ?
C7 O1 C1 105.1(5) . . ?
C17 O7 C21 115.8(5) . . ?
C8 O3 H3 109.5 . . ?
C18 O8 C22 116.0(5) . . ?
C16 O6 C20 115.7(6) . . ?
C8 C9 C10 118.4(5) . . ?
C8 C9 C12 110.5(5) . . ?
C10 C9 C12 101.2(5) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C12 C9 H9 108.8 . . ?
O3 C8 C9 112.6(5) . . ?
O3 C8 C5 112.0(4) . . ?
C9 C8 C5 109.5(4) . . ?
O3 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C5 C8 H8 107.5 . . ?
C11 C12 C13 120.6(5) . . ?
C11 C12 C9 101.0(5) . . ?
C13 C12 C9 113.6(5) . . ?
C11 C12 H12 106.9 . . ?
C13 C12 H12 106.9 . . ?
C9 C12 H12 106.9 . . ?
C17 C16 O6 121.1(5) . . ?
C17 C16 C15 119.7(6) . . ?
O6 C16 C15 119.2(6) . . ?
O8 C18 C17 120.2(5) . . ?
O8 C18 C19 119.5(6) . . ?
C17 C18 C19 120.2(5) . . ?
C12 C13 C4 109.0(4) . . ?
C12 C13 C14 113.1(4) . . ?
C4 C13 C14 112.0(4) . . ?
C12 C13 H13 107.5 . . ?
C4 C13 H13 107.5 . . ?
C14 C13 H13 107.5 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 C13 115.5(5) . . ?
C5 C4 C13 123.7(5) . . ?
C6 C7 C2 121.7(5) . . ?
C6 C7 O1 128.4(6) . . ?
C2 C7 O1 109.9(6) . . ?
C15 C14 C19 118.3(5) . . ?
C15 C14 C13 121.1(5) . . ?
C19 C14 C13 120.6(5) . . ?
O5 C11 O4 121.1(6) . . ?
O5 C11 C12 129.5(6) . . ?
O4 C11 C12 109.3(5) . . ?
C2 C3 C4 118.1(5) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 C8 122.6(5) . . ?
C6 C5 C8 117.9(5) . . ?
C16 C17 O7 122.6(6) . . ?
C16 C17 C18 119.7(5) . . ?
O7 C17 C18 117.7(6) . . ?
C3 C2 C7 121.4(5) . . ?
C3 C2 O2 128.6(5) . . ?
C7 C2 O2 110.0(5) . . ?
C14 C15 C16 122.4(6) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
O4 C10 C9 103.5(4) . . ?
O4 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
O4 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C7 C6 C5 118.5(6) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C18 C19 C14 119.7(5) . . ?
C18 C19 Se1 118.1(4) . . ?
C14 C19 Se1 121.9(4) . . ?
F2 C23 F1 107.1(8) . . ?
F2 C23 F3 106.0(8) . . ?
F1 C23 F3 105.4(7) . . ?
F2 C23 Se1 116.5(6) . . ?
F1 C23 Se1 108.9(6) . . ?
F3 C23 Se1 112.4(6) . . ?
O2 C1 O1 109.2(5) . . ?
O2 C1 H1A 109.8 . . ?
O1 C1 H1A 109.8 . . ?
O2 C1 H1B 109.8 . . ?
O1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
O8 C22 H22A 109.5 . . ?
O8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 C011 Cl2 116.5(5) . . ?
Cl1 C011 H01A 108.2 . . ?
Cl2 C011 H01A 108.2 . . ?
Cl1 C011 H01B 108.2 . . ?
Cl2 C011 H01B 108.2 . . ?
H01A C011 H01B 107.3 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C9 C8 O3 68.3(7) . . . . ?
C12 C9 C8 O3 -175.8(5) . . . . ?
C10 C9 C8 C5 -166.3(5) . . . . ?
C12 C9 C8 C5 -50.4(6) . . . . ?
C8 C9 C12 C11 -162.8(4) . . . . ?
C10 C9 C12 C11 -36.6(5) . . . . ?
C8 C9 C12 C13 66.6(6) . . . . ?
C10 C9 C12 C13 -167.2(4) . . . . ?
C20 O6 C16 C17 70.4(9) . . . . ?
C20 O6 C16 C15 -111.5(8) . . . . ?
C22 O8 C18 C17 72.0(8) . . . . ?
C22 O8 C18 C19 -111.7(7) . . . . ?
C11 C12 C13 C4 -163.3(5) . . . . ?
C9 C12 C13 C4 -43.3(6) . . . . ?
C11 C12 C13 C14 -38.1(7) . . . . ?
C9 C12 C13 C14 82.0(6) . . . . ?
C12 C13 C4 C3 -168.4(5) . . . . ?
C14 C13 C4 C3 65.7(7) . . . . ?
C12 C13 C4 C5 10.8(7) . . . . ?
C14 C13 C4 C5 -115.1(5) . . . . ?
C1 O1 C7 C6 -176.8(6) . . . . ?
C1 O1 C7 C2 5.0(6) . . . . ?
C12 C13 C14 C15 -84.0(6) . . . . ?
C4 C13 C14 C15 39.6(7) . . . . ?
C12 C13 C14 C19 96.4(6) . . . . ?
C4 C13 C14 C19 -139.9(5) . . . . ?
C10 O4 C11 O5 176.9(6) . . . . ?
C10 O4 C11 C12 -2.2(6) . . . . ?
C13 C12 C11 O5 -27.7(9) . . . . ?
C9 C12 C11 O5 -153.8(6) . . . . ?
C13 C12 C11 O4 151.3(5) . . . . ?
C9 C12 C11 O4 25.2(6) . . . . ?
C5 C4 C3 C2 -0.2(8) . . . . ?
C13 C4 C3 C2 179.1(5) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C13 C4 C5 C6 -178.5(5) . . . . ?
C3 C4 C5 C8 179.7(5) . . . . ?
C13 C4 C5 C8 0.5(8) . . . . ?
O3 C8 C5 C4 145.1(5) . . . . ?
C9 C8 C5 C4 19.4(7) . . . . ?
O3 C8 C5 C6 -35.9(7) . . . . ?
C9 C8 C5 C6 -161.6(5) . . . . ?
O6 C16 C17 O7 -3.3(9) . . . . ?
C15 C16 C17 O7 178.5(5) . . . . ?
O6 C16 C17 C18 -179.5(5) . . . . ?
C15 C16 C17 C18 2.4(8) . . . . ?
C21 O7 C17 C16 65.2(9) . . . . ?
C21 O7 C17 C18 -118.5(8) . . . . ?
O8 C18 C17 C16 175.3(5) . . . . ?
C19 C18 C17 C16 -1.0(8) . . . . ?
O8 C18 C17 O7 -1.0(8) . . . . ?
C19 C18 C17 O7 -177.3(5) . . . . ?
C4 C3 C2 C7 -0.4(9) . . . . ?
C4 C3 C2 O2 176.1(5) . . . . ?
C6 C7 C2 C3 0.5(9) . . . . ?
O1 C7 C2 C3 178.8(5) . . . . ?
C6 C7 C2 O2 -176.7(5) . . . . ?
O1 C7 C2 O2 1.7(6) . . . . ?
C1 O2 C2 C3 175.5(6) . . . . ?
C1 O2 C2 C7 -7.6(6) . . . . ?
C19 C14 C15 C16 -2.2(8) . . . . ?
C13 C14 C15 C16 178.3(5) . . . . ?
C17 C16 C15 C14 -0.8(9) . . . . ?
O6 C16 C15 C14 -179.0(5) . . . . ?
C11 O4 C10 C9 -22.0(6) . . . . ?
C8 C9 C10 O4 157.2(5) . . . . ?
C12 C9 C10 O4 36.3(5) . . . . ?
C2 C7 C6 C5 0.1(8) . . . . ?
O1 C7 C6 C5 -177.9(5) . . . . ?
C4 C5 C6 C7 -0.7(8) . . . . ?
C8 C5 C6 C7 -179.7(5) . . . . ?
O8 C18 C19 C14 -178.3(5) . . . . ?
C17 C18 C19 C14 -2.0(8) . . . . ?
O8 C18 C19 Se1 7.4(7) . . . . ?
C17 C18 C19 Se1 -176.3(4) . . . . ?
C15 C14 C19 C18 3.5(8) . . . . ?
C13 C14 C19 C18 -176.9(5) . . . . ?
C15 C14 C19 Se1 177.6(4) . . . . ?
C13 C14 C19 Se1 -2.9(7) . . . . ?
C23 Se1 C19 C18 -82.2(5) . . . . ?
C23 Se1 C19 C14 103.6(5) . . . . ?
C2 O2 C1 O1 10.7(7) . . . . ?
C7 O1 C1 O2 -9.8(7) . . . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2363185'
loop_
_audit_author_name
_audit_author_address
'congcong zhang'
;Shandong Agricultural University
China
;
_audit_update_record             
;
2024-06-17 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl2 F3 N O2 Se'
_chemical_formula_weight         457.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.132(11)
_cell_length_b                   11.467(4)
_cell_length_c                   16.411(7)
_cell_angle_alpha                90
_cell_angle_beta                 125.672(12)
_cell_angle_gamma                90
_cell_volume                     3689(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3373
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.75

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.363
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9015
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3232
_reflns_number_gt                2052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0966P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0353(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3232
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001

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 0.73044(3) 0.47781(5) 0.51624(4) 0.0582(3) Uani 1 1 d . . . . .
Cl2 Cl 0.50490(8) 0.27612(13) 0.05210(13) 0.0781(6) Uani 1 1 d . . . . .
Cl1 Cl 0.59688(9) -0.14058(15) 0.23153(14) 0.0845(6) Uani 1 1 d . . . . .
O1 O 0.74212(17) 0.0184(3) 0.2437(3) 0.0517(9) Uani 1 1 d . . . . .
O2 O 0.83655(16) 0.1242(3) 0.3343(3) 0.0565(10) Uani 1 1 d . . . . .
N1 N 0.61246(18) 0.1054(3) 0.1916(3) 0.0440(10) Uani 1 1 d . . . . .
H1 H 0.6205 0.1234 0.1485 0.053 Uiso 1 1 d R U . . .
C11 C 0.7248(2) 0.3332(4) 0.3695(3) 0.0355(11) Uani 1 1 d . . . . .
H11 H 0.7653 0.3706 0.3907 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6990(2) 0.2491(4) 0.2957(3) 0.0329(10) Uani 1 1 d . . . . .
C7 C 0.6384(2) 0.1922(4) 0.2648(3) 0.0355(11) Uani 1 1 d . . . . .
F3 F 0.6846(3) 0.6963(4) 0.4930(4) 0.1239(17) Uani 1 1 d . . . . .
C14 C 0.7697(2) 0.1113(4) 0.2715(4) 0.0390(11) Uani 1 1 d . . . . .
C10 C 0.6918(2) 0.3630(4) 0.4124(4) 0.0414(12) Uani 1 1 d . . . . .
C13 C 0.7329(2) 0.2265(4) 0.2434(4) 0.0426(12) Uani 1 1 d . . . . .
H13A H 0.6984 0.2282 0.1715 0.051 Uiso 1 1 calc R U . . .
H13B H 0.7651 0.2886 0.2601 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6066(2) 0.2210(4) 0.3098(4) 0.0478(13) Uani 1 1 d . . . . .
H8 H 0.5669 0.1822 0.2908 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5451(2) 0.0651(4) 0.1403(4) 0.0406(11) Uani 1 1 d . . . . .
F2 F 0.6830(4) 0.6399(4) 0.3692(4) 0.149(2) Uani 1 1 d . . . . .
C6 C 0.4902(2) 0.1360(5) 0.0731(4) 0.0516(14) Uani 1 1 d . . . . .
C9 C 0.6328(3) 0.3065(4) 0.3827(4) 0.0497(13) Uani 1 1 d . . . . .
H9 H 0.6104 0.3257 0.4117 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5303(3) -0.0482(5) 0.1504(4) 0.0521(14) Uani 1 1 d . . . . .
F1 F 0.6082(3) 0.5830(5) 0.3876(5) 0.163(3) Uani 1 1 d . . . . .
C15 C 0.8767(3) 0.0185(5) 0.3640(5) 0.0713(19) Uani 1 1 d . . . . .
H15A H 0.8777 -0.0087 0.3095 0.107 Uiso 1 1 calc R U . . .
H15B H 0.8566 -0.0401 0.3810 0.107 Uiso 1 1 calc R U . . .
H15C H 0.9223 0.0342 0.4212 0.107 Uiso 1 1 calc R U . . .
C1 C 0.4241(3) 0.0967(6) 0.0197(4) 0.0640(17) Uani 1 1 d . . . . .
H1A H 0.3884 0.1457 -0.0255 0.077 Uiso 1 1 calc R U . . .
C3 C 0.4639(3) -0.0875(6) 0.0981(5) 0.0688(18) Uani 1 1 d . . . . .
H3 H 0.4548 -0.1635 0.1067 0.083 Uiso 1 1 calc R U . . .
C2 C 0.4114(3) -0.0136(6) 0.0331(5) 0.072(2) Uani 1 1 d . . . . .
H2 H 0.3666 -0.0397 -0.0019 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6733(4) 0.6033(6) 0.4364(6) 0.083(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
Se1 C16 1.892(7) . ?
Se1 C10 1.912(5) . ?
Cl2 C6 1.723(6) . ?
Cl1 C4 1.727(6) . ?
O1 C14 1.196(5) . ?
O2 C14 1.322(5) . ?
O2 C15 1.447(6) . ?
N1 C7 1.396(6) . ?
N1 C5 1.403(6) . ?
N1 H1 0.8599 . ?
C11 C12 1.380(6) . ?
C11 C10 1.378(6) . ?
C11 H11 0.9300 . ?
C12 C7 1.400(6) . ?
C12 C13 1.512(6) . ?
C7 C8 1.379(6) . ?
F3 C16 1.334(7) . ?
C14 C13 1.507(6) . ?
C10 C9 1.369(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C8 C9 1.382(7) . ?
C8 H8 0.9300 . ?
C5 C4 1.384(7) . ?
C5 C6 1.388(7) . ?
F2 C16 1.321(9) . ?
C6 C1 1.373(7) . ?
C9 H9 0.9300 . ?
C4 C3 1.379(8) . ?
F1 C16 1.303(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 C2 1.349(8) . ?
C1 H1A 0.9300 . ?
C3 C2 1.373(9) . ?
C3 H3 0.9300 . ?
C2 H2 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
C16 Se1 C10 97.3(3) . . ?
C14 O2 C15 116.2(4) . . ?
C7 N1 C5 122.1(4) . . ?
C7 N1 H1 109.5 . . ?
C5 N1 H1 108.9 . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 119.0(4) . . ?
C11 C12 C13 120.1(4) . . ?
C7 C12 C13 120.7(4) . . ?
C8 C7 N1 121.5(4) . . ?
C8 C7 C12 119.0(4) . . ?
N1 C7 C12 119.5(4) . . ?
O1 C14 O2 123.5(4) . . ?
O1 C14 C13 124.5(4) . . ?
O2 C14 C13 112.0(4) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 Se1 120.5(4) . . ?
C11 C10 Se1 120.0(3) . . ?
C14 C13 C12 113.2(4) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C4 C5 C6 116.8(4) . . ?
C4 C5 N1 121.8(4) . . ?
C6 C5 N1 121.3(5) . . ?
C1 C6 C5 122.0(5) . . ?
C1 C6 Cl2 118.5(5) . . ?
C5 C6 Cl2 119.5(4) . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 Cl1 118.6(4) . . ?
C3 C4 Cl1 120.0(5) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C1 C6 119.6(6) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C1 C2 C3 120.7(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
F1 C16 F3 104.7(6) . . ?
F1 C16 F2 106.3(7) . . ?
F3 C16 F2 105.2(6) . . ?
F1 C16 Se1 114.9(6) . . ?
F3 C16 Se1 110.9(5) . . ?
F2 C16 Se1 114.1(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
C10 C11 C12 C7 -0.7(6) . . . . ?
C10 C11 C12 C13 174.3(4) . . . . ?
C5 N1 C7 C8 17.6(7) . . . . ?
C5 N1 C7 C12 -164.3(4) . . . . ?
C11 C12 C7 C8 -0.7(6) . . . . ?
C13 C12 C7 C8 -175.6(4) . . . . ?
C11 C12 C7 N1 -178.8(4) . . . . ?
C13 C12 C7 N1 6.3(6) . . . . ?
C15 O2 C14 O1 3.8(7) . . . . ?
C15 O2 C14 C13 -178.6(5) . . . . ?
C12 C11 C10 C9 1.3(7) . . . . ?
C12 C11 C10 Se1 178.7(3) . . . . ?
O1 C14 C13 C12 73.4(6) . . . . ?
O2 C14 C13 C12 -104.2(4) . . . . ?
C11 C12 C13 C14 109.3(5) . . . . ?
C7 C12 C13 C14 -75.8(5) . . . . ?
N1 C7 C8 C9 179.6(4) . . . . ?
C12 C7 C8 C9 1.5(7) . . . . ?
C7 N1 C5 C4 -114.8(5) . . . . ?
C7 N1 C5 C6 68.2(6) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
N1 C5 C6 C1 177.7(5) . . . . ?
C4 C5 C6 Cl2 -177.1(4) . . . . ?
N1 C5 C6 Cl2 0.0(6) . . . . ?
C11 C10 C9 C8 -0.5(7) . . . . ?
Se1 C10 C9 C8 -177.9(4) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
C6 C5 C4 C3 -1.7(7) . . . . ?
N1 C5 C4 C3 -178.7(5) . . . . ?
C6 C5 C4 Cl1 178.9(4) . . . . ?
N1 C5 C4 Cl1 1.9(7) . . . . ?
C5 C6 C1 C2 0.8(8) . . . . ?
Cl2 C6 C1 C2 178.6(5) . . . . ?
C5 C4 C3 C2 1.2(8) . . . . ?
Cl1 C4 C3 C2 -179.4(5) . . . . ?
C6 C1 C2 C3 -1.4(9) . . . . ?
C4 C3 C2 C1 0.4(9) . . . . ?
C10 Se1 C16 F1 55.5(6) . . . . ?
C10 Se1 C16 F3 173.9(6) . . . . ?
C10 Se1 C16 F2 -67.6(6) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.111

