# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_y20210103_1a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2mncth
_database_code_depnum_ccdc_archive 'CCDC 2432657'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d5ob01135c 2025
loop_
_audit_author_name
_audit_author_address
'Haoliang Shi'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2025-03-20 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2025-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 F10 Se2'
_chemical_formula_sum            'C12 F10 Se2'
_chemical_formula_weight         492.04
_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'
F F 0.0727 0.0534 '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                   5.7599(3)
_cell_length_b                   9.4957(5)
_cell_length_c                   25.7505(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1408.41(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      68.251
_cell_measurement_theta_min      4.964
_shelx_estimated_absorpt_T_max   0.578
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    7.685
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.3662.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_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            19971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_min         4.964
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2514
_reflns_number_total             2553
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(12)
_refine_ls_extinction_coef       0.0035(3)
_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   1.116
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.116
_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)+(0.0258P)²+0.7628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
Se12 Se 0.28719(12) 0.04645(6) 0.31315(2) 0.0659(2) Uani 1 1 d . . . . .
Se13 Se 0.54906(13) 0.20991(7) 0.28049(2) 0.0726(2) Uani 1 1 d . . . . .
F20 F 0.7537(6) 0.3785(4) 0.37114(13) 0.0789(9) Uani 1 1 d . . . . .
F24 F 0.1003(7) 0.3835(4) 0.26048(13) 0.0825(10) Uani 1 1 d . . . . .
F11 F 0.0785(7) 0.1722(4) 0.41167(14) 0.0826(10) Uani 1 1 d . . . . .
F23 F -0.0536(6) 0.6156(4) 0.30813(16) 0.0887(10) Uani 1 1 d . . . . .
F7 F 0.7245(7) -0.0982(4) 0.36049(14) 0.0923(11) Uani 1 1 d . . . . .
F21 F 0.5958(8) 0.6115(4) 0.41822(14) 0.0934(12) Uani 1 1 d . . . . .
F22 F 0.1913(8) 0.7296(3) 0.38708(17) 0.0964(13) Uani 1 1 d . . . . .
F10 F 0.2197(9) 0.1584(4) 0.51034(13) 0.1035(14) Uani 1 1 d . . . . .
F9 F 0.6103(8) 0.0172(5) 0.53519(14) 0.1054(14) Uani 1 1 d . . . . .
F8 F 0.8621(7) -0.1117(5) 0.46004(17) 0.1053(14) Uani 1 1 d . . . . .
C15 C 0.2291(9) 0.4371(5) 0.29938(17) 0.0551(11) Uani 1 1 d . . . . .
C19 C 0.5541(9) 0.4345(5) 0.35479(19) 0.0555(11) Uani 1 1 d . . . . .
C16 C 0.1480(9) 0.5562(6) 0.3233(2) 0.0611(13) Uani 1 1 d . . . . .
C17 C 0.2693(10) 0.6143(5) 0.3631(2) 0.0619(13) Uani 1 1 d . . . . .
C1 C 0.3963(9) 0.0371(5) 0.38270(18) 0.0514(11) Uani 1 1 d . . . . .
C6 C 0.5963(9) -0.0333(6) 0.3967(2) 0.0592(12) Uani 1 1 d . . . . .
C14 C 0.4334(9) 0.3743(5) 0.31432(18) 0.0512(10) Uani 1 1 d . . . . .
C2 C 0.2740(9) 0.1018(5) 0.42216(19) 0.0558(11) Uani 1 1 d . . . . .
C18 C 0.4740(11) 0.5543(6) 0.3792(2) 0.0624(13) Uani 1 1 d . . . . .
C4 C 0.5404(11) 0.0234(6) 0.4854(2) 0.0692(14) Uani 1 1 d . . . . .
C5 C 0.6673(9) -0.0418(6) 0.4477(2) 0.0655(13) Uani 1 1 d . . . . .
C3 C 0.3431(11) 0.0945(6) 0.4729(2) 0.0652(14) 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
Se12 Se13 2.3220(10) . ?
Se12 C1 1.900(5) . ?
Se13 C14 1.907(5) . ?
F20 C19 1.335(6) . ?
F24 C15 1.346(6) . ?
F11 C2 1.337(6) . ?
F23 C16 1.349(6) . ?
F7 C6 1.339(6) . ?
F21 C18 1.341(6) . ?
F22 C17 1.335(6) . ?
F10 C3 1.343(6) . ?
F9 C4 1.344(6) . ?
F8 C5 1.342(7) . ?
C15 C16 1.370(7) . ?
C15 C14 1.374(7) . ?
C19 C14 1.377(7) . ?
C19 C18 1.378(8) . ?
C16 C17 1.357(8) . ?
C17 C18 1.373(8) . ?
C1 C6 1.380(7) . ?
C1 C2 1.381(7) . ?
C6 C5 1.379(8) . ?
C2 C3 1.367(7) . ?
C4 C5 1.364(8) . ?
C4 C3 1.361(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se12 Se13 99.09(15) . . ?
C14 Se13 Se12 98.90(14) . . ?
F24 C15 C16 117.3(5) . . ?
F24 C15 C14 121.1(4) . . ?
C16 C15 C14 121.6(5) . . ?
F20 C19 C14 120.5(5) . . ?
F20 C19 C18 118.3(5) . . ?
C14 C19 C18 121.2(5) . . ?
F23 C16 C15 120.6(5) . . ?
F23 C16 C17 119.5(5) . . ?
C17 C16 C15 119.9(5) . . ?
F22 C17 C16 120.6(6) . . ?
F22 C17 C18 119.3(6) . . ?
C16 C17 C18 120.1(5) . . ?
C6 C1 Se12 123.0(4) . . ?
C6 C1 C2 116.7(4) . . ?
C2 C1 Se12 120.3(4) . . ?
F7 C6 C1 120.1(5) . . ?
F7 C6 C5 118.2(5) . . ?
C5 C6 C1 121.7(5) . . ?
C15 C14 Se13 121.8(4) . . ?
C15 C14 C19 117.6(5) . . ?
C19 C14 Se13 120.6(4) . . ?
F11 C2 C1 120.2(4) . . ?
F11 C2 C3 117.6(5) . . ?
C3 C2 C1 122.1(5) . . ?
F21 C18 C19 120.0(5) . . ?
F21 C18 C17 120.5(5) . . ?
C17 C18 C19 119.5(5) . . ?
F9 C4 C5 119.9(5) . . ?
F9 C4 C3 119.9(6) . . ?
C3 C4 C5 120.2(5) . . ?
F8 C5 C6 120.1(5) . . ?
F8 C5 C4 120.3(5) . . ?
C4 C5 C6 119.6(5) . . ?
F10 C3 C2 120.6(5) . . ?
F10 C3 C4 119.7(5) . . ?
C4 C3 C2 119.7(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
Se12 C1 C6 F7 0.5(7) . . . . ?
Se12 C1 C6 C5 -178.0(4) . . . . ?
Se12 C1 C2 F11 -0.3(7) . . . . ?
Se12 C1 C2 C3 178.2(4) . . . . ?
F20 C19 C14 Se13 -0.2(6) . . . . ?
F20 C19 C14 C15 180.0(4) . . . . ?
F20 C19 C18 F21 0.0(7) . . . . ?
F20 C19 C18 C17 179.9(4) . . . . ?
F24 C15 C16 F23 0.4(7) . . . . ?
F24 C15 C16 C17 179.4(4) . . . . ?
F24 C15 C14 Se13 0.9(6) . . . . ?
F24 C15 C14 C19 -179.3(4) . . . . ?
F11 C2 C3 F10 -1.2(8) . . . . ?
F11 C2 C3 C4 179.7(5) . . . . ?
F23 C16 C17 F22 -0.3(7) . . . . ?
F23 C16 C17 C18 179.5(4) . . . . ?
F7 C6 C5 F8 1.1(9) . . . . ?
F7 C6 C5 C4 179.9(5) . . . . ?
F22 C17 C18 F21 -0.7(7) . . . . ?
F22 C17 C18 C19 179.4(5) . . . . ?
F9 C4 C5 F8 -0.2(10) . . . . ?
F9 C4 C5 C6 -179.1(6) . . . . ?
F9 C4 C3 F10 0.2(9) . . . . ?
F9 C4 C3 C2 179.3(6) . . . . ?
C15 C16 C17 F22 -179.3(4) . . . . ?
C15 C16 C17 C18 0.5(8) . . . . ?
C16 C15 C14 Se13 -179.1(4) . . . . ?
C16 C15 C14 C19 0.7(7) . . . . ?
C16 C17 C18 F21 179.6(5) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C1 C6 C5 F8 179.7(5) . . . . ?
C1 C6 C5 C4 -1.5(9) . . . . ?
C1 C2 C3 F10 -179.8(5) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C6 C1 C2 F11 179.9(5) . . . . ?
C6 C1 C2 C3 -1.5(8) . . . . ?
C14 C15 C16 F23 -179.7(4) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C14 C19 C18 F21 -179.5(4) . . . . ?
C14 C19 C18 C17 0.4(8) . . . . ?
C2 C1 C6 F7 -179.7(5) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C18 C19 C14 Se13 179.2(4) . . . . ?
C18 C19 C14 C15 -0.6(7) . . . . ?
C5 C4 C3 F10 -179.9(6) . . . . ?
C5 C4 C3 C2 -0.8(9) . . . . ?
C3 C4 C5 F8 179.8(6) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?


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

data_shl_y20210103_04_38_0m
_database_code_depnum_ccdc_archive 'CCDC 2470472'
loop_
_audit_author_name
_audit_author_address
'Haoliang Shi'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 F8 N2 Se2'
_chemical_formula_sum            'C10 F8 N2 Se2'
_chemical_formula_weight         458.04
_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'
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      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                   9.8337(4)
_cell_length_b                   11.1932(5)
_cell_length_c                   24.2439(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.043(3)
_cell_angle_gamma                90
_cell_volume                     2653.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2494
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      53.163
_cell_measurement_theta_min      3.668
_shelx_estimated_absorpt_T_max   0.275
_shelx_estimated_absorpt_T_min   0.224
_exptl_absorpt_coefficient_mu    7.907
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1491 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.4625.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40007
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.512
_diffrn_reflns_theta_min         3.667
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4224
_reflns_number_total             4768
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.908
_refine_diff_density_min         -1.068
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.00104(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0445
_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)+(0.0456P)²+4.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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 1.08065(5) 0.34130(5) 0.52640(2) 0.06668(18) Uani 1 1 d . . . . .
Se02 Se 0.95553(5) 0.40998(5) 0.59518(3) 0.0751(2) Uani 1 1 d . . . . .
Se03 Se 0.01733(5) 0.78932(6) 0.62539(2) 0.0799(2) Uani 1 1 d . . . . .
Se04 Se 0.17432(6) 0.63632(6) 0.63922(3) 0.0946(2) Uani 1 1 d . . . . .
F005 F 1.1099(3) 0.0831(3) 0.48775(11) 0.0824(8) Uani 1 1 d . . . . .
F006 F 1.2570(3) 0.3216(3) 0.64307(12) 0.0825(8) Uani 1 1 d . . . . .
F007 F -0.1606(4) 0.6172(3) 0.68722(13) 0.0894(9) Uani 1 1 d . . . . .
F008 F 1.2462(4) -0.0997(3) 0.54022(13) 0.0919(9) Uani 1 1 d . . . . .
F1 F 0.4064(4) 0.6681(3) 0.56589(14) 0.0974(10) Uani 1 1 d . . . . .
F00A F 1.3819(3) 0.1261(3) 0.68863(13) 0.0965(10) Uani 1 1 d . . . . .
F00B F 0.6713(3) 0.5134(3) 0.56592(15) 0.0951(10) Uani 1 1 d . . . . .
F00C F 0.8812(3) 0.1360(3) 0.59105(16) 0.0957(10) Uani 1 1 d . . . . .
N00D N 1.3127(4) 0.0148(4) 0.61383(16) 0.0644(9) Uani 1 1 d . . . . .
F00E F 0.4308(3) 0.3991(4) 0.54705(18) 0.1231(14) Uani 1 1 d . . . . .
F00F F 0.2921(4) 0.7898(4) 0.74096(14) 0.1156(12) Uani 1 1 d . . . . .
F00G F 0.6475(4) 0.7811(4) 0.5899(2) 0.1280(15) Uani 1 1 d . . . . .
F00H F -0.2475(5) 0.6426(4) 0.78765(16) 0.1253(15) Uani 1 1 d . . . . .
F00I F 0.0647(4) 0.9864(3) 0.71646(17) 0.1195(13) Uani 1 1 d . . . . .
F00J F -0.0314(5) 0.9931(4) 0.81631(17) 0.1317(15) Uani 1 1 d . . . . .
C00K C 1.1737(4) 0.2094(4) 0.56386(17) 0.0519(9) Uani 1 1 d . . . . .
F00L F 0.5379(5) 0.8997(5) 0.75562(19) 0.1477(18) Uani 1 1 d . . . . .
F00M F 0.6311(5) 0.0390(4) 0.5699(2) 0.1372(17) Uani 1 1 d . . . . .
C00N C 1.1758(4) 0.1004(4) 0.53824(17) 0.0565(10) Uani 1 1 d . . . . .
C00O C 1.2462(5) 0.0079(4) 0.56468(19) 0.0623(11) Uani 1 1 d . . . . .
C00P C 0.3414(5) 0.7228(4) 0.6528(2) 0.0643(11) Uani 1 1 d . . . . .
N00Q N 0.5328(5) 0.2203(5) 0.5580(2) 0.0897(14) Uani 1 1 d . . . . .
C00R C -0.0426(4) 0.7994(4) 0.69770(17) 0.0588(10) Uani 1 1 d . . . . .
C00S C 0.7862(4) 0.3284(4) 0.57775(17) 0.0567(10) Uani 1 1 d . . . . .
N00T N 0.5897(5) 0.8390(5) 0.6732(3) 0.0953(16) Uani 1 1 d . . . . .
C00U C 1.2467(4) 0.2182(4) 0.61586(17) 0.0567(10) Uani 1 1 d . . . . .
C00V C 1.3124(4) 0.1181(5) 0.63821(19) 0.0636(11) Uani 1 1 d . . . . .
C00W C -0.1226(5) 0.7132(4) 0.71788(18) 0.0626(11) Uani 1 1 d . . . . .
C00X C 0.6676(5) 0.3938(5) 0.5663(2) 0.0675(12) Uani 1 1 d . . . . .
C00Y C -0.0125(5) 0.8964(5) 0.7318(2) 0.0746(13) Uani 1 1 d . . . . .
N00Z N -0.1381(5) 0.8182(5) 0.80115(18) 0.0853(13) Uani 1 1 d . . . . .
C010 C 0.4346(5) 0.7230(4) 0.6144(2) 0.0695(12) Uani 1 1 d . . . . .
C011 C 0.6448(7) 0.1569(5) 0.5689(3) 0.0860(16) Uani 1 1 d . . . . .
C012 C 0.7723(5) 0.2064(4) 0.5791(2) 0.0675(12) Uani 1 1 d . . . . .
C013 C 0.5454(5) 0.3352(6) 0.5574(2) 0.0811(15) Uani 1 1 d . . . . .
C014 C -0.1674(5) 0.7271(5) 0.7687(2) 0.0759(13) Uani 1 1 d . . . . .
C015 C 0.3778(6) 0.7837(5) 0.7017(2) 0.0767(13) Uani 1 1 d . . . . .
C016 C -0.0631(6) 0.9002(5) 0.7827(2) 0.0832(15) Uani 1 1 d . . . . .
C017 C 0.5563(5) 0.7823(5) 0.6272(3) 0.0852(17) Uani 1 1 d . . . . .
C018 C 0.5023(7) 0.8393(6) 0.7088(3) 0.0925(18) 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 Se02 2.3059(8) . ?
Se01 C00K 1.915(4) . ?
Se02 C00S 1.907(4) . ?
Se03 Se04 2.3064(10) . ?
Se03 C00R 1.911(4) . ?
Se04 C00P 1.905(5) . ?
F005 C00N 1.337(5) . ?
F006 C00U 1.331(5) . ?
F007 C00W 1.336(5) . ?
F008 C00O 1.342(5) . ?
F1 C010 1.329(6) . ?
F00A C00V 1.339(5) . ?
F00B C00X 1.338(6) . ?
F00C C012 1.337(6) . ?
N00D C00O 1.300(6) . ?
N00D C00V 1.299(6) . ?
F00E C013 1.336(6) . ?
F00F C015 1.338(6) . ?
F00G C017 1.339(7) . ?
F00H C014 1.342(6) . ?
F00I C00Y 1.337(6) . ?
F00J C016 1.338(6) . ?
C00K C00N 1.371(6) . ?
C00K C00U 1.387(6) . ?
F00L C018 1.336(7) . ?
F00M C011 1.328(7) . ?
C00N C00O 1.367(6) . ?
C00P C010 1.373(7) . ?
C00P C015 1.382(7) . ?
N00Q C011 1.313(8) . ?
N00Q C013 1.292(8) . ?
C00R C00W 1.368(6) . ?
C00R C00Y 1.378(7) . ?
C00S C00X 1.380(6) . ?
C00S C012 1.373(7) . ?
N00T C017 1.295(8) . ?
N00T C018 1.281(9) . ?
C00U C00V 1.376(6) . ?
C00W C014 1.361(7) . ?
C00X C013 1.367(8) . ?
C00Y C016 1.379(8) . ?
N00Z C014 1.301(7) . ?
N00Z C016 1.288(8) . ?
C010 C017 1.375(8) . ?
C011 C012 1.370(8) . ?
C015 C018 1.368(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00K Se01 Se02 100.30(12) . . ?
C00S Se02 Se01 101.54(12) . . ?
C00R Se03 Se04 100.17(13) . . ?
C00P Se04 Se03 101.53(14) . . ?
C00V N00D C00O 116.4(4) . . ?
C00N C00K Se01 120.1(3) . . ?
C00N C00K C00U 116.4(4) . . ?
C00U C00K Se01 123.5(3) . . ?
F005 C00N C00K 121.0(4) . . ?
F005 C00N C00O 119.5(4) . . ?
C00O C00N C00K 119.5(4) . . ?
F008 C00O C00N 119.7(4) . . ?
N00D C00O F008 115.7(4) . . ?
N00D C00O C00N 124.5(4) . . ?
C010 C00P Se04 120.6(4) . . ?
C010 C00P C015 116.7(5) . . ?
C015 C00P Se04 122.6(4) . . ?
C013 N00Q C011 117.4(5) . . ?
C00W C00R Se03 122.1(3) . . ?
C00W C00R C00Y 115.9(4) . . ?
C00Y C00R Se03 121.9(4) . . ?
C00X C00S Se02 119.4(4) . . ?
C012 C00S Se02 123.9(4) . . ?
C012 C00S C00X 116.6(4) . . ?
C018 N00T C017 117.0(5) . . ?
F006 C00U C00K 121.2(4) . . ?
F006 C00U C00V 120.3(4) . . ?
C00V C00U C00K 118.4(4) . . ?
F00A C00V C00U 118.6(4) . . ?
N00D C00V F00A 116.7(4) . . ?
N00D C00V C00U 124.7(4) . . ?
F007 C00W C00R 120.3(4) . . ?
F007 C00W C014 119.9(5) . . ?
C014 C00W C00R 119.8(5) . . ?
F00B C00X C00S 120.6(4) . . ?
F00B C00X C013 120.2(5) . . ?
C013 C00X C00S 119.2(5) . . ?
F00I C00Y C00R 121.3(5) . . ?
F00I C00Y C016 119.6(5) . . ?
C00R C00Y C016 119.1(5) . . ?
C016 N00Z C014 116.6(5) . . ?
F1 C010 C00P 120.4(5) . . ?
F1 C010 C017 121.3(5) . . ?
C00P C010 C017 118.3(5) . . ?
F00M C011 C012 119.5(6) . . ?
N00Q C011 F00M 117.1(6) . . ?
N00Q C011 C012 123.4(5) . . ?
F00C C012 C00S 120.8(4) . . ?
F00C C012 C011 119.9(5) . . ?
C011 C012 C00S 119.3(5) . . ?
F00E C013 C00X 118.9(6) . . ?
N00Q C013 F00E 117.1(5) . . ?
N00Q C013 C00X 124.1(5) . . ?
F00H C014 C00W 119.1(5) . . ?
N00Z C014 F00H 116.5(5) . . ?
N00Z C014 C00W 124.4(5) . . ?
F00F C015 C00P 120.7(5) . . ?
F00F C015 C018 120.6(6) . . ?
C018 C015 C00P 118.7(6) . . ?
F00J C016 C00Y 119.1(6) . . ?
N00Z C016 F00J 116.6(5) . . ?
N00Z C016 C00Y 124.3(5) . . ?
F00G C017 C010 118.1(7) . . ?
N00T C017 F00G 117.4(6) . . ?
N00T C017 C010 124.5(6) . . ?
F00L C018 C015 119.2(7) . . ?
N00T C018 F00L 116.1(6) . . ?
N00T C018 C015 124.7(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C00K C00N F005 -2.1(5) . . . . ?
Se01 C00K C00N C00O 177.9(3) . . . . ?
Se01 C00K C00U F006 -0.5(6) . . . . ?
Se01 C00K C00U C00V -178.4(3) . . . . ?
Se02 C00S C00X F00B 1.7(6) . . . . ?
Se02 C00S C00X C013 -175.7(4) . . . . ?
Se02 C00S C012 F00C -2.8(6) . . . . ?
Se02 C00S C012 C011 176.3(4) . . . . ?
Se03 C00R C00W F007 0.7(6) . . . . ?
Se03 C00R C00W C014 -177.2(4) . . . . ?
Se03 C00R C00Y F00I -2.5(7) . . . . ?
Se03 C00R C00Y C016 177.6(4) . . . . ?
Se04 C00P C010 F1 3.6(6) . . . . ?
Se04 C00P C010 C017 -177.1(4) . . . . ?
Se04 C00P C015 F00F -3.7(7) . . . . ?
Se04 C00P C015 C018 177.3(4) . . . . ?
F005 C00N C00O F008 -1.3(6) . . . . ?
F005 C00N C00O N00D -179.5(4) . . . . ?
F006 C00U C00V F00A 2.7(7) . . . . ?
F006 C00U C00V N00D -177.1(4) . . . . ?
F007 C00W C014 F00H 1.2(7) . . . . ?
F007 C00W C014 N00Z -178.7(5) . . . . ?
F1 C010 C017 F00G -1.5(7) . . . . ?
F1 C010 C017 N00T 178.9(5) . . . . ?
F00B C00X C013 F00E 1.7(8) . . . . ?
F00B C00X C013 N00Q -178.7(5) . . . . ?
F00F C015 C018 F00L 0.2(9) . . . . ?
F00F C015 C018 N00T -179.2(6) . . . . ?
F00I C00Y C016 F00J -1.4(8) . . . . ?
F00I C00Y C016 N00Z 180.0(5) . . . . ?
C00K C00N C00O F008 178.7(4) . . . . ?
C00K C00N C00O N00D 0.5(7) . . . . ?
C00K C00U C00V F00A -179.4(4) . . . . ?
C00K C00U C00V N00D 0.8(7) . . . . ?
F00M C011 C012 F00C -1.3(8) . . . . ?
F00M C011 C012 C00S 179.6(5) . . . . ?
C00N C00K C00U F006 176.5(4) . . . . ?
C00N C00K C00U C00V -1.4(6) . . . . ?
C00O N00D C00V F00A -179.4(4) . . . . ?
C00O N00D C00V C00U 0.4(7) . . . . ?
C00P C010 C017 F00G 179.2(4) . . . . ?
C00P C010 C017 N00T -0.3(8) . . . . ?
C00P C015 C018 F00L 179.2(5) . . . . ?
C00P C015 C018 N00T -0.3(9) . . . . ?
N00Q C011 C012 F00C 178.6(5) . . . . ?
N00Q C011 C012 C00S -0.5(8) . . . . ?
C00R C00W C014 F00H 179.0(5) . . . . ?
C00R C00W C014 N00Z -0.9(8) . . . . ?
C00R C00Y C016 F00J 178.5(5) . . . . ?
C00R C00Y C016 N00Z -0.1(9) . . . . ?
C00S C00X C013 F00E 179.1(5) . . . . ?
C00S C00X C013 N00Q -1.3(8) . . . . ?
C00U C00K C00N F005 -179.2(4) . . . . ?
C00U C00K C00N C00O 0.8(6) . . . . ?
C00V N00D C00O F008 -179.3(4) . . . . ?
C00V N00D C00O C00N -1.1(7) . . . . ?
C00W C00R C00Y F00I -179.9(5) . . . . ?
C00W C00R C00Y C016 0.2(7) . . . . ?
C00X C00S C012 F00C -178.6(4) . . . . ?
C00X C00S C012 C011 0.5(7) . . . . ?
C00Y C00R C00W F007 178.1(4) . . . . ?
C00Y C00R C00W C014 0.2(7) . . . . ?
C010 C00P C015 F00F 178.8(5) . . . . ?
C010 C00P C015 C018 -0.1(7) . . . . ?
C011 N00Q C013 F00E -179.1(5) . . . . ?
C011 N00Q C013 C00X 1.3(9) . . . . ?
C012 C00S C00X F00B 177.8(4) . . . . ?
C012 C00S C00X C013 0.4(7) . . . . ?
C013 N00Q C011 F00M 179.6(5) . . . . ?
C013 N00Q C011 C012 -0.4(9) . . . . ?
C014 N00Z C016 F00J -179.1(5) . . . . ?
C014 N00Z C016 C00Y -0.5(9) . . . . ?
C015 C00P C010 F1 -178.9(4) . . . . ?
C015 C00P C010 C017 0.4(7) . . . . ?
C016 N00Z C014 F00H -178.9(5) . . . . ?
C016 N00Z C014 C00W 1.0(9) . . . . ?
C017 N00T C018 F00L -179.1(5) . . . . ?
C017 N00T C018 C015 0.4(9) . . . . ?
C018 N00T C017 F00G -179.7(5) . . . . ?
C018 N00T C017 C010 -0.1(9) . . . . ?

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

data_y20210103_05_6_2nd_0m1_a
_database_code_depnum_ccdc_archive 'CCDC 2470475'
loop_
_audit_author_name
_audit_author_address
'Haoliang Shi'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_audit_creation_date             2025-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H7 F4 N O2 S Se'
_chemical_formula_sum            'C12 H7 F4 N O2 S Se'
_chemical_formula_weight         384.21
_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'
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      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                   6.5644(13)
_cell_length_b                   8.2458(16)
_cell_length_c                   13.659(3)
_cell_angle_alpha                102.402(5)
_cell_angle_beta                 98.371(6)
_cell_angle_gamma                103.685(5)
_cell_volume                     686.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2988
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      64.850
_cell_measurement_theta_min      5.713
_shelx_estimated_absorpt_T_max   0.431
_shelx_estimated_absorpt_T_min   0.212
_exptl_absorpt_coefficient_mu    5.631
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0939 after correction.
The Ratio of minimum to maximum transmission is 0.3620.
The λ/2 correction factor is Not present.
;
_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    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15394
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         5.718
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             2444
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.654
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.115
_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)+(0.1066P)²+0.7256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1558
_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. Uiso/Uaniso restraints and constraints
C4 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(N5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.75078(7) 0.84343(5) 0.41131(3) 0.0475(2) Uani 1 1 d . . . . .
S12 S 0.39150(15) 0.77877(11) 0.35224(8) 0.0422(3) Uani 1 1 d . . . . .
F8 F 0.7966(6) 0.7651(5) 0.1847(2) 0.0797(10) Uani 1 1 d . . . . .
O20 O 0.3076(5) 0.8367(4) 0.4404(3) 0.0559(7) Uani 1 1 d . . . . .
O21 O 0.3204(5) 0.5993(4) 0.2960(3) 0.0585(8) Uani 1 1 d . . . . .
F11 F 0.7783(7) 0.4961(6) 0.4560(3) 0.0952(12) Uani 1 1 d . . . . .
C2 C 0.7870(6) 0.6411(5) 0.3258(3) 0.0439(8) Uani 1 1 d . . . . .
F9 F 0.8518(8) 0.4751(7) 0.0699(3) 0.1176(16) Uani 1 1 d . . . . .
F10 F 0.8568(8) 0.2263(5) 0.3320(5) 0.132(2) Uani 1 1 d . . . . .
C13 C 0.3540(6) 0.9057(5) 0.2665(3) 0.0427(8) Uani 1 1 d . . . . .
C14 C 0.3386(7) 1.0711(5) 0.3042(3) 0.0490(9) Uani 1 1 d . . . . .
H14 H 0.348344 1.114577 0.373901 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2940(7) 1.1071(7) 0.1325(4) 0.0529(10) Uani 1 1 d . . . . .
C15 C 0.3087(8) 1.1708(6) 0.2371(4) 0.0547(10) Uani 1 1 d . . . . .
H15 H 0.298211 1.282020 0.262005 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8004(8) 0.5010(6) 0.3614(4) 0.0597(12) Uani 1 1 d . . . . .
C7 C 0.8067(7) 0.6320(6) 0.2251(3) 0.0543(10) Uani 1 1 d . . . . .
N5 N 0.8512(8) 0.3534(7) 0.2014(4) 0.0787(13) Uani 1 1 d . U . . .
C17 C 0.3091(8) 0.9403(7) 0.0970(3) 0.0593(11) Uani 1 1 d . . . . .
H17 H 0.299204 0.896296 0.027269 0.071 Uiso 1 1 calc R U . . .
C18 C 0.3384(7) 0.8389(6) 0.1626(3) 0.0538(10) Uani 1 1 d . . . . .
H18 H 0.347729 0.727249 0.137700 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8344(9) 0.4854(9) 0.1682(5) 0.0741(16) Uani 1 1 d . . . . .
C4 C 0.8387(9) 0.3603(7) 0.2956(6) 0.0733(14) Uani 1 1 d . U . . .
C19 C 0.2653(10) 1.2182(10) 0.0602(5) 0.0783(17) Uani 1 1 d . . . . .
H19A H 0.148544 1.266263 0.071854 0.117 Uiso 1 1 calc R U . . .
H19B H 0.234625 1.149149 -0.009162 0.117 Uiso 1 1 calc R U . . .
H19C H 0.394343 1.309975 0.071923 0.117 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 S12 2.2724(11) . ?
Se1 C2 1.906(4) . ?
S12 O20 1.432(3) . ?
S12 O21 1.442(3) . ?
S12 C13 1.759(4) . ?
F8 C7 1.341(6) . ?
F11 C3 1.329(6) . ?
C2 C3 1.362(6) . ?
C2 C7 1.388(6) . ?
F9 C6 1.351(8) . ?
F10 C4 1.328(7) . ?
C13 C14 1.383(6) . ?
C13 C18 1.387(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C16 C15 1.392(7) . ?
C16 C17 1.389(7) . ?
C16 C19 1.505(7) . ?
C15 H15 0.9300 . ?
C3 C4 1.404(8) . ?
C7 C6 1.356(7) . ?
N5 C6 1.287(9) . ?
N5 C4 1.291(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(7) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C2 Se1 S12 95.64(12) . . ?
O20 S12 Se1 104.95(15) . . ?
O20 S12 O21 120.0(2) . . ?
O20 S12 C13 108.78(19) . . ?
O21 S12 Se1 107.09(14) . . ?
O21 S12 C13 108.7(2) . . ?
C13 S12 Se1 106.53(14) . . ?
C3 C2 Se1 121.7(4) . . ?
C3 C2 C7 117.0(4) . . ?
C7 C2 Se1 121.3(3) . . ?
C14 C13 S12 119.1(3) . . ?
C14 C13 C18 121.0(4) . . ?
C18 C13 S12 119.9(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C15 C16 C19 120.4(5) . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 C19 121.0(5) . . ?
C14 C15 C16 120.9(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
F11 C3 C2 121.3(5) . . ?
F11 C3 C4 120.3(5) . . ?
C2 C3 C4 118.4(5) . . ?
F8 C7 C2 120.6(4) . . ?
F8 C7 C6 120.7(5) . . ?
C6 C7 C2 118.8(5) . . ?
C6 N5 C4 117.5(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
F9 C6 C7 119.1(6) . . ?
N5 C6 F9 116.0(5) . . ?
N5 C6 C7 124.9(6) . . ?
F10 C4 C3 117.8(6) . . ?
N5 C4 F10 118.8(6) . . ?
N5 C4 C3 123.3(5) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 S12 C13 C14 -87.1(4) . . . . ?
Se1 S12 C13 C18 93.4(4) . . . . ?
Se1 C2 C3 F11 3.3(7) . . . . ?
Se1 C2 C3 C4 -176.6(4) . . . . ?
Se1 C2 C7 F8 -1.2(6) . . . . ?
Se1 C2 C7 C6 179.3(4) . . . . ?
S12 C13 C14 C15 -179.9(4) . . . . ?
S12 C13 C18 C17 180.0(4) . . . . ?
F8 C7 C6 F9 0.0(8) . . . . ?
F8 C7 C6 N5 178.2(5) . . . . ?
O20 S12 C13 C14 25.5(4) . . . . ?
O20 S12 C13 C18 -154.0(4) . . . . ?
O21 S12 C13 C14 157.8(3) . . . . ?
O21 S12 C13 C18 -21.7(4) . . . . ?
F11 C3 C4 F10 -1.6(8) . . . . ?
F11 C3 C4 N5 176.5(5) . . . . ?
C2 C3 C4 F10 178.3(5) . . . . ?
C2 C3 C4 N5 -3.6(8) . . . . ?
C2 C7 C6 F9 179.4(5) . . . . ?
C2 C7 C6 N5 -2.4(8) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C13 C18 C17 0.5(7) . . . . ?
C16 C17 C18 C13 -0.3(7) . . . . ?
C15 C16 C17 C18 -0.1(7) . . . . ?
C3 C2 C7 F8 -179.6(4) . . . . ?
C3 C2 C7 C6 1.0(7) . . . . ?
C7 C2 C3 F11 -178.4(4) . . . . ?
C7 C2 C3 C4 1.8(7) . . . . ?
C17 C16 C15 C14 0.3(7) . . . . ?
C18 C13 C14 C15 -0.4(7) . . . . ?
C6 N5 C4 F10 -179.6(5) . . . . ?
C6 N5 C4 C3 2.3(9) . . . . ?
C4 N5 C6 F9 179.0(5) . . . . ?
C4 N5 C6 C7 0.7(9) . . . . ?
C19 C16 C15 C14 -178.9(5) . . . . ?
C19 C16 C17 C18 179.0(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
