# 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
_database_code_depnum_ccdc_archive 'CCDC 2432657'
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.	2025-08-18 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'
