# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2492387'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2025-09-30 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N2 Se, C F3 O3 S'

_chemical_formula_sum            'C16 H15 F3 N2 O3 S Se'
_chemical_formula_weight         451.32

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.5995(2)
_cell_length_b                   12.0655(3)
_cell_length_c                   14.2876(3)
_cell_angle_alpha                90.027(1)
_cell_angle_beta                 104.479(1)
_cell_angle_gamma                94.130(1)
_cell_volume                     1764.26(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      3.6736
_cell_measurement_theta_max      74.4801

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    4.460
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.741

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker venture d8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29546
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.195
_diffrn_reflns_theta_max         70.066
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6583
_reflns_number_gt                6442
_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       'APEX5 v2023.9-4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0153P)²+1.7825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6583
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Se2 Se 0.74066(2) 0.58750(2) 0.17043(2) 0.01455(6) Uani 1 1 d . . . . .
Se1 Se 0.26860(2) 0.12276(2) 0.32919(2) 0.01582(6) Uani 1 1 d . . . . .
S2 S 0.81669(4) 0.30751(3) 0.07302(3) 0.01490(9) Uani 1 1 d . . . . .
S1 S 0.17992(4) -0.17121(4) 0.42701(3) 0.01533(9) Uani 1 1 d . . . . .
F1 F 0.32205(11) -0.15440(11) 0.60582(8) 0.0273(3) Uani 1 1 d . . . . .
F2 F 0.38529(12) -0.27398(10) 0.51841(9) 0.0288(3) Uani 1 1 d . . . . .
F3 F 0.42487(11) -0.09889(10) 0.49999(9) 0.0293(3) Uani 1 1 d . . . . .
F5 F 0.57103(11) 0.34433(11) -0.00789(9) 0.0305(3) Uani 1 1 d . . . . .
F6 F 0.67688(12) 0.28445(12) -0.10550(8) 0.0314(3) Uani 1 1 d . . . . .
F4 F 0.61392(13) 0.17229(11) -0.00701(12) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.10019(13) -0.25961(12) 0.45685(10) 0.0252(3) Uani 1 1 d . . . . .
O2 O 0.14307(14) -0.06048(11) 0.44023(10) 0.0235(3) Uani 1 1 d . . . . .
O6 O 0.89851(13) 0.22845(12) 0.04695(10) 0.0233(3) Uani 1 1 d . . . . .
O5 O 0.84994(14) 0.42212(11) 0.05385(10) 0.0231(3) Uani 1 1 d . . . . .
O3 O 0.21284(15) -0.19128(12) 0.33667(10) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.78556(15) 0.28929(12) 0.16470(10) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.91271(14) 0.47752(12) 0.32490(10) 0.0128(3) Uani 1 1 d . . . . .
N1 N -0.00989(14) 0.07247(12) 0.26791(11) 0.0141(3) Uani 1 1 d . . . . .
N2 N 0.09497(14) -0.01055(12) 0.17711(11) 0.0141(3) Uani 1 1 d . . . . .
N4 N 1.01863(14) 0.57141(12) 0.23331(11) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.10777(17) 0.05807(14) 0.25381(12) 0.0133(3) Uani 1 1 d . . . . .
C21 C 0.90056(17) 0.54294(14) 0.24762(12) 0.0134(3) Uani 1 1 d . . . . .
C10 C 0.29391(18) 0.23241(14) 0.23569(12) 0.0151(3) Uani 1 1 d . . . . .
C15 C 0.18986(18) 0.28307(15) 0.17672(13) 0.0168(4) Uani 1 1 d . . . . .
H15 H 0.1028 0.2619 0.1794 0.020 Uiso 1 1 calc R U . . .
C31 C 0.70943(17) 0.68929(14) 0.26494(13) 0.0149(3) Uani 1 1 d . . . . .
C34 C 0.6513(2) 0.84484(16) 0.38734(14) 0.0234(4) Uani 1 1 d . . . . .
H34 H 0.6315 0.8990 0.4288 0.028 Uiso 1 1 calc R U . . .
C8 C -0.10336(18) 0.01071(14) 0.19829(13) 0.0149(3) Uani 1 1 d . . . . .
C7 C -0.23884(18) -0.00186(15) 0.18200(14) 0.0193(4) Uani 1 1 d . . . . .
H7 H -0.2838 0.0355 0.2209 0.023 Uiso 1 1 calc R U . . .
C32 C 0.80930(18) 0.75951(15) 0.32099(13) 0.0174(4) Uani 1 1 d . . . . .
H32 H 0.8968 0.7552 0.3167 0.021 Uiso 1 1 calc R U . . .
C13 C 0.3417(2) 0.39805(16) 0.11180(14) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.3580 0.4552 0.0697 0.028 Uiso 1 1 calc R U . . .
C22 C 0.80390(17) 0.42379(15) 0.35890(13) 0.0161(3) Uani 1 1 d . . . . .
H22A H 0.7425 0.4791 0.3641 0.024 Uiso 1 1 calc R U . . .
H22B H 0.8379 0.3916 0.4224 0.024 Uiso 1 1 calc R U . . .
H22C H 0.7588 0.3649 0.3128 0.024 Uiso 1 1 calc R U . . .
C36 C 0.58101(18) 0.69498(17) 0.27060(14) 0.0205(4) Uani 1 1 d . . . . .
H36 H 0.5137 0.6449 0.2336 0.025 Uiso 1 1 calc R U . . .
C23 C 1.04467(17) 0.46197(14) 0.36186(13) 0.0138(3) Uani 1 1 d . . . . .
C24 C 1.11006(18) 0.40074(14) 0.43973(13) 0.0169(4) Uani 1 1 d . . . . .
H24 H 1.0649 0.3599 0.4798 0.020 Uiso 1 1 calc R U . . .
C28 C 1.11149(17) 0.52213(14) 0.30364(13) 0.0143(3) Uani 1 1 d . . . . .
C3 C -0.03697(17) -0.04251(14) 0.14074(13) 0.0147(3) Uani 1 1 d . . . . .
C27 C 1.24741(18) 0.52568(15) 0.32042(14) 0.0184(4) Uani 1 1 d . . . . .
H27 H 1.2929 0.5676 0.2812 0.022 Uiso 1 1 calc R U . . .
C33 C 0.77983(19) 0.83617(15) 0.38345(14) 0.0202(4) Uani 1 1 d . . . . .
H33 H 0.8479 0.8829 0.4237 0.024 Uiso 1 1 calc R U . . .
C37 C 0.66111(18) 0.27542(16) -0.01556(14) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.42137(18) 0.26318(17) 0.23264(14) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.4919 0.2270 0.2720 0.026 Uiso 1 1 calc R U . . .
C2 C 0.20334(18) -0.05093(15) 0.14307(13) 0.0177(4) Uani 1 1 d . . . . .
H2A H 0.2615 0.0124 0.1331 0.027 Uiso 1 1 calc R U . . .
H2B H 0.1686 -0.0923 0.0819 0.027 Uiso 1 1 calc R U . . .
H2C H 0.2523 -0.0998 0.1914 0.027 Uiso 1 1 calc R U . . .
C30 C 1.04800(19) 0.63916(15) 0.15545(13) 0.0189(4) Uani 1 1 d . . . . .
H30A H 1.0794 0.5923 0.1113 0.028 Uiso 1 1 calc R U . . .
H30B H 1.1155 0.6982 0.1830 0.028 Uiso 1 1 calc R U . . .
H30C H 0.9687 0.6724 0.1199 0.028 Uiso 1 1 calc R U . . .
C16 C 0.33601(18) -0.17501(16) 0.51687(14) 0.0185(4) Uani 1 1 d . . . . .
C6 C -0.30398(19) -0.07185(16) 0.10600(15) 0.0228(4) Uani 1 1 d . . . . .
H6 H -0.3964 -0.0834 0.0923 0.027 Uiso 1 1 calc R U . . .
C35 C 0.55182(19) 0.77475(18) 0.33097(15) 0.0246(4) Uani 1 1 d . . . . .
H35 H 0.4639 0.7811 0.3335 0.030 Uiso 1 1 calc R U . . .
C9 C -0.03836(19) 0.13749(16) 0.34577(14) 0.0196(4) Uani 1 1 d . . . . .
H9A H -0.0688 0.0872 0.3907 0.029 Uiso 1 1 calc R U . . .
H9B H -0.1064 0.1876 0.3182 0.029 Uiso 1 1 calc R U . . .
H9C H 0.0411 0.1812 0.3805 0.029 Uiso 1 1 calc R U . . .
C4 C -0.10302(19) -0.11271(15) 0.06346(13) 0.0183(4) Uani 1 1 d . . . . .
H4 H -0.0584 -0.1488 0.0236 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4452(2) 0.34750(18) 0.17139(15) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.5324 0.3705 0.1703 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2143(2) 0.36468(15) 0.11402(14) 0.0209(4) Uani 1 1 d . . . . .
H14 H 0.1434 0.3981 0.0722 0.025 Uiso 1 1 calc R U . . .
C26 C 1.31192(18) 0.46489(16) 0.39716(14) 0.0210(4) Uani 1 1 d . . . . .
H26 H 1.4044 0.4648 0.4111 0.025 Uiso 1 1 calc R U . . .
C5 C -0.23708(19) -0.12636(15) 0.04849(14) 0.0216(4) Uani 1 1 d . . . . .
H5 H -0.2858 -0.1744 -0.0026 0.026 Uiso 1 1 calc R U . . .
C25 C 1.24455(19) 0.40315(15) 0.45510(14) 0.0201(4) Uani 1 1 d . . . . .
H25 H 1.2928 0.3616 0.5066 0.024 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
Se2 C21 1.8909(17) . ?
Se2 C31 1.9292(18) . ?
Se1 C1 1.8880(17) . ?
Se1 C10 1.9331(17) . ?
S2 O4 1.4419(14) . ?
S2 O6 1.4426(14) . ?
S2 O5 1.4457(14) . ?
S2 C37 1.8263(19) . ?
S1 O3 1.4434(14) . ?
S1 O1 1.4438(14) . ?
S1 O2 1.4440(14) . ?
S1 C16 1.8266(19) . ?
F1 C16 1.341(2) . ?
F2 C16 1.335(2) . ?
F3 C16 1.333(2) . ?
F5 C37 1.335(2) . ?
F6 C37 1.340(2) . ?
F4 C37 1.325(2) . ?
N3 C21 1.343(2) . ?
N3 C23 1.393(2) . ?
N3 C22 1.469(2) . ?
N1 C1 1.335(2) . ?
N1 C8 1.388(2) . ?
N1 C9 1.465(2) . ?
N2 C1 1.347(2) . ?
N2 C3 1.390(2) . ?
N2 C2 1.467(2) . ?
N4 C21 1.339(2) . ?
N4 C28 1.386(2) . ?
N4 C30 1.463(2) . ?
C10 C11 1.386(3) . ?
C10 C15 1.390(3) . ?
C15 C14 1.385(3) . ?
C15 H15 0.9500 . ?
C31 C32 1.388(3) . ?
C31 C36 1.390(3) . ?
C34 C35 1.386(3) . ?
C34 C33 1.389(3) . ?
C34 H34 0.9500 . ?
C8 C3 1.392(3) . ?
C8 C7 1.393(3) . ?
C7 C6 1.382(3) . ?
C7 H7 0.9500 . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C13 C14 1.389(3) . ?
C13 C12 1.389(3) . ?
C13 H13 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C36 C35 1.393(3) . ?
C36 H36 0.9500 . ?
C23 C28 1.393(2) . ?
C23 C24 1.397(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C28 C27 1.398(3) . ?
C3 C4 1.398(3) . ?
C27 C26 1.380(3) . ?
C27 H27 0.9500 . ?
C33 H33 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C6 C5 1.403(3) . ?
C6 H6 0.9500 . ?
C35 H35 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C26 C25 1.404(3) . ?
C26 H26 0.9500 . ?
C5 H5 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 Se2 C31 95.92(7) . . ?
C1 Se1 C10 95.83(7) . . ?
O4 S2 O6 115.26(9) . . ?
O4 S2 O5 114.96(8) . . ?
O6 S2 O5 115.00(9) . . ?
O4 S2 C37 103.80(9) . . ?
O6 S2 C37 102.23(8) . . ?
O5 S2 C37 103.06(9) . . ?
O3 S1 O1 115.15(9) . . ?
O3 S1 O2 115.15(8) . . ?
O1 S1 O2 115.02(9) . . ?
O3 S1 C16 103.53(9) . . ?
O1 S1 C16 102.75(8) . . ?
O2 S1 C16 102.68(8) . . ?
C21 N3 C23 108.38(14) . . ?
C21 N3 C22 125.41(15) . . ?
C23 N3 C22 126.00(15) . . ?
C1 N1 C8 108.60(15) . . ?
C1 N1 C9 126.85(15) . . ?
C8 N1 C9 124.49(15) . . ?
C1 N2 C3 108.37(15) . . ?
C1 N2 C2 125.31(15) . . ?
C3 N2 C2 126.16(15) . . ?
C21 N4 C28 108.44(14) . . ?
C21 N4 C30 127.08(15) . . ?
C28 N4 C30 124.44(15) . . ?
N1 C1 N2 109.59(15) . . ?
N1 C1 Se1 125.81(13) . . ?
N2 C1 Se1 124.61(13) . . ?
N4 C21 N3 109.74(15) . . ?
N4 C21 Se2 125.19(13) . . ?
N3 C21 Se2 125.08(13) . . ?
C11 C10 C15 120.69(17) . . ?
C11 C10 Se1 117.33(14) . . ?
C15 C10 Se1 121.91(13) . . ?
C14 C15 C10 119.41(17) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C32 C31 C36 120.84(17) . . ?
C32 C31 Se2 121.68(14) . . ?
C36 C31 Se2 117.36(14) . . ?
C35 C34 C33 120.21(18) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
N1 C8 C3 106.91(15) . . ?
N1 C8 C7 130.84(17) . . ?
C3 C8 C7 122.25(17) . . ?
C6 C7 C8 116.11(18) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
C31 C32 C33 119.24(17) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C14 C13 C12 119.74(18) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 C36 C35 119.46(18) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
N3 C23 C28 106.43(15) . . ?
N3 C23 C24 131.88(17) . . ?
C28 C23 C24 121.69(17) . . ?
C25 C24 C23 116.07(17) . . ?
C25 C24 H24 122.0 . . ?
C23 C24 H24 122.0 . . ?
N4 C28 C23 107.01(15) . . ?
N4 C28 C27 131.00(17) . . ?
C23 C28 C27 121.99(17) . . ?
N2 C3 C8 106.52(15) . . ?
N2 C3 C4 131.88(17) . . ?
C8 C3 C4 121.60(17) . . ?
C26 C27 C28 116.29(17) . . ?
C26 C27 H27 121.9 . . ?
C28 C27 H27 121.9 . . ?
C34 C33 C32 120.30(18) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
F4 C37 F5 108.34(16) . . ?
F4 C37 F6 107.16(17) . . ?
F5 C37 F6 107.01(15) . . ?
F4 C37 S2 111.37(13) . . ?
F5 C37 S2 112.42(14) . . ?
F6 C37 S2 110.30(13) . . ?
C10 C11 C12 119.45(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 C30 H30A 109.5 . . ?
N4 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N4 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
F3 C16 F2 107.56(15) . . ?
F3 C16 F1 107.35(15) . . ?
F2 C16 F1 107.31(15) . . ?
F3 C16 S1 111.61(13) . . ?
F2 C16 S1 112.04(13) . . ?
F1 C16 S1 110.73(12) . . ?
C7 C6 C5 121.69(18) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C34 C35 C36 119.87(18) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 115.99(18) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
C13 C12 C11 120.19(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C15 C14 C13 120.49(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C27 C26 C25 121.76(17) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C4 C5 C6 122.35(17) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C24 C25 C26 122.18(17) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 N2 0.29(19) . . . . ?
C9 N1 C1 N2 177.54(16) . . . . ?
C8 N1 C1 Se1 -179.52(12) . . . . ?
C9 N1 C1 Se1 -2.3(3) . . . . ?
C3 N2 C1 N1 -0.54(19) . . . . ?
C2 N2 C1 N1 -176.23(15) . . . . ?
C3 N2 C1 Se1 179.27(12) . . . . ?
C2 N2 C1 Se1 3.6(2) . . . . ?
C10 Se1 C1 N1 -104.88(15) . . . . ?
C10 Se1 C1 N2 75.33(15) . . . . ?
C28 N4 C21 N3 0.36(19) . . . . ?
C30 N4 C21 N3 178.18(16) . . . . ?
C28 N4 C21 Se2 -179.38(12) . . . . ?
C30 N4 C21 Se2 -1.6(3) . . . . ?
C23 N3 C21 N4 -0.59(19) . . . . ?
C22 N3 C21 N4 -175.62(15) . . . . ?
C23 N3 C21 Se2 179.16(12) . . . . ?
C22 N3 C21 Se2 4.1(2) . . . . ?
C31 Se2 C21 N4 -108.24(15) . . . . ?
C31 Se2 C21 N3 72.05(15) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
Se1 C10 C15 C14 177.15(14) . . . . ?
C1 N1 C8 C3 0.07(19) . . . . ?
C9 N1 C8 C3 -177.25(15) . . . . ?
C1 N1 C8 C7 -179.84(18) . . . . ?
C9 N1 C8 C7 2.8(3) . . . . ?
N1 C8 C7 C6 -179.13(17) . . . . ?
C3 C8 C7 C6 1.0(3) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
Se2 C31 C32 C33 175.84(13) . . . . ?
C32 C31 C36 C35 2.2(3) . . . . ?
Se2 C31 C36 C35 -173.80(15) . . . . ?
C21 N3 C23 C28 0.58(19) . . . . ?
C22 N3 C23 C28 175.57(16) . . . . ?
C21 N3 C23 C24 -178.97(18) . . . . ?
C22 N3 C23 C24 -4.0(3) . . . . ?
N3 C23 C24 C25 179.21(17) . . . . ?
C28 C23 C24 C25 -0.3(3) . . . . ?
C21 N4 C28 C23 0.00(19) . . . . ?
C30 N4 C28 C23 -177.88(16) . . . . ?
C21 N4 C28 C27 180.00(18) . . . . ?
C30 N4 C28 C27 2.1(3) . . . . ?
N3 C23 C28 N4 -0.35(18) . . . . ?
C24 C23 C28 N4 179.25(15) . . . . ?
N3 C23 C28 C27 179.66(16) . . . . ?
C24 C23 C28 C27 -0.7(3) . . . . ?
C1 N2 C3 C8 0.57(18) . . . . ?
C2 N2 C3 C8 176.21(16) . . . . ?
C1 N2 C3 C4 -179.31(18) . . . . ?
C2 N2 C3 C4 -3.7(3) . . . . ?
N1 C8 C3 N2 -0.39(18) . . . . ?
C7 C8 C3 N2 179.53(16) . . . . ?
N1 C8 C3 C4 179.51(15) . . . . ?
C7 C8 C3 C4 -0.6(3) . . . . ?
N4 C28 C27 C26 -179.08(18) . . . . ?
C23 C28 C27 C26 0.9(3) . . . . ?
C35 C34 C33 C32 1.9(3) . . . . ?
C31 C32 C33 C34 -2.1(3) . . . . ?
O4 S2 C37 F4 -58.52(16) . . . . ?
O6 S2 C37 F4 61.66(16) . . . . ?
O5 S2 C37 F4 -178.72(14) . . . . ?
O4 S2 C37 F5 63.28(15) . . . . ?
O6 S2 C37 F5 -176.53(14) . . . . ?
O5 S2 C37 F5 -56.92(15) . . . . ?
O4 S2 C37 F6 -177.38(13) . . . . ?
O6 S2 C37 F6 -57.19(15) . . . . ?
O5 S2 C37 F6 62.42(15) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
Se1 C10 C11 C12 -175.46(15) . . . . ?
O3 S1 C16 F3 58.76(15) . . . . ?
O1 S1 C16 F3 178.92(13) . . . . ?
O2 S1 C16 F3 -61.38(14) . . . . ?
O3 S1 C16 F2 -61.94(14) . . . . ?
O1 S1 C16 F2 58.23(15) . . . . ?
O2 S1 C16 F2 177.92(13) . . . . ?
O3 S1 C16 F1 178.30(13) . . . . ?
O1 S1 C16 F1 -61.54(15) . . . . ?
O2 S1 C16 F1 58.16(14) . . . . ?
C8 C7 C6 C5 -0.4(3) . . . . ?
C33 C34 C35 C36 0.3(3) . . . . ?
C31 C36 C35 C34 -2.3(3) . . . . ?
N2 C3 C4 C5 179.41(17) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C14 C13 C12 C11 0.4(3) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C10 C15 C14 C13 -1.8(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C28 C27 C26 C25 -0.1(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C7 C6 C5 C4 -0.7(3) . . . . ?
C23 C24 C25 C26 1.1(3) . . . . ?
C27 C26 C25 C24 -0.9(3) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2492388'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2025-09-30 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 F2 N2 Se, C F3 O3 S'
_chemical_formula_sum            'C16 H13 F5 N2 O3 S Se'
_chemical_formula_weight         487.30

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'

_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                   8.5695(3)
_cell_length_b                   11.3131(3)
_cell_length_c                   18.4784(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1791.44(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      3.9074
_cell_measurement_theta_max      74.4566


_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.614
_shelx_estimated_absorpt_T_min   0.444
_shelx_estimated_absorpt_T_max   0.491
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.49


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker venture d8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34599
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         5.691
_diffrn_reflns_theta_max         74.449
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3614
_reflns_number_gt                3612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.977

_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       'APEX5 v2023.9-4'

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0196P)²+0.6288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.010(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0156
_refine_ls_wR_factor_ref         0.0411
_refine_ls_wR_factor_gt          0.0410
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
C1 C 0.1139(2) 0.67581(17) 0.28584(11) 0.0124(4) Uani 1 1 d . . . . .
C2 C 0.0938(3) 0.64126(19) 0.42018(11) 0.0170(4) Uani 1 1 d . . . . .
H2A H 0.0096 0.5891 0.4077 0.026 Uiso 1 1 calc R U . . .
H2B H 0.0577 0.6988 0.4545 0.026 Uiso 1 1 calc R U . . .
H2C H 0.1775 0.5964 0.4411 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2521(2) 0.79673(17) 0.35520(11) 0.0126(4) Uani 1 1 d . . . . .
C5 C 0.3219(2) 0.85705(19) 0.41266(11) 0.0157(4) Uani 1 1 d . . . . .
H5 H 0.3053 0.8365 0.4608 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4169(2) 0.94894(18) 0.39258(11) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.4425(2) 0.98001(17) 0.32007(11) 0.0150(4) Uani 1 1 d . . . . .
C8 C 0.3749(2) 0.92175(16) 0.26311(10) 0.0136(4) Uani 1 1 d . . . . .
H8 H 0.3922 0.9428 0.2151 0.016 Uiso 1 1 calc R U . . .
C9 C 0.2773(2) 0.82771(17) 0.28311(11) 0.0120(4) Uani 1 1 d . . . . .
C10 C 0.1792(3) 0.7541(2) 0.16210(11) 0.0161(4) Uani 1 1 d . . . . .
H10A H 0.2590 0.7045 0.1420 0.024 Uiso 1 1 calc R U . . .
H10B H 0.1935 0.8338 0.1455 0.024 Uiso 1 1 calc R U . . .
H10C H 0.0786 0.7259 0.1470 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1189(2) 0.43531(16) 0.23396(10) 0.0132(4) Uani 1 1 d . . . . .
C12 C 0.1379(3) 0.39991(19) 0.16219(11) 0.0164(4) Uani 1 1 d . . . . .
H12 H 0.0859 0.4391 0.1251 0.020 Uiso 1 1 calc R U . . .
C13 C 0.2359(3) 0.3049(2) 0.14704(12) 0.0187(4) Uani 1 1 d . . . . .
H13 H 0.2488 0.2796 0.0995 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3147(3) 0.24784(18) 0.20282(12) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.3810 0.1850 0.1924 0.022 Uiso 1 1 calc R U . . .
C15 C 0.2947(2) 0.28440(19) 0.27417(11) 0.0173(4) Uani 1 1 d . . . . .
H15 H 0.3475 0.2458 0.3113 0.021 Uiso 1 1 calc R U . . .
C16 C 0.1961(2) 0.37851(18) 0.29015(11) 0.0159(4) Uani 1 1 d . . . . .
H16 H 0.1822 0.4030 0.3377 0.019 Uiso 1 1 calc R U . . .
C17 C 0.4904(3) 0.3905(2) 0.48437(12) 0.0256(5) Uani 1 1 d . . . . .
F1 F 0.54024(15) 1.07103(10) 0.30683(6) 0.0199(2) Uani 1 1 d . . . . .
F2 F 0.49218(16) 1.01245(11) 0.44341(7) 0.0247(3) Uani 1 1 d . . . . .
F3 F 0.34026(19) 0.38551(15) 0.50279(9) 0.0392(4) Uani 1 1 d . . . . .
F4 F 0.5187(2) 0.29937(12) 0.44031(9) 0.0413(4) Uani 1 1 d . . . . .
F5 F 0.5740(2) 0.37511(15) 0.54469(8) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.18890(19) 0.75122(14) 0.24155(9) 0.0122(3) Uani 1 1 d . . . . .
N2 N 0.1497(2) 0.70150(15) 0.35486(9) 0.0125(3) Uani 1 1 d . . . . .
O1 O 0.44106(18) 0.53049(14) 0.37703(8) 0.0230(3) Uani 1 1 d . . . . .
O2 O 0.70296(18) 0.52236(15) 0.42703(9) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.4934(2) 0.61704(13) 0.49490(8) 0.0247(4) Uani 1 1 d . . . . .
S1 S 0.53783(7) 0.53115(4) 0.44089(2) 0.01549(10) Uani 1 1 d . . . . .
Se1 Se -0.03025(2) 0.55874(2) 0.25513(2) 0.01477(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
C1 N2 1.344(3) . ?
C1 N1 1.346(3) . ?
C1 Se1 1.898(2) . ?
C2 N2 1.467(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N2 1.390(3) . ?
C3 C9 1.394(3) . ?
C3 C5 1.397(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 F2 1.347(2) . ?
C6 C7 1.402(3) . ?
C7 F1 1.350(2) . ?
C7 C8 1.370(3) . ?
C8 C9 1.403(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.383(3) . ?
C10 N1 1.471(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.389(3) . ?
C11 C12 1.395(3) . ?
C11 Se1 1.9329(19) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 F3 1.332(3) . ?
C17 F5 1.336(3) . ?
C17 F4 1.336(3) . ?
C17 S1 1.828(2) . ?
O1 S1 1.4424(16) . ?
O2 S1 1.4415(16) . ?
O3 S1 1.4440(15) . ?

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
N2 C1 N1 109.32(17) . . ?
N2 C1 Se1 125.72(14) . . ?
N1 C1 Se1 124.85(15) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C9 106.75(17) . . ?
N2 C3 C5 130.75(18) . . ?
C9 C3 C5 122.49(19) . . ?
C6 C5 C3 114.76(18) . . ?
C6 C5 H5 122.6 . . ?
C3 C5 H5 122.6 . . ?
F2 C6 C5 119.98(18) . . ?
F2 C6 C7 117.24(18) . . ?
C5 C6 C7 122.77(18) . . ?
F1 C7 C8 119.35(17) . . ?
F1 C7 C6 117.48(17) . . ?
C8 C7 C6 123.17(18) . . ?
C7 C8 C9 114.49(18) . . ?
C7 C8 H8 122.8 . . ?
C9 C8 H8 122.8 . . ?
N1 C9 C3 106.77(17) . . ?
N1 C9 C8 130.91(18) . . ?
C3 C9 C8 122.31(18) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.48(18) . . ?
C16 C11 Se1 119.87(14) . . ?
C12 C11 Se1 118.49(15) . . ?
C13 C12 C11 118.89(19) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 120.14(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.27(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.21(19) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C11 C16 C15 119.01(19) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
F3 C17 F5 107.39(18) . . ?
F3 C17 F4 107.3(2) . . ?
F5 C17 F4 108.1(2) . . ?
F3 C17 S1 111.34(17) . . ?
F5 C17 S1 111.18(17) . . ?
F4 C17 S1 111.32(15) . . ?
C1 N1 C9 108.70(16) . . ?
C1 N1 C10 126.44(17) . . ?
C9 N1 C10 124.86(16) . . ?
C1 N2 C3 108.46(16) . . ?
C1 N2 C2 127.29(17) . . ?
C3 N2 C2 124.25(17) . . ?
O2 S1 O1 114.75(9) . . ?
O2 S1 O3 115.35(10) . . ?
O1 S1 O3 114.66(10) . . ?
O2 S1 C17 103.66(11) . . ?
O1 S1 C17 103.14(11) . . ?
O3 S1 C17 102.90(10) . . ?
C1 Se1 C11 97.73(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C5 C6 -179.4(2) . . . . ?
C9 C3 C5 C6 0.0(3) . . . . ?
C3 C5 C6 F2 -179.09(18) . . . . ?
C3 C5 C6 C7 -0.1(3) . . . . ?
F2 C6 C7 F1 -0.1(3) . . . . ?
C5 C6 C7 F1 -179.04(18) . . . . ?
F2 C6 C7 C8 179.14(18) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
F1 C7 C8 C9 179.13(16) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
N2 C3 C9 N1 0.4(2) . . . . ?
C5 C3 C9 N1 -179.08(18) . . . . ?
N2 C3 C9 C8 179.59(17) . . . . ?
C5 C3 C9 C8 0.1(3) . . . . ?
C7 C8 C9 N1 178.87(19) . . . . ?
C7 C8 C9 C3 -0.1(3) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
Se1 C11 C12 C13 -175.06(15) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
Se1 C11 C16 C15 175.53(15) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
N2 C1 N1 C9 0.5(2) . . . . ?
Se1 C1 N1 C9 176.71(13) . . . . ?
N2 C1 N1 C10 -179.00(18) . . . . ?
Se1 C1 N1 C10 -2.8(3) . . . . ?
C3 C9 N1 C1 -0.6(2) . . . . ?
C8 C9 N1 C1 -179.63(19) . . . . ?
C3 C9 N1 C10 178.93(18) . . . . ?
C8 C9 N1 C10 -0.1(3) . . . . ?
N1 C1 N2 C3 -0.2(2) . . . . ?
Se1 C1 N2 C3 -176.39(14) . . . . ?
N1 C1 N2 C2 -179.89(18) . . . . ?
Se1 C1 N2 C2 3.9(3) . . . . ?
C9 C3 N2 C1 -0.1(2) . . . . ?
C5 C3 N2 C1 179.3(2) . . . . ?
C9 C3 N2 C2 179.54(18) . . . . ?
C5 C3 N2 C2 -1.0(3) . . . . ?
F3 C17 S1 O2 178.31(16) . . . . ?
F5 C17 S1 O2 58.60(18) . . . . ?
F4 C17 S1 O2 -62.0(2) . . . . ?
F3 C17 S1 O1 -61.74(18) . . . . ?
F5 C17 S1 O1 178.55(16) . . . . ?
F4 C17 S1 O1 58.0(2) . . . . ?
F3 C17 S1 O3 57.79(19) . . . . ?
F5 C17 S1 O3 -61.91(18) . . . . ?
F4 C17 S1 O3 177.52(18) . . . . ?
N2 C1 Se1 C11 -98.48(17) . . . . ?
N1 C1 Se1 C11 85.92(17) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

