# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2378943'
loop_
_audit_author_name
_audit_author_address
'Yuchao Yuan'
;Xuzhou Medical University
China
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2026-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15.75 H11 Cl N4 Se'
_chemical_formula_weight         370.69

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.5939(6)
_cell_length_b                   18.5686(11)
_cell_length_c                   17.3143(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3084.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8901
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             1476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    2.608
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22884
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.170
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2715
_reflns_number_gt                2395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+1.5059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2715
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Cl1 Cl 0.37197(9) 0.20426(3) 0.50628(4) 0.0725(2) Uani 1 1 d . . . . .
Se1 Se 0.43536(2) 0.53309(2) 0.61502(2) 0.04422(10) Uani 1 1 d . . . . .
N1 N 0.25697(17) 0.58100(8) 0.74021(9) 0.0329(3) Uani 1 1 d . . . . .
N2 N 0.28157(18) 0.46067(8) 0.73241(10) 0.0388(4) Uani 1 1 d . . . . .
N3 N 0.1995(2) 0.70174(9) 0.75702(12) 0.0492(5) Uani 1 1 d . . . . .
N4 N 0.3883(2) 0.66626(9) 0.67729(11) 0.0463(4) Uani 1 1 d . . . . .
C1 C 0.3192(2) 0.52222(10) 0.70344(12) 0.0350(4) Uani 1 1 d . . . . .
C2 C 0.1686(2) 0.55185(10) 0.79663(11) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.0750(2) 0.58181(12) 0.84846(12) 0.0391(5) Uani 1 1 d . . . . .
H3A H 0.061293 0.631318 0.851350 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0031(3) 0.53466(12) 0.89569(12) 0.0441(5) Uani 1 1 d . . . . .
H4A H -0.060945 0.552899 0.930968 0.053 Uiso 1 1 calc R U . . .
C5 C 0.0240(3) 0.46074(12) 0.89174(13) 0.0470(5) Uani 1 1 d . . . . .
H5A H -0.025103 0.430647 0.924956 0.056 Uiso 1 1 calc R U . . .
C6 C 0.1160(2) 0.43116(12) 0.83965(12) 0.0436(5) Uani 1 1 d . . . . .
H6A H 0.129668 0.381637 0.837135 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1876(2) 0.47754(10) 0.79104(11) 0.0357(4) Uani 1 1 d . . . . .
C8 C 0.2826(2) 0.65367(10) 0.72408(11) 0.0350(4) Uani 1 1 d . . . . .
C9 C 0.4105(3) 0.73518(13) 0.65954(14) 0.0551(6) Uani 1 1 d . . . . .
H9A H 0.483193 0.746597 0.626187 0.066 Uiso 1 1 calc R U . . .
C10 C 0.3305(3) 0.78954(12) 0.68852(14) 0.0532(6) Uani 1 1 d . . . . .
H10A H 0.346176 0.837447 0.675492 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2268(3) 0.76994(12) 0.73730(15) 0.0547(6) Uani 1 1 d . . . . .
H11A H 0.171387 0.806041 0.758342 0.066 Uiso 1 1 calc R U . . .
C12 C 0.4187(2) 0.43400(11) 0.58190(13) 0.0412(5) Uani 1 1 d . . . . .
C13 C 0.5036(3) 0.38130(13) 0.61290(14) 0.0531(6) Uani 1 1 d . . . . .
H13A H 0.568909 0.393355 0.650434 0.064 Uiso 1 1 calc R U . . .
C14 C 0.4918(3) 0.31069(13) 0.58835(16) 0.0566(6) Uani 1 1 d . . . . .
H14A H 0.549058 0.275066 0.608860 0.068 Uiso 1 1 calc R U . . .
C15 C 0.3941(3) 0.29407(12) 0.53310(13) 0.0484(5) Uani 1 1 d . . . . .
C16 C 0.3119(3) 0.34566(13) 0.50000(13) 0.0518(6) Uani 1 1 d . . . . .
H16A H 0.248362 0.333496 0.461571 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3247(2) 0.41660(12) 0.52470(13) 0.0465(5) Uani 1 1 d . . . . .
H17A H 0.269745 0.452350 0.502600 0.056 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
Cl1 C15 1.744(2) . ?
Se1 C1 1.904(2) . ?
Se1 C12 1.934(2) . ?
N1 C1 1.397(2) . ?
N1 C8 1.400(2) . ?
N1 C2 1.402(2) . ?
N2 C1 1.299(2) . ?
N2 C7 1.393(3) . ?
N3 C8 1.326(3) . ?
N3 C11 1.338(3) . ?
N4 C8 1.318(3) . ?
N4 C9 1.333(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.376(3) . ?
C6 C7 1.387(3) . ?
C9 C10 1.364(4) . ?
C10 C11 1.354(4) . ?
C12 C17 1.378(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.374(4) . ?
C15 C16 1.367(3) . ?
C16 C17 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C12 95.12(8) . . ?
C1 N1 C8 125.94(16) . . ?
C1 N1 C2 105.92(15) . . ?
C8 N1 C2 128.12(16) . . ?
C1 N2 C7 105.25(16) . . ?
C8 N3 C11 114.2(2) . . ?
C8 N4 C9 115.76(19) . . ?
N2 C1 N1 113.12(17) . . ?
N2 C1 Se1 124.47(14) . . ?
N1 C1 Se1 122.24(14) . . ?
C3 C2 C7 121.79(19) . . ?
C3 C2 N1 133.47(18) . . ?
C7 C2 N1 104.71(16) . . ?
C4 C3 C2 116.9(2) . . ?
C3 C4 C5 121.6(2) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 C7 117.9(2) . . ?
C6 C7 N2 128.56(18) . . ?
C6 C7 C2 120.47(19) . . ?
N2 C7 C2 110.97(17) . . ?
N4 C8 N3 127.41(18) . . ?
N4 C8 N1 115.38(17) . . ?
N3 C8 N1 117.21(17) . . ?
N4 C9 C10 122.4(2) . . ?
C11 C10 C9 116.3(2) . . ?
N3 C11 C10 123.9(2) . . ?
C17 C12 C13 119.9(2) . . ?
C17 C12 Se1 119.35(17) . . ?
C13 C12 Se1 120.67(17) . . ?
C12 C13 C14 120.3(2) . . ?
C15 C14 C13 118.8(2) . . ?
C16 C15 C14 121.9(2) . . ?
C16 C15 Cl1 119.21(19) . . ?
C14 C15 Cl1 118.89(19) . . ?
C15 C16 C17 118.9(2) . . ?
C12 C17 C16 120.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 N1 0.9(2) . . . . ?
C7 N2 C1 Se1 -174.46(15) . . . . ?
C8 N1 C1 N2 176.74(18) . . . . ?
C2 N1 C1 N2 -1.7(2) . . . . ?
C8 N1 C1 Se1 -7.8(3) . . . . ?
C2 N1 C1 Se1 173.75(13) . . . . ?
C1 N1 C2 C3 -176.3(2) . . . . ?
C8 N1 C2 C3 5.2(3) . . . . ?
C1 N1 C2 C7 1.8(2) . . . . ?
C8 N1 C2 C7 -176.69(18) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
N1 C2 C3 C4 179.1(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 N2 -177.6(2) . . . . ?
C5 C6 C7 C2 1.5(3) . . . . ?
C1 N2 C7 C6 179.5(2) . . . . ?
C1 N2 C7 C2 0.3(2) . . . . ?
C3 C2 C7 C6 -2.2(3) . . . . ?
N1 C2 C7 C6 179.42(19) . . . . ?
C3 C2 C7 N2 177.05(18) . . . . ?
N1 C2 C7 N2 -1.3(2) . . . . ?
C9 N4 C8 N3 -2.2(3) . . . . ?
C9 N4 C8 N1 177.8(2) . . . . ?
C11 N3 C8 N4 2.1(3) . . . . ?
C11 N3 C8 N1 -178.0(2) . . . . ?
C1 N1 C8 N4 -9.5(3) . . . . ?
C2 N1 C8 N4 168.63(18) . . . . ?
C1 N1 C8 N3 170.53(19) . . . . ?
C2 N1 C8 N3 -11.3(3) . . . . ?
C8 N4 C9 C10 0.8(4) . . . . ?
N4 C9 C10 C11 0.6(4) . . . . ?
C8 N3 C11 C10 -0.4(4) . . . . ?
C9 C10 C11 N3 -0.7(4) . . . . ?
C17 C12 C13 C14 -1.9(4) . . . . ?
Se1 C12 C13 C14 -179.4(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 2.3(4) . . . . ?
C13 C14 C15 Cl1 -176.2(2) . . . . ?
C14 C15 C16 C17 -2.0(4) . . . . ?
Cl1 C15 C16 C17 176.48(18) . . . . ?
C13 C12 C17 C16 2.2(3) . . . . ?
Se1 C12 C17 C16 179.73(17) . . . . ?
C15 C16 C17 C12 -0.3(4) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.053

