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

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

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2341428'
loop_
_audit_author_name
_audit_author_address
'lu chen'
;wuyi university
China
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O2 S Se'
_chemical_formula_sum            'C17 H13 N O2 S Se'
_chemical_formula_weight         374.30
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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                   5.852
_cell_length_b                   19.044
_cell_length_c                   14.544
_cell_angle_alpha                90
_cell_angle_beta                 101.05
_cell_angle_gamma                90
_cell_volume                     1590.7
_cell_formula_units_Z            4
_cell_measurement_reflns_used    993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.71
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.662
_shelx_estimated_absorpt_T_min   0.610
_exptl_absorpt_coefficient_mu    2.497
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5133
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.139
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1615
_reflns_number_total             2799
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      0.989
_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)+(0.0588P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1214
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
C1 C 0.3596(10) 0.1567(2) 0.4663(4) 0.0721(17) Uani 1 1 d . . . . .
H1A H 0.3811 0.1274 0.4149 0.108 Uiso 1 1 calc R U . . .
H1B H 0.2002 0.1544 0.4735 0.108 Uiso 1 1 calc R U . . .
H1C H 0.4589 0.1408 0.5228 0.108 Uiso 1 1 calc R U . . .
C2 C 0.6103(9) 0.2367(3) 0.4137(3) 0.0447(12) Uani 1 1 d . . . . .
C3 C 0.6508(8) 0.3112(2) 0.3923(3) 0.0364(11) Uani 1 1 d . . . . .
C4 C 0.5049(8) 0.3645(2) 0.4087(3) 0.0413(12) Uani 1 1 d . . . . .
H4 H 0.3792 0.3546 0.4371 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5444(8) 0.4329(2) 0.3829(3) 0.0437(12) Uani 1 1 d . . . . .
H5 H 0.4482 0.4689 0.3961 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7268(8) 0.4480(2) 0.3374(3) 0.0355(11) Uani 1 1 d . . . . .
C7 C 0.8753(9) 0.3938(3) 0.3244(3) 0.0491(13) Uani 1 1 d . . . . .
H7 H 1.0032 0.4033 0.2970 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8374(9) 0.3266(2) 0.3510(3) 0.0483(13) Uani 1 1 d . . . . .
H8 H 0.9387 0.2910 0.3410 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7780(7) 0.5214(2) 0.3117(3) 0.0357(11) Uani 1 1 d . . . . .
C10 C 0.7450(8) 0.5468(2) 0.2250(3) 0.0429(12) Uani 1 1 d . . . . .
H10 H 0.7803 0.5936 0.2163 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3587(10) 0.4848(3) 0.1367(3) 0.0551(14) Uani 1 1 d . . . . .
C12 C 1.0384(9) 0.6544(2) 0.3676(3) 0.0415(12) Uani 1 1 d . . . . .
C13 C 1.2230(9) 0.6468(3) 0.3212(4) 0.0538(14) Uani 1 1 d . . . . .
H13 H 1.2754 0.6021 0.3095 0.065 Uiso 1 1 calc R U . . .
C14 C 1.3280(10) 0.7047(3) 0.2924(4) 0.0672(16) Uani 1 1 d . . . . .
H14 H 1.4497 0.6995 0.2602 0.081 Uiso 1 1 calc R U . . .
C15 C 1.2545(11) 0.7699(3) 0.3110(4) 0.0656(16) Uani 1 1 d . . . . .
H15 H 1.3291 0.8092 0.2929 0.079 Uiso 1 1 calc R U . . .
C16 C 1.0716(11) 0.7782(3) 0.3561(4) 0.0631(16) Uani 1 1 d . . . . .
H16 H 1.0215 0.8231 0.3679 0.076 Uiso 1 1 calc R U . . .
C17 C 0.9603(9) 0.7197(3) 0.3845(3) 0.0536(14) Uani 1 1 d . . . . .
H17 H 0.8345 0.7251 0.4144 0.064 Uiso 1 1 calc R U . . .
N1 N 0.1722(9) 0.4752(3) 0.1429(4) 0.0901(18) Uani 1 1 d . . . . .
O1 O 0.7358(7) 0.18975(18) 0.4002(3) 0.0625(10) Uani 1 1 d . . . . .
O2 O 0.4175(6) 0.22780(16) 0.4479(2) 0.0552(10) Uani 1 1 d . . . . .
S1 S 0.6357(2) 0.49433(8) 0.12498(9) 0.0554(4) Uani 1 1 d . . . . .
Se1 Se 0.91403(10) 0.57402(3) 0.42012(3) 0.0521(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O2 1.433(5) . ?
C2 C3 1.481(6) . ?
C2 O1 1.197(5) . ?
C2 O2 1.328(6) . ?
C3 C4 1.375(6) . ?
C3 C8 1.375(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 C7 1.385(6) . ?
C6 C9 1.493(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.329(6) . ?
C9 Se1 1.909(4) . ?
C10 H10 0.9300 . ?
C10 S1 1.779(4) . ?
C11 N1 1.127(6) . ?
C11 S1 1.672(6) . ?
C12 C13 1.387(7) . ?
C12 C17 1.363(6) . ?
C12 Se1 1.916(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(7) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
O1 C2 C3 123.6(5) . . ?
O1 C2 O2 123.8(5) . . ?
O2 C2 C3 112.5(4) . . ?
C4 C3 C2 122.7(4) . . ?
C4 C3 C8 119.4(4) . . ?
C8 C3 C2 117.9(4) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C9 121.5(4) . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 C9 120.1(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C6 C9 Se1 110.9(3) . . ?
C10 C9 C6 125.3(4) . . ?
C10 C9 Se1 123.7(3) . . ?
C9 C10 H10 118.8 . . ?
C9 C10 S1 122.4(4) . . ?
S1 C10 H10 118.8 . . ?
N1 C11 S1 176.6(6) . . ?
C13 C12 Se1 120.1(4) . . ?
C17 C12 C13 120.2(5) . . ?
C17 C12 Se1 119.4(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.0(5) . . ?
C12 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C2 O2 C1 116.1(4) . . ?
C11 S1 C10 100.4(2) . . ?
C9 Se1 C12 102.72(19) . . ?

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
C2 C3 C4 C5 -176.7(4) . . . . ?
C2 C3 C8 C7 176.0(4) . . . . ?
C3 C2 O2 C1 177.2(4) . . . . ?
C3 C4 C5 C6 2.2(7) . . . . ?
C4 C3 C8 C7 -1.4(7) . . . . ?
C4 C5 C6 C7 -4.1(7) . . . . ?
C4 C5 C6 C9 -178.0(4) . . . . ?
C5 C6 C7 C8 3.3(7) . . . . ?
C5 C6 C9 C10 -110.1(5) . . . . ?
C5 C6 C9 Se1 72.9(5) . . . . ?
C6 C7 C8 C3 -0.6(8) . . . . ?
C6 C9 C10 S1 -1.0(7) . . . . ?
C7 C6 C9 C10 76.2(6) . . . . ?
C7 C6 C9 Se1 -100.8(4) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
C9 C6 C7 C8 177.3(4) . . . . ?
C9 C10 S1 C11 71.4(4) . . . . ?
C12 C13 C14 C15 1.3(8) . . . . ?
C13 C12 C17 C16 -1.3(7) . . . . ?
C13 C14 C15 C16 -1.8(9) . . . . ?
C14 C15 C16 C17 0.7(9) . . . . ?
C15 C16 C17 C12 0.9(8) . . . . ?
C17 C12 C13 C14 0.3(7) . . . . ?
O1 C2 C3 C4 -179.7(5) . . . . ?
O1 C2 C3 C8 2.9(7) . . . . ?
O1 C2 O2 C1 -1.8(7) . . . . ?
O2 C2 C3 C4 1.3(6) . . . . ?
O2 C2 C3 C8 -176.0(4) . . . . ?
Se1 C9 C10 S1 175.7(2) . . . . ?
Se1 C12 C13 C14 -173.0(4) . . . . ?
Se1 C12 C17 C16 172.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
