# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_231204h_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc2hxp48
_database_code_depnum_ccdc_archive 'CCDC 2321470'
loop_
_audit_author_name
_audit_author_address
yuanchengyue
;Xinjiang University
China
;
_audit_update_record             
;
2023-12-23 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_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         'C17 H14 N2 O S Se'
_chemical_formula_sum            'C17 H14 N2 O S Se'
_chemical_formula_weight         373.32
_chemical_absolute_configuration ad
_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      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                   6.5195(10)
_cell_length_b                   8.3597(13)
_cell_length_c                   29.903(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1629.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.793
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0984 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.6251.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9718
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3201
_reflns_number_total             3689
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.450
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.121
_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)+(0.0260P)²+0.4854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00J), C00J(H00K),
 C00K(H00L), C00L(H00M), C00M(H00N)
2.c Idealised Me refined as rotating group:
 C00H(H00C,H00H,H00I)
;
_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
Se01 Se 0.52117(6) 0.96948(6) 0.36134(2) 0.03336(14) Uani 1 1 d . . . . .
S002 S 0.4812(2) 0.78582(16) 0.26442(4) 0.0407(3) Uani 1 1 d . . . . .
N003 N 0.5707(5) 0.5802(5) 0.33412(12) 0.0269(9) Uani 1 1 d . . . . .
N004 N 0.7864(6) 0.5782(5) 0.27484(13) 0.0317(10) Uani 1 1 d . . . . .
O005 O 0.4039(5) 0.5748(5) 0.40034(12) 0.0491(10) Uani 1 1 d . . . . .
C006 C 0.7235(6) 0.4662(6) 0.34383(15) 0.0280(10) Uani 1 1 d . . . . .
C007 C 0.6232(6) 0.6411(6) 0.29186(15) 0.0272(10) Uani 1 1 d . . . . .
C008 C 0.5274(6) 0.9761(6) 0.42580(15) 0.0343(10) Uani 1 1 d . . . . .
C009 C 0.2628(7) 0.7963(7) 0.30185(15) 0.0314(11) Uani 1 1 d . . . . .
H00A H 0.188273 0.894398 0.295782 0.038 Uiso 1 1 calc R U . . .
H00B H 0.171741 0.707628 0.295299 0.038 Uiso 1 1 calc R U . . .
C00A C 0.3168(6) 0.7918(6) 0.35138(15) 0.0290(11) Uani 1 1 d . . . . .
C00B C 0.4269(6) 0.6418(6) 0.36496(17) 0.0301(10) Uani 1 1 d . . . . .
C00C C 0.8535(6) 0.4681(7) 0.30726(17) 0.0330(11) Uani 1 1 d . . . . .
C00D C 0.6613(8) 0.8772(8) 0.44926(19) 0.0453(14) Uani 1 1 d . . . . .
H00D H 0.739245 0.801723 0.434010 0.054 Uiso 1 1 calc R U . . .
C00E C 0.7536(8) 0.3663(6) 0.38014(18) 0.0394(13) Uani 1 1 d . . . . .
H00E H 0.663927 0.364633 0.404327 0.047 Uiso 1 1 calc R U . . .
C00F C 0.9263(9) 0.2684(7) 0.3783(2) 0.0552(17) Uani 1 1 d . . . . .
H00F H 0.954646 0.200375 0.402090 0.066 Uiso 1 1 calc R U . . .
C00G C 1.0558(9) 0.2699(7) 0.3420(2) 0.0585(17) Uani 1 1 d . . . . .
H00G H 1.168341 0.201578 0.341919 0.070 Uiso 1 1 calc R U . . .
C00H C 0.1235(7) 0.8132(7) 0.37915(19) 0.0409(14) Uani 1 1 d . . . . .
H00C H 0.159292 0.819070 0.410242 0.061 Uiso 1 1 calc R U . . .
H00H H 0.033519 0.723921 0.374340 0.061 Uiso 1 1 calc R U . . .
H00I H 0.055477 0.910131 0.370392 0.061 Uiso 1 1 calc R U . . .
C00I C 0.4133(8) 1.0867(8) 0.4488(2) 0.0546(17) Uani 1 1 d . . . . .
H00J H 0.324602 1.154131 0.433382 0.066 Uiso 1 1 calc R U . . .
C00J C 1.0252(8) 0.3688(7) 0.3058(2) 0.0503(14) Uani 1 1 d . . . . .
H00K H 1.114616 0.369344 0.281606 0.060 Uiso 1 1 calc R U . . .
C00K C 0.6787(9) 0.8910(9) 0.4951(2) 0.0595(19) Uani 1 1 d . . . . .
H00L H 0.768658 0.825227 0.510748 0.071 Uiso 1 1 calc R U . . .
C00L C 0.4297(11) 1.0984(9) 0.4946(2) 0.072(2) Uani 1 1 d . . . . .
H00M H 0.349606 1.172273 0.509935 0.086 Uiso 1 1 calc R U . . .
C00M C 0.5621(9) 1.0026(9) 0.5177(2) 0.066(2) Uani 1 1 d . . . . .
H00N H 0.573712 1.012567 0.548544 0.080 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
Se01 C008 1.929(4) . ?
Se01 C00A 2.017(5) . ?
S002 C007 1.730(5) . ?
S002 C009 1.814(5) . ?
N003 C006 1.409(6) . ?
N003 C007 1.405(6) . ?
N003 C00B 1.412(6) . ?
N004 C007 1.291(6) . ?
N004 C00C 1.406(7) . ?
O005 C00B 1.207(6) . ?
C006 C00C 1.384(6) . ?
C006 C00E 1.384(7) . ?
C008 C00D 1.392(7) . ?
C008 C00I 1.371(7) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00A 1.523(6) . ?
C00A C00B 1.501(6) . ?
C00A C00H 1.520(6) . ?
C00C C00J 1.394(7) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.381(8) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.394(7) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.374(9) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.376(8) . ?
C00H H00C 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00I H00J 0.9300 . ?
C00I C00L 1.377(8) . ?
C00J H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00K C00M 1.379(9) . ?
C00L H00M 0.9300 . ?
C00L C00M 1.365(9) . ?
C00M H00N 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
C008 Se01 C00A 100.51(19) . . ?
C007 S002 C009 99.3(2) . . ?
C006 N003 C00B 125.6(4) . . ?
C007 N003 C006 105.0(3) . . ?
C007 N003 C00B 128.1(4) . . ?
C007 N004 C00C 104.6(4) . . ?
C00C C006 N003 105.2(4) . . ?
C00C C006 C00E 122.7(5) . . ?
C00E C006 N003 132.1(4) . . ?
N003 C007 S002 123.4(3) . . ?
N004 C007 S002 122.6(4) . . ?
N004 C007 N003 114.0(4) . . ?
C00D C008 Se01 120.0(4) . . ?
C00I C008 Se01 120.6(4) . . ?
C00I C008 C00D 119.2(5) . . ?
S002 C009 H00A 108.6 . . ?
S002 C009 H00B 108.6 . . ?
H00A C009 H00B 107.6 . . ?
C00A C009 S002 114.7(3) . . ?
C00A C009 H00A 108.6 . . ?
C00A C009 H00B 108.6 . . ?
C009 C00A Se01 106.1(3) . . ?
C00B C00A Se01 105.0(3) . . ?
C00B C00A C009 113.2(4) . . ?
C00B C00A C00H 110.3(4) . . ?
C00H C00A Se01 112.4(4) . . ?
C00H C00A C009 109.7(4) . . ?
N003 C00B C00A 116.5(4) . . ?
O005 C00B N003 119.1(4) . . ?
O005 C00B C00A 124.5(4) . . ?
C006 C00C N004 111.2(4) . . ?
C006 C00C C00J 120.6(5) . . ?
C00J C00C N004 128.2(5) . . ?
C008 C00D H00D 119.9 . . ?
C00K C00D C008 120.2(5) . . ?
C00K C00D H00D 119.9 . . ?
C006 C00E H00E 122.0 . . ?
C006 C00E C00F 115.9(5) . . ?
C00F C00E H00E 122.0 . . ?
C00E C00F H00F 119.2 . . ?
C00G C00F C00E 121.5(5) . . ?
C00G C00F H00F 119.2 . . ?
C00F C00G H00G 118.8 . . ?
C00F C00G C00J 122.5(5) . . ?
C00J C00G H00G 118.8 . . ?
C00A C00H H00C 109.5 . . ?
C00A C00H H00H 109.5 . . ?
C00A C00H H00I 109.5 . . ?
H00C C00H H00H 109.5 . . ?
H00C C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C008 C00I H00J 119.9 . . ?
C008 C00I C00L 120.3(6) . . ?
C00L C00I H00J 119.9 . . ?
C00C C00J H00K 121.6 . . ?
C00G C00J C00C 116.8(5) . . ?
C00G C00J H00K 121.6 . . ?
C00D C00K H00L 120.1 . . ?
C00M C00K C00D 119.8(6) . . ?
C00M C00K H00L 120.1 . . ?
C00I C00L H00M 119.7 . . ?
C00M C00L C00I 120.7(6) . . ?
C00M C00L H00M 119.7 . . ?
C00K C00M H00N 120.1 . . ?
C00L C00M C00K 119.9(6) . . ?
C00L C00M H00N 120.1 . . ?

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 C008 C00D C00K 174.6(5) . . . . ?
Se01 C008 C00I C00L -175.3(5) . . . . ?
Se01 C00A C00B N003 -77.4(4) . . . . ?
Se01 C00A C00B O005 100.7(5) . . . . ?
S002 C009 C00A Se01 54.4(4) . . . . ?
S002 C009 C00A C00B -60.3(5) . . . . ?
S002 C009 C00A C00H 176.0(4) . . . . ?
N003 C006 C00C N004 -0.5(5) . . . . ?
N003 C006 C00C C00J 179.6(4) . . . . ?
N003 C006 C00E C00F -179.5(5) . . . . ?
N004 C00C C00J C00G -179.3(5) . . . . ?
C006 N003 C007 S002 179.6(3) . . . . ?
C006 N003 C007 N004 0.4(5) . . . . ?
C006 N003 C00B O005 -14.2(7) . . . . ?
C006 N003 C00B C00A 163.9(4) . . . . ?
C006 C00C C00J C00G 0.6(7) . . . . ?
C006 C00E C00F C00G -1.1(8) . . . . ?
C007 S002 C009 C00A 41.7(4) . . . . ?
C007 N003 C006 C00C 0.1(5) . . . . ?
C007 N003 C006 C00E -179.3(5) . . . . ?
C007 N003 C00B O005 -178.7(4) . . . . ?
C007 N003 C00B C00A -0.6(7) . . . . ?
C007 N004 C00C C006 0.8(6) . . . . ?
C007 N004 C00C C00J -179.4(5) . . . . ?
C008 C00D C00K C00M 0.3(10) . . . . ?
C008 C00I C00L C00M 1.3(11) . . . . ?
C009 S002 C007 N003 -7.3(4) . . . . ?
C009 S002 C007 N004 171.9(4) . . . . ?
C009 C00A C00B N003 38.0(5) . . . . ?
C009 C00A C00B O005 -144.0(5) . . . . ?
C00B N003 C006 C00C -167.3(4) . . . . ?
C00B N003 C006 C00E 13.2(8) . . . . ?
C00B N003 C007 S002 -13.4(7) . . . . ?
C00B N003 C007 N004 167.4(4) . . . . ?
C00C N004 C007 S002 -180.0(4) . . . . ?
C00C N004 C007 N003 -0.7(5) . . . . ?
C00C C006 C00E C00F 1.2(8) . . . . ?
C00D C008 C00I C00L -0.7(9) . . . . ?
C00D C00K C00M C00L 0.3(10) . . . . ?
C00E C006 C00C N004 179.0(4) . . . . ?
C00E C006 C00C C00J -0.9(8) . . . . ?
C00E C00F C00G C00J 0.9(9) . . . . ?
C00F C00G C00J C00C -0.6(8) . . . . ?
C00H C00A C00B N003 161.3(4) . . . . ?
C00H C00A C00B O005 -20.6(7) . . . . ?
C00I C008 C00D C00K -0.1(8) . . . . ?
C00I C00L C00M C00K -1.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
