# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_yx_1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2393134'
loop_
_audit_author_name
_audit_author_address
'Yu Xiao'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2024-10-23 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_audit_creation_date             2024-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N3 O S Se'
_chemical_formula_sum            'C13 H13 N3 O S Se'
_chemical_formula_weight         338.28
_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 0.0181 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'
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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.722(3)
_cell_length_b                   7.1939(8)
_cell_length_c                   8.2904(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1414.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    860
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      50.783
_cell_measurement_theta_min      3.731
_shelx_estimated_absorpt_T_max   0.470
_shelx_estimated_absorpt_T_min   0.237
_exptl_absorpt_coefficient_mu    4.939
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1741 before and 0.1027 after correction.
The Ratio of minimum to maximum transmission is 0.6421.
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    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28958
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.727
_diffrn_ambient_temperature      297.00
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_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         0.812
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2421
_reflns_number_total             2492
_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         0.335
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.201(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.108
_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)+(0.0515P)²+0.2714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0810
_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 Ternary CH refined with riding coordinates:
 C00D(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00E), C00E(H00G), C00H(H00K), C00I(H00L)
2.d Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J)
;
_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 0.57414(2) 0.59978(6) 0.05932(7) 0.04604(18) Uani 1 1 d . . . . .
S002 S 0.42920(4) 0.96734(14) 0.22869(13) 0.0394(2) Uani 1 1 d . . . . .
N003 N 0.35231(13) 0.7632(5) 0.4049(4) 0.0396(7) Uani 1 1 d . . . . .
N004 N 0.39199(14) 0.6367(5) 0.1754(4) 0.0400(7) Uani 1 1 d . . . . .
C005 C 0.38608(15) 0.7760(5) 0.2797(5) 0.0348(8) Uani 1 1 d . . . . .
O006 O 0.36847(15) 1.0681(5) 0.4778(5) 0.0543(8) Uani 1 1 d . . . . .
C007 C 0.29831(17) 0.7034(7) 0.7008(6) 0.0484(10) Uani 1 1 d . . . . .
H007 H 0.298482 0.610026 0.623178 0.058 Uiso 1 1 calc R U . . .
C008 C 0.32291(16) 0.8731(6) 0.6669(6) 0.0407(9) Uani 1 1 d . . . . .
C009 C 0.42822(16) 0.6731(7) 0.0375(5) 0.0447(10) Uani 1 1 d . . . . .
H00A H 0.406020 0.715060 -0.053743 0.054 Uiso 1 1 calc R U . . .
H00B H 0.448302 0.561153 0.006607 0.054 Uiso 1 1 calc R U . . .
C00A C 0.52097(17) 0.7560(6) 0.1817(5) 0.0410(8) Uani 1 1 d . . . . .
H00C H 0.508249 0.686325 0.275028 0.049 Uiso 1 1 calc R U . . .
H00D H 0.541160 0.864143 0.221147 0.049 Uiso 1 1 calc R U . . .
C00B C 0.32270(19) 1.0106(7) 0.7849(7) 0.0548(11) Uani 1 1 d . . . . .
H00E H 0.338848 1.125736 0.763252 0.066 Uiso 1 1 calc R U . . .
C00C C 0.35005(17) 0.9114(5) 0.5080(5) 0.0378(9) Uani 1 1 d . . . . .
C00D C 0.46932(17) 0.8227(5) 0.0890(5) 0.0404(9) Uani 1 1 d . . . . .
H00F H 0.481000 0.896257 -0.004678 0.048 Uiso 1 1 calc R U . . .
C00E C 0.2986(2) 0.9773(9) 0.9340(6) 0.0671(15) Uani 1 1 d . . . . .
H00G H 0.299490 1.068598 1.013370 0.080 Uiso 1 1 calc R U . . .
N00F N 0.5232(2) 0.2352(6) 0.1449(6) 0.0659(12) Uani 1 1 d . . . . .
C00G C 0.3579(2) 0.4671(6) 0.1804(6) 0.0522(11) Uani 1 1 d . . . . .
H00H H 0.329639 0.478837 0.262577 0.078 Uiso 1 1 calc R U . . .
H00I H 0.381735 0.362756 0.204350 0.078 Uiso 1 1 calc R U . . .
H00J H 0.340125 0.448599 0.077730 0.078 Uiso 1 1 calc R U . . .
C00H C 0.2733(2) 0.6710(8) 0.8499(6) 0.0624(13) Uani 1 1 d . . . . .
H00K H 0.256589 0.556773 0.871775 0.075 Uiso 1 1 calc R U . . .
C00I C 0.2734(2) 0.8086(10) 0.9645(6) 0.0686(15) Uani 1 1 d . . . . .
H00L H 0.256346 0.787684 1.063781 0.082 Uiso 1 1 calc R U . . .
C00J C 0.54156(18) 0.3759(6) 0.1134(5) 0.0448(10) 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
Se01 C00A 1.971(4) . ?
Se01 C00J 1.842(4) . ?
S002 C005 1.766(4) . ?
S002 C00D 1.825(4) . ?
N003 C005 1.314(5) . ?
N003 C00C 1.367(5) . ?
N004 C005 1.331(5) . ?
N004 C009 1.454(6) . ?
N004 C00G 1.463(5) . ?
O006 C00C 1.235(5) . ?
C007 H007 0.9300 . ?
C007 C008 1.382(6) . ?
C007 C00H 1.391(7) . ?
C008 C00B 1.391(7) . ?
C008 C00C 1.492(6) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00D 1.514(6) . ?
C00A H00C 0.9700 . ?
C00A H00D 0.9700 . ?
C00A C00D 1.524(6) . ?
C00B H00E 0.9300 . ?
C00B C00E 1.382(7) . ?
C00D H00F 0.9800 . ?
C00E H00G 0.9300 . ?
C00E C00I 1.376(9) . ?
N00F C00J 1.132(6) . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00H H00K 0.9300 . ?
C00H C00I 1.372(8) . ?
C00I H00L 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
C00J Se01 C00A 96.03(18) . . ?
C005 S002 C00D 90.55(18) . . ?
C005 N003 C00C 117.6(3) . . ?
C005 N004 C009 115.9(3) . . ?
C005 N004 C00G 123.4(4) . . ?
C009 N004 C00G 119.9(4) . . ?
N003 C005 S002 126.6(3) . . ?
N003 C005 N004 121.6(3) . . ?
N004 C005 S002 111.7(3) . . ?
C008 C007 H007 119.7 . . ?
C008 C007 C00H 120.6(5) . . ?
C00H C007 H007 119.7 . . ?
C007 C008 C00B 118.9(4) . . ?
C007 C008 C00C 121.7(4) . . ?
C00B C008 C00C 119.4(4) . . ?
N004 C009 H00A 110.4 . . ?
N004 C009 H00B 110.4 . . ?
N004 C009 C00D 106.7(3) . . ?
H00A C009 H00B 108.6 . . ?
C00D C009 H00A 110.4 . . ?
C00D C009 H00B 110.4 . . ?
Se01 C00A H00C 108.3 . . ?
Se01 C00A H00D 108.3 . . ?
H00C C00A H00D 107.4 . . ?
C00D C00A Se01 115.7(3) . . ?
C00D C00A H00C 108.3 . . ?
C00D C00A H00D 108.3 . . ?
C008 C00B H00E 119.8 . . ?
C00E C00B C008 120.5(5) . . ?
C00E C00B H00E 119.8 . . ?
N003 C00C C008 115.2(3) . . ?
O006 C00C N003 124.8(4) . . ?
O006 C00C C008 120.0(4) . . ?
S002 C00D H00F 110.0 . . ?
C009 C00D S002 104.4(3) . . ?
C009 C00D C00A 115.9(3) . . ?
C009 C00D H00F 110.0 . . ?
C00A C00D S002 106.2(3) . . ?
C00A C00D H00F 110.0 . . ?
C00B C00E H00G 120.1 . . ?
C00I C00E C00B 119.8(5) . . ?
C00I C00E H00G 120.1 . . ?
N004 C00G H00H 109.5 . . ?
N004 C00G H00I 109.5 . . ?
N004 C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 109.5 . . ?
C007 C00H H00K 120.2 . . ?
C00I C00H C007 119.6(5) . . ?
C00I C00H H00K 120.2 . . ?
C00E C00I H00L 119.7 . . ?
C00H C00I C00E 120.7(5) . . ?
C00H C00I H00L 119.7 . . ?
N00F C00J Se01 177.6(4) . . ?

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 C00A C00D S002 -178.5(2) . . . . ?
Se01 C00A C00D C009 66.1(4) . . . . ?
N004 C009 C00D S002 -33.3(4) . . . . ?
N004 C009 C00D C00A 83.1(4) . . . . ?
C005 S002 C00D C009 27.1(3) . . . . ?
C005 S002 C00D C00A -95.8(3) . . . . ?
C005 N003 C00C O006 14.6(6) . . . . ?
C005 N003 C00C C008 -165.4(3) . . . . ?
C005 N004 C009 C00D 25.7(5) . . . . ?
C007 C008 C00B C00E 0.5(7) . . . . ?
C007 C008 C00C N003 -4.6(5) . . . . ?
C007 C008 C00C O006 175.4(4) . . . . ?
C007 C00H C00I C00E -0.8(8) . . . . ?
C008 C007 C00H C00I -0.4(7) . . . . ?
C008 C00B C00E C00I -1.7(8) . . . . ?
C009 N004 C005 S002 -4.4(4) . . . . ?
C009 N004 C005 N003 176.7(4) . . . . ?
C00B C008 C00C N003 174.8(4) . . . . ?
C00B C008 C00C O006 -5.2(6) . . . . ?
C00B C00E C00I C00H 1.8(8) . . . . ?
C00C N003 C005 S002 -0.5(5) . . . . ?
C00C N003 C005 N004 178.3(4) . . . . ?
C00C C008 C00B C00E -178.9(4) . . . . ?
C00D S002 C005 N003 164.5(4) . . . . ?
C00D S002 C005 N004 -14.3(3) . . . . ?
C00G N004 C005 S002 -174.7(3) . . . . ?
C00G N004 C005 N003 6.4(6) . . . . ?
C00G N004 C009 C00D -163.7(4) . . . . ?
C00H C007 C008 C00B 0.5(7) . . . . ?
C00H C007 C008 C00C 180.0(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
