# 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_TK-401
_database_code_depnum_ccdc_archive 'CCDC 2506169'
loop_
_audit_author_name
_audit_author_address
'Aida I. Samigullina'
;Zelinsky Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-04-10 downloaded from the CCDC.
;
_audit_creation_date             2025-05-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N3 O Se'
_chemical_formula_sum            'C14 H15 N3 O Se'
_chemical_formula_weight         320.25
_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'
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                   7.8853(3)
_cell_length_b                   7.8504(3)
_cell_length_c                   21.1466(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.193(2)
_cell_angle_gamma                90
_cell_volume                     1307.00(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    291.0
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    2.868
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0821 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.7566.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            50591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.547
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_temperature      291.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3854
_reflns_number_total             4373
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.060
_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)+(0.0227P)²+0.8340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0556
_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:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Se7 Se 0.59612(2) 0.48352(2) 0.91771(2) 0.01535(4) Uani 1 1 d . . . . .
O5 O 0.78525(12) 0.69911(13) 0.77400(5) 0.01927(19) Uani 1 1 d . . . . .
N1 N 0.16069(13) 0.34332(14) 0.81326(5) 0.01465(19) Uani 1 1 d . . . . .
N4 N 0.52815(13) 0.57058(14) 0.76851(5) 0.01311(19) Uani 1 1 d . . . . .
C8 C 0.40579(15) 0.43468(16) 0.86244(6) 0.0134(2) Uani 1 1 d . . . . .
C9 C 0.24897(16) 0.35247(16) 0.86894(6) 0.0138(2) Uani 1 1 d . . . . .
C18 C 0.17710(18) 0.28448(18) 0.92770(6) 0.0185(2) Uani 1 1 d . . . . .
H18A H 0.137973 0.377331 0.952585 0.028 Uiso 1 1 calc R U . . .
H18B H 0.263372 0.222476 0.951841 0.028 Uiso 1 1 calc R U . . .
H18C H 0.083751 0.209903 0.916460 0.028 Uiso 1 1 calc R U . . .
N2 N 0.26131(13) 0.41909(14) 0.77030(5) 0.01342(19) Uani 1 1 d . . . . .
C10 C 0.21174(15) 0.41536(16) 0.70459(6) 0.0130(2) Uani 1 1 d . . . . .
C11 C 0.32511(15) 0.35404(16) 0.66196(6) 0.0138(2) Uani 1 1 d . . . . .
H11 H 0.434354 0.321553 0.675832 0.017 Uiso 1 1 calc R U . . .
C12 C 0.27229(15) 0.34203(16) 0.59802(6) 0.0140(2) Uani 1 1 d . . . . .
C16 C 0.39180(17) 0.27789(18) 0.55019(6) 0.0188(2) Uani 1 1 d . . . . .
H16A H 0.330704 0.206528 0.519914 0.028 Uiso 1 1 calc R U . . .
H16B H 0.481378 0.213426 0.571441 0.028 Uiso 1 1 calc R U . . .
H16C H 0.439450 0.372868 0.528755 0.028 Uiso 1 1 calc R U . . .
C13 C 0.10581(16) 0.38794(16) 0.57908(6) 0.0149(2) Uani 1 1 d . . . . .
H13 H 0.069718 0.377774 0.536625 0.018 Uiso 1 1 calc R U . . .
C14 C -0.00757(15) 0.44856(16) 0.62212(6) 0.0146(2) Uani 1 1 d . . . . .
C17 C -0.18819(17) 0.49204(18) 0.60107(7) 0.0190(2) Uani 1 1 d . . . . .
H17A H -0.259563 0.479170 0.636083 0.029 Uiso 1 1 calc R U . . .
H17B H -0.226536 0.416962 0.567406 0.029 Uiso 1 1 calc R U . . .
H17C H -0.193483 0.607667 0.586319 0.029 Uiso 1 1 calc R U . . .
C15 C 0.04759(15) 0.46481(16) 0.68558(6) 0.0142(2) Uani 1 1 d . . . . .
H15 H -0.024697 0.508273 0.714897 0.017 Uiso 1 1 calc R U . . .
C3 C 0.40772(15) 0.47700(15) 0.79917(6) 0.0122(2) Uani 1 1 d . . . . .
C5 C 0.69009(15) 0.59100(16) 0.79417(6) 0.0147(2) Uani 1 1 d . . . . .
C6 C 0.74577(16) 0.46838(17) 0.84653(6) 0.0164(2) Uani 1 1 d . . . . .
H6A H 0.861467 0.494389 0.861401 0.020 Uiso 1 1 calc R U . . .
H6B H 0.743731 0.353038 0.830051 0.020 Uiso 1 1 calc R U . . .
H4 H 0.495(2) 0.642(3) 0.7405(9) 0.024(5) Uiso 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
Se7 C8 1.8894(12) . ?
Se7 C6 1.9674(13) . ?
O5 C5 1.2251(16) . ?
N1 C9 1.3359(16) . ?
N1 N2 1.3743(14) . ?
N4 C3 1.3893(16) . ?
N4 C5 1.3688(15) . ?
N4 H4 0.845(19) . ?
C8 C9 1.4083(17) . ?
C8 C3 1.3797(16) . ?
C9 C18 1.4929(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N2 C10 1.4228(15) . ?
N2 C3 1.3541(15) . ?
C10 C11 1.3904(17) . ?
C10 C15 1.3891(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3956(17) . ?
C12 C16 1.5069(18) . ?
C12 C13 1.3982(17) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.3945(18) . ?
C14 C17 1.5074(17) . ?
C14 C15 1.3935(17) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15 0.9300 . ?
C5 C6 1.5137(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
C8 Se7 C6 90.23(5) . . ?
C9 N1 N2 105.52(10) . . ?
C3 N4 H4 119.0(13) . . ?
C5 N4 C3 121.58(11) . . ?
C5 N4 H4 116.4(13) . . ?
C9 C8 Se7 134.76(9) . . ?
C3 C8 Se7 119.99(9) . . ?
C3 C8 C9 105.19(10) . . ?
N1 C9 C8 110.85(11) . . ?
N1 C9 C18 120.74(11) . . ?
C8 C9 C18 128.39(11) . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 N2 C10 119.96(10) . . ?
C3 N2 N1 110.89(10) . . ?
C3 N2 C10 128.91(10) . . ?
C11 C10 N2 119.25(11) . . ?
C15 C10 N2 118.53(11) . . ?
C15 C10 C11 122.12(11) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.91(11) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C16 120.58(11) . . ?
C11 C12 C13 119.01(11) . . ?
C13 C12 C16 120.40(11) . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.79(11) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C17 120.94(11) . . ?
C15 C14 C13 118.86(11) . . ?
C15 C14 C17 120.18(12) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C15 C14 119.27(11) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C8 C3 N4 128.66(11) . . ?
N2 C3 N4 123.71(11) . . ?
N2 C3 C8 107.52(11) . . ?
O5 C5 N4 121.27(12) . . ?
O5 C5 C6 122.47(11) . . ?
N4 C5 C6 116.21(11) . . ?
Se7 C6 H6A 109.4 . . ?
Se7 C6 H6B 109.4 . . ?
C5 C6 Se7 111.06(8) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 N1 0.845(19) 2.27(2) 3.0829(15) 161.7(17) 2_556 yes

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
Se7 C8 C9 N1 -176.62(10) . . . . ?
Se7 C8 C9 C18 4.9(2) . . . . ?
Se7 C8 C3 N4 -7.33(18) . . . . ?
Se7 C8 C3 N2 176.44(8) . . . . ?
O5 C5 C6 Se7 123.68(12) . . . . ?
N1 N2 C10 C11 -126.57(12) . . . . ?
N1 N2 C10 C15 49.99(16) . . . . ?
N1 N2 C3 N4 -174.93(11) . . . . ?
N1 N2 C3 C8 1.53(14) . . . . ?
N4 C5 C6 Se7 -58.74(13) . . . . ?
C9 N1 N2 C10 173.62(11) . . . . ?
C9 N1 N2 C3 -1.19(14) . . . . ?
C9 C8 C3 N4 175.01(12) . . . . ?
C9 C8 C3 N2 -1.22(14) . . . . ?
N2 N1 C9 C8 0.38(14) . . . . ?
N2 N1 C9 C18 178.96(11) . . . . ?
N2 C10 C11 C12 176.52(11) . . . . ?
N2 C10 C15 C14 -174.72(11) . . . . ?
C10 N2 C3 N4 10.9(2) . . . . ?
C10 N2 C3 C8 -172.68(12) . . . . ?
C10 C11 C12 C16 179.38(12) . . . . ?
C10 C11 C12 C13 -1.59(18) . . . . ?
C11 C10 C15 C14 1.74(19) . . . . ?
C11 C12 C13 C14 1.32(19) . . . . ?
C12 C13 C14 C17 -178.02(12) . . . . ?
C12 C13 C14 C15 0.50(19) . . . . ?
C16 C12 C13 C14 -179.66(12) . . . . ?
C13 C14 C15 C10 -2.00(18) . . . . ?
C17 C14 C15 C10 176.54(11) . . . . ?
C15 C10 C11 C12 0.09(19) . . . . ?
C3 N4 C5 O5 -165.42(12) . . . . ?
C3 N4 C5 C6 16.98(17) . . . . ?
C3 C8 C9 N1 0.52(14) . . . . ?
C3 C8 C9 C18 -177.92(12) . . . . ?
C3 N2 C10 C11 47.19(19) . . . . ?
C3 N2 C10 C15 -136.25(13) . . . . ?
C5 N4 C3 C8 20.53(19) . . . . ?
C5 N4 C3 N2 -163.79(12) . . . . ?
C6 Se7 C8 C9 149.44(13) . . . . ?
C6 Se7 C8 C3 -27.38(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
