# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 2482127'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Cl N4 O'
_chemical_formula_sum            'C18 H11 Cl N4 O'
_chemical_formula_weight         334.76

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'
Cl Cl 0.3639 0.7018 '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'

_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'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.4130(11)
_cell_length_b                   22.3174(14)
_cell_length_c                   3.9518(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1447.53(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3980
_cell_measurement_theta_min      4.785
_cell_measurement_theta_max      78.404

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.449
_shelx_estimated_absorpt_T_min   0.357
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.99a (Rigaku Oxford Diffraction, 2025).
Numerical absorption correction based on gaussian integration
over a multifaceted crystal model.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -1 0.0134
1 1 -2 0.2443
0 -1 -1 0.0153
0 -1 0 0.0095
0 1 0 0.0095
0 -2 1 0.0175
1 1 2 0.2497
0 -1 1 0.0196
0 1 -2 0.0138
-1 -1 -2 0.2143
0 1 2 0.0180

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10280
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.343
_diffrn_reflns_theta_max         79.337
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             2709
_reflns_number_gt                2249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_max     0.726
_reflns_Friedel_fraction_full    0.811

_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       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_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)+(0.099P)²+5.5P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 608 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2133
_refine_ls_wR_factor_gt          0.2017
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_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 0.70976(9) 0.63102(7) 0.8970(6) 0.0225(4) Uani 1 1 d . . . . .
O1 O 0.6459(3) 0.49950(19) 0.3792(18) 0.0215(11) Uani 1 1 d . . . . .
N1 N 0.7801(3) 0.5147(2) 0.6934(16) 0.0141(12) Uani 1 1 d . . . . .
H1 H 0.720(5) 0.530(4) 0.64(2) 0.017 Uiso 1 1 d . U . . .
N2 N 0.8049(3) 0.4618(2) 0.5801(17) 0.0159(12) Uani 1 1 d . . . . .
N3 N 0.9048(3) 0.5280(3) 0.9837(16) 0.0174(13) Uani 1 1 d . . . . .
N4 N 0.8531(4) 0.6424(3) 1.1746(19) 0.0204(13) Uani 1 1 d . . . . .
C1 C 0.8315(4) 0.5489(3) 0.898(2) 0.0147(13) Uani 1 1 d . . . . .
C2 C 0.8065(4) 0.6063(3) 0.9979(19) 0.0158(15) Uani 1 1 d . . . . .
C3 C 0.9283(4) 0.6207(3) 1.257(2) 0.0216(16) Uani 1 1 d . . . . .
H3 H 0.965082 0.645578 1.377824 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9518(4) 0.5644(3) 1.169(2) 0.0177(14) Uani 1 1 d . . . . .
H4 H 1.003598 0.550337 1.241638 0.021 Uiso 1 1 calc R U . . .
C5 C 0.7556(4) 0.4299(3) 0.382(2) 0.0148(14) Uani 1 1 d . . . . .
C6 C 0.6716(4) 0.4494(3) 0.2955(19) 0.0164(15) Uani 1 1 d . . . . .
C7 C 0.6217(4) 0.4069(3) 0.099(2) 0.0171(14) Uani 1 1 d . . . . .
C8 C 0.5410(4) 0.4249(3) 0.0173(19) 0.0188(16) Uani 1 1 d . . . . .
H8 H 0.521856 0.463210 0.084676 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4910(4) 0.3870(4) -0.157(2) 0.0240(16) Uani 1 1 d . . . . .
H9 H 0.437265 0.399329 -0.213849 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5182(4) 0.3309(4) -0.253(2) 0.0241(17) Uani 1 1 d . . . . .
H10 H 0.483032 0.304651 -0.373183 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5978(4) 0.3125(3) -0.172(2) 0.0222(17) Uani 1 1 d . . . . .
H11 H 0.616222 0.274075 -0.241145 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6503(4) 0.3503(3) 0.0091(18) 0.0157(14) Uani 1 1 d . . . . .
C13 C 0.7355(4) 0.3327(3) 0.084(2) 0.0146(14) Uani 1 1 d . . . . .
C14 C 0.7662(4) 0.2778(3) -0.0133(19) 0.0199(16) Uani 1 1 d . . . . .
H14 H 0.731965 0.250397 -0.129475 0.024 Uiso 1 1 calc R U . . .
C15 C 0.8475(4) 0.2617(3) 0.056(2) 0.0220(16) Uani 1 1 d . . . . .
H15 H 0.867569 0.223612 -0.011165 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8977(4) 0.3016(3) 0.222(2) 0.0210(16) Uani 1 1 d . . . . .
H16 H 0.952831 0.291080 0.266037 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8685(4) 0.3564(3) 0.3254(19) 0.0171(15) Uani 1 1 d . . . . .
H17 H 0.903962 0.383853 0.434943 0.021 Uiso 1 1 calc R U . . .
C18 C 0.7864(4) 0.3721(3) 0.2698(19) 0.0148(15) 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
Cl1 C2 1.728(7) . ?
O1 C6 1.240(8) . ?
N1 N2 1.326(8) . ?
N1 C1 1.395(9) . ?
N1 H1 1.06(8) . ?
N2 C5 1.332(9) . ?
N3 C1 1.335(8) . ?
N3 C4 1.339(9) . ?
N4 C2 1.312(9) . ?
N4 C3 1.364(9) . ?
C1 C2 1.401(9) . ?
C3 C4 1.360(11) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C18 1.455(9) . ?
C5 C6 1.485(8) . ?
C6 C7 1.476(10) . ?
C7 C12 1.393(10) . ?
C7 C8 1.420(9) . ?
C8 C9 1.365(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.406(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.482(9) . ?
C13 C14 1.378(10) . ?
C13 C18 1.418(10) . ?
C14 C15 1.408(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.409(9) . ?
C17 H17 0.9500 . ?

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
N2 N1 C1 119.8(5) . . ?
N2 N1 H1 120(5) . . ?
C1 N1 H1 120(5) . . ?
N1 N2 C5 119.2(5) . . ?
C1 N3 C4 116.5(6) . . ?
C2 N4 C3 115.9(6) . . ?
N3 C1 N1 120.0(6) . . ?
N3 C1 C2 120.8(6) . . ?
N1 C1 C2 119.1(6) . . ?
N4 C2 C1 122.7(6) . . ?
N4 C2 Cl1 117.5(5) . . ?
C1 C2 Cl1 119.7(5) . . ?
C4 C3 N4 121.6(7) . . ?
C4 C3 H3 119.2 . . ?
N4 C3 H3 119.2 . . ?
N3 C4 C3 122.4(6) . . ?
N3 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
N2 C5 C18 116.2(6) . . ?
N2 C5 C6 122.8(6) . . ?
C18 C5 C6 120.8(6) . . ?
O1 C6 C7 122.1(6) . . ?
O1 C6 C5 121.3(6) . . ?
C7 C6 C5 116.6(6) . . ?
C12 C7 C8 120.9(6) . . ?
C12 C7 C6 121.9(6) . . ?
C8 C7 C6 117.1(6) . . ?
C9 C8 C7 120.0(7) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.3(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.2(7) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C7 C12 C11 117.8(6) . . ?
C7 C12 C13 120.6(6) . . ?
C11 C12 C13 121.5(6) . . ?
C14 C13 C18 118.6(6) . . ?
C14 C13 C12 121.7(6) . . ?
C18 C13 C12 119.7(6) . . ?
C13 C14 C15 121.3(7) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.6(7) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.4(7) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.5(7) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.4(6) . . ?
C17 C18 C5 120.4(6) . . ?
C13 C18 C5 120.2(6) . . ?

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
C1 N1 N2 C5 -179.3(7) . . . . ?
C4 N3 C1 N1 177.4(7) . . . . ?
C4 N3 C1 C2 0.2(11) . . . . ?
N2 N1 C1 N3 -1.3(11) . . . . ?
N2 N1 C1 C2 176.0(7) . . . . ?
C3 N4 C2 C1 0.0(11) . . . . ?
C3 N4 C2 Cl1 178.4(6) . . . . ?
N3 C1 C2 N4 1.0(12) . . . . ?
N1 C1 C2 N4 -176.3(7) . . . . ?
N3 C1 C2 Cl1 -177.4(6) . . . . ?
N1 C1 C2 Cl1 5.3(10) . . . . ?
C2 N4 C3 C4 -2.1(12) . . . . ?
C1 N3 C4 C3 -2.3(11) . . . . ?
N4 C3 C4 N3 3.4(13) . . . . ?
N1 N2 C5 C18 -179.4(6) . . . . ?
N1 N2 C5 C6 -3.2(10) . . . . ?
N2 C5 C6 O1 6.6(12) . . . . ?
C18 C5 C6 O1 -177.2(7) . . . . ?
N2 C5 C6 C7 -174.8(7) . . . . ?
C18 C5 C6 C7 1.3(11) . . . . ?
O1 C6 C7 C12 -179.0(7) . . . . ?
C5 C6 C7 C12 2.4(11) . . . . ?
O1 C6 C7 C8 -2.1(11) . . . . ?
C5 C6 C7 C8 179.3(7) . . . . ?
C12 C7 C8 C9 -1.5(12) . . . . ?
C6 C7 C8 C9 -178.5(7) . . . . ?
C7 C8 C9 C10 0.7(12) . . . . ?
C8 C9 C10 C11 -0.4(13) . . . . ?
C9 C10 C11 C12 0.8(12) . . . . ?
C8 C7 C12 C11 1.9(11) . . . . ?
C6 C7 C12 C11 178.7(7) . . . . ?
C8 C7 C12 C13 177.8(7) . . . . ?
C6 C7 C12 C13 -5.4(11) . . . . ?
C10 C11 C12 C7 -1.5(11) . . . . ?
C10 C11 C12 C13 -177.5(7) . . . . ?
C7 C12 C13 C14 -177.5(7) . . . . ?
C11 C12 C13 C14 -1.7(11) . . . . ?
C7 C12 C13 C18 4.6(11) . . . . ?
C11 C12 C13 C18 -179.6(7) . . . . ?
C18 C13 C14 C15 -2.7(11) . . . . ?
C12 C13 C14 C15 179.4(7) . . . . ?
C13 C14 C15 C16 -0.5(11) . . . . ?
C14 C15 C16 C17 1.1(12) . . . . ?
C15 C16 C17 C18 1.5(12) . . . . ?
C16 C17 C18 C13 -4.7(11) . . . . ?
C16 C17 C18 C5 179.4(7) . . . . ?
C14 C13 C18 C17 5.2(11) . . . . ?
C12 C13 C18 C17 -176.8(6) . . . . ?
C14 C13 C18 C5 -178.9(7) . . . . ?
C12 C13 C18 C5 -0.8(11) . . . . ?
N2 C5 C18 C17 -9.7(11) . . . . ?
C6 C5 C18 C17 173.9(7) . . . . ?
N2 C5 C18 C13 174.3(7) . . . . ?
C6 C5 C18 C13 -2.0(11) . . . . ?

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
N1 H1 O1 1.06(8) 1.73(9) 2.551(8) 131(7) . yes

_refine_diff_density_max         0.914
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_L4
_database_code_depnum_ccdc_archive 'CCDC 2482128'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-08-22 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N3 O S'
_chemical_formula_sum            'C23 H15 N3 O S'
_chemical_formula_weight         381.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.2762(5)
_cell_length_b                   5.30357(13)
_cell_length_c                   16.5308(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.649(2)
_cell_angle_gamma                90
_cell_volume                     1719.87(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23088
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      79.89

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.830
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.99a (Rigaku Oxford Diffraction, 2025).
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41624
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         80.128
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             3593
_reflns_number_gt                3412
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.01P)²+22P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3593
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.2271
_refine_ls_wR_factor_gt          0.2253
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_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
S1 S 0.85621(7) 0.6857(3) 0.37968(8) 0.0221(3) Uani 1 1 d . . . . .
O1 O 0.65704(19) 0.2371(8) 0.4745(2) 0.0232(8) Uani 1 1 d . . . . .
N1 N 0.7527(2) 0.4822(9) 0.4346(3) 0.0200(9) Uani 1 1 d . . . . .
H1 H 0.726(3) 0.484(13) 0.460(4) 0.024 Uiso 1 1 d . U . . .
N2 N 0.7456(2) 0.3291(9) 0.3686(3) 0.0196(9) Uani 1 1 d . . . . .
C2 C 0.8040(3) 0.6599(10) 0.4476(3) 0.0192(10) Uani 1 1 d . . . . .
N3 N 0.8153(2) 0.8145(8) 0.5106(2) 0.0196(9) Uani 1 1 d . . . . .
C4 C 0.8698(2) 0.9668(10) 0.5083(3) 0.0192(10) Uani 1 1 d . . . . .
C5 C 0.8973(3) 0.9273(11) 0.4421(3) 0.0222(11) Uani 1 1 d . . . . .
H5 H 0.934236 1.020859 0.431696 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8937(2) 1.1534(9) 0.5764(3) 0.0174(10) Uani 1 1 d . . . . .
C7 C 0.8725(3) 1.1347(10) 0.6504(3) 0.0210(10) Uani 1 1 d . . . . .
H7 H 0.841815 1.004937 0.656627 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8961(3) 1.3056(10) 0.7147(3) 0.0225(11) Uani 1 1 d . . . . .
H8 H 0.880877 1.292804 0.764357 0.027 Uiso 1 1 calc R U . . .
C9 C 0.9413(3) 1.4934(11) 0.7079(4) 0.0253(11) Uani 1 1 d . . . . .
H9 H 0.957502 1.608710 0.752470 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9627(3) 1.5112(11) 0.6344(3) 0.0247(11) Uani 1 1 d . . . . .
H10 H 0.993522 1.640750 0.628523 0.030 Uiso 1 1 calc R U . . .
C11 C 0.9397(3) 1.3434(10) 0.5705(3) 0.0218(11) Uani 1 1 d . . . . .
H11 H 0.955337 1.356981 0.521196 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6985(3) 0.1530(10) 0.3552(3) 0.0201(10) Uani 1 1 d . . . . .
C13 C 0.6537(3) 0.1048(10) 0.4108(3) 0.0204(10) Uani 1 1 d . . . . .
C14 C 0.6042(3) -0.1009(10) 0.3887(3) 0.0207(10) Uani 1 1 d . . . . .
C15 C 0.5562(3) -0.1305(11) 0.4363(3) 0.0227(11) Uani 1 1 d . . . . .
H15 H 0.556677 -0.018800 0.481399 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5084(3) -0.3206(11) 0.4179(4) 0.0260(12) Uani 1 1 d . . . . .
H16 H 0.475551 -0.338095 0.449482 0.031 Uiso 1 1 calc R U . . .
C17 C 0.5085(3) -0.4874(11) 0.3527(3) 0.0243(11) Uani 1 1 d . . . . .
H17 H 0.476430 -0.621323 0.340889 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5555(3) -0.4584(11) 0.3048(3) 0.0221(11) Uani 1 1 d . . . . .
H18 H 0.554995 -0.573919 0.260749 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6036(3) -0.2619(10) 0.3202(3) 0.0194(10) Uani 1 1 d . . . . .
C20 C 0.6502(3) -0.2165(10) 0.2659(3) 0.0191(10) Uani 1 1 d . . . . .
C21 C 0.6499(3) -0.3712(11) 0.1975(3) 0.0230(11) Uani 1 1 d . . . . .
H21 H 0.620577 -0.513755 0.186847 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6917(3) -0.3197(11) 0.1448(3) 0.0254(12) Uani 1 1 d . . . . .
H22 H 0.691920 -0.429465 0.099507 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7332(3) -0.1073(12) 0.1585(3) 0.0264(12) Uani 1 1 d . . . . .
H23 H 0.760789 -0.069107 0.121489 0.032 Uiso 1 1 calc R U . . .
C24 C 0.7343(3) 0.0482(11) 0.2258(3) 0.0222(11) Uani 1 1 d . . . . .
H24 H 0.762800 0.193078 0.234814 0.027 Uiso 1 1 calc R U . . .
C25 C 0.6937(3) -0.0059(10) 0.2814(3) 0.0194(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
S1 C5 1.722(6) . ?
S1 C2 1.733(5) . ?
O1 C13 1.253(6) . ?
N1 N2 1.338(6) . ?
N1 C2 1.379(7) . ?
N1 H1 0.77(7) . ?
N2 C12 1.313(7) . ?
C2 N3 1.299(7) . ?
N3 C4 1.378(7) . ?
C4 C5 1.364(7) . ?
C4 C6 1.485(7) . ?
C5 H5 0.9500 . ?
C6 C11 1.393(7) . ?
C6 C7 1.400(7) . ?
C7 C8 1.386(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.468(7) . ?
C12 C25 1.466(7) . ?
C13 C14 1.465(7) . ?
C14 C15 1.408(7) . ?
C14 C19 1.415(7) . ?
C15 C16 1.377(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.406(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.479(7) . ?
C20 C21 1.395(7) . ?
C20 C25 1.406(7) . ?
C21 C22 1.387(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.410(7) . ?
C24 H24 0.9500 . ?

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
C5 S1 C2 87.3(3) . . ?
N2 N1 C2 117.7(4) . . ?
N2 N1 H1 120(5) . . ?
C2 N1 H1 122(5) . . ?
C12 N2 N1 119.5(4) . . ?
N3 C2 N1 122.0(4) . . ?
N3 C2 S1 117.2(4) . . ?
N1 C2 S1 120.8(4) . . ?
C2 N3 C4 109.1(4) . . ?
C5 C4 N3 115.2(5) . . ?
C5 C4 C6 126.2(5) . . ?
N3 C4 C6 118.7(4) . . ?
C4 C5 S1 111.2(4) . . ?
C4 C5 H5 124.4 . . ?
S1 C5 H5 124.4 . . ?
C11 C6 C7 118.1(5) . . ?
C11 C6 C4 121.7(4) . . ?
C7 C6 C4 120.1(5) . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 121.3(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.7(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.4(5) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N2 C12 C13 123.8(5) . . ?
N2 C12 C25 116.2(4) . . ?
C13 C12 C25 120.0(5) . . ?
O1 C13 C14 121.0(5) . . ?
O1 C13 C12 121.2(5) . . ?
C14 C13 C12 117.8(4) . . ?
C15 C14 C19 120.8(5) . . ?
C15 C14 C13 118.1(5) . . ?
C19 C14 C13 121.1(4) . . ?
C16 C15 C14 120.3(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.3(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.5(5) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C14 117.2(5) . . ?
C18 C19 C20 122.1(5) . . ?
C14 C19 C20 120.6(5) . . ?
C21 C20 C25 119.3(5) . . ?
C21 C20 C19 121.5(5) . . ?
C25 C20 C19 119.1(4) . . ?
C22 C21 C20 120.9(5) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 119.9(5) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.7(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 119.0(5) . . ?
C20 C25 C12 121.0(4) . . ?
C24 C25 C12 119.9(5) . . ?

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 N1 N2 C12 178.3(5) . . . . ?
N2 N1 C2 N3 -179.1(5) . . . . ?
N2 N1 C2 S1 0.9(7) . . . . ?
C5 S1 C2 N3 0.1(4) . . . . ?
C5 S1 C2 N1 -180.0(5) . . . . ?
N1 C2 N3 C4 179.1(5) . . . . ?
S1 C2 N3 C4 -1.0(6) . . . . ?
C2 N3 C4 C5 1.6(6) . . . . ?
C2 N3 C4 C6 -177.8(4) . . . . ?
N3 C4 C5 S1 -1.6(6) . . . . ?
C6 C4 C5 S1 177.8(4) . . . . ?
C2 S1 C5 C4 0.8(4) . . . . ?
C5 C4 C6 C11 12.7(8) . . . . ?
N3 C4 C6 C11 -167.9(5) . . . . ?
C5 C4 C6 C7 -164.5(5) . . . . ?
N3 C4 C6 C7 14.9(7) . . . . ?
C11 C6 C7 C8 1.2(8) . . . . ?
C4 C6 C7 C8 178.5(5) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C8 C9 C10 C11 -0.6(8) . . . . ?
C9 C10 C11 C6 0.9(8) . . . . ?
C7 C6 C11 C10 -1.2(8) . . . . ?
C4 C6 C11 C10 -178.4(5) . . . . ?
N1 N2 C12 C13 -2.5(8) . . . . ?
N1 N2 C12 C25 179.7(4) . . . . ?
N2 C12 C13 O1 1.9(8) . . . . ?
C25 C12 C13 O1 179.6(5) . . . . ?
N2 C12 C13 C14 -179.0(5) . . . . ?
C25 C12 C13 C14 -1.3(7) . . . . ?
O1 C13 C14 C15 6.0(8) . . . . ?
C12 C13 C14 C15 -173.1(5) . . . . ?
O1 C13 C14 C19 -175.5(5) . . . . ?
C12 C13 C14 C19 5.4(7) . . . . ?
C19 C14 C15 C16 1.3(8) . . . . ?
C13 C14 C15 C16 179.8(5) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
C15 C16 C17 C18 -1.7(8) . . . . ?
C16 C17 C18 C19 -0.2(8) . . . . ?
C17 C18 C19 C14 2.6(8) . . . . ?
C17 C18 C19 C20 -175.1(5) . . . . ?
C15 C14 C19 C18 -3.1(7) . . . . ?
C13 C14 C19 C18 178.4(5) . . . . ?
C15 C14 C19 C20 174.7(5) . . . . ?
C13 C14 C19 C20 -3.8(7) . . . . ?
C18 C19 C20 C21 -1.6(8) . . . . ?
C14 C19 C20 C21 -179.3(5) . . . . ?
C18 C19 C20 C25 175.5(5) . . . . ?
C14 C19 C20 C25 -2.2(7) . . . . ?
C25 C20 C21 C22 0.0(8) . . . . ?
C19 C20 C21 C22 177.0(5) . . . . ?
C20 C21 C22 C23 -1.9(8) . . . . ?
C21 C22 C23 C24 1.9(8) . . . . ?
C22 C23 C24 C25 0.0(8) . . . . ?
C21 C20 C25 C24 2.0(7) . . . . ?
C19 C20 C25 C24 -175.2(5) . . . . ?
C21 C20 C25 C12 -176.5(5) . . . . ?
C19 C20 C25 C12 6.4(7) . . . . ?
C23 C24 C25 C20 -2.0(8) . . . . ?
C23 C24 C25 C12 176.5(5) . . . . ?
N2 C12 C25 C20 173.2(5) . . . . ?
C13 C12 C25 C20 -4.7(7) . . . . ?
N2 C12 C25 C24 -5.2(7) . . . . ?
C13 C12 C25 C24 176.9(5) . . . . ?

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
N1 H1 O1 0.77(7) 1.97(7) 2.556(6) 133(7) . yes

_refine_diff_density_max         1.195
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.121

