# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_HS_99_DCM_ACN_icecut
_database_code_depnum_ccdc_archive 'CCDC 2422011'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 N3 O2'
_chemical_formula_sum            'C26 H19 N3 O2'
_chemical_formula_weight         405.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   18.8524(11)
_cell_length_b                   8.0392(5)
_cell_length_c                   6.6161(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.022(5)
_cell_angle_gamma                90
_cell_volume                     1000.25(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      4.6950
_cell_measurement_theta_max      78.4990

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.548
_oxdiff_exptl_absorpt_empirical_full_max 1.765
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12332
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.703
_diffrn_reflns_theta_max         78.610
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_point_group_measured_fraction_full 0.777
_reflns_number_total             3112
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_max     0.497
_reflns_Friedel_fraction_full    0.563

_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 system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.1338P)²+0.5901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     281
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.2118
_refine_ls_wR_factor_gt          0.2048
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_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
O1_1 O 0.48901(19) 0.4148(4) 0.5555(6) 0.0437(10) Uani 1 1 d . . . . .
N1_1 N 0.3119(2) 0.6590(5) 0.3611(6) 0.0359(9) Uani 1 1 d . . . . .
C1_1 C 0.1865(3) 0.6667(8) 0.2565(8) 0.0398(12) Uani 1 1 d . . . . .
O2_1 O 0.9278(2) 0.2227(6) 0.2444(7) 0.0547(11) Uani 1 1 d . . . . .
N2_1 N 0.3708(2) 0.5790(5) 0.4172(7) 0.0352(9) Uani 1 1 d . . . . .
C2_1 C 0.1278(3) 0.5966(8) 0.1445(8) 0.0453(13) Uani 1 1 d . . . . .
H2_1 H 0.130275 0.485860 0.095452 0.054 Uiso 1 1 calc R U . . .
N3_1 N 0.2493(2) 0.4059(6) 0.2811(7) 0.0387(10) Uani 1 1 d . . . . .
C3_1 C 0.0665(3) 0.6890(9) 0.1058(10) 0.0527(15) Uani 1 1 d . . . . .
H3_1 H 0.027041 0.641640 0.029276 0.063 Uiso 1 1 calc R U . . .
C4_1 C 0.0623(3) 0.8505(10) 0.1779(11) 0.0585(17) Uani 1 1 d . . . . .
H4_1 H 0.020014 0.913335 0.151198 0.070 Uiso 1 1 calc R U . . .
C5_1 C 0.1195(3) 0.9193(9) 0.2881(10) 0.0534(15) Uani 1 1 d . . . . .
H5_1 H 0.116556 1.029783 0.337863 0.064 Uiso 1 1 calc R U . . .
C6_1 C 0.1814(3) 0.8285(8) 0.3268(9) 0.0457(13) Uani 1 1 d . . . . .
H6_1 H 0.220783 0.877466 0.402257 0.055 Uiso 1 1 calc R U . . .
C7_1 C 0.2520(3) 0.5690(7) 0.3009(7) 0.0363(11) Uani 1 1 d . . . . .
C8_1 C 0.3709(3) 0.4107(6) 0.4129(8) 0.0340(10) Uani 1 1 d . . . . .
C9_1 C 0.3094(3) 0.3216(7) 0.3361(8) 0.0396(12) Uani 1 1 d . . . . .
C10_1 C 0.4332(3) 0.3200(7) 0.4789(8) 0.0388(11) Uani 1 1 d . . . . .
C11_1 C 0.4344(3) 0.1516(7) 0.4615(9) 0.0452(13) Uani 1 1 d . . . . .
H11_1 H 0.476217 0.091192 0.502698 0.054 Uiso 1 1 calc R U . . .
C12_1 C 0.3724(4) 0.0658(7) 0.3810(9) 0.0497(14) Uani 1 1 d . . . . .
H12_1 H 0.373822 -0.051877 0.369132 0.060 Uiso 1 1 calc R U . . .
C13_1 C 0.3117(3) 0.1470(7) 0.3210(9) 0.0475(14) Uani 1 1 d . . . . .
H13_1 H 0.271017 0.086864 0.269151 0.057 Uiso 1 1 calc R U . . .
C14_1 C 0.5482(3) 0.3317(6) 0.6486(9) 0.0415(13) Uani 1 1 d . . . . .
C15_1 C 0.6084(3) 0.3262(6) 0.5476(9) 0.0411(12) Uani 1 1 d . . . . .
H15_1 H 0.608439 0.370818 0.414699 0.049 Uiso 1 1 calc R U . . .
C16_1 C 0.6712(3) 0.2543(6) 0.6394(9) 0.0396(12) Uani 1 1 d . . . . .
C17_1 C 0.6672(3) 0.1878(7) 0.8346(9) 0.0460(13) Uani 1 1 d . . . . .
H17_1 H 0.708298 0.137906 0.900259 0.055 Uiso 1 1 calc R U . . .
C18_1 C 0.6059(3) 0.1930(7) 0.9325(10) 0.0486(14) Uani 1 1 d . . . . .
H18_1 H 0.605296 0.146906 1.064562 0.058 Uiso 1 1 calc R U . . .
C19_1 C 0.5437(3) 0.2647(7) 0.8424(10) 0.0449(13) Uani 1 1 d . . . . .
H19_1 H 0.500766 0.267722 0.909440 0.054 Uiso 1 1 calc R U . . .
C20_1 C 0.7376(3) 0.2488(6) 0.5346(9) 0.0403(12) Uani 1 1 d . . . . .
C21_1 C 0.7490(3) 0.3506(7) 0.3670(10) 0.0483(14) Uani 1 1 d . . . . .
H21_1 H 0.712455 0.425535 0.320470 0.058 Uiso 1 1 calc R U . . .
C22_1 C 0.8107(3) 0.3466(7) 0.2672(10) 0.0484(13) Uani 1 1 d . . . . .
H22_1 H 0.815957 0.416741 0.153659 0.058 Uiso 1 1 calc R U . . .
C23_1 C 0.8654(3) 0.2392(7) 0.3337(9) 0.0461(14) Uani 1 1 d . . . . .
C24_1 C 0.8554(3) 0.1365(7) 0.4985(9) 0.0485(14) Uani 1 1 d . . . . .
H24_1 H 0.891997 0.061537 0.544244 0.058 Uiso 1 1 calc R U . . .
C25_1 C 0.7937(3) 0.1414(7) 0.5963(9) 0.0449(13) Uani 1 1 d . . . . .
H25_1 H 0.788702 0.070188 0.709018 0.054 Uiso 1 1 calc R U . . .
C26_1 C 0.9376(4) 0.3202(10) 0.0714(13) 0.068(2) Uani 1 1 d . . . . .
H26A_1 H 0.984205 0.295427 0.021366 0.102 Uiso 1 1 calc R U . . .
H26B_1 H 0.935334 0.438294 0.106860 0.102 Uiso 1 1 calc R U . . .
H26C_1 H 0.900219 0.294479 -0.034353 0.102 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
O1_1 C10_1 1.367(6) . ?
O1_1 C14_1 1.405(6) . ?
N1_1 N2_1 1.314(6) . ?
N1_1 C7_1 1.376(6) . ?
C1_1 C6_1 1.387(9) . ?
C1_1 C2_1 1.405(7) . ?
C1_1 C7_1 1.476(7) . ?
O2_1 C23_1 1.359(8) . ?
O2_1 C26_1 1.410(10) . ?
N2_1 C8_1 1.353(6) . ?
C2_1 C3_1 1.382(9) . ?
C2_1 H2_1 0.9500 . ?
N3_1 C7_1 1.318(7) . ?
N3_1 C9_1 1.347(7) . ?
C3_1 C4_1 1.387(11) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.375(9) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.386(8) . ?
C5_1 H5_1 0.9500 . ?
C6_1 H6_1 0.9500 . ?
C8_1 C10_1 1.425(7) . ?
C8_1 C9_1 1.426(7) . ?
C9_1 C13_1 1.408(8) . ?
C10_1 C11_1 1.359(8) . ?
C11_1 C12_1 1.427(8) . ?
C11_1 H11_1 0.9500 . ?
C12_1 C13_1 1.353(9) . ?
C12_1 H12_1 0.9500 . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.358(9) . ?
C14_1 C19_1 1.399(9) . ?
C15_1 C16_1 1.414(7) . ?
C15_1 H15_1 0.9500 . ?
C16_1 C17_1 1.404(8) . ?
C16_1 C20_1 1.475(8) . ?
C17_1 C18_1 1.365(9) . ?
C17_1 H17_1 0.9500 . ?
C18_1 C19_1 1.401(8) . ?
C18_1 H18_1 0.9500 . ?
C19_1 H19_1 0.9500 . ?
C20_1 C25_1 1.403(7) . ?
C20_1 C21_1 1.406(8) . ?
C21_1 C22_1 1.378(9) . ?
C21_1 H21_1 0.9500 . ?
C22_1 C23_1 1.392(8) . ?
C22_1 H22_1 0.9500 . ?
C23_1 C24_1 1.391(9) . ?
C24_1 C25_1 1.371(9) . ?
C24_1 H24_1 0.9500 . ?
C25_1 H25_1 0.9500 . ?
C26_1 H26A_1 0.9800 . ?
C26_1 H26B_1 0.9800 . ?
C26_1 H26C_1 0.9800 . ?

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
C10_1 O1_1 C14_1 117.7(4) . . ?
N2_1 N1_1 C7_1 119.0(4) . . ?
C6_1 C1_1 C2_1 118.9(5) . . ?
C6_1 C1_1 C7_1 120.6(5) . . ?
C2_1 C1_1 C7_1 120.5(5) . . ?
C23_1 O2_1 C26_1 117.8(5) . . ?
N1_1 N2_1 C8_1 119.1(4) . . ?
C3_1 C2_1 C1_1 119.9(6) . . ?
C3_1 C2_1 H2_1 120.0 . . ?
C1_1 C2_1 H2_1 120.0 . . ?
C7_1 N3_1 C9_1 116.6(4) . . ?
C2_1 C3_1 C4_1 120.4(6) . . ?
C2_1 C3_1 H3_1 119.8 . . ?
C4_1 C3_1 H3_1 119.8 . . ?
C5_1 C4_1 C3_1 119.8(6) . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 120.3(7) . . ?
C4_1 C5_1 H5_1 119.8 . . ?
C6_1 C5_1 H5_1 119.8 . . ?
C5_1 C6_1 C1_1 120.6(5) . . ?
C5_1 C6_1 H6_1 119.7 . . ?
C1_1 C6_1 H6_1 119.7 . . ?
N3_1 C7_1 N1_1 125.2(5) . . ?
N3_1 C7_1 C1_1 119.0(5) . . ?
N1_1 C7_1 C1_1 115.8(5) . . ?
N2_1 C8_1 C10_1 120.5(4) . . ?
N2_1 C8_1 C9_1 120.5(5) . . ?
C10_1 C8_1 C9_1 119.0(4) . . ?
N3_1 C9_1 C13_1 120.8(5) . . ?
N3_1 C9_1 C8_1 119.3(5) . . ?
C13_1 C9_1 C8_1 119.8(5) . . ?
C11_1 C10_1 O1_1 124.8(5) . . ?
C11_1 C10_1 C8_1 120.1(5) . . ?
O1_1 C10_1 C8_1 115.1(4) . . ?
C10_1 C11_1 C12_1 119.7(5) . . ?
C10_1 C11_1 H11_1 120.2 . . ?
C12_1 C11_1 H11_1 120.2 . . ?
C13_1 C12_1 C11_1 122.0(5) . . ?
C13_1 C12_1 H12_1 119.0 . . ?
C11_1 C12_1 H12_1 119.0 . . ?
C12_1 C13_1 C9_1 119.3(5) . . ?
C12_1 C13_1 H13_1 120.3 . . ?
C9_1 C13_1 H13_1 120.3 . . ?
C15_1 C14_1 C19_1 123.0(5) . . ?
C15_1 C14_1 O1_1 117.7(5) . . ?
C19_1 C14_1 O1_1 119.2(5) . . ?
C14_1 C15_1 C16_1 120.3(5) . . ?
C14_1 C15_1 H15_1 119.8 . . ?
C16_1 C15_1 H15_1 119.8 . . ?
C17_1 C16_1 C15_1 117.0(5) . . ?
C17_1 C16_1 C20_1 121.5(5) . . ?
C15_1 C16_1 C20_1 121.5(5) . . ?
C18_1 C17_1 C16_1 121.7(5) . . ?
C18_1 C17_1 H17_1 119.1 . . ?
C16_1 C17_1 H17_1 119.1 . . ?
C17_1 C18_1 C19_1 121.5(6) . . ?
C17_1 C18_1 H18_1 119.3 . . ?
C19_1 C18_1 H18_1 119.3 . . ?
C14_1 C19_1 C18_1 116.5(6) . . ?
C14_1 C19_1 H19_1 121.8 . . ?
C18_1 C19_1 H19_1 121.8 . . ?
C25_1 C20_1 C21_1 115.7(5) . . ?
C25_1 C20_1 C16_1 121.9(5) . . ?
C21_1 C20_1 C16_1 122.4(4) . . ?
C22_1 C21_1 C20_1 123.0(5) . . ?
C22_1 C21_1 H21_1 118.5 . . ?
C20_1 C21_1 H21_1 118.5 . . ?
C21_1 C22_1 C23_1 119.6(6) . . ?
C21_1 C22_1 H22_1 120.2 . . ?
C23_1 C22_1 H22_1 120.2 . . ?
O2_1 C23_1 C24_1 116.9(5) . . ?
O2_1 C23_1 C22_1 124.5(6) . . ?
C24_1 C23_1 C22_1 118.5(6) . . ?
C25_1 C24_1 C23_1 121.3(5) . . ?
C25_1 C24_1 H24_1 119.3 . . ?
C23_1 C24_1 H24_1 119.3 . . ?
C24_1 C25_1 C20_1 121.8(6) . . ?
C24_1 C25_1 H25_1 119.1 . . ?
C20_1 C25_1 H25_1 119.1 . . ?
O2_1 C26_1 H26A_1 109.5 . . ?
O2_1 C26_1 H26B_1 109.5 . . ?
H26A_1 C26_1 H26B_1 109.5 . . ?
O2_1 C26_1 H26C_1 109.5 . . ?
H26A_1 C26_1 H26C_1 109.5 . . ?
H26B_1 C26_1 H26C_1 109.5 . . ?

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
C7_1 N1_1 N2_1 C8_1 0.4(7) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.2(8) . . . . ?
C7_1 C1_1 C2_1 C3_1 179.3(5) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.4(9) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.2(10) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.2(10) . . . . ?
C4_1 C5_1 C6_1 C1_1 -0.5(9) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.3(8) . . . . ?
C7_1 C1_1 C6_1 C5_1 -178.9(6) . . . . ?
C9_1 N3_1 C7_1 N1_1 4.1(8) . . . . ?
C9_1 N3_1 C7_1 C1_1 -175.8(5) . . . . ?
N2_1 N1_1 C7_1 N3_1 -4.8(8) . . . . ?
N2_1 N1_1 C7_1 C1_1 175.1(4) . . . . ?
C6_1 C1_1 C7_1 N3_1 162.1(5) . . . . ?
C2_1 C1_1 C7_1 N3_1 -17.1(7) . . . . ?
C6_1 C1_1 C7_1 N1_1 -17.8(7) . . . . ?
C2_1 C1_1 C7_1 N1_1 163.0(5) . . . . ?
N1_1 N2_1 C8_1 C10_1 -178.0(5) . . . . ?
N1_1 N2_1 C8_1 C9_1 4.1(7) . . . . ?
C7_1 N3_1 C9_1 C13_1 179.8(5) . . . . ?
C7_1 N3_1 C9_1 C8_1 0.7(7) . . . . ?
N2_1 C8_1 C9_1 N3_1 -4.7(8) . . . . ?
C10_1 C8_1 C9_1 N3_1 177.3(5) . . . . ?
N2_1 C8_1 C9_1 C13_1 176.1(5) . . . . ?
C10_1 C8_1 C9_1 C13_1 -1.8(8) . . . . ?
C14_1 O1_1 C10_1 C11_1 -9.3(8) . . . . ?
C14_1 O1_1 C10_1 C8_1 171.3(5) . . . . ?
N2_1 C8_1 C10_1 C11_1 -175.6(5) . . . . ?
C9_1 C8_1 C10_1 C11_1 2.3(8) . . . . ?
N2_1 C8_1 C10_1 O1_1 3.8(7) . . . . ?
C9_1 C8_1 C10_1 O1_1 -178.3(4) . . . . ?
O1_1 C10_1 C11_1 C12_1 179.3(5) . . . . ?
C8_1 C10_1 C11_1 C12_1 -1.4(9) . . . . ?
C10_1 C11_1 C12_1 C13_1 -0.2(10) . . . . ?
C11_1 C12_1 C13_1 C9_1 0.6(10) . . . . ?
N3_1 C9_1 C13_1 C12_1 -178.8(5) . . . . ?
C8_1 C9_1 C13_1 C12_1 0.4(9) . . . . ?
C10_1 O1_1 C14_1 C15_1 107.2(5) . . . . ?
C10_1 O1_1 C14_1 C19_1 -75.3(6) . . . . ?
C19_1 C14_1 C15_1 C16_1 -1.7(8) . . . . ?
O1_1 C14_1 C15_1 C16_1 175.7(4) . . . . ?
C14_1 C15_1 C16_1 C17_1 1.2(7) . . . . ?
C14_1 C15_1 C16_1 C20_1 -179.1(4) . . . . ?
C15_1 C16_1 C17_1 C18_1 -0.4(8) . . . . ?
C20_1 C16_1 C17_1 C18_1 179.8(5) . . . . ?
C16_1 C17_1 C18_1 C19_1 0.2(9) . . . . ?
C15_1 C14_1 C19_1 C18_1 1.4(8) . . . . ?
O1_1 C14_1 C19_1 C18_1 -176.0(4) . . . . ?
C17_1 C18_1 C19_1 C14_1 -0.6(8) . . . . ?
C17_1 C16_1 C20_1 C25_1 17.2(7) . . . . ?
C15_1 C16_1 C20_1 C25_1 -162.5(5) . . . . ?
C17_1 C16_1 C20_1 C21_1 -162.7(5) . . . . ?
C15_1 C16_1 C20_1 C21_1 17.6(7) . . . . ?
C25_1 C20_1 C21_1 C22_1 0.3(8) . . . . ?
C16_1 C20_1 C21_1 C22_1 -179.9(5) . . . . ?
C20_1 C21_1 C22_1 C23_1 -0.7(9) . . . . ?
C26_1 O2_1 C23_1 C24_1 177.1(5) . . . . ?
C26_1 O2_1 C23_1 C22_1 -0.5(8) . . . . ?
C21_1 C22_1 C23_1 O2_1 178.6(5) . . . . ?
C21_1 C22_1 C23_1 C24_1 1.0(8) . . . . ?
O2_1 C23_1 C24_1 C25_1 -178.7(5) . . . . ?
C22_1 C23_1 C24_1 C25_1 -0.9(8) . . . . ?
C23_1 C24_1 C25_1 C20_1 0.5(8) . . . . ?
C21_1 C20_1 C25_1 C24_1 -0.1(8) . . . . ?
C16_1 C20_1 C25_1 C24_1 180.0(5) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and acetonitrile'
####################################################################### 
# 
# 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_HS100_cut
_database_code_depnum_ccdc_archive 'CCDC 2422013'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 N3 O2'
_chemical_formula_sum            'C26 H18 N3 O2'
_chemical_formula_weight         404.43

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'

_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                   11.76120(10)
_cell_length_b                   8.21020(10)
_cell_length_c                   19.2290(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.0730(10)
_cell_angle_gamma                90
_cell_volume                     1856.46(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    19530
_cell_measurement_theta_min      3.8260
_cell_measurement_theta_max      78.6150

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.123a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.844
_oxdiff_exptl_absorpt_empirical_full_max 1.441
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26021
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.759
_diffrn_reflns_theta_max         70.057
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3480
_reflns_number_gt                3350
_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.
;

_computing_data_collection       
'CrysAlisPro system (CCD 43.131a 64-bit (release 19-07-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0604P)²+0.5951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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
O1 O 0.57790(6) 0.87228(9) 0.63261(4) 0.02049(19) Uani 1 1 d . . . . .
N1 N 0.66180(8) 0.56963(11) 0.46782(5) 0.0191(2) Uani 1 1 d . . . . .
C1 C 0.62245(9) 0.46065(13) 0.35528(5) 0.0193(2) Uani 1 1 d . . . . .
O2 O 1.07013(7) 0.65427(10) 0.96553(4) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.62818(8) 0.65912(11) 0.52318(5) 0.0184(2) Uani 1 1 d . . . . .
C2 C 0.54859(9) 0.43670(13) 0.29848(6) 0.0210(2) Uani 1 1 d . . . . .
H2 H 0.477070 0.490476 0.296820 0.025 Uiso 1 1 calc R U . . .
N3 N 0.48328(8) 0.63287(11) 0.40979(5) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.57937(10) 0.33439(14) 0.24436(6) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.528747 0.318663 0.205866 0.029 Uiso 1 1 calc R U . . .
C4 C 0.68332(10) 0.25536(14) 0.24623(6) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.703588 0.184473 0.209434 0.031 Uiso 1 1 calc R U . . .
C5 C 0.75815(10) 0.28010(15) 0.30226(6) 0.0255(3) Uani 1 1 d . . . . .
H5 H 0.829777 0.226577 0.303496 0.031 Uiso 1 1 calc R U . . .
C6 C 0.72835(9) 0.38257(14) 0.35619(6) 0.0222(2) Uani 1 1 d . . . . .
H6 H 0.780057 0.399977 0.394005 0.027 Uiso 1 1 calc R U . . .
C7 C 0.58616(9) 0.56311(13) 0.41469(5) 0.0183(2) Uani 1 1 d . . . . .
C8 C 0.52786(9) 0.74775(13) 0.52257(5) 0.0183(2) Uani 1 1 d . . . . .
C9 C 0.45359(9) 0.72970(13) 0.46490(6) 0.0187(2) Uani 1 1 d . . . . .
C10 C 0.69795(9) 0.66101(13) 0.58325(6) 0.0183(2) Uani 1 1 d . . . . .
C11 C 0.66955(9) 0.76722(13) 0.63721(6) 0.0186(2) Uani 1 1 d . . . . .
C12 C 0.50264(9) 0.85154(13) 0.57746(6) 0.0185(2) Uani 1 1 d . . . . .
C13 C 0.79058(9) 0.55698(13) 0.59226(6) 0.0199(2) Uani 1 1 d . . . . .
H13 H 0.811148 0.484950 0.555929 0.024 Uiso 1 1 calc R U . . .
C14 C 0.85283(9) 0.55846(14) 0.65422(6) 0.0204(2) Uani 1 1 d . . . . .
H14 H 0.915745 0.486782 0.659814 0.024 Uiso 1 1 calc R U . . .
C15 C 0.82484(9) 0.66365(13) 0.70887(6) 0.0192(2) Uani 1 1 d . . . . .
C16 C 0.73267(9) 0.76991(13) 0.69841(6) 0.0191(2) Uani 1 1 d . . . . .
H16 H 0.713442 0.844788 0.733970 0.023 Uiso 1 1 calc R U . . .
C17 C 0.35047(9) 0.81599(13) 0.46520(6) 0.0205(2) Uani 1 1 d . . . . .
H17 H 0.297649 0.804719 0.427523 0.025 Uiso 1 1 calc R U . . .
C18 C 0.40188(9) 0.93742(13) 0.57661(6) 0.0201(2) Uani 1 1 d . . . . .
H18 H 0.384280 1.009158 0.613651 0.024 Uiso 1 1 calc R U . . .
C19 C 0.32586(9) 0.91731(13) 0.52033(6) 0.0210(2) Uani 1 1 d . . . . .
H19 H 0.255698 0.974669 0.520029 0.025 Uiso 1 1 calc R U . . .
C20 C 0.88767(9) 0.66068(13) 0.77668(6) 0.0195(2) Uani 1 1 d . . . . .
C21 C 0.99716(9) 0.59386(14) 0.78357(6) 0.0227(2) Uani 1 1 d . . . . .
H21 H 1.032196 0.548133 0.743966 0.027 Uiso 1 1 calc R U . . .
C22 C 1.05512(9) 0.59323(15) 0.84687(6) 0.0243(3) Uani 1 1 d . . . . .
H22 H 1.129029 0.546899 0.850286 0.029 Uiso 1 1 calc R U . . .
C23 C 1.00563(9) 0.66023(14) 0.90565(6) 0.0210(2) Uani 1 1 d . . . . .
C24 C 0.89677(9) 0.72573(14) 0.90045(6) 0.0221(2) Uani 1 1 d . . . . .
H24 H 0.861983 0.771404 0.940154 0.027 Uiso 1 1 calc R U . . .
C25 C 0.83939(9) 0.72376(14) 0.83669(6) 0.0216(2) Uani 1 1 d . . . . .
H25 H 0.764513 0.766941 0.833820 0.026 Uiso 1 1 calc R U . . .
C26 C 1.02303(10) 0.72572(15) 1.02633(6) 0.0259(3) Uani 1 1 d . . . . .
H26A H 1.074812 0.708000 1.066134 0.039 Uiso 1 1 calc R U . . .
H26B H 0.949355 0.675255 1.035631 0.039 Uiso 1 1 calc R U . . .
H26C H 1.012640 0.842917 1.018920 0.039 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
O1 C12 1.3792(13) . ?
O1 C11 1.3820(13) . ?
N1 C7 1.3431(14) . ?
N1 N2 1.3585(13) . ?
C1 C2 1.3967(15) . ?
C1 C6 1.4007(16) . ?
C1 C7 1.4876(15) . ?
O2 C23 1.3679(13) . ?
O2 C26 1.4289(14) . ?
N2 C8 1.3861(14) . ?
N2 C10 1.4043(13) . ?
C2 C3 1.3907(16) . ?
C2 H2 0.9500 . ?
N3 C7 1.3405(14) . ?
N3 C9 1.3751(14) . ?
C3 C4 1.3840(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3933(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3854(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C12 1.3927(16) . ?
C8 C9 1.4066(14) . ?
C9 C17 1.4047(15) . ?
C10 C13 1.3927(16) . ?
C10 C11 1.4006(15) . ?
C11 C16 1.3796(15) . ?
C12 C18 1.3788(16) . ?
C13 C14 1.3868(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.4040(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4031(15) . ?
C15 C20 1.4870(15) . ?
C16 H16 0.9500 . ?
C17 C19 1.3824(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.4007(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.3952(16) . ?
C20 C21 1.4037(15) . ?
C21 C22 1.3839(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.3941(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.3906(16) . ?
C24 C25 1.3885(15) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C12 O1 C11 117.43(8) . . ?
C7 N1 N2 114.79(9) . . ?
C2 C1 C6 119.02(10) . . ?
C2 C1 C7 119.80(10) . . ?
C6 C1 C7 121.14(10) . . ?
C23 O2 C26 117.18(8) . . ?
N1 N2 C8 122.52(9) . . ?
N1 N2 C10 118.45(9) . . ?
C8 N2 C10 119.03(9) . . ?
C3 C2 C1 120.23(10) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C7 N3 C9 115.76(9) . . ?
C4 C3 C2 120.39(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.78(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.15(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.40(10) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N3 C7 N1 128.37(10) . . ?
N3 C7 C1 117.33(9) . . ?
N1 C7 C1 114.28(9) . . ?
N2 C8 C12 120.54(10) . . ?
N2 C8 C9 117.86(10) . . ?
C12 C8 C9 121.60(10) . . ?
N3 C9 C17 121.76(10) . . ?
N3 C9 C8 120.38(10) . . ?
C17 C9 C8 117.85(10) . . ?
C13 C10 C11 119.11(10) . . ?
C13 C10 N2 122.63(10) . . ?
C11 C10 N2 118.20(10) . . ?
C16 C11 O1 116.82(9) . . ?
C16 C11 C10 120.66(10) . . ?
O1 C11 C10 122.53(10) . . ?
C18 C12 O1 119.01(10) . . ?
C18 C12 C8 119.95(10) . . ?
O1 C12 C8 121.03(10) . . ?
C14 C13 C10 120.04(10) . . ?
C14 C13 H13 120.0 . . ?
C10 C13 H13 120.0 . . ?
C13 C14 C15 121.40(10) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 117.81(10) . . ?
C16 C15 C20 120.39(10) . . ?
C14 C15 C20 121.78(10) . . ?
C11 C16 C15 120.95(10) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C19 C17 C9 119.99(10) . . ?
C19 C17 H17 120.0 . . ?
C9 C17 H17 120.0 . . ?
C12 C18 C19 119.01(10) . . ?
C12 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C17 C19 C18 121.58(10) . . ?
C17 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C25 C20 C21 116.99(10) . . ?
C25 C20 C15 121.06(10) . . ?
C21 C20 C15 121.95(10) . . ?
C22 C21 C20 121.36(10) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.35(10) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
O2 C23 C24 124.73(10) . . ?
O2 C23 C22 115.79(10) . . ?
C24 C23 C22 119.48(10) . . ?
C25 C24 C23 119.38(10) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C20 122.42(10) . . ?
C24 C25 H25 118.8 . . ?
C20 C25 H25 118.8 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and benzene'
####################################################################### 
# 
# 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_HS98_DCM_EtOH
_database_code_depnum_ccdc_archive 'CCDC 2422012'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Br N3 O'
_chemical_formula_sum            'C19 H12 Br N3 O'
_chemical_formula_weight         378.23

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'
Br Br -0.6763 1.2805 '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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   13.2163(3)
_cell_length_b                   8.3689(2)
_cell_length_c                   7.21920(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.320(2)
_cell_angle_gamma                90
_cell_volume                     785.57(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    22307
_cell_measurement_theta_min      3.3850
_cell_measurement_theta_max      78.4960

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.651
_shelx_estimated_absorpt_T_min   0.279
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.710
_oxdiff_exptl_absorpt_empirical_full_max 2.043
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23459
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         78.732
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3014
_reflns_number_gt                3010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.838
_reflns_Friedel_fraction_full    0.964

_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 system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0271P)²+0.2938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3014
_refine_ls_number_parameters     217
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0176
_refine_ls_wR_factor_ref         0.0460
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_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
Br1 Br 0.20677(4) 0.13071(3) -0.14999(4) 0.02357(9) Uani 1 1 d . . . . .
O1 O 0.33933(14) 0.4267(2) 0.4859(3) 0.0213(4) Uani 1 1 d . . . . .
N1 N 0.67294(16) 0.4154(3) 0.8639(3) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.7598(2) 0.6681(3) 0.9332(3) 0.0158(5) Uani 1 1 d . . . . .
N2 N 0.50585(17) 0.5810(3) 0.6644(3) 0.0155(4) Uani 1 1 d . . . . .
C2 C 0.7660(2) 0.8288(3) 0.8891(4) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.713830 0.876000 0.797902 0.024 Uiso 1 1 calc R U . . .
N3 N 0.58767(18) 0.6584(3) 0.7502(3) 0.0162(4) Uani 1 1 d . . . . .
C3 C 0.8482(2) 0.9213(3) 0.9778(4) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.851604 1.031764 0.949394 0.028 Uiso 1 1 calc R U . . .
C4 C 0.9255(2) 0.8499(3) 1.1087(4) 0.0220(6) Uani 1 1 d . . . . .
H4 H 0.981398 0.912347 1.170957 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9210(2) 0.6886(3) 1.1484(4) 0.0205(5) Uani 1 1 d . . . . .
H5 H 0.974706 0.640403 1.235502 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8385(2) 0.5967(3) 1.0616(4) 0.0183(5) Uani 1 1 d . . . . .
H6 H 0.835614 0.486015 1.089273 0.022 Uiso 1 1 calc R U . . .
C7 C 0.66924(19) 0.5724(3) 0.8442(3) 0.0149(5) Uani 1 1 d . . . . .
C8 C 0.5892(2) 0.3333(3) 0.7771(4) 0.0164(5) Uani 1 1 d . . . . .
C9 C 0.50490(19) 0.4198(3) 0.6730(3) 0.0148(5) Uani 1 1 d . . . . .
C10 C 0.5857(2) 0.1665(3) 0.7867(4) 0.0218(5) Uani 1 1 d . . . . .
H10 H 0.641141 0.109124 0.858862 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5017(2) 0.0863(3) 0.6916(4) 0.0210(5) Uani 1 1 d . . . . .
H11 H 0.500068 -0.027119 0.696362 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4168(2) 0.1705(3) 0.5856(4) 0.0183(5) Uani 1 1 d . . . . .
H12 H 0.359327 0.112945 0.520522 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4178(2) 0.3326(3) 0.5772(4) 0.0164(5) Uani 1 1 d . . . . .
C14 C 0.2574(3) 0.3546(3) 0.3654(5) 0.0169(6) Uani 1 1 d . . . . .
C15 C 0.1600(2) 0.3684(3) 0.4137(5) 0.0173(6) Uani 1 1 d . . . . .
H15 H 0.151220 0.416261 0.529149 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0757(2) 0.3094(3) 0.2863(4) 0.0193(5) Uani 1 1 d . . . . .
H16 H 0.008558 0.318396 0.315061 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0888(2) 0.2381(3) 0.1191(3) 0.0172(5) Uani 1 1 d . . . . .
H17 H 0.031542 0.198180 0.033017 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1877(2) 0.2263(3) 0.0802(3) 0.0155(5) Uani 1 1 d . . . . .
C19 C 0.2730(2) 0.2841(3) 0.2005(3) 0.0155(5) Uani 1 1 d . . . . .
H19 H 0.339972 0.275623 0.170622 0.019 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
Br1 C18 1.901(3) . ?
O1 C13 1.373(3) . ?
O1 C14 1.399(4) . ?
N1 C7 1.321(3) . ?
N1 C8 1.357(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.397(4) . ?
C1 C7 1.486(4) . ?
N2 N3 1.316(3) . ?
N2 C9 1.350(3) . ?
C2 C3 1.393(4) . ?
C2 H2 0.9500 . ?
N3 C7 1.371(3) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C10 1.399(4) . ?
C8 C9 1.425(4) . ?
C9 C13 1.432(4) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.426(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.358(4) . ?
C12 H12 0.9500 . ?
C14 C19 1.377(4) . ?
C14 C15 1.397(4) . ?
C15 C16 1.401(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 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
C13 O1 C14 119.0(2) . . ?
C7 N1 C8 116.3(2) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C7 119.9(2) . . ?
C6 C1 C7 120.2(2) . . ?
N3 N2 C9 118.9(2) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
N2 N3 C7 118.8(2) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 N3 125.9(2) . . ?
N1 C7 C1 118.5(2) . . ?
N3 C7 C1 115.6(2) . . ?
N1 C8 C10 120.9(2) . . ?
N1 C8 C9 118.8(2) . . ?
C10 C8 C9 120.2(2) . . ?
N2 C9 C8 121.3(2) . . ?
N2 C9 C13 120.0(2) . . ?
C8 C9 C13 118.7(2) . . ?
C11 C10 C8 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C8 C10 H10 120.2 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 O1 125.6(2) . . ?
C12 C13 C9 120.1(2) . . ?
O1 C13 C9 114.3(2) . . ?
C19 C14 C15 122.7(3) . . ?
C19 C14 O1 120.2(3) . . ?
C15 C14 O1 117.0(3) . . ?
C14 C15 C16 117.8(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.5(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 122.7(2) . . ?
C19 C18 Br1 118.41(19) . . ?
C17 C18 Br1 118.92(19) . . ?
C14 C19 C18 117.5(2) . . ?
C14 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?

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
C6 C1 C2 C3 -2.6(4) . . . . ?
C7 C1 C2 C3 177.2(2) . . . . ?
C9 N2 N3 C7 0.4(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C7 C1 C6 C5 -177.9(2) . . . . ?
C8 N1 C7 N3 2.4(4) . . . . ?
C8 N1 C7 C1 -178.8(2) . . . . ?
N2 N3 C7 N1 -2.7(4) . . . . ?
N2 N3 C7 C1 178.5(2) . . . . ?
C2 C1 C7 N1 169.0(3) . . . . ?
C6 C1 C7 N1 -11.2(4) . . . . ?
C2 C1 C7 N3 -12.1(3) . . . . ?
C6 C1 C7 N3 167.7(2) . . . . ?
C7 N1 C8 C10 179.1(3) . . . . ?
C7 N1 C8 C9 -0.1(3) . . . . ?
N3 N2 C9 C8 1.8(4) . . . . ?
N3 N2 C9 C13 -178.5(2) . . . . ?
N1 C8 C9 N2 -2.0(4) . . . . ?
C10 C8 C9 N2 178.8(2) . . . . ?
N1 C8 C9 C13 178.3(2) . . . . ?
C10 C8 C9 C13 -0.9(4) . . . . ?
N1 C8 C10 C11 -177.5(2) . . . . ?
C9 C8 C10 C11 1.7(4) . . . . ?
C8 C10 C11 C12 -1.2(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 O1 -177.4(2) . . . . ?
C11 C12 C13 C9 0.8(4) . . . . ?
C14 O1 C13 C12 -11.0(4) . . . . ?
C14 O1 C13 C9 170.7(2) . . . . ?
N2 C9 C13 C12 179.9(2) . . . . ?
C8 C9 C13 C12 -0.4(4) . . . . ?
N2 C9 C13 O1 -1.7(3) . . . . ?
C8 C9 C13 O1 178.1(2) . . . . ?
C13 O1 C14 C19 -67.2(4) . . . . ?
C13 O1 C14 C15 117.3(3) . . . . ?
C19 C14 C15 C16 -0.9(5) . . . . ?
O1 C14 C15 C16 174.5(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C16 C17 C18 Br1 -179.36(18) . . . . ?
C15 C14 C19 C18 0.2(4) . . . . ?
O1 C14 C19 C18 -174.9(2) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
Br1 C18 C19 C14 179.25(19) . . . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and ethanol'
