# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2331438'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 N2 O3'
_chemical_formula_sum            'C25 H18 N2 O3'
_chemical_formula_weight         394.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.3866(5)
_cell_length_b                   20.5762(16)
_cell_length_c                   14.5475(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.315(3)
_cell_angle_gamma                90
_cell_volume                     1908.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    30069
_cell_measurement_theta_min      1
_cell_measurement_theta_max      26.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.814
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27014
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3663
_reflns_number_gt                3337
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0242P)²+8.7997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3663
_refine_ls_number_parameters     272
_refine_ls_number_restraints     237
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.1021
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.2150
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_restrained_S_all      1.227
_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 O -0.2180(9) -0.05194(19) 0.6106(3) 0.0679(15) Uani 1 1 d . . . . .
C1 C 0.0741(6) 0.24783(18) 0.5623(3) 0.0143(8) Uani 1 1 d . . . . .
N1 N -0.0498(5) 0.29505(15) 0.5992(2) 0.0135(7) Uani 1 1 d . . . . .
O2 O 0.8670(5) 0.14307(15) 0.2419(2) 0.0293(8) Uani 1 1 d . . . . .
C2 C 0.2166(6) 0.28122(18) 0.5131(3) 0.0137(8) Uani 1 1 d . . . . .
N2 N 0.1869(5) 0.34692(15) 0.5211(2) 0.0155(7) Uani 1 1 d . . . . .
C5 C 0.0411(6) 0.17761(19) 0.5790(3) 0.0148(8) Uani 1 1 d . . . . .
C4 C -0.2171(6) 0.28249(19) 0.6612(3) 0.0171(8) Uani 1 1 d . . . . .
H4A H -0.351794 0.280105 0.625557 0.026 Uiso 1 1 calc R U . . .
H4B H -0.221498 0.317741 0.706367 0.026 Uiso 1 1 calc R U . . .
H4C H -0.190144 0.241197 0.693328 0.026 Uiso 1 1 calc R U . . .
C3 C 0.0251(6) 0.35369(18) 0.5723(3) 0.0162(8) Uani 1 1 d . . . . .
O3 O -0.0986(5) 0.64929(14) 0.7194(2) 0.0259(7) Uani 1 1 d . . . . .
C9 C 0.1750(8) 0.0736(2) 0.6299(3) 0.0293(10) Uani 1 1 d . . . . .
H9 H 0.287599 0.047280 0.653916 0.035 Uiso 1 1 calc R U . . .
C8 C -0.0188(9) 0.0457(2) 0.6088(3) 0.0303(10) Uani 1 1 d . . . . .
C7 C -0.1849(8) 0.0836(2) 0.5716(3) 0.0290(10) Uani 1 1 d . . . . .
H7 H -0.317618 0.064343 0.556298 0.035 Uiso 1 1 calc R U . . .
C6 C -0.1540(7) 0.1495(2) 0.5573(3) 0.0200(9) Uani 1 1 d . . . . .
H6 H -0.266392 0.175578 0.532530 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2066(7) 0.1394(2) 0.6164(3) 0.0210(9) Uani 1 1 d . . . . .
H10 H 0.339246 0.158481 0.632356 0.025 Uiso 1 1 calc R U . . .
C11 C -0.0522(12) -0.0253(2) 0.6254(4) 0.0494(15) Uani 1 1 d . . . . .
H11 H 0.063591 -0.050519 0.648748 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3811(6) 0.25709(18) 0.4544(3) 0.0125(7) Uani 1 1 d . . . . .
C13 C 0.3743(6) 0.19469(19) 0.4158(3) 0.0158(8) Uani 1 1 d . . . . .
H13 H 0.262193 0.166308 0.428363 0.019 Uiso 1 1 calc R U . . .
C14 C 0.5273(6) 0.17392(19) 0.3599(3) 0.0161(8) Uani 1 1 d . . . . .
H14 H 0.521426 0.131275 0.334886 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6918(6) 0.2156(2) 0.3400(3) 0.0173(8) Uani 1 1 d . . . . .
C16 C 0.7007(6) 0.27772(19) 0.3781(3) 0.0172(8) Uani 1 1 d . . . . .
H16 H 0.812863 0.306051 0.365417 0.021 Uiso 1 1 calc R U . . .
C17 C 0.5465(6) 0.29820(19) 0.4345(3) 0.0167(8) Uani 1 1 d . . . . .
H17 H 0.553204 0.340696 0.460071 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8575(7) 0.1952(2) 0.2800(3) 0.0216(9) Uani 1 1 d . . . . .
H18 H 0.966276 0.225560 0.270424 0.026 Uiso 1 1 calc R U . . .
C19 C -0.0509(6) 0.41799(18) 0.6022(3) 0.0160(8) Uani 1 1 d . . . . .
C20 C 0.0999(6) 0.46780(19) 0.6102(3) 0.0193(9) Uani 1 1 d . . . . .
H20 H 0.239845 0.459244 0.594796 0.023 Uiso 1 1 calc R U . . .
C21 C 0.0467(6) 0.52924(19) 0.6403(3) 0.0189(8) Uani 1 1 d . . . . .
H21 H 0.150145 0.562335 0.647032 0.023 Uiso 1 1 calc R U . . .
C22 C -0.1604(6) 0.54202(19) 0.6605(3) 0.0172(8) Uani 1 1 d . . . . .
C23 C -0.3098(6) 0.4937(2) 0.6494(3) 0.0206(9) Uani 1 1 d . . . . .
H23 H -0.450934 0.502830 0.662153 0.025 Uiso 1 1 calc R U . . .
C24 C -0.2572(7) 0.4317(2) 0.6197(3) 0.0217(9) Uani 1 1 d . . . . .
H24 H -0.361968 0.399052 0.611603 0.026 Uiso 1 1 calc R U . . .
C25 C -0.2187(7) 0.60583(19) 0.6976(3) 0.0190(9) Uani 1 1 d . . . . .
H25 H -0.363502 0.613429 0.704952 0.023 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 C11 1.201(8) . ?
C1 C2 1.374(5) . ?
C1 N1 1.381(5) . ?
C1 C5 1.482(5) . ?
N1 C3 1.364(5) . ?
N1 C4 1.460(5) . ?
O2 C18 1.212(5) . ?
C2 N2 1.371(5) . ?
C2 C12 1.478(5) . ?
N2 C3 1.316(5) . ?
C5 C6 1.394(6) . ?
C5 C10 1.402(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 C19 1.483(5) . ?
O3 C25 1.208(5) . ?
C9 C8 1.382(7) . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C8 C7 1.400(7) . ?
C8 C11 1.498(6) . ?
C7 C6 1.388(6) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.396(5) . ?
C12 C13 1.401(5) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(6) . ?
C15 C18 1.471(6) . ?
C16 C17 1.384(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.386(6) . ?
C19 C20 1.407(5) . ?
C20 C21 1.387(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(6) . ?
C22 C25 1.475(5) . ?
C23 C24 1.394(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25 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
C2 C1 N1 105.2(3) . . ?
C2 C1 C5 132.6(4) . . ?
N1 C1 C5 122.2(3) . . ?
C3 N1 C1 107.0(3) . . ?
C3 N1 C4 128.0(3) . . ?
C1 N1 C4 124.8(3) . . ?
N2 C2 C1 110.5(3) . . ?
N2 C2 C12 119.1(3) . . ?
C1 C2 C12 130.4(3) . . ?
C3 N2 C2 105.6(3) . . ?
C6 C5 C10 120.0(4) . . ?
C6 C5 C1 120.1(4) . . ?
C10 C5 C1 119.9(4) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C3 N1 111.7(3) . . ?
N2 C3 C19 122.8(3) . . ?
N1 C3 C19 125.4(3) . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 C11 120.2(5) . . ?
C7 C8 C11 119.6(5) . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C9 C10 C5 119.4(4) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
O1 C11 C8 123.3(6) . . ?
O1 C11 H11 118.4 . . ?
C8 C11 H11 118.4 . . ?
C17 C12 C13 118.6(3) . . ?
C17 C12 C2 119.2(3) . . ?
C13 C12 C2 122.2(3) . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 C18 118.9(4) . . ?
C14 C15 C18 121.5(4) . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
O2 C18 C15 125.5(4) . . ?
O2 C18 H18 117.2 . . ?
C15 C18 H18 117.2 . . ?
C24 C19 C20 119.4(4) . . ?
C24 C19 C3 124.5(4) . . ?
C20 C19 C3 116.1(4) . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.4(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 C25 119.8(4) . . ?
C21 C22 C25 120.4(4) . . ?
C22 C23 C24 121.2(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 119.4(4) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
O3 C25 C22 125.8(4) . . ?
O3 C25 H25 117.1 . . ?
C22 C25 H25 117.1 . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.085

