# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2240816'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H26 N2 O4'
_chemical_formula_sum            'C42 H26 N2 O4'
_chemical_formula_weight         622.65

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   25.526(6)
_cell_length_b                   5.3037(18)
_cell_length_c                   23.743(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.390(9)
_cell_angle_gamma                90
_cell_volume                     2879.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1524
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      31.32


_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   0.961
_exptl_transmission_factor_max   0.979
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.8492.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13613
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.915
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3816
_reflns_number_gt                2703
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0702P)²+1.7715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3816
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.49805(6) 0.1467(3) 0.65682(6) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.43882(6) 0.4794(3) 0.60724(7) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.50804(7) 0.3143(3) 0.56991(8) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.38055(5) 0.8136(3) 0.55717(6) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.55177(8) 0.1498(4) 0.57570(8) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.57612(8) 0.1589(4) 0.53311(9) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.55651(7) 0.3312(3) 0.48498(8) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.51224(7) 0.5045(3) 0.47843(7) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.48219(7) 0.3010(3) 0.61496(8) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.41761(7) 0.6650(3) 0.56016(8) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.41663(7) 0.4829(3) 0.65393(8) 0.0189(4) Uani 1 1 d . . . . .
C9 C 0.38028(8) 0.2920(4) 0.65553(8) 0.0215(4) Uani 1 1 d . . . . .
C10 C 0.35975(8) 0.3004(4) 0.70091(8) 0.0212(4) Uani 1 1 d . . . . .
C11 C 0.37582(7) 0.4978(3) 0.74463(8) 0.0202(4) Uani 1 1 d . . . . .
C12 C 0.41249(8) 0.6862(4) 0.74148(8) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.43263(8) 0.6808(4) 0.69590(8) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.35537(8) 0.5219(4) 0.79318(8) 0.0223(4) Uani 1 1 d . . . . .
C15 C 0.31619(8) 0.3817(4) 0.80181(8) 0.0228(4) Uani 1 1 d . . . . .
C16 C 0.29704(7) 0.4236(4) 0.85105(8) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.31637(9) 0.6266(4) 0.89303(10) 0.0316(5) Uani 1 1 d . . . . .
C18 C 0.29801(9) 0.6572(4) 0.93944(10) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.25892(8) 0.4876(4) 0.94427(9) 0.0254(4) Uani 1 1 d . . . . .
C20 C 0.23861(9) 0.2883(4) 0.90288(9) 0.0278(4) Uani 1 1 d . . . . .
C21 C 0.25788(8) 0.2554(4) 0.85704(9) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.5668(8) 0.033(4) 0.6111(9) 0.026(5) Uiso 1 1 d . . . . .
H9 H 0.3699(9) 0.154(4) 0.6249(10) 0.026(5) Uiso 1 1 d . . . . .
H10 H 0.3343(9) 0.163(4) 0.7013(9) 0.023(5) Uiso 1 1 d . . . . .
H12 H 0.4238(9) 0.828(4) 0.7720(10) 0.030(6) Uiso 1 1 d . . . . .
H19 H 0.2444(9) 0.513(4) 0.9747(9) 0.028(6) Uiso 1 1 d . . . . .
H3 H 0.6073(9) 0.050(4) 0.5386(10) 0.028(6) Uiso 1 1 d . . . . .
H21 H 0.2434(9) 0.121(4) 0.8274(9) 0.026(5) Uiso 1 1 d . . . . .
H13 H 0.4564(9) 0.815(4) 0.6931(9) 0.021(5) Uiso 1 1 d . . . . .
H14 H 0.3744(9) 0.662(4) 0.8224(10) 0.030(6) Uiso 1 1 d . . . . .
H15 H 0.2982(10) 0.237(5) 0.7746(11) 0.035(6) Uiso 1 1 d . . . . .
H18 H 0.3113(11) 0.796(6) 0.9674(12) 0.052(8) Uiso 1 1 d . . . . .
H20 H 0.2113(11) 0.168(5) 0.9055(11) 0.043(7) Uiso 1 1 d . . . . .
H17 H 0.3431(10) 0.747(5) 0.8892(10) 0.037(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.210(2) . ?
N1 C6 1.405(2) . ?
N1 C7 1.405(2) . ?
N1 C8 1.452(2) . ?
C1 C2 1.375(2) . ?
C1 C5 1.407(2) 5_666 ?
C1 C6 1.487(2) . ?
O2 C7 1.209(2) . ?
C2 C3 1.404(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.411(2) . ?
C4 C7 1.488(2) 5_666 ?
C5 C5 1.418(3) 5_666 ?
C8 C9 1.385(2) . ?
C8 C13 1.378(3) . ?
C9 C10 1.393(2) . ?
C9 H9 0.98(2) . ?
C10 C11 1.401(2) . ?
C10 H10 0.98(2) . ?
C11 C12 1.394(2) . ?
C11 C14 1.467(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.99(2) . ?
C13 H13 0.96(2) . ?
C14 C15 1.333(2) . ?
C14 H14 0.98(2) . ?
C15 C16 1.471(2) . ?
C15 H15 0.98(2) . ?
C16 C17 1.399(3) . ?
C16 C21 1.394(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.97(2) . ?
C18 C19 1.386(3) . ?
C18 H18 0.95(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.96(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.97(3) . ?
C21 H21 0.95(2) . ?

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
C6 N1 C7 125.33(14) . . ?
C6 N1 C8 117.46(14) . . ?
C7 N1 C8 117.10(14) . . ?
C2 C1 C5 120.18(16) . 5_666 ?
C2 C1 C6 119.89(16) . . ?
C5 C1 C6 119.93(15) 5_666 . ?
C1 C2 C3 120.40(17) . . ?
C1 C2 H2 118.7(11) . . ?
C3 C2 H2 120.8(11) . . ?
C4 C3 C2 120.57(16) . . ?
C4 C3 H3 119.7(13) . . ?
C2 C3 H3 119.7(13) . . ?
C3 C4 C5 120.23(15) . . ?
C3 C4 C7 119.62(15) . 5_666 ?
C5 C4 C7 120.15(15) . 5_666 ?
C4 C5 C1 121.40(15) . 5_666 ?
C4 C5 C5 119.14(19) . 5_666 ?
C1 C5 C5 119.46(19) 5_666 5_666 ?
O1 C6 N1 121.29(15) . . ?
O1 C6 C1 121.95(15) . . ?
N1 C6 C1 116.75(14) . . ?
O2 C7 N1 121.21(15) . . ?
O2 C7 C4 122.37(16) . 5_666 ?
N1 C7 C4 116.42(14) . 5_666 ?
C9 C8 C13 121.58(16) . . ?
C9 C8 N1 120.34(15) . . ?
C13 C8 N1 118.08(15) . . ?
C8 C9 C10 119.01(17) . . ?
C8 C9 H9 119.3(12) . . ?
C10 C9 H9 121.7(12) . . ?
C9 C10 C11 120.67(16) . . ?
C9 C10 H10 117.6(12) . . ?
C11 C10 H10 121.8(12) . . ?
C12 C11 C10 118.57(15) . . ?
C12 C11 C14 117.49(16) . . ?
C10 C11 C14 123.92(16) . . ?
C13 C12 C11 121.13(17) . . ?
C13 C12 H12 119.7(12) . . ?
C11 C12 H12 119.2(12) . . ?
C8 C13 C12 119.03(17) . . ?
C8 C13 H13 120.6(12) . . ?
C12 C13 H13 120.3(12) . . ?
C15 C14 C11 128.69(18) . . ?
C15 C14 H14 118.7(12) . . ?
C11 C14 H14 112.6(12) . . ?
C14 C15 C16 125.09(18) . . ?
C14 C15 H15 120.0(13) . . ?
C16 C15 H15 114.9(13) . . ?
C17 C16 C21 117.50(16) . . ?
C17 C16 C15 123.08(17) . . ?
C21 C16 C15 119.42(17) . . ?
C16 C17 C18 121.33(18) . . ?
C16 C17 H17 118.8(13) . . ?
C18 C17 H17 119.9(14) . . ?
C19 C18 C17 120.01(19) . . ?
C19 C18 H18 119.5(15) . . ?
C17 C18 H18 120.4(16) . . ?
C20 C19 C18 119.71(17) . . ?
C20 C19 H19 119.8(14) . . ?
C18 C19 H19 120.4(14) . . ?
C19 C20 C21 120.18(18) . . ?
C19 C20 H20 120.9(14) . . ?
C21 C20 H20 118.9(14) . . ?
C20 C21 C16 121.25(18) . . ?
C20 C21 H21 121.1(12) . . ?
C16 C21 H21 117.6(12) . . ?

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
C5 C1 C2 C3 -0.7(3) 5_666 . . . ?
C6 C1 C2 C3 179.41(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C7 -179.11(17) . . . 5_666 ?
C3 C4 C5 C1 179.01(17) . . . 5_666 ?
C7 C4 C5 C1 -0.7(3) 5_666 . . 5_666 ?
C3 C4 C5 C5 -1.0(3) . . . 5_666 ?
C7 C4 C5 C5 179.27(18) 5_666 . . 5_666 ?
C7 N1 C6 O1 -179.91(17) . . . . ?
C8 N1 C6 O1 4.1(2) . . . . ?
C7 N1 C6 C1 1.0(2) . . . . ?
C8 N1 C6 C1 -174.95(14) . . . . ?
C2 C1 C6 O1 -0.8(3) . . . . ?
C5 C1 C6 O1 179.36(17) 5_666 . . . ?
C2 C1 C6 N1 178.31(16) . . . . ?
C5 C1 C6 N1 -1.6(2) 5_666 . . . ?
C6 N1 C7 O2 -179.20(16) . . . . ?
C8 N1 C7 O2 -3.2(2) . . . . ?
C6 N1 C7 C4 0.4(2) . . . 5_666 ?
C8 N1 C7 C4 176.36(14) . . . 5_666 ?
C6 N1 C8 C9 -72.5(2) . . . . ?
C7 N1 C8 C9 111.20(19) . . . . ?
C6 N1 C8 C13 107.72(19) . . . . ?
C7 N1 C8 C13 -68.6(2) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
N1 C8 C9 C10 179.92(15) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C14 179.06(17) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C14 C11 C12 C13 -178.39(16) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
N1 C8 C13 C12 -179.18(15) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C12 C11 C14 C15 173.01(19) . . . . ?
C10 C11 C14 C15 -5.7(3) . . . . ?
C11 C14 C15 C16 -178.30(18) . . . . ?
C14 C15 C16 C17 3.1(3) . . . . ?
C14 C15 C16 C21 -176.78(19) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C15 C16 C17 C18 -178.96(19) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C16 -1.1(3) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C15 C16 C21 C20 -179.90(18) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.065

