# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2250023'
loop_
_audit_author_name
_audit_author_address
'Rita De Zorzi'
;Universita degli Studi di Trieste
Italy
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;

_audit_creation_date             2023-03-20T09:42:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C32 H28 N2 O5'
_chemical_formula_sum            'C32 H28 N2 O5'
_chemical_formula_weight         520.56
_chemical_compound_source        synthesis
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9250(10)
_cell_length_b                   21.683(4)
_cell_length_c                   24.350(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2600.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11998
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      25.905
_cell_measurement_wavelength     0.7

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            colorless
_exptl_crystal_description       stick
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source_type              Synchrotron
_diffrn_source                   'Elettra BL XRD1'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_monochromator  Si(111)
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Pilatus 2M detector'
_diffrn_measurement_device       'Huber 4-circles kappa goniometer'
_diffrn_measurement_device_type  'Single axis'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1323
_diffrn_reflns_av_unetI/netI     0.1442
_diffrn_reflns_number            11998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.905
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.941
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.917
_reflns_Friedel_coverage         0.68
_reflns_number_total             4974
_reflns_number_gt                2669
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1178P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4974
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2266
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.9(10)
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C01_1 C 0.4783(15) 0.5545(4) 0.5045(3) 0.0340(18) Uani 1 1 d . . . . .
O01_1 O 0.4456(12) 0.4997(2) 0.4902(2) 0.0409(14) Uani 1 1 d . . . . .
C02_1 C 0.3455(15) 0.6038(3) 0.4715(3) 0.0317(17) Uani 1 1 d . . . . .
C03_1 C 0.1301(16) 0.5877(4) 0.4368(4) 0.0362(18) Uani 1 1 d . . . . .
H03_1 H 0.065435 0.546472 0.436464 0.043 Uiso 1 1 calc R U . . .
C04_1 C 0.0102(17) 0.6310(4) 0.4030(4) 0.041(2) Uani 1 1 d . . . . .
H04_1 H -0.136957 0.619784 0.379803 0.049 Uiso 1 1 calc R U . . .
C05_1 C 0.1089(17) 0.6922(4) 0.4032(4) 0.043(2) Uani 1 1 d . . . . .
H05_1 H 0.028802 0.722399 0.380082 0.051 Uiso 1 1 calc R U . . .
C06_1 C 0.3192(17) 0.7077(4) 0.4368(4) 0.042(2) Uani 1 1 d . . . . .
H06_1 H 0.384443 0.748892 0.436538 0.05 Uiso 1 1 calc R U . . .
C07_1 C 0.4408(15) 0.6650(3) 0.4712(4) 0.0356(18) Uani 1 1 d . . . . .
H07_1 H 0.586977 0.676909 0.4943 0.043 Uiso 1 1 calc R U . . .
C08_1 C 0.6439(15) 0.5681(3) 0.5536(3) 0.0320(17) Uani 1 1 d . . . . .
C09_1 C 0.5890(14) 0.6152(3) 0.5897(3) 0.0299(17) Uani 1 1 d . . . . .
H09_1 H 0.44327 0.642605 0.582016 0.036 Uiso 1 1 calc R U . . .
C10_1 C 0.7412(14) 0.6240(3) 0.6374(4) 0.0299(17) Uani 1 1 d . . . . .
C11_1 C 0.9535(14) 0.5841(3) 0.6486(4) 0.0321(17) Uani 1 1 d . . . . .
H11_1 H 1.059891 0.589863 0.680718 0.038 Uiso 1 1 calc R U . . .
C12_1 C 1.0121(16) 0.5357(4) 0.6130(4) 0.0367(19) Uani 1 1 d . . . . .
H12_1 H 1.156799 0.508294 0.621263 0.044 Uiso 1 1 calc R U . . .
C13_1 C 0.8617(16) 0.5273(3) 0.5658(4) 0.0354(18) Uani 1 1 d . . . . .
H13_1 H 0.903432 0.49429 0.541575 0.042 Uiso 1 1 calc R U . . .
C14_1 C 0.6547(14) 0.6716(3) 0.6773(3) 0.0306(17) Uani 1 1 d . . . . .
O02_1 O 0.4102(10) 0.6868(2) 0.6811(2) 0.0336(13) Uani 1 1 d . . . . .
N_2 N 0.8473(12) 0.6965(3) 0.7099(3) 0.0294(14) Uani 1 1 d . . . . .
H0_2 H 1.019158 0.690809 0.701375 0.035 Uiso 1 1 calc R U . . .
CA_2 C 0.7819(14) 0.7319(3) 0.7579(3) 0.0287(17) Uani 1 1 d . . . . .
HA_2 H 0.580605 0.737598 0.759433 0.034 Uiso 1 1 calc R U . . .
CB_2 C 0.9198(16) 0.7967(3) 0.7580(4) 0.0346(18) Uani 1 1 d . . . . .
HB1_2 H 1.119608 0.79183 0.757002 0.042 Uiso 1 1 calc R U . . .
HB2_2 H 0.863877 0.819966 0.724863 0.042 Uiso 1 1 calc R U . . .
CG_2 C 0.8386(15) 0.8322(3) 0.8090(4) 0.0330(18) Uani 1 1 d . . . . .
CD1_2 C 0.6162(15) 0.8735(3) 0.8073(4) 0.0354(19) Uani 1 1 d . . . . .
HD1_2 H 0.526727 0.881167 0.773413 0.042 Uiso 1 1 calc R U . . .
CD2_2 C 0.9649(16) 0.8230(3) 0.8589(4) 0.0345(18) Uani 1 1 d . . . . .
HD2_2 H 1.117794 0.796408 0.86078 0.041 Uiso 1 1 calc R U . . .
CE1_2 C 0.5292(16) 0.9025(3) 0.8539(4) 0.0360(19) Uani 1 1 d . . . . .
HE1_2 H 0.382648 0.930872 0.851725 0.043 Uiso 1 1 calc R U . . .
CE2_2 C 0.8735(19) 0.8521(3) 0.9073(4) 0.040(2) Uani 1 1 d . . . . .
HE2_2 H 0.962 0.845216 0.941453 0.048 Uiso 1 1 calc R U . . .
CZ_2 C 0.6495(17) 0.8914(3) 0.9038(4) 0.040(2) Uani 1 1 d . . . . .
HZ_2 H 0.580166 0.910472 0.936017 0.048 Uiso 1 1 calc R U . . .
C_2 C 0.8712(14) 0.6969(3) 0.8083(3) 0.0263(16) Uani 1 1 d . . . . .
O_2 O 1.1147(10) 0.6824(2) 0.8139(2) 0.0328(12) Uani 1 1 d . . . . .
N_3 N 0.6791(12) 0.6836(3) 0.8446(3) 0.0274(13) Uani 1 1 d . . . . .
H0_3 H 0.510607 0.694301 0.837251 0.033 Uiso 1 1 calc R U . . .
CA_3 C 0.7351(15) 0.6526(3) 0.8957(3) 0.0291(17) Uani 1 1 d . . . . .
HA_3 H 0.935113 0.645083 0.897874 0.035 Uiso 1 1 calc R U . . .
CB_3 C 0.5896(15) 0.5897(3) 0.8991(4) 0.0331(18) Uani 1 1 d . . . . .
HB1_3 H 0.636279 0.569359 0.934295 0.04 Uiso 1 1 calc R U . . .
HB2_3 H 0.390695 0.596153 0.898342 0.04 Uiso 1 1 calc R U . . .
CG_3 C 0.6712(14) 0.5482(3) 0.8518(3) 0.0309(17) Uani 1 1 d . . . . .
CD1_3 C 0.5388(16) 0.5514(3) 0.8011(4) 0.0346(19) Uani 1 1 d . . . . .
HD1_3 H 0.388263 0.578373 0.796693 0.042 Uiso 1 1 calc R U . . .
CD2_3 C 0.8895(15) 0.5075(3) 0.8583(4) 0.0351(18) Uani 1 1 d . . . . .
HD2_3 H 0.980054 0.504122 0.892612 0.042 Uiso 1 1 calc R U . . .
CE1_3 C 0.6238(15) 0.5160(3) 0.7573(4) 0.0348(18) Uani 1 1 d . . . . .
HE1_3 H 0.532837 0.519061 0.723003 0.042 Uiso 1 1 calc R U . . .
CE2_3 C 0.9730(15) 0.4716(4) 0.8130(3) 0.0346(18) Uani 1 1 d . . . . .
HE2_3 H 1.121762 0.444077 0.81693 0.041 Uiso 1 1 calc R U . . .
CZ_3 C 0.8422(16) 0.4758(3) 0.7631(4) 0.0370(19) Uani 1 1 d . . . . .
HZ_3 H 0.90058 0.451436 0.7329 0.044 Uiso 1 1 calc R U . . .
C_3 C 0.6537(14) 0.6927(3) 0.9440(3) 0.0306(17) Uani 1 1 d . . . . .
O_3 O 0.7991(10) 0.7020(3) 0.9833(3) 0.0389(14) Uani 1 1 d . . . . .
O_4 O 0.4077(11) 0.7169(3) 0.9378(3) 0.0417(14) Uani 1 1 d . . . . .
H0_4 H 0.359055 0.733662 0.967307 0.063 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C01_1 O01_1 1.251(9) . ?
C01_1 C08_1 1.476(12) . ?
C01_1 C02_1 1.488(11) . ?
C02_1 C03_1 1.400(11) . ?
C02_1 C07_1 1.408(11) . ?
C03_1 C04_1 1.381(12) . ?
C04_1 C05_1 1.413(12) . ?
C05_1 C06_1 1.361(12) . ?
C06_1 C07_1 1.384(12) . ?
C08_1 C09_1 1.376(11) . ?
C08_1 C13_1 1.422(11) . ?
C09_1 C10_1 1.394(11) . ?
C10_1 C11_1 1.384(10) . ?
C10_1 C14_1 1.480(11) . ?
C11_1 C12_1 1.391(11) . ?
C12_1 C13_1 1.379(12) . ?
C14_1 O02_1 1.252(9) . ?
C14_1 N_2 1.349(10) . ?
N_2 CA_2 1.435(10) . ?
CA_2 C_2 1.509(11) . ?
CA_2 CB_2 1.561(10) . ?
CB_2 CG_2 1.515(12) . ?
CG_2 CD2_2 1.380(12) . ?
CG_2 CD1_2 1.416(10) . ?
CD1_2 CE1_2 1.366(12) . ?
CD2_2 CE2_2 1.411(12) . ?
CE1_2 CZ_2 1.374(13) . ?
CE2_2 CZ_2 1.396(12) . ?
C_2 O_2 1.247(9) . ?
C_2 N_3 1.327(9) . ?
N_3 CA_3 1.440(10) . ?
CA_3 C_3 1.518(11) . ?
CA_3 CB_3 1.543(10) . ?
CB_3 CG_3 1.514(11) . ?
CG_3 CD1_3 1.400(12) . ?
CG_3 CD2_3 1.400(10) . ?
CD1_3 CE1_3 1.379(12) . ?
CD2_3 CE2_3 1.412(12) . ?
CE1_3 CZ_3 1.392(11) . ?
CE2_3 CZ_3 1.378(12) . ?
C_3 O_3 1.212(10) . ?
C_3 O_4 1.329(9) . ?

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
O01_1 C01_1 C08_1 119.1(7) . . ?
O01_1 C01_1 C02_1 118.3(7) . . ?
C08_1 C01_1 C02_1 122.6(7) . . ?
C03_1 C02_1 C07_1 118.9(7) . . ?
C03_1 C02_1 C01_1 118.8(7) . . ?
C07_1 C02_1 C01_1 122.2(7) . . ?
C04_1 C03_1 C02_1 121.0(7) . . ?
C03_1 C04_1 C05_1 119.2(8) . . ?
C06_1 C05_1 C04_1 119.7(8) . . ?
C05_1 C06_1 C07_1 121.8(8) . . ?
C06_1 C07_1 C02_1 119.3(8) . . ?
C09_1 C08_1 C13_1 118.5(7) . . ?
C09_1 C08_1 C01_1 123.8(7) . . ?
C13_1 C08_1 C01_1 117.6(7) . . ?
C08_1 C09_1 C10_1 121.8(7) . . ?
C11_1 C10_1 C09_1 119.0(7) . . ?
C11_1 C10_1 C14_1 121.6(8) . . ?
C09_1 C10_1 C14_1 119.1(7) . . ?
C10_1 C11_1 C12_1 120.3(8) . . ?
C13_1 C12_1 C11_1 120.5(7) . . ?
C12_1 C13_1 C08_1 119.8(7) . . ?
O02_1 C14_1 N_2 121.9(7) . . ?
O02_1 C14_1 C10_1 120.5(7) . . ?
N_2 C14_1 C10_1 117.6(6) . . ?
C14_1 N_2 CA_2 122.4(6) . . ?
N_2 CA_2 C_2 109.1(6) . . ?
N_2 CA_2 CB_2 112.7(6) . . ?
C_2 CA_2 CB_2 109.0(6) . . ?
CG_2 CB_2 CA_2 110.1(7) . . ?
CD2_2 CG_2 CD1_2 117.8(8) . . ?
CD2_2 CG_2 CB_2 122.1(7) . . ?
CD1_2 CG_2 CB_2 120.1(8) . . ?
CE1_2 CD1_2 CG_2 120.6(8) . . ?
CG_2 CD2_2 CE2_2 121.9(8) . . ?
CD1_2 CE1_2 CZ_2 121.3(8) . . ?
CZ_2 CE2_2 CD2_2 118.3(8) . . ?
CE1_2 CZ_2 CE2_2 120.1(9) . . ?
O_2 C_2 N_3 123.9(7) . . ?
O_2 C_2 CA_2 119.8(7) . . ?
N_3 C_2 CA_2 116.3(6) . . ?
C_2 N_3 CA_3 122.7(6) . . ?
N_3 CA_3 C_3 110.5(6) . . ?
N_3 CA_3 CB_3 111.8(6) . . ?
C_3 CA_3 CB_3 110.0(6) . . ?
CG_3 CB_3 CA_3 111.1(6) . . ?
CD1_3 CG_3 CD2_3 119.2(7) . . ?
CD1_3 CG_3 CB_3 121.2(7) . . ?
CD2_3 CG_3 CB_3 119.5(7) . . ?
CE1_3 CD1_3 CG_3 120.9(8) . . ?
CG_3 CD2_3 CE2_3 118.9(8) . . ?
CD1_3 CE1_3 CZ_3 120.3(8) . . ?
CZ_3 CE2_3 CD2_3 121.1(7) . . ?
CE2_3 CZ_3 CE1_3 119.5(8) . . ?
O_3 C_3 O_4 124.2(7) . . ?
O_3 C_3 CA_3 123.5(7) . . ?
O_4 C_3 CA_3 112.3(7) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
