# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1p
_database_code_depnum_ccdc_archive 'CCDC 2335938'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C16 H20 N2 O4'
_chemical_formula_sum            'C16 H20 N2 O4'
_chemical_formula_weight         304.34

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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

_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'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   7.30610(10)
_cell_length_b                   7.30610(10)
_cell_length_c                   29.5083(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.13(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4211
_cell_measurement_theta_min      6.0140
_cell_measurement_theta_max      79.2860

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.765
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_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, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            5610
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         5.998
_diffrn_reflns_theta_max         79.560
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.737
_diffrn_reflns_point_group_measured_fraction_full 0.765
_reflns_number_total             2524
_reflns_number_gt                2375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_max     0.478
_reflns_Friedel_fraction_full    0.521

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0472P)²+0.0762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
C1 C 0.3398(3) 0.6228(3) 0.25313(7) 0.0421(4) Uani 1 1 d . . . . .
C2 C 0.5269(3) 0.6417(3) 0.26085(8) 0.0444(5) Uani 1 1 d . . . . .
H2 H 0.570526 0.647403 0.290429 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6490(3) 0.6520(3) 0.22493(8) 0.0436(5) Uani 1 1 d . . . . .
H3 H 0.773436 0.666736 0.230458 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5849(3) 0.6403(3) 0.18064(7) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.3984(3) 0.6188(3) 0.17296(8) 0.0482(5) Uani 1 1 d . . . . .
H5 H 0.355071 0.609697 0.143413 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2773(3) 0.6108(4) 0.20865(8) 0.0490(5) Uani 1 1 d . . . . .
H6 H 0.152762 0.597298 0.203012 0.059 Uiso 1 1 calc R U . . .
O1O O 0.8829(2) 0.7020(3) 0.14966(6) 0.0550(4) Uani 1 1 d . . . . .
C2O C 0.7089(3) 0.6475(3) 0.14130(7) 0.0400(4) Uani 1 1 d . . . . .
N3O N 0.6657(2) 0.6079(3) 0.10080(6) 0.0449(4) Uani 1 1 d . . . . .
C4O C 0.8292(3) 0.6402(4) 0.07210(8) 0.0491(5) Uani 1 1 d . . . . .
C5O C 0.9793(3) 0.6789(4) 0.10712(9) 0.0578(6) Uani 1 1 d . . . . .
H5OA H 1.064525 0.577372 0.108878 0.069 Uiso 1 1 calc R U . . .
H5OB H 1.046339 0.789069 0.099321 0.069 Uiso 1 1 calc R U . . .
C6O C 0.7933(5) 0.8040(5) 0.04181(12) 0.0765(9) Uani 1 1 d . . . . .
H6OA H 0.897871 0.825267 0.022844 0.115 Uiso 1 1 calc R U . . .
H6OB H 0.771097 0.910124 0.060204 0.115 Uiso 1 1 calc R U . . .
H6OC H 0.688056 0.780368 0.023223 0.115 Uiso 1 1 calc R U . . .
C7O C 0.8701(4) 0.4714(5) 0.04393(12) 0.0711(8) Uani 1 1 d . . . . .
H7OB H 0.766555 0.443593 0.025133 0.107 Uiso 1 1 calc R U . . .
H7OC H 0.894645 0.369812 0.063641 0.107 Uiso 1 1 calc R U . . .
H7OA H 0.975110 0.494042 0.025178 0.107 Uiso 1 1 calc R U . . .
CC C 0.1995(3) 0.6241(3) 0.29032(7) 0.0467(5) Uani 1 1 d . . . . .
OC O 0.0483(3) 0.6916(3) 0.28394(7) 0.0670(5) Uani 1 1 d . . . . .
NA N 0.2473(3) 0.5466(3) 0.32987(7) 0.0489(4) Uani 1 1 d . . . . .
HA H 0.361(4) 0.503(4) 0.3341(11) 0.049(7) Uiso 1 1 d . . . . .
C1A C 0.1258(3) 0.5541(3) 0.36864(8) 0.0458(5) Uani 1 1 d . . . . .
H1A H 0.000012 0.553997 0.357080 0.055 Uiso 1 1 calc R U . . .
C2A C 0.1543(3) 0.7333(3) 0.39392(9) 0.0486(5) Uani 1 1 d . . . . .
C3A C 0.1470(4) 0.3865(4) 0.39890(9) 0.0552(6) Uani 1 1 d . . . . .
H3AC H 0.131030 0.277655 0.381124 0.083 Uiso 1 1 calc R U . . .
H3AA H 0.056498 0.389969 0.422459 0.083 Uiso 1 1 calc R U . . .
H3AB H 0.266982 0.386411 0.412177 0.083 Uiso 1 1 calc R U . . .
O1A O 0.2512(4) 0.8546(3) 0.38228(9) 0.0808(7) Uani 1 1 d . . . . .
O2A O 0.0564(3) 0.7364(3) 0.43155(7) 0.0711(6) Uani 1 1 d . . . . .
CMA C 0.0715(5) 0.8981(4) 0.45916(11) 0.0743(9) Uani 1 1 d . . . . .
HMAB H 0.022200 1.001010 0.443030 0.111 Uiso 1 1 calc R U . . .
HMAC H 0.198017 0.920444 0.466041 0.111 Uiso 1 1 calc R U . . .
HMAA H 0.004554 0.880770 0.486813 0.111 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
C1 C6 1.392(3) . ?
C1 C2 1.393(3) . ?
C1 CC 1.502(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.390(3) . ?
C4 C2O 1.474(3) . ?
C5 C6 1.377(3) . ?
O1O C2O 1.355(3) . ?
O1O C5O 1.449(3) . ?
C2O N3O 1.269(3) . ?
N3O C4O 1.483(3) . ?
C4O C6O 1.517(4) . ?
C4O C7O 1.517(4) . ?
C4O C5O 1.533(3) . ?
CC OC 1.225(3) . ?
CC NA 1.343(3) . ?
NA C1A 1.449(3) . ?
C1A C2A 1.521(3) . ?
C1A C3A 1.523(3) . ?
C2A O1A 1.185(3) . ?
C2A O2A 1.321(3) . ?
O2A CMA 1.440(3) . ?

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 C1 C2 118.8(2) . . ?
C6 C1 CC 117.7(2) . . ?
C2 C1 CC 123.3(2) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 119.9(2) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 C2O 118.57(19) . . ?
C3 C4 C2O 122.08(19) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C1 120.5(2) . . ?
C2O O1O C5O 105.29(18) . . ?
N3O C2O O1O 118.2(2) . . ?
N3O C2O C4 125.48(19) . . ?
O1O C2O C4 116.35(18) . . ?
C2O N3O C4O 107.51(18) . . ?
N3O C4O C6O 108.8(2) . . ?
N3O C4O C7O 110.0(2) . . ?
C6O C4O C7O 110.7(3) . . ?
N3O C4O C5O 102.73(19) . . ?
C6O C4O C5O 112.1(2) . . ?
C7O C4O C5O 112.2(2) . . ?
O1O C5O C4O 104.96(18) . . ?
OC CC NA 122.5(2) . . ?
OC CC C1 120.4(2) . . ?
NA CC C1 117.1(2) . . ?
CC NA C1A 120.74(19) . . ?
NA C1A C2A 109.60(19) . . ?
NA C1A C3A 111.73(19) . . ?
C2A C1A C3A 113.0(2) . . ?
O1A C2A O2A 123.7(3) . . ?
O1A C2A C1A 125.7(2) . . ?
O2A C2A C1A 110.7(2) . . ?
C2A O2A CMA 116.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA N3O 0.90(3) 2.24(3) 3.119(3) 166(3) 4_565 yes

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.053


####################################################################### 
# 
# 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_1n4
_database_code_depnum_ccdc_archive 'CCDC 2335941'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C20 H22 N2 O4'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.39

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   22.688(4)
_cell_length_b                   5.2784(6)
_cell_length_c                   16.099(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.082(17)
_cell_angle_gamma                90
_cell_volume                     1861.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    598
_cell_measurement_theta_min      4.1410
_cell_measurement_theta_max      50.1640


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.52933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            2235
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         51.376
_diffrn_reflns_theta_full        51.376
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.792
_reflns_number_total             1615
_reflns_number_gt                1209
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.399
_reflns_Friedel_fraction_max     0.526
_reflns_Friedel_fraction_full    0.527

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0641P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1615
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.0826(3) 0.6777(16) 0.5322(5) 0.064(2) Uani 1 1 d . . . . .
H1 H 0.057899 0.820908 0.524361 0.077 Uiso 1 1 calc R U . . .
C2 C 0.0854(3) 0.5274(16) 0.6011(5) 0.064(2) Uani 1 1 d . . . . .
C3 C 0.1233(3) 0.3085(16) 0.6132(5) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.124521 0.201838 0.659604 0.081 Uiso 1 1 calc R U . . .
C4 C 0.1576(3) 0.2534(17) 0.5579(5) 0.073(2) Uani 1 1 d . . . . .
H4 H 0.183368 0.113220 0.568149 0.088 Uiso 1 1 calc R U . . .
C4A C 0.1547(3) 0.4061(16) 0.4855(5) 0.062(2) Uani 1 1 d . . . . .
C5 C 0.1888(3) 0.3502(16) 0.4248(5) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.215519 0.213161 0.434558 0.080 Uiso 1 1 calc R U . . .
C6 C 0.1831(3) 0.4939(17) 0.3528(5) 0.061(2) Uani 1 1 d . . . . .
C7 C 0.1447(3) 0.7100(16) 0.3399(5) 0.069(2) Uani 1 1 d . . . . .
H7 H 0.141575 0.811924 0.291831 0.083 Uiso 1 1 calc R U . . .
C8 C 0.1126(3) 0.7684(16) 0.3974(5) 0.068(2) Uani 1 1 d . . . . .
H8 H 0.087183 0.909661 0.387137 0.081 Uiso 1 1 calc R U . . .
C8A C 0.1160(3) 0.6237(16) 0.4720(5) 0.064(2) Uani 1 1 d . . . . .
O1O O 0.2560(3) 0.2322(12) 0.3113(3) 0.0887(18) Uani 1 1 d . . . . .
C2O C 0.2137(4) 0.4179(17) 0.2875(6) 0.070(3) Uani 1 1 d . . . . .
N3O N 0.2034(3) 0.5009(14) 0.2123(5) 0.078(2) Uani 1 1 d . . . . .
C4O C 0.2394(4) 0.3478(18) 0.1661(5) 0.075(2) Uani 1 1 d . . . . .
C5O C 0.2795(4) 0.193(2) 0.2380(5) 0.092(3) Uani 1 1 d . . . . .
H5OA H 0.277681 0.014915 0.222562 0.111 Uiso 1 1 calc R U . . .
H5OB H 0.321573 0.249134 0.249840 0.111 Uiso 1 1 calc R U . . .
C6O C 0.2770(5) 0.511(2) 0.1216(7) 0.130(4) Uani 1 1 d . . . . .
H6OA H 0.301133 0.403807 0.095012 0.195 Uiso 1 1 calc R U . . .
H6OB H 0.303492 0.618365 0.163130 0.195 Uiso 1 1 calc R U . . .
H6OC H 0.250339 0.612923 0.078464 0.195 Uiso 1 1 calc R U . . .
C7O C 0.1964(4) 0.181(2) 0.1023(6) 0.127(4) Uani 1 1 d . . . . .
H7OB H 0.168564 0.284666 0.060912 0.190 Uiso 1 1 calc R U . . .
H7OC H 0.173793 0.076329 0.131862 0.190 Uiso 1 1 calc R U . . .
H7OA H 0.219247 0.075839 0.073319 0.190 Uiso 1 1 calc R U . . .
CC C 0.0520(3) 0.5997(19) 0.6657(5) 0.067(2) Uani 1 1 d . . . . .
OC O 0.0429(3) 0.8244(11) 0.6798(4) 0.0807(18) Uani 1 1 d . . . . .
NA N 0.0314(4) 0.4126(17) 0.7077(5) 0.079(3) Uani 1 1 d . . . . .
HA H 0.047(4) 0.285(18) 0.703(5) 0.08(4) Uiso 1 1 d . . . . .
C1A C 0.0075(4) 0.4697(16) 0.7805(5) 0.069(2) Uani 1 1 d . . . . .
H1A H -0.020200 0.614562 0.765399 0.083 Uiso 1 1 calc R U . . .
C2A C 0.0574(4) 0.5389(18) 0.8576(6) 0.080(3) Uani 1 1 d . . . . .
C3A C -0.0289(4) 0.2432(18) 0.7999(6) 0.099(3) Uani 1 1 d . . . . .
H3AC H -0.059188 0.195587 0.748636 0.149 Uiso 1 1 calc R U . . .
H3AA H -0.048471 0.288796 0.843864 0.149 Uiso 1 1 calc R U . . .
H3AB H -0.001750 0.103279 0.819272 0.149 Uiso 1 1 calc R U . . .
O1A O 0.1103(3) 0.4963(17) 0.8687(4) 0.121(3) Uani 1 1 d . . . . .
O2A O 0.0362(2) 0.6739(14) 0.9137(4) 0.101(2) Uani 1 1 d . . . . .
CMA C 0.0799(4) 0.755(3) 0.9903(6) 0.128(5) Uani 1 1 d . . . . .
HMAC H 0.116910 0.659113 0.997426 0.192 Uiso 1 1 calc R U . . .
HMAA H 0.063735 0.727758 1.039083 0.192 Uiso 1 1 calc R U . . .
HMAB H 0.088478 0.931641 0.985867 0.192 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
C1 C2 1.352(9) . ?
C1 C8A 1.406(9) . ?
C2 C3 1.422(10) . ?
C2 CC 1.487(10) . ?
C3 C4 1.359(9) . ?
C4 C4A 1.405(10) . ?
C4A C8A 1.426(10) . ?
C4A C5 1.427(9) . ?
C5 C6 1.363(10) . ?
C6 C7 1.417(10) . ?
C6 C2O 1.458(10) . ?
C7 C8 1.354(9) . ?
C8 C8A 1.409(9) . ?
O1O C2O 1.356(10) . ?
O1O C5O 1.431(8) . ?
C2O N3O 1.251(9) . ?
N3O C4O 1.480(9) . ?
C4O C7O 1.504(11) . ?
C4O C5O 1.512(11) . ?
C4O C6O 1.517(11) . ?
CC OC 1.235(9) . ?
CC NA 1.348(11) . ?
NA C1A 1.444(10) . ?
C1A C2A 1.492(11) . ?
C1A C3A 1.531(11) . ?
C2A O1A 1.188(9) . ?
C2A O2A 1.334(9) . ?
O2A CMA 1.432(10) . ?

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 C8A 121.8(7) . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 CC 120.0(8) . . ?
C3 C2 CC 120.8(7) . . ?
C4 C3 C2 120.9(7) . . ?
C3 C4 C4A 120.6(8) . . ?
C4 C4A C8A 118.9(7) . . ?
C4 C4A C5 122.2(8) . . ?
C8A C4A C5 118.9(7) . . ?
C6 C5 C4A 121.2(7) . . ?
C5 C6 C7 119.4(7) . . ?
C5 C6 C2O 120.1(8) . . ?
C7 C6 C2O 120.4(8) . . ?
C8 C7 C6 120.2(8) . . ?
C7 C8 C8A 122.6(8) . . ?
C1 C8A C8 123.8(8) . . ?
C1 C8A C4A 118.6(7) . . ?
C8 C8A C4A 117.5(7) . . ?
C2O O1O C5O 105.0(6) . . ?
N3O C2O O1O 117.9(7) . . ?
N3O C2O C6 126.6(9) . . ?
O1O C2O C6 115.5(8) . . ?
C2O N3O C4O 107.8(7) . . ?
N3O C4O C7O 108.5(7) . . ?
N3O C4O C5O 102.2(6) . . ?
C7O C4O C5O 111.2(8) . . ?
N3O C4O C6O 112.3(8) . . ?
C7O C4O C6O 110.7(8) . . ?
C5O C4O C6O 111.5(8) . . ?
O1O C5O C4O 105.9(7) . . ?
OC CC NA 121.0(8) . . ?
OC CC C2 121.0(8) . . ?
NA CC C2 118.0(8) . . ?
CC NA C1A 120.4(8) . . ?
NA C1A C2A 111.3(7) . . ?
NA C1A C3A 109.8(7) . . ?
C2A C1A C3A 110.7(7) . . ?
O1A C2A O2A 121.8(9) . . ?
O1A C2A C1A 126.6(8) . . ?
O2A C2A C1A 111.4(8) . . ?
C2A O2A CMA 116.8(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA OC 0.77(9) 2.46(9) 3.158(11) 152(8) 1_545 yes

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.044


####################################################################### 
# 
# 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_1m6
_database_code_depnum_ccdc_archive 'CCDC 2335939'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C33 H36 N4 O6, C H4 O'
_chemical_formula_sum            'C34 H40 N4 O7'
_chemical_formula_weight         616.70

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.85790(10)
_cell_length_b                   21.1948(4)
_cell_length_c                   15.9374(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.905(2)
_cell_angle_gamma                90
_cell_volume                     1640.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4259
_cell_measurement_theta_min      3.4770
_cell_measurement_theta_max      75.7630

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            8050
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.471
_diffrn_reflns_theta_max         76.043
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.726
_reflns_number_total             4801
_reflns_number_gt                4108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.386
_reflns_Friedel_fraction_max     0.402
_reflns_Friedel_fraction_full    0.437

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0736P)²+0.2653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4801
_refine_ls_number_parameters     423
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.169
_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
C1 C 0.4666(9) 0.5381(2) 0.5787(3) 0.0557(10) Uani 1 1 d . . . . .
C2 C 0.6339(9) 0.4962(2) 0.5365(2) 0.0523(9) Uani 1 1 d . . . . .
H2 H 0.635495 0.453654 0.550492 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8002(9) 0.5187(3) 0.4726(2) 0.0545(10) Uani 1 1 d . . . . .
C4 C 0.7960(12) 0.5821(3) 0.4514(3) 0.0730(14) Uani 1 1 d . . . . .
H4 H 0.904770 0.596783 0.408624 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6323(14) 0.6231(3) 0.4933(4) 0.0830(16) Uani 1 1 d . . . . .
H5 H 0.629438 0.665578 0.478813 0.100 Uiso 1 1 calc R U . . .
C6 C 0.4694(12) 0.6013(3) 0.5578(4) 0.0735(13) Uani 1 1 d . . . . .
H6 H 0.361687 0.629578 0.586837 0.088 Uiso 1 1 calc R U . . .
O1O O 1.1173(8) 0.4973(2) 0.3644(2) 0.0773(11) Uani 1 1 d . . . . .
C2O C 0.9800(9) 0.4739(3) 0.4296(2) 0.0583(12) Uani 1 1 d . . . . .
N3O N 1.0175(10) 0.4165(2) 0.4477(2) 0.0682(11) Uani 1 1 d . . . . .
C4O C 1.2130(11) 0.3903(3) 0.3875(3) 0.0702(14) Uani 1 1 d . . . . .
H4O H 1.381171 0.377169 0.418398 0.084 Uiso 1 1 calc R U . . .
C5O C 1.2788(12) 0.4473(3) 0.3330(3) 0.0774(17) Uani 1 1 d . . . . .
H5OA H 1.473285 0.457526 0.337691 0.093 Uiso 1 1 calc R U . . .
H5OB H 1.229800 0.438966 0.274500 0.093 Uiso 1 1 calc R U . . .
C3B C 1.0907(10) 0.3340(3) 0.3420(3) 0.0652(13) Uani 1 1 d . . . . .
C4B C 1.1835(14) 0.2730(4) 0.3613(4) 0.0851(17) Uani 1 1 d . . . . .
H4B H 1.324271 0.267286 0.401511 0.102 Uiso 1 1 calc R U . . .
C5B C 1.0662(16) 0.2208(4) 0.3205(5) 0.0942(19) Uani 1 1 d . . . . .
H5B H 1.125751 0.180442 0.334925 0.113 Uiso 1 1 calc R U . . .
C6B C 0.8674(14) 0.2285(4) 0.2605(4) 0.0882(19) Uani 1 1 d . . . . .
H6B H 0.793266 0.193426 0.232894 0.106 Uiso 1 1 calc R U . . .
C7B C 0.7745(13) 0.2872(4) 0.2402(4) 0.0841(17) Uani 1 1 d . . . . .
H7B H 0.637826 0.292155 0.198421 0.101 Uiso 1 1 calc R U . . .
C8B C 0.8836(11) 0.3402(3) 0.2817(4) 0.0733(14) Uani 1 1 d . . . . .
H8B H 0.815221 0.380040 0.268307 0.088 Uiso 1 1 calc R U . . .
CC C 0.2845(9) 0.5171(3) 0.6477(3) 0.0607(12) Uani 1 1 d . . . . .
OC O 0.2060(11) 0.5551(3) 0.6997(3) 0.1027(16) Uani 1 1 d . . . . .
NG N 0.2098(8) 0.4570(2) 0.6473(2) 0.0606(10) Uani 1 1 d D . . . .
HG H 0.278(12) 0.431(3) 0.613(3) 0.078(18) Uiso 1 1 d D . . . .
C1G C 0.0331(9) 0.4321(3) 0.7108(3) 0.0659(13) Uani 1 1 d . . . . .
H1GB H -0.063065 0.395284 0.688642 0.079 Uiso 1 1 calc R U . . .
H1GA H -0.103923 0.463554 0.724014 0.079 Uiso 1 1 calc R U . . .
C2G C 0.1918(8) 0.4139(2) 0.7905(3) 0.0528(10) Uani 1 1 d . . . . .
O1G O 0.4438(6) 0.4139(3) 0.7960(2) 0.0818(13) Uani 1 1 d . . . . .
NV N 0.0313(6) 0.39835(18) 0.85398(19) 0.0479(8) Uani 1 1 d D . . . .
HV H -0.147(5) 0.402(2) 0.845(2) 0.036(10) Uiso 1 1 d D . . . .
C1V C 0.1422(7) 0.37914(19) 0.9360(2) 0.0420(8) Uani 1 1 d . . . . .
H1V H 0.338788 0.369807 0.931613 0.050 Uiso 1 1 calc R U . . .
C2V C -0.0059(7) 0.3198(2) 0.9620(2) 0.0444(8) Uani 1 1 d . . . . .
C3V C 0.1071(9) 0.4307(2) 1.0018(3) 0.0551(10) Uani 1 1 d . . . . .
H3V H -0.089396 0.440504 1.005018 0.066 Uiso 1 1 calc R U . . .
C4V C 0.2601(12) 0.4906(3) 0.9765(4) 0.0720(13) Uani 1 1 d . . . . .
H4VC H 0.453122 0.481587 0.973313 0.108 Uiso 1 1 calc R U . . .
H4VA H 0.233087 0.522866 1.017653 0.108 Uiso 1 1 calc R U . . .
H4VB H 0.189851 0.504759 0.922757 0.108 Uiso 1 1 calc R U . . .
C5V C 0.2134(18) 0.4090(4) 1.0876(3) 0.096(2) Uani 1 1 d . . . . .
H5VC H 0.104949 0.374011 1.105863 0.143 Uiso 1 1 calc R U . . .
H5VA H 0.200214 0.443040 1.126981 0.143 Uiso 1 1 calc R U . . .
H5VB H 0.402258 0.396164 1.084297 0.143 Uiso 1 1 calc R U . . .
O1V O -0.2576(5) 0.31813(17) 0.9628(2) 0.0648(9) Uani 1 1 d . . . . .
NP N 0.1534(6) 0.27069(16) 0.9840(2) 0.0435(7) Uani 1 1 d D . . . .
HP H 0.329(5) 0.273(2) 0.991(2) 0.038(10) Uiso 1 1 d D . . . .
C1P C 0.0306(8) 0.21241(19) 1.0120(3) 0.0463(8) Uani 1 1 d . . . . .
H1P H -0.126788 0.224126 1.045660 0.056 Uiso 1 1 calc R U . . .
C2P C 0.2331(7) 0.1787(2) 1.0701(2) 0.0452(8) Uani 1 1 d . . . . .
C3P C -0.0830(8) 0.1718(2) 0.9391(3) 0.0540(9) Uani 1 1 d . . . . .
H3PA H -0.160046 0.133624 0.962215 0.065 Uiso 1 1 calc R U . . .
H3PB H -0.232513 0.194692 0.911057 0.065 Uiso 1 1 calc R U . . .
C4P C 0.1219(9) 0.1533(3) 0.8742(3) 0.0587(11) Uani 1 1 d . . . . .
C5P C 0.2489(12) 0.0952(3) 0.8775(4) 0.0765(15) Uani 1 1 d . . . . .
H5P H 0.208734 0.067184 0.920373 0.092 Uiso 1 1 calc R U . . .
C6P C 0.4372(15) 0.0778(5) 0.8174(5) 0.102(2) Uani 1 1 d . . . . .
H6P H 0.521688 0.038409 0.820176 0.123 Uiso 1 1 calc R U . . .
C7P C 0.4968(16) 0.1189(6) 0.7544(5) 0.113(3) Uani 1 1 d . . . . .
H7P H 0.620581 0.107189 0.713885 0.135 Uiso 1 1 calc R U . . .
C8P C 0.3779(17) 0.1760(6) 0.7506(4) 0.110(3) Uani 1 1 d . . . . .
H8P H 0.421991 0.203983 0.708107 0.131 Uiso 1 1 calc R U . . .
C9P C 0.1874(14) 0.1937(4) 0.8105(3) 0.0805(16) Uani 1 1 d . . . . .
H9P H 0.104471 0.233198 0.807046 0.097 Uiso 1 1 calc R U . . .
O1P O 0.4523(6) 0.1994(2) 1.0920(2) 0.0703(10) Uani 1 1 d . . . . .
O2P O 0.1342(7) 0.12471(16) 1.0963(2) 0.0657(8) Uani 1 1 d . . . . .
CMP C 0.3028(13) 0.0907(3) 1.1580(4) 0.0751(14) Uani 1 1 d . . . . .
HMPC H 0.491041 0.090875 1.141535 0.113 Uiso 1 1 calc R U . . .
HMPA H 0.238862 0.047944 1.161651 0.113 Uiso 1 1 calc R U . . .
HMPB H 0.289922 0.110734 1.211775 0.113 Uiso 1 1 calc R U . . .
OM O 0.715(2) 0.3308(7) 0.5541(7) 0.192(4) Uani 1 1 d D . . . .
HM H 0.744277 0.345246 0.507528 0.289 Uiso 1 1 calc DR U . . .
CM C 0.914(6) 0.2828(14) 0.5744(12) 0.36(2) Uani 1 1 d D . . . .
HMC H 1.094937 0.300994 0.576642 0.537 Uiso 1 1 calc DR U . . .
HMA H 0.904649 0.250512 0.532193 0.537 Uiso 1 1 calc DR U . . .
HMB H 0.875146 0.264765 0.627995 0.537 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
C1 C6 1.380(8) . ?
C1 C2 1.392(7) . ?
C1 CC 1.501(6) . ?
C2 C3 1.403(5) . ?
C3 C4 1.386(8) . ?
C3 C2O 1.474(7) . ?
C4 C5 1.366(9) . ?
C5 C6 1.396(8) . ?
O1O C2O 1.347(5) . ?
O1O C5O 1.420(8) . ?
C2O N3O 1.262(7) . ?
N3O C4O 1.480(6) . ?
C4O C3B 1.510(8) . ?
C4O C5O 1.528(9) . ?
C3B C8B 1.374(8) . ?
C3B C4B 1.399(10) . ?
C4B C5B 1.395(10) . ?
C5B C6B 1.346(10) . ?
C6B C7B 1.360(11) . ?
C7B C8B 1.399(9) . ?
CC OC 1.225(7) . ?
CC NG 1.325(7) . ?
NG C1G 1.449(5) . ?
C1G C2G 1.513(6) . ?
C2G O1G 1.225(5) . ?
C2G NV 1.339(5) . ?
NV C1V 1.456(5) . ?
C1V C2V 1.514(5) . ?
C1V C3V 1.527(6) . ?
C2V O1V 1.224(5) . ?
C2V NP 1.336(5) . ?
C3V C5V 1.518(8) . ?
C3V C4V 1.531(7) . ?
NP C1P 1.449(5) . ?
C1P C2P 1.508(5) . ?
C1P C3P 1.533(6) . ?
C2P O1P 1.193(5) . ?
C2P O2P 1.315(5) . ?
C3P C4P 1.511(7) . ?
C4P C9P 1.373(8) . ?
C4P C5P 1.378(8) . ?
C5P C6P 1.396(9) . ?
C6P C7P 1.368(14) . ?
C7P C8P 1.342(14) . ?
C8P C9P 1.403(10) . ?
O2P CMP 1.451(6) . ?
OM CM 1.432(16) . ?

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 C1 C2 119.4(4) . . ?
C6 C1 CC 118.4(5) . . ?
C2 C1 CC 122.2(5) . . ?
C1 C2 C3 119.6(5) . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 C2O 121.0(4) . . ?
C2 C3 C2O 119.0(4) . . ?
C5 C4 C3 120.1(5) . . ?
C4 C5 C6 120.2(6) . . ?
C1 C6 C5 120.6(6) . . ?
C2O O1O C5O 106.9(5) . . ?
N3O C2O O1O 117.4(5) . . ?
N3O C2O C3 126.6(4) . . ?
O1O C2O C3 116.0(5) . . ?
C2O N3O C4O 107.7(4) . . ?
N3O C4O C3B 110.9(4) . . ?
N3O C4O C5O 102.9(5) . . ?
C3B C4O C5O 115.9(4) . . ?
O1O C5O C4O 105.1(4) . . ?
C8B C3B C4B 117.7(6) . . ?
C8B C3B C4O 121.9(6) . . ?
C4B C3B C4O 120.4(5) . . ?
C5B C4B C3B 120.4(6) . . ?
C6B C5B C4B 120.5(7) . . ?
C5B C6B C7B 120.3(7) . . ?
C6B C7B C8B 120.3(6) . . ?
C3B C8B C7B 120.7(7) . . ?
OC CC NG 122.9(5) . . ?
OC CC C1 120.4(6) . . ?
NG CC C1 116.7(4) . . ?
CC NG C1G 121.0(4) . . ?
NG C1G C2G 112.5(4) . . ?
O1G C2G NV 123.5(4) . . ?
O1G C2G C1G 122.7(3) . . ?
NV C2G C1G 113.8(3) . . ?
C2G NV C1V 122.7(3) . . ?
NV C1V C2V 108.2(3) . . ?
NV C1V C3V 111.7(3) . . ?
C2V C1V C3V 110.0(3) . . ?
O1V C2V NP 123.0(4) . . ?
O1V C2V C1V 120.7(4) . . ?
NP C2V C1V 116.3(3) . . ?
C5V C3V C1V 111.1(4) . . ?
C5V C3V C4V 109.5(5) . . ?
C1V C3V C4V 110.3(4) . . ?
C2V NP C1P 120.2(3) . . ?
NP C1P C2P 109.0(3) . . ?
NP C1P C3P 112.7(3) . . ?
C2P C1P C3P 114.2(3) . . ?
O1P C2P O2P 124.0(4) . . ?
O1P C2P C1P 124.3(4) . . ?
O2P C2P C1P 111.7(3) . . ?
C4P C3P C1P 115.9(3) . . ?
C9P C4P C5P 118.1(5) . . ?
C9P C4P C3P 121.2(5) . . ?
C5P C4P C3P 120.7(5) . . ?
C4P C5P C6P 120.8(7) . . ?
C7P C6P C5P 119.7(8) . . ?
C8P C7P C6P 120.4(7) . . ?
C7P C8P C9P 120.2(8) . . ?
C4P C9P C8P 120.7(7) . . ?
C2P O2P CMP 116.4(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NV HV O1G 0.88(2) 2.13(2) 2.988(4) 167(4) 1_455 yes
NP HP O1V 0.86(2) 2.28(3) 3.062(4) 151(4) 1_655 yes
OM HM N3O 0.82 2.24 2.916(11) 139.3 . yes

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.040


####################################################################### 
# 
# 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_1n2
_database_code_depnum_ccdc_archive 'CCDC 2335940'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37

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                   14.4335(2)
_cell_length_b                   13.2892(2)
_cell_length_c                   9.4990(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.099(2)
_cell_angle_gamma                90
_cell_volume                     1759.10(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8945
_cell_measurement_theta_min      4.5910
_cell_measurement_theta_max      78.8170

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_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, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12736
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         79.704
_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 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3615
_reflns_number_gt                3143
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0952P)²+0.2712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3615
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.59556(9) 0.30589(10) 0.46772(14) 0.0354(3) Uani 1 1 d . . . . .
C2 C 0.55488(10) 0.23680(10) 0.54016(15) 0.0402(3) Uani 1 1 d . . . . .
H2 H 0.592603 0.185667 0.592592 0.048 Uiso 1 1 calc R U . . .
C3 C 0.45730(10) 0.24179(11) 0.53666(16) 0.0413(3) Uani 1 1 d . . . . .
H3 H 0.430935 0.192967 0.584749 0.050 Uiso 1 1 calc R U . . .
C4 C 0.40007(9) 0.31764(10) 0.46334(15) 0.0375(3) Uani 1 1 d . . . . .
C4A C 0.43902(9) 0.39054(9) 0.38299(14) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.38311(11) 0.46831(12) 0.30042(17) 0.0464(3) Uani 1 1 d . . . . .
H5 H 0.318548 0.473862 0.298390 0.056 Uiso 1 1 calc R U . . .
C6 C 0.42264(12) 0.53532(12) 0.22369(18) 0.0540(4) Uani 1 1 d . . . . .
H6 H 0.384391 0.584945 0.168336 0.065 Uiso 1 1 calc R U . . .
C7 C 0.51989(12) 0.53007(12) 0.22754(18) 0.0512(4) Uani 1 1 d . . . . .
H7 H 0.546177 0.576808 0.176108 0.061 Uiso 1 1 calc R U . . .
C8 C 0.57645(10) 0.45680(11) 0.30628(16) 0.0426(3) Uani 1 1 d . . . . .
H8 H 0.641225 0.454385 0.308593 0.051 Uiso 1 1 calc R U . . .
C8A C 0.53800(9) 0.38408(9) 0.38483(13) 0.0345(3) Uani 1 1 d . . . . .
O1O O 0.26643(9) 0.23509(10) 0.5172(2) 0.0745(5) Uani 1 1 d . . . . .
C2O C 0.30078(10) 0.32319(11) 0.47776(16) 0.0420(3) Uani 1 1 d . . . . .
N3O N 0.24669(9) 0.39916(10) 0.46447(18) 0.0544(4) Uani 1 1 d . . . . .
C4O C 0.15875(10) 0.36906(13) 0.5063(2) 0.0532(4) Uani 1 1 d . . . . .
C5O C 0.17106(14) 0.25559(16) 0.5276(4) 0.0849(8) Uani 1 1 d . . . . .
H5OA H 0.163548 0.235777 0.622251 0.102 Uiso 1 1 calc R U . . .
H5OB H 0.124250 0.219689 0.452573 0.102 Uiso 1 1 calc R U . . .
C6O C 0.07118(13) 0.3967(2) 0.3863(3) 0.0816(7) Uani 1 1 d . . . . .
H6OB H 0.072478 0.361320 0.298750 0.122 Uiso 1 1 calc R U . . .
H6OC H 0.070996 0.467857 0.368994 0.122 Uiso 1 1 calc R U . . .
H6OA H 0.014377 0.378429 0.415033 0.122 Uiso 1 1 calc R U . . .
C7O C 0.15788(17) 0.4233(2) 0.6453(3) 0.0924(8) Uani 1 1 d . . . . .
H7OB H 0.157797 0.494611 0.629256 0.139 Uiso 1 1 calc R U . . .
H7OC H 0.213887 0.405028 0.720442 0.139 Uiso 1 1 calc R U . . .
H7OA H 0.101394 0.404739 0.674620 0.139 Uiso 1 1 calc R U . . .
CC C 0.70045(9) 0.29764(10) 0.47679(14) 0.0370(3) Uani 1 1 d . . . . .
OC O 0.73359(7) 0.30308(9) 0.36959(11) 0.0485(3) Uani 1 1 d . . . . .
NG N 0.75816(8) 0.28263(10) 0.61004(13) 0.0438(3) Uani 1 1 d . . . . .
HG H 0.7324(13) 0.2698(13) 0.684(2) 0.048(4) Uiso 1 1 d . . . . .
C1G C 0.85965(10) 0.26860(13) 0.62774(18) 0.0488(4) Uani 1 1 d . . . . .
H1GB H 0.890854 0.263174 0.731057 0.059 Uiso 1 1 calc R U . . .
H1GA H 0.884902 0.328069 0.591546 0.059 Uiso 1 1 calc R U . . .
C2G C 0.88609(10) 0.17768(13) 0.55154(16) 0.0470(4) Uani 1 1 d . . . . .
O1G O 0.95630(9) 0.17381(12) 0.50688(18) 0.0746(4) Uani 1 1 d . . . . .
O2G O 0.82516(8) 0.10253(9) 0.54371(16) 0.0617(3) Uani 1 1 d . . . . .
CMG C 0.84650(17) 0.01203(17) 0.4764(3) 0.0870(7) Uani 1 1 d . . . . .
HMGA H 0.799195 -0.038163 0.479314 0.131 Uiso 1 1 calc R U . . .
HMGB H 0.908829 -0.011990 0.527982 0.131 Uiso 1 1 calc R U . . .
HMGC H 0.845769 0.025601 0.376875 0.131 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
C1 C2 1.3681(19) . ?
C1 C8A 1.4315(18) . ?
C1 CC 1.4978(17) . ?
C2 C3 1.4018(19) . ?
C3 C4 1.3725(19) . ?
C4 C4A 1.4356(19) . ?
C4 C2O 1.4765(18) . ?
C4A C5 1.4159(19) . ?
C4A C8A 1.4267(17) . ?
C5 C6 1.366(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.362(2) . ?
C8 C8A 1.4192(19) . ?
O1O C2O 1.3614(18) . ?
O1O C5O 1.432(2) . ?
C2O N3O 1.2622(19) . ?
N3O C4O 1.4803(19) . ?
C4O C7O 1.507(3) . ?
C4O C6O 1.510(3) . ?
C4O C5O 1.526(3) . ?
CC OC 1.2348(16) . ?
CC NG 1.3366(18) . ?
NG C1G 1.4425(18) . ?
C1G C2G 1.508(2) . ?
C2G O1G 1.1973(19) . ?
C2G O2G 1.320(2) . ?
O2G CMG 1.433(3) . ?

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 C8A 120.02(12) . . ?
C2 C1 CC 118.79(12) . . ?
C8A C1 CC 121.19(12) . . ?
C1 C2 C3 121.10(12) . . ?
C4 C3 C2 120.99(13) . . ?
C3 C4 C4A 119.88(12) . . ?
C3 C4 C2O 117.38(12) . . ?
C4A C4 C2O 122.66(12) . . ?
C5 C4A C8A 118.36(12) . . ?
C5 C4A C4 122.79(12) . . ?
C8A C4A C4 118.85(11) . . ?
C6 C5 C4A 120.96(14) . . ?
C5 C6 C7 120.67(14) . . ?
C8 C7 C6 120.30(14) . . ?
C7 C8 C8A 120.99(13) . . ?
C8 C8A C4A 118.69(12) . . ?
C8 C8A C1 122.21(12) . . ?
C4A C8A C1 119.09(11) . . ?
C2O O1O C5O 106.31(13) . . ?
N3O C2O O1O 117.09(13) . . ?
N3O C2O C4 128.36(13) . . ?
O1O C2O C4 114.48(12) . . ?
C2O N3O C4O 107.95(13) . . ?
N3O C4O C7O 108.01(15) . . ?
N3O C4O C6O 109.86(16) . . ?
C7O C4O C6O 110.38(18) . . ?
N3O C4O C5O 102.96(12) . . ?
C7O C4O C5O 112.6(2) . . ?
C6O C4O C5O 112.71(18) . . ?
O1O C5O C4O 105.06(14) . . ?
OC CC NG 120.66(12) . . ?
OC CC C1 123.44(12) . . ?
NG CC C1 115.89(11) . . ?
CC NG C1G 119.55(12) . . ?
NG C1G C2G 115.09(12) . . ?
O1G C2G O2G 124.09(16) . . ?
O1G C2G C1G 123.23(15) . . ?
O2G C2G C1G 112.66(13) . . ?
C2G O2G CMG 116.28(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NG HG OC 0.89(2) 2.01(2) 2.8208(16) 150.8(16) 4_566 yes

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.123


####################################################################### 
# 
# 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_1a1
_database_code_depnum_ccdc_archive 'CCDC 2335943'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C24 H24 N2 O4'
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45

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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   13.2430(4)
_cell_length_b                   20.7980(6)
_cell_length_c                   7.7513(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2134.92(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4841
_cell_measurement_theta_min      3.9460
_cell_measurement_theta_max      76.3430

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.700
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_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, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            8620
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.957
_diffrn_reflns_theta_max         79.578
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             4022
_reflns_number_gt                3596
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_max     0.777
_reflns_Friedel_fraction_full    0.880

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0806P)²+0.0975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4022
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.083
_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
C1 C 0.0615(2) 0.42157(12) 0.3150(4) 0.0545(6) Uani 1 1 d . . . . .
H1 H 0.057263 0.450760 0.224432 0.065 Uiso 1 1 calc R U . . .
C2 C -0.0246(2) 0.40028(15) 0.3907(4) 0.0627(7) Uani 1 1 d . . . . .
H2 H -0.086882 0.414993 0.351631 0.075 Uiso 1 1 calc R U . . .
C3 C -0.0203(2) 0.35596(15) 0.5283(4) 0.0634(7) Uani 1 1 d . . . . .
H3 H -0.079770 0.341531 0.579133 0.076 Uiso 1 1 calc R U . . .
C4 C 0.0697(2) 0.33431(13) 0.5869(4) 0.0558(6) Uani 1 1 d . . . . .
H4 H 0.071151 0.305297 0.678152 0.067 Uiso 1 1 calc R U . . .
C4A C 0.16271(19) 0.35502(11) 0.5117(3) 0.0443(5) Uani 1 1 d . . . . .
C10 C 0.25724(19) 0.33243(10) 0.5664(3) 0.0453(5) Uani 1 1 d . . . . .
C10A C 0.3469(2) 0.35186(11) 0.4862(3) 0.0469(5) Uani 1 1 d . . . . .
C5 C 0.4431(2) 0.32569(14) 0.5295(4) 0.0575(6) Uani 1 1 d . . . . .
H5 H 0.446946 0.293101 0.611364 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5288(2) 0.34713(16) 0.4544(4) 0.0666(8) Uani 1 1 d . . . . .
H6 H 0.590414 0.328694 0.483557 0.080 Uiso 1 1 calc R U . . .
C7 C 0.5254(2) 0.39729(17) 0.3320(5) 0.0687(8) Uani 1 1 d . . . . .
H7 H 0.585032 0.413404 0.285809 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4356(2) 0.42203(14) 0.2814(4) 0.0596(7) Uani 1 1 d . . . . .
H8 H 0.434390 0.454509 0.198987 0.072 Uiso 1 1 calc R U . . .
C8A C 0.34276(18) 0.39934(11) 0.3521(3) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.2485(2) 0.42180(10) 0.2964(3) 0.0471(5) Uani 1 1 d . . . . .
C9A C 0.15836(18) 0.40021(11) 0.3713(3) 0.0451(5) Uani 1 1 d . . . . .
O1O O 0.25282(19) 0.22493(8) 0.6823(2) 0.0631(5) Uani 1 1 d . . . . .
C2O C 0.26314(18) 0.28836(10) 0.7166(3) 0.0452(5) Uani 1 1 d . . . . .
N3O N 0.27741(18) 0.30520(9) 0.8709(3) 0.0541(5) Uani 1 1 d . . . . .
C4O C 0.2820(2) 0.24572(12) 0.9777(3) 0.0565(7) Uani 1 1 d . . . . .
C5O C 0.2525(4) 0.19376(13) 0.8490(4) 0.0775(9) Uani 1 1 d . . . . .
H5OA H 0.300742 0.158681 0.851442 0.093 Uiso 1 1 calc R U . . .
H5OB H 0.185973 0.176869 0.875265 0.093 Uiso 1 1 calc R U . . .
C6O C 0.2094(4) 0.25054(17) 1.1257(5) 0.0909(12) Uani 1 1 d . . . . .
H6OB H 0.142179 0.256518 1.082118 0.136 Uiso 1 1 calc R U . . .
H6OC H 0.227446 0.286462 1.197123 0.136 Uiso 1 1 calc R U . . .
H6OA H 0.212059 0.211744 1.192649 0.136 Uiso 1 1 calc R U . . .
C7O C 0.3884(4) 0.2376(3) 1.0417(8) 0.1157(17) Uani 1 1 d . . . . .
H7OC H 0.432447 0.229667 0.945754 0.174 Uiso 1 1 calc R U . . .
H7OA H 0.391306 0.202005 1.120265 0.174 Uiso 1 1 calc R U . . .
H7OB H 0.409330 0.276120 1.100053 0.174 Uiso 1 1 calc R U . . .
CC C 0.24266(19) 0.46959(10) 0.1499(3) 0.0485(5) Uani 1 1 d . . . . .
OC O 0.22929(17) 0.52711(8) 0.1747(3) 0.0639(5) Uani 1 1 d . . . . .
NA N 0.25270(19) 0.44408(10) -0.0081(3) 0.0529(5) Uani 1 1 d . . . . .
HA H 0.267(3) 0.3991(18) -0.028(5) 0.071(9) Uiso 1 1 d . . . . .
C1A C 0.2366(2) 0.48154(12) -0.1644(3) 0.0589(6) Uani 1 1 d . . . . .
H1A H 0.260381 0.455168 -0.260964 0.071 Uiso 1 1 calc R U . . .
C2A C 0.2978(2) 0.54327(13) -0.1676(4) 0.0618(7) Uani 1 1 d . . . . .
C3A C 0.1268(3) 0.49502(19) -0.1967(6) 0.0847(11) Uani 1 1 d . . . . .
H3AA H 0.119498 0.517612 -0.304021 0.127 Uiso 1 1 calc R U . . .
H3AB H 0.100372 0.520883 -0.104625 0.127 Uiso 1 1 calc R U . . .
H3AC H 0.090323 0.455180 -0.202248 0.127 Uiso 1 1 calc R U . . .
O1A O 0.2676(2) 0.59230(11) -0.2257(4) 0.1010(10) Uani 1 1 d . . . . .
O2A O 0.39138(16) 0.53465(10) -0.1105(3) 0.0682(6) Uani 1 1 d . . . . .
CMA C 0.4590(3) 0.5881(2) -0.1318(6) 0.0888(11) Uani 1 1 d . . . . .
HMAA H 0.526511 0.574975 -0.103642 0.133 Uiso 1 1 calc R U . . .
HMAB H 0.438852 0.622522 -0.056753 0.133 Uiso 1 1 calc R U . . .
HMAC H 0.456848 0.602612 -0.249378 0.133 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
C1 C2 1.357(4) . ?
C1 C9A 1.426(4) . ?
C2 C3 1.411(4) . ?
C3 C4 1.353(4) . ?
C4 C4A 1.429(4) . ?
C4A C10 1.403(4) . ?
C4A C9A 1.439(3) . ?
C10 C10A 1.400(4) . ?
C10 C2O 1.484(3) . ?
C10A C5 1.425(4) . ?
C10A C8A 1.435(4) . ?
C5 C6 1.351(4) . ?
C6 C7 1.411(5) . ?
C7 C8 1.354(4) . ?
C8 C8A 1.426(4) . ?
C8A C9 1.401(4) . ?
C9 C9A 1.402(4) . ?
C9 CC 1.511(3) . ?
O1O C2O 1.353(3) . ?
O1O C5O 1.446(3) . ?
C2O N3O 1.260(3) . ?
N3O C4O 1.490(3) . ?
C4O C6O 1.500(5) . ?
C4O C7O 1.504(5) . ?
C4O C5O 1.521(4) . ?
CC OC 1.224(3) . ?
CC NA 1.341(3) . ?
NA C1A 1.456(3) . ?
C1A C3A 1.502(5) . ?
C1A C2A 1.519(4) . ?
C2A O1A 1.184(4) . ?
C2A O2A 1.328(4) . ?
O2A CMA 1.438(4) . ?

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 C9A 121.5(3) . . ?
C1 C2 C3 120.4(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C4A 121.5(3) . . ?
C10 C4A C4 123.0(2) . . ?
C10 C4A C9A 118.9(2) . . ?
C4 C4A C9A 118.1(2) . . ?
C10A C10 C4A 121.7(2) . . ?
C10A C10 C2O 118.8(2) . . ?
C4A C10 C2O 119.4(2) . . ?
C10 C10A C5 122.9(2) . . ?
C10 C10A C8A 119.2(2) . . ?
C5 C10A C8A 117.9(2) . . ?
C6 C5 C10A 121.5(3) . . ?
C5 C6 C7 120.5(3) . . ?
C8 C7 C6 120.3(3) . . ?
C7 C8 C8A 121.4(3) . . ?
C9 C8A C8 122.6(2) . . ?
C9 C8A C10A 119.2(2) . . ?
C8 C8A C10A 118.2(2) . . ?
C8A C9 C9A 121.6(2) . . ?
C8A C9 CC 119.8(2) . . ?
C9A C9 CC 118.6(2) . . ?
C9 C9A C1 122.7(2) . . ?
C9 C9A C4A 119.2(2) . . ?
C1 C9A C4A 118.1(2) . . ?
C2O O1O C5O 105.16(19) . . ?
N3O C2O O1O 118.2(2) . . ?
N3O C2O C10 125.5(2) . . ?
O1O C2O C10 116.26(19) . . ?
C2O N3O C4O 107.6(2) . . ?
N3O C4O C6O 110.1(2) . . ?
N3O C4O C7O 108.3(3) . . ?
C6O C4O C7O 110.8(4) . . ?
N3O C4O C5O 102.4(2) . . ?
C6O C4O C5O 112.6(3) . . ?
C7O C4O C5O 112.2(3) . . ?
O1O C5O C4O 105.5(2) . . ?
OC CC NA 123.0(2) . . ?
OC CC C9 122.1(2) . . ?
NA CC C9 114.87(19) . . ?
CC NA C1A 122.2(2) . . ?
NA C1A C3A 112.4(3) . . ?
NA C1A C2A 112.8(2) . . ?
C3A C1A C2A 110.9(2) . . ?
O1A C2A O2A 123.9(3) . . ?
O1A C2A C1A 123.7(3) . . ?
O2A C2A C1A 112.2(2) . . ?
C2A O2A CMA 116.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA N3O 0.97(4) 2.11(4) 3.054(3) 165(3) 1_554 yes

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_1n5
_database_code_depnum_ccdc_archive 'CCDC 2335942'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C20 H22 N2 O4'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.39

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.18300(10)
_cell_length_b                   5.51200(10)
_cell_length_c                   64.5994(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1845.52(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10313
_cell_measurement_theta_min      8.0790
_cell_measurement_theta_max      77.5890

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.73480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_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, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14023
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -81
_diffrn_reflns_limit_l_max       81
_diffrn_reflns_theta_min         8.069
_diffrn_reflns_theta_max         79.716
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3887
_reflns_number_gt                3813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.987

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.1757P)²+1.2541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2865
_refine_ls_wR_factor_gt          0.2856
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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
C1 C 0.3632(9) 0.2870(9) 0.11430(7) 0.0389(10) Uani 1 1 d . . . . .
H1 H 0.257309 0.153523 0.111981 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5623(9) 0.3372(9) 0.10064(7) 0.0398(10) Uani 1 1 d . . . . .
C3 C 0.7176(9) 0.5432(10) 0.10396(7) 0.0430(11) Uani 1 1 d . . . . .
H3 H 0.853473 0.575347 0.094959 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6721(10) 0.6967(9) 0.12017(8) 0.0435(11) Uani 1 1 d . . . . .
H4 H 0.772126 0.835599 0.121711 0.052 Uiso 1 1 calc R U . . .
C4A C 0.4731(9) 0.6459(8) 0.13472(7) 0.0370(9) Uani 1 1 d . . . . .
C5 C 0.4316(11) 0.7952(9) 0.15233(7) 0.0454(11) Uani 1 1 d . . . . .
H5 H 0.529053 0.935264 0.154147 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2483(11) 0.7332(9) 0.16660(8) 0.0451(11) Uani 1 1 d . . . . .
H6 H 0.220985 0.831880 0.178067 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1005(9) 0.5204(9) 0.16403(7) 0.0385(9) Uani 1 1 d . . . . .
C8 C 0.1290(9) 0.3783(8) 0.14684(7) 0.0376(9) Uani 1 1 d . . . . .
H8 H 0.023815 0.243232 0.145010 0.045 Uiso 1 1 calc R U . . .
C8A C 0.3196(9) 0.4365(8) 0.13168(7) 0.0357(9) Uani 1 1 d . . . . .
O1O O -0.2359(8) 0.2578(8) 0.17671(5) 0.0538(10) Uani 1 1 d . . . . .
C2O C -0.0745(9) 0.4452(8) 0.18096(7) 0.0372(9) Uani 1 1 d . . . . .
N3O N -0.0714(9) 0.5278(9) 0.19912(6) 0.0466(10) Uani 1 1 d . . . . .
C4O C -0.2505(9) 0.3780(10) 0.21175(7) 0.0446(12) Uani 1 1 d . . . . .
C5O C -0.3883(11) 0.2213(11) 0.19537(8) 0.0515(13) Uani 1 1 d . . . . .
H5OA H -0.389230 0.051737 0.199400 0.062 Uiso 1 1 calc R U . . .
H5OB H -0.564749 0.274962 0.193355 0.062 Uiso 1 1 calc R U . . .
C6O C -0.4330(14) 0.5402(14) 0.22357(11) 0.0690(18) Uani 1 1 d . . . . .
H6OB H -0.543433 0.623939 0.214018 0.104 Uiso 1 1 calc R U . . .
H6OC H -0.335656 0.656264 0.231437 0.104 Uiso 1 1 calc R U . . .
H6OA H -0.535887 0.443678 0.232779 0.104 Uiso 1 1 calc R U . . .
C7O C -0.0930(15) 0.2213(15) 0.22627(10) 0.0727(19) Uani 1 1 d . . . . .
H7OA H -0.206606 0.121581 0.234359 0.109 Uiso 1 1 calc R U . . .
H7OB H 0.006625 0.322990 0.235302 0.109 Uiso 1 1 calc R U . . .
H7OC H 0.020734 0.119875 0.218353 0.109 Uiso 1 1 calc R U . . .
CC C 0.6290(9) 0.1697(10) 0.08318(7) 0.0425(10) Uani 1 1 d . . . . .
OC O 0.8530(8) 0.1387(10) 0.07818(7) 0.0630(12) Uani 1 1 d . . . . .
NA N 0.4319(9) 0.0508(9) 0.07420(6) 0.0447(10) Uani 1 1 d . . . . .
HA H 0.263(12) 0.095(10) 0.0759(9) 0.037(14) Uiso 1 1 d . . . . .
C1A C 0.4803(9) -0.1224(10) 0.05774(7) 0.0439(11) Uani 1 1 d . . . . .
H1A H 0.630403 -0.220274 0.061659 0.053 Uiso 1 1 calc R U . . .
C2A C 0.5428(15) 0.0065(12) 0.03781(9) 0.0604(15) Uani 1 1 d . . . . .
C3A C 0.2529(12) -0.2907(13) 0.05514(10) 0.0631(15) Uani 1 1 d . . . . .
H3AB H 0.106359 -0.199939 0.050375 0.095 Uiso 1 1 calc R U . . .
H3AC H 0.212892 -0.365005 0.068193 0.095 Uiso 1 1 calc R U . . .
H3AA H 0.294715 -0.414075 0.045209 0.095 Uiso 1 1 calc R U . . .
O1A O 0.458(2) 0.1949(12) 0.03276(9) 0.137(4) Uani 1 1 d . . . . .
O2A O 0.6949(13) -0.1247(12) 0.02594(8) 0.092(2) Uani 1 1 d . . . . .
CMA C 0.772(3) -0.012(3) 0.00664(16) 0.152(6) Uani 1 1 d . . . . .
HMAC H 0.629191 -0.014515 -0.002851 0.228 Uiso 1 1 calc R U . . .
HMAA H 0.913959 -0.100274 0.000803 0.228 Uiso 1 1 calc R U . . .
HMAB H 0.822709 0.152472 0.009184 0.228 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
C1 C2 1.386(6) . ?
C1 C8A 1.411(6) . ?
C2 C3 1.408(7) . ?
C2 CC 1.498(6) . ?
C3 C4 1.367(7) . ?
C4 C4A 1.423(7) . ?
C4A C8A 1.416(6) . ?
C4A C5 1.420(6) . ?
C5 C6 1.367(7) . ?
C6 C7 1.411(7) . ?
C7 C8 1.367(6) . ?
C7 C2O 1.480(6) . ?
C8 C8A 1.427(6) . ?
O1O C2O 1.357(6) . ?
O1O C5O 1.455(6) . ?
C2O N3O 1.258(6) . ?
N3O C4O 1.486(6) . ?
C4O C6O 1.509(8) . ?
C4O C7O 1.514(8) . ?
C4O C5O 1.541(7) . ?
CC OC 1.218(6) . ?
CC NA 1.345(7) . ?
NA C1A 1.451(6) . ?
C1A C2A 1.505(7) . ?
C1A C3A 1.509(9) . ?
C2A O1A 1.173(9) . ?
C2A O2A 1.316(8) . ?
O2A CMA 1.448(11) . ?

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 C8A 120.6(4) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 CC 121.9(5) . . ?
C3 C2 CC 118.7(4) . . ?
C4 C3 C2 121.1(4) . . ?
C3 C4 C4A 120.6(5) . . ?
C8A C4A C5 119.9(4) . . ?
C8A C4A C4 118.4(4) . . ?
C5 C4A C4 121.6(4) . . ?
C6 C5 C4A 120.0(5) . . ?
C5 C6 C7 120.4(4) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 C2O 120.4(4) . . ?
C6 C7 C2O 118.6(4) . . ?
C7 C8 C8A 120.2(4) . . ?
C1 C8A C4A 119.8(4) . . ?
C1 C8A C8 121.7(4) . . ?
C4A C8A C8 118.5(4) . . ?
C2O O1O C5O 105.8(4) . . ?
N3O C2O O1O 118.1(4) . . ?
N3O C2O C7 125.4(4) . . ?
O1O C2O C7 116.2(4) . . ?
C2O N3O C4O 107.6(4) . . ?
N3O C4O C6O 109.9(5) . . ?
N3O C4O C7O 108.7(4) . . ?
C6O C4O C7O 111.3(6) . . ?
N3O C4O C5O 102.9(4) . . ?
C6O C4O C5O 112.9(5) . . ?
C7O C4O C5O 110.8(5) . . ?
O1O C5O C4O 103.9(4) . . ?
OC CC NA 122.8(5) . . ?
OC CC C2 120.4(5) . . ?
NA CC C2 116.7(4) . . ?
CC NA C1A 120.3(4) . . ?
NA C1A C2A 110.7(5) . . ?
NA C1A C3A 110.5(4) . . ?
C2A C1A C3A 111.3(5) . . ?
O1A C2A O2A 123.2(6) . . ?
O1A C2A C1A 125.1(6) . . ?
O2A C2A C1A 111.6(5) . . ?
C2A O2A CMA 115.5(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA OC 0.91(6) 2.14(6) 3.050(6) 171(5) 1_455 yes

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.093


####################################################################### 
# 
# 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_2m1
_database_code_depnum_ccdc_archive 'CCDC 2335945'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C16 H20 N2 O6'
_chemical_formula_sum            'C16 H20 N2 O6'
_chemical_formula_weight         336.34

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   6.4358(2)
_cell_length_b                   8.0804(3)
_cell_length_c                   16.4380(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.198(3)
_cell_angle_gamma                90
_cell_volume                     846.10(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1057
_cell_measurement_theta_min      8.1620
_cell_measurement_theta_max      70.0670

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.856
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.67466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            1358
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         8.172
_diffrn_reflns_theta_max         70.186
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.611
_diffrn_reflns_point_group_measured_fraction_full 0.635
_reflns_number_total             994
_reflns_number_gt                980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.252
_reflns_Friedel_fraction_max     0.265
_reflns_Friedel_fraction_full    0.281

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0979P)²+0.2690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         994
_refine_ls_number_parameters     116
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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
C1 C 0.4052(4) 0.4151(5) 0.43120(18) 0.0389(8) Uani 1 1 d . . . . .
C2 C 0.500000 0.3286(7) 0.500000 0.0412(10) Uani 1 2 d S T P . .
H2 H 0.500004 0.213467 0.499999 0.049 Uiso 1 2 calc R U P . .
C5 C 0.500000 0.6719(7) 0.500000 0.0455(11) Uani 1 2 d S T P . .
H5 H 0.500002 0.786950 0.500000 0.055 Uiso 1 2 calc R U P . .
C6 C 0.4026(5) 0.5867(5) 0.43205(19) 0.0434(8) Uani 1 1 d . . . . .
H6 H 0.335396 0.644521 0.386912 0.052 Uiso 1 1 calc R U . . .
CC C 0.3128(5) 0.3164(4) 0.3576(2) 0.0412(8) Uani 1 1 d . . . . .
OC O 0.3927(4) 0.1872(4) 0.33927(17) 0.0600(8) Uani 1 1 d . . . . .
NA N 0.1380(5) 0.3781(4) 0.31284(17) 0.0441(7) Uani 1 1 d . . . . .
HA H 0.081(6) 0.471(6) 0.325(2) 0.032(9) Uiso 1 1 d . . . . .
C1A C 0.0463(5) 0.2963(4) 0.23811(19) 0.0428(8) Uani 1 1 d . . . . .
H1A H 0.049079 0.176495 0.247613 0.051 Uiso 1 1 calc R U . . .
C2A C 0.1749(6) 0.3348(5) 0.1697(2) 0.0511(9) Uani 1 1 d . . . . .
C3A C -0.1798(6) 0.3500(6) 0.2134(2) 0.0587(11) Uani 1 1 d . . . . .
H3AB H -0.185028 0.467831 0.205820 0.088 Uiso 1 1 calc R U . . .
H3AC H -0.261024 0.319778 0.255717 0.088 Uiso 1 1 calc R U . . .
H3AA H -0.236299 0.296462 0.162906 0.088 Uiso 1 1 calc R U . . .
O1A O 0.2885(9) 0.4474(6) 0.1676(3) 0.1120(18) Uani 1 1 d . . . . .
O2A O 0.1505(6) 0.2193(5) 0.11241(17) 0.0733(10) Uani 1 1 d . . . . .
CMA C 0.2760(12) 0.2379(11) 0.0464(3) 0.098(2) Uani 1 1 d . . . . .
HMAA H 0.212657 0.176739 -0.000754 0.147 Uiso 1 1 calc R U . . .
HMAB H 0.414935 0.196341 0.063998 0.147 Uiso 1 1 calc R U . . .
HMAC H 0.283625 0.352793 0.032351 0.147 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
C1 C6 1.386(5) . ?
C1 C2 1.394(4) . ?
C1 CC 1.500(4) . ?
C5 C6 1.384(4) 2_656 ?
C5 C6 1.384(4) . ?
CC OC 1.221(4) . ?
CC NA 1.349(4) . ?
NA C1A 1.445(4) . ?
C1A C3A 1.517(5) . ?
C1A C2A 1.521(5) . ?
C2A O1A 1.171(6) . ?
C2A O2A 1.319(5) . ?
O2A CMA 1.450(6) . ?

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 C1 C2 119.9(3) . . ?
C6 C1 CC 122.4(3) . . ?
C2 C1 CC 117.7(4) . . ?
C1 C2 C1 119.8(5) . 2_656 ?
C6 C5 C6 120.3(5) 2_656 . ?
C5 C6 C1 120.1(3) . . ?
OC CC NA 122.0(3) . . ?
OC CC C1 121.4(3) . . ?
NA CC C1 116.6(3) . . ?
CC NA C1A 120.2(3) . . ?
NA C1A C3A 110.9(3) . . ?
NA C1A C2A 109.6(3) . . ?
C3A C1A C2A 110.2(3) . . ?
O1A C2A O2A 122.7(4) . . ?
O1A C2A C1A 126.0(4) . . ?
O2A C2A C1A 111.2(3) . . ?
C2A O2A CMA 116.0(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA OC 0.87(4) 2.16(5) 3.019(4) 170(3) 3_455 yes

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044


####################################################################### 
# 
# 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_2n5
_database_code_depnum_ccdc_archive 'CCDC 2335947'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C20 H22 N2 O6'
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.39

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   6.5044(4)
_cell_length_b                   8.0195(6)
_cell_length_c                   18.7137(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.141(6)
_cell_angle_gamma                90
_cell_volume                     972.22(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1276
_cell_measurement_theta_min      4.7170
_cell_measurement_theta_max      69.5320

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.819
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            1845
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.745
_diffrn_reflns_theta_max         70.188
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_point_group_measured_fraction_full 0.745
_reflns_number_total             1343
_reflns_number_gt                1261
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.418
_reflns_Friedel_fraction_max     0.459
_reflns_Friedel_fraction_full    0.481

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0800P)²+0.3541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1343
_refine_ls_number_parameters     134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
C1 C 0.4222(5) 0.4015(5) 0.43759(17) 0.0475(9) Uani 1 1 d . . . . .
H1 H 0.426190 0.285596 0.436753 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3400(5) 0.4862(5) 0.37748(18) 0.0469(9) Uani 1 1 d . . . . .
C3 C 0.3375(5) 0.6619(5) 0.37882(18) 0.0498(9) Uani 1 1 d . . . . .
H3 H 0.281268 0.719924 0.338702 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4155(5) 0.7479(5) 0.43751(18) 0.0498(9) Uani 1 1 d . . . . .
H4 H 0.413305 0.863816 0.436653 0.060 Uiso 1 1 calc R U . . .
C4A C 0.500000 0.6646(7) 0.500000 0.0452(11) Uani 1 2 d S T P . .
C8A C 0.500000 0.4860(6) 0.500000 0.0440(11) Uani 1 2 d S T P . .
CC C 0.2630(5) 0.3877(5) 0.31292(18) 0.0481(8) Uani 1 1 d . . . . .
OC O 0.3440(5) 0.2571(4) 0.29709(15) 0.0690(9) Uani 1 1 d . . . . .
NA N 0.0981(5) 0.4503(4) 0.27289(15) 0.0505(8) Uani 1 1 d . . . . .
HA H 0.044(6) 0.535(5) 0.2857(18) 0.034(9) Uiso 1 1 d . . . . .
C1A C 0.0185(5) 0.3675(4) 0.20763(16) 0.0465(8) Uani 1 1 d . . . . .
H1A H 0.018951 0.246855 0.216068 0.056 Uiso 1 1 calc R U . . .
C2A C 0.1556(6) 0.4053(5) 0.1483(2) 0.0563(9) Uani 1 1 d . . . . .
C3A C -0.2022(6) 0.4234(6) 0.1859(2) 0.0626(11) Uani 1 1 d . . . . .
H3AB H -0.203364 0.540347 0.175016 0.094 Uiso 1 1 calc R U . . .
H3AC H -0.286019 0.402890 0.224683 0.094 Uiso 1 1 calc R U . . .
H3AA H -0.256254 0.362023 0.144340 0.094 Uiso 1 1 calc R U . . .
O1A O 0.2715(9) 0.5171(6) 0.1472(3) 0.126(2) Uani 1 1 d . . . . .
O2A O 0.1351(6) 0.2920(5) 0.09741(16) 0.0792(10) Uani 1 1 d . . . . .
CMA C 0.2709(11) 0.3083(11) 0.0405(3) 0.106(2) Uani 1 1 d . . . . .
HMAA H 0.219809 0.241017 0.000341 0.159 Uiso 1 1 calc R U . . .
HMAB H 0.407108 0.271744 0.057558 0.159 Uiso 1 1 calc R U . . .
HMAC H 0.275858 0.422870 0.025920 0.159 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
C1 C2 1.380(5) . ?
C1 C8A 1.405(4) . ?
C2 C3 1.409(5) . ?
C2 CC 1.492(5) . ?
C3 C4 1.356(5) . ?
C4 C4A 1.415(4) . ?
C4A C8A 1.432(7) . ?
CC OC 1.221(5) . ?
CC NA 1.349(4) . ?
NA C1A 1.445(4) . ?
C1A C2A 1.516(5) . ?
C1A C3A 1.524(5) . ?
C2A O1A 1.173(6) . ?
C2A O2A 1.314(5) . ?
O2A CMA 1.449(6) . ?

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 C8A 121.6(4) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 CC 118.5(3) . . ?
C3 C2 CC 122.7(3) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C4A 121.2(4) . . ?
C4 C4A C4 123.6(5) . 2_656 ?
C4 C4A C8A 118.2(2) . . ?
C4 C4A C8A 118.2(2) 2_656 . ?
C1 C8A C1 122.3(5) 2_656 . ?
C1 C8A C4A 118.8(2) 2_656 . ?
C1 C8A C4A 118.8(2) . . ?
OC CC NA 121.6(3) . . ?
OC CC C2 122.0(3) . . ?
NA CC C2 116.4(3) . . ?
CC NA C1A 120.3(3) . . ?
NA C1A C2A 109.7(3) . . ?
NA C1A C3A 110.3(3) . . ?
C2A C1A C3A 110.3(3) . . ?
O1A C2A O2A 122.6(4) . . ?
O1A C2A C1A 126.0(4) . . ?
O2A C2A C1A 111.4(3) . . ?
C2A O2A CMA 116.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA OC 0.81(4) 2.23(4) 3.020(4) 166(3) 3_455 yes

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_4m5
_database_code_depnum_ccdc_archive 'CCDC 2335946'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C24 H24 N2 O4'
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   20.892(2)
_cell_length_b                   4.9926(3)
_cell_length_c                   21.517(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.246(12)
_cell_angle_gamma                90
_cell_volume                     2091.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2738
_cell_measurement_theta_min      4.2210
_cell_measurement_theta_max      75.4330

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.30629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            11420
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.269
_diffrn_reflns_theta_max         77.035
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             3874
_reflns_number_gt                2974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.590
_reflns_Friedel_fraction_max     0.734
_reflns_Friedel_fraction_full    0.775

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0862P)²+0.5380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3874
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1677
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.1184(2) 0.4466(9) 0.2613(2) 0.0495(9) Uani 1 1 d . . . . .
C2 C 0.1757(2) 0.3502(9) 0.2495(2) 0.0488(9) Uani 1 1 d . . . . .
H2 H 0.201086 0.209503 0.275015 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1948(2) 0.4632(9) 0.2000(2) 0.0483(9) Uani 1 1 d . . . . .
C4 C 0.1542(2) 0.6610(11) 0.1589(2) 0.0556(10) Uani 1 1 d . . . . .
H4 H 0.166493 0.734313 0.125070 0.067 Uiso 1 1 calc R U . . .
C5 C 0.0955(3) 0.7491(13) 0.1684(3) 0.0643(13) Uani 1 1 d . . . . .
H5 H 0.067933 0.879305 0.140429 0.077 Uiso 1 1 calc R U . . .
C6 C 0.0780(2) 0.6428(10) 0.2195(2) 0.0553(10) Uani 1 1 d . . . . .
H6 H 0.038745 0.703315 0.225866 0.066 Uiso 1 1 calc R U . . .
CC1 C 0.1009(2) 0.3376(9) 0.3174(2) 0.0484(9) Uani 1 1 d . . . . .
OC1 O 0.1041(2) 0.0983(7) 0.3314(2) 0.0639(9) Uani 1 1 d . . . . .
NB1 N 0.0808(2) 0.5230(8) 0.3522(2) 0.0564(9) Uani 1 1 d . . . . .
HB1 H 0.088(3) 0.693(16) 0.346(3) 0.066(16) Uiso 1 1 d . . . . .
C1B1 C 0.0556(2) 0.4504(10) 0.4047(2) 0.0511(9) Uani 1 1 d . . . . .
H1B1 H 0.032953 0.275792 0.393394 0.061 Uiso 1 1 calc R U . . .
C2B1 C 0.0013(3) 0.6569(10) 0.4046(2) 0.0580(11) Uani 1 1 d . . . . .
H2BB H -0.017584 0.605629 0.437972 0.070 Uiso 1 1 calc R U . . .
H2BA H 0.023406 0.829551 0.417470 0.070 Uiso 1 1 calc R U . . .
OB1 O -0.0528(2) 0.6842(8) 0.34304(19) 0.0673(9) Uani 1 1 d . . . . .
HOB1 H -0.070042 0.537041 0.330388 0.101 Uiso 1 1 calc R U . . .
C3B1 C 0.1109(2) 0.4281(10) 0.4729(2) 0.0538(10) Uani 1 1 d . . . . .
C4B1 C 0.1043(3) 0.2469(12) 0.5189(3) 0.0641(12) Uani 1 1 d . . . . .
H4B1 H 0.065340 0.139194 0.506978 0.077 Uiso 1 1 calc R U . . .
C5B1 C 0.1537(4) 0.2211(17) 0.5819(3) 0.0843(17) Uani 1 1 d . . . . .
H5B1 H 0.147866 0.098545 0.611987 0.101 Uiso 1 1 calc R U . . .
C6B1 C 0.2116(4) 0.3777(17) 0.5999(4) 0.091(2) Uani 1 1 d . . . . .
H6B1 H 0.245719 0.358532 0.641769 0.109 Uiso 1 1 calc R U . . .
C7B1 C 0.2188(3) 0.5626(18) 0.5558(4) 0.096(2) Uani 1 1 d . . . . .
H7B1 H 0.257762 0.670146 0.568245 0.116 Uiso 1 1 calc R U . . .
C8B1 C 0.1685(3) 0.5916(13) 0.4925(3) 0.0751(15) Uani 1 1 d . . . . .
H8B1 H 0.173615 0.720425 0.463415 0.090 Uiso 1 1 calc R U . . .
CC2 C 0.2598(2) 0.3729(8) 0.1917(2) 0.0501(9) Uani 1 1 d . . . . .
OC2 O 0.2763(2) 0.1354(7) 0.1964(3) 0.0786(13) Uani 1 1 d . . . . .
NB2 N 0.29636(19) 0.5682(7) 0.1779(2) 0.0510(9) Uani 1 1 d . . . . .
HB2 H 0.286(3) 0.754(15) 0.181(3) 0.068(17) Uiso 1 1 d . . . . .
C1B2 C 0.3634(2) 0.5185(9) 0.1739(2) 0.0506(10) Uani 1 1 d . . . . .
H1B2 H 0.375406 0.330866 0.185889 0.061 Uiso 1 1 calc R U . . .
C2B2 C 0.4167(2) 0.6939(11) 0.2252(3) 0.0579(11) Uani 1 1 d . . . . .
H2BD H 0.462146 0.641351 0.227458 0.069 Uiso 1 1 calc R U . . .
H2BC H 0.409559 0.878883 0.210502 0.069 Uiso 1 1 calc R U . . .
OB2 O 0.4136(2) 0.6758(8) 0.28926(19) 0.0729(10) Uani 1 1 d . . . . .
HOB2 H 0.426007 0.526094 0.304597 0.109 Uiso 1 1 calc R U . . .
C3B2 C 0.3653(2) 0.5638(10) 0.1054(3) 0.0543(10) Uani 1 1 d . . . . .
C4B2 C 0.4069(3) 0.4078(15) 0.0831(3) 0.0784(17) Uani 1 1 d . . . . .
H4B2 H 0.431387 0.267171 0.109417 0.094 Uiso 1 1 calc R U . . .
C5B2 C 0.4130(4) 0.457(2) 0.0222(4) 0.097(2) Uani 1 1 d . . . . .
H5B2 H 0.442480 0.352891 0.008537 0.116 Uiso 1 1 calc R U . . .
C6B2 C 0.3753(4) 0.6599(18) -0.0186(3) 0.092(2) Uani 1 1 d . . . . .
H6B2 H 0.380664 0.698975 -0.058712 0.110 Uiso 1 1 calc R U . . .
C7B2 C 0.3305(4) 0.8006(18) 0.0011(4) 0.094(2) Uani 1 1 d . . . . .
H7B2 H 0.302688 0.929240 -0.027283 0.113 Uiso 1 1 calc R U . . .
C8B2 C 0.3254(3) 0.7562(14) 0.0627(3) 0.0766(16) Uani 1 1 d . . . . .
H8B2 H 0.294768 0.857113 0.075356 0.092 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
C1 C6 1.390(7) . ?
C1 C2 1.394(6) . ?
C1 CC1 1.487(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.390(7) . ?
C3 CC2 1.501(5) . ?
C4 C5 1.386(6) . ?
C5 C6 1.384(7) . ?
CC1 OC1 1.228(6) . ?
CC1 NB1 1.349(6) . ?
NB1 C1B1 1.455(5) . ?
C1B1 C3B1 1.506(7) . ?
C1B1 C2B1 1.533(6) . ?
C2B1 OB1 1.402(6) . ?
C3B1 C4B1 1.385(7) . ?
C3B1 C8B1 1.388(7) . ?
C4B1 C5B1 1.382(8) . ?
C5B1 C6B1 1.372(11) . ?
C6B1 C7B1 1.371(12) . ?
C7B1 C8B1 1.393(10) . ?
CC2 OC2 1.229(6) . ?
CC2 NB2 1.337(5) . ?
NB2 C1B2 1.455(5) . ?
C1B2 C3B2 1.504(7) . ?
C1B2 C2B2 1.528(7) . ?
C2B2 OB2 1.406(6) . ?
C3B2 C4B2 1.377(7) . ?
C3B2 C8B2 1.382(8) . ?
C4B2 C5B2 1.384(9) . ?
C5B2 C6B2 1.384(12) . ?
C6B2 C7B2 1.355(10) . ?
C7B2 C8B2 1.385(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
C6 C1 C2 119.0(4) . . ?
C6 C1 CC1 120.9(4) . . ?
C2 C1 CC1 120.1(4) . . ?
C3 C2 C1 120.3(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 CC2 119.6(4) . . ?
C4 C3 CC2 120.5(4) . . ?
C5 C4 C3 120.0(4) . . ?
C6 C5 C4 119.9(5) . . ?
C5 C6 C1 120.7(4) . . ?
OC1 CC1 NB1 122.2(4) . . ?
OC1 CC1 C1 123.1(4) . . ?
NB1 CC1 C1 114.7(4) . . ?
CC1 NB1 C1B1 122.2(4) . . ?
NB1 C1B1 C3B1 114.2(4) . . ?
NB1 C1B1 C2B1 107.9(4) . . ?
C3B1 C1B1 C2B1 110.9(4) . . ?
OB1 C2B1 C1B1 114.2(4) . . ?
C4B1 C3B1 C8B1 117.8(5) . . ?
C4B1 C3B1 C1B1 120.3(4) . . ?
C8B1 C3B1 C1B1 121.8(5) . . ?
C5B1 C4B1 C3B1 122.0(6) . . ?
C6B1 C5B1 C4B1 119.5(7) . . ?
C7B1 C6B1 C5B1 119.7(7) . . ?
C6B1 C7B1 C8B1 120.9(7) . . ?
C3B1 C8B1 C7B1 120.0(6) . . ?
OC2 CC2 NB2 123.8(4) . . ?
OC2 CC2 C3 121.3(4) . . ?
NB2 CC2 C3 115.0(4) . . ?
CC2 NB2 C1B2 121.9(4) . . ?
NB2 C1B2 C3B2 113.6(4) . . ?
NB2 C1B2 C2B2 108.9(4) . . ?
C3B2 C1B2 C2B2 110.5(4) . . ?
OB2 C2B2 C1B2 113.1(4) . . ?
C4B2 C3B2 C8B2 117.7(5) . . ?
C4B2 C3B2 C1B2 120.0(5) . . ?
C8B2 C3B2 C1B2 122.2(4) . . ?
C3B2 C4B2 C5B2 121.1(6) . . ?
C4B2 C5B2 C6B2 120.2(6) . . ?
C7B2 C6B2 C5B2 118.7(6) . . ?
C6B2 C7B2 C8B2 121.1(7) . . ?
C3B2 C8B2 C7B2 120.8(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NB1 HB1 OC1 0.88(8) 2.10(8) 2.974(5) 179(5) 1_565 yes
OB1 HOB1 OB2 0.82 1.98 2.772(6) 161.2 3_445 yes
NB2 HB2 OC2 0.96(7) 1.96(7) 2.911(5) 173(6) 1_565 yes
OB2 HOB2 OB1 0.82 1.88 2.696(6) 174.2 3_545 yes

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_1t4
_database_code_depnum_ccdc_archive 'CCDC 2335944'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C37 H35 N3 O7'
_chemical_formula_sum            'C37 H35 N3 O7'
_chemical_formula_weight         633.68

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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.8070(2)
_cell_length_b                   18.8070(2)
_cell_length_c                   19.0641(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6743.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5709
_cell_measurement_theta_min      4.0310
_cell_measurement_theta_max      67.3780

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             2672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.29523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            14949
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.323
_diffrn_reflns_theta_max         68.589
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             5899
_reflns_number_gt                4958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.947

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.0557P)²+0.3781P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.26(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5899
_refine_ls_number_parameters     434
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.06702(14) 0.24789(14) 0.37745(16) 0.0475(6) Uani 1 1 d . . . . .
C2 C 0.04154(13) 0.31118(14) 0.34967(14) 0.0444(6) Uani 1 1 d . . . . .
H2 H 0.019685 0.311128 0.305912 0.053 Uiso 1 1 calc R U . . .
C3 C 0.04828(13) 0.37454(14) 0.38641(13) 0.0422(5) Uani 1 1 d . . . . .
C4 C 0.07829(14) 0.37346(14) 0.45303(14) 0.0447(6) Uani 1 1 d . . . . .
H4 H 0.081738 0.415442 0.478581 0.054 Uiso 1 1 calc R U . . .
C5 C 0.10319(13) 0.31031(14) 0.48190(15) 0.0461(6) Uani 1 1 d . . . . .
C6 C 0.09885(14) 0.24778(14) 0.44309(16) 0.0486(6) Uani 1 1 d . . . . .
H6 H 0.117353 0.205766 0.461225 0.058 Uiso 1 1 calc R U . . .
O1O O 0.14573(12) 0.37597(11) 0.58022(11) 0.0625(6) Uani 1 1 d . . . . .
C2O C 0.13599(14) 0.31028(15) 0.55187(15) 0.0491(6) Uani 1 1 d . . . . .
N3O N 0.15663(13) 0.25664(12) 0.58698(13) 0.0531(6) Uani 1 1 d . . . . .
C4O C 0.19395(17) 0.28590(16) 0.65045(16) 0.0564(7) Uani 1 1 d . . . . .
H4O H 0.176398 0.261969 0.692708 0.068 Uiso 1 1 calc R U . . .
C5O C 0.1705(2) 0.36348(18) 0.65103(17) 0.0671(9) Uani 1 1 d . . . . .
H5OA H 0.132639 0.371050 0.684748 0.080 Uiso 1 1 calc R U . . .
H5OB H 0.209996 0.394585 0.662438 0.080 Uiso 1 1 calc R U . . .
C3B C 0.27310(18) 0.27386(17) 0.64336(18) 0.0614(8) Uani 1 1 d . . . . .
C4B C 0.3086(2) 0.22668(18) 0.6868(3) 0.0776(11) Uani 1 1 d . . . . .
H4B H 0.283868 0.203439 0.722279 0.093 Uiso 1 1 calc R U . . .
C5B C 0.3798(3) 0.2139(2) 0.6780(4) 0.1060(19) Uani 1 1 d . . . . .
H5B H 0.403086 0.181919 0.707269 0.127 Uiso 1 1 calc R U . . .
C6B C 0.4166(3) 0.2479(4) 0.6264(4) 0.113(2) Uani 1 1 d . . . . .
H6B H 0.464891 0.239045 0.620510 0.136 Uiso 1 1 calc R U . . .
C7B C 0.3831(3) 0.2947(4) 0.5836(3) 0.1098(17) Uani 1 1 d . . . . .
H7B H 0.408422 0.317781 0.548412 0.132 Uiso 1 1 calc R U . . .
C8B C 0.3114(2) 0.3080(3) 0.5920(2) 0.0886(12) Uani 1 1 d . . . . .
H8B H 0.288832 0.340486 0.562704 0.106 Uiso 1 1 calc R U . . .
CC1 C 0.05935(16) 0.18278(16) 0.33294(17) 0.0561(7) Uani 1 1 d . . . . .
OC1 O 0.01272(15) 0.17853(13) 0.28839(16) 0.0866(9) Uani 1 1 d . . . . .
NP1 N 0.10581(13) 0.12922(12) 0.34329(14) 0.0552(6) Uani 1 1 d D . . . .
HP1 H 0.1465(14) 0.1348(17) 0.3663(18) 0.062(9) Uiso 1 1 d D . . . .
C1P1 C 0.10146(19) 0.06771(16) 0.29689(18) 0.0627(8) Uani 1 1 d . . . . .
H1P1 H 0.053762 0.046996 0.300138 0.075 Uiso 1 1 calc R U . . .
C2P1 C 0.1152(3) 0.09016(19) 0.2222(2) 0.0822(12) Uani 1 1 d . . . . .
C3P1 C 0.1565(2) 0.01133(17) 0.3169(2) 0.0688(9) Uani 1 1 d . . . . .
H3PA H 0.163949 -0.019911 0.277114 0.083 Uiso 1 1 calc R U . . .
H3PB H 0.201357 0.034798 0.326841 0.083 Uiso 1 1 calc R U . . .
C4P1 C 0.13599(19) -0.03283(17) 0.3793(2) 0.0661(9) Uani 1 1 d . . . . .
C5P1 C 0.1210(2) -0.10407(18) 0.3725(3) 0.0775(10) Uani 1 1 d . . . . .
H5P1 H 0.121728 -0.125025 0.328307 0.093 Uiso 1 1 calc R U . . .
C6P1 C 0.1048(3) -0.1448(2) 0.4305(3) 0.0968(15) Uani 1 1 d . . . . .
H6P1 H 0.095384 -0.193013 0.425096 0.116 Uiso 1 1 calc R U . . .
C7P1 C 0.1024(3) -0.1153(2) 0.4951(3) 0.0993(14) Uani 1 1 d . . . . .
H7P1 H 0.091336 -0.143183 0.533927 0.119 Uiso 1 1 calc R U . . .
C8P1 C 0.1161(3) -0.0452(3) 0.5031(3) 0.1074(16) Uani 1 1 d . . . . .
H8P1 H 0.114138 -0.024530 0.547366 0.129 Uiso 1 1 calc R U . . .
C9P1 C 0.1328(3) -0.0047(2) 0.4456(2) 0.0959(14) Uani 1 1 d . . . . .
H9P1 H 0.142249 0.043478 0.451805 0.115 Uiso 1 1 calc R U . . .
O1P1 O 0.1598(2) 0.13230(18) 0.20424(18) 0.1082(10) Uani 1 1 d . . . . .
O2P1 O 0.0722(2) 0.05510(16) 0.17834(17) 0.1197(13) Uani 1 1 d . . . . .
CMP1 C 0.0814(6) 0.0720(4) 0.1044(3) 0.183(4) Uani 1 1 d . . . . .
HMPA H 0.054401 0.039220 0.076467 0.274 Uiso 1 1 calc R U . . .
HMPB H 0.130787 0.068499 0.092258 0.274 Uiso 1 1 calc R U . . .
HMPC H 0.065003 0.119576 0.095665 0.274 Uiso 1 1 calc R U . . .
CC2 C 0.02441(13) 0.44125(14) 0.35048(14) 0.0424(5) Uani 1 1 d . . . . .
OC2 O 0.01916(11) 0.44287(10) 0.28635(10) 0.0552(5) Uani 1 1 d . . . . .
NP2 N 0.00942(13) 0.49784(13) 0.39014(13) 0.0515(5) Uani 1 1 d D . . . .
HP2 H 0.0150(18) 0.4955(18) 0.4353(13) 0.064(9) Uiso 1 1 d D . . . .
C1P2 C -0.02078(15) 0.56199(14) 0.36051(16) 0.0501(6) Uani 1 1 d . . . . .
H1P2 H -0.009461 0.562754 0.310339 0.060 Uiso 1 1 calc R U . . .
C2P2 C -0.10107(16) 0.56115(18) 0.36796(18) 0.0601(7) Uani 1 1 d . . . . .
C3P2 C 0.01115(17) 0.62887(16) 0.3939(2) 0.0655(8) Uani 1 1 d . . . . .
H3PC H -0.018070 0.669555 0.381740 0.079 Uiso 1 1 calc R U . . .
H3PD H 0.010388 0.623816 0.444494 0.079 Uiso 1 1 calc R U . . .
C4P2 C 0.08574(18) 0.64244(17) 0.3706(2) 0.0661(8) Uani 1 1 d . . . . .
C5P2 C 0.0991(3) 0.6819(3) 0.3115(3) 0.1079(16) Uani 1 1 d . . . . .
H5P2 H 0.061156 0.699446 0.285406 0.129 Uiso 1 1 calc R U . . .
C6P2 C 0.1670(4) 0.6959(4) 0.2905(4) 0.147(3) Uani 1 1 d . . . . .
H6P2 H 0.175314 0.723819 0.251021 0.176 Uiso 1 1 calc R U . . .
C7P2 C 0.2242(3) 0.6681(4) 0.3286(4) 0.131(2) Uani 1 1 d . . . . .
H7P2 H 0.270636 0.678019 0.315075 0.157 Uiso 1 1 calc R U . . .
C8P2 C 0.2117(2) 0.6273(3) 0.3845(3) 0.1069(15) Uani 1 1 d . . . . .
H8P2 H 0.249573 0.607427 0.409039 0.128 Uiso 1 1 calc R U . . .
C9P2 C 0.1428(2) 0.6146(2) 0.4062(3) 0.0848(11) Uani 1 1 d . . . . .
H9P2 H 0.134859 0.586631 0.445615 0.102 Uiso 1 1 calc R U . . .
O1P2 O -0.13482(15) 0.52089(16) 0.4023(2) 0.0971(9) Uani 1 1 d . . . . .
O2P2 O -0.12943(12) 0.61320(16) 0.33006(16) 0.0870(8) Uani 1 1 d . . . . .
CMP2 C -0.2051(2) 0.6231(4) 0.3342(3) 0.123(2) Uani 1 1 d . . . . .
HMPD H -0.217936 0.666220 0.310290 0.184 Uiso 1 1 calc R U . . .
HMPE H -0.219173 0.626277 0.382455 0.184 Uiso 1 1 calc R U . . .
HMPF H -0.228680 0.583589 0.312451 0.184 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
C1 C6 1.387(4) . ?
C1 C2 1.388(4) . ?
C1 CC1 1.497(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.390(4) . ?
C3 CC2 1.498(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.392(4) . ?
C5 C2O 1.470(4) . ?
O1O C2O 1.361(3) . ?
O1O C5O 1.447(4) . ?
C2O N3O 1.271(4) . ?
N3O C4O 1.503(4) . ?
C4O C3B 1.512(5) . ?
C4O C5O 1.524(4) . ?
C3B C8B 1.375(6) . ?
C3B C4B 1.385(5) . ?
C4B C5B 1.372(7) . ?
C5B C6B 1.362(9) . ?
C6B C7B 1.355(9) . ?
C7B C8B 1.381(7) . ?
CC1 OC1 1.223(4) . ?
CC1 NP1 1.348(4) . ?
NP1 C1P1 1.459(4) . ?
C1P1 C2P1 1.508(6) . ?
C1P1 C3P1 1.531(5) . ?
C2P1 O1P1 1.204(5) . ?
C2P1 O2P1 1.338(5) . ?
C3P1 C4P1 1.500(6) . ?
C4P1 C9P1 1.373(6) . ?
C4P1 C5P1 1.375(5) . ?
C5P1 C6P1 1.379(7) . ?
C6P1 C7P1 1.351(8) . ?
C7P1 C8P1 1.353(6) . ?
C8P1 C9P1 1.371(7) . ?
O2P1 CMP1 1.456(7) . ?
CC2 OC2 1.227(3) . ?
CC2 NP2 1.336(4) . ?
NP2 C1P2 1.448(4) . ?
C1P2 C2P2 1.517(4) . ?
C1P2 C3P2 1.532(4) . ?
C2P2 O1P2 1.186(4) . ?
C2P2 O2P2 1.329(4) . ?
C3P2 C4P2 1.493(5) . ?
C4P2 C5P2 1.371(6) . ?
C4P2 C9P2 1.373(5) . ?
C5P2 C6P2 1.366(8) . ?
C6P2 C7P2 1.399(9) . ?
C7P2 C8P2 1.334(9) . ?
C8P2 C9P2 1.381(6) . ?
O2P2 CMP2 1.437(5) . ?

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 C1 C2 119.6(2) . . ?
C6 C1 CC1 123.5(2) . . ?
C2 C1 CC1 116.9(3) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 CC2 117.4(2) . . ?
C4 C3 CC2 123.5(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C2O 120.1(2) . . ?
C6 C5 C2O 120.5(2) . . ?
C1 C6 C5 120.2(2) . . ?
C2O O1O C5O 105.4(2) . . ?
N3O C2O O1O 118.0(2) . . ?
N3O C2O C5 127.3(3) . . ?
O1O C2O C5 114.6(2) . . ?
C2O N3O C4O 106.0(2) . . ?
N3O C4O C3B 109.4(3) . . ?
N3O C4O C5O 102.8(2) . . ?
C3B C4O C5O 115.4(3) . . ?
O1O C5O C4O 104.0(2) . . ?
C8B C3B C4B 118.2(4) . . ?
C8B C3B C4O 120.6(3) . . ?
C4B C3B C4O 121.1(3) . . ?
C5B C4B C3B 120.6(5) . . ?
C6B C5B C4B 120.1(5) . . ?
C7B C6B C5B 120.2(5) . . ?
C6B C7B C8B 120.1(6) . . ?
C3B C8B C7B 120.6(5) . . ?
OC1 CC1 NP1 121.2(3) . . ?
OC1 CC1 C1 121.1(3) . . ?
NP1 CC1 C1 117.8(3) . . ?
CC1 NP1 C1P1 117.9(3) . . ?
NP1 C1P1 C2P1 109.9(3) . . ?
NP1 C1P1 C3P1 111.1(3) . . ?
C2P1 C1P1 C3P1 108.3(3) . . ?
O1P1 C2P1 O2P1 124.7(4) . . ?
O1P1 C2P1 C1P1 124.9(4) . . ?
O2P1 C2P1 C1P1 110.4(4) . . ?
C4P1 C3P1 C1P1 114.0(3) . . ?
C9P1 C4P1 C5P1 117.0(4) . . ?
C9P1 C4P1 C3P1 121.8(3) . . ?
C5P1 C4P1 C3P1 121.2(4) . . ?
C4P1 C5P1 C6P1 120.7(4) . . ?
C7P1 C6P1 C5P1 120.7(4) . . ?
C6P1 C7P1 C8P1 119.7(4) . . ?
C7P1 C8P1 C9P1 119.7(5) . . ?
C8P1 C9P1 C4P1 122.1(4) . . ?
C2P1 O2P1 CMP1 115.2(5) . . ?
OC2 CC2 NP2 121.8(2) . . ?
OC2 CC2 C3 120.0(2) . . ?
NP2 CC2 C3 118.1(2) . . ?
CC2 NP2 C1P2 121.7(2) . . ?
NP2 C1P2 C2P2 110.2(2) . . ?
NP2 C1P2 C3P2 111.6(2) . . ?
C2P2 C1P2 C3P2 111.1(3) . . ?
O1P2 C2P2 O2P2 123.8(3) . . ?
O1P2 C2P2 C1P2 126.3(3) . . ?
O2P2 C2P2 C1P2 109.9(3) . . ?
C4P2 C3P2 C1P2 112.7(3) . . ?
C5P2 C4P2 C9P2 118.0(4) . . ?
C5P2 C4P2 C3P2 120.5(4) . . ?
C9P2 C4P2 C3P2 121.5(3) . . ?
C6P2 C5P2 C4P2 121.1(5) . . ?
C5P2 C6P2 C7P2 119.6(5) . . ?
C8P2 C7P2 C6P2 119.7(5) . . ?
C7P2 C8P2 C9P2 120.2(5) . . ?
C4P2 C9P2 C8P2 121.3(4) . . ?
C2P2 O2P2 CMP2 117.6(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NP1 HP1 N3O 0.89(2) 2.29(2) 3.175(3) 173(3) 7_556 yes
NP2 HP2 OC2 0.87(2) 2.13(3) 2.956(3) 159(3) 3 yes

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.026


####################################################################### 
# 
# 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_3t3
_database_code_depnum_ccdc_archive 'CCDC 2335948'
loop_
_audit_author_name
_audit_author_address
'Berislav Peric'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-04 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         'C37 H37 N3 O8'
_chemical_formula_sum            'C37 H37 N3 O8'
_chemical_formula_weight         651.69

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.8640(2)
_cell_length_b                   18.8640(2)
_cell_length_c                   19.6976(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7009.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      3.9880
_cell_measurement_theta_max      51.7960

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             2752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.719
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.76273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            22636
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.244
_diffrn_reflns_theta_max         75.839
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7226
_reflns_number_gt                4601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material  
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_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)+(0.1592P)²+0.1723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(19)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7226
_refine_ls_number_parameters     443
_refine_ls_number_restraints     219
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2762
_refine_ls_wR_factor_gt          0.2386
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.0547(2) 0.2921(3) 0.4924(2) 0.0681(11) Uani 1 1 d . . . . .
C2 C 0.1162(3) 0.2653(3) 0.4625(3) 0.0710(11) Uani 1 1 d . . . . .
H2 H 0.136207 0.223551 0.478618 0.085 Uiso 1 1 calc R U . . .
C3 C 0.1475(3) 0.3010(3) 0.4086(2) 0.0666(10) Uani 1 1 d . . . . .
C4 C 0.1185(3) 0.3646(3) 0.3861(2) 0.0689(11) Uani 1 1 d . . . . .
H4 H 0.138893 0.388046 0.349505 0.083 Uiso 1 1 calc R U . . .
C5 C 0.0595(3) 0.3933(3) 0.4176(2) 0.0707(12) Uani 1 1 d . . . . .
C6 C 0.0265(3) 0.3556(3) 0.4688(2) 0.0705(11) Uani 1 1 d . . . . .
H6 H -0.015103 0.372989 0.487784 0.085 Uiso 1 1 calc R U . . .
CC1 C 0.0158(3) 0.2564(3) 0.5488(3) 0.0731(12) Uani 1 1 d . . . . .
OC1 O -0.04908(19) 0.2605(2) 0.5505(2) 0.0899(11) Uani 1 1 d . . . . .
NP1 N 0.0527(2) 0.2215(3) 0.5957(3) 0.0865(13) Uani 1 1 d D . . . .
HP1 H 0.0984(14) 0.224(3) 0.599(3) 0.076(16) Uiso 1 1 d D . . . .
C1P1 C 0.0172(3) 0.1948(3) 0.6558(3) 0.0867(15) Uani 1 1 d . . . . .
H1P1 H -0.027586 0.172813 0.642085 0.104 Uiso 1 1 calc R U . . .
C2P1 C 0.0009(4) 0.2568(4) 0.7040(4) 0.0944(17) Uani 1 1 d . . . . .
C3P1 C 0.0610(5) 0.1407(4) 0.6925(4) 0.104(2) Uani 1 1 d . . . . .
H3PB H 0.109054 0.158366 0.697012 0.124 Uiso 1 1 calc R U . A 1
H3PA H 0.041969 0.134390 0.737900 0.124 Uiso 1 1 calc R U . A 1
C4PA C 0.0630(6) 0.0713(6) 0.6582(7) 0.107(2) Uani 0.550(16) 1 d G U P B 1
C5PA C 0.0033(5) 0.0295(8) 0.6476(11) 0.165(10) Uani 0.550(16) 1 d G U P B 1
H5PA H -0.041285 0.046379 0.659446 0.198 Uiso 0.550(16) 1 calc R U P B 1
C6PA C 0.0104(6) -0.0376(8) 0.6193(12) 0.205(15) Uani 0.550(16) 1 d G U P B 1
H6PA H -0.029442 -0.065662 0.612218 0.246 Uiso 0.550(16) 1 calc R U P B 1
C7PA C 0.0772(8) -0.0629(6) 0.6016(9) 0.186(6) Uani 0.550(16) 1 d G U P B 1
H7PA H 0.081901 -0.107824 0.582696 0.224 Uiso 0.550(16) 1 calc R U P B 1
C8PA C 0.1368(6) -0.0210(6) 0.6122(9) 0.139(7) Uani 0.550(16) 1 d G U P B 1
H8PA H 0.181403 -0.037946 0.600401 0.166 Uiso 0.550(16) 1 calc R U P B 1
C9PA C 0.1297(5) 0.0461(5) 0.6405(8) 0.123(6) Uani 0.550(16) 1 d G U P B 1
H9PA H 0.169562 0.074096 0.647629 0.148 Uiso 0.550(16) 1 calc R U P B 1
C4PB C 0.0659(11) 0.0646(7) 0.6547(8) 0.107(2) Uani 0.450(16) 1 d G U P B 2
C5PB C 0.0441(14) 0.0072(9) 0.6938(7) 0.167(12) Uani 0.450(16) 1 d G U P B 2
H5PB H 0.029711 0.014152 0.738458 0.201 Uiso 0.450(16) 1 calc R U P B 2
C6PB C 0.0437(14) -0.0606(7) 0.6661(11) 0.171(10) Uani 0.450(16) 1 d G U P B 2
H6PB H 0.029124 -0.098953 0.692208 0.205 Uiso 0.450(16) 1 calc R U P B 2
C7PB C 0.0652(11) -0.0710(7) 0.5993(12) 0.186(6) Uani 0.450(16) 1 d G U P B 2
H7PB H 0.064949 -0.116318 0.580770 0.224 Uiso 0.450(16) 1 calc R U P B 2
C8PB C 0.0870(16) -0.0136(11) 0.5603(9) 0.196(15) Uani 0.450(16) 1 d G U P B 2
H8PB H 0.101363 -0.020580 0.515581 0.236 Uiso 0.450(16) 1 calc R U P B 2
C9PB C 0.0874(15) 0.0541(9) 0.5880(9) 0.216(18) Uani 0.450(16) 1 d G U P B 2
H9PB H 0.101952 0.092526 0.561830 0.260 Uiso 0.450(16) 1 calc R U P B 2
O1P1 O 0.0310(4) 0.3101(4) 0.7053(5) 0.158(3) Uani 1 1 d . . . . .
O2P1 O -0.0563(4) 0.2439(3) 0.7415(3) 0.127(2) Uani 1 1 d . . . . .
CMP1 C -0.0756(6) 0.2978(6) 0.7931(4) 0.136(3) Uani 1 1 d . . . . .
HMPB H -0.078699 0.343488 0.771867 0.205 Uiso 1 1 calc R U . . .
HMPC H -0.040013 0.298928 0.827905 0.205 Uiso 1 1 calc R U . . .
HMPA H -0.120553 0.285824 0.812828 0.205 Uiso 1 1 calc R U . . .
CC2 C 0.2114(3) 0.2670(3) 0.3765(3) 0.0728(12) Uani 1 1 d . . . . .
OC2 O 0.2259(2) 0.2044(2) 0.3884(3) 0.0956(13) Uani 1 1 d . . . . .
NP2 N 0.2508(3) 0.3070(2) 0.3363(3) 0.0876(14) Uani 1 1 d D . . . .
HP2 H 0.240(4) 0.3502(17) 0.338(4) 0.10(2) Uiso 1 1 d D . . . .
C1P2 C 0.3118(4) 0.2812(3) 0.2985(4) 0.104(2) Uani 1 1 d . . . . .
H1P2 H 0.316008 0.229935 0.305201 0.124 Uiso 1 1 calc R U . . .
C2P2 C 0.3794(4) 0.3170(4) 0.3236(6) 0.114(3) Uani 1 1 d . . . . .
C3P2 C 0.3046(5) 0.2964(5) 0.2232(5) 0.128(3) Uani 1 1 d . . . . .
H3PD H 0.309095 0.346996 0.215844 0.154 Uiso 1 1 calc R U . . .
H3PC H 0.343083 0.273217 0.199265 0.154 Uiso 1 1 calc R U . . .
C4P2 C 0.2356(4) 0.2718(4) 0.1939(4) 0.127(3) Uani 1 1 d G . . . .
C5P2 C 0.2189(6) 0.2001(4) 0.1913(5) 0.182(5) Uani 1 1 d G . . . .
H5P2 H 0.250153 0.166757 0.209144 0.218 Uiso 1 1 calc R U . . .
C6P2 C 0.1556(7) 0.1781(5) 0.1620(6) 0.239(9) Uani 1 1 d G . . . .
H6P2 H 0.144466 0.130104 0.160198 0.287 Uiso 1 1 calc R U . . .
C7P2 C 0.1090(5) 0.2279(8) 0.1353(6) 0.257(9) Uani 1 1 d G . . . .
H7P2 H 0.066607 0.213159 0.115634 0.309 Uiso 1 1 calc R U . . .
C8P2 C 0.1256(5) 0.2996(7) 0.1379(6) 0.257(9) Uani 1 1 d G . . . .
H8P2 H 0.094436 0.332866 0.120015 0.308 Uiso 1 1 calc R U . . .
C9P2 C 0.1890(6) 0.3215(4) 0.1672(5) 0.182(5) Uani 1 1 d G . . . .
H9P2 H 0.200123 0.369521 0.168961 0.219 Uiso 1 1 calc R U . . .
O1P2 O 0.3813(4) 0.3552(4) 0.3724(5) 0.150(3) Uani 1 1 d . . . . .
O2P2 O 0.4350(3) 0.3010(4) 0.2871(5) 0.169(3) Uani 1 1 d . . . . .
CMP2 C 0.5028(6) 0.3289(8) 0.3105(11) 0.222(8) Uani 1 1 d . . . . .
HMPD H 0.525101 0.354774 0.274301 0.333 Uiso 1 1 calc R U . . .
HMPE H 0.532908 0.290403 0.324080 0.333 Uiso 1 1 calc R U . . .
HMPF H 0.495143 0.359949 0.348371 0.333 Uiso 1 1 calc R U . . .
CC3 C 0.0329(3) 0.4653(3) 0.3950(2) 0.0807(14) Uani 1 1 d . . . . .
OC3 O 0.0409(2) 0.4867(3) 0.33711(18) 0.0964(13) Uani 1 1 d . . . . .
NB N 0.0011(3) 0.5031(3) 0.4432(2) 0.0896(14) Uani 1 1 d D . . . .
HB H -0.002(3) 0.484(3) 0.4824(18) 0.084(17) Uiso 1 1 d D . . . .
C1B C -0.0261(5) 0.5754(4) 0.4335(4) 0.105(2) Uani 1 1 d . . . . .
H1B H -0.020485 0.588799 0.385751 0.126 Uiso 1 1 calc R U . . .
C2B C 0.0169(5) 0.6262(4) 0.4776(6) 0.132(3) Uani 1 1 d . . . . .
H2BA H -0.006450 0.671950 0.479019 0.158 Uiso 1 1 calc R U . . .
H2BB H 0.019279 0.607926 0.523601 0.158 Uiso 1 1 calc R U . . .
C3B C -0.1053(3) 0.5793(4) 0.4525(3) 0.122(3) Uani 1 1 d G . . . .
C4B C -0.1421(4) 0.6389(4) 0.4307(4) 0.195(7) Uani 1 1 d G . . . .
H4B H -0.119667 0.672405 0.403512 0.234 Uiso 1 1 calc R U . . .
C5B C -0.2125(4) 0.6486(5) 0.4496(5) 0.195(6) Uani 1 1 d G . . . .
H5B H -0.237089 0.688475 0.434974 0.234 Uiso 1 1 calc R U . . .
C6B C -0.2460(3) 0.5985(6) 0.4902(5) 0.184(5) Uani 1 1 d G . . . .
H6B H -0.293102 0.604990 0.502816 0.221 Uiso 1 1 calc R U . . .
C7B C -0.2092(3) 0.5389(5) 0.5120(5) 0.197(6) Uani 1 1 d G . . . .
H7B H -0.231693 0.505435 0.539196 0.237 Uiso 1 1 calc R U . . .
C8B C -0.1389(3) 0.5293(4) 0.4932(4) 0.147(4) Uani 1 1 d G . . . .
H8B H -0.114271 0.489365 0.507736 0.176 Uiso 1 1 calc R U . . .
OB O 0.0878(4) 0.6345(4) 0.4510(7) 0.184(4) Uani 1 1 d . . . . .
HOB H 0.102179 0.596217 0.436891 0.276 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
C1 C6 1.390(7) . ?
C1 C2 1.396(7) . ?
C1 CC1 1.492(7) . ?
C2 C3 1.388(7) . ?
C3 C4 1.391(7) . ?
C3 CC2 1.505(7) . ?
C4 C5 1.383(7) . ?
C5 C6 1.382(7) . ?
C5 CC3 1.515(8) . ?
CC1 OC1 1.226(6) . ?
CC1 NP1 1.330(7) . ?
NP1 C1P1 1.451(7) . ?
C1P1 C3P1 1.499(10) . ?
C1P1 C2P1 1.538(10) . ?
C2P1 O1P1 1.154(9) . ?
C2P1 O2P1 1.331(9) . ?
C3P1 C4PA 1.473(12) . ?
C4PA C5PA 1.3900 . ?
C4PA C9PA 1.3900 . ?
C5PA C6PA 1.3900 . ?
C6PA C7PA 1.3900 . ?
C7PA C8PA 1.3900 . ?
C8PA C9PA 1.3900 . ?
C4PB C5PB 1.3900 . ?
C4PB C9PB 1.3900 . ?
C5PB C6PB 1.3900 . ?
C6PB C7PB 1.3900 . ?
C7PB C8PB 1.3900 . ?
C8PB C9PB 1.3900 . ?
O2P1 CMP1 1.482(10) . ?
CC2 OC2 1.236(6) . ?
CC2 NP2 1.320(7) . ?
NP2 C1P2 1.454(8) . ?
C1P2 C3P2 1.516(13) . ?
C1P2 C2P2 1.525(13) . ?
C2P2 O1P2 1.202(13) . ?
C2P2 O2P2 1.307(10) . ?
C3P2 C4P2 1.497(12) . ?
C4P2 C5P2 1.3900 . ?
C4P2 C9P2 1.3900 . ?
C5P2 C6P2 1.3900 . ?
C6P2 C7P2 1.3900 . ?
C7P2 C8P2 1.3900 . ?
C8P2 C9P2 1.3900 . ?
O2P2 CMP2 1.458(16) . ?
CC3 OC3 1.219(6) . ?
CC3 NB 1.331(7) . ?
NB C1B 1.469(8) . ?
C1B C2B 1.527(13) . ?
C1B C3B 1.542(10) . ?
C2B OB 1.445(12) . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B C6B 1.3900 . ?
C6B C7B 1.3900 . ?
C7B C8B 1.3900 . ?

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 C1 C2 119.1(4) . . ?
C6 C1 CC1 116.8(4) . . ?
C2 C1 CC1 124.1(5) . . ?
C3 C2 C1 120.1(5) . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 CC2 117.2(4) . . ?
C4 C3 CC2 123.3(4) . . ?
C5 C4 C3 120.8(4) . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 CC3 121.8(5) . . ?
C4 C5 CC3 119.1(4) . . ?
C5 C6 C1 121.0(5) . . ?
OC1 CC1 NP1 122.4(5) . . ?
OC1 CC1 C1 118.8(5) . . ?
NP1 CC1 C1 118.8(4) . . ?
CC1 NP1 C1P1 119.7(5) . . ?
NP1 C1P1 C3P1 112.1(6) . . ?
NP1 C1P1 C2P1 109.4(5) . . ?
C3P1 C1P1 C2P1 109.3(6) . . ?
O1P1 C2P1 O2P1 123.1(8) . . ?
O1P1 C2P1 C1P1 125.3(7) . . ?
O2P1 C2P1 C1P1 111.4(6) . . ?
C4PA C3P1 C1P1 113.4(8) . . ?
C5PA C4PA C9PA 120.0 . . ?
C5PA C4PA C3P1 123.6(8) . . ?
C9PA C4PA C3P1 116.2(8) . . ?
C4PA C5PA C6PA 120.0 . . ?
C7PA C6PA C5PA 120.0 . . ?
C6PA C7PA C8PA 120.0 . . ?
C7PA C8PA C9PA 120.0 . . ?
C8PA C9PA C4PA 120.0 . . ?
C5PB C4PB C9PB 120.0 . . ?
C4PB C5PB C6PB 120.0 . . ?
C7PB C6PB C5PB 120.0 . . ?
C6PB C7PB C8PB 120.0 . . ?
C9PB C8PB C7PB 120.0 . . ?
C8PB C9PB C4PB 120.0 . . ?
C2P1 O2P1 CMP1 117.0(7) . . ?
OC2 CC2 NP2 122.4(5) . . ?
OC2 CC2 C3 120.3(4) . . ?
NP2 CC2 C3 117.4(4) . . ?
CC2 NP2 C1P2 124.1(5) . . ?
NP2 C1P2 C3P2 111.5(6) . . ?
NP2 C1P2 C2P2 110.4(7) . . ?
C3P2 C1P2 C2P2 108.0(7) . . ?
O1P2 C2P2 O2P2 123.7(10) . . ?
O1P2 C2P2 C1P2 123.3(7) . . ?
O2P2 C2P2 C1P2 113.0(10) . . ?
C4P2 C3P2 C1P2 113.4(7) . . ?
C5P2 C4P2 C9P2 120.0 . . ?
C5P2 C4P2 C3P2 120.8(7) . . ?
C9P2 C4P2 C3P2 119.1(7) . . ?
C6P2 C5P2 C4P2 120.0 . . ?
C5P2 C6P2 C7P2 120.0 . . ?
C8P2 C7P2 C6P2 120.0 . . ?
C9P2 C8P2 C7P2 120.0 . . ?
C8P2 C9P2 C4P2 120.0 . . ?
C2P2 O2P2 CMP2 116.5(11) . . ?
OC3 CC3 NB 123.1(6) . . ?
OC3 CC3 C5 122.1(5) . . ?
NB CC3 C5 114.9(4) . . ?
CC3 NB C1B 124.2(5) . . ?
NB C1B C2B 108.8(7) . . ?
NB C1B C3B 110.6(6) . . ?
C2B C1B C3B 110.3(7) . . ?
OB C2B C1B 110.8(10) . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C1B 116.6(5) . . ?
C8B C3B C1B 123.3(5) . . ?
C3B C4B C5B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C7B C6B C5B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C7B C8B C3B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NP1 HP1 OC2 0.87(3) 2.01(3) 2.879(6) 177(6) 7_556 yes
NB HB OC3 0.85(3) 2.13(3) 2.967(6) 168(6) 4_455 yes
NP2 HP2 OC1 0.84(3) 2.04(4) 2.813(6) 153(7) 3_554 yes
OB HOB O1P1 0.82 2.09 2.744(10) 136.0 3_554 yes
OB HOB NB 0.82 2.59 2.973(10) 109.7 . yes

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.060



