# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_BUD
_database_code_depnum_ccdc_archive 'CCDC 2374652'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-10-02 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         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.22790(10)
_cell_length_b                   13.8547(4)
_cell_length_c                   20.1340(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1458.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.44
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            45414
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.784
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4467
_reflns_number_gt                4249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     1.000
_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       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.3091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4467
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4955(2) 0.73806(7) 0.34907(5) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.2269(2) 0.76931(8) 0.26850(6) 0.0212(2) Uani 1 1 d . . . . .
O3 O 1.0295(2) 0.86272(8) 0.41721(5) 0.0215(2) Uani 1 1 d . . . . .
O4 O 0.5811(2) 0.47294(8) 0.43480(5) 0.0224(2) Uani 1 1 d . . . . .
N1 N 0.6938(2) 0.76869(9) 0.39221(6) 0.0166(2) Uani 1 1 d . . . . .
C1 C 0.8477(3) 0.84553(10) 0.38027(7) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.7764(3) 0.90618(9) 0.32280(6) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.9227(3) 0.98759(10) 0.30834(7) 0.0161(3) Uani 1 1 d . . . . .
H3 H 1.063142 1.004835 0.335810 0.019 Uiso 1 1 calc R U . . .
C4 C 0.8606(3) 1.04316(10) 0.25333(7) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.958999 1.098942 0.243306 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6551(3) 1.01799(10) 0.21251(7) 0.0189(3) Uani 1 1 d . . . . .
H5 H 0.616700 1.055935 0.174487 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5069(3) 0.93783(10) 0.22730(7) 0.0173(3) Uani 1 1 d . . . . .
H6 H 0.365735 0.921018 0.199922 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5676(3) 0.88197(9) 0.28302(6) 0.0138(2) Uani 1 1 d . . . . .
C8 C 0.4144(3) 0.79620(10) 0.29789(7) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.7387(3) 0.69559(10) 0.44288(7) 0.0156(2) Uani 1 1 d . . . . .
H9A H 0.575101 0.662729 0.452952 0.019 Uiso 1 1 calc R U . . .
H9B H 0.797714 0.727721 0.484040 0.019 Uiso 1 1 calc R U . . .
C10 C 0.9357(3) 0.62016(10) 0.42246(7) 0.0183(3) Uani 1 1 d . . . . .
H10A H 1.102509 0.651994 0.414608 0.022 Uiso 1 1 calc R U . . .
H10B H 0.881215 0.589251 0.380442 0.022 Uiso 1 1 calc R U . . .
C11 C 0.9659(3) 0.54310(10) 0.47625(8) 0.0184(3) Uani 1 1 d . . . . .
H11A H 1.126398 0.506965 0.468275 0.022 Uiso 1 1 calc R U . . .
H11B H 0.980606 0.575133 0.520042 0.022 Uiso 1 1 calc R U . . .
C12 C 0.7444(3) 0.47261(9) 0.47813(7) 0.0147(2) Uani 1 1 d . . . . .
C13 C 0.7307(3) 0.40072(9) 0.53363(7) 0.0140(2) Uani 1 1 d . . . . .
C14 C 0.5271(3) 0.33488(10) 0.53421(7) 0.0167(3) Uani 1 1 d . . . . .
H14 H 0.404054 0.335944 0.499509 0.020 Uiso 1 1 calc R U . . .
C15 C 0.5046(3) 0.26800(11) 0.58539(7) 0.0196(3) Uani 1 1 d . . . . .
H15 H 0.365516 0.223896 0.585770 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6858(3) 0.26561(11) 0.63609(7) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.668979 0.220464 0.671337 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8911(3) 0.32920(11) 0.63511(7) 0.0201(3) Uani 1 1 d . . . . .
H17 H 1.016509 0.326573 0.669198 0.024 Uiso 1 1 calc R U . . .
C18 C 0.9135(3) 0.39695(10) 0.58417(7) 0.0168(3) Uani 1 1 d . . . . .
H18 H 1.053500 0.440656 0.583849 0.020 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3750(17) . ?
O1 N1 1.4174(15) . ?
O2 C8 1.2040(17) . ?
O3 C1 1.2301(17) . ?
O4 C12 1.2205(17) . ?
N1 C1 1.3560(17) . ?
N1 C9 1.4565(17) . ?
C1 C2 1.4777(18) . ?
C2 C3 1.3935(19) . ?
C2 C7 1.3947(18) . ?
C3 C4 1.3873(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3995(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4641(19) . ?
C9 C10 1.524(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5291(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5156(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4986(18) . ?
C13 C18 1.3969(18) . ?
C13 C14 1.4015(19) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 N1 120.63(10) . . ?
C1 N1 O1 124.07(11) . . ?
C1 N1 C9 125.06(12) . . ?
O1 N1 C9 109.82(10) . . ?
O3 C1 N1 120.20(12) . . ?
O3 C1 C2 123.94(12) . . ?
N1 C1 C2 115.83(12) . . ?
C3 C2 C7 120.27(12) . . ?
C3 C2 C1 119.05(12) . . ?
C7 C2 C1 120.68(12) . . ?
C4 C3 C2 119.20(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.73(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.22(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.23(13) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 120.33(12) . . ?
C2 C7 C8 120.39(12) . . ?
C6 C7 C8 119.25(12) . . ?
O2 C8 O1 115.99(12) . . ?
O2 C8 C7 126.59(13) . . ?
O1 C8 C7 117.39(12) . . ?
N1 C9 C10 113.38(11) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 110.96(11) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 112.86(12) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O4 C12 C13 120.13(12) . . ?
O4 C12 C11 120.95(12) . . ?
C13 C12 C11 118.91(12) . . ?
C18 C13 C14 119.28(12) . . ?
C18 C13 C12 122.36(12) . . ?
C14 C13 C12 118.37(12) . . ?
C15 C14 C13 120.27(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.09(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.99(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.15(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.20(13) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 N1 C1 -12.68(19) . . . . ?
C8 O1 N1 C9 178.52(12) . . . . ?
O1 N1 C1 O3 -173.79(13) . . . . ?
C9 N1 C1 O3 -6.7(2) . . . . ?
O1 N1 C1 C2 8.08(19) . . . . ?
C9 N1 C1 C2 175.17(12) . . . . ?
O3 C1 C2 C3 0.6(2) . . . . ?
N1 C1 C2 C3 178.66(12) . . . . ?
O3 C1 C2 C7 179.88(13) . . . . ?
N1 C1 C2 C7 -2.07(19) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 178.19(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C3 C2 C7 C6 1.6(2) . . . . ?
C1 C2 C7 C6 -177.70(12) . . . . ?
C3 C2 C7 C8 179.69(13) . . . . ?
C1 C2 C7 C8 0.43(19) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C5 C6 C7 C8 -178.77(13) . . . . ?
N1 O1 C8 O2 -171.99(12) . . . . ?
N1 O1 C8 C7 10.12(18) . . . . ?
C2 C7 C8 O2 177.91(13) . . . . ?
C6 C7 C8 O2 -3.9(2) . . . . ?
C2 C7 C8 O1 -4.45(19) . . . . ?
C6 C7 C8 O1 173.70(12) . . . . ?
C1 N1 C9 C10 -79.39(17) . . . . ?
O1 N1 C9 C10 89.27(14) . . . . ?
N1 C9 C10 C11 -177.51(11) . . . . ?
C9 C10 C11 C12 75.17(15) . . . . ?
C10 C11 C12 O4 8.7(2) . . . . ?
C10 C11 C12 C13 -172.37(11) . . . . ?
O4 C12 C13 C18 179.59(13) . . . . ?
C11 C12 C13 C18 0.69(19) . . . . ?
O4 C12 C13 C14 -0.06(19) . . . . ?
C11 C12 C13 C14 -178.96(12) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
C12 C13 C14 C15 -178.91(13) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 1.4(2) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C12 C13 C18 C17 179.43(13) . . . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.047

