# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KA152-3
_audit_block_doi                 10.5517/ccdc.csd.cc26hp9q
_database_code_depnum_ccdc_archive 'CCDC 2040863'
loop_
_audit_author_name
_audit_author_address
'Alex Kostenko'
;Zelinsky Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-02-01 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 H13 N O5'
_chemical_formula_sum            'C19 H13 N O5'
_chemical_formula_weight         335.30

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'
O O 0.0106 0.0060 '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'

_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                   12.42180(14)
_cell_length_b                   12.42180(14)
_cell_length_c                   9.8189(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1515.07(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      33.42

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7971
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_process_details   
;
 SADABS 2016/2 (Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 2015, 48, 3-10).
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_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            59697
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.644
_diffrn_reflns_theta_max         33.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5899
_reflns_number_gt                5688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.996

_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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_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.
 
 Aspherical scattering factors5 were applied at the final refinement steps
 (Lübben, Wandtke, Hübschle, Ruf, Sheldrick, Dittrich, Acta Cryst.
 2019, A75, 50-62).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.0846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5899
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0526
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03455(5) 0.71327(5) 0.33366(7) 0.01781(12) Uani 1 1 d . . . . .
O2 O 0.35632(5) 0.65700(6) 0.58059(7) 0.02014(12) Uani 1 1 d . . . . .
O3 O -0.03645(5) 0.83103(6) 0.53720(8) 0.02345(14) Uani 1 1 d . . . . .
O4 O 0.02452(7) 0.43845(8) 0.22718(11) 0.0411(2) Uani 1 1 d . . . . .
O5 O 0.09449(6) 0.46366(6) 0.42712(9) 0.03039(17) Uani 1 1 d . . . . .
N5 N 0.08646(6) 0.48409(6) 0.30591(10) 0.02369(16) Uani 1 1 d . . . . .
C2 C 0.08069(7) 0.66741(8) 0.21276(9) 0.02018(16) Uani 1 1 d . . . . .
H2A H 0.1270(13) 0.7271(13) 0.1646(18) 0.032(4) Uiso 1 1 d . . . . .
H2B H 0.0209(13) 0.6416(13) 0.1536(19) 0.038(4) Uiso 1 1 d . . . . .
C3 C 0.15439(7) 0.57369(7) 0.24532(9) 0.01832(15) Uani 1 1 d . . . . .
H3 H 0.1805(12) 0.5414(12) 0.1566(17) 0.026(3) Uiso 1 1 d . . . . .
C4 C 0.24529(6) 0.60884(6) 0.33993(8) 0.01447(13) Uani 1 1 d . . . . .
H4 H 0.2789(12) 0.5429(12) 0.3799(16) 0.026(4) Uiso 1 1 d . . . . .
C4A C 0.19977(6) 0.67875(6) 0.45113(8) 0.01362(13) Uani 1 1 d . . . . .
C5 C 0.26523(6) 0.69491(6) 0.57408(8) 0.01421(13) Uani 1 1 d . . . . .
C5A C 0.21824(6) 0.75658(7) 0.68945(8) 0.01446(13) Uani 1 1 d . . . . .
C6 C 0.27657(7) 0.76754(7) 0.81007(8) 0.01825(15) Uani 1 1 d . . . . .
H6 H 0.3488(13) 0.7340(12) 0.8186(18) 0.033(4) Uiso 1 1 d . . . . .
C7 C 0.23239(8) 0.82347(8) 0.91931(9) 0.02155(17) Uani 1 1 d . . . . .
H7 H 0.2764(13) 0.8303(13) 1.0094(18) 0.032(4) Uiso 1 1 d . . . . .
C8 C 0.13103(8) 0.87006(8) 0.90816(10) 0.02329(17) Uani 1 1 d . . . . .
H8 H 0.0985(14) 0.9099(14) 0.984(2) 0.044(4) Uiso 1 1 d . . . . .
C9 C 0.07235(7) 0.85935(8) 0.78845(10) 0.02135(16) Uani 1 1 d . . . . .
H9 H -0.0012(12) 0.8941(12) 0.7775(16) 0.029(4) Uiso 1 1 d . . . . .
C9A C 0.11555(6) 0.80177(7) 0.67899(8) 0.01541(14) Uani 1 1 d . . . . .
C10 C 0.05166(6) 0.78952(7) 0.55267(9) 0.01575(14) Uani 1 1 d . . . . .
C10A C 0.10079(6) 0.72375(6) 0.44140(8) 0.01441(13) Uani 1 1 d . . . . .
C11 C 0.33187(6) 0.66432(6) 0.25506(8) 0.01417(13) Uani 1 1 d . . . . .
C12 C 0.35276(7) 0.77401(7) 0.26685(9) 0.01559(13) Uani 1 1 d . . . . .
H12 H 0.3131(12) 0.8164(12) 0.3345(16) 0.027(3) Uiso 1 1 d . . . . .
C13 C 0.43184(7) 0.82243(7) 0.18656(9) 0.01833(15) Uani 1 1 d . . . . .
H13 H 0.4451(12) 0.8996(12) 0.1980(16) 0.030(4) Uiso 1 1 d . . . . .
C14 C 0.48913(7) 0.76183(8) 0.09213(9) 0.02079(16) Uani 1 1 d . . . . .
H14 H 0.5472(13) 0.7976(12) 0.0349(18) 0.034(4) Uiso 1 1 d . . . . .
C15 C 0.46843(7) 0.65192(8) 0.07968(10) 0.02136(16) Uani 1 1 d . . . . .
H15 H 0.5115(13) 0.6090(13) 0.0161(18) 0.035(4) Uiso 1 1 d . . . . .
C16 C 0.39050(7) 0.60362(7) 0.16135(9) 0.01818(15) Uani 1 1 d . . . . .
H16 H 0.3787(11) 0.5274(11) 0.1518(15) 0.021(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10A 1.3466(10) . ?
O1 C2 1.4361(11) . ?
O2 C5 1.2272(10) . ?
O3 C10 1.2194(10) . ?
O4 N5 1.2291(12) . ?
O5 N5 1.2210(13) . ?
N5 C3 1.5182(12) . ?
C2 C3 1.5151(13) . ?
C2 H2A 1.051(16) . ?
C2 H2B 0.996(17) . ?
C3 C4 1.5260(12) . ?
C3 H3 1.012(16) . ?
C4 C4A 1.5053(11) . ?
C4 C11 1.5251(11) . ?
C4 H4 1.000(15) . ?
C4A C10A 1.3540(11) . ?
C4A C5 1.4693(11) . ?
C5 C5A 1.4869(11) . ?
C5A C6 1.3950(11) . ?
C5A C9A 1.3975(11) . ?
C6 C7 1.3908(12) . ?
C6 H6 0.993(16) . ?
C7 C8 1.3900(14) . ?
C7 H7 1.043(17) . ?
C8 C9 1.3894(14) . ?
C8 H8 0.98(2) . ?
C9 C9A 1.3981(12) . ?
C9 H9 1.017(15) . ?
C9A C10 1.4803(12) . ?
C10 C10A 1.4945(11) . ?
C11 C12 1.3919(11) . ?
C11 C16 1.3949(11) . ?
C12 C13 1.3958(12) . ?
C12 H12 0.980(15) . ?
C13 C14 1.3902(13) . ?
C13 H13 0.979(15) . ?
C14 C15 1.3947(14) . ?
C14 H14 1.017(17) . ?
C15 C16 1.3928(12) . ?
C15 H15 0.980(17) . ?
C16 H16 0.962(14) . ?

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
C10A O1 C2 116.35(6) . . ?
O5 N5 O4 124.64(9) . . ?
O5 N5 C3 119.26(8) . . ?
O4 N5 C3 116.08(9) . . ?
O1 C2 C3 111.81(7) . . ?
O1 C2 H2A 108.1(9) . . ?
C3 C2 H2A 107.8(9) . . ?
O1 C2 H2B 108.2(10) . . ?
C3 C2 H2B 109.1(10) . . ?
H2A C2 H2B 111.9(14) . . ?
C2 C3 N5 108.07(7) . . ?
C2 C3 C4 110.84(7) . . ?
N5 C3 C4 112.49(7) . . ?
C2 C3 H3 108.5(9) . . ?
N5 C3 H3 102.9(8) . . ?
C4 C3 H3 113.6(8) . . ?
C4A C4 C11 113.62(6) . . ?
C4A C4 C3 109.19(7) . . ?
C11 C4 C3 108.57(7) . . ?
C4A C4 H4 110.2(9) . . ?
C11 C4 H4 106.9(8) . . ?
C3 C4 H4 108.2(8) . . ?
C10A C4A C5 120.27(7) . . ?
C10A C4A C4 121.88(7) . . ?
C5 C4A C4 117.83(7) . . ?
O2 C5 C4A 120.04(7) . . ?
O2 C5 C5A 121.33(7) . . ?
C4A C5 C5A 118.63(7) . . ?
C6 C5A C9A 119.82(7) . . ?
C6 C5A C5 119.55(7) . . ?
C9A C5A C5 120.61(7) . . ?
C7 C6 C5A 119.91(8) . . ?
C7 C6 H6 120.1(10) . . ?
C5A C6 H6 120.0(10) . . ?
C8 C7 C6 120.30(8) . . ?
C8 C7 H7 120.5(9) . . ?
C6 C7 H7 119.2(9) . . ?
C9 C8 C7 120.13(8) . . ?
C9 C8 H8 118.3(11) . . ?
C7 C8 H8 121.6(11) . . ?
C8 C9 C9A 119.87(9) . . ?
C8 C9 H9 121.3(9) . . ?
C9A C9 H9 118.8(9) . . ?
C5A C9A C9 119.95(8) . . ?
C5A C9A C10 120.64(7) . . ?
C9 C9A C10 119.40(7) . . ?
O3 C10 C9A 122.83(8) . . ?
O3 C10 C10A 120.44(8) . . ?
C9A C10 C10A 116.73(7) . . ?
O1 C10A C4A 124.78(7) . . ?
O1 C10A C10 112.19(7) . . ?
C4A C10A C10 123.02(7) . . ?
C12 C11 C16 119.12(7) . . ?
C12 C11 C4 121.89(7) . . ?
C16 C11 C4 118.97(7) . . ?
C11 C12 C13 120.41(8) . . ?
C11 C12 H12 119.2(9) . . ?
C13 C12 H12 120.3(9) . . ?
C14 C13 C12 120.24(8) . . ?
C14 C13 H13 121.4(9) . . ?
C12 C13 H13 118.4(9) . . ?
C13 C14 C15 119.61(8) . . ?
C13 C14 H14 119.7(9) . . ?
C15 C14 H14 120.6(9) . . ?
C16 C15 C14 119.96(8) . . ?
C16 C15 H15 120.8(10) . . ?
C14 C15 H15 119.2(10) . . ?
C15 C16 C11 120.65(8) . . ?
C15 C16 H16 118.2(9) . . ?
C11 C16 H16 121.1(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
C10A O1 C2 C3 41.23(10) . . . . ?
O1 C2 C3 N5 65.21(9) . . . . ?
O1 C2 C3 C4 -58.48(9) . . . . ?
O5 N5 C3 C2 -108.50(9) . . . . ?
O4 N5 C3 C2 69.93(10) . . . . ?
O5 N5 C3 C4 14.19(11) . . . . ?
O4 N5 C3 C4 -167.38(8) . . . . ?
C2 C3 C4 C4A 44.08(9) . . . . ?
N5 C3 C4 C4A -77.03(8) . . . . ?
C2 C3 C4 C11 -80.27(8) . . . . ?
N5 C3 C4 C11 158.61(7) . . . . ?
C11 C4 C4A C10A 105.17(9) . . . . ?
C3 C4 C4A C10A -16.17(10) . . . . ?
C11 C4 C4A C5 -76.43(9) . . . . ?
C3 C4 C4A C5 162.23(7) . . . . ?
C10A C4A C5 O2 -177.55(8) . . . . ?
C4 C4A C5 O2 4.03(11) . . . . ?
C10A C4A C5 C5A 3.12(11) . . . . ?
C4 C4A C5 C5A -175.30(7) . . . . ?
O2 C5 C5A C6 -3.01(12) . . . . ?
C4A C5 C5A C6 176.30(7) . . . . ?
O2 C5 C5A C9A 178.22(8) . . . . ?
C4A C5 C5A C9A -2.46(11) . . . . ?
C9A C5A C6 C7 -0.09(12) . . . . ?
C5 C5A C6 C7 -178.86(8) . . . . ?
C5A C6 C7 C8 -1.05(14) . . . . ?
C6 C7 C8 C9 1.16(15) . . . . ?
C7 C8 C9 C9A -0.13(15) . . . . ?
C6 C5A C9A C9 1.11(12) . . . . ?
C5 C5A C9A C9 179.87(8) . . . . ?
C6 C5A C9A C10 -179.00(8) . . . . ?
C5 C5A C9A C10 -0.24(12) . . . . ?
C8 C9 C9A C5A -1.00(13) . . . . ?
C8 C9 C9A C10 179.11(8) . . . . ?
C5A C9A C10 O3 -177.11(8) . . . . ?
C9 C9A C10 O3 2.78(13) . . . . ?
C5A C9A C10 C10A 2.24(11) . . . . ?
C9 C9A C10 C10A -177.87(8) . . . . ?
C2 O1 C10A C4A -11.56(12) . . . . ?
C2 O1 C10A C10 169.76(7) . . . . ?
C5 C4A C10A O1 -179.63(7) . . . . ?
C4 C4A C10A O1 -1.27(12) . . . . ?
C5 C4A C10A C10 -1.09(12) . . . . ?
C4 C4A C10A C10 177.27(7) . . . . ?
O3 C10 C10A O1 -3.53(11) . . . . ?
C9A C10 C10A O1 177.10(7) . . . . ?
O3 C10 C10A C4A 177.77(8) . . . . ?
C9A C10 C10A C4A -1.60(11) . . . . ?
C4A C4 C11 C12 -9.77(11) . . . . ?
C3 C4 C11 C12 111.92(8) . . . . ?
C4A C4 C11 C16 171.32(7) . . . . ?
C3 C4 C11 C16 -66.99(10) . . . . ?
C16 C11 C12 C13 -0.42(12) . . . . ?
C4 C11 C12 C13 -179.33(8) . . . . ?
C11 C12 C13 C14 1.21(13) . . . . ?
C12 C13 C14 C15 -1.09(13) . . . . ?
C13 C14 C15 C16 0.19(14) . . . . ?
C14 C15 C16 C11 0.61(14) . . . . ?
C12 C11 C16 C15 -0.49(13) . . . . ?
C4 C11 C16 C15 178.45(8) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.026

