# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_220701sjt_0m
_database_code_depnum_ccdc_archive 'CCDC 2257602'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O6'
_chemical_formula_sum            'C23 H17 N O6'
_chemical_formula_weight         403.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   11.6847(3)
_cell_length_b                   13.9633(3)
_cell_length_c                   23.2986(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3801.33(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.985
_cell_measurement_theta_min      3.301
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.8069.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            41038
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.980
_diffrn_reflns_theta_min         3.301
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3000
_reflns_number_total             3619
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.68705(8) 0.37833(7) 0.49039(4) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.83398(14) 0.47135(12) 0.37541(8) 0.0846(5) Uani 1 1 d . . . . .
O3 O 0.76896(14) 0.62220(10) 0.38138(6) 0.0742(5) Uani 1 1 d . . . . .
O4 O 0.36659(11) 0.47628(9) 0.42297(5) 0.0529(3) Uani 1 1 d . . . . .
H4 H 0.308488 0.510237 0.420570 0.079 Uiso 1 1 calc R U . . .
O5 O 0.19941(12) 0.56552(11) 0.37245(6) 0.0678(4) Uani 1 1 d . . . . .
O6 O 0.16615(9) 0.53788(8) 0.27992(5) 0.0496(3) Uani 1 1 d . . . . .
N1 N 0.67483(11) 0.51040(9) 0.42758(6) 0.0390(3) Uani 1 1 d . . . . .
C1 C 0.63836(12) 0.41868(10) 0.44185(6) 0.0339(3) Uani 1 1 d . . . . .
C2 C 0.55805(12) 0.36346(10) 0.41806(6) 0.0325(3) Uani 1 1 d . . . . .
C3 C 0.55019(12) 0.27953(10) 0.45426(6) 0.0349(3) Uani 1 1 d . . . . .
C4 C 0.48139(14) 0.19811(11) 0.45533(7) 0.0458(4) Uani 1 1 d . . . . .
H4A H 0.426598 0.187084 0.426536 0.055 Uiso 1 1 calc R U . . .
C5 C 0.49587(16) 0.13423(13) 0.49973(8) 0.0561(5) Uani 1 1 d . . . . .
H5 H 0.448680 0.079805 0.501685 0.067 Uiso 1 1 calc R U . . .
C6 C 0.57833(17) 0.14823(14) 0.54161(8) 0.0577(5) Uani 1 1 d . . . . .
H6 H 0.586733 0.102516 0.570923 0.069 Uiso 1 1 calc R U . . .
C7 C 0.64875(15) 0.22813(13) 0.54127(7) 0.0486(4) Uani 1 1 d . . . . .
H7 H 0.705439 0.237760 0.569306 0.058 Uiso 1 1 calc R U . . .
C8 C 0.63068(12) 0.29280(10) 0.49727(6) 0.0361(3) Uani 1 1 d . . . . .
C9 C 0.49042(12) 0.38574(10) 0.36587(6) 0.0330(3) Uani 1 1 d . . . . .
C10 C 0.39453(13) 0.44278(11) 0.37024(6) 0.0381(4) Uani 1 1 d . . . . .
C11 C 0.32768(12) 0.46509(11) 0.32082(7) 0.0371(4) Uani 1 1 d . . . . .
C12 C 0.35896(12) 0.42896(10) 0.26841(6) 0.0370(4) Uani 1 1 d . . . . .
H12 H 0.314113 0.443267 0.236029 0.044 Uiso 1 1 calc R U . . .
C13 C 0.45652(13) 0.37102(10) 0.26192(6) 0.0342(3) Uani 1 1 d . . . . .
C14 C 0.49004(13) 0.33427(11) 0.20783(6) 0.0424(4) Uani 1 1 d . . . . .
H14 H 0.446723 0.348909 0.174985 0.051 Uiso 1 1 calc R U . . .
C15 C 0.58481(15) 0.27775(12) 0.20307(7) 0.0459(4) Uani 1 1 d . . . . .
H15 H 0.605971 0.253193 0.167036 0.055 Uiso 1 1 calc R U . . .
C16 C 0.65047(14) 0.25620(12) 0.25135(7) 0.0447(4) Uani 1 1 d . . . . .
H16 H 0.715543 0.217158 0.247473 0.054 Uiso 1 1 calc R U . . .
C17 C 0.62160(12) 0.29101(10) 0.30422(6) 0.0379(4) Uani 1 1 d . . . . .
H17 H 0.667349 0.276196 0.336199 0.045 Uiso 1 1 calc R U . . .
C18 C 0.52334(11) 0.34922(10) 0.31126(6) 0.0317(3) Uani 1 1 d . . . . .
C19 C 0.22611(13) 0.52698(11) 0.32747(7) 0.0435(4) Uani 1 1 d . . . . .
C20 C 0.06364(15) 0.59616(13) 0.28440(10) 0.0609(5) Uani 1 1 d . . . . .
H20A H 0.022970 0.595149 0.248112 0.091 Uiso 1 1 calc R U . . .
H20B H 0.084774 0.661514 0.293715 0.091 Uiso 1 1 calc R U . . .
H20C H 0.014676 0.570742 0.314376 0.091 Uiso 1 1 calc R U . . .
C21 C 0.76541(16) 0.52773(13) 0.39316(7) 0.0500(4) Uani 1 1 d . . . . .
C22 C 0.66989(18) 0.66808(13) 0.40436(9) 0.0623(5) Uani 1 1 d . . . . .
H22A H 0.616713 0.685405 0.373532 0.075 Uiso 1 1 calc R U . . .
H22B H 0.691411 0.726362 0.425160 0.075 Uiso 1 1 calc R U . . .
C23 C 0.61602(16) 0.59755(12) 0.44406(10) 0.0599(5) Uani 1 1 d . . . . .
H23A H 0.630405 0.613888 0.484325 0.072 Uiso 1 1 calc R U . . .
H23B H 0.533346 0.592614 0.437626 0.072 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 C1 1.3857(17) . ?
O1 C8 1.3731(18) . ?
O2 C21 1.197(2) . ?
O3 C21 1.348(2) . ?
O3 C22 1.427(3) . ?
O4 H4 0.8300 . ?
O4 C10 1.3545(18) . ?
O5 C19 1.219(2) . ?
O6 C19 1.320(2) . ?
O6 C20 1.452(2) . ?
N1 C1 1.3902(19) . ?
N1 C21 1.350(2) . ?
N1 C23 1.449(2) . ?
C1 C2 1.335(2) . ?
C2 C3 1.447(2) . ?
C2 C9 1.4831(19) . ?
C3 C4 1.393(2) . ?
C3 C8 1.387(2) . ?
C4 H4A 0.9400 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9400 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.382(2) . ?
C9 C10 1.3784(19) . ?
C9 C18 1.424(2) . ?
C10 C11 1.426(2) . ?
C11 C12 1.371(2) . ?
C11 C19 1.476(2) . ?
C12 H12 0.9400 . ?
C12 C13 1.406(2) . ?
C13 C14 1.416(2) . ?
C13 C18 1.422(2) . ?
C14 H14 0.9400 . ?
C14 C15 1.364(2) . ?
C15 H15 0.9400 . ?
C15 C16 1.394(2) . ?
C16 H16 0.9400 . ?
C16 C17 1.367(2) . ?
C17 H17 0.9400 . ?
C17 C18 1.4162(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 C23 1.491(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?

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 C1 104.59(11) . . ?
C21 O3 C22 109.75(14) . . ?
C10 O4 H4 109.5 . . ?
C19 O6 C20 116.25(14) . . ?
C1 N1 C23 124.38(13) . . ?
C21 N1 C1 123.21(13) . . ?
C21 N1 C23 112.25(13) . . ?
O1 C1 N1 116.36(12) . . ?
C2 C1 O1 113.12(12) . . ?
C2 C1 N1 130.40(13) . . ?
C1 C2 C3 105.69(12) . . ?
C1 C2 C9 126.43(13) . . ?
C3 C2 C9 127.87(13) . . ?
C4 C3 C2 135.11(14) . . ?
C8 C3 C2 105.66(13) . . ?
C8 C3 C4 119.18(13) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.13(16) . . ?
C5 C4 H4A 120.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.57(17) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.50(15) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 122.0 . . ?
C8 C7 C6 116.06(16) . . ?
C8 C7 H7 122.0 . . ?
O1 C8 C3 110.92(12) . . ?
O1 C8 C7 125.55(14) . . ?
C7 C8 C3 123.52(15) . . ?
C10 C9 C2 119.59(12) . . ?
C10 C9 C18 119.50(13) . . ?
C18 C9 C2 120.91(12) . . ?
O4 C10 C9 117.54(13) . . ?
O4 C10 C11 121.66(13) . . ?
C9 C10 C11 120.79(13) . . ?
C10 C11 C19 118.92(13) . . ?
C12 C11 C10 119.53(13) . . ?
C12 C11 C19 121.55(14) . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.58(13) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 121.90(13) . . ?
C12 C13 C18 118.77(13) . . ?
C14 C13 C18 119.33(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.43(14) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.39(14) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.97(14) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.57(14) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C9 119.82(12) . . ?
C17 C18 C9 121.87(13) . . ?
C17 C18 C13 118.32(13) . . ?
O5 C19 O6 122.34(14) . . ?
O5 C19 C11 123.69(15) . . ?
O6 C19 C11 113.97(14) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O3 123.55(16) . . ?
O2 C21 N1 127.75(18) . . ?
O3 C21 N1 108.70(16) . . ?
O3 C22 H22A 110.5 . . ?
O3 C22 H22B 110.5 . . ?
O3 C22 C23 106.18(15) . . ?
H22A C22 H22B 108.7 . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
N1 C23 C22 100.96(14) . . ?
N1 C23 H23A 111.6 . . ?
N1 C23 H23B 111.6 . . ?
C22 C23 H23A 111.6 . . ?
C22 C23 H23B 111.6 . . ?
H23A C23 H23B 109.4 . . ?

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
O1 C1 C2 C3 1.23(16) . . . . ?
O1 C1 C2 C9 -179.77(12) . . . . ?
O3 C22 C23 N1 -14.3(2) . . . . ?
O4 C10 C11 C12 -179.56(14) . . . . ?
O4 C10 C11 C19 0.5(2) . . . . ?
N1 C1 C2 C3 -174.68(14) . . . . ?
N1 C1 C2 C9 4.3(2) . . . . ?
C1 O1 C8 C3 0.54(15) . . . . ?
C1 O1 C8 C7 -178.45(14) . . . . ?
C1 N1 C21 O2 -9.0(3) . . . . ?
C1 N1 C21 O3 171.65(14) . . . . ?
C1 N1 C23 C22 -164.13(16) . . . . ?
C1 C2 C3 C4 176.45(17) . . . . ?
C1 C2 C3 C8 -0.82(15) . . . . ?
C1 C2 C9 C10 -82.92(19) . . . . ?
C1 C2 C9 C18 96.91(18) . . . . ?
C2 C3 C4 C5 -176.46(16) . . . . ?
C2 C3 C8 O1 0.16(15) . . . . ?
C2 C3 C8 C7 179.17(14) . . . . ?
C2 C9 C10 O4 0.1(2) . . . . ?
C2 C9 C10 C11 -179.79(14) . . . . ?
C2 C9 C18 C13 179.52(12) . . . . ?
C2 C9 C18 C17 -0.4(2) . . . . ?
C3 C2 C9 C10 95.87(18) . . . . ?
C3 C2 C9 C18 -84.30(19) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C4 C3 C8 O1 -177.64(13) . . . . ?
C4 C3 C8 C7 1.4(2) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 O1 176.90(14) . . . . ?
C6 C7 C8 C3 -2.0(2) . . . . ?
C8 O1 C1 N1 175.39(11) . . . . ?
C8 O1 C1 C2 -1.13(16) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C9 C2 C3 C4 -2.5(3) . . . . ?
C9 C2 C3 C8 -179.81(13) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C9 C10 C11 C19 -179.60(14) . . . . ?
C10 C9 C18 C13 -0.7(2) . . . . ?
C10 C9 C18 C17 179.43(13) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C10 C11 C19 O5 4.8(2) . . . . ?
C10 C11 C19 O6 -175.70(14) . . . . ?
C11 C12 C13 C14 -179.32(14) . . . . ?
C11 C12 C13 C18 0.5(2) . . . . ?
C12 C11 C19 O5 -175.14(17) . . . . ?
C12 C11 C19 O6 4.4(2) . . . . ?
C12 C13 C14 C15 -179.59(14) . . . . ?
C12 C13 C18 C9 0.2(2) . . . . ?
C12 C13 C18 C17 -179.83(13) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C13 C18 C9 -179.97(13) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C9 179.35(14) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C18 C9 C10 O4 -179.74(14) . . . . ?
C18 C9 C10 C11 0.4(2) . . . . ?
C18 C13 C14 C15 0.6(2) . . . . ?
C19 C11 C12 C13 179.18(13) . . . . ?
C20 O6 C19 O5 -2.0(2) . . . . ?
C20 O6 C19 C11 178.49(13) . . . . ?
C21 O3 C22 C23 13.2(2) . . . . ?
C21 N1 C1 O1 89.43(18) . . . . ?
C21 N1 C1 C2 -94.8(2) . . . . ?
C21 N1 C23 C22 11.5(2) . . . . ?
C22 O3 C21 O2 174.7(2) . . . . ?
C22 O3 C21 N1 -6.0(2) . . . . ?
C23 N1 C1 O1 -95.36(18) . . . . ?
C23 N1 C1 C2 80.4(2) . . . . ?
C23 N1 C21 O2 175.3(2) . . . . ?
C23 N1 C21 O3 -4.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_220704sjt_0m
_database_code_depnum_ccdc_archive 'CCDC 2257604'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O6'
_chemical_formula_sum            'C23 H17 N O6'
_chemical_formula_weight         403.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4331(2)
_cell_length_b                   11.3391(2)
_cell_length_c                   17.0360(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.5160(10)
_cell_angle_gamma                90
_cell_volume                     1810.45(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6738
_cell_measurement_temperature    214.00
_cell_measurement_theta_max      54.867
_cell_measurement_theta_min      4.084
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1070 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8382.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13399
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.936
_diffrn_reflns_theta_min         4.460
_diffrn_ambient_temperature      214.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2727
_reflns_number_total             3425
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C15(H15), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.25363(10) 0.66166(9) 0.57752(6) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.02171(11) 0.64831(9) 0.51913(6) 0.0281(3) Uani 1 1 d . . . . .
O3 O -0.08255(12) 0.90464(11) 0.56618(7) 0.0405(3) Uani 1 1 d . . . . .
O4 O -0.10071(12) 0.83730(11) 0.68811(7) 0.0392(3) Uani 1 1 d . . . . .
O5 O 0.46845(12) 0.51401(12) 0.64194(8) 0.0468(4) Uani 1 1 d . . . . .
O6 O 0.68695(11) 0.54733(11) 0.60882(7) 0.0402(3) Uani 1 1 d . . . . .
N1 N 0.08068(12) 0.77136(11) 0.62693(7) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.12713(15) 0.72831(13) 0.55472(9) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.16065(15) 0.82012(13) 0.49134(8) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.139535 0.901956 0.506606 0.028 Uiso 1 1 calc R U . . .
C3 C 0.06379(15) 0.77868(14) 0.42013(9) 0.0249(3) Uani 1 1 d . . . . .
C4 C 0.03912(16) 0.82068(15) 0.34309(9) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.087488 0.887642 0.327428 0.038 Uiso 1 1 calc R U . . .
C5 C -0.05852(18) 0.76166(17) 0.28969(10) 0.0374(4) Uani 1 1 d . . . . .
H5 H -0.074916 0.788264 0.237189 0.045 Uiso 1 1 calc R U . . .
C6 C -0.13210(18) 0.66401(16) 0.31288(10) 0.0357(4) Uani 1 1 d . . . . .
H6 H -0.198152 0.625946 0.275831 0.043 Uiso 1 1 calc R U . . .
C7 C -0.11009(17) 0.62140(15) 0.38971(10) 0.0308(4) Uani 1 1 d . . . . .
H7 H -0.160407 0.555892 0.405972 0.037 Uiso 1 1 calc R U . . .
C8 C -0.01069(15) 0.68013(14) 0.44083(9) 0.0256(3) Uani 1 1 d . . . . .
C9 C -0.03820(16) 0.84331(14) 0.62105(9) 0.0287(4) Uani 1 1 d . . . . .
C10 C 0.07156(17) 0.68824(15) 0.69237(9) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.165862 0.670424 0.720130 0.037 Uiso 1 1 calc R U . . .
H10B H 0.024164 0.614662 0.674196 0.037 Uiso 1 1 calc R U . . .
C11 C -0.0185(2) 0.75957(16) 0.74338(10) 0.0395(4) Uani 1 1 d . . . . .
H11A H -0.081272 0.708141 0.770153 0.047 Uiso 1 1 calc R U . . .
H11B H 0.041917 0.804875 0.783181 0.047 Uiso 1 1 calc R U . . .
C12 C 0.31825(15) 0.79926(13) 0.48901(9) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.36132(15) 0.70819(13) 0.53802(9) 0.0242(3) Uani 1 1 d . . . . .
C14 C 0.50345(15) 0.66646(14) 0.54940(9) 0.0249(3) Uani 1 1 d . . . . .
C15 C 0.59995(16) 0.72350(14) 0.50709(9) 0.0267(4) Uani 1 1 d . . . . .
H15 H 0.695069 0.697232 0.512256 0.032 Uiso 1 1 calc R U . . .
C16 C 0.56124(15) 0.81938(14) 0.45657(9) 0.0240(3) Uani 1 1 d . . . . .
C17 C 0.66358(16) 0.87956(14) 0.41667(9) 0.0283(4) Uani 1 1 d . . . . .
H17 H 0.758665 0.853206 0.422066 0.034 Uiso 1 1 calc R U . . .
C18 C 0.62558(17) 0.97544(14) 0.37047(9) 0.0302(4) Uani 1 1 d . . . . .
H18 H 0.694532 1.014371 0.344242 0.036 Uiso 1 1 calc R U . . .
C19 C 0.48366(17) 1.01627(14) 0.36192(9) 0.0295(4) Uani 1 1 d . . . . .
H19 H 0.458839 1.082527 0.330141 0.035 Uiso 1 1 calc R U . . .
C20 C 0.38157(16) 0.96069(14) 0.39931(9) 0.0262(4) Uani 1 1 d . . . . .
H20 H 0.287384 0.989181 0.393187 0.031 Uiso 1 1 calc R U . . .
C21 C 0.41692(16) 0.86017(13) 0.44734(9) 0.0236(3) Uani 1 1 d . . . . .
C22 C 0.54671(16) 0.56843(14) 0.60444(9) 0.0275(4) Uani 1 1 d . . . . .
C23 C 0.73901(18) 0.45423(17) 0.66143(11) 0.0405(5) Uani 1 1 d . . . . .
H23A H 0.692619 0.380788 0.644333 0.061 Uiso 1 1 calc R U . . .
H23B H 0.718306 0.472664 0.714548 0.061 Uiso 1 1 calc R U . . .
H23C H 0.841301 0.446304 0.660966 0.061 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 C1 1.4285(17) . ?
O1 C13 1.3851(17) . ?
O2 C1 1.4292(18) . ?
O2 C8 1.3821(18) . ?
O3 C9 1.2015(19) . ?
O4 C9 1.3456(18) . ?
O4 C11 1.449(2) . ?
O5 C22 1.2004(18) . ?
O6 C22 1.3382(18) . ?
O6 C23 1.4350(19) . ?
N1 C1 1.4374(18) . ?
N1 C9 1.3812(19) . ?
N1 C10 1.4697(19) . ?
C1 C2 1.558(2) . ?
C2 H2 0.9900 . ?
C2 C3 1.509(2) . ?
C2 C12 1.5103(19) . ?
C3 C4 1.391(2) . ?
C3 C8 1.387(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.391(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9400 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.377(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C11 1.516(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.361(2) . ?
C12 C21 1.413(2) . ?
C13 C14 1.414(2) . ?
C14 C15 1.384(2) . ?
C14 C22 1.481(2) . ?
C15 H15 0.9400 . ?
C15 C16 1.409(2) . ?
C16 C17 1.417(2) . ?
C16 C21 1.429(2) . ?
C17 H17 0.9400 . ?
C17 C18 1.366(2) . ?
C18 H18 0.9400 . ?
C18 C19 1.408(2) . ?
C19 H19 0.9400 . ?
C19 C20 1.367(2) . ?
C20 H20 0.9400 . ?
C20 C21 1.421(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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
C13 O1 C1 107.60(11) . . ?
C8 O2 C1 108.10(11) . . ?
C9 O4 C11 109.19(12) . . ?
C22 O6 C23 115.62(12) . . ?
C1 N1 C10 118.76(12) . . ?
C9 N1 C1 117.54(12) . . ?
C9 N1 C10 108.48(12) . . ?
O1 C1 O2 107.41(11) . . ?
O1 C1 N1 105.86(11) . . ?
O1 C1 C2 108.24(11) . . ?
O2 C1 N1 108.28(11) . . ?
O2 C1 C2 108.44(11) . . ?
N1 C1 C2 118.15(12) . . ?
C1 C2 H2 112.4 . . ?
C3 C2 C1 101.37(12) . . ?
C3 C2 H2 112.4 . . ?
C3 C2 C12 115.99(12) . . ?
C12 C2 C1 101.03(11) . . ?
C12 C2 H2 112.4 . . ?
C4 C3 C2 132.34(15) . . ?
C8 C3 C2 108.94(13) . . ?
C8 C3 C4 118.72(15) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.69(16) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.88(16) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.32(16) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.8 . . ?
C8 C7 C6 116.50(16) . . ?
C8 C7 H7 121.8 . . ?
O2 C8 C3 113.14(13) . . ?
C7 C8 O2 122.97(14) . . ?
C7 C8 C3 123.86(15) . . ?
O3 C9 O4 122.84(14) . . ?
O3 C9 N1 127.34(14) . . ?
O4 C9 N1 109.81(13) . . ?
N1 C10 H10A 111.7 . . ?
N1 C10 H10B 111.7 . . ?
N1 C10 C11 100.23(13) . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10A 111.7 . . ?
C11 C10 H10B 111.7 . . ?
O4 C11 C10 104.21(12) . . ?
O4 C11 H11A 110.9 . . ?
O4 C11 H11B 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C2 109.21(12) . . ?
C13 C12 C21 120.75(13) . . ?
C21 C12 C2 130.02(13) . . ?
O1 C13 C14 122.82(13) . . ?
C12 C13 O1 113.76(12) . . ?
C12 C13 C14 123.40(13) . . ?
C13 C14 C22 121.78(13) . . ?
C15 C14 C13 116.20(14) . . ?
C15 C14 C22 122.01(13) . . ?
C14 C15 H15 118.7 . . ?
C14 C15 C16 122.59(14) . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C17 121.40(14) . . ?
C15 C16 C21 119.64(13) . . ?
C17 C16 C21 118.91(14) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.74(14) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.36(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.78(15) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.43(14) . . ?
C21 C20 H20 119.8 . . ?
C12 C21 C16 117.38(13) . . ?
C12 C21 C20 123.82(13) . . ?
C20 C21 C16 118.77(13) . . ?
O5 C22 O6 122.83(15) . . ?
O5 C22 C14 125.51(14) . . ?
O6 C22 C14 111.66(13) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O1 C1 C2 C3 115.66(12) . . . . ?
O1 C1 C2 C12 -3.99(15) . . . . ?
O1 C13 C14 C15 -178.57(14) . . . . ?
O1 C13 C14 C22 0.5(2) . . . . ?
O2 C1 C2 C3 -0.57(14) . . . . ?
O2 C1 C2 C12 -120.21(12) . . . . ?
N1 C1 C2 C3 -124.16(13) . . . . ?
N1 C1 C2 C12 116.19(13) . . . . ?
N1 C10 C11 O4 26.55(17) . . . . ?
C1 O1 C13 C12 -1.29(17) . . . . ?
C1 O1 C13 C14 177.17(14) . . . . ?
C1 O2 C8 C3 -1.12(16) . . . . ?
C1 O2 C8 C7 -179.33(13) . . . . ?
C1 N1 C9 O3 -25.4(2) . . . . ?
C1 N1 C9 O4 155.37(13) . . . . ?
C1 N1 C10 C11 -164.53(13) . . . . ?
C1 C2 C3 C4 179.73(15) . . . . ?
C1 C2 C3 C8 -0.08(15) . . . . ?
C1 C2 C12 C13 3.26(16) . . . . ?
C1 C2 C12 C21 -174.89(15) . . . . ?
C2 C3 C4 C5 179.74(15) . . . . ?
C2 C3 C8 O2 0.74(17) . . . . ?
C2 C3 C8 C7 178.93(14) . . . . ?
C2 C12 C13 O1 -1.46(18) . . . . ?
C2 C12 C13 C14 -179.90(14) . . . . ?
C2 C12 C21 C16 -179.75(14) . . . . ?
C2 C12 C21 C20 2.2(3) . . . . ?
C3 C2 C12 C13 -105.32(15) . . . . ?
C3 C2 C12 C21 76.5(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C3 C8 O2 -179.10(12) . . . . ?
C4 C3 C8 C7 -0.9(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 O2 179.54(13) . . . . ?
C6 C7 C8 C3 1.5(2) . . . . ?
C8 O2 C1 O1 -115.74(12) . . . . ?
C8 O2 C1 N1 130.35(12) . . . . ?
C8 O2 C1 C2 1.02(14) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C9 O4 C11 C10 -18.47(18) . . . . ?
C9 N1 C1 O1 177.49(12) . . . . ?
C9 N1 C1 O2 -67.59(16) . . . . ?
C9 N1 C1 C2 56.09(18) . . . . ?
C9 N1 C10 C11 -26.84(17) . . . . ?
C10 N1 C1 O1 -48.57(16) . . . . ?
C10 N1 C1 O2 66.35(16) . . . . ?
C10 N1 C1 C2 -169.97(13) . . . . ?
C10 N1 C9 O3 -163.72(17) . . . . ?
C10 N1 C9 O4 17.10(18) . . . . ?
C11 O4 C9 O3 -177.77(17) . . . . ?
C11 O4 C9 N1 1.46(18) . . . . ?
C12 C2 C3 C4 -71.9(2) . . . . ?
C12 C2 C3 C8 108.30(15) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C12 C13 C14 C22 178.85(14) . . . . ?
C13 O1 C1 O2 120.28(12) . . . . ?
C13 O1 C1 N1 -124.21(12) . . . . ?
C13 O1 C1 C2 3.39(15) . . . . ?
C13 C12 C21 C16 2.3(2) . . . . ?
C13 C12 C21 C20 -175.73(14) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C13 C14 C22 O5 2.2(3) . . . . ?
C13 C14 C22 O6 -177.00(14) . . . . ?
C14 C15 C16 C17 177.13(15) . . . . ?
C14 C15 C16 C21 -0.5(2) . . . . ?
C15 C14 C22 O5 -178.76(16) . . . . ?
C15 C14 C22 O6 2.1(2) . . . . ?
C15 C16 C17 C18 -177.26(14) . . . . ?
C15 C16 C21 C12 -1.3(2) . . . . ?
C15 C16 C21 C20 176.83(13) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C16 C21 C12 -178.98(14) . . . . ?
C17 C16 C21 C20 -0.9(2) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C19 C20 C21 C12 178.79(15) . . . . ?
C19 C20 C21 C16 0.8(2) . . . . ?
C21 C12 C13 O1 176.89(13) . . . . ?
C21 C12 C13 C14 -1.6(2) . . . . ?
C21 C16 C17 C18 0.4(2) . . . . ?
C22 C14 C15 C16 -177.83(14) . . . . ?
C23 O6 C22 O5 0.3(2) . . . . ?
C23 O6 C22 C14 179.46(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
