# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_5aa
_database_code_depnum_ccdc_archive 'CCDC 2410198'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O6'
_chemical_formula_sum            'C23 H21 N O6'
_chemical_formula_weight         407.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   20.404(5)
_cell_length_b                   9.4554(19)
_cell_length_c                   22.554(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.201(17)
_cell_angle_gamma                90
_cell_volume                     4350.3(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.5700
_cell_measurement_theta_min      2.2140
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11810
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.472
_diffrn_reflns_theta_min         1.997
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  89.00   1.00   60.00    --   13.93  57.00 120.00   96
  2  ω    -13.00  16.00   1.00   60.00    --   13.93  77.00 -30.00   29
  3  ω     42.00 107.00   1.00   60.00    --   13.93 178.00 -60.00   65
  4  ω    -77.00 -44.00   1.00   60.00    --  -14.24 134.00 -92.13   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0278179000
_diffrn_orient_matrix_UB_12      0.0452166000
_diffrn_orient_matrix_UB_13      0.0008565000
_diffrn_orient_matrix_UB_21      -0.0019973000
_diffrn_orient_matrix_UB_22      0.0069547000
_diffrn_orient_matrix_UB_23      -0.0312680000
_diffrn_orient_matrix_UB_31      -0.0206643000
_diffrn_orient_matrix_UB_32      0.0597138000
_diffrn_orient_matrix_UB_33      0.0029546000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2680
_reflns_number_total             5141
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0046(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5141
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1161P)²+0.5808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.2446
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19-C20
 1.5 with sigma of 0.02
 C19A-C20A
 1.5 with sigma of 0.02
 O4-C22 \\sim O4-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 O4-C23 \\sim O4-C23A
 with sigma of 0.04
 O6-C18 \\sim O6A-C18
 with sigma of 0.02
 C18-C19 \\sim C18-C19A
 with sigma of 0.04
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 O6-C19 \\sim O6A-C19A
 with sigma of 0.02
 O6-C20 \\sim O6A-C20A
 with sigma of 0.04
2. Rigid bond restraints
 C22A, C22, C23, C23A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O6, O6A, C19A, C19, C20A, C20
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C22A \\sim C22 \\sim C23 \\sim C23A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
O6 \\sim O6A \\sim C19A \\sim C19 \\sim C20A \\sim C20: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(O6A)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=1-FVAR(2)
 Sof(O6)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19A(H19C,H19D), C19(H19A,H19B), C22A(H22C,H22D), C22(H22A,H22B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
5.c Idealised Me refined as rotating group:
 C20A(H20D,H20E,H20F), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C23A(H23D,
 H23E,H23F)
;
_atom_sites_solution_hydrogens   mixed
_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 0.29512(9) 0.6386(2) 0.78686(7) 0.0634(5) Uani 1 1 d . . . . .
N1 N 0.34723(9) 0.4243(2) 0.78084(8) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.31379(11) 0.5378(3) 0.75630(10) 0.0467(6) Uani 1 1 d . . . . .
O2 O 0.27117(9) 0.6446(2) 0.66768(8) 0.0582(5) Uani 1 1 d . . . . .
H2 H 0.2570(17) 0.706(4) 0.6929(15) 0.101(12) Uiso 1 1 d . . . . .
C2 C 0.30402(11) 0.5358(3) 0.69312(10) 0.0469(6) Uani 1 1 d . . . . .
C3 C 0.32780(10) 0.4273(3) 0.66001(10) 0.0451(6) Uani 1 1 d . . . . .
O3 O 0.42002(10) 0.1881(2) 0.61718(9) 0.0804(7) Uani 1 1 d . . . . .
O4 O 0.33949(10) 0.0723(2) 0.66197(9) 0.0724(6) Uani 1 1 d D . . . .
C4 C 0.35674(10) 0.3082(3) 0.68879(10) 0.0457(6) Uani 1 1 d . . . . .
C5 C 0.36722(10) 0.3068(3) 0.74838(10) 0.0449(6) Uani 1 1 d . . . . .
O5 O 0.29311(13) 0.3391(3) 0.56626(9) 0.0952(8) Uani 1 1 d . . . . .
O6 O 0.3552(17) 0.527(3) 0.5688(7) 0.095(4) Uani 0.450(13) 1 d D U P A 1
C6 C 0.36498(11) 0.4327(3) 0.84376(10) 0.0482(6) Uani 1 1 d . . . . .
O6A O 0.3528(15) 0.539(2) 0.5736(6) 0.097(3) Uani 0.550(13) 1 d D U P A 2
C7 C 0.42112(13) 0.5041(3) 0.86039(11) 0.0651(8) Uani 1 1 d . . . . .
H7 H 0.446211 0.549585 0.832196 0.078 Uiso 1 1 calc R U . . .
C8 C 0.43947(16) 0.5072(4) 0.91902(13) 0.0881(11) Uani 1 1 d . . . . .
H8 H 0.477233 0.555160 0.931089 0.106 Uiso 1 1 calc R U . . .
C9 C 0.40210(17) 0.4394(5) 0.95986(13) 0.0891(12) Uani 1 1 d . . . . .
H9 H 0.415294 0.439848 0.999578 0.107 Uiso 1 1 calc R U . . .
C10 C 0.34563(16) 0.3709(4) 0.94320(12) 0.0798(10) Uani 1 1 d . . . . .
H10 H 0.320292 0.326465 0.971500 0.096 Uiso 1 1 calc R U . . .
C11 C 0.32645(13) 0.3681(3) 0.88423(12) 0.0634(8) Uani 1 1 d . . . . .
H11 H 0.287894 0.322923 0.872310 0.076 Uiso 1 1 calc R U . . .
C12 C 0.40065(12) 0.1869(3) 0.77964(10) 0.0498(6) Uani 1 1 d . . . . .
C13 C 0.46747(14) 0.1781(4) 0.78274(15) 0.0790(9) Uani 1 1 d . . . . .
H13 H 0.492670 0.249993 0.766707 0.095 Uiso 1 1 calc R U . . .
C14 C 0.49809(16) 0.0632(4) 0.80951(17) 0.0941(11) Uani 1 1 d . . . . .
H14 H 0.543637 0.058945 0.810826 0.113 Uiso 1 1 calc R U . . .
C15 C 0.46340(19) -0.0422(4) 0.83364(14) 0.0858(10) Uani 1 1 d . . . . .
H15 H 0.484678 -0.117540 0.852258 0.103 Uiso 1 1 calc R U . . .
C16 C 0.39642(19) -0.0373(4) 0.83047(16) 0.0921(11) Uani 1 1 d . . . . .
H16 H 0.371559 -0.110142 0.846182 0.111 Uiso 1 1 calc R U . . .
C17 C 0.36612(15) 0.0779(4) 0.80350(15) 0.0786(9) Uani 1 1 d . . . . .
H17 H 0.320573 0.081040 0.801590 0.094 Uiso 1 1 calc R U . . .
C18 C 0.32155(13) 0.4286(3) 0.59421(11) 0.0563(7) Uani 1 1 d D . . . .
C19A C 0.3705(8) 0.5295(16) 0.5101(5) 0.134(4) Uani 0.550(13) 1 d D U P A 2
H19C H 0.378408 0.431648 0.499605 0.161 Uiso 0.550(13) 1 calc R U P A 2
H19D H 0.334537 0.564510 0.485424 0.161 Uiso 0.550(13) 1 calc R U P A 2
C19 C 0.3438(11) 0.5425(16) 0.5039(7) 0.125(4) Uani 0.450(13) 1 d D U P A 1
H19A H 0.378687 0.495611 0.483038 0.150 Uiso 0.450(13) 1 calc R U P A 1
H19B H 0.302736 0.497106 0.492630 0.150 Uiso 0.450(13) 1 calc R U P A 1
C20A C 0.4284(9) 0.612(2) 0.5001(5) 0.266(10) Uani 0.550(13) 1 d D U P A 2
H20D H 0.427657 0.645994 0.459944 0.400 Uiso 0.550(13) 1 calc R U P A 2
H20E H 0.466559 0.554492 0.506743 0.400 Uiso 0.550(13) 1 calc R U P A 2
H20F H 0.429585 0.691106 0.526843 0.400 Uiso 0.550(13) 1 calc R U P A 2
C20 C 0.3413(14) 0.6892(12) 0.4867(5) 0.224(10) Uani 0.450(13) 1 d D U P A 1
H20A H 0.299567 0.728298 0.496706 0.337 Uiso 0.450(13) 1 calc R U P A 1
H20B H 0.347244 0.696767 0.444723 0.337 Uiso 0.450(13) 1 calc R U P A 1
H20C H 0.375552 0.740215 0.507260 0.337 Uiso 0.450(13) 1 calc R U P A 1
C21 C 0.37747(12) 0.1833(3) 0.65230(11) 0.0518(6) Uani 1 1 d . . . . .
C22A C 0.3676(13) -0.057(3) 0.6327(15) 0.089(8) Uani 0.291(10) 1 d D U P B 2
H22C H 0.409454 -0.036712 0.614855 0.107 Uiso 0.291(10) 1 calc R U P B 2
H22D H 0.372953 -0.134557 0.660554 0.107 Uiso 0.291(10) 1 calc R U P B 2
C22 C 0.3459(5) -0.0559(11) 0.6255(5) 0.075(2) Uani 0.709(10) 1 d D U P B 1
H22A H 0.359348 -0.031489 0.585783 0.090 Uiso 0.709(10) 1 calc R U P B 1
H22B H 0.304477 -0.106019 0.622741 0.090 Uiso 0.709(10) 1 calc R U P B 1
C23 C 0.3964(3) -0.1446(7) 0.6555(3) 0.104(2) Uani 0.709(10) 1 d D U P B 1
H23A H 0.400507 -0.232496 0.634644 0.156 Uiso 0.709(10) 1 calc R U P B 1
H23B H 0.383700 -0.162826 0.695539 0.156 Uiso 0.709(10) 1 calc R U P B 1
H23C H 0.437663 -0.095826 0.655818 0.156 Uiso 0.709(10) 1 calc R U P B 1
C23A C 0.3154(7) -0.0888(14) 0.5863(6) 0.089(5) Uani 0.291(10) 1 d D U P B 2
H23D H 0.327513 -0.171497 0.564401 0.133 Uiso 0.291(10) 1 calc R U P B 2
H23E H 0.311043 -0.009887 0.559733 0.133 Uiso 0.291(10) 1 calc R U P B 2
H23F H 0.274404 -0.105225 0.605250 0.133 Uiso 0.291(10) 1 calc R U P B 2


_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 1.241(3) . ?
N1 C1 1.381(3) . ?
N1 C5 1.396(3) . ?
N1 C6 1.459(3) . ?
C1 C2 1.435(3) . ?
O2 H2 0.87(4) . ?
O2 C2 1.349(3) . ?
C2 C3 1.364(3) . ?
C3 C4 1.422(3) . ?
C3 C18 1.487(3) . ?
O3 C21 1.188(3) . ?
O4 C21 1.326(3) . ?
O4 C22A 1.509(15) . ?
O4 C22 1.473(7) . ?
C4 C5 1.357(3) . ?
C4 C21 1.505(3) . ?
C5 C12 1.492(3) . ?
O5 C18 1.197(3) . ?
O6 C18 1.296(10) . ?
O6 C19 1.484(15) . ?
C6 C7 1.375(3) . ?
C6 C11 1.362(3) . ?
O6A C18 1.312(10) . ?
O6A C19A 1.486(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(4) . ?
C12 C17 1.365(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.344(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9300 . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C20A 1.438(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.440(13) . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.508(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.480(11) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?

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
C1 N1 C5 123.74(19) . . ?
C1 N1 C6 117.24(18) . . ?
C5 N1 C6 118.95(18) . . ?
O1 C1 N1 121.9(2) . . ?
O1 C1 C2 121.6(2) . . ?
N1 C1 C2 116.4(2) . . ?
C2 O2 H2 114(2) . . ?
O2 C2 C1 118.0(2) . . ?
O2 C2 C3 121.3(2) . . ?
C3 C2 C1 120.7(2) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 C18 121.1(2) . . ?
C4 C3 C18 119.2(2) . . ?
C21 O4 C22A 109.9(15) . . ?
C21 O4 C22 120.1(6) . . ?
C3 C4 C21 119.4(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 C21 119.6(2) . . ?
N1 C5 C12 119.50(19) . . ?
C4 C5 N1 118.0(2) . . ?
C4 C5 C12 122.4(2) . . ?
C18 O6 C19 115.8(14) . . ?
C7 C6 N1 118.7(2) . . ?
C11 C6 N1 119.5(2) . . ?
C11 C6 C7 121.8(2) . . ?
C18 O6A C19A 115.1(12) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(3) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 118.8(3) . . ?
C6 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C5 121.1(2) . . ?
C17 C12 C5 121.7(2) . . ?
C17 C12 C13 117.2(3) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 C16 122.5(3) . . ?
C12 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
O5 C18 C3 123.4(3) . . ?
O5 C18 O6 121.9(8) . . ?
O5 C18 O6A 127.5(7) . . ?
O6 C18 C3 114.3(9) . . ?
O6A C18 C3 109.1(7) . . ?
O6A C19A H19C 109.7 . . ?
O6A C19A H19D 109.7 . . ?
H19C C19A H19D 108.2 . . ?
C20A C19A O6A 109.7(10) . . ?
C20A C19A H19C 109.7 . . ?
C20A C19A H19D 109.7 . . ?
O6 C19 H19A 109.3 . . ?
O6 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 O6 111.4(15) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 O4 125.3(2) . . ?
O3 C21 C4 123.5(2) . . ?
O4 C21 C4 111.1(2) . . ?
O4 C22A H22C 111.5 . . ?
O4 C22A H22D 111.5 . . ?
H22C C22A H22D 109.3 . . ?
C23A C22A O4 101.2(13) . . ?
C23A C22A H22C 111.5 . . ?
C23A C22A H22D 111.5 . . ?
O4 C22 H22A 110.5 . . ?
O4 C22 H22B 110.5 . . ?
O4 C22 C23 106.2(6) . . ?
H22A C22 H22B 108.7 . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 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 O2 -2.8(3) . . . . ?
O1 C1 C2 C3 176.7(2) . . . . ?
N1 C1 C2 O2 179.60(19) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
N1 C5 C12 C13 -95.4(3) . . . . ?
N1 C5 C12 C17 88.2(3) . . . . ?
N1 C6 C7 C8 -177.2(3) . . . . ?
N1 C6 C11 C10 176.7(2) . . . . ?
C1 N1 C5 C4 4.2(3) . . . . ?
C1 N1 C5 C12 -177.4(2) . . . . ?
C1 N1 C6 C7 -83.4(3) . . . . ?
C1 N1 C6 C11 97.8(3) . . . . ?
C1 C2 C3 C4 6.4(3) . . . . ?
C1 C2 C3 C18 -176.2(2) . . . . ?
O2 C2 C3 C4 -174.1(2) . . . . ?
O2 C2 C3 C18 3.3(4) . . . . ?
C2 C3 C4 C5 -6.8(3) . . . . ?
C2 C3 C4 C21 174.6(2) . . . . ?
C2 C3 C18 O5 -120.3(3) . . . . ?
C2 C3 C18 O6 66(2) . . . . ?
C2 C3 C18 O6A 61.0(16) . . . . ?
C3 C4 C5 N1 1.6(3) . . . . ?
C3 C4 C5 C12 -176.7(2) . . . . ?
C3 C4 C21 O3 65.3(3) . . . . ?
C3 C4 C21 O4 -110.7(2) . . . . ?
C4 C3 C18 O5 57.1(4) . . . . ?
C4 C3 C18 O6 -116(2) . . . . ?
C4 C3 C18 O6A -121.5(16) . . . . ?
C4 C5 C12 C13 82.9(3) . . . . ?
C4 C5 C12 C17 -93.5(3) . . . . ?
C5 N1 C1 O1 177.9(2) . . . . ?
C5 N1 C1 C2 -4.6(3) . . . . ?
C5 N1 C6 C7 93.8(3) . . . . ?
C5 N1 C6 C11 -85.1(3) . . . . ?
C5 C4 C21 O3 -113.2(3) . . . . ?
C5 C4 C21 O4 70.7(3) . . . . ?
C5 C12 C13 C14 -177.1(3) . . . . ?
C5 C12 C17 C16 177.2(3) . . . . ?
C6 N1 C1 O1 -5.1(3) . . . . ?
C6 N1 C1 C2 172.4(2) . . . . ?
C6 N1 C5 C4 -172.7(2) . . . . ?
C6 N1 C5 C12 5.6(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C6 C11 C10 -2.1(4) . . . . ?
C7 C8 C9 C10 -1.5(6) . . . . ?
C8 C9 C10 C11 1.0(6) . . . . ?
C9 C10 C11 C6 0.8(5) . . . . ?
C11 C6 C7 C8 1.6(5) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C12 C17 C16 0.6(5) . . . . ?
C13 C14 C15 C16 1.5(6) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C12 0.3(6) . . . . ?
C17 C12 C13 C14 -0.5(5) . . . . ?
C18 C3 C4 C5 175.7(2) . . . . ?
C18 C3 C4 C21 -2.9(3) . . . . ?
C18 O6 C19 C20 139(3) . . . . ?
C18 O6A C19A C20A -152(2) . . . . ?
C19A O6A C18 C3 160.1(18) . . . . ?
C19A O6A C18 O5 -19(3) . . . . ?
C19 O6 C18 C3 -173(2) . . . . ?
C19 O6 C18 O5 14(4) . . . . ?
C21 O4 C22A C23A -114.6(19) . . . . ?
C21 O4 C22 C23 88.6(9) . . . . ?
C21 C4 C5 N1 -179.85(19) . . . . ?
C21 C4 C5 C12 1.9(3) . . . . ?
C22A O4 C21 O3 13.0(12) . . . . ?
C22A O4 C21 C4 -171.0(12) . . . . ?
C22 O4 C21 O3 -3.5(6) . . . . ?
C22 O4 C21 C4 172.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.811
####################################################################### 
# 
# 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_3ca
_database_code_depnum_ccdc_archive 'CCDC 2410200'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H18 Cl N O7'
_chemical_formula_sum            'C23 H18 Cl N O7'
_chemical_formula_weight         455.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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'
Cl Cl 0.1484 0.1585 '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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.3507(19)
_cell_length_b                   11.705(2)
_cell_length_c                   17.151(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.734(14)
_cell_angle_gamma                90
_cell_volume                     2271.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.9120
_cell_measurement_theta_min      2.5320
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   -7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -50.0000 -105.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   20.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   36.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978   38.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978   57.0000 -120.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0294160000
_diffrn_orient_matrix_UB_12      -0.0450924000
_diffrn_orient_matrix_UB_13      -0.0214659000
_diffrn_orient_matrix_UB_21      0.0445153000
_diffrn_orient_matrix_UB_22      -0.0385313000
_diffrn_orient_matrix_UB_23      0.0146377000
_diffrn_orient_matrix_UB_31      -0.0327177000
_diffrn_orient_matrix_UB_32      -0.0127297000
_diffrn_orient_matrix_UB_33      0.0324120000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3177
_reflns_number_total             5480
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²+0.6021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C7-O7 \\sim C7A-O7
 with sigma of 0.02
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
 O7-C8 \\sim O7-C8A
 with sigma of 0.04
2. Rigid bond restraints
 C8, C8A, C7A, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C7A \\sim C8 \\sim C8A \\sim C7: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
4. Others
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=1-FVAR(1)
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7A(H7AA,H7AB)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C8A(H8AA,H8AB,H8AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl -0.03261(7) 0.73786(11) 0.62220(6) 0.1074(4) Uani 1 1 d . . . . .
O1 O 0.50870(16) 0.57874(16) 0.75390(10) 0.0567(5) Uani 1 1 d . . . . .
N1 N 0.35177(17) 0.52069(16) 0.82145(10) 0.0404(4) Uani 1 1 d . . . . .
C1 C 0.4660(2) 0.5209(2) 0.80226(13) 0.0430(5) Uani 1 1 d . . . . .
O2 O 0.63388(16) 0.41094(16) 0.85320(10) 0.0562(5) Uani 1 1 d . . . . .
C2 C 0.5305(2) 0.4284(2) 0.85175(13) 0.0420(5) Uani 1 1 d . . . . .
O3 O 0.45365(16) 0.39284(15) 1.03602(10) 0.0541(5) Uani 1 1 d . . . . .
C3 C 0.4427(2) 0.37108(19) 0.89914(13) 0.0400(5) Uani 1 1 d . . . . .
O4 O 0.19613(18) 0.39731(17) 0.97383(11) 0.0627(5) Uani 1 1 d . . . . .
C4 C 0.3300(2) 0.43524(19) 0.87860(12) 0.0393(5) Uani 1 1 d . . . . .
C5 C 0.3394(2) 0.3112(2) 0.85448(13) 0.0428(6) Uani 1 1 d . . . . .
H5 H 0.296458 0.256587 0.884854 0.051 Uiso 1 1 calc R U . . .
O5 O 0.24114(16) 0.57736(16) 0.94683(10) 0.0561(5) Uani 1 1 d . . . . .
C6 C 0.3411(2) 0.2847(2) 0.76964(14) 0.0483(6) Uani 1 1 d . . . . .
O6 O 0.41244(18) 0.32220(17) 0.72918(10) 0.0633(5) Uani 1 1 d . . . . .
C7 C 0.236(2) 0.210(4) 0.6606(9) 0.088(6) Uani 0.314(13) 1 d D U P A 1
H7A H 0.298448 0.163238 0.641000 0.106 Uiso 0.314(13) 1 calc R U P A 1
H7B H 0.236896 0.284397 0.636281 0.106 Uiso 0.314(13) 1 calc R U P A 1
O7 O 0.25137(16) 0.21870(18) 0.74658(10) 0.0633(5) Uani 1 1 d D . . . .
C8 C 0.1189(11) 0.154(3) 0.6458(9) 0.122(7) Uani 0.314(13) 1 d D U P A 1
H8A H 0.097446 0.150886 0.590520 0.182 Uiso 0.314(13) 1 calc R U P A 1
H8B H 0.060726 0.196515 0.670967 0.182 Uiso 0.314(13) 1 calc R U P A 1
H8C H 0.122786 0.077329 0.666437 0.182 Uiso 0.314(13) 1 calc R U P A 1
C9 C 0.2486(2) 0.4658(2) 0.93927(13) 0.0430(6) Uani 1 1 d . . . . .
C10 C 0.1589(3) 0.6194(3) 0.99998(18) 0.0723(9) Uani 1 1 d . . . . .
H10A H 0.182855 0.593857 1.052079 0.108 Uiso 1 1 calc R U . . .
H10B H 0.081194 0.590931 0.984439 0.108 Uiso 1 1 calc R U . . .
H10C H 0.158017 0.701404 0.998772 0.108 Uiso 1 1 calc R U . . .
C11 C 0.2578(2) 0.5738(2) 0.77537(13) 0.0442(6) Uani 1 1 d . . . . .
C12 C 0.1530(2) 0.5159(3) 0.75820(16) 0.0589(7) Uani 1 1 d . . . . .
H12 H 0.143099 0.443031 0.778179 0.071 Uiso 1 1 calc R U . . .
C13 C 0.0629(3) 0.5664(3) 0.71132(19) 0.0724(9) Uani 1 1 d . . . . .
H13 H -0.007606 0.527478 0.698938 0.087 Uiso 1 1 calc R U . . .
C14 C 0.0785(3) 0.6740(3) 0.68334(18) 0.0694(9) Uani 1 1 d . . . . .
C15 C 0.1796(3) 0.7325(3) 0.70173(17) 0.0666(8) Uani 1 1 d . . . . .
H15 H 0.187899 0.806529 0.683298 0.080 Uiso 1 1 calc R U . . .
C16 C 0.2705(2) 0.6822(2) 0.74792(15) 0.0540(7) Uani 1 1 d . . . . .
H16 H 0.340412 0.722066 0.760329 0.065 Uiso 1 1 calc R U . . .
C17 C 0.4799(2) 0.3338(2) 0.98236(14) 0.0432(6) Uani 1 1 d . . . . .
C18 C 0.5451(2) 0.2262(2) 0.99402(14) 0.0474(6) Uani 1 1 d . . . . .
C19 C 0.5715(3) 0.1874(3) 1.07017(16) 0.0660(8) Uani 1 1 d . . . . .
H19 H 0.546566 0.228922 1.112011 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6339(4) 0.0889(3) 1.0837(2) 0.0916(12) Uani 1 1 d . . . . .
H20 H 0.651501 0.063144 1.134610 0.110 Uiso 1 1 calc R U . . .
C21 C 0.6707(4) 0.0276(3) 1.0215(2) 0.0958(12) Uani 1 1 d . . . . .
H21 H 0.714358 -0.038961 1.030814 0.115 Uiso 1 1 calc R U . . .
C22 C 0.6434(3) 0.0638(3) 0.9456(2) 0.0833(10) Uani 1 1 d . . . . .
H22 H 0.667317 0.021353 0.903873 0.100 Uiso 1 1 calc R U . . .
C23 C 0.5805(3) 0.1632(2) 0.93212(17) 0.0623(8) Uani 1 1 d . . . . .
H23 H 0.561791 0.188070 0.881099 0.075 Uiso 1 1 calc R U . . .
C7A C 0.2337(9) 0.1848(14) 0.6642(4) 0.073(3) Uani 0.686(13) 1 d D U P A 2
H7AA H 0.211324 0.104944 0.659901 0.088 Uiso 0.686(13) 1 calc R U P A 2
H7AB H 0.305853 0.195785 0.638527 0.088 Uiso 0.686(13) 1 calc R U P A 2
C8A C 0.1373(8) 0.2585(10) 0.6272(4) 0.128(4) Uani 0.686(13) 1 d D U P A 2
H8AA H 0.119207 0.235345 0.573845 0.191 Uiso 0.686(13) 1 calc R U P A 2
H8AB H 0.162723 0.336797 0.628537 0.191 Uiso 0.686(13) 1 calc R U P A 2
H8AC H 0.068110 0.250886 0.655354 0.191 Uiso 0.686(13) 1 calc R U P A 2


_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
Cl1 C14 1.741(3) . ?
O1 C1 1.203(3) . ?
N1 C1 1.364(3) . ?
N1 C4 1.436(3) . ?
N1 C11 1.418(3) . ?
C1 C2 1.525(3) . ?
O2 C2 1.189(3) . ?
C2 C3 1.496(3) . ?
O3 C17 1.208(3) . ?
C3 C4 1.500(3) . ?
C3 C5 1.518(3) . ?
C3 C17 1.519(3) . ?
O4 C9 1.186(3) . ?
C4 C5 1.516(3) . ?
C4 C9 1.491(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.490(3) . ?
O5 C9 1.316(3) . ?
O5 C10 1.444(3) . ?
C6 O6 1.192(3) . ?
C6 O7 1.314(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 O7 1.475(15) . ?
C7 C8 1.489(19) . ?
O7 C7A 1.466(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.378(4) . ?
C11 C16 1.365(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(5) . ?
C14 C15 1.351(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.466(4) . ?
C18 C19 1.392(4) . ?
C18 C23 1.379(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9300 . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.493(14) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?

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
C1 N1 C4 112.72(19) . . ?
C1 N1 C11 123.47(19) . . ?
C11 N1 C4 121.46(18) . . ?
O1 C1 N1 127.7(2) . . ?
O1 C1 C2 125.5(2) . . ?
N1 C1 C2 106.66(19) . . ?
O2 C2 C1 124.1(2) . . ?
O2 C2 C3 127.7(2) . . ?
C3 C2 C1 108.1(2) . . ?
C2 C3 C4 103.96(19) . . ?
C2 C3 C5 117.02(19) . . ?
C2 C3 C17 119.6(2) . . ?
C4 C3 C5 60.30(15) . . ?
C4 C3 C17 122.04(19) . . ?
C5 C3 C17 119.01(19) . . ?
N1 C4 C3 108.54(18) . . ?
N1 C4 C5 117.44(18) . . ?
N1 C4 C9 117.4(2) . . ?
C3 C4 C5 60.43(15) . . ?
C9 C4 C3 121.45(19) . . ?
C9 C4 C5 118.8(2) . . ?
C3 C5 H5 115.5 . . ?
C4 C5 C3 59.27(15) . . ?
C4 C5 H5 115.5 . . ?
C6 C5 C3 121.2(2) . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 115.5 . . ?
C9 O5 C10 116.8(2) . . ?
O6 C6 C5 123.8(2) . . ?
O6 C6 O7 126.0(2) . . ?
O7 C6 C5 110.1(2) . . ?
H7A C7 H7B 109.1 . . ?
O7 C7 H7A 111.1 . . ?
O7 C7 H7B 111.1 . . ?
O7 C7 C8 103.2(14) . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 O7 C7 111.5(10) . . ?
C6 O7 C7A 119.4(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C4 123.6(2) . . ?
O4 C9 O5 125.6(2) . . ?
O5 C9 C4 110.8(2) . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 120.0(2) . . ?
C16 C11 N1 120.2(2) . . ?
C16 C11 C12 119.8(2) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 Cl1 120.0(3) . . ?
C15 C14 Cl1 118.9(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.9(3) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O3 C17 C3 119.0(2) . . ?
O3 C17 C18 122.8(2) . . ?
C18 C17 C3 118.3(2) . . ?
C19 C18 C17 118.4(2) . . ?
C23 C18 C17 122.0(2) . . ?
C23 C18 C19 119.6(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(3) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.7(3) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
O7 C7A H7AA 110.3 . . ?
O7 C7A H7AB 110.3 . . ?
O7 C7A C8A 106.9(9) . . ?
H7AA C7A H7AB 108.6 . . ?
C8A C7A H7AA 110.3 . . ?
C8A C7A H7AB 110.3 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 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
Cl1 C14 C15 C16 -177.8(2) . . . . ?
O1 C1 C2 O2 7.7(4) . . . . ?
O1 C1 C2 C3 -175.3(2) . . . . ?
N1 C1 C2 O2 -174.9(2) . . . . ?
N1 C1 C2 C3 2.2(2) . . . . ?
N1 C4 C5 C3 96.7(2) . . . . ?
N1 C4 C5 C6 -14.6(3) . . . . ?
N1 C4 C9 O4 156.6(2) . . . . ?
N1 C4 C9 O5 -21.5(3) . . . . ?
N1 C11 C12 C13 -178.0(3) . . . . ?
N1 C11 C16 C15 178.7(2) . . . . ?
C1 N1 C4 C3 -0.4(3) . . . . ?
C1 N1 C4 C5 -66.1(3) . . . . ?
C1 N1 C4 C9 142.1(2) . . . . ?
C1 N1 C11 C12 133.1(3) . . . . ?
C1 N1 C11 C16 -46.9(3) . . . . ?
C1 C2 C3 C4 -2.4(2) . . . . ?
C1 C2 C3 C5 61.1(3) . . . . ?
C1 C2 C3 C17 -142.7(2) . . . . ?
O2 C2 C3 C4 174.6(2) . . . . ?
O2 C2 C3 C5 -121.9(3) . . . . ?
O2 C2 C3 C17 34.3(4) . . . . ?
C2 C3 C4 N1 1.8(2) . . . . ?
C2 C3 C4 C5 113.4(2) . . . . ?
C2 C3 C4 C9 -139.0(2) . . . . ?
C2 C3 C5 C4 -91.2(2) . . . . ?
C2 C3 C5 C6 15.3(3) . . . . ?
C2 C3 C17 O3 100.3(3) . . . . ?
C2 C3 C17 C18 -80.6(3) . . . . ?
O3 C17 C18 C19 3.9(4) . . . . ?
O3 C17 C18 C23 -176.1(3) . . . . ?
C3 C4 C5 C6 -111.3(2) . . . . ?
C3 C4 C9 O4 -65.9(3) . . . . ?
C3 C4 C9 O5 116.0(2) . . . . ?
C3 C5 C6 O6 -11.5(4) . . . . ?
C3 C5 C6 O7 170.8(2) . . . . ?
C3 C17 C18 C19 -175.2(2) . . . . ?
C3 C17 C18 C23 4.8(4) . . . . ?
C4 N1 C1 O1 176.3(2) . . . . ?
C4 N1 C1 C2 -1.1(3) . . . . ?
C4 N1 C11 C12 -28.2(3) . . . . ?
C4 N1 C11 C16 151.7(2) . . . . ?
C4 C3 C5 C6 106.5(2) . . . . ?
C4 C3 C17 O3 -32.7(3) . . . . ?
C4 C3 C17 C18 146.4(2) . . . . ?
C4 C5 C6 O6 57.8(4) . . . . ?
C4 C5 C6 O7 -119.9(2) . . . . ?
C5 C3 C4 N1 -111.6(2) . . . . ?
C5 C3 C4 C9 107.6(2) . . . . ?
C5 C3 C17 O3 -104.0(3) . . . . ?
C5 C3 C17 C18 75.2(3) . . . . ?
C5 C4 C9 O4 5.2(3) . . . . ?
C5 C4 C9 O5 -172.9(2) . . . . ?
C5 C6 O7 C7 168.6(17) . . . . ?
C5 C6 O7 C7A 178.1(7) . . . . ?
C6 O7 C7A C8A -101.6(9) . . . . ?
O6 C6 O7 C7 -9.0(17) . . . . ?
O6 C6 O7 C7A 0.4(8) . . . . ?
C8 C7 O7 C6 -169(2) . . . . ?
C9 C4 C5 C3 -111.9(2) . . . . ?
C9 C4 C5 C6 136.8(2) . . . . ?
C10 O5 C9 O4 -2.2(4) . . . . ?
C10 O5 C9 C4 175.9(2) . . . . ?
C11 N1 C1 O1 13.5(4) . . . . ?
C11 N1 C1 C2 -163.9(2) . . . . ?
C11 N1 C4 C3 162.8(2) . . . . ?
C11 N1 C4 C5 97.1(3) . . . . ?
C11 N1 C4 C9 -54.7(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C11 C16 C15 -1.4(4) . . . . ?
C12 C13 C14 Cl1 178.4(2) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C16 C11 C12 C13 2.1(4) . . . . ?
C17 C3 C4 N1 140.8(2) . . . . ?
C17 C3 C4 C5 -107.6(2) . . . . ?
C17 C3 C4 C9 0.0(3) . . . . ?
C17 C3 C5 C4 112.5(2) . . . . ?
C17 C3 C5 C6 -141.1(2) . . . . ?
C17 C18 C19 C20 -178.8(3) . . . . ?
C17 C18 C23 C22 178.8(3) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C18 C23 C22 -1.2(5) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C23 1.1(6) . . . . ?
C21 C22 C23 C18 0.0(5) . . . . ?
C23 C18 C19 C20 1.2(5) . . . . ?

_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_6aa
_database_code_depnum_ccdc_archive 'CCDC 2410199'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2024-12-13 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N O7'
_chemical_formula_sum            'C23 H19 N O7'
_chemical_formula_weight         421.39
_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 0.0033 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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.3392(19)
_cell_length_b                   16.5142(19)
_cell_length_c                   19.544(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4305.3(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3683
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.3090
_cell_measurement_theta_min      2.5990
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_min         1.963
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  48.00   1.00   45.00    --   13.93 -19.00 -90.00  118
  2  ω   -105.00 -77.00   1.00   45.00    --  -14.09 178.00 150.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0087868000
_diffrn_orient_matrix_UB_12      0.0017296000
_diffrn_orient_matrix_UB_13      0.0357674000
_diffrn_orient_matrix_UB_21      -0.0509428000
_diffrn_orient_matrix_UB_22      0.0108891000
_diffrn_orient_matrix_UB_23      0.0055416000
_diffrn_orient_matrix_UB_31      -0.0130138000
_diffrn_orient_matrix_UB_32      -0.0413555000
_diffrn_orient_matrix_UB_33      0.0031624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             5264
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²+0.6386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C20-C21 = C20A-C21A
 1.5 with sigma of 0.02
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C13-C18 \\sim C13A-C18A
 with sigma of 0.02
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C14-C18 \\sim C14A-C18A
 with sigma of 0.04
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C12-C14 \\sim C12-C14A
 with sigma of 0.04
 C12-C18 \\sim C12-C18A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C13-C17 \\sim C13A-C17A
 with sigma of 0.04
 O5-C20 \\sim O5-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 O5-C21 \\sim O5-C21A
 with sigma of 0.04
2. Rigid bond restraints
 C13, C13A, C14, C14A, C15, C15A, C16, C16A, C17, C17A, C18, C18A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C20, C20A, C21, C21A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C13 \\sim C13A \\sim C14 \\sim C14A \\sim C15 \\sim C15A \\sim C16 \\sim C16A
\\sim C17 \\sim C17A \\sim C18 \\sim C18A: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.7A
C20 \\sim C20A \\sim C21 \\sim C21A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
4. Others
 Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=1-FVAR(1)
 Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=
 Sof(H17)=Sof(C18)=Sof(H18)=FVAR(1)
 Sof(C20A)=Sof(H20D)=Sof(H20C)=Sof(C21A)=Sof(H21E)=Sof(H21D)=Sof(H21F)=1-FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21C)=Sof(H21A)=Sof(H21B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20A(H20D,H20C)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C14A(H14A), C15(H15),
 C15A(H15A), C16(H16), C16A(H16A), C17(H17), C17A(H17A), C18(H18), C18A(H18A)
5.c Idealised Me refined as rotating group:
 C21(H21C,H21A,H21B), C21A(H21E,H21D,H21F), C23(H23C,H23A,H23B)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.55358(16) 0.58719(11) 0.35777(11) 0.0486(5) Uani 1 1 d . . . . .
O1 O 0.48241(12) 0.61172(8) 0.32352(7) 0.0610(4) Uani 1 1 d . . . . .
N1 N 0.56473(12) 0.60950(8) 0.42555(8) 0.0451(4) Uani 1 1 d . . . . .
O2 O 0.63092(14) 0.52090(10) 0.26312(8) 0.0684(5) Uani 1 1 d . . . . .
H2 H 0.586(2) 0.5522(17) 0.2446(15) 0.101(11) Uiso 1 1 d . . . . .
C2 C 0.63265(16) 0.53692(12) 0.33057(11) 0.0520(5) Uani 1 1 d . . . . .
O3 O 0.86839(17) 0.50206(15) 0.32240(14) 0.1193(9) Uani 1 1 d . . . . .
C3 C 0.70787(16) 0.50878(12) 0.37082(12) 0.0541(5) Uani 1 1 d . . . . .
O4 O 0.83815(17) 0.43502(13) 0.46639(12) 0.1085(8) Uani 1 1 d . . . . .
C4 C 0.70755(16) 0.52630(11) 0.44267(11) 0.0515(5) Uani 1 1 d . . . . .
O5 O 0.78740(16) 0.51478(12) 0.54869(10) 0.0967(7) Uani 1 1 d D . . . .
C5 C 0.63562(15) 0.57630(11) 0.46840(11) 0.0466(5) Uani 1 1 d . . . . .
C6 C 0.49773(16) 0.67209(11) 0.45097(10) 0.0480(5) Uani 1 1 d . . . . .
O6 O 0.56151(16) 0.55081(11) 0.57669(9) 0.0850(6) Uani 1 1 d . . . . .
C7 C 0.40158(18) 0.65365(13) 0.46931(14) 0.0722(7) Uani 1 1 d . . . . .
H7 H 0.377822 0.600976 0.464761 0.087 Uiso 1 1 calc R U . . .
O7 O 0.66349(13) 0.65668(9) 0.56534(8) 0.0723(5) Uani 1 1 d . . . . .
C8 C 0.3403(2) 0.71328(16) 0.49446(18) 0.0912(9) Uani 1 1 d . . . . .
H8 H 0.274892 0.701278 0.507328 0.109 Uiso 1 1 calc R U . . .
C9 C 0.3757(2) 0.78961(16) 0.50043(17) 0.0877(9) Uani 1 1 d . . . . .
H9 H 0.334851 0.830043 0.518278 0.105 Uiso 1 1 calc R U . . .
C10 C 0.4709(2) 0.80764(14) 0.48044(18) 0.0894(9) Uani 1 1 d . . . . .
H10 H 0.494242 0.860514 0.484285 0.107 Uiso 1 1 calc R U . . .
C11 C 0.53305(19) 0.74853(12) 0.45462(13) 0.0680(7) Uani 1 1 d . . . . .
H11 H 0.597624 0.760947 0.440071 0.082 Uiso 1 1 calc R U . . .
C12 C 0.7936(2) 0.46462(16) 0.33644(14) 0.0748(7) Uani 1 1 d D . . . .
C13 C 0.7919(18) 0.3812(9) 0.3137(18) 0.084(4) Uani 0.44(2) 1 d D U P A 1
C13A C 0.7714(12) 0.3773(6) 0.3194(11) 0.068(3) Uani 0.56(2) 1 d D U P A 2
C14 C 0.8735(13) 0.3570(12) 0.2746(10) 0.102(4) Uani 0.44(2) 1 d D U P A 1
H14 H 0.925668 0.391451 0.262318 0.122 Uiso 0.44(2) 1 calc R U P A 1
C14A C 0.8445(10) 0.3299(6) 0.2868(6) 0.080(3) Uani 0.56(2) 1 d D U P A 2
H14A H 0.906718 0.352854 0.277690 0.096 Uiso 0.56(2) 1 calc R U P A 2
C15 C 0.8691(15) 0.2762(12) 0.2559(11) 0.114(4) Uani 0.44(2) 1 d D U P A 1
H15 H 0.921615 0.253937 0.230880 0.137 Uiso 0.44(2) 1 calc R U P A 1
C15A C 0.8274(13) 0.2496(8) 0.2675(10) 0.094(4) Uani 0.56(2) 1 d D U P A 2
H15A H 0.875631 0.220212 0.243681 0.113 Uiso 0.56(2) 1 calc R U P A 2
C16 C 0.789(2) 0.2283(10) 0.2735(13) 0.101(5) Uani 0.44(2) 1 d D U P A 1
H16 H 0.791543 0.173872 0.261357 0.121 Uiso 0.44(2) 1 calc R U P A 1
C16A C 0.7377(13) 0.2157(6) 0.2846(7) 0.090(3) Uani 0.56(2) 1 d D U P A 2
H16A H 0.724983 0.162102 0.272911 0.108 Uiso 0.56(2) 1 calc R U P A 2
C17 C 0.7063(16) 0.2563(9) 0.3081(10) 0.100(4) Uani 0.44(2) 1 d D U P A 1
H17 H 0.649989 0.224141 0.315226 0.120 Uiso 0.44(2) 1 calc R U P A 1
C17A C 0.6650(12) 0.2598(6) 0.3193(9) 0.101(3) Uani 0.56(2) 1 d D U P A 2
H17A H 0.605879 0.234680 0.332925 0.121 Uiso 0.56(2) 1 calc R U P A 2
C18 C 0.7117(15) 0.3346(9) 0.3315(14) 0.087(4) Uani 0.44(2) 1 d D U P A 1
H18 H 0.661300 0.355667 0.359108 0.104 Uiso 0.44(2) 1 calc R U P A 1
C18A C 0.6804(11) 0.3411(6) 0.3336(11) 0.080(3) Uani 0.56(2) 1 d D U P A 2
H18A H 0.628977 0.371462 0.352999 0.096 Uiso 0.56(2) 1 calc R U P A 2
C19 C 0.78543(19) 0.48759(14) 0.48610(14) 0.0675(7) Uani 1 1 d . . . . .
C20 C 0.8773(8) 0.4951(6) 0.5951(5) 0.112(4) Uani 0.612(11) 1 d D U P B 1
H20A H 0.933967 0.474851 0.569085 0.134 Uiso 0.612(11) 1 calc R U P B 1
H20B H 0.898007 0.541699 0.621800 0.134 Uiso 0.612(11) 1 calc R U P B 1
C20A C 0.8527(16) 0.4664(9) 0.5937(7) 0.116(6) Uani 0.388(11) 1 d D U P B 2
H20D H 0.822053 0.414548 0.604200 0.140 Uiso 0.388(11) 1 calc R U P B 2
H20C H 0.917318 0.456937 0.572403 0.140 Uiso 0.388(11) 1 calc R U P B 2
C21 C 0.8337(8) 0.4330(8) 0.6374(6) 0.197(6) Uani 0.612(11) 1 d D U P B 1
H21C H 0.878932 0.420001 0.674034 0.296 Uiso 0.612(11) 1 calc R U P B 1
H21A H 0.821586 0.385496 0.610379 0.296 Uiso 0.612(11) 1 calc R U P B 1
H21B H 0.771515 0.452161 0.656128 0.296 Uiso 0.612(11) 1 calc R U P B 1
C21A C 0.8633(11) 0.5144(9) 0.6543(6) 0.149(6) Uani 0.388(11) 1 d D U P B 2
H21E H 0.916551 0.492887 0.681896 0.224 Uiso 0.388(11) 1 calc R U P B 2
H21D H 0.801808 0.513257 0.679748 0.224 Uiso 0.388(11) 1 calc R U P B 2
H21F H 0.878743 0.569203 0.641774 0.224 Uiso 0.388(11) 1 calc R U P B 2
C22 C 0.61667(17) 0.59225(13) 0.54358(12) 0.0569(6) Uani 1 1 d . . . . .
C23 C 0.6468(3) 0.6765(2) 0.63752(16) 0.1195(13) Uani 1 1 d . . . . .
H23C H 0.648104 0.627760 0.664239 0.179 Uiso 1 1 calc R U . . .
H23A H 0.582780 0.702386 0.642559 0.179 Uiso 1 1 calc R U . . .
H23B H 0.698627 0.712441 0.653053 0.179 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 O1 1.230(2) . ?
C1 N1 1.383(3) . ?
C1 C2 1.444(3) . ?
N1 C5 1.377(2) . ?
N1 C6 1.454(2) . ?
O2 H2 0.87(3) . ?
O2 C2 1.345(3) . ?
C2 C3 1.357(3) . ?
O3 C12 1.205(3) . ?
C3 C4 1.434(3) . ?
C3 C12 1.514(3) . ?
O4 C19 1.182(3) . ?
C4 C5 1.362(3) . ?
C4 C19 1.486(3) . ?
O5 C19 1.303(3) . ?
O5 C20 1.539(9) . ?
O5 C20A 1.474(10) . ?
C5 C22 1.514(3) . ?
C6 C7 1.366(3) . ?
C6 C11 1.349(3) . ?
O6 C22 1.195(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(3) . ?
O7 C22 1.305(3) . ?
O7 C23 1.465(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.351(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.449(11) . ?
C12 C13A 1.509(8) . ?
C13 C14 1.388(12) . ?
C13 C18 1.362(12) . ?
C13A C14A 1.403(9) . ?
C13A C18A 1.383(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(12) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.399(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(15) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.362(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(14) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.389(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(12) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.387(9) . ?
C18 H18 0.9300 . ?
C18A H18A 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.440(11) . ?
C20A H20D 0.9700 . ?
C20A H20C 0.9700 . ?
C20A C21A 1.432(12) . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21F 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?

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
O1 C1 N1 121.10(18) . . ?
O1 C1 C2 123.6(2) . . ?
N1 C1 C2 115.30(18) . . ?
C1 N1 C6 116.79(15) . . ?
C5 N1 C1 123.39(16) . . ?
C5 N1 C6 119.82(16) . . ?
C2 O2 H2 107.7(19) . . ?
O2 C2 C1 117.49(19) . . ?
O2 C2 C3 120.9(2) . . ?
C3 C2 C1 121.6(2) . . ?
C2 C3 C4 119.77(19) . . ?
C2 C3 C12 117.8(2) . . ?
C4 C3 C12 122.3(2) . . ?
C3 C4 C19 118.07(19) . . ?
C5 C4 C3 119.08(19) . . ?
C5 C4 C19 122.8(2) . . ?
C19 O5 C20 119.7(5) . . ?
C19 O5 C20A 112.7(6) . . ?
N1 C5 C22 113.97(17) . . ?
C4 C5 N1 120.03(19) . . ?
C4 C5 C22 125.55(18) . . ?
C7 C6 N1 120.55(17) . . ?
C11 C6 N1 117.94(19) . . ?
C11 C6 C7 121.5(2) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C22 O7 C23 115.1(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 118.2(2) . . ?
C6 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
O3 C12 C3 118.6(2) . . ?
O3 C12 C13 115.6(8) . . ?
O3 C12 C13A 127.0(5) . . ?
C13 C12 C3 125.6(8) . . ?
C13A C12 C3 114.2(5) . . ?
C14 C13 C12 115.5(11) . . ?
C18 C13 C12 118.1(12) . . ?
C18 C13 C14 126.5(11) . . ?
C14A C13A C12 119.8(8) . . ?
C18A C13A C12 122.8(8) . . ?
C18A C13A C14A 117.4(7) . . ?
C13 C14 H14 123.6 . . ?
C15 C14 C13 112.9(11) . . ?
C15 C14 H14 123.6 . . ?
C13A C14A H14A 118.7 . . ?
C15A C14A C13A 122.6(8) . . ?
C15A C14A H14A 118.7 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(13) . . ?
C16 C15 H15 119.2 . . ?
C14A C15A H15A 121.1 . . ?
C16A C15A C14A 117.8(10) . . ?
C16A C15A H15A 121.1 . . ?
C15 C16 H16 118.2 . . ?
C15 C16 C17 123.6(13) . . ?
C17 C16 H16 118.2 . . ?
C15A C16A H16A 119.4 . . ?
C15A C16A C17A 121.2(9) . . ?
C17A C16A H16A 119.4 . . ?
C16 C17 H17 122.1 . . ?
C18 C17 C16 115.8(11) . . ?
C18 C17 H17 122.1 . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A C16A 120.2(8) . . ?
C18A C17A H17A 119.9 . . ?
C13 C18 C17 119.2(12) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C13A C18A C17A 120.5(8) . . ?
C13A C18A H18A 119.7 . . ?
C17A C18A H18A 119.7 . . ?
O4 C19 C4 123.1(3) . . ?
O4 C19 O5 123.2(2) . . ?
O5 C19 C4 113.7(2) . . ?
O5 C20 H20A 111.8 . . ?
O5 C20 H20B 111.8 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 O5 100.0(8) . . ?
C21 C20 H20A 111.8 . . ?
C21 C20 H20B 111.8 . . ?
O5 C20A H20D 110.8 . . ?
O5 C20A H20C 110.8 . . ?
H20D C20A H20C 108.9 . . ?
C21A C20A O5 104.6(9) . . ?
C21A C20A H20D 110.8 . . ?
C21A C20A H20C 110.8 . . ?
C20 C21 H21C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21C C21 H21A 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21E C21A H21D 109.5 . . ?
H21E C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
O6 C22 C5 121.9(2) . . ?
O6 C22 O7 125.8(2) . . ?
O7 C22 C5 112.2(2) . . ?
O7 C23 H23C 109.5 . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23C C23 H23A 109.5 . . ?
H23C C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?

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
O2 H2 O1 0.87(3) 1.89(3) 2.721(2) 159(3) 3_655 yes

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
C1 N1 C5 C4 8.5(3) . . . . ?
C1 N1 C5 C22 -164.28(17) . . . . ?
C1 N1 C6 C7 79.7(3) . . . . ?
C1 N1 C6 C11 -99.2(2) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C1 C2 C3 C12 -173.2(2) . . . . ?
O1 C1 N1 C5 171.84(17) . . . . ?
O1 C1 N1 C6 -8.9(3) . . . . ?
O1 C1 C2 O2 4.5(3) . . . . ?
O1 C1 C2 C3 -177.6(2) . . . . ?
N1 C1 C2 O2 -172.98(17) . . . . ?
N1 C1 C2 C3 5.0(3) . . . . ?
N1 C5 C22 O6 84.1(2) . . . . ?
N1 C5 C22 O7 -93.3(2) . . . . ?
N1 C6 C7 C8 178.7(2) . . . . ?
N1 C6 C11 C10 -178.2(2) . . . . ?
O2 C2 C3 C4 -179.58(18) . . . . ?
O2 C2 C3 C12 4.7(3) . . . . ?
C2 C1 N1 C5 -10.7(3) . . . . ?
C2 C1 N1 C6 168.58(16) . . . . ?
C2 C3 C4 C5 -5.0(3) . . . . ?
C2 C3 C4 C19 174.0(2) . . . . ?
C2 C3 C12 O3 96.0(3) . . . . ?
C2 C3 C12 C13 -79.1(19) . . . . ?
C2 C3 C12 C13A -80.2(11) . . . . ?
O3 C12 C13 C14 -4(3) . . . . ?
O3 C12 C13 C18 176(2) . . . . ?
O3 C12 C13A C14A 4(3) . . . . ?
O3 C12 C13A C18A -175.5(15) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C22 171.67(19) . . . . ?
C3 C4 C19 O4 -10.9(4) . . . . ?
C3 C4 C19 O5 171.7(2) . . . . ?
C3 C12 C13 C14 170.9(17) . . . . ?
C3 C12 C13 C18 -8(4) . . . . ?
C3 C12 C13A C14A 179.4(14) . . . . ?
C3 C12 C13A C18A 0(2) . . . . ?
C4 C3 C12 O3 -79.6(3) . . . . ?
C4 C3 C12 C13 105.3(19) . . . . ?
C4 C3 C12 C13A 104.2(11) . . . . ?
C4 C5 C22 O6 -88.3(3) . . . . ?
C4 C5 C22 O7 94.4(2) . . . . ?
C5 N1 C6 C7 -101.1(2) . . . . ?
C5 N1 C6 C11 80.1(2) . . . . ?
C5 C4 C19 O4 168.1(2) . . . . ?
C5 C4 C19 O5 -9.3(3) . . . . ?
C6 N1 C5 C4 -170.70(17) . . . . ?
C6 N1 C5 C22 16.5(2) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C6 C11 C10 2.9(4) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C9 C10 C11 C6 -1.3(4) . . . . ?
C11 C6 C7 C8 -2.5(4) . . . . ?
C12 C3 C4 C5 170.4(2) . . . . ?
C12 C3 C4 C19 -10.6(3) . . . . ?
C12 C13 C14 C15 178(2) . . . . ?
C12 C13 C18 C17 177(2) . . . . ?
C12 C13A C14A C15A -177.7(16) . . . . ?
C12 C13A C18A C17A -177.5(18) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C13A C14A C15A C16A -4(3) . . . . ?
C14 C13 C18 C17 -2(5) . . . . ?
C14 C15 C16 C17 3(4) . . . . ?
C14A C13A C18A C17A 3(3) . . . . ?
C14A C15A C16A C17A 1(3) . . . . ?
C15 C16 C17 C18 -7(4) . . . . ?
C15A C16A C17A C18A 4(3) . . . . ?
C16 C17 C18 C13 6(4) . . . . ?
C16A C17A C18A C13A -6(3) . . . . ?
C18 C13 C14 C15 -2(4) . . . . ?
C18A C13A C14A C15A 1(3) . . . . ?
C19 C4 C5 N1 -179.18(18) . . . . ?
C19 C4 C5 C22 -7.3(3) . . . . ?
C19 O5 C20 C21 -103.5(10) . . . . ?
C19 O5 C20A C21A 167.4(14) . . . . ?
C20 O5 C19 O4 16.0(6) . . . . ?
C20 O5 C19 C4 -166.6(5) . . . . ?
C20A O5 C19 O4 -7.2(11) . . . . ?
C20A O5 C19 C4 170.2(10) . . . . ?
C23 O7 C22 C5 178.9(2) . . . . ?
C23 O7 C22 O6 1.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.957
_oxdiff_exptl_absorpt_empirical_full_min 0.397
