# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JA1493
_database_code_depnum_ccdc_archive 'CCDC 2373464'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-02-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H16O4
_chemical_oxdiff_usercomment     JA1493
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   20.5214(2)
_cell_length_b                   5.73430(5)
_cell_length_c                   22.2387(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9766(9)
_cell_angle_gamma                90
_cell_volume                     2591.64(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10886
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8730
_cell_measurement_theta_min      4.0050
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0332
0 0 -1 0.0629
-1 -2 0 0.2535
-2 0 -1 0.0655
1 0 0 0.0804
-1 0 0 0.0556
2 1 2 0.1652
11 1 3 0.1102
3 -3 -7 0.2404
-6 -3 -6 0.2205
-10 0 11 0.0559
10 2 -8 0.1040
7 0 -13 0.0442
8 1 -11 0.0857
4 1 -14 0.0547
-1 1 14 0.0672
5 0 12 0.0395

_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.096
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -0.0001 1.0001 0.0278 -0.0542 0.0345
-0.0002 0.0001 -1.0001 -0.0278 0.0542 -0.0345
-0.9948 -2.0000 0.0000 0.1198 -0.2287 -0.4772
-2.0000 -0.0000 -0.9986 -0.1636 -0.0067 -0.0634
0.9999 0.0000 -0.0007 0.0679 0.0304 0.0144
-0.9999 -0.0000 0.0007 -0.0679 -0.0304 -0.0144
1.9977 0.9999 1.9990 0.0975 0.0516 0.3292
11.4423 1.3827 3.3131 0.7396 0.3055 0.5997
3.2703 -3.2241 -6.7140 0.3379 0.1433 -0.9302
-5.6575 -2.8291 -6.1794 -0.2907 -0.1179 -0.9495
-10.3564 0.0704 10.5462 -0.4174 -0.8791 0.2300
10.3152 1.6128 -8.1462 0.3235 0.9148 0.2417
7.1036 -0.0281 -13.1629 0.1199 0.9262 -0.3574
8.2671 1.2348 -11.4027 0.1295 0.9915 0.0123
4.0178 0.6570 -14.0001 -0.1771 0.9457 -0.2724
-1.3043 0.9367 13.9611 0.2110 -0.7030 0.6791
5.0045 0.0328 12.4945 0.6836 -0.5215 0.5106

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.048
_diffrn_reflns_theta_min         4.014
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00 142.00   0.50    0.20    --  115.25 -79.00-138.60  198
  2  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00 120.00  124
  3  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00 150.00  124
  4  ω     43.00 101.00   0.50    0.20    --  115.25 -78.00 171.14  116
  5  ω     85.00 110.00   0.50    0.20    --  115.25 -78.00 171.14   50
  6  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00 150.00   56
  7  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00  60.00  124
  8  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00   0.00   56
  9  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00 -30.00   56
 10  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00 -60.00   56
 11  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00 -30.00  124
 12  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00 -90.00  124
 13  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00-150.00   56
 14  ω     43.00 105.00   0.50    0.20    --  115.25 -77.00-120.00  124
 15  ω     43.00  69.00   0.50    0.20    --  115.25 -61.00 -90.00   52
 16  ω     43.00  71.00   0.50    0.20    --  115.25 -61.00  30.00   56
 17  ω     43.00  68.00   0.50    0.20    --  115.25 -61.00  90.00   50
 18  ω     45.00 111.00   0.50    0.20    --  115.25-125.00  90.00  132
 19  ω     43.00 105.00   0.50    0.20    --  115.25 -95.00  90.00  124
 20  ω     -1.00  80.00   0.50    0.05    --   44.91 -99.00 -30.00  162
 21  ω     45.00 111.00   0.50    0.20    --  115.25-125.00-120.00  132
 22  ω     44.00  70.00   0.50    0.20    --  115.25 -86.00-175.06   52
 23  ω    118.00 144.00   0.50    0.20    --  115.25 -83.00  15.09   52
 24  ω     90.00 178.00   0.50    0.20    --  115.25  15.00 -90.00  176
 25  ω     96.00 178.00   0.50    0.20    --  115.25  61.00 -90.00  164
 26  ω     96.00 178.00   0.50    0.20    --  115.25  61.00-120.00  164
 27  ω     97.00 178.00   0.50    0.20    --  115.25  45.00 -30.00  162
 28  ω    105.00 131.00   0.50    0.20    --  115.25  61.00  90.00   52
 29  ω     98.00 124.00   0.50    0.20    --  115.25  45.00 150.00   52
 30  ω     89.00 178.00   0.50    0.20    --  115.25  77.00 150.00  178
 31  ω     89.00 178.00   0.50    0.20    --  115.25  77.00  90.00  178
 32  ω     89.00 178.00   0.50    0.20    --  115.25  77.00  90.00  178
 33  ω     97.00 178.00   0.50    0.20    --  115.25  30.00 150.00  162
 34  ω     27.00 120.00   0.50    0.05    --   44.91  40.00  30.00  186
 35  ω     97.00 178.00   0.50    0.20    --  115.25  40.00  30.00  162
 36  ω     97.00 178.00   0.50    0.20    --  115.25  45.00 -30.00  162
 37  ω     95.00 178.00   0.50    0.20    --  115.25 125.00-120.00  166
 38  ω     95.00 134.00   0.50    0.20    --  115.25 125.00-120.00   78
 39  ω    -30.00  45.00   0.50    0.05    --   44.91 -40.00-123.00  150
 40  ω    -51.00 -20.00   0.50    0.20    --  -93.75  45.00 120.00   62
 41  ω    -51.00 -20.00   0.50    0.20    --  -93.75  45.00 150.00   62
 42  ω    -45.00 -18.00   0.50    0.20    --  -93.75  40.00  30.00   54
 43  ω    -45.00  31.00   0.50    0.05    --  -44.91  40.00  30.00  152
 44  ω    -51.00 -20.00   0.50    0.20    --  -93.75  45.00-120.00   62
 45  ω    -51.00 -20.00   0.50    0.20    --  -93.75  45.00-150.00   62
 46  ω    -51.00 -20.00   0.50    0.20    --  -93.75  45.00-180.00   62
 47  ω    -27.00  33.00   0.50    0.05    --  -44.91  19.00-180.00  120
 48  ω   -119.00 -27.00   0.50    0.05    --  -44.91 -40.00-123.00  184
 49  ω   -169.00 -75.00   0.50    0.20    --  -93.75 -40.00-123.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0679270000
_diffrn_orient_matrix_UB_12      -0.0936917000
_diffrn_orient_matrix_UB_13      0.0277486000
_diffrn_orient_matrix_UB_21      0.0303940000
_diffrn_orient_matrix_UB_22      0.0992093000
_diffrn_orient_matrix_UB_23      -0.0541745000
_diffrn_orient_matrix_UB_31      0.0144659000
_diffrn_orient_matrix_UB_32      0.2314173000
_diffrn_orient_matrix_UB_33      0.0344670000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             2825
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00062(10)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.058
_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)+(0.0461P)²+1.2598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0965
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_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 0.65928(4) 0.80076(13) 0.60291(3) 0.02529(18) Uani 1 1 d . . . . .
O2 O 0.60892(4) 0.57700(15) 0.52693(3) 0.0311(2) Uani 1 1 d . . . . .
O3 O 0.53848(4) 0.23324(14) 0.67670(3) 0.0300(2) Uani 1 1 d . . . . .
O4 O 0.67091(4) -0.15294(15) 0.92745(4) 0.0336(2) Uani 1 1 d . . . . .
H4 H 0.6497(9) -0.123(3) 0.9596(9) 0.050 Uiso 1 1 d . U . . .
C1 C 0.73105(6) 1.1213(2) 0.59284(6) 0.0321(3) Uani 1 1 d . . . . .
H1A H 0.748956 1.224308 0.564006 0.048 Uiso 1 1 calc R U . . .
H1B H 0.767283 1.046093 0.619138 0.048 Uiso 1 1 calc R U . . .
H1C H 0.704599 1.213055 0.617714 0.048 Uiso 1 1 calc R U . . .
C2 C 0.68850(5) 0.9379(2) 0.55855(5) 0.0292(2) Uani 1 1 d . . . . .
H2A H 0.653669 1.011971 0.529523 0.035 Uiso 1 1 calc R U . . .
H2B H 0.715356 0.836788 0.535523 0.035 Uiso 1 1 calc R U . . .
C3 C 0.62023(5) 0.62367(18) 0.58125(5) 0.0232(2) Uani 1 1 d . . . . .
C4 C 0.59404(5) 0.50215(18) 0.62964(4) 0.0238(2) Uani 1 1 d . . . . .
C5 C 0.55325(5) 0.31687(18) 0.62335(5) 0.0244(2) Uani 1 1 d . . . . .
C6 C 0.52164(6) 0.18760(19) 0.56914(5) 0.0287(2) Uani 1 1 d . . . . .
H6A H 0.534926 0.256860 0.532425 0.043 Uiso 1 1 calc R U . . .
H6B H 0.473701 0.196725 0.567101 0.043 Uiso 1 1 calc R U . . .
H6C H 0.535455 0.023921 0.572124 0.043 Uiso 1 1 calc R U . . .
C7 C 0.61251(6) 0.5555(2) 0.69615(5) 0.0311(3) Uani 1 1 d . . . . .
H7A H 0.604658 0.721640 0.704936 0.037 Uiso 1 1 calc R U . . .
H7B H 0.659190 0.517130 0.710122 0.037 Uiso 1 1 calc R U . . .
C8 C 0.56608(6) 0.39534(19) 0.72567(5) 0.0285(2) Uani 1 1 d . . . . .
H8 H 0.529381 0.491905 0.737627 0.034 Uiso 1 1 calc R U . . .
C9 C 0.59531(5) 0.25454(18) 0.77966(5) 0.0251(2) Uani 1 1 d . . . . .
C10 C 0.64745(5) 0.10125(19) 0.77659(5) 0.0270(2) Uani 1 1 d . . . . .
H10 H 0.666456 0.090156 0.740106 0.032 Uiso 1 1 calc R U . . .
C11 C 0.67193(6) -0.03512(19) 0.82600(5) 0.0281(2) Uani 1 1 d . . . . .
H11 H 0.707053 -0.140695 0.823163 0.034 Uiso 1 1 calc R U . . .
C12 C 0.64475(5) -0.01674(18) 0.88004(5) 0.0254(2) Uani 1 1 d . . . . .
C13 C 0.59370(5) 0.1380(2) 0.88420(5) 0.0264(2) Uani 1 1 d . . . . .
H13 H 0.575701 0.153084 0.921132 0.032 Uiso 1 1 calc R U . . .
C14 C 0.56904(5) 0.27114(19) 0.83387(5) 0.0269(2) Uani 1 1 d . . . . .
H14 H 0.533582 0.375371 0.836575 0.032 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 C2 1.4545(13) . ?
O1 C3 1.3411(13) . ?
O2 C3 1.2275(13) . ?
O3 C5 1.3523(13) . ?
O3 C8 1.4832(13) . ?
O4 H4 0.90(2) . ?
O4 C12 1.3612(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5053(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.4467(14) . ?
C4 C5 1.3477(15) . ?
C4 C7 1.5065(14) . ?
C5 C6 1.4856(14) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5351(15) . ?
C8 H8 1.0000 . ?
C8 C9 1.5010(15) . ?
C9 C10 1.3937(16) . ?
C9 C14 1.3905(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3849(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3974(15) . ?
C12 C13 1.3858(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3909(15) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 116.59(8) . . ?
C5 O3 C8 108.22(8) . . ?
C12 O4 H4 108.7(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 107.39(9) . . ?
O1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O1 C3 C4 111.26(9) . . ?
O2 C3 O1 122.72(10) . . ?
O2 C3 C4 126.01(10) . . ?
C3 C4 C7 124.31(9) . . ?
C5 C4 C3 126.30(9) . . ?
C5 C4 C7 109.27(9) . . ?
O3 C5 C6 114.16(9) . . ?
C4 C5 O3 113.59(9) . . ?
C4 C5 C6 132.26(10) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 111.3 . . ?
C4 C7 H7B 111.3 . . ?
C4 C7 C8 102.23(9) . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
O3 C8 C7 104.91(8) . . ?
O3 C8 H8 108.5 . . ?
O3 C8 C9 108.65(8) . . ?
C7 C8 H8 108.5 . . ?
C9 C8 C7 117.46(9) . . ?
C9 C8 H8 108.5 . . ?
C10 C9 C8 121.63(9) . . ?
C14 C9 C8 119.78(10) . . ?
C14 C9 C10 118.57(10) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.92(10) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.70(10) . . ?
C12 C11 H11 120.1 . . ?
O4 C12 C11 117.47(10) . . ?
O4 C12 C13 122.42(9) . . ?
C13 C12 C11 120.10(10) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.45(10) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 121.24(10) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O2 0.90(2) 1.83(2) 2.7356(11) 176.6(18) 8 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
O1 C3 C4 C5 179.92(10) . . . . ?
O1 C3 C4 C7 -4.53(14) . . . . ?
O2 C3 C4 C5 0.44(18) . . . . ?
O2 C3 C4 C7 175.98(11) . . . . ?
O3 C8 C9 C10 61.79(13) . . . . ?
O3 C8 C9 C14 -116.46(11) . . . . ?
O4 C12 C13 C14 -179.66(10) . . . . ?
C2 O1 C3 O2 -0.19(14) . . . . ?
C2 O1 C3 C4 -179.70(8) . . . . ?
C3 O1 C2 C1 -178.78(9) . . . . ?
C3 C4 C5 O3 177.74(10) . . . . ?
C3 C4 C5 C6 -2.19(19) . . . . ?
C3 C4 C7 C8 174.61(10) . . . . ?
C4 C7 C8 O3 12.71(11) . . . . ?
C4 C7 C8 C9 133.46(10) . . . . ?
C5 O3 C8 C7 -12.58(11) . . . . ?
C5 O3 C8 C9 -138.98(9) . . . . ?
C5 C4 C7 C8 -9.20(12) . . . . ?
C7 C4 C5 O3 1.64(13) . . . . ?
C7 C4 C5 C6 -178.29(11) . . . . ?
C7 C8 C9 C10 -56.99(14) . . . . ?
C7 C8 C9 C14 124.77(11) . . . . ?
C8 O3 C5 C4 7.18(12) . . . . ?
C8 O3 C5 C6 -172.87(9) . . . . ?
C8 C9 C10 C11 -177.08(10) . . . . ?
C8 C9 C14 C13 178.10(10) . . . . ?
C9 C10 C11 C12 -0.95(16) . . . . ?
C10 C9 C14 C13 -0.20(16) . . . . ?
C10 C11 C12 O4 -179.42(10) . . . . ?
C10 C11 C12 C13 -0.27(17) . . . . ?
C11 C12 C13 C14 1.23(16) . . . . ?
C12 C13 C14 C9 -1.00(17) . . . . ?
C14 C9 C10 C11 1.18(16) . . . . ?

_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.515
####################################################################### 
# 
# 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_JA1513
_database_code_depnum_ccdc_archive 'CCDC 2373466'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O9'
_chemical_formula_sum            'C22 H23 N O9'
_chemical_formula_weight         445.41
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H23NO9
_chemical_oxdiff_usercomment     JA1513
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.59853(9)
_cell_length_b                   11.65212(15)
_cell_length_c                   21.5751(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2161.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1260
_cell_measurement_theta_min      4.0740
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0183
0 0 1 0.0262
2 1 0 0.1750
0 1 0 0.0207
0 -1 2 0.0199
-1 -1 -1 0.0583
-2 1 1 0.0691
0 1 1 0.0238
0 -1 -1 0.0178
0 1 -1 0.0189
0 -1 1 0.0229

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.041
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 -1.0000 -0.0354 -0.0462 0.0413
0.0000 -0.0000 1.0000 0.0354 0.0462 -0.0413
2.0000 1.0000 0.0000 -0.1203 -0.1860 -0.3111
-0.0000 1.0000 0.0000 -0.1148 0.0505 -0.0418
0.0000 -1.0000 2.0000 0.1856 0.0420 -0.0407
-1.0000 -1.0000 -1.0000 0.0822 0.0215 0.2177
-2.0000 1.0000 1.0000 -0.0740 0.3332 0.1861
-0.0000 1.0000 1.0000 -0.0794 0.0967 -0.0831
0.0000 -1.0000 -1.0000 0.0794 -0.0967 0.0831
-0.0000 1.0000 -1.0000 -0.1502 0.0043 -0.0006
0.0000 -1.0000 1.0000 0.1502 -0.0043 0.0006

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.892
_diffrn_reflns_theta_min         4.098
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -47.55   0.55    0.85    --  -45.04 -55.00-162.00   99
  2  ω      5.00  45.15   0.55    0.85    --   45.04 -99.00 103.00   73
  3  ω   -158.00-131.05   0.55    3.40    --  -93.75 -55.00-162.00   49
  4  ω    -54.00 -27.60   0.55    3.40    --  -93.75  99.00-150.00   48
  5  ω    142.00 167.30   0.55    3.40    --  115.25  99.00-150.00   46
  6  ω     99.00 123.75   0.55    3.40    --  115.25  55.00 -19.00   45
  7  ω     73.00 105.45   0.55    3.40    --  115.25 -99.00 103.00   59
  8  ω     59.00  91.45   0.55    3.40    --  115.25 -74.00 -11.00   59
  9  ω    -10.00  31.25   0.55    0.85    --  -45.04  19.00-150.00   75
 10  ω    -31.00   4.20   0.55    0.85    --   45.04 -19.00-150.00   64
 11  ω    -32.00   3.20   0.55    0.85    --   45.04 -19.00   0.00   64
 12  ω     43.00  67.75   0.55    3.40    --  115.25 -61.00  30.00   45
 13  ω     51.00 105.45   0.55    3.40    --  115.25-104.00 170.80   99
 14  ω     65.00 107.35   0.55    3.40    --  115.25-125.00-120.00   77
 15  ω     45.00  69.75   0.55    3.40    --  115.25 -61.00-150.00   45
 16  ω    144.00 175.35   0.55    3.40    --  115.25 125.00-180.00   57
 17  ω     96.00 138.35   0.55    3.40    --  115.25  61.00   0.00   77
 18  ω     57.00  83.40   0.55    3.40    --  115.25 -95.00  30.00   48
 19  ω    104.00 157.35   0.55    3.40    --  115.25  30.00  60.00   97
 20  ω     44.00  70.40   0.55    3.40    --  115.25 -61.00-120.00   48
 21  ω     97.00 123.40   0.55    3.40    --  115.25 125.00-180.00   48
 22  ω     43.00  67.75   0.55    3.40    --  115.25 -61.00  60.00   45
 23  ω     43.00  77.10   0.55    3.40    --  115.25 -77.00-150.00   62
 24  ω    122.00 156.10   0.55    3.40    --  115.25  45.00-150.00   62
 25  ω     43.00  94.70   0.55    3.40    --  115.25 -77.00 -60.00   94
 26  ω    138.00 164.40   0.55    3.40    --  115.25  45.00 -90.00   48
 27  ω     55.00  79.75   0.55    3.40    --  115.25 -95.00 -30.00   45
 28  ω    112.00 166.45   0.55    3.40    --  115.25  61.00-180.00   99
 29  ω     43.00  67.75   0.55    3.40    --  115.25 -61.00 120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0027394000
_diffrn_orient_matrix_UB_12      -0.1148373000
_diffrn_orient_matrix_UB_13      0.0353955000
_diffrn_orient_matrix_UB_21      -0.1182427000
_diffrn_orient_matrix_UB_22      0.0504942000
_diffrn_orient_matrix_UB_23      0.0462389000
_diffrn_orient_matrix_UB_31      -0.1346039000
_diffrn_orient_matrix_UB_32      -0.0418448000
_diffrn_orient_matrix_UB_33      -0.0412839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                4277
_reflns_number_total             4408
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_coef       0.0015(2)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.043
_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)+(0.0284P)²+0.3892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0661
_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 Ternary CH refined with riding coordinates and stretchable bonds:
 C9(H9), C10(H10), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.41194(15) 0.63260(11) 0.92512(5) 0.0228(3) Uani 1 1 d . . . . .
O2 O 0.56727(13) 0.67275(10) 0.84471(5) 0.0175(2) Uani 1 1 d . . . . .
O3 O -0.14896(14) 0.76226(12) 0.88568(5) 0.0231(3) Uani 1 1 d . . . . .
H3 H -0.233(3) 0.727(2) 0.8795(12) 0.035 Uiso 1 1 d . U . . .
O4 O 0.67681(14) 0.52180(11) 0.69519(6) 0.0238(3) Uani 1 1 d . . . . .
O5 O 0.48573(16) 0.49341(12) 0.63203(5) 0.0289(3) Uani 1 1 d . . . . .
O6 O 0.26281(14) 0.94559(11) 0.59361(6) 0.0223(3) Uani 1 1 d . . . . .
O7 O 0.02885(14) 0.88939(11) 0.55746(6) 0.0229(3) Uani 1 1 d . . . . .
O8 O 0.18674(15) 0.64434(13) 0.53077(6) 0.0282(3) Uani 1 1 d . . . . .
O9 O -0.02250(14) 0.61638(11) 0.59134(5) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.53917(16) 0.52845(12) 0.68116(6) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.4755(3) 0.73169(18) 0.95651(8) 0.0346(5) Uani 1 1 d . . . . .
H1A H 0.422005 0.742378 0.996203 0.052 Uiso 1 1 calc R U . . .
H1B H 0.460808 0.799995 0.930670 0.052 Uiso 1 1 calc R U . . .
H1C H 0.586794 0.719845 0.963944 0.052 Uiso 1 1 calc R U . . .
C2 C 0.46981(17) 0.61176(14) 0.86877(7) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.40170(17) 0.50575(14) 0.84106(7) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.34692(18) 0.42163(14) 0.88149(7) 0.0176(3) Uani 1 1 d . . . . .
H4 H 0.351091 0.434657 0.924921 0.021 Uiso 1 1 calc R U . . .
C5 C 0.28658(18) 0.31945(15) 0.85936(8) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.250360 0.262558 0.887398 0.024 Uiso 1 1 calc R U . . .
C6 C 0.27935(18) 0.30067(15) 0.79584(8) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.237974 0.230758 0.780303 0.023 Uiso 1 1 calc R U . . .
C7 C 0.33258(19) 0.38407(14) 0.75503(7) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.326908 0.370503 0.711672 0.022 Uiso 1 1 calc R U . . .
C8 C 0.39432(17) 0.48756(13) 0.77659(7) 0.0141(3) Uani 1 1 d . . . . .
C9 C 0.43033(18) 0.58086(13) 0.72919(7) 0.0142(3) Uani 1 1 d . . . . .
H9 H 0.4819(12) 0.6424(15) 0.7493(5) 0.017 Uiso 1 1 calc R U . . .
C10 C 0.28047(17) 0.62622(14) 0.69885(7) 0.0139(3) Uani 1 1 d . . . . .
H10 H 0.2343(11) 0.5639(14) 0.6754(5) 0.017 Uiso 1 1 calc R U . . .
C11 C 0.16726(18) 0.65984(13) 0.74982(7) 0.0139(3) Uani 1 1 d . . . . .
C12 C 0.19267(18) 0.75782(15) 0.78581(7) 0.0171(3) Uani 1 1 d . . . . .
H12 H 0.283441 0.802645 0.779173 0.021 Uiso 1 1 calc R U . . .
C13 C 0.08678(19) 0.79050(15) 0.83121(7) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.104856 0.857691 0.855089 0.023 Uiso 1 1 calc R U . . .
C14 C -0.04539(19) 0.72484(15) 0.84159(7) 0.0176(3) Uani 1 1 d . . . . .
C15 C -0.07013(18) 0.62488(15) 0.80752(7) 0.0171(3) Uani 1 1 d . . . . .
H15 H -0.158502 0.578251 0.815541 0.021 Uiso 1 1 calc R U . . .
C16 C 0.03554(18) 0.59393(13) 0.76170(7) 0.0157(3) Uani 1 1 d . . . . .
H16 H 0.017520 0.526481 0.738037 0.019 Uiso 1 1 calc R U . . .
C17 C 0.30913(18) 0.72699(14) 0.65389(7) 0.0154(3) Uani 1 1 d . . . . .
H17A H 0.350728 0.793673 0.676987 0.019 Uiso 1 1 calc R U . . .
H17B H 0.386649 0.704360 0.622236 0.019 Uiso 1 1 calc R U . . .
C18 C 0.15575(17) 0.75988(14) 0.62225(7) 0.0153(3) Uani 1 1 d . . . . .
H18 H 0.0769(18) 0.76292(16) 0.6533(7) 0.018 Uiso 1 1 calc R U . . .
C19 C 0.11017(19) 0.66849(14) 0.57568(7) 0.0169(3) Uani 1 1 d . . . . .
C20 C -0.0734(3) 0.52815(17) 0.54895(9) 0.0303(4) Uani 1 1 d . . . . .
H20A H -0.172177 0.495894 0.563481 0.045 Uiso 1 1 calc R U . . .
H20B H 0.005102 0.467314 0.546993 0.045 Uiso 1 1 calc R U . . .
H20C H -0.087803 0.561375 0.507619 0.045 Uiso 1 1 calc R U . . .
C21 C 0.16003(18) 0.87576(15) 0.58973(7) 0.0167(3) Uani 1 1 d . . . . .
C22 C 0.0069(2) 0.99867(16) 0.52714(8) 0.0250(4) Uani 1 1 d . . . . .
H22A H -0.091164 0.997740 0.504014 0.037 Uiso 1 1 calc R U . . .
H22B H 0.093334 1.012664 0.498506 0.037 Uiso 1 1 calc R U . . .
H22C H 0.003705 1.059773 0.558328 0.037 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 1.446(2) . ?
O1 C2 1.3359(18) . ?
O2 C2 1.215(2) . ?
O3 H3 0.84(3) . ?
O3 C14 1.374(2) . ?
O4 N1 1.2240(19) . ?
O5 N1 1.2254(19) . ?
O6 C21 1.204(2) . ?
O7 C21 1.3350(19) . ?
O7 C22 1.444(2) . ?
O8 C19 1.205(2) . ?
O9 C19 1.336(2) . ?
O9 C20 1.444(2) . ?
N1 C9 1.5241(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.492(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.408(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(2) . ?
C8 C9 1.524(2) . ?
C9 H9 0.95(2) . ?
C9 C10 1.539(2) . ?
C10 H10 0.97(2) . ?
C10 C11 1.520(2) . ?
C10 C17 1.543(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.392(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 C15 1.394(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.534(2) . ?
C18 H18 0.95(2) . ?
C18 C19 1.516(2) . ?
C18 C21 1.522(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C2 O1 C1 115.51(14) . . ?
C14 O3 H3 106.8(18) . . ?
C21 O7 C22 116.84(13) . . ?
C19 O9 C20 114.99(14) . . ?
O4 N1 O5 123.74(14) . . ?
O4 N1 C9 116.80(13) . . ?
O5 N1 C9 119.44(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 111.66(13) . . ?
O2 C2 O1 122.64(15) . . ?
O2 C2 C3 125.70(14) . . ?
C4 C3 C2 117.64(14) . . ?
C4 C3 C8 119.80(15) . . ?
C8 C3 C2 122.55(14) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.05(15) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.52(16) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.02(16) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.20(15) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C9 123.10(14) . . ?
C7 C8 C3 118.40(14) . . ?
C7 C8 C9 117.99(13) . . ?
N1 C9 C8 107.17(12) . . ?
N1 C9 H9 109.1 . . ?
N1 C9 C10 111.25(12) . . ?
C8 C9 H9 109.1 . . ?
C8 C9 C10 111.12(12) . . ?
C10 C9 H9 109.1 . . ?
C9 C10 H10 107.9 . . ?
C9 C10 C17 113.27(12) . . ?
C11 C10 C9 108.48(12) . . ?
C11 C10 H10 107.9 . . ?
C11 C10 C17 111.16(13) . . ?
C17 C10 H10 107.9 . . ?
C12 C11 C10 120.82(14) . . ?
C16 C11 C10 120.80(14) . . ?
C16 C11 C12 118.39(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.84(15) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.92(15) . . ?
C14 C13 H13 120.0 . . ?
O3 C14 C13 117.86(15) . . ?
O3 C14 C15 122.10(15) . . ?
C13 C14 C15 120.03(15) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.47(15) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.30(15) . . ?
C15 C16 H16 119.3 . . ?
C10 C17 H17A 109.8 . . ?
C10 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 C10 109.43(12) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18 107.9 . . ?
C19 C18 C17 109.99(13) . . ?
C19 C18 H18 107.9 . . ?
C19 C18 C21 108.90(12) . . ?
C21 C18 C17 113.95(13) . . ?
C21 C18 H18 107.9 . . ?
O8 C19 O9 124.33(16) . . ?
O8 C19 C18 123.78(15) . . ?
O9 C19 C18 111.87(13) . . ?
O9 C20 H20A 109.5 . . ?
O9 C20 H20B 109.5 . . ?
O9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 O7 125.17(15) . . ?
O6 C21 C18 125.81(14) . . ?
O7 C21 C18 108.99(13) . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O3 H3 O2 0.84(3) 1.98(3) 2.7969(17) 164(3) 1_455 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
O1 C2 C3 C4 -26.2(2) . . . . ?
O1 C2 C3 C8 155.14(14) . . . . ?
O2 C2 C3 C4 152.95(16) . . . . ?
O2 C2 C3 C8 -25.7(2) . . . . ?
O3 C14 C15 C16 177.30(14) . . . . ?
O4 N1 C9 C8 -80.02(17) . . . . ?
O4 N1 C9 C10 158.33(14) . . . . ?
O5 N1 C9 C8 98.40(16) . . . . ?
O5 N1 C9 C10 -23.3(2) . . . . ?
N1 C9 C10 C11 171.23(12) . . . . ?
N1 C9 C10 C17 -64.85(17) . . . . ?
C1 O1 C2 O2 -1.3(2) . . . . ?
C1 O1 C2 C3 177.90(15) . . . . ?
C2 C3 C4 C5 -177.99(15) . . . . ?
C2 C3 C8 C7 178.15(14) . . . . ?
C2 C3 C8 C9 -10.1(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C8 C9 N1 132.72(15) . . . . ?
C3 C8 C9 C10 -105.54(16) . . . . ?
C4 C3 C8 C7 -0.5(2) . . . . ?
C4 C3 C8 C9 171.23(14) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C3 0.1(2) . . . . ?
C6 C7 C8 C9 -172.08(15) . . . . ?
C7 C8 C9 N1 -55.54(17) . . . . ?
C7 C8 C9 C10 66.19(17) . . . . ?
C8 C3 C4 C5 0.7(2) . . . . ?
C8 C9 C10 C11 51.91(16) . . . . ?
C8 C9 C10 C17 175.83(12) . . . . ?
C9 C10 C11 C12 72.19(18) . . . . ?
C9 C10 C11 C16 -107.95(15) . . . . ?
C9 C10 C17 C18 175.58(12) . . . . ?
C10 C11 C12 C13 178.07(14) . . . . ?
C10 C11 C16 C15 -178.93(14) . . . . ?
C10 C17 C18 C19 -72.07(15) . . . . ?
C10 C17 C18 C21 165.34(12) . . . . ?
C11 C10 C17 C18 -61.98(16) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
C12 C13 C14 O3 -178.16(15) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C16 -2.3(2) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
C16 C11 C12 C13 -1.8(2) . . . . ?
C17 C10 C11 C12 -52.98(18) . . . . ?
C17 C10 C11 C16 126.88(15) . . . . ?
C17 C18 C19 O8 -62.5(2) . . . . ?
C17 C18 C19 O9 115.90(14) . . . . ?
C17 C18 C21 O6 -9.6(2) . . . . ?
C17 C18 C21 O7 172.26(13) . . . . ?
C19 C18 C21 O6 -132.78(17) . . . . ?
C19 C18 C21 O7 49.07(16) . . . . ?
C20 O9 C19 O8 -1.7(2) . . . . ?
C20 O9 C19 C18 179.92(14) . . . . ?
C21 C18 C19 O8 63.0(2) . . . . ?
C21 C18 C19 O9 -118.57(14) . . . . ?
C22 O7 C21 O6 -2.7(2) . . . . ?
C22 O7 C21 C18 175.44(14) . . . . ?

_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.474
####################################################################### 
# 
# 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_JA1642
_database_code_depnum_ccdc_archive 'CCDC 2382844'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-09-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O7'
_chemical_formula_sum            'C20 H21 N O7'
_chemical_formula_weight         387.38
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21NO7
_chemical_oxdiff_usercomment     JA1642
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.57151(5)
_cell_length_b                   14.07632(12)
_cell_length_c                   23.5481(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1846.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17498
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.3010
_cell_measurement_theta_min      3.6430
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0702
0 1 2 0.1079
-1 -2 2 0.0613
1 2 -2 0.0515
2 0 -1 0.0432
1 0 1 0.0377
1 -2 2 0.0447
1 0 2 0.0424
-1 0 -2 0.0683
-1 2 -2 0.0772
0 -1 1 0.0625
0 1 -1 0.0840
0 1 -2 0.0645
0 -1 2 0.0519
0 0 1 0.0608
-3 0 4 0.0447
-3 -6 -1 0.0549
3 -3 -3 0.0436
-4 2 2 0.0503
-4 -2 -1 0.0404

_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.086
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -1.0000 -2.0000 0.0767 0.1042 0.1112
-0.0000 1.0000 2.0000 -0.0767 -0.1042 -0.1112
-1.0000 -2.0000 2.0000 -0.1380 -0.1635 0.3095
1.0000 2.0000 -2.0000 0.1380 0.1635 -0.3095
2.0000 -0.0000 -1.0000 -0.0647 0.4593 -0.3082
1.0000 0.0000 1.0000 -0.1206 0.1909 -0.1724
1.0000 -2.0000 2.0000 -0.2615 0.2700 -0.0109
1.0000 0.0000 2.0000 -0.1795 0.1650 -0.1846
-1.0000 -0.0000 -2.0000 0.1795 -0.1650 0.1846
-1.0000 2.0000 -2.0000 0.2615 -0.2700 0.0109
-0.0000 -1.0000 1.0000 -0.0999 0.0266 0.0746
0.0000 1.0000 -1.0000 0.0999 -0.0266 -0.0746
0.0000 1.0000 -2.0000 0.1587 -0.0008 -0.0625
-0.0000 -1.0000 2.0000 -0.1587 0.0008 0.0625
-0.0000 0.0000 1.0000 -0.0589 -0.0258 -0.0122
-3.4897 -0.0703 4.0047 -0.0231 -0.8561 0.5163
-2.8837 -5.5030 -0.6219 -0.0110 -0.3201 0.9473
3.2769 -3.4802 -2.8146 -0.1795 0.9656 -0.1884
-3.5282 1.6155 1.9950 0.1668 -0.9010 0.4006
-3.5512 -1.6758 -0.7480 0.1947 -0.6623 0.7235

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.994
_diffrn_reflns_theta_min         3.658
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  70.00   0.50    0.50    --   44.91 -74.00  41.00  194
  2  ω    -27.00  70.00   0.50    0.50    --   44.91 -74.00  41.00  194
  3  ω    -83.00 -24.00   0.50    2.00    --  -93.75 113.00-110.00  118
  4  ω    -96.00 -20.00   0.50    2.00    --  -93.75  74.00 170.00  152
  5  ω    -57.00 -21.00   0.50    2.00    --  -93.75  50.00  21.00   72
  6  ω   -113.00 -74.00   0.50    0.50    --  -44.88 -50.00-125.00   78
  7  ω    -17.00   9.00   0.50    0.50    --  -44.88  74.00 170.00   52
  8  ω     91.00 118.00   0.50    0.50    --   44.88  77.00 150.00   54
  9  ω   -146.00-121.00   0.50    2.00    --  -93.75-113.00 157.00   50
 10  ω   -145.00-120.00   0.50    2.00    --  -93.75 -50.00-125.00   50
 11  ω     77.00 103.00   0.50    2.00    --  115.25-113.00 157.00   52
 12  ω    140.00 165.00   0.50    2.00    --  115.25 113.00-110.00   50
 13  ω     45.00  70.00   0.50    2.00    --  115.25 -74.00  41.00   50
 14  ω    102.00 137.00   0.50    2.00    --  115.25  50.00  21.00   70
 15  ω    117.00 156.00   0.50    2.00    --  115.25  74.00 170.00   78
 16  ω    -14.00  20.00   0.50    0.50    --   44.88 -19.00-120.00   68
 17  ω     84.00 110.00   0.50    2.00    --  115.25-125.00  60.00   52
 18  ω     58.00  83.00   0.50    2.00    --  115.25-125.00 -60.00   50
 19  ω    114.00 140.00   0.50    2.00    --  115.25  15.00 -60.00   52
 20  ω     97.00 122.00   0.50    2.00    --  115.25  45.00 150.00   50
 21  ω    137.00 176.00   0.50    2.00    --  115.25  45.00 150.00   78
 22  ω     43.00  68.00   0.50    2.00    --  115.25 -61.00-120.00   50
 23  ω     61.00 103.00   0.50    2.00    --  115.25 -77.00 -90.00   84
 24  ω     47.00  98.00   0.50    2.00    --  115.25-125.00  30.00  102
 25  ω    101.00 137.00   0.50    2.00    --  115.25  61.00  90.00   72
 26  ω     59.00 105.00   0.50    2.00    --  115.25 -77.00 150.00   92
 27  ω     85.00 111.00   0.50    2.00    --  115.25-125.00-150.00   52
 28  ω     40.00  94.00   0.50    2.00    --  115.25   0.00-150.00  108
 29  ω    108.00 147.00   0.50    2.00    --  115.25   0.00-150.00   78
 30  ω     64.00  90.00   0.50    2.00    --  115.25 -77.00   0.00   52
 31  ω    109.00 135.00   0.50    2.00    --  115.25  61.00 -60.00   52
 32  ω     44.00  82.00   0.50    2.00    --  115.25 -77.00  30.00   76
 33  ω     98.00 123.00   0.50    2.00    --  115.25  45.00 120.00   50
 34  ω    146.00 178.00   0.50    2.00    --  115.25  45.00 120.00   64
 35  ω    146.00 171.00   0.50    2.00    --  115.25 125.00  60.00   50
 36  ω     43.00  68.00   0.50    2.00    --  115.25 -61.00   0.00   50
 37  ω     68.00  94.00   0.50    2.00    --  115.25 -95.00  60.00   52
 38  ω     50.00  76.00   0.50    2.00    --  115.25 -87.00  81.43   52
 39  ω     86.00 146.00   0.50    2.00    --  115.25 -87.00  81.43  120
 40  ω     97.00 142.00   0.50    2.00    --  115.25 125.00   0.00   90
 41  ω     48.00  98.00   0.50    2.00    --  115.25 -77.00-150.00  100
 42  ω     45.00  72.00   0.50    2.00    --  115.25 -77.00  60.00   54
 43  ω     43.00  72.00   0.50    2.00    --  115.25 -95.00  30.00   58
 44  ω     73.00  98.00   0.50    2.00    --  115.25 -95.00  30.00   50
 45  ω     51.00  77.00   0.50    2.00    --  115.25-125.00-180.00   52
 46  ω     44.00  70.00   0.50    2.00    --  115.25 -61.00 120.00   52
 47  ω     85.00 110.00   0.50    2.00    --  115.25-125.00 120.00   50
 48  ω     43.00  68.00   0.50    2.00    --  115.25 -61.00 -90.00   50
 49  ω     69.00 104.00   0.50    2.00    --  115.25 -95.00 -30.00   70
 50  ω   -117.00 -26.00   0.50    0.50    --  -44.88 -57.00 -90.00  182
 51  ω   -117.00 -19.00   0.50    0.50    --  -44.88 -77.00 150.00  196
 52  ω   -117.00 -26.00   0.50    0.50    --  -44.88 -57.00  60.00  182
 53  ω   -120.00 -28.00   0.50    0.50    --  -44.88 -38.00 -60.00  184
 54  ω   -117.00 -20.00   0.50    0.50    --  -44.88 -74.00  41.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0617694000
_diffrn_orient_matrix_UB_12      0.0410127000
_diffrn_orient_matrix_UB_13      -0.0588668000
_diffrn_orient_matrix_UB_21      0.2167188000
_diffrn_orient_matrix_UB_22      -0.0524772000
_diffrn_orient_matrix_UB_23      -0.0258466000
_diffrn_orient_matrix_UB_31      -0.1601854000
_diffrn_orient_matrix_UB_32      -0.0868282000
_diffrn_orient_matrix_UB_33      -0.0121862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3902
_reflns_number_total             3993
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.079
_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)+(0.0563P)²+0.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5(2)
 0.5(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.6740(3) 0.48663(11) 0.51930(6) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.9324(3) 0.50827(11) 0.45269(7) 0.0345(3) Uani 1 1 d . . . . .
O3 O 0.6211(4) 0.08626(11) 0.43193(8) 0.0420(4) Uani 1 1 d . . . . .
H3 H 0.483(7) 0.071(3) 0.4521(15) 0.063 Uiso 1 1 d . U . . .
O4 O 0.2009(3) 0.31148(12) 0.28162(8) 0.0412(4) Uani 1 1 d . . . . .
O5 O 0.5671(3) 0.34819(11) 0.24847(7) 0.0375(4) Uani 1 1 d . . . . .
O6 O -0.0709(3) 0.54624(12) 0.27228(7) 0.0372(4) Uani 1 1 d . . . . .
O7 O 0.1072(3) 0.48746(13) 0.19434(6) 0.0385(4) Uani 1 1 d . . . . .
N1 N 0.7274(3) 0.50942(11) 0.47049(7) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.7456(4) 0.68407(15) 0.39053(9) 0.0321(5) Uani 1 1 d . . . . .
H1 H 0.863376 0.642631 0.375140 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7650(5) 0.78132(16) 0.38220(10) 0.0357(5) Uani 1 1 d . . . . .
H2 H 0.897297 0.806520 0.361692 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5898(5) 0.84210(15) 0.40402(10) 0.0382(5) Uani 1 1 d . . . . .
H3A H 0.602529 0.908770 0.398541 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3987(5) 0.80481(16) 0.43349(10) 0.0367(5) Uani 1 1 d . . . . .
H4 H 0.277292 0.845931 0.447573 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3813(4) 0.70735(15) 0.44291(9) 0.0321(5) Uani 1 1 d . . . . .
H5 H 0.250597 0.682484 0.464150 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5538(4) 0.64693(14) 0.42140(8) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.5253(4) 0.54109(14) 0.43179(9) 0.0275(4) Uani 1 1 d . . . . .
H7 H 0.369352 0.530134 0.451745 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5317(4) 0.47858(14) 0.37803(8) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.676924 0.496130 0.355402 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5496(4) 0.37380(14) 0.39369(8) 0.0271(4) Uani 1 1 d . . . . .
C10 C 0.3765(4) 0.32864(15) 0.42672(9) 0.0308(4) Uani 1 1 d . . . . .
H10 H 0.242457 0.363864 0.440064 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3964(4) 0.23276(15) 0.44054(9) 0.0326(5) Uani 1 1 d . . . . .
H11 H 0.277400 0.202963 0.463279 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5913(5) 0.18117(14) 0.42085(9) 0.0320(4) Uani 1 1 d . . . . .
C13 C 0.7674(5) 0.22544(15) 0.38884(10) 0.0344(5) Uani 1 1 d . . . . .
H13 H 0.902614 0.190359 0.376007 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7461(4) 0.32105(15) 0.37554(9) 0.0312(4) Uani 1 1 d . . . . .
H14 H 0.867745 0.350993 0.353666 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3084(4) 0.50202(14) 0.34274(8) 0.0274(4) Uani 1 1 d . . . . .
H15A H 0.277058 0.571086 0.345620 0.033 Uiso 1 1 calc R U . . .
H15B H 0.169089 0.468602 0.359533 0.033 Uiso 1 1 calc R U . . .
C16 C 0.3251(4) 0.47535(15) 0.27976(9) 0.0298(4) Uani 1 1 d . . . . .
H16 H 0.465299 0.508959 0.262475 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3539(4) 0.36832(16) 0.27044(9) 0.0310(4) Uani 1 1 d . . . . .
C18 C 0.6186(6) 0.24818(18) 0.24029(12) 0.0474(6) Uani 1 1 d . . . . .
H18A H 0.517405 0.223119 0.209719 0.071 Uiso 1 1 calc R U . . .
H18B H 0.585121 0.213535 0.275515 0.071 Uiso 1 1 calc R U . . .
H18C H 0.787939 0.240272 0.230124 0.071 Uiso 1 1 calc R U . . .
C19 C 0.0958(4) 0.50743(15) 0.24977(8) 0.0291(4) Uani 1 1 d . . . . .
C20 C -0.1059(5) 0.5108(2) 0.16188(10) 0.0420(6) Uani 1 1 d . . . . .
H20A H -0.070210 0.506137 0.121230 0.063 Uiso 1 1 calc R U . . .
H20B H -0.156578 0.575784 0.170906 0.063 Uiso 1 1 calc R U . . .
H20C H -0.234992 0.466418 0.171577 0.063 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 N1 1.230(2) . ?
O2 N1 1.217(2) . ?
O3 H3 0.93(4) . ?
O3 C12 1.371(2) . ?
O4 C17 1.199(3) . ?
O5 C17 1.326(3) . ?
O5 C18 1.450(3) . ?
O6 C19 1.201(3) . ?
O7 C19 1.337(2) . ?
O7 C20 1.450(3) . ?
N1 C7 1.515(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C6 C7 1.518(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.542(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.524(3) . ?
C8 C15 1.532(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.533(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.531(3) . ?
C16 C19 1.528(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C12 O3 H3 103(2) . . ?
C17 O5 C18 115.9(2) . . ?
C19 O7 C20 115.34(19) . . ?
O1 N1 C7 117.32(18) . . ?
O2 N1 O1 123.07(18) . . ?
O2 N1 C7 119.60(16) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 122.14(19) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 118.2(2) . . ?
N1 C7 C6 107.95(16) . . ?
N1 C7 H7 108.5 . . ?
N1 C7 C8 108.00(16) . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 115.17(17) . . ?
C8 C7 H7 108.5 . . ?
C7 C8 H8 108.4 . . ?
C9 C8 C7 110.80(16) . . ?
C9 C8 H8 108.4 . . ?
C9 C8 C15 113.15(17) . . ?
C15 C8 C7 107.69(16) . . ?
C15 C8 H8 108.4 . . ?
C10 C9 C8 122.12(19) . . ?
C14 C9 C8 119.63(19) . . ?
C14 C9 C10 118.25(19) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.3 . . ?
O3 C12 C11 122.8(2) . . ?
O3 C12 C13 117.1(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C8 C15 H15A 108.5 . . ?
C8 C15 H15B 108.5 . . ?
C8 C15 C16 115.02(18) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C15 C16 H16 109.0 . . ?
C17 C16 C15 112.72(17) . . ?
C17 C16 H16 109.0 . . ?
C19 C16 C15 108.92(17) . . ?
C19 C16 H16 109.0 . . ?
C19 C16 C17 108.20(17) . . ?
O4 C17 O5 125.5(2) . . ?
O4 C17 C16 123.4(2) . . ?
O5 C17 C16 111.12(19) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O7 124.3(2) . . ?
O6 C19 C16 125.25(19) . . ?
O7 C19 C16 110.45(19) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O3 H3 O1 0.93(4) 2.02(4) 2.929(3) 166(3) 4_456 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
O1 N1 C7 C6 110.09(19) . . . . ?
O1 N1 C7 C8 -124.79(19) . . . . ?
O2 N1 C7 C6 -69.3(2) . . . . ?
O2 N1 C7 C8 55.8(2) . . . . ?
O3 C12 C13 C14 179.2(2) . . . . ?
N1 C7 C8 C9 48.5(2) . . . . ?
N1 C7 C8 C15 172.76(16) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C6 C7 N1 67.4(2) . . . . ?
C1 C6 C7 C8 -53.3(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 N1 -113.3(2) . . . . ?
C5 C6 C7 C8 125.9(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C7 C8 C9 169.23(18) . . . . ?
C6 C7 C8 C15 -66.5(2) . . . . ?
C7 C8 C9 C10 59.4(3) . . . . ?
C7 C8 C9 C14 -119.5(2) . . . . ?
C7 C8 C15 C16 159.19(17) . . . . ?
C8 C9 C10 C11 180.0(2) . . . . ?
C8 C9 C14 C13 -179.7(2) . . . . ?
C8 C15 C16 C17 62.7(2) . . . . ?
C8 C15 C16 C19 -177.16(16) . . . . ?
C9 C8 C15 C16 -78.0(2) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C9 C14 C13 1.4(3) . . . . ?
C10 C11 C12 O3 -178.9(2) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C15 C8 C9 C10 -61.6(3) . . . . ?
C15 C8 C9 C14 119.5(2) . . . . ?
C15 C16 C17 O4 66.7(3) . . . . ?
C15 C16 C17 O5 -113.6(2) . . . . ?
C15 C16 C19 O6 -0.8(3) . . . . ?
C15 C16 C19 O7 178.35(17) . . . . ?
C17 C16 C19 O6 122.1(2) . . . . ?
C17 C16 C19 O7 -58.8(2) . . . . ?
C18 O5 C17 O4 -3.1(3) . . . . ?
C18 O5 C17 C16 177.21(19) . . . . ?
C19 C16 C17 O4 -53.8(3) . . . . ?
C19 C16 C17 O5 125.85(19) . . . . ?
C20 O7 C19 O6 -3.6(3) . . . . ?
C20 O7 C19 C16 177.26(18) . . . . ?

_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 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.822
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5(2)
2 0.5(2)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JA1545
_database_code_depnum_ccdc_archive 'CCDC 2373468'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-07-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 O5'
_chemical_formula_sum            'C19 H26 O5'
_chemical_formula_weight         334.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H26O5
_chemical_oxdiff_usercomment     JA1545
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.97868(11)
_cell_length_b                   13.67544(13)
_cell_length_c                   12.12795(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.4557(9)
_cell_angle_gamma                90
_cell_volume                     1796.13(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14369
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.6550
_cell_measurement_theta_min      4.8760
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -1 0.0488
-2 -1 1 0.0562
-1 1 2 0.0562
-1 -2 1 0.0650
0 -2 -8 0.0305
2 6 -6 0.0551
-2 -6 6 0.0629
0 0 8 0.0559
3 7 3 0.0381
-3 -7 -3 0.0428
0 4 -7 0.0493
-3 -3 -6 0.0406
3 -3 6 0.0764
-5 -6 0 0.0443
3 -6 4 0.0939
6 -5 0 0.0990
-4 7 0 0.0407
0 6 6 0.0367
0 -6 -6 0.0492
5 6 -2 0.0442
5 -5 3 0.0901

_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.081
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0000 1.0000 -1.0000 0.1443 -0.1577 0.2291
-2.0000 -1.0000 1.0000 -0.1443 0.1577 -0.2291
-1.0000 1.0000 2.0000 -0.2951 0.0069 -0.0098
-1.0000 -2.0000 1.0000 -0.0550 0.0081 -0.2801
0.1364 -1.9870 -7.5909 0.8776 0.4779 0.0384
2.4436 5.8634 -5.6298 0.4175 0.2303 0.8790
-2.4194 -5.7559 5.7298 -0.4316 -0.2379 -0.8701
0.0018 0.0573 7.7628 -0.8010 -0.5526 -0.2302
2.9136 6.7640 3.3782 -0.5298 -0.4506 0.7186
-2.9171 -6.7801 -3.3531 0.5278 0.4489 -0.7211
-0.0824 3.5339 -7.1046 0.5655 0.5998 0.5661
-2.6565 -3.1962 -6.1587 0.6638 0.6999 -0.2638
2.6427 -2.8292 6.2893 -0.4022 -0.8482 -0.3447
-5.3449 -5.6417 -0.4666 0.0729 0.5759 -0.8143
3.1698 -6.3775 3.5720 0.0625 -0.8037 -0.5917
5.5022 -5.4386 0.3000 0.4578 -0.8427 -0.2833
-3.7950 7.4133 -0.3770 -0.4658 0.6789 0.5676
-0.0496 6.0534 5.6922 -0.8645 -0.2584 0.4311
0.0819 -5.9925 -5.7468 0.8687 0.2596 -0.4218
5.4388 5.5481 -2.2752 0.2175 -0.3943 0.8929
5.0000 -5.0000 3.0000 0.1382 -0.9617 -0.3462

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21043
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.940
_diffrn_reflns_theta_min         4.912
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -26.50   0.55    0.35    --  -44.88 -36.00-105.00  170
  2  ω     27.00 120.50   0.55    0.35    --   44.88  36.00  51.00  170
  3  ω    -30.00  41.50   0.55    0.35    --   44.88 -36.00-105.00  130
  4  ω   -169.00 -75.50   0.55    1.40    --  -93.75 -36.00-105.00  170
  5  ω     97.00 162.45   0.55    1.40    --  115.25  36.00  51.00  119
  6  ω     97.00 162.45   0.55    1.40    --  115.25  36.00  51.00  119
  7  ω    -40.00  30.95   0.55    0.35    --  -44.88  36.00  51.00  129
  8  ω    -26.00  30.10   0.55    0.35    --  -44.88  19.00-180.00  102
  9  ω    -84.00 -19.65   0.55    0.35    --  -44.88 125.00-180.00  117
 10  ω    -16.00  26.35   0.55    0.35    --   44.88 -19.00 150.00   77
 11  ω    -46.00 -19.60   0.55    1.40    --  -93.75  45.00 -90.00   48
 12  ω     43.00  67.75   0.55    1.40    --  115.25 -61.00 -60.00   45
 13  ω     46.00  96.60   0.55    1.40    --  115.25-125.00 -30.00   92
 14  ω     50.00  85.75   0.55    1.40    --  115.25-125.00 120.00   65
 15  ω     43.00  67.75   0.55    1.40    --  115.25 -61.00 120.00   45
 16  ω    103.00 129.40   0.55    1.40    --  115.25  61.00  60.00   48
 17  ω     45.00  89.00   0.55    1.40    --  115.25 -77.00-180.00   80
 18  ω     43.00  84.25   0.55    1.40    --  115.25 -82.00-105.99   75
 19  ω    101.00 143.35   0.55    1.40    --  115.25 -82.00-105.99   77
 20  ω     75.00  99.75   0.55    1.40    --  115.25-125.00  60.00   45
 21  ω     43.00  69.95   0.55    1.40    --  115.25 -61.00 -30.00   49
 22  ω     63.00  88.85   0.55    1.40    --  115.25 -95.00-180.00   47
 23  ω     44.00  70.95   0.55    1.40    --  115.25 -61.00 -90.00   49
 24  ω    138.00 175.40   0.55    1.40    --  115.25  45.00-180.00   68
 25  ω     96.00 133.40   0.55    1.40    --  115.25  77.00-120.00   68
 26  ω    146.00 172.40   0.55    1.40    --  115.25  61.00  60.00   48
 27  ω     90.00 133.45   0.55    1.40    --  115.25  77.00 120.00   79
 28  ω    137.00 166.15   0.55    1.40    --  115.25  77.00 120.00   53
 29  ω     65.00 100.20   0.55    1.40    --  115.25 -77.00 120.00   64
 30  ω     80.00 104.75   0.55    1.40    --  115.25-125.00 -60.00   45
 31  ω     65.00  90.85   0.55    1.40    --  115.25 -87.00 -60.12   47
 32  ω    103.00 143.15   0.55    1.40    --  115.25 -87.00 -60.12   73
 33  ω     47.00  72.85   0.55    1.40    --  115.25 -95.00 150.00   47
 34  ω     43.00  71.60   0.55    1.40    --  115.25 -77.00 150.00   52
 35  ω     77.00 101.75   0.55    1.40    --  115.25 -77.00 150.00   45
 36  ω    113.00 139.40   0.55    1.40    --  115.25  61.00   0.00   48
 37  ω     43.00  68.85   0.55    1.40    --  115.25 -61.00-180.00   47
 38  ω     46.00  72.95   0.55    1.40    --  115.25 -77.00 -30.00   49
 39  ω    142.00 173.35   0.55    1.40    --  115.25  61.00   0.00   57
 40  ω     53.00 107.45   0.55    1.40    --  115.25-125.00 150.00   99
 41  ω    104.00 130.40   0.55    1.40    --  115.25  45.00-180.00   48
 42  ω    143.00 169.40   0.55    1.40    --  115.25  30.00-150.00   48
 43  ω    115.00 141.40   0.55    1.40    --  115.25  61.00 -60.00   48
 44  ω    130.00 175.10   0.55    1.40    --  115.25  15.00-180.00   82
 45  ω     44.00  69.85   0.55    1.40    --  115.25 -61.00-120.00   47
 46  ω     61.00  97.85   0.55    1.40    --  115.25 -95.00-120.00   67
 47  ω     45.00  70.85   0.55    1.40    --  115.25-125.00  30.00   47
 48  ω     89.00 129.15   0.55    1.40    --  115.25  77.00-180.00   73
 49  ω    118.00 144.95   0.55    1.40    --  115.25 -87.00  47.54   49
 50  ω     47.00  72.85   0.55    1.40    --  115.25 -77.00 -60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0436118000
_diffrn_orient_matrix_UB_12      -0.0457355000
_diffrn_orient_matrix_UB_13      -0.1028556000
_diffrn_orient_matrix_UB_21      -0.1261734000
_diffrn_orient_matrix_UB_22      0.0233596000
_diffrn_orient_matrix_UB_23      -0.0713357000
_diffrn_orient_matrix_UB_31      0.0492203000
_diffrn_orient_matrix_UB_32      0.1002142000
_diffrn_orient_matrix_UB_33      -0.0304034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3668
_reflns_number_total             3903
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_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         0.286
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00113(19)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.069
_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)+(0.0312P)²+0.6807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0817
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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 0.51240(7) 0.14009(5) 0.78836(6) 0.02130(17) Uani 1 1 d . . . . .
H1 H 0.4379(15) 0.1186(11) 0.7846(13) 0.032 Uiso 1 1 d . U . . .
O2 O 0.58843(7) 0.74074(5) 0.75180(6) 0.02060(16) Uani 1 1 d . . . . .
O3 O 0.41226(6) 0.74139(5) 0.62402(6) 0.01750(16) Uani 1 1 d . . . . .
O4 O 0.22367(6) 0.56715(5) 0.72115(6) 0.01875(16) Uani 1 1 d . . . . .
O5 O 0.35140(6) 0.53588(5) 0.59723(5) 0.01629(15) Uani 1 1 d . . . . .
C1 C 0.51161(9) 0.23924(7) 0.80349(8) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.62118(9) 0.28950(8) 0.79987(8) 0.0194(2) Uani 1 1 d . . . . .
H2 H 0.693324 0.254873 0.789122 0.023 Uiso 1 1 calc R U . . .
C3 C 0.62447(9) 0.39052(8) 0.81205(8) 0.0190(2) Uani 1 1 d . . . . .
H3 H 0.699589 0.424255 0.809471 0.023 Uiso 1 1 calc R U . . .
C4 C 0.52009(9) 0.44381(7) 0.82800(8) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.41249(9) 0.39164(8) 0.83489(8) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.341055 0.425921 0.848196 0.023 Uiso 1 1 calc R U . . .
C6 C 0.40741(9) 0.29059(8) 0.82274(8) 0.0191(2) Uani 1 1 d . . . . .
H6 H 0.333037 0.256552 0.827540 0.023 Uiso 1 1 calc R U . . .
C7 C 0.52884(9) 0.55255(7) 0.83432(8) 0.0185(2) Uani 1 1 d . . . . .
H7 H 0.615542 0.577544 0.843993 0.022 Uiso 1 1 calc R U . . .
C8 C 0.44346(10) 0.61700(8) 0.88615(8) 0.0209(2) Uani 1 1 d . . . . .
H8A H 0.479537 0.674881 0.928464 0.025 Uiso 1 1 calc R U . . .
H8B H 0.375387 0.585175 0.917017 0.025 Uiso 1 1 calc R U . . .
C9 C 0.43510(9) 0.61866(7) 0.76011(8) 0.0158(2) Uani 1 1 d . . . . .
C10 C 0.48935(9) 0.70642(7) 0.71214(8) 0.01596(19) Uani 1 1 d . . . . .
C11 C 0.44706(9) 0.82735(7) 0.56074(8) 0.0173(2) Uani 1 1 d . . . . .
C12 C 0.55789(10) 0.80148(8) 0.50588(9) 0.0219(2) Uani 1 1 d . . . . .
H12A H 0.577286 0.856540 0.460037 0.033 Uiso 1 1 calc R U . . .
H12B H 0.538650 0.743649 0.458497 0.033 Uiso 1 1 calc R U . . .
H12C H 0.629132 0.787573 0.563774 0.033 Uiso 1 1 calc R U . . .
C13 C 0.46964(11) 0.91565(7) 0.63785(9) 0.0228(2) Uani 1 1 d . . . . .
H13A H 0.477442 0.974483 0.593390 0.034 Uiso 1 1 calc R U . . .
H13B H 0.545896 0.905891 0.691283 0.034 Uiso 1 1 calc R U . . .
H13C H 0.400129 0.923430 0.678494 0.034 Uiso 1 1 calc R U . . .
C14 C 0.33305(10) 0.84186(8) 0.47243(9) 0.0227(2) Uani 1 1 d . . . . .
H14A H 0.347410 0.895750 0.422874 0.034 Uiso 1 1 calc R U . . .
H14B H 0.262141 0.857424 0.508919 0.034 Uiso 1 1 calc R U . . .
H14C H 0.316137 0.781749 0.428599 0.034 Uiso 1 1 calc R U . . .
C15 C 0.32368(9) 0.57186(7) 0.69111(8) 0.01454(19) Uani 1 1 d . . . . .
C16 C 0.25595(9) 0.48879(7) 0.51163(8) 0.0175(2) Uani 1 1 d . . . . .
C17 C 0.33214(10) 0.46041(8) 0.42283(9) 0.0236(2) Uani 1 1 d . . . . .
H17A H 0.278887 0.428388 0.360461 0.035 Uiso 1 1 calc R U . . .
H17B H 0.397856 0.415343 0.455033 0.035 Uiso 1 1 calc R U . . .
H17C H 0.368835 0.519191 0.395687 0.035 Uiso 1 1 calc R U . . .
C18 C 0.20388(10) 0.39848(8) 0.56075(9) 0.0213(2) Uani 1 1 d . . . . .
H18A H 0.153519 0.361275 0.500848 0.032 Uiso 1 1 calc R U . . .
H18B H 0.152657 0.418562 0.615779 0.032 Uiso 1 1 calc R U . . .
H18C H 0.271968 0.357469 0.597246 0.032 Uiso 1 1 calc R U . . .
C19 C 0.15732(10) 0.56304(8) 0.46659(9) 0.0237(2) Uani 1 1 d . . . . .
H19A H 0.101581 0.534641 0.403284 0.036 Uiso 1 1 calc R U . . .
H19B H 0.196572 0.621628 0.441834 0.036 Uiso 1 1 calc R U . . .
H19C H 0.110176 0.580742 0.525603 0.036 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 H1 0.863(16) . ?
O1 C1 1.3686(12) . ?
O2 C10 1.2096(12) . ?
O3 C10 1.3379(12) . ?
O3 C11 1.4877(11) . ?
O4 C15 1.2139(12) . ?
O5 C15 1.3210(12) . ?
O5 C16 1.4944(11) . ?
C1 C2 1.3923(14) . ?
C1 C6 1.3942(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3892(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3981(14) . ?
C4 C5 1.3943(14) . ?
C4 C7 1.4913(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.3898(15) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.4979(15) . ?
C7 C9 1.5434(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5164(13) . ?
C9 C10 1.4991(13) . ?
C9 C15 1.5067(13) . ?
C11 C12 1.5213(14) . ?
C11 C13 1.5225(14) . ?
C11 C14 1.5207(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.5186(14) . ?
C16 C18 1.5228(14) . ?
C16 C19 1.5190(14) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 H1 108.5(10) . . ?
C10 O3 C11 120.81(8) . . ?
C15 O5 C16 121.65(8) . . ?
O1 C1 C2 117.40(9) . . ?
O1 C1 C6 123.02(9) . . ?
C2 C1 C6 119.57(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.67(9) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.70(9) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C7 118.66(9) . . ?
C5 C4 C3 117.60(9) . . ?
C5 C4 C7 123.73(9) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.47(9) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.92(9) . . ?
C5 C6 H6 120.0 . . ?
C4 C7 H7 113.5 . . ?
C4 C7 C8 124.66(9) . . ?
C4 C7 C9 121.53(8) . . ?
C8 C7 H7 113.5 . . ?
C8 C7 C9 59.79(6) . . ?
C9 C7 H7 113.5 . . ?
C7 C8 H8A 117.6 . . ?
C7 C8 H8B 117.6 . . ?
C7 C8 C9 61.59(6) . . ?
H8A C8 H8B 114.7 . . ?
C9 C8 H8A 117.6 . . ?
C9 C8 H8B 117.6 . . ?
C8 C9 C7 58.62(6) . . ?
C10 C9 C7 115.21(8) . . ?
C10 C9 C8 116.18(8) . . ?
C10 C9 C15 117.55(8) . . ?
C15 C9 C7 118.54(8) . . ?
C15 C9 C8 117.56(8) . . ?
O2 C10 O3 126.05(9) . . ?
O2 C10 C9 123.02(9) . . ?
O3 C10 C9 110.90(8) . . ?
O3 C11 C12 109.48(8) . . ?
O3 C11 C13 109.85(8) . . ?
O3 C11 C14 102.41(8) . . ?
C12 C11 C13 113.07(9) . . ?
C14 C11 C12 110.32(8) . . ?
C14 C11 C13 111.18(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O5 125.92(9) . . ?
O4 C15 C9 123.21(9) . . ?
O5 C15 C9 110.85(8) . . ?
O5 C16 C17 101.40(8) . . ?
O5 C16 C18 110.07(8) . . ?
O5 C16 C19 109.81(8) . . ?
C17 C16 C18 110.86(9) . . ?
C17 C16 C19 111.04(9) . . ?
C19 C16 C18 113.06(9) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 H1 O4 0.863(16) 1.899(16) 2.7618(10) 177.9(15) 2_546 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
O1 C1 C2 C3 178.45(9) . . . . ?
O1 C1 C6 C5 -178.56(9) . . . . ?
C1 C2 C3 C4 0.00(15) . . . . ?
C2 C1 C6 C5 1.87(15) . . . . ?
C2 C3 C4 C5 1.99(14) . . . . ?
C2 C3 C4 C7 -176.77(9) . . . . ?
C3 C4 C5 C6 -2.07(14) . . . . ?
C3 C4 C7 C8 -159.40(9) . . . . ?
C3 C4 C7 C9 127.66(10) . . . . ?
C4 C5 C6 C1 0.18(15) . . . . ?
C4 C7 C8 C9 -109.46(10) . . . . ?
C4 C7 C9 C8 114.51(11) . . . . ?
C4 C7 C9 C10 -138.99(9) . . . . ?
C4 C7 C9 C15 7.95(14) . . . . ?
C5 C4 C7 C8 21.92(15) . . . . ?
C5 C4 C7 C9 -51.02(14) . . . . ?
C6 C1 C2 C3 -1.96(15) . . . . ?
C7 C4 C5 C6 176.62(9) . . . . ?
C7 C8 C9 C10 -104.84(9) . . . . ?
C7 C8 C9 C15 108.24(9) . . . . ?
C7 C9 C10 O2 -21.33(14) . . . . ?
C7 C9 C10 O3 160.54(8) . . . . ?
C7 C9 C15 O4 96.36(11) . . . . ?
C7 C9 C15 O5 -82.18(10) . . . . ?
C8 C7 C9 C10 106.50(9) . . . . ?
C8 C7 C9 C15 -106.57(10) . . . . ?
C8 C9 C10 O2 44.47(14) . . . . ?
C8 C9 C10 O3 -133.66(9) . . . . ?
C8 C9 C15 O4 29.00(14) . . . . ?
C8 C9 C15 O5 -149.55(9) . . . . ?
C10 O3 C11 C12 64.31(11) . . . . ?
C10 O3 C11 C13 -60.42(11) . . . . ?
C10 O3 C11 C14 -178.63(8) . . . . ?
C10 C9 C15 O4 -117.47(10) . . . . ?
C10 C9 C15 O5 63.98(11) . . . . ?
C11 O3 C10 O2 3.23(15) . . . . ?
C11 O3 C10 C9 -178.71(8) . . . . ?
C15 O5 C16 C17 -179.88(8) . . . . ?
C15 O5 C16 C18 -62.47(11) . . . . ?
C15 O5 C16 C19 62.61(11) . . . . ?
C15 C9 C10 O2 -168.61(9) . . . . ?
C15 C9 C10 O3 13.27(12) . . . . ?
C16 O5 C15 O4 3.85(14) . . . . ?
C16 O5 C15 C9 -177.65(8) . . . . ?

_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.900
####################################################################### 
# 
# 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_ja1515
_database_code_depnum_ccdc_archive 'CCDC 2382845'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-09-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N O9'
_chemical_formula_sum            'C20 H27 N O9'
_chemical_formula_weight         425.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H27NO9
_chemical_oxdiff_usercomment     JA1515
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.97285(13)
_cell_length_b                   10.4324(2)
_cell_length_c                   10.6019(3)
_cell_angle_alpha                85.062(2)
_cell_angle_beta                 67.0587(17)
_cell_angle_gamma                89.0992(15)
_cell_volume                     1011.82(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19864
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5500
_cell_measurement_theta_min      4.2540
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.665
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.0614
1 0 1 0.0939
0 -1 0 0.0330
0 1 0 0.0432
-2 -1 2 0.1633
-2 1 2 0.1709
2 1 2 0.0863
-1 2 2 0.1542
2 -1 -1 0.2779
-1 -1 -1 0.0402
-2 1 1 0.1592
1 1 1 0.0736
1 2 1 0.0577
-2 -6 -2 0.0289
-4 4 -4 0.0619
4 -4 4 0.0852
0 0 6 0.1697
0 0 -6 0.2545
-5 -3 0 0.1333
5 3 0 0.2143
-2 -5 3 0.1252

_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.076
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 0.0000 -1.0000 0.1565 0.0191 0.0875
1.0000 -0.0000 1.0000 -0.1565 -0.0191 -0.0875
-0.0000 -1.0000 0.0000 -0.0184 0.1461 -0.0168
0.0000 1.0000 -0.0000 0.0184 -0.1461 0.0168
-2.0000 -1.0000 2.0000 -0.2576 0.2063 0.4680
-2.0000 1.0000 2.0000 -0.2209 -0.0860 0.5015
2.0000 1.0000 2.0000 -0.2946 -0.1843 -0.1582
-1.0000 2.0000 2.0000 -0.2210 -0.2567 0.3534
2.0000 -1.0000 -1.0000 0.0828 0.0915 -0.4241
-1.0000 -1.0000 -1.0000 0.1381 0.1652 0.0707
-2.0000 1.0000 1.0000 -0.0828 -0.0915 0.4241
1.0000 1.0000 1.0000 -0.1381 -0.1652 -0.0707
1.0000 2.0000 1.0000 -0.1198 -0.3114 -0.0539
-2.3201 -6.3107 -2.2004 0.2307 0.9672 0.1063
-4.0527 4.3014 -4.0901 0.7184 -0.5516 0.4239
4.0527 -4.3014 4.0901 -0.7184 0.5516 -0.4239
-0.0112 0.1005 6.3164 -0.8700 0.0204 0.4927
0.0112 -0.1005 -6.3164 0.8700 -0.0204 -0.4927
-5.4583 -2.7481 -0.1588 0.0721 0.5349 0.8418
5.4618 2.7362 0.1552 -0.0719 -0.5332 -0.8429
-2.3246 -4.6809 2.6570 -0.4099 0.7559 0.5106

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29410
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.218
_diffrn_reflns_theta_min         4.254
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -10.00   0.50    0.15    --  -45.04 121.00 138.00  148
  2  ω   -117.00 -53.00   0.50    0.15    --  -45.04-154.00-102.00  128
  3  ω    -84.00 -10.00   0.50    0.15    --  -45.04 121.00 138.00  148
  4  ω     49.00 113.00   0.50    0.15    --   45.04-154.00-102.00  128
  5  ω     32.00  92.00   0.50    0.15    --   45.04-121.00  55.00  120
  6  ω    -84.00 -23.00   0.50    0.45    --  -93.75 121.00 138.00  122
  7  ω   -164.00 -76.00   0.50    0.45    --  -93.75-121.00  55.00  176
  8  ω   -106.00 -28.00   0.50    0.45    --  -93.75 154.00 -63.00  156
  9  ω     49.00 132.00   0.50    0.45    --  115.25-154.00-102.00  166
 10  ω     75.00 163.00   0.50    0.45    --  115.25 154.00 -63.00  176
 11  ω     45.00 110.00   0.50    0.45    --  115.25-121.00  55.00  130
 12  ω     98.00 178.00   0.50    0.45    --  115.25 121.00 138.00  160
 13  ω    -27.00  33.00   0.50    0.15    --  -45.04  19.00  60.00  120
 14  ω   -106.00 -28.00   0.50    0.15    --  -45.04 154.00 -63.00  156
 15  ω    -71.00  28.00   0.50    0.15    --  -45.04  77.00  30.00  198
 16  ω    -27.00  33.00   0.50    0.15    --  -45.04  19.00 150.00  120
 17  ω   -117.00 -27.00   0.50    0.15    --  -45.04 -57.00 -90.00  180
 18  ω    -71.00  28.00   0.50    0.15    --  -45.04  77.00  30.00  198
 19  ω    -32.00  27.00   0.50    0.15    --   45.04 -19.00 -90.00  118
 20  ω    -51.00 -20.00   0.50    0.45    --  -93.75  45.00-120.00   62
 21  ω   -167.00 -71.00   0.50    0.45    --  -93.75 -70.00 129.06  192
 22  ω     45.00 111.00   0.50    0.45    --  115.25-125.00   0.00  132
 23  ω     43.00 105.00   0.50    0.45    --  115.25 -95.00 -90.00  124
 24  ω     43.00 105.00   0.50    0.45    --  115.25 -95.00 -90.00  124
 25  ω     90.00 178.00   0.50    0.45    --  115.25  15.00 -60.00  176
 26  ω     96.00 178.00   0.50    0.45    --  115.25  61.00-180.00  164
 27  ω     97.00 178.00   0.50    0.45    --  115.25  45.00 120.00  162
 28  ω     43.00  71.00   0.50    0.45    --  115.25 -61.00 -90.00   56
 29  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00  30.00  124
 30  ω     45.00 111.00   0.50    0.45    --  115.25-125.00  30.00  132
 31  ω     45.00 111.00   0.50    0.45    --  115.25-125.00  90.00  132
 32  ω     96.00 178.00   0.50    0.45    --  115.25  61.00 150.00  164
 33  ω     45.00 111.00   0.50    0.45    --  115.25-125.00  30.00  132
 34  ω     45.00 111.00   0.50    0.45    --  115.25-125.00 120.00  132
 35  ω     43.00 105.00   0.50    0.45    --  115.25 -95.00-120.00  124
 36  ω     43.00 105.00   0.50    0.45    --  115.25 -95.00-120.00  124
 37  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00 120.00  124
 38  ω     90.00 178.00   0.50    0.45    --  115.25  15.00 -30.00  176
 39  ω     43.00 105.00   0.50    0.45    --  115.25 -95.00 -60.00  124
 40  ω     90.00 178.00   0.50    0.45    --  115.25  15.00  90.00  176
 41  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00 -30.00  124
 42  ω     89.00 178.00   0.50    0.45    --  115.25  77.00  90.00  178
 43  ω     96.00 178.00   0.50    0.45    --  115.25  61.00-150.00  164
 44  ω     90.00 178.00   0.50    0.45    --  115.25  15.00-120.00  176
 45  ω     95.00 178.00   0.50    0.45    --  115.25 125.00 -90.00  166
 46  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00  90.00  124
 47  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00  60.00  124
 48  ω     45.00 111.00   0.50    0.45    --  115.25-125.00-180.00  132
 49  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00-120.00  124
 50  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00   0.00  124
 51  ω     43.00 105.00   0.50    0.45    --  115.25 -77.00 150.00  124
 52  ω     97.00 178.00   0.50    0.45    --  115.25  30.00-120.00  162
 53  ω     96.00 178.00   0.50    0.45    --  115.25  61.00 -90.00  164
 54  ω     96.00 178.00   0.50    0.45    --  115.25  61.00 -90.00  164
 55  ω    131.00 165.00   0.50    0.45    --  115.25 125.00  60.00   68
 56  ω     43.00  69.00   0.50    0.45    --  115.25 -61.00-180.00   52
 57  ω     43.00  68.00   0.50    0.45    --  115.25 -61.00   0.00   50
 58  ω     44.00  70.00   0.50    0.45    --  115.25 -61.00 120.00   52
 59  ω     43.00  70.00   0.50    0.45    --  115.25 -61.00 150.00   54
 60  ω     75.00 101.00   0.50    0.45    --  115.25 -95.00-150.00   52
 61  ω    116.00 142.00   0.50    0.45    --  115.25 -88.00 -38.52   52
 62  ω     96.00 152.00   0.50    0.45    --  115.25 125.00 120.00  112
 63  ω     44.00  69.00   0.50    0.45    --  115.25 -77.00 -90.00   50
 64  ω     74.00 103.00   0.50    0.45    --  115.25 -95.00-180.00   58
 65  ω     65.00 102.00   0.50    0.45    --  115.25 -95.00   0.00   74
 66  ω     80.00 105.00   0.50    0.45    --  115.25 -95.00  30.00   50
 67  ω     80.00 105.00   0.50    0.45    --  115.25 -95.00  90.00   50
 68  ω     73.00  99.00   0.50    0.45    --  115.25 -95.00 150.00   52
 69  ω     68.00 111.00   0.50    0.45    --  115.25-125.00 -90.00   86
 70  ω    129.00 177.00   0.50    0.45    --  115.25  45.00-120.00   96
 71  ω    106.00 170.00   0.50    0.45    --  115.25  41.00 110.74  128
 72  ω    100.00 158.00   0.50    0.45    --  115.25 125.00   0.00  116
 73  ω     99.00 171.00   0.50    0.45    --  115.25  77.00-180.00  144
 74  ω     86.00 112.00   0.50    0.45    --  115.25 -83.00  58.26   52
 75  ω     56.00  82.00   0.50    0.45    --  115.25 -88.00 -38.52   52
 76  ω    107.00 133.00   0.50    0.45    --  115.25 -88.00-104.36   52
 77  ω    129.00 155.00   0.50    0.45    --  115.25  61.00-180.00   52
 78  ω     43.00  68.00   0.50    0.45    --  115.25 -61.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0184422000
_diffrn_orient_matrix_UB_12      0.0183552000
_diffrn_orient_matrix_UB_13      -0.1380578000
_diffrn_orient_matrix_UB_21      -0.0245730000
_diffrn_orient_matrix_UB_22      -0.1461478000
_diffrn_orient_matrix_UB_23      0.0055086000
_diffrn_orient_matrix_UB_31      -0.1649379000
_diffrn_orient_matrix_UB_32      0.0167901000
_diffrn_orient_matrix_UB_33      0.0774390000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4195
_reflns_number_total             4376
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0031(4)
_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   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.036
_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)+(0.0446P)²+0.4225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C3-C4A \\sim C3-C4B
 with sigma of 0.02
 O2-C4A \\sim O2-C4B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C4A) = Uanis(C4B)
4. Others
 Sof(H3C)=Sof(H3D)=Sof(C4B)=Sof(H4D)=Sof(H4C)=1-FVAR(1)
 Sof(H3A)=Sof(H3B)=Sof(C4A)=Sof(H4B)=Sof(H4A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3(H3C,H3D), C5(H5A,H5B), C6(H6A,H6B), C15(H15A,H15B), C4A(H4B,
 H4A), C4B(H4D,H4C)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.45932(8) 0.10168(7) 0.87272(8) 0.01841(17) Uani 1 1 d . . . . .
O2 O 0.35413(8) 0.03430(8) 0.73466(8) 0.01927(17) Uani 1 1 d D . . . .
O3 O -0.05085(8) 0.38798(8) 0.90485(8) 0.02312(19) Uani 1 1 d . . . . .
O4 O 0.08167(9) 0.37205(9) 0.69021(8) 0.02316(18) Uani 1 1 d . . . . .
H5 H 0.870(2) 0.6849(17) 0.7093(19) 0.035 Uiso 1 1 d . U . . .
O5 O 0.79804(9) 0.68940(9) 0.78227(9) 0.02475(19) Uani 1 1 d . . . . .
O6 O 0.04905(8) 0.67514(8) 0.54346(8) 0.01937(17) Uani 1 1 d . . . . .
O7 O 0.28450(8) 0.71093(8) 0.40793(8) 0.01885(17) Uani 1 1 d . . . . .
O8 O 0.04267(9) 0.90856(8) 0.78731(9) 0.02285(18) Uani 1 1 d . . . . .
O9 O 0.16192(9) 0.96423(7) 0.56083(8) 0.02012(18) Uani 1 1 d . . . . .
N1 N 0.06674(9) 0.39230(8) 0.80691(9) 0.01498(18) Uani 1 1 d . U . . .
C1 C 0.24817(13) -0.04311(11) 0.97624(12) 0.0207(2) Uani 1 1 d . . . . .
H1A H 0.158788 -0.068701 0.966502 0.031 Uiso 1 1 calc R U . . .
H1B H 0.224083 -0.017198 1.069147 0.031 Uiso 1 1 calc R U . . .
H1C H 0.314442 -0.115827 0.960616 0.031 Uiso 1 1 calc R U . . .
C2 C 0.32151(12) 0.06945(10) 0.87122(11) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.55976(12) 0.01285(11) 0.79026(12) 0.0216(2) Uani 1 1 d D . . . .
H3A H 0.571360 -0.062416 0.848470 0.026 Uiso 0.735(18) 1 calc R U P A 1
H3B H 0.656308 0.054773 0.738305 0.026 Uiso 0.735(18) 1 calc R U P A 1
H3C H 0.554248 -0.071725 0.842318 0.026 Uiso 0.265(18) 1 calc R U P A 2
H3D H 0.661134 0.046856 0.753428 0.026 Uiso 0.265(18) 1 calc R U P A 2
C5 C 0.22709(11) 0.18818(10) 0.89614(11) 0.0169(2) Uani 1 1 d . . . . .
H5A H 0.200294 0.208295 0.992435 0.020 Uiso 1 1 calc R U . . .
H5B H 0.136020 0.168252 0.884597 0.020 Uiso 1 1 calc R U . . .
C6 C 0.30010(11) 0.30706(10) 0.80053(11) 0.0160(2) Uani 1 1 d . . . . .
H6A H 0.325036 0.288244 0.704114 0.019 Uiso 1 1 calc R U . . .
H6B H 0.391870 0.326929 0.810817 0.019 Uiso 1 1 calc R U . . .
C7 C 0.20255(11) 0.42460(10) 0.83073(10) 0.0141(2) Uani 1 1 d . U . . .
H7 H 0.174514 0.442264 0.928901 0.017 Uiso 1 1 calc R U . . .
C8 C 0.27111(11) 0.54752(10) 0.73649(10) 0.0133(2) Uani 1 1 d . . . . .
H8 H 0.295637 0.527638 0.639462 0.016 Uiso 1 1 calc R U . . .
C9 C 0.41188(11) 0.58582(9) 0.74823(10) 0.0134(2) Uani 1 1 d . . . . .
C10 C 0.41581(11) 0.61131(10) 0.87437(11) 0.0160(2) Uani 1 1 d . . . . .
H10 H 0.328692 0.603972 0.954920 0.019 Uiso 1 1 calc R U . . .
C11 C 0.54508(12) 0.64716(11) 0.88353(11) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.545766 0.664515 0.969783 0.021 Uiso 1 1 calc R U . . .
C12 C 0.67376(11) 0.65766(10) 0.76618(11) 0.0165(2) Uani 1 1 d . . . . .
C13 C 0.67148(11) 0.63573(10) 0.63951(11) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.7595(17) 0.6421(14) 0.5586(16) 0.023(4) Uiso 1 1 d . . . . .
C14 C 0.54085(11) 0.60033(10) 0.63188(11) 0.0153(2) Uani 1 1 d . . . . .
H14 H 0.539839 0.585727 0.545035 0.018 Uiso 1 1 calc R U . . .
C15 C 0.16431(11) 0.66051(10) 0.76550(10) 0.0144(2) Uani 1 1 d . . . . .
H15A H 0.064413 0.627396 0.787979 0.017 Uiso 1 1 calc R U . . .
H15B H 0.164602 0.702380 0.845717 0.017 Uiso 1 1 calc R U . . .
C16 C 0.20769(11) 0.75913(10) 0.64054(10) 0.0138(2) Uani 1 1 d . . . . .
H16 H 0.314893 0.776996 0.605145 0.017 Uiso 1 1 calc R U . . .
C17 C 0.17073(11) 0.70969(9) 0.52667(10) 0.0141(2) Uani 1 1 d . . . . .
C18 C 0.25351(13) 0.67587(12) 0.29187(12) 0.0238(2) Uani 1 1 d . . . . .
H18A H 0.345160 0.668834 0.212251 0.036 Uiso 1 1 calc R U . . .
H18B H 0.193787 0.742144 0.269216 0.036 Uiso 1 1 calc R U . . .
H18C H 0.200728 0.593046 0.316034 0.036 Uiso 1 1 calc R U . . .
C19 C 0.12700(11) 0.88487(10) 0.67568(11) 0.0153(2) Uani 1 1 d . . . . .
C20 C 0.09636(16) 1.08921(11) 0.57942(15) 0.0298(3) Uani 1 1 d . . . . .
H20A H 0.119792 1.137005 0.489489 0.045 Uiso 1 1 calc R U . . .
H20B H 0.134322 1.136780 0.634602 0.045 Uiso 1 1 calc R U . . .
H20C H -0.009545 1.078707 0.626789 0.045 Uiso 1 1 calc R U . . .
C4A C 0.4933(4) -0.0279(6) 0.6930(5) 0.0213(7) Uani 0.735(18) 1 d D . P A 1
H4B H 0.555704 0.000765 0.596556 0.026 Uiso 0.735(18) 1 calc R U P A 1
H4A H 0.480467 -0.122586 0.701735 0.026 Uiso 0.735(18) 1 calc R U P A 1
C4B C 0.5011(11) 0.0042(13) 0.6722(11) 0.0213(7) Uani 0.265(18) 1 d D . P A 2
H4D H 0.553069 0.066656 0.592633 0.026 Uiso 0.265(18) 1 calc R U P A 2
H4C H 0.512594 -0.083495 0.640737 0.026 Uiso 0.265(18) 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
O1 C2 1.4264(13) . ?
O1 C3 1.4332(13) . ?
O2 C2 1.4342(13) . ?
O2 C4A 1.444(3) . ?
O2 C4B 1.396(10) . ?
O3 N1 1.2246(12) . ?
O4 N1 1.2239(12) . ?
O5 H5 0.828(19) . ?
O5 C12 1.3647(13) . ?
O6 C17 1.2118(13) . ?
O7 C17 1.3253(13) . ?
O7 C18 1.4563(13) . ?
O8 C19 1.1987(14) . ?
O9 C19 1.3395(13) . ?
O9 C20 1.4434(14) . ?
N1 C7 1.5190(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5233(15) . ?
C2 C5 1.5220(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C3 C4A 1.516(3) . ?
C3 C4B 1.584(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5272(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5296(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5441(14) . ?
C8 H8 1.0000 . ?
C8 C9 1.5194(13) . ?
C8 C15 1.5447(13) . ?
C9 C10 1.4011(14) . ?
C9 C14 1.3914(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3893(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3939(15) . ?
C12 C13 1.3904(15) . ?
C13 H13 0.957(16) . ?
C13 C14 1.3938(15) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5275(14) . ?
C16 H16 1.0000 . ?
C16 C17 1.5230(14) . ?
C16 C19 1.5246(14) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C4A H4B 0.9900 . ?
C4A H4A 0.9900 . ?
C4B H4D 0.9900 . ?
C4B H4C 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 105.54(8) . . ?
C2 O2 C4A 106.05(16) . . ?
C4B O2 C2 110.1(4) . . ?
C12 O5 H5 110.2(12) . . ?
C17 O7 C18 115.56(8) . . ?
C19 O9 C20 115.26(9) . . ?
O3 N1 C7 118.47(8) . . ?
O4 N1 O3 123.82(9) . . ?
O4 N1 C7 117.71(8) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 O2 104.76(8) . . ?
O1 C2 C1 111.30(9) . . ?
O1 C2 C5 108.99(8) . . ?
O2 C2 C1 110.25(9) . . ?
O2 C2 C5 109.51(8) . . ?
C5 C2 C1 111.78(9) . . ?
O1 C3 H3A 110.7 . . ?
O1 C3 H3B 110.7 . . ?
O1 C3 H3C 111.7 . . ?
O1 C3 H3D 111.7 . . ?
O1 C3 C4A 105.24(15) . . ?
O1 C3 C4B 100.6(4) . . ?
H3A C3 H3B 108.8 . . ?
H3C C3 H3D 109.4 . . ?
C4A C3 H3A 110.7 . . ?
C4A C3 H3B 110.7 . . ?
C4B C3 H3C 111.7 . . ?
C4B C3 H3D 111.7 . . ?
C2 C5 H5A 108.8 . . ?
C2 C5 H5B 108.8 . . ?
C2 C5 C6 114.01(9) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.27(8) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
N1 C7 C6 107.36(8) . . ?
N1 C7 H7 109.4 . . ?
N1 C7 C8 106.74(8) . . ?
C6 C7 H7 109.4 . . ?
C6 C7 C8 114.38(8) . . ?
C8 C7 H7 109.4 . . ?
C7 C8 H8 107.6 . . ?
C7 C8 C15 112.08(8) . . ?
C9 C8 C7 111.14(8) . . ?
C9 C8 H8 107.6 . . ?
C9 C8 C15 110.63(8) . . ?
C15 C8 H8 107.6 . . ?
C10 C9 C8 121.63(9) . . ?
C14 C9 C8 120.42(9) . . ?
C14 C9 C10 117.91(9) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.06(9) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.01(10) . . ?
C12 C11 H11 120.0 . . ?
O5 C12 C11 117.35(10) . . ?
O5 C12 C13 122.86(10) . . ?
C13 C12 C11 119.79(10) . . ?
C12 C13 H13 120.3(9) . . ?
C12 C13 C14 119.50(10) . . ?
C14 C13 H13 120.2(9) . . ?
C9 C14 C13 121.68(9) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C8 110.59(8) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16 109.1 . . ?
C17 C16 C15 111.13(8) . . ?
C17 C16 H16 109.1 . . ?
C17 C16 C19 106.47(8) . . ?
C19 C16 C15 111.82(8) . . ?
C19 C16 H16 109.1 . . ?
O6 C17 O7 124.03(10) . . ?
O6 C17 C16 123.00(9) . . ?
O7 C17 C16 112.95(9) . . ?
O7 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
O7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 O9 124.99(10) . . ?
O8 C19 C16 125.82(10) . . ?
O9 C19 C16 109.17(9) . . ?
O9 C20 H20A 109.5 . . ?
O9 C20 H20B 109.5 . . ?
O9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C4A C3 104.87(19) . . ?
O2 C4A H4B 110.8 . . ?
O2 C4A H4A 110.8 . . ?
C3 C4A H4B 110.8 . . ?
C3 C4A H4A 110.8 . . ?
H4B C4A H4A 108.8 . . ?
O2 C4B C3 103.7(6) . . ?
O2 C4B H4D 111.0 . . ?
O2 C4B H4C 111.0 . . ?
C3 C4B H4D 111.0 . . ?
C3 C4B H4C 111.0 . . ?
H4D C4B H4C 109.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O6 0.828(19) 1.969(19) 2.7949(12) 175.7(17) 1_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
O1 C2 C5 C6 52.15(12) . . . . ?
O1 C3 C4A O2 -4.0(4) . . . . ?
O1 C3 C4B O2 -26.0(8) . . . . ?
O2 C2 C5 C6 -61.93(11) . . . . ?
O3 N1 C7 C6 116.36(10) . . . . ?
O3 N1 C7 C8 -120.57(10) . . . . ?
O4 N1 C7 C6 -63.64(11) . . . . ?
O4 N1 C7 C8 59.43(11) . . . . ?
O5 C12 C13 C14 178.30(10) . . . . ?
N1 C7 C8 C9 -177.85(8) . . . . ?
N1 C7 C8 C15 57.78(10) . . . . ?
C1 C2 C5 C6 175.60(9) . . . . ?
C2 O1 C3 C4A 25.0(3) . . . . ?
C2 O1 C3 C4B 38.2(5) . . . . ?
C2 O2 C4A C3 -18.4(4) . . . . ?
C2 O2 C4B C3 4.5(8) . . . . ?
C2 C5 C6 C7 -179.01(8) . . . . ?
C3 O1 C2 O2 -37.06(10) . . . . ?
C3 O1 C2 C1 82.07(10) . . . . ?
C3 O1 C2 C5 -154.19(9) . . . . ?
C5 C6 C7 N1 -61.59(11) . . . . ?
C5 C6 C7 C8 -179.82(8) . . . . ?
C6 C7 C8 C9 -59.27(11) . . . . ?
C6 C7 C8 C15 176.36(8) . . . . ?
C7 C8 C9 C10 -58.10(12) . . . . ?
C7 C8 C9 C14 123.84(10) . . . . ?
C7 C8 C15 C16 -157.50(8) . . . . ?
C8 C9 C10 C11 -179.53(9) . . . . ?
C8 C9 C14 C13 179.81(9) . . . . ?
C8 C15 C16 C17 74.12(10) . . . . ?
C8 C15 C16 C19 -167.05(8) . . . . ?
C9 C8 C15 C16 77.84(10) . . . . ?
C9 C10 C11 C12 -0.31(16) . . . . ?
C10 C9 C14 C13 1.68(15) . . . . ?
C10 C11 C12 O5 -178.05(10) . . . . ?
C10 C11 C12 C13 1.82(16) . . . . ?
C11 C12 C13 C14 -1.57(16) . . . . ?
C12 C13 C14 C9 -0.20(16) . . . . ?
C14 C9 C10 C11 -1.42(15) . . . . ?
C15 C8 C9 C10 67.08(12) . . . . ?
C15 C8 C9 C14 -110.98(10) . . . . ?
C15 C16 C17 O6 56.29(13) . . . . ?
C15 C16 C17 O7 -124.89(9) . . . . ?
C15 C16 C19 O8 2.28(15) . . . . ?
C15 C16 C19 O9 -175.93(8) . . . . ?
C17 C16 C19 O8 123.83(11) . . . . ?
C17 C16 C19 O9 -54.38(10) . . . . ?
C18 O7 C17 O6 4.18(15) . . . . ?
C18 O7 C17 C16 -174.63(9) . . . . ?
C19 C16 C17 O6 -65.71(12) . . . . ?
C19 C16 C17 O7 113.12(9) . . . . ?
C20 O9 C19 O8 3.51(16) . . . . ?
C20 O9 C19 C16 -178.25(9) . . . . ?
C4A O2 C2 O1 34.4(3) . . . . ?
C4A O2 C2 C1 -85.4(3) . . . . ?
C4A O2 C2 C5 151.2(3) . . . . ?
C4B O2 C2 O1 19.1(6) . . . . ?
C4B O2 C2 C1 -100.7(6) . . . . ?
C4B O2 C2 C5 135.9(6) . . . . ?

_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.864
