# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_nr97
_audit_block_doi                 10.5517/ccdc.csd.cc2pmm43
_database_code_depnum_ccdc_archive 'CCDC 2491505'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-9mgc4 2025
loop_
_audit_author_name
_audit_author_address
'Alexander D. Volodin'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2025-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N O8'
_chemical_formula_sum            'C20 H25 N O8'
_chemical_formula_weight         407.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6316(14)
_cell_length_b                   14.5653(19)
_cell_length_c                   12.9547(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.980(4)
_cell_angle_gamma                90
_cell_volume                     2004.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6057
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.360
_cell_measurement_theta_min      2.373
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1245 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8656.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21328
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         1.917
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3656
_reflns_number_total             4628
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.060
_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)+(0.0561P)²+0.2579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,
 H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56644(8) 0.62409(6) 0.50195(7) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.71515(9) 0.48014(6) 0.48933(8) 0.0278(2) Uani 1 1 d . . . . .
O3 O 0.82246(11) 0.54235(7) 0.36204(9) 0.0408(3) Uani 1 1 d . . . . .
O4 O 0.81550(9) 0.97625(6) 0.55396(7) 0.0242(2) Uani 1 1 d . . . . .
O5 O 0.90555(9) 0.83855(7) 0.57847(8) 0.0326(3) Uani 1 1 d . . . . .
O6 O 0.79715(8) 0.89143(6) 0.33065(7) 0.0229(2) Uani 1 1 d . . . . .
O7 O 0.59623(9) 0.93424(7) 0.34828(8) 0.0276(2) Uani 1 1 d . . . . .
O8 O 0.13267(8) 0.73377(6) 0.83049(7) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.61228(9) 0.71079(7) 0.54469(8) 0.0159(2) Uani 1 1 d . . . . .
C00P C 0.52100(13) 0.56313(9) 0.33426(11) 0.0249(3) Uani 1 1 d . . . . .
H00A H 0.4842 0.5113 0.3708 0.037 Uiso 1 1 calc R U . . .
H00B H 0.5589 0.5411 0.2710 0.037 Uiso 1 1 calc R U . . .
H00C H 0.4551 0.6080 0.3165 0.037 Uiso 1 1 calc R U . . .
C1 C 0.70809(11) 0.74419(8) 0.47295(9) 0.0158(2) Uani 1 1 d . . . . .
H1 H 0.7931 0.7206 0.4953 0.019 Uiso 1 1 calc R U . . .
C2 C 0.70381(11) 0.84985(8) 0.48585(9) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.58690(12) 0.86663(8) 0.55162(10) 0.0201(3) Uani 1 1 d . . . . .
H3A H 0.6116 0.8754 0.6254 0.024 Uiso 1 1 calc R U . . .
H3B H 0.5392 0.9211 0.5268 0.024 Uiso 1 1 calc R U . . .
C4 C 0.50977(11) 0.77916(8) 0.53592(10) 0.0167(3) Uani 1 1 d . . . . .
H4 H 0.4715 0.7781 0.4643 0.020 Uiso 1 1 calc R U . . .
C5 C 0.66794(12) 0.70182(8) 0.36873(10) 0.0176(3) Uani 1 1 d . . . . .
H5A H 0.6000 0.7377 0.3336 0.021 Uiso 1 1 calc R U . . .
H5B H 0.7398 0.6962 0.3225 0.021 Uiso 1 1 calc R U . . .
C6 C 0.62138(12) 0.60810(8) 0.40317(9) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.82113(12) 0.88519(9) 0.54397(10) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.91594(14) 1.01737(10) 0.61691(12) 0.0301(3) Uani 1 1 d . . . . .
H8A H 0.9971 0.9932 0.5958 0.045 Uiso 1 1 calc R U . . .
H8B H 0.9040 1.0026 0.6897 0.045 Uiso 1 1 calc R U . . .
H8C H 0.9145 1.0842 0.6077 0.045 Uiso 1 1 calc R U . . .
C9 C 0.69037(12) 0.89803(8) 0.38126(10) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.79254(15) 0.92947(10) 0.22664(11) 0.0307(3) Uani 1 1 d . . . . .
H10A H 0.7320 0.8947 0.1834 0.046 Uiso 1 1 calc R U . . .
H10B H 0.8761 0.9254 0.1973 0.046 Uiso 1 1 calc R U . . .
H10C H 0.7664 0.9939 0.2292 0.046 Uiso 1 1 calc R U . . .
C11 C 0.73249(13) 0.54125(8) 0.41563(10) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.80875(15) 0.40814(10) 0.49806(13) 0.0348(4) Uani 1 1 d . . . . .
H12A H 0.8159 0.3777 0.4311 0.052 Uiso 1 1 calc R U . . .
H12B H 0.7835 0.3632 0.5497 0.052 Uiso 1 1 calc R U . . .
H12C H 0.8902 0.4348 0.5193 0.052 Uiso 1 1 calc R U . . .
C13 C 0.40852(11) 0.76519(8) 0.61301(9) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.30069(12) 0.81887(9) 0.60571(10) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.2918 0.8626 0.5515 0.025 Uiso 1 1 calc R U . . .
C15 C 0.20538(12) 0.81011(9) 0.67602(10) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.1319 0.8470 0.6695 0.027 Uiso 1 1 calc R U . . .
C16 C 0.21892(12) 0.74687(9) 0.75568(10) 0.0196(3) Uani 1 1 d . . . . .
C17 C 0.32517(12) 0.69126(8) 0.76279(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.3335 0.6469 0.8163 0.024 Uiso 1 1 calc R U . . .
C18 C 0.41894(11) 0.70056(8) 0.69181(10) 0.0177(3) Uani 1 1 d . . . . .
H18 H 0.4912 0.6623 0.6971 0.021 Uiso 1 1 calc R U . . .
C19 C 0.01537(13) 0.78083(11) 0.81890(12) 0.0306(3) Uani 1 1 d . . . . .
H19A H -0.0262 0.7633 0.7531 0.046 Uiso 1 1 calc R U . . .
H19B H 0.0302 0.8472 0.8197 0.046 Uiso 1 1 calc R U . . .
H19C H -0.0384 0.7642 0.8759 0.046 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 1.4561(13) . ?
O1 C6 1.4438(15) . ?
O2 C11 1.3228(16) . ?
O2 C12 1.4474(16) . ?
O3 C11 1.2012(16) . ?
O4 C7 1.3341(15) . ?
O4 C8 1.4505(16) . ?
O5 C7 1.1996(16) . ?
O6 C9 1.3338(15) . ?
O6 C10 1.4561(16) . ?
O7 C9 1.1970(16) . ?
O8 C16 1.3704(15) . ?
O8 C19 1.4263(16) . ?
N1 C1 1.4844(15) . ?
N1 C4 1.4778(15) . ?
C00P H00A 0.9800 . ?
C00P H00B 0.9800 . ?
C00P H00C 0.9800 . ?
C00P C6 1.5163(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.5489(16) . ?
C1 C5 1.5318(17) . ?
C2 C3 1.5505(17) . ?
C2 C7 1.5240(17) . ?
C2 C9 1.5282(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5249(17) . ?
C4 H4 1.0000 . ?
C4 C13 1.5072(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5240(16) . ?
C6 C11 1.5351(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3881(17) . ?
C13 C18 1.3902(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3915(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3870(19) . ?
C16 C17 1.3905(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3861(17) . ?
C18 H18 0.9500 . ?
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
C6 O1 N1 109.68(8) . . ?
C11 O2 C12 115.55(11) . . ?
C7 O4 C8 115.50(11) . . ?
C9 O6 C10 115.18(11) . . ?
C16 O8 C19 117.56(11) . . ?
O1 N1 C1 105.90(8) . . ?
O1 N1 C4 108.60(9) . . ?
C4 N1 C1 104.55(9) . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?
C6 C00P H00A 109.5 . . ?
C6 C00P H00B 109.5 . . ?
C6 C00P H00C 109.5 . . ?
N1 C1 H1 109.8 . . ?
N1 C1 C2 103.57(9) . . ?
N1 C1 C5 104.10(9) . . ?
C2 C1 H1 109.8 . . ?
C5 C1 H1 109.8 . . ?
C5 C1 C2 119.15(10) . . ?
C1 C2 C3 104.06(9) . . ?
C7 C2 C1 111.25(10) . . ?
C7 C2 C3 109.47(10) . . ?
C7 C2 C9 109.43(10) . . ?
C9 C2 C1 111.27(10) . . ?
C9 C2 C3 111.27(10) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 103.45(9) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
N1 C4 C3 99.26(9) . . ?
N1 C4 H4 109.6 . . ?
N1 C4 C13 113.56(10) . . ?
C3 C4 H4 109.6 . . ?
C13 C4 C3 114.68(10) . . ?
C13 C4 H4 109.6 . . ?
C1 C5 H5A 111.6 . . ?
C1 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
C6 C5 C1 100.73(9) . . ?
C6 C5 H5A 111.6 . . ?
C6 C5 H5B 111.6 . . ?
O1 C6 C00P 107.06(10) . . ?
O1 C6 C5 105.10(9) . . ?
O1 C6 C11 110.03(10) . . ?
C00P C6 C5 116.34(11) . . ?
C00P C6 C11 108.14(10) . . ?
C5 C6 C11 110.02(10) . . ?
O4 C7 C2 110.18(11) . . ?
O5 C7 O4 124.22(12) . . ?
O5 C7 C2 125.57(12) . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C9 C2 110.34(10) . . ?
O7 C9 O6 124.86(12) . . ?
O7 C9 C2 124.76(12) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C6 112.13(11) . . ?
O3 C11 O2 124.04(12) . . ?
O3 C11 C6 123.78(12) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 119.07(11) . . ?
C14 C13 C18 118.43(11) . . ?
C18 C13 C4 122.50(11) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.48(12) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.25(12) . . ?
C16 C15 H15 120.4 . . ?
O8 C16 C15 124.32(12) . . ?
O8 C16 C17 115.72(12) . . ?
C15 C16 C17 119.95(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.03(12) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.82(11) . . ?
C17 C18 H18 119.6 . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 152.31(9) . . . . ?
O1 N1 C1 C5 27.05(11) . . . . ?
O1 N1 C4 C3 -163.16(9) . . . . ?
O1 N1 C4 C13 74.65(12) . . . . ?
O1 C6 C11 O2 32.87(14) . . . . ?
O1 C6 C11 O3 -149.69(13) . . . . ?
O8 C16 C17 C18 -178.79(11) . . . . ?
N1 O1 C6 C00P -143.04(10) . . . . ?
N1 O1 C6 C5 -18.74(12) . . . . ?
N1 O1 C6 C11 99.67(10) . . . . ?
N1 C1 C2 C3 -9.51(12) . . . . ?
N1 C1 C2 C7 108.26(11) . . . . ?
N1 C1 C2 C9 -129.43(10) . . . . ?
N1 C1 C5 C6 -37.20(11) . . . . ?
N1 C4 C13 C14 -173.30(11) . . . . ?
N1 C4 C13 C18 6.92(17) . . . . ?
C00P C6 C11 O2 -83.75(13) . . . . ?
C00P C6 C11 O3 93.68(15) . . . . ?
C1 N1 C4 C3 -50.46(11) . . . . ?
C1 N1 C4 C13 -172.64(9) . . . . ?
C1 C2 C3 C4 -20.55(12) . . . . ?
C1 C2 C7 O4 179.87(10) . . . . ?
C1 C2 C7 O5 -1.88(18) . . . . ?
C1 C2 C9 O6 -71.36(12) . . . . ?
C1 C2 C9 O7 106.67(14) . . . . ?
C1 C5 C6 O1 34.07(12) . . . . ?
C1 C5 C6 C00P 152.27(11) . . . . ?
C1 C5 C6 C11 -84.35(11) . . . . ?
C2 C1 C5 C6 -151.86(10) . . . . ?
C2 C3 C4 N1 42.78(11) . . . . ?
C2 C3 C4 C13 164.16(10) . . . . ?
C3 C2 C7 O4 -65.68(13) . . . . ?
C3 C2 C7 O5 112.57(14) . . . . ?
C3 C2 C9 O6 173.10(10) . . . . ?
C3 C2 C9 O7 -8.87(17) . . . . ?
C3 C4 C13 C14 73.52(15) . . . . ?
C3 C4 C13 C18 -106.26(13) . . . . ?
C4 N1 C1 C2 37.69(11) . . . . ?
C4 N1 C1 C5 -87.57(11) . . . . ?
C4 C13 C14 C15 -178.73(12) . . . . ?
C4 C13 C18 C17 178.40(11) . . . . ?
C5 C1 C2 C3 105.43(12) . . . . ?
C5 C1 C2 C7 -136.80(11) . . . . ?
C5 C1 C2 C9 -14.49(15) . . . . ?
C5 C6 C11 O2 148.21(11) . . . . ?
C5 C6 C11 O3 -34.36(18) . . . . ?
C6 O1 N1 C1 -5.33(12) . . . . ?
C6 O1 N1 C4 106.47(10) . . . . ?
C7 C2 C3 C4 -139.55(10) . . . . ?
C7 C2 C9 O6 52.00(13) . . . . ?
C7 C2 C9 O7 -129.97(13) . . . . ?
C8 O4 C7 O5 -4.14(19) . . . . ?
C8 O4 C7 C2 174.14(10) . . . . ?
C9 C2 C3 C4 99.37(11) . . . . ?
C9 C2 C7 O4 56.51(13) . . . . ?
C9 C2 C7 O5 -125.25(14) . . . . ?
C10 O6 C9 O7 -2.12(18) . . . . ?
C10 O6 C9 C2 175.91(10) . . . . ?
C12 O2 C11 O3 -4.3(2) . . . . ?
C12 O2 C11 C6 173.16(11) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C13 C18 C17 -1.38(18) . . . . ?
C14 C15 C16 O8 178.52(12) . . . . ?
C14 C15 C16 C17 -1.88(19) . . . . ?
C15 C16 C17 C18 1.58(19) . . . . ?
C16 C17 C18 C13 0.08(19) . . . . ?
C18 C13 C14 C15 1.06(19) . . . . ?
C19 O8 C16 C15 7.36(18) . . . . ?
C19 O8 C16 C17 -172.26(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kb1523102
_audit_block_doi                 10.5517/ccdc.csd.cc2pmm54
_database_code_depnum_ccdc_archive 'CCDC 2491506'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-9mgc4 2025
loop_
_audit_author_name
_audit_author_address
'Alexander D. Volodin'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2025-09-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O9'
_chemical_formula_sum            'C21 H22 N2 O9'
_chemical_formula_weight         446.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.598(6)
_cell_length_b                   10.180(6)
_cell_length_c                   12.966(12)
_cell_angle_alpha                71.30(3)
_cell_angle_beta                 80.52(3)
_cell_angle_gamma                76.20(3)
_cell_volume                     1039.1(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    64
_cell_measurement_temperature    120
_cell_measurement_theta_max      15.64
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16774
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         1.666
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3358
_reflns_number_total             5364
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.3510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C10(H10)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28974(16) 0.43170(15) 0.24221(12) 0.0231(3) Uani 1 1 d . . . . .
O9 O 0.43060(19) 0.35917(17) 0.48202(12) 0.0305(4) Uani 1 1 d . . . . .
O14 O 0.78715(19) 0.23598(17) 0.20654(13) 0.0325(4) Uani 1 1 d . . . . .
O23 O 0.01140(19) 0.46666(18) 0.34690(13) 0.0349(4) Uani 1 1 d . . . . .
O26 O 0.60176(19) 0.80098(17) 0.03418(13) 0.0325(4) Uani 1 1 d . . . . .
O30 O 0.1542(2) 0.77592(18) 0.28345(14) 0.0410(5) Uani 1 1 d . . . . .
O31 O 0.22734(19) 0.92082(17) 0.11918(13) 0.0350(4) Uani 1 1 d . . . . .
O27 O 0.5504(2) 0.86749(17) 0.18682(13) 0.0345(4) Uani 1 1 d . . . . .
N2 N 0.4367(2) 0.46057(18) 0.16836(14) 0.0203(4) Uani 1 1 d . . . . .
N4 N 0.59289(19) 0.33216(18) 0.32318(13) 0.0193(4) Uani 1 1 d . . . . .
O22 O -0.1066(2) 0.6179(2) 0.20008(16) 0.0504(5) Uani 1 1 d . . . . .
C25 C 0.5294(3) 0.7957(2) 0.12213(18) 0.0230(5) Uani 1 1 d . . . . .
C6 C 0.7324(3) 0.1035(2) 0.39794(18) 0.0241(5) Uani 1 1 d . . . . .
C15 C 0.4671(3) 0.5935(2) 0.28437(17) 0.0233(5) Uani 1 1 d . . . . .
H15A H 0.5459 0.6260 0.3133 0.028 Uiso 1 1 calc R U . . .
H15B H 0.3780 0.5711 0.3418 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5466(2) 0.4669(2) 0.24208(16) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.6471 0.4904 0.1958 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7146(2) 0.2249(2) 0.29646(18) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.5334(2) 0.2895(2) 0.43486(17) 0.0217(4) Uani 1 1 d . . . . .
C16 C 0.4045(2) 0.7037(2) 0.17928(17) 0.0216(4) Uani 1 1 d . . . . .
C19 C 0.1606(2) 0.4900(2) 0.17239(18) 0.0243(5) Uani 1 1 d . . . . .
C11 C 0.7078(3) -0.0821(3) 0.6049(2) 0.0364(6) Uani 1 1 d . . . . .
H11 H 0.7000 -0.1477 0.6758 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6249(3) 0.1436(2) 0.48018(18) 0.0241(5) Uani 1 1 d . . . . .
C20 C 0.1318(3) 0.3754(3) 0.1288(2) 0.0333(6) Uani 1 1 d . . . . .
H20A H 0.2267 0.3471 0.0816 0.050 Uiso 1 1 calc R U . . .
H20B H 0.0380 0.4127 0.0867 0.050 Uiso 1 1 calc R U . . .
H20C H 0.1124 0.2931 0.1904 0.050 Uiso 1 1 calc R U . . .
C21 C 0.0084(3) 0.5361(2) 0.24056(19) 0.0288(5) Uani 1 1 d . . . . .
C13 C 0.8300(3) -0.0300(3) 0.4174(2) 0.0326(5) Uani 1 1 d . . . . .
H13 H 0.9042 -0.0572 0.3615 0.039 Uiso 1 1 calc R U . . .
C29 C 0.2481(3) 0.8017(2) 0.20271(19) 0.0271(5) Uani 1 1 d . . . . .
C12 C 0.8149(3) -0.1224(3) 0.5223(2) 0.0376(6) Uani 1 1 d . . . . .
H12 H 0.8791 -0.2152 0.5380 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6119(3) 0.0529(3) 0.58500(19) 0.0314(5) Uani 1 1 d . . . . .
H10 H 0.5402 0.0816 0.6414 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3841(2) 0.6118(2) 0.10609(17) 0.0211(4) Uani 1 1 d . . . . .
H17 H 0.4549 0.6346 0.0360 0.025 Uiso 1 1 calc R U . . .
C18 C 0.2145(3) 0.6162(2) 0.08103(19) 0.0278(5) Uani 1 1 d . . . . .
H18A H 0.2166 0.6044 0.0079 0.033 Uiso 1 1 calc R U . . .
H18B H 0.1417 0.7066 0.0839 0.033 Uiso 1 1 calc R U . . .
C28 C 0.6711(4) 0.9538(3) 0.1469(2) 0.0441(7) Uani 1 1 d . . . . .
H28A H 0.6379 1.0302 0.0812 0.066 Uiso 1 1 calc R U . . .
H28B H 0.7739 0.8953 0.1288 0.066 Uiso 1 1 calc R U . . .
H28C H 0.6834 0.9944 0.2034 0.066 Uiso 1 1 calc R U . . .
C32 C 0.0895(3) 1.0309(3) 0.1316(3) 0.0437(7) Uani 1 1 d . . . . .
H32A H 0.0930 1.1154 0.0687 0.066 Uiso 1 1 calc R U . . .
H32B H 0.0923 1.0542 0.1989 0.066 Uiso 1 1 calc R U . . .
H32C H -0.0097 0.9974 0.1356 0.066 Uiso 1 1 calc R U . . .
C24 C -0.1346(3) 0.5035(3) 0.4151(2) 0.0440(7) Uani 1 1 d . . . . .
H24A H -0.2266 0.4864 0.3891 0.066 Uiso 1 1 calc R U . . .
H24B H -0.1519 0.6037 0.4110 0.066 Uiso 1 1 calc R U . . .
H24C H -0.1235 0.4452 0.4910 0.066 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 N2 1.483(2) . ?
O1 C19 1.441(3) . ?
O9 C8 1.208(3) . ?
O14 C5 1.213(3) . ?
O23 C21 1.334(3) . ?
O23 C24 1.456(3) . ?
O26 C25 1.197(3) . ?
O30 C29 1.210(3) . ?
O31 C29 1.339(3) . ?
O31 C32 1.451(3) . ?
O27 C25 1.332(3) . ?
O27 C28 1.443(3) . ?
N2 C3 1.475(3) . ?
N2 C17 1.489(3) . ?
N4 C3 1.448(3) . ?
N4 C5 1.409(3) . ?
N4 C8 1.416(3) . ?
O22 C21 1.202(3) . ?
C25 C16 1.534(3) . ?
C6 C5 1.488(3) . ?
C6 C7 1.390(3) . ?
C6 C13 1.386(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C3 1.529(3) . ?
C15 C16 1.542(3) . ?
C3 H3 1.0000 . ?
C8 C7 1.485(3) . ?
C16 C29 1.521(3) . ?
C16 C17 1.584(3) . ?
C19 C20 1.532(3) . ?
C19 C21 1.518(3) . ?
C19 C18 1.547(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(4) . ?
C11 C10 1.393(4) . ?
C7 C10 1.381(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.389(4) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C17 H17 1.0000 . ?
C17 C18 1.534(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C19 O1 N2 104.67(15) . . ?
C21 O23 C24 115.0(2) . . ?
C29 O31 C32 117.11(19) . . ?
C25 O27 C28 116.44(18) . . ?
O1 N2 C17 101.53(15) . . ?
C3 N2 O1 103.32(15) . . ?
C3 N2 C17 103.21(16) . . ?
C5 N4 C3 120.83(17) . . ?
C5 N4 C8 111.08(17) . . ?
C8 N4 C3 128.06(17) . . ?
O26 C25 O27 124.1(2) . . ?
O26 C25 C16 126.2(2) . . ?
O27 C25 C16 109.70(18) . . ?
C7 C6 C5 107.47(19) . . ?
C13 C6 C5 131.2(2) . . ?
C13 C6 C7 121.3(2) . . ?
H15A C15 H15B 109.3 . . ?
C3 C15 H15A 111.5 . . ?
C3 C15 H15B 111.5 . . ?
C3 C15 C16 101.20(17) . . ?
C16 C15 H15A 111.5 . . ?
C16 C15 H15B 111.5 . . ?
N2 C3 C15 106.07(17) . . ?
N2 C3 H3 106.9 . . ?
N4 C3 N2 112.50(17) . . ?
N4 C3 C15 117.00(18) . . ?
N4 C3 H3 106.9 . . ?
C15 C3 H3 106.9 . . ?
O14 C5 N4 124.1(2) . . ?
O14 C5 C6 129.3(2) . . ?
N4 C5 C6 106.61(18) . . ?
O9 C8 N4 126.4(2) . . ?
O9 C8 C7 128.1(2) . . ?
N4 C8 C7 105.44(18) . . ?
C25 C16 C15 109.74(18) . . ?
C25 C16 C17 110.46(17) . . ?
C15 C16 C17 104.23(17) . . ?
C29 C16 C25 107.65(18) . . ?
C29 C16 C15 112.28(18) . . ?
C29 C16 C17 112.48(18) . . ?
O1 C19 C20 109.53(18) . . ?
O1 C19 C21 108.30(18) . . ?
O1 C19 C18 105.51(17) . . ?
C20 C19 C18 113.2(2) . . ?
C21 C19 C20 107.89(19) . . ?
C21 C19 C18 112.31(19) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(2) . . ?
C6 C7 C8 109.38(19) . . ?
C10 C7 C6 121.6(2) . . ?
C10 C7 C8 129.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O23 C21 C19 113.00(19) . . ?
O22 C21 O23 124.4(2) . . ?
O22 C21 C19 122.3(2) . . ?
C6 C13 H13 121.4 . . ?
C6 C13 C12 117.2(2) . . ?
C12 C13 H13 121.4 . . ?
O30 C29 O31 124.6(2) . . ?
O30 C29 C16 125.6(2) . . ?
O31 C29 C16 109.85(18) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C10 H10 121.3 . . ?
C7 C10 C11 117.5(2) . . ?
C7 C10 H10 121.3 . . ?
N2 C17 C16 107.04(17) . . ?
N2 C17 H17 109.4 . . ?
N2 C17 C18 102.55(16) . . ?
C16 C17 H17 109.4 . . ?
C18 C17 C16 118.70(18) . . ?
C18 C17 H17 109.4 . . ?
C19 C18 H18A 111.0 . . ?
C19 C18 H18B 111.0 . . ?
C17 C18 C19 103.80(17) . . ?
C17 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C3 N4 65.32(19) . . . . ?
O1 N2 C3 C15 -63.79(18) . . . . ?
O1 N2 C17 C16 82.59(17) . . . . ?
O1 N2 C17 C18 -43.06(18) . . . . ?
O1 C19 C21 O23 -24.4(3) . . . . ?
O1 C19 C21 O22 161.5(2) . . . . ?
O1 C19 C18 C17 3.2(2) . . . . ?
O9 C8 C7 C6 -179.7(2) . . . . ?
O9 C8 C7 C10 1.6(4) . . . . ?
O26 C25 C16 C15 115.2(2) . . . . ?
O26 C25 C16 C29 -122.3(2) . . . . ?
O26 C25 C16 C17 0.9(3) . . . . ?
O27 C25 C16 C15 -62.8(2) . . . . ?
O27 C25 C16 C29 59.6(2) . . . . ?
O27 C25 C16 C17 -177.20(17) . . . . ?
N2 O1 C19 C20 91.81(19) . . . . ?
N2 O1 C19 C21 -150.76(16) . . . . ?
N2 O1 C19 C18 -30.3(2) . . . . ?
N2 C17 C18 C19 24.7(2) . . . . ?
N4 C8 C7 C6 -0.2(2) . . . . ?
N4 C8 C7 C10 -178.9(2) . . . . ?
C25 C16 C29 O30 -143.0(2) . . . . ?
C25 C16 C29 O31 38.3(2) . . . . ?
C25 C16 C17 N2 116.67(18) . . . . ?
C25 C16 C17 C18 -128.1(2) . . . . ?
C6 C7 C10 C11 -1.6(3) . . . . ?
C6 C13 C12 C11 -0.9(4) . . . . ?
C15 C16 C29 O30 -22.1(3) . . . . ?
C15 C16 C29 O31 159.16(18) . . . . ?
C15 C16 C17 N2 -1.1(2) . . . . ?
C15 C16 C17 C18 114.1(2) . . . . ?
C3 N2 C17 C16 -24.23(19) . . . . ?
C3 N2 C17 C18 -149.88(16) . . . . ?
C3 N4 C5 O14 -0.4(3) . . . . ?
C3 N4 C5 C6 179.29(17) . . . . ?
C3 N4 C8 O9 0.9(3) . . . . ?
C3 N4 C8 C7 -178.59(18) . . . . ?
C3 C15 C16 C25 -93.41(19) . . . . ?
C3 C15 C16 C29 146.90(18) . . . . ?
C3 C15 C16 C17 24.9(2) . . . . ?
C5 N4 C3 N2 80.2(2) . . . . ?
C5 N4 C3 C15 -156.62(18) . . . . ?
C5 N4 C8 O9 178.9(2) . . . . ?
C5 N4 C8 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C5 C6 C7 C10 179.7(2) . . . . ?
C5 C6 C13 C12 -178.2(2) . . . . ?
C8 N4 C3 N2 -102.0(2) . . . . ?
C8 N4 C3 C15 21.2(3) . . . . ?
C8 N4 C5 O14 -178.6(2) . . . . ?
C8 N4 C5 C6 1.1(2) . . . . ?
C8 C7 C10 C11 177.0(2) . . . . ?
C16 C15 C3 N2 -41.86(19) . . . . ?
C16 C15 C3 N4 -168.29(17) . . . . ?
C16 C17 C18 C19 -93.0(2) . . . . ?
C19 O1 N2 C3 153.29(16) . . . . ?
C19 O1 N2 C17 46.56(18) . . . . ?
C7 C6 C5 O14 178.5(2) . . . . ?
C7 C6 C5 N4 -1.2(2) . . . . ?
C7 C6 C13 C12 0.6(3) . . . . ?
C20 C19 C21 O23 94.1(2) . . . . ?
C20 C19 C21 O22 -80.0(3) . . . . ?
C20 C19 C18 C17 -116.6(2) . . . . ?
C21 C19 C18 C17 121.0(2) . . . . ?
C13 C6 C5 O14 -2.6(4) . . . . ?
C13 C6 C5 N4 177.7(2) . . . . ?
C13 C6 C7 C8 -178.2(2) . . . . ?
C13 C6 C7 C10 0.7(3) . . . . ?
C29 C16 C17 N2 -123.02(18) . . . . ?
C29 C16 C17 C18 -7.7(3) . . . . ?
C12 C11 C10 C7 1.3(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C17 N2 C3 N4 170.78(16) . . . . ?
C17 N2 C3 C15 41.67(19) . . . . ?
C17 C16 C29 O30 95.1(3) . . . . ?
C17 C16 C29 O31 -83.7(2) . . . . ?
C18 C19 C21 O23 -140.5(2) . . . . ?
C18 C19 C21 O22 45.4(3) . . . . ?
C28 O27 C25 O26 -1.3(3) . . . . ?
C28 O27 C25 C16 176.8(2) . . . . ?
C32 O31 C29 O30 5.7(4) . . . . ?
C32 O31 C29 C16 -175.5(2) . . . . ?
C24 O23 C21 O22 -3.9(4) . . . . ?
C24 O23 C21 C19 -177.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kb1803102
_audit_block_doi                 10.5517/ccdc.csd.cc2pmm65
_database_code_depnum_ccdc_archive 'CCDC 2491507'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-9mgc4 2025
loop_
_audit_author_name
_audit_author_address
'Alexander D. Volodin'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2025-09-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N O9'
_chemical_formula_sum            'C20 H25 N O9'
_chemical_formula_weight         423.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.647(3)
_cell_length_b                   9.670(3)
_cell_length_c                   13.495(4)
_cell_angle_alpha                95.771(6)
_cell_angle_beta                 105.308(6)
_cell_angle_gamma                111.831(7)
_cell_volume                     985.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    120
_cell_measurement_theta_max      19.118
_cell_measurement_theta_min      2.727
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0803 before and 0.0384 after correction.
The Ratio of minimum to maximum transmission is 0.9065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14170
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.582
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4041
_reflns_number_total             6502
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.051
_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)+(0.0667P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1451
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C5(H5), C8(H8)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C29(H29A,H29B,
 H29C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O24 O 0.55505(15) 0.60608(13) 0.14881(8) 0.0213(3) Uani 1 1 d . . . . .
O28 O 0.90862(14) 0.76838(12) 0.47758(8) 0.0198(3) Uani 1 1 d . . . . .
O9 O -0.05397(15) -0.22473(13) 0.04175(9) 0.0236(3) Uani 1 1 d . . . . .
O16 O 1.10598(14) 0.45902(13) 0.27258(9) 0.0235(3) Uani 1 1 d . . . . .
H16 H 0.9977 0.4034 0.2450 0.035 Uiso 1 1 calc R U . . .
O30 O 0.76007(14) 0.30519(13) 0.18989(9) 0.0249(3) Uani 1 1 d . . . . .
O23 O 0.71847(15) 0.83035(13) 0.26544(9) 0.0259(3) Uani 1 1 d . . . . .
O20 O 1.28390(15) 0.81343(14) 0.45658(9) 0.0270(3) Uani 1 1 d . . . . .
O19 O 1.21836(16) 0.57586(15) 0.48197(10) 0.0307(3) Uani 1 1 d . . . . .
O27 O 0.63029(15) 0.71560(14) 0.47321(10) 0.0300(3) Uani 1 1 d . . . . .
N1 N 0.69335(16) 0.38009(14) 0.23990(10) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.3880(2) 0.18400(18) 0.18590(12) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.3933(2) 0.07932(18) 0.10807(12) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.4980 0.1018 0.0904 0.022 Uiso 1 1 calc R U . . .
C13 C 0.81399(19) 0.53239(17) 0.31213(12) 0.0149(3) Uani 1 1 d . . . . .
H13 H 0.8727 0.5155 0.3814 0.018 Uiso 1 1 calc R U . . .
C26 C 0.7350(2) 0.69915(18) 0.43413(12) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.0893(2) 0.00740(18) 0.16417(13) 0.0209(3) Uani 1 1 d . . . . .
H7 H -0.0131 -0.0181 0.1847 0.025 Uiso 1 1 calc R U . . .
C11 C 0.51039(19) 0.45137(17) 0.30876(12) 0.0163(3) Uani 1 1 d . . . . .
H11A H 0.5025 0.4234 0.3764 0.020 Uiso 1 1 calc R U . . .
H11B H 0.4038 0.4661 0.2728 0.020 Uiso 1 1 calc R U . . .
C6 C 0.0945(2) -0.09338(18) 0.08519(12) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.67917(19) 0.59630(17) 0.32641(12) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.53118(19) 0.33180(17) 0.24036(12) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.95682(19) 0.63073(18) 0.27042(12) 0.0168(3) Uani 1 1 d . . . . .
H14A H 0.9822 0.7394 0.2946 0.020 Uiso 1 1 calc R U . . .
H14B H 0.9096 0.6054 0.1925 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2465(2) -0.05699(18) 0.05670(12) 0.0193(3) Uani 1 1 d . . . . .
H5 H 0.2497 -0.1252 0.0023 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2331(2) 0.14435(18) 0.21252(13) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.2273 0.2136 0.2651 0.023 Uiso 1 1 calc R U . . .
C15 C 1.1314(2) 0.61192(18) 0.30446(12) 0.0186(3) Uani 1 1 d . . . . .
C22 C 0.65402(19) 0.69261(18) 0.24526(12) 0.0172(3) Uani 1 1 d . . . . .
C18 C 1.2144(2) 0.66124(19) 0.42430(13) 0.0207(3) Uani 1 1 d . . . . .
C17 C 1.2585(2) 0.7128(2) 0.25411(13) 0.0235(4) Uani 1 1 d . . . . .
H17A H 1.3719 0.7054 0.2785 0.035 Uiso 1 1 calc R U . . .
H17B H 1.2763 0.8192 0.2745 0.035 Uiso 1 1 calc R U . . .
H17C H 1.2087 0.6783 0.1772 0.035 Uiso 1 1 calc R U . . .
C10 C -0.0588(2) -0.32831(19) -0.04299(14) 0.0272(4) Uani 1 1 d . . . . .
H10A H -0.0321 -0.2747 -0.0983 0.041 Uiso 1 1 calc R U . . .
H10B H -0.1764 -0.4125 -0.0717 0.041 Uiso 1 1 calc R U . . .
H10C H 0.0289 -0.3690 -0.0173 0.041 Uiso 1 1 calc R U . . .
C25 C 0.5296(2) 0.6901(2) 0.06709(14) 0.0282(4) Uani 1 1 d . . . . .
H25A H 0.4414 0.6190 0.0020 0.042 Uiso 1 1 calc R U . . .
H25B H 0.6415 0.7419 0.0544 0.042 Uiso 1 1 calc R U . . .
H25C H 0.4889 0.7659 0.0897 0.042 Uiso 1 1 calc R U . . .
C29 C 0.9732(2) 0.8662(2) 0.58208(13) 0.0290(4) Uani 1 1 d . . . . .
H29A H 0.8984 0.9205 0.5856 0.044 Uiso 1 1 calc R U . . .
H29B H 1.0946 0.9404 0.5961 0.044 Uiso 1 1 calc R U . . .
H29C H 0.9701 0.8036 0.6349 0.044 Uiso 1 1 calc R U . . .
C21 C 1.3808(2) 0.8741(2) 0.56862(14) 0.0337(4) Uani 1 1 d . . . . .
H21A H 1.4117 0.9839 0.5858 0.050 Uiso 1 1 calc R U . . .
H21B H 1.4887 0.8569 0.5861 0.050 Uiso 1 1 calc R U . . .
H21C H 1.3074 0.8222 0.6094 0.050 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
O24 C22 1.3368(19) . ?
O24 C25 1.452(2) . ?
O28 C26 1.3249(18) . ?
O28 C29 1.4556(18) . ?
O9 C6 1.3585(18) . ?
O9 C10 1.4237(19) . ?
O16 H16 0.8400 . ?
O16 C15 1.414(2) . ?
O30 N1 1.3157(15) . ?
O23 C22 1.2057(19) . ?
O20 C18 1.339(2) . ?
O20 C21 1.456(2) . ?
O19 C18 1.194(2) . ?
O27 C26 1.2104(18) . ?
N1 C13 1.4964(19) . ?
N1 C2 1.3049(19) . ?
C3 C4 1.405(2) . ?
C3 C2 1.452(2) . ?
C3 C8 1.403(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C13 H13 1.0000 . ?
C13 C12 1.552(2) . ?
C13 C14 1.532(2) . ?
C26 C12 1.522(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.392(2) . ?
C7 C8 1.378(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.542(2) . ?
C11 C2 1.500(2) . ?
C6 C5 1.396(2) . ?
C12 C22 1.531(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.542(2) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C15 C18 1.528(2) . ?
C15 C17 1.534(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C22 O24 C25 115.08(13) . . ?
C26 O28 C29 115.67(12) . . ?
C6 O9 C10 117.70(13) . . ?
C15 O16 H16 109.5 . . ?
C18 O20 C21 115.86(14) . . ?
O30 N1 C13 118.83(11) . . ?
C2 N1 O30 127.06(13) . . ?
C2 N1 C13 113.91(12) . . ?
C4 C3 C2 124.66(14) . . ?
C8 C3 C4 118.04(14) . . ?
C8 C3 C2 117.30(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.62(14) . . ?
C5 C4 H4 119.7 . . ?
N1 C13 H13 108.5 . . ?
N1 C13 C12 100.88(11) . . ?
N1 C13 C14 113.72(12) . . ?
C12 C13 H13 108.5 . . ?
C14 C13 H13 108.5 . . ?
C14 C13 C12 116.25(13) . . ?
O28 C26 C12 112.13(12) . . ?
O27 C26 O28 125.05(14) . . ?
O27 C26 C12 122.82(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C8 C7 C6 119.79(15) . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C2 C11 H11A 111.1 . . ?
C2 C11 H11B 111.1 . . ?
C2 C11 C12 103.55(12) . . ?
O9 C6 C7 115.46(14) . . ?
O9 C6 C5 124.54(14) . . ?
C7 C6 C5 119.99(14) . . ?
C26 C12 C13 114.13(12) . . ?
C26 C12 C11 110.80(12) . . ?
C26 C12 C22 106.47(13) . . ?
C11 C12 C13 103.54(12) . . ?
C22 C12 C13 109.57(12) . . ?
C22 C12 C11 112.47(12) . . ?
N1 C2 C3 126.80(13) . . ?
N1 C2 C11 110.16(13) . . ?
C3 C2 C11 123.03(13) . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C13 C14 C15 115.12(13) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C4 C5 C6 119.94(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.57(14) . . ?
C7 C8 H8 119.2 . . ?
O16 C15 C14 111.89(13) . . ?
O16 C15 C18 108.59(13) . . ?
O16 C15 C17 108.31(12) . . ?
C18 C15 C14 109.73(12) . . ?
C18 C15 C17 109.11(13) . . ?
C17 C15 C14 109.17(14) . . ?
O24 C22 C12 112.06(13) . . ?
O23 C22 O24 123.87(15) . . ?
O23 C22 C12 124.06(14) . . ?
O20 C18 C15 111.18(14) . . ?
O19 C18 O20 124.11(16) . . ?
O19 C18 C15 124.71(16) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O9 C10 H10A 109.5 . . ?
O9 C10 H10B 109.5 . . ?
O9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O28 C26 C12 C13 27.58(19) . . . . ?
O28 C26 C12 C11 143.98(13) . . . . ?
O28 C26 C12 C22 -93.43(15) . . . . ?
O9 C6 C5 C4 -178.42(15) . . . . ?
O16 C15 C18 O20 163.57(12) . . . . ?
O16 C15 C18 O19 -15.9(2) . . . . ?
O30 N1 C13 C12 164.41(13) . . . . ?
O30 N1 C13 C14 39.21(18) . . . . ?
O30 N1 C2 C3 0.2(3) . . . . ?
O30 N1 C2 C11 179.00(14) . . . . ?
O27 C26 C12 C13 -153.42(16) . . . . ?
O27 C26 C12 C11 -37.0(2) . . . . ?
O27 C26 C12 C22 85.56(19) . . . . ?
N1 C13 C12 C26 147.51(13) . . . . ?
N1 C13 C12 C11 26.97(14) . . . . ?
N1 C13 C12 C22 -93.21(14) . . . . ?
N1 C13 C14 C15 -91.17(15) . . . . ?
C3 C4 C5 C6 -2.5(2) . . . . ?
C4 C3 C2 N1 -12.4(3) . . . . ?
C4 C3 C2 C11 168.99(15) . . . . ?
C4 C3 C8 C7 -0.2(2) . . . . ?
C13 N1 C2 C3 -174.49(14) . . . . ?
C13 N1 C2 C11 4.28(18) . . . . ?
C13 C12 C22 O24 75.38(15) . . . . ?
C13 C12 C22 O23 -103.33(16) . . . . ?
C13 C14 C15 O16 58.30(17) . . . . ?
C13 C14 C15 C18 -62.30(17) . . . . ?
C13 C14 C15 C17 178.17(12) . . . . ?
C26 C12 C22 O24 -160.73(12) . . . . ?
C26 C12 C22 O23 20.56(19) . . . . ?
C7 C6 C5 C4 0.7(2) . . . . ?
C11 C12 C22 O24 -39.19(16) . . . . ?
C11 C12 C22 O23 142.09(15) . . . . ?
C6 C7 C8 C3 -1.6(3) . . . . ?
C12 C13 C14 C15 152.30(13) . . . . ?
C12 C11 C2 N1 14.06(17) . . . . ?
C12 C11 C2 C3 -167.11(14) . . . . ?
C2 N1 C13 C12 -20.39(16) . . . . ?
C2 N1 C13 C14 -145.59(14) . . . . ?
C2 C3 C4 C5 -177.09(15) . . . . ?
C2 C3 C8 C7 179.15(15) . . . . ?
C2 C11 C12 C13 -25.48(15) . . . . ?
C2 C11 C12 C26 -148.26(13) . . . . ?
C2 C11 C12 C22 92.70(14) . . . . ?
C14 C13 C12 C26 -89.02(16) . . . . ?
C14 C13 C12 C11 150.44(13) . . . . ?
C14 C13 C12 C22 30.26(17) . . . . ?
C14 C15 C18 O20 -73.85(16) . . . . ?
C14 C15 C18 O19 106.72(18) . . . . ?
C8 C3 C4 C5 2.2(2) . . . . ?
C8 C3 C2 N1 168.32(15) . . . . ?
C8 C3 C2 C11 -10.3(2) . . . . ?
C8 C7 C6 O9 -179.51(15) . . . . ?
C8 C7 C6 C5 1.3(2) . . . . ?
C17 C15 C18 O20 45.71(17) . . . . ?
C17 C15 C18 O19 -133.72(17) . . . . ?
C10 O9 C6 C7 176.94(14) . . . . ?
C10 O9 C6 C5 -3.9(2) . . . . ?
C25 O24 C22 O23 0.3(2) . . . . ?
C25 O24 C22 C12 -178.38(12) . . . . ?
C29 O28 C26 O27 2.5(2) . . . . ?
C29 O28 C26 C12 -178.55(13) . . . . ?
C21 O20 C18 O19 4.9(2) . . . . ?
C21 O20 C18 C15 -174.56(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
