# 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_me95
_database_code_depnum_ccdc_archive 'CCDC 2467397'
loop_
_audit_author_name
_audit_author_address
'Alexei A. Anisimov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N O7'
_chemical_formula_sum            'C24 H19 N O7'
_chemical_formula_weight         433.40
_chemical_absolute_configuration unk
_chemical_melting_point          420
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.6947(5)
_cell_length_b                   17.4535(12)
_cell_length_c                   14.9070(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2002.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3548
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.9012.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21640
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.586
_diffrn_reflns_theta_min         1.797
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4140
_reflns_number_total             6045
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.229
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         6045
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      0.997
_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)+(0.0204P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0972
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6080(2) 0.80935(9) 0.55173(12) 0.0226(4) Uani 1 1 d . . . . .
N1 N 0.5853(3) 0.68668(11) 0.59165(15) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.6363(3) 0.73398(14) 0.53019(16) 0.0201(6) Uani 1 1 d . . . . .
O2 O 0.3066(2) 0.69271(9) 0.87979(11) 0.0264(4) Uani 1 1 d . . . . .
C2 C 0.5161(3) 0.73229(14) 0.65958(16) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.3158(2) 0.56514(10) 0.89809(12) 0.0300(5) Uani 1 1 d . . . . .
C3 C 0.5299(3) 0.80760(14) 0.63522(17) 0.0222(6) Uani 1 1 d . . . . .
O4 O 0.9050(3) 0.58862(11) 0.15632(12) 0.0348(5) Uani 1 1 d . . . . .
C4 C 0.4766(4) 0.88261(15) 0.67342(18) 0.0286(6) Uani 1 1 d . . . . .
H4A H 0.567758 0.920614 0.662223 0.043 Uiso 1 1 calc R U . . .
H4B H 0.458532 0.877283 0.738200 0.043 Uiso 1 1 calc R U . . .
H4C H 0.368180 0.899401 0.645037 0.043 Uiso 1 1 calc R U . . .
O5 O 0.9381(3) 0.71470(11) 0.13262(13) 0.0374(5) Uani 1 1 d . . . . .
C5 C 0.3671(4) 0.74660(14) 0.81402(17) 0.0230(6) Uani 1 1 d . . . . .
H5A H 0.455975 0.781037 0.840109 0.028 Uiso 1 1 calc R U . . .
H5B H 0.269669 0.778049 0.791095 0.028 Uiso 1 1 calc R U . . .
O6 O 0.7194(2) 0.59474(10) 0.87760(11) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.4439(3) 0.69882(13) 0.74028(16) 0.0193(5) Uani 1 1 d . . . . .
O7 O 0.8058(2) 0.47259(10) 0.88467(12) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.4398(3) 0.62460(14) 0.76578(16) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.3517(3) 0.62047(15) 0.85354(16) 0.0231(6) Uani 1 1 d . . . . .
C9 C 0.5046(3) 0.55415(14) 0.72170(16) 0.0204(5) Uani 1 1 d . . . . .
C10 C 0.6289(3) 0.50700(14) 0.76279(17) 0.0218(6) Uani 1 1 d . . . . .
C11 C 0.6814(4) 0.43976(15) 0.72004(18) 0.0283(6) Uani 1 1 d . . . . .
H11 H 0.765927 0.407801 0.747588 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6118(4) 0.41914(16) 0.63797(19) 0.0328(7) Uani 1 1 d . . . . .
H12 H 0.647453 0.372963 0.609700 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4906(4) 0.46577(15) 0.59732(19) 0.0294(6) Uani 1 1 d . . . . .
H13 H 0.443977 0.452067 0.540529 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4366(3) 0.53249(14) 0.63901(18) 0.0242(6) Uani 1 1 d . . . . .
H14 H 0.351993 0.563943 0.610793 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7180(3) 0.53066(14) 0.84703(16) 0.0208(5) Uani 1 1 d . . . . .
C16 C 0.9186(3) 0.49281(16) 0.95863(19) 0.0296(7) Uani 1 1 d . . . . .
H16A H 1.006203 0.529546 0.938007 0.044 Uiso 1 1 calc R U . . .
H16B H 0.976358 0.446642 0.981202 0.044 Uiso 1 1 calc R U . . .
H16C H 0.849499 0.515941 1.006771 0.044 Uiso 1 1 calc R U . . .
C17 C 0.7102(4) 0.71539(14) 0.44297(17) 0.0213(6) Uani 1 1 d . . . . .
C18 C 0.7052(4) 0.63918(15) 0.41414(18) 0.0251(6) Uani 1 1 d . . . . .
H18 H 0.659390 0.600609 0.452380 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7672(4) 0.61990(15) 0.32970(17) 0.0255(6) Uani 1 1 d . . . . .
H19 H 0.762880 0.568188 0.309922 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8355(4) 0.67629(15) 0.27403(17) 0.0243(6) Uani 1 1 d . . . . .
C21 C 0.8431(4) 0.75161(15) 0.30352(18) 0.0253(6) Uani 1 1 d . . . . .
H21 H 0.891575 0.789862 0.265717 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7809(4) 0.77162(14) 0.38718(18) 0.0252(6) Uani 1 1 d . . . . .
H22 H 0.786174 0.823377 0.406698 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8947(4) 0.65338(17) 0.18278(17) 0.0270(6) Uani 1 1 d . . . . .
C24 C 0.9937(5) 0.69794(18) 0.04154(19) 0.0437(8) Uani 1 1 d . . . . .
H24A H 0.897189 0.674850 0.008207 0.066 Uiso 1 1 calc R U . . .
H24B H 1.091787 0.662170 0.043062 0.066 Uiso 1 1 calc R U . . .
H24C H 1.029523 0.745514 0.011919 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 C1 1.372(3) . ?
O1 C3 1.382(3) . ?
N1 C1 1.294(3) . ?
N1 C2 1.394(3) . ?
C1 C17 1.456(3) . ?
O2 C5 1.436(3) . ?
O2 C8 1.365(3) . ?
C2 C3 1.368(3) . ?
C2 C6 1.448(3) . ?
O3 C8 1.204(3) . ?
C3 C4 1.485(3) . ?
O4 C23 1.200(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O5 C23 1.348(3) . ?
O5 C24 1.453(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.501(3) . ?
O6 C15 1.208(3) . ?
C6 C7 1.350(3) . ?
O7 C15 1.341(3) . ?
O7 C16 1.447(3) . ?
C7 C8 1.475(3) . ?
C7 C9 1.481(3) . ?
C9 C10 1.403(3) . ?
C9 C14 1.391(4) . ?
C10 C11 1.395(4) . ?
C10 C15 1.489(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.398(3) . ?
C17 C22 1.397(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(3) . ?
C20 C21 1.387(4) . ?
C20 C23 1.489(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9500 . ?
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
C1 O1 C3 104.99(18) . . ?
C1 N1 C2 105.41(19) . . ?
O1 C1 C17 119.0(2) . . ?
N1 C1 O1 113.5(2) . . ?
N1 C1 C17 127.5(2) . . ?
C8 O2 C5 109.07(19) . . ?
N1 C2 C6 121.3(2) . . ?
C3 C2 N1 109.0(2) . . ?
C3 C2 C6 129.6(2) . . ?
O1 C3 C4 116.5(2) . . ?
C2 C3 O1 107.1(2) . . ?
C2 C3 C4 136.4(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C23 O5 C24 115.6(2) . . ?
O2 C5 H5A 110.7 . . ?
O2 C5 H5B 110.7 . . ?
O2 C5 C6 105.29(19) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C2 C6 C5 122.4(2) . . ?
C7 C6 C2 129.0(2) . . ?
C7 C6 C5 108.5(2) . . ?
C15 O7 C16 115.9(2) . . ?
C6 C7 C8 107.9(2) . . ?
C6 C7 C9 131.6(2) . . ?
C8 C7 C9 120.5(2) . . ?
O2 C8 C7 109.0(2) . . ?
O3 C8 O2 121.6(2) . . ?
O3 C8 C7 129.3(2) . . ?
C10 C9 C7 121.5(2) . . ?
C14 C9 C7 119.5(2) . . ?
C14 C9 C10 118.9(2) . . ?
C9 C10 C15 121.3(2) . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 C15 119.0(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
O6 C15 O7 122.5(2) . . ?
O6 C15 C10 125.4(2) . . ?
O7 C15 C10 112.0(2) . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C1 118.4(2) . . ?
C22 C17 C1 121.8(2) . . ?
C22 C17 C18 119.7(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C23 118.1(2) . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 C23 122.1(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.7(2) . . ?
C21 C22 H22 120.2 . . ?
O4 C23 O5 123.3(2) . . ?
O4 C23 C20 125.0(3) . . ?
O5 C23 C20 111.7(2) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 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 C1 C17 C18 -166.9(2) . . . . ?
O1 C1 C17 C22 11.4(4) . . . . ?
N1 C1 C17 C18 10.1(4) . . . . ?
N1 C1 C17 C22 -171.6(3) . . . . ?
N1 C2 C3 O1 0.0(3) . . . . ?
N1 C2 C3 C4 176.7(3) . . . . ?
N1 C2 C6 C5 -179.5(2) . . . . ?
N1 C2 C6 C7 4.3(4) . . . . ?
C1 O1 C3 C2 0.3(3) . . . . ?
C1 O1 C3 C4 -177.2(2) . . . . ?
C1 N1 C2 C3 -0.3(3) . . . . ?
C1 N1 C2 C6 179.5(2) . . . . ?
C1 C17 C18 C19 177.1(2) . . . . ?
C1 C17 C22 C21 -177.4(3) . . . . ?
O2 C5 C6 C2 178.5(2) . . . . ?
O2 C5 C6 C7 -4.6(3) . . . . ?
C2 N1 C1 O1 0.5(3) . . . . ?
C2 N1 C1 C17 -176.6(2) . . . . ?
C2 C6 C7 C8 -180.0(2) . . . . ?
C2 C6 C7 C9 -0.3(5) . . . . ?
C3 O1 C1 N1 -0.5(3) . . . . ?
C3 O1 C1 C17 176.9(2) . . . . ?
C3 C2 C6 C5 0.4(4) . . . . ?
C3 C2 C6 C7 -175.8(3) . . . . ?
C5 O2 C8 O3 179.7(2) . . . . ?
C5 O2 C8 C7 -2.1(3) . . . . ?
C5 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C9 -176.9(3) . . . . ?
C6 C2 C3 O1 -179.8(2) . . . . ?
C6 C2 C3 C4 -3.1(5) . . . . ?
C6 C7 C8 O2 -0.9(3) . . . . ?
C6 C7 C8 O3 177.1(3) . . . . ?
C6 C7 C9 C10 120.4(3) . . . . ?
C6 C7 C9 C14 -61.9(4) . . . . ?
C7 C9 C10 C11 177.7(2) . . . . ?
C7 C9 C10 C15 -8.0(4) . . . . ?
C7 C9 C14 C13 -178.0(2) . . . . ?
C8 O2 C5 C6 4.0(3) . . . . ?
C8 C7 C9 C10 -59.9(3) . . . . ?
C8 C7 C9 C14 117.8(3) . . . . ?
C9 C7 C8 O2 179.4(2) . . . . ?
C9 C7 C8 O3 -2.6(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C15 O6 -14.8(4) . . . . ?
C9 C10 C15 O7 168.0(2) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C10 C15 O6 159.5(3) . . . . ?
C11 C10 C15 O7 -17.7(3) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C9 0.8(4) . . . . ?
C14 C9 C10 C11 0.0(4) . . . . ?
C14 C9 C10 C15 174.3(2) . . . . ?
C15 C10 C11 C12 -174.7(2) . . . . ?
C16 O7 C15 O6 -6.7(3) . . . . ?
C16 O7 C15 C10 170.6(2) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C18 C19 C20 C23 -177.9(2) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C19 C20 C23 O4 -8.2(4) . . . . ?
C19 C20 C23 O5 172.6(2) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C21 C20 C23 O4 173.4(3) . . . . ?
C21 C20 C23 O5 -5.9(4) . . . . ?
C22 C17 C18 C19 -1.3(4) . . . . ?
C23 C20 C21 C22 177.4(3) . . . . ?
C24 O5 C23 O4 2.1(4) . . . . ?
C24 O5 C23 C20 -178.6(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_sn14
_database_code_depnum_ccdc_archive 'CCDC 2467399'
loop_
_audit_author_name
_audit_author_address
'Alexei A. Anisimov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_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         'C19 H16 O5'
_chemical_formula_sum            'C19 H16 O5'
_chemical_formula_weight         324.32
_chemical_melting_point          387
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.642(8)
_cell_length_b                   12.087(4)
_cell_length_c                   11.817(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.960(9)
_cell_angle_gamma                90
_cell_volume                     3109.2(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    881
_cell_measurement_temperature    120
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.7575.
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    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1256
_diffrn_reflns_av_unetI/netI     0.2150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13845
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.590
_diffrn_reflns_theta_min         1.871
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1953
_reflns_number_total             4738
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.323
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2247
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.2201
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.38252(10) 0.35684(18) 0.2717(2) 0.027(2) Uani 1 1 d . . . . .
C1 C 0.33913(16) 0.3670(3) 0.3214(3) 0.027(2) Uani 1 1 d . . . . .
O2 O 0.30162(11) 0.2954(2) 0.3064(2) 0.035(2) Uani 1 1 d . . . . .
C2 C 0.34793(14) 0.4724(3) 0.3866(3) 0.020(2) Uani 1 1 d . . . . .
O3 O 0.52840(11) 0.9013(2) 0.6211(2) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.39721(14) 0.5236(3) 0.3819(3) 0.020(2) Uani 1 1 d . . . . .
O4 O 0.38312(11) 0.3361(2) 0.5959(2) 0.033(2) Uani 1 1 d . . . . .
C4 C 0.42185(15) 0.4518(3) 0.3062(3) 0.024(2) Uani 1 1 d . . . . .
H4A H 0.420662 0.492212 0.232466 0.028 Uiso 1 1 calc R U . . .
H4B H 0.464776 0.429503 0.355376 0.028 Uiso 1 1 calc R U . . .
O5 O 0.30327(11) 0.2777(2) 0.6367(2) 0.034(2) Uani 1 1 d . . . . .
C5 C 0.42961(14) 0.6243(3) 0.4394(3) 0.021(2) Uani 1 1 d . . . . .
C6 C 0.41581(15) 0.6830(3) 0.5295(3) 0.023(2) Uani 1 1 d . . . . .
H6 H 0.383004 0.658510 0.550579 0.028 Uiso 1 1 calc R U . . .
C7 C 0.44896(15) 0.7744(3) 0.5865(3) 0.026(2) Uani 1 1 d . . . . .
H7 H 0.439030 0.812424 0.646678 0.032 Uiso 1 1 calc R U . . .
C8 C 0.49701(15) 0.8118(3) 0.5568(3) 0.026(2) Uani 1 1 d . . . . .
C9 C 0.51139(15) 0.7569(3) 0.4679(3) 0.026(2) Uani 1 1 d . . . . .
H9 H 0.543699 0.782785 0.445951 0.031 Uiso 1 1 calc R U . . .
C10 C 0.47803(15) 0.6646(3) 0.4123(3) 0.026(2) Uani 1 1 d . . . . .
H10 H 0.488516 0.626707 0.352721 0.031 Uiso 1 1 calc R U . . .
C11 C 0.58142(17) 0.9369(3) 0.6013(4) 0.045(2) Uani 1 1 d . . . . .
H11A H 0.569459 0.957723 0.514864 0.067 Uiso 1 1 calc R U . . .
H11B H 0.611446 0.876613 0.621626 0.067 Uiso 1 1 calc R U . . .
H11C H 0.599726 1.000946 0.653716 0.067 Uiso 1 1 calc R U . . .
C12 C 0.30255(14) 0.5067(3) 0.4387(3) 0.020(2) Uani 1 1 d . . . . .
C13 C 0.29110(14) 0.4433(3) 0.5286(3) 0.020(2) Uani 1 1 d . . . . .
C14 C 0.24391(15) 0.4741(3) 0.5634(3) 0.026(2) Uani 1 1 d . . . . .
H14 H 0.235902 0.430808 0.622621 0.032 Uiso 1 1 calc R U . . .
C15 C 0.20816(15) 0.5660(3) 0.5146(3) 0.028(2) Uani 1 1 d . . . . .
H15 H 0.176434 0.586346 0.540945 0.033 Uiso 1 1 calc R U . . .
C16 C 0.21906(15) 0.6285(3) 0.4263(3) 0.027(2) Uani 1 1 d . . . . .
H16 H 0.194505 0.691651 0.391364 0.032 Uiso 1 1 calc R U . . .
C17 C 0.26572(15) 0.5985(3) 0.3895(3) 0.024(2) Uani 1 1 d . . . . .
H17 H 0.272789 0.641722 0.329082 0.029 Uiso 1 1 calc R U . . .
C18 C 0.33078(15) 0.3480(3) 0.5865(3) 0.022(2) Uani 1 1 d . . . . .
C19 C 0.33897(16) 0.1824(3) 0.6994(4) 0.035(2) Uani 1 1 d . . . . .
H19A H 0.354246 0.143517 0.644158 0.052 Uiso 1 1 calc R U . . .
H19B H 0.313028 0.132345 0.723547 0.052 Uiso 1 1 calc R U . . .
H19C H 0.373797 0.206833 0.772773 0.052 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 1.373(4) . ?
O1 C4 1.433(4) . ?
C1 O2 1.202(4) . ?
C1 C2 1.461(5) . ?
C2 C3 1.339(4) . ?
C2 C12 1.489(4) . ?
O3 C8 1.363(4) . ?
O3 C11 1.429(4) . ?
C3 C4 1.515(4) . ?
C3 C5 1.458(4) . ?
O4 C18 1.207(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O5 C18 1.341(4) . ?
O5 C19 1.449(4) . ?
C5 C6 1.419(4) . ?
C5 C10 1.392(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(4) . ?
C8 C9 1.392(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.419(4) . ?
C12 C17 1.391(4) . ?
C13 C14 1.382(4) . ?
C13 C18 1.475(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(4) . ?
C17 H17 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
C1 O1 C4 108.4(2) . . ?
O1 C1 C2 109.1(3) . . ?
O2 C1 O1 120.3(3) . . ?
O2 C1 C2 130.6(3) . . ?
C1 C2 C12 118.9(3) . . ?
C3 C2 C1 109.1(3) . . ?
C3 C2 C12 131.9(3) . . ?
C8 O3 C11 118.0(3) . . ?
C2 C3 C4 107.5(3) . . ?
C2 C3 C5 132.3(3) . . ?
C5 C3 C4 120.0(3) . . ?
O1 C4 C3 105.7(3) . . ?
O1 C4 H4A 110.6 . . ?
O1 C4 H4B 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
C18 O5 C19 116.3(3) . . ?
C6 C5 C3 122.3(3) . . ?
C10 C5 C3 121.0(3) . . ?
C10 C5 C6 116.6(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
O3 C8 C7 116.0(3) . . ?
O3 C8 C9 124.0(3) . . ?
C7 C8 C9 120.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C5 C10 H10 118.5 . . ?
C9 C10 C5 122.9(3) . . ?
C9 C10 H10 118.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C2 122.5(3) . . ?
C17 C12 C2 118.9(3) . . ?
C17 C12 C13 118.3(3) . . ?
C12 C13 C18 119.8(3) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 C18 120.9(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
O4 C18 O5 122.7(3) . . ?
O4 C18 C13 125.4(3) . . ?
O5 C18 C13 111.7(3) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 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 C1 C2 C3 -2.7(4) . . . . ?
O1 C1 C2 C12 174.4(3) . . . . ?
C1 O1 C4 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C1 C2 C3 C5 -173.8(3) . . . . ?
C1 C2 C12 C13 60.3(4) . . . . ?
C1 C2 C12 C17 -113.4(3) . . . . ?
O2 C1 C2 C3 178.1(4) . . . . ?
O2 C1 C2 C12 -4.8(6) . . . . ?
C2 C3 C4 O1 -0.8(3) . . . . ?
C2 C3 C5 C6 7.7(6) . . . . ?
C2 C3 C5 C10 -175.4(3) . . . . ?
C2 C12 C13 C14 -173.3(3) . . . . ?
C2 C12 C13 C18 8.7(5) . . . . ?
C2 C12 C17 C16 174.1(3) . . . . ?
O3 C8 C9 C10 177.3(3) . . . . ?
C3 C2 C12 C13 -123.3(4) . . . . ?
C3 C2 C12 C17 63.0(5) . . . . ?
C3 C5 C6 C7 176.8(3) . . . . ?
C3 C5 C10 C9 -177.5(3) . . . . ?
C4 O1 C1 O2 -178.5(3) . . . . ?
C4 O1 C1 C2 2.2(3) . . . . ?
C4 C3 C5 C6 -167.7(3) . . . . ?
C4 C3 C5 C10 9.2(5) . . . . ?
C5 C3 C4 O1 175.7(3) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C5 C10 C9 -0.4(5) . . . . ?
C6 C7 C8 O3 -178.1(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C5 1.1(5) . . . . ?
C10 C5 C6 C7 -0.3(5) . . . . ?
C11 O3 C8 C7 174.7(3) . . . . ?
C11 O3 C8 C9 -3.8(5) . . . . ?
C12 C2 C3 C4 -174.6(3) . . . . ?
C12 C2 C3 C5 9.6(6) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C12 C13 C18 O4 24.7(5) . . . . ?
C12 C13 C18 O5 -159.8(3) . . . . ?
C13 C12 C17 C16 0.1(5) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C14 C13 C18 O4 -153.3(3) . . . . ?
C14 C13 C18 O5 22.2(4) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 0.4(5) . . . . ?
C17 C12 C13 C18 -177.6(3) . . . . ?
C18 C13 C14 C15 176.9(3) . . . . ?
C19 O5 C18 O4 -2.6(5) . . . . ?
C19 O5 C18 C13 -178.3(3) . . . . ?

_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_me148ab
_database_code_depnum_ccdc_archive 'CCDC 2467398'
loop_
_audit_author_name
_audit_author_address
'Alexei A. Anisimov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C18 H14 O5'
_chemical_formula_sum            'C18 H14 O5'
_chemical_formula_weight         310.309
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00270 0.00180 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.00940 0.00690 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.6200(15)
_cell_length_b                   7.8600(16)
_cell_length_c                   13.160(3)
_cell_angle_alpha                104.32(3)
_cell_angle_beta                 95.25(3)
_cell_angle_gamma                101.42(3)
_cell_volume                     740.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2567
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.342
_cell_measurement_theta_min      1.356
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XSCALE (Kabsch, 2010)'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prism
_exptl_crystal_F_000             324.191
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.9896
_diffrn_reflns_Laue_measured_fraction_max 0.9883
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12597
_diffrn_reflns_point_group_measured_fraction_full 0.9896
_diffrn_reflns_point_group_measured_fraction_max 0.9883
_diffrn_reflns_theta_full        26.8477
_diffrn_reflns_theta_max         30.89
_diffrn_reflns_theta_min         1.71
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Rayonix SX 165 area detector'
_diffrn_measured_fraction_theta_full 0.9896
_diffrn_measured_fraction_theta_max 0.9883
_diffrn_measurement_device       'Rayonix CCD'
_diffrn_measurement_device_type  'Marexperts dtb goniostat'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.75270
_diffrn_source                   'Belok beamline of NIC "Kurchatov Institute"'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3306
_reflns_number_total             3894
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3602
_refine_diff_density_min         -0.2634
_refine_diff_density_rms         0.0524
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             12.6110
_refine_ls_goodness_of_fit_ref   1.0250
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.0250
_refine_ls_shift/su_max          -0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.2148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1168
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17)
1.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
C1 C 0.22309(15) 0.61500(16) 0.46389(9) 0.0251(2) Uani 1.000000 .
O1 O 0.13603(11) 0.46606(11) 0.39281(7) 0.0282(2) Uani 1.000000 .
H1 H 0.0391(11) 0.4242(13) 0.4128(7) 0.0422(3) Uiso 1.000000 GR
C2 C 0.40318(14) 0.69942(15) 0.44158(9) 0.0238(2) Uani 1.000000 .
O2 O 0.16624(12) 0.67816(13) 0.54601(7) 0.0344(2) Uani 1.000000 .
C3 C 0.52956(15) 0.80314(17) 0.52942(10) 0.0274(2) Uani 1.000000 .
H3 H 0.49445(15) 0.82417(17) 0.59805(10) 0.0329(3) Uiso 1.000000 R
O3 O 0.06647(11) 0.54488(12) 0.12170(7) 0.0294(2) Uani 1.000000 .
C4 C 0.70536(16) 0.87592(17) 0.51814(10) 0.0306(3) Uani 1.000000 .
H4 H 0.79076(16) 0.94487(17) 0.57859(10) 0.0367(3) Uiso 1.000000 R
O4 O 0.08889(12) 0.75122(13) 0.27715(7) 0.0321(2) Uani 1.000000 .
C5 C 0.75523(16) 0.84712(18) 0.41791(11) 0.0328(3) Uani 1.000000 .
H5 H 0.87627(16) 0.89409(18) 0.40960(11) 0.0393(3) Uiso 1.000000 R
O5 O 0.86330(11) 0.05238(12) 0.07031(7) 0.0295(2) Uani 1.000000 .
C6 C 0.62934(16) 0.74998(17) 0.32948(10) 0.0297(3) Uani 1.000000 .
H6 H 0.66451(16) 0.73442(17) 0.26096(10) 0.0357(3) Uiso 1.000000 R
C7 C 0.45143(14) 0.67449(15) 0.33938(9) 0.0241(2) Uani 1.000000 .
C8 C 0.32207(14) 0.58336(15) 0.24124(9) 0.0238(2) Uani 1.000000 .
C9 C 0.15106(15) 0.63954(16) 0.22101(9) 0.0261(2) Uani 1.000000 .
C10 C 0.17386(15) 0.42523(16) 0.07293(9) 0.0264(2) Uani 1.000000 .
H10a H 0.10534(15) 0.29813(16) 0.05471(9) 0.0317(3) Uiso 1.000000 R
H10b H 0.21034(15) 0.45331(16) 0.00753(9) 0.0317(3) Uiso 1.000000 R
C11 C 0.33663(14) 0.45710(15) 0.15440(9) 0.0236(2) Uani 1.000000 .
C12 C 0.47572(14) 0.35382(15) 0.13431(9) 0.0240(2) Uani 1.000000 .
C13 C 0.57615(16) 0.31743(17) 0.21742(10) 0.0278(2) Uani 1.000000 .
H13 H 0.55501(16) 0.36300(17) 0.28799(10) 0.0334(3) Uiso 1.000000 R
C14 C 0.70571(16) 0.21664(17) 0.19957(10) 0.0278(2) Uani 1.000000 .
H14 H 0.77122(16) 0.19197(17) 0.25714(10) 0.0334(3) Uiso 1.000000 R
C15 C 0.73895(15) 0.15196(15) 0.09667(10) 0.0250(2) Uani 1.000000 .
C16 C 0.63990(15) 0.18617(16) 0.01213(9) 0.0264(2) Uani 1.000000 .
H16 H 0.66282(15) 0.14211(16) -0.05823(9) 0.0317(3) Uiso 1.000000 R
C17 C 0.50879(15) 0.28399(16) 0.03089(9) 0.0250(2) Uani 1.000000 .
H17 H 0.44000(15) 0.30425(16) -0.02709(9) 0.0300(3) Uiso 1.000000 R
C18 C 0.96946(18) 0.0177(2) 0.15552(11) 0.0356(3) Uani 1.000000 .
H18a H 1.0560(11) -0.0516(13) 0.12691(14) 0.0534(4) Uiso 1.000000 GR
H18b H 1.0353(12) 0.1325(2) 0.2051(5) 0.0534(4) Uiso 1.000000 GR
H18c H 0.8896(2) -0.0513(13) 0.1928(6) 0.0534(4) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3125(15) . ?
C1 C2 1.4897(16) . ?
C1 O2 1.2277(15) . ?
O1 H1 0.8400 . ?
C2 C3 1.3955(17) . ?
C2 C7 1.4040(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3852(16) . ?
O3 C9 1.3610(15) . ?
O3 C10 1.4382(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3833(19) . ?
O4 C9 1.2036(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3869(18) . ?
O5 C15 1.3603(14) . ?
O5 C18 1.4347(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3996(16) . ?
C7 C8 1.4774(17) . ?
C8 C9 1.4786(16) . ?
C8 C11 1.3450(17) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.5005(16) . ?
C11 C12 1.4622(16) . ?
C12 C13 1.3972(17) . ?
C12 C17 1.4017(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3847(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3891(17) . ?
C15 C16 1.3981(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3804(16) . ?
C17 H17 0.9500 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 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 C1 O1 115.42(10) . . ?
O2 C1 O1 123.25(10) . . ?
O2 C1 C2 121.25(10) . . ?
H1 O1 C1 109.5 . . ?
C3 C2 C1 116.43(10) . . ?
C7 C2 C1 123.67(10) . . ?
C7 C2 C3 119.87(10) . . ?
H3 C3 C2 119.47(7) . . ?
C4 C3 C2 121.06(11) . . ?
C4 C3 H3 119.47(7) . . ?
C10 O3 C9 109.38(9) . . ?
H4 C4 C3 120.35(7) . . ?
C5 C4 C3 119.29(11) . . ?
C5 C4 H4 120.35(7) . . ?
H5 C5 C4 119.85(7) . . ?
C6 C5 C4 120.31(11) . . ?
C6 C5 H5 119.85(7) . . ?
C18 O5 C15 117.11(9) . . ?
H6 C6 C5 119.41(7) . . ?
C7 C6 C5 121.19(11) . . ?
C7 C6 H6 119.41(7) . . ?
C6 C7 C2 118.21(11) . . ?
C8 C7 C2 123.68(10) . . ?
C8 C7 C6 117.98(10) . . ?
C9 C8 C7 121.13(10) . . ?
C11 C8 C7 130.48(10) . . ?
C11 C8 C9 108.11(10) . . ?
O4 C9 O3 121.85(11) . . ?
C8 C9 O3 108.73(10) . . ?
C8 C9 O4 129.41(11) . . ?
H10a C10 O3 110.72(6) . . ?
H10b C10 O3 110.72(6) . . ?
H10b C10 H10a 108.8 . . ?
C11 C10 O3 105.13(9) . . ?
C11 C10 H10a 110.72(6) . . ?
C11 C10 H10b 110.72(6) . . ?
C10 C11 C8 108.65(10) . . ?
C12 C11 C8 130.25(10) . . ?
C12 C11 C10 121.07(10) . . ?
C13 C12 C11 120.95(10) . . ?
C17 C12 C11 121.05(10) . . ?
C17 C12 C13 117.98(10) . . ?
H13 C13 C12 119.15(7) . . ?
C14 C13 C12 121.70(11) . . ?
C14 C13 H13 119.15(7) . . ?
H14 C14 C13 120.33(7) . . ?
C15 C14 C13 119.34(11) . . ?
C15 C14 H14 120.33(7) . . ?
C14 C15 O5 124.19(11) . . ?
C16 C15 O5 115.77(10) . . ?
C16 C15 C14 120.03(11) . . ?
H16 C16 C15 120.01(7) . . ?
C17 C16 C15 119.99(11) . . ?
C17 C16 H16 120.01(7) . . ?
C16 C17 C12 120.93(11) . . ?
H17 C17 C12 119.54(7) . . ?
H17 C17 C16 119.54(7) . . ?
H18a C18 O5 109.5 . . ?
H18b C18 O5 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O5 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 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
C1 C2 C3 C4 174.93(11) . . . . ?
C1 C2 C7 C6 -175.23(12) . . . . ?
C1 C2 C7 C8 8.95(14) . . . . ?
C2 C3 C4 C5 0.91(15) . . . . ?
C2 C7 C6 C5 -0.06(13) . . . . ?
C2 C7 C8 C9 52.37(13) . . . . ?
C2 C7 C8 C11 -134.36(12) . . . . ?
C3 C4 C5 C6 1.50(15) . . . . ?
O3 C9 C8 C7 174.60(8) . . . . ?
O3 C9 C8 C11 -0.02(10) . . . . ?
O3 C10 C11 C8 0.02(10) . . . . ?
O3 C10 C11 C12 177.99(8) . . . . ?
C4 C5 C6 C7 -1.93(16) . . . . ?
O4 C9 C8 C7 -3.86(16) . . . . ?
O4 C9 C8 C11 -178.48(14) . . . . ?
C5 C6 C7 C8 176.00(12) . . . . ?
O5 C15 C14 C13 179.77(11) . . . . ?
O5 C15 C16 C17 179.10(10) . . . . ?
C6 C7 C8 C9 -123.46(11) . . . . ?
C6 C7 C8 C11 49.81(14) . . . . ?
C7 C8 C11 C10 -173.94(13) . . . . ?
C7 C8 C11 C12 8.33(16) . . . . ?
C8 C11 C12 C13 27.39(15) . . . . ?
C8 C11 C12 C17 -154.45(12) . . . . ?
C10 C11 C12 C13 -150.10(11) . . . . ?
C10 C11 C12 C17 28.06(12) . . . . ?
C11 C12 C13 C14 178.63(11) . . . . ?
C11 C12 C17 C16 -179.85(10) . . . . ?
C12 C13 C14 C15 0.94(14) . . . . ?
C12 C17 C16 C15 1.50(13) . . . . ?
C13 C14 C15 C16 -1.09(14) . . . . ?
C14 C15 C16 C17 -0.12(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_melting_point          448
_refine_special_details          synchrotron
