# 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. 
# 
#######################################################################

data_full
_database_code_depnum_ccdc_archive 'CCDC 2426778'
loop_
_audit_author_name
_audit_author_address
"Alexander Smol'yakov"
;Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-02-25 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2025-02-25
_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         'C17 H17 N2 O, C2 H3 O2, C2 H4 O2'
_chemical_formula_sum            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
_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                   7.6144(9)
_cell_length_b                   9.7829(11)
_cell_length_c                   14.1330(15)
_cell_angle_alpha                78.875(5)
_cell_angle_beta                 83.922(4)
_cell_angle_gamma                70.003(4)
_cell_volume                     969.81(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0365 after correction.
The Ratio of minimum to maximum transmission is 0.9425.
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    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14029
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.247
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3065
_reflns_number_total             3792
_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         0.679
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.085
_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)+(0.0673P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C28(H28A,H28B,
 H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O18 O 0.09328(15) 1.18714(12) 0.43745(8) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.59778(17) 0.58354(13) 0.67017(9) 0.0156(3) Uani 1 1 d . . . . .
N20 N 0.69934(19) 0.46782(14) 0.74127(10) 0.0221(3) Uani 1 1 d . . . . .
H20A H 0.661089 0.489862 0.797744 0.027 Uiso 1 1 d R U . . .
H20B H 0.681565 0.386774 0.737073 0.027 Uiso 1 1 d R U . . .
C2 C 0.6414(2) 0.57614(17) 0.57290(11) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.5495(2) 0.69179(17) 0.50613(11) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.577037 0.686405 0.439525 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4143(2) 0.81968(16) 0.53314(11) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.3191(2) 0.94032(17) 0.46440(11) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.341848 0.936433 0.397414 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1929(2) 1.06375(17) 0.49509(11) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.1563(2) 1.06989(17) 0.59500(12) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.070077 1.156593 0.614960 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2426(2) 0.95401(17) 0.66205(12) 0.0193(3) Uani 1 1 d . . . . .
H8 H 0.214572 0.959100 0.728652 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3757(2) 0.82389(16) 0.63361(11) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.4679(2) 0.70093(16) 0.70154(11) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.4241(2) 0.69589(16) 0.80685(11) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.4706(2) 0.78746(18) 0.85631(12) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.534047 0.852280 0.823054 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4248(2) 0.7846(2) 0.95408(12) 0.0265(4) Uani 1 1 d . . . . .
H13 H 0.458783 0.846172 0.987895 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3297(2) 0.6923(2) 1.00249(12) 0.0285(4) Uani 1 1 d . . . . .
H14 H 0.298785 0.690033 1.069548 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2799(2) 0.60328(19) 0.95288(13) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.212796 0.541048 0.985933 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3269(2) 0.60400(18) 0.85560(12) 0.0239(4) Uani 1 1 d . . . . .
H16 H 0.292919 0.542004 0.822123 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7896(2) 0.44138(17) 0.54680(12) 0.0203(4) Uani 1 1 d . . . . .
H17A H 0.908879 0.432612 0.571824 0.030 Uiso 1 1 calc R U . . .
H17B H 0.802328 0.449050 0.476416 0.030 Uiso 1 1 calc R U . . .
H17C H 0.754820 0.354032 0.575043 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1185(2) 1.19124(18) 0.33538(12) 0.0227(4) Uani 1 1 d . . . . .
H19A H 0.042252 1.287871 0.302324 0.034 Uiso 1 1 calc R U . . .
H19B H 0.079828 1.113960 0.317771 0.034 Uiso 1 1 calc R U . . .
H19C H 0.250596 1.174715 0.316071 0.034 Uiso 1 1 calc R U . . .
O21 O 0.10386(16) 0.43462(13) 0.70208(9) 0.0303(3) Uani 1 1 d . . . . .
O24 O 0.39770(15) 0.29584(12) 0.72811(8) 0.0243(3) Uani 1 1 d . . . . .
C22 C 0.2216(2) 0.33558(18) 0.75215(12) 0.0208(4) Uani 1 1 d . . . . .
C23 C 0.1623(3) 0.2584(2) 0.84641(13) 0.0347(5) Uani 1 1 d . . . . .
H23A H 0.269001 0.174321 0.872346 0.052 Uiso 1 1 calc R U . . .
H23B H 0.061149 0.223166 0.835770 0.052 Uiso 1 1 calc R U . . .
H23C H 0.118141 0.327373 0.892466 0.052 Uiso 1 1 calc R U . . .
O25 O 0.59515(16) 0.08106(13) 0.83386(9) 0.0286(3) Uani 1 1 d . . . . .
H25 H 0.534167 0.159852 0.799361 0.043 Uiso 1 1 calc R U . . .
O26 O 0.83758(16) 0.14606(13) 0.76504(9) 0.0284(3) Uani 1 1 d . . . . .
C27 C 0.7713(2) 0.06567(17) 0.82392(11) 0.0200(4) Uani 1 1 d . . . . .
C28 C 0.8910(2) -0.0612(2) 0.89207(13) 0.0290(4) Uani 1 1 d . . . . .
H28A H 0.858083 -0.042968 0.958503 0.044 Uiso 1 1 calc R U . . .
H28B H 1.023009 -0.071226 0.876946 0.044 Uiso 1 1 calc R U . . .
H28C H 0.870198 -0.152217 0.885275 0.044 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
O18 C6 1.3494(19) . ?
O18 C19 1.4296(19) . ?
N1 N20 1.4199(18) . ?
N1 C2 1.390(2) . ?
N1 C10 1.3493(19) . ?
N20 H20A 0.8617 . ?
N20 H20B 0.8624 . ?
C2 C3 1.359(2) . ?
C2 C17 1.493(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(2) . ?
C4 C5 1.408(2) . ?
C4 C9 1.425(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(2) . ?
C6 C7 1.419(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.350(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.428(2) . ?
C9 C10 1.407(2) . ?
C10 C11 1.485(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.393(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O21 C22 1.233(2) . ?
O24 C22 1.289(2) . ?
C22 C23 1.506(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O25 H25 0.8400 . ?
O25 C27 1.293(2) . ?
O26 C27 1.223(2) . ?
C27 C28 1.500(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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 O18 C19 117.94(12) . . ?
C2 N1 N20 119.82(12) . . ?
C10 N1 N20 117.20(12) . . ?
C10 N1 C2 122.88(13) . . ?
N1 N20 H20A 109.3 . . ?
N1 N20 H20B 109.9 . . ?
H20A N20 H20B 109.2 . . ?
N1 C2 C17 118.11(13) . . ?
C3 C2 N1 118.82(13) . . ?
C3 C2 C17 123.07(14) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.72(14) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C9 117.70(14) . . ?
C5 C4 C3 122.08(14) . . ?
C5 C4 C9 120.22(14) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.43(14) . . ?
C6 C5 H5 120.3 . . ?
O18 C6 C5 125.69(14) . . ?
O18 C6 C7 113.63(13) . . ?
C5 C6 C7 120.68(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.81(14) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.50(15) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.34(14) . . ?
C10 C9 C4 119.66(13) . . ?
C10 C9 C8 122.00(14) . . ?
N1 C10 C9 119.15(14) . . ?
N1 C10 C11 119.03(13) . . ?
C9 C10 C11 121.81(13) . . ?
C12 C11 C10 120.67(14) . . ?
C12 C11 C16 119.53(15) . . ?
C16 C11 C10 119.72(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.19(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.16(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.71(16) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.61(16) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.79(16) . . ?
C15 C16 H16 120.1 . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
C2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 C22 O24 122.50(15) . . ?
O21 C22 C23 120.00(15) . . ?
O24 C22 C23 117.49(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 O25 H25 109.5 . . ?
O25 C27 C28 113.94(14) . . ?
O26 C27 O25 124.13(15) . . ?
O26 C27 C28 121.92(15) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O18 C6 C7 C8 178.88(14) . . . . ?
N1 C2 C3 C4 1.3(2) . . . . ?
N1 C10 C11 C12 112.36(17) . . . . ?
N1 C10 C11 C16 -71.00(19) . . . . ?
N20 N1 C2 C3 -176.42(13) . . . . ?
N20 N1 C2 C17 2.9(2) . . . . ?
N20 N1 C10 C9 174.35(12) . . . . ?
N20 N1 C10 C11 -6.52(19) . . . . ?
C2 N1 C10 C9 -2.0(2) . . . . ?
C2 N1 C10 C11 177.08(13) . . . . ?
C2 C3 C4 C5 179.67(14) . . . . ?
C2 C3 C4 C9 -0.3(2) . . . . ?
C3 C4 C5 C6 -178.03(14) . . . . ?
C3 C4 C9 C8 178.47(13) . . . . ?
C3 C4 C9 C10 -1.9(2) . . . . ?
C4 C5 C6 O18 179.48(14) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C9 C10 N1 3.0(2) . . . . ?
C4 C9 C10 C11 -176.08(13) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
C5 C4 C9 C10 178.18(13) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 1.4(2) . . . . ?
C7 C8 C9 C4 -0.2(2) . . . . ?
C7 C8 C9 C10 -179.81(14) . . . . ?
C8 C9 C10 N1 -177.34(13) . . . . ?
C8 C9 C10 C11 3.6(2) . . . . ?
C9 C4 C5 C6 1.9(2) . . . . ?
C9 C10 C11 C12 -68.5(2) . . . . ?
C9 C10 C11 C16 108.10(17) . . . . ?
C10 N1 C2 C3 -0.1(2) . . . . ?
C10 N1 C2 C17 179.18(13) . . . . ?
C10 C11 C12 C13 178.32(14) . . . . ?
C10 C11 C16 C15 -177.58(15) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C16 C11 C12 C13 1.7(2) . . . . ?
C17 C2 C3 C4 -177.96(14) . . . . ?
C19 O18 C6 C5 0.5(2) . . . . ?
C19 O18 C6 C7 -179.28(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
