# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2517247'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H29 N O2'
_chemical_formula_weight         315.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   26.224(3)
_cell_length_b                   6.2897(6)
_cell_length_c                   22.147(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.901(4)
_cell_angle_gamma                90
_cell_volume                     3609.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2928
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      26.47

_exptl_crystal_description       platelet
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14821
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3092
_reflns_number_gt                2220
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1073P)²+12.0630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3092
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.1093
_refine_ls_wR_factor_ref         0.2923
_refine_ls_wR_factor_gt          0.2758
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.65704(10) 0.5854(4) 0.59921(12) 0.0368(7) Uani 1 1 d . . . . .
N N 0.63879(12) 0.3658(5) 0.59284(15) 0.0338(8) Uani 1 1 d . . . . .
C15 C 0.84265(16) 0.5363(7) 0.65561(18) 0.0414(11) Uani 1 1 d . . . . .
C1 C 0.60316(16) 0.3372(7) 0.63899(19) 0.0387(10) Uani 1 1 d . . . . .
C6 C 0.56093(18) 0.5054(8) 0.6384(2) 0.0514(12) Uani 1 1 d . . . . .
H6C H 0.535919 0.489085 0.602178 0.077 Uiso 1 1 calc R U . . .
H6A H 0.576035 0.644510 0.638850 0.077 Uiso 1 1 calc R U . . .
H6B H 0.544349 0.488056 0.673815 0.077 Uiso 1 1 calc R U . . .
C5 C 0.61712(16) 0.3361(7) 0.52684(18) 0.0400(10) Uani 1 1 d . . . . .
C7 C 0.63598(19) 0.3395(9) 0.7016(2) 0.0553(13) Uani 1 1 d . . . . .
H7A H 0.615461 0.295791 0.731719 0.083 Uiso 1 1 calc R U . . .
H7B H 0.648789 0.480697 0.710755 0.083 Uiso 1 1 calc R U . . .
H7C H 0.664485 0.243520 0.701958 0.083 Uiso 1 1 calc R U . . .
C10 C 0.71062(15) 0.6043(7) 0.61798(18) 0.0366(10) Uani 1 1 d . . . . .
O2 O 0.77924(15) 0.8163(6) 0.6496(3) 0.119(2) Uani 1 1 d . . . . .
C12 C 0.78721(16) 0.5936(7) 0.6427(2) 0.0416(10) Uani 1 1 d . . . . .
C2 C 0.57951(18) 0.1148(7) 0.6282(2) 0.0518(12) Uani 1 1 d . . . . .
H2A H 0.606545 0.009555 0.637964 0.062 Uiso 1 1 calc R U . . .
H2B H 0.554597 0.093423 0.655721 0.062 Uiso 1 1 calc R U . . .
C3 C 0.55335(19) 0.0797(8) 0.5639(3) 0.0582(14) Uani 1 1 d . . . . .
H3B H 0.524719 0.177876 0.554207 0.070 Uiso 1 1 calc R U . . .
H3A H 0.539931 -0.064075 0.559362 0.070 Uiso 1 1 calc R U . . .
C8 C 0.66153(19) 0.3364(10) 0.4905(2) 0.0601(14) Uani 1 1 d . . . . .
H8A H 0.675654 0.477200 0.490234 0.090 Uiso 1 1 calc R U . . .
H8C H 0.649298 0.292367 0.449288 0.090 Uiso 1 1 calc R U . . .
H8B H 0.687793 0.239974 0.508886 0.090 Uiso 1 1 calc R U . . .
C9 C 0.57857(18) 0.5059(8) 0.4990(2) 0.0534(13) Uani 1 1 d . . . . .
H9A H 0.592827 0.644588 0.508678 0.080 Uiso 1 1 calc R U . . .
H9B H 0.546966 0.490978 0.515411 0.080 Uiso 1 1 calc R U . . .
H9C H 0.571794 0.488565 0.455413 0.080 Uiso 1 1 calc R U . . .
C16 C 0.85841(18) 0.3425(9) 0.6805(2) 0.0565(13) Uani 1 1 d . . . . .
H16 H 0.833983 0.247591 0.690831 0.068 Uiso 1 1 calc R U . . .
C4 C 0.59207(18) 0.1150(8) 0.5212(2) 0.0563(13) Uani 1 1 d . . . . .
H4B H 0.575015 0.095160 0.479527 0.068 Uiso 1 1 calc R U . . .
H4A H 0.618956 0.008288 0.529410 0.068 Uiso 1 1 calc R U . . .
C20 C 0.87968(18) 0.6776(9) 0.6414(2) 0.0540(13) Uani 1 1 d . . . . .
H20 H 0.869895 0.809974 0.624876 0.065 Uiso 1 1 calc R U . . .
C14 C 0.75352(17) 0.5425(11) 0.5821(2) 0.0669(16) Uani 1 1 d . . . . .
H14A H 0.753554 0.394297 0.569954 0.080 Uiso 1 1 calc R U . . .
H14B H 0.757803 0.637366 0.548715 0.080 Uiso 1 1 calc R U . . .
C13 C 0.74424(16) 0.4973(10) 0.6723(2) 0.0598(14) Uani 1 1 d . . . . .
H13B H 0.740750 0.555523 0.711977 0.072 Uiso 1 1 calc R U . . .
H13A H 0.743115 0.343142 0.672052 0.072 Uiso 1 1 calc R U . . .
C19 C 0.93138(19) 0.6202(10) 0.6521(3) 0.0667(15) Uani 1 1 d . . . . .
H19 H 0.956125 0.714960 0.642464 0.080 Uiso 1 1 calc R U . . .
C18 C 0.94652(19) 0.4263(11) 0.6767(3) 0.0684(16) Uani 1 1 d . . . . .
H18 H 0.981268 0.389401 0.684083 0.082 Uiso 1 1 calc R U . . .
C17 C 0.9095(2) 0.2870(10) 0.6902(3) 0.0714(17) Uani 1 1 d . . . . .
H17 H 0.919318 0.153710 0.706187 0.086 Uiso 1 1 calc R U . . .
C11 C 0.7238(2) 0.8344(10) 0.6326(5) 0.121(4) Uani 1 1 d . . . . .
H11A H 0.714554 0.925432 0.597229 0.145 Uiso 1 1 calc R U . . .
H11B H 0.707451 0.886250 0.666128 0.145 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 C10 1.407(5) . ?
O1 N 1.462(4) . ?
N C5 1.496(5) . ?
N C1 1.498(5) . ?
C15 C16 1.375(7) . ?
C15 C20 1.387(6) . ?
C15 C12 1.482(6) . ?
C1 C7 1.514(6) . ?
C1 C6 1.530(6) . ?
C1 C2 1.534(6) . ?
C6 H6C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C5 C8 1.515(6) . ?
C5 C9 1.533(6) . ?
C5 C4 1.535(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 C11 1.511(7) . ?
C10 C14 1.525(6) . ?
C10 C13 1.532(6) . ?
C10 C12 1.999(6) . ?
O2 C12 1.428(6) . ?
O2 C11 1.449(7) . ?
C12 C13 1.514(6) . ?
C12 C14 1.523(6) . ?
C2 C3 1.498(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.507(7) . ?
C3 H3B 0.9700 . ?
C3 H3A 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8B 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 C17 1.370(7) . ?
C16 H16 0.9300 . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C20 C19 1.387(7) . ?
C20 H20 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C19 C18 1.369(8) . ?
C19 H19 0.9300 . ?
C18 C17 1.374(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C10 O1 N 113.9(3) . . ?
O1 N C5 106.3(3) . . ?
O1 N C1 106.1(3) . . ?
C5 N C1 118.0(3) . . ?
C16 C15 C20 118.7(4) . . ?
C16 C15 C12 121.2(4) . . ?
C20 C15 C12 120.0(4) . . ?
N C1 C7 107.3(3) . . ?
N C1 C6 116.0(3) . . ?
C7 C1 C6 108.0(4) . . ?
N C1 C2 106.4(3) . . ?
C7 C1 C2 108.1(4) . . ?
C6 C1 C2 110.8(4) . . ?
C1 C6 H6C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N C5 C8 108.2(3) . . ?
N C5 C9 115.7(3) . . ?
C8 C5 C9 107.4(4) . . ?
N C5 C4 106.6(4) . . ?
C8 C5 C4 108.2(4) . . ?
C9 C5 C4 110.6(4) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C10 C11 109.2(4) . . ?
O1 C10 C14 127.4(3) . . ?
C11 C10 C14 101.1(5) . . ?
O1 C10 C13 128.4(3) . . ?
C11 C10 C13 99.7(5) . . ?
C14 C10 C13 85.2(3) . . ?
O1 C10 C12 173.1(3) . . ?
C11 C10 C12 77.7(3) . . ?
C14 C10 C12 49.0(2) . . ?
C13 C10 C12 48.6(2) . . ?
C12 O2 C11 101.9(4) . . ?
O2 C12 C15 111.9(4) . . ?
O2 C12 C13 102.4(4) . . ?
C15 C12 C13 126.3(4) . . ?
O2 C12 C14 103.1(4) . . ?
C15 C12 C14 122.5(4) . . ?
C13 C12 C14 85.9(3) . . ?
O2 C12 C10 80.7(3) . . ?
C15 C12 C10 167.1(4) . . ?
C13 C12 C10 49.4(2) . . ?
C14 C12 C10 49.1(2) . . ?
C3 C2 C1 113.4(4) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 108.7(4) . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
H3B C3 H3A 108.3 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C3 C4 C5 113.8(4) . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
H4B C4 H4A 107.7 . . ?
C15 C20 C19 119.6(5) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C12 C14 C10 82.0(3) . . ?
C12 C14 H14A 115.0 . . ?
C10 C14 H14A 115.0 . . ?
C12 C14 H14B 115.0 . . ?
C10 C14 H14B 115.0 . . ?
H14A C14 H14B 112.0 . . ?
C12 C13 C10 82.0(3) . . ?
C12 C13 H13B 115.0 . . ?
C10 C13 H13B 115.0 . . ?
C12 C13 H13A 115.0 . . ?
C10 C13 H13A 115.0 . . ?
H13B C13 H13A 112.0 . . ?
C18 C19 C20 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C18 C17 118.9(5) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
O2 C11 C10 99.6(4) . . ?
O2 C11 H11A 111.8 . . ?
C10 C11 H11A 111.8 . . ?
O2 C11 H11B 111.8 . . ?
C10 C11 H11B 111.8 . . ?
H11A C11 H11B 109.6 . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.085

