# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3f
_database_code_depnum_ccdc_archive 'CCDC 2332462'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT
Germany
;
_audit_update_record             
;
2024-02-12 deposited with the CCDC.	2025-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H31 N O3'
_chemical_formula_weight         297.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.0699(3)
_cell_length_b                   9.3359(5)
_cell_length_c                   19.6712(11)
_cell_angle_alpha                92.250(3)
_cell_angle_beta                 96.251(3)
_cell_angle_gamma                103.900(3)
_cell_volume                     896.37(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5750
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      66.63

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microfocus
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13069
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         66.662
_diffrn_reflns_theta_full        66.662
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3133
_reflns_number_gt                2733
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0809P)²+0.2942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     199
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1 C 1.1051(4) -0.0187(3) 0.30965(11) 0.0602(6) Uani 1 1 d . . . . .
H1C H 1.286494 -0.004433 0.335771 0.090 Uiso 1 1 calc R U . . .
H1D H 1.123775 -0.012990 0.260708 0.090 Uiso 1 1 calc R U . . .
H1E H 0.991078 -0.115981 0.317472 0.090 Uiso 1 1 calc R U . . .
C2 C 0.9717(4) 0.1009(2) 0.33291(10) 0.0520(5) Uani 1 1 d . . . . .
H2A H 0.789693 0.086541 0.305905 0.062 Uiso 1 1 calc R U . . .
H2B H 1.084801 0.198586 0.323432 0.062 Uiso 1 1 calc R U . . .
C3 C 0.9375(4) 0.1009(2) 0.40870(9) 0.0475(5) Uani 1 1 d . . . . .
H3A H 1.119312 0.112599 0.435461 0.057 Uiso 1 1 calc R U . . .
H3B H 0.821507 0.003707 0.417797 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8099(4) 0.2219(2) 0.43373(9) 0.0484(5) Uani 1 1 d . . . . .
H4A H 0.924628 0.319107 0.424197 0.058 Uiso 1 1 calc R U . . .
H4B H 0.626999 0.209498 0.407449 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7797(4) 0.2221(2) 0.50965(9) 0.0480(5) Uani 1 1 d . . . . .
H5A H 0.962506 0.233632 0.535877 0.058 Uiso 1 1 calc R U . . .
H5B H 0.663846 0.125195 0.519081 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6543(4) 0.3439(2) 0.53512(9) 0.0470(5) Uani 1 1 d . . . . .
H6A H 0.769480 0.440916 0.525546 0.056 Uiso 1 1 calc R U . . .
H6B H 0.470849 0.332112 0.509184 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6265(4) 0.3436(2) 0.61126(9) 0.0463(4) Uani 1 1 d . . . . .
H7A H 0.809734 0.353665 0.637016 0.056 Uiso 1 1 calc R U . . .
H7B H 0.509468 0.246908 0.620588 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5051(4) 0.4659(2) 0.63786(9) 0.0435(4) Uani 1 1 d . . . . .
H8A H 0.624936 0.563091 0.630241 0.052 Uiso 1 1 calc R U . . .
H8B H 0.323597 0.457919 0.611583 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4736(4) 0.45848(19) 0.71377(9) 0.0416(4) Uani 1 1 d . . . . .
H9A H 0.655439 0.464845 0.739524 0.050 Uiso 1 1 calc R U . . .
H9B H 0.353818 0.360953 0.720887 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3549(4) 0.57870(18) 0.74366(8) 0.0390(4) Uani 1 1 d . . . . .
H10A H 0.177594 0.577545 0.716745 0.047 Uiso 1 1 calc R U . . .
H10B H 0.481047 0.676684 0.740711 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3128(3) 0.55426(18) 0.81825(8) 0.0362(4) Uani 1 1 d . . . . .
H11A H 0.494513 0.572666 0.845835 0.043 Uiso 1 1 calc R U . . .
H11B H 0.218370 0.449302 0.821565 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1483(3) 0.65124(16) 0.84953(7) 0.0318(3) Uani 1 1 d . . . . .
H12 H -0.025559 0.641079 0.818354 0.038 Uiso 1 1 calc R U . . .
C13 C 0.0750(3) 0.59078(16) 0.91730(8) 0.0318(3) Uani 1 1 d . . . . .
C14 C 0.1494(3) 0.90552(17) 0.87331(8) 0.0348(4) Uani 1 1 d . . . . .
C15 C 0.3054(4) 1.0646(2) 0.88725(11) 0.0503(5) Uani 1 1 d . . . . .
C16 C 0.4708(5) 1.1270(2) 0.84131(12) 0.0617(6) Uani 1 1 d . . . . .
H16A H 0.515432 1.231195 0.838425 0.074 Uiso 1 1 calc R U . . .
H16B H 0.542343 1.066509 0.811928 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1874(4) 1.1541(2) 0.93459(13) 0.0635(6) Uani 1 1 d . . . . .
H17A H 0.293214 1.257307 0.937859 0.095 Uiso 1 1 calc R U . . .
H17B H 0.194738 1.115111 0.980114 0.095 Uiso 1 1 calc R U . . .
H17C H -0.003394 1.148519 0.916911 0.095 Uiso 1 1 calc R U . . .
N1 N 0.2908(3) 0.80664(14) 0.85761(6) 0.0318(3) Uani 1 1 d D . . . .
O1 O -0.1172(2) 0.47595(13) 0.91439(6) 0.0424(3) Uani 1 1 d D . . . .
H1B H -0.154(5) 0.437(2) 0.9515(8) 0.064 Uiso 1 1 d D U . . .
O2 O 0.2163(2) 0.65353(13) 0.97217(6) 0.0444(3) Uani 1 1 d . . . . .
O3 O -0.0997(2) 0.86731(14) 0.87498(7) 0.0470(3) Uani 1 1 d . . . . .
H1A H 0.4611(19) 0.8314(18) 0.8635(9) 0.031(4) Uiso 1 1 d D . . . .


_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
C1 C2 1.518(3) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.523(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.523(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N1 1.4509(19) . ?
C12 C13 1.517(2) . ?
C12 H12 1.0000 . ?
C13 O1 1.2582(19) . ?
C13 O2 1.2655(19) . ?
C14 O3 1.232(2) . ?
C14 N1 1.344(2) . ?
C14 C15 1.505(2) . ?
C15 C16 1.353(3) . ?
C15 C17 1.491(3) . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1A 0.832(9) . ?
O1 H1B 0.847(10) . ?

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 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C1 C2 C3 112.92(18) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 114.02(17) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 113.63(17) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 113.85(17) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 113.39(17) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 114.15(17) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 112.27(16) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 114.85(15) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 110.44(14) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 114.84(13) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
N1 C12 C13 111.86(12) . . ?
N1 C12 C11 113.09(12) . . ?
C13 C12 C11 107.61(12) . . ?
N1 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C11 C12 H12 108.0 . . ?
O1 C13 O2 124.44(14) . . ?
O1 C13 C12 116.69(13) . . ?
O2 C13 C12 118.78(13) . . ?
O3 C14 N1 121.04(15) . . ?
O3 C14 C15 121.36(15) . . ?
N1 C14 C15 117.59(14) . . ?
C16 C15 C17 122.30(19) . . ?
C16 C15 C14 118.43(17) . . ?
C17 C15 C14 115.11(16) . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 N1 C12 118.31(12) . . ?
C14 N1 H1A 119.3(12) . . ?
C12 N1 H1A 120.1(12) . . ?
C13 O1 H1B 118.1(17) . . ?

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 178.73(16) . . . . ?
C2 C3 C4 C5 -179.30(15) . . . . ?
C3 C4 C5 C6 179.53(15) . . . . ?
C4 C5 C6 C7 -179.67(15) . . . . ?
C5 C6 C7 C8 179.19(14) . . . . ?
C6 C7 C8 C9 178.32(14) . . . . ?
C7 C8 C9 C10 179.57(14) . . . . ?
C8 C9 C10 C11 175.86(14) . . . . ?
C9 C10 C11 C12 -169.52(13) . . . . ?
C10 C11 C12 N1 -67.83(17) . . . . ?
C10 C11 C12 C13 168.12(13) . . . . ?
N1 C12 C13 O1 158.26(13) . . . . ?
C11 C12 C13 O1 -76.95(17) . . . . ?
N1 C12 C13 O2 -24.97(19) . . . . ?
C11 C12 C13 O2 99.83(16) . . . . ?
O3 C14 C15 C16 -128.3(2) . . . . ?
N1 C14 C15 C16 50.4(3) . . . . ?
O3 C14 C15 C17 29.3(3) . . . . ?
N1 C14 C15 C17 -151.97(18) . . . . ?
O3 C14 N1 C12 -6.2(2) . . . . ?
C15 C14 N1 C12 175.03(14) . . . . ?
C13 C12 N1 C14 -69.70(17) . . . . ?
C11 C12 N1 C14 168.61(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.832(9) 2.156(10) 2.9830(17) 172.8(16) 1_655 yes
O1 H1B O2 0.847(10) 1.773(10) 2.6186(16) 176(2) 2_567 yes

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042



