# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_abs
_database_code_depnum_ccdc_archive 'CCDC 2491262'
loop_
_audit_author_name
_audit_author_address
'Prof. Alireza Abbasi'
;University of Tehran
Iran
;
_audit_update_record             
;
2025-09-24 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N3 O2'
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.287(3)
_cell_length_b                   9.0210(18)
_cell_length_c                   16.890(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.57(2)
_cell_angle_gamma                90
_cell_volume                     1715.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.989
_cell_measurement_theta_min      1.808
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.09581
_exptl_absorpt_correction_T_min  0.91028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, R. H. (1995).Acta Cryst.A51,33?38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8803
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.808
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  Marresearch
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2613
_reflns_number_total             2949
_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       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    PLATON
_computing_publication_material  DIAMOND
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.066
_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)+(0.0814P)²+0.6362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1630
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C13(H13), C7(H7), C10(H10), C4(H4), C12(H12), C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.04672(13) 0.30579(18) 0.19852(10) 0.0593(4) Uani 1 1 d . . . . .
O2 O 0.39175(12) -0.11170(16) 0.47823(9) 0.0587(4) Uani 1 1 d . . . . .
N1 N 0.35782(14) 0.18115(18) 0.38785(11) 0.0506(5) Uani 1 1 d . . . . .
H1 H 0.418308 0.192409 0.435943 0.061 Uiso 1 1 calc R U . . .
N2 N 0.14944(14) 0.21060(18) 0.33289(11) 0.0468(4) Uani 1 1 d . . . . .
N3 N 0.32592(15) -0.28532(18) 0.37356(11) 0.0519(5) Uani 1 1 d . . . . .
C15 C 0.24983(16) 0.1138(2) 0.38470(13) 0.0458(5) Uani 1 1 d . . . . .
H15 H 0.253234 0.107356 0.443568 0.055 Uiso 1 1 calc R U . . .
C1 C 0.14038(18) 0.2577(2) 0.25342(13) 0.0461(5) Uani 1 1 d . . . . .
C17 C 0.32366(16) -0.1496(2) 0.40474(13) 0.0444(5) Uani 1 1 d . . . . .
C9 C 0.02190(18) 0.3912(2) 0.36172(14) 0.0503(5) Uani 1 1 d . . . . .
H9 H 0.052469 0.464706 0.337817 0.060 Uiso 1 1 calc R U . . .
C16 C 0.23171(17) -0.0422(2) 0.34570(13) 0.0482(5) Uani 1 1 d . . . . .
H16A H 0.152833 -0.077041 0.336355 0.058 Uiso 1 1 calc R U . . .
H16B H 0.237592 -0.038655 0.290147 0.058 Uiso 1 1 calc R U . . .
C3 C 0.36031(18) 0.2268(2) 0.31078(14) 0.0504(5) Uani 1 1 d . . . . .
C2 C 0.25263(18) 0.2571(2) 0.24079(14) 0.0483(5) Uani 1 1 d . . . . .
C8 C 0.06038(17) 0.2460(2) 0.36457(13) 0.0461(5) Uani 1 1 d . . . . .
C13 C 0.0132(2) 0.1385(3) 0.40054(15) 0.0589(6) Uani 1 1 d . . . . .
H13 H 0.037179 0.040364 0.402493 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2540(2) 0.3070(3) 0.16295(16) 0.0660(6) Uani 1 1 d . . . . .
H7 H 0.182655 0.324592 0.116121 0.079 Uiso 1 1 calc R U . . .
C11 C -0.1091(2) 0.3217(3) 0.43081(15) 0.0612(6) Uani 1 1 d . . . . .
C10 C -0.06119(19) 0.4272(3) 0.39404(14) 0.0565(6) Uani 1 1 d . . . . .
H10 H -0.086079 0.525117 0.391197 0.068 Uiso 1 1 calc R U . . .
C4 C 0.4669(2) 0.2507(3) 0.30133(19) 0.0713(7) Uani 1 1 d . . . . .
H4 H 0.538873 0.231627 0.347279 0.086 Uiso 1 1 calc R U . . .
C12 C -0.0693(2) 0.1770(3) 0.43341(16) 0.0658(6) Uani 1 1 d . . . . .
H12 H -0.099164 0.103759 0.458015 0.079 Uiso 1 1 calc R U . . .
C19 C 0.4118(2) -0.3934(3) 0.42721(18) 0.0722(7) Uani 1 1 d . . . . .
H19A H 0.466963 -0.416624 0.401728 0.108 Uiso 1 1 calc R U . . .
H19B H 0.371092 -0.481889 0.431403 0.108 Uiso 1 1 calc R U . . .
H19C H 0.454021 -0.352786 0.483858 0.108 Uiso 1 1 calc R U . . .
C18 C 0.2431(2) -0.3375(3) 0.28917(16) 0.0661(7) Uani 1 1 d . . . . .
H18A H 0.172326 -0.278335 0.270044 0.099 Uiso 1 1 calc R U . . .
H18B H 0.223291 -0.439243 0.293482 0.099 Uiso 1 1 calc R U . . .
H18C H 0.279365 -0.329234 0.248437 0.099 Uiso 1 1 calc R U . . .
C14 C -0.2005(3) 0.3614(4) 0.4654(2) 0.0918(10) Uani 1 1 d . . . . .
H14A H -0.167577 0.347677 0.526898 0.138 Uiso 1 1 calc R U . . .
H14B H -0.268782 0.298847 0.439312 0.138 Uiso 1 1 calc R U . . .
H14C H -0.223460 0.463158 0.452142 0.138 Uiso 1 1 calc R U . . .
C6 C 0.3598(3) 0.3307(4) 0.1546(2) 0.0894(9) Uani 1 1 d . . . . .
H6 H 0.360079 0.365351 0.102821 0.107 Uiso 1 1 calc R U . . .
C5 C 0.4658(3) 0.3021(4) 0.2245(2) 0.0902(9) Uani 1 1 d . . . . .
H5 H 0.537374 0.318033 0.219241 0.108 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 1.232(2) . ?
O2 C17 1.236(2) . ?
N1 H1 0.8600 . ?
N1 C15 1.441(3) . ?
N1 C3 1.377(3) . ?
N2 C15 1.479(2) . ?
N2 C1 1.369(3) . ?
N2 C8 1.433(3) . ?
N3 C17 1.337(3) . ?
N3 C19 1.456(3) . ?
N3 C18 1.459(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.531(3) . ?
C1 C2 1.478(3) . ?
C17 C16 1.520(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.387(3) . ?
C9 C10 1.375(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C3 C2 1.404(3) . ?
C3 C4 1.398(3) . ?
C2 C7 1.396(3) . ?
C8 C13 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.381(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.378(4) . ?
C11 C10 1.389(3) . ?
C11 C12 1.389(4) . ?
C11 C14 1.502(3) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C12 H12 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C5 1.389(4) . ?
C5 H5 0.9300 . ?

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
C15 N1 H1 121.3 . . ?
C3 N1 H1 121.3 . . ?
C3 N1 C15 117.34(16) . . ?
C1 N2 C15 119.01(17) . . ?
C1 N2 C8 121.45(16) . . ?
C8 N2 C15 119.43(16) . . ?
C17 N3 C19 119.46(18) . . ?
C17 N3 C18 124.33(17) . . ?
C19 N3 C18 116.15(19) . . ?
N1 C15 N2 108.08(16) . . ?
N1 C15 H15 108.8 . . ?
N1 C15 C16 112.14(17) . . ?
N2 C15 H15 108.8 . . ?
N2 C15 C16 110.16(15) . . ?
C16 C15 H15 108.8 . . ?
O1 C1 N2 122.16(19) . . ?
O1 C1 C2 122.50(18) . . ?
N2 C1 C2 115.19(17) . . ?
O2 C17 N3 122.45(17) . . ?
O2 C17 C16 120.64(18) . . ?
N3 C17 C16 116.91(17) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 C15 111.20(16) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N1 C3 C2 118.97(19) . . ?
N1 C3 C4 122.0(2) . . ?
C4 C3 C2 119.0(2) . . ?
C3 C2 C1 119.93(19) . . ?
C7 C2 C1 119.89(19) . . ?
C7 C2 C3 119.6(2) . . ?
C9 C8 N2 119.89(18) . . ?
C9 C8 C13 118.6(2) . . ?
C13 C8 N2 121.50(19) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C10 C11 C14 121.8(3) . . ?
C12 C11 C10 116.8(2) . . ?
C12 C11 C14 121.4(3) . . ?
C9 C10 C11 122.0(2) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?

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 168.3(2) . . . . ?
O1 C1 C2 C7 -2.5(3) . . . . ?
O2 C17 C16 C15 8.1(3) . . . . ?
N1 C15 C16 C17 68.0(2) . . . . ?
N1 C3 C2 C1 7.5(3) . . . . ?
N1 C3 C2 C7 178.4(2) . . . . ?
N1 C3 C4 C5 -177.3(3) . . . . ?
N2 C15 C16 C17 -171.57(16) . . . . ?
N2 C1 C2 C3 -7.3(3) . . . . ?
N2 C1 C2 C7 -178.2(2) . . . . ?
N2 C8 C13 C12 177.62(19) . . . . ?
N3 C17 C16 C15 -172.51(18) . . . . ?
C15 N1 C3 C2 23.0(3) . . . . ?
C15 N1 C3 C4 -160.1(2) . . . . ?
C15 N2 C1 O1 161.45(19) . . . . ?
C15 N2 C1 C2 -22.9(2) . . . . ?
C15 N2 C8 C9 134.12(19) . . . . ?
C15 N2 C8 C13 -44.2(3) . . . . ?
C1 N2 C15 N1 50.2(2) . . . . ?
C1 N2 C15 C16 -72.7(2) . . . . ?
C1 N2 C8 C9 -49.5(3) . . . . ?
C1 N2 C8 C13 132.2(2) . . . . ?
C1 C2 C7 C6 169.2(3) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
C3 N1 C15 N2 -49.3(2) . . . . ?
C3 N1 C15 C16 72.3(2) . . . . ?
C3 C2 C7 C6 -1.7(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C7 C6 C5 0.9(5) . . . . ?
C8 N2 C15 N1 -133.39(18) . . . . ?
C8 N2 C15 C16 103.8(2) . . . . ?
C8 N2 C1 O1 -14.9(3) . . . . ?
C8 N2 C1 C2 160.74(17) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C8 C13 C12 C11 0.9(4) . . . . ?
C7 C6 C5 C4 0.1(5) . . . . ?
C10 C9 C8 N2 -178.27(18) . . . . ?
C10 C9 C8 C13 0.1(3) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C4 C3 C2 C1 -169.5(2) . . . . ?
C4 C3 C2 C7 1.4(3) . . . . ?
C12 C11 C10 C9 -0.1(3) . . . . ?
C19 N3 C17 O2 -0.4(3) . . . . ?
C19 N3 C17 C16 -179.8(2) . . . . ?
C18 N3 C17 O2 176.5(2) . . . . ?
C18 N3 C17 C16 -2.9(3) . . . . ?
C14 C11 C10 C9 -179.6(2) . . . . ?
C14 C11 C12 C13 178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
